Related Free Sites Related Free Sites
All Me | Teen Stories | Taboo Stories | Porn Stories

Back to more "Virgin" and "First time" Sex Stories

Teen Sex Stories
Virgin Stories - First Time Sex Situations

Welcome to the TOP Teen Sex Story Sites!

Archive-name: First/

Archive-author: Bobbi C.

Archive-title: Education of Bill, The

Part 1

We had moved into the new Condo a month or so ago. It was nice

enough, but I was seventeen, and starting to feel the urges that

a young boy of that age should start feeling. It was a city

high-rise building with its own pool, but most of the tenants

were older than I. My friends lived a good distance away, so I

really only saw them at school. I was a bit of a loner in a lot

of ways, so that did not bother me all that much. I guess I

should tell you that my name is Bill.  

I spent a lot of time at home except for a part-time job that I

had delivering groceries for the market on the first floor of

the building. I sort of enjoyed the pool, so I spent a lot of

time down there. It was late spring, and warm enough already for

swimming. I usually went for a dip when I came home from school

just before I went down to the market to start my job. There were

a few women there, and I enjoyed watching them in their bathing

suits, but they were all too old to be approachable by a boy of

my age. Some of them looked at me too, and I liked that.  

There was one especially that always seemed to be watching me

when I came down for my daily swim. She was in her early to

mid-thirties, and while not as pretty as the models that I looked

at in the magazines that I kept in my secret drawer, was very

pretty indeed. She was about 5'6" tall, and well built. She

always seemed to prefer bikinis to any other sort of swim suit.

She also seemed to like me sneaking looks at her.  

She was there today too, and wearing a skimpy green bikini that

got my hormones raging. I horsed around in the pool, and surfaced

in front of her a few times to get a better look. She smiled at

me each time I did. Finally it was time to go to work. Dad was

away on a business trip like he always seemed to be, and mom was

working late. That was normal for us, so I just dried off, and

got ready for work.  

Things at the market went as they did on any other day. There

were the usual rush orders from the tenants that had to be

delivered before dinner, so I busied myself with running up and

down in the elevators like always. Finally it was seven o'clock,

and time for me to go home to do homework. Mr. Cucci, the owner,

said that there was just one more order to go, and since it was

in the building and a charge order, I could take it, and then

just go straight home. I picked up the large bag, and headed out

the door to take it where it belonged.  

The apartment to which the order was destined was on the

twenty-first floor, so it took a few minutes to get there. I

really did not want to go home to that homework. I would be alone

as usual since mom would not get there until about nine. I rang

the bell at the apartment, and was greeted by the woman whom I

had seen in the bikini down by the pool earlier.  

She was dressed in a blue dress with buttons down the front. Her

darkblonde hair hung down to her shoulders, and on her feet she

had blue leather pumps with high spike heels. She looked

beautiful, and I could not help staring for a moment when she

opened the door.  

"Oh! Hi," she said, "you're the boy from the pool, aren't you?

Could you bring that into the kitchen for me?" I nodded. It was

about all I could manage at that point. I carried the package

into the kitchen, and heard her close the door to follow me.  

"Thanks," she said when we reached the kitchen. "I don't think

that I could have managed that on my own, and I know the sort of

muscles that you have from seeing you outside." I thanked her for

the compliment, and placed the bag on the counter. "There," I

said. "I like that pool a lot. I've see you out there too." 

"I know you have," she said with a knowing smile on her face.

"What's your name?" I told her my name, and she said, "Mine's

Judy. We are always down by the pool together, so we ought to

know each other. You are working late tonight, aren't you? Cucci

usually brings things up himself when I call this late." "No," I

answered, "this is my last delivery. I go after this." 

"Oh?," Judy said with a touch of irony in her voice. "I guess

your mom has dinner waiting?" "Nah," I answered, "mom won't be

home for a couple of hours yet. I just have to read a few pages

of History, and then watch television until she gets there." 

Judy looked at me strangely for a moment, and then her face

changed back into a smile. "Why don't you stay here for a little

while? I'm all alone, and I would not mind the company. We could

watch television, or talk, or something. If we're friends now,

we should get to know each other a little. What about it?" 

It did not sound like a bad idea. I was a little tired of

spending all that time at home alone anyway, and she looked and

smelled so good. I would like to sit with her for a while.

"Sure," I said. "I can do my homework later. It isn't much." 

"Great," Judy said. "Why don't you go sit on the sofa, and I'll

get us a couple of sodas, that is... unless you would like a

beer?" "No," I said, "soda is fine. I don't think that mom would

like it if she smelled beer on me when she came home. Maybe

some other time" Judy laughed at this, and said, "Okay, you go

on inside, and I'll be there in a minute." 

It did not take long for Judy to join me on the sofa. She put two

sodas down on the coffee table, and we each took one for a sip.

