Working with Trista Ch. 05

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Working with Trista Ch. 05
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.


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.

I was obviously mortified as Trista and I went into our hotel. Some sales guy that I was going to have to work with saw me dressed as a woman and not only felt my ass up gave it a couple of slaps as well. In the elevator, I mentioned that to Trista and she told me, Oh, pffttt, that s nothing. He didn t recognize you and most likely won t remember it. You will though, every time you talk to him now. She had an evil grin on her face.

Back in the room, Trista had me remove my skirt and blouse along with the tape she had put on me to make me appear more womanly. Don t worry, you ll be feeling plenty like a woman before this night is over, she warned me.

I was in heels, thigh-high stockings, a thong, bra, wig and complete makeup. Oh and of course the ever present cage that prevented my cock from ever getting hard. There was a knock on the door and Trista went to let in our dinner friends. (It was amazing how relieved I was to see Jake and Alana as opposed to Bill or anyone else. Jake and Alana I figured I didn t have much to hide from at this point.)

Trista had me serve everyone drinks in my risqué attire. Once everyone was comfortable, it was finally Alana who said, Well let s get this show started shall we? While I had figured there was going to be more to my night than just serving drinks, I had been holding out hope that running into Bill would be enough.

Trista stood up and said, Ok well Alana, why don t you start, everything you ll need is in that bag on the floor, help yourself.

Alana immediately went to the bag and brought out the black paddle that I had become quite familiar with over the past week. Alana asked Jake how many he thought that she should give me, he settled quickly on 30 swats. Alana forcefully bent me over the back of the couch, my even higher in the air than it normally would have been because of the heels. 30 swats later I was nearly in tears and my ass felt like it was on fire.

Trista shortly followed after, she gave me 5 swats on each side of my ass with the crop she had dug out of the bag. I thought that the paddle had hurt, but with my ass already quite sore the localized sting of the crop was even worse.

They then asked Jake if he wanted to take a turn. He laughed and said that if he were to swing something that I d be in tears in no time. I couldn t agree more and was happy to hear him say that. Alana then suggested, Then just use your bare hand.

Trista giggled, That s a great idea; this little slut has already had one man s hands all over her ass tonight, why not another.

They didn t want me to simply standing behind the couch though for the spanking I was going to get from Jake. Instead as he was sitting on the couch, I had to straddle him, reverse cowgirl style and lean forward with my hands on the floor. That way, my ass was right in front of him and he could strike it without moving. Trista took this opportunity to take many more photos of me in this compromising position. For his part Jake s blows didn t hurt as much physically as the ones from Alana and Trista, though emotionally they were much worse.

They made me count out 20 spankings before Alana told me come over to her. She had lifted up her skirt, her bare pussy on display. Come over here and get to work. I got between her legs and quickly began to lick her pussy. She was quite wet and she pulled my head closer to her to get my tongue even deeper. That s right you little bitch, lick my pussy, she moaned. I d never let your little cock inside me but I m going to cum all over your tongue.

I soon felt Alana s legs clench around my head and soon enough she was cumming on my tongue. My cock as usual was struggling to get hard and my balls were starting to ache once again from being so heavy with cum.

I heard Trista ask Alana, Do you want him again or should we move on? Alana responded, Oh I want another one but make him work for it will you? I didn t know what that meant but unfortunately I soon found out.

As I tried to bring Alana to a second orgasm, Trista was behind me. I found that making me work for it meant Trista running the crop lightly along my ass and between my legs while I licked Alana. Occasionally, Trista would bring the crop down on my ass, making me yelp into Alana s pussy. Before Alana came again, Trista would also bring the crop up against my balls three times. It wasn t as hard as it could have been because of the angle, but it did the trick. My balls now ached with every movement I made.

After Alana came again I was literally gasping for air; she had had her legs wrapped around me so tight. As she allowed me to lift my head up, Trista was standing right next to me. In front of her was a fake cock kept in place with her strap on harness. This cock wasn t the one from the night before, however. Instead this one was much bigger. I had about 2 seconds to process all of this before she said, Open up slut and she forced the large rubber black cock into my mouth. She then began to thrust the cock in and out of my mouth.

