This is the third of a set of stories about our main character’s experiences with TS escorts. While I’d like for you to read the previous stories (“Lisa, the TS escort” and “Back for seconds”), this story should read fairly well on it’s own. Thanks for reading, and I hope you enjoy it.
*****
Tom hung up the phone. It had been an old fraternity buddy who called to let him know about a reunion that was being planned in a few months. It was going to be a weekend event. Nothing fancy. Staying at a hotel that was offering a special rate. Hitting bars, dining out as a group, and some group activities during the day. Tom was definitely up for it. The location was about a 8-hour drive away. Yea, he could fly, but that’d mean a 2-hour drive to the nearest airport, then going through all the hassles of flying, renting a car. And the route went right through the city where he had previously spent time with his favorite, well only transsexual escort, Lisa.
His mind started spinning. Tom was sure his wife wouldn’t want to go. She didn’t like going to bars, and really didn’t know any of these guys that well. Sure, she’d met a few over the years, and all of Tom’s groomsmen were fraternity brothers. Still, she didn’t really click with any of them, with the possible exception of his best friend while in college. That wouldn’t be reason enough for her to endure a long drive. In addition, they had the pets that would need to be boarded if they both went, a significant expense. His wife also frequently babysat the grand-kids.
He didn’t like deceiving her, but in his mind, it wasn’t really cheating if he wasn’t with another genetic female. Besides, the two times before had been amazing, and the memory stayed with him. He frequently thought about the next time he would be able to make it to see her. That had been another 8 months away, but now, it might be sooner.
He talked about it with his wife, and sure enough, she wasn’t very interested in going. He said that it was alright, while his mind was doing cartwheels. Tom was not surprised at all with her decision – she genuinely did not like to drive long distances, and a trip to a hotel in a small city wasn’t worth the effort.
So he started making plans. He’d leave a day early, for the sole purpose of spending an evening with Lisa. It’d take about 5 hours do drive to her location. He’d get a hotel, have his fun, then get up the next day and make the additional 3-hour drive to the reunion. That way he’d arrive without being all funked up from a long drive, and ready to party with the guys.
On Tom’s last visit with her, he had asked her to bring a friend. While that had been a once in a lifetime experience, he did feel that his attentions were spread out a bit between the two. He wanted to be with just Lisa this time. He did a quick check to Lisa’s website to make sure she was still there, and that she hadn’t made and posted any travel plans for that weekend. Sure enough, she appeared to be available. He fired off a quick e-mail to her from his anonymous e-mail account.
“Hey Lisa, this is Tom. I’ve seen you a couple of times before. I’ll be in your area on a trip on Thursday, August 14th. I’d sure love to see you. Do you think you’ll be in town and available? I hope so.”
By now, he had learned not to expect an immediate response. How people could not check their emails every day was hard for him to understand, but he knew her habits. A couple of days later, she did respond.
“Hi Love. I think I remember you. I will be here. Please let me know when it gets closer. Thank you, Lisa.”
‘Yahoo!’ Tom thought. Another check of her website showed that her in-call location was the same. So he made a reservation at a hotel he knew was very close to that location. Walking distance in fact.
That night, he had a great masturbation experience. As usual, he was watching transsexual porn videos. And he had something new. Ever since his last encounter with Lisa, he became curious about anal play and prostate stimulation. He wasn’t ready to be a bottom. It didn’t appeal to him. But fingering Lisa and fucking her in the ass made him think about what she was feeling. She and many other people obviously enjoyed it. This led to him purchasing a prostate massager toy to investigate what the feelings were. He was using that, and his orgasm was mind blowing. It was going to be a super trip.
The Sunday before he was going to leave, he sent Lisa another email to remind her of his plans, and to double check she would be available.
“Lisa, this is Tom. I emailed you a while ago and have seen you a couple times in the past. I wanted to let you know that I’ll be in town this Thursday, the 14th. I’d love to see you for a couple of hours that evening, possibly starting around 7 pm. Will that be OK with you? I hope so. Let me know.”
The next morning, Lisa had replied.
