tagTranssexuals & CrossdressersWorking with Trista Ch. 02

Working with Trista Ch. 02

byamberbmaid©

This is the second chapter of an on-going story of working with Trista. All feedback is welcomed.

Day 3:

That morning I was awakened as my phone rang; Trista was calling me telling me it was time to get up. She said that she would be over shortly. I hoped it was to let me out of the chastity device. That moment couldn't come soon enough, and neither could I!

A few minutes later Trista knocked on my door. I opened it, and she was dressed in a pair of spandex shorts and a zip up workout vest. My cock tried to stiffen at the sight of her outfit. It didn't happen. She smiled and reached for my boxers. She fondled me, feeling the device, "I see you still have it on. Is it still working do you think?" she said will a bit of sarcasm in her voice.

It definitely was still working especially as I watched her in the skin tight outfit. She told me, "Well I have good news, because it's important to keep up your exercise routine I'm going to take off this device for your workout. But don't you dare think of cumming. Also, after the workout it goes back on each day. Sound good?"

At this point, I figured I'd best take this offer as I just wanted to get out of this thing, no matter how brief, and there was always the chance she'd change her mind. She kneeled down to unlock the device and immediately my cock sprang to life. It was fully hard in a matter of seconds just from being released.

"Ok go put on your tights," Trista said, "we're going to go work out."

I couldn't go like this I tried to explain to her, but she was insistent that we were going in just the tights and nothing more. Finally she said, "Ok, I've heard enough, today is the last day you're wearing black tights. I'm going to go shopping today and get you different colors, so your little hard cock will be even more noticeable." At that point I quit protesting, figuring I could only dig myself deeper into a hole.

The workout went as expected. I was hard almost the entire time, from my room, the elevator trip downstairs, throughout the workout, back up the elevator and back into my room. Watching Trista in her skin tight clothing certainly played a large part. By this time, my balls were aching and it wasn't even 10 am yet. I felt this could be a long day.

"Time to put your device back on," Trista said as we returned to my room. She went to the bathroom, and told me to come in with her. She then lowered my tights and touched my rock hard cock ever so lightly. I moaned instantly, wanting so badly to cum. She then got her hands ice cold under the water before returning to my cock. Immediately it softened and she locked the device back on me before I knew it. Oh the frustration. She then pulled up my tights and patted my ass.

Trista then stood up and unzipped her workout vest, revealing a very thin sports-bra that barely held her breasts. She took my hands and put them on her chest, my cock now straining against the device again.

She led me to the bed and said, "I wasn't planning on doing this until later but I did tell you I was going to make use of your tongue again. Just watching you struggle and knowing I control your little cock gets me so wet." With that she slipped off her spandex shorts, pushed me back on the bed, and climbed up me, straddling my face with her wet pussy inches from my mouth.

"Lick me slut," she said as she grinded her pussy into my face. I brought her to quite a few orgasms over the next hour. My face was covered in her juices and my tongue was sore by the end of it. Trista finally crawled off of me and said that it was great. She then patted my still sensitive and aching balls and told me she wanted to go down to the pool and that I should get my thong on.

She stood there watching me as I put on the thong. She said it'd be ok if I put on the board shorts today, which I thanked her for. We then went to her room and she went into the bathroom to change while I waited on the bed. She came out of the bathroom in a white bikini with some sequins on them. She looked magnificent. It was probably a good thing she kept the chastity device on me at this point as I would be rock hard at the pool the entire time looking at her.

We went down to the pool, and once again I was made to remove the board shorts immediately. I applied the lotion while having to half stand up again. When Trista was to put some on me, I was made to stand up and she slapped my ass quite hard which drew snickers from some of the people sitting near us.

After an hour or so, Trista told me that she wanted to go shopping. The pool was getting rather busy with people, so it was time to go. Back in our own rooms we had each showered and changed and Trista stopped by my room to pick me up. She was dressed in a tight top and jeans. She looked very good in such a simple outfit.

