Back for Seconds

This story is a follow up to "Lisa, the TS escort." While it's not necessary to read that story before this one, doing so may provide some background that won't be covered here. Again, 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. So much for the PSA part of this reading.

It had almost a year since Tom had been with Lisa, his first TS experience ever. He had thought about it now and then, each time brought a smile to his face and a rise in his pants. To him, it was truly a magical moment. A few months ago, he starting planning for another trip back to the city where it all happened. He'd be going back for another conference for his work, and of course, would be making plans to visit Lisa once again.

He had been following her website, making sure she was still in the same city. He had provided a review of his experience to one of the online escort review sites, and noticed that she routinely had high ratings. That was certainly his findings. He'd be heading back there in about a week, and it was time to initiate contact once more. Tom still had her e-mail address, and fired off a quick note to start things up.

"Hello, Lisa.

This is Tom. I saw you almost a year ago and had a great time. I am planning on

being back in town in about a week and was hoping I could meet up with you again.

Hopefully you're in town and will be free. I'm looking forward to hearing from you.

T."

Naturally, he didn't expect an immediate response, but he found himself checking his "hobby" email account several times a day over the next few days. Finally, she returned his email.

"Hi Love,

Of course I'll be here and would like to see you. Do you know any details as to the date and approximate time? Let me know.

Lisa"

Tom found himself already getting excited about the concept. But there was something else he was wondering about on this trip. He had read on her review page that she would be agreeable to bringing another provider. This was one of his favorite fantasies - being with two T-girls at the same time. The online videos where one guy was with two transsexuals were, to him anyway, the hottest, and ever since his encounter with Lisa, he wondered if it was possible to experience that first hand. He wanted to ask, but didn't want to offend her, so he carefully crafted a follow up email.

"Lisa,

Tom again. I am thinking about Thursday evening, the 4th, and likely around 7 pm, if that's good with you. In addition, I've read on your reviews that you might be amenable to bringing another provider. Do you know another T-girl escort that would be willing to have a 3-way session with us?

T."

This time it only took a day for a response. But it wasn't exactly what he had hoped to hear.

"Love,

You may have misunderstood. I can arrange to someone else to our session, but all of the local T-girls are a bit scary to me. I do know a girl who I've done some work with. She is beautiful and I'm sure you'd be happy with her. Let me know if I need to ask her if she is available.

Lisa"

Well damn, thought Tom. He was a little bit let down. But he thought about it. Yes, it would be exciting to do that. He'd never done a three-way before, and he guessed that it would be exciting either way, whether the third was a cis girl or a T-girl. He instantly started imagining all the options of sexual play with a T-girl and a genetic female. So he responded to let her know that's what he wanted.

"Lisa,

That's sounds great to me. Please make those arrangements. Let me know if you need more information. Like last time, I'll call you the day of the meeting to make sure all is set up and to confirm. Looking forward to seeing you then,

T."

For the next week, it was all Tom could think about. It was hard to concentrate on anything else. Work, home-life, and even play took a back seat in his mind. He bought a month of service for his "hobby" phone and even picked up a small pack of condoms, just in case. He watch videos of three-ways in order to figure out what he wanted to do and how. Although, truth be told, he'd probably forget all that once things got rolling. He checked out Lisa's web site and ascertained that Lisa's in-call location was the same as last year.

It was a long drive to the city, or at least it felt like it took a long time. He checked into the conference hotel, which fortunately was fairly close to where he had to go later. Tom decided to grab a quick late lunch, then went to the room to get cleaned up for his adventure. About mid-afternoon, while sipping on some whiskey he'd brought with him, he gave her a call.

"Hello?" she answered with a soft voice.

"Lisa?"

"Yes, Love?"

"Hi, it's me, Tom. I talked with you by email recently. I'm calling to see if things are still a go for this evening." Even though he'd been through this before he was still nervous, and was sure it showed in the tone of his voice. "We had talked about you bringing someone else. Is that all set up?"

"Yes, Love. My good friend Jessica will be joining us. I think you'll like her. She's fun."

'Lisa and Jessica' Tom thought. 'Wow, this is going to be a blast.' He almost couldn't help beginning to fantasize about it right there and then. But there were a few things to take care of first. "Is 7 still a good time?" he asked.

