27 [m]arried businessman, [f]un with tinder. Part 2 – bridesmaid

So a little more backstory from me: My wife and I got married when I was 23 years old, I had just earned my bachelors degree in college and moved to a town back near where we were both from for work. We both have very large families and a lot of friends so we had a huge wedding. I had 12 groomsmen and she had 12 bridesmaids in the wedding. It was a hell of a time.

A lot of the bridesmaids and groomsmen were mutual friends from college, guys and girls we had both become close with over the years. In fact in college I had slept with 2 of her bridesmaids (before we dated) and fooled around on drunken nights with another 2. My wife knew these stories and didn't care too much. In fact. when it gets brought up I can tell she gets very very turned on.

Anyway, life goes on and I am going away on another business trip. This time to charleston SC. Same routine, I get to my hotel with a day to kill and start swiping on tinder while having a drink at the hotel bar. I end up having a couple of more drinks than I intended. This is important because I come across one of the bridesmaids in our wedding. I forgot she had moved to SC to work for boing, the air company or something and I immediately panicked. I was still new to this whole charade and I thought I'd be caught. But, I'd been drinking and thought it'd be funny to swipe her yes thinking no way she would swipe me back. This bridesmaid – Natalie, had given me half a blowjob at a party one night in college before we both passed out from being way too drunk. She is gorgeous. 5'6 tan long dark hair. Big chested with a waist to hip ratio that you thank god for. She was a cheerleader for the university of Florida and avid yoga instructor.

Well I went in to panic mode when we matched and I immediately started to think of ways to get out of this situation.

She messaged me and it said "away on business and decided to play huh ;)" the wonky face helped a bit so I said "just bored looking for people to have a good talk with over a drink, don't really know what this is about." She responds "yeah yeah."

So I decide to just jump in. "I'm in town for a couple of days and it would be nice to catch up." She is all for it. She tells me she has been homesick and would love to see someone from home.

We meet at this cigar shop/bar downtown. It is pretty small and quiet. I can't remember the name exactly, king something or another. The seating comfortable and close but private. She was there before me and had ordered me a drink that was already sitting at my seat. She knew I am a big fan of KY bourbon. We chat for about 2 hours, casual simple stuff but I can't help but notice how hot she looks. Her skirt is short and her blouse is low. She keeps leaning on her hands resting on the table and I can see her Lacey red bra. She caught me looking and I blushed and looked away and said "sorry old habits, can't help it you look good." She said "I, know. Soooo you know tinder is a hookup/dating app right?" I decide to act dumb "I didn't but I'm starting to realize that." She laughed and we begin to talk about our night we never finished. By this time we are bith a bit drunk. I decide it's time to go, nothing was happening, so I paid my tab. I pick up hers, and I guess she was looking for a reason to touch me I guess because she got over excited and she said "that's so sweet," and comes and throws her arm around my neck kissing my cheek. She pulled away and looks me in the eye for a solid second. I started to get hard thinking about what that look meant and she kissed me passionately. "Omg I've wanted to do that for so long, come home with me?" I agree but instead offer my hotel which is only a few blocks away. She said yes.

The walk back wasn't sexual, in fact we talked more casually laughed and had a great time. We got to my room and she slowly lays her things down. I go to the cabinet and grab a bottle And start making drinks. She seems a bit unsure at this point, maybe having second thoughts. Like I said I am respectful so I hand her the drink kiss her softly on the side of her lips and said "you know if you're uncomfortable we can chat and I'll call you a cab when you are ready to go home." She shook her head and smiled and said "it's ok." But she visibly relaxed. We finished our drinks, still chatting and she started this motion with her hand tracing her fingers from her hair which was loose curled down her chest then legs. Very sexual, I had to cross my legs because I got so hard watching her thinking of the things I would do. She noticed, leaned in and kissed me hard on my lips. I slowly but strongly grabbed her lower back and slid her closer to me and at the same time she ran her hand up my thigh on to my dick outside my pants. I let out a little sigh and got a bit too excited and begin pulling her clothes off. Her body is perfect and she is wearing panties to match her bra. These sexy see through red things (she wanted this).

I picked her up and set her on the desk in the hotel and make out with her. Pulling her bra and panties off I begin to kiss her neck and nipples. I'm completely clothed and I begin to massage her clit lightly. Her panties had been wet and she was soaking wet. She definitely was expecting this. I alternated playing with her clit and fingering her which I think frustrated her because she jumped off the table walking me backwards to the bed which I fell backwards on to. She undid my pants and pulled them down and my cock sprang out. She didn't waste time and she began taking the whole shaft into her mouth. I was excited bc I knew I'd been drinking bourbon and when I do that I fuck like a champ. She wasn't the best at head but she was fucking herself so I didn't stop her. She came loudly with my dick in her mouth while on her knees. As I mentioned before I'm a dominant person and I pull her up and lay her on her stomach on the bed. I kneel over top of her and lean low over her back. I put my dick slowly in and it was so perfectly wet and tight. I didn't use a condom, probably bc I was drunk. Later I found out I was only the second guy she fucked. Laying on top of her from behind using my arm to hold myself up while on my knees I fucked her rather hard and she was being so loud. I moved my other hand to her neck lifted her head back to chest and slid some fingers in her mouth which she sucked and licked. It was so hot but like I said I'd been drinking bourbon. We rolled over and she turned around riding me reverse cowgirl. I loved watching her massage her pussy into my groin playing with her own nipples looking at the ceiling just taking it all in. At that point I began to get excited and I told her I was going to come. she looked back at me and smiled "cum in my pussy." I didn't think that was the best idea but she ground harder and harder. I felt her come twice more and her wetness running down my balls to my ass. I told her I was coming and she grabbed my tighs and started twerking fast on the tip of my dick until I came hard into her pussy. I let out at satisfied moan and she loved it because she started to come again. We just sat there laughing at nothing for a couple of minutes just enjoying the ecstasy of it all. She got off me and tried to lick her self off of my cock and all my cum that dripped out but it tickled too much so I just cleaned up in the bathroom before coming back to the bed.

We spent the whole night laughing and talking. The next morning we had a quick fuck in the spooning position and I came in her again. It felt amazing. But overall it was like old days two friends getting together having a blast and putting the cherry on top by letting me fuck her. The night couldn't have gone better. We still keep in touch and I see her when all of our friends get together. We just smile and go our own way.

Source: reddit.com/r/gonewildstories/comments/3vf6xt/27_married_businessman_fun_with_tinder_part_2