The First Time
One night I had laid between her legs and licked her to a nice cum. She grabbed my head and pulled me up toward her. Fuck me now, she hissed. Put that boy dick in me and fuck me good, she said. As I laid down on her and she guided my cock to her wet and slippery pussy I said how I wished I could slide a real cock into her and fuck her brains out.
She just smiled and away we went, fucking hard like always. Soon I felt her raise her hips up and press hard against me signaling her climax. I drove down as hard as I could and rammed my little dick as far inside her as I could and let go with my squirts of cum. She finished her climax and so did I. I filled her hot pussy with my cream and we laid there a little while resting. Then, as happens often, my wife decided she wanted another orgasm.
My little cock was deflating so she chose her usual routine that we both enjoy very much. She got up on her knees and straddled my face. I put my hands on her hips and guided her cum filled pussy down to my mouth. Suck hard baby, clean me out good, she said. I stuck my tongue inside her and closed my lips over her clit. As I sucked my load of cum out of her I felt her orgasm start. As usual it was a big one. She cums so good when I lick and suck her after we have sex. And lots of times it turns me on so much I get hard again and we fuck again. And this time was one of those. Carol Ann reached down behind her and played with my little cock while I continued to eat my cum out of her.
Soon we were both horny enough to fuck again. Come on sissy, put that boy dick in me and do it to me again she said as she laid back down on top of me. My cock slid into her velvet feeling pussy and she started rocking back and forth on it. I wish it was 10 inches long and fat, I whispered to her. She just smiled down at me and increased the pressure and motion. Soon she was moaning and groaning through another climax.
After that she laid next to me and we cuddled and kissed. You know, your cock is just fine for me, she assured me. I told her I knew that but that it would be nice for her to feel a big cock for a change. And where are we going to get this monster cock, she laughed. I was going to have to think about that. The same things kept coming up. Usually with me mentioning it during or after sex. I asked her once if she ever had a big cock. She told me she Haydn’t and that mine was just fine. But I kept after her, telling her how good a big cock would feel inside her. And I started telling her how turned on I would be watching her get fucked by a big one. She had a hard time believing that one.
But I said it enough that finally it dawned on her that I would be turned on by watching her get fucked by another man. One night we were watching television and there was a movie about wife swapping. It did’t show much but the innuendos and ideas were all there. My wife asked if that is what I was talking about. I told her that the idea of her having sex with another man was a huge turn on to me and that my having sex with another woman was not at all interesting to me. She had a hard time figuring that one out. But she got kind of playful during the movie.
She disappeared into the bedroom and came out a few minutes later wearing a teddy and thigh high stockings. She was carrying my favorite pair of pink satin panties. I had bought the panties for her but she somehow convinced me to wear them instead. And they felt great on my skin. That is where the sissy boy thing came from. It turns my wife on to see me get hard and horny in women’s underwear and lingerie. She dresses me in sexy undies, dresses in her own lingerie and then has us play sexy games. Some times we role play with us both dressed up sexy. We will be lesbian lovers. Or I will be a sissy boy who is seduced by the local slut. Or she will “catch” me cross dressing and “force” me to perform naughty sex with her. Maybe she will make me jack off while she watches. Or she will stroke me through the panties until I cum and then make me lick the cum out of them. Or cum on her and then have to clean her up. Anything that is hot and fun.
We’ve tried lots of different things. But this night was a little different. I got into my panties and she came and sat next to me on the couch. She played with my hard little cock through the panties. I put my hand between her legs and rubbed her through the smooth material of her teddy. I felt the material getting wet. Suddenly the new game was on. That’s it sissy boy, get me wet for my big cock lover who is coming over, she said. I almost came in my panties as that idea went through my mind. She kept it up and I joined in to her new role playing fantasy. I’ll get you nice and wet and slippery, so his big cock will fit inside you, I told her. And I’ll get your sissy little boy cock hard so you can sit and jerk off while he fucks me good, she said. She leaned over and kissed me and pushed her tongue in my mouth. Then she looked me right in the eyes and said, and he will squirt a huge load of cum up inside me for you to enjoy later too sissy boy. With that she squeezed my cock hard and I lost it. I was gushing my cum into the panties and groaning. My wife laughed as she finished me off. Boy, that sure got you off good didn't’t it, she said. I told her it was so hot I lost it and apologized for cumming so fast. She laughed and spread her legs and pointed to her pussy and told me it was her turn. I knew what she wanted. I got down on the floor between her legs and opened the snaps on the crotch of her teddy. She scooted forward and pulled my face to her wet pussy and told me to give her what she needed. She rubbed my wet panties over my cock with her foot as I licked and sucked on her pussy and her hard clit. She pulled my face tight against her as she climaxed on my face. It didn't’t take her long to cum so I knew her little game turned her on too.