"Yes, 7 is good."

"I think I remember where your location is from last year. Is the map on your website up to date?"

"Yes, Love, it is. I've moved to a different apartment but I'm still in the same location." Lisa gave him the URL of the website where the map was, but Tom had already looked it up several times while making his plans.

"One last question, and I hope I'm not out of line. The donation - how much more is this going to be?" Tom asked. He had absolutely no clue. He guessed it'd be 3-4 times the usual rate, with scheduling hassles and everything. Plus, he knew from checking things out online that genetic female escorts tended to run a bit higher. He had prepared for it and had the cash.

"It'll be twice as much as usual, Love." Lisa answered.

"OK" said Tom. "Well I'll plan on getting to the location at 7, and I'll give you a call when I get there. Should I bring some wine again?" he asked.

"Sure, Love, that'll be great. Talk to you later."

"Bye." With that Tom hung up the phone. He glanced at the clock - it was just after 5. He had a little over an hour before he had to head out. He poured himself another glass of whiskey, and got everything ready. He put the cash in a hotel envelope and added a note of thanks, just to be nice. He got his condoms and some breath mints. He pulled his drivers license and a credit card from his wallet and enough cash for anything he might need, then stashed everything else in the hotel room safe. After finishing off his whiskey, he brushed his teeth and double checked everything.

Tom headed down to the hotel bar. He asked the bartender for a recommendation of a good bourbon. The bartender's choice was actually pretty good. Pricey, but good. He sipped the neat whiskey until it was time to go.

It took him a little longer than he had planned to get to the location. Just as he pulled into the parking lot, his phone rang. It was Lisa.

"Hello, Lisa. I just pulled into the parking lot. Traffic was a bit congested. Do you still want me to pick up some wine at the market?"

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

"OK, Bye."

Tom walked into the market and picked up a bottle of wine; the same brand he had bought last year. He didn't know wine at all, but remembered that it was fairly drinkable. He paid for it and walked out the store. He called Lisa.

"It's Tom. I'm all set."

"OK, Love. Are you in front of the market?"

"Yes" Tom replied.

"If you look ahead, you'll see apartment buildings. Go towards them." He started walking as she gave the instructions. "Turn in front of the first building. Keep on going till you see the entrance."

"I've just walked in and I'm at the elevator." Tom said.

"Go to the third floor." He walked into the elevator and pushed the button for the third floor. It rumbled up. His heart was beating strong. He felt that he could almost hear it beating. The elevator door opened, and he walked out.

"I'm on the third floor."

"It's apartment number 342."

He walked down the hallway, counting down the rooms as they went by. When he stepped in front of the door to apartment 342, he was about to tell he was there when the door opened. He ended the call and walked in.

Like last time, it was dark inside. While his eyes were adjusting to the dim light, the door closed behind him. He turned and there was Lisa. Just as before, she was beautiful. Somewhat tall, with long legs in black stockings, a short dark skirt, and a dark bra. Her long auburn hair fell along the side of her face.

"Hello" he said, still with a nervous tremble. He wasn't sure why he was nervous. He'd been through this before.

"Hello, Love." She said in a soft sexy voice. "This is Jessica" she said, pointing across the room.

Tom hadn't even noticed her, but he turned to see a short blonde with a cute face. She had a t-shirt and blue panties on. She was beautiful as well, sort of the girl next door type of look, if you were lucky enough to live next to someone so cute.

"Hello Jessica, it's nice to meet you." Tom said.

"Let me take that wine." Lisa took the wine from Tom's hands. She grabbed three glasses. "Come on, Love, let's go to the bedroom."

She and Jessica turned and walked into the bedroom. It was dimly lit, but a bit lighter than the first room. There was a queen size bed. A dresser was against the far wall. On it was a small television playing pornographic video. The same old lava lamp was on the night stand. They must have just turned it on as the 'lava' was a solid clump and not moving at all. It cast a red glow across the room.

Tom walked over to the dresser and placed the envelope with the donation on the dresser. Then he turned to the girls. Lisa was opening the bottle of wine, and Jessica was standing there smiling. "Jessica, you're very beautiful" Tom said. She grinned a bit more and giggled.

Lisa poured the wine into a glass, and handed it to Tom. She followed with one for Jessica, then one for herself. "Sit down" she told Tom.

