tagTranssexuals & CrossdressersHow My Wife Became a Swinger

How My Wife Became a Swinger

bySS_Swing©

Hello, my name is Jackson, Jack for short, and I'd like to tell you about my wife and I and how we became swingers. I've changed the names of people and places to preserve privacy. Just so you know this does involve male on male sex and inter course with a transsexual. So let me begin.

For the first few years of our marriage were pretty standard or at least what I think is standard. How many people actually look at their friends and know that they love: talking dirty, pulling hair, anal sex, cum play or anything else during sex? So when I say normal for us I mean oral sex, some ass play, and just plain old animalistic fucking. On occasion we would also bring in a toy. I would be on the receiving end more than my wife. We had acquired an assortment of dildos and vibrators over the years. Early in our relationship I had introduced anal play to my wife. She had grown up sheltered from a lot of things and I think the first time I ran my tongue across her tight little ass the world she knew got put on its head.

Anal play became a regular theme in our playing, rim-jobs being our favorite, and it was during a rim-job that my wife confessed to me that she had fantasized about us having a threesome. Most guys would flip over this. That is because most guys are assuming that I'm talking about another woman. She was referring to another man. I'm bi, up until I got married I was a regular cruiser. At about fifteen or sixteen I made an astounding discovery, sex is great with both boys and girls. On the other hand, my wife waited a little longer to discover sex and is- was straight laced enough to not find the same sex attractive.

For years she's known that I am bi. In fact, we have an assortment of toys that allow her to... roleplay. Anyway, that night she had just the right button. I was on my back, legs opened wide with her going between licking my hole and sucking my cock when she told me. Angela was laying on her stomach her cute tight ass pointing at the ceiling her big gray eyes looking up at me from behind my cock. She smiled and went back to licking me as it set in what she had said. She lifted her face from her work on my hole and smiled from behind my cock again before taking it into her mouth. She sucked me like a champ. Once my cock was out of her mouth she asked me what I thought about her fantasy... I fucked her silly and the next day I set out to bring that fantasy to life. I had no idea at the time what this would lead to, and how it would change us, and our marriage.

Finding a guy for my wife, as any man knows, is difficult for a number of reasons least of which you want someone who is quasi normal. So after three months, nine online ads, five blowjobs and a single exchange of man-on-man anal sex and I found a guy named Jason. He Lives just outside the country where my wife, Angela, and I live. His location allowed for us to be discreet and close enough for him to get to our place if certain needs arouse. As always, there was a hitch. My wife didn't want me to bring in just some guy. So Jason "accidentally" met my wife where she works and got to know her. She had no idea who he was or that I even knew him.

Jason took his time. It was almost three months before the threesome actually happened. He would show up at her work and just be a good friend. It's been a few years so I can't recall exactly how he broached her and told her that he was bi. I remember that night though. I came home from work before her. I was in the shower when she came in. Through the shower curtain she talked about her day. I wanted to save Angela some hot water so a rinsed quickly and hopped out of the shower

Angela was sitting on the bed as I toweled off. Her long dirty blond hair was up in a bun. She was naked her feet up on the bed heels drawn up spreading her legs displaying her bald pussy. Half out of her pussy was one of our favorite toys, a blue double-headed dildo. There wasn't much need for words. I walked up to her and lifted the dildo off of the sheets. I worked it in and out of her. Her head fell back as she moaned.

"Get up here so I can fuck you." She barely managed the words between moans. It was all she really ever needs to say.

I laid on my back as Angela moved into a modified missionary position and produced a bottle of lube. She wasted zero time lubing me up and sliding her plastic cock into me. It took about three minutes for me to fully relax, and by then we were asshole to pussy. I had never seen her that excited before. She fucked me like there was no tomorrow. She had one hand on my cock while the other massaged her beasts. Again and again I would come close to exploding but she would become lost in the own quest for pleasure. She was trying to make me cum but I wasn't going to have it, although she managed to get off twice before she pulled her dick out of my ass. She sprawled onto her back and I went to work cleaning up the mess she had made in her pussy. It was maybe ten minutes later that she rolled onto her stomach and said it was her turn. I went to slide into her pussy, but she pulled away from me as I was about to push in.

"I fucked you like a man, it's your turn."

