Archive-author: Karen Shane
Archive-title: Doug and Cindy
Hesitantly Doug entered the shop. He was nervous and was
sure everyone was watching him. But, as he looked around he
saw nobody paying any attention to him so he stepped farther into
the little boutique. It was a specialty shop and Doug was sure
he could get what he needed here. It had taken him a long time
to work up the courage to get this far and he wasn't going to
back down now.
"Can I help you?" said the pretty young sales clerk.
"Uh, well, I'd like to look around first," Doug responded.
"O.K., just call if you need any help, I'll be right over
here if you need anything." And the clerk turned and left him to
wander around the store by himself.
Dougs heart was pounding as he drifted among the isles of
clothing. He had always wanted to check out this tall girls shop
but he had been too afraid in the past. Now he was determined to
go through with it, and he had the hardest part over. He was in
the store now and nothing would stop him from completing what he
had set out to do today.
Towards the back of the store Doug found what he had been
looking for, the lingerie section. He quickly selected a Platex
Thank-Goodness-It-Fits brassire in size 38 nearly B. He looked
at the package and made sure it was the right bra. It was, and
it was in the color he wanted, black, so he turned to the next
He found the Platex panty girdles and picked out a thigh
high style and made sure it was size 7. With both foundation
boxes under his arm he looked around a little more and found some
pretty lace trimmed garter belts. He picked one out with red
satin trim and added that to the growing collection of packages.
Next he journyed deeper into the store and began examining
the rack containing slips. He selected a black lace trimmed
nylon tricot slip in size 38 tall. After assuring himself that
it would fit properly he picked out a pair of sandlewood nylons
stockings and headed for the sales counter.
"Did you find everything you wanted?" Inquired the pretty
Doug stammered for a second, cleared his throat and then
said, "Uh, I think so. Perhaps you could recommend a nice
inexpensive outfit to complete this ensemble."
The clerk looked up from the sales tickets she had been
checking and examined the items he had placed on the counter.
"Well, let's see now. Pretty underthings here deserve a pretty
dress. Did you want a skirt and blouse, or is a dress more in
line with what you had in mind?" she inquired.
"I really hadn't thought about that," Doug returned, "What
do you suggest?"
The clerk was making her way through the isles and Doug
followed close behind. He had left the other articles on the
counter and was startled when the girl turned and held a dress up
next to him and said, "This would look pretty with what you've
already picked out."
Doug turned red as she held the dress against his body. He
wanted to protest, but could not find the courage to deny what
the clerk had infered. The clerk noticed his embarassment and
tried to ease it somewhat, "Don't worry. We get lots of men in
here who like the items we sell. If it does'nt bother me, why
let it bother you."
He thought about it for a minute and felt a little better
with her confiding in him in such a frank manner. "Well, it's
just that I never, well..., I mean I never...,"he stammered.
"Don't worry about it. If you'd like, you can try
everything on in back. We have a special room and no one will
Doug couldn't believe what he was hearing. "Uh, are you
She drapped the dress over her arm and said, "Come on,
follow me." Then she turned and headed back to the counter and
picked up the other packages he had selected earlier. She
continued on to a curtain hanging at the back of the store and
held it open for him.
Doug stepped through and then the clerk entered and pointed
towards another door. "Right in there, no one will disturb you.
If you need any help, just press the little buzzer and I'll come
back and help however I can." With that she handed him the dress
and other articles, turned and left Doug standing there by
Hesitantly, he thought about it and then hurried to the
door. As he pulled the door open he was somewhat surprised to
find such a large dressing room. Inside he found that he could
bolt the door and he quickly did so. He crossed over to the
dressing table and laid the items down.
Doug looked around the room and found that in addition to
the dressing table, there was a stand with half a dozen different
wigs and another dressing table with all kinds of make up on it.
He quickly removed his clothing and hung them from a
hook next to the table. Standing there naked he began to
shake as he removed the lycra panty girdle from its box. He
had selected the thigh high type to help hide his maleness
and quickly pulled the garment from the box. Nervously he
put one foot into the panty and then rapidly slipped the
panty over his other foot. Before pulling the garment up he
pulled his testicles back between his legs and pressed his
thighs together to hold them there.
He then pulled the panties up and adjusted them to the
contours of his body. Next he removed the brassire from its
carton and noticed his hands were shaking badly. He had a little
difficulty fastening the clasps because of shakiness, but managed
to get them hooked properly.
He removed the slip from its hanger, pulled off the tags and
then slid it over his head. The feeling of constriction from the
bra and panty girdle gave him a sense of pleasure. The coolness
of silk against his body from the slip sent shudders of delight
Before trying on the dress he admired his own reflection in
the mirror and marveled at how well he could mimic the female
form. He was delighted with what he saw and then picked up the
dress from the table. After unzipping it full length, he stepped
into the dress and then adjusted the shoulders and bust to his
With difficulty he managed to get the zipper all the way
back up and was just admiring the fit when he heard a knock at
the door. He recognize the clerks voice when she said, "If
you're ready, I've picked out a couple of accessories that will
go very nicely with that outfit."
Doug was scared! He had'nt planned to try the things on in
the store. And now here he was completely dressed in the clothes
he had been wanting so long and someone was at the door. Slowly
he stepped over to the door and drew the bolt back.
The young clerk briskly entered the room and placed some
jewelery items on the table. "My but that's a pretty outfit.
I'll bet you'd really like to wear those things out of here."
Doug was too stuned. "I don't think that's possible. I'd
get into trouble for sure."
"Well listen," she continued, "I'll be closing the shop in a
few minutes and you can come by my place. Here, try a couple of
these wigs on and I'll be back in a few minutes." With that she
left Doug alone to ponder what had just happened.
He picked up the necklace she had left on the table and
fastened it around his neck. After slipping the braclet on his
wrist he realized he had not tried on the nylons or garter belt
yet so he pulled up his dress and slip and fastened the flimsy
garment around his waist.
Doug removed the nylons from the container and gathered one
up in a ball and slowly fitted it to his leg. After hooking the
garters to it he began to put the other one on and was just
fastening it when the clerk returned. Since he had forgotten to
bolt the door after she had departed, she walked in as he was
fastening the other nylon.
"Here," she said as she crossed the room to him "always hook
the straps through your panties. That way if you need to take
your panties down, you don't have to undo everything." With that
she unhooked the garters and threaded the straps through Dougs
panty. After she had it properly adjusted she reattached it to
the nylon and saw that he was finishing the other nylon.
He quickly dropped the slip and smoothed the dress down as
the clerk selected a pretty auborn wig and removed it from its
stand. "Let's try this one," she said as she motioned for him to
set down in the chair in front of the dressing table.
Doug meakly obeyed and she expertly fitted the hair piece in
place. After adjusting the wig, she stepped back and allowed him
to see the full effect in the mirror. He could not believe what
his eyes saw. The reflection in the mirror was beautiful! Even
without make up the red head returning his gaze from the mirror
As the clerk picked up a stick of foundation make up she
said, "My name's Cindy. What's yours?"
"Doug," he responded quietly as she began smoothing the
foundation on his face and neck. Quickly and expertly she
blended the make up in with her finger tips and then selected a
light green eye shadow for his eyes.
"Green will go good with that wig," Cindy stated as she
brushed the light powder on his eyelids. "We don't want to
overdo it though. Here, see if you can apply this lipstick
properly," she said as she handed Doug a tube of rose petal lip
Slowly and carefully he traced the outline of his lips with
the tube and then pressed his lips together. When he finished
Cindy was holding a small kleenex for him to blot his lips
with. "Thanks," he said as he took the kleenex and completed the
Cindy picked up a brush and made minor adjustments to the
wig as she inquired, "Have you been doing this long?"
Doug answered tentatively, "Privately I've enjoyed dressing
as a woman for a couple of years now. But this is the first time
I've ever had the opportunity to share it with anyone else.
That's why I came to this boutique. I wanted to make sure I got
everything in the right size. I must admit, I was quite
surprised with how well you put me at ease in here."
"We get lots of guys in here that are into womens clothes,
but you're the first one I've ever given special attention to,"
Cindy finished with the brush and was satisfied with the
look. "One last thing, we'd better get some shoes for you.
Follow me and we'll try a couple pair on." She headed for the
door and Doug followed after taking one last look in the mirror.
Amazing he thought, absolutely amazing. He followed her out
the door and back to the store. Cindy was standing near the
shoe department and asked him what size shoe he wore. Doug told
her the male size he normally bought and she went over to a rack
and pulled a box down. "Here, let's try these," she said as she
opened the box and removed a pair of woven straw sandels.
Doug sat down and slipped the sandels on. It took him a
second to figure out how the straps laced around his ankel and
then he buckled them and stood back up. "Perfect," he said as he
admired them in the floor mirror.
"Come on then, let's go. I'll get your other things and put
them in a bag. You can change back if you want to at my place."
With that Cindy disappeared in the other room for a minute and
then reappeared with a boutique plastic bag in hand. Doug
followed her as she headed for the door and waited patiently
outside as she turned the key in the lock and dropped the keys in
"I'm parked right around the corner. Let's go across the
street for a quick drink before we take off."
