tagTranssexuals & CrossdressersWorking with Trista Ch. 01

Working with Trista Ch. 01


Day 1:

I had just started my new job; only a month in and so far it was ok. I was laid off months earlier and forced to start working in a temp firm. The hours were all right, the pay was reasonable, and I couldn't complain about the commute. I was told this position could potentially turn into a full-time role if all went well during the 3 month "probationary period." The marketing department I was temping in was made up of all women so that was a nice little perk. This story is about one of those people and my first business trip.

I had met Trista on my first day, while she wasn't my boss on the official org-chart, I did take all my work direction from her. She was definitely one of those people you notice from across the room, at least I sure had. She was probably in her early 40's, but you couldn't tell by looking at her. She had a very intimidating personality though, and I wasn't sure what to make of her at first. But I did enjoy admiring her from a distance.

I thought I hit the jackpot when my boss told me I would be flying to Las Vegas with Trista for a convention our company was participating in. As it was explained to me that my main duties out there would be helping her set up our display, taking down our display and checking in daily to see if our sales staff needed anything, but for the most part there was a lot of downtime. I couldn't wait. I had been out there once before, and loved it. This time, not only was the company paying for it, I was going with the gal I somewhat had the hots for in the office. I figured worse case, I could see her in a bikini by the pool one day, best case she might let her guard down a little, one thing would lead to another and we'd have one fun night or two together. I mean after all, as the saying goes, "What happens in Vegas stays in Vegas" right?

The day before we were to fly out, her and I went over what we needed to bring, she told me to bring a couple of dressier outfits for going out to dinner, she told me to bring some clothes I could get dirty while we were setting up the displays, and she reminded me not to forget to bring something to wear at the pool. She specifically made mention that her bikini was already packed. I felt a sudden twinge in my pants as she told me that. I must have been blushing a little because she said, "well it is May in Las Vegas, and I'm going to lay out by the pool at some point."

Finally the day had arrived. We met at the airport and flew out that morning, arriving in Vegas just after noon. We checked into the hotel and Trista told me to get settled, change into some clothes to work in, and she'd pick me up in a half an hour or so. We'd get something to eat before going to the convention center to set up the display.

The half hour went quickly; I changed into my work clothes, some gym shorts and a tee shirt along with some Nike Pro spandex compression shorts and shirt underneath, and was halfway through unpacking my suitcase when Trista knocked on my door. I let her in and she checked the view outside of my window, noticing that it over-looked the pool. I was grabbing my stuff to go as she noticed some of the clothing I had sticking out of my suitcase; she pulled out a pair of spandex running tights.

"What are these for?" she asked. I stammered that sometimes I wear them when I work out, if it's cold out or just want to work up a better sweat. "Do you wear these tights all by themselves?" she asked.

I told her no and when she asked why not, I blushed and explained to her that they don't leave much to the imagination. She just laughed and said good to know. So we headed out.

Setting up the display was tougher work than I imagined. There was a booth we had to set up, various products we had to unpack and a lot of heavy lifting; not to mention that the convention center doesn't turn on the A/C until the start of the conference! I actually managed to work up a sweat. Trista noticed I had, and she started poking fun, saying that "maybe you should have worn your spandex tights if this is such a workout." Trying to make a witty comeback, I told her that I had compression shorts and a shirt on underneath. That piqued her interest. She said, "Well, let's see them." I lifted up the leg of my shorts to show her the navy spandex I had on underneath.

"No, not like that, let's see the whole thing," said as she stopped working and stared at me. I started to make the excuse that it wouldn't be exactly proper attire, and others might see. She said "Nonsense, I'll make you a deal." She said she had on something similar under her shorts and tee shirt. She'd go down to what amounted to volleyball shorts and a sports bra if I were to remove my clothing and go in just the spandex I had on underneath.

This is one of those decisions where taking the time to think things through would have helped. She already had told me she planned to lie out at the pool; my window overlooked the pool, so I would see basically the same outfit the next afternoon. However, sometimes patience is hard to come by.

