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She would tease me relentlessly at work, giving me sneak peaks up her skirt, shoe dangling in the break room, coming over to my cubicle to "talk" but more like to bend over so I could look down her blouse at her breasts. Sometimes when no one else was around she would play with my caged penis. She genuinely enjoyed teasing the heck out of me knowing there was nothing I could do about it. She got me to admit that I used to masturbate and fantasize about her before we started going out. And at first I had a real difficult time adjusting to the chastity. The first week she had me come over… Read more

There was this woman where I worked at. She had a thing for retro and would wear business skirts, high heels and actual real stockings every now and then. She had a body to die for and legs that just simply made me melt. When she walked by I would simply melt. Could not explain it this power she had over me, it was more than just sex or lust, it was like the magnetic pull that keeps the Earth in orbit. I started small talk with her and over time we began chatting now and then. I WANTED TO HAVE SEX WITH HER SOOOOO BAD!!! But would not even flirt with her in that direction because I knew from of… Read more

As you can see I have my real name posted. My name is Brandon Hippel and I am a 26-year-old exposed sissy webslut from Abington, PA. When I was 19, I got fully exposed online as a sissy without my permission or knowledge of it about to happen. It all started when I was 18. I started searching through Tumblr and became interested in sissy porn. When I was 19 I started to dress up in my sister's clothing and take a few pictures. Then after a while, I got brave enough and started posting a few of them on ImageFap. I was too afraid to show my face at the time so they were just body pictures. Then… Read more

She unbuttoned his pants and pulled down the zipper. She reached her hand under the waist band of his boxers and I caught my breath as his cock came out view . It was just semi hard and still almost 6 inches long, I have only seen others cocks on the internet. This one was real and it looked huge . I heard Mark let out a sigh,”Oh Susan that feels good””” Susan told me to slide my skirt up a little . To give Mark a glimpse of my panties . I slowly edged my skirt up. She commented on what sexy panties I had on and for me to turn around and show them my ass butt . Mark has started unbuttoning S… Read more

When he invited me to come along on a road trip with him, I didn't realize he was an owner operator of his own big rig. I was expecting perhaps a guy who wanted to take a trip down the interstate to some seedy motel for the weekend, but this was a welcome surprise. "You ready?" he said to me as I stepped out of my vehicle at the long term car-park just outside my city. I was dressed rather conservatively on the outside.. just a set of high heeled boots, stockings, below-the-knee length skirt, and a rather fashionable sweater top I had just picked up online. Underneath I was dressed in standar… Read more

I frequent adult bookstores on occasions and suck some cock. My wife does not know that I’m Bi curious and it turns me on to look at other cocks. I have never been with another man other than the occasional cock at glory holes until the other day. The morning started out as any other when my neighbor called me and asked me to come over, he had a plumbing issue. So I went over and the two of us were able to fix the small leak. He offered me coffee and we sat in his family room and just talked. I wondered where his wife was and he said she was out shopping, I told him mine was too. I noticed a p… Read more

I decided to use Halloween as a way to come out to my wife as a cross dresser. I had grown sick and tired of hiding my clothes and only having play time in my panties when she was not home. She was going as a sexy cop and asked me what I wanted to be. I suggested, in a joking way, that I go as a trashy hooker that she arrested. Her face lit up at the idea, so I decided to run with this limited opportunity that I had. I went out and bought more clothes and make up (always an excuse to shop!), grabbed a few items from my stash, and was dressed before she got home. Her response was bet… Read more

The k** next door was a delinquent, the last person I would have wanted to catch me. When he saw me dressed in my wife’s lingerie he laughed, called me his bitch and forced me to my knees. Every day, before my wife comes home from work, he has me on my knees, sucking his cock and swallowing his cum. At first he was happy to just humiliate me as he fucked my face. After a few months he started making me stroke my own cock as I sucked him. I had to start stroking the moment his cock touched my lips and had to cum immediately after he filled my mouth with his cum. After several months of that he… Read more

