First Time With Jenna

Introduction:
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. Jenna, with a smile on her face told the lady “this isn’t my daddy it’s my boyfriend”. I laughed and the clerk was left with an embarrassed look. Jenna grabbed my hand and told the lady that it was our anniversary and that I’m so good to her and kissed me (still on the cheek). I was left with nothing to do but laugh and walk away as fast as I could. Jenna grabbed my hand and walked out with me playfully continuing the joke.
When we leave the store she’s still holding my hand. She says to me, “if it were our anniversary, where would we go for dinner” … I tell her that since the first place she and I ever went to eat was Ciccante’s (small Italian restaurant) that that’s where we would go. She asked if we could go there and I said of course.
At dinner Jenna decided to take the lead. She insisted that I buy a bottle of wine, right in front of the waitress she complains that it’s our anniversary and why won’t I buy a bottle of wine. I was not in the habit of buying alcohol for her and she had never even asked before. Well dinner was interesting. Jenna was really into pretending we were a couple. When she went to the ladies room, as she walked by me she reached out and caressed my cheek. I never told her this but when she did that I got Goosebumps. I blamed it on the 4 glasses of wine. She had 2 and I was thinking that’s why she did it too. Jenna was very involved in pretending we were out celebrating our anniversary. She asked me during dinner if I would want to take her out for our anniversary. Now I’m a little buzzed and I tell her sure, let’s do the whole anniversary thing. Even in the car she kept reaching over to hold my hand. She would say things like “red light honey” any opportunity to pretend she was my lady. Call me honey or baby. I was having fun.
We stop at home and she says she’ll be right back and when she does come back she has changed. I must tell you she looked hot as hell. She steps to me and into my arms with a sweet hug she says “thanks daddy for my new clothes”, she steps back to show off and my mouth is dropped open. She says “you’ve been around so long you might as well be my daddy.”
I take her out to a club, one of my good friends is in charge of the door there and I slip her right in. Jenna loved being there. The music, the people. I bought her a drink … she was beaming. A little girl playing grown up. I was beaming. You can’t imagine how sexy she was looking. YES I LOVED THE ROLE. I LOVED IT THAT THIS WAS OUR ANNIVERSARY.
Jenna went right up to the D.J. and started talking to him. she looked right at home, as if his club was no different than her high school prom she had been to only 2 months earlier. she came back to me and said “ready”. just then a really cool techno song came on, she grabbed me by the hand and pulled me toward the dance floor. We danced for about an hour, she’s a very good dancer and i’m sure I wasn’t imagining that we were getting a ton of attention. A couple times she turned away from me and ground against me. I tried to convince myself that she couldn’t feel my hardening cock, but I later started to realize she kept doing it and the reason was that she was checking to make sure I was still hard. At one point there was a slower song. Not a love song but more of a grinding song…she threw her right arm around my neck and pressed her face against my neck. She surprised me when she nipped me with her teeth. She was writhing against me; I had my hand on her waist. She pushed it down to her bottom. She whispered in my ear, John you’re supposed to be my boyfriend, stop acting like my daddy!
I took her back to the bar and this time she told me she wanted what I was drinking. I ordered us two captain & cokes and she put her arm around my waist standing at the bar. We went to the back of the club… it’s a little quieter there. I got us another drink and we sat together. Jenna says ‘you liked dancing with me, didn’t you’. I asked her “how are you so sure” … she says… “Just a feeling I got….. Against my back side!”
The night took a definite turn now. There was no little girl in her anymore. She decided right then that she was going to be my lover. I think she had decided a long time before but right then she knew she was going to follow thru
Jenna stands up, bends over to my ear, “Come on John, it’s our anniversary”, and grazes her lips along my cheak to my lips. Her tongue barely past her lips i feel it on my bottom lip, then her lips gently touch both of mine and our tongues press lightly against each other. now her’s pushes against mine. and our lips press harder. her fingers along the nape of my neck pulling our mouths together tightly. her breath slightly harder, i can taste her breath. her hand goes to my wrist and pulls me to the edge of the booth. Our kiss breaks, it felt at the same time like it lasted forever and as if it was barely a second.
i get up from the booth, my wrist in her hand, she leads me to the door. now we are holding hands and walking together without talking. When we get to the car she kisses me again. a bit harder yet still soft as though a breeze could seperate us. I feel a little dizzy, totally taken away by the moment. the smell of her breath and mouth, the taste of her tongue. the bumps on her tongue against mine. eventually the kiss breaks. she presses her cheek against my shoulder, she asks me where we are going next.
We drive over to station square and to the marriott. we walk in and to the lounge, i order a drink for us and we sit at a small table. she tells me how much she’s loving our anniversary, she says that it’s even better than she thought it would be. there’s a twinkle in her eye kind of telling me she really wants me to go along with the idea that it’s our anniversary. She asks if i’m happy with how our nights going. i smile and say “far better than i could imagine” … she excuses herself to the ladies room, and while she’s gone i go to the desk and get us a room. i’m back before she returns. we sit near each other. she’s being a little coy now. she tells me how she loved dancing with me. She says she doesn’t want the night to end. this let’s me know that getting the room is exactly what she wanted and hoped for. i choose this time to pull out the keycard for the room and she smiles. a moment later we’re leaving the lounge. to the elevator. to the room.
