Diane and I never had sex or even dated in highschool in the 60s. We never really talked much until the summer following our first year in university.
That began when we ran into each other in Toronto one day after work, had dinner together at Swiss Chalet, then took the late commuter train together. I had my Dad's car at the station and drove Diane home.
I walked her to her door; she put her arms around my neck, pulled my head down, and our lips touched for a few seconds. Our first-ever kiss. I got an erection right away, and didn't want to hug her in case my hard cock pressed against her through my clothes.
Then she asked me to come in to meet her parents. Well, as it turned out her parents weren't home. She found a note saying where they were, they wouldn't be home until 11. It was only 8:00pm. She put on water to boil for tea, then went to the bathroom.
Then she said she was going upstairs to her room to change. A few minutes later she called for me to turn off the stove for a minute and come up and see her room. When I got there she was laying on the bed, naked.
She asked me to take off my clothes and lay down with her. I did as I was asked. I was trying to hide my cock and hold my erection down at the same time. She announced that ejaculation fascinated her. I had never heard a girl say that word. She put her arms around me and kissed me, she reached down and started to stroke my penis. It was sort of flopping all over as she worked away at it.
I didn't know what to do with my hands, they just sort of landed on her tits. I remember her nipples were hard. Pretty soon I was feeling like I was going to lose control and 'shoot'. I told her this, and she slowed right away.
She got me to stand up beside the bed and she sat on the edge with her knees far apart and began rubbing my cockhead in her pubic hair. I was still a virgin back then, and this felt very intense and even though I wasn't 'in' her I started involuntarily thrusting with my hips, my hands on her shoulders. She still had her hand around my cock, and this felt really good. All of a sudden I could feel I was starting to cum. The first stream shot in her pubic hair. She was kind of startled and jerked my cock. The next stream went in her ear and hair, then on her breasts, then past her side and onto the bed.
This was the second time that a girl had ever jacked me off, and this time it felt much better, maybe because I wasn't quite so self-conscious as the first time. She was amazed at how far I could shoot my cum. It was nothing special to me, I had never watched another guy jerk off. To this day I have a restricted flow of urine, it takes me a long time to pee and empty my bladder. I guess this restriction causes the cum to be a thin stream but to shoot out really far under the pressure. She said it was a lot farther than her first lover.
She was having trouble on The Pill and we had to stop having sex as I found condoms were too tight and she didn't like them either. She still gave me hand-jobs. I would finger her until she came, or sometimes we would find a quiet place where she was comfortable undressing and I would rub her clit until she moaned, bucked her hips, then lay quiet. She said it produced a really intense orgasm.
All this time we were best of friends but we were both dating other people. Then one day she called me in tears. I went right over, we lived only a couple of miles apart. She told me she was pregnant by 'R', he was going to marry her, and we would have to stop seeing each other in case he found out. By the time I left I had agreed with her, our secret was our secret. I was devastated. I wasn't invited to the wedding.
About a year and a half later she called me; 'R' hadn't made love to her since the baby arrived, and she was horny but tired of masturbating. This was the first time I ever heard of a woman masturbating, I thought it was a guy thing.
The next day she left her son with her mother and met me in a motel room. She said she felt like a whore but she just had to get off. We tore off our clothes. Her tits were huge, what with the breast-feeding. We were hugging and kissing and I came almost immediately, she barely touched my cock. I said I was sorry and would be able to cum again in about 20 minutes. She said she couldn't wait, and she was trying to shove my hand into her pussy. I began to finger her, and she started to relax, then moan. Her hips were thrusting and she was very wet, very slick. I had three fingers inside her, with my thumb rubbing her clit the way she liked.
She couldn't seem to cum. After a few minutes I was getting hard again. She said we couldn't have sex, she wasn't on any birth control and she was afraid of getting pregnant again so soon. I kept rubbing her, and she was stroking my cock. She said that feeling my cock really hard and thick like that was helping her cum. All of a sudden she stopped thrusting her hips. I kept rubbing her clit, she went rigid, then gasped and stilled my hand. She virtually collapsed.
I was really eager to cum, and began to stroke myself. I like to cum sitting up, so I knelt on the bed beside her and when my cum welled up I sprayed over her belly and breasts, milking the last drop out of my distended prick. She dozed off, then awhile later we got cleaned up and she left to go feed the baby.
We did this again the next week, then I didn't hear from her for awhile. When she finally called, she was crying.'R' had finally made love to her, but she was now pregnant again. I tried to console her. This time we mutually masturbated almost every week of her (2nd) pregnancy. She couldn't get enough of my hand except near the end where I would just hold her in my arms.
