Pretty boy to Sissy girl

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Married pretty boy enjoys being cuckolded.
2.2k words
4.59
111.1k
170

Part 1 of the 4 part series

Updated 06/12/2023
Created 07/25/2022
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moonsissy
moonsissy
251 Followers

I first met my wife Tara at a new year's eve party. I was wearing eyeliner and my hair was relatively long. She would call me "pretty boy" as we danced. She was very sexy with a petite body, long dark hair and big brown eyes. We had a drink or two and were feeling quite turned on by each other. We ended up in her bed sometime after midnight.

As I got undressed she noticed I was wearing a g-string and she said she thought it was so sexy that I was wearing women's panties and that my body was so smooth.

"It's such a nice change to meet a guy who is in touch with his feminine side. I tend to always gone out with masculine, alpha males but I am so turned on by your lean smooth body and round butt, she purred as she glided her hands all over me.

I fell for her at that moment.

Now here we were four years later, a happily married couple. Me, sitting back in a chair watching as she was pleasuring one of those masculine alpha males who she gravitated towards before we were married. As he thrust his big, rock hard cock into her I rubbed my panty covered dick. Tara had met this Adonis through work. She talked about him for weeks before I agreed to have him come over to the house. His name was Michael and though he was married, his wife, had no idea of his sexual adventures outside of their marriage.

Now, as this bull fucked my wife all I could think about was how big his gorgeous cock was and how strong he looked. All the things Tara had told me about Michael were true. She kept telling me how sexy and charismatic he was. And how just being in his presence made her wet. Now as she was screaming and moaning in pleasure in front of me, I was sort of shocked to realize I was more enthralled by his big dick than my wife's sexy body.

I was so turned on by the muscles in his body, his powerful presence, his creamy brown skin, his deep voice. I rubbed my little hard-on and then took it in my fingers to stroke it.

I was bisexual and my wife knew this. At night we would often share our fantasies which aligned with each others. She always had fantasies of threesomes and gang-bangs with strong alpha males, often they were athletes, black men and white guys using her like she was their slut. This was fine with me, because my fantasies were always about her with other men. And the more alpha the men, the better. At first I was embarrassed to admit to her that I wanted to be submissive to other guys, especially while in front of her. I told her how I wanted to eat their cum from her pussy once they were done using her. I told her I would be the fluffer at her gang-bangs.

She wasn't surprised and just said, "Honey, you are a pretty boy who shaves his legs and wears panties. Why would I be surprised that you would like to be dominated by masculine men? I married you knowing if I was with a cocksucker, I would be able to continue having sex with other men. "

Soon our open fantasies led us to this point - me in panties watching and playing with my little cock (I was at best 5 inches) as a hot, muscular black athletic man pleasured himself with my wife in front of me. I craved his big cock. I wanted him in me, making me scream with that same intense pleasure that was making my wife, Tara, scream. I knew he must have seen me looking at his big dark prick, I couldn't take my eyes off it. He must have suspected I wanted to touch it, and stroke it and put it in my mouth and even get down on all fours and have it in me. Of course he knew. I was in panties and had smooth legs and eyeliner on. For god sake I had a tiny dick and was letting him fuck my wife. He knew I lusted for him. I was a cuckold, a sissy cuckold, who was turned on by that fact.

After he had fucked Tara for awhile my wife told me to come over to the bed. I was almost shaking with excitement as I stood in front of this alpha man, with my smooth, thin, feminine body wearing eyeliner and panties. Even with my raging hard-on, the panties I wore covered my small penis. My wife told me to remove my panties and when I did Michael sort of let out a laugh and said to Tara, "I see why you need a bull like me babe. That is one tiny, pink, pretty boy dick."

"I know," replied Tara, " But he is pretty to look at and he knows how to lick my pussy."

Even though it was a bit humiliating to hear, it also excited me. My wife and I got into a 69. I could taste their sex. Just knowing his big black cock was in her moments before was driving me wild. While I licked her wet pussy and swollen clit he got behind her and started to slide that big cock into her wetness. Just the sight of that hard rod entering her almost made me cum. As he fucked her I couldn't help but lick his cock and balls as he thrust in and out of her. At one point his big dick slipped out of that drenched cunt and flopped on my face. I eagerly took it in my mouth. I think he slid it out on purpose to see what I would do. It was another way of showing his dominance, and letting me know I was just a pretty sissy. At least that's what I wanted to believe, because at that moment I knew that's what I was, a sissy bitch with a tiny white dick sucking on a big black cock. It was the most exciting sexual experience I had ever had. And I orgasmed at that moment. It was so intense. He pulled that hard dick out of my mouth and slid it back into my wife's pussy leaving me forever more craving black cock. As he continued to thrust into her, she was screaming, even with my spent little cock still in her mouth. When he came inside her I continued to lick her pussy as his cum tricked out. I was so excited at how wonderful it tasted and how hot it was to eat another man's cum from my wife. As his cock got softer and slipped from her well fucked pussy, he let it lay on my face. I didn't want him to move as I continued licking his seed from my wife and his shaft.