1) Sissies need cocks & cum. Once you are alone with a sissy, just pull out your cock & she will instinctively drop to her knees to suck you. 2) Sissies live to please, their pleasure comes from pleasing you, so don’t feel bad about using your sissy for all your kinky & questionable desires... They love it & it is one of the many reasons that sissies are better than girls;) 3) Keep your sissy in chastity, this will ensure she is in full heat for your cock! 4) Keep your sissy plugged, so whenever you like, you can just remove it & slide your cock into her prelubed fuck hole.… Read more

My little girl jumped in my panties as Steve held me so close.I understand now why girls wear lovely ladies lingerie and gorgeous short dresses. To attract men and get their handsome cocks inside them.To welcome the swimming sperms hoping their eggs get fertilized.I kept having visions of marrying S. wearing a virgin white lacy gown.The Princess marrying her Prince. I had to go easy because I was taped & tucked.Then he dances with Sarah and they kissed and hugged.I was so jealous of her butt managed to control myself.The party began breaking up.Sarah and Cindy came over to us holding hands… Read more

My sister knocked on my door.”Timmie you been in there 5 hours .May I come in?”I stood before her in the black pink mini dress.My long honey blonde hair was pulled back like a pony tail.I put a pink elastic to hold it in place."You look adorable. Let me do your make up and you are instant 21 st century girl.First go shower up and shave your body hair. Lucky again you don't have much body hair." I was soon shaved excepting my privates. I put on the pink panties with the little flowers and matching pink lacy bra walked in to show Sarah."You little cutie. Oh my you have a little boner in your pan… Read more

My first marriage was to a biological female. 5 yrs of misery until she dumped me for some black stud.Can’t blame her.My tiny white pee pee was not up to the task.She had often told me to wear panties because tiny dickies Love girly panties. I moved in with my sister Sarah and her hubby Kyle. One evening we watched a sad romantic movie .The guy got dumped and suffered a nervous breakdown. I cried out loud as my brother in law turned off the TV. My sweet sister comforted me. One night she said Timmie you have really nice legs and you don’t have much body hair.Your long hair is prettier than mos… Read more

A cousin of my then wife sadly died at quite a young age. I didn’t know her other than having been introduced at family events. However, my wife had been close to her and wanted to pay her respects but as she couldn’t get out of an important meeting I attended the funeral on her behalf. After the ceremony there was a meal provided at a local hotel which I, of course, attended. Pre-lunch drinks were provided and then we went in to a private dining room where everyone was seated at small tables of just four or six persons. I ended up sitting with five other people, none of whom I knew, and who… Read more

Jake and I lived in the same apartment house and often met at the pool. He was manly and muscular so I didn’t think anything about his looks at my slim, girlish figure or teasing compliments that I would make a pretty girl. Hearing I was out of work, he invited me for a weekend to a friend’s mountain cabin before I started hunting for a job, and I accepted. The area was isolated, and the quiet was a nice change. That night we played strip-poker (as I couldn’t afford to lose any money), and I was soon down to my briefs while Jake had only lost his shoes and socks. When I lost again, he offer… Read more

Last Friday we had a date scheduled. We were going out to dinner to meet Jay and we had a room booked at a nice hotel. Mandy and I checked in early. We relaxed for a while, sipping a glass of wine before Mandy headed off to take a bath and start getting ready. Just as Mandy settled into the tub, Jay sent her a text. I didn't read the text, I just took her phone to her. She read the text and looked at me with a grin on her face. "It looks like I'm not the only one that needs to shave her legs." She said to me. I had an idea of what she was talking about. Whenever we meet Jay, Mandy… Read more

I have always wanted to wear pretty things since I can remember. I watched my older sister getting ready to go out with her friends, to school, or just hang out. I watched her pamper herself with soft sexy lingerie, stockings, garter belt and everything else a pretty girl would wear. I wanted to be a girl, just like her. I started my journey into womanhood in my teen years by borrowing a pair of my sister's panties, then it was her bra, then her stockings and garter belt. This borrowing went on for a while until I was discovered, not caught but discovered. The memory is as clear today as it wa… Read more

