T Party Ch. 01

T Party Ch. 1

"That would be great! See you then!" I replied excitedly before I disconnected from the Zoom call.

I smiled to myself as Ivanka's image disappeared from my screen. Ivanka (actually called Ira IRL) just informed me of a weekend gathering for T's; Transsexuals and Transvestites. It was an opportunity to dress up and enjoy myself with others. I immediately registered myself and reserved a room at the hotel where the T Party event (a number of weeks away) would take place. I could barely wait.

I placed my wig back on its stand and used cold cream to remove my make-up before having a shower. I loved soaping my smooth, soft body. All body hair save for a small pubic patch, removed via electrolysis so I didn't have to shave any more. I dried off with a big, fluffy, pink towel and lightly dusted on some perfumed powder. I stepped into some cream-coloured satin tap pants then then buttoned up the matching short sleeved top to sleep in.

In bed, my mind was raced thinking of the T Party. Friday night was a social mixer followed the next day by a day of golf or spa and then the final banquet with a special guest speaker. It was quite an expensive weekend but well worth it. My mind drifted to how I started dressing up.

I remember going to a Cosplay party dressed up as Superman. Even with the costume, my scrawny physique didn't make much of an imposing superhero. I remember pulling on some blue tights and the red panties and thought how wonderful they felt. I was embarrassingly hard all party. Thank goodness for the cape. Afterwards, I'd put on the panties first and then the tights. I just loved the way they felt.

I went through a number of tights and pantyhose before I discovered stockings. Oh my gawd, how I loved the different styles, patterns and textures and how they felt encasing my legs. But they always slipped; even stay-ups. Garters were the obvious solution. The straps and buckles were constant reminders of my feminine under things.

Bras quickly followed along with many accoutrements. Now I have a complete fem wardrobe to choose from. Of course I couldn't wear my girl clothes to work but that didn't stop me from wearing some sexy panties and such.

It was at work where I met up with Ivanka. Actually it was after work. On Fridays after work, some of us get together for drinks to unwind from the week. That day, I wore my black mesh cheeky panties. They had a lace front panel with a red bow just above my bum crack. I wore them over my high waist, plain black garter belt. It had a four hook and eye rear closure and six thick, dangling straps to hold up my fashioned seamed stockings. I adjusted the big buckles so the straps were tight against my skin just as a reminder with each step I took.

I was standing at the bar waiting to get served when Ira came up to me. "Hi there, Jeremy. I hope you don't think me a too forward but I would love to see you in just your garters and stockings!"

"Wha... What?" I stammered. "I... I'm not wearing..."

"Oh, it's okay. I'm wearing some myself." He said. "Your garter straps are so tight, they make a slight indenting line in the material of your trousers. Very unmistakable to the eye."

I looked around to see if anyone was overhearing his accusation. I couldn't deny the truth though.

"Don't worry. I won't tell anyone." He smiled. He perched his foot on the bar rail to prove his point. Along the top of his thigh was an impression and a bump. The impression was from his garter strap and the bump was the strap buckle. "I sometimes go as Ivanka. And yes, like Ivanka Trump."

"Uh... I'm... Uh..." I stammered back automatically. "Si...Siobhan."

"Really nice name. Irish isn't it?"

Ira was a co-worker in the area adjacent to mine. We knew each other to say "hello" but not socially. He and his group frequent the same bar we did.

Ira pulled out his phone; swiped it a few times and then showed me a picture of Ivanka Trump. He grinned. "No, that's me!"

My mouth dropped as I took a second look. He swiped a few more pictures. He looked exactly like Ivanka!

Long story short (maybe for another time), we became friends. I learned a lot from Ivanka during our time together but unfortunately a sickness in the family required him to move away. We still kept in touch though. When he told me about the T party, we'd be able to meet up again. But first I would need to get my party gear together.

The event was a short drive across the Canada-US border. Since my passport showed me as a male, I couldn't go fem until I passed customs. That didn't mean I couldn't dress up a bit though.

Friday morning, I finished packing my two huge suitcases and my big make-up kit and stuck them in the back of my Lexus LX570 before I changed into my driving attire. I carefully attached my Double-D, custom, self-adhering breast forms and supported them with my red bullet bra. My matching panties were tight fitting, high waist, nylon mesh under my six strap, red satin garter belt. I decided on some wide leg black slack and a crisp, white linen, button up (mostly unbuttoned) blouse. Finally, I slipped my male size sixes into a pair of women's red size eight, open toed pumps. The pointy heels were only three and a half inches to make it easier to drive.

The female customs agent gave me a funny look as I handed her my passport. While the high doorframe hid my big bosoms from her, my long, sparkly red painted acrylic nails were very obvious. Once clear, I knew of a place to complete my look.

I fixed my make-up with eye shadow and mascara and painted my lips a bright cherry red. I opted for my bob cut, red wig since it was getting warmer out. My big brimmed hat and cat-eye glasses finished everything off for the short two hour drive to my hotel. My hand was inside my pants for at least one hour, fifty-five minutes.

"You have arrived at your destination." My GPS informed me.

There were a number of cars lined up. The car hops were hopping and jockeying cars. She smiled at me as she pulled out my luggage. "Welcome to the Belmont. Registration is just inside but please check in first."

"Thank you!" I smiled back and opened my purse to tip her when I realized she was a he. I gave him...her a fiver. "Wow, really going all out aren't they?"

A bell hop helped me with my bags as I walked to the front desk. I looked around at all the "girls" already lingering in the lobby. Some friends; others just taking it all in.

"Good afternoon! Welcome to the Belmont." Said Regina behind the counter. Check-in was very quick and efficient. "Ms. Siobhan. There is a message for you as well. Enjoy your stay."