When I asked her where we were headed, she said she wanted to make a few stops. Our first stop was an athletic store. We went in and she told me that I could feel free to browse around for a while. About 15 minutes later, Trista came and got me and told me she had some stuff for me to try on. The first was a pair of running tights similar to the ones that I had worn the past two days while working out. However, instead of black, this pair was a very bright royal blue; something that would sure to be noticed. Also in the pile she handed me was a red spandex short sleeved top. The final item was a sports-bra. I handed this back to her saying I think you messed up the piles.

She just smiled and said, "No I want you to try that on too. Don't worry no harm in just trying it on. But I want to be able to see for sure so don't take it off before you show me."

I slipped the sports-bra on in the changing room, shaking my head at the absurdity of it all. I also put on the spandex tights and the spandex top. My cock was definitely pushing against the device wanting to be free at this point.

When everything was on, I opened the door to the dressing room, there were three dressing rooms in a little area and I saw Trista looking at some shirts, standing away from the dressing rooms. I got her attention and told her to come take a look.

She told me to come out to where she was, away from the "safety" of the dressing rooms. I shook my head no but she made a face that seemed to suggest that this wasn't up for any sort of debate.

Much like crossing the street I peered both ways before exiting the dressing room. "Oh hurry up," Trista said exasperated. I took a deep breath and went out, the sports-bra clearly visible underneath the skin tight shirt.

"Oh I like these. Very nice and shiny," she said as she ran her hands over my shoulders and down my back. She grabbed my chest and said, "How do you like this sports-bra?" I told her it felt funny and she just laughed and told me it looked good. Her hands continued down my back over my ass. She told me to turn around and there she slapped my ass. It was loud enough for others to hear because as I looked up I noticed others had too in my direction.

"That is for making me wait. You have 9 more of those coming as punishment. I doubt you want it administered here so I will cut you a break, ok?" I readily agreed to that, no way did I want her spanking me in the store where others could see. She told me to get changed and to just leave the clothes in the dressing room and meet her up front in 5 minutes.

I changed out of the clothes, my ass stung a little bit from her slap. She had some good power behind that one. I met her at the register; she was checking out and had 2 or 3 bags. I asked her what she got and said, "Don't worry about that, none of your concern."

As we pulled up to our next stop, I recognized it immediately as it was the adult store where the device was put on my cock the day before. Bolt was behind the counter once again, he laughed at his own joke when he asked me "how's it hanging."

When asked what brought us in today, Trista explained that she was looking for something to "keep me in line."

Bolt laughed a little and said, "Well the chastity device should be doing just that, but we have a few other things that might work."

We walked through the restraint section; Bolt showed us cuffs, some rope and a variety of things in the bondage section. Trista found a couple of Velcro cuffs that had a piece of rope attached so it could be tied to just about anything or to each other. It was pretty slick actually.

Next, Bolt took us through an array of whips, paddles, crops and floggers, showing Trista how each one works and how to properly use them to get the most out of them. And when I say that he took "us" though, I mean Trista, I wasn't much more than an afterthought and my opinion on things wasn't being asked at all. Trista couldn't decide between a crop and a paddle so she picked up both.

Bolt, being the salesman he is, started showing us the gags. It is amazing how many different kinds there are. He said that if Trista was going to use the crop or the paddle correctly, she may want one of these. She eventually chose a traditional ball-gag over a penis gag thankfully. Like I said; a good salesman.

Another couple, about in their late 30's came into the store and Bolt said hello to them before turning his attention back to Trista and explaining all the benefits of collars and their many uses. I didn't know how useful this was, but Trista picked one out regardless. It was black leather, had multiple D-rings on it, and could be locked on with a small lock. As far as my limited knowledge of collars went, it looked like a good selection.

Bolt asked if we needed anything else and Trista said she thought this should be enough for today, though we may be back tomorrow for something else. Bolt just laughed and said that'd be just fine. He rang us up and then said to Trista, "As you know, some of this stuff once used you can't exchange, but some, like the crop or paddle, that isn't a problem, same with cuffs. So if you want to try them out before you go, you can certainly feel free to do so."