I took off my tee shirt, leaving the navy spandex shirt I had on underneath and looked at Trista. "Keep going," she instructed as she waved her hand indicating her impatience. I felt my cock growing harder in the spandex shorts, knowing that it would be fully on display. I slipped my loose basketball shorts down, revealing only the compression shorts underneath, my hardness pushing against the Lycra material. Standing before her in only the spandex attire, I looked up at Trista who was smiling.

"Seems like you really enjoy being in just that tight little outfit," she smirked. I started to stammer a response or an excuse and mumbled something about being seen by others, but she just laughed and said, "Don't worry about being seen by others; unless they're up close, they won't be able to tell. It's just not all that noticeable." Talk about a low-blow.

Trista went back to work and I asked her about her taking off part of her clothing. "Oh we took that break so I sort of cooled off. Plus it looks like you have enough trouble controlling that little thing without me in skimpy attire." I couldn't understand it but I was harder than ever being out in the open like this in just spandex, everything on display and being picked on about my size by my co-worker.

We finished the setup, Trista continually laughing at me hiding behind boxes or some part of the display booth anytime someone would come near as I tried to hide my attire and my hardness within it. When we were finished, I looked around for my tee shirt and shorts and saw Trista, holding them in her hand. I asked for them back and she said sternly, "No, you can have these when we get out to the car." I was about to protest, but her tone made it seem that it wasn't up for debate. She told me to lead the way; I hesitated for a bit but finally started walking.

On the way out, I felt fully on display and my face was beet red as I must have passed about 20 people walking out to the car, Trista following behind me. I could feel her eyes on my ass, and the people I passed all noticed my rock hard cock being constricted by the spandex. When we got to the car, she tossed me my clothing saying, "Cover that little thing up already." I quickly got dressed and into the car.

When we returned to the hotel, Trista told me that we had reservations at a pretty nice steakhouse so get dressed up and be ready to go in a couple of hours. She said to meet her downstairs at the sports book at around 8:00 and not spend my time relieving myself starting down at the girls around the pool. I just blushed and said ok, as that was exactly what I had planned on doing.

A couple of hours later, I had cleaned up pretty well. I had showered, shaved and had on a nice suit. My hair was looking as good as it was going to, I had on my best cologne, and yet I was as nervous as could be. I felt like it was a first date. Granted we were going out to eat, but I had just spent the afternoon being humiliated by this woman who I found a bit brash and sometimes downright bossy, yet very s3xy still. For some reason, I had this overwhelming desire to please her.

I was in the sports book bar watching the Minnesota Twins take on the Chicago White Sox, waiting for Trista to meet me. While I had found her s3xy before and was excited to see her all dressed up, this was beyond my expectations.

She was wearing a very low-cut black mini dress. It accented her in all the right ways and I couldn't take my eyes off of her. She must have sensed that I was a bit overwhelmed and she smiled and said, "Well how do I look?" I told her she looked great and she thanked me. Trista sat down at the bar and ordered a merlot as the bartender gave me a second vodka/tonic; my first one had gone down pretty easily with how nervous I was. We talked about the game and baseball in general. I tried to impress her with the fact that I pitched in high school and I was impressed with her baseball knowledge as well. That didn't alleviate my nervousness however, as I was soon on my third drink as I continued to try to steal glances at her.

I was definitely tipsy, the vodka/tonics doing the trick, as we headed off to dinner. Trista was turning quite a few heads and I was very pleased to be dining with her. Over dinner, we got to know each other better, her controlling the conversation for the most part, asking all the usual questions. I was still trying to steal glances at her low cut dress, probably not doing a very good job due to the whiskey sours, having a couple of more over dinner too.

As we finished our dinner, Trista asked me if I wanted to join her to do some gambling. I suggested we go back to her room. She laughed and asked why we should do that. I told her that she looked very good and I would love to see her without that dress on. I suggested we make a bet and if she lost I'd get to see her without that dress. After some deliberation, we ended up deciding we were going to go to across the street to the casino and place one bet on roulette. The loser would have to do what the winner wanted for the remainder of the trip. I readily agreed.

