Taylor Ch. 02

This is the continuing story of Taylor and Barbara.

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CHAPTER 2

Taylor and Barbara met in our last chapter on the street in downtown Richmond. Taylor was going home and Barbara picked him up under the pretense of soliciting a date. He was dressed in drag and didn't know when he looked in the window that Barbara was a woman. He got in and the rest is history.

The next day Barbara drove Taylor home and he went to his apartment to dress for class. The events of the evening and recently the morning swirled in his brain. She had made him question everything he thought he believed in. Did he want to be a woman? Did he want to keep working on the female persona? Did he want to continue to be a gay man? Did this glimpse into a real woman in a sexual situation change everything.

Suddenly he considered having a girlfriend. Never had he had the desire to be with a woman more than he did right now. Barbara awakened feelings he didn't think existed. What should he do? He agreed to see her tonight, so, he needed to get on with the day and see how it went later. Maybe a social setting and conversation would turn him off. Right now he just wanted to fuck her again and again. His dick was raging and he was going to have to jerk off before he went to class. This was embarrassing.

Barbara drove to her office and parked in the private garage. She was a senior partner in a large corporate law firm. She worked mostly on discrimination cases. Big companies always found ways to discriminate against employees, weather it was sexual, job performance, gender, personal and on to infinity.

She flashed back to Taylor as she rode up to the top floor in her private elevator. The thought of them recently in the shower made her panties damp, her nipples tighten and she almost blushed. Being with men was not something she did. She was a woman's woman, she loved being in the company of women, and she loved being intimate with women and having sexual relations with women.

Taylor had attracted her because she thought maybe he was a woman with a dick. She did love the male appendage. She just didn't like men. They were unsophisticated brutes, gross bores with the necessary tool for pleasure. Taylor offered her what she hoped was the best of both worlds. Let's face it she thought, a real dick beat a strap on any day. Tonight she would find out if they could be something other than sex partners. She would dine him and wine him and see if he was a prick or the real deal.

Barbara walked past her secretary and said a curt hello. The secretary, who was quite efficient, handed her a stack of messages without saying a word.

She looked through the stack of pink message slips and selected several that needed her immediate attention.

"Joanne? Barbara here."

"Hi Barb, I needed to know if we were going to work on the new corporate counsel minutes today?"

"If you have read through them and like what you read send them up and I will edit if I think something needs a touch up. Thanks for your help."

"OK, I am almost done. You want to have dinner some time?"

"I am a little tied up this week, maybe next week."

"See you later."

"Bye."

And so it went, she took messages and calls for several hours. Every three minutes she had thoughts of Taylor and what they had done. Work was not helping her take her mind of what she really wanted. Suddenly she noticed dampness in her panties.

"Damn, what has he done to me?" She thought out loud.

The day continued that way. Lunch came and went with a deli sandwich her secretary got for her.

Finally about two o'clock she pulled out a file she had been working on for some time and sorted the pages. She opened her laptop, logged into the corporate network and opened a file of the same name. This was a draft of a corporate finding that needed a lot of work and she managed to spread all the paper out and concentrate on the typing. Losing her self in the work the time flew by and before she knew it, her secretary stuck her head in the door and announced she was leaving for the day.

Barbara looked up in surprise and said, "Uh, OK, good night."

"Do you need anything before I go?"

"No, I am just finishing up, I will be right behind you."

"Good night."

Barbara went back to her work, saved her changes, read some more of the comments and put the file back in the drawer, closed the computer and stood up from her executive swivel recliner chair. Her delicate silk panties were stuck to her from her earlier damp excursion into thoughts of Taylor. She wiggled, stuck her hands into them and unstuck herself. Not something she usually had to do and she was glad she was alone.

She called Taylor as soon as she got home and he didn't pick up. She wanted to take him out to dinner and hoped he would dress for her and they could dine without interruption.

A long hot shower was in store and she stripped naked and stepped into the large glass enclosure. The water and the spray massage stimulated her and she found herself soaping and rubbing her female regions much longer and more vigorously than normal. She wanted to get off, she was aroused, sensitive and in need of an orgasm.

