27 [m]arried business man, [f]un with tinder part 3 – awkward Night

This story is a bit different from my other posts, in that, I was using tinder as normal, I didn't actually succeed in finding someone on the app, but it did help me in finding a match. It goes a little something like this.

I was in Chicago, middle of the winter. It was blistering cold, and when I say cold, I mean chilled to the bone, frozen solid cold. The usual routine of unpacking, checking in with work, settling in and getting comfortable while using tinder ensued. This time though I wasn't having any luck. It was a weekday, and I was matching with women but none of them seemed interested in getting out. I attribute this to below zero wind chill and the fact that it was Wednesday in the middle of the college school year. I started to get frustrated because my work schedule wouldn't allow me any late nights and I had been on a particularly long dry spell and I was getting antsy. To blow off some steam I decided to go for a walk downtown. My hotel was near the lake so I decided to take a pit stop at this bar I heard some piano music coming out of. I'm not too sure of the name but I remember the sign had a girl winking on it all lit up in red.

The bar was a oldish style piano bar with only a few people here and there sitting around but it was mostly empty. The guy playing the piano was feeling some low key bluesy style music which I love, so I thought if I'm not getting lucky I may as well enjoy myself with some entertainment.

I popped a squat at the bar and ordered bourbon on the rocks (woodford) and sipped on it while swiping on tinder, trying to be smooth with the matches I'd already made. Still no luck. While I was swiping this cute, short black girl (I think half black actually) comes and sits by me and introduces herself as Charlie. She made some comment about me swiping on tinder like "not having any luck" or something stupid like that. I laughed it off and shot back "not tonight." I don't remember how our conversation went specifically bc I wasn't paying her too much attention.

Charlie ordered a vodka tonic and continues to talk to me, noticing things that make me a bit uncomfortable like "why are you wearing a wedding ring and on tinder." I made up a bullshit excuse that I was in the middle of a divorce and just drinking my blues away with some bluesy music. The more she talked the more i noticed she was cute. Milano skin color, dark hair dark eyes, petite, her boobs a bit small and covered (due to cold) but she has a nice ass. She explains that she is a masters student at the university of Chicago and she got bored and she loves the bar we are at. Our conversation picks up and I buy her a few cocktails.

We are hitting it off pretty well and she tells me she uses tinder too when she gets bored on weekends and that she met her current boyfriend on there and is now really close with his family thanks to meeting him (this is important later). I asked where he was and her response was "somewhere being an asshole." I laughed and apologized and flirted a bit more and made some comments that it's a shame we didn't match on tinder and jabbed at her saying she probably swiped me no. I got the vibe she liked me so I asked her to dance. She reluctantly accepted and we danced to one slow song and I took the opportunity to kiss her innocently enough, and she kissed me back. Her lips were soft and it was surprisingly intimate given I didn't really know her too well. She smiled at me and we went back and had a few more drinks before I offered her a drink at my hotel. She said "I live an a condo downtown a few blocks from her you can come to my place." I accepted and we march through the cold.

In hindsight I shouldn't have gone but at the time I wasn't thinking with the right head. We walk up to the condo and it is an insanely nice apartment. Heated floors huge windows overlooking downtown Chicago, but inside are two people sitting on the couch. A guy and a girl. She introduces me to her roommate and presumably her boyfriend and I keep thinking about the boyfriend charlie mentioned. They obviously look at me Suspiciously but I smile and introduce myself. She grabs me a bud light from fridge and I follow her to her room.

It doesn't take long before we start getting to it, she takes her coat off and grabs my face gently and we share another intimate kiss, the kind you share with someone you really care about the kind that lingers. Following the feeling of the kiss I slowly slide her sweater over her head, not breaking lips except to get the sweater off and she starts working on the button of my jeans. After we are both undressed, having never stopped kissing, I really notice how pretty she actually is. She has a very nice body and small perky tits. I'd never been with a black girl before and her skin was really turning me on as I rubbed her body admiring her. I grabbed a condom and put it on the bed then I slowly pull her on top of me as I fall backeards on to it. she doesn't waste time, grabbing the condom she unwraps it and rolls it over my shaft then raises her body and gently slides me inside of her by lowering her body on to mine. I don't know why, maybe it was the cold but her pussy felt so amazing, it was warm and wet. I wanted to fuck her but she was intent on taking it slow.

She was strattling me while on her knees, leaned backwards supporting her petite body with one hand while massaging clit in slow circles with her other hand. I slowly moved in and out of her holding her hips with both my hands. She shamelessly started to moan and when she was about to cum i push myself deep into her and she shivers a bit and then tightens all her body and gasps. She picks up the pace leaning over me but still doesn't go too fast. She kept starting into my eyes which made me uncomfortable but she was doing this slow twerk on the head of my dick and it felt so amazing. I told her to stop or I would come and she just kept going. It wasnt long before I was gasping and breathing hard and I couldn't hold it anymore and filled the condom while she made sure to squeeZe every bit of cum out of me while massaging my cock with her pussy. She kissed me lightly and jumped off and walks to the door swinging her hips saying she will be right back. I take the condom and kinda laugh when i throw it in the trash can by her computer desk wondering if she will remember to dump it before her boyfriend comes back. My good mood and humor doesn't last very long….

She goes to the bathroom, which is in the hall just right outside of her door and comes back in the room with PJs on. She says "want to watch a movie before we go to sleep?" And all I can think is "oh no" she is a clinger. I am frantically trying to make excuses. I have work, I have no clothes, I should go. But she counters saying we aren't far, I can wear some of her bfs we are the same size etc.

At this point her roommate knocks and says "I need to talk to you" Charlie steps out and they proceed to have a very loud argument about her cheating on her bf who is evidently her roommates brother and that they are about to tell on her. I decide to just leave. She doesn't have my number and she doesn't really know me so I put my Clothes on exit the room and literally fast walk right out of the apartment right past her and her roommate arguing. They stared as i walked by, probably wondering what I was doing. I got to the door but she realizes what was happening and she came after me. I threw the door open and took off down the hall, Charlie hot on my heals saying shit like "it's ok, don't go, I really like you, I want you to stay, I want to talk, I want to get to know you more." I had completely misjudged the situation. I opted for the stairs and not the elevator and the crazy is still following me. Props to her, I am a pretty fast guy, I ran in college, and she was taking those stairs pretty fast. It isn't my most proud moment but, i will admit, I got outside and hoofed it, sprinting back to the hotel. Thank god she didn't know where I was staying. I made a promise to be very clear with women from that moment on. Sex and fucking only. No intimate making love stuff.

If there is anyone on here that wants to PM and exchange info, interested in meeting, then we can have some confirmation posts in the future. Thanks for keeping up with my previous experiences.

Source: reddit.com/r/gonewildstories/comments/3vph88/27_married_business_man_fun_with_tinder_part_3

2 comments

Comments are closed.