When we get in the room, she comes to me, pushes against my chest letting me know she wants me to sit in the chair. then she sits on my lap. her lips come down toward mine, in what felt like slow motion. i felt her breath against my lips first and that’s always a huge turn on for me. our lips barely touch yet her tongue is heavy against mine. it’s a short kiss and she seperates, she says to me softly, “i wasn’t sure we’d end up here”, then another hot kiss, “i’m so glad we did”.
she stands and slips the straps of her tiny dress from her shoulders and let it drop to the floor. she covers her breasts at first then slowly takes her hands down. she takes my hand and leads me to the bed. she puts her hand on my belt and in no time has it undone and then she lets my pants fall to the floor. i take my own shirt off, half bewildered at what’s going on. her breasts were gorgeous though. i lie on the bed with my boxers still on. she goes to the foot of the bed.. seperates my feet so my legs are spread. she gets up on the bed, between my feet on her knees. she reaches out, touches my left knee and caresses my leg in a sort of circular motion. slowly inching up. as she does this she kisses the inside of my right knee, not something i had ever felt before but it was so nice i shivered. she continued her caressing and kissing, not saying a word, with an occasional glance at my eyes. her expression never changed. she was intent, she was refusing to give me a chance to back out. as she moved up my leg i could see her eyes were more on the tent forming in my boxers. i held my breath the first time she slipped her fingers under my boxers but she didn’t go very far. as it turned out i’d have to wait a few minutes before she’d touch my cock. but when she did OH BOY. she ran her fingers up my balls to the underside of my cock. then she slipped her fingers around it, and gave the sweetest squeaze that i can remember. she ran her thumb up to the tip and rubbed on the underside of the mushroom head. she rubbed me there for a few seconds and i’ll never forget the smile on her face when she rubbed my precum off my hole and over the tip of my cock.
her chin was no more than an inch from the tip of my cock. only seperated by the thin material of my boxers, when she spoke for the first time since we moved to the bed. she touched my cock to her chin and sweetly asked “can i see your cock daddy? then may i taste it please?” finished that off with a sweet smile.
i simply lifted my ass a little off the bed allowing her to pull them down. now we get to the part that even now get’s me hard just thinking about. she sucks my head between her lips and runs her tongue over my cock’s head. she takes my guy out of her mouth and she’s decided it’s time to talk a little. she tells me that she’s heard her mother and i make love a thousand times since she was younger. she says this to me with her mouth at the tip of my cock, her eyes on my head as if my cock is a microphone almost, or maybe she’s talking to my cock. she thoughtfully continues, as if she’s trying to remember a dream, she says that she wants to know if when her mother and i play daddy and lil girl if i ever imagined her mom being her. i tell her mmmmaybe. to be honest it had never happened when Jenna was actually a little girl.. but in the last few weeks it had happened more than once.
Jenna wiggles up my body, my cock against her tummy, she looks into my eyes now, as if she wants to make sure i hear this next part. she tells me that for years now, when she would listen to her mother and i having sex thru the wall she would touch herself with her eyes closed wishing she were her mother. imagining me being her lover. what do you think of that? i didn’t say a word. she was gazing in my eyes, i’m not sure if i smiled or what but something let her know that i loved hearing this. it was the sexiest thing i’d ever heard in my life.
my hands are on her ass rubbing my cock back and forth against her clit. feeling her juices on my shaft …. wow. i keep doing this… waiting to see how long she can wait. when she’s waited as long as she can she whispers in my ear “Do it, daddy, fuck me, put your cock inside your lil girl!”. i don’t think i’ll ever forget how it felt as i slipped inside her. tight and wet and warm. she moved so well against me. we moved so well together.
she rode me for a while. as her breath became heavier and her body began to sweat, i reached up behind her and grabbed a handful of her hair, and rolled her over on her back beneath me. i spread her legs wide and raised her knees up to her shoulders. my arms under her knees against the bed. i raised up on my hands and toes and slid deep inside her. i continued with long smooth strokes, then i began bumping against her as i sank deep within her. harder and harder, i told her to hold her lips open with her fingers. i wanted to get as deep inside her as possible. my face down near hers, she threw her arm around my neck and pulled me closer. i knew she was close to orgasm. as she clung to me, i drove inside her harder and harder. her ass bouncing off the bed and her girly slamming against me as i was coming down. she came so fuckin hard. i loved it. “oh my god, oh god”… i harshly whispered in her ear… “jenna, tell me, fuck me daddy” .. she did… then i tell her “say fuck your lil girl daddy” she did. i’m loving it.. she’s loving it…she cums so hard…….my hand under her arms and holding her hair while i’m holding myself up by my elbows and toes. her arm around my neck… now as she cums she wraps her legs around my back… i drive in as deep as i can… her chest and belly are coated in sweat. i have to fight like hell to keep from cumming. when she said ” fuck me daddy ” i wasn’t even close but after she said it twice i was on the verge. she humps against me as she cums… i stay as still as i can. my cock is on fire, if i move inside her at all i’m sure i’ll cum. i want to wait… i want to wait a long time. hell this girl told me a little while ago she’s imagined fucking me for a long time. i am going to make sure this is one night she won’t ever forget.
