Sissy Time

XXX Sissy Time

nylontoni

A summer time tradition at the sissyest place on earth

Posted on December 20th, 2015 ~ 2:02 am

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Chapter 1

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Every summer I pack my sissy suitcase and I head to the sissiest place in the world. Cherry Grove on Fire Island. It has always been known as a haven for people like me. To get there, I have to fly into Long Island MacArthur Airport in Ronkonoma. I usually get a hotel room at the nearby hotel. I have a few gay friends who live in the area and they love to come by my hotel room for a night of sissy love making before we all go over to the grove for a few days of sissy fun. My God! My suitcase is loaded with lingerie, dresses, shoes, make-up and wigs. You had to see the looks on the Airport Security when the had to wand my legs for the metal garter clasps holding up my nylons. I also went through x ray so they saw my women's underwear I had on. My bra wasn't underwire but it did have metal adjustments on the shoulder straps. My luggage was inspected and they saw lots of lacy pink bras & panties, garter belts and fuck me heels, wigs and make up. No doubt they knew they were looking at a sissy queer fairy's luggage. They called me "Miss" even though I still looked like a man. I felt girly underneath. Arriving at the hotel, I swished my way up to the front desk and got my room. I would be here for the week so I unloaded my suitcase into the drawers in my room. I put my make up out on the table top along with my wig, wig stand and high heel shoes went on the floor. Hopping into the shower, I got myself washed, shaved my legs, plucked my brows, polished my toenails & fingernails. I pulled up a chair and got out my make up mirror. I did my make up which included false eyelashes and red lipstick. I picked out a black pocket bra, breast forms, matching panties and a long line garter belt with six straps. Looking at myself in the mirror after attaching the garters to the nylons, I looked hot! I put on my soft satin nylon dress and zippered the back. Putting on my wig and adjusting my dress I called my friends on the phone asking them to join me at the hotel. My friends met me in the restaurant bar just off the lobby. Jack who was a rough biker dude had a soft spot for beautiful trannys. I knew him for years. Bob who was mainly a closet queen was always rather shy and loved the company of sissies & drag queens. Bob came to the hotel in men's clothes. I'm not sure what he had on underneath but I suspected lingerie. I could tell he regretted not wearing a dress after seeing the fun I was having being dressed totally sissy. I'll bet he was wishing he was me. Doris was a fun loving butch lesbian. The four of us drank all night, laughing and remembering great times from the past. We danced to the DJ music which was mainly fast with a few slow songs. I glided and twirled my dress so high I'm sure I exposed my panties nylon tops & garters on a few occassions. I was a beacon of femininity as I swished the hem of my dress from side to side to the music. Jack was horny that night, he was turned on from watching me and continued grinding and pressing his huge erection up against me every chance he got. His hand was under my dress most of the time stroking my panties. The rest of the time he hiked up the back of my dress and was fondling my ample round ass through my panties. I was enjoying it knowing the whole time he was giving everyone a show and the hornier he got the harder he was going to fuck me.The whole time on the dance floor he kept telling me how beautiful I looked and smelled and much he wanted to be deep inside me. Doris was enjoying the view watching Jack and I on the dance floor. When Jack and I returned from the dance floor, Doris reminded everyone that she would never wear female clothes. It was Jockey or Fruit of the Loom only for her. Looking at me she said, I know, Maidenform, Playtex, Vanity Fair.She was right again! Indeed she was more macho than most men I know.We laughed again!

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Prissie

Posted December 23rd, 2015 ~ 3:43 pm

I like to think of the lady above, as a thirtysomething divorcee or a woman who's not yet married, getting ready for a Saturday rendezvous with a younger guy to give him his first sexual experience.

Part of the foreplay could include him trying on things like we see above.

MC&HNY to all my sisters in love of all that is sweet and feminine and divine,

Prissie

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BBBillie

Posted October 25th, 2016 ~ 3:10 pm

What a wonderful story!

What I'd give to be on that island!!!

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nylontoni

Posted October 26th, 2016 ~ 1:14 am

@ BBBillie

Some places are make believe. THIS PLACE IS REAL!

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nylontoni

Posted October 30th, 2016 ~ 3:17 pm

@ BBBillie

Every summer this place is REAL. Sissies & Transvestites from all over the world go to "The Miss Fire Island Beauty Pagent". If you're lucky, you'll be called up on stage to have the back of your dress pulled up and get spanked in front of everybody!

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