[MF] The longest, guiltiest, and hottest one night stand of my life.

So I [M] have not written many stories yet, but I love reading erotic lit and decided to try my hand at it! I have had some experiences that feel story-worthy, and decided to start with one night that, after a few years and partners later, still is one of the most memorable I’ve ever had. I welcome any feedback, and my DMs are open if any folks want to chat! I also have photos of myself available (maybe posted, tbd) if that helps with your reading experience, I know it does for me when I read some of the stories here.

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I met Esme in college, at a birthday party in someone’s dorm sophomore year. Back then, she hardly gave me the time of day. I was pretty much a square, had recently gotten out of a long distance relationship, and was very new to the partying scene that my friends enjoyed. I was trying to get her attention at the beer pong table to little success. She had a reputation as a bit of a wild girl. Esme was white with shoulder-length brown hair, and sported a very fit body, with small but very perky breasts and noticeably pierced nipples, a very well-rounded ass, and legs that I would die to feel wrapped around my head. It became clear that she wasn’t interested that night. We didn’t become friends, really, and didn’t interact much, if at all, during the rest of college.

However, soon after graduation, I started dating my last ex (who will most definitely appear in later stories). Esme was best friends with my ex’s close friends, so we would run into each other pretty frequently at parties around the city we stayed in. Nothing ever happened between Esme and I while I was dating my ex, but that didn’t stop her from continuing her old partying ways that were pretty hard to ignore. Regardless, she was a blast in a crowd and always a fun flirt (I am very guilty of this as well), so she and I became friends while I was dating my ex.

My ex and I eventually broke up, and a few months later Esme and I were chatting on Instagram casually when I suggested she and I catch up. We agreed to get drinks the following week. When the fateful day came around, she texted me.

“Hey John! Soo my company got a keg to celebrate getting a big contract, wanna meet me at my office before we go out??”

Shit, I was already feeling a bit tired and a keg sounded fun but also exhausting. I decided fuck it, it’d be free drinks and she and I could dip soon after I got there.

Lo and behold, when I walked into Esme’s office I was immediately greeted by her yelling “OH MY GOD THANK YOU FOR COMING” and shoving a cup of beer into my hand. Some things never change, y’know. And Emma still looked great. She wore a tight black sweater that showed off her slim figure, and black pants that hugged her backside and legs very well. We drank and laughed for a while, I got to meet her coworkers (I also learned that night she had slept with one of them previously), and then wound up bar-hopping as we made our way back towards her apartment. We became more flirty as the night went on, even bordering on slightly inappropriate for someone who had only recently stopped dating one of Esme’s friends.

Soon enough, we found ourselves at Esme’s apartment, sharing a nightcap joint on her balcony. We sat across the table from each other, still drunk before we had even got the joint lit, and talking about something inconsequential. We smoked and talked for a while, sinking into a comfortably crossed conversation as the temperature dipped and the night came on.

“It’s getting late, how are you feeling?” I asked Esme.

“I’m pretty fucking tired and want to listen to some music inside. How about you?”

“Same here, so I should probably get going, too. It’s getting cold.”

“Ah, did you take the metro to meet me? I don’t know if it’s running this late, you’re welcome to crash here if you want!”

“You sure? That’d be much better than taking an Uber, as long as you don’t mind. I’ll be out early once the trains are running again.”

“Yeah it’s totally fine, consider it a ‘thank you’ for that joint.”

And I knew at this point where things were heading. We moved inside and I sat on Esme’s bed. She walked past me toward her dresser and put on some slow hip-hop, then to the closet and told me that she needed to change into her pajamas.

“I can look away if you want,” I joked.

What Esme did next was one of the hottest memories I have. She walked back to the bed, carrying a fresh white tank top with her, and sat down next to my right side. She faced the wall in front of me and, without hesitation, pulled her turtleneck straight up and off. She was wearing nothing else underneath. Esme sat there, at my side with her chest bared to me, for an extended moment. I forgot to breathe for a few seconds as I drank in the sight of her perky breasts and her dark, pierced nipples that I had wanted to see for years but had never had the circumstances to do so. Our only source of light was a lamp in the corner of the room, which cast slight shadows from her nipples. I was immediately turned on, and could feel my heart beating in my chest as I noticed my penis beginning to swell. To this day I imagine what would have happened had I decided to initiate right there, but I was too intoxicated by the sight of her to do anything other than watch.

Rather, Esme picked up her tank top and pulled it over her. While her chest was now covered, her piercings pushed against the fabric, and I could make out the dark shapes of her nipples against the white cloth. She pulled the covers open, and laid down. If there was any question left as to what would happen between Esme and I that night, it was simply as to when the tension would break.

I stripped to my boxer-briefs, and got down next to Esme. We laid in her bed, with me spooning her loosely. Before long, Esme scooched backwards into me, and I pulled her closer. I moved my hands along her body, up her waist and over her arms, massaging lightly as I went. A few seconds of this passed, and Esme turned her head towards me, and brought her lips close to me. I could feel her breath on my lips, and moved to meet her. Despite our inebriated state, that kiss was controlled and deep. It was the resolution of a tension that had been building all night, perhaps all year, and I wanted to make the most of this moment before exploring further.

