Trust Me

By

Julie O

Edited

By

Itinerant

Mike Doyle’s life is changed forever when he accepts the business offer of Heather Green

Chapter 1

Mike Doyle stood outside the three-story brownstone house and checked the address that he had entered into his phone. He suspected that Heather Green was well off, but he hadn’t expected her to live in a home like this. He walked up the steps and rang the doorbell.

The front door opened, and he was greeted by a shapely redheaded woman.

“Mike, it’s good to see you. Did you have any trouble finding the place?” she asked as she motioned him inside.

“No, you gave me great directions,” he replied as he walked inside.

“Did you have any trouble parking?” she asked as she led him into the living room.

“I caught the bus and then walked the final three blocks,” he replied. “I don’t have a car, just a bike.”

Mike was in his third year of college and money was tight. He had earned an academic scholarship, so that was taken care of, but he struggled to pay the rest of his bills. He worked at a coffee house located near campus and it was how he had met Heather.

The coffee house was in an area known for its art galleries and he had always suspected that she ran one of them. Over the past few months they had become friendly as he took her order.

“Please sit down Mike,” said Heather. “We need to talk.”

Mike did as she asked as he was curious why she had invited him up to her home.

Heather smiled as she ran her eyes over Mike. She was several inches taller than the thin young man. She suspected he was around five-eight in height.

“I will get right to the point. I have a proposition for you,” she stated. “I want you to listen to what I have to say before you make a decision, okay?”

Mike nodded.

“I will be blunt, I need you to test a sexual device,” she stated in a matter of fact manner. “I am a professional escort and I get a certain sort of clientele. Recently I came across a rather unique item that could make me a lot of money. However, I need to test it first, to see that it does everything advertised before I can use it on a client.”

Mike’s eyes opened up wide as he took in what she was saying.

“In my line of work, I have learned to read people,” she continued. “Now, please answer the next question honestly. Are you submissive?”

After a moment’s hesitation, Mike nodded. As he did, he lowered his head.

“Honey, there’s nothing to be ashamed about. It’s just who you are,” she stated in a comforting tone. “I have suspected this, and it will help in the testing of the device.”

Mike raised his head up.

“Have you ever had anal sex?” she asked.

Mike shook his head vigorously.

“I’m not gay,” he replied.

“I didn’t ask if you were. I know many men who consider themselves straight who like anal,” she replied. “I’m also not into the whole gay-straight labeling either. I think sex is something that should be enjoyed, much like fine food.”

Mike laughed.

“Sorry, but I never thought of it that way,” he replied.

“It’s okay. Anyway, I have a device that I want to use on you and as you have probably surmised, it will require me fucking you. The dildo has a connection to a sleeve that will fit around your cock. As I make love to you, a signal is sent from the dildo to the sleeve. I have been told that the orgasms it produces are exquisite.”

“Will it hurt, I mean, the dildo?” asked Mike.

“Not at all. It has a special lubricant that enhances the sexual pleasure,” she replied. “In exchange for your time, I will pay you $1000 for each night I test it on you.”

Mike’s jaw dropped slightly. A grand was a lot of money and would make his life easier.

“If you agree to my offer, I promise not to tell a soul,” said Heather. “And if you say no, I will still buy my coffee from you.”

Mike stood up and walked over to look out the window. As he did, he rubbed his chin. It was a strange offer, but he could definitely use the money. He ran his fingers through his shoulder length hair as he debated the offer.

“Um, when would we do it?”? he asked.

“No time like the present,” she replied. “So, are you game?”

“Sure, why not,” he replied.

Chapter 2

“This is my working bedroom,” she replied as she motioned for him to sit down on the king-sized bed.

Mike looked at the expensive oak furniture in the room.

“It’s nice,” he replied.

“I wanted to look like a bedroom from the 1800’s,” she replied. “Now, why don’t we get undressed?”

Mike nodded and began to take off his clothes. By the time he was done, Heather was also naked and standing in front of him. Mike’s eyes opened wide as he stared at her body. She had a very shapely body with large breasts.

“You like?” she asked in a playful manner.

“Sorry,” he replied as he felt his face grow warm.

“It’s okay, dear. I take pride in my body. I’m 35 and this is all natural,” she replied as she cupped her breasts. “You have been with a woman, right?”

Mike nodded.

“A few times, but not like you,” he admitted. “I never saw someone, in real life, who was, um, had no hair…”

She smiled back as she ran her fingers over her smooth vagina.

“I hate body hair and had all mine, from the head down, removed,” she replied. “So, let’s get started.”

She set down an eight inch long dildo on the bed. There was a cable attached to a sleeve.

“Now, slip the sleeve over your cock,” she ordered.

“What’s it made out of?” asked Mike as he picked it up.

“Silk and some sort of alloy,” she replied. “I’ve been told that it will adjust to the size of the wearer. I do want you to pay attention to every detail and sensation. There will be a quiz afterwards.”

She then laughed.

Mike smiled back.

“Okay,” he replied as he slipped the sleeve over his cock. As soon as it was on, it shrunk to match the size of his cock. “Wow.”

