Lisa, the TS Escort

This is my second transsexual story for Literotica.com. (By the way, I wish they'd separate the transsexual and cross-dressing category.) I had a mixed reaction to my first, but c'est la vie. I write these stories for me. It's good to hear feedback, and I learn a bit from everyone's input (thanks). The author does not condone or recommend illegal activity, and unprotected sex is a risk that is not worth taking in real life, especially anal and vaginal intercourse. Even unprotected oral sex has risks, as antibiotic-resistant infections are growing in frequency. Still, one can dream, no?

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He was nervous as hell. Like being on a first date. Tom thought how odd it was that even though he had planned everything as much as possible, the excitement of doing something real for which he had been fantasizing for so long was unbearable. He was literally shaking. It was time to make the call.

Let's go back in time a bit...

Tom had to be in the city for several days for a work-related conference, and had finally made the decision to realize his dreams. He'd always been a bit of an internet porn addict. He jacked off several times a week. It had started with the usual scenes - blow jobs, three-ways, and double penetration being his favorite. He had even had a short run where bestiality was his thing. But several years ago he had run across the she-male movies. They became his go to porn. He especially liked the scenes where men would be sucking hard she-male dicks and the t-girls would come in the mouth or on the face of the guy. It didn't take him long to blow his load with those movies.

He thought he knew why they were so appealing to him. His very first sexual encounters had been homosexual. He was 12 and in scouting. One night on a camp out, his patrol group was having the usual late night bull session in a large tent, when someone mentioned the phrase blow job. He didn't know what that meant and asked. Everyone laughed, and someone said they'd tell him if he'd do it. He agreed, wanting to fit in. After learning, of course he wanted to back out, but the idea of using a plastic bag (as a makeshift condom) was presented, and he agreed. After being explained the mechanics, everyone of his 5 tent-mates got a blow job. Not to completion by any means, just a few motions up and down.

Out of that evolved a special relationship with one of his buddies over the next year. Tom ended up giving short blow jobs, usually on camp outs to his new friend. Again never to the point of an orgasm. And Tom had gotten a couple of great hand jobs in return, although he felt that was never really fair or equitable. One night at summer camp, where he and his buddy shared a tent, his buddy asked Tom to fuck him in the ass. Tom did. It had felt OK, but again, no orgasm. The last encounter happened when Tom was visiting his friend's house one afternoon. They decided to walk around the neighborhood, and while exploring a house that was being built, his friend asked Tom to give him another blow job. This time he wanted to role play a bit. He walked into a room in the house, and pulled out his hard dick in front of Tom who was already on his knees. Tom took him in his mouth and moved back and forth. His friend must have been extremely horny with the role play as he came in Tom's mouth in less than a minute. It was unexpected. The taste was not bad, but the consistency was odd. He had swallowed some, but ended up spitting the rest out. Shortly after that, his friend moved away, and that was the end of Tom's homosexual experiences. Or so he thought.

He became a raging and exclusive heterosexual. Dating girls in high school. Having long term sexual relationships with women in college and graduate school. And marrying a great woman and having two children after that. But with time, the sex started becoming routine, and occurring less often. He turned to internet pornography and masturbation to relieve his needs.

He had decided to go part-time at work. He was only 52 but had made good investments and felt that he was close to being ready to retire and wanted to test the waters. But going part-time meant that the company no longer paid for his continuing education trips. In the past, he had taken his wife with him, but it no longer was financially viable. Besides, they had dogs to take care of and grandchildren to help out with.

This was going to be his second trip without his wife. About five months before the conference, he happened to notice a title of one of the porn movies. "Escort TS Fucks" was the title. While the movie was not a great one, it did get him thinking. Of course Tom knew about the usual female whores and escorts. They never interested him. Not when he was younger as he could get laid without them, and not now as he was married. But he got to thinking more and more about a TS escort. In his mind, it probably wouldn't be really cheating if he wasn't having sex with another female.

