Back in 1981, when I was 17, I had a best friend named Mike. We were constantly together, and I spent a lot of time over his house. His parents were loaded (his dad owned his own business) and they had great big house with a huge pool in his backyard we used to hang out in all summer long. There was a pool house that had 2 big changing rooms, a bar, a shower and a bathroom.
Mike had a younger sister named Lisa, who was 10 or 11 at the time. She was a really wild kid, very street smart for her age, and she liked to hang out with us a lot. She was beautiful, with an angelic face, gorgeous blue eyes and long flowing blonde hair. She had an amazing smile and an infectious laugh; when she grew up she absolutely had the potential to be a model, that's how pretty she was at 10 years old.
Lisa and I got along really well, and she was always teasing me - about girls I liked, how my hair was cut, etc. She was actually like a little sister to me, and although I never admitted it to anyone then (or now, except for here) I had a bit of a 'crush' on her. I had fantasized about her while I masturbated a few times, and I had seen her often in her bathing suit at the pool and although her body was still girlish, I always managed to stare at he ass; it was very round, small and very tight.
On this one particular day shortly after the Fourth of July Mike invited me over for the day. His parents were going down the shore and wouldn't be back til late that night, and he told me his cousin (Sara) would be there as well. Sara was Lisa's age, maybe a year older (12 or 13). When I showed up around 3:00 they were already at the pool and I went into the pool house to quickly change, and then I jumped in and joined them.
They said they had been waiting for me to show up as they wanted to have 'chicken fights' (those are where you have 2 teams of 2 people, one sits on the other's shoulders and tries to push the other person off). I immediately suggested that Lisa be with me, and Sara would be teamed with Mike. We were in the shallow end of the pool and I squatted down, and as I did so Lisa pushed my head under the water so she could mount my shoulders.
I should pause and tell you what kind of bathing suits we were all wearing. I had on a regular pair of pale blue gym shorts; not tight but not very loose either (no underwear or jock strap underneath). Mike had on a regular, bright orange bathing suit. Lisa was wearing a one-piece black suit with hot pink stripes running down each side, with thin straps holding up the top, and the suit was cut high at the hips. Sara had on a two-piece yellow suit, the bottoms were briefs rather than bikinis, and the top was like a regular bra (she was just beginning to develop and had small breasts, probably around a 30A or 32A).
As I went under the water Lisa's hand remained on top of my head and I found myself about 2 inches from the front crotch of her bathing suit. I could clearly make out the cleft of her vagina as her suit was quite tight there, and my heart started beating furiously. She quickly swung around and sat on my shoulders and I stood up. As we waited for Sara and Mike to get in position Lisa sat up straight with her hands resting on the top of my head, and I felt a very slight but noticeable rocking of her hips against my neck, and she was giggling. Before I could do or say anything, Sara and Mike charged forward and the first chicken fight was on. After much laughing, shouting, pushing and shoving we lost as Lisa flipped back off my shoulders. We rested for a moment and it was time for Round #2. I submerged myself behind Lisa, with thoughts in my head of my up close look at her vagina and her humping my neck, and at that point I was semi-aroused. As I went underwater this time I approached her from behind, and she was standing still waiting for me to duck under her legs. I paused for about 3 seconds and this time stared at her ass; because of the make of the suit (remember the high cut hips...) it had ridden up the crack of her ass and given her a considerable wedgie. While it wasn't completely stuck in her butt like a g-string, a large part of both ass cheeks were visible, and I broke out of my very short trance as both her hands reached down and put her suit 'back into place'. I dove between her legs and rose to the surface with her secured on my shoulders.
