Working with Trista Ch. 03

This is the next day in my experience of working with Trista. If you haven't read the prior chapters, please do so. Don't hesitate to contact me with feedback.

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Day 4:

I awoke to the sound of my phone ringing; Trista of course was on the other end. She told me to have my stuff packed up, that I'd be switching rooms. She explained that instead of us having two separate rooms we may as well upgrade and get one nicer room since she was spending a large majority of her time in mine. I wasn't going to argue with that, these Vegas hotels have some very nice rooms.

I also thought that maybe if we were sharing a room, I might have a better chance of getting some relief.

Each morning my balls were still sore and throbbing from being so full, but it was so much better than at night. It was like they got some rest themselves as I was sleeping. Trista had told me that I had 20 minutes to pack before she got to my room. She told me to pack up everything but the clothes I had on. When I reminded her that I still had on her bra and thong from the night before, she said that's fine, to pack everything up but what I was wearing.

I didn't like the sound of that but I wasn't in much position to argue, nor did I have time to put much thought into arguing. I had a lot of packing to do.

I finished just in time, as I heard a knock on the door. I confirmed via the peephole that it was indeed Trista and let her in. She came in carrying a plastic bag and immediately looked me over. She had on black spandex tights and a red zip up vest. (Naturally I looked her over too in that outfit.)

"Well how did you like sleeping in my lingerie," she asked. I admitted that the outfit was and is a turn-on, but also said I had a fitful night of sleep and mentioned the reasons why. She seemed sympathetic as she listened although she made no promise of any sort of relief coming my way anytime soon.

She asked if I had packed everything and I told her that I had. She dug out my tennis shoes and a pair of socks from my bags as there was another knock on the door. Trista told me to sit on the bed and not to move. It was a bellhop from the hotel staff who was there to move my bags. Unfortunately for me, Trista let him in the room as I was sitting on the bed. He saw me and tried to stifle a mocking smile but couldn't totally suppress it as he saw me sitting there in Trista's undergarments. Trista noticed his laugh and said, "I suppose you see something like this a lot." Ramon (whose name I learned via his nametag) sort of laughed and said that not as often as people think. Trista then introduced herself and said that since it doesn't happen often he should have a story to tell so she made me stand up and turn around so the bellhop could fully see me. When Trista asked what he thought, Ramon said, "he looks pretty good in it actually, but not really my type." That made Trista laugh and she thanked Ramon and asked him to bring the bags up to our new room telling him we would return the keys to the front desk soon.

My face was now as red as the lingerie I had on, and I was growing concerned about what it was that I exactly was supposed to wear now that all my clothing had been removed by Ramon, except for what I had on and the shoes and socks Trista had dug out of my bag. It would certainly make a strange ensemble I thought.

My question was answered immediately as Trista pulled out of the bag a pair of royal blue spandex tights and a long sleeved red spandex shirt similar to what I had tried on the day before.

I started to protest that I couldn't wear this outfit, but Trista cut me off. "Look, you're going to take off the lingerie, we're going to take off the chastity device, you're going to put on nothing but spandex, we're going to go work out, you're going to be hard the entire time, everyone will see your hard cock in the spandex, then we're going to go our new room and we're going to put that little cock of yours back in the cage where it belongs. Is that understood?"

I answered, "Yes Ma'am." At the present time, I didn't have many bargaining chips. All of my luggage had been moved, the only clothes I had were the ones I was wearing and Trista didn't seem to be open to any type of discussion on the subject.

I followed her instructions. Immediately my cock sprang to full attention as soon as it was released and remained that way for basically the entire workout. That includes the trip down the hall and the elevator and past the 30 or so people we passed on the way to the workout room. It also includes the 6 or 7 people in the fitness center. You know how they have those Viagra commercials that if you have an erection that lasts four or more hours to contact a doctor? That's what I felt like.