“Does it feel okay?” she asked.

Mike nodded.

“Okay, I want you to get on all fours and position yourself on the bed. I have stacked some pillows that you can rest on. Don’t worry about making a mess,” she said.

A short time later, Heather was positioned behind Mike on the bed.

“Are you ready?” she asked.

“As ready as I ever will be,” he replied.

“That’s the spirit. Now relax and enjoy yourself,” she stated.

Mike felt the dildo press against his ass. He felt something warm and slippery begin to rub against him.

“Okay, I’m going to start,” she said.

Mike gasped as he felt the dildo begin to enter his body. To his surprise, there was no pain or even discomfort. As the dildo slowly slipped inside, he felt his cock harden and as it did, the sleeve expanded.

“You’re doing well,” she stated as she pressed in deeper.

A few moments later he felt the dildo begin to slip in and out. As it did, he felt his cock grow very hard. Additionally he felt waves of pleasure sweeping through his body.

As if she could sense his pleasure, she began to fuck him faster.

“That’s it, enjoy yourself,” she moaned.

Mike closed his eyes and cast off all apprehension as he surrendered to the pleasure that was running through his body. His cock was throbbing to the rhythm of Heather’s motions.

He lost all track of time as she fucked him. The sleeve seemed to be delaying his orgasm in order to maximize it. His cock was the hardest it had ever been, yet he wasn’t ready to cum.

When his orgasm hit, he let out a long cry of desire. At the same time he was aware that Heather had reached orgasm as the same time. The sexual explosion lasted for what seemed like an eternity. When it was over, he drifted off into darkness.

Chapter 3

“Good morning sleepyhead,” greeted Heather.

Mike opened up his eyes and saw her sitting next to him. She was wearing a silk robe and was drinking a cup of coffee. He slowly sat up and looked around. He was in a different bedroom, and the morning light was starting to stream through the windows.

“What time is it?” he asked as he rubbed his eyes.

“Nearly seven,” she replied. “Did you sleep well?”

“Very much so,” he replied.

“I thought you would. I carried you in here last night so you could recover. Please tell me everything you can remember about last night,” she ordered.

For the next thirty minutes Mike described what he had experienced.

“Impressive. From what you had told me, the sleeve sounds like it works even better than was described by the manufacturer,” said Heather. “To be honest, I thought they were exaggerating.”

“I have to admit that it was the best sex that I have ever had,” said Mike.

“So, are you willing to do it again?” she asked.

“Really?’ asked Mike.

Heather nodded.

“I have to test it a few different ways,” she replied.

“When?” asked Mike.

“Next week,” she replied. “You need time to recover, and I have clients to see.”

“Okay,” he replied.

“Great. Now, why don’t you grab a shower, and I’ll give you a lift home,” she said.

“Sounds good, thanks,” he replied.

“I do have one request,” she said.

“What is it?” he asked.

“Do you mind getting rid of your body hair?” she asked.

“You mean, shave it off?” he asked.

“No, I prefer waxing. I will make an appointment for you at a great salon, and I’ll even pay for it,” she said.

Mike thought about it for a moment and then nodded.

“Great. I’ll take care of the details and text you later today,” she said as she leaned over and kissed him on the cheek. “You’re going to love the way it feels.”

Chapter 4

The next day Mike reported for his shift at the coffee house. He found it hard to concentrate due to constantly thinking about the sensations he had experienced with Heather and the fact that he had spent the morning having his body waxed. From the neck down, he was now totally smooth and hairless. His new sensation was both pleasurable and worrisome. He found that he liked the new smooth feeling of his body, but it also brought up thoughts that he preferred to keep deeply buried in his mind.

He then thought about how good it had felt when Heather had fucked him. He had always known he was submissive, but this was the first time he had given in to the feelings. And what a way to give in! He couldn’t wait until the next time he was with Heather. He also wondered what other ways she wanted to try with him.

“Mike! Is that cappuccino ready?” asked his shift manager, a brunette named Brandy.

He snapped out of his daydreaming at the sound of her voice.

“Almost done,” he replied as he turned his attention back to his job.

“Cool, for a second I thought you zoned out on me,” she replied. “You seem to be on a different planet today.”

“Sorry, I’m thinking about a class assignment,” he lied.

“Okay, but right now we’re jammed, and we need to make the customers happy,” she replied. “With the snow coming down, we’re going to be busy all shift.”

Mike nodded and he focused on his job. He liked Brandy a lot and he had even tried to ask her out a few times. She always declined, stating she’d rather just be friends. While disappointed, he knew it was probably for the best. He had never been in a successful relationship and now he knew it was due to his submissive side. He decided that he would ask Heather about it and maybe get some suggestions on what to do.

He handed the cappuccino to Brandy and began to work on the next order. It would be a long week he thought.

Chapter 5

Mike arrived at Heather’s place and was greeted by her at the front door.

“Good to see you,” she said as she gave him a hug. “You looking forward to tonight?”

“Yes,” he replied.

Once inside, he told her how he was thinking about it all week.

She nodded knowingly.