As she was fucking my mouth Trista said, I hope you ll notice that this particular dildo is a bit bigger than the one you had before. The one before was about the size of your cock. This one however, as you can tell is much bigger. It s the size of a real man. The way a real cock should be. While you ll never know what it s like to have a real cock hang between your legs, you now know what it s like to have one this size in your mouth. And you better do a good job because soon you re going to know what it s like to have a cock this size up your ass. Pretty soon you ll know why you never had a chance to put your pathetic little dick in my pussy. It would never fulfill me.

He appears to be a natural, Jake chuckled. While the commentary on my lack of any chance with Trista was demoralizing, my cock strained to get hard as they continued to humiliate and insult me. I couldn t understand why my body was betraying me once again, but I knew that without a doubt being treated like this was turning me on.

Trista continued fucking my mouth for about 10 minutes. Finally she said to Alana, well you think he s ready?

Alana laughed and responded, No I don t think he s ready for this but I don t see him becoming ready anytime soon. That got a giggle from Trista and a laugh from Jake.

Trista told me to stand and to remove the thong I had on. When my balls were exposed, Trista knelt down in front of them. She squeezed them in her hands and asked how bad I wanted to cum. The pressure she applied kept increasing until the point it was hard for me to stand. I begged for her to let me cum.

Wrong question, my little whore. You can beg me to fuck your ass though, then at that point I may consider letting you cum.

Oh please, please fuck my ass, please fuck me if you will allow me to cum, I begged Trista.
Trista smiled, Since you asked so nicely, I will. Now turn around and bend over the side of the couch, offer your ass to me.

Embarrassed beyond belief, but yet unbelievably turned on, I turned around and bent over the side of the couch. My ass up in the air, presenting myself for her. I felt her begin placing lube around my ass and I felt her slide a finger inside of me.

Now slut, if you re good, you may be allowed to cum. The key word is may. Keep in mind that you asked for this and so I m going to grant your request. I m going to fuck you up the ass. I m going to treat you like a real whore. We re doing it here because no one would actually take you to the bed to fuck you. Whores like you get fucked on couches, or tables or the hoods of cars. I m going to take your ass hard, and it is going to hurt. I actually want it to hurt. I want you to be walking awkwardly tomorrow in the airport; I want you to be sore. I m going to stick this long thick cock up your ass. You re going to moan, you may even cry, but it s going to fill you up like you ve never felt before. You see, you thought you had a chance with me but I m going to show you what a real cock feels like. As a matter of fact, you may think of begging me to stop. But the only thing I want you to beg for is for me to fuck you harder and deeper. Now ask me again to fuck your ass with my big cock because yours is so small and pathetic that you shouldn t be allowed to use it. That instead of using your own cock, you should be fucked with one.

My balls were about to burst. If I was ever going to break the steel cage that entrapped my cock it was going to be now as I couldn t possibly strain against it any more than I presently was.

Please Mistress, put your big cock in my ass and fuck me. My own cock is small and worthless and I should only be fucked with cocks instead of being able to use my own, I cried.
With that, I felt her begin to push the large head of her cock against my ass. She continued applying pressure, telling me to relax as her thick cock slipped slowly into me more and more.

As she kept slowly pushing she kept whispering to me, just relax bitch, take all 9 inches..
After what seemed like an eternity, the dildo was fully inside of me as I felt Trista s hips resting against my ass. I moaned out as she slowly withdrew from me and pushed back in. Soon enough she began a rhythm of sliding the cock in and out of my ass. I was already breathing heavy and she was right, it did hurt quite a bit, but was also starting to feel good I hated to admit.

Trista was soon fucking me hard, and my balls I felt swinging between my legs. Each time they would come in contact with anything it was enough to almost make me scream. They were so filled with cum that so desperately wanted to escape. Trista began to slap my ass on occasion, it was still red and tender from the earlier abuse it had endured.

How does that feel slut, do you like having a cock in your ass like this? Do you like being treated like a whore with a little useless dick?

