Choosing the right bridesmaid (m/f) | 2016

Note: I have been very lucky to have a lot of sex with a lot of beautiful woman, so I wanted to document some of these experiences. They are all 100% true (except names). Just as a point of reference, I am often told I look like Vin Diesel (though I don't see it)-I am 6'1, 210, shaved head, blue eyes, tattoos, muscular build, mid-late 30's, live in South Florida and have a successful career. I will try to answer any and all questions! If you are looking strictly for the sex part, scroll down awhile.

I had recently broken up with someone after a long relationship when one of my closest friends announced he was getting married. I was really happy for them both; they were/are a perfect complement to each other. They did explain to their friends that as a rule they weren't allowing their guests to bring a date unless they were married/engaged to the person. I understood, though I thought it was cheap. In my opinion, you want your guests to have a good time, and having a bunch of strangers without dates might damper that. I also assumed that as the best man, I would/should be excluded from this. Much to my chagrin I was told the rule applied to me as well. To be honest, I was fairly annoyed though I kept that to myself. As the best man, there is a fairly large financial obligation, as well as time spent to help plan bachelor parties, etc.

So, fast forward a few months and the wedding is getting closer; and I talked to the bride, Lisa, and she was telling me who her bridesmaids were. There were going to be five bridesmaids, 2 of which were married, that I knew well. And 3 of which were single, I had only met one and did not know any of the three well. I warned/joked to Lisa that this was her last chance to allow me to bring a date, and if she didn't I PROMISED I was going to fuck one of her bridesmaids. She told me they were off limits, and besides, "they aren't into guys like you." Which truth be known, did nothing to deter me as I took it as a personal challenge.

The day of the wedding came and everything was going smoothly, I was three Johnnie Walker's in (trying to keep the groom calm), and we were ready for pictures. The bridesmaids started to file in shortly thereafter, I said hello to the ones that I knew and introduced myself to the ones that I didn't. I quickly decided that there were two different yet very attractive ones. The first one was Jennifer, mid 20's, tall and thin, long straight hair, one of those model types that look fairly normal until you look closer at their features. She was a girl that looks beautiful in the morning. I had met Jennifer once or twice before; though she was really good looking I hadn't made a move on her because she was Lisa's close friend and I knew it could get messy. One thing I have learned is I prefer not to do messy. The other bridesmaid was Dawn, who was a college roommate of Lisa's and lived in California, and had just flown in for the wedding. Dawn was shorter, with a nice tan, average size tits, but a really fat (in an amazing way) ass. The kind that you can’t keep your hands off while fucking. Dawn was a little shy and reserved, though really sweet.

As we were taking pictures and waiting around for the rest of the bridal party to finish, I spent some time with each of them (honestly trying to figure out where my best chance to get laid was), and I couldn't figure out if I had a shot with either. I did find it funny, that Lisa (bride) conveniently had me walk the sister of the groom down the aisle, instead of the two single women; as if that was going to keep me away from trying to nail them.
After the ceremony, I was hanging with my other guy friends and just enjoying the party. Another Johnnie Walker down, and I was feeling no pain. The wedding was in a large hotel, and as the line to the bar got way too long (it wasn't an open bar, don't get me started on how cheap that is), so I went to the bar in the main hotel to get a drink. I figured as long as I am paying, why wait in line. As I was walking out, Jennifer was walking in from outside with another guest (girl), and we made a little small talk, and they came to the bar with me. I bought them each a drink and we made small talk. Jennifer told me a little more about herself, and actually had told me that Lisa had warned her that I was a complete pussy hound. She asked me flat out if that were true. I told the absolute truth. Hell yes, I am. When I am single, I see nothing wrong with fucking beautiful consenting women as much as possible. As long as both parties are into it, why not. She seemed to appreciate the honesty, and the conversation heated up a little after that. I could tell her friend was getting bored, as she began to more or less pound her drinks. Jennifer had to use the restroom, so I escorted her there and waited right outside. When she came out, we locked eyes, and I could tell it was on. I stepped to her and she stepped closer, I then pulled her toward me and we kissed. We were in this little corridor, sort of hidden, and the kissing got a little more intense. I asked if she wanted to go out by the pool for a little fresh air, but also being cognizant that we had to get back to the wedding (though by this time, people were pretty plastered). So, we are out by the pool, leaning against a chickee hut kissing, and I have my hands on her ass, and with the other hand I reach under her dress and just sort of linger my hand over her panty covered pubic mound, and I can feel the dampness. Now we are kissing even more fervently, and I am about to attempt to finger her, when another of her friends appears, and tells us that the other girl that was pounding drinks at the bar is now in the bathroom puking. What an erection killer. Hard on-gone.