"Gee, I don't know if I'm ready for all this. Maybe we'd
better just get going," he said.
Doug woke from the dream covered with persperation and with
a tremendous hard on. He was in his own bed and could sense his
wifes' body next to him. He thought about the dream and could
recall every detail as if he had really lived the experience. It
disturbed him that he had had the dream again. This was the
third time this week alone and each time it was the same.
If only he could see how the dream ended he thought. Or
better yet, if he could really experience it. Doug got up from
the damp bed and quietly padded out to the kitchen. As he
prepared the coffee pot for the morning ritual, he lit a
cigarette and pondered the dream again.
The aroma of caffine invaded his nostrils and Doug snubbed
out the butt as he reached for a cup. While pouring the hot
liquid he heard Cindy stirring in the bedroom and knew she would
soon be joining him.
"Have that dream again?" Cindy inquired as she joined him at
the kitchen bar. She was the image of his perplexing nocturnal
adventure and he only nodded affirmatively as he avoided her
gaze. "Come on honey, talk about it. It might help if we can
work it out together. I love you dear."
"I don't understand it Cindy," he started, "Why am I having
this same reoccuring dream? What does it all mean?"
"Doug, I love you very much. Maybe if we actually acted out
the dream, it wouldn't bother you anymore." Cindy peered deeply
into his eyes questioningly as Doug turned toward her.
He considered her suggestion and then responded, "I really
don't know. We've been married for two years now and why does
something like this start affecting me so much? I'm no
homosexual and I've never had thoughts like this before. Why
now," he inquired.
"Look," Cindy began, "it's friday and we have the weekend
ahead of us. Let's make reservations at a motel in town and just
get away from here for awhile. The change will be good for us.
And," she lingered for a minute, "perhaps we can explore this a
Doug considered the idea and then stated, "I'll call from
work and make the arrangements. Maybe you're right." As he got
up from the bar and started for the bathroom to get ready for
work Cindy hugged him tightly and placed an affectionate kiss on
his ear lobe.
Doug put the dream from his mind and quickly showered.
Cindy was busy in the bedroom when he left for work and the rest
of the day was quite normal for him. During his lunch hour from
the parts department he worked in, he called and made the
reservations at a Holiday Inn on the outskirts of town. "Maybe
Cindys' right," he muttered to himself as he hung up the phone.
Doug arrived home shortly after five o'clock to find Cindy
waiting in the living room with three suitcases setting next to
the door. "What's this?" he inquired.
"I hope you didn't forget to make reservations. These are
our bags, let's go." With that, Cindy grabbed one of the
traveling cases and headed out the door.
Half an hour later the two were climbing the carpeted stairs
to their room at the motel. As Doug placed the luggage on the
traveling stand Cindy darted into the bathroom and said, "I'll
get a bath ready for you and then call room service for a few
drinks while you relax and unwind from the day."
Doug nodded and absent mindedly flipped on the television
set. A few minutes later Cindy reappeared and informed him every
thing was ready. Entering the bathroom, he noticed she had drawn
a hot bubble bath for him and had placed his shaving gear on the
counter next to the sink. After removing his clothes and easing
into the foamy liquid, Doug heard her requesting a bottle of
champagne from room service.
Cindy came into the bathroom and sat on the edge of the tub.
She let her hand slip into the warm water and slowly swim its way
towards Dougs' naked thigh. Just as she made contact with his
groin they both heard a knock at the door. "Must be room
service," Cindy said as she stood and scooped up the clothing
Doug had dropped on the rack above the toilet.
Cindy had pulled the bathroom door shut when she opened the
door to the hallway to allow the bellhop to bring in the cart
with the champagne. After thanking the bellhop she handed him a
twenty dollar bill and said, "I'd really appreciate it if you
could dispose of these items immediately." With that she handed
the bellhop the clothing she had brought from the bathroom with
The bellhop smiled quickly as he tucked the bill in his
pocket and took the articles she held in his direction. He then
disappeared as she closed the door behind him and locked the
Cindy carried the champage and two glasses back into the
bathroom and sat them on the floor next to the tub. She removed
her blouse and skirt and tossed them out onto the bed as she
lowered herself to edge of the tub again.
Doug admired her ample breast and the way they strained at
the skimpy brassire she was wearing. Cindy filled the glasses
with the bubbely liquid and then handed one to Doug. As he
started sipping the drink, Cindy picked up the razor from the
counter and lowered it into the tub. Doug looked at her
inquisitively as she reached into the water with her other hand
and grasped his ankle.
"Enjoy every minute of this, Doug. I love you and want you
to be as happy as I can make you." Cindy said as she slowly
began drawing the razor along his leg. Doug started to protest
but she merely handed him another glass of champagne and
continued with her task.
Moments later she had finished one leg and was busy with the
other while Doug helped himself to another drink. When she
stopped to admire her handiwork, she noticed he had dozed off and
was sleeping with his arms folded behind his head. Carefully and
ever so gently she began shaving his underarms and was able to
complete the task without awakening him. Satisfied that she had
done properly, she left Doug nap a little longer while she went
into the other room and set about arranging the rest of her
surprise for him.
Doug opened his eyes and felt Cindy massaging his flacid
penis. The water was now tepid and most of the bubbles had
dissapated. "Boy, I must have really been tired. How long have
I been in here?" Doug asked.
"Not long, honey. It's a little past eight. We ought to
get dressed and go down to the lounge for something to eat. Come
on and I'll help you." Cindy stood and handed him a towel. Doug
quickly dried off and then followed her out of the bathroom.
Looking around the room, Doug was unable to find any of his
clothing. He picked up each suitcase and noticed they all felt
empty. "What'd you do with my things?" he inquired.
"Everything you wore in here is gone. I've packed enough
for us for the weekend." With that, Cindy handed Doug a pair of
pastel lycra spandex panties and watched the expression on his
face. Slowly the look of terror was replaced with a peaceful
smile as he reached out and took the garment from her hand.
Tentatively Doug placed one foot in the panty and then
quickly stepped into them with the other foot. As he began
pulling the slinky fabric up his body he felt a sense of urgency
compelling him onward.
After adjusting the hiphuggers, Doug looked at Cindy and
noticed she was holding a matching brassire for him. He put out
his hands to accept the bra and Cindy threaded it over his hands
and up his arms. As he positioned the boned-underwire cups to
his chest, Cindy cinched the garment from behind and hooked the
Doug admired her selection. The bra fit very comfortably.
It was a deep plunge, underwire affair with strech straps and
lace trim everywhere. Before he could inspect the garment any
farther, Cindy was wrapping a combination garter belt, waist
cincher around his midsection.
It too, he noticed, matched the pastel panties and bra. On
each of the elastic garter straps was a small silky ribbon
hanging from a little ribbon bow. Cindy had finished hooking the
hooks and was trying to zip up the zipper. "You'll have to hold
your tummy in as much as possible. I got this a little tight in
order to give you a little better figure." She said.
Doug had a hard time believing what was happening, and, he
had an equally hard time holding his stomach in enough for Cindy
to get the girdle affair zipped up. But somehow she managed and
then stepped around in front of him.
She started threading the garter straps through his panties
and Doug was quick to follow suit with the other leg. After the
eight dangling straps were properly adjusted by Cindy, she handed
him a pair of smoke colored nylons and then went over to the
Doug was busy sliding the smooth silk up his freshly shaven
legs and didn't notice Cindy removing the wig from a hat box. He
was enjoying the slick feeling the material produced against his
bare legs. As he donned the second nylon he became accutely
aware of the erection between his legs. The feel of slippery
legs, the underwire bra and the constriction of lycra spandex
panties were too much for him.
"I thought that might happen." Cindy said as she observed
Dougs prediciment, "so I've got a little idea how to handle that
Cindy crossed the room to Doug and rolled his panties down.
She then stepped behind him and reached through his legs and
grabbed his testicles. As she tugged them back she forced his
rigid cock back and held it against the two smaller sacks. Next
she applied pieces of surgical tape to the head of his penis and
pressed the ends to his crotch. She put one more long piece of
tape across the length of his hard on and pressed the end of it
deep into his anus.
"O.k., now adjust your panties and I'll bet that'll take
care of it," she said.
Doug pulled the panties back up and smoothed them in place.
He couldn't help but admire the appearance of a feminine pubic
mound and glanced at Cindy. She was smiling at the effect of her
handiwork and said, "Here, put this slip on and we'll see what a
little make up will do." With that she handed him a dainty satin
slip of the same pastel color.
Doug quickly slid the slip over his head and let it drop
down his body. He liked the way the lace trim bodice drapped
over his bra, and the way the cool, soft fabric felt. As he
smoothed the garment in place with his hands his body became
charged with a tingling sensation.
Cindy had him set in a chair beside the dressing table while
she sat on the edge of the bed and began by trimming his eye
brows with a small pair of tweezers. After she had thinned them
considerably she picked up a styling pencil and lightly filled
out a soft, feminine arch.
