Working with Trista Ch. 05

This is the final two days of my trip working with Trista. If you haven't read the other portions of this story, I would suggest it.
Feedback is welcome, especially of the message variety as I would love to discuss these adventures. Otherwise if leaving public comments, please make them constructive.
Thanks.

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Day 6

When Trista woke me up the next morning it took me a while to get my bearings. I had a slight headache and was sore all over. After getting my bearings, I realized that it was an alcohol type of stiffness I felt throughout my body. I had crashed hard. As I stretched out, I was reminded of what exactly happened the night before. My cock immediately pressed against the cage it was in as I thought of Trista thrusting the dildo in and out my ass the evening before.

My concentration was broken when Trista said to me, "Get in the shower, we have to get going." It was 8 am but it felt so much earlier.

In the shower, I thought back to everything that had happened to me on this trip. Having all my hair removed professionally, wearing only a thong at the pool, being allowed to wear only spandex when working out, wearing lingerie almost exclusively the past couple of days, being spanked repeatedly, being forced to try on and purchase high stiletto heels, watching as Trista had sex with Jake, tasting a drop of cum, taking a dildo up my ass, and maybe most importantly of all, having my cock locked in a cage to which only Trista had a key. She had warned me that a lot more was to come today, though I didn't think I could imagine it. So much had happened already that I didn't ask for nor was prepared for. I had made a little bet and it seemed to just spiral out of control.

The worst part of it all was that I was turned on more and more by everything that Trista did to me. Every time she spanked me, my cock tried to get hard. When sucking on her dildo, my cock leaked pre-cum. When she dressed me as a woman and treated me like a slut, my balls ached. I had to laugh as I remembered it was only 6 days ago that I thought I was going to get to fuck her and it was what I had been most looking forward to. That hadn't happened, and instead it was I who was taking it up the ass from her strap-on dildo. If someone had told me of the predicament I would be in now I would not have believed it.

Once again, Trista snapped me out of my trance as she knocked on the door and told me to pick up the pace. I got out of the shower and dried off. I walked out of the bathroom in just a towel and Trista told me she had put out clothes for me to wear.

I looked at the bed and there was a pair of black spandex tights and a matching black spandex long sleeved shirt. I asked her if we were going down to the gym in the hotel. She said no but that I would get a workout. She explained to me that being that yesterday was the last day of the convention; we had some cleanup work to do.

I already knew the answer but I asked Trista if I could wear something over this outfit instead of just spandex. She laughed and said, "Nonsense, our first day here, we were there in nothing but spandex, there's no reason why we shouldn't end the trip the way we started it. Don't worry; I'll be in similar attire so that you do not feel on display."

On the walk through the hotel I once again felt that all eyes were on me though as strange as this sounds I felt like I was getting used to it. I thought to myself that maybe this cleanup thing wouldn't be too bad. Trista had worn a pair of black spandex tights herself and an over-sized gray sweatshirt.

Once we arrived, Trista asked me if I was ready. I felt that I was as ready as I would be and told her as much. She just smiled and said, "I've decided that since you were so good last night that I am going to let you out of the cage for the cleanup."

At first, I was so excited to hear the news but then I realized what she was doing. With my cock out of the cage, I would immediately get hard; if not from being turned on and unable to cum for the past 6 days, but I would be hard from seeing Trista in her skin-tight pants. Also it seemed that my cock always would try to get hard whenever I was on display, as if the humiliation turned me on.

I knew better than to protest being let out of the cage, but at the same time this was the worst possible scenario of freedom.

As soon as Trista produced the key and unlocked the cage that had been stifling any sort of erection my cock immediately proceeded to become hard. Trista took it in her hand and began to stroke me. "Awwww look that little cock is all hard now. It's bigger but it still could never satisfy me. But I bet you do want to cum don't you. Those balls look so full; I bet you'd cum harder than you ever had before. Are you excited to cum?" she asked as she continued to fondle my cock.

