My first time going out dressed like a woman

My first time going out dressed like a woman
A few months back I met a dominant woman. We got along really well. After dating a couple of weeks, Melissa and I were out having drinks. She began asking me super personal questions. I was reluctant to answer her questions. She began buy whiskey shots. I believe in the intent to make me confide in her my most inner fantasy secrets. After a couple of shots, I confessed to her that when I feel submissive I’ll put on some female items I had bought. Then I’d watch Shemale and crossdressing porn and masturbate. She continued to ask questions along these lines and asked me if I thought I could ever go out in public dressed like a woman or pursue the things I saw in those videos I watched. I told her I wasn’t sure, that I didn’t think so.

A couple of days went by and Melissa called me up and asked me to come over. She told me she wanted to take me shopping. We got in her car and drove about an hour to a larger town. The first place she pulled into was a plus size woman’s dress shop. I asked what we were doing here since she is not plus size. She informed me she was going to help my fantasy become a reality and part of that was going through the humiliation and giving into my true desire. She took me into the dress shop and we looked around. After a few minutes she asked a saleslady if she could help her friend (me) find the perfect dress. I was shocked, but went along with it. The woman found several dresses for me to try on. I went into the changing room and changed into each dress. Coming out of the changing room and getting the opinion of Melissa and the lady. I felt so humiliated. With there advice I picked out a blue floral dress. I made the purchase and we left the store.

Our next stop was at a woman’s shoe store. We browsed shoes for a little bit. Then again Melissa asked the salesman if he could find me a pair of heels that would fit me. He brought out several pair and I tried them on. He kept glancing at Melissa. After trying on several pairs of heels and walked around in them I settled on a black, short heeled pair. We made the purchase and he kept looking at Melissa as he rang up my purchase.

She drove for a little bit and asked me if I was satisfied with my purchases? I told her I like what I had bought, but felt awkward and humiliated trying those things on in front of others. She told me that’s part of the excitement of it all. She then pulled into the mall. She walked directly to the lingerie store. She found a few pair of panties and stockings and suddenly stopped one of the workers and asked, “Do you think these would look good on my friend?” She clerk blushed and replied, sure. She had picked out a pair of black satin panties and black stockings.

On the drive home, Melissa said our next purchases will have to be made online. I was fairly silent on the drive home, but felt strangely excited about my new items of clothing. Once we got back to her house she went online and started looking at wigs. She asked me what color of hair do I want to have. We picked out a nice blonde wig. She then maneuvered to an online transformation site. She said we want you to look as real as possible when you make your debut. She found a sleeve to hide my cock in so I would have a bulge. Then she found a padded girdle so I had a more feminine looking butt. It was padded as to look real. Then she found some fake breast with the right touch I would look like I had real boobs.

Over the next couple of days she showed me how to apply makeup and lipstick. She told me before I go out, I have to shave my entire body. She had found some makeup to hide my 5 O’clock shadow when I finally went out. Melissa took me out to get a manicure and pedicure. Finally she had me put everything together and get dressed so she could see how I looked. Melissa said she was amazed, although I was tall and had an athletic build, I could pass for a woman. She told me it was almost time for us to go out in public.

With short notice I was told at work I would have to go out of town for several days for a conference. Melissa said it would be good for me to make my first appearance as Kathy out of town. That way I wouldn’t be so nervous and there would be a lot less chance somebody might recognize me. She suggested that I pack my Kathy clothes in a separate suitcase and when I got the chance I should go out in public. She told me to call her and she would help me get ready.

I flew out to a large East Coast city. The first two days I was too busy with the conference and was too tired afterwards to go out. On the last night I was there I called Melissa and she took me step by step to get ready to go out as Kathy. She talked me through applying my makeup and lipstick, getting my wig on right and secure so it wouldn’t come off. After almost two hours of prepping I was finally ready to go out and make my debut as Kathy. I thought it would be best my first time to go to a dark club or bar. I got a taxi and in my best female voice, I asked him where I could go have a couple of drinks.

He drove for only a few minutes and stopped in front of a nightclub and told me it was a popular place. I got out and walked into the club. I was sitting at a table by myself having drinks and watching the crowd when two men sat down and asked to join me. I said sure and they sat down. They bought several rounds of drinks and made small talk. They complimented me on how I looked. That made me feel good. I wanted to text Melissa and tell her what was going on, but suddenly I felt dizzy and light headed. I tried to excuse myself, but the next thing I knew I was in someone’s basement blindfolded and restrained to a padded device.

I heard one of the men say, “We don’t care that you are some sissy crossdresser, we are still going to fuck you like a dirty whore and there’s nothing you can do about it. I felt one of them move behind me and force his cock into my boipussy. It hurt bad and I screamed. He laughed and said, Nobody is going to hear you down here. He just kept fucking me. Then another one came up and shoved his musky, small cock into my mouth. I sucked it reluctantly. I didn’t want to be hurt. I felt so humiliated because after a few minutes the pain subsided and began to feel good with him fucking me. My clit got hard and I began moaning. I sucked the other’s cock eagerly and loved being fucked and used like that. They laughed at me seeing that I was turned on by their actions. They took turns fucking me and having me suck their cocks. I felt like I didn’t want it to end.

After about 30 minutes both of them had cum in me. I swallowed a load and taken a load deep inside my boipussy. They kept the blindfold on and drove me back to the club. I was barely dressed, my panties were soaked from the cum leaking from me. They shoved me out of the car with the blindfold still on. I didn’t bother getting a cab. I walked back to my hotel feeling so humiliated yet turned on.

I got make to the room and took a shower. I stroked my clit while I showered. I didn’t text Melissa, but I told her what had happened while I was out of town. She asked me how I felt about it. I told her I couldn’t believe how turned on I was by it and how good it felt.


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