This is the continued story of working with Trista. If you haven't read the prior chapters please do so, to see how exactly the story got to this point. As always, feedback is appreciated, and comments welcome. Thanks for reading.
I woke up in much the same state that I had fallen asleep. My balls were full and aching and my cock was once again unable to attain an erection. My balls and ass were not nearly as sore as they had been the night before though due to the crop that Trista had used.
I looked around the room and didn't see or hear any sign of Trista. At first, I was relieved, but then I started to panic. If I lose track of her I would really be in a tough spot with her still having the key. I sprang up out of bed and walked towards the kitchenette. There on the counter was a handwritten note.
Good morning slut,
I had to run out to do a few errands, after all, remember we are here for a work-related reason. I should be back in a few hours. In the meantime, I left what you should wear in the bathroom. Be sure to put on each item after your shower. I'll be back to lay at the pool this afternoon if it's nice.
Naturally I was both interested and a little worried to see what she had laid out for me. My cock began to strain as I imagined the possibilities. I walked across the room to the bathroom and saw sitting on the sink what she had left for me.
Folded neatly on the sink were a red bra and thong. On top of those items was a bottle of red nail polish, similar to the color that I had suggested she paint her nails earlier in our trip. Finally, in the middle of everything was a bottle of lube, and another plug. This one even bigger than the one I had in me currently. There also was another note.
Hi again slut,
I hope you like the outfit I have put out for you. Use the facilities as necessary and then shower and shave. Insert the plug up your ass, I would love to do that myself, but I want that ass filled as soon as possible. After you are filled up, paint your toe nails and your finger nails. When they are dry put on the attire I have left out for you. When you're done, go downstairs and eat some lunch, it's going to be a long day. In the top drawer of the dresser I put out what you should wear while you eat.
Well needless to say, my cock was leaking non-stop with pre-cum and was straining to get hard.
I followed the instructions that Trista had left me. When I removed my plug, it was certainly an odd sensation. Nothing like removing the smaller one the day before, this one was much different and I felt my ass stretching as I removed it. I looked over at the large one sitting on the bathroom counter and I couldn't imagine how that was going to feel. I knew however that I best have it in me by the time Trista returned.
After I got out of the shower, I stared at the plug sitting in front of me on the counter. I felt very over-whelmed but my caged cock was also straining at the thought of the plug being inside of me. It didn't go in all that easy, I had to continually remind myself to just relax and not tense up, but eventually the plug slipped inside of me.
When it finally slipped into place, I found out that I had been holding my breath, gritting my teeth and was tense all over. I let out a deep breath and felt myself relax. With each movement I made though I could feel the plug inside of me. I had a feeling this would be a constant reminder as I couldn't imagine ever becoming used to this feeling.
I then started to paint my nails, both my toes and then my hands. The red was certainly eye catching. I wondered if it would be as noticeable to others as it was to me. But then I thought that whenever a woman had on this shade of red I always noticed without fail.
When my nails were dry I walked over to the dresser that Trista's note had directed me to. I was relieved when I opened the drawer and on top was a white tee shirt and a pair of shorts.
Yes, I want you to wear the red bra, underneath your white tee shirt. Yes, I know that others will see you. And yes, I know that right now your tiny little cock is straining against that cage just thinking about all of this. Call me when you've sat down, I'll head back then as I want to see you with your new bra on. I can't wait!
She was right; my cock was straining to get hard but to no avail in this cage. I got dressed and as I walked down the hall to the elevator, my balls were already aching. I knew it was going to be a long day when it was still not even noon yet and my balls were already hurting this much. Normally they do not ache as much in the morning, but when I get as riled up as this as soon as I get up, they immediately start hurting again. And that was exactly the way Trista wanted them.
I sat down and ordered my lunch from the waitress who gave me a funny look. At that time, I also called Trista as she had asked.
Trista: Hey little whore, glad you called. I'm just on my way back.
Me: I just ordered.
Trista: Oh yeah? Are some people looking at you funny?