By the time we got across the street to the casino, my mind was racing with all the things I was going to have her do. The main thing was first remove that dress and after that, it was going to be repeated acts of debauchery. We went to the roulette wheel and she handed me a $5 chip. She said, "Black or red, your choice. If you lose, you have to do whatever I say the rest of the trip. Agreed?" I smiled and told her she was on. I figured there was so much s3xual tension in the air that even if I lost this bet, I'd end up a winner anyway as the end result would be the same. So I threw the $5 chip on black. When the ball finally stopped, it was on red 28 and I had lost.

Trista just smiled at me and said, "Well you win some, you lose some right?" I agreed but I was pretty deflated because even though I assumed that the end result would be us having s3x no matter who won, I was no longer in control of when that was going to happen. After staring at Trista's chest all night, my cock wanted it to happen immediately.

We stayed at the casino a little while longer, Trista telling me she wanted me to cheer her on as she played blackjack. She told me that was her first demand. She ended up winning $50 and we headed back to the hotel. At this point, my balls were aching from watching her work the room all night and her boobs almost spill out of her dress.

Back at the hotel, in the elevator, Trista said to me, "so did you get enough glances of my chest tonight? I swear every time I looked at you, you were staring at my boobs." I started to apologize immediately but she doubted that I was truly sorry. When the elevator door opened I sheepishly asked if she was going to go to bed. She looked at me and said, "Would you rather I go to bed or go back to your room and suck your cock?" My eyes were wide as I couldn't believe my ears and I told her definitely back to my room.

I couldn't get the door to my room open fast enough. Once in the room, I threw my jacket on the bed, turned around and Trista grabbed my crotch. "Let's take this out," she said and she slipped down to her knees. I stood there; still a little tipsy from the drinks I had as she unzipped my pants and took my cock out. "What a site" I thought to myself. Staring down at Trista hold my hard cock in her hands, being able to look down her dress as her boobs almost spilled out of her shirt.

I watched as she took her lips and placed them around my cock and watched as my cock slowly disappeared into her mouth. She held my balls in one hand and stroked me with the other as she gave me a mind-numbing blowjob. I stood there for a 2 to 3 minutes, her squeezing my balls occasionally as her lips worked their magic. Occasionally she would squeeze my balls which caused me to moan out but I was not going to complain.

"Does that feel good on your little cock?" she asked. I didn't even mind her demeaning comment at this point and just said yes.

All of a sudden she stood up, still holding my balls in her hand. "That's all for tonight," she told me, "remember our bet, you do what I say, and I am telling you, no cumming tonight. If these balls aren't as full tomorrow as they are now, that little blowjob will be all you get the entire time we're here. Do you understand?"

I nodded and she squeezed even harder, almost bringing me to my knees. "Good, I'll see you in the morning. I'll be stopping by at 9 am so we can go work, out so be ready. And remember, no cumming."

With that she let go of my now aching balls and retired to her room. I thought about relieving the ache in my balls but remembered her threat. Eventually I was able to fall asleep, my balls, full of cum, aching all night long.

Day 2:

At 9 am sharp, Trista knocked on my door. I was ready to go work out like she told me and I had even listened to her and not masturbated. She came in wearing a pair of spandex tights and a zip-up sweatshirt. I had put on the tights she had seen yesterday with wind-pants over them, along with a similar spandex shirt I had on and a tee shirt over that.

When we got down to the fitness center at the hotel, there were a few people but it wasn't exactly bustling. She immediately went to a row of elliptical machines, turned on her I-pod and began her workout. I went to a stationary bike a couple rows behind her and a few feet over. From there I had a great view of her ass in her tightly clad spandex tights as she swayed from side to side. I was definitely lost in thought as I couldn't wait to get my hands on that ass and finish what we started last night. Before long I felt my cock straining against the spandex I was wearing myself. Without realizing it, a half hour had past, and I was drenched in sweat. Snapping me out of my trance, Trista turned around and caught me staring at her backside and was walking towards me.

