My (33M at the time) first time cheating [MF] – hotel gym and bar encounter

I’ve cheated with a number of women. The first time was a chance encounter during a business trip. This was almost 11 years ago now, how time flies!

After a long day of meetings in downtown Chicago, I headed to my hotel room. Emails and voicemails filled my computer screen. I was stiff from sitting all day and needed to hit the gym before diving into work. I changed out of my suit and get into gym clothes and headed to the treadmill and weights. There were two other men in the gym, and one woman, who looked to be pushing 40 and also had a few extra pounds, but still had curves which made you stare a second longer than you probably should. She also had a wedding ring. She finished her workout, another anonymous man walked in, I finished my routine, and headed back to my room to shower.

I ordered room service and tackled my tasks for the evening. Before I knew it, it was 9:00pm and I was mentally shot, I couldn’t do any more work. I called home, said good night to the kids, and my wife was short with me and didn’t really want to talk.

After the call, I decided, as I typically do, to head to the hotel bar for a night cap. I threw on my suit pants and shirt, made myself minimally presentable, and headed down. Usually hotel bars are full of other out of shape 30 to 60 year old men sitting at the bar alone, staring at their fantasy football lineups on their phones. Tonight was no different. I slid up to the bar and ordered a drink.

About half way through my drink a woman walked into the bar. She was wearing a fairly modest blouse, but it did show of just enough cleavage to catch your eye. Her jeans hugged her hips perfectly. Yes, predictably it was the woman from the gym. She sat down two bar stools from me and ordered a glass of wine. We made eye contact, and at the same time we both said “have a good workout?”. We laughed, and I slid one seat closer and struck up a conversation. Nothing heavy, just small talk. What brings you to town, yeah work sucks, kids have dance and soccer practice tonight, whats your workout routine, typical small talk. We each order another drink.

Then, her husband called. She excused herself, but left her purse. I could see her getting animated in the lobby, but it’s none of my business so I didn’t stare, I just went back to my twitter feed or whatever was interesting on my phone at that moment. A few minutes later, she sat down and apologized. I told her not to sweat it. Under her breath she muttered “he’s just such a fucking ass hole sometimes.” I commiserate, as any married person could, and we traded barbs back and forth about how our spouses annoy us. Then, after another drink is half gone, she thew in “and he can’t eat pussy worth a damn either.”

I gave her a look with a half smile, and she blushed and says “oh shit, I’m so sorry.” I responded, “it sounds like your husband is the sorry one, that’s my favorite thing do to in bed”, which is true. “I get marital sexual issues, my wife and I haven’t had sex in 14 months…”

She bit her lip, looked at her drink, and looked up at me with a half smile. I looked her in the eye, smiled and shifted my eyes to the elevator. She smiled even bigger and said “ok”. I grabbed a napkin and a pen, wrote my room number and last name and a note for the bar tender that said “put the drinks plus 20% on my room bill.”

We headed to the elevator. Waiting for it to open felt like an eternity. Once it opened, we steped in. “What floor are you on?” she asked. “Top floor, what about you?” She hits my floor number and says “your room it is”, and she steped towards me and we kissed. Our tongues tangled, my hands found their way to her ass and I pulled her close to me. My cock stiffened, and then the door opened. We steped out, and I lead her by the hand towards my room.

She stopped for a second and says “Just so you know, this is not something I typically do.” “Me either, lets not worry about that right now” I replied. She smiled, we walked again, and I unlocked my room. As soon as the door shuts, I kissed her and pressed her against the wall. She melted in my mouth and caressed my cock through my pants. We broke the kiss and headed towards the bed. “Do you like to eat pussy?” she asked. “Mmmhmm” is all I could muster in the moment, as all I could think of is fucking her brains out.

I walked to her, kissed her, and pushed her to the bed. I unbuttoned her jeans and pulled them off of her. She was wearing pink cotton panties, and I removed those as well. I spread her legs apart and caught my first look at her pussy. It’s magnificent. Perfect lips, trimmed but not shaved bald, and glistening with her wetness. I pulled her to the edge of the bed and I knelt down. With my left hand, I spread her pussy lips, which exposed her clit. My tongue flicked her clit, and I entered two fingers in a hook shape inside her. She squirmed, and I placed my whole mouth on her clit and gently sucked. My fingers moved in and out, looking for a spot to send her up the wall.