We talked about the little game as we cuddled on the couch. I asked her who her big cocked lover was. She told me she had no idea and I should come up with one for her. I asked if she was serious and she told me that if I wanted it, she would do it. But I had to find the guy and she had to approve of him. We talked about how it would be and ended up both getting hot again and fucking on the couch. She asked me questions about how things might go with another man. We talked about different scenes of her having sex while I watched. She asked if I would jack off while I watched and I told her I would have to. She asked if I would want to have sex with her after the other guy was done and I told her I wanted that more than anything. She asked what I thought about having sex with her when her pussy was going to be full of cum from another man. I told her that would turn me on a lot. She had a hard time with that until I put her hand on my stiff little cock to show her how much the idea turned me on.
My wife suggested we find someone we already knew to take part in our game. I thought about it and suggested Steve. Steve is a guy I work with and a guy I know has a huge cock. I know that from a fishing trip we took one weekend. I saw Steve with a half hard cock one evening as we got ready for bed in the cabin. I have no idea why his dick was hard but I know it was huge compared to mine. And Steve is laid back and easy going too. He is single and wants to stay that way. Some say he is gay because he doesn't’t go out much but I know that is not the case. Bi, maybe, but I know from our work place banter that he likes pussy as much as I do. My wife has met Steve a few times and thinks he is hot and good looking in her words. So all I had to do was figure out how to set this up. I did it as simple as I could.
I invited Steve to our house for a few drinks and a movie. He jumped at the chance and even asked if my hot wife would be there. I laughed and told him she would be there and wouldn't’t miss it. Then he laughed. If he only knew. I then talked to my wife about how we would go about getting her and Steve together. After talking about all sorts of ideas, she finally told me to leave it to her and just play along. I agreed.
Steve arrived and he and I settled in for a drink and turned on the TV. My wife made her appearance then. I hope you boys don’t mind if I dressed comfortable for lounging, I had a tough day, she said. She was wearing a nice robe and I noticed nylon stockings on her feet. But that is all I noticed. Later, when helping her make another round of drinks in the kitchen, she opened the robe for me. She was wearing a satin bustier, matching panties, and thigh high stockings. My cock got hard just looking at her. She laughed at the tent in my pants. I had to hide it when I went back to the living room. Carol Ann then started flirting with both Steve and I. She told us how hot it was in the room with two hot studs like us and other things like that. She is very good at that sort of thing and soon had Steve relaxed and comfortable. I left the room several times for bathroom breaks and more drinks, but nothing was happening.
Finally my wife took me aside and suggested I head for bed and leave her and Steve alone. I did as she asked. At the end of the present movie I suggested I was to tired to continue and needed some sleep and that Carol Ann and Steve should watch the next movie without me. My wife jumped in and told me that would be fine and she would take good care of Steve and not to worry about a thing. Steve just grinned and nodded, having no idea what was coming. My wife led me to the bedroom to tuck me in, as she told Steve. Inside the bedroom she again opened her robe and took my hand and put it on her pussy.
The next time you feel this, it might be full of another guys cum, and all stretched out from his big dick, she told me. She then reached inside my sweat pants and fondled my hard cock. I kissed her and told her how much I loved her. She told me the same thing back and then turned out the bedroom light and turned to leave. When she left the room she left the door open a half a foot. She did that so I could watch. I have a good view of the couch from the bedroom door and with the light out, no one could see I was watching. Carol Ann then returned to the living room and sat down on the couch with Steve. I could make out what they were saying and see everything they did. I got out of my clothes and pulled on my sissy panties. My cock was already hard in anticipation.
My wife lost no time. She sat next to Steve and took his arm and wrapped it around her shoulders. She took his hand and put it inside her robe and rested it on her breast. I watched Steve to see how he would react. He left his hand on my wife’s breast but made no movement at all. My wife then placed her hand on Steve’s thigh and started rubbing and tickling it. Steve looked uncomfortable. Carol Ann, he stammered, I um, we, ah, I mean. My wife reached up and put a finger over his lips. Relax she told him. Don’t worry about a thing. But what about Jack, he asked. Jack is sound asleep, and besides, we have permission to do whatever we wish, she told him. Don’t worry about anything, she continued, just do what you wish, it is all ok with Jack. It must have dawned on Steve just what my wife was telling him. I saw his hand move on her breast and he turned and kiss her gently on the lips. My wife kissed him back and rubbed his thigh. Then she stood and asked if he wanted another drink. He nodded and she got up and took the glasses to the kitchen.
