Bi-Sexual Male / 36
Too Much $ To Pass Up
I was 18, fucking a 54 year old grandma who was sexy as hell. We went nude in her apartment all the time, even in front of her friends, many of whom would strip also. I fucked several of them also. One time I went there and she was getting fucked by a man I'd seen a few times. He had the thickest cock I'd ever seen, about 7inches long but very very thick. He blasted in her just as I was coming in then he pulled out and what looked like a load from three or four guys dropped out of her gaping pussy hole. I knew about them, she would have me go after him many times getting very sloppy seconds. This time he watched as I licked her of the goo he deposited and then deposited my "normal" load in her used, hairy pussy. All the time he was rubbing my butt. I didn't say anything but he stuck a finger in my hole a couple of times while I was fucking her. Pulling out of her sent his finger in to me.
A week later she explained that though he was married his wife wouldn't take his favorite sex which was anal, and wouldn't let him cum her mouth. In fact he was bi if not actually gay he preferred younger guys. She told me that he would give me $1000 if I'd let him have my cherry butt. She insisted it wouldn't change anything, that I'd still be straight, still sexy, in fact even sexier to her. I was a student and needed money, so I did it. She took a week finger fucking me with up to 4 fingers (still not up to his girth) and introduced me to fucking her while wearing some of her lingerie. I had long hair and finally the day came. She styled my hair, put on lipstick and make up, a bustier that pushed up my pecs like tiny titties, and put on a matching garter belt and stockings with panties over that. She explained that the panties could come off and I'd still have on the rest of the lingerie. I remember my mom undressing after work, she always did it in front of me, and she'd pull off her panties first. I guess it made it easier for my dad to get at her when he wanted some.
Here I am, all in white lingerie and my friend leaves when my new "lover" arrived. He placed 10 each $100 bills on the dresser. I sucked him hard, my friend had already put vaseline in my hole so it would stay lubed for his entrance. he wasn't going to wear a rubber, he wanted to "have me" completely he said. I didn't realize he took me and drinks to the balcony and there I was being looked at by the neighbors. I sucked him some more, then went to the bedroom. He was fairly gentle, even though she'd opened me up some it was still a bit painful. He waited while I got used to the intrusion into my formerly virgin hole. Then he started fucking. I was being kissed, fucked, my tits tweeked, whispered to and everything I did with women, he was doing to me. Then he changed position, putting me on my back and entering me missionary pulling my legs up to wrap around him. Soon I felt jet after jet of his sperm entering my body. I actually liked that part, it felt good knowing that I had given him that pleasure, that he was using me as a place to put his cock and cum. After a while he pulled out but my hole was leaking something awful and he wouldn't let me get up. Instead he sucked me and when I was about to cum he put me in his ass while he was riding me on top. I shot and he was hard again. I got my second fuck soon after.
I got my money, he left and my older lady came back and had me stay like a girl while we had sex that night and the next morning. I have to say that even now, I really only have body hair on my arms (and very light there) and on my pubes. About a month later, he had paid me two more time for sex, $300 each time then one time another $1000 for a full weekend spent at his mansion with him while his wife was out of town. During that time he let one of his friends fuck me also. He made me an offer, if I went out of town to a vacation island with him and acted as a gay, girly, femme he would pay me $3000 for the week. I went.
On the island, I was acting obviously feminine gay, he would embarrass me by kissing me in public, grabbing me on the beach and then had me wear a girls bikini bottom with a wrap around skirt on the beach. One night there was a private party and couples were there, everyone nude, and fucking. Mostly straight couples swapping. He fucked me there in front of everyone, had me suck a few guys and at the end of the night I went home with a man whose wife went with mr. thickcock. I got fucked 3 times and sucked him to completion once. He was much thinner but had a nice 9" and by now I was really enjoying getting fucked. Finally the week was over, we returned home. My older lady had moved on and didn't see me anymore so I used all I learned and got some college age girls. I still went with Mr. Thickcock a few times a month for money. I got one of them pregnant and we got married and that is up to today. 3 kids and a little plumper, tiny titted wife. I haven't had any men since I stopped in college after I got married. I did let thickcock and 3 of his friends have me all dressed and made up two nights before my wedding, but that was the last time. I think about it many times, I love my wife and love my life but still think about my time as his little fuckbunny all dressed as a girl for him. My wife, a ministers daughter would freak out if she knew, much less realized I did it for money, a paid crossdressing prostitute.