"You spend a lot of time hanging around here. Don't you have a

girlfriend, or someone to pal around with?" "No," I answered, "my

friends all live elsewhere, and I don't have a girlfriend. I just

like being alone." "No one likes being alone," Judy said in a low

voice. "You do like girls, don't you?" I was a little surprised

by the question, but I answered, "Yeah, but I just don't know any

real well." 

Judy shifted a bit on the sofa, and the skirt of her dress hiked

up just enough for me to see above her knees, and a bit of her

thigh. She noticed where I was looking, but did not do anything

to adjust her skirt. "You have gone out with a girl?," she asked.  

I was becoming a little uneasy with the way her questioning was

going, but I was also becoming rather aroused with looking at

her. She was wearing a perfume that was getting to me too! I

liked her, and I wanted to be her friend. I also wanted to talk

to someone about the things that I was feeling. My dad was away

too much for me to get a good talk going with him, and mom was

not the right one to talk to. I decided to see just where the

conversation was going to go.  

"No," I said, "I've never been out with a girl on a real date. I

dance with them sometimes when I go to the school dances, but

that is about as far as things have gone. I don't go to many

dances anyway." Judy looked me straight in the eye, and asked,

"Then you're still a virgin?" "Yes!," I blurted out. The question

had hit hard. The last thing that a boy wants to admit to a woman

like Judy is that he is a virgin, but the question had taken me

by surprise. I had answered truthfully, but I was sort of already

regretting that I did.  

"That's all right," Judy said. "It won't be a permanent

condition. Have you ever kissed a girl?" "No," I answered not

knowing what she had in mind. "Would you like to kiss me?," she

asked. This was definitely not what I had expected when I came

up here, but I had to admit that I did want very much to kiss

her. "Yes," I said. "Could I do it?" 

Judy leaned closer to me, and brought her face close to mine. The

aroma of that perfume filled my nostrils, and I could feel

other parts of me lower down reacting too! I pressed my face to

her's, and our lips met. I had never felt anything like this

before. I did not know what to think about it, but I did know

that it felt very good!

"There," Judy said when she broke the kiss, "now you know what it

feels like to kiss a girl. Did you like it?" That was a silly

question. I answered, "Yeah! It was nice. I never kissed anyone

but my mom and my aunt. This was different." Judy giggled. "Well,

I should hope so," she said. "Would you like to know more about

women?" I eagerly said, "Yeah!" 

"Put your arms around me, and we'll try another kiss," Judy said.

She slid over on the sofa, so her thigh was pressing against

mine. That felt good too! I put an arm around her back, and she

nestled into it. Again our lips pressed together, and again I

felt those same stirring in my crotch. It was all I could do to

keep from messing my pants! We kissed longer this time, and I

could feel her breasts pressing against my chest. I moved my hand

down a bit, and felt her bra under her dress. She did not

protest. We broke the kiss, and Judy said, "Do you like my

breasts?" I swallowed hard, and said, "Yeah," in a strained

voice. "Would you like to see them?" "Yeah!," I said.  

Judy sat up on the sofa, and unbuttoned her dress down to the

waist. Under it, she was wearing a bra of aqua lace. It was

sheer, and I could see the shadow of the dark circles of her

areola and nipples through it. "Would you like to touch them?,"

she asked. "Yeah," I answered.  

I cupped her breasts in my hands, and lifted them. They were

large and firm, and weighed more than I had expected. I had seen

them under her bikini top out by the pool enough times, but I

never thought I would get the chance to hold them like this.

"When you do get a girlfriend," Judy said, "make sure she has big

breasts like mine. Would you like to see more of me?" "Yeah!," I


Judy stood in front of me, and said, "This dress is only in the

way now," and unbuttoned the rest of it letting it slip from her

shoulders. She tossed it over a chair. Below her waist, she was

wearing a sheer aqua garter-belt and panties that matched the

bra. Her stockings were sheer too, and I could see the dark

V-shaped outline of her pussy at her crotch. I was fully hard

now, and my cock was straining for release in my pants. I did

not know how much more of this I could stand before I had to do

something about that.  

"I think we can dispense with my bra too, if you don't mind.

Would you unhook it for me?," she asked. Judy turned her back to

me, and lifted up her long hair, so it no longer covered the

clasp. I stood, and clumsily unhooked it. She held it up with her

hands at her breasts, and said, "Okay, sit down again, please." 

Judy turned to face me again, and let the bra fall to the floor.

Her breasts spilled out in front of me, and I could not help but

stare at them. I had seen women's breasts before in the

magazines, but not this way. They were beautiful! They were round

and globular, and each one ended with a dainty nipple at its tip.

Judy posed for me that way for a moment, and then bent over me

letting her breasts hang in front of my face. "Would you like to

suck my nipples?," she asked. "Yeah," I answered.  

