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Archive-name: First/amy-i.txt

Archive-author: Amy

Archive-title: Amy and I

Disclaimer- You can do whatever you want with this as long as you don't claim

authorship. Everything below is true. I have received permission from Amy 

(not her real first name) to publish this. She has read it and made a few

slight corrections. Enjoy.

1. The First Time 

I've spoken with other people about their "first time" and asked questions 

like when, where, how it happened, what was it like, etc. Talking about those 

types of things is guaranteed to keep my attention. But I've never gone into 

detail about my own experience. I've talked about it in a general sense, but 

have never descibed the whole experience the way it exists in my memory. I'd 

like to tell the story now. Although I could start at the point where 

everything actually happened, it is necessary to back up so that you 

can understand what happened and also see why. For this reason I need to 

relate the sequence of events that led up to my story:

I had known Amy for years, ever since I was about five or six years old. She 

lived across the street from myself and my mother, and used to baby-sit me. I 

would stay at her house from the time I got home from school until my 

mother came home from work. Amy was able to do this since she didn't 

work. She was fifteen years older than I, and our relationship was almost like 

that of a little brother/big sister. We touched each other; hugs and kisses 

were exchanged frequently. As a single parent, my mother had very little 

spare time to spend with me. After she came home she had to get supper 

ready, and there was always housework or laundry to do. My bedtime was 9:00 

until I turned thirteen, which meant that I might see my mother for two or 

three hours at most. Since Amy had no children of her own back then, she 

was able to spend a lot of time with me. 

I can remember sitting on her lap while she helped me with my homework. 

We played games together. I learned how to throw and hit a baseball in her 

back yard. We wrestled all the time; the kind of stuff a kid does. When I was 

twelve her son was born. Two or three years later she and her husband split 

up. She received some child care support from him, but not much. Because of 

that, she went to work. At that time there weren't any day care centers, 

and I don't think she could have afforded them anyway. She worked part 

time on the evening shift in a hospital (from 4 to 10) but had to work 

every other weekend.

After she went back to work my job was to baby-sit David, her son. I was paid 

$3.00 a night, which was a bargain for her and a lot of money for me. I got 

home from school around 3:00, changed my clothes, and walked across the 

street. She would get home a little after 10, and I would then go back home. 

Often I would stay there and we would just chat. If she went out after work 

(or stayed out late on a weekend night) I would sleep in the guest bed at her 

house, sharing a room with David. 

I need to say a few words about Amy. She was not very tall, maybe 5'3'' or so. 

After she had David she gained a few pounds, mainly in her hips and thighs, 

but she still looked good. She rarely dated. Each night the first thing she 

would do after walking in the door would be to get out of her uniform. 

Usually she would change into shorts and a tee shirt or sometimes a 

nightgown. As I said, it was no different than seeing your sister dressed 

that way.

I was seventeen the night the big event occurred. It was a Saturday night and 

she had gone out with some of her friends. She didn't get home until well 

after midnight, and I had fallen asleep on the floor in front of the TV.  

She had a few drinks in her and was feeling playful. I heard her come in, and 

had rolled over on my back, still half asleep. The next thing I knew, she was 

sitting on me and had my wrists pinned above my head. It was summertime, 

and I was wearing nothing but gym shorts. She had on a sleeveless top and a 

skirt, but the skirt had fanned out when she dropped on top of me. Her thighs 

and lower legs were resting alongside my rib cage with her knees just under 

my armpits. I could feel her bare legs against my torso. More importantly, her 

pussy was touching my penis, and the only thing separating the two was my 

thin nylon shorts and her panties. 