So Tom started doing research. He searched she-male escorts and found a great deal of information. Everything from them not appreciating the "she-male" terminology, to finding websites where trans escorts advertised. He even found sites where the escorts were rated and very specific details, including their "functionality," of the escorts were provided. He looked into what to watch out for as the possibility of being arrested was something he had to avoid. He read about scammers. Tom read about what to expect from a TS escort. He determined that he was going to have to have a "versatile" escort. Not because he wanted to be topped, but because he had a real desire to give a blow job.

In fact, he decided he had to practice at the art of giving a blow job. After all, it had been decades since his last one, and it was given to someone inexperienced, so technique was probably not an issue at the time. He read online and watch "instructional" videos. He read about how to give deep throat. He learned that being sure to take a deep breath before attempting it was the key. Tom bought long sausages at the grocery store and practiced with them. He got pretty good at sliding the sausage down past the back of his mouth and into his throat without gagging. Even practicing was exciting.

He read ads online, and the various trans escort sites. Many were immediately dismissed, due to looks, something in the wording, or that they were "tops" only. He researched the others on review sites and did phone and image searches in an attempt to verify, at least to some extent, their authenticity. He also checked out the information on how much the service would cost him. He was amazed that it was not as much as he thought it would be. After a couple of months, he found a few that he was definitely interested in. About a month before the trip, he created a new e-mail persona, and sent e-mails to the three. He indicated when he was going to be in the city, that he was interested in meeting them, and if that was possible. He got return e-mails from two, and decided to try to meet them both on different nights. He purchased a "hobby" no-contract phone and got a month's worth of service. The night before he left home he e-mailed them again stating he was definitely going to be in the city and would call them the day of the potentially agreed upon "dates."

Tom arrived at his hotel in the middle of the afternoon and checked in. He took a long shower and shaved. Then, after relaxing with a few glasses of the bourbon he brought with him, he made a call to the first night's escort. He had already programmed her contact information into the phone. Her name was Lisa. The phone rang a few times and a feminine voice answered "Hello?"

"Lisa?" he said.

"Yes?"

"Hi, this is Tom. We've talked a bit by e-mail. I'm in town and wanted to set up for a meeting tonight." His voice was shaky. Despite the alcohol, he felt nervous, like the very first time he asked a girl out on a date.

"Hi Love, what time were you thinking" she replied.

"About seven would be great for me. Is that good for you?" he asked.

"Sure, Love. Now, on my website, there's a hidden page that has a map of how to get to my location." She gave him the URL and waited while he looked it up on his laptop. She told him where to park when he was there. "Give me a call when you get there, OK Love?"

"Yes, I will. Looking forward to seeing you" he said. "Goodbye."

"Goodbye, Love."

He hung up the phone, then went over the map trying to memorize a route from his hotel to the designated parking area. He got the directions and calculated a driving time. Tom added about 10 minutes in case of traffic or if he made a wrong turn.

As it became time to get ready to go, he got dressed. He took a hotel envelope and placed the $250 "donation" in it, and put it in his back pocket. He retrieved his drivers license, a credit card, and a small amount of cash from his wallet and left the rest in his room safe. Tom made his way to the hotel lounge for one last bourbon before he left. He then got into his truck and headed towards her place.

He arrived almost on time, glad he had given himself more time as traffic was a bit congested and it was tough to find a good parking spot. He parked, and made his way to the location she had indicated to call from, which was in front of a small market. Tom then called her once again.

"Hello, it's Tom."

Hi, Love. Are you here?" she asked.

"Yes, I'm in the front of the market."

"A bottle of wine would be great. Can you pick one up? They have a good selection in the market."

He was a bit put off by this. She could have mentioned it earlier. But what the hell. As nervous as he was, he could use a glass of wine. He didn't know anything about wine. He could talk beer and whiskey all day long, but wine? "Yes, I can do that."

"Great, Love. Give me a call when you're ready."

He asked the clerk for a recommendation. He picked it up and headed back out. He dialed her once more. "Lisa, it's me, Tom."

"OK. If you stand in front of the market, and look forward, you'll see a series of apartment buildings."

"Yes, I see them."

"Go past the first one, then turn right and enter the second one. I'll stay on the phone while you head the way."

