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I was a long time cross dresser. I had girl friends cuckold me and dress me as a slut. I enjoyed being a girl and became sexually excited putting on female clothing. When I got married I never told my wife but she found my stash of female clothing. She thought I was steeling items of clothing from women I was having sex with.
I had to confess I was a cross dresser which she did not believe. I has to dress to prove it to her. She was disturbed by all this at first but after several months later she told me to dress like a girl when at home. This was not a choice it was a demand. I dressed with the items I had which made me look like a whore/prostitute. When she told me she was going to take me down town to get some new outfits dressed like a whore I broke down and cried bagging her to not make me go. I won and did not have to go to town dressed like I was.
. She returned with plastic pants and diapers which I now wear all the time. She told me that since I was a baby she would have to treat me like one. My pacifiers are all little short fat cocks that I suck on. I am only allowed to dress as an adult baby girl now at all times. When she goes to town her sister comes over and watches me. When my wife leaves her sister spanker me and makes me nurse on her tits. I am referred to as "sissy baby" or "babykins".
So I'm straight but I enjoy anal play...so one day I found an object (dildo like) and whilst showering fucked my ass.
It was the best orgasm I ever had, when it goes to the second sphincter the feeling is amazing...
I get high on meth every day and when I get high, I rage with the desire to dress up as a woman (I'm a guy) and have sex with straight men who love to abuse sissies. I like being bullied, mistreated, and fucked, anything the guy wants to do I'll let him, the more humiliating the better.
#meth #sissy #cumdump #humiliation
I am obsessed with female clothing. Yes, I am a closet cross dresser. My girlfriend knows nothing about my cross dressing. We had an argument so I left and went into the city which is fours away. Taking one of my slutty cross dressing outfits with me. I had a room and decided to finally go out in public like the sissy slut I have always wanted to be. I went to a bar and was hit on right away. I hooked up with the guy and ended up back at his place. When he took his close off he had the biggest cock I had ever seen. I felt a strong sensation to suck it. He walked over to me and stood with his big cock inches from my face. I picked the semi erect mammoth and with out hesitation started sucking on it as if my life depended upon it.
When he had me straddle his cock so he could take my virginity. He also stroked my little sissy cock at the same time as I humped his cock. When he climaxed so did I in the most mind shattering orgasm I ever have had. I spent the night with him and found it hard to leave the next day. I want to be with him more than my girlfriend so I broke up with her. Looking forward to visiting my new lover and his wonderful cock.
I'm a sissy crossdresser obsessed with wearing women's lingerie and clothing. One time, I was over at my friends house who was having a small party. The girl who was throwing the party was this sexy asian girl with tan skin and beautiful body. While everyone was in the living room, I slipped away down the hallway to her room pretending to go the bathroom. I looked on the floor and found two pairs of used panties and a pair of stockings. I took them into the bathroom and I stripped down. I wore one of them, a blue hipster cotton panties and then I put the stockings over them. Then I started masturbating while I brought the other pair of used panties up to my face and started inhaling the sweet perfume of her pussy. I could hear everyone having still drinking and having fun and nobody knew what I was doing. As I was about to cum, I took the sweet smelling panties I had up to my face and brought it down and came into them. Because I made a mess, I decided to clean it up by licking my cum off her panties. Once I was done, I put my clothes back on again and put everything back where they belonged and went back to the party.
I lost the prettiest girl pretending to be a man younger than her and talking dirty to her through emails and allowing her to turn the real me into her sissy bitch while she flirts with the younger guy which she didnt know was me. When she did find out she dumped me and now has another guy and I am so depressed. I am fucking stupid.
Several months ago I met this guy online. We are both males, both married and in our late 40's. He put feelers out there as a feminine guy, wanted someone to meet while crossdressed and he wanted to be sub to a dom man. I'd not had any strange pussy or ass in over 20 years but was interested. We talked exchanged pictures and he started showing me pictures of his fat wife with huge titties and ass. He would even write my name on her while she was nude and take pictures to send me. I had some old pics of my wife and showed them to him.
We met, and started a fem/masculine get together in which he would dress and I would fuck him and dom him. He wouldn't suck cock though. I finally made him do it and he got mad and I finally got him back to meeting me. He had been fucked by 4 guys before me, I'd parade him around and call him slut, cunt, and other names. I would even open the drapes in the hotel/motel rooms so that people would see this chubby older woman getting banged in her butt through the window. They didn't know I was fucking a guys ass. I always started the session by making him stand up and stick my finger up his butt and make him walk around the suite, opening drapes, windows anything I wanted. He got really sub and I even more dom and I would make him do things to his wife, and take pictures to send me. She dommed him in real life (not sex life) even making him wear cotton panties all the time usually in pink, pastels, and white. So he wouldn't mess them up she made him wear a panty liner or a full pad, just as she did everyday. Sometimes she would make him wear a bra as he had cubby manboobs. Even when they first started fucking she refused to let him stick his cock in her mouth, or in her ass. So I told him he should take his wife and force the bitch to take cum up her ass or mouth. His cock had gotten to where he could barely get it up (usually with injections) so I wrote a story about her being passed out and my fucking her.