That night when we were alone I didn't attempt to fuck Tara, I felt I'd be a bit inadequate with my 5 inches after Michael's big manhood had been in her. But this didn't bother me, I was very happy licking her pussy which still tasted of him.

As I licked her pussy she said, "That was so hot today, having Michael fuck me with that big black cock in front of you. And when you were licking my pussy and he was fucking me at the same time, I thought I was in heaven. I can't even tell you how many orgasms I had. And I know how turned on you were. You came so hard in my mouth. This is going to be the start of something fantastic. He has such a sexy muscular body and what a great cock, don't you agree?"

I simply replied, "For sure."

Two weeks later Michael came over to our place and as he sat on our couch I watched my wife kneel down in front of him. He smiled at me as he took off his shirt to reveal his powerful muscular chest and abs and then Tara unzipped his pants and pulled out his quickly growing erection. I couldn't take my eyes off it. The size and the darkness of it was so erotic. My cock seemed so tiny in comparison.

I watched as my wife stroked it and as she opened her mouth to suck on it, I instinctively opened mine.

Michael said " it looks like your pretty boy is hungry for a big black cock in his mouth, too."

My wife replied, "oh really. Come here honey and let me watch you be a cock sucker for our man."

I gladly walked over and got on my knees next to Tara, and started licking and kissing his cock and balls. Then I took it between my lips and starting sucking.

My wife just said, "that's it baby get that big dick ready to fuck me. It's so cool being married to a pretty boy cocksucker."

He put his hand on the back of my head and had me bobbing up on down on that hard post. When his shaft was ready he pulled out of my mouth, got off the couch, laid Tara down on her back and fucked her on the coffee table as I jerked off. When he was finished he pulled up his pants and left. Tara laid there with his cum dripping from her. I sat there with my own pre-cum running down my fingers.

"Come on baby clean up this mess," Tara said, "You know you want to".

Again I found myself lapping up Michael's cum from my wife's pussy. I was stroking myself as I did. When I was about to cum I stood up and came on her pussy and tummy.

She smiled and said, "Pretty boy, you better clean that up too."

I gladly got back down on my knees and did as she asked.

A week or so later we went out to dinner with Michael and his wife, who still had no idea that he was having sex with others. He was driving, she was sitting next to him and as I sat in the back seat with Tara I couldn't help but think how he was this lucky guy, driving his car with 3 of his cocksuckers in it. I am sure the moment didn't escape him. And I wondered how many other cocksuckers he had on the side. I wasn't jealous that he was such a lucky stud. I was just happy to be one of his cock sucking bitches. He was so strong and masculine. I couldn't believe how excited I'd get when I was around him. How feminine I felt when I was in his masculine presence. I always made sure my legs and body were smooth and that I was wearing sexy panties when I knew he would be around.

After we got to the restaurant and placed our orders I went to the men's room. A minute or so later Michael came in and he locked the door.

"Aren't you in the wrong bathroom," he said as he pulled down his zipper and pulled out his already hardening big black cock, "This is the men's room."

He smile and took a step closer as his BBC got bigger and said "Well girl, what are you waiting for?"

I couldn't take my eyes off it, my heart was pounding. In an instant I was on my knees sucking him.

He looked down and said, "Since we both know you are my sissy bitch the next time we get together I want you dressed like a sissy bitch, panties, bra, lipstick and heels. You hear me sissy?"

I looked up at him with his big dick already sliding between my lips and nodded my submissive, "yes."

Dinner hadn't even been served yet and I was already blowing this sexy bull. He came quickly but made sure I swallowed every drop. He put that beautiful dick back in his pants and said, "That's your appetizer."

My little cock was hard as rock in my pants and I needed to wait a couple minutes before I went back to the table. When I arrived he was already seated with Tara while his wife had gone to the ladies' room. She was laughing when she saw me and I knew that he had told her about our tryst in the men's room.

At first I was embarrassed but she leaned into me, kissed me and said, "Oh, I can taste cum on your lips! Have you been sucking dick without me? Such a naughty pretty boy. Ha, ha, Don't worry honey, I'm teasing you. I don't mind that you sucked him off without me. I've sucked him off plenty of times when you weren't around, and now I don't have to hide it from you. Oh and I promised our man here that I would help you pick out some sexy lingerie, for the next time he comes to see his two girls, as he calls us. I'm losing my pretty boy but I suppose I am gaining a sissy girl."

My little penis was again hard in my pants and I leaned in, kissed my wife and thanked her.

moonsissy
moonsissy
251 Followers
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cdCindy1cdCindy15 months ago

Read this story again. I love it every time because i'm also a sissy faggot cocksucking bottom bitch -- AND I LOVE IT !!!!!

MatureandkinkyMatureandkinkyabout 1 year ago

Love it, even if I felt envious!

Sissyjackie2008Sissyjackie2008over 1 year ago

As a bi crossdressing cuckold got my wife, this story hits all my buttons. It is so relatable to me. Can’t wait for the rest.

Lily PegLily Pegover 1 year ago

Hot hot hot! Very hot

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