Like a good friend, Jennifer went to tend to her friend, and told me she would find me after in the wedding. I returned, and just in time as the DJ was looking for me to do the best man speech. I delivered the speech and just hung out and talked to a lot of the guests. I saw Dawn and we made small talk for a few minutes; I was wondering if I chose wrong. Dawn smelled so good and that ass; all I could think about was getting my head up there.

I went back to the bar (a common theme this evening), and Jennifer approached, and apologized profusely but she had just said goodbye to the bride as she had to leave because her friend was throwing up all over the place. I was disappointed but totally understood, and we exchanged numbers, and I walked them to her car, helped her friend get in, kissed her goodbye and returned to the wedding.

The thing was, I already had gotten a room in the hotel and would hate for it to go to waste...I was wondering if there was enough time for me to circle back and try to pick up Dawn, whom had I thought this through might have been my first choice anyway. When I got back in the wedding it had already gotten a tad rowdy, people drunken dancing all over the place, and generally having a blast. I felt a tap on the shoulder and there was Dawn. She made some sort of reference to Jennifer; I don't remember the specifics but the gist was she wanted me to know that she knew that I was outside with Jennifer. I may be a dog, but I am no liar. I admitted it, and mentioned something about her appearing to have no interest. We sat down at a table and had a really deep and genuine conversation about serious life events...it was a great talk but I could tell this wasn't headed towards my goal of her ending up in my bed. She had a long drive in the morning to visit some family, so I did offer her my room (she was supposed to stay with some family that was a little further south). It was funny because she had said that she had been warned that I was pretty smooth and that if she weren't careful she would end up in my bed.

Soon enough the wedding ended and everyone said their goodbyes, Dawn found me and asked if the offer stood. I said of course. I also knew if the bride saw us leave together she would try to cock block me; so we snuck to my room like a couple of teenagers. When we got inside Dawn admired the view, there was a large balcony with a beautiful ocean view. I made her a drink and we chatted on the balcony, and Dawn said she had an idea; she said let’s get into bed, make it look like we are naked and take a picture and text it to the bride. I pulled my shirt out of my tux pants and as I began to unbutton it, Dawn's eyes were fixated on my chest. I locked eyes with her, and walked over and pulled her towards me and kissed her hard on the mouth; one of those full open mouth with lots of tongue. I had leaned her back against the wall, and reached to put my hands on that perfect ass. She gently untangled herself, and said that she still wanted to take the picture but she wasn’t going to fuck me. I said ok, and she went in to the bathroom to get undressed. I learned later she was this odd mix of 2 parts shyness and 1 part total slut.

When she came out she was down to these tiny sheer black boy shorts; the kind where more than half her ass was hanging out the bottom…and no top, but her hands were covering her chest. I was wearing nothing but my boxer briefs and we got into bed. I have to say it was sort of awkward, almost like we were filming one of those movies where we had to appear as if we were naked, but really weren’t. We got under the covers, and she was lying beside me and she grabbed her phone (camera) and snapped a couple of really innocent shots to send to Lisa (bride). I told Dawn that this wasn’t that believable and I wouldn’t try anything, but she should get on top of me so we could get more seductive shots. She laughed and climbed on top of me. The first shot was with Dawn’s gently biting my nipple, which was her idea. That was my first clue that maybe she wasn’t quite as innocent as she portrayed. She brought her mouth up to mine, and kissed me this time. The kiss was good, hot, and she lightly bit my lip, and then a little harder…second clue she was not so innocent. And now she was grinding her pussy all over me, our damn undergarments were blocking the good time. But she was now grinding her clit so hard on me, and said if I don’t move she is going to cum…about 30 seconds later the tell-tale signs were there, the heavy breathing, the tensing up, and I could actually feel her getting wetter and soaking my boxers. And then the screaming, and I mean screaming….I was afraid someone would call hotel security it was so loud. Her body actually shook, and she put her head to my chest. As she came down from her orgasm she was a little embarrassed, and sheepishly said she hadn’t cum in like 3 months (she said she doesn’t like to play with herself and didn’t have a bf; poor girl.)