This time as I was leaning in she reached over her hips guiding me to her tight butt. I took my time sliding into her. Unlike me, her ass isn't penetrated on a regular basis. She had lubed up before she had taken her pose on the bed, and before too long I was completely buried in her. I playfully gnawed on the back of her neck as I started to pump. She worked with me pulling away slightly as I withdrew, and pushing as I thrust. Slowly I caressed her tits and rubbed at her stomach as I moved in and out of her ass. I worked my way down to her clit and started to rub slow circles around it until she came. Her ass clamped down on me as she rocked in orgasm. I let her recover for a minute before we started to it again. We built up and worked each other for what seemed like an hour before she finally demanded that I cum. At that instant I emptied my balls into her bowels.

As my cock started to go limp in her she turned her head and kissed me. Angela pulled away from me and found a shirt to cover her ass with and she slid off of me.

"Would you fuck a guy like that?" She asked pressing the shirt to her cum filled hole.

"Everything but the kissing...yeah."

"I want to watch you fuck a friend of mine. He told me that he was bi and I got talking to him about it and he hasn't been with a guy for a while."

"Who?" I knew damn well who.

"He's a customer, a great customer, and he bought me lunch the other day. It just kind of came up."

"So you want him to come over and fuck me?"

"He'll be here at nine." She said smiling looking over at the bedside clock. It was seven thirty and some change. "I wanted to make sure that there was enough time so that I could call the whole thing off. So what do you think?"

"We should go shower because I doubt that I'm the only thing that he'll want to put his dick in when he gets here."

Jason was a little over ten minutes late getting to the house. Angela and I were in robes when he knocked on the door. He came in and my wife introduced the two of us. The three of us went into the living room and tried for small talk. As you could imagine things were a little awkward right then. I thought I had an opening.

"So," I asked Jason "When was the last time you had a real blow job?"

"I had a girlfriend for about four months and she broke it off about two weeks ago. She hadn't been... you know... for a while though." I got up and walked over to him.

"I mean a real blowjob."

My hard-on should have been visible to the both of them just as Jason's was to me. I Dropped to my knees in front of him and shrugged off my robe before undoing his jeans and pulling them and his boxers to the floor. Jason's uncut dick stood seven and half inches. From balls to tip he keeps his jewels shaved, one of the big reasons that I picked him. Angela and I both keep ourselves clean shaven as well. I placed my hand around the base and heard my wife shutter as I pulled the skin tight exposing Jason's mushroom head. Angela watched as I licked his head twice before deep-throating him. It wasn't long before my wife joined me. She replaced my hand at the base of Jason's cock and we started to take turns sucking on him. Angela was lost in servicing Jason and I worked down to his balls, carefully licking and sucking, before I moved lower and began to rim him.

Angela looked down at me with Jason's cock in her mouth with a question in her eyes as my tongue pushed into him. I winked and she released his dick from her mouth. She went to the bedroom and came back with a fist full of condoms. Automatically she opened one and rolled it on to Jason before she mounted him. I watched to two of them fuck for a minute or two before I rolled a condom onto my cock. Jason has his mouth latched onto my wife's right tit when I shoved a lubed finger up his ass. He moaned around her nipple and my wife looked down at me. I could see the grin on Angela's face as I fingered him. He cried out as I entered him, and my wife picked up her pace. Angela and I built a rhythm as we fucked Jason. Reaching around I found Angela's clit and stared to lightly rub her. My other hand massaged her breasts as I humped Jason. Her moaning pushed Jason over the top and he filled the condom inside of her.

She kept going, riding his softening cock, as I got closer to cumming. But she stopped me and pushed me back making my dick pop out of Jason's ass. Angela took my cock, guided me to the bedroom, and beckoned Jason to follow. The two of us climbed into bed where she laid me on my back before removing the condom I had on, and started jerking me off. She was on all fours with her pussy and ass pointing at the door when Jason walked in with his softening cock hanging between his legs.

"Jason, there's a bottle of lube on the night stand. Would you take some and lube up my butt please?"

She never missed a beat as Jason slipped a finger into her butt. Her eyes were locked on mine as she stroked my cock. Her breathing picked up as Jason fingered her harder and harder. Every now and then she would look back to see if he was hard. Finally when he was ready Angela slipped off of his fingers and straddled my hips reverse cowgirl and slid my cock into her ass. She leaned back, one hand supporting her weight, as she rubbed a circle around my ass to show Jason where to put his cock.

