My Dream Vacation in Hawaii

XXX My Dream Vacation in Hawaii

nylontoni

A Young Man goes looking for a Transvestite Paradise and He finds it

Posted on October 16th, 2016 ~ 7:55 pm

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Chapter 1

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A magazine article caught my attention as I sat on the bus wearing lingerie under my mens business suit. The spread of pictures in the magazine was of transvestites hanging out on street corners and sitting on the stairs outside buildings that lined the street. This dream view was, "My crossdressing heaven". I was caught staring intensely as my heart raced with excitement. An old woman sitting across from me on the bus said to me, "Boy that must be an interesting article". I told her "Yes! Yes it is!" I continued reading the article and stared at all the beautifully crossdressed men. I examined carefully each "sissy" pictured in sexy poses. I noticed the stocking tops & garters showing, much like the one's I had on under my clothes. I looked at all the frilly dresses, lace, frills, ruffles, earrings, hair bows, pretty dainty purses being held by delicate fingers with nails painted red. These Beautiful men pictured were wearing many beautiful dresses, nylons stockings, and sexy high heels shoes that struck my fancy. These were the same kind of female clothes I dreamed of wearing some day. The hairdos and make up of each gorgeous transvestite was done up so beautifully feminine. I read and reread the article before realizing, this was a real place, in Hawaii. A place where everyone was a sissy crossdresser, transvestite, just like me. I decided I was going to go there SOON. I was filled with joy. All of my sexual fantasies could be realized if I went there! I even pictured myself dressed like a girl, having gay sex with a man. The name of this "Transvestite Area" went over & over in my mind, "Hotel Street". Under my male clothes, my huge erection rubbed against the silky panties. My cock was throbbing my balls ached to shoot the load of cum building up inside me. Getting up from my seat on the bus at my stop, the garters under my pants holding my nylons massaged my freshly shaved legs. When I got to work I was totally stimulated with an erection that felt as hard as a bone. When I got to my desk, I opened the magazine again to the transvestite article. I imagined myself joining these transvestite sissies walking the streets, putting on a dress, nylons, heels, a wig and make up and venturing outdoors. The thought of making these female fantasies a reality made my cock pulsate with ejaculate, I couldn't take it anymore. I read that "Hotel Street" was filled with Crossdressers, Transvestites, Gay men, male prostitutes, Sissy clothing stores, bars and everything this sissy mind ever fantasized about. I knew I had to get to a bathroom stall NOW, drop my pants & masturbate myself to orgasm. I was daydreaming about going to Hawaii now with a suitcase full of female clothes. I had my hands inside my satin pants pockets massaging my rock hard cock inside the silky frilly panties. My mind raced as I pictured myself walking the streets in a dress, wearing sexy lingerie. I hurried into the mens room and raced to get in the bathroom stall, unbuckle my pants and take my cock out of my panties. The buckle made noise as the pants dropped around my ankles. I reached inside my silky pink lace trimmed panties, I wrapped my hand around my stiff cock and faster & faster stroked the shaft of my cock. The cool air conditioning hit my shaved legs. It felt wonderful to feel the elastics on my garter belt stretching my nylons on my smooth legs. I trembled, I shook, I arched my back, I felt the eruption of semen coming from deep inside me. There it was! Spurting out of me with great force! Gushes of hot cum pulsating out of me in waves. I caught most of it inside the palm of my left hand. A pool of milky white cum also dripped down off my palm onto my pants. By body tingled especially my dick. I brought my left hand full of cum up to my mouth. I used my tongue to lick up all my cum. While I cleaned my hand, I thought "tasting my own cum was something I better get used to if I was going to begin sucking cocks. I washed my hands and went back to work at my desk. The taste of my cum remained in my mouth all day. I found myself looking at men's crotches thinking about giving all those men blow jobs. I fantasized about being a gay sissy, fairy on Hotel Street.

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nylontoni

Posted October 18th, 2016 ~ 3:51 pm

Re-wrote this story. How do you like the changes?

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nylontoni

Posted October 30th, 2016 ~ 3:27 pm

Hotel Street on the large island Hawaii is real! I'd still love to go there and sit with other sissies!

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Diaper Fantasies

Posted January 15th, 2023 ~ 3:36 am

I'm so glad I decided to look into the archives. I'm only on chapter 5 and this story has me so horny! If my sissy clit wasn't locked safely in a cage, I would be stroking it and feeding myself like the little sissy I want to be.

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nylontoni

Posted January 16th, 2023 ~ 8:54 pm

@ Diaper Fantasies

I'm glad you're massaging you clitty under a frilly dress while you read my story. I'm getting an erection under my pink frilly dress thinking about it. Feel free to subscribe and read my other stories. Lots of gay transvestite fantasy from my real life experience! Another story I wrote "Diaper Lovers Discovered and Shared" is also in the story archives, it's another good one written about real life experience!

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nappyon

Posted January 16th, 2023 ~ 7:50 pm

i love it i dress up all the time call anthony 706 7150633

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nylontoni

Posted January 16th, 2023 ~ 8:47 pm

@ nappyon

Thank you so much for contacting me. I too dress & wear diapers daily (entire life). I have a supporting wife & mistress who takes care of me. Please understand postings & contacts are constricted. You can contact me here & private message, OK? Stay dressed and stay in touch (subscribe even!) Try this story (also by me "Diaper Lovers Discovered and Shared"

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