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As a kid, I loved to call a taxi or order a pizza and tell them the address of one of my neighbours or of someone I don't like.
I was house watching my old aunts house for two weeks while she was on holiday. I had her whole house to myself and all her clothes to dress up in. I love getting strapped up in her corselets and barely black tights and put on one of her wigs. One morning I did this when her window cleaner came. I put on a show for the old window cleaner pretending not to see him looking in as I was pulling up my tights. He quickly moved away from the window and the next thing was I heard him coming in the room. He had his cock out and ordered me to suck it. When he realised I was a bloke he said he was going to take it out on my backside and made me bend over pulled down my tights and unhooked the corselet gusset. The thing is that when he shot his load in my bum it made me cum. We both ended up in a 69 shooting in each others mouth.
#crossdress #cum #mouth
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'm a crossdresser, and have been for over 20 years. A few weeks ago, I met another crossdresser and we sucked each other off, the first time I ever sucked a dick. Since then, I've sucked two more, and I want more. I love it.
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'm a 50 year old divorced crossdresser almost my whole life. I love being feminine and am rather pretty. I love being a black c*** slut and have been since I was a teenager. My wife divorced me when she caught me in bed with two black men while dressed in her wedding gown and having sex. It's Sunday afternoon and 11 black men had sex with me this weekend and I love it the sex, shame and humiliation makes me the slut I am.
I've always had a panty fetish but last year I developed a new one. My sister was getting married and I found her wedding dress and lingerie at our parent's house. A month later I was at my sister's house babysitting and after the kids were put to bed I started searching and found her wedding dress hanging in the closet. I remembered it being so soft and decided.
Well a lot of my ‘sins’ began back when I was 14, I am 16 now. Then I would post a lot of pictures of me online on reddit claiming to be 18. I loved the attention from the guys and girls I got because I didn’t feel comfortable with myself and they actually liked me for me. They loved my body and made me confident in myself. I loved wearing girls clothing and began stealing cloths from my sister and aunt, trying on anything that I liked. I would show pictures of me masturbating, or ones of me twerking, trying new things, everything, I loved being a little slut like that. But eventually I calmed down on the whole posting thing as life took its toll on me and I couldn’t keep up with it. But that didn’t me from getting kinkier. I went deeper and deeper into the web, finding all the craziest of shit.
But one thing I did that I really loved was when my aunt and uncle were out of town, they had my house and dog sitting so I had free rain of their house. I went into their room and began looking around for toys, but wasn’t able to find anything. I did find some dirty underwear I played with and eventually came in. But also I went through their closet and tried on a bunch of her cloths as I loved them. At one point I was dressed in a pair of sexy thong panties, a lacy matching bra, silk teddy and silk robe. I’m not crazy chubby, but my chest area kind of looks like I have boobs even though I’m a boy so they fit her cloths perfectly. I took one of their dog collars and put it around my throat and painted my lips and put lipstick on. I jerked off everywhere and came in a bottle of her lotion. I then also used random things I found around the house as dildos as I’m pretty brave. But also, I wanted to try something out, so I took one of the male dogs to the bathroom and I began jerking him off. I then also began to suck him off, but when it tried to get him to fuck me he was too small and didn’t seem interested. That’s definitely a dream of mine, to be fucked by a big hung dog…
But that was my confession, hope I’m not too much of a weirdo for here…thanks for reading if you’ve gotten this far
#femboy #confession #young #teen #beast #posting #crossdressing #incest #sneaky
I love shopping for 2nd hand dresses especially vintage modest ones. Crossdressing in a dress with very naughty underwear or none at all is amazing. I love thinking about the women who owned the dress first and wonder if they wore the dress with out panties too and if they enjoyed being sexy in it too. I love contacting the and telling them how much I love the dress. It’s fun to make a story of me wearing their dress to a Burlesque show and stripping full nude on state. Many women have loved when they hear of me stripping in their old dress.
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.
I'm a 16 year old male (for real; I'm not trying to bait anyone, or anything). I've always looked somewhat feminine, taking a lot more after my mom than my dad. When I was younger, I was even occasionally mistaken for a girl. That said, I'm a junior at a fairly progressive high school, and in my Drama class before Winter Break, I played the role of Juliet in Shakespeare's Romeo and Juliet. My Drama teacher is sort of weird. He's also VERY particular about the craft, so I was fully costumed and wore makeup the day of. To top it all off: it was a kiss scene! Now for the confession: my partner, playing Romeo, wanted to do the "thumb trick", where I would end up kissing his thumbs instead of his lips. I said okay, but when the kiss happened at the climax of the scene...I moved his thumbs away! He was really embarrassed, and so was I, but in the moment I felt really compelled to do it. I tried to apologize afterwards, but he just dismissed it...I'm not sure what to do now...
#juliet #shakespeare #drama #highschool #romance #crossdressing #embarrassed #dress #makeup
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'm a straight guy who sometimes likes girly stuff: I'm completely shaved on all my body, my toenails are painted and I like certain articles of women's clothes. I usually mix and match male/female clothing. For example, right now I'm wearing jeans, a hoodie, panty hose and panties.
I also love having sex with prostitutes, especially when I wear a skirt or a dress to the whore house. For some reason or another, that's my sex fetish. I live in a country where there is no stigma concerning prostitution, so I'm at the whorehouse twice a week on average.
I know that no woman in her right mind would ever understand this fetish, so I've given up the idea of ever being in a relationship with any woman who isn't a sex worker.