He took a seat on the bed and they followed. "So, girls, is there anything that's not on the menu?" he asked. "Anything off limits?"

Jessica said "I don't do anal" paused, then said "as far as everything else, let's see how it goes."

"That's cool." Tom replied. The girls stood up. Tom followed and they walked to either side of him. He placed his half-drank glass of wine on the dresser. He turned to Lisa, and gave her a soft kiss on the lips. She responded with some soft "mmms" and opened her mouth. Her tongue licked Tom's lips and he opened them to let her in. Lisa's tongue darted in and danced around the inside of his mouth. He did the same to her.

Tom broke away, turned to Jessica, bent over, and kissed her. She also responded with some deep French kissing, but she was not as talented at it as Lisa was. She giggled a few times during the kiss, which Tom thought was amusing. The kissing continued, alternating between Lisa and Jessica. Their hands caressed Tom's hair, chest, and eventually began rubbing the front of his jeans. His erection shortly was straining to be released from it's confines.

The girls broke away and Jessica dropped to her knees. Lisa followed. Jessica unbuttoned then unzipped Tom's jeans and both girls slowly pulled them down. "Just a minute" Tom said, as he stepped back, kicked off his shoes, and stepped out of his pants. He hadn't wore underwear, and he felt his dick at attention in front of him.

"Oooh, he's already hard" Jessica said, then she moved forward and kissed the tip. She looked up at Tom, who was smiling in ecstasy, giggled once more, then engulfed his member. She bobbed a few times up and down, then pulled off. Lisa immediately leaned in and repeated the mover, but he could feel her tongue rolling along the shaft and then flicking the head as she moved up and down.

After a few minutes of alternating cock worship, Tom reached down and pulled Jessica up. He kissed her again, and of course, she giggled. "Take your top off" he said. She pulled the t-shirt off, revealing a blue bra that matched her panties. Tom caressed the long blond hair on the side of her face, traced his fingers down her neck and into her cleavage. Then he gently cupped and caressed both breasts. They were not huge. Maybe even smaller than average, but nice. A handful (as the old saying goes). Jessica reached behind her, unlatched the bra, and removed it, revealing her beautiful tits. She had soft pink nipples. Tom leaned forward and took her left nipple in his mouth. He swished his tongue across the tip. At the same time, he was gently moving his left hand over and around her right breast. Jessica giggled, and then softly moaned.

While all this was going on, Lisa had continued to lick and suck Tom's cock. It was hard for Tom to concentrate on Jessica's breasts with all the oral attention he was getting. But then Lisa stopped. Tom turned to see her stand up, and remove her skirt followed by her panties.

Lisa's circumcised cock was fully erect. It head had a darker red color than the shaft, and there was a slight curvature to the right. "You like?" she asked.

"Oh, yes" Tom replied. He broke away from Jessica and gently grasped her cock, moving his hand slowly up and down. He felt Jessica drop down beside him, and she began to lick the tip of Lisa's cock as he softly jacked her. Lisa moaned softly, then said "That feels nice." She then pulled back from the group.

She laid down on the bed, on her back, with her head toward Tom. Then she scooted forward so her head hung down a bit off the edge of the bed. Lisa reached up and grabbed Tom's hips, pulling him forwards. "Put you cock in my mouth and fuck me" she said.

'Jeez' Tom thought. He obliged. It was a bit hard to get his fully erect cock to bend in the correct direction, but Lisa helped, and soon he was moving his cock in and out of her mouth. He was going slow, and tried to not be too aggressive. He didn't want to hurt Lisa. But even though his movements became more exaggerated, she didn't gag. He could feel his cock pressing against the back of her mouth. It was unbelievable.

At the same time, Jessica began to caress Tom's body all over, and continued with the French kisses. And of course, the giggles continued as well.

Tom pulled his cock out of Lisa's mouth, turned to Jessica, and said "come with me."

He got on the bed next to Lisa, and Jessica followed on the other side. "Lisa, scooch down a bit so your head isn't hanging off the bed." Lisa inched back down. "Jessica, would you be so kind as to help me give Lisa a blow job?"

