Working with Trista Ch. 05

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."