I told her that I was excited to cum and I begged her to let me do so. She just giggled and said, "But if I let you cum now, then others won't see your cock hard. And let's be honest, its better they see it hard, otherwise they might laugh at how small it is. At least when it's hard it's somewhat respectable."

She took her finger and ran it over my cock head, getting it wet with the pre-cum that had formed. She brought it to my mouth and told me to open up. I did and she put the pre-cum on my tongue. "I bet you love that taste, don't you?"

I didn't even get a chance to respond before she pulled my waistband back up over my hard cock and patted it through my tights, telling me it was time to head in. When we opened the door, I was not ready for what I saw. When we had set up and I was in only spandex, there were others around but no one was close to us. What I saw when we walked in was tons of people. It seemed like a mix of people there, some to do what we were doing and others more the blue-collar type, taking down exhibit booths and displays. It was safe to say though that I was the only guy there in skin-tight clothing.

The next three hours were a workout. We were busy boxing up items all the while I was on display with a hard cock. Trista was not a help at all, for about a half hour in, she removed her sweatshirt revealing a bright red zip up the front spandex top. Not only that but the shirt was short enough to fully show off her ass and her top was zipped down enough to give a very healthy shot of her cleavage. While this display of hers naturally had an effect on me, it also got the attention of just about everyone else there, especially the blue collar guys. There was an endless parade past where we were working. A few stopped to talk to Trista to see if she needed help, others to hit on her, a couple made a few comments about me.
The worst was when one guy asked her if I was going to rob the place, apparently as a joke on my all black attire. Trista called me over and introduced me to the guy. She then directed me to apologize for my erection I had.

As I did so the guy laughed and said, "So long as it's not directed at me." Trista then said that it always seemed to be directed to her but that, "it wasn't nearly enough to satisfy her." The guy was a little stunned at her bluntness to say the least.

Those three hours were embarrassing but my cock was erect the entire time. Trista commented as much in the car on the way back to the hotel, occasionally reaching over to my lap and stroking my cock through the spandex tights.

When we arrived back at our hotel room, Trista once again used the bucket of ice to soften my cock and place me back into the cage. She then proceeded to have me kneel in front of her once she had removed her clothing and told me to use my tongue to bring her to orgasm.

I knelt down in front of her once again, a place I had become familiar with on this trip. I let my tongue dance around her soaking wet pussy, flicking it in and out of her. She ran her fingers through my hair and pulled my face deeper into her. A few short minutes later she was once again cumming all over my tongue. "Lick it all up you little whore," Trista moaned as she clamped her legs around my head.

When she had finished cumming and regained her breath Trista told me she was going down to the pool for a little while, that I was free to join her or I could just hang out in the room and watch tv or take a nap. She did tell me that I was in for a big night so that resting up would definitely be a good idea.

I watched as she changed into her bikini, a white number with a few sparkles on it, and I was so tempted to go down to the pool with her but I was exhausted and felt that it would be best to lay down for a nap for a while after Trista's warning that I was in for a long night.

Trista went down to the pool and I went to lay in bed, my cock still straining occasionally against the cage as I thought back to all that had happened on the trip. Before long I drifted off to sleep.

I was awakened by Trista when she returned from the pool. She hopped in the shower quickly and emerged totally naked. I looked at her in her naked form and as usual my cock tried to get hard. I wish my cock would know better; it didn't really hurt but was incredibly frustrating to be constantly reminded that I was unable to achieve an erection unless Trista allowed it.

Trista came over to me and suggested that I get into the shower as we had a hot date tonight and had to get ready. She told me to be sure to shave my face, even though I had done so that morning.

When I emerged from the shower, Trista was dressed simply in a maroon bra and matching thong. She looked spectacular as usual. She rubbed her hands across my face, and felt how smooth it was, she smiled, "very nice."

"Now come over to the table and sit down, we have to get you ready for going out tonight," Trista told me.

Walking over to the table, I saw her makeup bag contents all spread out. Immediately, I knew that this was for me. I started to protest, but Trista cut me off, "One more night is all and this has been what you've been working towards right; now sit down."