He headed towards the second apartment, making small talk and indicating his progress as he went, although he was sure she was probably checking things out from a window.

"OK, Love, turn in between the first and second buildings and go about halfway in. You'll see the entrance on your left."

"I see it." When he got there, he went inside. "I'm inside."

"You'll see some elevators. Go to the third floor." She gave him the room number.

Tom got in the elevator and pushed the button for the third floor. He got out, and looked to see which direction to go. He headed right, and determined that the apartment would be on the left. When he got to the door, he was about to tell her he was there when the door opened.

He stepped into the room. It was dark, but he could see a figure behind the door, which shut behind him. His eyes quickly adjusted to the dim light in the apartment. Tom saw her there, dressed in a black bra, black lace panties, and stockings with a garter belt. She was a bit on the tall side, with legs that wouldn't quit, and long auburn hair. She was as beautiful as her pictures were on her website. He had done well. He was still nervous, but it was due to his excitement.

She stepped up to him, took the bottle of wine, and said "Grab my ass."

What a great opening line, he thought. Of course he stepped in close, wrapping his arms around her, and grabbing each ass cheek with a hand. He gave a gentle squeeze. They were face to face, and he leaned in and gave her a light kiss on the lips. He pulled back a bit and looked her in the eyes. They were beautiful as well. He leaned in again, this time leaving his lips open as he kissed her. She darted her tongue into his mouth. Not the gross slug-like tongue, but a soft, playful, dancing tongue. He responded in kind. She made soft moaning sounds. They kissed for several minutes. He was already hard.

She stepped back, grabbed him by the hand, and led him into the bedroom. There was a large queen size bed, a dresser, and a night stand. A lava lamp was on the dresser giving off a red glow. In the corner was a small television playing a porn movie. His eyes had already adapted to the dark, so it seemed as light as day to him. She stopped in front of the bed and turned to him. He reached in his back pocket, grabbed the envelope, and placed it on the dresser.

She grabbed something from the dresser, which turned out to be a wine bottle opener. Lisa opened the wine, and poured two glasses, handing one to Tom. They each took a drink. "It's good" she said.

"I don't know anything about wine. It was the market clerks suggestion. But it is good" he said.

She said something about the area code on his phone indicating where he was from. Tom said that he lived in that general area, but of course, did not offer specific details. They made small talk while they kissed and drank the wine.

Tom's wine was gone quickly. He sat the glass down on the dresser, then reached toward her and brushed her long red hair from her face. He had a huge thing for redheads and this was just perfect. Once again, he told her how sexy she was.

"Thanks, Love" she said, then closed in for another kiss. She sat down on the bed, grabbed his hand, and gently pulled him down. They both lied down next to each other. They continued to kiss, and he began to gently caress her body, starting with her neck, then moving to her shoulders and stomach. Tom didn't make the move to her breasts or genitals yet.

"Why don't you get comfortable?" she asked.

With that, Tom got back up, and slipped his shoes and jeans off. He had gone commando, so underwear wasn't an issue. He left his shirt on, and laid back down next to her. His cock was at full attention.

Lisa started to caress him, which was something that Tom loved. She went slow, but eventually made her way to his penis. She caressed it softly, not really jacking him off, but slowly and gently running her fingers up and down, occasionally making a detour to his balls. It was great.

Tom began working his way down her body with kisses. From the neck, to her stomach, then up to her breasts. She still had her bra on, and he could tell that she didn't have large breasts. In fact, they were small, almost pubescent. But Tom had always had a thing for smaller breasts. He had no idea where that came from, but is was what it was. Lisa gave up trying to continue caressing his cock, and laid back. He worked his way to her stomach and then lifted up to look at her panties.

Her rigid cock was evident through the lace panties. He began to gently caress it through the panties, appreciating her firmness. It was about 6 inches long, and normal in girth. He moved his fingers up and down it's length. Eventually, he reached up to the panties and pulled them up and down away from her penis.

"Just a minute" she said. Lisa reached down and gracefully removed her panties, exposing herself, then laid back down.