“I was told that the device would have that effect on some people. It’s performing just as they said it would,” she replied. “Thank you for being so honest and open with me.”

“You’re welcome,” he replied.

“Why don’t we head right up stairs and get started?” she suggested.

“Okay,” he replied.

“You should handle it better this time and not immediately go to sleep like last time,” she said as she headed up the stairs.

Once in the bedroom, Mike undressed.

“Very nice, I love how smooth your body looks. Do you like it?” she asked.

“It has taken some getting used to, but overall, I like the sensation,” he admitted.

“Good. If you want I can refer you to an excellent laser hair removal service,” she remarked.

“I’ll think about it,” he replied.

She nodded knowingly.

“Okay, tonight we’re going to try it a little different. I will do you face-to-face,” she remarked.

Mike cocked his head.

“Is that possible?” he asked.

“Yes, the dildo is very flexible. This will give you the idea what a woman feels,” she said as she set things up.

Mike was skeptical, but he did as she said. She had him lie down on his back under some pillows, which served to lift up his rear slightly.

A short time later, Heather mounted him. The dildo slipped in easily as before and soon she was fucking him, slowly picking up the pace.

Mike was soon lost in sexual bliss. The sensation was different than the last time. While he knew that his cock was fully erect, it also felt as if she was entering him from the front. He didn’t try to rationalize these thoughts as it all felt so good. When he came he ended up shooting his cum all over his own chest. Heather leaned down and licked it off. He laid back and let her lick his chest and nipples. Then she did something unexpected. She leaned down and kissed him. It took him a moment to realize that he was taking in his own cum. Instead of stopping, he took what she fed him.

Afterwards, they lay together on the bed.

“How was it?” she asked.

He described the sensations and she nodded.

“Was that the first time you swallowed cum?” she asked.

Mike nodded.

“And you liked it, didn’t you? It’s okay, Honey,” she said. “I want to expand your boundaries.”

“It’s not what I expected,” he replied.

She smiled back at him.

“So, you feel up for another session tomorrow?” she asked.

“Really?” he asked.

“I had a cancellation, and you seem ready for something different,” she replied. “I’ll take you home tonight and we’ll meet again tomorrow night, okay?”

Mike nodded.

“I won’t ask what you have in mind,” he replied. “But I do have some questions.”

“Okay, go ahead,” she said as she rolled on her side and faced him.

“You’re really an escort?” he asked.

“That’s right. I’ve been doing this ever since college. In fact it paid for my graduate degree,” she replied. “I did it part time to pay for tuition and found that I wasn’t just good at it, but that I liked doing it. I pick my clients and when I want to work.”

“And do you have sex with all of them?” he asked.

She shook her head.

“Some just want company. Others want to be dominated and controlled. I’m not a dominatrix, but they want a woman in control. Many are professional men, other in great power and they want to surrender it. I do some creative role playing too. I was planning on being a therapist, and in a way I am.”

Mike laughed.

“I never thought of it that way,” he said. “I thought you were the owner of the art galleries near the coffeehouse.”

“Actually, I’m part owner of two of them,” she admitted.

Mike smiled back at her.

“I have a question for you,” she said. “How are you dealing accepting that you’re a submissive?”

“It, it explains a few things,” he admitted. “One thing is that I know now why I have never had a long-term girlfriend. I just don’t know what will happen now.”

“You’ll find the right person; things seem to have a way of happening,” she replied. “Well, you better get cleaned up.”

Chapter 6

The next night, Heather positioned Mike on the bed as he was the first night, on all fours. The difference occurred when she tied him up.

“Some of my clients like to be tied up. Don’t worry, if you want to be freed, I will accommodate you,” she said as she attached leather cuffs to his wrists and ankles. “I want to see if the lack of freedom changes the effect of the sleeve.”

Mike was soon unable to move his arms and legs.

“Okay, are you ready?” she asked.

Mike nodded.

“I think you’ll enjoy this,” she said as she leaned up against him.

Mike felt the dildo enter him. It felt different this time as if it was slightly bigger, both in girth and length. There was no pain and he was soon getting lost in the sexual pleasure. As she fucked him, he felt her hands on his chest. She began to rub and pinch his nipples, which increased the sexual sensation.

He knew that he still had a cock, but the pleasure felt seemed it as if it was all internal, as if she was really fucking him. It was only when he came, that the illusion evaporated. She reached her hand around and placed it front of his face. He looked down and saw that it was full of cum.

Without a word, she moved it up to his mouth. He could feel the dildo still inside of him and she began to pump him again. The feeling was so good and moaned and begged her not to stop.

“Do you want this treat?” she whispered as she fucked him.

He nodded.

“Then take it my dear,” she said as she moved her hand closer.

Mike eagerly began to lick up the cum. There was no thought process, just a very natural urge and reaction.

“Very good. I knew you would like that,” she said as she began to fuck him harder.

Chapter 7

There was another surprise when they finished. Heather showed him the dildo, and he was shocked to see that she had used a different one.

“It looks like a real cock,” he said as she held it out.

“And did you like it?” she asked. “Please be honest.”

“It was even better than the other one,” he admitted softly.