That fact hit me instantly. I probably became erect in a fraction of a second, 

which was embarrassing to me. I started to squirm away, but she used her 

knees to tighten her grip on me. My arms were pinned down and she was 

leaning forward to keep them there. With most of her weight on my 

midsection, I was trapped. I had turned my head away from her, but she said, 

"Look me in the eyes". I did, and remember that the look in her eyes was 

unlike any I had seen there before. She loosened the grip her knees had on 

me and began slowly moving her hips back and forth, so that her pussy was 

rubbing along the length of my penis. This lasted for less than a 

minute, until she reached underneath her skirt and lowered the waistband of 

my shorts, tucking it under my scrotum. She then moved her panties aside, 

grasped my penis, and pointed it vertically. The next thing I knew, I was 

inside her. That felt incredible.

We were still maintaining eye contact, although I couldn't have seen 

anything down there anyway; her skirt covered everything up. She started to 

move up and down, but I came on about the second stroke. Instead of getting 

up, she stayed where she was. I never lost my erection, but it did soften. 

After a few minutes I was hard again (at seventeen this is not unusual) and 

she started sliding up and down again. This time it lasted longer, but I still 

ejaculated pretty quickly. Obviously I didn't know then that it was a short 


After the second time I lost my erection and slid out. I remember being 

surprised at how wet things were down there, although it was probably 

mostly semen. I could also feel her pubic hair against my penis and was 

surprised at how much hair there was. She stayed where she was for a short 

time, then reached underneath, pulled my shorts up, and stood up. 

It was kind of a wierd situation. She sat on the couch and patted 

the cushion next to her. I got up and sat there. She became very serious and 

told me that I must never mention this to anyone. I said that she had nothing 

to worry about. I went home a few minutes later.

After that nothing really changed between us. I still baby-sat for her, and we 

would sit and chat after she came home from work. We did not discuss what 

had happened. She started to wear a robe over her nightgown, which was a 

disappointment to me. Up to that point I had never seen a nude woman. 

Some of her nightgowns had allowed me to see the outline of her panties or 

her nipples, but now I wanted to see her without clothes. At home I would try 

to picture her while I was masturbating. Eventually I figured out a way to 

solve the problem, but it took a while before I actually saw her nude body.

Once while baby-sitting I moved the curtains in her bedroom so that I could 

see in from outside the house without being seen from the bedroom. I figured 

that I could just circle by her window when I went home, or stand outside on 

a night she wasn't working. The problem was that she always changed as soon 

as she got home, while I was still inside the house. The nights she wasn't 

working she stayed up very late, well beyond my curfew. I spent hours 

lurking around that window with no success. It had almost become an 

obsession with me. 

One night I pretended to be sleeping on the couch when she arrived home 

from work. As soon as she went into her bedroom to change, I got up and 

walked quietly toward the bathroom, which was next to her bedroom. I 

figured that if she saw me I could pretend I was going to use the bathroom. 

Her door was ajar a few inches and I was able to peer inside. She was turned 

sideways, and I got a quick glimpse of her wearing nothing but her panties. I 

turned around and went back to the couch. When she came out I was still 

pretending to be asleep, but I had changed position to hide my erection.

She turned me over to wake me up, and spotted the obvious bulge. As I was 

opening my eyes she reached out and began to squeeze my penis. I lay there 

enjoying it, not knowing what to do next. Finally I reached out and placed my 

hand on one of her breasts, expecting a reprimand. She did nothing except to 

half close her eyes. Then, she acted as if she had just made up her mind and 

stood up. She took me by the hand and led me into her bedroom.

Amy turned off the light and undressed me, then took off her own clothes. 

She pulled back the covers, and I climbed into the bed. She left the room, 

telling me that she would be right back. I found out that she went to the 

bathroom to put in her diaphragm. I quickly jumped out of bed and closed the 

gap in the curtains I had made earlier, afraid that we would be seen. She 

came back and got into the bed next to me. 

We did not go to sleep at all that night. I could not keep my hands off her. 

Not knowing if I would have the opportunity ever again, I did a lot of 

exploring. I loved putting my fingers inside her; the slippery feeling amazed 

me. I had never kissed anyone using my tongue, and was shown how. I 

discovered how to make her nipples erect. We had intercourse five or six 

times. It was an incredible experience.

