Doing Debbie - Some Years Later

by Tom Land

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Romantic, Oral Sex, Masturbation, Pregnancy, .

Desc: Sex Story: Tom asked Debbie out on a date when they were in high school. She was too shy and turned him down. He dreamed about her for years after that and several years later, Tom met Debbie again and this time things were slightly different.

It didn't happen the first time. I'd wanted to take Debbie out but she'd said her father didn't want her to go on the date because he thought she was too young. Some years later, I found out by asking Debbie directly that the reason she didn't go on the date with me was because she was too shy. Ah, what a loss for both me and Debbie, but sometimes in life we have a chance to do things that we messed up the first time. Going out with Debbie was one such experience.

I asked Debbie out because I thought she was one of the cutest and nicest girls at school. She was a freshman and I was a junior and I wanted to spend the entire evening with her. She was shy and I'd dredged up enough courage to ask her out only to have her say "No". Because she'd turned down the invitation, I asked another girl out and had a great time, but I hadn't gotten over my infatuation with Debbie. After some years, I still had a very special place in my heart for Debbie and I got a second time to enjoy spending an evening with her.

When I'd first asked Debbie out for a date, she'd been a typical shy young teenage girl who had never dated and who was scared to death of going out with a boy that she found attractive and interesting. I was crushed. I really wanted to date her, but when she didn't take me up on the offer, I did manage to get another very pretty and very fun girl to go with me. But, there was always that desire to have spent time with Debbie. When she was a young teenager, Debbie was very cute and had an obviously budding set of nice breasts, a very trim and shapely figure and a winning personality although she was very shy and quiet.

When I met Debbie several years later, she was now an adult woman, had been married and divorced and had given birth to two children. That put Debbie squarely in the category of "mommy pussy" and made her even more attractive to me than when she'd been a shy, virginal young teenager. I wanted her back then; I wanted her even more now as a young adult.

When I saw Debbie again, I instantly recognized her -- she'd only grown more attractive -- and found her as sexy as ever. A few years of maturing, having two children, and the normal sexiness that a woman picks up as she becomes a real woman had all added to make Debbie much hotter. When I'd thought about Debbie over the years, I often wondered what that "missed date" would have been like. I'd fantasized and imagined it many times.

I had never actually expected to see Debbie again -- but when I did my mind began churning to see what I could manage to make happen. Finally, I just decided to try what I'd tried several years earlier -- ask Debbie out on a date and see if this time she'd agree. We'd call it" going out for dinner" but the result would be the same -- time alone with Debbie.

When Debbie and I met at the restaurant, we both immediately moved towards each other and hugged and I knew that there had been much much more between me and Debbie from the feel of that hug than I'd ever hoped could be true on her end. She hugged me close and I resisted the temptation to do anything naughty, but finally after too many years, I was feeling Debbie's womanly body in my arms, and I loved the feel of her nicely rounded B-cup breasts firmly pressed against my chest.

The dinner was like something out of a Hollywood film. Here were two people who'd made some crucial mistakes in their past and had almost missed ever being with each other. As we sat there eating and talking quietly, I finally said some very pointed and honest things and I could see tears begin to form in the corners of Debbie's eyes and then they started to stream down over her smooth beautiful cheeks.

"What?? Did I say something wrong, Debbie?" I asked, not wanting to hurt her in any way.

"Oh no, Tom. You didn't hurt me at all. It just suddenly struck me how much I'd loved you for so many years and how silly I was that night to tell you that I couldn't go out on a date with you. I cried for hours that night, knowing that by telling you that I had probably lost you forever. And I had. Tom, is there any way I can make it up to you for the lie I told you that night and for not being honest with either of us?? Can I do anything to make something out of a very bad decision that I made as a shy introverted young teenage girl?"

"Yes, there is, Debbie. There's one thing that I would love for you to do -- would you let me make love to you?"

"Oh, Tom, if you were any other man in the whole world, I'd be offended by your question and I'd probably smack your face right now and get up and walk out. But, you, Tom, if you'd asked me any other question but that one, I'd have been so disappointed. I'd have been so crushed that you didn't want to make love to me. Oh yes, Tom, oh yes, I would so much love for you to me tonight, Tom, more than anything I can think of. Oh yes, Tom, please take me and make love to me."

With that, Debbie stood and walked hand in hand with me out to my car and we drove to a nearby hotel where I'd booked a room for us. Debbie looked even sexier to me as we went to our room than she had earlier. Earlier I'd only hoped that I could make love to this beautiful woman, now she told me that she wanted me every bit as badly as I wanted her -- and she was gorgeous. Oh man, I could hardly wait.

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Story tagged with:
Ma/Fa / Consensual / Romantic / Oral Sex / Masturbation / Pregnancy /