“I’m pleased to hear that. This will give me more options with my clients,” she said.

“I have to admit that I’m confused about my sexuality now,” he admitted.

“Don’t be. Just take things as they come, my dear. Many people repress their true sexual feelings. As long as sex is done between consenting adults, I see no reason not to experiment. I would never hurt you,” she explained.

“I appreciate that,” he replied.

She then ran her fingers through his hair.

“When was the last time you had it cut?” she asked.

“A while. Haircuts cost money, and even though you have paid me, I need that for more important things like rent. I can get by with it long as I just pull it into a ponytail at work,” he said. “I also like it long.”

“You need it cut. I will pay for it, and you can go to my stylist,” said Heather. “She won’t too much off, I promise.”

“Okay,” he replied. “I trust you.”

Chapter 8

The next week, when Mike arrived at Heather’s home, he was wearing a knit hat.

“What’s with the cap? It’s not that cold outside,” she said as he came inside.

“It’s not that,” he said as he took off the hat. “Your stylist went a little too far. It makes me look like a girl.”

Heather looked at Mike’s hair. It was a layer look and combined with his natural curl, it did look quite feminine.

“I keep trying to style it so it looks masculine, but it keeps slipping back into this,” he said.

“When did you get it cut?” she asked.

“Two days ago. I thought it would get better,” he said. “She also trimmed my eyebrows, which makes matters worse. I know that I’ve never been that macho, but now I look like a girl.”

They sat down in the living room.

“Has anyone said you look like a girl?” asked Heather.

“I was called Miss several times,” said Mike.

“Please tell me about it,” said Heather.

Mike reached up and ran his fingers through his hair. Without realizing it, his nervous reaction only made his hair look even more feminine.

“I kept my hat on in class, but I forgot about it on the way home. I stopped for something to eat and without thinking about it I took off my hat and ran my fingers through my hair. When I my order at the front counter the guy called me ‘Miss’,” said Mike.

“And how were you dressed?”

“A hoody, leather coat, and jeans,” replied Mike. “I had my computer bag over my shoulder. I guess he thought it was a handbag.”

Heather nodded. The layered look would make it difficult to make out Mike’s body.

“And did you have your studs in your ears?” asked Heather.

Mike nodded.

“I can see how he was mistaken. So what did you do?” asked Heather.

“It was really noisy in there, so I thought I misunderstood what he said. I asked where the bathroom was and he pointed to the ladies room,” said Mike. “I nodded and left.”

“Was that the only time?” asked Heather.

“No. It happened at work too. The girls on my shift thought it was funny and my manager, made me a new name-tag with the name Mia on it,” continued Mike.

“Did you wear it?” asked Heather.

Mike shook his head.

“Of course not! I mean, I like Brandy a lot, but that would have been nuts to do that,” he said.

“Brandy is the name of your manager?” asked Heather.

“My shift manager. She’s really cool, and I like her a lot,” admitted Mike. “I’m just hoping that in a few more days the style will look less feminine.”

“That’s not likely,” said Heather as she reached over and touched his hair. “You can try some product, but that might make it worse. You might have to have it cut short to look masculine.”

“Damn, I like it long,” he said. “But I’m also tired of being mistaken for a woman.”

“Well, I have an idea that will at least work tonight,” said Heather.

“What’s that?” he asked.

“Come with me,” she said as she stood up and took him by the hand.

“What do you have in mind?” he asked.

“You’ll see, Mia,” she replied.

Chapter 9

“Okay, turn and look at the mirror,” ordered Heather.

Mike did as he was ordered and gasped.

“Holy shit, I look like a girl,” he exclaimed as he looked at his refection.

“Yes, you do Mia,” said Heather.

Mike didn’t correct her, as he was too busy looking at the mirror. His hair was now much curlier thanks to the product that Heather had worked into his hair. His eyes were heavily made up with dark eye shadow, mascara and eyeliner. His lips looked thick and pouty due to the dark red lipstick and gloss. His studs had been replaced with large gold hoops to complete the look from the neck up.

“Okay, time to get you dressed. As we’ll be having sex, I’m just going with stockings, garter belt, heels and a padded bra,” said Heather. “I have to admit that you’re very cute, Mia. I also think that you should think of yourself as a woman for tonight; you’ll enjoy this much more if you do. Okay?”

“Okay,” replied Mia.

“So, tell me your name,” said Heather.

“Do I have to?”

“What’s the harm?” asked Heather.

“Okay, my name is Mia.”

“Softer,” said Heather. “Get into character.”

“My name is Mia,” she replied.

“Very good. Okay now let’s get you dressed.”

Chapter 10

“How was it?” asked Heather.

“It was really good,” replied Mia as she looked over at Heather.

“You’re a natural,” noted Heather. “Your reaction to being fucked was very feminine.”

“I was just in character, as you suggested,” said Mia.

“If you say so,” replied Heather.

Mia didn’t reply.

“It’s rather late, why don’t you stay here tonight?’ suggested Heather.

“Sure, sounds good. I am really tired,” said Mia.

“Okay, let’s get that makeup off and I’ll pick you out something pretty to sleep in,” said Heather. “You might as well stay in character the rest if the night.”