I took one of Judy's nipples in my mouth. I guess there is some

remembrance of the technique from when we are suckled by our

mothers, and I sucked gently on it making Judy give out a little

moan. "Let me sit down," she said, "where we can be more


Judy turned to sit on my lap. Her bottom came down softly, but

she got a sort of surprised look on her face, and said, "Oh! What

have we here? I feels as if there is something hard in your lap

under my tush. I just wonder what that could be?" I looked at her

with a little bit of embarrassment, but she said, "Well, we'll

soon take care of that. I've shown you what I have. How about

showing me some of what you've got down there?" 

Judy stood up again, and gently tugged me to standing too. She

took the bottom of my T-shirt in her hands, and pulled it up and

off of me. It joined her dress and bra over on the chair. Her

hands went to my waist, unbuckled my belt, and pulled down my

zipper. One hand entered my fly, and touched my cock through my

briefs. "Oh," she said, "you're big down there. I like a man like

that!" She tugged my pants down, and made me sit again. She

kneeled in front of me, and removed my sneakers and socks. Then

she pulled off my pants, and tossed them on the chair as well.  

Judy stood again, and got me to stand in front of her. My cock

was bulging my briefs way out, and she looked down at in with a

big smile on her face. "Well, we will just have to see what all

that swelling is," she said.  

Judy dropped to her knees, and caressed my cock through the

fabric. Her hands went to the waistband of my briefs, and she

slipped her thumbs inside. In a swift motion, she pulled them

down to my ankles, and my cock jumped forward pointing straight

at her face. I stepped out of the briefs, and they too were

tossed aside. "My, but you do have a big one for someone of your

age," Judy said. "Sit down, and I'll see what I can do about the


I sat down, and Judy moved between my legs on her knees. Her long

nails raked gently over my thighs, and the pressure in my young

balls grew even more. "Don't worry," she said with a playful

giggle, "I'm not going to bite you." 

Judy opened her mouth, and took the length of my cock inside. My

cock is almost seven inches long, so it surprised me that she got

it all in. She let it slide back out again running her warm lips

over it all the way. She ran her tongue around the head, and

poked the tip of it into my pee-slit to taste the drop of pre-cum

that was already oozing from it. "I don't think that this will

take long," she said, and took my cock back into her mouth.  

It did not take long at all. I was almost ready to cum right

there and then, but I tried to hold back as long as I could. Judy

began a smooth up and down motion sliding my cock in and out of

her mouth. It felt absolutely wonderful! Her warm. moist lips

were all over my cock, and I leaned my head back, closed my eyes,

and began to moan with pleasure until I could hold out no longer,

and unloaded all the pressure that was in my balls in a hot jet

of cum into Judy's waiting mouth.  

Judy took all I had to give, and did not miss a drop. She

swallowed it all down, and licked me clean when I was finished. I

could see her savoring the last few drops on her tongue before

she swallowed them too. Then she moved up to sit on the sofa next

to me. She just sat there playing with my cock in her hand while

I recovered. "Did you like your first blow-job?," she asked.

"Yeah," I answered.  

"You have a nice cock," Judy said. "I like it. I hope this isn't

the last time I'm going to see it." Before I could say anything

by way of answering her, she said, "Now that I've seen your cock,

would you like to see my pussy?" "Yeah!," I answered.  

Judy stood in front of me again. She bent forward letting her

breasts hang down, and unhooked her stockings from her

garter-belt. She reached behind her, and unsnapped the

garter-belt to toss it aside with the other clothes. She sat on

the edge of the chair that had all the clothes on it, and took

off her shoes. Then she slid off her stockings, and stood again

before me. "Pull them down, Billy," Judy said.

I reached up, and took hold of the narrow elastic band at her

waist that held up her panties. Her skin felt so soft when I

touched it that I wanted to spend some time just doing that, but

the shadow of the dark patch at Judy's crotch was beckoning me to

other things. I slid her panties down very gently, and there

before my eyes was her pussy! I had also seen this in the

magazines, but never this way. I stared at it for some moments,

and Judy put her hand on my shoulder to steady herself while she

stepped out of her panties. I tossed them on the chair. We were

both completely nude.  

"I know a more comfortable place for the rest of this," Judy

said. "Follow me." I stood, and walked after her. I could not

take my eyes off her buttocks as we walked. I liked the way the

cheeks bounced up and down as her legs moved, and the gently sway

in her hips. My cock was hard again by now if it had ever really

gotten soft, and was waving back and forth in front of me as we

walked. Judy led me into her bedroom, and turned down the

covers on the bed. She layed down on her back with her legs

spread just a little bit. I could not help but to let out a

little gasp, and just stare at her lying there. "Would you like

to join me in bed?," she asked. "Yeah," I answered.  