She stepped out of the shower and got her waterproof buzzer and placed it inside her with the pull cord hanging out. The sensation was instant and she eased back under the hot water. Pinching each of her nipples she let her concentration go to her orgasm while thinking of Taylor inside her, and after several minutes her toes curled and the wave of pleasure moved up her body. What was she doing? She never did this. She never thought of a man inside her, making her cum. What was going on?

She dried off, put on a dressing gown over her nakedness and went about brushing out her hair and putting on new make-up. Where is he, he should have called her back by now. "Fuck." She said out loud.

Taylor went to class and made copious notes. Went home and transcribed all of the notes into a word file on his laptop. It was his way of reviewing information and storing it while it was fresh in his mind.

When he started to close the laptop he decided to look up Barbara and see what he could find.

She was a corporate lawyer, big firm, and well respected as a corporate consul. That was pretty strong praise for such a nice lady. You always expect high power broads to be stuck up and snotty. Barbara sure wasn't that. The more he thought about her the more he liked what had happened. He checked his phone and saw her name and number pop up. She had called and not left a message. Hmmm, wonder what that was about?

He dialed her number and she picked up on the first ring.

"You called?" He started with.

"I did, can I ask a favor?" She replied.

"Anything."

"I want you to dress up for dinner."

"In geech?"

"Is that like a woman?"

"Yea, sorry about that."

"So, will you? Dress like a woman for me?"

"I would love to, sexy or elegant?"

"Can you do cocktail dress?"

"Sure, if that's what you want."

"I would love to see your long legs exposed."

"It will be done."

"I will pick you up in an hour, is that ok?"

"You want me to be gorgeous and sexy in an hour?"

"I can't wait any longer to see you."

"Am I staying the night?

"You better be."

"OK, see you in an hour."

Taylor grinned to himself; this was getting interesting. The check Barbara wrote him this morning would pay the rent for next month and the promise of more would help her add to her wardrobe. He better look good for this tonight.

Tight cocktail dress in silver, five-inch heels, diamond earrings, and a silver choker that he loved to wear and was standing on the curb when Barbara drove up. Taylor stuck out his thumb and she laughed as she rolled down the window.

"Going my way?" She quipped.

"All the way." Taylor replied.

Barbara reached for his hand as Taylor got in the car and squeezed saying, "I want to kiss you but think we should wait."

"Then you will have to give me an extra kiss later." Taylor replied.

The both laughed and off she drove toward the restaurant.

Hondo's was out of the city, located in a suburb shopping area and easy to reach by car. Barbara parked out front and the valet took her keys and gave her a stub. They walked to the entrance and a doorman greeted them.

"Good evening ladies, do you have a reservation?"

Barbara said, "Yes, Kelly and Associates."

"Very good madam, please go in and the hostess will show you to your table."

The hostess was a very tall, very well endowed knock out with hair down to her ass and the biggest blue eyes Taylor had ever seen.

Barbara took one look at her and almost drooled. She did appreciate good female flesh.

Taylor saw the look and whispered, "Do you think she is on the take out menu?"

"Shush!"

They were both grinning when they sat down and ordered wine and picked up the menu. .

The waiter appeared almost instantly with the Merlot and poured two glasses.

"When you are ready I will take your order. Would you care for an appetizer?"

Barbara said, "We would like to share one of the cocktail prawns."

"Very good madam."

Taylor looked at her curiously and she said. "They are huge."

The prawn was a giant shrimp and was delicious, complementing the wine perfectly. Barbara knew how to do dinner out.

The steaks were served hot, sizzling and melted in your mouth. Taylor was not used to succulent steak and concentrated on enjoying the meal.

When they had both eaten their fill, Barbara looked at Taylor with a hungry stare. Her eyes were large pools of desire as she looked across the table.

"You want some dessert?" Taylor asked.

"I want you, I would eat you right here if I could."

"Just for the record, I would let you."

"We need to talk."

"What about?"

"Our arrangement."

"Do we have one?"

"Taylor, please. I want an arrangement. You know I am enamored with you; you are something I have dreamed I wanted for a long time. Now that I am on the cusp of getting what I think I want, I don't know how to get it."