“Okay,” replied Mia. “I’m too beat to argue.”

“Do you have to work tomorrow?” asked Heather.

Mia shook her head.

“Good, then we can play again tomorrow night,” said Heather. “Now, let’s get you to the bathroom and clean you up.”

Chapter 11

“Good evening Mia,” greeted Heather.

Mike shook his head.

“I’m Mike right now,” he said.

“Not for much longer,” said Heather. “Come with me.”

Heather led Mia upstairs and into the bedroom. On the bed there was a complete outfit laid out.

“What’s this?” asked Mia.

“I thought we’d take this to the next level and go out for a drink first,” said Heather. “Don’t worry, the place I’m taking you is very cool, and no one will hassle you. Besides, I doubt they’ll know that you’re really a guy, especially by the time I’m done with you.”

“I don’t know,” said Mia as she stared at the clothes on the bed.

There was a black bra and matching panties, a garter belt, stockings, high heels, a gray knit dress and a pair of breast pads.

“It will make the sex even more fun and exciting,” said Heather. “I have a few clients who cross-dress, and I have done this sort of thing with them many times. You pass quite well, Mia; no one will suspect the truth.”

“Okay,” replied Mia. “I trust you.”

“That’s the spirit,” said Heather. “Get undressed and we’ll get started.”

Chapter 12

Heather drove Mia to a local club where she often took her cross-dressing clients. She knew the owner and knew that she’d have no trouble getting in. She also knew that Mia wouldn’t be carded.

After checking in their coats, Heather led Mia directly to the bar.

“Walk slowly and relax,” whispered Heather as she escorted Mia. “Just remember, any guy looking at you is just checking you out, and any woman looking at you is checking out the competition.”

“That doesn’t make me feel more at ease,” replied Mia.

“You look lovely. I think you’re better looking as a woman than a man,” said Heather.

They sat down at the bar and Heather ordered their drinks.

“You really think that I’m better looking as a woman?” asked Mia.

Heather nodded.

“I’m not trying to push you in any direction, but the truth is the truth. You are a very attractive woman, and with some changes you’d look even better,” said Heather.

The bartender set down two glasses of wine in front of them and left.

“What sort of changes?” asked Mia as she took a sip of her wine.

“Add some highlights to your hair and curls for a start. I would also make your eyebrows even thinner and arched. Add a few more piercings and you could pull off a more alternative look. I would start with additional studs in ears, maybe one in the nose, tongue, oh and some nice tattoos,” said Heather. “Next, I would have you get breast implants and also hip and butt ones too, to give you a more natural shape.”

Mia listened without comment.

“I can help you with these changes and more,” continued Heather.

Mia took a sip of her wine.

“Do you really think that I’m transgendered?” she asked.

“A more important question is do you think that you’re transgendered,” countered Heather. “However, I suspect that you have a gender issue. The way you reacted when I made love to you was very telling.”

Mia took another sip of her wine.

“It didn’t take much effort to get you out here tonight,” continued Heather. “I think you should explore these feelings.”

“I don’t know,” said Mia.

“I doubt I’m the only one who sees this more feminine side of you,” continued Heather.

“What do you mean?” asked Mia.

“Your coworkers obviously suspect something. I bet that your manager Brandy not only suspects that you’re transgendered, but she will keep pushing you. The name-tag was just the start,” said Heather.

“It was just a joke, due to my hair,” countered Mia.

“You want to place a bet on it?” asked Heather.

“What kind of a bet?” asked Mia.

Heather motioned to the bartender for refills.

“If you don’t change your hair style, I bet that she will confront you about your gender. In fact, I wouldn’t be shocked if she dressed you up,” continued Heather. “If she pressed you, I know you’d give in.”

“And if I don’t?” asked Mia.

“I will pay you five grand,” said Heather. “But if you give in, then you have to get breast implants. Don’t worry, I will pay for them.”

“Breast implants? If I get those then…” said Mia.

“Then you’d end up as Mia full-time,” interjected Heather. “I feel you’re on that path anyway, so I might as well help you. So are you willing to make the bet?”

Mia thought about it for a moment and then nodded.

“How long do we set the wager for?” asked Mia.

“How about three weeks?” replied Heather.

“Okay,” said Mia.

“You’re going to love having real breasts,” said Heather as she got up. “I need to use the ladies room. Don’t worry, I’ll be back shortly.”

Mia nodded as she watched Heather walk away. She then thought about the bet and if she wanted to win or lose it.

Chapter 13

Once they got back to the house, Heather wasted no time in taking Mia upstairs and into the bedroom. She only partially undressed Mia as she wanted her to maintain the feminine illusion. She made sure that Mia still had on her bra, garter belt and stockings. She also made love to Mia, face-to-face. She used a slightly bigger cock shaped dildo. As she suspected, Mia had no trouble taking it all.

“Did you enjoy that?” asked Heather.

Mia nodded.

“How realistic is that, I mean the way it feels?” asked Mia.

“It feels very much like a real cock,” replied Heather. “Maybe someday you’ll be able to make your own comparison.”