I'm a married man. Love my wife. Also have a guy who is bisexual just like me. He loves me and i love him too. We have crazy sex when ever we meet. He considers me top but I'm more of bottom slave. I like to be roughed up. He makes me feel good. Lovely person.
#gay #married #bottom #slave #crossdress
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".
I am a long time crossdresser who now fantasizes about having sex with an older man. I would love to dress up in a slutty skirt and top along with a sexy bra, panties, stockings and high heels. I would be completely made up as a woman and try to be as sexy as I could. I would then like to meet an older married man in his sixties who would take me home to his place. Perhaps his wife was on a trip and he had the place to himself. We could have a drink and then and then engage in some long lasting foreplay so he would get really turned on. I would let him take me to bed and I would suck his cock for a little while until I got on my back and opened my legs to fuck. It would feel wonderful to feel his cock in me and have the weight of him on me. I would wrap my legs around him and wiggle my ass to the rythym of his cock going in and out. When he came it would be an explosion of hot cum in me and would feel so good. If his wife was going to be gone for a while I would try to stay there and fuck him as much as I could. It would be our little secret and his wife would never know about the hot fucking that took place in her bed.
I am a boy, late teens. I am not too big, not a jock, and girls never notice me. I finally got a girlfriend who is great for me. She is a bit of a fatty, not too big but about 5ft. 8in and weighs about 185. She was quite experienced in sex already, in fact very very experienced but I don't mind. I get to have sex in all ways, places and do everything I wanted and even more. She has red hair, and is 3 years older than me. She is pretty kinky in sex and I do whatever she wants so I can keep having sex. I rather like some of the kinky stuff. She has made me be the submissive one in our relations, she is definitely dominant. She has even taken me to a public beach wearing a girls bikini bottom and a collar with a leash. When we were walking back to the parking lot she moved me behind some trees and bushes and we had great sex then left. She even did it with another girl and let me be in bed with them, then insisted I do it to the girl too. The other girl was really totally lesbian and didn't want a guy at all, but my girlfriend made her do it, and made me do it to her.
About 4 days ago, she took me over her lap while I was naked and started spanking me, she spanked with her hand and then a hair brush for about 20 minutes I was in a lot of pain, my butt was red as a Crayola crayon. She then rubbed some lotion on my butt to soothe it a bit, and started sticking her fingers in my hole. After three fingers were in, she started fucking me with her fingers, I objected and she pushed me down and told me if I ever want to feel her ass, mouth or pussy again I'll just lay there and take it. She fucked me with three fingers for about 10 minutes all the while talking nasty and calling me names, saying I was gay and liked getting it up the butt. Then she stuck in one of her vibrators, and turned it on. Then she called me all kinds of names because my cock got hard. She fucked me with that vibe for about 30 minutes, then let me up, made me clean up "my" vibe, and put it in a special drawer. About two hours later she let me fuck her and I again had to lay across her lap endure an endless spanking, and a 30 minute fuck with the vibe. She then stuck in a plug. I had to go home, and she told me to leave it in until I came back, to take it out only when I had to sit on the toilet. I did it and the next day didn't see her until about 5 or 6 o'clock, by then the vibe was quite loose in my backside. We sat on the couch and were kissing, I was playing with her very big titties and sucking her nipples. As I reached under her skirt I felt something strange. I pulled up her skirt and there was a cock in her pants, she also was wearing a pair of my underpants. She stood up, pulled off her dress and then the bra and had me pull down the male underpants. She had a strapon cock and was wearing it. "Start sucking bitch" she almost snarled, "or get a real spanking not just one of those love paddles I've been giving you".
I was on my knees and started sucking the very large artificial cock. She made me suck for a while, then we went to the bedroom and she had some stockings and lingerie for me to wear. I didn't want to, but she kept reminding me of how much I liked sticking my "little wussy cock" into her pussy, mouth and asshole. As I got on all fours on the bed after dressing for her, she pulled out my plug and stuck the very lubed, very large strapon up my shithole. She didn't give me anytime to get used to it, just started fucking me, very rough, very hard.
This has become our normal sex now, she fucked me dressed up like a girl, and I jack off while she does it. She even had that lesbian girl who she made me fuck, come to watch, and she was wearing her own cock and fucked me too. The lesbian also took me home to clean her house, all the while, even riding in the car I had on the lingerie and just a robe to cover but it didn't cover my stocking'd legs and high heels. While there she spanked me and tied up my cock and balls very painfully because she said I raped her. My girlfriend says next week we're going to the beach with me wearing both halves of the tiny girls bikini.
#bd #nc #crossdress #strapon
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'm a straight guy but I have to confess that since I was 14 I took a interest in sexy lingerie and began secretly dressing in it. My wife thinks she got me into it 9yrs ago so I let her think that. So I have really been wearing women's clothing for nearly 20yrs..I feel comfatable and relax in female clothing.I wear lingerie every day under my work clothes. At home I get around wearing either a nice dress or a nice skirt and blouse
Too often I find myself creating slideshows of women and girls wearing short skirts/dresses and masturbate to them. In real life, I'm just so turned on by short skirts that I often can't help myself whenever I see one. On top of that, if I happen to witness or find an image of a female curtsying in a skirt/dress or a panty upskirt shot, I get even more horny. And the weirdest part is that, for some silly reason, I enjoy jerking off to these pictures most when I replace the female's heads with an elephant's head. As someone who believes in Jesus Christ, I am easily able to recognize this as a habitual sin that I need to break because it often damages the way I look at the opposite sex when I see them wearing such attire.
#fetish #weirdness #pictures #masturbation #girls #skirt #dress #panties #elephant #habit #sin
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