I layed down next to her, and put my arms around her without her

asking me to do it. I guess I felt that we knew each other well

enough by now to do that while we were in bed together. I pressed

my lips against Judy's, and we kissed again. This time, however,

the kiss was just a little different than earlier. Judy parted

her lips, and pressed her tongue forward. It pressed against my

teeth, so I opened my mouth, and her tongue touched mine. It felt

very good! Our tongues began to roll around each other in my

mouth, and then I pressed mine forward to taste the sweetness

inside of Judy's mouth.  

Her hand went back to my cock, and began to play with it again.

In between kisses, Judy said, "You can touch my pussy too, if

you like." I moved my hand onto the soft flesh of her thighs, and

they parted. I ran my hand gently along the skin, and felt hair

against my fingers. I pressed further, and found that under the

hair was a warm, moist slit that felt very good when I put my

fingers into it, and apparently made Judy feel good too if the

gentle sigh that I heard when I touched her was any indication.

She broke our kissing again to ask, "Would you like to fuck me?"

"Yeah!," I answered.  

Judy rolled over on her back, and spread her legs. "Get on your

knees between my legs," she instructed me. When I had done so,

she reached up to pull me closer, and took hold of my cock to

position it at the opening of her vagina. "Push," she said


My cock slid into Judy easily. She was thoroughly lubricated from

all the sexual play that we had been indulging in, and my cock

was now warmly encased in her pussy. That left me with a small

problem. Up to this point I had been a virgin. I was just not

sure what to do next. I had read some pornographic paperbacks,

and I knew that I was supposed to move my cock in and out of her,

but I had never done that with a girl before. I decided that I

had better try, and somehow the motion came very naturally to me.

Just instinct, I guess.  

I buried my cock deeply into Judy's pussy. It felt good there! I

began to plunge it in and out of her. I felt like my penis was

encased in wet velvet, and I could not get enough of the feeling.

Without realizing it, my thrusts were getting stronger. I thought

of backing off a bit so as not to hurt her, but just then Judy

urged, "Harder. Oh, baby, make me feel it! Fuck me harder!!" 

I increased the tempo and the power of my thrusts, and layed on

top of her. Judy lifted her legs high, and curled them around me

the same way her arms were wrapped about my neck. I slid one arm

under her, and hugged her too. We were totally entwined together,

and I was fucking her for all we were worth! Our lips met again,

and this time it was I who pressed the first tongue forward into

her mouth. Her's met mine, and our tongues fenced back and forth

behind out teeth as we copulated there on her bed.  

Then I felt like I could hold out no longer. Sweat was starting

to bead up on my skin, and my cock was beginning to throb inside

of her. At that point I felt a strong tingling all over my body.

I broke the kiss, and let out a strong guttural sound as I felt

my cock spasm deep in her pussy. I was cumming! It felt like

there was a Fourth of July fireworks display was going on inside

my head. I drove my cock to its full length into Judy, and

unloaded my second charge of cum into her hot pussy. Judy too was

reacting, and kept saying, "Oh! Oh! Oh!," over and over again

while I came.  

After a time, it was over, and I layed limply on top of her with

all my energy spent. We lay that way for a few minutes catching

our breath, and then I rolled off of her. Judy and I held each

other in our arms for a little while, and then she asked, "Do you

feel different now that you're not a virgin anymore?" "Yeah," I

answered with a long sigh.  

Judy looked at the clock on her nightstand, and said, "It's

twenty to nine. Isn't your mother going to be home soon?" "Yeah,"

I said, "I guess I had better be going, but I don't want to."

Judy giggled at this, and said, "I really don't want you to leave

either, but maybe we will have longer the next time." "Yeah," I

said, "my mom and dad are going away for the weekend next week. I

asked if I could stay home alone, and they said they would think

about it if they can find someone to look in on me while their

gone." Judy smiled, and said, "Well, tell them that I'd be glad

to take care of you. Your mother knows me from the times she and

I have talked at the pool. I think that she'll agree." 

I got up weakly, and Judy stood next to me for another kiss. We

went back to the living room, and I untangled my clothes from

her's to get dressed. When I finished dressing Judy walked me to

the door. She was still nude except for the shoes that she had

put back on. They made her legs look even better that way.  

At the door we kissed deeply one last time. "I'll see you soon at

the pool," she said as I left, and she closed the door after

letting me have one more look at her naked body as she posed in

the doorway for me.  

I went back to our Condo. Mom was not home yet, but got there

only about ten minutes after I did. "Sorry I was so late," mom

said as she came in. "Did you find something to occupy yourself

with?" "Yeah," I answered thinking about Judy, and what it was

going to be like spending an entire weekend with her.



See All Our Feature Hardcore Sites!
Taboo Stories | Porn Stories