A million things were running through my mind at this point. To my surprise, one of them was that I actually was to some extent enjoying it. I wasn t sure if I liked the humiliation, the pain, the lack of control, not being able to cum or what, but something was making my cock try to get hard as it strained against the cage.

As Trista continued to fuck my ass as hard as she could, she once again asked me if I wanted to cum. And I did, I answered her more than anything. She then asked, if I d swallow my own cum. I answered without thinking that I would, at this point I was pretty agreeable. Alana asked if I had ever tasted a full load of cum before. I managed to respond that I hadn t.
Trista then said, Well it s high time you start. With that, Alana lifted my head up and in front of me was Jake s hard cock. I had seen it before of course, but it was much closer this time around. Suck his cock, Alana whispered.

As Trista continued to pound my ass from behind Alana held my chin up as Jake s cock moved slowly towards my mouth. I noticed drops of pre-cum on the head of his cock. As his cock passed between my lips, I tasted the pre-cum on my tongue. I heard Alana again as she said softly, good girl, now make him cum.

Jake s cock filled my mouth just as well as the one behind me filled my ass. It was as if I was being pushed in two directions. Trista would slam her plastic cock into my ass pushing me forward, making me gag slightly as Jake s cock would inevitably slide to the back of my throat. He would thrust his hips forward pushing my ass into Trista. I felt like a piston between the two of them. They double-teamed me for a good 5 minutes. Trista kept slapping my ass and calling me names as Jake would hold onto the back of my head and push his stiff cock deeper into my mouth. Had you told me a week ago that I would be in the position; I could not have imagined it. Nor would I have imagined how turned I was. My cock was once again straining against the cage and my balls felt like they might explode.
Finally, I felt Jake stiffen and I heard Alana in my ear again. She whispered, Swallow his cum, be a good little whore. At that moment, Jake s cock erupted and he filled my mouth with his thick cum. It was a huge load that I had no choice but to try to swallow.

After Jake came Trista removed her large plastic dildo from my ass. I immediately collapsed on the couch and in a matter of moments I was asleep. The last thing I thought before I fell asleep was that I was exhausted, sore, humiliated, and felt cheap and used. And that I had loved it for some reason.

Day 7

The next morning I awoke on the couch. My ass was sore, my balls ached and my chin felt all crusty which I knew wasn t from drool. Any chance I had to pretend that last night didn t happen wasn t an option as I was still wearing the stockings and heels along with the wig. Trista was packing our stuff up as our flight left in a couple of hours. She was already dressed and had showered.

Oh hey sleepyhead. I was just going to wake you up, Trista said to me as she smiled. You best get in the shower we have to head to the airport soon.

I stumbled up off the couch. I was about to take off the heels and Trista said, Oh no sweetie. It is best you learn to do the old walk of shame. A slut like you will do it often I m sure. So on wobbly legs I stumbled to the bathroom.

Once in the bathroom, I looked in the mirror as my jaw hurt in a way I had never experienced before. I saw that I still had a ton of makeup from the night before though it was all smeared. The lipstick was smudged and I had a trace of Jake s cum down my chin.

I began to think of how I had gotten to this point and immediately I was met with an ugly reality. I still had this cage on. My cock was still off limits to me and the only person with the key was the temptress in the other room. She had to let me out though. It was made of metal and I had to go through security in the airport. There was no way I would be able to wear it through.

It was funny how perspectives change. A week ago when I arrived in Vegas, my only thought had been trying to get my cock inside of Trista. A few days later it had been wanting to cum. And now I wanted to simply have the freedom to touch it myself for fear of being pulled aside in the airport.

Had she forgotten? Was she going to let me out after my shower? Did I have some other task to perform yet?

No way could she forget, I walked right by her in thigh highs stockings and heels with nothing covering up the cage this morning. So she clearly saw it was still on. She hadn t forgotten. What other task could there be that I had to perform? She fucked me in front of strangers and made me suck another man s cock in front of his wife last night. Plus there wasn t time for anything else was there? Needless to say, my shower wasn t enjoyable as I tried to piece together the puzzle.

I emerged from the shower and Trista had out a butt plug and a pair of panties and another pair of thigh high stockings and garter belt.