Mia just stared back. She didn’t argue, as the same thought was going through her head.

“There are many men who like women like you. I have several clients who would love to be with you,” continued Heather.

“You mean pay to be with me?” asked Mia.

Heather nodded.

“I think you have the makings of an excellent escort,” replied Heather. “Especially after you get breast implants.”

“You make it sound like I’ve already lost the bet,” said Mia.

“And it’s obvious that you’re thinking about that possibility too,” replied Heather. “I’m not going to force you into anything, but I will continue to push you so you can find who you really are.”

“This is crazy, I mean if I changed, how would people react?” asked Mia.

“Your real friends would accept you,” replied Heather.

“And what about college?” asked Mia.

“Your school is very progressive. I doubt there would be any issues,” replied Heather.

Mia sighed.

“And what about my family?” she asked.

“Tell me about them,” ordered Heather.

“My parents live in the suburbs outside Chicago. Mom works in a bank and Dad is in construction,” replied Mia.

“Any brothers or sisters?”

“One each, both are older. My brother Jack is a paramedic and my sister Joan is a dental technician. They’re both married.”

“And do they all live in the Chicago area?” asked Heather.

“Joan lives in Downers Grove, and Jack is in Madison, Wisconsin. He stayed there after he dropped out of college,” replied Mia.

“And how would you describe them? Are they open-minded?”

“Mom and Dad are conservative and so is Joan. Jack is a little more moderate,” replied Mia.

“I see, so there may be problems if you came out as transgendered?” asked Heather.

“That’s a good description -- problems,” replied Mia.

“Well, we’ll cross that bridge when we get to it,” said Heather.

“You mean if we get to it,” said Mia.

“If that works for you, then if it is,” replied Heather.

Chapter 14

When Mia stepped out of the shower the next morning she was shocked to see a female wardrobe laid out for on the bed. It was a pair of panties, bra, breast pads, a sweater and a pair of jean. Additionally there was a pair of boots.

“What’s this?” asked Mia.

“I thought we’d go to breakfast,” said Heather.

“But what about the clothes? Why can’t I go as a guy?” asked Mia.

“I prefer you go as Mia, and I also think that you need some time to explore your feminine side in a safe manner,” countered Heather. “Honey, you pass quite well; no one will suspect you’re physically a man. I also want to do some shopping, I want to expand your wardrobe and you also need some makeup and toiletries.”

“And if I say no?” asked Mia as she sat down next to the clothes.

“I don’t see that as a possibility. Now get dressed, and I’ll help you with your makeup,” said Heather. “However, pay attention, as you’ll soon be doing it yourself.”

“Will we come back here afterwards?” asked Mia.

Heather shook her head.

“I can’t go into my apartment dressed as a girl! What will people think?” asked Mia.

“They will think you are a lovely young woman, which is what you are becoming,” replied Heather. “Deep down, you want to do this, right?”

Mia nodded.

“Good girl! Now let’s get you ready, I’m hungry,” said Heather.

Chapter 15

The next two days were a blur for Mike. Whenever he wasn’t in class or working, he rushed home to immediately change into her female clothes.

Heather had bought him several outfits, including casual clothes that weren’t that different from his male items. She also had given him a large supply of makeup. Mike began to practice applying his own makeup. He quickly realized how difficult it was and that there was no way he could go out in public on his own, even if he got up the nerve.

He had dressed up one evening and waited until he figured it was late enough that he would not be seen. However, he just stood by the door, unable to leave.

It was very confusing to him. He had always though that his urges to dress was just a fantasy that he could keep deep inside. Now, he was questioning his gender. Was he really a man, or a woman?

He wished he could have talked to Heather, but she was out of town that week.

As he arrived at work, he was so lost in his thoughts that he didn’t see Brenda, and he almost walked into her in the employee break room.

“Oh, sorry,” he apologized.

“You okay? You seem to be in a different world,” she replied.

“I’m just thinking about a test,” he lied.

“Uh-huh,” she replied with skepticism.

Mike hung up his coat and took off his hat. As he did he ran his fingers through his hair.

“I love that you haven’t gotten your hair cut! It’s so cute Mia,” kidded Brandy.

“I haven’t had the time,” he lied.

“No, I think you like it,” she countered. “You should wear the name-tag that I gave you, it’s more fitting for the way you look, Mia.”

“I’m not going to wear it,” he said nervously. “And please don’t call me Mia.”

“Mia, I think we need to talk, please sit down,” she said softly.

Mike looked at her and then sat down on the couch. Brandy sat down next to him.

“What is it?” he asked.

“Do you really need to ask, Mia?” she asked. “It’s obvious that you’re struggling with your gender identity.”

“I just got a bad haircut,” he countered.

Brandy shook her head.

“Actually you have a great hair style; it looks very cute and sexy. There’s more. First off, your eyebrows are much thinner and feminine, also your nails are longer than before,” she said.

Mike instinctively covered up his hands.

“Anything else?” he asked.

“If you insist,” she replied as she took out her phone. “Take a look at these.”

Mike gasped as he saw photos of him dressed as Mia at the club.

