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First Time With Jenna

In 97 after I separated from my wife I moved into an apartment building. It turns out one of my neighbors was a girl I went to college with. Eileen was 2 years younger than me and I had taken her out a couple times in college. At the time she had a boyfriend she wasn’t totally happy with, although we liked each other nothing ever happened because she’d always patch it up with him. We left school and barely saw each other for 9 years. Eileen had been a teenage mom. Another reason we didn’t get together in college. The boyfriend was the dad. well here 9 years later the bf was out of the picture. Even still Eileen and I were no better than hit and miss. We’d have great sex but neither of us wanted a serious relationship. We enjoyed our friendship much more I guess, or had no faith in love. Anyway… for the last ten years Eileen and I have been lovers off and on. But the bigger deal is that we’ve been close friends all along. Her daughter Jenna and I were also close. Her dad had moved to Texas and lost touch, we did picnics together and all the family things for years.

In 2003 Eileen and I were in the off stage of our relationship. But we still spent time together. Jenna was graduating high school and we had a lot of things to do that summer. Graduation party, vacation to the beach, we got closer and closer. Jenna had me thinking about her a lot. She had grown to 5’9″ with lovely long brown hair with lots of auburn in it. A sweet body but more importantly the most gorgeous smile you’d ever see. It was that summer that things got kooky. Jenna showed a great dislike for the girlfriend I had been seeing for 6 months or so. She’d visit my apt while the gf was there and would watch movies with us and those sorts of things. Jenna would act like the sweet younger sister looking out for me. Warning me that the gf was just horrible for me. When the gf and I broke up (really wasn’t anything to do with Jenna’s advice but I let her take the credit) Jenna was spending even more time with me. She’d tease me that I needed a girl around to keep me from going back to the psycho girlfriend. Jenna would help me out with chores and she even cooked once in a while. She’d be at my place, sometimes with mom sometimes not, till late hours of the night just talking. I remember as she was getting closer to 18 she’d tell me stories about older men hitting on her. She was very interested in if I thought that was right or wrong. At the time I would tell her that she was approaching her 18th birthday and she could do what she felt was right when she got there but inside I was jealous. I fought to convince myself that I was being protective of this young lady who I’d cared about for close to ten years.

Around this time her mother and I began seeing each other again. This means wild sex 3 or 4 times a week. It was great. There’s nothing like being with your best friend. This was the summer of 2004. Jenna turned 18 and nothing really interesting came of it. She started college she had a new boyfriend and we were all as close as ever.

One night Jenna was at my place while her mom was sleeping at theirs. Eileen had a big meeting the next day and I had the long weekend off. Jenna decided to ask a lot of questions about her mom and I, was I going to marry her, how did we meet those sorts of things. She asked me if I liked her boyfriend and I told her no. now it started to get weird. She wanted an explanation why I didn’t like her boyfriend. And she was persistent. I couldn’t give her a good answer at first but in the end told her that because I had known her since she was tiny I probably wouldn’t like any boy she was with. Now she goes in another direction. She ‘confesses’ that her and her boyfriend have had sex, and that he was her first and that it wasn’t as good as she expected. I try to give her innocuous answers but she finally says to me “john! Give it up! I’ve slept in the room next to my mothers all my life, the room where you’ve been with my mom. I hear you making her make all kinds of noises and scream and I wonder why I can’t get that from sex’. She tells me that she’s listened to her mom tell her friends about being with me and that her mom says how great it is. Now the gleam leaves her eyes and she asks some question about if I think it could ever be like that for her. I give her some supposedly grown up answer about how love is more important than sex and that she’ll find love someday… etc. There was more very close talk and about 4 am she asks me if I think she’s pretty. This is a first. I tell her that I think she’s beautiful. She asks me if I think she’s prettier than her mom. Now there’s a gleam in my eye. I tell her that they are both beautiful women and I hope to be a part of both of their lives forever. At this she gets up comes to me and says “thank you john, I love you” then leaves a sweet kiss on my cheek.

The next day her mom leaves town early in the morning for her big meeting. As I said before I have the long weekend off, it’s Friday afternoon and Jenna comes to my door crying. I let her in and she tells me that her and her boyfriend had just fought and broken up. In retrospect I should have noticed that the tears were fake. She told me that I was so right about him the night before and that she was so glad to be rid of him. I sit next to her with my arm around her comforting her. I tell her that I know what would fix her up that I would take her shopping then to dinner. This is something we had done for years. Trips to the mall, her trying on clothes for me… me buying then take her to dinner.

This time it took longer for her to find something she wanted to buy. I watched her try on about 15 different things. I loved it. She would pose for me each time and the choices were all on the sexy side. Now it was common when we would go shopping together that I would get mistaken for her father. We would always pretend that I was. When we checked out at the department store the lady made a remark about how sweet it was to see a girl and her daddy shopping together.

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