Events of the last two months have changed my life completely. I met my
lover, Debby over a year ago, and we started our relationship after I
changed jobs. Our physical relationship has been fireworks ever since
our first night in bed over six months ago. It was as if we had just
discovered sex. We wasted no time getting acquainted. This lady's
performance in bed, or the floor, or wherever we get the urge, can be
described as outstanding. One of the things that we explored early in
our relationship was anal sex, and it became a regular part of our
sexual repertoire. We usually indulge in an ass fucking at least once a
day. Her response to having my cock up her rear passage causes me to
get even harder. She said that she had tried anal sex before, but with
me it was great. When I fuck her ass, she enjoys it so much. She can
fuck me for hours that way and stay continually turned on. Her favorite
position is when I lay on my back and she eases my dick up her ass.
After seeing how turned on she gets when I fuck her ass, I began to
wonder what it was like. After all, I have an ass too! One of the great
things about our relationship is the honesty and openness. After another
one of our great sex bouts, I asked her if it really felt that good.
She said that it was her greatest turn on. Well, if she can cum that
way, I reasoned that I should be able to also. She just smiled and said
that we should investigate that. One of the other nice aspects of our
relationship is that we move between roles, sometimes she is the
aggressor and sometimes I am. She said that has created problems in her
previous relationships, but I really enjoy it. We discussed the fact
that there is a bit of the other sex in all of us, some masculine and
some feminine. After all, we have both hormones in our systems, don't
we? It was then that I confessed that several years ago I had gone in
drag to a Halloween party and I had enjoyed it a lot. It was then that
we decided to explore that aspect of sexuality a little further.
That next Friday, she came home from work with a new outfit for me and
makeup. She had bought a leather skirt, a red silk blouse, a garter
belt and black hose, and a wicked pair of black five-inch heels. First
I was sent to the bathroom and told to shave, everything. Off went the
moustache, and hair on my legs and for good measure I shaved my crotch.
After my shower, she went to work on my face. After my face was done, I
donned a curly dark wig that she had. When I looked in the mirror, I
was shocked. I looked good, I would have asked myself out. I put on a
bra with some water balloons, and the garters and hose. I then
slipped into the skirt and blouse. For the first time in my life I
felt really dressed up. I felt sexier than I ever had in men's clothes.
After she had gotten dressed, she decided to go out so she could show
off her new "girl" friend. When she pulled into a topless bar, I got
worried. She explained that this was the perfect place to go, I liked
to go to them as a man, they were dark and the men in there would think
we were hookers, so I should get lots of attention. After a few drinks I
got more comfortable in my role as a lady. I decided to go play a
little pinball. While I was on the machine, a tall, good looking guy
came up and began fondling my ass. On one hand, I was really enjoying
the attention, but I was a little scared that he might discover my
secret. He started nibbling my ear, and invited me to leave. I
responded in my best imitation female voice that my girl friend and I
had other plans for the evening. I left him and headed for the ladies
room to cool off. When I returned to the table, he was gone and Debby
said that we should go home before I got into trouble.
On the drive home, she said, "Now you know what we have to put with all
of the time!" I had very mixed feelings at that point, although I had
enjoyed the attention, the feminine side of me was coming out I had this
fear of being discovered. When we got back home, Debby told me to sit
down and let her fix me a drink. I was calming down a bit with my
Scotch and water when the doorbell rang. She told me to stay seated
while she answered the door. It was our friend from the bar. I was
panicked. How did this happen? Debby invited him in and offered him a
drink. I did my best to remain calm, and excused myself to the bedroom.
Debby came in and told me that this was her was of fulfilling my
fantasy. She said, "You always wanted to know how good it felt to be
ass-fucked, well, you are about to find out." It was too late to back
out now. She was right, I did want to find out, but I had kind of
expected a strap-on dildo or something, not real live cock.
She said, "Let's go get him ready." I followed her out of the bedroom
and headed for the couch. After we sat down, Debby asked him if he had
ever made it with two girls at once. He was delighted with the idea.
She grabbed my hand and we took our places on either side of him on the
couch. As she went to work on one ear, I did the other. Debby began to
unzip his fly as I unbuttoned his shirt. Debby had his hard eight inch
dick in her hand and was slowly masturbating him as I slipped his jeans
off. Debby help his hard dick up and motioned for me to go down on it.
I began to suck his dick in the same way I like to have mine sucked.
While I was doing this, Debby was getting undressed. She moved around
and took off my skirt. We then laid him out on the couch.
Debby then grabbed me and kissed me deeply. It was then that I realized
that this guy still thought that we were both women. While Debby
explored my mouth with her tongue, he started feeling my ass. Debby
broke off our kiss and asked him if he wanted to eat her pussy. As she
settled on his face she pulled me over his crotch. His hard dick was
slick with cum. Debby smiled as I eased his cock up my ass. I could
hear him groaning as I felt his cock move into my ass. After I became
accustomed to the feel, I began to slowly move up and down on his cock.
I was so turned on by then, that I was ready to cum any moment. Debby
grabbed my dick and began to stroke it. I was now feeling the
tremendous turn on that she knew all so well, and she could tell that I
understood. As I relaxed, I knew the pleasure of feeling a good hard
dick inside me. I began to cum, not just an ordinary cum, but the kind
of orgasm that women feel. It washed over me, and lasted for a long
time. When I looked in Debby's eyes as she rode his face, I could tell
that she was cumming too.
When he came, I came again, I could feel him shooting into my ass. He
kept driving deeper into me and I was loving it. I could feel his cum
splashing into my bowels, and I came again. When his dick shrank, I
uncoupled myself and put on my panties. He lay there, totally fucked
out. He sat up and said that he really couldn't take any more. He got
dressed and we both kissed him at the door. After he left, Debby and I
had a good laugh, he never even caught on. I had explored another side
of my sexuality that not too many men ever get a chance to do. I had
thoroughly enjoyed the experience and I now knew what it was like to be
fucked in the ass.
Since then I have been able to truly enjoy both sides of my sexuality.
Few people realize that everyone has a little bit of both sexes in them,
and even fewer have the opportunity to enjoy both sides of their being.
I have fallen even more in love with Debby since that night, and we have
explored even more exciting experiences since then. One evening we
included one of her girlfriends in our special relationship. We have
opened up sides of each other that few people get the chance to explore
nd it's only a going to get better.
Enjoy...... Love.......... Huggs ........ Shauna ........