“Oh, my, God,” he gasped.

“It’s okay, Mia, you look lovely. You’re much better looking as a woman than a man,” comforted Brandy. “I want to help you become the girl that you obviously want to be.”

“What do you mean?”

Brandy got and retrieved several bags.

“Mia, it’s time that you dressed like the other girls here,” said Brandy.

The female employees all worse short skirts and heels.

“Just so you know, it really does increase the amount of tips we get,” she said. “Now, undress and I’ll help you change.”

Mike began to open his mouth, but instead he just stood up and began to take off his clothes.

“Don’t worry, the girls out front will make sure we won’t be disturbed,” said Brandy.

“So they know?” asked Mike.

“Yes, we have been talking about this for a while. I showed them the photos, and they think that you look lovely,” replied Brandy.

“You showed the pics to other girls?” asked Mia.

“Of course,” replied Brandy. “Ooooh, I love the fact that you’re hairless. This will make things much easier. Do you wax?”

Mike nodded as he felt Mia take over.

She helped Mia get dressed in the outfit which consisted of a bra, panties, stocking, black high heels, black skirt and company t-shirt.

Mia cupped her breasts.

“Aren’t these too big?” she asked.

“No, you look good with big breasts,” replied Brandy. “They’re 34-DD and you look great.”

Mia wasn’t sure and stared down at her chest.

“Besides, don’t you know, big tits equal big tips!” said Brandy.

Mia rolled her eyes.

“Now, sit down, and I’ll do you hair, nails and makeup,” said Brandy.

Thirty minutes later Mia stared at her reflection in the mirror.

Her hair was styled out with product, which gave her a wilder look. Her makeup made her look like many of the other college girls, with heavy eyeliner and dark eye shadow. Her lipstick color was a dark maroon. Her nails were colored a similar dark red. She completed the look with some hoop earrings and other pieces of jewelry. On her fingers, Mia now had several silver rings.

“I’m not sure about the heels,” said Mia.

“You’ll get used to them, we all do,” replied Brandy.

“I’m surprised none of the other girls have complained about wearing them,” said Mia.

Brandy smiled.

“What?” asked Mia.

“That’s the second time you said ‘other girls’. Yes, this is the right path for you,” said Brandy.

“I’m not sure about the makeup,” said Mia. “I look a little like Fiona.”

Fiona was a Goth girl who worked the early morning shift.

“Yes, but not as extreme, not that you couldn’t pull that look off. You look good with a slight alternative appearance,” said Brandy. “In fact, I want to get your hair cut, dyed darker and streaked, maybe red or purple. You’ll look really hot. Oh, and you should get some piercings.”

“Where?” asked Mia as she stared at her new look.

“More in the ears, nose, tongue, for a start,” said Brandy. “Also some tattoos.”

“Seriously?” asked Mia.

“Yes, you’ll look really hot,” said Brandy. “I’ve been thinking about this for a while, but for the time being this will do. No one will know that you’re not a real woman.”

Mia slipped on her apron and put on her name-tag. The apron did little to hide her large breasts.

“What about David?” asked Mia, referring to the owner of the coffee house.

“He’s cool about it. I talked to him and showed him the photos. He was very impressed with how feminine you look. He said that he would be in today and would talk to you.”

“Was it that obvious?” she asked. “I mean, about this?”

“We knew you were hiding something, but in the last few days it came to us. When I saw you at the club I knew that this charade had to end. Don’t worry about anyone here, we’re all in this to help you become the woman you were meant to be,” said Brandy. “Oh, and just so you know, I think you look pretty hot.”

She then leaned over and gave Mia a quick kiss on the lips.

“Well, let’s go out and get to work. The other girls will want to see you,” said Brandy.

Chapter 16

Just as Brandy said, the girls on the off-going shift were very supportive of Mia. Leslie -- a short thin blonde -- gave Mia a big hug. The other woman was a grad student in her mid-twenties named Vanessa. She was full figured and had short black hair. She adjusted her black framed glasses, as she inspected Mia.

“Good to see that you are finally out,” she said as she gave Mia a hug.

The two other girls on the on-coming shift were also supportive.

“See, everyone is fine with this,” said Brandy.

Thankfully the coffeehouse was very busy for the first part of their shift and Mia didn’t have much time to think. She found that she quickly adjusted to being on heels. Her new large breasts took longer to get used to.

An hour to go in their shift, David Carr, the owner arrived. He was in his mid-forties and had owned the shop for the past five years. He was six-one and very fit. He took pride in his physical appearance. His dark brown hair was starting to turn gray, but he didn’t mind as long as it all still there.

“Good afternoon Brandy,” he greeted. “How’s the shift going?”

“Very well, thanks,” she replied.

He stopped and ran his eyes over Mia and nodded.

“Mia, when you get a chance, come back to my office,” he said pleasantly.

“Okay,” replied Mia.

Chapter 17

Twenty minutes later, Mia walked back to David’s office. She was very nervous and it felt as if her heart was about to come out of her chest.

She walked up to his door and knocked.

“Come in,” he said.

Mia opened the door and stepped into his office.