"Barbara, tell me what you want to do. The sex is automatic; the arrangement is what can be difficult. I don't know if I want to be a man or a woman. You make me question everything I ever thought about myself. I sit here in female persona at your request and all I want to be is a man in your arms. You want a feminine man in your bed, what do you want in public?"

"I guess the true answer is I don't know." She replied. "I do know we have to figure out what we each want and what is best for us."

"Ok, do you have something to propose?" Taylor asked.

"Yes, until further notice I want to spend every weekend with you. Preferably in my bed but maybe we can go to the beach or mountains sometime. That way I hope it won't interfere with your school or my work schedule. If we want to spend more time together we can talk about it then."

"Barbara that sounds like a very good solution. The ugly part of this is I would like to stop walking the streets and for that I need some money. I don't want to ask you for money. That is not what this is about. But, having said that, street walking is the only way I can earn enough to pay my bills."

"Can I put you on my corporate payroll?"

"You can do that?"

"Yes Love, I am the senior partner and managing partner. You will become my personal investigator, reporting only to me and go on the staff roster. How much do you earn on the street, average for a week?"

"On a good week, I can do a thousand but most weeks are average. Around six hundred."

"Then two thousand a week will cover your expenses and allow me access to your free time? I also want you to continue going to school."

"Oh my God. Yes."

"Then the deal is done. Lets talk about your appearance."

"Something wrong with my appearance?"

"No dear, you know I want your maleness in my apartment. I would like to have you sometime like this, two girls in public."

"That is ok with me. I enjoy this as well."

"Then we have an arrangement." She said.

"I guess we do. Thank you for your job offer. You really are going to change my life."

"I know that and I am somewhat concerned how the future will treat both of us and our partnership. Only time will answer that question so in the mean time we enjoy it."

"I will do my best to make you happy Barbara." Taylor said in his most serious voice.

"If I take you home now will you fuck me silly?"

"With pleasure." He responded.

They left the restaurant and Barbara drove the two of them back to her apartment. As they walked from the garage to the side door into the house, another lady was exiting the second door.

"Taylor, I would like you to meet Betty. She lives in the apartment adjacent to mine and we are long time friends."

"Hi." Betty said and offered her hand.

Taylor took the offered hand and gripped it softly like a lady should and whispered, "It's so nice to meet you. Barbara has spoken of you often."

"Likewise I am sure." Betty said, as she looked funny at Barbara.

"Would you like to join us for a nightcap?" Barbara asked.

"I can't, I have a previous engagement that I can't miss."

"Another time maybe?" Barbara offered.

"Certainly. It was nice meeting you Taylor."

"For me too." Taylor offered.

They all parted and Barbara and Taylor went into Barbara's apartment.

"If she had stayed, would that have resulted in a threesome?" Taylor asked when they were in the kitchen."

"It most certainly would have. I didn't want that on our first night in partnership but I couldn't afford to piss off the landlord."

Taylor laughed out loud and suddenly realized that this was going to be a fun relationship. There would be seriousness but not anytime soon.

Barbara stepped out of her spike heels and opened a bottle of merlot to breathe and found two wine goblets in the cabinet. She poured a healthy amount in each.

Barbara led Taylor to the bedroom and they both removed their outer clothing.

"Shower?" Barbara asked.

"Wonderful."

They finished stripping off under garments and walked into the large glass shower. Barbara turned all the heads on and once it warmed up they stepped in.

Mutual soaping was getting Barbara aroused and Taylor's dick was already fully engorged.

Taylor decided to take a bit of a lead and moved up behind Barbara and reached around to grasp her soapy breasts with his hands and slide his erection between her large cheeks.

"Hmmm, I feel a friend." She cooed.

"I just feel good." He responded.

"Would you like my ass here in the shower?" She said.

"You do that?" Taylor asked.

"I would for you, I have never done it before."

"That can be difficult the first time."

"Do you want me that way?" Barbara asked softly.

"To be honest I just want to put my dick in a hole, if you want me to do your ass then I am ready to go."

Without another word Barbara bent at the waist and offered her rather large plumb ass to Taylor.