After completing the eyebrows, Cindy dabbed small amounts of
light aqua colored powder to the tops of his eyelids and then
blended it with a cotton swab. Next she applied a Cover Girl
foundation to his cheeks, forehead, chin and neck. She also
blended this with a cotton ball and then applied a light coating
of powder to the same areas.
When she was satisfied with the softness of the skin
texture, she applied a thin coating of blusher to his cheeks and
used her fingers to fade the edges of the blusher. Happy with
the effect she was creating, Cindy removed a mascara wand from
her make up case and applied a thin coat to Dougs eye lashes.
She sat back on the bed and admired her handiwork. "Damn,
you're pretty," she remarked. Doug turned towards the mirror and
gasped at how beautiful and womanly he had become. It was
difficult for him to imagine that beneath the reflection staring
back at him was really a man.
Cindy handed Doug a pair of silver clip on earrings to put
on while she fastened a matching silver necklace around his neck.
When she finished with the necklace she bent down and hooked a
smaller version of the necklace around his left ankle.
"Just a few more details and we'll be ready, honey." She
said as she produced a dark brown wig Doug immediately recognized
from her collection of wigs at home. She slipped the trusses
over his scalp and fitted it to his head. With a small styling
brush she teased a few curls into place and patted a few others
with the palm of her hand.
"After you have your dress on, we'll take care of your hands
and then we can go." Cindy then pulled a beige ruffled blouse
from the hangers she had previously hung in the closet and helped
Doug into the garment. As she buttoned the buttons in back, he
straigtened the collor and fluffed up the ruffles in front.
Doug glanced in the mirror and noticed the ruffled blouse
created the illusion of a larger bust line than he actually had.
He turned back to find Cindy holding a tweed, straight skirt for
him to step into. He pulled the garment on and Cindy zipped and
fastened the clasps in back for him. As he reached under the
skirt to adjust his slip, Cindy retrieved the matching jacket
from another hanger and handed it to Doug.
After tucking his blouse into the skirt, Doug slipped into
the jacket and turned to admire himself in the mirror. Cindy
handed him a package and said, "Here, see if you can put these
plastic finger nails on while I get dressed." She then
disappeared into the bathroom while he tore open the package.
When he finished with the nails, Doug walked around the room
and enjoyed the feel of female garments swaying against his body.
The sensations were electric and he felt ecstatic. He was still
enjoying the slick nylon charge when Cindy stepped out of the
bathroom dressed equally as beautiful as he was.
She stepped into a pair of patent leather spiked heels and
said, "Perhaps you'd better wear these lower heeled slippers. It
takes a little getting used to walking around before you'll be
able to handle high heels." She then handed him a pair of beige
leather low heeled slippers and he quickly slipped them on his
nylon covered feet.
Doug stood before her; both the picture of feminity. She
stepped closer and hugged him tightly. They kissed passionately
and both could sense the arousal in the other. Cindy pulled away
from the embrace and said, "Now for the lipstick and we're ready
to go. You can carry this little purse for effect and I'll take
mine along with everything we'll need." She handed Doug a tube
of pale pink lipstick and watched as he traced it on his lips.
When he finished applying it, she gave him a small beige handbag
and he placed the lipstick in it.
She picked up her purse and opened the door. "Well, let's
go to the lounge and get something to eat. I'm famished." Doug
followed her out the door and stood in the hallway as she locked
Pangs of guilt and apprehension invaded him as another
couple appeared down the hall. Cindy saw the fear in his eyes
and quickly linked her arm in his. "Believe me darling, no one
but I know who, or what you really are. Come on, let's go."
Cindy led him down the hallway and could feel his sense of
confidence returning. The closer they got to the stairway, the
more she could tell he was loosening up and begining to enjoy the
"I'll do the ordering as your voice may give you away." They
descended the stairs and crossed the lobby to the lounge. Doug
glanced about and noticed the clerks paid them no mind. A few
guest mingled in the lobby and they too paid no attention to the
two well dressed women headed for the lounge.
The hostess guided them through the dimly lit bar to a small
table near the rear of the lounge. Before departing she accepted
Cindys order for drinks and then disappeared amid the tingle of
glasses and music from the band.
Soon their waitress delivered the drinks and Cindy selected
entrees from the menu for them both. Before their meal arrived,
the waitress brought another round of drinks and said, "The
gentlemen next to the bar hope you'll accept these with their
compliments." She nodded towards a table with two well dressed
business men and sat the glasses down.
Doug and Cindy both glanced toward the men. Cindy smiled
and tipped her glass in the air to the men and then turned back
to Doug. "See, I told you no one could tell but me."
Doug felt a little nervious and wispered to her, "What do we
do if someone trys to hit on us?"
"Honey, this is your fantasy. Enjoy it. Just do what ever
comes naturally. But when it's all over, we're the ones that are
Doug smiled at Cindy and rubbed his knee against hers under
the table. The feel of nylon against nylon excited them both and
Cindy responded by slipping her hand beneath the table cloth and
placing it on his leg.
As he finished his drink she slowly slid her hand up his leg
and toyed with the top of his nylon. Doug felt the tension of
his garter strap as she traced the outline of the fastening. He
also felt his growing erection and was thankful Cindy had been so
thorough in taping his member back.
When their meal arrived, Cindy ordered another round of
drinks and both attacked the food with a passion. As they
finished the dinner Doug saw the two gentlemen head toward their
table. He pressed his knee against Cindys and indicated for her
to look in their direction.
Cindy looked up as the two arrived at the table. She smiled
demurely as the taller of the two asked her, "Would you two young
ladies care to dance?"
The music was slow and so was she in responding, "Why, I
think we'd love to. Wouldn't we Darla?" She looked directly at
Doug when she said that and could tell he was nervous. Then she
accepted the outstreched arm of the shorter of the two men and
accompanied him to the dance floor.
"Darla, eh? Pretty name, shall we join them?" said the
Doug placed his hand on the mans arm and slowly stood up
from the table. The two made their way between the other tables
and were soon on the dance floor.
Fighting instinct, Doug allowed the man to place his arms
around him and then tried hard to follow his lead. As if it came
naturally, Doug found out he had no trouble assuming the proper
role and soon the two were tightly pressed together.
The music drifted among them as Doug became keenly aware of
the bulge in his partners pants. He found it exciting that
another man was becoming turned on by him and he increased the
pressure of his own pelvic area against his partner. The two
danced slower, while Doug sensed the urgency of his own masculine
Rythmatically he began pressing his hips harder and harder
against his dance partner. The husky gentlemen responded with
equal pressure and Doug found himself placing his head deeper
into the mans shoulder.
As they continued to dance, Doug became very aware of the
mans hand pressing more firmly against his back. He could feel
his partners hand against the hooks of his bra and this only
excited him more. He did not realize the music had stopped when
he felt the mans hand slid from his back and drift across his
With a meaningful pat on Dougs feminine derrire, the man
said, "We'll have to do it again, Darla." And as a gentleman, he
escorted Doug back to the table.
Doug pursed his pink lips and smiled affectionately at the
gentleman as he retook his seat. Cindy was now joining them and
her partner asked, "How 'bout if we join you two and make an
evening of it?"
Doug nervously pulled a cigarette from Cindys purse and
placed it in his lips. He was searching for the lighter when his
dance partner offered a light. As he puffed on the cigarette he
heard Cindy feign an excuse of returning to awaiting husbands
upstairs and the two men reluctanly bid farwell and departed.
Cindy signaled the waitress for the check and told Doug, "I
think it's time the two of us get out of here." Doug nodded
eagerly and departed with her after she had signed the room
number to the tab.
They arrived back in their room minutes later without
incident and Cindy was only too happy to kick off her shoes and
sink into the bed. Doug retrieved the champagne from the
bathroom and poured them both a drink.
"Well, what did you think of your dream now that you've had
a chance to act it out?" Cindy inquired.
"It was a little scary at first. And then when those guys
asked us to dance, I nearly died. Do you know he got a big hard
on and kept rubbing it against me."
Cindy chuckled and said, "Well can you blame him. Look at
yourself, you really are a beautiful woman. But right now I want
that beautiful woman to climb on top of me, or better yet," she
hesitated, "I'd rather climb on top of that beautiful woman."
Doug dropped to the bed and the two clung desperately
together. "Wait," Cindy said, "let's shed a little of this
clothing first. I've got another surprise for you."
With that she hopped up from the bed and crossed the room to
the closet. Deftly she removed two identical floor length satin
pegnoir sets and returned to the bed side. "Take everything from
your slip on out off," she said as she began also stripping to
just her panties, garters, nylons and bra.
Doug was quick to follow suit. As soon as the two were shed
of their outer garments, Cindy handed one of the gowns to Doug
while she placed the other on her own body. Before climbing back
in bed she turned down the covers and then placed her small over
night bag on the floor next to the bed.
Doug laid back on the bed and realized he was extremely
excited by the wisps of nylon drapped across his body. Cindy
knelt and stradled his hips. The rustle and feel of nylon tricot
was everywhere. She slowly started rocking her hips back and
forth and could sense Doug enjoyed the smooth frictionless feel
of the mingeling female garments.
