Transvestite

Instructor Mike’s Academy – Part 4 – Becoming a Girl

/ Categories: Anal, Asian, Ass to mouth, Authoritarian, BDSM, Boy, Cock & ball torture, Discipline, Domination/submission, Enema, Exhibitionism, First Time, Gay, Humiliation, Interracial, Male Domination, Role-playing, School, Teen, Transvestite, True Story, Young / Anal, Asian, Ass to mouth, Authoritarian, BDSM, Boy, Cock & ball torture, Discipline, Domination/submission, Enema, Exhibitionism, First Time, Gay, Humiliation, Interracial, Male Domination, Role-playing, School, Teen, Transvestite, True Story, Young / By

Warning: This is an explicit semi-fictional/semi-autobiographical multipart series involving White Daddy / south asian teen raceplay, crossdressing, and more. If you are not over 18 and/or find the notion of White Cock superiority to be offensive, then please do not read on. Instructor Mike’s Academy – Part 4 – Becoming a Girl Sadly, it was time to head back. I had cleaned myself well in Instructor Mike’s shower, and when my mother came home she was none the wiser to my day’s lesson plan or psychological transition. I went to bed with a smile on my face thinking of the amazing feeling when he made my little peepee dribble, but more so with the knowledge that I pleased my Sir and helped him shoot his Glorious White Man Cum all over his little sissy’s face. …

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Rick’s Wife_(0)

/ Categories: Anal, Blowjob, Fiction, Transgendered, Transsexual, Transvestite / Anal, Blowjob, Fiction, Transgendered, Transsexual, Transvestite / By

Rick and I grew up in the same town, a half a mile from each other. We were best friends. We went to school, fished, rode bikes and hung out together at every waking moment. Rick was tall, tanned and athletic with wavy black hair and brown eyes. I was shorter, thin and blonde with petite features. When we went swimming, I couldn’t help but notice his huge cock when we got dressed in the locker room and I’m sure he noticed my smaller one, but was too polite to say anything. When Rick and I were teenagers, we would hang out by the river, drink beer and smoke a little pot. Rick and I were both interested in girls, but neither of us seemed to get lucky. After high school, Rick had a car …

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Sissy Pussy BBC

/ Categories: Anal, Blowjob, Domination/submission, Transvestite, True Story / Anal, Blowjob, Domination/submission, Transvestite, True Story / By

Prior to this incident I’m about to tell you about, I hadn’t been with a man in 3 years, but the stories I’ve been writing, and the feedback I’ve received have inspired me to get back out and find some cock. There’s only so far you can go with vibrators, dildos, and memories, and at this point, I have definitely taken that road as far as it can go. I figured it was time to make some new memories, and so here we are. Most stories I’ve written on here have been about my exploits when I was much younger, and figuring out that I was a sissy, or describing encounters that shaped me into the sissy I am today. This particular story is about something that happened just a few weeks ago. I’m in …

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Denver and Alex

/ Categories: Blowjob, Fiction, Transgendered, Transsexual, Transvestite / Blowjob, Fiction, Transgendered, Transsexual, Transvestite / By

Throughout my childhood and adolescence I had one friend above all else; Alex. We were neighbors when we were five and first met, doing normal kid things. When we hit middle school our bodies and personalities started to change. I started getting muscular and tall, he grew little height ways and his muscles seemed to slender out. I started getting a lot of attention from girls and Alex always seemed to just tag along. Still there was nothing that had really changed, we were just as inseparable. With high school though came a whole mess of change that could have stressed our friendship. I had continued to develop into nothing short of a mixture of a Calvin Klein underwear model and a NCAA linebacker; I stood six foot flat and 215 lbs of muscle. As …

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Deal with the devil 2

/ Categories: Bestiality, Boy, Fiction, Horror, Humiliation, Masturbation, Mind Control, Monster, Pregnant, Rape, Reluctance, Transgendered, Transsexual, Transvestite, Violence, Virginity / Bestiality, Boy, Fiction, Horror, Humiliation, Masturbation, Mind Control, Monster, Pregnant, Rape, Reluctance, Transgendered, Transsexual, Transvestite, Violence, Virginity / By