A week later she explained that though he was married his wife wouldn't take his favorite sex which was anal, and wouldn't let him cum her mouth. In fact he was bi if not actually gay he preferred younger guys. She told me that he would give me $1000 if I'd let him have my cherry butt. She insisted it wouldn't change anything, that I'd still be straight, still sexy, in fact even sexier to her. I was a student and needed money, so I did it. She took a week finger fucking me with up to 4 fingers (still not up to his girth) and introduced me to fucking her while wearing some of her lingerie. I had long hair and finally the day came. She styled my hair, put on lipstick and make up, a bustier that pushed up my pecs like tiny titties, and put on a matching garter belt and stockings with panties over that. She explained that the panties could come off and I'd still have on the rest of the lingerie. I remember my mom undressing after work, she always did it in front of me, and she'd pull off her panties first. I guess it made it easier for my dad to get at her when he wanted some.
Here I am, all in white lingerie and my friend leaves when my new "lover" arrived. He placed 10 each $100 bills on the dresser. I sucked him hard, my friend had already put vaseline in my hole so it would stay lubed for his entrance. he wasn't going to wear a rubber, he wanted to "have me" completely he said. I didn't realize he took me and drinks to the balcony and there I was being looked at by the neighbors. I sucked him some more, then went to the bedroom. He was fairly gentle, even though she'd opened me up some it was still a bit painful. He waited while I got used to the intrusion into my formerly virgin hole. Then he started fucking. I was being kissed, fucked, my tits tweeked, whispered to and everything I did with women, he was doing to me. Then he changed position, putting me on my back and entering me missionary pulling my legs up to wrap around him. Soon I felt jet after jet of his sperm entering my body. I actually liked that part, it felt good knowing that I had given him that pleasure, that he was using me as a place to put his cock and cum. After a while he pulled out but my hole was leaking something awful and he wouldn't let me get up. Instead he sucked me and when I was about to cum he put me in his ass while he was riding me on top. I shot and he was hard again. I got my second fuck soon after.
I got my money, he left and my older lady came back and had me stay like a girl while we had sex that night and the next morning. I have to say that even now, I really only have body hair on my arms (and very light there) and on my pubes. About a month later, he had paid me two more time for sex, $300 each time then one time another $1000 for a full weekend spent at his mansion with him while his wife was out of town. During that time he let one of his friends fuck me also. He made me an offer, if I went out of town to a vacation island with him and acted as a gay, girly, femme he would pay me $3000 for the week. I went.
On the island, I was acting obviously feminine gay, he would embarrass me by kissing me in public, grabbing me on the beach and then had me wear a girls bikini bottom with a wrap around skirt on the beach. One night there was a private party and couples were there, everyone nude, and fucking. Mostly straight couples swapping. He fucked me there in front of everyone, had me suck a few guys and at the end of the night I went home with a man whose wife went with mr. thickcock. I got fucked 3 times and sucked him to completion once. He was much thinner but had a nice 9" and by now I was really enjoying getting fucked. Finally the week was over, we returned home. My older lady had moved on and didn't see me anymore so I used all I learned and got some college age girls. I still went with Mr. Thickcock a few times a month for money. I got one of them pregnant and we got married and that is up to today. 3 kids and a little plumper, tiny titted wife. I haven't had any men since I stopped in college after I got married. I did let thickcock and 3 of his friends have me all dressed and made up two nights before my wedding, but that was the last time. I think about it many times, I love my wife and love my life but still think about my time as his little fuckbunny all dressed as a girl for him. My wife, a ministers daughter would freak out if she knew, much less realized I did it for money, a paid crossdressing prostitute.
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