Taylor Ch. 14 - The Ritz

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Taylor makes some new friends.
2k words
4.2
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Part 14 of the 19 part series

Updated 06/10/2023
Created 09/06/2020
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The Ritz

Taylor walked the two blocks to the Ritz and entered the lobby and then the bar. It was not crowed but there were a few business types sitting around drinking.

She approached the bar and caught the attention of the barkeeper.

"What can I get you?"

"Glass of Merlot."

"Coming right up."

The wine was delicious after what she had just swallowed and she used it to clear her throat. The burn felt good and she felt cleaner.

About that time someone sat on the stool next to her and asked for a glass of white wine.

Taylor looked and saw what was obviously a professional lady of the evening.

"Hi she said to Taylor."

"Hi."

"This is my lounge and I don't like competition."

"Okay."

"You need to leave."

"Not until I am ready."

"No, now!"

"Hey, look, I just want to enjoy my wine and I will leave you to your crowd of patrons."

"Don't get smart."

"I can see you don't have any business so lets chat some. I am not a threat."

"Why do you say that?" She said.

"First off I am a tranny and we don't have the same clientele."

"What do you mean a tranny?"

"Christ bitch, I am a guy in drag." Taylor hissed at her.

"Then what are you doing in here?"

"Having a glass of wine."

"You're not working?"

"No, I am done for the evening."

"How much you make?'

'I had a good night, almost a thou."

"It's not even midnight and your done?"

"Yea, I had a date earlier and picked up a blow job in the lounge down the street, I just stopped in her for a drink."

The stranger got a little friendlier as she got her wine and they both drank a little.

"What's a tranny do?"

"Same thing you do, just different equipment I guess."

They chatted a while, ordered another glass of wine and slowly relaxed into each other's stories.

Blanch introduced herself to Taylor and they even laughed a few times before two gentlemen approached them from the back and asked to buy them drinks.

The two girls looked at each other and nodded yes.

The boys led them to a table and the four of them sat and paired up.

Taylor's guy was Sam and he was young and cute, Blanch got the older one and his name was Peter.

They chatted for a while, had another glass of wine and Blanch asked Peter what he wanted to do?

"What do you mean? Peter said.

"I get donations for my time Peter. I get two hundred an hour for whatever you want to do."

Peter looked at Taylor and she nodded.

Sam looked at Taylor and said, "You're a hooker."

"Shhh, someone might hear you."

Peter took the lead; he had been in this situation before.

"How much for both of you, up stairs in my suite?"

"Four hundred an hour."

"No discounts."

"For the second hour." Blanch said.

"How about all night?" Peter asked.

"Five hundred each."

"Now that's a deal."

Blanch turned to Taylor and smiled. "You ok with these two guys."

"Fine with me." Taylor answered.

"Take me to bed lover." Blanch said as she stood up and drained her wine glass.

The four of them walked to the elevator and Peter took them to the top floor and one of the three suites on that floor.

"Wow, pretty nice spread." Blanch said.

"We work for a generous company."

"Show me the money." Blanch said.

Peter opened his wallet and pulled out ten one hundred dollar bills, lay them on the dresser and said. "That work?"

Blanch scooped up the cash, handed Taylor half and started to take her clothes off.

The suite had two bedrooms and Taylor took Sam into one of them and shut the door.

"Tell me what you like Sam." Taylor said as she eased up to him and pressed her lips to his neck.

"I don't know, I guess I like most anything."

"Are you and adventurous person?" Taylor asked.

"I guess so."

Taylor reached between their bodies and unbuckled his belt. His pants fell to his ankles and she leaned down and held them while he stepped out.

He was already hard and she reached up for the waistband to his briefs. Pulling them down his giant cock sprang forth.

"Wow baby, that's quite a tool."

"Uh, thank you."

"Are you married honey?" Taylor said as she began to stroke his hardness and kiss the tip.

"No, but I have a girl friend."

"Does she suck your dick?"

"No, I have never had that done."

"Is it ok if I suck on it for a while?"

Sam was taking his shirt and tie off as she stood and led him to the bed.

"Lay down baby, let me pleasure you."

He did and moved to the center of the bed.

Taylor took her dress of slowly but left her gaf on hiding her manhood.

He watched her and his dick got harder and harder.

Taylor began to stroke his thighs, running her hands around his groin and lowering her face to his stiffy.

Cupping his balls with her hand she slowly engulfed his cock all the way down.

She watched his face to see how he took it and his eyes were big as saucers as her nose entered his pubic hair.

She came up and straddled his erection and slowly nursed his nipples and then moved to his mouth. He seemed hesitant until she took him fully and pushed her tongue into his mouth. He tasted of scotch and she of red wine and it was pleasant. The taste of cum was gone.

After several kisses and much stroking by her she got up off the bed and turned the lights out. Moving back to the bed she climbed on and began to suck his dick in earnest.

