Confessions tagged with 'crossdress'.

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#3016

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Since my divorce I spend a great deal of time dressed as my feminine persona, Lucie. I have secretly crossdressed since a young teen and revealed myself to very few people until recently. I met a guy named Tom on a dating site and I have been his dirty little secret for nearly a year. He is married with a couple of grown kids like me. We are quite similar except I like to dress like a woman. We meet a few times a month at my place and on two occasions he fucked me in his marital bed while I wore his wife's lingerie. The second time he fucked me bareback and when he came inside me it made me feel so utterly feminine.

His wife went away for the weekend so Tom invited me over to his place. I sat at his wife Kim's dressing table and started on my makeup, he had already laid out an outfit for me to wear. Twenty minutes later and dressed in his wife's sexy lingerie I slipped on my heels and went down the stairs. I heard voices from the stairs and thought it must be the television. Instead to my shock there was another guy there, Tom told me to suck his cock and began taking pictures. This was a first and made me uncomfortable, but I still took his friend John's big dick in my mouth. Tom put his phone down and worked his cock up my ass. The feeling that came over me as these two men used me is indescribable, I was their source of pleasure and they fed and fucked me till the next morning. I love my life as a slut.

#2359

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The black closet sissy again so I just went out I had met guy earlier at park he seen me dressed we exchanged numbers he had to go to work, so i text him told him to meet me back at park, I parked on street beside because I closes at 11 so its like 1 am i slip on my red dress stockings and heels i walk to park and there a trail with bench so i walk back its a light near I say a figure sitting there shadows moving ask if jerking off but i wasnt that guy i approached he said damn so i switch my walk and ask does he need help I sit beside him and take a look big black uncut had to be alittle bigger than my 9. The rush came over me I grab it jerked it felt it getting bigger i put my knees on bench my head in him lap and begin sucking it was a weird taste but the rush had me licking all over it he pulls his pants all the way down his balls are hanging i deepthroat all the wau to balls and sucking them my phone alerts text its guy from early i tell him where i am, i get on ground and begin sucking again he now its slapping my ass and running finger in hole. With face sloppy i ask do he want to fuck me he says hell yeah i stand up this time he is rock hard vieny cock forskin up over head I finger my ass i rub my ass on his dick feeling it all wet his head pushing against my hole my heels are shaking i hear him spit I ask Mister are you clean He reply dont worry and chuckled, i ease down and feel skin pullback in my ass to feel his head inside me i text guy back told him have dick already out. I begin bouncing on dick feeling the wetness i see a phone light on path getting closer its the other guy he says can I join with white 7inches out pants I grab and pull towards my mouth wig hair in my mouth to I go to work on it, i get off dick and suck bbc again wit my ass up i feel his face near my ass the white guy start eating my ass he ask am I readu I say yes that white cock slide into my ass black guy stands up he is tall i grab his balls and suck his meat again other guy stops and come to front too, so I suck both the black guy then hold his meat and rubs it on my lips white cock slapping my cheeks i feel black dick throb alittle and I feel which i thought was cum but it was watery i thought he is pissing my rush kicked in again i open mouth soon hit my throat I puked alittle got back sucking it was to much i was drowning, i pull dress up and let him finish peeing on me it taste stail and nasty as fuck. I bent back over they took turns fucking me my heels are now off, white guy sits on bench while my ass getting fucked i feel my soul leaving my body as he moans saying he is cummin, i suck sloppier i feel a fast skeet in my throat and a slow thick load in my mouth by this time i hear I'm coming to his hands grab my neck and pelvis as he shove in i feel his dick unload in me it felt like overflowing i hold it in and sit on white guy dick its getting soft but he managed to put head back in I grind on him by this time I am ready to come I stand up tell white man suck me I feel it he got it wet I stand back and jerk my load into his mouth. We leave no words spoken now I am sitting her with my gf

#827

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I buy used school girl uniforms and I wear them and jerk off on the dress while imagining the teenage hotty who wore the dress before me. I have all the uniforms in my area and I watch teen girls in the same dress then I go home and put the school girl uniform on and wank over the uniform while imagining she is riding my old man cock with her young underage body. I wear bras and panties. I have jerked off so much times to preteen underage school girls I cant remember how much. I actually would like to suck a young boys cock and have him cum in my old mouth. ALL men want this to be real,it is everyman on planets fantasy to fuck underage school girls and suck young boy penis till shoot hot young load in my dirty old mouth. YUM.