That night was the actual beginning of a relationship that lasted over ten 

years. Both of us eventually married other people, but we continued to have 

sex occasionally. It finally ended when she and her husband moved to 

Arizona. We still call each other once in a while, but I doubt if we'll ever 

sleep together again.

2. Related Stuff

Even though our relationship lasted over ten years, the level of intensity was 

never very high. Yet, in some ways, we were able to achieve an intimacy that 

would not have been possible if we were closer in age. Amy was a single 

parent, and was reluctant to look for a husband, knowing that it would 

change her relationship with her son. With me, nothing ever changed 

between them, since I had been close to both of them since he was born. The 

amount of time and affection that Amy was able to give to David did not 

diminish because of me. I was also able to fill some of the role of a father 

figure, combined with that of a big brother. The biggest factor, however, was 

that I would never become her husband, and we could simply relax and enjoy 

ourselves and each other.

Two of Amy's best friends were aware of our arrangement. She used to tell 

me how these friends were jealous of her situation, and once showed me an 

article that talked about the different ages that men and women reach their 

sexual prime (men in their late teens, women in their late thirties). We were 

very close to these ideal ages. One of her friends used to refer to me (with 

some envy) as Amy's "teenage sex slave". 

After graduation from high school, I attended a local college. I could live 

at home with my mother (saving a considerable amount of money) and 

continued to baby-sit for Amy by scheduling my last class to end by 3:00. I 

could do my homework after David went to bed, and earned money that 

covered most of my expenses. We were having sex almost every night back 

then. Amy was not shy about telling me what she liked and what I could do 

to excite her, and I was a very willing student.

One of Amy's friends was in the process of divorcing her husband, and she 

stayed at Amy's for a few months. I was attracted to her, and according to 

Amy the reverse was true also. She learned of this when she once asked me if 

I found Audrey attractive, and I answered truthfully that I did. Even though 

Audrey was living there and could watch David, I still continued to go over 

after school to do my homework. We never did anything behind Amy's back, 

even though I would frequently make up scenarios in my head that resulted 

in the two of us screwing. 

Audrey and Amy were very different physically. Amy was short, had short 

arms and legs, and carried a few extra pounds that she could never get rid of. 

Audrey was about the same height, but had long arms and legs, and was very 

thin. Amy used to get jealous of Audrey's figure, but if you looked at her 

objectively, Audrey was too skinny. She had very short hair, and from the 

back could have passed for a teenaged boy if she had the right clothes on. 

Audrey was also a prude. Amy would walk around the house in her 

nightgown or wearing a slip, but Audrey was always fully clothed. 

We celebrated Audrey's thirtieth birthday a day early because Amy had to 

work the next night. Amy left David at her parents, and the three of us went 

out to dinner at a nice restaurant, drinking wine during the meal. On the way 

home we bought two bottles of champagne. After we returned to Amy's 

house we gave Audrey her presents. One of the presents that she received 

from Amy was a two-piece bathing suit. After a fairly substantial amount of 

persuasion, Amy and I talked her into putting it on and modelling it for us. 

She came out of the bedroom with a light robe over the outfit, although it 

was open in front. Both of us started booing. Amy ordered me to help her 

take off the robe, and I was more than ready to assist. I stood behind Audrey 

and slipped the robe off her shoulders, and tossed it onto the couch. She 

crossed her arms over her chest. Still standing behind her, I put my arms 

around her stomach and squeezed, drawing her toward me. Feeling my 

erection against her buttocks, she pushed back against me. Amy could tell by 

the look on Audrey's face that she was becoming aroused, and stood up. She 

walked over and stood beside us, and then said, "I'm driving over to get 

David, but I'm going to spend the night there. I want you two to get it out of 

your system. Please don't worry about me, you have my blessing". 

After she left, Audrey and I just stood there, unsure of what to do next. 