i roll over on my back.. .rolling her on top of me. my hands on her bum as my cock slips out of her. i’m still stiff as hell but i’m just waving in the air between her legs. she sighs deeply and lays her cheek on my chest. i stroke her hair and we say nothing for a while. she slides off my chest… and she grabs my cock. a huge smile on her face. she wraps her fingers around the base of my cock … squeezing it tight… she licks the palm of her other hand and starts rubbing my head. now, i don’t know about all couples.. but this is something that i like very much. it’s something that i had often asked her mom to do for me. in fact we’d make a game of it. i’d ask her to squeeze it harder and she’d tease me by taking her time getting to a full squeeze. knowing that as she went from a gentle squeeze to a firmer and firmer one.. she was driving me crazy. i’d ask her “please squeeze me harder”… now…with jenna there, between my legs with her hand wrapped around my cock.. i see this huge smile on her face. i smile back and ask her… “how did you know i like that lil girl” … she grins and says “i told you daddy, the walls are very thin at moms place”… “i know a lot of things you like daddy! … and i want to show you them all.” at this she redirects her attention to my cock, now she spits on her palm…then spits on the head of my cock and she rubs the head then strokes the staff… all the while squeezing the base of my cock… just like i like it. she does know what i like. it’s amazing. she bangs the head of my cock on her tongue and sucks on the tip…she runs her hand up and down as she goes from stroking me with her hand to sucking me into her mouth. Oh my god what a beautiful site. I love watching her face down there by my cock. i love her eyes on me as she puts her lips around the head of my cock. i love how she tugs on my ring, the piercing i’ve had done on the head of my cock. i love seeing her lips and eyes smile. “daddy, am i a good cocksucker” … oh definitely jenna, you have me sweating, i’m getting a little light headed… i’m trying so hard to hold back that it’s driving me crazy. “why hold back daddy, we’re gonna be here all night… let me get you off pleeease. i want it to be me that gets you off”…. MY GOD… SHE KNOWS… you see.. her mother had never been able to get me off with her mouth… sure if i helped her by stroking myself as she licked my head, yeah, i could cum. but her mom had never ever gotten me off “on her own” .. i lay my head back… i close my eyes… and simply concentrate on how great she’s making me feel with her smallish hands running up and down my cock, and her lips and tongue making love to the head. funny thing is that while my eyes are closed trying to relax i’m picturing her face.. so i decide to open my eyes and watch. she stops and with my head right on her lips she asks “daddy, do you want to fuck my mouth, you can y’know, do you want to”… i grab her hair, without saying a word, and start moving her face down and up my cock. i push into the back of her mouth, gagging her slightly, she doesn’t back off… she is waiting for me. now i know i’m gonna cum. just a few fucks into her mouth, feeling the head of my cock hit the back of her throat… and i release… OH WOW… i hadn’t cum that hard in a long time… my thighs shiver, it feels like i’m losing my breath… i see her as the cum shoots out of my cock against the back of her throat, then comes spilling out her mouth onto my upper thigh, she takes over now, i can’t move. she fucks my cock with her mouth and sucks on the head… her sucking causes a whole new wave of shivers throughout my body…. her hands on my thighs as i arch my back off the bed… her mouth will not let go of the head of my cock…. finally i can speak ‘good girl…. ohhh good girl’ .. she smiles at this … she squeezes the base of my cock harder..and takes me out of her mouth.. .she rubs the head of my cock on her lips in a circular motion …. wow… i could never describe how fantastic it was… never. “oooh daddy, i dropped some” as jenna wipes my cum off of my thigh. she wipes my cum on her tits then holds it up to her nose. it’s very cute that she’s checking out my goo. she’s tasted it now she’s smelling it.
she’s still on her knees between my legs…my cock is still hard, laying against my belly. she starts at my knees and rubs my thighs. very nice long strokes… very relaxing. she tells me she can feel the tension in my legs and i tell her it’s because of how hard she made me cum. “so i did good”, she asks. i light up and say “oh wow, you did excellent… the best i’ve ever had.” she likes this, a warm smile on her face, and she says “i want to do a lot of things to you better than you’ve ever had”.
there’s more . a lot more… jenna and i have been lovers ever since. Eileen and i have been lovers as well. eileen doesn’t know about jenna and it makes it all the more sexy to jenna and me. jenna has since moved to college and i see her far less often but we do get together several times a year. it’s really interesting. not many would possibly understand but who cares. i don’t expect to be accepted. it is what it is… that’s all.

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