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A Shopping Trip Surprise By Tricia

I had been secretly going on a crossdressers web site for about a year. At first, I was very cautious and did not communicate with anyone. I would usually just browse the pictures while being dressed myself. I slowly began to be more comfortable and started to build my own profile along with uploading some pictures of myself. At one point after a few drinks, I tried to contact “Cindy”, one of the gurls that lived in my area. She did not reply but in my last post to her I let her know that I shop and browse in the woman’s department at one of the shops in the local mall on Sunday mornings if she would ever like to join me. I nervously waited to hear a response from her, but when she did not respond in over a week I figured the whole thing was behind me.

The following Sunday I slipped on a pair of stocking under my jeans (to get me in the mood) and headed to the mall for my usual shopping session. While I was browsing through the dresses I heard a voice from behind me say, “I think you would look lovely in that Tricia”. I was paralyzed, Tricia was my screen name on the crossdressers web site, I tried to swallow and closed my eyes as I turned to see wear the voice had come from. As I opened my eyes there stood Cindy in front of me, she smiled at me and said “well do you want my help picking out and outfit? I just nodded my head yes, as I was still to shocked to say anything. As we shopped, I started to become more at ease with Cindy and I found a stretchy pullover dress that we agreed would be perfect for me. With my dress in hand I headed for the check out, Cindy said she would meet me outside as she had a few more things to get. All the lines were long and I was glad that I did not recognize anyone as I looked around. I finally approached the sales clerk and handed her the dress, she asked will that be all for today? Before I could reply, Cindy yelled from several isles over “Hey Tricia, wait a minute I picked out some stocking for you to go with your new dress”. As she approached she handed me several pairs of stockings, all eyes in the store now seemed to be focused on me as she asked, I wasn’t sure if you would want suntan or nude so I got both, is size B ok? As the redness of shame filled my face, I took the stockings and handed them to the clerk. She looked up at me and smiled as the women in the nearby isles began giggling and laughing at me, one of them even leaned forward and said, “With your completion sweetie I’d go with the suntan”. I was completely humiliated as Cindy continued her onslaught, “Tricia do you have shoes to go with your new outfit, or should that be our next stop dear”? The woman from the next isle again chimed in saying “you can never have to many pairs of shoes dear” and another girl added, “nothing gets a man stirred up like a nice pair of heels.” Cindy replied well I guess it is settled then; we will have to get you some new shoes for your date tonight and with that, she took me by the arm as we headed to the parking lot.

When we arrived at a local discount shoe store, it was very crowded. We headed straight for the women’s shoes and Cindy wasted no time in having me try on several pairs and model them for her. I tried to focus on Cindy, as I knew all of the women in the isle were watching in amazement as I continued modeling women’s shoes for Cindy. As if that was not bad enough, after Cindy decided on a pair for me and we stood in line at the checkout, the clerk asked Cindy if she knew about the sale, buy one get one at half price. Cindy turned to me and announced “Tricia why don’t you run back and get that pair of stilettos that you were eyeing up”. Almost without hesitation, I quickly went back and grabbed the shoes, as I returned to the checkout I suddenly realized how long the line was and that everyone was staring at me as I approached with the stilettos. Cindy asked did you get the right size dear, I nodded my head yes, she then added you should really try them on because high heels can run a little different in size. She looked at me smiling and said well Tricia what are you waiting for, go ahead and try them on. I felt like running out of the store I mean there were other men along with several women in line behind me already starting to snicker and giggle at me. Cindy glared at me at which point I knew that I had little choice, so I removed my sneakers, which revealed my stockings and tried the high heels on. Cindy then motioned her head for me to walk across the store and model them. As I walked the giggles turned to all out laughter, I heard one of the guys in line mutter what a sissy, and the woman next to Cindy in line complement her on how well I was trained.