“Love, I am available then. Give me a call that day to set everything up. See you then ;)”
Wednesday night Tom was packing things up. sex hikayeleri He had already packed away things he thought he’d need for his “date.” Condoms and breath mints for example. But at the last minute he had another thought. He went to his office and retrieved his prostate massager toy. He cleansed it once again, although he did so after every use. He made sure the batteries were charged up, then packed it away. It might be interesting to bring it along. He wondered how Lisa would react.
The 5-hour drive was uneventful, although it did seem longer than usual. As he got closer to the city, he felt his nervousness increase. Maybe it wasn’t really nervousness. More like anticipation with a little anxiety mixed in. He checked into the hotel about two o’clock in the afternoon. After getting to his room, he called Lisa. After a few rings, she answered with a soft, feminine voice.
“Hello?”
“Hi Lisa, this is Tom. I’ve been e-mailing you.”
“Hi Love. Are we still on for tonight?”
“That’s why I’m calling. I wanted to confirm that I’ll be there about seven. Is that still good?”
“Yes, Love. I’ll be at my in-call location by then.”
“Lisa, I’d like to spend a couple of hours with you this time, is that OK?”
“Sure. That sounds great” she replied.
“Is the donation amount on your website correct for two hours?”
“Yes, Love. It’s four hundred.”
“Good. And your in-call location – I checked your website – is it still the same location?”
“Yes, dear. Same as last time.”
He was a little flattered that she had recalled they had met up before. “I assume you’d like some wine again?” he asked.
“Sure, Love. Give me a call when you’re at the market.”
“OK. One more thing. I loved the stockings you wore last time, so if I have options, I’d like that. I’ll give you a call around seven. Looking forward to seeing you.”
“Bye, Love.” She hung up.
Tom looked at the clock. He had about four hours before he’d have to leave for the short walk to the market. As was his routine, he retrieved a bottle of bourbon from his suitcase and poured a glass. He tried to calm down. He was surprised at how even just talking to her made him woozy. Giddy like a school girl. He sat down and sipped the bourbon. After finishing it, he shaved, then took a long, hot shower, being sure to clean all his intimate areas. He brushed his teeth good, and used the hotel mouthwash afterwards. Tom put on a limited amount of cologne, then sat down again for another short pour of bourbon.
By the time it was gone, it was time to head out. Tom gathered what he needed. The condoms, mints, and sex toy. He put them in a small bag he brought with him. He placed the donation in a hotel envelope, then double checked to make sure he had everything.
He walked to the market, went inside and purchased the same bottle of red wine he had bought before. ‘Why change what works?’ he thought. He stepped outside, and pulled his phone from his pocket. It read 6:56. He sat down on a bench and took a few deep breaths, trying to calm himself down. ‘Why am I so nervous?’ he thought to himself. ‘This is my third time. I know how it’s going to go.’ He tried to reason things out, but only came to the conclusion that it had been so spectacular in the past, he was afraid of things not turning out the same.
He looked at his phone again. It was time to call. After a single ring, Lisa answered.
“Hello Love, are you at the market.”
“Yes, Lisa. I’m ready to head your way.”
“OK dear, walk to the apartments, turn in front of the first building, and walk in the entrance at the middle.”
He stayed on the phone while he walked to the door, updating her with his progress. He walked inside and found the elevators. “I’m in front of the elevators.”
“OK, I’m on the third floor.”
He got in and pushed the button for the third floor. “I’m headed up” he told her.
When the door opened on the third floor, he told he had arrived.
“OK. I’m in apartment 342.”
He remembered it was the same as before. He walked down the hallway and found the door to the apartment. As last time, the door opened before he could say anything on the phone or knock. He turned his phone off and walked in.
“Hi Lisa, you’re as beautiful as ever.”
She smiled, and embrace him. They immediately started kissing. Soft superficial kisses at first, then she began to French kiss him. ‘Damn, she was talented at that,’ he thought. He broke away, handed the wine towards her saying “Here’s the wine.”
She took it, grabbed an opener and two glasses from the counter, and said “Follow me.”
He watched her walk in front of him. She had long legs. Legs that didn’t want to quit. She had worn the long stockings and they were spectacular. Her has was firm and round. Perfect. He was already getting a partial erection.