Trista asked for more information and Bolt pointed her to where they had applied the device earlier by the dressing rooms or an open spot in the middle of the store. "We're sort of open-minded here if you hadn't noticed," he laughed.

Smiling Trista turned to me and said, "Yes we will try these out here, that's a great idea. He already earned a punishment earlier this afternoon so this will be a good time to administer it." To say I was against this would be an understatement, but Trista whispered in my ear, "Any whining about this will only make it worse, trust me."

I knew she wasn't kidding and so I followed her and Bolt to the area in the middle of the store, because of course, Trista couldn't pick the more private spot of the two. Once there, she asked Bolt his opinion and they whispered back and forth for a bit. Finally Trista turned to me with a grin.

She told me to take off my shirt and as soon as I complied she put the cuffs on my wrists as well. Bolt stood on a stool and tied the attached rope for the cuffs to a bar running overhead so my arms were above my head and I wasn't going anywhere.

Bolt standing on the stool got the attention of the other couple in the store and they came over to see what the commotion was all about. Trista introduced herself to them, explaining that she was going to test out her new purchases. She invited them to watch, though it looked like that was what they had planned on doing anyway.

The couple introduced themselves as Jake and Alana. Jake was a tall guy and was pretty well dressed while Alana was short, very pale with long brown hair, but had curves in all the right places. She had on black high heeled boots too which always catch my eye. When Bolt was finished tying me to the overhead bar, he stepped back and said to Trista, "he's all set." Trista walked up to me, and I pleaded with her not to do this in front of these strangers. She just smiled and told me to open my mouth as she forced the ball gag in. She strapped the gag in place and then began to go to work on my zipper.

In a matter of moments I was stepping out of my jeans and boxers with assistance from Trista, leaving me fully nude now in front of all of them. Alana commented on the chastity device, and Trista gave Bolt the credit for recommending it. I was utterly embarrassed obviously and just wanted this to be over with as soon as possible. But I could feel my cock wanting to get hard as it strained against the device, being on display in front of everyone.

"Well," Trista said, "let's get this show on the road." With that she brought the paddle down hard against my ass. I wasn't expecting it at all and let out a yelp into the gag. I immediately felt my ass cheek redden exactly where the paddle had hit.

Trista let me have 4 more on the same check, each one hurting more than the last. She switched sides and gave me 5 on the other side. By this time I had had enough as my ass felt very warm. She rubbed her hand over my backside telling me she liked the way my ass felt all hot and looked when it was all red. She said, "I was only going to try this out, but I think now we're going to do a lot more."

Turning to Alana, she offered her the paddle asking her if she wanted to try. Alana, smiled, shrugged and said, "Why not."

She stood behind me and laughed at her line of "This is going to hurt you much more than it will hurt me." With that, she proceeded to give me 10 smacks on each cheek. I gritted my teeth into the gag, as each blow rang down. I could feel my backside growing warmer.

Then I heard exactly what I didn't want to hear. Trista said, "Do you want to try Jake?" I was not at all excited by this prospect. Well let me rephrase that, while my cock was straining against its cage, I knew what was coming was going to hurt like hell. Jake of course accepted Trista's offer and Trista thought that another 10 total would be just right. After the first one I screamed into the gag, my ass hurting immediately as he must have put all he had into it. I opened my eyes, and saw Trista smiling deviously back at me. Five more and I had some tears welling up in my eyes. After what seemed like forever he finished up the 10 swings and sort of laughed as he said, "Wow, that's pretty red," in reference to my ass.

Trista walked around me and inspected the damage done behind me, "Oh my," she said, "that looks like it hurts. Well luckily for you, we only have to try the crop out yet and then we'll be done. I heard Alana laugh and Jake say to himself something like, "oh man."

Trista grabbed the crop and walked around me, she asked if I was enjoying myself and when I shook my head no, she tapped the crop against the steel cage holding my cock and said, "It seems this little guy wants to straighten out though. That tells me you're enjoying this quite a bit." And it was true, for some reason my cock was trying to get hard. Not sure if it was the actual beating my ass had taken, being tied up, or the humiliation of this happening in front of other people but it was true, my cock ached to be free, and my balls definitely were full.

