Working with Trista Ch. 02

After dinner, we headed back to the hotel, Trista said the entire dinner got her riled up and she needed some relief. Back in my hotel room, she ordered me to strip down to just the red thong. She eyed me over and said that she really loved that look but that it seemed to be missing something. She slipped off her dress and then removed her bra, leaving her totally naked, and leaving me with my tongue hanging out as usual. She then told me, "This is a set, the bra goes with the thong," as she put the bra on me.

She stepped back and smiled as she looked at me in her bra and thong. "That looks so nice. Though red is a little whorish. But no matter, you're dressed for the occasion. Now my little whore, let's get down to business." She had me lay on the bed, and she grinded on my face for the next 30-45 minutes. She came multiple times. She paid a lot of attention to my nipples too, squeezing and pulling at them through the thin bra. My cock was trying like mad to escape from its imprisonment. Being dressed up and treated as a whore was really having an effect on me.

When Trista finally let me up, she was covered in sweat and looked so sexy. My nipples were aching as were my balls. I was very excited when Trista said, "Now it's your turn for some attention." I thought the torment of the past two days was finally going to pay off.

She wanted me to kneel on the bed, with my ass facing the door. I got into position. The red thong and bra the only things I had on. She lightly ran her hand over my exposed ass, and said, "Now my dear slut, hold this exact position. I have to run to my room to grab some things, but I will be right back down before you know it. Don't move if someone comes by and looks in here. I want them to get a clear view of exactly the type of gal you are."

I watched over my shoulder as she got dressed and then propped the door open with the doorstop and then went to her room. It seemed like an eternity she was gone. Every time I heard a voice, I started to look over my shoulder but I didn't want to actually make eye contact with anyone so I would quickly put my head back down. It ended up being about 15 minutes that she was gone. I heard two giggles and a whistle at different times. Each time my face turned about as red as the bra and thong set I had on.

Trista entered the room and was pleased to see I was still in the same position she left me. After asking me the details about the time she was gone, she was quite pleased with how it had worked out. She then looked me over and said, "You know you look so good in that outfit, we're going to have to get you some of your own tomorrow as I can't have you wearing mine all the time."

She asked if I would like that and when I stammered, she got me to admit that I was turned on when others saw me in the lingerie. "Well that seals it, if you were turned on, then we definitely need to get you your own outfits. That's tomorrow though. Tonight, I want to use the toys we got again, your ass looks so good in red; I want to see if I can get it to match. Get on your hands and knees again."

This wasn't exactly what I was hoping for when she said that I was going to get some attention, but I obediently turned around. I heard a couple of clicks and I turned and saw Trista was taking a couple of pictures of me in this position. I just hung my head in shame, hoping she would never show those to anyone. She came up behind me and said, "Ok slut, how many do you think you deserve?" When I told her that I had been very well behaved and did everything she asked she said, "That's true you did, but part of this is to make sure that you continue to behave as well. How about we give you a good 20 and then we can move onto more fun things?"

That seemed fair and a lot better than I was anticipating, and what I had gone through earlier in the afternoon, so I readily agreed. She started on the right side and brought the crop down on one side and then on the other side, alternating back and forth. It seemed that my backside wasn't as healed up as it appeared from just looking at it, as these hurt a lot more than they had earlier in the day. Trista finished all 20 and my ass was very warm. She giggled and said it was a very deep red and actually did match the red thong quite nicely.

She ran her hands over my ass, feeling the heat it was giving off, and then reached between my legs, and started fondling my aching balls. Occasionally she would run her hand over the chastity device too, just to emphasize the control she had over my cock. "Would you like to see me masturbate," she asked, "maybe use a toy as well? Sort of get me in the mood for more to come?"

I couldn't say yes fast enough. Trista smiled and went to the bag she had brought to my room. She pulled out a purple dildo and brought it over to the bed and she began to undress once again in front of me. I was still on my hands and knees as told me to hold that pose as I watched her strip once more. When she was fully disrobed she sat in front of me and spread her legs, one on each side of me. She took the dildo in her hand and said to me, "Get it wet," as she brought the dildo up to my mouth.

I just stared at it, frozen, a million things running through my mind. First and foremost the thought of "Um no," called out to me but quickly my mind raced to other things such as I was already dressed in a bra and thong it seemed a natural progression. And if I did this, maybe I would get some relief for my aching balls. If I did this, I would get to watch Trista masturbate with it. As all these things were running through my mind I once again felt my cock straining against the chastity device it was encased in.

I bent my head down and slowly took the tip of the dildo into my mouth. It was a good 8 inches long and about an inch wide. After I had the tip in my mouth Trista whispered, "That's it, you're doing great." She pushed a little more into my mouth and she whispered again, "You're doing great, pretend it's a real cock: suck on it like you would a real one."

Well speaking of real cocks, mine couldn't have tried to escape its cage any more than it was right now. My balls were aching and I couldn't have been more turned on than I was at this moment.

Trista continued inching more of the dildo into my mouth, encouraging me with each inch. Of course her encouragement consisted of calling me a cock sucking whore and mentioning that this dildo was much bigger than I was. But in the moment, it did the trick and turned me on. Occasionally she would take a picture of me with the dildo in my mouth as well.

Finally, she pushed the remainder of the dildo into my throat causing me to gag on it. She giggled and said, "You have to watch out for that, a real cock, with a man on the other end, won't go as slowly. You have to be ready." I absent mindedly nodded as she began to withdraw the dildo from my mouth.

"Now that you got this cock nice and hard, do you want to see me take it?" Trista asked. She knew the answer but I nodded immediately that I did. With that, she laid back, her glistening pussy on display and she slowly slipped the wet dildo into her. She let out moans as she adjusted to its size, and soon after began to slowly slide the fake cock in and out of her. It was quite a site to see her naked on the bed, her legs spread, her gorgeous tits moving with each stroke of the dildo pumping in and out of her. Finally, she reached the point of cumming and let out a loud moan and her entire body shuddered. After bringing her to multiple orgasms with my tongue the past couple of days you would think that it wouldn't have been as intriguing to see, but it was a real thing of beauty; this being the first time I was not preoccupied and could just watch and admire her.

Once she regained her composure, she sat up, a big smile on her face. "That felt great," she told me. Withdrawing the plastic cock from her pussy she brought it up to my lips again and said, "Now you get to clean it off," as she pushed it between my lips.

She was much less gentle this time around; forcing the dildo into my mouth and making me gag a few times before she deemed that the toy was clean enough. "I'm sure you wish it were a real cock you were cleaning my juices off of, but not bad for your first time. I think you should sleep in this bra and thong, it looks so sexy." I groaned as at that point I knew I wouldn't be getting any relief once again.

Trista retired to her room, leaving me in her bra and thong, exhausted, humiliated, aching and honestly somewhat questioning my sexuality after what just happened. There was a lot going through my mind and it took a while for me to finally fall asleep.