Me: Yeah the waitress gave me a few weird looks.
Trista: Why was that?
Me: Because of the outfit you had me wear.
Trista: Oh the bra?
Me: That and the bright nail polish.
Trista: (Laughing) Hey, you picked out that color.
Me: For you not for me.
Trista: How's your little dick doing?
Me: It's frustrated.
Trista: Oh, poor you. How's the plug doing?
Me: It is quite a feeling; it's much bigger than the last one.
Trista: It's the next size up. Plus a slut like you I'm sure likes having something up your ass. Ok, I have to go; I'll be there before you're done eating. I'll call you when I'm coming in.
I was just finishing lunch when Trista came in and sat down. She was laughing as she looked across the table at me. I asked her what was so funny. "You can REALLY see that bra through that tee shirt. I saw it as soon as I walked in."
When she saw I wasn't laughing about it as much, she said, "I would apologize as I didn't think it would show that much, however, I'm not really sorry to be honest. Plus I think you need to get used to wearing one anyway."
I must have given her a puzzled look and she said, "Oh sweetie, a bra is going to be a full-time thing for you the rest of this trip. We only have a few more days here and we have to make the most of it. I did think however, that we deserved a little pampering. I booked couples massage this afternoon. The weather doesn't look that great anyway; I thought we might enjoy this."
We then went upstairs, I simply watched television and Trista showered and got ready for our massage. I had assumed it was in our hotel at one of the spas but she explained to me she got a better deal at some other place we had to drive to and soon we were off.
On the way over, Trista had asked me if I was nervous. I actually wasn't, and told her so. She simply smiled at my response and the rest of the 10 minute car ride had left my mind wandering. My legs, chest, everything else was hairless that was true, but I have to imagine that the people giving the massage had seen all that before. My nails were painted but I could just remain on my back and they wouldn't notice. Yes I had a bra and thong on underneath my clothing but I was pretty sure they let you undress privately. I had a large plug in that I was reminded of every single time I sat down but I couldn't think of a scenario where that would be an issue. Finally, my cock was still in its cage. While maddening, I couldn't envision how that would be an issue either. I decided I would just try to enjoy myself, after all, this trip was nowhere close to what I had been expecting and I could use a relaxing massage.
We arrived, and it was just one of those massage places in a strip mall. It was off the strip and it didn't quite seem like the stereotypical massage place you see on the movies, you know the ones where they ask you in some foreign language if you want a "happy ending." This seemed like a respectable establishment.
I followed Trista inside and she talked with the receptionist, a cute young girl named Mandy. I tried to hide behind Trista as I didn't need the gal seeing the bra through my shirt. I was shocked when I heard someone say, "Trista! So good to see you."
I turned to where that voice was coming from, and I then knew this wouldn't be the massage I had been hoping for. It was Alana, the woman who had "helped" Trista try some things out in Bolt's store on our third day in Vegas.
They exchanged pleasantries and Alana told us that we would be in room 4, straight down the hall. She told us to go in, relax, put a sheet on and lay down on the tables; she would be in, in a few minutes. We walked down the hall, and I thought to myself that maybe this massage wouldn't be too bad. I was as nervous as could be as Trista and I disrobed. She kept smiling at me and that made me more nervous than anything else.
I watched as Trista disrobed. She was quite a site. Her large full breasts were incredibly intoxicating and her legs were incredibly sexy. As I watched her strip off one piece of clothing after another, my cage continued to prevent my cock from getting hard. Trista eventually noticed me staring at her and she crossed the room and took my swollen balls in her hand and gave me a squeeze, "It's not nice to stare," she said.
I gasped as she squeezed my balls. "My these feel full, do they hurt?" Trista asked. I could only nod as her grip held firm. Finally she released them, and I struggled to catch my breath.
Trista slid onto the massage table and covered herself up with her sheet. I followed suit, of course laying on my stomach was an issue with the cage. Trista just looked at me and smiled.
