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When I was in my early 20’s,
When I was in my early 20’s, I was so desperately on finding a wife, that I would make a fool of myself with every ladies that I went out with. You would think that I would have no problem finding a wife. I had a good job, I just bought a house, I was good in bed, I was not demanding, I Looked good ( 5’ 11” & 175 Lb), and did I say that I was good in bed. I would try so hard, and change myself to be what I thought they wanted, that after a few dates I would scare them all away. My last, so called girlfriend, (more like a infatuation on my part ) that I had only been dating for 5 weeks, dumped me the day I was going to propose. After that I just gave up on dating all together.
When I was about 26 YO, I was working for a large frim in a large city. I did a lot of harmless flirting with the ladies that were married, at least the ones that I thought liked it. I found out that as long as I thought that they were not marriage materiel, that I could be myself.
Well one Sunday afternoon, I was at work, finishing up a report for a meeting on Monday morning. I was all alone and was just finishing up, when Megan came in. Now Megan was 38 YO at the time and is a tall skinny lady with small breasts. ( A guy I knew in collage use to say “anything bigger that a mouth full is a waste” so ladies with small breath look great to me). It was a hot day so she was only waring a tank-top and a pair of shorts. She must not even had a bra on because you could see the outline of her nipples through her tank-top.
Now she was married so she was one of the ladies that I flirted with A LOT, and today was no different. She only needed to get something from her desk, then she came over to me and said “How is it hanging”. I replied “Now that you are hear it will not be hanging at all”. We bated comments like this, back and forth a couple of times, then she put her hand lightly on my chest and said “you are all talk and no action”. I took that as a dare, so I put a hand lightly on one of her breaths and leaned in to give a quick kiss. To my surprise, she did not stop kissing me back. Well I have not even been on a date for over 14 mouths so I did not want it to stop either. We kissed for about 5 minutes but then while we were still kissing, she lowered her hand to my crotch. I only had on a pair of old gym shorts and a t-shirt so by now she could feel how turn-on I was. She stop kissing me just long enough to say ” I see something it ready for action and I think it wants to get out to play”. Since Megan was rubbing my dick through my gym short, I figured that it was OK to start playing with her breasts. I put a hand under her tank-top and started to fondle her nipples. Megan stopped kissing and playing with my cock. I figured that I had crossed the line and stopped playing with her tits, but then she took off her tank-top and said “that should make it easier”. That gave me the green light and I really started using both hands on her lovely breasts. We kissed and fondled each other for a few minutes more. She then tried to put her hand inside my gym shorts to get to my hard cock, but it was accord for her. I thought I would make easier for her, so I took my shorts and underwear off. Megan smiled when she saw my hard cock and then took off her pants and underwear. She had a completely shaved pussy, which was a first for me. I thought we would go back to kissing but she dropped to her knees and took my cock in her mouth. I never would have thought when I woke up that morning, that a beautiful, sexy, and totally naked lady would be sucking my dick. Well Megan continued to suck my dick for a few minutes, then she stood up and kissed me. She was about to say something but before she got a word out, I picked her up, took her over to my desk and laid her down on top of my desk. I through her lags over each shoulder and then buried my head into her pussy. (Now I like eating pussy, or I should say, I LOVE eating pussy. One time in collage I licked and sucked a ladies pussy for over an hour). Well in about 15 minutes I had Megan clawing at my head and screaming that she was cumming. She was not even done with her orgasm when she was ordering me to fuck her. I continued to suck on her pussy, even thou my face was now soaked with her cum. I sucked her pussy for a minute or two, then I stood up, and pulled Megan over so her butt was barely on the desk. I placed my cock at the entrance to her cunt and was rubbing it along her pussy slit, to get it lubed up with her juices but also to tees Megan. I knew she was ready when she yelled at me “quite fucking around and just fuck me”. I grabbed ahold of Megan’s legs and slowly started to push my cock into her sweat love hole. It only took a minute before I was fucking her hard and fast. It had been a while since I fucked anything other than my hand, so I wanted this to last. I would fuck her until just before I was ready to cum, then pull out, lick her sweet pussy for a minute, then go back to fucking her. The whole time Megan was rubbing her clit and telling me how good it feels. I lasted about 15 minutes, but I could not hold out any longer and shoved my dick in Megan’s pussy as deep as I could go, then dump my load. I finally pulled out and fell back into my chair. Megan jumped off the desk, sat on my lap and gave me big kiss. We sat like that for a while, just talking. Megan said that I was a great fuck but I forgot something. I asked her what was it that I forget? She said “you did not ask if I was on birth control”. I thought “oo shit I made her pregnant” to myself. Then Megan smiled and told me she was on the pill. A little while later Megan said that she had to get going. As we were putting our clothes back on, Megan said “I cannot wait to show my husband my freshly fucked pussy. He just loves to eat my pussy after someone has fucked me”. I said in a load and frighten voice “you are going to tell your husband that we just fuck?????”. She replied “I been telling my husband that you are this sexy guy at work, and that I would like to fuck you. He said to go ahead but to tell him all about it”. She went ahead and told me that her and her husband are swingers and usually there play together with another person or couples but sometime he let her play without him as long as she ask he first and tells him all about it later. Megan could see that I was still confused. She gave me a quick kiss and told me to not to worry about her husband, that everything will be alright. She also indicated that her husband will be so turned-on that he will probably eat her out, then fuck her, while she is telling him all about the great fuck I was. Well I was still a little concerned about want her husband might do but I said OK.
