The true confessions of a sissy transvestite.
Honey, the most humiliating thing I did was wrap my red lips around an 8" dick and suck it hard before I held it while I guided it into my wife. I sat by the bed and watched as he fucked her, listening to her cum over and over. When he finished flooding her with cum, he got up and offered it back to me so I sucked it clean for him.
Some random moments:* Visiting my parents. Going to the mall that's 15 minutes from where I grew up, where I could still run into people from my hometown. But was in such a sissy daze that I couldn't help myself. Bought some floral panties and white women's pants that made the panties completely visible through them.Went traipsing off to the mall. Had three teenage girls spot me and follow me around. I wanted to lose them but at the same time craved the humiliation. Could hear the outright laughter right at me and them telling each other to take pictures with their phones. Went into Sears to look at panties as they followed me right into the lingerie department and one finally said, "Now he's BUYING panties for himself." I went out a side door and masturbated in the parking lot, spooging into my panties in the car.* My wife discovering that I had been emailing with dominant men through craigslist and seeking sissy humiliation. I had not actually met any of them but exchanged pics, me in a bikini, panties, bra, saying terribly nasty things. I convinced her I wasn't gay (she knew I had sissy desires) and that it was just a phase. We're still together. We have not had sex since. I feel terrible for her. Still want to meet a dominant man who will actually force me to be a sissy slut.* Summer after freshman year of college, I bought a bikini bottom, pink, girls, that I wore to a lake about three hours away. Got laughed at by all kinds of hot girls and their hot, manly boyfriends. One day I accidentally left the bikini hanging on a hanger in my closet after I had rinsed it out and was drying it. My mom went to hang up my clothes and discovered it. She didn't ask questions, simply said, "I put your bikini in your drawer." She had to have known it was a women's bikini but she apparently didn't want to picture her son parading around in it, or to imagine that he was a sissy fag.* First time I ever ejaculated was into a pair of my sister's panties. That branded me for life.* Years later. I'm again back home and this time visiting sister and her kids. I had went to Walmart to buy a bikini bottom, hoping to make a trip to a lake. I stuck the bikini in my shorts pocket and just went about my day. Later, I'm standing around with sister, 10-year-old niece, two aunts, two cousins. My niece suddenly goes, "Why do you have a girls bikini in your pocket?" Other people in the group were talking so only a couple others head but she was persistent and I simply said it was a "handkerchief," but did not pull it out. Jesus. What the fuck would have been my explanation? My niece forgot about it and moved on, I think. A few months later I'm visiting again and we're playing basketball and I have some loose shorts that go down a bit. She says, "I can see your panties." her friend giggled and I got all red, even though it was actually boxers that were showing. Still, it humbled me.* Going to adult video store and having to ask 20 year old black guy to open up the DVD section that has sissy maid videos. Every other fucking video is out in the open but the sissy stuff was behind a glass window in lock and key. Another pervert customer, old man, watched me go back as he opened it and pulled some down for me. I had to pick the one I wanted out then give him the other two to put back.
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the most humiliating thing for me?knowing that no matter how manly, how gruff, hardcore, mean looking i am (i pretty much look like your stereotypical biker) the first time i ever had sex... I took it up the ass. I was 15 years old and got my butt stuffed with dick from a grown man. At the time I was living with my mom until she had a nervous breakdown and ended up in the psych ward of this hospital.... long story short, i didn't have anywhere to go so one of the staff members at the hospital offered to let me stay at his place.he was cool, played video games and everything. we'd stay up late watching movies and stuff. but of course the day came when he saw that i had panties on under my jeans...he was cool about it. he told me dude, its no problem. you can wear whatever you want to around my place. be yourself. eventually i took him up on the offer. It was late one night, i went to the bathroom and put on a little lacy pink nightie, matching garter-belt, thigh-highs, lacy pink thong, etc. i pulled my hair up into pig tails even. i couldn't believe what i was about to do! nobody had EVER seen me wearing girly things, EVER.so i walked into the living room... and he glanced over at me and asked "you ready to start the movie?"i said yes, so he pressed play. he didn't even seem to notice what i was wearing at all! i couldn't believe it!that night i was in such a daze, i was so horny and feeling so girly... i snuck down the hall to his bedroom and crawled into bed with him.I remember pressing my girly body against his back, kissing his neck and reaching around to play with his cock. i remember how much bigger his cock was than mine, and i remember getting it hard with my hand and how much pre-cum i had on my fingers...i'll never forget that the first time i ever had any intimate sexual contact with another human being was with a man. my first kiss, my first... everything.he pushed my head down and i wrapped my lips around his cock. i had no idea how to do it, i just knew thats what he wanted me to do. i sucked his dick as best as i could... then he reached around and stared rubbing my little butthole with his finger tip.around and around he rubbed it, with his finger lubbed with spit. pushing in the fist nuckle in and out, around and around, in and out, until i was moaning around his cock.slowly he went deeper and added another finger... before i knew it i was drooling around his cock dying to have it up my ass. so i begged. i literally BEGGED him to fuck me. and he did. thats how i lost my virginity: me on my hands and knees in lacy pink lingerie with a grown mans dick in my butt. and i came from it. i very distinctly remember being on all fours, not touching my little dick when i felt my orgasm coming. i have an extremely vivid memory of this, looking down between my arms, across my lacy lingerie covered body towards my rock hard cock sticking up out of my panties, pre-cum flowing freely, the hair manly legs of the man fucking my ass right behind me... and me in disbelief realizing i'm about to cum from getting fucked in the ass. i remember saying it out loud "oh my god... i'm gonna cum... i'm gonna cum... "my knuckles going white as i clenched the blanket, i hooked my legs around the backs of this thighs, and it happened: i shot my little sissy load hands free, all from having a cock in my ass. and right about that moment he came inside me. i will never forget that. no matter how manly and gruff i get, no matter how tough and mean i can be, no matter how much i talk about girls and how hot they are and which ones i would fuck and how, no matter how many women i date, live with, fuck, etc. I can never forget that i lost my virginity not as a man... but as a sissy faggot.