When the workout finally ended, which was about an hour later, we headed back up to what I thought was going to be our room. Instead we headed to the front desk. It turned out that "conveniently" we had to return our keys from our previous rooms. So I stood there as Trista conversed with a cute young gal at the front desk named Kristin. I stood there nervously. On full display, I didn't know if I should leave my back to the rest of the lobby allowing everyone to see my ass in the royal blue spandex or to turn around and cover my cock with my hands crossed in front of me. Neither seemed like good options as I tried to avert the humiliation of being in that outfit in the lobby. I wasn't paying much attention to Trista's conversation when I suddenly saw Ramon coming up to the front desk. "Ah, Ramon was so helpful this morning," Trista told Kristin. I felt my face become totally flushed as Ramon received Trista's praise. I knew he was going to tell others what he had seen earlier if he hadn't already done so.

Finally Trista wrapped up her conversation and we got directions to our new room. I was very happy to finally get out of there. As we walked down the hall to the elevators, Trista kept the pressure on me, telling me things like people were probably staring at my ass or that the people we just passed looked down at my cock or that Ramon was telling Kristin about what he had seen earlier. I have to admit, the mental games she was playing certainly had an effect. While they were frustrating, it was such a turn-on at the same time. My cock had been hard for about 2 hours now and it wasn't going down until she wanted it to.

We finally arrived back at our new room and before I was able to look around and admire the upgraded suite, Trista led me immediately to the kitchenette. There she had a bucket of half ice, half cold water on the counter. She had me lower my tights and she grabbed my cock in her hand. She stroked me up and down very sensually and whispered to be sure not to cum no matter how much I wanted to or I would be sorry. But boy did I want to.

Her hand then moved to my balls and she took them in her hand and squeezed, gradually increasing the pressure. I moaned. She smiled and then slowly she dunked my cock into the frigid water. Trista then knelt down in front of me and put me back into the chastity device as soon as I was flaccid enough to do so. "Now you can look around the room," she told me as she went to shower.

I did look around the room, and it was a much nicer upgrade that the one I'd had before. Instead of my window overlooking the pool, there was now a little balcony off a patio window. We were 6 stories up, but below us was the strip. It was a pretty sweet view. The entire room was wide open, similar to what I remember seeing in a few movies with the floor to ceiling windows and the balcony that overlooked the strip. The only part that was separate was the bathroom. Also, we had a kitchenette, a couple of couches and a huge king sized bed. I liked that, I figured worst case, with only one bed; I could at least fondle Trista as we slept. Always the optimist I am.

Trista came out of the shower stark naked and into the room. She told me that we had a big day planned and that we had to get going, but first I had something I had to do. She had me kneel before her and she grabbed my head and pulled it into her pussy. I knew what to do from here and my tongue went to work. She ran her fingers through my hair as I ran my hands up and down her legs as my tongue darted all around her pussy. When Trista caught her breath after cumming she said, "You lick pussy almost as well as you sucked that fake cock last night. I am beginning to wonder which one you like best." With that she told me to shower quickly so that we could get going.

In the shower, I watched as the water cascaded down my waxed legs, looking at my cock in its chastity device, and my mind kept wondering why in the hell I kept getting so turned on. I never before had any interest in any of this stuff, why was it turning me on so much now? And of course, as I kept wondering and replaying the past few days in my head, my cock tried to stiffen and my balls began to ache even more. I quickly flipped the shower to cold and decided to give the old cold shower remedy a chance. At this point, I was so frustrated with not being allowed to cum that I would try anything.

The cold shower didn't hurt at all but it didn't help as much as I would have liked. Trista told me to quickly get dressed. Getting to choose my own outfit this time, I went with jeans and a tee shirt.

In the car, I asked Trista where we were going and she told me we were heading out shopping. We pulled up to a little strip mall and went into a boutique that upon walking in seemed to specialize in lingerie.

As we walked in and were greeted by a very cute clerk who introduced herself as Kim. Naturally, when Kim asked what she could help us with, Trista said that she we were there looking for lingerie, however I think I was more surprised than Kim was when Trista told her we were there for things for me to wear.