She reminded me about the no sex; but said she would give me a blow job. So, she took my boxers off, and started to lick my rigid cock, lightly at first…she looked up with my cock in hand and said that I should take a few more shots to send to the bride; I didn’t have to be told twice. I tried to keep my cock out of the shots, as I didn’t think the groom (my best friend) would enjoy me sending cock shots to his new wife. But I took some shots that you could clearly see what was going on. Now she was licking my balls, and doing it right, with some purpose. You could tell she really liked it; she was slurping on my balls, had as much as she could in her mouth, and took them out with a pop. She put my cock back in her mouth and put some pressure right on that spot underneath my balls; to my surprise she starts talking a little dirty…”you like this, don’t you…..my mouth on your big fuckin’ cock, are you gonna cum, where do you want to cum.” It takes a lot to surprise me; where did that girl go that came out of the bathroom hiding her tits. Well, I am a sucker for a girl that talks dirty; and that sent me over the edge. I warned that I was going to cum, and she told me to cum in her mouth. I shot once hard, I am sure it hit the back of her throat, she kept on going up and down on my cock, very little hand –mostly mouth up and down taking shot two and three, and just then she put her hand on my cock to keep it going, it was one of the longer orgasms I have had. She cleaned me up with her mouth; there wasn’t any cum anywhere, she had swallowed it all.
We took a shower (it had been a long day), and made out a bit (she did remind me about the no sex rule, she said she had never had sex without a relationship). But it was nice nonetheless, I was soaping up that perfect ass, and was rubbing my now growing dick between her ass cheeks. *There is nothing that makes me want to fuck more than a woman saying we aren’t going to fuck. I kneeled down and went to lick her pussy, but she pulled me up and said she hadn’t shaved as she didn’t expect this. I assured her that I didn’t mind (in actuality, as a change of pace, I LOVE a hairy snatch). So, I went back down and started to kiss her at the bottom of her pussy, very lightly…I licked her starting right at the bottom of her pussy, and all the way stopping right at her clit (I think it’s a mistake to go right for the clit too fast.) The shower had like a tiled seat so I told her to lean against it as it would give me better access-so I licked back down to her pussy and as I got to her asshole, I could tell she was getting nervous (she tensed up)…of course, because I am obviously a perverted assman with an asslicking fetish, I licked her ass, she moaned lightly, which surprised me as I thought she might pull away. Now I am picking up the pace, and taking turns between licking/and now sucking her clit…and I worked two fingers into her, right underneath her pubic bone, and with my fingers I’m making that ‘come here’ gesture inside of her, hitting her g-spot. Her legs literally went a little limp. I suggested we take it back to bed. She didn’t say a word, just got out of the shower, didn’t even dry off and got into bed. I jumped right back in (literally), i told her to lie on her stomach, it would give me better access to her g-spot, so she spreads her legs as she is on her stomach, and I reinsert my two fingers into her and go back to work, and now start licking her ass while furiously rubbing her g-spot with my fingers.

I could tell by the way her body was tensing that she wasn’t far off from cumming, and she was moaning really loudly now, but suddenly she pushed me out of her pussy, rolled over and grabbed me by my cock and without a word shoved me right into her, I sank into her up to the balls. She said wait…she grabbed her phone and said she wanted to take a picture of the moment I put my cock in her, that she was going to send that to the bride too. It wasn’t x-rated or anything, just a selfie where all you can really see is that I am laying on top of her. Back to the fucking, it was fast and furious, my balls are banging hard against her asshole, and I have both hands on her asscheeks, spreading them apart, and within like 3 minutes she starts moaning loudly, and says “im going to cum, im going to cum all over your cock.”

Dawn wanted me to fuck her on the balcony. We went outside, and I bent her over the balcony; it was pretty hot; the combination of the salt in the air, the moon, and that pussy and asshole from behind was amazing. I had one hand on her hip and the other had a fistful of her hair and I was pounding her hard from behind, her pussy had a chokehold on my cock, and I loved it but knew I couldn't take much more so I gave her the ‘I’m going to cum’, not knowing where she wanted it…she jumped off my cock, and went to her knees and told me to cum all over her face (which I’m not a huge fan of, but its ok every now and then), the funny thing is the first shot missed completely and went over the balcony (I hope no innocent bystander wasn’t hit), and the next two shots hit her right on the cheek, and then she milked the rest out of me by rubbing my cock all over her cum soaked face. It was pretty hot.

The next morning Dawn did send those pictures to Lisa (the bride), who actually was pretty pissed that I fucked one of her best friends. She wasn’t any happier a few months later when I fucked Jennifer (the other bridesmaid.) I guess she should have allowed me to bring a date!