Gently she reached beneath Dougs buttocks and pulled the
tape restraining his testicles. When she freed his semi-rigid
cock she rolled the front of his panties down and pulled his
growing member out. After she hooked the panties beneath his
warm balls, she leaned over and retrieved two soft vibrators from
her night bag.
As Dougs penis became harder she rolled off of him and
quickly shed her own panties. Cindy then lubricated both toys
and gently inserted one in Dougs quivering anus. As she lowered
herself upon his erection she guided the other vibrator into her
"Oh baby," Doug moaned. He was so worked up from all the
excitement of the evening he knew he would not be able to hold
back much longer.
Cindy knew he was near the edge. She sat up as straight as
she could and buried his cock deep within herself. Dougs hands
were massaging her anal cheeks as he worked the vibrator in and
out of her.
Cindy used one hand to work the vibrator back and forth in
Doug while she kneeded his nipples beneath the bra he wore. With
a violent shudder Doug shot cum deep in Cindy.
She orgasimed twice as he spent his load. They both
remained motionless for an eternity and then slowly Doug started
pumping in and out of her again. Within seconds he had regained
a rock hard rigidity that Cindy knew would last throughout the
"Oh darling, darling," she moaned, "I love you so much."
Doug continued to pump as she rubbed her hands all over the
nylon and lace he wore. With each stroke of her hand the
intensity of his movements increased. The effect of lace was so
great that Cindy knew she had discovered a means to highten the
pleasure both of them shared.
After they had both enjoyed countless orgasims they lay
cuddled together in a mixture of sensuous clothing. Cindy could
not believe the profound effect her suggestion of acting out a
dream had had on Doug. Or, for that matter, the effect it had on
her. She slowly drifted off to sleep vowing she would continue
to live his dream.
Doug woke first. The realization of saturday morning at the
motel flickered through his mind. Awareness of the lingerie he
wore flooded his senses. Cindy was still snuggled up next to him
and he enjoyed looking at their two bodies dressed similiarly.
He caressed her with one hand while he caressed his own body with
She woke slowly. She was vaguely sore and suddenly
remembered why. Cindy smiled as she opened her eyes and leaned
closer to Doug to kiss him. "Feel like a morning swim," she
Doug looked at her questioningly.
"I've got a really nice one piece suit for you. You'll love
it!" She said.
Cindy hopped from the bed and dashed to the bathroom. Doug
sat up and looked into the mirror. The wig was a little awry,
but the make up was intact. He adjusted the hair piece and
flipped on the television set.
Cindy reappeared from the other room and tossed him the
swim suit. She had alreay pulled on a skimpy suit and had towels
in her hand.
Doug examine the swim suit and looked puzzled. "How we
gonna pull this off," he asked.
"Strip down to just your panties, I've got another idea."
He did as she bid and then Cindy re-taped his flacid penis
back the way she had last night. "Now, pull on the suit and
Doug stepped into the fucia swim suit and pulled it up. The
skirted bottom hid any traces of his masculinity and Cindy helped
him adjust the blouson top. She then inserted a pair of breast
prosthesis into the built in bra of the suit and adjusted them in
"Well, maybe," Doug mused as he looked into the mirror.
"But what about the wig?"
"You'll just have to keep your head out of the water, or
wear this swim cap." Cindy said as she tossed him a rubber cap.
She grabbed a pair of towels from the bathroom and picked up the
key from on top of the television. "Come on, it's early. We'll
have the pool to ourselves."
Doug followed her down the hall way and she was right, they
had the pool to themselves. After about a half an hour two
skinny teenagers showed up and began splashing each other in
another corner of the pool. Doug and Cindy decided they had
better not press their luck so they got out of the water and
With towels draped over their shoulders they headed back to
the room and were just crossing the second floor lobby when the
dance partners from the previous evening came up the stairway.
Cindy saw the two men and smiled. "Morning," she said as she
The two men returned the smile and said "Good Morning" in
unison. As Doug and Cindy passed by them, the husky fellow that
had danced with Doug reached out and patted him on the ass as he
walked by. Doug let out a gasp while Cindy just chuckled.
"That's something I don't know how to handle." Doug told
Cindy as he closed the door behind him.
"You'll learn how to play the part." She responded while
stepping into the bathroom and adjusting the shower. "How about
we shower together?"
Doug quickly joined her. When they had finished showering,
Cindy laid out a complete outfit on the bed for Doug. Standing
with the towel wrapped around himself, he carefully examined the
items and then picked up the sanitary belt and pad.
"That will probably be more comfortable than wearing tape
all day. And it'll be a lot easier to remove when ever you need
to go to the toilet." Cindy told him.
Doug nodded in acknowledgement and slowly stepped into the
contraption. Before pulling it up all the way, he pressed his
testicles back and then wiggled the pad into place. The straps
rode high on his hips, while the end of the belt disappeared into
the cheeks of his ass.
Next, he donned the light blue nylon tricot panties and
admired the lace trim around the waist and leg bands. He
marvelled at how the sanitary pad produced a feminine pubic
mound. He quickly picked up the corset and was examining the
garment while Cindy dressed.
He noticed it had heavy boned stays. The corset laced and
hooked in the back, so Doug slid the affair over his arms and
positioned it in place. Cindy stepped over and drew the laces
tight and then hooked the corset for him.
He slipped the silicone prosthesis in each cup of the
corsets brassire and then sat on the edge of the bed. While
putting on the nylons and fastening them to the garters of the
corset, Doug could feel an erection growing. He was thankful the
sanitary pad held him secure.
Cindy tossed him an embrodiered lace slip and he quickly
fitted the sensuous garment to his body. "All of these clothes
fit so nicely, and they feel terrific. How did you ever get the
right size in everything?"
"You forget, dear, I've been buying your clothes for a long
time. It wasn't hard to convert your men clothes size to womens
clothing." She said.
Doug enjoyed the feeling of nylon swaying against his body
as he crossed the room to the closet. "Which dress is mine?" He
"Why don't you try the blue one hanging next to the outfit
you wore last night."
Doug removed a sky blue dress from the hanger and stepped
into it. He pulled the dress on and slipped his arms into it.
As he adjusted the puffy sleeves, Cindy zipped it up for him. He
liked the mandrin collar and the way the garment clung to his
curves. "It's beautiful," he murmered.
"I thought you'd like it." Cindy handed him her braclet
watch and he fastened it to his wrist.
She motioned for him to set at the dressing table and then
carefully began applying a light make up. "We'll skip the
mascare for daylight wear. I think this blue will match your
dress." She said as she dabbed a light powder blue to his
She blended on small amounts of Cover Girl foundation and
said, "We don't want to over do it or that'll just call attention
He picked up the lipstick she had set before him and slowly
traced the outline of his lips. Cindy was fastening a pair of
dangling blue plastic ear rings to his ears and Doug sat
patiently observing the process in the mirror. The illusion
being created excited him and he could feel his rock hard penis
straining at the cotton pad.
When Cindy finished she handed him the wig and had him place
it on his head. She took a small brush and teased the hair piece
until confident it looked proper. "There, I think we're done."
Doug slid on a pair of woven straw sandles and fastened the
straps around his nylon encased legs. The feel of the nylons
rubbing together as he moved his legs about was too much for him.
He hoped Cindy did not notice as he shuddered and felt a warm
liquid oozing between his legs. He was thankful for the sanitary
napkin and made a mental note to take along a spare.
When he stood up, Doug took one last look in the mirror and
couldn't believe the picture of feminity that stared back at
him. "Let's go." Cindy said as she opened the door and waited
for him to join.
"Where we going." Doug inquired as he stepped into the
hallway with Cindy.
"I thought we'd get some breakfast and then tour the art
museum." She answered.
They walked side by side to the stairs and then crossed the
lobby to the front door. Again Doug noticed that no one paid any
attention to them and he felt comfortable that he could
masquerade so easily.
"I'll drive." Cindy said as she opened the passenger door
They had not gotten out of the parking lot before
discovering they had a flat tire. "Damn," Cindy said, "of all
times for this to happen."
She slammed the door as she started to walk around the
vehicle to assess the situation. Doug was comming around the
front of the car to join her when he heard, "Can we be of
Doug and Cindy looked up to see their two dance partners
nearing the dissabled car. "Hi, I'm Dave and this is Dan." Said
the fellow Cindy had been dancing with. "We'll have that fixed
in no time. Got a spare in the trunk?" He inquired.
"Oh, thank you." Cindy said as she went around the car and
placed the key in the trunk. "I don't know what we'd have done
if you hadn't come along."
Dave removed the jack and wrench from the trunk as Dan set
the spare tire on the ground. While Dave began positioning the
jack, Dan stepped next to Doug and inquired, "How's Darla this
Dougs heart was pounding rapidly as he whispered, "Got a
little case of laringitist."
"Aw, that's too bad." Dan responded. "Maybe you'd like to
join us for breakfast. We were just planning to go down the
street here to the pancake house. How about it?"
Doug shot Cindy a glance and saw her perk up at Dan's
suggestion. "That would be wonderful, wouldn't it Darla."