The next time I saw her was about three months after the second son was born. She said she really needed me.'R' was back to making love to her but he was pulling out before her pleasure and she was really frustrated. One afternoon in a hotel I fingered her to a total of seven orgasms. She welcomed me with the best hand-job ever, then brought me off, and finished me again later with a wonderful hand-job.
After that we met for an afternoon of pleasure every couple of months. She said that 'R' didn't suspect a thing. I thought that if he did then he simply wasn't saying anything.
Then in the midst of this I married and we didn't see each other for quite a while. Then I had to go away on a special training course in Ottawa and I called her, asked her to meet me. She wasn't sure she could pull this off, but sure enough, she met me on the Tuesday night. We had a wonderful three evenings together, we were actually able to go out in public without worrying that we'd be seen, and we enjoyed this 'dating' always followed by very hot mutual masturbation. My marriage was already on the skids so I welcomed the diversion.
We went back to our prior habit of getting together every month or two. All this time we never had penetration sex. She got pregnant by 'R' again, she said he didn't pull out the last few times. She wasn't very happy with him but couldn't leave because of the boys. Number three was a boy as well. After that, 'R' didn't touch her. She figured he was fooling around and it didn't take much to confirm that. We met every month for hand-jobs and fingering.
A couple of years later she was very distracted during one of our visits. Finally she told me that she and 'R' had gotten very drunk at a Robbie Burns party and he had impregnated her sometime during the night. He wanted her to have an abortion, he didn't want a fourth child. She refused, and things had gone downhill from there.
Just then my job was transferred across the country and I left my first wife behind ... she wouldn't move. A year later I met someone else and we married two years later.
A few more years went by and I managed to attend my highschool reunion. Diane was there, with 'R', and they were holding hands. She looked stunning for a woman in her early 50s now. I was unable to talk with her alone. I came away thinking they had resolved their differences. I put her out of my mind.
Five years went by and I decided to write to her. We exchanged emails for months, never touching on our earlier trysts. One day I had business near her home and called before dropping by. It was then I learned she had left him, and this was HER new home; she had waited until the youngest was close to finishing highschool. We talked over tea for three hours, then I went back to my motel.
Several days later I called her, told her that I needed to be with her. As soon as I arrived she asked 'would you like to go to bed?' Of course I did. She led me to her bedroom. She quickly removed her slacks and top, then turned away from me and removed her bra and underpants. I saw this out of the corner of my eye as I was concentrating on stripping off my clothes. She turned toward me, covering her pubic area with one hand and trying to conceal her ample breasts with her other arm. Things quickly escaped her grasp. She had magnificent breasts, quite large, with beautiful full erect nipples.
I had not seen her naked in years. She had the sexiest body, with soft curved hips, a slightly-rounded stomach, and a small sparse bush. I almost came right then. She sat down with me on the edge of her bed and we kissed, long and passionately. We lay back on the bed, and soon I felt her hand on my very hard cock. She was stroking me in a very sexy way. I slipped my finger into her pussy. She spread her legs slightly, inviting me in. Slowly I slipped a second finger in and began to move the fingers in and out of her slit. As I did this not only did I get even more turned on but suddenly the way she was stroking me changed pace. I moaned. I stopped kissing her long enough to say we had to slow down or I was going to shoot cum and we'd be done for awhile.
She looked at me very seriously, dropped her eyes a bit, and asked if I would give her pleasure by masturbating her to orgasm. I said, 'of course, we're friends, anything you want!'. She told me she missed heavy petting with me. We were laying facing each other. She pressed my fingers into her pussy, 'that feels so good when you rub me there'. She grasped my cock and commenced stroking me. Within a minute I was intensely aroused; I asked if I could cum inside her and she said no, that she hadn't finished menopause yet, and she didn't want to get pregnant at this stage of her life.
With that I reached down, put my hand over hers, and between the feel of her wet pussy and the combined stroking of my member by both our hands, I brought myself off. She moaned as I shot jet after jet of cum over her belly and pubic hair. She then started to direct my hand upon her pussy. With her other hand she grasped her left breast and began to massage it, squeezing her nipple. After about thirty seconds she asked me to move my finger back and forth faster. Seconds later I heard a low moan, and she started taking rapid breaths. These rapid breaths started becoming louder and faster. Then a loud OOOOOOOOHHHHHH!!!
We continue these sessions whenever we can sneak time together. Just the other day I was lying on my left side next to her, stroking my penis as we lay on her bed. She was lying on her back and had her eyes closed, with the fingers of her right hand inside her panties, on her vulva. I kissed her once in awhile but she was really off in her own little world, stroking herself and moaning and breathing heavily. She could hear my breathing, and when I started to gasp she started to rub herself more frantically, and my cock spurted just as she came.
After almost 40 years we are still the best of friends when naked together.