The next day (Monday) Megan came over to me with a big smile. She said that her husband fucked her twice, and sucked her pussy, before and after each time. She also said that her husband liked the taste of my cum. We talked some more about the Swinging lifestyle. She finally asked me to come over Saturday, for dinner and she would show me some of the internet sites that they use to find other swinger. I said that I would make it. Well Saturday at 6:00, I showed up at their home. Megan greeted me with a kiss and introduced me to her husband, Carl. They also had Megan’s aunt, Lilly, that was visiting for the weekend. Now Carl was a bit older than Megan, I would say about mid 40’s. He was only about 5’- 8” but he looked like he worked out a lot. Lilly was around 50. She was also tall like Megan but was a little bit heaver and defiantly had bigger breast than Megan. It was summer so we all were wearing short pants and a nice shirt. Dinner went fine. We talked about work, where they all went on vacation and other things but did not get into swinging. I guess that was because Lilly was there. After a few hours Megan said that she wanted to show me something on the internet, so she and I went into one of their bedrooms where the computer was. She was showing me difference sites, full of couples that was looking for singles and/or couples to have sex with. Some with pictures and even some with video. My dick was getting hard just looking at them. Megan was sitting at the computer desk and I was standing right behind her. She turned to tell me something and noticed the bulge in my pants. She smiled and then said “so you like want you see”. Without me saying anything, she then unbuckled my pants and pulled them and my underwear down to my knees. Then she started sucking on my dick. It was feeling really, really good but after about 5 minutes, I stopped her, I was afraid that we may get caught. I pulled up my pants and said let us get back with the others. She just gave me this devilish smile and said OK let us go. Megan and I went back to the living room where Carl and Lilly were. But when we got there, I could not believe my eyes. Carl was slumped down on the couch with no clothes on at all and Lilly was sitting on Carl’s lap, naked, riding Carl’s cock. Carl said with Lilly bouncing on his cock “I thought that you two got started in the bedroom, so Lilly and I thought we would play out hear”. I looked over at Megan and she had this big smile on her face. She must have known that we would find the two of them fucking. Then Megan started telling me that, she and Carl like to play with Lilly and her husband now and then but Lilly’s husband could not make it. Megan went on to say that she told Lilly that she knows of a young stud (meaning me) that might be willing to show her a good time. I asked if her husband is Ok with this. Lilly then chimed in and said between moans “Yes, I got a pass for this weekend and besides he has a couple of guy friends showing up and not to play cards. He likes men also”. Megan and I, went over and sat on the love seat just watching the other two fuck. Lilly was a real live wire, she was attacking Carl’s dick with all the energy of a 20 YO and also ordering Carl to fuck her harder. Carl was smiling at Lilly but also had his hands on each of her breasts, pinching her nipples. This was the first time that I really saw another couple having sex live. (I did accidently walk in on my older sister and her boyfriend when I was 15 but it was nothing like this). Megan and I watched just for a minute or two, then we joined in on the fun. We started kissing and taking all our clothes off. Soon I was laying on my back, on the love seat, eating Megan’s sweet pussy, while she was on top of me with a mouth full of my cock. We all continued like this for a few minutes, Lilly riding