The tone of her voice, told me that this was not up for debate. Granted she had plenty on me at this point being that she had been taking photos of me in various compromising positions for the previous 5 days. As she started to apply the makeup, I thought of how she didn't even bother to threaten me this time, instead she just raised her voice and she knew I would obey. What did that say about me?

I sat down, wearing only my towel and of course the ever present cock cage and Trista immediately started to apply the makeup. She started first with concealer, and then followed with foundation. Next she went to work on my eyebrows running a pencil through them. She explained exactly what she was doing to me and why she was doing it though I have to admit, her words were sort of lost on me. I did feel like I was being pampered though.

Next she went to work on my eyes. Applying first eye shadow, then eye liner and finally mascara. When she finished with my eyes, she applied blush and finally lipstick and lip gloss. Honestly, the only thing I would have known how to apply myself without looking ridiculous would have been the lipstick.

When she was done she held up a mirror and I was amazed at what I saw. Looking back at me in the mirror was a look that I had never seen before. I looked like a female. Now if someone were to look close enough, they would see I was a male but from a quick look or even without having some suspicion, I thought I was pretty passable. Trista had done a marvelous job. She had used smoky eye-shadow and black eye liner and mascara. She also had used ruby colored blush and lipstick. All I could say as I stared at myself in the mirror was "wow."

Trista laughed and said, "Well I will take that as a compliment."

I told her that she should; that I didn't think such a transformation was possible.

Trista then told me to get dressed with the clothing she had left on the bed, and that we had to get going shortly. I wanted to ask where exactly it was we were going, but I just kept staring at myself in the mirror.

When I finally made my way over to the bed I found exactly what Trista had laid out for me. It was a short, black dress, some fishnet stockings and red stiletto heels. Trista came behind me and said, "How do you like your outfit?"

I told her it didn't look like much and she responded, "Well that sort is the point. See, you're sort of the slut in this relationship, you're sort of the one who will be on display, and you're going to be the one getting the attention tonight so yeah, it's a tad bit short. But first, we have to give you some cleavage."

She showed me the tape she had purchased for this reason and proceeded to give me cleavage by using the tape to push my chest up and together. She also used a few pieces of tape to hold the cage down between my legs.

"That may be a bit uncomfortable for you between your legs like that but we can't have you giving away your secret can we?" she laughed.

I thought it looked a bit ridiculous as I looked in the mirror but when Trista helped me slip the dress on, it did look like I had a bit of cleavage and I had no sign of a bulge in the front. Trista smiled at her handiwork. "Now put on the stockings and the heels and you'll be all set."

Trista had changed into a dress similar to mine though, hers was noticeably longer and red. She had put on nude stockings and her heels didn't have quite the same "fuck me" look that mine did. All around she looked quite a bit classier than I; however while classy, she still looked quite sexy.

As the last touch, Trista put the wig on me and we looked at each other in the full length mirror in the room.

Trista asked me what I thought and I said, "I can't believe it."

She laughed and responded, "Yeah we clean up pretty good. You look a little like a whore but still good. But we better get going, we have dinner reservations."

I started to protest that I couldn't go sit at a restaurant but Trista told me nonsense. Just be sure to use a female voice when I speak or simply nod, don't look people right in the eye and no one will know for sure. Some people might suspect but no one will know for sure.

We walked through the hotel, I was trembling with excitement but Trista kept walking and I was struggling to keep up to her. I felt that everyone was looking at me, but yet at the same time I refused to make eye contact with people as Trista had advised me.

Soon enough we were out front and hopping in a cab. As we got in, Trista told the cab driver where we wanted to go to as she laughed hysterically. When I asked her what was so funny she said, "I'm pretty sure that everyone in front of the hotel saw all your business up your skirt you stupid slut. You can't even keep your legs closed getting into a cab."

My face turned beet red. We arrived at the restaurant and I concentrated on getting out of the cab in a half respectable manner. Trista giggled at my concentration of simply leaving the cab.