Audrey had put the robe back on while Amy was getting her jacket. I finally 

walked over to her, slipped my arms around her waist inside the robe, and 

started to kiss her. Her mouth opened to receive mine, and she immediately 

put her arms around my neck. It felt very strange for me to be doing that, 

since Amy was the only person I had ever touched intimately, or even kissed 

for that matter. All night long I was very aware of differences between the 

two of them. Amy's kissing was very soft, even when she was aroused. 

Audrey was much more aggressive once she got started.

After the first kiss Audrey pressed herself up against me. As we continued to 

kiss, she lifted one of her legs and curled it around mine, eventually 

straddling one of my thighs and rubbing against it. Her arms around my neck 

were pulling me against her. I moved my hands down to her buttocks and 

pulled her against me, bent my knees slightly so that my erection was 

pressing against her pussy, then pulled against her buttocks even harder. She 

started squirming like crazy and I was having trouble maintaining contact 

with her mouth. 

I lifted her up, and she immediately locked her legs around me. This allowed 

me to remove the robe from her shoulders, and she removed her arms from 

my neck long enough for me to take them out of the robe, which fell to the 

floor. I started toward the bedroom, carrying her in front of me with her legs 

around my waist. I set her on the bed, but she didn't let go; I fell on top of 

her and started humping her. She was pushing back, and I finally moved my 

chest away from her and pushed her bathing suit top over her breasts. They 

were about the same size as Amy's, but looked larger owing to Audrey's 

smaller build. I slid down a bit and started to suck on them. She told me to 

bite them and I did. It wasn't enough so I bit one even harder, and instead of 

her telling me to ease off, she seemed to enjoy it. Amy did not like it when I 

tried to nibble there.

I reached my arms around behind me and unclasped her legs so that I could 

remove her bottom. She wouldn't let me until I had turned off the light. I 

did, and she lifted her hips for me and removed it herself. I placed my mouth 

on her pussy and tried to lick it (as taught by Amy), but she stopped 

me immediately, and pulled my head up to her mouth. After a couple of 

kisses she asked me to remove my clothes. Standing up, I took them off, then 

climbed onto the bed next to her. I ran my hands over her chest and stomach, 

again noticing the difference between her and Amy. The contrast became 

even more evident when I placed my hand down between her thighs. Her 

pubic hair was much thinner and there was none on the lips of her pussy. 

Amy's had hair all over it, including some on her thighs and anus. Also, 

Amy had a fleshier pussy than Audrey and produced a much greater amount 

of fluid.

As I climbed on top of her to enter her, she told me to go easy, since it had 

been a while since she had had sex. It took some effort to get inside her, 

she did not get as wet as Amy. I eased in. Once inside, her vaginal 

grip on my penis was looser (compared to Amy's), which compensated for the 

lack of lubrication. As soon as I was all the way in, she wrapped her legs 

around me (which Amy rarely did) and began to grind her mound against 

me. I could feel her vagina start to moisten at the tip of my penis, and 

eventually it spread up to the opening. We then started making love in 


Since all of my experience had been with Amy, I had assumed that it would 

be the same with anyone, but learned differently. Sex with Amy was almost a 

relaxing experience. She preferred to spread herself wide open and flatten 

herself down against the bed, while Audrey was very intense during 

lovemaking. Frequently Amy just wanted me to pump away; she took them 

as they came. She tended to come in a series of small orgasms, occasionally 

finding the Big One. On more than one occasion she would feel my orgasm 

inside her and not be sure whether I had come or whether she was having a 

small one. 

None of this was true with Audrey. She grabbed, squeezed, grunted, and 

forced me to just hold on. Audrey worked very hard for her orgasms, and had 

to concentrate deeply in order to come. She was very hard to satisfy, but when 

she came there was no doubt in anyone's mind. She couldn't stand direct 

stimulation of her clitoris with my fingers (which Amy loved) and would not 

allow me to perform oral sex. I also had to withdraw before ejaculation, since 

she was totally unprotected. We didn't fall asleep until it was almost light 


When Amy arrived home, I had already left for classes. She and Audrey 

talked about the previous night, and that was that. Although Audrey stayed 

for a few more weeks, I never slept with her again (or any other friends of 

Amy's for that matter). Amy and I continued where we had left off. She asked 

me to tell her about the experience, which I did.