Carl’s cock, while Megan and I were tasted each other. Then Lilly started saying (more like screaming) that she was cumming. Carl then pinched Lilly’s tits really hard, which made her cry out even loader “Harder, OO fuck , Harder ”. Megan and I stopped sucking each other for a minute to enjoy watching Lilly. Lilly finally collapsed on top of Carl. Megan and I went back to sucking each other. Carl let Lilly relax for a minute but then scooted out from under her. He got behind Lilly, picked her butt up a little and jammed his cock back into her pussy. I was finally able to see Carl’s dick and my male ego was pleased to know that my dick was a little longer and thicker. Carl was fucking Lilly hard doggy style and I love fucking doggy style so I thought that I would do the same. I stopped licking Megan’s pussy, got behind her, grabbed her hips and started to stick my cock in her very, very wet pussy. Then I remembered something that Megan said to me. With a grin on my face, I ask her “Are you on birth control or should I use a condom”. Megan turned her head and said with a devilish look “You smart-ass, just fuck me”. My cock went into Megan’s soaking wet pussy easily so I got up to speed fast. Carl was already breathing heave so did not thing he was going to last much longer. While I was fuck Megan, she reached her hand down and started to finger her clit. Megan had only been play with herself a few seconds when Carl grunted and was dump his cum in Lilly’s pussy. I stopped fucking Megan for a second to watch Carl but then went back to fucking her, but much faster. As Carl fell back on the couch, Lilly turned over to her back, spread and brought her legs up to her chest. I guess Lilly knew what was next. As Carl recovered, he dove head first into Lilly’s pussy and was sucking up all of his and her cum. Watching Carl eat Lilly did it for Megan. Her orgasm hit and it was all I can do to keep my dick in her pussy. I lasted maybe another minute and then was filling Megan’s pussy with my cum. As I pulled my cock out of Megan, she sat up on the Love set and gave me a big kiss. Then she slumped down and said to her husband “Hay honey, would you like some more”, as my cum was leaking out of her. Carl jumped right up and came over to start sucking my cum out of Megan’s pussy. I moved over to the couch where Lilly was now setting. This gave Megan more room to spread her legs so Carl could feast on her tasty pussy.
Carl sat on the love seat, next to his wife after he was done cleaning her up. Lilly had cuddled up to me on couch and for the next 20 minutes we talked about everything, completely naked. I was just about to say that it was time for me to leave, when Lilly said “I think it is time for me to try out this stud, so we will see you in the morning”. With that she then said to me “come on you stud. Let us see if you can buck me off”. Well she led me into one of the bedrooms and we fucked and fucked and fucked all night. The next morning after a slow fuck, a quick shower, a lovely breakfast, and a big kiss good-by from both the ladies, I headed home.
Over the next two months, I would go over to Megan and Carl’s house a few times, to learn some more about the Swinging lifestyle and of course, to fuck Megan. I thought I would give it a try and started checking some of the sites that they had showed me. As I was looking at one of the sites, I got a message from a gentlemen that was wanting a guy to show his wife a good time for her birthday. He said that they would like someone under 40 YO. I checked there profiles and found out that he was 61 YO, 6’-1”, and 220 LB. His wife was 56 YO, 5’-5”, and 145 LB. There was a picture of the two of them with clothes on and a picture of just her showing her breasts. She must have been turn-on when they took the picture because her nipples stuck way out.