Since we re still in Vegas and the bet is still on, you can still wear this. Once we re in the air though, you can feel free to go to the bathroom on the plane and remove whatever you wish. Though keep in mind that those spaces are a bit cramped, Trista said as she smiled at me.

Without complaint I began to get dressed and included those items that she laid out for me. Putting the plug in was a terribly painful ordeal from the abuse my ass had taken the night before.

When I was fully dressed Trista said we had better finish packing and head to the airport. I was about to ask her about the cage but she stopped me. I know what you re going to ask, and don t worry, it will be taken care of. I haven t forgotten, you ve been very good and I will keep my promise to let you out of the cage.

The next hour was spent finishing packing, checking out of the hotel and driving to the airport. In the car, Trista told me to lower my jeans as she drove. I followed her instructions and lowered my pants exposing the panties and garter belt I had on.

At a stoplight she removed the key from around her neck and said, Ok take it off, but I ask that you wait for an hour before you cum yet. You waited a week, and I promise that I will not do anymore teasing but I would like to discuss this past week with you before you are allowed to cum. That sound ok?

While I wanted to masturbate right there, I had to admit that it wasn t an unreasonable request and so I obliged. When I unlocked my cock, it immediately sprang to life. Trista looked over, seeing my cock as hard as it could be, she giggled, Oh look at that, it s cute.

She told me to pull my pants back up and to put the cage in her purse.

We made it through security; Trista simply left the cage in her purse, and it went through the x-ray machine without incident. I asked her what she would have said if they had asked her about it. She said, I ve found it best to tell the truth to TSA. She then added that she wouldn t have had anything to be embarrassed about anyway. That it would have been my face that would have been red as she explained it to them. It was a fair point.

We made it through security and as the case in today s world we had some time to kill. Trista asked if I wanted to get a drink (it was already 10 am after all haha.) I didn t really need one but then I didn t have anything else to do. Plus it had been a while since I tried the hair of the dog remedy for the hangover I had.

We sat down and ordered our drinks. I had to admit this was strangely ironic as this was how our week had started out. Over a drink when I made what turned out to be an unwise wager. Trista then told me she wanted to talk about what had all happened.

She asked me what thoughts I had on the week. What I liked, what I didn t. I went on for quite a while but I admitted that all in all the week had turned out to be a huge turn on and that I did have a lot of fun. Fun that I didn t think I would have ever tried to have on my own had I not been forced. She laughed and she said she preferred the phrase strongly encouraged instead of forced.

As we talked, Trista noticed me adjusting myself. She laughed, I see you re getting used to not having the cage on again. I know I said I wouldn t tease you, so you know, that s not my intention here. I told her I knew that but that talking about it was almost as big of a turn on as actually doing the actions.

She then asked me if I knew how it would have all turned out, if I would do it all over again. I thought about this for a minute. My response was, In all honesty, most likely not. But it s not because I didn t enjoy it. It s because I would chicken out. That s why I used the word forced. I felt like I had no choice. I know I did, I mean I could have run away and had a locksmith help me. It would have been a heck of a story but I could have done so. But I wouldn t choose to do it again. However, I would want you to make me do it again. That s the key part. I really enjoyed not being in control and not having a say in the matter. Did I enjoy everything we did? No not really. But I did enjoy the not having a say in the matter. The lack of control is what was enjoyable, especially as you proceeded to humiliating me at every opportunity. But it was undeniably the greatest sexual week of my life, and I didn t even orgasm.

Trista smiled and said, That s a good answer. I can appreciate that. I know you said you liked having no choice in the matter. But here s where you have to make a decision. You said you enjoyed it. When we get back home, we can do one of two things. First, we can go back to the way things were before we came out here. You can have your freedom and leer at me and go home at night and probably masturbate to thoughts of me and others.

With that she reached into her purse and produced the cage and set it on the table.

The second option, she began, is that we continue what we started here.

She let that hang there in the air. I think she was seeing if I would flat out refuse. She smiled when I asked her what that would all entail.

Well, the first thing it would entail is for you to go put on the cage, lock it and return the key to me.

What else does it entail?

