Confessions tagged with 'sissy'.

#3849

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I had been married 2 months and our first time having sex was our honeymoon. I was giving her all I had and all I heard from her was, "I don't think you are in me". I assured her I was in her. When I finished and pulled out she saw it and busted out laughing. When she was calm enough to tell me what was so funny she said, "I see why I couldn't feel it, that thing is tiny as a babies. Then two months later she came home from work and I was finishing my house cleaning and handed me a bag and said, "Ok, this is the beginning of your new wardrobe and life. She worked at a law office as the senior paralegal and in school getting her law degree, and I was the housewife basically. The bag had 2 dresses and package of panties and all the things I needed then. She handed me a Playgirl magazine, this was the 1990s, and told me that this is my new dirty magazine and then burnt all the men's dirty mags. She said, "Now you will be a good girl and shower and shave like a girl and get dressed with nylons and high heels too. I did and then she said we were going out. We went to the local mall where people I knew could be. We went to the ladies department and I tried on many things and had to walk out to show her how it looked. At one point the sales lady said he sure makes a pretty woman. I didn't say anything. Then I got a name when my wife said, "Lisa she just said youre a pretty woman don't you think you should say something"? I said, "I'm sorry, and thank you for the compliment". Then we went to feminine hygiene and she said to find the biggest tampons for myself and the big box. I was at the register alone when my best friend got in line behind me and said I never knew you dressed up and so pretty too. Then my wife walked up and said she is not dressing up she has asked to be totally feminized and to find a man to love this girl, her penis is so small I couldn't tell she was in me so she is now the woman. Then she told my best friend that she needed some male company because it has been over 3 years since she was with a man. He said yes. When he got there he told me that he wanted to do me also. My wife said, "She needs cock bad do anything you want with her and don't let her be masculine". My throat was fucked by 8 1/2 inches of my best friend and when I got him hard again I was fucked and my wife said good I video recorded it and she was into it. I wasn't until halfway through the blowjob when I really began to enjoy it. I was begging him to thrust in me harder and cum in me. After it was over my wife said I was so good that tomorrow I would have 2 men all over me. I said is it ok if I look at my Playgirl. She said of course you can Lisa. I saw a big cock and said that looks so tasty. I said I wanted a cum facial, and she said that I would have to go to the store with cum on my face. I am so lucky to be only 5'4" and 108 lbs and in ladies high heels I am 6 1/2. I don't have muscle arms like a man and I love cock. The next day I was so into the guy I sucked and I told him I really liked him maybe loved him. I now have "C" cup breasts and I had myself castrated in 1992 . I didn't know that one cock would make me crave cock. I am so into big cock and I want to be fucked over and over. I am happy that my wife was so smart. She said that I would buy hers and my tampons. Come one boys tell me how you would fuck me.

#3776

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I’m 15 and it’s been a while since I serviced someone older. I miss sucking a cock and swallowing all of his cum. I miss my ass being stretched by adult cock. I’ve never been with a woman but it seems like so much fun to pleasure one by sucking her tits and pussy. Maybe I could even fuck her. Please I will be such a good slut for you

#3209

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I want to be dressed in pink silk nylon gown.pink nylon panties .with a pink tribute vibrator in my ass.given poppers and meth for 2 hours .have men let me suck them and cum all over me every 30 min hit meth. And the poppers till i have the Cum of 100 men on me. the money i make from the vibrator in my ass will pay the meth and poppers .

#2894

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When I was around 6yr old my older brother was 15yr old and I always wanted to follow him, but he'd tell me no because he was going to his forte. One day he agreed I can go, but I had to become a member of the club, when he got there it was an old shack back behind our house in the woods, and we went in where another older boy opened the door. As my eyes adjusted to the light, I seen there was three other boys in there around my brother's age, and one of them asked if I want to become a member. Well I did more then anything, so I said yes, and the boy pulled out his dick saying "Okay you have to suck all of our dicks until we cum, and then you have to drink our cum. I didn't know what cum was and I didn't want to sound stupid, I looked over at my brother, and he said "Go ahead and do it or you can't become a member".