As Jason rolled on another condom Angela worked two fingers into my ass as she rolled her hips around my dick. She sat up straight when he put the head of his cock up to my hole.

"Six years he's talked about fucking men and getting fucked." She flexed her ass around my cock and sank down it further than she had ever taken, me stopping when her ass cheeks were resting on my hips. She kissed Jason on the mouth, and she caught her breath from the effort her ass was making to accommodate me.

"Fuck him slow I want to enjoy this."

Jason took his time, and Angela made sure that I couldn't cum. She was methodical, only working my dick as much as she needed to, to keep me hard. I lost track of time but I was in heaven. My cock inside my wife's gorgeous ass, and a beautiful seven and a half inch cock fucking me. I know Jason tried his best not to cum but in the end my ass won out and he filled his second condom of the night. Jason slipped out of me out of breath. Angela motioned for him to lean in. She thanked him for the show with a kiss then directed him to her bald pussy and told him to lick. All too happy he complied, and before long she was again humping my cock while Jason ate her out. I only lasted about five minutes once she started humping, but the sensation of her bowels being filled with cum as her pussy was being licked was too much, and she joined me in orgasm. Her entire body flexed as the sensations sent her over the edge. Her ass clamped down on my cock almost painfully, sending my cum squirting out around my dick. Jason was there a second later lapping up the leaking cum.

Angela finally relaxed and I was pulling out of her when she stopped me. She told Jason to go wash off his cock and get another condom. She started talking dirty to me about how much she had enjoyed the show and that it was her turn for fun.

Jason reappeared with a fresh condom and Angela opened her legs and told him to get back in her pussy. I could feel him slide into her. She cooed and moaned as the two of us fucked her like she had never experienced. The two of us rubbed her body with our hands as we ground our cocks into her holes. Between the two of us, Angela came three times before we climaxed for the last times that night. The three of us shared a shower, where Jason ate my cum from Angela's ass. We set Jason up in the guest room for the night, and that was how the door opened for my wife.

Jason became a regular part of our sex life. After a while we stopped using condoms, we were all tested and came back clean so it was decided that bare back was just fine since Angela was on birth control. Angela and I would stop by his apartment every now and then, and Angela even blew him in the parking lot of her store one night before she came home. He and I would meet up from time to time for some one on one. Angela caught us once while I was fucking Jason on our living room floor. I had caught them in the same position as well. It was all fun and games. Once a week or so he'd come over for the night. It was just before Christmas that same year that Angela and Jason conspired to get me a very interesting present.

I was running late from work one night and came home to Jason and my wife naked on the living room floor. Angela was on all fours with Jason up to his balls in her pussy. I should mention that Angela, to this day, will only let me in her ass, with the acceptation of toys. I stripped and offered my dick to them. Jason went down on me while Angela moaned from the assault on her pussy. Before Angela could climax he emptied his balls into her pussy. She got out from under him and the three of us retired to the bedroom. Jason flopped down in his back and Angela straddled his face as I took his cock in hand.

I sucked on him for a few minutes while Angela sat on his face looking towards me so we could share his cock. We worked on him for a minute before she mounted him. She fingered him with lube then told me to slide into Jason's ass. He didn't last too long. He came and slipped out of Angela and off my cock. Angela rolled onto her back and I slipped into her twat while Jason licked at my ass. I almost came right them. I settled down and then I felt the rubber-covered head of a cock at my ass. I thought that it was Jason, and so I pushed against the dick and let it slip into me. Jason is larger than me by an inch and a half but this cock, sliding into my ass, was almost nine. I also felt a beautiful pair of tits press against my back. My mind raced and I realized what was going on.

Eva, the owner of his beautiful appendage went into me up to her balls she cooed in my ear as Angela gave me a slutty little grin and said Merry Christmas. I didn't even last five minutes. It was my greatest fantasy being fulfilled.

