One of my earliest sexual experiences happened when I was just about to turn 20. I had broken up with my girlfriend whom I had regularly fingered to orgasm; she would 'take it out' and stroke me but not let me cum. We had been dating three years.
My parents had many church friends and one woman, I'll call her 'Mrs. W' for this story, was a youth counsellor. She sort of took me under her wing after my failure in college and then this breakup with the girlfriend of three years. My parents paid her for the counselling by the hour; I usually saw her once a week.
Mrs W was in her late 40s, a bit older than my own mom. The Ws had had their family a bit later than my parents, Mr. W was very close to retiring at 65 and their daughters were 16 and 14. Mrs. W was very pretty, a smart dresser, with big hazel eyes, small breasts and an outgoing personality. They had a pool surrounded by his elaborate prize-winning rose gardens. The W's had extended a standing invitation to swim in their pool as part of my learning to relax. I only saw Mr. W once all summer although I was there almost every weekday.
At the start of August the two girls were seen off to camp for the month, and Mrs. W and I were alone in the pool most afternoons (I went to work for 8:00pm). Over the course of the summer we had become very friendly and I always looked forward to our time together. Our conversations were about all sorts of things. One day she asked me about my dating experiences. I thought she wanted to know what might be going on with her daughters and their friends (my younger brother briefly dated her older daughter).
I felt comfortable telling her that all I had done was kissing and 'petting'. She asked if I masturbated and I told her yes I did. She asked how far I had gone with my various girlfriends. Then I explained in great detail what I had done with the recent ex-girlfriend, how I had started out just 'feeling her up' through her clothes and then we had progressed to taking her bra off, then me rubbing her pussy through her pants and then with my hand on the outside of her underwear and then eventually inside her underwear. She would take my cock out through my zipper and stroke it but would stop when I warned her I was about to cum. Then one day in my college dorm we had actually both been naked together but she still wouldn't jack me off. I also explained that 'P' not letting me cum meant that I had to go home and relieve myself after every date.
I got unexpectedly-bold and asked Mrs. W if she masturbated and much to my surprise she replied 'all the time'. She explained that her and Mr. W didn't have sex anymore 'because he was too old' and she found this frustrating. This conversation was exciting me. We were getting cold now in the pool and we got out. We wrapped ourselves in our towels and went into the pool change house. It had five small interconnected rooms; a tiny mens changeroom, a tiny ladies changeroom, and a larger central kitchenette with a small lounge. There was a bathroom off the kitchen.
We were shivering, she made tea. As we sat there wrapped in our towels and drinking mugs of steaming tea, she asked what I thought about when I masturbated, did I ever think about her? I said yes, I thought she was beautiful, very sexy. She asked if I wanted to masturbate now. I said yes but I could wait until I got home. She drew the drapes and assured me that no one would see us. She made me promise I would never tell anybody. She smiled. She said she had never done this before, and asked how we should start. I said that I would like to see her completely naked.
She pulled off the top of her two-piece bathing suit, revealing breasts about the size of very large oranges, sagging a bit, but with huge nipples already erect from the cool pool water. She took my hand and showed me how to massage and roll the nipples and squeeze them. My pecker was at full attention. I was shy, but not paralyzed.
I pulled off my bathing suit and let it fall to the floor. She noticed I was hard, took me by the hand, drew me to her, and said that we mustn't kiss, this was for fun, not love. We just stood there for a few minutes with our arms around each other. I put my hands on her hips and pushed her wet bathing suit bottoms down. She stepped out of them. We hugged again, and I could feel my cock along her flat belly, nestled in her wet pubic hair, my tip poking her navel. Her belly was warm against me.
There was a couch like a pullout bed. We sat down on it. I felt her hand grasp my member, so I grasped a handful of tit. Before long she was stroking my peter, and I had my long finger in her pussy. She made me agree not to cum in her. After a while she asked me to rub her clit, showing me where to find it. We lay down facing each other on the narrow couch. I gave her clit a firm finger rub and soon began to feel pussy juice. She was slowly stroking me, enough to keep me hard but not make me cum. Then her body stiffened, she began to shake and moan, and then she came with a loud shriek.
After she had relaxed she started jerking me harder, she did this better even than I did myself. After a couple of minutes I said she should stop, I was going to cum. She said just relax, enjoy it. A few seconds later I ejaculated, shooting at least five thick jets of cum onto her. I think I had at least eight or nine contractions in total. I continued to dribble for several minutes after the spasms, but my penis stayed hard.
She asked me to start stroking myself. While I was stroking she started fingering herself. She was pushing her belly toward me, then she started to direct the tip of my cock to rub against her. Her eyes were closed, and her hips were really thrusting while her hand grasped me firmly. By this point my knob was very sensitive, and it was actually starting to hurt. But I didn't want to disappoint her.
I told her I was about to cum. She continued to thrust onto me as she said 'Pull away! Oh, please pull away! Don't cum on me!'. I pushed away from her on the couch and she frantically stroked her slit. I grasped my cock, rubbing oh so quickly.
My cum exploded onto her belly as she also started to cum, she made some REALLY wild noises!!! I couldn't believe the pain, everything from my anus thru the base of my cock out to the tip was sore and VERY sensitive. We lay there gasping.
The next afternoon in the pool she asked for a repeat performance. I told her I was still very sore from the previous day. She asked would I do something to please her? We undressed and dried in the lounge. We lay down and cuddled for awhile. I began fingering her. I got hard right away, and it hurt. I was rubbing her clit, going to the 'well' with my long finger for lubrication whenever she became dry. She said I was very good at this, that 'P' had trained me well. I told her it wasn't 'P', my very first fingering instruction came from 'H', several years older than me. She was quite surprised, she knew 'H' well, had also counselled her.
She started to stroke me then and I cried out in pain. I asked her to suck me, that would be more-gentle and her saliva would ease the discomfort. She said that she wouldn't do that, wouldn't put my penis in her mouth. I asked her to stop stroking me, I was too sore. She took the bottle of sunburn lotion off the table and squirted some in her hand. She started to stroke me with this, it was very cold, and must have had a pain-numbing medicine in it. I felt better almost right away.
I was still fingering her. Her eyes were closed, and her hips were thrusting. She was very aroused by now, and trying to pull me on top of her and pull my dick into her pussy. Finally I was over her, on my hands and knees between her spread legs. With her hand guiding me, I was thrusting in the air over her. She wrapped her legs and arms around me and rocked violently. I came instantly without being inside her. We hugged, gasping, for a few moments, then I began to feel my aching, painful dick. She was horrified to find my white semen was leaking all over her pink pussy lips.
She ran to the bathroom, and was very distracted after that and the next day. By the third day in the pool I was bugging her for sex. She had been strangely silent. She told me she was waiting for her period, hoped she wasn't pregnant. I said well we might as well have some enjoyment in the meantime. She smiled, said I was right, and we hurried into the change house. I wasn't sore anymore. I was rock hard as soon as I stripped off, and she told me that she needed more time, some foreplay first. I was fingering her and after awhile she was bleeding. She was so happy about that, she cried! She went and put a tampon in, and she said she was imagining that the tampon was me inside of her while she masturbated. Her head was someplace else now, I watched her fingering herself until she came, then I jerked myself off as she slept there beside me.
Things changed after that day. We had a few more visits, no sex, then I moved away to another college in another city and I didn't see her until the next summer. She was very cool, I guess I should have phoned her a few times through the year. She was my 'Mrs. Robinson' from 'The Graduate'.