The Shopping Trip

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The Shopping TripHi, this piece is true fiction, but I wouldn’t be disappointed if it became a reality :)A little background before we begin, my name is Alexis and I’m a 33-year-old transgender male, while in a less than supportive relationship I try to dress as much as possible. But purging and self-doubt have caused me to throw away all my pretty things 🙁 Starting a new, and with no funds, I’ve explored alternate means to meet my needs, almost like having a habit I can’t shake.It all started when I casually posted online in search of someone that could help push and guide me further in my journey to become the woman that I know I am. Early in life the thrill of wearing women’s clothes, observing the way women dressed and all the styles drove me crazy! Whenever I have to tag along as my SO goes shopping is absolute torture, being able to see all the pretty things and just wish you could try them on is such a tease, oh what I would do to start with just one day of that experience. It pushed me to the edge, I had to do something to get things back on track.I had been chatting with my new potential maste for a couple of weeks, I feel we were really feeling each other out. I was putting a lot of trust in him to guide me and push me at just the right pace, I didn’t want to move to quick and my lack of money, of course, didn’t help, but he was so caring and amazing, I quickly discovered there was very little that I wouldn’t do for him. Lessons at first were small and quick, he would have me buy pink lipstick and lip liner and do up my lips just as he likes, I would take photos and post them to fetlife for him to approve. He would always say that I had the best-looking cocksucker lips, I would blush at the comment, thinking to myself am I that kind of girl? Weeks would go by and he would request different colors and I would oblige and do everything he said, then he requested that I get some panties, either bought or borrowed, so I saved what could and bought a few pairs in various colors, black/pink/purple/blue, just as instructed. More pictures followed, master said he loved the way my fat ass looked in my purple thing, the string disappearing between my ass cheeks ;). Master was so patient through all of this, he would make sure I was wearing my panties and lipstick when we chatted, and I was instructed not to jerk off, master said girlies weren’t allowed to touch their big clities, I ached for release, but perhaps Master had something bigger planned?While online training is great, you don’t always get the true sub/Dom experience, and I was ok for now with that but Master canlı bahis had other plans, and I could hardly wait! Master insisted that I start to dress and that I would need a few outfits, but I told him I didn’t really have much money, but he said he would be willing to invest a little if we could agree on repayment in other ways, I didn’t know how but I didn’t care so I agreed. He said that he would plan a day and that I should be prepared to follow his directions. The morning came and I received an email from Master, it instructed me to meet him at the Lakeview Mall at 11 am, shave my face, wear just a t-shirt and light running shorts, be sure to wear that cute thong, and sandals only! I was out the door by 10:30 and sitting waiting for him in the corner of the food court right at 11 am. I sat nervously, not fully sure what to expect, my hands were sweating, my stomach hurt, a few minutes went by and no master, thoughts ran through my head, did he give up on me? And then behind me I heard, Hello Alexis, the excitement came over me.I turned around and there was Master, in the flesh, he asked how I was and gave me a quick hug and I curtseyed as I had been taught, seemed weird in boy clothes but that was fine, I didn’t care! We started on, he said he had a couple great hours planned and that clothes were first. We stopped at Torrid first, I am by no means a skinny girl and I love my curves, Master knew the right store to start with. We walked in and he chatted with the lead that was working, they giggled a little and then proceeded to give us a changing room to get started, one girl Kelly was assigned to help us. Kelly started with “How can I help you two today?” Master said we were looking for 3 outfits, the first was something casual, the second something formal/classy, the third, something sexy, as well as any accessories we might need, so full outfits for each. My heart was beating a million miles a minute, Kelly walked around with me and took some measurements and then we went to work. The first casual outfit we picked out were these tight black jeggings, with blue trim, master said they made my ass look great (note: I probably blushed twenty times that day) To a little bit of chub got in the way, Kelly had me put on Spanx to get everything put in place. I was the outfitted with a bra and given to punk style long t-shirts, I was really starting to feel amazing. To complete the look I was given some black strappy wedges, Master applauded, I blushed again.Next came formal/classy, Master insisted this be a flowy dress, also I had to wear stockings to cover my bahis siteleri hairy legs for now. I tried on a bunch of dresses and