Eva is a transsexual from Hawaii who was on vacation visiting her brother. Jason had met her a few days before and conspired with Angela. Jason had been bragging about bedding Eva the night before one day while he and Angela ate lunch. Angela knew that it was the one thing that I hadn't done. So Eva and Jason came over that afternoon. They sat around talking until they heard me coming up the driveway, and Eva hid in the spare room while Jason and Angela started fucking in the living room.

Once she had recovered from her orgasm and pulled out of me, I got my first look at her. All I could think was WOW. Without the nine inch long dick there was no way anyone could have been able to tell she wasn't a woman. Jason took his time sucking her while I recovered in Angela's hands, then we started a daisy chain. I was that the back in Eva's very nice ass while she butt fucked Jason and while he fucked Angela's pussy. She was tight, and hands down an amazing fuck. I reach around and fondled her chest as she fucked Jason. I had never heard him moan as hard as he was that that moment. I came to find out that the largest cock he had taken, to that point and been mine. Angela didn't make it easy on Jason either, rotating her hips as he humped her. Jason came first, then Eva. Angela sucked her off while I fucked her. Eva came all over her chest and face. Jason quickly started licking the rope of cum off of my wife as she lay next to Eva and me. My wife started to finger me when I got close, and sent me over the edge for the second time, and I emptied my balls.

After that we all took a bit of a break, before Eva and Jason left we went around one more time. Jason and Eva fucked while Angela and I went at each other doggy style with Angela sucking off Eva. Jason came in Eva, Angela and I laid her on her back and went to work in her cock and asshole. She came in my mouth as Angela's tongue was buried in her ass. While Angela and I serviced Eva, Jason had been feeding her his dick to get hard again. As she came, he moved behind me and slid in up to his balls in one motion. Angela kissed me before mounting Eva's face and riding our new friend's tongue to three orgasms while Jason and I fucked.

Eva joined us one more time before she had to head home and it was an equally entertaining evening. Angela was focused on sucking me off while Jason was fucking Eva. She was on all fours with her ass in the air inviting someone to put something up her pussy or to lick her ass. She thought that it was Jason sliding into her pussy for a moment. Eva is the largest dick Angela had ever had in her too. She quickly realized it wasn't Jason when Eva was about half way inside her. My cock fell out of her mouth as she moaned and arched her back. Jason came over and laid next to me so he could watch my wife getting fucked by a tranny. Angela sat up and wrapped a leg backwards around Eva exposing her pussy and Eva's cock to us as they fucked. Eva's hands were all over my wife, rubbing her tits and playing with her clit. Jason started to jerk me off as we watch one of the most amazing things I have ever seen. Jason and I rearranged ourselves I wanted to be under the two "ladies." I lay on my back between their legs and ran my tongue along Eva's cock as it went in and out of my wife slit.

I had thought Jason was just going to jerk me off, but instead he mounted my cock and began to make out with my wife, sucking on her tits and kissing her. Angela came hard and stopped Eva's fucking cold as her pussy clamped down on that beautiful dick. I took the break in the action to move a few inches forward and slid my tongue up Eva's cum filled ass. Angela came one more time before Eva and I shot our loads. I came first but stayed under the ladies. Eva's orgasm was powerful; she drove the entire length of her cock into my wife as she came. Once she pulled her cock from Angela's hairless cunt my mouth was glued to it drinking every last drop I could. Angela came twice more as I was cleaning her pussy. When I was done, all three descended onto me to lick my face clean. It was all in all a great Christmas present.

Things kind of went back to their natural rhythm until Jason broke up with us. He had met a stunning young woman who was very opposed to gay sex. They lasted three years, the end came after he had proposed and had told her that he was bi. Still he broke up with us and Angela and I were satisfied for and I the time being with just us. We used toys and had sex about three times a week always talking about how much fun Jason had been.

Angela got promoted the next year and went up to Seattle for a three day long training seminar. I drove up the last night of the seminar, and we extended the arrangements for the hotel room she had been staying in. We had a great round of sex before going out for dinner. Angela was in a cute outfit with no panties while I was in a pair of slacks and a nice shirt. It was at dinner that she was asking about cruising. I had lived near Seattle before our marriage and she knew that I had spent many a Friday night in an adult theater or in a video booth blowing some guy through a gloryhole. She wanted to see a few of the places I had frequented.

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bySS_Swing© 6 comments/ 71602 views/ 12 favorites

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