Onec Upon A Cross Dresers Life #4 free porn video

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An Incident in a Cross Dresser's Life Part 4

I always dressed in pantyhose while teaching class. I had on an extra tight pair of panties to hold in my butt plug. Every movement sent shivers across my nipples. The only person who knew was my fuck buddy and fellow teacher. She was the first to let me explore my cross-dressing (see previous stories). After school, we would go to the park in her van that had dark windows that no one could see in. She would sit back and I would eat her pussy until her eyes crossed. The most amazing thing was that when she came, she would lock her legs around my head and burst a load of female juice into my open and wanting mouth. Then, she would cum again with a torrent of piss as her bladder opened with the intensity of her orgasm. I did not care at all. I learned to clamp my mouth high up after teasing her clit into convulsions to await the stream of golden delight. She came so hard that her golden nectar shot to the back of my throat and I swallowed or drowned. I loved it! She always claimed it was a "normal" female discharge. Fuck if I cared! While in her hot tub, I would have her stand and piss all over my face and I would lick her clean. None of her other lovers would let her piss on them or would eat her pussy after the first massive discharge. Their Loss!

Back to the van: After driving her crazy, it was my turn. She would pull my pantyhose down, pull aside my tight red panties and start to ram the butt pug in and out as she deep throated my cock. All 5 and a half inches LOL. She would call me her bitch as she porked me and slobbered my pecker. She would belay the plug to pinch the shit out on my sensitive nipples as she licked the head of my cock. That dove me insane. She would make me cum in her mouth and then snowball my load in a deep kiss. Once we cleaned up, she would go home to her vanilla husband. Sometimes I would put her up on all fours and fuck her up the ass. She loved the way my nylon pantyhose felt on the down thrust. It reminded her of her girlfriend fucking her with her strap-on. Once, she let me watch! I could not resist forcing my head between them and licking her clits. She came so hard she damn near broke my nose. There was blood everywhere. Nothing new to me as I loved eating her out on her period! Afterwards, they took turns using the dildo on me until my make-up ran and I was bull-legged.

Once, I met up with her in the park and opened the van door. To my surprise, dread, and excitement was a young endogenous student of ours. I figured blackmail, getting fired, and possibly jail all in one thought. I always thought Sarah was cute. She learned to be a great student and very fond of me after I taught her how to learn and was immune to her manipulating charms as a defense mechanism for getting over on the "system." She offered me d**gs, sex, and a hard time if I would let her "sake" and pass her without doing any of the work. I was a hard mother fucker when it came to my students.

Sarah was about 5'4" and very thin. Elfish in looks with large deep brown eyes. Not much in the way of tits but a nice small firm set. She loved showing off her bellybutton piercing. Short brown hair that framed her cute face. Lovely waist to hip ratio. I always wanted to lick her long legs from her toes to her pussy. Needless to say… It was a serious heart attack moment when she was in the van face down in my fuck buddies' pussy!

I climbed in and said to myself… "what the fuck!" If I'm going to jail, then just call the cops now! She looked up with juice smeared all over her face and just smiled. What the fuck was I supposed to do now!!! I sat next to my buddy and started deep kissing her. As Sarah intensified her licking, Buddy was barely able to keep her ass in the seat! I pulled her blouse over her head (bra less) I pinched her nipples, sucked them and then held her as she went into convulsions. Sarah then sat up and planted a very wet kiss on me and said next!
She sat up in the seat, changed places with Sarah and I started to take off her shoes and suck on her toes. All this time, Buddy kept prompting me to pay more attention to sucking then licking. She started to play with herself and ordered me to lick higher and higher up Sarah's legs. I wanted to take my time if I was going to get fucked up the ass in jail for doing this. I snaked my tongue up her thighs as she moaned and withered. I got to her p*o-Bear panties and started to nuzzle and lick her crotch. What!!! There was a small cock behind the Bear!!!! Well just fuck me (OK LOL). Buddy and I did not know she was a he!!!