This is a true story that happened to me a few years ago. I was working in a small village down in Devon and was lodging with a woman in her early forties named Elaine. Elaine was very attractive for her age and she had many younger friends that were about my age (23 at the time). I got on well with Elaine and often thought about having sex with her if the opportunity arose, but I didn't want to ruin our friendship and living arrangements. I had the day off work one day and Elaine was working till five. I had been working late the previous evening so I woke up about twelve midday and ha… Read more

Jim is at my house every night, and every time he comes over he brings me something new either a new outfit, or a watch, or rings and necklaces. The nights that he comes over he makes sure he is the one to remove the big plug and reinsert it, and every night I suck his delicious cock. One night I asked him while giving him this pouty look, daddy when are you going to make love to me. He told me when he felt I was ready. Guess the sad look didn’t work. After four days of asking him to make love to me he got tired of hearing it. He told me to strip and go to the bed. Sitting on the edge of the b… Read more

Three months go by and all is going great. I am with Jim and every night I get to worship his wonderfully huge cock, and get his load. I keep asking then turning to begging for him to fuck me. Every time he just says not now baby gurl, I will hurt you. One night I am laying with my head in his lap rubbing on his cock, as it starts to thicken I sat up and pulled it out. As it sprang out I grab it with both my hands, lean down placing his head on my lips slowly parting my lips letting it slid in. I start sucking his massive manhood like the good cock slut I am. Rubbing on his ball I can feel the… Read more

Almost two weeks go by and Jim is the perfect man, he takes me out to eat for nearly every meal, and he has got me tons of stuff from clothing, to jewelry. I have gold rings and necklaces; I am on top of the world. One day he calls me and tells me that two girls are coming over; when they get there I am to do everything they tell me to. When they got there they had me shower, shave and go to the living room and to stay naked. When I got there I see a full outfit on the couch and by the looks of things they were going to dress me up not to look too sluty but close. One of the girls told me t… Read more

I guess I was worn out because I passed out on the couch. I woke up to the sound of my door opening, as I looked it I saw Jim, and in one hand he had a bunch of flowers, and in the other a small bag. I jumped up and started to say I was sorry for not being ready for him and that I would get dressed right away. He told me to relax, and that he believed I had learned my lesson. He handed me the flowers and said they were for his new gurl, with a semi smile I took them, after I grabbed them I got closer to him and reached out to give him a hug. When I felt his arms wrap around me I got this wa… Read more

Monday morning comes and I know I got to head to work, as I was sitting on the edge of my bed I was contemplating what I should do. I know what Jim wants of me but I did not know how I would work all day wearing panties, hosiery, and a plug in my ass… oops pussy, and a sports bra. I said the hell with it I know I can go to work and not have all that stuff on or in me, and Jim would never know. So I undressed, took the plug out, put my work clothes on and headed out. To my surprise I made it through a whole day of work and back home without Jim finding out anything. I went right to my room j… Read more

The whole weekend I was kept in my own house with Jim and his friend, and other than telling me what to do or pushing me into place Jim never touched me. The other guy however fucked me in every way he could think of cumming in me, on me and making me swallow is loads. By that Sunday when this guy had enough of fucking me he just left, and Jim told me to go take a shower, shave again and clean myself inside and out. I did as I was told, and when I got out of the shower he told me to lie on the bed. When I laid on the bed he pulled out a bottle of lotion, it looked like some high dollar stuf… Read more

Jim told me that I was to drive home and he was going to fallow me because we had things to do, I asked him like what. With a hard slap to my very tender ass he said that was his little secret. I got in my car and when I sat down I could feel the burn from the beating I just took. I was so scared while driving home I had no clue what this very large man was going to do to me. He was so big all over and he over powered me from the first moment he looked at me. He stood nearly six four very wide shoulders and huge hands. And he had the commanding voice that sent chills down my spine all the w… Read more