• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Paul and Becky Get Kinky Ch. 01

Paul and Becky Get Kinky Ch. 01

It had been a long, productive week of meetings and Paul was exhausted. He debated flying home on the red-eye, but the suite was already paid for so he decided to relax and spend one more night. Besides, he had barely had any chance to play this week. He opened a beer and walked over to the suitcase sitting in the corner. Opening it, he carefully laid the contents out on the bed survey the wide variety of pantyhose, leotards, catsuits, heels, and bondage devices he had brought. It was only a small part of the large collection he had acquired over the years, all carefully hidden from his wife in a storage locker he kept. They had a wonderful relationship and a decent sex life, but she absolutely refused to participate in his kinky hobby even to the point of making his get rid of the few items he had shared with her early in their marriage. So he had hidden his interests from her completely and only shared his secret with a few partners that included a wonderful professional dominatrix in San Francisco and a few men he had met online that loved to dress as much as he did.

He took the ice lock from the bed, filled it with water, and put it in the freezer. He then gave himself a quick enema. He enjoyed the rest of his first beer while he waited for it to do its job. The pleasant feeling of fullness made his cock spring to life, but that wasn't the only reason he did it. He knew it would make cleanup a lot less messy later in the evening. Once he was thoroughly clean inside, he began to clean himself outside. First, he took a long, hot shower and shaved his body. Lycra felt so amazing on freshly shaved skin.

While in the shower, he thought back to his first hotel encounter with another cross dresser. He was shocked that he had actually gone through with it, but later he realized it wasn't a big deal. He had sucked on his mistress's latex cock many times, a real cock in a condom was not much different. Jeri, as he called himself, had a serious oral fixation and loved sucking on his cock so their meetings were fun for both of them. It wasn't until their third meeting where Paul found himself tying Jeri up and sucking on his cock with wild abandon that he realized he was probably a bit bi.

The last of his body hair swirled down the drain as he toweled himself off. He carefully applied a bit of makeup and brushed his long hair down as he blow dried it. It was usually in a ponytail, but when it was down, it came almost to his shoulders. The first part of his transformation was complete, a decent looking woman looked back at him in the mirror. Next, he put some lube on his cock and balls and forced them into a tight latex sheath. The base of the sheath was a thick latex band so once it was on, it wasn't going anywhere. This was a good thing since even when playing alone, he could get pretty physical. The latex decreased the sensation enough to make an orgasm difficult, if not impossible. He hesitated for a moment before deciding on which butt plug to use tonight. At this point, he was so horny, he knew he would pick one that was too big and he was right. As he eased the huge plug into his ass, he gasped. It took almost 20 minutes of slow stretching before the plug slid past his sphincter. It would become even more painful as the hours wore on, but the feeling of being stretched was intoxicating. He had bought the plug in San Francisco at Mr. S Leather and it was 5 pounds of solid stainless steel. He loved the way it felt when he moved his body around, it massaged his prostate in all the right places.

The rest of his dressing went quickly. First a pair of thick Danskin tights, then a bra with huge DDD fake boobs, then a turtleneck leotard followed by a gloved / footed shiny lycra catsuit and 6" pumps with ankle straps. He completed the look with a heavy leather corset that crushed his waist from 34" to 28" By the time he finished pulling the laces by using the closet doorknob trick, he was gasping for air. Finally he buckled on a large, red ballgag, zipped on his favorite leather hood, and put on his leather ankle / wrist cuffs. Removing the ice lock from the freezer, he used a small padlock to lock it to one of his wrist cuffs. This was the moment he loved... He took another small padlock and locked the other wrist cuff to the ice lock. Now he was trapped until the ice melted.

He slowly teetered over to the full length mirror in the living room and was greeting with the image of a shiny, fetish doll. His cock strained again the latex sheath and the buttplug was already beginning to hurt. He tried to push it out, but the leotard and tights insured it wasn't going anywhere. A moment of panic set in. Why did he use such a large plug? What if he choked on his saliva from the ballgag? He walked around the large suite and the plug began to work its magic on his prostate making his cock harder than it had even been. This was his best self bondage so far. He tried rubbing himself against the arm of the couch and while it was exciting, he realized that he probably wasn't going to able to cum like this.

10 minutes into his self imposed torture, his feet and jaw were beginning to ache so he sat down and enjoy the kinky thoughts running through his mind. Sitting pushed the plug into a new and even more enjoyable position. He had already setup his laptop to watch his favorite pantyhose porn from Strapless Dildo dot com. The women on the screen were wearing shiny pantyhose and leotards too and he squirmed with desire as one woman penetrated the other with a Feeldoe dildo.

A moment later, his worst fear was realized. The door of the suite opened.

Oh my god, who are you and where is Mr. Carlson? It was the new intern in marketing Becky.

Paul could only mumble into his gag as he lurched into the bedroom. Even though Becky was an intern, she had come to the company after a short music career. Paul had always enjoyed working with her, she was smart and creative. Her tattoos hinted at a bit of a wild side and Paul now silently prayed that this was true.

"Mr. Carlson... Is that you?!"

Becky unzipped Paul's hood and unbuckled the ball gag, releasing a flood of drool onto the tile floor.

"You kinky little fuck." Becky laughed as she smoothed out Paul's hair. "I thought I saw a hint of shine above your black socks earlier this week. You were wearing pantyhose weren't you?"

"Shit Becky, what are you doing back here? You should be on a flight back to New York."

"Yeah, well that obviously didn't happen. Stupid airlines and their maintenance problems. I realized I still had a key to a beautiful empty suite so I came back instead of staying in some fleabag airport hotel, but enough about me, you look amazing!"

"So you're not going to tell anybody?" Paul would have breathed a sign of relief if the corset hadn't been so tight.

"No way! You're the hottest thing I've ever seen. My boyfriend likes to tie me up and I just hate it. I try to get him to let me tie him up, but he always refuses. I guess this is my opportunity to finally be in control and have some fun."

"You're joking Becky. This kind of stuff only happens in the erotic fiction I read..."

"No, I'm not joking and I see this conversation has only fueled your fetish imagination." Becky confirmed her suspicions by grabbing Paul's cock and rubbing. "What have you got on under there? It's so slippery! And where are the keys to these padlocks, that ice lock is making a mess.

"The keys are in the hallway under the trashcan by the elevator. You have to have a backup escape plan, right?"

"Yeah, right Mr. Carlson. I can just see you dressed like that creeping out into that hallway with a jammed ice lock..."

"Now that we know a bit about each other, why don't you call me Paul?"

"No can do. It's Paula or Slave, you can pick."

"Ok, Slave it is."

(to be continued)

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Paul and Becky Get Kinky Ch. 01

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 27 milliseconds