But that came to a quick end. Esme pulled away and said to me “I don’t know how far I want to go with this.” Undoubtedly she was thinking about the strange circumstances of our friendship, and what her friends may think if they were to find out something happened between us. I was thinking about that too; I’ve made my share of regrettable decisions, and this was definitely up there. But this story would not exist if that’s where things ended. Neither Esme nor I were strong-willed enough to stop what was already happening.

Shortly after we broke away from our first kiss, we found ourselves in that same situation again. Tasting each other, and our wayward hands moving closer to the points of no return. Every time a new step was taken, we broke off, and went back to spooning. But every time we resumed, our actions only became more and more lustful.

The kissing turned to our tongues being buried deep in each others’ mouths. My hands on Esme’s waist turned to my hands on her stomach, and then to reaching around, massaging her breasts through her shirt. Esme was soon grinding her ass into my crotch, feeling me now fully hard and rubbing against her. We no longer broke away to stop, only to catch our breath or for Esme to let out a delicate moan.

Esme turned her body to face me and we began in earnest. I softly led her onto her back and moved myself between her legs. At this point we were fully in the process. Each time I pushed my groin into her I elicited a moan, and her hands tightened against my back. I kissed Esme’s neck, on my way to revisit the same sight that had captivated me moments before. While my lips made their way down her neck and to her shoulders, my hands grabbed at the bottom of her tank top and lifted it ever so slowly. Esme moved her hands above her head and I slid her top up and off of her.

My mouth now had full access to her nipples, and I was not coy about diving in. I switched between each one, swirling Esme’s piercings with my tongue and teasing the tips of each nipple with my teeth. She let out long, cooing moans when I took nearly her whole breast into my mouth, flicking with my tongue, and massaging the other breast with my free hand.

I sat up and looked down at the sight in front of me. Esme was topless, her brown hair fanned around her face while she looked up to me, and her nipples were pointing straight up at me as well, the silver bars running through them accentuating their shape and perkiness. My cock was straining against the fabric of my underwear, and was bulging precariously over the fabric of her underwear, through which I could make out the shape of a landing strip leading down towards her lips. I slid my left hand down Esme’s neck with a slight squeeze to which she gasped, and then onto her breast. My right hand moved to her mound, and I could feel the heat radiating from her through the fabric.

At the same time, Esme pulled the elastic band of my underwear down, and my cock burst out and stood at attention. She began stroking me and I moved my hand that was resting on her panties under the fabric, and swirled my fingers over the top of her slit.

I pushed one finger at first into Esme, feeling how wet she was. A deep “Oooh” escaped her lips and she arched her pelvis towards me, and my finger went in deeper. I stroked the ceiling of the inside of her vagina, finding the sweet spot where her moans became louder and less restrained every time I rubbed it. Soon I had her gasping and riding my palm as I inserted another finger and worked both of them against this spot. Her breasts were bouncing slightly with every thrust she made against my hand; I bent over to put them back into my mouth. Esme interrupted her surprised gasp to say:

“I need you to fuck me.”

I grabbed a condom from my coat and put it on, and then crawled up the bed and between her legs. Esme wrapped them around my hips, and I lined up the tip of my cock where her labia met. Slowly, I pushed myself inside of Esme. Her eyes widened as her pussy stretched to accommodate me. I’ll never forget how it felt to bottom out inside of Esme, bring my lips down to hers, and feel her breathe with me as I began to move my penis in and out of her tight opening.

We stayed in missionary, because honestly it is one of the best positions. I adjusted my thrusts to have a slight up-and-down motion, to stimulate closer to her clit. Esme responded by grabbing my ass and pulling me into her, grinding her pussy against the top of my cock and taking me deeper. I grabbed and squeezed her tits, tightening my hold on her nipple in sync with my thrusts and her grinding. Esme got wetter and wetter — I could soon hear the slipping sound of my cock going in and out of her and my penis was covered in her wetness. I began one of my favorite techniques, where I pull out almost entirely on every pull, and go progressively deeper on every thrust back in, starting with just going in up to the head of my cock. After a few thrusts, Esme said:

“Oh my god. Please John, please. Keep going.”

I obliged, accentuating every motion.

“Deeper. Fuck, please.”

I began pushing deeper into Esme than I had been doing during this exercise, and holding it inside for a pause before pulling nearly out again. I bottomed out inside of Esme again.

“Oooooh my fucking god. John. John, fuck, I’m cl-.”

Esme’s voice cut off and her body tightened up. Her eyes slammed shut and her face tensed, at the same time I felt her pussy squeeze down harder on my cock. We stayed like this for what felt like the longest second, and then Esme’s whole body released, she let out a deep and long moan, and I felt a new wave of wetness engulf my cock.