3. More Stuff

Although Amy and I were lovers for a long time, we never fell into any kind 

of a rut. Amy was always getting me to try new things. For a while she was 

into having sex in different places. She always talked about having sex in an 

elevator, but we were never able to pull it off.

One night she came over to my bedroom at my mother's house right after I 

left her and started talking to me through the screen, eventually convincing 

me to let her in. She crawled through the window head first, and ended up 

on her knees in front of me. She was wearing loose shorts and a light 

sweater. Without even standing up, she pulled my underwear down and 

took me into her mouth. I just stood there and let her do her thing. 

As soon as I was fully erect, she pushed me back so I was sitting on the edge 

of the bed. She stood up, moved her shorts aside, and lowered herself onto 

me (without even taking them off). To lift her feet off of the floor, she 

wrapped her arms around my neck. Her legs ended up across the bed fully 

extended. I was very deep inside her, and her weight kept me there. Using my 

feet for leverage,I was able to move slightly up and down within her until I 

came. She raised herself off of me and crawled back out the window. My 

mother was in the next room and never had a clue.

Amy's parents rarely came over to visit, even though they lived less than 15 

miles away. For her birthday one year they showed up a couple of hours 

before she finished work and put up some balloons and streamers. After the 

initial surprise, she went into her bedroom. Instead of changing, she just 

removed her panty hose. Since she always changed her clothes when she got 

home, I should have known she was up to something. While we were sitting 

at the table eating cake, she reached under the table and pulled my hand to 

her lap. She had moved her skirt up to give me access. It became evident that 

she had removed her panties also. Although my hand was under the table, I 

still felt uncomfortable with her parents across from me. She didn't care. For 

the next half hour or so I played with her. She didn't have any orgasms, but 

enjoyed it quite a bit. As soon as the front door closed behind her parents, 

Amy was lying on the floor with her skirt pulled up, beckoning me... 

The ultimate place, though, was in a swimming pool. We were at a party at 

my next door neighbor's house. Early in the evening people were swimming 

in their pool, but the party had moved indoors as soon as it got dark. Amy 

had brought a co-worker with her, and the two of them drank quite a few 

glasses of wine. Her friend (Beth) and I had spent some time chatting in the 

pool while it was pretty full of people. Later on she and Amy had made a bet 

(I never got the full story) that involved me. Amy bet Beth that she could 

seduce me at the party. Beth was unaware of our relationship, and bet Amy 

that she couldn't.

Soon after the two of them came over to me and suggested a swim. The three 

of us went out to the pool and hopped in. There were maybe half a dozen 

people out back, and two other people in the pool. We stood in about four feet 

of water with our arms up on the deck where our drinks were. I knew 

nothing of the bet. Eventually, Amy reached over (I was in the middle) and 

slid her hand inside my trunks. Because of the cold water it took a while, but 

eventually I grew to size. Beth could not see what was going on. I could tell 

Amy was slowly removing her bottoms. She lowered mine a foot or so, and 

then started manipulating my penis again. 

Beth was saying something about diving boards, when Amy moved over so 

that she was facing me, about a foot away. The next thing I knew, Amy 

hopped up using the water's bouyancy, wrapped her legs around me, and 

impaled herself on me. She leaned back against the side and put her elbows 

on the deck; to a casual observer it looked like the three of us were having a 

conversation. She looked over at Beth (they were both pretty drunk) and said, 

"I win."  She then grabbed Beth's hand and moved it down between us to 

show her that she had indeed lost the bet. Amy did most of the moving, 

which was very little. I was inside her for quite a while. Beth stood there 

talking to us the whole time. At one point I tried to reach over and put my 

hand into Beth's bathing suit, but she wouldn't let me. After it was over Amy 

pulled up my trunks, put on her bottoms, and the three of us went back 


And that's my story...



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