We walked into the restaurant and Trista talked to the hostess. My knees were literally shaking as I assumed that every eye in the place was on me. In a way it was true, everyone seemed to be checking out my outfit, but no one was really gasping that I was a guy who had been made to cross-dress.

Trista came over and said that our table was ready. I followed her as she followed the hostess through the restaurant. This time all eyes were on my short skirt and high heels. I wondered if they thought I was a hooker. We had a table in the corner of the restaurant fortunately. When we sat down I mentioned to Trista that this seemed like a table for 4 people not just two. Trista smiled and said, "Of course it's for 4 people, we couldn't let your big coming out party be just between the two of us, I know you would've wanted some company."

I swallowed hard and while I knew that Trista had planned for a big night, I didn't imagine that we'd be dining in a public place like this with me fully dressed as a woman.

Our waitress came by and took our drink orders. Trista was nice enough to order a couple of shots for us on top of a drink. She later said it would help calm my nerves. She took the time to introduce us to the waitress. Trista introduced me as her friend Amber. The waitress's name was Renee, and she was pretty hot. She smiled at me and said, "Nice to meet you Amber, I really like your shoes." I blushed beyond belief; it felt my face was on fire. I couldn't quite get the nerve to say thank you so I just smiled instead.

As soon as our drinks arrived, we downed our shot and I started to work immediately on my drink. Within a few minutes, Jake and Alana arrived and Trista explained that they would be joining us for dinner. The dinner went well, all things considered. Trista kept making sure that my drink was filled and I did my part by continuing to try to empty it.

When Renee brought our check, she once again thanked everyone and said what a pleasure it was to meet all of us. Once again, I was a bit too embarrassed to say much of anything in response to her, but I will admit the attention she paid to me did make my still full balls ache even more.

Trista said to me, "Look at this, Renee put her number on the check. And a little note, "Call me if you need some help with Amber, if I'm correct, she requires much discipline. Would love to help xoxo."

I blushed again, and Trista said, "It's too bad we're leaving tomorrow otherwise Renee certainly would get a chance to help out. Would you like that Amber?"

I had to admit that I would.

As we walked outside, Jake and Alana said that they would see me soon. I must have had a puzzled look on my face as Jake slapped my ass and said, "The night is young yet."

Trista and I hopped back into a cab and I started to question her as to what Jake meant. She told me that she had invited them over for a night cap. I didn't really respond but she said, "I told you that this last night was going to be a big night."

Back at our hotel, we exited the cab and I heard someone yelling Trista's name. I turned and it was our sales guy Bill stumbling towards us. Trista said, "Just don't say anything, don't look at him and let me handle him." I just nodded. I'll admit it, I was worried.

Trista turned to Bill as he approached and said hello. He was obviously pretty drunk and as a result pretty "hands-on" it seemed as he talked to Trista. They spoke for a couple of minutes and Trista then said, "Bill, let me introduce you to my friend Amber."

Bill looked at me and in a voice too loud said, "Oh I like her outfit, much shorter than yours Trista."

Trista laughed and said to Bill, "Yeah well she's much sluttier than I am." That got Bill's interest. Trista then said, "Yeah, I bet she'd let you feel her ass if you wanted to."

"Really?" Bill asked wide-eyed.

"Oh yeah, lift up her skirt, she won't even object. Run your hands over her ass, even give it a slap or two, but do it quick, we don't want to get arrested out here," Trista told him.

Bill came over towards me and reached his hand under my skirt, I felt his cold hand on my ass. He rubbed his hand all over it, squeezing it roughly and then gave it a few slaps for good measure. Trista had an evil smile on her face as she watched Bill roughly fondle me. I was as nervous as I could be but I could feel my cock trying to get hard again as Bill ran his hands all over my ass. Finally she came over and told Bill that was enough and that we'd catch up with him later. Bill being under the influence of alcohol didn't bother to ask where or when fortunately for me.