I am 53 years old. I am married to my 2nd wife now for 17 years. At the last part of my first marriage we got into swinging but it didn't work out. This story is how after a few years I got back into swinging and it actually helped make me sucessful. When I was 33 (1997) and single again, I bought an adult video and magazine store. I purchased it for a bargain. The old guy that previously owned it was reluctant to switch from VHS to DVD's and his health was failing. I had an uncle who had connections in the porn distribution business and was able to stock the store with thousands of DVDs without going into debt. I also added adult toys, club clothing, lube and condoms, etc..(you get the picture) Business really picked up. The store also had a mini theater with just three couches. I hired 3 women (in their early 30's) and a transgender (23 years old) to run the store. I only had it opened from Noon to 2AM and I spent very little time there except for checking the accounting books. Mostly I was day trading stocks at this point and felt everything else was a distraction. I dated very little and went to night clubs once a week to pick up a one night stand. I am 6'2" and heavily muscled and back then I was into weight lifting so I was always sucessful at the clubs. And on the rare chance I picked up a woman who wanted to wait and not get fucked on the first date I would arrange to get an emergency call and drop her back off at the club then I would go to another club and choose a different woman. I won't pretend I am I good guy. I'm not. After about 6 months when I was back in my store I went into the mini-theater area because I was considering converting it into several video preview rooms. The Tranny (I will call Emily) came into the theater and started cleaning the vinyl couches with a disinfectant spray. I noticed "she" had her tits done with implants and I complimented her. She thanked me and then start flirting with me. I told her it was flattering but I was only into girls. She seemed Ok with it but I could tell she was a little disappointed. I then said "I do get turned on watching porn with a shemale having sex with a women" Emily then said "Whenever you want me to put on a show just let me know" I think I just smiled at that and said "OK" About a month later I went back to check the books again and kind of jokingly said to Emily "So how about that show you mentioned?" She just went over and picked up the phone and said "I will call someone right now" I was a little stunned and did not say anything until she finished talking to someone and put the phone back down. She said "Rebbecca is on the way over". Rebbeca turned out to be a petite blonde that I found out later was 22 and married to an accountant named Tom. It was really sureal because just by looking at this blonde she could seduce any man.. and yet here she was ready to put on a show with a shemale just for me. We left Sandy (another women that worked for me) in charge of the store and went into the theater. There was already two guys in there that were sitting on the rear couch next to each other watching a gangbang on screen and wanking off. Emily and Rebbecca just walked to the front couch and started making out. It ended up that me and the other two guys watched Emily slip a condom onto a surprisingly large cock. It was as long as mine (8") but a little skinner. I guess I was surprised because I just find it difficult to see why a man with a large cock would become feminine. I guess she wasn't too feminine because she fucked Rebbecca to an orgasm and then had one "herself". When Rebbecca was leaving the store she started to call a cab because that was how she got there. I offerred her a ride and instead of dropping her off at home we went to a cheap hotel for a couple hours. When we got to the hotel she asked me if I had condoms. I told her I only had one right now but we could get some more if she thinks we will need them. Then she said "I don't want to do this if you use them" Then I said " Ok , I can pull out before I come in you " Then she said " If your not going to come in me I don't want to do this" I asked if she was trying to get pregnant. She said she was on the pill and her husband let's her have sex with other guys but he recently told her he doesn't like the taste of condoms when she gets home. I was really curious about if her husband knows everthing she does when he is at work. She told me "he knows because I tell him everything". After a couple hours at the hotel she had two loads of my cum in her pussy. I took her home and dropped her off just minutes before her husband was suppose to get home. This is when she told me they were swingers and they were going to a club on Saturday "couples only" night. She told me I should go also and then me and her could have some more fun, but I needed to bring a date. I said "I will have to find someone...unless