Doug nodded meekly and wondered how he would handle the
situation. Dave had finished changing the tire and was putting
everything back in the trunk. "Why don't you park your car and
we'll walk down to the restuarant. It's only half a block away."
Cindy agreed and backed the car into the slot. Dan offered
his arm to Doug and he limply placed his wrist in the crook of
Dans arm. He was glad he still had the false finger nails on as
they gave his hands a distinct female appearance.
Dave escorted Cindy as the two couples strolled down the
side walk. Doug began enjoying the attention Dan was showering
upon him. He even appreciated the way Dan held doors open for
him and treated him as a woman. He was glad Dan offered to order
for him so that 'Darla' wouldn't strain her throat.
Nearing the end of their meal, Doug felt Dan place his hand
upon his nylon covered leg and his eyes went wide open. Cindy
saw the look in her mates eyes and realized what must have
happened. She smiled back at Doug and said, "Enjoying yourself,
Doug could only manage a week nod and continued to pick at
the food on his plate. Dans hand had gotten bolder and was
slowly inching up his leg. He could feel Dan toying with the top
of his nylons and tracing the outline of the garter.
Cindy saved him by announcing, "I need to use the powder
room. Care to join me Darla?"
Doug and Cindy quickly crossed the dining room to the womens
rest room. Once inside, Doug looked around and saw they were
alone. "He's putting his hands all over me. I don't know what
"Don't be so worried honey. He can't do anything as long as
we're in a crowd. Enjoy it, and tease him a little. Surely
you've been teased by some girl in the past."
She made sense, Doug thought. "Well maybe," he started, "I
just didn't expect anything like this to happen."
"Have all the fun you want, 'cause when we go home we're the
ones that are together. I love you and I don't care what I have
to do to make you happy." Cindy stopped talking when another
women entered the room. She checked her own make up in the
mirror as she handed Doug a tube of lipstick.
They both returned to the table and Dave and Dan stood up to
hold the chairs for the women. Doug had not been seated for
more than a minute until he felt Dans' hand once again on his
nylon covered knee.
As Dans fingers began creeping under the dress, Doug let his
own hand rest upon the thigh of his partner. Dan accepted the
touch as a signal and quickly slipped his fingers to the crotch
of Dougs panties. Feeling the sanitary napkin, Dan momentarily
withdrew his hand and then replaced it on the panty covered pad.
Dan slowly began applying pressure to the pad and
rhythmatically started rubbing it up and down. The feel of the
moist pad against Dougs flacid penis caused him to get an instant
hard on and he found himself becoming quite excited. As Dan
continued to rub the pad, Dan let his own hand drift farther up
Dans thigh until he felt a familiar bulge.
Cindy and Dave had lapsed into small talk, while it appeared
Dan and Doug were slowly finishing their meal. Doug heard Dave
mention something about stepping outside for a cigar and Cindy
agreeing to join him. Dan too quickly announced he would take
care of the bill and Doug looked up to see Cindy departing with
With the other couple gone, Dan increased the frequency of
his movements and Doug was breathing quite heavily. He grasped
Dans bulge with the tips of his false fingernails and pinched
lightly as he began stroking the stiffening member in time to the
movements Dan was applying to him.
Doug exploded warm, thick juices as he felt Dan shudder and
cease his activities with the pad. Doug squirmed slightly to
allow the last few drops to drain from him into the awaiting
sanitary napkin. For the second time today he was glad the pad
was in place as he with drew his hand from Dans crotch.
Doug had a contented smile on his face and noticed Dan was
wearing a sheepish grin. Both glanced down and saw a small spot
appearing as the tent shaped fabric of Dans trousers began to
sink back down. "I guess I'd better head back to the room." Dan
He left some bills on the guest check and then escorted
Darla from the restuarant. Cindy and Dave appeared to be deep in
an animated conversation and nearly missed them as they came out.
They all quickly returned to the motel where Dan bid farewell as
he rapidly crossed the lobby and bounded the stairs two at a
Dave looked questioningly after him and then turned and
shrugged to Cindy and Darla. "I guess I'd better go make sure
he's alright. Will we see you girls again?"
Cindy smiled at Doug and then said, "We'll be in the lounge
again tonight. Perhaps we can slip away from our husbands again.
They're out playing golf now, and are usually too tired to go out
when they've completed eighteen holes."
Dave bid them farewell and then departed. "What ever
happened after we left?" She inquired of Doug.
"I think I have to go up to the room for a minute too. You
said to enjoy myself, and well, I just did what he did to me."
Cindy chuckled to herself and thought outloud, "You sure
learn fast." They returned to the room and before Doug had a
chance to replace the soiled napkin, Cindy crossed the room to
him and gently pushed him onto the bed.
Caught unaware, Doug fell back on the bed as Cindy bounced
on to it next to him. She rapidly slid her hand under his dress
and began massaging the panties against his napkin. He
instinctively parted his legs for her and felt the wettness from
his earlier excitement.
Cindy hiked her own dress above her thighs and straddled
Doug with her head facing his feet. She bent over to reach her
night case and he nuzzled his face against the fabric of her
panties. She continued massaging the sanitary pad against his
growing erection as she pulled one of the toys from her case.
Doug could feel his penis growing as he buried his face in
Cindys pantied rump. He began to nibble on the tricot barrier
and could feel her vaginal lips slidding beneath the soft fabric.
His own panties strained at the pressure of his emerging hard on
pushing against the pad Cindy was massaging.
Cindy slid the leg band of his panties aside and lubricated
the object in her hand with the dampness from his pad. As he
continued to tease her with his mouth against her own panties she
slid the soft, firm vibrator into his anus. She slowly worked
the toy in and out as she increased her movement of the sanitary
napkin against his rigid cock.
Doug felt like he was in heaven. He nibbled harder and
caught her lips between the fabric of her panties as she plunged
the vibrator back and forth in his anus. The sensation of nylons
and tricot intermingling with the constraint of the corset and
her actions on his body were over powering.
Cindy knew he was nearing the moment and she released his
cock from the pad which held it. It pointed straight in the air
as she climbed from his body and quickly stripped her own panties
as quick as she could. She turned and positioned herself above
him and then lowered her body to his. Her moistness engulfed him
as she continued to plunge the vibrator in and out.
Garters snagged against garters as lace mixed with nylon and
nylon. He exploded like never before. She quivered, then
shuddered and exploded too. Wetness drained everywhere as they
continued to pump feverishly.
And then they were motionless.
Cindy sat breathing heavily as Doug grasped for air. The
vibrator was buried deep within him as he remained buried deep
Moments later, an eternity, he slowly felt himself fading.
As his penis returned to a flacid state, she slowly withdrew the
vibrator. Cindy contracted her muscles and he popped from within
her. At the same instant she totally with drew the toy and
dropped it to the floor.
"We've never, I mean never, had sex with such urgency. I
think it was great!" Cindy said as she got up from the bed. She
picked up her panties and stepped back into them as Doug sat up.
He could not say anything. He knew she was right. He got
up and headed for the bathroom after picking up a fresh napkin
from the box Cindy had in the suitcase.
"Now you really see why the garters go underneath the
panties, don't you." Cindy called out to him.
Doug only responded by flushing the toilet and completing
the task at hand. Seconds later he stepped from the other room
and joined Cindy on the edge of the bed. "I guess the museums
out for this morning. What other little surprises did you have
"Oh, I've got a little idea in mind you might enjoy."
Cindy got up from the bed and opened the door. Doug
followed her out and they both headed for the car. She drove for
a few minutes and Doug realized they were headed downtown. She
circled one block a few times and then pulled into a vacant spot
in front of an adult book store. Doug smiled.
She opened the door for him and they both stepped into the
store. It was still early in the day and few other customers
were among the racks of magazines and video cassettes. Cindy
walked from one isle to the next until she spotted the section
containing literature on female impersonators. Doug stepped next
to her as she picked up one magazine from each holder and began
cradling them in her arm.
After she was sure she had one of each selection she
wandered around a bit and then settled in front of the counter
containing toys of every description. She selected a few items
and the gaunt male clerk nonchalauntly dropped them into a bag.
She paid him and then turned to find Doug still browsing through
the titles she had made her choices from.
Cindy caught his attention and signalled him that she was
ready to leave. Doug replaced the magazine he'd been thumbing
through and accompanied her to the car. "I got one of each and
we can look at them later back at the motel. For now, let's head
to the mall. I have a few more things to pick up and we can grab
some lunch at one of the lounges there."
Doug was only to happy to be dressed as he was and didn't
really care where they went. He enjoyed the breeze as it wafted
gently through his wig and chilled his lace clad body. The trip
to the mall passed rapidly as Cindy drove among the week end
She led him through the window shoppers and squalling
children to a womens longerie shop at the end of one passageway.
It only took her seconds to scoop up oodles of pastel colored
panties and deposit them in Dougs arms. She selected a few more
packaged panties and dropped them on top of the growing armful
held by Doug.