I was not about to stop now. I mentioned to Buddy to come down and help me slurp her pussy / cock. She got down on the floor next to me and started to lick up her thigh. I waited until she got to the panties and found the surprise! Buddy did not slow down for an instant; we popped out her little wiener and took turns feeding it to each other. I would suck both of her hairless balls into my mouth while Buddy licked her cockhead. Switch! I had her cock all the way into the back of my throat when Buddy stuck a finger in her tight little ass. She bucked hard into my face nearly breaking my jaw. I wrapped my arms around her back and forced her cock deep into my mouth. She shot off so hard, I thought she was going to have a heart attack! I had no choice but to swallow (dear me). I held her in my mouth until she caught her breath and then let her cock pop out of my mouth. Buddy then lick her clean and gave me a lovely wet kiss.
Now what? A dilemma? Who was going to do what to whom? Sarah was crying. Great! A girl crying after I just sucked the cum out of her. Buddy calmed her down and we learned that she had been living as a girl since she was 13. Lucky for me she was 18 (legal consent but we could still get fired). She had never been with another man or women. She fell victim to Buddies' charms and gave into her long dormant lust. After a long conversation and a few beers, it was off to Buddies' place. Once she was composed and decided she really liked what had happened, she cuddled up between the two of us. Fuck was she cute! We slowly started to caress her and she just purred! After eating her first pussy and having her first blowjob, she wanted more.

Buddy was kissing her and playing with her nipples. She place her hand down on my crotch and started to gently rub my very hard bulge. Buddy told her to get down on her knees. Buddy stood behind her and pulled off Sarah's blouse. Sarah had lovely tits and very hard and perky nipples. Buddy was making hand love to her breast as she whispered "pull his zipper down." Sarah slowly complied with shaky hands. Once my zipper was down she reached in and stopped dead. There was a layer of pantyhose and red panties restraining my smallish cock. She looked up confused and then smiled!

Buddy ordered me to stand up and take my trousers off. I have very shapely legs and the nude pantyhose looked great on my legs. The red panties were highlighting my very hard pecker which was straining to get out. Sarah did not know what to do? Buddy knelt down and ripped the hose apart, pulled the panties aside and grabbed my purple enraged boy clit. She ordered Sarah to suck it! Sarah tentatively held onto it and giggled. Buddy told her to squeeze it just as hard as she could. Damn did I like that! She asked if it hurt? No I said, it felt great. She tried to make it harder and I just moaned. Buddy then told her to lick the head of my penis. Slowly she tasted it and put her pointed tongue into my pee hole and licked the pre-cum off like a kitten licking milk from her face. She did not need to be told what to do next! It was her lifelong fantasy and desire. Buddy gently guided her head up and down. We were both in heaven. I was not sure how much longer I could take it. Buddy put a stop to the blow job and Sarah just whimpered as the loss of the cock in her mouth.

Fuck!!!! Not now!!!! I was SO close! Buddy then knelt next to Sarah and coached her on how to give the world's best blowjob! She took to it like a pro. Buddy would take my cock from her and demonstrate and then pass it back to her. My toes hurt so bad felt so good. I saw God! Buddy then jerked my hose all the way down and pressed Sarah into my cock from behind. Her large breast smashed into Sarah's back. She then took one of Sarah's fingers, sucked it and told her to reach around and poke up it up my ass. That was it!!!! With Bundies breast forcing her against me, driving my cock down her throat, and a finger up my ass, I cut loose so hard I nearly passed out. When I was aware I was still alive (what a way to die) I saw them in a deep soul kiss. They stopped and kissed me with the remains of my cum fresh on their lips.

Sarah just whispered "more." I guess I'm not losing my job or getting ass fucked in prison. Just at home!
More later.



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My bride to be cheated on me as a girlfriend, again when she was my fiancé, and thereafter as my hot wife for 23 years. I guess the stars aligned for us.Me-For some reason I turned to slutty, tight black satin gloves in bed, without ejaculation, a year before I accidently discovered masturbation and gushing in the bathtub. I was 12 the first time I ejaculated, rubbing my cock with slippery shampoo. An overwhelming surge of floating and pleasure washed through my virgin boner as my sudsy palms...

3 years ago
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After hours with the lifeguard

“That’s one pound fifty change, and your band. Pool closes in twenty-five minutes.” “Do I need to wear this?” The receptionist had given me a blue band such as one would receive at a gig. “Yes, the lifeguard will need to see it,” she replied. The receptionist was a petite girl, blonde hair sitting on her shoulders, wearing the supplied blue polo shirt all the staff wore. For a petite girl she had an impressive cleavage, pushing at the buttons on her shirt. I thought I’ll just show it to the...