I was completely humiliated as we finally left the store, while we were walking through the parking lot Cindy asked me if I would like to go back to her house and try on my new clothes. I paused for a second thinking about how humiliating the day was, I also realized how turned on the days events had made me, and so I accepted her invitation. She insisted on driving so I left my car in the mall parking lot, as we headed for the interstate she handed me a blindfold and told me to put it on so that her place of residence would remain unknown to me, since we just met on the Internet. I reluctantly agreed and put it on. When we arrived at her house she lead me in before removing the blindfold, I had no idea were I was or how I would get back to my car if something unseen were to happen. She invited me to sit as she opened a bottle of wine; as we sat across from each other talking, I started to become more comfortable with the situation and after finishing my third glass I realized that I was starting to get aroused so much in fact that I wondered if she slipped something in my drink. I could barely contain myself; she stood to pour me another drink and asked if I would like to try on my outfit. As I agreed, she handed me my shopping bags and led me to her bathroom. Cindy agreed to help me get started with my transformation. First, she had me take off all of my clothes and rub a “moisturizing” lotion over my entire body. After ten minutes or so passed, she turned on the shower and told me to get in. As I started to lather up, I began to notice large amounts of hair gathering in the drain, that’s when I realized that the lotion was actually a hair removal product. When I exited the shower and toweled off I become conscious of the fact that my skin was smooth and hairless. Cindy told me to sit and continued my makeover. She applied foundation, blush, eye shadow, eyeliner, and topped it off with dark red lipstick. She then stood up and handed me a box, she told me that it had some additional accessories and that I should feel free to use whatever I wanted as she left the room. I rummaged through the contents of the box and picked out a long curly haired wig, large hoop earrings, a thick black choker necklace with a matching bracelet and then in the bottom of the box I found a pair of silicon breast forms. I picked then up and held them to my chest; they were about a size c and looked to be perfect for me.  In the package was a bottle of adhesive, without further hesitation, I applied the adhesive and held the breast forms in place for several minutes before letting go to see if they were secure. Pleased with my new breasts I continued to dress, putting on my bra and stockings. Next, I pulled my dress over my head and slid it across my breasts, (the feeling was quiet wonderful) and lastly I strapped on my 4” stilettos. I stepped back to view myself in the full-length mirror, as I did I could not believe my eyes, there was a beautiful woman staring back at me. It was like a dream come true, I was finally not only passable but I was actually attractive. I stared at myself for a minute realizing that I was dressed like a total slut before finally getting the nerve to show myself publicly for the first time as Tricia.

I exited the bathroom, walked down the hall and as I turned the corner, I was shocked to see a man sitting on the sofa looking at me. He stood and introduced himself to me; “Hi Tricia I’m Steve” he paused for a second looking me up and down and continued “wow, your more beautiful than Cindy described”. I gave him a smile and replied  “its nice to meet you Steve” and then I added  “your very handsome yourself” as I slowly looked him over with my eyes. Steve must have taken my comments as an invitation as he started to approach me, and he did not stop until we were face to face. He reached his hand down to about me knee and ran it up my stockings and across my butt. The feeling sent chills up my spine and it was at that moment I leaned forward and began to kiss him. We kissed passionately for several minutes, I remember thinking to myself that I couldn’t believe how aroused I was getting by kissing a man. I was enjoying it so much that I unconsciously began to unbutton his shirt as I started to caress his chest. He was in great shape and had rock hard pecks and abs, he seemed to be enjoying the way I was touching him so I proceeded to remove his pants and lower myself to my knees. I hesitated for a moment as I was just inches away from his manhood, Steve noticed my hesitation and gently put his hand on the back of my head to lead me in. I almost instinctively took him in my mouth; I licked and caressed the head of Steve’s cock for several minutes just teasing him until he was fully erect. When I was sure he was completely aroused, I settled in on his entire shaft, slowly taking him in and out of my mouth while circling my tongue around his manhood. I was enjoying myself so much that I did not notice that three of his roommates had entered the room until they began cheering me on. I became empowered by their cheers and began to increase the rhythm to which I was sucking his now massive cock. I felt Steve tense up and I knew what was cumming next, and then he let out a loud moan as he began to fill my mouth with his man juice. I tried to savor every drop, as the taste was even better than I imagined. It was sweet and slightly salty with a creamy almost satin like texture. It must have been awhile since his last release as he continued filling my mouth until it began to run down my face. Steve began to quiver, as I continued to worship him as I licked him clean. When he was completely satisfied, he looked down at me and said “Tricia you are going to work out just fine, in fact I think I will schedule your first procedure for tomorrow”.  Puzzled by his comment I asked “What procedure”? Steve then began to tell me that he was not actually a crossdresser, but rather he and his three roommates were all in pre-med and did not have time to find girlfriends so they devised this plan to find a crossdresser and make him their sex slave and at the same time use him to practice their cosmetic surgery skills. They figured that I was going to be a case study in which they would completely transform me into a woman, an entire sex change operation! I was mortified what had I gotten myself into, and more importantly how was I going to get out of this situation…

Steve then told me that I had no choice in the matter, if I refused to go along with the first procedure; he would go public with today’s events as he had the entire day on video. It seemed that I had little choice so I agreed to the first procedure, without knowing the details, Steve smiled at me and said “that’s a good girl, now why don’t you go show the other doctors how appreciative you are”. I walked over to his roommates, introduced myself as Tricia and dropped to my knees. I began to think; was this to be my fate, was I really going to be a sissy cocksucker sex slave for the rest of my life? Or, would I be able to figure a way out of this awkward situation? I paused for a moment and then leaned forward taking one of them in my mouth as I began stroking the other two, all the while hoping that I wouldn’t put a run in my stockings

To be continued…

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