"When we get home, I'm going to get rid of all your cotton
underwear. If what's happened to us in the last two days is
caused by these, I intend to keep you well dressed from now on."
Doug caressed the items he held and considered the words she
said. He could feel his manhood growing and realized what she
was telling him was the cause for it. As he walked behind her
the constant strain of the napkin against his cock and the
thought of such beautiful under garments caused him to become
Cindy picked out a couple of varieties of teddies and panty
slips and also handed them to Doug. His arms were so full he had
to get a basket from next to the counter to carry everything she
was getting. When he returned to her, Cindy handed him another
armful of silk and lace.
The basket was overflowing when she finally decided to add a
few brassires to his growing collection of feminine attire. As
he waited patiently while Cindy paid for the items he discovered
he was unconsciously squeezing his thighs together rythmatically
and was causing his rigid cock to strain even more at the pad.
He watched the young teenaged clerk carefully folding and
placing the wealth of silk and nylon in packages and he pressed
his thighs tightly together one last time. He felt the warm,
damp liquid exploded from within and fill the waiting sanitary
napkin. For yet another time today, he was greatful for the
security of the pad and hoped no one noticed the little shudder
he gave as the final drops spent from his penis.
They left the store and wandered among the mall. Doug
savoured the way his softening member slid among the lubrication
of the pad and he likened the feeling to that of being buried
deep within Cindy.
They enjoyed a leisurely lunch in one of the mall
restuarants and then continued window shopping until deciding to
return to the motel. Cindy returned to the car for the last of
the days purchases as Doug sank into a chair and absently flipped
on the television set.
When Cindy returned from the car, she found Doug had fallen
asleep in the chair with his wig slightly awry. She quietly
removed it and then began sorting items from the days shopping
spree. After she had packed everything away, she took a hot bath
and then prepared one for Doug.
She awoke him with a kiss and said, "I've got a nice hot
bath ready for you. Why don't you relax in the tub awhile and
I'll pick out some things for us to wear tonight. "
He nodded and groggily made his way to the bathroom. He
slipped out of the blue dress before going in the bathroom and
drapped it over a chair. He kicked off the sandels and then
padded into the bathroom clad in his dainty underwear.
He let the slip fall to the floor as he began unfastening
the garters and removed the nylons. The corset was a little
difficult to remove by himself, but he managed to shed to garment
and stood for a second looking at the reflection of his pantied
backside in the mirror. He could see the indentation of the
sanitary belt beheath his panties and suddenly realized it was
He quickly peeled off the remaining garments and then slid
into the tub. The hot, bubbly liquid comforted him as he picked
up the safety razor Cindy had left on the side of the tub. Even
though his legs did not need it, he slowly drew the razor against
them and made sure they were closely shaven. The feeling created
by the ritual caused him to acknowledge a deep feminine urging
from somewhere within himself.
Doug pondered the emotions welling up and then asked Cindy,
"Were you serious about what you said when we were in that one
"Definetely," she responded. "The way soft womens clothing
has excited you the last two days is fantastic. I intend to see
that you remain as happy as you've been this weekend. Besides,
who will know?"
He had dried off, and wrapped the towel around himself the
way Cindy usually did, high on his chest. He paused and gazed at
his reflection in the mirror. With all the make up washed off,
you didn't notice his eyebrows had been plucked and took on a
feminine appearance, he thought.
Cindy came into the bathroom and began preparing a bath for
herself. "I've set everything out for you on the bed." She
said. "I'm going to get cleaned up while you dress, and then
I'll slip into something and we'll go down to the lounge again
Doug left her alone while he went out to check what she had
selected for him. He found the sanitary napkin and belt on top
of all the articles she had piled on the bed and he quickly
stepped into the garment and tucked his maleness between his
legs. Before pulling the pad into place, he sprinkled some of
her fragrant powder on it and then snuggled it against his soft
She had chosen a deep plunging front closure brassire for
him and he had little difficulty fastening the bra. He admired
the way the clasp fitted securely behind a pretty little bow of
ribbon and the mounds of decorative lace on the cups of the bra.
Before putting on the matching garter belt, he slid the prothesis
in place and marveled at the way they giggled as he moved about.
He fastened the lace belt around his waist and then decided
to paint his toe nails with a shade of nail polish that would
match the false nails he still wore on his fingers. After
completing the task, he put on the mint colored slip Cindy had
left for him and then sat on the bed while the polish dried.
Cindy stepped out of the bathroom and detected the aroma of
nail polish. "Oh, good idea." She said as she dropped the towel
from around her and slipped into her own brassire. Doug quietly
noticed she had selected matching intimate apparal for herself
and he was pleased they could share such lovely attire. As she
pulled on her panties, she said, "Why don't you sit down over
here and I'll fix your make up."
He obediently took the chair next to the dressing table and
Cindy expertly applied a light cream foundation to his face and
neck. "Now, blend it in with this pad." She said as she handed
him a small foam make up pad.
Doug smoothed the foundation until he could not detect a
line between the make up and his skin and then Cindy started
applying a frosty eye shadow on his eye lids. After she had
finished each eye she handed him the mascara and watched as he
brushed the dark cream on his lashes. Next, he picked up the lip
stick she had placed before him and carefully traced the outline
of his lips.
She used a small brush and dabbed a light coating of blusher
on his cheeks and then took an eye brow pencil and rounded out
the contour of his brows. Doug picked up her perfume and placed
a small drop behind each of his ears and on each of his wrists.
He returned to the side of the bed and put on his nylons and
then pulled on a pair of dainty, pretty hip huggers made of
lycra spandex. He smoothed and brushed the slip in place and
could feel the urgings welling up within himself. The soft
fabric clunge to his body and the cool feel of lace against nylon
Cindy tossed a pair of opened toed high heels on the floor
in front of him and he slipped his feet into them. She had
thoughtfully selected large heels so that he would not have too
much difficulty in learning to walk in them. He tested his
ability to manuver with the heels by strutting around the room.
He noticed the heels caused his calfs to appear even more
feminine and he stood admiring his legs for a minute. Cindy
brought him a soft woolen skirt and helped him step into it. She
fastened the clasp and then handed him a matching mohair sweater.
Doug slid the sweater over his head and adjusted the cowl neck to
fall partially over his back.
Cindy gave him a large beaded necklace and ear rings to put
on while she finished dressing and Doug stepped over to the
mirror to accomplish the task. When he finished putting on the
jewerly he picked up the wig and placed it on his head. He used
her styling brush to fluff it out and brush a few stray hairs in
place. Cindy smiled at how naturally he performed the deed and
noted how beautiful he looked.
Without saying anything to each other, they picked up their
purses and left the room. Cindy dropped the key in her purse as
they started down the hallway toward the lounge. Doug noticed
the heels caused him to sway slightly as he walked and his skirt
rippled rythmatically as they descended the stairs to the lobby.
A few guest glanced casually at them as they crossed the
lobby and entered the shadows of the lounge. Cindy spotted
Dave and Dan seated at a far corner of the adjacent dining room
and noticed Doug had also seen them. Dan had risen from their
table and was making his way toward them. "Looks like we're in
for a little more fun." She wispered to Doug.
"Good evening Cindy. How's the throat Darla?" Without
waiting for a reply, Dan said, "How about joining us for diner.
We just got here and haven't ordered yet." He took Doug by the
arm and began escorting the two to their table. Cindy walked
behind the two and chuckled inwardly at the way Dan had placed
his arm around Darla's waist.
Dave stood up and held Cindys chair for her as Dan assisted
Darla in taking a seat next to him. "I take it your husbands
won't be joining you for diner this evening." Dave said as he
took his own seat again.
"They've got some kind of business meeting and should be
returning around ten o'clock or so." Cindy said. She knew that
would give them enough time for a little fun, but would still
provide Doug with the excuse he may need later.
"Well, at least let us have the pleasure of your company
until then." Dan said as he placed his hand on Darla's knee.
Doug smiled. He we go again, he thought to himself. At
least Cindy had put a time limit on it, he thought, and he was
grateful for that. He started to whisper something to Dan, but
the band began playing a loud, fast rendition of some familiar
song and all chance of conversation was lost.
Somehow, Dave managed to place orders for them all with the
waiter standing at their table now and Doug heard him order a
large bottle of champagne. The waiter disappeared shortly and
then returned with a cart bearing the beverage and fine glasses.
He watched as Dave sampled the bubbly liquid and nodded approval.
Glasses passed around and they all shared the champagne as Doug
felt Dan's hand begining its upword trek.
Doug had finished a third glass of champagne by the time Dan
had his fingers toying with the edge of the sanitary pad. In an
effort to keep his wandering fingers from exploring beyond that
point, Doug placed his own hand on Dans crotch and could feel the
mans soft bulge respond to his touch.
The waiter appeared with their dinner and Doug coyly brushed
Dans hand from between his legs. He crossed his legs to prevent
further advances from Dan and enjoyed the meal before him. Dan
ate feverishly and they all drank heartily from the dwindling
supply of champagne.