then found this amazing blue, knee length dress, with white polka dots, we finished it off with a small jacket and black Mary Jane heels, two down, and the sexy outfit was next. From time to time, Torrid has some really sexy lingerie, and I had my eye on one piece the whole time. There was a red/black bustier, with black garters called my name, I took it off the rack and could hardly wait to try it on, it slid on like second skin, the straps bouncing on my ass. Kelly handed me a pair of tights with little red bows on the back, I put everything on as quick as I could. To finish it off, a pair of strappy heels and little silk robe to cover me a little. As I came out of the dressing room, the smile on masters face was worth it, he said I was stunning. I smiled and changed back to my boring male clothes, and Master paid, I don’t know how much but it wasn’t cheap, on to the next destination!Master said he loved all my outfits and asked if I love them too, I said it was one of the best experiences I’ve ever had, he said good, just a few more stops. We went quick to coach and we picked out this girly little purse, and the to Clair’s for a few pairs of clip-on earring. One other stop was at the Wig store, I hadn’t thought of this until now, but this would indeed complete the look. We browsed the wall of wigs. Master picked out a few styles and we settled on a light brown with blond highlights wig, it fell beyond my shoulders, it made me feel amazing. We finished up with that and were walking around Master asked if I had a great day, I nodded in agreement and said I don’t know how I could ever repay you. He said I have a few ideas but it requires real dedication and one more stop, I said Yes, anything, he said follow me. We ended up at MAC, he said Steph is waiting for you and also take your wig and earrings, see you in an hour. I met Steph, she looked amazing, heavy makeup, really alternative looking, this would be fun. She went to work, foundation, eyeliner, lipstick, mascara, shaped my eyebrows, etc and then we put on my wig and the way he spun me around, beside the boy clothes I couldn’t believe the woman staring back at me, amazing, I smiled. Master came back and was so happy and thanked Steph and paid them. We then left but I said I feel a little out of place but then he pointed to the bathroom and said take your casual outfit and go to the women’s room and get dressed, you have 10 mins. As I organized my things and was starting to dress, bahis şirketleri I heard master call in, everything good in there? I replied yes but he came in anyway, I heard the door lock behind him, he could see I was in the handicap stall, he said Alexis, let me help. I let him into the stall, he had my purse with him, he said we need to discuss repayment and next steps, I could see his bulge grow as I sat nervously on the toilet, he said here is the plan. First, he took out a chastity cage, he motioned for me to come over, he said we won’t lock this, but we had to put it in now, and he squeezed my clitty into its cage, that’s a good girl he said. Second, as he undid his pants and his 8in cock came out, you need to please master now, I hadn’t done this before, he pulled my head closer, he said kiss it, so I did and the precum hit my nicely painted lips, now open wide and suck. I tried to think back to all the porn I had watched and tried really hard, he was moaning and then he grabbed my head and shot his load down my throat, I was in heaven and smiling, he finished up. He said good, only 50 more of those and you’ll be paid off. My own clitty was throbbing in its cage, nothing I could do about it, he said and Third, turn around, a quick slap to my ass, and he grabbed it and remove a metal/jeweled plug and some lube from my bag, started to push it against my hole, I’ll want this ready for next time he said, I moaned as it went all the way in and he slapped my ass.As he left, he took my boy clothes, he said the rest of my girl clothes were in my car (how did he get into my car?) and that he would be in touch. He said to dress and leave and that he would be watching, and then he was gone. I sat for a few, in shock a little and really so happy, I finished getting dressed in my casual outfit, my sexy ass in my jeggings, and my cute top and jean jacket. I fixed my hair and makeup and grabbed my purse, I glanced at myself in the way out, this cute 33-year-old woman stared back at me, this is who I’m supposed to be I thought to myself as I smiled. Out I walked, wondering if mater would be there, I saw him in the distance and he smiled and turned away but not before taking a picture. I walked back to my car, getting a few looks but happy as can be, my cage and plug reminding me of my place and what is in store for the future.As I got to the car, I checked fetlife and to my surprise, Master had messaged me, said that he had an amazing time and that he uploaded some new pics as insurance to make sure he would get paid back. To my surprise the day was documented in pictures, he had someone following us. Pics at Torrid, the wig store, MAC and even some shots from the bathroom. He said he would remove them when repayment was done and to let him know when I was avail again, time was of the essence.

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