I bent over taking this boy's dick in my hand he said "No you have to take your cloths off first", i again looked at my brother, and he said "Come on do it", so I stripped down. I walked over to the boy, which by this time they're all hard, I took the boy's cock in my hand. and started sucking on his dick. I remember him telling me to slide my mouth up and down his dick, so I did. Then the other boys gathered around, one of them started rubbing my butt, which felt good, and then he spread my butt cheeks open saying "Look at that little bootie hole"! I then felt him plunge his finger into my butt hole, pulling it out, spitting on my butt, and plunged his finger back into me. By this time I felt the boy's dick I was sucking squirt something into my mouth as he's moaning and gowning, and it didn't taste bad, so I swallowed it. I then heard a boy say it's my turn now and he shoved his dick in my face, so I started sucking him now as the other boy was still shoving his fingers in my butt.

It was not long before I heard the boy I was sucking say "Oh fuck he can suck cock", then started grunting, and again I felt the boy squirt something in my mouth. Then my brother stepped in front of me, I took his dick in my mouth and started sucking his dick. The boy that was fingering my butt says "I can't wait, I want his little butt, and as I have my brother's dick in my mouth, I feel something big being pushed into my butt hole. It hurt but I didn't want to say anything because I wanted to show them I was tough, as I looked back for a second I realized the boy was pushing his dick in my butt, and I started sucking my brother's dick again. The boy fucking my butt hole announces in a rather loud voice "Oh fuck his ass is tight, I'm going to cum", I feel my butt hole become wet and sloppy as 'the boy is still fucking my butt, I hear my brother moan, and then he started pumping his cum in my mouth.

The three boys and my brother spent the rest of the afternoon using my mouth or butt hole. Needless to say they let me became a member of their club, that night my brother told me to come sleep in his bed, I walked over to his bed, and I knew what he wanted, so I got naked then climbed into bed with him. He was already rock hard, so he told me to lay on my belly, and I felt him spit on my butt, and then I felt his dick enter my butt hole. He started fucking me slow at first, then he started really driving his dick into my butt hole hard, again it hurt a little, and I remember him lean down whispering in my ear "Damn your little butt feels so good on my cock", he then grunted, and then I felt my butt hole get sloppy as he's still driving his dick into me.

The next day we went to the club house, when I want in they were all naked, and there was two new boys, so there was five boys and then my brother. They all took turns fucking my butt that day and I remember feeling their cum leaking out of my butt home as I was walking home with my brother that night. I became their little fuck toy and a lot of times they had a new boy with them. After a couple summers of me letting all the boys in this club fuck me, I was around 8yr old when I was at the local park waiting on my brother, and there was a guy in a car that kept flashing his dick. So I kind of walked over closer to get a better view, he opened his car door so I walked even closer, he motioned me over, and I walked right up to him setting in his car stroking his dick. So I simple bent over and stated sucking his cock, he didn't last long at all, and then he started filling my mouth with cum. The guy left in a hurry, but I remember that really excited me sucking some strange man's cock, and drinking his cum.

So I was around 8yr old when I started hanging around that park after school, then one day there was a guy kept going into the restroom at the park, so I went into the restroom, and he's standing there jacking his cock, so I walked up to him taking his cock in my hand, and then sucked him off. Just as the guy was pumping cum in my mouth, the guy I sucked off the day before walked in, and scared the fuck out of the guy I was sucking off. The other guy took me into a stall, he sat on the toilet, and I started to suck him. I looked up asking "You want to put it in my butt", of course he says yes, and I climb up on him taking his cock, and lining it up to my hole, and then I sat all the way down on his dick. I remember him moaning when I sat down, he then took me by my hips, and started fucking my butt hole. I had a few regulars at that park that would wait for me to show, I'd let them fuck me, and cum in my ass.

I was an 8yr old little cum slut and I loved letting men use my butt hole to get off.

#2519

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After my divorce I met a woman with a stern demeaner. I was attracted to her and asked her out. We had dinner and she took me to a party. She teased me, got me very horny but no sex.