Trista stopped tapping the cage, and tapped my exposed balls. She didn't do this very hard, really nothing more than a light tap, but I had been turned on for so long now and with no relief, the slightest touch was excruciating. My knees nearly buckled as she tapped my swollen testicles. "Oh my, looks like I will have to revisit that location soon," Trista said as she smiled at me. She went behind me and then said, "Ok my little slut spread those legs, and you have only 10 from me using the crop."

I spread my legs, still delirious from the perfectly placed tap she had given me moments ago. I soon snapped out of it as the crop cut through the air and landed perfectly on my backside. I yelped into the crop. While Jake definitely swung the paddle harder, Trista was at least able to match that with this device. With the paddle, everyone had taken their time and made sure that I was cowering in anticipation of the next blow. Not this time, Trista quickly administered all 10. It was quick but very painful. She put her hands on my ass and said, "Oh I love this warm feeling, we're going to have to try to keep it like this."

Trista and Bolt un-cuffed me and I was told to get dressed. Alana & Jake thanked Trista for the show and they made small-talk until I was dressed. When I was ready to go, Trista said her goodbyes to Alana & Jake, thanked Bolt and we headed to the car. I sat down in the car, very gingerly.

We got back to our hotel right around dinner time. I was still moving gingerly and in my room Trista ordered me to remove my pants so that she could see how red my ass still was. She smiled when she saw how it still looked. She showed me in the mirror and was very pleased with the handiwork.

She told me to relax and get ready for dinner; she wanted to go shower and get ready. I was exhausted, as this had been a pretty full day for me and I used the downtime to take a little nap.

I was ready to go when Trista knocked on my door for dinner. I opened the door and as usual I wasn't disappointed. In what is commonly referred to as a "little black dress" Trista looked wonderful, and as seemed to be the theme of her outfits, her breasts seemed almost destined to have some sort of wardrobe malfunction.

Once again, Trista wanted to see my backside and ordered me to remove my pants and boxers. She was a disappointed that a lot of the redness had faded, even though I tried to explain to her that the tenderness lingered. She told me as much as she'd like to make sure it was red for dinner she had a better idea. She took my hand and walked me over by the window, sat on the desk and pushed me to my knees. She leaned back, spread her legs, and said "you know what to do." I was pleasantly surprised to see she was not wearing underwear, and was anxious to get to work. She grabbed my hair and shoved my head between her legs. I started with my tongue, and added a finger to her wet pussy. For the next half hour, I brought her to multiple orgasms, my cock straining against my restraints. She pushed me back onto the bed, and removed her underwear and climbed up on my face. She said I knew what to do and for the next half hour I did exactly that bringing her to multiple orgasms.

When she had had enough she pushed me away and tossed me some underwear saying, "Here, since I'm not wearing these, you should tonight." I asked her why as obviously I wasn't all that interested in wearing women's underwear. She said that I had a choice, I could either wear her red thong, or she would redden my ass with the paddle until it was the same shade. It was an easy decision as I slipped the thong on.

Once it was on, I looked up right as Trista was taking a picture with her camera phone. "Very nice," she proclaimed, "now finish getting dressed and let's go."

I dressed and we went out to dinner to a nice restaurant. The thong of course didn't feel natural but I was making the best of it. As you can expect, every time I managed to forget about it for a few minutes Trista would remind me about it. Either asking how it felt, or if I liked the look or even saying that she wondered what the other people in the restaurant would think if they knew. All of this talk started to get my cock going again, or at least as much as it could while being stuck in the restraint.

Trista made a point to flirt with the waiter, Chaz, in front of me all throughout dinner. She kept saying she was thinking of asking for his phone number and bringing him back to the room. Since my cock was all locked up she said I wouldn't mind. She added insult to injury when she said that he probably had a bigger cock to satisfy her anyway.

When the check came, Trista actually did ask if she could have Chaz's phone number who gladly gave it to her. He smirked at me as he wrote it down.

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