Sara and Mike were having some difficulty getting her up on his shoulders, so Lisa and I were again left waiting. Like she was reading my mind, Lisa began rocking her hips again, this time more noticeably. The other 2 were splashing around and laughing, and I heard from over my head Lisa say 'Jeez, I REALLY gotta pee, I hope I don't go on your head!' and she laughed that very special laugh of hers. I made a comment to the effect that if she did, I would kill her. Sara and Mike were ready, and as we began the second fight there was lots of giggling, especially when Lisa grabbed hold of the strap of Sara's top and yanked down, exposing her small left breast for me and Lisa to see. Sara freaked out, and at this point I had a full erection. As Sara swam away to the other end of the pool to rearrange her bathing suit, Lisa accidentally backed into me and my erection was momentarily pressed up against the side of her thigh. I didn't think she noticed until she coyly smiled at me and dipped under the water. As I looked down I noticed her not swimming, but treading just under the surface, looking directly at my crotch! I quickly turned, dove in and swam to the other end of the pool.
As I did this Lisa climbed up the ladder and out of the pool (with another wedgie, which she took her time fixing) and said she had to pee and she would be right back. Mike said he was going into the house to get some drinks and chips. Sara was still pretty pissed, and said she was going with Mike and she was going to watch TV for a while. As they walked up towards the house (probably about 100 yards up a small hill from the pool), I decided to go into the pool house and get a towel (I didn't bring my own and the pool house had shelves of them).
As I entered, I heard the distinct noise of someone urinating, and of course knew it must be Lisa. As I mentioned the pool house was, like the rest of the property/home/pool, VERY nice. Immediately across the main room (which was like a rec room) from the entrance was a long bar; to the left was a short hallway with a changing room on either side. On the right was an additional small hallway, with a large linen closet on one side and the bathroom directly opposite. As I looked down the hall, I could tell the bathroom door was open. Lisa had apparently gone in there not thinking anyone else would be entering the pool house, and left the door open for a 'quick pee'.
My mind was racing. Should I go down the hall and 'accidentally' see Lisa in the bathroom? What would she do? Would she scream and freak out? Would she tell her brother I was spying on her? Being completely worked up from the activity in the pool (and being a horny 17 yr old who hadn't jacked off in 2 days...) I decided to take a chance. I slipped down the hall and, being as discreet as possible, opened the linen closet and yanked out a towel and turned around, not knowing what to expect. As I glanced into the bathroom, Lisa's head was turned to the left, and she was looking directly at me. She was seated on the toilet, and she was still peeing. Her suit was around her ankles and he arms rested on the tops of her knees. I could clearly see the left side of her chest and her nipple. She showed the early signs of breast development (her breasts were slightly raised off her chest, and her nipple, the one I could see, was rather large and prominent - 'puffy' would probably be the best way to describe it). As I was taking all this in (over the period of about a second) Lisa said, 'What, you never saw a girl pee before?' As she was saying this she unwound some toilet paper and began wiping herself.
'I'll be done in a second if you have to go'. I was mesmerized, and hard as a rock, and I realized that she could easily see my erection through my wet suit. To my surprise she stood up, reached back and flushed the toilet with her suit still around her ankles. As she did so I got a complete view of her naked body from the side, and was very tempted to start jerking off right there. She then pulled up her suit without any hint of embarrassment and walked towards the door of the bathroom. As she did I walked in and passed her. I thought she was leaving and that would be the end of it - in fact I was HOPING she would leave so I could have a quick masturbation session before I went back to swimming.
My back was to her when I heard 'Can you pee when your thing is hard like that?' I turned to face her and she was smiling, and pointing directly at my crotch.
'I, um - none of your business!' I managed to get out.
'Hey, you got to see me pee, now I get to see you do it' she said. 'Fair is fair. Come-on, I always wanted to see how a boy pees'.
Should I? Would I get in trouble? What would she do when she saw my hard on?
I was thinking with my penis and not with my mind, so I of course said, 'OK, but you can't tell ANYONE. You have to promise'.
'I promise,' she said. 'I won't tell'. With that she walked back towards me and leaned against the edge of the sink facing the toilet.
I dropped my suit, intending only to have it low enough to be able to aim my penis at the toilet. Instead, they dropped all the way to the floor. As I stood there, I knew her eyes were locked on my hard-on, and I knew there was no way I was going to be able to piss. I didn't have to go, and even if I did I wouldn't be able to. I stood there for at least 10 seconds and finally told her I couldn't go.