When she returned, she had lost her robe. Steve obviously liked what he saw and smiled broadly. He took his drink and patted the couch next to him for my wife to sit down. When she settled on the couch they were all over each other. Kissing and touching, rubbing, and petting each other. Moaning and groaning and obviously getting hot. Carol Ann reached for Steve’s belt and insisted he get more comfortable. After all, she told him, I am have naked and you are fully dressed. Now stand up and let me fix that, she told him. Steve stood and let my wife open his shirt and remove it. Then she opened his pants and pulled them down.
She made sure he was facing in a way that I would be able to see what she was doing. As he pants came down I saw a huge bulge in his briefs. My wife stopped and stared at it for a long time. It was like they were both paralyzed. I was excited and lightly fondling my little hard on. Finally my wife got down on her knees in front of Steve. She touched his hard cock through his briefs, rubbing it with both hands. Finally she reached up and grasped the waist band of his briefs and worked them down over that huge cock and pulled them down and off. Steve’s big cock sprang free and stood straight out away from his body. It was the biggest cock I had ever seen. From where I was I could see it was almost a foot long and as big around as my wrist. I worried for a bit that my wife would be able to handle it. But that feeling went away when I saw her guide it to her mouth. She opened her mouth and took the head of it inside. She twisted her head and slid her hand up and down the big shaft as she sucked. She ran her lips up and down his cock and took him inside her mouth again and again. Finally she pushed him toward the couch and had him sit down. She knelt before him and continued to service him with her mouth, taking more and more of him inside. She was only able to take a quarter of his length inside her mouth. I thought about how she can easily take my entire length in her mouth when she sucks me and I had to laugh. I almost gave myself away.
Steve finally switched places with my wife. He pulled off her panties and stuck his face between her legs. She spread her legs wide to give him access to what I knew was her very wet pussy. He ate her with enthusiasm. He soon had her moaning in orgasm. Then I heard the words I was waiting for. Fuck me, she hissed at him, stick that big cock in me and fuck me hard. I opened the door a little more. Steve knelt between my wife’s legs and they both held his cock and guided it to her hot pussy. I watched as the head slipped inside he. I had to take my hand away from my cock to keep from cumming right then. I watched as they buried that huge cock in my wife’s little pussy. Soon she was moaning about how good it felt to be filled with a real cock. I know the remark was for my benefit. Steve seemed to get caught up in her game and said, Jack should see you now, filled full of cock like this. My wife told him not to worry, I could see just fine. Steve turned and looked down the hall toward me. I wondered if he could see me standing there in my sissy panties with a tent poking out in front. Steve reached for Carol Ann’s breasts and kneaded them while he pushed and pulled his huge cock in and out of her stretched pussy.
My wife was cumming over and over on his big cock. She was telling him how good it felt compared to my little boy wiener. Steve laughed and pushed it in even further. Look Jack, look at your wife take this big cock, Steve said. I almost came in my panties. Yes honey, look at me full of cock, my wife said. I knew that they both knew I was watching and then wanted to give me a good show. I opened the door wider and I knew then that they could both see me standing there with a hard little sissy boy cock in my pink satin panties. But I didn't’t care. And I knew they didn't’t care either. Steve then pulled his big cock out of my wife. It was wet and shiny with her juices. Steve sat on the couch and pulled my wife down onto his lap. She was facing me and I could see perfectly when she guided his cock to her opening. As his cock slipped inside her, she bobbed up and down in short strokes, taking more and more of the giant tool inside her each time.
She moaned a long low moan as she sat down hard and buried the rest of the huge dick inside her tight pussy. Look Jack, look at this, Steve suddenly said, look at your wife sitting on my big cock, she is taking it all. They were both looking straight at me. I knew the could see me. Honey look at this, my wife said. Look at the big cock I have inside me. This is what you wanted, she continued, are you happy now that I am fucking a big huge dick? Come out Jack, said Steve, come out and see your wife get fucked if you want. I walked like I was hypnotized. I had to see. I forgot all about my pink panties. I heard Steve chuckle as he saw my panties. My wife explained to him that I enjoyed being a sissy boy with my tiny cock. I was very embarrassed but also very turned on. The closer I got the better view I had of Steve’s big cock buried inside my wife. She was still bouncing up and down on the big cock and it looked so good. Steve was playing with her breasts as he fucked her.
Come close honey, my wife said, come close and see what you wanted to see all this time. I walked across the room and knelt in front of them. My face was only two feet from the hot sex in front of me. I could smell the odor of sex. I saw Carol Ann’s juices running down his shaft and over his big balls. It was the hottest thing I had ever seen. Look at the sissy panty boy, my wife told Steve. I see him, Steve answered. Fuck her, I told Steve, fuck my wife with your big cock and make her cum.