Fetish
3 years ago
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My Road to Crossdressing part 2

I had dressed up since I was a teenager but it was only occasionally. Usually, it was just lingerie and it was always for me and just for masturbation. It was about ten years ago that I decided I wanted to go further and start using makeup and breast forms and wigs etcetera.Quite by chance one day, I rang an old friend just for a chat. I found out that he had rented his house out while he was travelling. The person on the other end of the line was a woman, or so I thought. We got talking and I...

Crossdressing
3 years ago
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The twin sisters of the cross dresser policewoman

(This post is a fictional story on a bondage forum in China, and I am the prototype of the story. I just translated it into English. The copyright belongs to the original author, and the portrait right of the photos in the original link belongs to the original author and me)In the middle of a gloomy and horrible room stood a woman with a shawl. She was wearing a sexy red cheongsam, a pair of sparkling flesh-colored stockings like cicada wings wrapped around the beautiful woman's slender legs....

4 years ago
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AutoRide Made Me A Cross Dresser Whore 8211 Part 1

I’m a male, and cross-dresses occasionally in private. After cross dressing I get hard and then get off rubbing my dick against bed. Sometimes I post my cross-dressing photos online and get excited by comments and chats. I fantasizes about being seduced/forced to cross-dress and made to serve like a whore by dominant stranger(s). I’m darkish brown, lean. Has little hair on my upper body. Thin. Have slender arms. Soft face. And thick lips. And finger thick but long. My butt is rather fine and...

Gay Male
2 years ago
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Highlights of the Day A Jo Cross Story

A LITTLE PSA FROM JO: Kirsten has finished writing her update on the day for you all, but I've just taken the netbook from her to add a little something of my own. I want to thank you all for taking an active part in her adventures. The truth and the fantasy. If I sometimes seem a little pushy in the feedback comments about the targets I set....That is because I can only have Kirsten at certain times and days because of work, personal lives, etc. And as I read your amazing suggestions, I...

1 year ago
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My neighbor blackmailed and fucked me for Cross dressing

I had recently moved in a townhouse unit in Oklahoma. Still trying to adjust to the new neighborhood, I was also doing my best to keep my hobbies a secret. You see, I am a cross-dresser by passion. But my new neighborhood is strictly catholic and I can imagine the uproar my fantasies might stir. My next-door neighbor was an old man in his 60’s. He looked younger and stronger than his age. But, my secret unfolded and the neighbor fucked me for cross dressing. Within a couple of days of...

Cross Dresser
2 years ago
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An arrogant husband gets his comeuppance on a cross country trip with his beautiful wife of twenty years and their passenger a young black man

I couldn’t help staring at it. It was not only the biggest cock I’d seen, there was an aesthetic quality to it that begged a lingering look. Veins coursed over thick black flesh ending in a perfect golfball sized half-dome. It had to be eight inches long and, Lord Almighty, it was still soft! The first word that jumped to mind was “superior” I was staring at a superior penis. The kid’s voice snapped me back to reality. “Wanna hold it for me, Prof.?” he...

1 year ago
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Cross Dressing Lover

The weekend started off the same as any other for Dhiren. He threw off his drab male work clothes with alacrity and stepped into the shower. He shaved his face, legs and pubic area as was his custom, then, after turning off the tap, moisturized his legs, stepped into a pair of lacy pink panties and hooked on a matching bra. The feel of the light, soft, feminine fabric had always been a thrill to Dhiren, ever since that fateful day when, aged fourteen, he found himself alone in the house all...

Gay Male
3 years ago
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Katie and Jenns CrossCountry Nightmare

“What the hell?” Jenn quietly asked. Her car started to sputter and struggle. ‘I don’t know if we’ll make it very far’ she thought. She’d never been broken down before. She didn’t know what to do. She’d never been on a trip like this before either. She’d always been with Mommy and Daddy on trips like this. Her car was getting worse too. She wondered if she should just pull over to the shoulder of the interstate or try to make it to where they had planned to stay for the night. Katie and...

1 year ago
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Crossroads RulesChapter 5

Sid arrived in class early to watch the arrival of Cynthia. It was her grand unveiling - the first day in which she was going public, wearing her new wardrobe. He wondered which of the new outfits she would wear. He hoped that it was the blue dress since it was the sexiest of them. When Cynthia glided into the room, even Sid was surprised at the transformation. The loose fitting blue dress came down to her knees, was tight at the waist, and had a plunging neckline that just begged a man to...