When he got to the bedroom, he checked things out. It was pretty much the same as last time. A queen bed in the porno hikayeleri middle. A night stand. And the same old lava lamp that obviously had been turned on just recently. It’s red “lava” was still thickly clumped together, and it cast the same red glow across the room. A dresser was on the other side of the bed, with the same small television playing a porn video. The volume was very low. He took the time to see what was playing – it was a blonde giving a guy a blow job.
Lisa made her way across the room to the dresser, and began to uncork the wine. He followed her and laid the envelope on top of the dresser. With his other hand, he put the small bag on the dresser as well. He watched as she gazed at the bag with curiosity. “Don’t worry, it’s something good” he said to dismiss any concerns she might have. Lisa smiled and picked up the bottle of wine. She poured to glasses of wine and handed one to Tom.
“I remember you” she said. “You’re nice to me.”
“You deserve it. You’ve been very nice to me.” Tom replied. He leaned toward her and placed his free hand around her waist. He kissed her again, slipping his tongue gently into her. She responded, and their tongues danced for a minute.
He broke away, and took another swig of wine. He noticed that by now his glass was almost empty compared to her nearly full glass. Lisa noticed as well, picked up the bottle, and poured him some more.
Tom decided to take a little time. He sat down on the bed, and motioned for her to sit beside him. When she did, he caressed her face and neck with his free hand. “You are very beautiful. And sexy.” Before she could react or respond, he leaned in for another kiss.
“Thanks, Love,” she replied after the kiss ended. “I like being with you.”
Tom knew that this might just be her catering to his desires, making him feel great. It was her job after all. But he hoped that there was some genuineness to her statement. He felt they did have some chemistry. He wasn’t stupid. He knew that she was a professional. But he wanted to believe that there was some real connection between them.
He finished off his wine, and stood up to place his glass on the dresser. He reached down to her hand, gently grasped it, and pulled her up. When she was standing, he stepped back to appreciate everything. Her eyes were amazing. Bedroom eyes. Dark and beckoning. Her auburn hair was long and cascaded down the sides of her face. She wore a black bra. Lisa’s breasts were not huge, but comparable to what some may call prepubescent. In his reading of transsexual information on the web, they might be called “hormonal breasts.” That was OK with Tom. He wasn’t a huge fan of large breasts. Not that he would reject someone with double-D’s, but his preference was for something smaller, more natural.
Her stomach was flat and looked soft. She had a pair of black lace panties on. He could see the outline of her already erect cock. That was so hot to him. He wanted to grab it right then and there, but that wasn’t the plan. Not yet.
Then his gaze fell down her legs. Those long graceful legs covered in black stockings. All the way down to a pair of black high heels. She was amazing. 95% woman. And the other 5% was perfect as well.
Tom dropped to his knees, leaned forward, and kissed her cock through the panties. Lisa moaned softly. He traced the outline of her with his fingers. Very gently, up and down the shaft. Then he ran both of his hands down the back of her legs while he again kissed her penis along it’s full length. She smelled great. He couldn’t wait to taste her.
Tom reached up and pulled the top of her panties up, and slowly down. He let them ease back against her when her cock head was free. Then he went to work. He kissed the tip of her magnificent penis and followed that with several flicks of his tongue. He tasted her salty pre-cum from the tip, and concentrate his efforts on the frenulum area just under the tip. He could hear her breathing in and out, and was pleased that he knew he was giving he pleasure. He pulled her panties completely down, and Lisa stepped out of them.
Tom then stopped, stood up, and kissed Lisa again. “Your cock is amazing, and it tastes great” he said.
“That felt wonderful. Why’d you stop?” she replied.
“We’ve got some time. I want to savor our time together.”
“Take your clothes off.” Lisa said.
Tom reached down and undid his belt. He kicked his shoes off, then let his pants drop to the floor. He wasn’t wearing underwear; he felt it would just be a waste of effort. Then he reached down and pulled his shirt over his head. When it was covering his face, he felt Lisa touch him on the sides of his chest. ‘How nice’ he thought. She knew enough to go slow – to not rush to his genitals right away. He yanked the shirt off, and let it fall.
He felt her kiss his nipples. First one, then the other. Then she moved back to the first and gently sucked on it. He was in heaven. It really felt good. He had always seks hikayeleri liked it when his lovers kissed and sucked on his nipples. Then she kissed her way down his stomach to his fully erect cock. She kissed the tipped, then licked up and down the shaft. She gently cupped his balls in her hand at the same time, softly rolling them to and fro.