Lisa giggled, bent over, and didn't hesitate at all, taking Lisa's cock in her mouth. She began to bob up and down, and every so often, she went all the way down, taking Lisa's firm 6 inches fully into her mouth. She pulled off, and Tom did the same, but he went a bit slower. He concentrated on using his tongue as much as possible, and softly played with Lisa's balls at the same time. Before pulling off to let Jessica have another go, he took a good breath, and went as far down as he could. He felt his face against her belly, and her cock pushed past the back of his mouth just into his throat. He held it there for a few seconds, then eased back up. Lisa moaned loudly. "Oh God, that feels good" she said.

Tom felt a bit of pride in that he was able to make Lisa feel that good. Yes, she was an escort and her job was to make the client feel good, but there was no doubt in Tom's mind that she genuinely felt pleasure. And past experience told him that at a certain point, she would confirm that with an eruption.

But Tom wasn't ready for that now. Too much to do, so little time. He worked his way around to get between Lisa's legs. Jessica started to move, but he said "Wait there." She giggled again. "Lisa, do you have a condom?"

Lisa turned to Jessica and told her "In the top drawer of the night stand. And there's some lube in there too."

Jessica retrieved the condom, leaving a couple more on top of the night stand. Tom raised up a bit, and without even asking, Jessica rolled the condom down his dick. "Can I have the lube?" he asked.

Jessica handed him the lubricant. He put a small amount on his finger, then playfully pressed it against Lisa's ass, which by this time was well exposed by her widely spread legs. He rolled it around the surface, then popped his finger in. He slowly pushed it in past the second knuckle, then rotated his hand around so that he could play with her prostate. Lisa squirmed and moaned again.

Tom removed his hand, squirted a bit more lube on it, then applied it to his covered cock. Then he leaned forward and held his cock head at the entrance to her ass. He slowly pushed in. Lisa's ass was tight, but it gave way slowly but surely, and it wasn't long before Tom was all the way in. He began to pump in and out of her. The sensation was superb. He was enjoying it. But what Jessica did made it even better. She began to give Lisa a hand job, then added a blow job on top of that. He leaned back so he could take it all in. Lisa must have been getting a good deal out of it as he could feel her anal muscles tensing up now and then.

He continued to fuck Lisa's ass, all the while watching Jessica blow her. It was the most excitement he had ever experienced. Lisa began to move her hips up and down, so much so that Tom hardly had to move at all, her movements making her ass glide up and down on his cock. Lisa was moaning loudly now.

"Oh God, I'm going to cum" she almost grunted. "Ohhh, Ohhh, Ohhhhhhhh, Yesssssss." Lisa's movements stopped. Her hips were raised up with her cock pushed nearly all the way into Jessica's mouth. Tom could feel that she was ejaculating, as her ass muscles were pulsing around his cock.

It felt great, but in a slight way, he was a bit disappointed. He wanted her love juice in his mouth. He realized he still could. "Jessica, don't spit it out" Tom said. He pulled out of Lisa and then laid on his back on the bed. "Spit the cum into my mouth" he said. He opened his mouth, and watched as Jessica smiled, then bent over. Her mouth was hovering inches above his, and he watch open-mouthed as she let Lisa's cum drip out of her mouth into his.

Tom waited until no more was coming, then closed his mouth, swirling his prize around. It was mixed with Jessica's spit, but he could still appreciate the gooey texture and the slightly off taste. He loved it. He savored it for a minute then swallowed.

When he sat up, he saw that Lisa had sat up as well. He grabbed another condom from the night stand. "Jessica, I want to fuck you doggy style."

Jessica smiled and giggled. He pulled the used condom off, the was about to open the second when Lisa grabbed it from his hands. "Let me" she said.

Lisa opened the packet, and placed the condom over his cock head, then rolled it down his shaft.

"Lisa, I want you to eat Jessica's pussy while I fuck her." Jessica giggled again, and got up on all fours. Lisa scooted under Jessica so that she was in position. Tom knew that this might not work, but it was worth a try. He got in position behind Jessica and placed his cock against her pussy. It was already wet. He pushed in. He moved slowly in and out, not wanting to make Lisa's job more difficult, or her position more precarious. Tom could feel Lisa's nose every now and then on his balls, and it was a wonderful feeling at that. At first, Tom was doing all of the work, but soon Jessica got into the groove and was moving back and forth, and then began to roll her ass up and down on his cock.