I could taste her juices as I keep sucking her clit. She arched her back, grabed the bed cover and let out a loud moan. I found her spot! I kept doing this as it’s clearly working, until I tasted a flood of juices in my mouth, and she screamed “FUUUUUCK!” and collapsed her back on the bed. I came up for air and say “Well?” She looked at me and says “I havent cum like that in YEARS! Oh my God!” I stood up and took my pants off, showing her my hard cock. “Oh my…” she said, and she got off the bed, droped to her knees, and took me into her mouth. She has skills – she squeezed my balls with the exact right pressure, stroked my cock as she sucked, and never touched her teeth to my head.

I guided her head up and down my shaft, and I could hear her gulping on my rod. “I’m going to cum” I excitedly proclaimed, and she kept sucking me. As my balls contracted, I pushed her head down on me and exploded down the back of her throat. She slowly pulled my cock out of her mouth, not leaving a drop on me, and swallowed my load. This was so sexy to see. I remained hard through this, as I was very turned on.

“You ready to get fucked?” I asked her. “Oh my God yes.” She stood up and removed the rest of her clothes, revealing her plump tits. My vision of her from the gym was accurate – a little extra, but very curvy and sexy. She climbed on the bed, and I joined her. She was on her back, and I half knelt in front of her and grabed her ankles. I pushed my swollen cock into her drenched pussy, and it slid right in. She let out a moan and a small yell. Feeling out her preferences, I lifted her legs and pumped her at a medium pace, which her body motions and moans told me are what she likes. I reached down with one hand to press on her clit as I fucked her. When I did this she let out a loud noise, almost a grunt, followed by a yell. I picked up my pace and was really pounding her now. “FUCK FUCK FUCK” she yelled, over and over. My balls were slapping against her, and she pushed against the bed headboard. If anyone was in the next room, they surely knew what was happening in here.

She yelled “oh god FUCK!” and grabbed a pillow and yelled into it. After I’m sure she came, I stoped and suggest she rides me. She agreed, I moved on to my back, and she straddled my cock. She rocked back and forth, her tits swaying with her motions. I rubbed her nipples, squeezed them a bit, took them into my mouth and sucked as she rode me. She sat straight up and bounced harder on me, and I could feel myself about to cum. I tell her “I’m fixed, can I cum in you?” and she replied “me too, so yes!” She grinded on me for about 30 seconds more and I exploded inside her. As I did, I grabbed her hips and pulled them close to me. She leaned over and kissed me deeply, then rolled on to the bed next to me.

“Holy shit, I needed that!” “Me too! That was the best sex I’ve had in YEARS!” I exclaimed, which to that point was true. “OH my God yes” she agreed. She got up to go to the bathroom. By the time she returned, I was hard again. As she walked back to the bed, I stood up with my cock sticking straight out. She grabbed it, rubbed the head, and we kissed deeply. I turned her around and pressed her against the window and entered her from behind. The view of the Chicago skyline illuminated our fucking. I sat down on the love seat (my legs were staring to cramp) and she straddled me reverse cowgirl so she was still facing the window. After a while I stood up and bent her over the arm of the love seat and she begged me to fuck her from behind, which I gladly did. I entered her, grabbed her hips, and pounded her hard. She clearly enjoyed this, and muffled her yells into a pillow again.

I was feeling good, obviously, so I gave her a light spank on her ass, just to feel out her reaction. “Yes!” she yelled. I spanked her harder, over and over, and grabbed her hair, till we were really going at it in a good rhythm. She came at least one more time, and I blew my load inside her again. We both laughed with pleasure, but then realized it’s almost 1am! She was startled by the time. She jumped up and grabbed her phone, her husband had been trying to call this entire time. She looked at me and said “look at this, he texted me 8 times!”, laughed, and put her phone back down. She got dressed, as did I, and I walked her to the door. “When do you leave?” She asked. “Tomorrow afternoon, how about you?” “That’s too bad, I’m here another night.” “Maybe our paths will cross again. Is this a frequent stop for you?” It was for me at the time. “No, unfortunately. But this was great, thank you so much!” she kissed me deeply, walked out, and we never saw each other again.

I went home the next day, thinking my wife would suspect something, but she did not. She barely acknowledged my existence to be honest. I thought I would have a rush of guilt, but I did not. We went about our lives, and I pretended nothing happened. Maybe I am a sociopath, but this lack of guilt and the amazing sex pointed to me repeating this behavior over and over as the years passed.

Source: reddit.com/r/gonewildstories/comments/t10gy7/my_33m_at_the_time_first_time_cheating_mf_hotel