Even though I was nerves, I figured it was time to jump in. I messaged he back and told he that I was 26 YO, 5’ 11” & 175 Lb. I also told him that I am not married, that I have a good job, and that I think his wife looks great. Well I did not hear back from him for about a week. He finally messaged me back and said that his name is Doug and his wife name is Rose, this would be the first time that she is with another man since they have been together, over 36 years ago. Over the next few days we talk a lot about our likes and dislikes. He said that Rose’s birthday is this weekend and he wants to be in the room just to watch and to make sure she is ok. He suggested that we all meet at 8:00 for drinks at the hotel and if we all agree, then we would get a room. Well right at 8:00 PM I meet up with Doug and Rose. I gave Rose a Happy Birthday card and a bouquet of flowers. We talked for an hour or so, then I said I needed to go to the bathroom just to give them some time to talk it over between themselves. When I came back, Doug said “Are you ready for Rose to open her present”. Rose nodded her head yes and I said “you bet-ya, lead the way”. They had already got a room so we walked to the room with Rose holding my arm and Doug leading the way. When we got to the room I gave Rose a hug and a quick kiss. I started to sit down thinking that they would want to talk a little but Doug quickly pulled on a tie strip on the back of Rose’s dress and it fell to the floor. Rose was now completely naked. No bra, no panties. I took that as a sign “let’s get started“. I walked up to Rose and gave her a big hug and a long kiss. Of course my hands was all over her breast. Doug was still behind Rose, rubbing her back and shoulders at the same time. As we continued to kiss, I guided Rose over to a nearby chair. I sat down and pulled Rose up close to me. This put me in a perfect position to start suck on Rose’s tits. With my lips sucking hard on one of her tits and one hand on the other tit, this left my other hand to start rubbing her clit. This continued for about 4 or 5 minutes. Rose was breathing heavy by now and all hesitation was gone. She dropped to her knees in front of me and with a smile, she started to take off my pants and underwear. My dick was already hard as a rock. She grabbed my dick and smiled then turned to her husband and said “I really love my Birthday present”, then she turned back and started licking up and down the sides of my cock along with fondling my balls. After about two minutes of this, she opened her mouth and tried to swallow as much of my cock as she could. I noticed that Doug had taken all of his clothes off and was stroking his dick, trying to get it hard. Rose was doing such a great job of suck my dick that after about 6 or 7 minutes, I was about to cum. I did not want to cum just yet, so I stood up bringing Rosa with me. I then guiled her over to the end of the bed and had her lay down. Her feet were a little off the end of the bed. I grabbed her knees and forced then up towards her head and then bared my head between her legs. I licked and sucked on Rose’s clit and pussy. Every now and then I would probe her pussy with two fingers as I continued to suck on her clit. As I was eating Rose out, Doug went and sat on the side of the bed near Rose’s head just watching us play. He was still rubbing his dick, trying to get it hard.
I continued sucking on Rose’s sweet spot with Rose breathing heave and moaning every now and then. Rose lasted about 10 minutes with this action before she reached her climaxes. With a loud moan, she through her head back, grabbed my head and pulled it into her, and then clamped her legs hard on my head. I kept eating her pussy until I was sure her orgasms was over.
It was my turn now. As soon as I was able to get my head free, I moved up her body, stopping for a few seconds to suck on her tits again, then continued up to her lips for more kissing. I reached back and grabbed both of her knees, bringing then up towards her head and spread them wide apart. This made it easy for my cock to line up and enter her pussy. Doug still just sat back and watched, as I was now fucking his wife fast and hard. As I was still fucking Ruse, I told her that she needed to thank her husband for the great Birthday. She motioned for Doug to get closer so she could give him a kiss. Then she grabbed ahold of his dick and pulled him closer so she could suck on it. Doug lasted about 5 minutes with the great job that Rose was doing on his dick. I lasted not much longer fucking Rose, then I was dumping my load of cum into Rose’s pussy. I wanted Doug and Rose to know that I was coming so I let several loud moans. I rolled off of Rose and laid next to her trying to catch my breath.
We all just laid there and relaxed. Doug and Rose for the next 30 minutes or so, was tell me about how they met and about their kids. I said that this was the first time that I had sex this others (mostly true). Rose finally said “You were a wonderful Birthday present. I hope we can do this again soon”. I smiled and said “How about now, is that soon enough”, then I pointed to my hard cock. Rose smiled and then looked at Doug with a devilish look. Doug just said “It is your Birthday”. Well over the next hour, I eat and fucked Rose in difference positions. We finally ended up with me fucking Rose from behind as she was on her knees, sucking her husband’s cock. This started my swinging days. Over the next two years, I meet up with ladies, mostly with their husbands, for fun and sex. I fucked Lilly again when she and her husband was visiting Megan. I tried being one of the guys in a gang bang (it was ok but not great). Some ladies I would get together more than once and some I even became good friends with. Tall, short, big, small, as long as I thought that they did not want to get married, I could be myself. Then I meet Susan but that is another story.