you know someone" She said "I do know someone." Saturday came and I picked up her friend "Cat". Back then I drove a blue dodge Viper. She was also petite and had brown hair and green eyes. She was dressed in a miniskirt and tubetop. She got into the car and then I got in and the first thing she said was "do you have a towel?" I probably looked a little puzzeled so she said "This car is turning me on and I don't want to ruin your leather" Believe it or not I always have a towel. I keep one in every car that I have owned. I read the book "Hitchhikers Guide to the Galaxy" when I was young and for some reason the towel thing stuck with me. I retrieved the towel and spread it on the seat for her. She hiked up her skirt to show she was pantiless and sat on the towel. She explained she didn't want to make a wet spot on her skirt either. After a 35 minute drive we finally arrived at the club and met Rebbeca and her husband Tom inside at a table. They had reserved a couple seats for us and the table also had two more empty seats. Eventually the hostess sat another couple that were newcomers in their late 20's... Tammy and Stephen. The club rules were that in the main area (seating area, dancefloor and bar) the men had to stay dressed and the women could dress as risque as they wanted but no sex. The club had a VIP play area that had two hot tubs, shower, lockers, two rooms with beds, one open large room with couches and a voyeur viewing area and another room with a mini stage with a pole. In this VIP area clothing was optional and full sex was allowed. The club was a "bring your own booze" establishment and the bar was just serving mixers. I had brought a bottle of J W blue and we all had a shot. Cat was squirming in her seat and brought my hand to her pussy. I think we were both on edge sexually and needed some relief. We excused ourselves and said we will be a few minutes. It was early and nobody else was in the VIP area. We went into one of the rooms with a bed and left the door open. We both raced to see who could get naked first. She won because she only had two items that came off in just a few seconds. We skipped any preliminaries and I realized I was balls deep inside her before we even had a first kiss. Also I only knew her nickname and practically nothing else about her. She was a squirter. It wasn't a spray but a little bit constantly. When we were finished we were soaked. In the room was some shelves with stacks of sheets. We pulled the wet sheets off the bed and put on new ones. When we came back to the table Rebbeca gave Cat a scolding look. I sat between Cat and Rebecca and then asked Rebbecca and Tom "So when do you two start to play?" I looked at Tom and he pointed to his wife and he said "don't look at me. She's in charge" I looked back to Rebbecca and she said "When we come here we come to play with others" That explained why she gave that look to Cat. Clearly Rebbeca wanted first shot at me. All of us danced for a while with me dancing with Rebbeca and then Tammy and then Cat. Mostly the dancing was grinding against each other. When I went back up to dance with Rebbecca I had a hardon and she felt it and suggest we go to the VIP. We went back to the table and Rebbecca told Tom to stay and keep Cat company. We coaxed Tammy and Stephen to go with us. They were very nervous as this was the first time they visited a swing club. We all went to one of the rooms with a bed. We undressed and I started to perform oral on Rebbecca. Stephen was following my lead with his wife. After Rebbecca had an orgasm I retreived a condom and Rebbecca shook her head. I whispered to her "are you sure?" She told me "Tom likes it sloppy" I started to fuck her and Stephen was fucking his wife and after awhile Tammy and Rebbeca were trying to get closer to feel each other. I suggested they get into a 69.. I am sure they both were a little Bi. They went right for it. Me and Stephen withdrew and watched for a few minutes. We swapped ends so he could watch his wife eat Rebbecca's pussy. I watched Rebbecca eat pussy and then I had her come up for air and give me a few sucks before she went back to work. It looked like Stephen was starting to do the same on his side. After a few minutes of alternating eating pussy and sucking cock Rebbecca pulled my cockhead to the entrance of Tammy's pussy. I didn't have permission from Tammy or Stephen yet so I held back and just let Rebbecca rub my cockhead on Tammy's slit. I was trying to think of some way to ask Stepen when I felt another hand on my cock. Tammy had reached down and was trying to stuff my cock into her pussy. I took this as an OK. I slid in and noticed her pussy felt hotter than normal. I'm not sure if she had a fever or if it was her excitement or if she was ovulating but it was noticeably hotter than a normal pussy. I was doing long slow strokes and then I noticed Stephen was getting a condom. Rebbecca