Tranny/Shemale

57 Free Gay Erotic Stories in Tranny/Shemale

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Mein erstes Mal in Nylons

by biboyvienna

Es war ein Faschingdienstag! Mein bester Freund und ich hatten uns entschlossen auf eine Faschingsparty zu gehen! Er gind als Exhibitionist (mit braunem Regenmantel) und ich ging als Nutte (weil ich schon immer gerne Frauenkleider trug)! Wir hatten jedenfalls genug getrunken, als wir gegen 3 Uhr frùh zu mir kamen! Er wollte an diesem Tag bei mir schlafen, da er weiter drauöen wohnte! Ich...

Gay Erotic Story

Black Daddy

by xzibit

I’m Steven I have been cross dressing for years but have never gone out in public. I love big black men and dream of the size of their cock every time I see one. I was partying one night and arrived home late; I noticed everyone was asleep in the neighborhood as I have always wanted to dress and go out as a hot whore. So I began my transformation; I have a hot body so I was looking alright. I...

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Merchandise in Malaysia

by EugeneTB

I was stuck in a hotel in Jakarta. My trip to buy merchandise for the store chain that I worked for was not going well. I had stayed at the hotel a few times and I had seen her before, slim, well-dressed, permed hair wavy. Not a great looker but definitely more than presentable. My guess was Chinese origin. We had exchanged pleasantries at the bar but no more. Usually she left with very rich...

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Angled Entries: Painted Laddie

by Habu

When Ms. Elisha came off the stage at the Bourbon Street female impersonators’ club and swished into her dressing room, Chas Angle was waiting for her. The meta hunk had worn a muscle shirt barely covering the superhuman bulges of his torso and a silky pair of shorts that barely held the bulge of his twelve thick inches. So, when he asked her if she’d come pose for him for photos, her quick...

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She's A He

by Hardcharge

Warning: this is my first story I was sent to Singapore for a six week assignment--a fairly easy, but time consuming type of assignment. I worked seven days a week getting back to my Orchard Road hotel about 7 pm every night. The routine was a couple of drinks in the hotel lobby then out to diner and back to the hotel around 10 and to bed. Every night as I walked back to the hotel I would...

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Try These

by cggiym01

I went over to visit Gus at his home in the suburbs the other day and found him outside by the pool. I had been seeing Gus on and off for about 2 years and we have done almost everything. He is 62 years old and I am 52 both married, with me being a bottom and him a top. We have had a great time of things. I walked over to the lounge where he was sunning himself and dropped to my knees along...

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Subic Bay Port Call

by dickandy50

Transvestite Cum Loads While in the navy, my ship pulled in for a port call at Subic Bay in the Philippines. It was during the time of the Marcos regime, which meant martial l law. All Americans had to be off the streets from midnight to 4 in the morning or you were locked up. No one had any problems with the rules, since it gave a reason to make a decision by midnight whether you were...

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Joe's Plaything

by cggiym01

Joe was on his way to my house. I’d told him to enter through the back door, which would be unlocked. As always, I prepare for his visit with a few warm soapy enemas to clean myself up. After the enemas, I put on a garter belt with hose, bra and panties. I walked to the window to see if he’d arrived, as I took a little longer to get ready. As I got to the window, my neighbor Betty was...

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Meeting my Haitian King Pt. 1; Gwo Zozo Met

by teachmedeepthroat

Last Thursday I connected with a man online. His profile had no significant content, but his stats were impressive. Almost as impressive as the two photos he included of his huge soft penis. We began chatting and then he mentioned that he wanted to own. I gave him my number and we began talking. It turns out we were better matched than I had imagined. He was a Haitian Man, 53,...

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