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My First Time

A true Halloween cross-dressing story
I met Lydia while living in Florida. I had recently won a law suit and didn’t need to find employment for a while, so I spent the first three months partying. A good friend had sponsored my membership at a well known and popular yacht club. They had a public side and a members-only side; the members-only side had better bands and more folks.

If you parked your yacht and paid the docking fees, admission to the members' side was free. Otherwise, admission was for members, or in the company of one, and rigidly enforced. I paid the yearly membership and spent countless nights up there. It was on one of those nights that I met Lydia. She was a tall, tanned brunette whose looks made her a much desired target of men, and some women, on the prowl.

I tried to start a conversation and was ignored, I figured she had heard every pick-up line that started a simple conversation. So I ignored the cold shoulder she gave me. Later I just happened to bump into her while enjoying breakfast at a local Denny’s. We started chatting and we both felt an attraction . We started dating and sleeping together shortly after that chance meeting.

Halloween was less than month away, so one evening we stayed in deciding what we would wear. Now, I love Halloween, and won many prizes back home for my Dracula and Frankenstein Monster costumes over the years. She had a different idea. "I want to dress you as a Dominatrix . . . and I will be your slave," she stated.

"You want to dress me up as a woman? Not going to happen," was my response.

"Oh come on, it's Halloween, what's it going to hurt?" she questioned.

"I am not going out in public dressed as a woman," I responded.

She begged for me to to change my mind.

"Look, even if I said yes I would still look like a man wearing a dress," I insisted.

“You need to have faith in me. I would not let you look ridiculous,” she added.

This discussion lasted for 2 days, until finally I agreed to her wishes.The next time I spent the night she measured me as though for a new suit, and just smiled when I asked why. Finally Halloween arrived. It was on a Saturday.

Lydia asked me to come over and spend the day and I agreed. The party didn’t start until 8:00 pm so we had plenty of time. It was at about 5:00 pm that there was a knock on her door. Lydia admitted a tall woman laden down with suitcases.

"This is Queenie," she said in the way of an introduction.

Lydia poured wine and we all had a drink and chatted. Queenie studied my face at different angles; it was a little uncomfortable. She finally spoke. " Well, you are correct,” she said addressing Lydia, “he has excellent skin. This shouldn't be a problem."

Lydia took me to the bathroom where she assisted me in shaving my underarms and legs. Thankfully I was, and am not one of those males covered with hair, but I was beginning to regret agreeing to her request, as this had not been discussed.

After a shower and wrapped in a towel, I returned to the living room. Lydia then excused herself, heading to the bathroom to begin her own Halloween makeup. Queenie had opened a professional makeup case and set up some extra lighting. She bade me take a seat where she combed my hair back and then secures it under a net.

She immediately went to work on mw. The only mirror was face down on that table, so I could not track her progress.

I expressed my doubt in her efforts and she responded with a laugh.

"I am one of the top makeup artists in South Florida. If I charged you for this, it would cost you big-time."

I remained silent as she worked, and about 2 1/2 hours later she handed me a long dark wig and gave me instructions on how to don it. She double checked it and then ran a brush through it and sprayed some hairspray.

"OK," she said, "tell me what you think now." She held up the large mirror that had been face down. I could not believe my eyes – there staring back at me was an attractive girl's face on my body.

"This is unbelievable," I stated.

Queenie packed up her gear and was out the door in a flash."Say goodbye to Lydia for me,” she said, “because I have to fly, as Halloween is a very busy night for me."

I knocked on Lydia's bedroom door and was told that my costume was in the back room. There laid across the desk was what she expected me to wear . . . I almost told her I was sick and left. A black mock-leather miniskirt with a slit up both sides and a skin tight mock-leather top, black leather gloves, black studded bra and numerous spiked wrist bands.

It was the nylons, garter belt, black speedo and the set of fake breasts that I had a problem with, but I had gone too far to turn back now. Following the instructions, I took the bottle of adhesive and applied it to the breasts, placed them on my chest and held them in place for a minute, and then slipped the bra on over them.

It took a long time to dress as, “thin silky nylon things can tear easily,” Lydia had been telling me through the closed door. Finally, fully dressed, I looked in the mirror. I still could not believe it. Not bad , I thought to myself. My engineer boots gave me 2 inches of extra height, so I was now about 6'3". I knocked on Lydia's door and she opened.

She was clad in a white lace body suit, a white leather garter belt on the outside holding up white thigh-highs. "Wow, you look totally HOT," was her comment to me. She then affixed a white dog collar to her neck and attached a chain.

"Ready?" she asked.

"Not really,"I answered.

En route to the nightclub she gave me instructions on how to sit and stand in a short skirt. Upon our arrival, the valets that knew me could not believe their eyes. The sensation of my nylon clad legs brushing together as I walked really turned me on.

We entered the members side and 98% of those in attendance were in costume. It was one of the best parties I ever attended. Whenever she was asked to dance Lydia would always ask for permission.

"Mistress, may I have permission to dance?"

I always allowed it. I was also asked to slow dance by a number of ladies, their hands always seeming to wind up under my skirt. More than one male asked me to dance, and of course I refused.

 The party ended around 4:00 am and we returned to Lydia's and I got ready to take off the costume and remove my makeup. Lydia stopped and pulled me into her bedroom.

"You are so dammed hot," she stated as she started kissing and touching me. The reflection in her bedroom mirror showed two women locked in a lovers embrace.

"I want you Mistress," was all she could say. I removed her bodysuit, leaving her nylons on, and began to kiss her neck and breasts as I worked my way down.

"Yes, lick my hot pussy", Lydia begged in between kissing my neck and the fake boobs through the bra.

When I could not stand it any longer. I tore off the speedo.

"Are you ready bitch?" I asked.

"Yes Mistress, fuck me hard." Lydia's answered in a breathy voice.

I then pulled her off the bed and took her before the full length mirrors that covered her closet doors.

"Get down on all 4's bitch", I commanded.

I then entered her from behind. I had never seen her this turned on, and I was more turned on than I had ever been.The mirrors reflection showed an amazon of a Dominatrix fucking her little submissive. I lost track of the number of orgasms she had. Finally, I couldn’t hold out any longer and finished.

"Next time I have a nightie picked out for you," she said, continuing, "I would have loved to see you in a sexy nightie."

"Who knows what the future holds," I answered.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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