'Guys usually can't pee when they have an erection,' I told her.
'I didn't think so. My friend Beth said her brother told her that boys can't pee when their things get hard, but they rub them and other stuff, sperm, comes out. Can you do that?'
Just what I wanted! It was like a dream! I slowly took hold of my cock with my right hand and began stroking it.
'Yea, its called masturbating and all guys do it once they're like 13 yrs old. Girls do it too when they get older. You can't tell ANYONE I'm doing this, right? I'd get in BIG trouble.'
'I told you I wouldn't tell.' Her eyes were locked on my cock, and I was incredibly aroused, with lots of pre-cum making me very slippery.
I told her, 'Guys like to look at pictures of naked girls when they masturbate, or think about naked girls. Since you just have on your bathing suit, and I just saw you peeing, can you just take it off for a second while I do it?'
No words. She simply hooked both straps of the top of her suit with her thumbs and pulled them down, wiggled her hips and let her suit drop down once again to her ankles. I stepped towards her, my cock sticking straight out. I told her I could show her how girls do it, and she said 'I know how - my friend showed me last month' and she moved her left hand down to her hairless vagina and her middle finger disappeared into the folds of her labia. I was now next to her, leaning against the sink with her, our hips a mere few inches apart. Her head was rolled back slightly as she rubbed her finger up and down. I reached over and placed my hand on her chest, and lightly pinched her nipple between my thumb and forefinger. As I did this my cock pressed against her thigh, and I instinctively began humping against her. Deep within my mind I knew this was all quite wrong, but also new I was so horny there was no way I could stop.
Lisa was now looking down at my cock as she fingered herself, and I noticed her face was flush. No, there wasn't any load moaning or groaning, but her breath was coming a bit fast, as was mine. We turned to face each other and as we did so, she began to giggle and said 'I can't believe were doing this!!!' She had a very carefree attitude, was not uptight about it at all, and she was very obviously enjoying this new type of experience, as was I. I knew from my previous fantasies I wanted to see her ass, to feel it, so I asked her to turn around for a minute.
'Your not going to stick it in me are you. We can't do THAT!'
'No, no - I just want to give you a special hug,' I told her.
She turned around, and I got my first uninhibited view of her ass; it was everything I thought it would be. I stepped forward and gingerly placed my throbbing, slippery erection directly between her ass cheeks, with the base and bottom of my cock pressed tightly against her. I leaned forward and put my arms around her, with my hands linking in front of her in the middle of her chest. She pushed her rear end back against me and arched her back towards me with her long blonde hair falling back over my left shoulder. I unclasped my hands and moved them each to a nipple, rubbing them momentarily until I let my right hand drop down between her legs, where I began to finger her. I had never touched a girl there before, but I had seen pictures and knew that the clitoris was the most sensitive spot. As my middle finger explored her folds I noticed how moist and warm it was, and I found her clit quickly (I must have been lucky...) and began rubbing it up and down. As I did so her hips were grinding against my cock, which was now sliding exquisitely up and down her ass. I could only take 2 minutes of this, and I told her I was going to shoot my sperm. She extracted herself from me and turned to face me, and I grabbed my cock and began jerking like there was no tomorrow. The first spurt came out hard and fast, and landed just above her belly button. The next 2 spurts were not quite as potent, yet managed to hit her right in her pubic area, just above the opening of her vagina. Several more spasms caused more globs to fall on the floor between us.
Once I had come, I was embarrassed. Lisa looked at me and put me at ease.
'That was SO cool. Thank you so much Pete. I promise I won't tell anyone, OK'. She grabbed the towel that was on the floor and began to clean the come off her stomach and legs, which is a site that will be imprinted in my mind forever. She put on her suit and gave me a kiss on the cheek and ran out the pool. I followed just a few minutes later.
The whole episode lasted maybe 15 minutes (max) yet was the most memorable of my life. We had one more encounter 18 months later (another story....) and then they moved to England when my friend's dad sold his company. I think about Lisa and that day often now when I masturbate. TRUE STORY!