In an email she told me she liked men to wear girls panties and would I wear them for her. I agreed and we had a second date. She had a pair of bikini lace lined pink panties for me to put on. I started to go to the bathroom to put them on but she said, no, put them on in front of me. I undid my belt dropped my pants and under pants and put on the panties. She grabbed my genitals squeezed and said that's nice. I was roaring horny and hard as a rock. My cock was too big for the panties but she demanded that it all be covered. Somehow I squeezed it all in. The next night we went to a party. After a couple drinks she came up behind me, undid my belt and pulled my pants down, revealing my pink panties for all to see.

Then she pulled my hands behind my back and I felt hand cuffs put on me. My cock was rock hard and the head had pushed out of the top of the panties.

A woman came up to me and kneed me in the balls very hard. I lost my breath and fell to the floor. There she started kicking me in the balls as I tried to escape. Then a guy got on top of me, with my hands still cuffed behind my back and he forced his cock into my mouth.

I was totally straight until then. I did not have to suck long before he shot his load down my throat. My new GF said I was a natural fag. They pushed me on my stomoch, pulled my butt up and another woman with a strap on fucked my ass. I shot my load all over the floor. They made me lick it all up.

then they put my cock and balls in a chastity cage and padlocked it. They said I would be a good bitch and they would have fun with me.

I went to work the next day in my pink panties locked in chastity. Everytime I moved or walked my cock got hard and it hurt.

I got a phone call from a woman I did not know. She said I was to meet her in the parking lot at 5 pm. I went to get in my car and from behind I was blindfolded, hands cuffed behind my back and I was put in the trunk of a car. I was taken to a wooded area, stripped, ass and mouth fucked by at least 3 people. One was definitely a man because he fucked me with his cock. They uncuffed me, left me there nude except for my cage and I had no idea where I was. I found my panties but no other clothes. It took me almost 5 hours to find my way home. I had no keys and was hiding behind bushes. But, I had to go to my neighbors to help me climb in a window. He was nice enough to help me but fucked my ass after. Remember I was still cuffed and in chastity.

It was the next day when my GF came and unlocked the cuffs but not the cage.

I am now a total sex slave, bitch sissy fag. I love it now.

#2489

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I am an older white guy. Divorced twice and had at least 30 other women. Now I want to have sex with a man. I want to see if maybe I would prefer guys to women now.

#1666

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I grew up with two older twin sisters. They are three years older than me and both are bigger than me. Growing up they called me "Pussy boy," "Faggot," and things like that. They were slowly turning me into a girl. I was short, thin and had a tiny cock. From Junior High on they would dress me up and put make up on me, taking pictures of their pretty "Little faggy sister."

When I was a Sophomore in High School they started "helping" me shave my legs and armpits just like they did. About that time they also started telling me now great it was to suck a man's big cock, and since every cock was bigger than mine, they were all big cocks they told me. They made me watch videos of each of them sucking and fucking their boyfriends. After a while it kinda turned me on watching them. I assumed it was because of them being naked, but at 18 I found out differently.

When they turned 21 they started going to bars. Over Christmas vacation in my Senior year they started taking me, and Denise finally introduced me to her boyfriend. They took me to the drive-in one Friday night, and during the first movie while they were in the back seat I looked back and she had his pants undone and was sucking his cock. He caught me looking and pulled her head up. He said, "I want little sis to suck my cock now." "Great idea," she said. "Get back here, cock lover. Don't worry, hon, she sucks cock better than me." I was flattered but scared. I figured this was my chance to learn so I crawled in the back on one side of him with her on the other.

No sooner was I seated and he put his hand on the back of my head and pushed me down to his lap. I put his cock in my mouth and tried to do like they had done so many times. The farther he pushed my head down the more I liked it. "Oh, honey, you were right. She's a natural." Then he grabbed my hair and held my head down, "Oh, baby, I'm gonna blow." He started to cum, right in my mouth. I didn't expect that. By the third spurt I was wanting more. Even when he stopped cumming I kept my mouth on his cock and didn't stop until he came a second time nearly 30 minutes later.

She didn't tell him I was a male, but he found out the next Friday night when we were at his apartment and she decided it was time for me to get fucked. It was, and he did. And he did until he moved two years later.