When they leave, I change into a bird, then take off. “Whew, that was something.” I think. “I can’t wait to try some other animals.” I fly down to the zoo, and only then do I realize a flaw to my plan. There are people at the zoo, so how am I going to have sex I decide that I don’t care, I need more sex, and I have a quick solution. I’ll be a fly, I’ll hide in some cranny in the pen, transform, then have some fun. I’m flying over the zoo when I see the first lucky animal, a wolf in the woodland exhibit. I change into a fly and drift down toward the caged play area. As soon as I land behind a rock I morph back into a human, then …

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Suzy Unleashed Chapter 5

/ Categories: Blowjob, Domination/submission, Fiction, Transsexual, Transvestite / Blowjob, Domination/submission, Fiction, Transsexual, Transvestite / By

I woke up on Saturday horny and ready for the next part of my adventure. In the back of my mind I still harbored nagging doubts about being introduced to Kathy’s anonymous friend, but knowing that I’d be sandwiching him between Steve and Ron allowed me to concentrate on how much fun I was going to have with them. Besides, I rationalized, Kathy wouldn’t be setting me up with another guy unless she believed he’d enjoy it, so maybe even the stranger would be enjoyable. While Kathy prepared breakfast, I showered, shaved and applied my makeup and wig, then completed my transformation with my standard outfit of a teeny, tiny miniskirt and sky-high heels. Looking in the mirror, I couldn’t help smiling at my appearance. “Not bad,” I told myself. “It’s pretty obvious that I’m …

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Jaclyn part one

/ Categories: Fantasy, Transsexual, Transvestite / Fantasy, Transsexual, Transvestite / By

Let me start off by saying that I have always enjoyed wearing women’s clothing, as far back as I can remember I love the feel of satin against my body. My first experience was when I was 13. I was in the bathroom, taking a piss, when I saw a pair of my mom’s black satin panties in the hamper, so I took my mom’s panties and off to my room I went. That night was my first experience, with women’s panties. The feeling of them hugging my little cock was intense needless to say I came very fast, When I was finished I couldn’t very well put them back in the hamper, so I stuck them between my mattress’s. Not too long after that I discovered transvestite website’s, I was stunned how these men …

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Hot Chocolate

/ Categories: Blowjob, Coercion, Cum Swallowing, Fiction, Interracial, Transgendered, Transsexual, Transvestite / Blowjob, Coercion, Cum Swallowing, Fiction, Interracial, Transgendered, Transsexual, Transvestite / By

“C-come on sis, I don’t want to do this!” His sister, Joanna, smirked and shrugged, “Aww, Casey, I really don’t care! Now, come on, pucker your lips up some more, hm?” After a reluctant sigh, he did so, quickly feeling her fingers on his chin, steadying him as she applied the red matte lipstick to his plump lips, “Yeah, yeah just like that, perfect…” “C-come on, you can’t be serious?” He complained, voice soft once she was finished applying it, looking at his sister with wide anxious eyes as she glanced in a mirror, pursing her own lips before glancing back to Casey, as if comparing them. “Yeah, you look perfect… One second, let me just do your eyelashes.” Casey let out another sigh, feeling the butterflies float around in his stomach as his sister …

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Something Extra_(0)

/ Categories: Anal, Bi-sexual, Blowjob, Fantasm, Transgendered, Transsexual, Transvestite / Anal, Bi-sexual, Blowjob, Fantasm, Transgendered, Transsexual, Transvestite / By

The date had gone really well. Way better than I’d expected actually. Which was both good news and bad. I enjoy being wined and dined like any lady would. And I really had enjoyed dinner with this guy. He was quite funny which is always a turn-on. And he was just touchy-feely enough to make my heart flutter (and a few other pieces) but wasn’t forward enough to make me think I was just going to be another piece of tail. Not that I would have minded as this guy was CUTE. And built. I’d gone to extra lengths for this date too. Normally I’m pretty laid back on the whole girly-thing. My hair is short, black and usually a mess. I’m pretty pale as I’m terrified of skin cancer which is what got one …

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Kelly – Part 1

/ Categories: Consensual Sex, Fantasy, Teen, Teen Male / Teen Male, Transgendered, Transvestite / Consensual Sex, Fantasy, Teen, Teen Male / Teen Male, Transgendered, Transvestite / By