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A new guy moved into the next door apartment. One night I was sitting in a lace bra and panties, garter belt with stockings, heels and a sheer robe when there was a knock on my door.I quickly realized my curtains weren't completely closed, so I went to the window to close them. He had seen me watching gay porn, a crossdresser sucking cock. I didn't know what to do so I looked out the peephole in my door and there he was. He looked really hot, and I could see he was wearing only jogging shorts and rubbing a huge bulge in the front. I asked what he wanted and he said just to talk as he was new here. I opened the door and let him in, he could see my cock (small but erect) in my sissy panties. he said he missed his gf and really needed some company. I went to get him a beer and when I came. Back his shorts were off and he was sitting there with a huge(about 8") cock . He had changed the channel and was watching a girl sucking cock. He pulled me down on the couch and took my hand, placing it on his penis and told me to stroke it while he watched the movie. I had never felt a cock orher than mine and was amazed it dould be so hard yet so smooth at the same time. I pumped his dick and suddenly just creamed my panties, not even touching myself. He stood up and made me crawl to the window, where he made me kneel as he opened the drapes. He pushed his cock in my mouth and made me suck it. I could see other people watching and felt like a total slut. Now I let other guys come over for me to suck. I like getting my face cummed on like he did that day to me. I. Have had up to 3 guys at onetime come over when I am dressed like the sissy fag cocksucker i am and let them party in my mouth and ass. I love being used by big cock, and left on a Saturday night with cum on my face and dripping out my ass. They all say that other than my sissy penis I am the best pussy they have ever had. I also go to ABS when I travel and like to dress and get used there.is there anything more humiliating than walking to your car at 1 am in girls clothes covered in cum? I don't know but it makes me want more sperm on my face. As I guess you can tell I like to dress like a girl and let real men humiliate me with big, strong cocks.
I was dressed like a slut when he got here,bra, panties garter bely and stockings, fuck me heels and a tight black dress. I had put on make-up extra heavy because I knew we were staying at my place. We had a couple of drinks and I could see he was getting aroused. Of course I was teasing him, "accidentally" letting my hand brush the front of his pants if you know what I mean. We started kissing and he was feeling me up pretty good. . I got on my knees in front of him and unzipped his pants. A big erect penis fell out onto my face. My sissy penis was already throbbing in my black full cut panties, but I just creamed right there. I began kissing his penis, knowing that I was meant to be his cocksucker. He began to call me his faggot and whore while I sucked him and I could feel my little dick get hard again because I knew he was right.i was humiliated when he pulled out of my mouth and shot sperm all over my face but I loved it so much. He could see my sissy penis bulging in me black panties and told me to stand up. I did, and he yanked my panties down to my knees and slapped my sissy cock. I could not believe it but I creamed again, most on the floor but some on his chest. He made me lick it off.
How very humiliating that would be for me! To sit there, feminized like a sissy by my wife, so that I could appear as a sissy to her lover. Then being ordered by my wife (as her sissy) to clean him and her both after they have sex in front of me. I would be almost beside my self with shame!
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Finally my dream cum true. I was 14 , he was 17 . His parents out for the weekend, his sister just off to college. We went so his sisters room and found a bra and panties, his erect cock brushed my face as I knelt while he fastened my bra. I was pretty naive back then but I knew he wanted to push his erect penis into my mouth. I wanted it too. It was so humiliating, I could see my reflection I the mirror, dressed like a gurl and a cock in my mouth. What was worse was we were so young, he told other guys at the school we went to and when they found out we would be alone they came over and ihad to blow them.
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