My wife told me to come closer and take a good look at her getting fucked with a big cock. I leaned closer. My wife then grabbed my hair and pulled my face into them. She told me to lick her clit while Steve fucked her. I licked her clit. I licked her all over her stretched pussy. And I could feel my tongue touch Steve’s big cock too but I didn't’t mind. I was so hot and turned on that I didn't’t care at all. I just kept licking and soon I knew I was licking them both. They were fucking and my wife was holding my head against them and I was licking them both as they fucked. I wondered what would happen when Steve came inside her. But I kept licking and my wife kept forcing my face tight against them. Come up here sissy boy, my wife said. She pulled my hair upward and I half stood. She pulled my head to hers and kissed me and pushed her tongue into my mouth. I felt her hand pull my cock out of my panties and start to jerk it. Steve was moaning and Carol Ann was cumming as she kissed me and jerked my little hard on. It was the hottest moment of my entire life.
Do you like this, my wife asked me? I could only moan yes as I felt my cum start to shoot out of my cock. I looked down and saw that she had aimed my little cock right at the place where Steve’s cock and her pussy met. I watched as spurt after spurt of my cum squirted out and splashed onto the two of them. I had never cum so hard in my life. My goodness, sissy boy, you had to cum bad didn't’t you, my wife moaned as she started to cum again. She kissed me once more and then pushed me roughly downward. Lick sissy, lick up your mess, she ordered. I looked and saw huge gobs of my cum juice on her pussy lips, on her clit, and on Steve’s cock.
My wife pulled my face against them again. I started to lick. I licked all over. I licked both of them. I didn't’t care any more about licking another man’s cock. What did it matter? I tasted my cum on my tongue. But that was nothing new. I had licked my cum off my wife hundreds of times, and sucked it out of her hot pussy just as often. I sucked at her clit and heard her start to cum again. Just then I heard Steve moan that he was cumming. I just kept sucking at her clit. Suddenly my lips and tongue got very wet and slippery and I realized Steve was pumping a huge load of cum into my wife’s pussy. His cum coated his cock, it coated her pussy, and it coated my entire face as my wife ground my face against them.
I stuck my tongue out to lick more. I felt my wife start to raise up. I did’t even think about it. She kept my face pulled against them. I heard her hiss, yesssssss and suddenly she was raised up off Steve’s wet cock. Suck it sissy, I heard her say. It was like a dream. I felt her push my head downward and felt Steve’s cock enter my mouth. Suck it hard baby, she cried. I sucked. I was sucking another man’s cock. A huge cock. I was licking and sucking and actually liking it. I was enjoying it. And Steve was enjoying it. He was telling me to suck it. Calling me a sissy boy and telling me to suck his hard cock. I kept doing it. My wife was calling me a cock sucker and a queer, Steve was calling me a sissy boy and I was sucking his cock.
All of a sudden I heard him say he was going to cum again. My wife said, oh no, no, not this. Steve said he couldn't’t help it. And I just kept sucking. I tasted it before I felt it. I tasted Steve’s hot load of cum in my mouth. Then I felt it. I felt the forceful jets of cum squirting into my mouth. Over and over. I took it all. When Steve finished shooting into my mouth I raised myself up. I looked my wife in the eye and I placed my mouth over hers. I opened my mouth and pushed some of Steve’s cum right into her mouth. I felt her struggle but I was determined to share his cum. Finally I felt her tongue push into my mouth and take the cum. When she broke the kiss I heard her tell Steve, watch this. She pushed me backward and I fell to the floor on my back. I saw her move toward me and straddle my head. I looked up and say her wide stretched open pussy. Steve’s cum was starting to ooze out of her as she lowered her crotch to my face. I opened my mouth and suck on her and pushed my tongue up inside her. I was amazed at how open her pussy was. It was like a tunnel. Her pussy was wide open from having taken that huge cock inside. I thought that if I tried to stick my cock in her she would never even feel it and neither would I.
Suck it all sissy boy, suck out all his sticky hot cum, my wife was telling me. Then I felt a hand on my cock. Rubbing my little cock back to life inside my pink panties. But my wife’s hands were both pulling on my hair, forcing my face tight against her sloppy wet pussy. It was Steve. Steve was playing with my hard little cock inside my panties. I sucked hard on my wife and let go with a second load of cum, right inside my pretty sissy panties. Steve told my wife that he had made me cum. Steve spent the night in our bed. He fucked my wife over and over all night. She loved it when I would take his cock and guide it to her pussy and help him get it inside her. They both loved it when I would lick them both as they fucked. And they both got a big kick out of making me suck Steve’s cock in between the fucking. And Carol Ann even got Steve to suck on my little cock a little bit. But it was clear that I was the little sissy boy in our group. I got Steve hard to fuck, and I cleaned them both up afterward. And I jerked my hard little cock as much as I wanted. What a night that was. There have been many nights since then too. But that was the first one.