He started experimenting with her drinking and slipping in a sleeping pill. She would pass out and he took pics of him dildoing her cunt and sticking his limp cock on her lips. At his suggestion I waited till I got word from him that she was passed out and went to his house. I played with her for a while, ate her pussy out, let him play with my nipples, then I laid on top of her and she automatically spread her legs. Instead of fucking her then I just put my cock into her sopping pussy and got it really wet, then laid him down in his girly clothes next to his wife and fucked him right next to her, in the bed the two of them shared.
After that I made him do some kinky shit, and got my cock hard again, then fucked his wife while he placed my cock at her entrance. I shot a load up her slit all the while sucking, mashing and bruising her tits. I kissed hickies on her neck, and stuck the business end of a wine bottle up her loose cunt after I was done. I made him make me dinner, while dressed in his nightie with stockings and heels. Then told him it was time her virgin asshole got fucked by a real man. We went up to the bedroom and rolled her fat ass over, I made him grease her up with some lube she had and I got on top of her while she was lying face down on the bed. I put my cock into her, and reminded him that this was the position in which I first fucked him. After having shot two loads already, it took me about 45 minutes to cum up her virgin ass. It was certainly tight, I think she was indeed a virgin, but after a 45 minute reaming with a pretty thick 7 inch cock, and her being passed out, it was gaping open bigger than a quarter.
He started to panic wondering how he was going to explain the cum in her cunt and ass. I didn't give a shit and instead jacked him off all over her face and tits. I then told him that her cunt was way too loose for her to only be fucked by his scrawny little cock. She was having an affair. I then told him the best way for him to not be accused of fucking her while she was asleep would be to suck all my cum from her cunt and her ass, and lick his off her face and tits. Then I left. I don't know what he did, but it worked out.
I fucked her about 12 times that way, and finally he told her that he liked being fucked and dressing up and she liked the idea of him being a "woman" too. So he had permission to get dressed and fucked in front of her. I went and fucked him several times, then going off with her to the store, or out to eat (using his credit card each time) then I'd go back and get off again. She made him start sucking my cock to orgasm many times, and eventually she let me fuck her in front of him. She took my cock up her cunt, her mouth, her ass, she even did ass2mouth in front of her husband. I even made him clean my shitty cock with his mouth after it was in his wifes ass.
It's a very rewarding relationship, but we still like to get her drunk and passed out so I can abuse her cunt and ass and bruise those big tits of hers. She just laughs about it now.
A while back, after a breakup, I had been using phone sex services regularly. I usually used Femdom providers.
One woman I called kept telling me I needed to get peach colored lipstick to give blowjobs. She figured had a slutty alter ego.
After using her regularly, I got a notification for registered mail waiting at the post office. I got the parcel and opened it up in the car. It was a pair of silky panties and a note from the provider. I called her later that day and she made me put on the panties and lipstick and promise I’d suck cock.
That started my secret fetish. I dress up in stockings, 4”heels, and lingerie and act as a cock hungry sissy slut.
I am a 24 year old male and I absolutely love to wear women's clothing, lingerie, panties,bras, skirts, etc. I love to wear Hello Kitty, Disney Princess and Victoria's Secret Pink panties. I am completely obsessed with wearing girl's clothing and have done it since I was 16. I love women's clothing and I wish I was born a girl. I am jealous of women for getting to wear those clothes all the time.
I got married and found out I married a sissy male, so I decided he will become my sissy girlfriend. Without his knowledge I have been feeding him female hormones and getting him to dress like me in the bedroom.
I am a married man in my 50s and have been crossdressing since my teens in secret. Last year my wife caught me and ended our sex, exiling me to the guest bedroom. Late at night now I surf porn and craigslist. I recently hooked up with another married guy in his 50s, dressed in a slip and bra and sucked his cock. It was my first time but OMG I loved it. When he held my head and shot his load on my mouth I got so excited I leaked a little cum. He just texted me to come by and wants me to wear his wife's clothes. I am so excited.
i am a closeted faggot and i love looking like a female, with lingerie, skirt, jewelery, makeup, high heels shoes and wig.and i love fat over 50s men to fuck me and take pictures, telling me they will show to my family.
I have cross dressed since the age of ten. I still do in privet, now days. I have always wished I had transitioned to female when I got out of high school or by the age of thirty. Then find a hansom Man with a large Cock to marry me for life. I would be his wife and service his every need. CK
I want a group of girls to force me to wear women's underwear and then laugh at me and taunt me
I wish my best friend impregnates my wife. I would love to raise the child as my own. I just want my child to have better genes than mine. My friend is triple the size of me, you know i dont deserve to have a child.
I female friend of mine always asks me to give her money and I usually do. She wanted twenty bucks the other day and I said she had to show me her tits. She laughed and said I wasn't going to see her tits for twenty bucks. She said to give her the twenty bucks and take all of my clothes off in front of her. That's what I did. Not sure how that got turned around but it was fun.
#sissy #exhibitionist #voyeur #nude
I am a sissy and I have probably sucked 20 miles of cock so far while dressed up like a slut.
I look back at the pictures and feel like such a sissy. My totally hot young neighbor girl stopped by a few times. She got naked in my pool, she let me eat her pussy but wouldn't let me fuck her unless I wore her panties. I gladly did and she has pics of it but I never got to fuck her. This happened more then once too.
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