1 year ago
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Confessions of a Sex Crazy Cross Dresser

The Confessions of a Sex-Crazy Cross Dresser Book I: The incredible first few weeks Chapter 1: Panties Thief and the Late Night Swim My name is Sandy. My name is Tony. I know it sounds confusing, but when you are a cross dresser life is always confusing. Just the terminology alone to describe you…crossdresser or cross dresser? Transvestite, tranny, she-male and many other names used to describe people like me can make you confused. I prefer to be called a cross dresser and yes you can call me...

2 years ago
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Cross One Mans Journey into Darkness Part One

No light reached this part of the room. The solitary sunbeam that had managed to poke its way through the curtains fell on a dirty heap of ripped up clothing in the far corner. But here, there was only darkness, and the ragged breathing of the room's sole inhabitant. Tyler lay naked, his arms and legs strapped to the corners of the bed with leather belts, allowing him no room to move or stretch his sagging limbs. Premature wrinkles lined the strong, angular features of his now gaunt visage....

Supernatural
3 years ago
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A Cross Dressing Fantasy ndash Chapter 5

A Cross Dressing Fantasy – Chapter 5In the low light of our bedroom, late on that Friday night after Beth had transformed me from a former cross dresser into her new girlfriend she had asked if I liked being her girlfriend. I did not hesitate for one second, “Yes Beth,” I said lying naked against her naked body, “I love being your girlfriend, something inside of me seems to have changed and this seems so natural and I feel complete.”My crotch was wet with my cum and her creamy arousal but I was...

1 year ago
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Dogging Cross Dressing and Porno

This new friendship proved to be fun and fulfilling, the girlfriend and the wife quickly became best buddies and the location of our nights together changed to her house. If we had nothing organised and they were free we spend Fridays or Saturday evenings in each other company. Usually just talking and drinking but more often than not some form of sexual encounter. Even vanilla fucking was done in each other company and the girls enjoyed playing with each other exploring the lesbian side of...

2 years ago
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CrossDressed Fairy Tales 3 The Adventures of Pierrot

Cross-Dressed Fairy Tales Part 3 By Dawn DeWinter In parts 1 and 2, Sherry and Sadie, two married men, went to a lesbian bar on their "girl's night out." There they came into the clutches of Mike and Big Sue, and are in danger of being raped - or worse - if Sherry cannot keep Big Sue entertained with "original" stories. This task has just become a mite more difficult with the arrival of two more people. Can they too be kept satisfied? Part 3 is based on Pinocchio, the story of the...

2 years ago
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Confessions of a Sex Crazy Cross Dresser Part 10

Only 1 chapter left after this installment....I hope you are still enjoying Sandy's adventures Chapter 19: Last Day in Vegas The next morning Tanya left for her house after exchanging numbers with us and promising to visit Peggy in Phoenix next month. The hotel had arranged a car to take Peggy to the airport for her 9:00 flight. I was sad to see them go, but at the same time, I knew I had work to do and I wanted to have some time to myself. I had to go to two accounts and I finished by noon....

Crossdressing
3 years ago
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Confessions of a Sex Crazy Cross Dresser Part 2

Chapter 3: New York with Linda I didn’t really get a lot of time to think about what I had just done with Carlos. I fell asleep shortly after he left due to all the drinks I put away during the night. I actually fell asleep on my couch, still full dressed except for my jacket and shoes. When I woke up, I had a headache and was starving; I never even had a piece of the pizza Carlos brought. It was 2:00 in the morning and I was scared to look in the mirror.I took a shower to clean off the make up...

Crossdressing
2 years ago
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Confessions of a Sex Crazy Cross Dresser

The Confessions of a Sex-Crazy Cross Dresser Book I: The incredible first few weeksChapter 1: Panties Thief and the Late Night Swim My name is Sandy. My name is Tony. I know it sounds confusing, but when you are a cross dresser life is always confusing. Just the terminology alone to describe you…crossdresser or cross dresser? Transvestite, tranny, she-male and many other names used to describe people like me can make you confused. I prefer to be called a cross dresser and yes you can call me...

Crossdressing

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