We currently have 44663 stories with more being added every day

First Time with a Woman

Posted by: Author: Age: 50+ Posted on: 0 comments
0 likes 517 views Category: Masturbation Male-Female Tags:


I was definitely a late bloomer sexually. True, I used to play with myself frequently as a child and discovered full-fledged masturbation with ejaculation by the time I was 13, but I was very shy around girls, though certainly very interested in their bodies. I dated very infrequently and instead beat off to Playboy and Oui and other soft-core magazines. The hard core stuff didn't really appeal to me that much. I was thrilled when Playboy decided to show pubic hair on its models and I'm appalled by the current trend to shave it all off.

Anyway, it took me to my late 20s before I got serious with a woman. Her brother and sister-in-law had introduced us and we got to spend a little time together during her first visit to my town. She explored my apartment and quickly uncovered my stash of porno, such as it was, and flipped through the Playboys, etc. with interest. Dummy that I was, I was too awkward to pursue any serious physical contact with her. In retrospect, it seems like she probably was looking for something more than conversation.

She went home, but we kept in touch by telephone over the next weeks and our conversations began to burn up the lines as we got more 'friendly' and sexy in our remarks. We knew that if and when we got together again, there would indeed be some action even if we felt, for religious reasons, that full intercourse should be delayed until marriage.

Sure enough, she came down to visit again and we arranged for her to stay, very properly, with an older female friend of mine who then invited me to join them for lunch. While my older friend was in the kitchen getting the food ready, I got reacquainted with my telephone partner in the livingroom, knowing there was one more room between us. This time, instead of giving her a very chaste kiss as before, we ended up with tongues in each other's mouths and a little preliminary groping.

After lunch, we were both anxious to go for a walk and naturally ended up at my apartment, a mile away. Once there, we continued our kissing and groping. I began unbuttoning her blouse and reaching behind her for the fastener on her bra. She looked at me and said, 'I hope you're not disappointed.' Her bra, it turned out was heavily padded and her left breast was significantly smaller than her right (which wasn't all that big either). Though their shape was odd, I found that tactilely they were still breasts and fun to play with and the nipples worked just fine.

Meanwhile, I made it clear that she was free to explore my body anywhere she wanted and so she wasted no time taking off my T-shirt and unbuttoning my pants. Fortunately, this was at one of my low points weight wise, so my body was fairly trim, for me. Soon she was playing with my erect penis. She didn't indicate if she was disappointed by its size, but it has never been terribly impressive in magnitude even when the fat on the pubic area retreats and makes it look a little longer than usual.

I meanwhile had stripped her down to her pantyhose and she asked me to stop at that point because, as she put it, 'her friend was visiting' or as we used to say in college 'she was on the rag'. That was disappointing, but she now was on her knees in the middle of the living room topless in pantyhose and I was naked behind her. She urged me to play with her titties and I was only too glad to oblige. Apparently, she got off from that stimulation. Perhaps I didn't notice some added stimulation by her hands in her crotch.

After that, she returned the favor by having me lie on my back as she stroked my penis to orgasm. It took a while as usual for me to relax enough to come and she wondered if I'd ever reach orgasm as her hand got tired. But soon enough I did come and made a mess on my stomach. I don't know about 'cords of cum' that you guys write about, it looks to me more like puddles of glop and I can't wait to get it off me. Things pretty much ended after that for the day. I washed up and both of us put on our clothes once more and walked her back to her chaperone's place. I don't think we really fooled anyone into thinking we were totally chaste, but we maintained the appearances anyway.

Things escalated pretty quickly after this visit and within six months we were married but, unfortunately, not for long. More next time on the road to the wedding hall and back.



You must be logged in to post wall comments or like a story. Please login or signup (free).

Other Stories You May Enjoy