Do you know what it’s like be stuck in a dorm room with a male roommate, in an all-male residence hall, during a dry spell? When you can’t even masturbate because either your roommate is around, or you have homework or studying to do? I’ll tell you what it’s like. It’s like being starved. Red-blooded guys like me need a woman’s touch. We need to be between their legs, making them utter sounds only real men get to hear. We need the warmth and softness of a girl, or we go insane. And I was going insane. I hadn’t jacked off in a month. A month. And I hadn’t been able to score. Either I fucked things up, or luck came in and fucked it up for me; there was no getting laid. It was …

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Suzy Unleashed Chapter 10

/ Categories: Exhibitionism, Fiction, Slavery, Transgendered, Transsexual, Transvestite / Exhibitionism, Fiction, Slavery, Transgendered, Transsexual, Transvestite / By

By the time the alarm went off on Thursday morning, I was already awake, lying in bed thinking about what would be my second day on my new job. I couldn’t decide which of the emotions I was feeling was stronger: fear, shame or excitement. The one thing I did know was that in a short time I would be facing all three. Again, by the time I finished showering and shaving Kathy had laid out my wardrobe for the day. I was surprised to see that she had selected a red blouse and a relatively modest black skirt that was at least six inches longer than the dress I had worn the day before. I breathed a sigh of relief until I noticed that lying beside the skirt were a garterbelt and stockings. Knowing …

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Suzy Unleashed Chapter 9

/ Categories: Fantasy, Transgendered, Transvestite / Fantasy, Transgendered, Transvestite / By

I slept very little on Tuesday night, tossing and turning as I tried to come to grips with the step I was about to take. At about 5:00 I decided I wasn’t going to get any more sleep, so I got out of bed, and, with nothing else to do, started to prepare myself. I showered and shaved both my face and my entire body, making sure there was absolutely no stubble left behind, then spent over an hour carefully applying my makeup and another half hour applying bright red polish to my artificial nails. By the time Kathy got out of bed, I was satisfied that I looked as good as possible. Kathy immediately confirmed my belief, telling me how beautiful I looked and what a great job I had done with my makeup. …

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Meeting my on-line lover

/ Categories: Fiction, Gay, Transvestite / Fiction, Gay, Transvestite / By

I met Mark online. I’d joined a gay chat room. I had been fantasizing about being with a man for a while and this was a harmless, anonymous way to explore my interest. To begin with, I was very shy and didn’t know how to respond to the occasional message that came my way. Then I got into a conversation with a guy who made all the running. I only had to go along with his messages. I’ve discovered that the best cybersex is to be had by going along with the person you are playing with. Unless it takes you somewhere that is a turn-off, if you build on whatever comes from the other person, it can be very arousing. I allowed myself to forget all my inhibitions and commit to the scene. It …

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MORGANA AND RAELINE

/ Categories: Ass to mouth, Bi-sexual, Blowjob, Erotica, Exhibitionism, Female/Female, Group Sex, Hardcore, Lesbian, Male / Older Female, Oral Sex, Transvestite, True Story, Voyeurism / Ass to mouth, Bi-sexual, Blowjob, Erotica, Exhibitionism, Female/Female, Group Sex, Hardcore, Lesbian, Male / Older Female, Oral Sex, Transvestite, True Story, Voyeurism / By

My hands moved quickly behind her. Holding one arm around her waist, I pulled her back against me, with my other hand hoisting up the back of her skirt. Her wonderful creamy thighs and magnificent ass cheeks were naked above her stockings. I cupped my hand over her pubis. “You’re dripping wet,” I said huskily. She still didn’t move. “I’m always wet,” she replied. She heard the zipper of my fly snap open, then with one hand in the centre of her back, I bent her over the windowsill. A moment later she felt me large and hard inside her. She gasped, her concentrated gaze out the window broken, her hands resting against the windowsill for support. She gasped again. A mew like groan came from her throat. My hands grasped like vices against her …

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Life long TV

/ Categories: Bi-sexual, Cum Swallowing, Transgendered, Transvestite, True Story / Bi-sexual, Cum Swallowing, Transgendered, Transvestite, True Story / By

Hello all you sexy readers! I’m Lori, a transvestite, and here are a few little tidbits about me. I can remember loving girly things ever since I was very young. I had three sisters and my mom’s stuff to admire. I was about four or five years old when I noticed nthat I loved the feel of soft, silky under garments. By the time I was seven I would sneak a pair of panties from the hamper and wear them to bed. Soon I would take a bra on occasion and wear it too. I steadily progressed to include nylons, slips and even girdles! I loved trying on new things as often as possible. By the time I reached thirteen I was dressing from head to toe. Being the oldest, and only “boy” in the …

