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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 confess that my fetish is dressing as a sissy, I have so many outfits, wigs, breast forms, etc. I love to fish and know many places where I can fish without too many people around, but am always cautious. I love fishing in only panties and bra, so as I can get my tan lines set. Last year caught a few nice fish and poised for selfies dressed and holding fish and even put them online in a few places.
One day as I was waiting for it to get light, staying at motel along the highway, where the speed limit is reduced to 35 mph, was dressed slutty and was un-tarping boat, many truckers drove by and this sissy was in plain view for them to see. It was very exciting. I also dressed wearing a long fishnet pink dress, pink bra and pink panties with wig on, filled the truck up full of gas and drove home and on the way, stopped for an espresso, another thrill.
This sissy has been online searching for new outfits for this years journey. So looking forward to playing dressup in cabin and being displayed outside for all the truckers and fishing, looking like a sissy. Deep down, have always wished I were a female
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.
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.
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.
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 wore a sissy baby dress and red very shiny and bright panties when I answered the door when my wife's boyfriend came to pick her up for their date. My wife didn't know I was going to do that. When she stood at the top of the stairs she was just wide eyed staring at me. Her boyfriend kept his cool and was talking to me on our couch. My wife came down the stairs and started appoligizing to her boyfriend about me but he stopped her and said he understands why she and I both needed a real man in this household. I said if he would like to move in our home he would be considered the only man in the house. He said he would like to talk with my wife about it and let us know when he made a decision. Needless to say he moved in about two days later. I and my wife have worn nothing but dresses ever since. He moved in to their bedroom . I have moved in one of the other bedroom s on the first floor. My wife tried to embarrass me once after that by inviting several of my friends over for a party one night what she learned was all my friends thought I was a woman they always saw me in nothing but a dress. None of them had any idea that I was married. And certainly not to another woman she was glad she didn't tell them she was my wife.
My wife turned me into a sissy, I'm 23 been on female hormones for about a year now I have nice set of 36 d breast and curvy body just like a girl. She is having few black guys over tonight to train me. I can't wait
I'm secretly a sissy slut to all my friends my girlfriend gets me sissified and takes me to her friends house and let's all her big dicked men fuck my sissy hole relentlessly while she makes fun of my sissy clitty(that's what she calls my little dick )
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 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 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 am a sissy male and enjoy it immensely. I dream of finding a tall dark and handsome Man and he loves me for the sissy I am. He asks me to marry him and I say YES. I am his wife and lay curled up next to my Man every night playing with his Big Man Cock.. I m his wife and take care of him doing what I wife needs to do for her man. He treats me like the sissy cock slut I am and keeps me dressed like a whore. This is the life I want to live.
Sissy Boy C.
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.
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 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'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.
When I was about 13 I sneaked into my younger sister's room and looked through her wardrobe. I found this blouse that I didn't remember ever seeing her wear, it was a pink satin slip on with a round peter pan collar placket and short frilly sleeves. It was so ultra girly that she'd probably never be seen dead in it. I'm not sure why but I sort of dared myself to put it on even though it was far too small. I had to put my arms really close together inside it and put my hands into the arm holes. Gradually I pulled it down until finally I had it on. Then I did up the buttons one by one, right up to the top. I couldn't believe how sissy I looked in the mirror, or how hard my cock was getting. Looking through her drawer, I found a pair of short pink nylon pyjama panties with flowers on them. Trembling, I put them on over my hard cock. The feel of them hugging my ass was amazing. Finally I put a pink skirt on to complete the outfit. Seeing myself dressed as a little girl in the mirror was too much, I masturbated like crazy and came half way across the room.
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
When I was younger (I won't say how old) I used to talk with older gay guys online. I eventually started taking pics and even taking requests for what they wanted to see. A few wanted to see me in panties so I would swipe from my sister's dresser and put them on. I guess they looked good because more and more guys wanted to see it. Eventually it led me to buying a wig and putting on my sisters clothes & makeup for them. It then went from pics to vids of me stripping and masturbating for them. Thinking back now about it turns me on so much. I often times wish I was a girl.
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