A short story of the time my ex-girlfriend showed up at my college apartment and challenged me to a sexual supremacy match (first to cum wins).
Realism Rating: 4 stars.
"Jamie" and I really did date for just under a year. I met her on a study-abroad trip my freshman year. We dated until spring semester of my sophomore year. We really did "play-wrestle" as a form of foreplay more than once. On one of those occasions, she pinned me down, sat on my face, and made me go down on her.
This short story pulls from that experience, plus the one or two times after we broke up that we would randomly see each other out, once or twice resulting in her coming back to my apartment.
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My apartment was a bit of a mess, empty coffee cups, crumpled up notes, flashcards everywhere. I was pulling an all-nighter to study for my Accounting Mid-Term. I was a bit of a night-owl, so the late hours didn't bother me so much, the Accounting terms on the other hand made it very difficult!
It was just after 1am, the bars around campus had just closed. I lived in a nice apartment with my best friend Matt. We were lucky enough to find this place only a few blocks off Main Street, where many of the bars were located. I heard a knock at my door. Thinking nothing of it, assuming Matt had forgotten to take his keys with him, I opened the door without looking to see who it was.
She was through the door before I knew what had even happened. "No, not tonight. Absolutely not" I stammered looking at my ex-girlfriend. Jamie was 5'4, blonde hair, athletic build. She had strong legs (former cross country runner) and perky B cup tits. It was an unseasonably warm day in early October, and she was wearing a short skirt.
"Thanks for letting me in baby. I wore your favorite outfit thinking you'd be out having fun. Are you all alone studying? We'll have to fix that now won't we?" Jamie said as she went in to hug me.
"Not that skirt!!" I thought to myself as I was seemingly powerless to resist. She knew about my weakness for "skirt weather", she knew about other weaknesses too...
As she hugged me, she brought her lips close to my ear and whispered "wanna wrestle?" before sliding her lips over and kissing me. I should have resisted, I should have told her I had to study, that my midterm was important, but what would YOU have done in that situation?
"I, ahh, I really should keep studying." I weakly protested between kissing my ex-girlfriend. "Is that what you REALLY want?" She asked moving her hand over my now fully erect cock as she lightly licked my ear.
My eyes rolled into the back of my head as I couldn't possibly say no at this point. Before I could muster any sort of additional resistance, she had taken off my belt. She playfully put it over my neck and led me into my own bedroom, like I was her dog on a leash.
My brain was spinning on how I ended up in this predicament, but I wasn't exactly complaining. "I know how important your mid-term is baby, and I'm really tired. So we'll make this match a quick one okay? But it'll be special, because I want to do a first to cum wins match with you!"
My eyes widened, they had to be the size of saucers. She playfully giggled as she added "I'll take THAT as a yes then huh?" Again, my brain completely failed me, I was unable to even speak. She took off her shirt and smirked "Well, what are you waiting for, do you want to wrestle with me or your stupid flashcards?" She said teasingly, telling me to take off my jeans and shirt and get ready.
The night had totally gotten away from me. I had no idea how I ended up in this situation, with my ex-girlfriend standing in front of me in a short skirt and her bra challenging me to a wrestling match. Yet here I was, in only my boxer shorts standing in the middle of my room.
Knowing she had me right where she wanted me, Jamie moved in quickly, grabbed me and went in for a kiss. I closed my eyes, and before I know what she was actually up to, it was too late. She slid one leg behind me, pushed me forward roughly and tripped me onto the ground. I crashed hard onto my back.
Landing with a thud, my eyes opened in time to find her on top of me, pinning me down, her eyes glinting with triumph. "Looks like it's my turn to be on top, baby," she purred, her voice alluring and teasing.
She grinded her hips against mine, dry humping me as she kept me pinned. "That's it baby, you know how much I like teasing you. It turns me on so much!" She whispered into my ear as she pinned my arms down over my head and continued dry humping me.
Jamie straddled me, her strength surprising as she pinned my wrists above my head. A triumphant gleam shimmered in her blue eyes, a smirk playing on her lips. That knowing smirk. I HATED how much that smirk turned me on! "Looks like I've got you right where I want you, bitch," she teased, her voice a sultry whisper.
Leaning down, she brought her face close to mine, her blonde hair cascading around her shoulders. Her hips continued to grind against me rhythmically, her own arousal evident as she rocked against the hardness of my cock. "Mmm, that's right baby, we both know this is where you belong," she murmured, her competitive spirit relishing the dominant position she held as she pinned me captive beneath her.
I tried to move my arms, to overpower her and escape the pin. Jamie's grip tightened around my wrists, her lean muscles flexing with exertion as she kept me pinned.
"Struggle all you want, bitch," she taunted, her voice dripping with confidence. Her hips continued their relentless rhythm, dry-humping me with an increasing intensity that betrayed her own arousal. "But I think we both know who's in control here," she said, a playful smirk on her face, clearly enjoying the power dynamic she created, leaving me helpless beneath her.
Jamie loved dry humping me, loved teasing my dick. She once gave me a brutally long handjob just to see how long I could last. I didn't have that kind of time, nor energy, not tonight. I tried to get her off by bridging my hips up.
"Ohh, is that what you want? Okay then." Jamie purred into my ear as she moved herself forward and locked in a school girl pin, my arms helplessly pinned over my head.
"No wait, no, not like this." I protested, but before I could get out another word, my ex-girlfriend yanked her thong to the side, slid her crotch forward onto my face, grabbed my hands and leaned up towards my head. Before I could think of finding a way to kick out of her school girl pin, Jamie had locked me into a facesit pin, her clit brushing against my lips as I struggled underneath her.
Jamie's smirk widened as she felt me struggle beneath her, the heat of my breath against her most intimate area. "That's it baby, give it up. I'm going to cum all over your face." she teased, her voice filled with triumph and arousal.
Sensing the humiliation of being pinned down by my ex-girlfriend while she wore a skirt and yanked her panties to the side, I tried to kick out of the facesit pin. But Jamie's thighs were too powerful, and she had the facesit locked in too tight. I had no other choice, I had to eat my ex-girlfriend's pussy as she built up her orgasm while sitting on my face and pinning me down.
Straddling my face, she settled herself onto me harder now, virtually eliminating any chance I had of sneaking in a breath. Her body shuddering with anticipation, a soft moan escaping her lips as she took control of the situation. Her competitive spirit enjoying the power she held over me.
"That's it bitch. Eat that pussy. Show me you still know your place." she purred, as she looked down at me with that same knowing smirk.
My tongue worked over my ex-girlfriend's clit as she kept me facesit pinned. Jamie moaned softly, her grip on my wrists loosening slightly as her body began to succumb to the pleasure of my tongue's attentions.
"That's it, Dale," she murmured, her voice a breathy whisper of encouragement and arousal. Her hips began to rock back and forth across my face. She built up the power and the thrusts as she began face-fucking me as she continued to pin me.