Soon after, there was a knock on the door and Alana came into the room. She spoke directly to Trista and ignored me. She said that she would get started and that Jake was finishing up with some other customer and would be in soon. (Being the bright mind that I am I assumed that Jake was her husband who I had also met at Bolt's store.) Alana told Trista that they could start with the massage without Jake and that I would just have to be patient.
As if I wasn't riled up enough and wanting to cum already, watching one hot girl give a massage to another one wasn't helping matters at all. I watched as Alana moved her hands up and down Trista's legs. This was for about 10 minutes before another knock came on the door and Jake stuck his head in. My earlier suspicions were correct and it was Alana's husband. He said he would be about 10 more minutes. He smiled at Trista and looked quickly at me but his look was dismissive.
For the next 10 minutes, I watched as Alana massaged Trista's back, the sheet exposing more and more flesh, all the while my cock straining to get hard but to no avail.
Jake came back into the room and had said that he sent Mandy home. I must have looked nervous as Alana said, "you guys are our last appointments of the day." Jake apologized for running a little late and he switched spots with Alana and continued Trista's massage as Alana began my massage.
It felt really good, she commented a few times how stressed I felt, jokingly adding that I must be spending too much time in certain specialty stores.
I heard Jake instruct Trista to flip over onto her back and Alana suggested that I do the same. Shortly after, Trista said to Alana, "be sure to give him the full treatment, just like we talked about." With a couple of minutes, Alana's hands were very high on my thighs and my cock was straining to get hard once again as I felt her hands go up my thigh. Before I knew it, this great feeling was gone as I felt her hands wrap around my swollen and full balls. I felt her squeeze and I let out a whimper.
I heard Trista laugh as Alana continued squeezing my balls. Trista then said, "Keep up his massage as long as you want, but whenever you're ready, his tongue is magnificent." I looked over at Trista and saw that her sheet was up around her waist and at that point Jake seemed to be fingering her, playing with her pussy.
Alana kept up my "massage" for the next couple of minutes, finally she let up her pressure and she said told me to lay still. Within moments, she was on top of the table, straddling my face. Her pubic hair had been shaven into just a bare strip. She brought her pussy in front of my face and then leaned in and told me, "Now lick me slut."
I was happy to do so, for one thing my balls were no longer being tormented, but Alana was a beautiful woman and I was happy to let my tongue dive into her wet pussy. I was busying myself in my work with Alana and I could hear Trista moaning. I couldn't tell from what exactly, but I had my suspicions. Either it was from Jake's tongue or he was fucking her. Doing what I had initially hoped to do on my trip out here.
It was 10 minutes later and Alana had cum a couple of times as she kept grinding her pussy into my face. I hadn't heard Trista moaning for a couple minutes but I could tell that she had also cum a couple of times as well. Alana slid back onto my chest, she remained sitting there but she continued to play with her pussy in front of my face. I turned my face to the side and I saw Trista standing there naked, and in her hand was Jake's cock.
"Do you see this cock?" she asked me. "This is a real cock. This is one that can please me. Not that little thing you have. If you have been wondering why your little dick is locked up, it's because your cock could never please me."
I stared at the cock in her hands, and I have to admit, I wasn't much of a comparison to Jake. His cock didn't seem fully hard and it still appeared to be about 8 inches long and very thick. Trista continued to slowly stroke his cock near my face as Alana continued to play with herself in front of me.
"Jake's cock is bigger than that dildo you had in your mouth a couple of days ago, you little whore. I bet you wish you had had Jake's cock in your mouth don't you," Trista continued. "Your little cock deserves to be locked up and not near our pussies."
As Trista continued to stroke Jake's cock, Alana reached back and started to play with my balls again, cupping and squeezing them. My cock was straining against the cage and this was by far the closest I had ever been to another man's cock in my life. My head was spinning. I didn't know if Trista was going to push Jake's cock into my mouth and make me suck him or what was going to happen but I couldn't take my eyes off of Trista stroking that large cock next to me.
Finally I heard Alana say, "Make him cum on me." Trista replied what a good idea it was and before long Jake's cock was spurting out his cum onto Alana's chest, stomach and dripping down to her pussy and my chest.