#435

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When I came home from work on a Friday night, a few weeks ago, my beautiful wife was waiting for me at the top of the steps.

"Are you horny?", Kim asked.

"Yes!", I replied.

"Good! Then take off all your clothes, and, let's play our little game!", she giggled.

Gone were the days when she'd bring one of her girlfriends home for a menage a trois. And, so were the days of our forays into some S&M. For the past year, we'd started playing with cross dressing. It started when she dared me to put her panties on, on New Years Eve. I guess she didn't think I would, but, I did, and, we wound up having some really hot sex, afterward. It, soon, began to become a regular part of our sex play, and, we, both, loved it.

Before long, she started asking me to try on a bra, too. Then, she started putting make-up on me. At first, it was her things. None of it fit too well. But, after a while, she started buying me my own things, while I was at work. Gradually, she made adjustments, until the things she wanted me to wear fit perfectly. Over time, it got to be more and more. She started buying shoes, skirts, dresses, tops, stockings, garter belts, jewelry, wigs, and, even falsies. I never complained because I always knew there would be plenty of hot sex, afterward, and besides, it was all in the privacy of our own home.

A few months ago, she started taking me with her to her waxing appointments, and, had me waxed, too. She even had me get laser hair removal on my face. Sometimes, I'd spend the whole weekend dressed up. She worked with me on walking and talking, too. By the time she was done, I could easily pass for a girl. And, I'm not just saying that, either. When she dressed me, and, showed me myself in the full length mirror on the back of our bedroom door, I thought I'd fuck me!

That Friday night it was all about to change, though. I peeled off my clothes, eagerly, unaware of what she had planned. The clothes were all laid out, on the bed, for me. There was my favorite pair of pink bikini panties and matching bra, from Victoria's Secret. Black back seamed thigh high stockings, and, a garter belt. A very short black skirt. A really nice top. And, a new pair of black over the knee pump boots.

Once Kim had me dressed, and, my make-up done, she informed me that we were going out. I'd grown my hair long, so a wig was no longer needed. I protested, but, Kim was insistent. Finally, I gave in and agreed to go.

We went to a dance club, where all of the wild people went. It was a known hangout for the S&M set, as well as the gay and bi-sexuals. Lots of young hip people went there, too. We met Kim's friends, had a few drinks, and started to dance. None of them seemed to notice, and, Kim introduced me to them as her friend, Jennifer.

Then, as I was sitting out a song, a guy came over and asked me to dance. Seeing my situation, Kim hurried over to the table. I thought she would bail me out, but, instead, she told me to go ahead and dance with the guy. Fearing my cover would be blown, if I didn't, I got up to dance with him. His name was Sean. He was bi, and, had come to the club looking for another bi guy, but, after seeing me, he thought he'd go with a girl. After all, it was one of the advantages of being bi-sexual, he joked.

He followed me back to our table, and, Kim invited him to join us. I was not happy about that! Then, she started making out with one of the other girls. Sean leaned over and kissed me! He started grabbing my thighs, too, much to my dismay. I pushed his hand away. We danced and drank some more, then, Kim suggested we all go back to our place.

When we got there, the girls started pairing off, and making out. Before long, clothes started coming off. Sean kissed me. I was a little drunk. I kissed him back. Before long, he started trying to take my clothes off. I stopped him, fearing he was about to find out. But, another part of me wanted to see what it would be like. I started undoing his belt, and, unzipping his pants. He pulled his shirt over his head. It wasn't long before I tugged his shorts down, and, had his cock in my hand. He was as hard as a rock. He was about the same size as me. I liked the way his cock felt. Before I knew it, I was on my knees, with his beautiful cock in my face. He'd only managed to get my top off, so I was on my knees, in my bra, but, I still had my skirt and everything else on. I started kissing his cock, a little bit reluctantly, at first, but, soon, started to lick it. Finally, I parted my lips and took the tip of his dick in my mouth. I liked the way it felt. I started trying to get more and more of his cock in my mouth, until I gagged a little. I fought off the urge to gag, and, started breathing through my nose, as I sucked him.

A short while later, I felt something warm in my mouth. I felt him jerk. Soon, my mouth began to fill up with his warm sticky cum. I didn't like the taste, but, swallowed anyway. Afterward, he pulled me up and started taking off my bra. He sighed when my silicone falsies fell out, and, said he really had no idea, until then! He knelt before me, pulled my skirt and panties off, and, started sucking me. It was really good, and, he had me cumming hard, after just a few minutes.

Now, we all get together all the time!

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