"Oh god, that's good." He said.

"You want to cum for me?" She whispered to his dick.

"Oh yea, I am going to do that, and soon." He said as his hips bounced up into her mouth and he reached for her head.

"No no, baby, let me take care of it."

She slipped between his thighs and cupped his balls while stroking is dick with her lips. He was big and sweet, she was having a good time with it.

"I can't stop, baby, I am going to cum. Oh shittttttt, fuckkkkkkk, achhhhhhh."

He let it go and Taylor took it all in her mouth and swallowed it.

She moved up to his face again and offered him her lips. Not sure, he opened up and she gave him a tongue full of sweet salty cum.

"That's so good, you taste wonderful." She said.

"Wow, I never knew what it tasted like. It's not bad at all."

"You can have all you want honey."

"I don't think I have any more in me." He allowed.

"I know where to get some more if you not shy."

"Where would that be?"

Taylor got up on her knees and slid her gaf down and sprung her cock out in his face.

"Oh god, you have a dick, you're a man."

"No baby, I am a transgender woman. I was born a man but I am going to be a woman some day."

"Really. I never met someone like that."

"Well here I am."

"Can I hold it?"

"I was hoping you might want to do that."

Sam reached out for Taylor's cock and gripped it tenderly, squeezing the shaft, feeling how soft it was and yet firm and stiff.

"I never really felt one before. It feels different than mine."

"I hope you like it."

"I do, can I kiss it?"

"Sure baby, suck it if you want."

Sam moved up on his side and gently put his lips over the head of Taylor's cock. Licking it with his tongue he gently moved it deeper into his mouth. He remembered how Taylor had swallowed his cock and wondered to himself if he could do that too.

Sitting up he pushed Taylor back on her back and began to lick and suck her dick and take it as deep as he could. Quickly he hit the gag reflex and almost vomited.

"Relax your jaw and keep your mouth open." Taylor said.

He tried that and managed to get almost three quarters of it down.

"I can't get it all in."

"That's fine sweetie, only the head counts anyway."

He licked and sucked her cock for twenty minutes.

"Are you going to cum?" He asked.

"It's a lot harder for me than you."

"What can I do to get you to cum?" He said.

"I could fuck you."

"In the ass?"

"Yea baby, that's where it goes."

"I don't know about that."

Taylor started stroking his rising cock and said, "Well you could fuck me and that would help."

Taylor leaned over and took him in her mouth again and felt him rise some more.

Without saying anything she reached for her bag and got a condom out. Peeling the wrapper she popped it in her mouth and slowly slipped it over his now straining manhood.

"Oh shit, that feels good." He said.

Taylor slipped out of the gaf and rose up over him; sitting up over his groin and gripping his tool she squatted and pushed him straight up into her rectum.

"Now that feels good." She said as she relaxed over him.

"That's amazing." He said as he reached down to hold her cock.

Leaning back on her hands Taylor thrust his cock and balls towards him and he fondled both.

"Does that feel good to you baby?" She said.

"Oh yea, it's really tight."

"If we roll over you can fuck me if you want."

"Okay, I think I would like to do that."

Taylor withdrew and moved to her belly, pushing her ass up in the air for him to see and find.

She hoped he had done doggie before and soon realized that he seemed to know a little about where they were going.

He moved behind her and saw the point of entry, held his dick in his hand and moved to penetrate. Taylor sensed where he was and as soon as he had his head on the spot she leaned back into him and he slid inside. Taking his advantage he quickly slammed to the bottom pressed his thighs against her ass.

"Oh, that's so good baby." Taylor growled out.

Inspired, Sam started pumping her. He pulled back and hammered her again and again. His confidence was growing and it felt good to him.

"Can I cum in here?" He gasped.

"Whenever you want baby. I am going to ease forward and you should bring your knees up alongside my hips."

Taylor started to flatten out and he did what she wanted. He was now sitting astride her ass with his hard dick buried to the hilt. He got the hint and leaned forward putting his hands on her shoulders and started pumping her faster. The intensity of the tightness and the position soon moved him to exploding his second orgasm of the evening.

"Don't pull back." She counseled him.

He collapsed on her back and stayed buried.

She reached back and grabbed his thighs and pulled him tight against her.

He could feel her clinching her sphincter and then suddenly her whole body began to convulse. She was having a full body orgasm.

"Are you ok baby?" He said.

"Yes, just don't leave me yet."

"Okay, I don't want to."

He kissed her shoulders as she pulled him tighter and tighter to her. It felt amazing to both of them. The explosion of passion and tension made for a union of body and soul.

Finally he felt her relax totally.

"You can get off now." She said.

He slid down next to her and pulled her body tight against him as they both recovered.

"Thank you baby, that was amazing for me." He whispered.

"Me too."

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