Taylor massaged her globes and soaped the cleavage as best hr could. Pressing a finger onto the petal he penetrated her slowly and felt her tension rise.

"Is that your dick?" Barbara asked.

"No baby, that's a finger."

"Oh my god that hurts."

"This is not going to work in the shower, you need to be acclimated to anal sex. It's not just a matter of poking you in another hole."

"Okay, pussy?"

"That I can get in without any problem."

Taylor slid up into her warm wet pussy and gripped her hips firmly.

"Oh baby that feels wonderful." She said.

"For me too." He replied and began to pound her out.

Barbara put both hands on the shower wall and pushed back as hard as she could. The hot shower water cascading over them made them feel like they were under water having sex in the most intimate way.

Dog style was very stimulating to Barbara and she started to orgasm shortly thereafter. Her spasms were huge and Taylor noticed her starting to relax under him.

Sensing he should ease out, he allowed her to stand and he exited her pussy.

She turned into him, offered her lips and took his still hard cock in her hand.

"You didn't cum, you are still hard?" She queried.

"No, it's okay, I got some relief."

She kneeled on the hard shower floor, took Taylor in her mouth and began to deep throat him. The taste of her pussy and the soap was all over him and she reveled in the flavor. She seemed determined to get his semen but the pain in her knees from the tile floor was just too much and she stood back up and kissed him again.

"Can't stay on that floor baby." She cooed.

"It is hard."

"So are you."

"That's a good thing."

"Let's go to bed."

"I thought you would never ask."

It was early and Taylor mounted her in missionary to start the pleasure trip. They both liked it with him on top, deep inside her and comfortable. He would sit up in his knees, prop her ass up on a pillow and just caress and rub her belly and breasts. She felt him inside her and worked her pelvic muscles to massage his long wide penetration.

"Fuck me baby." Barbara whispered after several minutes.

"Yes ma'am."

Leaning forward and taking his weight on his hands beside her head Taylor began to pull back and push in. Barbara raised her knees and began a rocking motion matching Taylor's strokes. The combination was erotic as hell and both of them felt the impending eruption begin to form.

Barbara cried out first. "I'm cumming. Give it to me baby, give me all of it."

With that Taylor doubled his speed and began to pleasure himself into an orgasm.

"OH yea, baby, here it comes."

They came almost simultaneously and with panting breaths collapsed into a molten heap of hot flesh.

"Wow, that was intense." She whispered as she finally caught her breath.

"Better than anything I have ever done." Panted Taylor.

Barbara snuggled up against Taylor's chest and whispered, "good night sweetie."

Taylor hugged her close and began to wonder what was happening.

Sleep didn't come easy to Taylor that night. His mind constantly turned over what had happened with Barbara and how it was going to affect his life.

He had always thought he would be a woman some day. He had dreamed of having the surgery, having breasts to put in his bra, taking the hormones that would expand his hips and raise his voice. Now he was uncertain. Sex was business and this defiantly was not business. This was something way more personal and loving. Yes loving. He genuinely enjoyed her company and in his entire life he had never experienced the kind of sex he just had with her. It was too much, it was too good and he worried that if he committed to this relationship would he lose his life's dream? Would he lose who he was? Would he become somebody else? Who would he be?

Taylor had slept fitfully and was laying half awake when Barbara stirred, snuggled in closer and started moving her hand down Taylor's stomach. Taylor wasn't sure she was awake but she certainly wanted to hold his flaccid manhood.

Her hand cupped him and gently stroked the corner of his thigh and groin, lifting his scrotum and fondling the large sac. If she was dreaming it was certainly a good dream.

Taylor was enjoying the contact. Once again it was something he had never felt before, someone else holding his balls and gently massaging him. His penis also took note and started to react to the attention. Soon it was standing tall and Barbara shifted her attention to the pole within her grasp. She could tell it was dry and knew to be careful, so she just gripped it and squeezed it gently, squeeze and release, squeeze and release.

Taylor was enjoying the massage and his ardor was just beginning to rise. He squeezed her with the arm she was laying on and whispered. "If your not awake, this is the best dream I ever had."

"I am sound asleep." Came the soft reply.