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sinning with the schoolteacher
amongst some guys there is an urban legend that the guy that takes a woman’s virginity can always have her. while i can’t say that’s definitely true or not, as i’ve only taken one woman’s virginity, in the case of me and jackie (not her real name) it is. i think jackie fell in love with me the moment she saw me about 25 years ago. i can say that because her eyes got as big as dinner plates and her jaw dropped the day i went to my friend’s house where she happened to be babysitting. while cupid’s arrow didn’t exactly hit me, i have to say that she was definitely attractive, a perfect spinner at barely 5 feet and 90lbs of dancer’s body. guys also say that a woman knows within a minute of meeting a man whether or not she’s going to sleep with him (provided he doesn’t do something to screw it up), and i’m pretty sure her mind was already made up, it would just take a little patience on my part as she was, after all, a virgin. once the flood gates were opened, however, she was a true nymph. we fucked any and every chance we could get, in public, in private, in the car, in hotels, you name it. she couldn’t get enough and i was happy to oblige, our sessions would often last hours on end, with both of us having the energy and stamina to burn. we were together a couple of years, until a coworker introduced me to paula, a woman so gorgeous i saw her cause a car accident one day (all four guys in the car had their eyes locked on paula’s ass, which was…amazing). jackie has never forgiven me for breaking her virgin heart, but that hasn’t stopped her from fucking me from time to time. sorta.
fast-forward 25 years to saturday. now jackie is a 40-something year old school teacher who’s never been married. she doesn’t have the dancer’s body anymore, she’s become a mini-bbw but she’s still quite attractive (don’t get me wrong, i’ve dated/fucked bbws, but my preference is for the petite). i didn’t realize it was her, and i remember thinking she had that “boom pow” combination of phat ass and big boobs, which got my attention. at least that’s what i thought when i walked up behind her in the d**gstore, and i didn’t know it was her until i accidentally/on purpose brushed up against her. she turned around and our eyes met, almost like that first time, only this time i could tell she caught herself, not wanting to give away what i know crossed both our minds.
in the years we’ve been going back & forth jackie has gotten uber-religious, always praising jesus or quoting scripture or something. not that i’m an athiest or anti-religion, like anything, it has a time and a place, and it’s not in my bedroom. it also has made it increasingly difficult to get jackie to give in to our carnal desires, which is a shame because she’s fantastic in bed and gives the best head i’ve ever had. it’s as if her mouth were made to fit my dick and her lips were created to caress my balls. even with the extra pounds on her once-tiny frame, she can still get her legs up over her head. if she would only let me fuck her sweet ass i probably would have married her by now. but i digress.
now that jackie is a bible-thumper, getting her naked and sticky is much more of a challenge, and i think that’s why i go after her so hard when we run across one another. it’s been several years since our last encounter, and i was really wondering if i was up to the task. we stood in the store chatting for a while and i invited her to grab some sushi, our favorite meal to share. this was perhaps a dead giveaway that i was trying to get in her panties again, but she said yes and off we went. the japanese restaurant was only a few minutes away so we were having sake and spicy tuna rolls in no time. thank goodness she’s not a tea-totaller, i’d need all the help i could get to have the kind of dessert i had in mind, and sake is a great wingman.
i have to say, it was a great lunch whether or not jackie wanted to fuck afterwards. she’s always been fun to hang out with and is usually the life of the party wherever we go. this case was no exception and the owner of the restaurant enjoyed having a free floor show so much he sent us some more sake as thanks. by the time we left, we were both feeling good and i could tell by the way she was touching me as i walked her to her car that my afternoon was going to be full as long as i played the next move correctly. this was one of those i knew that she knew that i knew that she wanted to fuck, but i couldn’t let on that i knew she knew i knew. the games we have to play in order to get laid sometimes.
i went for the simple approach and asked her what she was doing with the rest of her day and if she’d like to hang out, fully expecting her to have some sort of church function or chior practice to go to. she surprised me by saying she had something she needed to do but would come by later, not a complete no but not quite a yes either. i figured she was giving herself time to let the sake wear off and keep my evil ways away from her virtue. when she told me to meet her at her place in an hour, i realized that teacher was inviting me over for private tutoring and i planned to stay after class.
a fresh shower and touched up manscaping and i was ringing the buzzer to her apartment building, trying to think neutral thoughts so i didn’t knock on her door with an obvious boner. guys say you should think of baseball but i kept imagining my bat in her catcher’s mitt… as it turned out, all that effort trying to keep my pants from bulging was wasted effort, as she answered the door wearing nothing but the wetness from her just-finished shower.