Tom gazed at her. Her cock was just plain beautiful. It was circumcised, neat, and basically perfect in shape and form. He reached down and again caressed it as before. Something deep inside him took over and he leaned down and gently licked it. A slow tonguing from just above the scrotum up to the tip. He continued to slowly taste her. She was clean and tasted great, nothing at all disgusting.

Tom reached down and lifted her cock a bit so that he could look at the entire specimen. It was magnificent. There was a bit of mucus at the tip. Just a small amount. "Pre-cum" if you will. He leaned in and gently licked it off. It was salty and he thought it tasted great. Lisa softly moaned.

He needed no more encouragement than that. Tom took her cock head into his mouth and brushed his tongue across the tip and around the head. Again, Lisa moaned, seemingly urging him to continue. He pulled her dick up a bit more and dove down on it, taking most of it in his mouth. Again, some more soft moans were heard. Tom then began to bob his head up and down. When he'd get to the top, he swirl his tongue around the head, and when he was at the bottom, he moved his tongue in a somewhat swallowing motion. He had no experience, it was just coming to him.

It was time. He took a good breath and dove down, taking her entire length into his mouth. He felt the head pass his uvula and palate and enter his throat. Tom's chin was pressed against her body and he gave a couple of swallowing movements.

"Oh, God, that's good, Love" she moaned more than said.

Her use of the word "Love" was turning him on even more. He continued to alternate tonguing and deep throating and Lisa continued to moan. She started to slowly move her hips back and forth, almost fucking his mouth. The fact that he was getting her off this much was pure excitement for him.

After a few minutes of Tom's cock worship, Lisa let out a "Mmmmph" and he felt her squirt her first load into his mouth. He savored the flavor. Then swallowed as the next deposit came. It was heaven. He slowed his operations, knowing that he needed to allow for her post-orgasmic sensitivity. When he thought she was done, he lifted off her and took her orgasmic beauty in. She was breathtaking.

He was a bit exhausted, and laid down on his back. A minute later, she was caressing his rock hard cock again. Lisa quickly moved down and took Tom in her mouth. She tongued his cock head, then started bobbing up and down. Tom was enjoying the sensations, but maybe it was a bit too quick. "Wait a minute" he said. She lifted off and he sat up to remove his shirt. "Lick my nipples" he said.

Lisa moved up and softly licked his right nipple. Then she pressed her lips against it and sucked hard. She continued to lick and suck, even nibble at his right, then left nipple. Tom enjoyed the sensation. Yes, even guys like to have the nipples sucked and nibbled. At least Tom did. He imagined most men did, and if they denied it, they were lying.

Then, without needing a que, Lisa worked her way slowly down to his cock again. That was the key. Going slow. She started licking and sucking his cock. It had all this time remained firm and erect. Tom felt himself getting close. He reached down, and pulled her up to him. He kissed her and they played with each others tongue. He could taste his pre-cum in her mouth.

"I want to fuck you babe" he said. There was no nicer way of saying it. No, it wouldn't be making love, even though Tom felt a special attraction to Lisa. As much as Tom loved cumming with a blow job, he wanted to put his cock in her ass and blow his load there.

"Oh yeah, that's want I want too" Lisa said. She got up and knelt on the floor next to the bed, laying her upper body onto the bed. Tom got behind her and began to rub his rock hard cock in her ass crack, then under her ball sack. He was super hard, and tempted to ram his dick into her. But he knew better. Precaution is better, so he stopped and asked for a condom.

"You can bare back. I trust you" she said.

"Let's use a condom. It's safer for both you and me." Tom returned.

She reached into the night stand and retrieved a condom. After unwrapping it, she rolled it down Tom's cock. Then she quickly reached for something and he felt her apply lubricant to his covered penis. She turned around, knees on the floor, and bent over. She reached back and pulled her ass cheeks apart. Tom dropped to his knees and leaned forward. His cock entered her easily. He guessed she had pre-lubricated and maybe had even pre-dilated. He didn't really care. It felt great. He slowly moved in and out. At first, it was hard to keep his cock in her ass, but eventually he got the hang of things and began to pump her hard.