Dave had managed to signal the waiter for another bottle as
they finished their meals and he quickly replenished the empty
bottle as he cleared a few items from the table. Doug was
thankful they were so close to the band and could not carry on
conversations at the table. He was also begining to feel a
little gidish from all the champagne he had consumed and hoped he
wasn't getting careless in the illusion he was trying to
Somehow the four managed to deplete the new bottle of
champagne in less than two songs from the band. Dave signalled
the waiter once again and then signed the check and motioned for
them all to leave.
Dan escorted him from the lounge as Cindy took Daves arm and
accompanied them to the lobby. "Why don't we stop up to our room
and have a quick night cap before bidding ado?" Dave said to the
Doug looked at Cindy and found her agreeing to the
suggestion. He wasn't sure what to do and was quickly hurried
along by Dans insistent pressure on his waist. They crossed the
lobby to the elevator and were wisked to the second floor before
he had a chance to think of anything.
They entered Daves room and soon discovered the two were
sharing adjoining rooms. Dan opened the small passageway to his
room and quickly disappeared from sight. Dave offered Cindy a
chair by the window as he picked up the plastic bucket from the
sink and said he would fetch some ice. Alone for a second in the
room, Doug looked questioningly at Cindy and realized she too was
feeling the effect of the champagne.
Dan returned from the adjoining room carrying a small bong
and stopped in front of the television set to light the marijuana
packed tightly in the bowl. He drew deeply from the mouth piece
and then passed the bong to Doug. Darla accepted the bong and
hesitated briefly before inhaling the rich pungent smoke into his
lungs. He passed the bong to Cindy and she too inhaled deeply on
the mouth piece.
Dave returned with the ice and rapidly mixed drinks for them
all before joining in the activites already in progress. Cindy
enjoyed watching Doug squirm nervously in his feminine attire as
Dan began running his hand up and down Darlas back. She stood up
and crossed the room to the television and flipped it on.
"I'm afraid it may be the wrong time for either of us to
fully demonstrate our appreciation, but," she said as she stepped
over to the light switch and turned it off, "if you'd care to lay
down on the bed, perhaps we can at least show you a little bit of
Dan and Dave needed no further prompting. They both got on
the bed and laid down. Cindy took Dougs hand and pulled him
along as she neared the bed. She let his hand go as she knelt on
the bed next to Dave and began unbuckling his trousers. Doug
hesitated and then mimiced Cindys actions by unbuckling Dans
He watched her roll Daves cotton briefs down and expose his
growing cock. Dans rigid member was already straining at his own
briefs as Doug pulled the waistband over the stiff, erect cock.
He saw Cindy brush her hair away from her head as she lowered her
lips toward the now hard cock and realized what he must also do.
He wrapped his hand around Dans cock and began massaging it
as he lowered himself to a seated position on the bed. Cindy was
now taking Daves organ in her mouth as Doug lowered his head to
Dans eager cock. He placed the tip of it in his mouth and let
his tounge dance upon the head of the cock as he continued his
stroking motions on the long shaft.
Doug could taste a hint of salt as he realized Dan was
becoming extremly excited. He let the shaft bury deeper into his
mouth and pressed his lips firmly around it. His hand moved down
from the shaft and cuped the two hairy balls as he began slidding
his lips up and down the thick cock. He found that his own cock
was begining to strain against the sanitary napkin and he started
squeezing his thighs together as he had done earlier today at the
store with Cindy.
Doug gribbed the sacks of skin in his hand tightly as he
continued to pump his lips up and down the shaft. He could feel
Dan tensing and knew it would only be seconds before he exploded.
Doug sensed his own urgency and locked his legs together as Dan
began spending his load. He felt the warm liquid hitting the
roof of his mouth as his own orgasim spilled into the napkin. He
took everything Dan offered and then traced the length of his
shaft with his tounge as Dan laid motionless.
He felt Cindy place her hand on his shoulder and looked up
to see her headed through the adjoining doorway. He quickly
followed behind and saw her pick up a small plastic bag from the
dresser as she opened the door to the hallway. He pulled the
door behind him as she said, "Small price for them to pay." And
then saw her drop the plastic bag of marijuana into her purse.
They quickly made their way down one flight of stairs and
through the hallway to their room. Doug was thankful they had
not given their room number out as he locked the door behind
them. Cindy was stepping out of her dress as he drew the
"I'm going to run down to the store and get a bottle. Why
don't you get comfortable and I'll be right back." Cindy had
pulled on a pair of levi's and was just slipping into a sweat
shirt when Doug realized what she had said.
She left before he could say anything, so Doug lit a
cigarette and relaxed on the bed for awhile. He picked up the
package of magazines they had bought earlier and began thumbing
through them absentmindedly. The sight of so many she-males
brought him to a state of ecstasy quicker than he thought
He gazed at the glossy color pictures of professional female
impersonators and could feel his cock sliding in a sea of
lubrication as it grew larger. The pictures of such beautiful
men draped in silken finery brought him near the edge and Doug
put the magazines down as he realized he was breathing heavily.
He got up from the bed and shed the skirt and angora sweater he
had been wearing.
After hanging up the garments he let the slip slid down his
hips and fall billowing to the floor. He picked up a pegnoir set
Cindy had left on top of a suit case and put the frilly nightgown
on. He then donned the matching sheer robe and laced the gown at
Doug returned to the bed and had just laid down when Cindy
returned carrying some sodas and a bottle of rum. She deposited
the containers on the counter next to the sink and grabbed the
plastic bucket for ice. While she went for ice, Doug mixed two
drinks and awaited her return.
"Oh good. I see you found the gown I left out for you.
Pretty isn't it?" Cindy said as she plopped some ice in each of
the glass Doug held.
"Yes. I like it."
Cindy placed a box near the bed and then quickly peeled off
her own outer garments. She stood near the bed as she up ended
the glass and drained the last drops of rum and coke from her
glass. Doug mixed her another as she dropped to the bed and then
he too joined her on the bed.
"Lay on your tummy, here." Cindy said as she patted the
mattress next to her. Doug did as she asked and then felt her
hand as she slowly stroked the back of his leg. Cindy allowed
her hand to toy with his the edge of his panties as she reached
into the box next to the bed. She withdrew a soft, firm rubber
penis with a strap on it. She stood next to the bed and strapped
the artificial devise to her hips and then knelt on the bed next
Before doing anything else, she pulled another rubber penis
from the box and slid the leg band of her own panties aside. She
inserted the second dildo in herself and released the leg band of
her panties so that the crotch of the soft fabric held the toy in
With the rubber penis dangling from the straps around her
hips, she crawled between Dougs legs and leaned forward. The tip
of it pressed against the sanitary napkin and she reached down
and pulled his panties down. She pulled the napkin aside and
then pressed the head of the shaft against his anus.
Dougs own erect cock strained at the pad as he felt Cindy
pressing harder with the dildo. As she rocked back and forth the
rubber cock slid into his ass and he raised his hips instictively
to allow her better access.
Cindy drove the false appendage deep within Doug and could
feel the second dildo deep within herself. He let out a gasp as
the shaft buried deeper and then felt Cindy sink into a rhythm of
pumping the dildo in his ass.
As she pressed the rubber cock into him, Dougs own cock slid
among the lubricant he had previosly deposited on the sanitary
napkin. With each thrust she made, he pressed back against her
while pressing his own thighs together.
Cindys tempo had increased and she began massaging her clit
with one hand. Dougs breathing matched the frequency of Cindys
thrusts and he felt himself explode as she shuddered rapidly and
plunged the dildo as deep as she could.
She sat there a long while with the dildo buried deep in
Dougs anus and then unstrapped the device from her body. She
rolled over next to him and slid the other dildo from between her
own legs. She dropped it to the floor and then slowly pulled the
rubber cock from Dougs ass and dropped it next to the first.
Spent and exhausted, they both found sleep a welcome
companion. Even deep asleep, Doug could sense the frilly
garments clinging to his body and he retained a nocturnal
erection that slid among his own juices as he ocassionaly tossed
Morning came too soon, but Doug awoke with a sense of
urgency and rapidly became aware of the straining pad between his
legs. Cindy was still asleep and he let his hands drift over the
soft gown draping his body. The feel of nylon tricot against his
body excited him even more, so he rolled his panties down and
freed his throbbing penis from its prison.
As Cindy slept, he found himself manipulating his cock
through the gown and realized he was going to climax soon. Not
wanting to be apprehended, he quickly pushed his manhood back
into the sanitary napkin and rolled the panties back up. Just as
he finished adjusting the waist band of the hip huggers he felt
himself exploded once again into the napkin. The warm, moist
liquid ran from his cock and trickled between the napkin and his
buttocks. He enjoyed the sensation and laid motionless while the
warmness crept deeper and traced the contours created by the pad
against his ass.
When he could no longer feel the warmth, Doug quietly got up
and padded off to the bathroom. He adjusted the shower and then
ever so slowly, slipped the pegnoir set off and admired the
reflection of his scantily clad body in the mirror. He had to
admit that he really loved the feminine under garments he was
wearing. With great reluctance, he slowly removed the nylons,
garter belt, panties, bra and sanitary napkin and stepped into
He was just finishing drying off when Cindy woke and joined
him in the bathroom. "You should have woke me sooner. We
haven't got long before check out. I'm going to take a quick
shower too, and then we'd better get going. I'll pick out some
things for you in a minute, why don't you try putting on your
make up." She didn't wait for a reply as she stepped into the
shower and realized she hadn't felt so refreshed in a long time.
