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This took place almost a decade ago but is still of my most memorable and favorite nights having sex.
Cheyenne and I met in law college and were classmates. We had a lot in common—emotionally we were both children of broken homes suddenly surrounded by trust fund babies and others who had a much easier and more predictable road to law college than either of us. Physically, we were a match. She’s 5’7 and was around 175 when we first started dating and dropped into the 150s during one of our little breakups. Curvy, raven-haired, pale, cute heart-shaped face and a pleasant little smile, medium-size lips with a broad smile with a grin I’d describe as “mischievous.” Her body was curvy and strong, with C-cup breasts, wide hips, and a big, full, round ass attached to very firm, thick, and strong legs. I have a lot of types, but she was just my type. She fit organically against my body: 6’2 and athletic, carrying a little extra fat in the middle but with arms, chest, shoulders, and legs toned by years of weightlifting, sprinting, cycling, and all sorts of cross-training therein. And working manual jobs. Foiled by an eating disorder that created some inconsistent diets.
She grew up with a style that was a little goth and a little bit hard rock/heavy-metal, but was transitioning into looking professional, as we are were in law college. I was the same way but a little more punky and a little more jockish, but keeping a pile of wavy hair atop my head with glasses and a beard, I only looked a -little- out of place as a law student.
We dated on and off. I think our physical chemistry was clear from the beginning, and we seemed to be right for each other in a few key methods – she loves giving blowjobs, and I love receiving them. She’s a bit of a size queen, and I was just big enough to get her off. For her, this meant a deep, slow, sustained set of thrusts inside her. If I did this just right, she could cum from penetration. Her moans, unlike many of my other girls to that point, were heavy and deep instead of high and fast.
My favorite thing to hear, relaxing between classes, was words whispered directly Cheyenne, from her back into my ear, with me on top of her:
“just like, that, just like that.”
“don’t stop. Don’t stop.”
“Mmm, mmm, MMMMMMMMMMMMMM”
And then a few moments after she came with me pushing deep inside her, she’s snap out of it with a snarky little “nice job” or “good work” or a perky little “your turn!”
And with my turn, especially if we were short on time, I would do my favorite move – sitting up on my heels and pumping my cock in and out of Cheyenne quickly, fucking her hard and fast, evoking more of the classic higher-pitched vocalizations out of her that were characteristic of her only after I made her cum, and I would explode—occasionally inside her, if we had the pleasure of redundant birth-control ways (everybody sleeps on the spermicidal lubricant!) or onto her curvy hips and stomach and pretty natural tits.
It was great fun, and we knew how to get each other off.
We dated on and off, and after our final official breakup, we weren’t seeing much of each other. In fact, our correspondences became limited to when either of us (usually Cheyenne) was drunk. She texts me a photo of her in a little black dress downtown, looking extremely fuckable in the eyes of any guy there (and probably a lot of girls):
“What if I showed up to your door in this?”
“What if I showed up to your door naked?”
I was buzzed myself but back home and I told her “yes to both, the door is unlocked” and she says “I’ll find a ride and let myself in.”
She arrives and lets herself in and it’s dark in my apartment as I’m drifting away in bed, knowing that I’ll perk up when Cheyenne gets here (if she gets here, you never know). I heard the door open and, well-trained as I was apparently, my cock jumped to life. I played coy and wanted her to strip naked and jump in bed but she had other ideas.
“This is the last time. So, make this count.”
She instructed me to take off her dress and her top and then pushed me away so she could do the same to me. I was down to boxers and a T-shirt, but she pulled off my shirt and playfully grazed the top of my boxers.
“I see you’re ready to go, just this once more.”
I can smell alcohol on her breath and I ask if she really wants to do this.
“Absolutely, this is a nice buzz.”
She takes off her panties (a pink thong I loved seeing her ass in) and pulls my shorts down.
“Sit there.”
I sit on the side of the bed.
“I love sucking on this and want to enjoy it filling up all of my mouth once more.”
She sucks on me in her characteristic style – a little bit self-serving, enjoying it for her as much as she is to give me pleasure. She tickles my balls a little bit and licks the shaft. Licks my balls just a bit, just enough to tease me. She’s never so completely in control, it’s usually me calling the shots to some degree, so I can see this is all different. It’s got more emotional charge for her than it does for me, and I feel like I am along for the ride and she is the rollercoaster.
She pushes me up on to my bed, sticks two fingers into my mouth, and uses my spit to lubricate her pussy. She’s getting on top first.
Cheyenne gets quiet and climbs on my cock, inserting me slowly and at this point I’m in satiable. I had less sensitivity (astonishingly) back then than I do now, so there was little risk of my finishing in this position. She told me to be quiet and she rides me with some intensity. She has a little bit of “whiskey clit”—she’s not finishing fast like she usually does.
After a few minutes with just music playing lightly, Cheyenne says “tell me you love me while I ride your dick for the last time.”
This might be getting weird, I think.
“No, it’s okay, I don’t know if I believe it about you either but we can just pretend, and it’ll be hot.”
“I love you Cheyenne.”
“I love you Jack,” she says.
We repeat it and mix in some more standard dirty talk at a level we didn’t usually. And she leans forward and kisses me deeply—more deeply than maybe ever before, and certainly more deeply than in a long time. She’s processing and letting go. But she’s also gushingly wet, like I’ve never felt her.
Finally, she gets up, flaunting her body, the fittest it’s been, and I’m stroking her stomach that she’s now proud of. She is letting me imprint this image in my mind, but she says no photos. She sits up and grinds me all the way deep.
“mmm, Mmmmm, MMMMMMMMMMMMMMMM.” I feel her walls clench, her tight quads convulse, and she collapses on me.
She’s shifting emotional gears now. “Fuck me from behind and cum inside me. I want to feel your balls smacking against my ass while you do it.” I think she’s letting go other things, now.
I don’t protest to that and enjoy handfuls of her ass, still delightfully big despite her little body transformation, and it’s not long before I unload all of my cum inside of Cheyenne for the last time.
***
In the morning, we didn’t speak. She put clothes on to sleep and I honored the gesture and did the same in kind. She wasn’t cuddly that night and I assume that our sexiness ended with that load of cum after our long session. I went to take a shower.
I was surprised when she walked into the shower and I got to watch her strip. I loved (hell, still would) showering with Cheyenne and it was often a precursor to sex. She got in the shower, saying nothing, totally nude, and looked down and watched my cock swell back to its full and insatiable-for-her size. She washed herself but did not touch me. I touched her, though, which she allowed. I rubbed soap all over her body, caressed her breasts and nipples, made more than a passing graze into her slit, made sure to spread her cheeks a bit to wash her delicious round ass. Once she rinsed off, she still hadn’t touched me. She looked me in the eyes and reached out her hand. With her middle finger, she tapped the tip of my rock-hard cock one time before stepping out of the shower, drying off, and getting dressed.
We never had sex again.
Even though I want to, I think it ended perfectly, and how often does a sexual relationship end like that?
NSFW: yes
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