I looked at Trista, and she said in an even tone, right in front of Kim, "Well we can't have you always wearing mine like you did last night." My face turned as red as could be as Kim giggled at that comment. Trista then added, "He really seemed to like it" with a wink.

From that point on, it didn't seem that I had much need of being there, as Trista discussed with Kim exactly what I should get and didn't include me in the conversation at all. Occasionally, they would hold something up in front of me but by and large I was forgotten for much of the next hour. That was just fine as I was embarrassed as could be and my balls were continually aching as I kept picturing myself in the outfits they were looking at.

Finally, all the outfits were picked out and Trista called me over and held up three outfits: a black teddy, a red chemise with matching thong and a black with white pinstripe baby-doll with a matching thong. Trista asked, which outfit I liked best of these three. I looked them over and selected the pinstriped one.

Trista then handed me the outfit, and said, "Ok, here you go, try it on." When I started to stammer she also handed me a package of black thigh high stockings that she said would complete the look. I looked at Kim who just had a smile on her face as Trista pushed me into the dressing room.

As I stripped down, my heart was racing, my balls were aching and my cock was testing its bonds. I put on the thong first, and then I began to put on the stockings. I have to admit, that was quite the sensual experience, and the feel of the stockings against my smooth legs was definitely pleasurable as I was testing the cage once again. I finally slipped on the baby-doll top as Trista was telling me to hurry it up.

When I was ready, I opened the door, and peeked out seeing Trista still talking to Kim. I got their attention and even though there was no one else in the store, I didn't think they wanted me to go over to them. I was wrong.

"Come over here," Trista demanded. I walked over, feeling very much on display as they had me turn around a few times. My cheeks were burning with humiliation. They both said I looked very nice and to which I thanked them. Kim mentioned that it seemed I filled up the thong quite a bit. Trista laughed and explained that that was definitely not the case. She told me to pull down the thong to show Kim the chastity device I had on.

Both Trista and Kim knelt down in front me as Kim inspected it and Trista took her through the highlights of the device, namely that she held the key and I couldn't get hard at all. Trista then explained how she basically owned my cock and could do with it what she pleased. With that she wrapped her hand around my still exposed balls and squeezed, gradually tightening her grip until my knees began to go weak. "Isn't that right slut?" she asked me.

I couldn't form any words as she crushed my balls in her hand but managed to get out a nod and she then released them from her grip. She told me to change back into my regular clothes but to leave the thong and the stockings on which I did. Trista then had me thank Kim for all her help and we headed to our next stop.

Our next stop was at a shoe store. This wasn't your typical Payless place, this specialized in very high heeled shoes, that I believe this store could be best be described as a place where strippers would shop for their shoes. Upon entering, once again we were greeted by a clerk; she was a short brunette who introduced herself as Heather. When she asked us what we were looking for Trista told her that we were in the market for some "eye-popping fuck me shoes, something that leaves no doubt." Heather giggled a bit and said she had plenty of options as she led us across the store.

We arrived at a large wall of high heeled shoes, almost all at least 5 inches. Trista eyed the wall before selecting a black strappy pair, with a 5 inch stiletto heel. Heather complimented her taste and asked what size she was. Trista smiled and said, "oh no dear, these aren't for me, these are for him." As was becoming standard for me, I could feel my face blush as I could also feel myself strain against the cage once again. When I told her my shoe size she got out a pair for me. Trista told me to take off my shoes and socks to try them on. That was when I was reminded that I had left the thigh high stockings on and now my nylon covered feet would be seen. Trista must have noticed my hesitancy and decided to explain, in full detail to Heather exactly why I had nylon covering my feet. "We just came from a lingerie store, last night he was wearing mine and while he looked quite nice in them, I felt it would be better if he had his own and he wanted to keep the stockings on." Heather had a sly smile on her face as I was putting the shoes on. My jaw dropped when I heard Trista ask Heather if she wanted to see some pictures.