I watched as his cum dripped down Alana's body, it was hot no doubt about it, but at the same time, I didn't think I could have felt more submissive. Here I was, watching this large cock cum inches from my face onto his hot wife who I had been made to pleasure with only my tongue and my cock was locked up and hadn't been allowed to cum all week. The fact that there was constant reference to his much larger size than mine also didn't help at all either.
Remember though I said I didn't think I could feel more submissive. I was wrong.
Trista let go of Jake's cock and ran her fingers through the cum that was accumulating on my chest as it ran down Alana's body. She took two fingers and rubbed through the cum off of Alana's chest, coating her fingers in Jake's cum.
"Open up," I don't know why I didn't put up a fight, but I didn't as I opened my mouth as soon as she told me. She put her fingers onto my tongue and then ran them along my lips. I could taste the cum and Trista said, "I knew he was a natural cum-eater."
After that, everyone got up and was getting dressed. I just hung my head in shame and didn't even try to look anyone in the eyes. Trista thanked them for the massage, and I was told to thank Alana for allowing me to eat her pussy and to thank Jake for letting me have a taste of his cum.
On the way back to the hotel, I was pretty quiet. I admit that while I had done a lot of things this past week that I hadn't planned on experiencing, I can honestly say that tasting another man's cum, no matter how small an amount was definitely not on that list. I hadn't said anything when Trista asked if I was all right. When I mumbled that I was fine, she asked if tasting the cum was all that bad. I had to admit that it wasn't, there really wasn't much to the cum, it was more of a mental thing. It was the feeling of submission.
She giggled and said, "Well you have tonight and tomorrow yet, and trust me, you're going to be feeling a lot of submission." For some reason, I felt nervous, fearful and worried from that statement, all the while my cock was once again straining hard against the cage as I thought about the possibilities. We arrived back at the hotel and Trista told me to go shower and get all of the massage oil (and Alana) off of me. I was showering and once again I looked down at my caged cock. Jake had been noticeably bigger than I was. He wasn't a monster by any means, not like you see on some websites, but his cock was something I definitely couldn't measure up to. Trista's words kept ringing in my head saying that Jake had a real cock that could please her. Oh how this trip had not turned out as planned.
When my shower was finished, Trista took a shower as well. Most likely to wash Jake off of her. When she was finished, she told me we were going out to dinner. Once again, she put me into a bra and thong, complete with thigh high stockings. A pair of pants and a shirt went over but I was still self-conscious about going out with these on again. Especially after what happened earlier today.
Our dinner was surprisingly uneventful. It was similar to our first night. Drinks were flowing and I admit I may have had a bit too much. However, I felt that if anyone had earned the right to have one drink too many, it was me after my day. Trista didn't scold me for it either; she kept making sure my glass was full.
We arrived back to our hotel, a few hours and many drinks later. Trista told me that she wanted me to remove my clothing except for the lingerie underneath and to add the wig and heels. I did as I was told, though I must admit that while I had been a little wobbly on the heels before, the drinks I had were doing me no favors. I stumbled up and out to the kitchenette where Trista was waiting.
"My don't you make a sexy little slut. You wouldn't mind if I took advantage of you would you?" she asked coyly.
While the other tasks earlier in the day I may not have been a totally willing participant to, at this point with the drinks I had, I was fully up for any sort of fun. I proceeded to tell her as much. She smiled when she heard that.
Trista told me to wait patiently and she would return in a minute. I watched her walk sexily into the bathroom after grabbing another one of those bags she had purchase from Bolt's store. About 5 minutes later she walked out, in black stiletto high heels that were similar to mine though hers seemed more "powerful."
Her legs were covered in nylons, and she had on a black silk robe. She smiled as she walked over to me, and she told me, "Get on your knees whore."
I knelt down immediately following her commands. Trista then opened up her robe and in front of me was a black dildo sticking out in front of her. "Now suck my strap-on you little slut" she told me.