Tranny Surprise Stories

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Punishment for my Tranny Virgin

by Creamyirish on Sep 16, 2017
Transsexuals & Crossdressers

He and I know each other very well, though we live in separate states. I shared a rape fantasy with him that was to happen when he came to visit me. Instead, he caught me off guard when I visited him and he raped me. I fought and fought but he had more strength and he raped my pussy and raped my ass and left me bruised and bleeding. We share many fantasies...

Private Eye's Birthday

by Selbryth on Sep 16, 2017
Transsexuals & Crossdressers

In the dimness of the evening light, it looked like two pale bodied women sitting together on the couch. Al could see them quite clearly now through the three story high plate glass windows of the estate. They sat there watching the sun going down. He thought perhaps they were really dedicated sun worshipers because they sat there with almost no light, compl...

Greg Tries a New Angle Ch. 02

by kjherts on Sep 15, 2017
Transsexuals & Crossdressers

In part 1, Greg posts a selfie in his ex-wife's panties to lure a man's man on an adult dating site. To his delight, he meets Drew, who talks lightly but carries a big stick. Earlier in the afternoon, Drew unloaded in Greg's mouth, with the promise to return that evening to take care of unfinished business... ***** It was approaching 10 pm and three candle...

Discovery by Disguise

by jenniferjoannarose on Mar 14, 2018
Transsexuals & Crossdressers

He bent me over and fucked me with a vicious hunger. This was my very first time. This gorgeous hunk of man was popping my gay cherry. He was so big, so very big, that I was afraid he was going to break my ass. I was hurting, but I was nowhere near wanting him to stop. He was bigger than the largest butt plug I had using to train my ass for just a moment as...

Forced Into Submission

by lonejackman on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 1 "Oh shit, fuck my black ass with that thick white cock you fucking tranny." He moaned. "Harder, rape my tight fucking ass baby." He screamed "Quit screaming like a bitch and take it like a man cock-whore." She exclaimed. He could feel a growing sensation of pleasure in his taint, a feeling of unnatural pleasure building up inside his loins that...

First Dawn

by Winterloverm on Sep 16, 2017
Transsexuals & Crossdressers

I had treated myself to a beautifully luxurious bath with scented candles adding that little extra to the occasion. I was just putting the finishing touches to my makeup when I heard "Come here Dawn. I have laid out your clothes". I'm a lucky girl my Tina looks after me so well. I went into the bedroom and laid out on the bed were my stockings, suspender b...

First Bi MMF

by synn14 on Sep 13, 2017
Group Sex

My boyfriend and I had just gotten home from going out for a few drinks. He seemed anxious to get home; normally he is in no rush and probably would have had a few more. I asked him if everything was okay and he said he had a surprise for me tonight. A surprise from him could be just about anything. We have a very active sexual relationship, including swing...

The Sexy Cuckold Couple Pt. 13

by cuckcpl4play on Sep 19, 2017
Fetish

Part 13 Vegas Arrival We quickly departed the plane and as expected, Master had a limousine waiting for all of us. Getting into the limo, Master asked his slut / my wife loudly enough for all of us to hear, "Is that stretched out pussy already tender and sore?" My wife immediately responded that it was hoping that Master might express some niceties or co...

Mistress Chantel, Tranny Dominatrix Ch. 12-13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twelve: Another Play Day Work Day at Our Studio. I arrive at my studio dressed for another day of fun and exciting dominatrix work. I park my "Plum Crazy Girl." step out in my red leather thigh high boots over my black sheer pantyhose. On my feminine looking body is a red leather form fitted mini dress with loose pleated, A-line skirt barely coverin...

Sexual Adventures of a Horny Tranny

by sheer2waist21 on Sep 13, 2017
Transsexuals & Crossdressers

My heart was beating uncontrollably with anticipation. No matter how many times I do it, it never loses its arousing appeal. As I slowly and carefully finished running the razor over my thighs, I continued on to my chest and then my ass. The feeling was mesmerizing as my newly shaved asshole and balls were left bare and ready to be violated by the next lucky...