Doug followed her suggestion and began by applying a light
foundation. He remembered what she had taught him earlier about
not over doing it, so he sparingly applied the foundation and
then blended it in. He put the mascara on lightly also and then
carefully used an eyebrow pencil to fill in his brows. He
selected a pale color lipstick and was just finishing with it
when Cindy popped out of the bathroom. As she busied herself
with choosing various clothing for the two, he finished off by
dabbing a light coating of eyeshadow to his eyelids and then
complimented himself as he stared at the reflection in the
He crossed over to the bed and picked up the fresh sanitary
napkin Cindy had placed on the top his clothing pile. With a
deftness usually reserved to an art practiced for a long time,
Doug slipped into the sanitary belt and threaded the napkin in
place. He tucked himself away and adjusted the napkin to hold
him secure as he picked up the long line brassire and slipped it
over his arms. Somehow he managed to hook all eight of the bras
hooks and noticed that the increased pressure from the long line
bra caused his loose flesh to swell and create an illusion of
cleavage. He quickly tossed out the notion of doing without the
prosethisis and slipped the artificial breast in place.
Next, he pulled on the full cut panties and picked up the
girdle Cindy had selected for him. He struggled to pull the
constraining item on, but soon had it adjusted properly. He
followed by slidding into a knee length slip and then sat on the
bed to put on his nylons.
He completed the outfit with a simple cotton blouse and a
dark, knit skirt that she had also laid out on the bed. When he
had fastened the clasp and pulled the zipper up, he put on the
same woven sandles he had worn the day before and picked up the
wig he now thought of as his own.
Cindy had already taken one load of luggage to the car, so
Doug picked up a few more of the things in the room and carried
them down to the car. Cindy passed him in the lobby and told him
she would get the last of their belongings and be right back.
While waiting in the car, he picked up one of the magazines
Cindy had purchased yesterday and began thumbing through it. He
read with interest, the letters submitted by readers describing
how they had been introduced to the world of cross dressing. As
he read the detailed accounts he could feel his sanitary napkin
straining against his growing erection.
Cindy returned with the last of the luggage from the room
and they started for home. "I really enjoyed this weekend." Doug
confided in her. "In fact, I kind of hate to see it end."
"Oh, it's not ended. When we get home, it's just begining."
Doug pondered her words as she manuvered through the Sunday
traffic. The pleasure he experienced dressed as a woman was
over whelming and he savoured the drive home. Ocassionally he
would shift in the seat to glimpse something out the window and
would quickly be reminded of the tight girdle and nylons he wore.
Doug could'nt imagine being happier.
Cindy pulled into the underground garage at their apartment
and the two women stepped from the car. A quick ride up the
elevator and short walk down the hallway brought them to their
own apartment. As he closed the door behind them, Doug could'nt
help but reflect how his whole attitude and outlook had changed
from just a few days ago when he stood in the same spot.
Cindy had disappeared into the bedroom and Doug headed that
way to see what she was up to. When he entered the room he saw
her standing before his dresser with a couple of drawers pulled
open. He stood hypnotized as he watched her scooping out
handfuls of his male cotton underwear and drop them in a paper
bag. She really was doing what she said she would, he realized.
"From now on, you'll wear pretty lace panties under
everything you wear. When you're home on the week ends, and
after work, I'll expect you to wear at least a bra, too." Cindy
told him as she began putting oodles of pastel colored frilly
garments in the now empty drawers.
Her words, and the thoughts cascading through his mind,
caused Doug to become acutely aware of the stiffness returning
between his legs. He watched her pick up the bag full of male
underwear and carry it out to the trash chute in the kitchen
hallway. He knew she ment what she had just said as he watched
the bag disappear down the chute.
Cindy busied herself with the coffee maker and Doug sat down
on one of the bar stools at the breakfast bar. She finished
pouring the water in and said, "In a couple of months, I'll be
able to style your hair and you won't need a wig any longer. Of
course, you can use any of the ones I have now until then."
"I noticed in one of those magazines that there are some
clubs and organizations in the area that offer support for
couples like ourselves." Doug said tentatively, "Perhaps we
could investigate them."
"If you like, but from now on, I intend to see you become my
sister as well as my husband." She said. "It will be wonderful
being able to share so much more with you. I only wish we'd have
discovered this sooner."
The aroma of caffine drifted through the kitchen so Doug
retrived two cups from the counter. He had kicked off the
sandles in the bedroom and marveled at the way his nylon covered
feet felt as he crossed the linolium floor. The tug of the
nylons against his girdle excited him and he could feel the
elastic stretch slightly as he walked.
"Let's go try on a few things I think you might like. I've
got a lot of cloths in the back of my closet that might fit you
just perfect." Cindy said as she accepted the cup of coffee Doug
held out for her.
They returned to the bedroom and she quickly started tossing
various articles from her closet onto the bed. Doug watched
silently for a few seconds and then unhooked his skirt and
stepped from it. He shed the blouse he had been wearing and
picked up a black one piece jumpsuit from on top of the growing
He managed to zip up the jumpsuit without assistance and
then noticed the girdle created unsightly lines through the skin
tight fabric. "You'll have to learn to wear different types of
underwear depending on what you'll be wearing." Cindy said as
she noticed him checking his appearance in the mirror. "Panty
hose would be best for something like that."
He shed the jumpsuit and tried on a few more garments. He
noticed that with every new piece of feminine apparal he tried
on, he became more excited and the straining at his sanitary
napkin increased. He stepped out of the house dress he had just
tried on and stood in just the matronly under garments Cindy had
provided at the motel this morning.
Without having to say anything to her, Cindy looked deep
into his eyes and then slipped out of her own skirt and blouse.
She crossed to the bed and brushed the pile of clothing aside as
she laid down. Doug quickly joined her and as he began kissing
her deeply he felt her unzipping the girdle at his waist. She
rolled the heavy garment down his hips and then he assisted by
removing it with the nylons still attached.
The slip pulled taugnt against his panty clad ass as he
rolled back toward her and embraced her once again. The feeling
of her breast pressed hard against his own bra clad chest caused
him to become more excited and he loved the sensations shooting
throughout his body.
Quite by surprise, Doug felt her pressing an anal plug into
his ass and he welcomed the sensations it created. Cindy buried
the plug as far as she could and then pulled his rigid cock from
beneath the napkin and through one leg band of his panties. He
wasted no time in mounting her and thrusting his eager cock deep
between her open legs.
With each penetrating thrust, Doug could feel the plug
within himself. Cindy was becoming more excited and he could
feel her hands pressing hard against the long line bra hooked
behind his back. He continued to pump deep into her and then
felt her move one hand down to his quivering asshole. With each
thrust of his cock deep within her, Cindy pressed the plug with
His movements increased in frequency corresponding to the
pressure Cindy placed upon the plug. Within seconds he exploded
dynamically and felt her shudder with her own climax as she
pushed the anal plug as deep as she could.
They lay spent and coupled together for long moments as each
tried to regain their breath. After a few minutes Doug could
feel himself loosing rigidity and withdrew to lay at her side.
He saw that deep satisfied look on her face and knew she had
needed him as much as he had wanted her.
"This is the reason I plan to keep you in skirts." She
said. "You're just so much more sexually active, I'm going to
see to it that you always have lace and nylon on your body."
Doug smiled to himself as he trudged off to the bathroom for
a quick shower. She was right, he thought to himself, the frilly
garments did cause him to need her more. He stripped naked and
relaxed as the hot water streamed down his body. Moments later,
he dried off and returned to the bed.
Cindy had put all of the clothing away so he pulled open
one of his drawers and fingered the fine silk now his to choose
from. He selected a pair of floral patterned hip huggers and a
matching whispy floral brassire. He tossed the frilly underwear
on the bed and then took out a new sanitary belt from the box she
had put in his drawer.
The new belt was more like a string bikini and it took him a
second to discover how to thread a napkin in place. He quickly
learned how to adjust the belt and then started to pull it in
place. He hesitated for a second after tucking his flacid penis
back, and then picked up a bottle of hand lotion on the dresser
and traced a small line of lotion along the inside of his pad.
As he pulled the napkin securely against his body he could feel
the cold lotion come in contact with his penis and then felt the
lotion spread along the shaft of his manhood. As he walked over
to the bed to retrieve his bra and panties he could feel the
slippery lubricant and it reminded him of the feelings he had
experienced so often the last couple days.
He quickly pulled on the hip huggers and slipped into the
flimsy bra. After hooking the clasps behind his back he decided
not to use the prosthesis and went instead to the closet. He
selected a sleeveless tank top blouse and a pair of pink stretch
shorts to wear. He put on the pretty apparel and then joined
Cindy who was now watching television in the living room.
(to be continued -- if there is enough demand)