I didn’t last much longer after Esme came. Experiencing this put me so close to the edge, and just a few thrusts later I was bottomed out inside of her, filling up the condom with my cum, holding Esme tightly while she wrapped herself around me.

The feeling of unloading the pent up lust of a year subsided, and I pulled out of Esme. We lay in the strangest post-sex feeling I have had to date. Both Esme and I were silent, before she excused herself to go to the bathroom. Did I make a mistake by hooking up with my ex’s friend? Undoubtedly. Was it worth it? I had no way of knowing definitively at the time, but absolutely it was. I could tell the same thoughts had been running through her head. But we both came to the same conclusion of “fuck it, can’t take it back now,” because as soon as she came back to the room, Esme jumped on top of me and we ended up in Round 2. Round 2 was honestly more of a blur, so I am skipping ahead to Round 3.

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Esme woke up at some point in the middle of the night, with the lamp still on since we passed out after Round 2. We were spooning, and Esme began grinding her ass against me. I quickly woke up and reciprocated her grinding motion, and started to play with her nipples. Esme was all business this time. She leaned back and kissed me aggressively before sitting up and getting on her knees.

I took the cue and grabbed another condom, then lined up the head of my cock with her wet hole. Esme arched her back and pushed towards me slowly, pushing her pussy along my cock, swallowing it inch by inch. And what she said next I will never forget.

“Normally I can’t fuck this much,”

She pushed further. Every wall of her warm, tight hole squeezed against me.

“But with you, I can’t resist.”

I was buried inside Esme to the hilt, looking down at her incredible ass, while she began to sway herself forward and back, releasing my cock slightly before impaling herself back on it. I reached around to grab her tits and massaged her nipples. Esme moaned in response, and began fucking me from the front in earnest. I grabbed her soft breasts while they bounced back and forth and played with her piercings while she rocked on my cock.

We fucked harder and harder until she was prone with her face buried in her pillow, and me pounding away at her pussy from behind. She was practically yelling with each thrust as I buried my entire cock inside of her. I fucked her for a few minutes before unloading again. As I came this time, she pushed back against me, engulfing me as deeply as she possibly could, feeling me pulse with every spurt of cum that came out of me.

.

I woke up again to the early morning light coming from behind Esme’s blinds, and her just beginning to stir next to me. We kissed lightly, waking up to each other’s bodies and movements. I caressed the smooth skin of her sides, tracing the slope from her waist up to her breasts, and lightly cupping them. I brought my hand up to her face, and she coaxed me on top of her with her legs. I took the chance to slide my index finger into her, only to find that she was already soaked.

“We have to be quick, I still have work at 9,” Esme said to me.

Don’t have to tell me twice.

Esme sat up while I put on another condom, and got into position to ride me. She held my cock and lined it up with her vagina before lowering herself onto me, moaning quietly as she did. She rested her hands on my chest for support, and I did the same because really have I not mentioned enough how nice her boobs were? Speaking of, I sat up while Esme picked up her pace riding me, so I could suck on her now-hard nipples. She tasted like sweat and spit, and the room must have been bathed in the smell of sex by now.

Suddenly, Esme let out a concerned groan. I looked down, and noticed that the condom had stayed inside of her after her last movement. She pulled off of me, and pulled the condom out of her. God, I did not want this to end, and my head was spinning with how to put into words the question of continuing. Thankfully, Esme had other plans.

With her eyes locked on mine, Esme lowered herself onto me before I could even ask “are you clean,” and I felt her raw wetness and warmth surround my cock. I gasped and moaned as she slid fully over me, taking my full length in an instant. My cock had slid perfectly into Esme. We were both sitting up, looking into each other’s eyes, and she began to work her hips forward and back. I could feel how smooth Esme was inside, and how tight she was the deeper my cock went.

We switched to missionary, and I switched to my favorite rhythm: long, slow strokes, where I teased the outer edge of her vagina with the head of my cock. Esme was gasping as she sat up to watch me slide in and out of her slowly. She reached one hand up and placed it behind my head, and pulled me towards her. I leaned in to kiss her and brought my body on top of hers, leveling out fully inside of her. Kissing Esme turned into Esme moaning into my mouth as I picked up my pace; at this point she was fully wet and I was able to pump into her with no resistance. I broke off the kiss to watch her tits bounce every time I thrust into her. Between the sight of her tight body, her perky breasts moving rhythmically with us fucking, and the feeling of being inside of her raw, I was nearing the end. I grabbed Esme’s hips and gave her a few more deep thrusts, then pulled out and unleashed an honestly incredible amount of cum (considering this was our fourth round) onto her stomach and chest.

I collapsed next to Esme, admiring the ropes of cum covering her body (this is a thing for me), and thinking about how thoroughly fucked-out we both were. This story has gotten long enough and I honestly don’t have much more to add besides that she got showered and ready for work, and I left. We hooked up once after that, but haven’t since then. Kudos if you got to this point, I hope it was a good read!

Source: reddit.com/r/gonewildstories/comments/r4kl2p/mf_the_longest_guiltiest_and_hottest_one_night