Then she licked back up to the tip. She flicked her tongue across the top, and like he had done her, tickled his frenulum area with the tip of her tongue. It felt wonderful. The next thing he knew, she had taken him into her mouth. She only mouthed the tip of his dick. Her tongue played and swirled around the tip. She was taking her time. He looked down, and she glanced up at him. The sight nearly put him over the edge.
But coming so soon was not in his plans. Not that he could definitively plan this night’s encounter, but he wanted to wait. He pulled back away. Lisa tried to follow and continue her attentions, but he wanted to be in control.
“Lay down on the bed” Tom said. “On your back.”
Lisa followed his commands. She laid on her back. Tom reached into bag on the dresser and pulled out the prostate massager. She looked wide-eyed at it. “You know what this is?” he asked. She shook her head to say she did. “Is it OK? It’s clean, but if you want, we can put a condom over it.”
“No, Love. We’re good to go.”
“I don’t have any lube. You have some I can borrow?”
She motioned to the night stand. He walked around to it, his cock still at full attention. He knew what was coming and it had him as sexually excited as he had ever been. He opened the night stand drawer, found the lube, and pulled it out. Then he walked back over to where her legs were extending past the edge of the bed. He crawled onto the bed in between her legs, nudging them aside as he advanced towards her ass.
From past experience, he knew that Lisa pre-lubricated. To check, he crouched down and played with her rose bud. She gasped, and then he inserted his middle finger. It went in easily, and he knew she had taken care of things. He pulled his finger out, then squeezed a bit of lube on the business end of the massager. “Are you ready?” he asked.
“Yes, put it in Love” she replied. It was almost as if she were begging.
Tom pressed the massager against her anus and applied a slight pressure. At first, it didn’t go in, but with a bit more pressure, it slipped in. He advanced it to the hilt, hoping the tip was in the correct position. He looked at Lisa’s face, and asked “Are you ready?”
She said nothing, only nodded her head.
Tom pushed the button to start the action of the massager. Slow at first. Almost immediately, Lisa let go a deep moan. He thought she was really enjoying the sensations. Her eyes were closed and she was moving both of her hands back and forth across her abdomen. Tom’s gaze lowered to her erect cock. He couldn’t wait any more.
He lowered his mouth to her genital region. Not wanting to ‘go for the gold’ just yet, he kissed just above the base of her cock, then bypassed her cock and kissed her inner upper thighs. She still smelled great. As her hand continued to move, she slowly began to gyrate her hips side to side and slightly back and forth. He watched her dick bob slightly up and down with the movements.
It was time. Tom began to kiss the tip of her cock. He flicked his tongue across it, but didn’t yet take her into his mouth. He wanted to tease her a bit. Softly, he asked “Do you want me to increase the massaging motion?”
Lisa let out a guttural sound, somewhat like a low “mmmm” that wasn’t really committal, but she was slightly nodding. Tom reached down and increased the motion of the massager. Lisa almost immediately let out a moan, louder than the ones before. He knew she was enjoying it. It was time to push things to the next level. He lowered himself to her hard dick, and took the tip in his mouth. With his right hand, he slowly stroked her shaft up and down. His left hand reached down to the massager, and pressed it so that it would be pressed more firmly against her prostate.
After tickling her sensitive areas with his tongue, he slowly descended down her shaft. He went all the way down, feeling the head of her cock slide past the back of his mouth into his throat. He almost gagged. He pulled back a bit, then took a good breath. Then he went back down all the way, letting the tip of her dick slide into the top part of his throat. Trying the best to suppress his gag reflex, he did some quick up and down motions, and swallowed against her cock. By this time Lisa was moaning loudly.
Tom continued his blow job and deep throat activity. He was only guided by what he thought he would like to feel, but judging by her reactions, he was on the right track. He occasionally nudged the massager with his left hand, each time eliciting more vocalization from Lisa. He had given up using his right hand on her cock, instead using it to gently caress her scrotum. He only now realized that her balls were a bit on the small size, contained in a hairless, yet beautiful scrotum. He was tempted to let go of her cock and suck her balls, but he was on a mission. A mission to have her erupt sending her sweet semen into his mouth.