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Sub

/ Categories: Cuckold, Domination/submission, Erotica, Fiction, Foot or shoe fetish, Transsexual, Transvestite, Voyeurism, Wife / Cuckold, Domination/submission, Erotica, Fiction, Foot or shoe fetish, Transsexual, Transvestite, Voyeurism, Wife / By

I might be the luckiest man on the planet. I was born an only child to a family of great wealth, I have all the things money can buy, and the most beautiful wife in the world who I love, worship and adore with all my heart and soul. She is literally a beauty queen who won competitions in one of the largest states in America for her statuesque, fit but voluptuous body, cascading golden hair, and a face that could launch a thousand ships. My wife would never have noticed me, as I am hardly a specimen of masculinity, except that I was persistent in my pursuit of her, which consisted of constantly showering her with gifts, a Ferrari, a thoroughbred horse, diamonds and rubies, and use of my private jet to go on …

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Pleasing Bill: A Crossdressing Story #3

/ Categories: Anal, Blowjob, Discipline, Domination/submission, Fantasm, Slavery, Transgendered, Transsexual, Transvestite / Anal, Blowjob, Discipline, Domination/submission, Fantasm, Slavery, Transgendered, Transsexual, Transvestite / By

[b]Chapter 3: Mom’s Talk [/b]I woke up early the morning after my first day of being Bill’s live in slut. I got up to listen and hear my dad and siblings leaving for work around 7. I was going to wait for all of them to leave before I dress and go back to Bill’s at 12. I went to lie back down but before I could, I heard my mom call me. “James, honey. Can you come down here?” I didn’t know what to say a first. She probably wants to talk about how she saw me last night. I guess there was nothing else I could do but go down there. I was in my pajama pants and a white tank top on with the black and pink Daddy’s slut colr on. I …

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our walk part 1 & 2

/ Categories: Gay, Group Sex, Older Female / Males, Threesome, Transvestite, True Story, Wife / Gay, Group Sex, Older Female / Males, Threesome, Transvestite, True Story, Wife / By

***********************************************our walk**************************** Recently my wife asked me if I jerk off, And I said yes, she then asked me what i thought about while doing it. I told her my many fantasies. She agreed to help me fullfil one. I got home from work last week, it was late, my wife told me to take a shower and put on the outfit she laid out in the spare bedroom for me. When I got out of shower i went into the backroom and found A pair of black tights (with hole cut out for my cock) a black leotard , oversize hooded sweatshirt and sneakers. I was trembling as I got changed, My cock was rock hard sticking out of the tights but covered barely by the nylon of the leotard. I went into the …

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Nerves, Shivers, Cum

/ Categories: Anal, Transsexual, Transvestite, True Story / Anal, Transsexual, Transvestite, True Story / By

The panties were tight. My legs and underarms were shaved, and the panties clung to my cock, smushing it between my legs where it was hidden and not in the picture. He met me at the door and led me into his room, walking slowly behind me, breathing heavily. I walked in and stood with my back to him, nervous, vulnerable, and dressed in pants and a baggy shirt. Beneath my clothing were black satin panties and a matching black satin bra, and pantyhose. As I stood there, anxiously, he could sense my nervousness. I could sense his presence, as his panting drew closer and closer to me, and I began to shiver. He quickly got up behind me and wrapped an arm around my neck and an arm around my waist, his hand reaching …

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Working ‘Girl’_(1)

/ Categories: Blowjob, Boy, Fantasy, Gay, Prostitution, Transvestite, Young / Blowjob, Boy, Fantasy, Gay, Prostitution, Transvestite, Young / By

Brian sat impatiently on the park bench, fidgeting in anticipation and excitement. He quickly checked his phone for the time yet again, seeing it was just after 1AM. It was the perfect time for meeting a customer. He reached over to run his fingers along the signature red bracelet over his left wrist, which let men in the area know he was ‘working’. His ears perked up when he heard some noises off in the distance, a gentle rustling in the bushes. Brian smiled slightly, knowing someone else must be doing just what he was about to do now. He thought about that video game he wanted, the one all the other kids at school were talking about. But at 14, he was too young to have a job, and too old to convince his …

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