Those specifics would be revealed once you have the cage back on. I d like to tell you some stuff but I don t want to ruin any surprises. You yourself said that one of the things you liked best was that you didn t know what was coming.

That was true I had said that.

When I asked for at least a hint she said, I will tell you what. If you return with the cage on and locked, and return the key to me. I will have ready for you a list of 5 rules. There may be more added, they may be amended in the future or they may be removed entirely. However, these will be the rules we will have from the start. You will have to follow them or there will be consequences.

I asked her what type of consequences. She laughed and said, You should have a pretty good idea by now. But it will be most likely one of three things. 1) Your next orgasm will be pushed back. 2) You will be disciplined and it won t be pleasant. 3) You will be forced to do something you may not entirely enjoy. Of course, keep in mind it could be all three things too, depending on what I decide.

I then asked how long she was thinking this arrangement would be for. She replied, Obviously, it will have to be for some length of time otherwise the threat of your next orgasm wouldn t mean much. I mean if we only do it for a week, what s the big deal. You ve already done a week. I would propose that we would revisit at one year, or put another way, after one year, you could choose to opt out. I can terminate the arrangement at any time.

I thought for a moment. A year seemed like such a long time, but the more I thought about being locked up in the cage again the harder my cock got. The more I thought about Trista having complete control over my cock the more my cock leaked pre-cum. The more I thought about her having the power to humiliate, use me and abuse me as she saw fit the more my balls ached. And the more I thought about not having control and handing it over to her the more I knew what my decision would be.

So what do I have to do? I asked.

Simply go to the restroom and put the cage back on. I would prefer you not cum before you do, though I did promise you that you would be able to. So if you choose to masturbate in the stall before you put it on I cannot control that and it is your choice. Though I have to say that I would prefer it if you did not. So put it on, return to me and hand me the key.

I started to stand up and she said, Wait one more thing. Be sure you realize what you re handing over. You re handing over the power to cum. When you do it will be the way I choose. This was in a town full of people you do not know. When we get back home, you will be surrounded by people you know and who know you. Some of which may be collateral damage, in that they may see a different side of you. That may be intentional on my part or not. But over the next year, undoubtedly, no matter how careful, someone may stumble onto something.

The thought of that caused me to have to adjust myself once again. I told her I would be right back. I went into the restroom and I was tempted beyond belief to quickly masturbate and cum, but instead I waited for my erection to die down on its own and finally placed the cage on and locked it.

As I was walking back, I would be lying if I didn t think about reconsidering. After all if seemed like Trista had tried to warn me. I was about to walk away and she called me back. However, I continued on and handed her the key. She told me to sit down and she had an evil grin on her face.

Did you cum? she asked.

When I told her I didn t, her grin turned into a full-fledged smile.

She slid me a piece of paper and said, Here are your rules/tasks for the next year for right now. Remember I can choose to revise them as I see fit.

I opened the piece of paper and immediately my cock began to do its all too familiar strain against the cage as it tried to become hard.

1. No body hair at all. Remain shaven at all times.
2. 6 orgasms in the next year to be decided by Trista
3. All cum I produce I must eat.
4. A minimum once per week, Trista will use the strap-on.
5. A minimum once per week, Trista will punish me.
6. No more male underwear.
7. Only spandex allowed at the gym.
8. Only lingerie outfits allowed to be worn at home.
9. I will need to clean Trista s house in a maid outfit or lingerie, at least once per month.
10. I will need to start an online blog which I will need to update at least once a week. Complete with pictures, though they need not show my face.

After I had read these rules I looked up at Trista. I m not quite sure what my reaction said exactly but she said, These of course are just the start. I also want you to think of a few things on the flight home. Of your Facebook friends, I want you to do the following: make a list and pick one male and one female friend that will see you in complete lingerie. Furthermore, pick one male and female friend that will see you take it up the ass, keep in mind they may want to join in. Finally, pick one male from your Facebook friends whose cock you will suck. They may not be the same person either. It has to be five different people. The male and female can be a couple though. While in the air, you can think it over. You can tell me their names and show me their profiles when we land. If you don t pick, I will pick for you. Now let s go catch our flight.

It s going to be a fun and frustrating year.

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