“don’t stand there staring, you know this is what we wanted from the moment u bumped into me in the d**g store, pretending it was an accident.” i didn’t know she knew i knew she knew, but i was glad she did. “hurry up and close the door you’re letting a draft in.” one thing i do know is that men love to be seduced. we always feel like we have to do something extra special to get women to sleep with us so it’s nice when the woman takes the initiative. not only did jackie take the initiative, she was firmly in the driver’s seat. the only light was from the dozen or so candles she had lit, and her apartment had the subtle scent of jasmine. once again, i had stumbled into a woman who was determined to fuck me and i’d had no clue. and fuck me she did, well, right after she tried to suck me inside out.
i didn’t even try to hold back, even if i could have, which i’m sure i couldn’t. she knew she gave head like an angel and never stopped staring at me from the time she pulled my cock out until the moment i exploded in her mouth. she never blinked and kept sucking even after i finished giving her my load. she knew this was my weakness, as a great blow job will usually put me to sleep, but she wasn’t having any of that and sucked a second load out of me before i knew what happened (i haven’t had orgasms that close together in ages). i honestly thought i was going to lose consciousness, as i was seeing spots and was dizzy, but then she slowly climbed on top of me and guided my brick hard dick inside her.
i’ve said this before but it deserves repeating: there is nothing like the feeling of the first time your dick enters a woman’s pussy. the way it resists opening at first then engulfs you and pulls you deeper insde. that sensation alone is almost enough to make me cum instantly, and then the warm wetness surrounds my shaft and it feels like a little piece of heaven. jackie may be a bible-thumping school teacher but she hadn’t forgotten how to fornicate and could teach a masters class on sinning. she rode me ever so slowly, rocking her hips and leaning over me so her nipples brushed my lips. i could see that she was in charge and that i was just along for the ride, so i just grabbed her ass and held on while she made herself cum over and over. feeling her tremble and shake each time she came turned me on so much that i didn’t even realize i was screaming and cumming right along with her. then she shocked me: she raised up and sat on my dick, then wiggled until i was balls deep in her ass. i don’t know who squealed louder, her or me, but this time, instead of the slow rhythmic way she rode me before, once i was balls deep in her ass she started bouncing up and down on my cock like it was a pogo stick.
jackie and i had never done anal before and the shock on my face had her smiling like the cat that ate the canary. “yeah, i’ve been exploring some things since our last encounter, and i had you in mind” she said as she fucked me with her ass. and by fucked i mean fucked. once she built up momentum she was pounding her asshole so hard it had to hurt like hell, but she never slowed down and stared at me the same way she did while she sucked my cock, with the same end result. she had to feel my cock start to convulse in her ass because she sat all the way down on it and whispered to me “that’s right, fill me up baby.”
her wish was my command and i came and screamed even harder than the last time. at this point i started to wonder if this was payback for me having broken up with her all those years ago, if she was trying to fuck me to death. i’m not saying i saw my life flash before my eyes but i do recall making some promises if god let me live.
i don’t know if god was listening, but jackie eventually relented and poured us some wine while i caught my breath. “you better drink up cowboy, this rodeo ain’t gonna be over for a while” she said with that mischevious smile and my dick started to wake up again. she wasn’t k**ding either, we fucked in just about every square inch of her apartment over the next 36 hours. “you’re lucky i have class tomorrow or we’d be at it all day again.”
i finally staggered to my car around 6 monday morning, as she was getting ready to head off to shape the minds of little k**s. as she kissed me good bye she had one more surprise for me, “if you ever want this pussy again there are gonna be some ‘i dos’ invovled, and i mean it this time.”
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