went onto her back and Stephen entered her in the missionary position. Tammy was already on her back with my cock in her but wanted to watch the moment her husband entered Rebbecca. After about 10 minutes I was getting ready to come and I could tell Stephen was too. Stephen said "about 1 more minute" I adjusted my stroke rate and said "me too" In my mind I had the plan to pull out and see if Tammy would allow me to finish in her mouth. But then I heard Stephen say "I'm going to make a deposit in your wife" I thought "WTF" I am sure he knew Rebbecca was not my wife. And he had a condom on so he wasn't going to make a deposit. I decided to play along a little and said "I'm going to shoot a big load of sperm in your wife". Stephen immediatedly started bellowing like a cow and having an orgasm into his condom. Tammy also had an orgasm simultaneously. Tammy started squirting and that set me off and pulling out just was not an option anymore. Also Tom's bellowing started Rebbecca laughing and her laughing started me laughing. Tom flopped back on the bed and I am not sure if he noticed that I actually did make a deposit into his wife. We cleaned up and eventually got back to the table. About 2 hours later I had sex with Cat again in the room that had a voyeur window with her in reverse cowgirl position to give the voyeurs a good view of my cock sliding in and out. And then near closing time Rebbecca told me that her pussy was not sloppy. I said "we will have to rectify that won't we?" We made a quick trip to the VIP area and I got her sorted out emptying my forth load of the night into her pussy. While she was still on her back she pulled a small roll of wide medical tape out of her purse. She tore off a segment and covered her entire slit with it. Then she put her panties back on and said "that way it won't leak out on the way home". I assumed Tom had some cleanup work ahead of him. I ended up taking Cat back to my apartment and we started dating and that lasted a few months. But I eventually found out she was a socialist and boderline communist and we saw a lot of things very differently. But I think that night at the swing club was what solidified my desire to find a girlfriend and eventually a wife that would be ok with swinging. Monogamous sex is somewhat boring after fulfilling so many desires I could not see myself going back to it. It was 2 more years and dating many more women that I eventually found my wife. I think over that 2 year period I dated about 60 women and about 20 went to the swing club with me but most of those wanted to only be "fuck buddies" if we were going to swing. In their minds if I was the swinging type I was not the marrying type. The 40 or so that would not get into swinging were really nice and a few were stunningly beautiful but I had my mind made up. There was a couple women that were into swinging, and marriage was not out of the question, but they had other issues like one was into wiccan witchcraft and crystals and another was into cocaine and another said her swinging partners would be limited to big black cocks only. I guess earlier I mentioned swinging actually helped make me sucessful. This "sucess" happened a few years later when my current wife Anna and my sister in law (my wifes twin) Sylvia and their cousin Maria and me were all into the swinging scene. It was mostly because of the girls and the somewhat exotic looks that we eventually got invited to some exclusive parties which lead to even more exclusive parties. I made social contacts that lead to some really great real estate deals that were normally reserved for "politicians". At one point I even put on an act and pretended I was going to run for a public office in order to get a "deal". Normally an individual is not supposed to be able to buy land worth millions for a few hundred thousand dollars. And then eventually that land worth millions is worth millions more when the land is rezoned as "commercial" by a zoning commision. The thing is, on paper the deals I obtained were all perfectly legal I can't tell you about those "exclusive" swinging parties without violating Non Disclosure Agreements that we signed. I can say that some parties were on private megayachts and even a private island. But eventually we got away from those people. The amount of corruption and criminality of politicians and the ultra rich is staggering. And there was too many attempts to get me "dirty" so to speak. This meant trying to get me involved in not quite legal deals in order to have the "leverage" on me and keep me in their pocket. We eventually sold everything and moved to a different state. We are still involved in swinging but the private parties we go to now are more for the sex and freindships and not to make business contacts. We go to swinging clubs too but usually go with other friends and usually keep the sex within the same group of friends.