Disclaimers: If you hate wife sharing fantasies don't read this story; instead click on the "romance" tag for some great stories of hot one on one monogamous sex. The true events forming the kernel of truth on which this story is based took place in the days before HIV.
*
At the time of VU my wife Dianne and I had been married and faithful to one another for 13 years. Diane tells me that she enjoys sex with me so much, and more than any of the lovers she had before we married, that she couldn't even think about cheating. And I feel the same way about her. She's also about the sexiest woman I've ever known. She has long brown hair and soulful brown eyes, full pouting lips made for kissing. Oh and her other lips, the ones on her pussy, were also just made for kissing. When she's aroused they swell up and open out begging for the touch of my tongue, and later for the deep sensual penetration of my cock. She's medium height with full hips and medium breasts that still stand up high and firm, with pencil eraser sized nipples that stiffen whenever she thinks about sex - which is plenty often. Yes, life with Dianne has been good. I'm 36 and Dianne is 35.
Our friend Steve hadn't had it so good. Although he's a good looking guy with a good job, funny, intelligent, and a truly nice guy, he never actually seemed to be dating. It was like he was just terrified of women. He and I had talked about women a few times and I knew he wasn't gay. Just scared, though loathe to admit it. He always just said he was busy with his job, and "not now."
I said the time of VU was significant. VU stands for Virgin University. No, there isn't really a VU. That was our creation. I came home after a night drinking with Steve to celebrate his birthday and told Dianne that Steve was still a virgin at 25, swearing her to secrecy since Steve was very embarrassed about it. Dianne was adamant that we had to do something to help him.
"How?" I asked. "Sign him up for a dating service?"
"That wouldn't help, Alan," Dianne said, "he's terrified of them. Those women would eat him alive."
"What then?" I asked. "Buy him a prostitute?"
"Ugh no," Dianne replied. "What a horrible way to lose your virginity. No, Steve is a darling and he deserves a nice girl who will treat him right. We don't need to find him dates. He's a good looking guy. Women will find him. We have to teach him how to date. We need to create VU, Virgin University."
And so we did. Though we didn't put it that way to Steve of course. But when we finally broached the subject he agreed that he didn't know anything about going on a date, and was grateful for our offer to teach him. Our first lesson felt a little awkward because Steve was our "third wheel." Dianne and I went out to a nice restaurant for dinner making sure with our reservations that Steve, who arrived alone, sat at a table nearby. We made small talk over dinner and Steve was able to overhear bits and pieces of it. More importantly he could hear the tone and see our body language. After dinner we went to a movie and Steve was sitting in the row behind us. After a while I casually put my arm around Dianne and she snuggled against me and put her head on my shoulder. That was it, nothing serious.
That was the point of the second lesson, in our home. Two people on a date could just enjoy one another's company and get to know each other, with nothing serious, nothing threatening, and nothing to be afraid of. He could do this. He practiced with Dianne across our kitchen table, chatting about this and that, Dianne correcting him whenever he got overly serious, maudlin, argumentative, or flippant. Finally he seemed to get the right tone. We moved on to flirting, teaching him first how to read when his date was flirting with him and how not to accidentally rebuff her. Then he learned some double entendre of his own, and how to deliver them with a glint in his eye.
We told him not to expect sex right away, but not to be surprised whenever it did come, as we assured him it would. When? He would just know when the time was right, and he had to be ready, but relaxed, not tense. Act confident and it would make him confident. He had to know what to do when the time came. Not sex education. He knew all the mechanical stuff about what went where from school. He needed to know how men and women got to that point, with their bodies and with their emotions. We repeated the movie scenario with me and Dianne on our sofa and Steve sitting across from us. This time after I put my arm around her I caressed her upper arm and then her shoulder. I massaged her shoulders and neck, then moved down her back and up along her sides lightly brushing the sides of her breasts. I pointed out to Steve that I had just felt her breasts, but it all happened naturally and the point was to see whether she was going to stop me.
"Since she didn't stop me," I said, "now I'm going to get a really good feel."
I massaged from her shoulders up to caress her neck then turned her face towards me and kissed her gently. While we kissed my right hand caressed her cheek while my left hand slid down to cup her breast full in my hand. Then I showed him how to unfasten a bra strap. Dianne brought out three different types of clasps and showed him how each of them worked. Then turning her back to me and Steve she pulled off her shirt and asked him to unfasten her bra. His hands were shaking with nervousness and he couldn't do it. She told him not to worry and to look again at the pink one she had brought out which had the same type of clasp. He worked that one a couple of times and announced he was ready to try again. This time he did it and her bra fell to the floor. Did I mention that Dianne has the most beautiful back?! She congratulated him, pulled her shirt back on without the bra, and turned back around to give him a little kiss on the forehead. Her nipples were hard, standing out against the thin fabric of her shirt. I'm sure Steve noticed too. Anyway, that was it for that lesson.
Finally it was time for his final exam at VU. He would go on a date with Dianne to a restaurant and movie, chat, and flirt a little. Then they'd come back to his house for a nightcap. I waited at his house and watched TV. When they arrived Dianne told me that Steve was doing very well. They talked some more. Steve put on some music and they danced, holding each other close for one slow song at the end. Dianne told him she was proud of his new confidence and asked him if he thought he was ready to date now. He said no.
Dianne had him sit on the sofa with her and instructed him to put his arm around her as I had done. She snuggled against him with her head on his shoulder. Then she surprised me by telling him to massage her neck and work his way to cop a good feel of her breasts, as I had done in the earlier lesson. He looked at me questioningly, and I nodded. Dianne must know what she's doing. This could be just what he needed to really gain confidence. And secretly, the thought of our friend feeling Dianne's breasts and wanting her turned me on too. I wanted to see it. She cautioned him that he must not rush it too fast, nor go too slow. Just move at a natural pace. Steve had learned his lessons well, and before long he was locked in a passionate kiss with my wife while groping both her breasts.
Dianne broke off their embrace. "That was good Steve," she giggled. "And I have to say I enjoyed my part as your teacher. So once you get to this point you know where it's going and what to do, right?"
"No!" Steve looked distraught. "I couldn't take it any further. I can't date. I don't even want to, okay? Thanks for trying to help me but I guess I'm just hopeless."
"But why?" Dianne asked. Steve didn't want to say but she persisted.
"The thing is," Steve said, "my penis is really small."
Dianne began, "Size isn't..."
"Yeah, yeah," Steve interrupted, "I know, size isn't everything. But the sad truth is that isn't really true. Size means a lot to a lot of women."
Dianne tried to argue with him, but he couldn't be moved. Finally he told the story of the last real date he had, six year earlier. Things had moved very fast, but when she opened his pants and pulled out his penis she had laughed at him and left.
"Oh Steve," Dianne said. "some women are assholes, like that one. Some men are assholes too. Not most of them, thank God. And a lot of 19 year olds can be pretty stupid. There are plenty of women out there who would be perfectly satisfied with your body. You're not bad looking you know."
"I don't want to be laughed at again," Steve said.
"Come on then," Dianne said, "Show it to me."
"What?" said Steve.
"Do you trust me? Show me your penis and I promise I'll give you my honest opinion. I'll even tell you if I think it's funny."
Steve hesitated. "N-n-no, I can't."
"Tell you what," Dianne said. "Show me yours and I'll show you mine. Here's a down payment." She turned her back to him and slipped off her shirt. "Do you remember how to undo one of these?"
Steve remembered. This time when her bra fell to the floor she turned back to him, proudly displaying her luscious breasts.
Steve stared open mouthed at my wife's beauty. "You're so sexy Dianne!"