"Enjoy the view?" she asked me. I nodded and was about to make an excuse when she said, "Ok good, time to give me a view now, off with the wind-pants." I started to stammer remembering what happened when I was on display yesterday and this time with more people nearby. "No sense in stalling, we're not leaving until you're in just spandex for a half hour on a treadmill, besides, I won the bet remember."

I knew it was useless to protest, she would wait here until I did it and I really wanted to finish what we started the night before. I slipped off the wind-pants leaving only the skin tight spandex on. "Mmmmm very nice," she said, "are your balls still full?" I looked around to see if anyone else had heard her. I told her they were and that I had followed her instructions. "I knew you would," she said and she went back to her machine.

Trista standing in front of me didn't help to tone done my hardness at all. I felt that everyone was looking at me, and everyone was noticing my hard cock. Realistically I knew that half the people there didn't care either way, most probably didn't even notice, but that didn't help at all as I felt fully on display.

Mercifully, the half hour ended. Trista giggled as she looked at me in just the tights and said we were done and had to get going. Thankfully, she had allowed me to put the wind-pants back on for the trip back up to the room. Trista told me that she had made an appointment at the salon for both of us which started in a half hour.

I showered and was ready to go to the salon when she picked me up. First was a massage, which we got side by side. We were lying next to each other, only a sheet over each of us and were waiting for the masseuses to enter the room when Trista made sure to tell me, "This massage does not have a 'happy ending'."

For the next 45 minutes, the masseuse did a masterful job. I was in heaven as she worked my muscles and was totally relaxed. For a brief while, I was even able to forget that lying on the table next to me was Trista totally naked underneath her sheet. Of course, every once in a while I had to take a look over at her table to see if there was any skin showing.

Once the massage was over, Trista told me that she was going to get a manicure and pedicure. She asked what color she should get her nails done in. I suggested red. "A little slutty, don't you think?" she asked. I shrugged and said yes but she asked. She said fair enough. She told me she had set me up for some waxing, saying that I had way too much hair on me last night.

I must have looked at her skeptically because she reminded me that I had lost the bet and that it'd be growing back by the time we went home anyway, so just go with whatever the esthetician says. She also explained to me how much more she likes smooth skin on a guy. No sooner had I said ok than the esthetician came in and introduced herself, showing me to a different room. Once there, she explained the process and what was going to be done. When she said complete hair removal I asked what she meant by that. She told me that Trista had set up a complete hair removal from the neck down.

"Shaven legs?" I thought to myself. I wasn't too sure about this.

The esthetician sensed my skepticism and assured me that the procedure was not uncommon for men, and was increasing in popularity. She asked me if I liked feeling smooth legs on a woman and when I said yes, she asked how this would be any different. She also reminded me that Trista must like it since that is what she set up.

I decided in for a penny in for a pound and as Trista said, it will be growing back by the time we were done with the trip anyway.

The esthetician started with my back and then my chest. It wasn't too bad. It hurt some but nothing like in that movie the 40 year old virgin. When she was working on my groin I found myself growing aroused yet again and was embarrassed, but she assured me that it actually helped to get all the hair off. Anytime I started to go a little soft, she seemed to accidentally brush against my cock, making it spring back to life. I'm not sure if that was truly an accident but she apologized each time.

To finish, she explained to me that I had to get on my hands and knees so she could do my ass. I felt very exposed in this position and while it didn't take all that long, by the time I was done, there was a little pool of cum on the table beneath me that leaked out of my cum-filled cock. She noticed it and giggled a little, but was a professional about it all.

The whole procedure took a little over an hour and I met Trista and her new bright red nails out in the lobby of the salon. She was reading a magazine and asked as soon as she saw me, "How does it feel to be totally hairless?" More than a few people looked up and the girl at the reception desk couldn't stifle her laugh. My face turned red, but I answered that I was surprised that it felt really good and I liked it.

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byamberbmaid© 8 comments/ 95241 views/ 27 favorites

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