Trista then took Heather through picture by picture of the previous night and all the pictures she had taken of me in her lingerie complete with the pictures of me sucking on the dildo. I was mortified.

Finally I had the heels on and I tried my best to stand up. Trista told me to walk down the aisle so they could see how they looked. I went slowly, making sure that I would not topple over and putting one foot in front of the other. Trista laughed as Heather mentioned to her that I appeared to be a natural in heels and said I was "workin' it." Trista loved them on me, and thought they looked great. So great in fact, she told Heather that I would just be wearing them out to the car. When I started to protest, Trista said we parked right in front of the store, at worst people who I would never see again would see me, what would be the big deal. I relented and after we paid, I did a little walk of shame out to the car in my new high heels. Trista however wouldn't let me in the car right away, she made me stand outside the door, pleading with her to let me in until an older couple walked by and saw me standing five inches taller than I normally would be in my new heels.

In the car, Trista told me that she had a couple stops left. We had an uneventful (surprisingly) stop for a wig for me. Luckily Trista had allowed me to switch back into my normal shoes before we went in. For our final stop we pulled up once again to the sex toy store we had visited the previous day. Trista told me to just wait in the car, she was picking something up. She was inside for no more than 5 minutes before coming out with a large plastic bag that seemed very full. When I asked what she had all gotten, my fears were confirmed when she told me to be patient and that I would find out soon enough.

We arrived back at the hotel and went back to the room and she told me how much fun she had had with me today. She wanted to see how I would look in my new outfit. She told me to go into the bathroom and to remove my clothing and to come out in the black bra and thong set, complete with the wig, stockings and heels.

I went into the bathroom and stripped off my normal clothing. I put on the outfit as directed. When everything was on, I looked at myself in the mirror. I had to admit, that I thought I looked pretty good. Not a supermodel by any means but from across a room I could certainly be mistaken for a woman. I turned around and admired my ass in the mirror. I was amazed at how different it looked with the heels on. Once again, I thought I looked pretty good all things considered. The more I admired myself the more my cock tried to strain against the cage it was still locked in and the more my balls started to ache once again. I didn't know where this was going but I had to admit that it did seem I was being turned on by it all.

I opened the door to the bathroom and walked out, looking for Trista. She was sitting at a table across the room with a robe on sipping on a glass of wine. "Come over here and let me see you," she told me. Once again, I slowly walked across the room, trying to keep my balance. I was watching where I was walking and I heard the click of her cell phone taking a picture of me in this outfit. I looked up and she just smiled. "You looked so cute I had to have a picture," she said.

Once in front of her she was glowing, telling me she definitely liked what she saw. She ran her hands across my smooth body, up and down my legs and my ass. She cupped my balls through the thong and asked how these were doing I told her that they hurt and ached, even to the touch. She said, "Oh no, that's not good. At least not for you, I happen to like you having that feeling."

Trista then told me to kneel down in front of her and opened her legs. She had nothing on under her robe and her pussy was once again in my face. "Now, you know you that you weren't fully cooperative today. You'll have to be punished for that, but if you do a good job on your knees I might take go a little easy on you. Now get to work."

With that she pulled me into her pussy and I did indeed go to work. She was so incredibly wet, which she told me, was from watching me walk in my new outfit. That stirred my cock even more and made me work all that much harder to try to get her off. After 10 minutes and 2 orgasms she stood up in front of me, her robe still open, her large breasts and shaven pussy still visible to me, which didn't help my aching balls at all.

Trista walked across the room and came back with the paddle in her hand. She told me to bend over the table and to accept my punishment. I did as was told and she took a lot of time running her hands over my ass. She asked me, "Do you like being in this position? Knowing what's coming, so open and exposed and me being behind you like this?" When I admitted that I was turned on by it she cupped my balls and said that was what she wanted to hear. She had me lower my thong and she proceeded to give me 20 smacks with the paddle alternating from side to side. When she was done he told me to hold still that she wanted to get some lotion to rub on my ass as it appeared to be pretty red.