I took the note from Regina and opened it up. It was from Ira/Ivanka.

Hi Siobhan.

Unfortunately I can't get there today but will be there for dinner tomorrow.

Love Ivanka.

I was disappointed but I was sure I would enjoy myself anyways.

The hop helped me to my oversized room. Over the top for sure but I really wanted to indulge myself. I placed my purse on the desk and snuck a look in the mirror to make sure I still looked presentable. I pulled a twenty to give Greg but as I handed it to him I "accidentally" dropped it. "Oopsy! I'll get it."

I knelt down in front of him and pulled down his pants. My mouth drooled as I saw that he was wearing the cutest, pink lace, bikini panties. His dick was already hard and sticking out the waistband. I pulled his panties down his thighs and took his knob into my mouth. He was at least seven thick inches but I managed to get my lips around his base.

"Oh gawd!" He groaned. "No one has been able to take it all like that!"

One hard thrush and I was swallowing his hot cream.

Greg left with a grin and a bit little wobbly and my twenty. The welcome get together wouldn't be for another couple of hours yet so I stripped off and enjoyed the big whirlpool bath in my room. The swirling hot water felt great after my travels and that liquid snack.

I didn't stay in too long; didn't want to get too wrinkly. I had to lay out my attire for the evening. Since the gala evening was tomorrow, I stayed with my Double-D's and supported them in a black demi-cup bra. Panties were a small G-string; big enough to control my uncontrollable penis. The string ran deep along my ass crack and hard on my asshole. I slipped on some 15 denier, black seamed stockings with reinforced toes and Havana heels and clipped the wide lace welt to my black eight strap garter belt. I opted for medium make-up but laid on heavy mascara and ruby red painted lips.

I placed my burnt orange wig in place and combed out the shoulder length hair. Careful not to muss it up, I gingerly shimmied into my sleeveless LBD. The front had a nice Vee neck to show off some cleavage while the skirt hem was mid-thigh and long enough to hide my stocking welts. The outfit would go perfect with my simple, matched cultured pearl necklace and drop earrings. I slipped my feet into some red Jimmy Choo, pumps. The stiletto heels were over four and a half inches. They swayed my back so my bum and boobs stuck out more.

I checked myself out one more time before I grabbed my Gucci clutch and left the room. Typically, I love the echoing sounds of my clacking heels against a hard floor but all the hotel floors were carpeted dulling any clicking noise. While I waited for the elevator, I was joined by a gentleman and his lady. We smiled at each other. I spoke first. "Hi. I'm Siobhan. Are you going down to the reception?"

The lady spoke. "Yes, we are. I'm Rochelle and this is Tim. Happy to meet you, Siobhan."

When the elevator arrived and the door opened, we joined the three other ladies inside the car. I immediately noticed how Tim shied away into the back of the car as the doors slide shut.

When we arrived at the ballroom, there was already a big crowd. I sauntered up to the bar and got a glass of Chard. I didn't know anyone there so I just hung around the bar. Rochelle approached with Tim bringing up the rear. "Hi again, Siobhan! Would you like some company? We don't know anyone here."

It was the first time I really looked at the pair. She stood only five feet but had a very confident aura about her. She was dressed in a business casual outfit with low heel pumps. Tim stood almost six feet with his head bowed and shoulders curved slightly.

"Hi again, Rochelle and Tim. Yes, please. I was expecting to meet with a friend but she won't be here until the banquet tomorrow."

After a bit of small talk, I found out that Rochelle was the dom of the relationship. She was a transsexual but didn't complete the change. "It was too nice to cut off." We found a table to sit at and I discovered that my hem rose up higher than I expected; almost high enough to show my stocking welts. Embarrassed I brushed the skirt down.

"What a pretty outfit you have on, Siobhan!" Rochelle commented. "Very classy. Some of the other girls are dressed kind of skanky, don't you think?"

"Yes, I agree. I guess the dress requirements didn't include taste." Many of the others were dressed too loud or applied too much make-up screaming "Look at ME!"

Rochelle suppressed a giggle.

Our conversation flowed and the evening went quickly. Many had already left with the bar closing up. Rochelle asked me. "Would you like to join me in my room for a night cap?"

"Oh, yes! That would be great." I answered. "But I do have to get up for golf tomorr... later this morning."

We barely made it into her room when Rochelle took hold of me and planted a hard kiss on my lips. "I wanted to do that all night. You look so sexy with your stockings teasing me from under your dress."

I guess I was a little stunned but I didn't protest. Rochelle helped me off with my dress and handed it to Tim who handed us some wine. As Tim hung my dress up, Rochelle knelt before me. She pulled down my thong and freed my hard six inch erection. Rochelle pulled my foreskin slightly to expose my tip and kissed it. Her swirling tongue was making my knees shake. Rochelle easily swallowed the rest of me.

I looked at Tim and noticed he was just standing off to the side waiting.

Rochelle instructed me to sit lie on the bed. Tim finally moved and from behind started to undress Rochelle. Her suit hid a lot and I was surprised when she exposed herself to me. A firm body with large full breasts and hard pointy nipples. Tim pulled down her panties and exposed a beautiful, thick, eight inch, uncut cock.

Rochelle moved between my legs. She lifted them from under my knees. Meanwhile, Tim spread some lube on her cock and my ass hole before aiming it on my rear entrance. My mouth gaped slightly as I nodded "Okay!"

Slowly Rochelle pushed forward. My eyes closed as my mouth opened wider; no noise came from it. She back off a bit and then pushed forward more. My hole spread open for her and allowed her knob to pop through. I groaned. "Oh! Fuck! Yes!"

Rochelle continued to enter me until her haunches were pressed against my ass. I knew then it was going to be a long night and playing golf was going to be a bit difficult with a sore ass.