“Hi,” she said.

“Mia, please sit down,” he replied.

Mia did as he said and sat down on the love seat that sat across from his desk.

“I have to admit that you look even better than I had expected. The photos Brandy showed me didn’t do you justice,” he said.

“Thank you,” replied Mia softly.

“I have no issues with you still working here, but it has to be either Mike or Mia, not both, is that clear?” he stated.

“I understand,” she replied.

Things we accelerating so quickly that she could barely keep track of what was happening.

“Personally, I prefer you as Mia. It has been my goal to have only a female staff. It does bring in the customers,” he said. “Obviously you don’t mind wearing a skirt and heels.”

“I’m getting used to it,” she replied.

“Well, you have the legs for it,” he replied with a smile. “If you work here as Mia, I will give you a slight raise, as I’m sure your expenses will be going up.”

“Thank you,” she replied.

“So, is that a yes?”

Before she realized what she was say, Mia replied.

“Yes, I will be Mia,” she replied. “Thank you.”

David got up and walked over to her. When she stood up, he gave her a hug and then a kiss on the cheek.

“Welcome to the team, Mia,” he replied.

Chapter 18

“David is a nice guy,” said Brandy. “Although he has slept with almost everyone here. I will tell him to hold off with you for the time being. Oh, do you like men?”

“I prefer women, but I’m curious about being with a man,” admitted Mia.

“Cool, I’m bi too,” said Brandy.

“I can’t believe that this is happening so quickly,” said Mia.

“Sometimes it’s better that way. Besides, you’re what? 22? So you’ve been holding this in for all that time, it’s about time you came out as the real you,” said Brandy. “Now, do you have any plans after work?”

Mia shook her head.

“Good, then we’re going shopping. How big is your wardrobe?”

“Not very big,” replied Mia.

“Well, that has to change. All the girls want to help you, but I have first shot,” said Brenda. “We’ll go out shopping after work.”

Chapter 19

“Well, that’s the last of it,” said Brandy.

They had just spent the last hour putting away Mia’s new clothing.

Mia was dressed in a long skirt, tights, boots and a sweater. Brandy had brought the outfit to work and had Mia change into it their shift.

“Now, until you get the hang of makeup, I’ll stop by to help you,” said Brandy. “You’ll get the hang of it pretty quickly.”

Mia nodded as she looked at her nails.

“These will take some getting used to,” she said.

After hitting a few stores, Brandy took Mia into get her nails done. She now hand long extensions on each nail.

“Yes, but it looks so good,” said Brandy. “I made an appointment with my salon; they’ll get you in tomorrow afternoon. Don’t worry, I’ll go with you.”

“I’m going to have to go to the college admin office tomorrow to explain this,” said Mia.

“You won’t have any trouble. They’ll make the changes for you,” said Brandy. “You’ll have a new student ID tomorrow.”

“I thought I would need more proof than just showing up,” said Mia.

“For a driver license you will, but the college is very liberal. Now, why don’t we go out to dinner, my treat,” said Brandy. “And before you say anything, you look great.”

“Okay,” replied Mia.

“You look great in skirts and dresses,” continued Brandy.

Mia felt her face get warm.

“You also look cute when you blush,” said Brandy as she ran her fingers through Mia’s hair.

Mia smiled.

“The main reason that I wanted to transform you is that I want you to be my girl,” confessed Brandy.

“Um, so is this a date?” asked Mia.

Brandy leaned closer and kissed Mia.

“What do you think?” asked Brandy.

Chapter 20

After dinner, they went back to Mia’s place.

“Thanks, I had a great time tonight, and well, thanks for everything,” said Mia as they sat down on the couch.

“It was my pleasure,” replied Brandy. “I must admit that I have always liked you, but I prefer the new female version. You aren’t as uptight.”

“I guess you’re right, I was too busy holding all this in,” replied Mia.

Brandy slipped her arm around Mia.

“Things like your submissive nature?” asked Brandy.

Mia nodded.

“How did you know?” asked Mia.

“You were trying too hard to be something you weren’t. We thought it might have been because you’re short and thin, but over time we suspected that you were submissive. I dated a boy in high school that liked to be controlled, and it turned me on.”

“I thought I was able to hide these feelings from others,” said Mia.

“It must be a relief to be out now,” replied Brandy.

“Yes and no. I’m really comfortable being Mia, but I still have to deal with my family. I thought that I would have more time to think about this, but so much for the best laid plans. I know that I can’t go back to being a guy.”

“When do you plan on telling them?” asked Brandy.

“Soon. I don’t want them to hear about this from someone else. I owe them that much,” said Mia.

“Well, don’t worry about that right now,” said Brandy as she leaned down and kissed Mia slowly on the lips.

As they kissed Mia felt Brandy’s arms pull her closer. She offered no resistance. It was funny that as Mike she had never gotten up the nerve to ask her out, and now that she was living as Mia, they were together.

“Tonight will be another lesson in your road to womanhood,” said Brandy. “I’m going to teach you how to pleasure another woman. Will you obey?”

“Yes,” sighed Mia.

Brandy stood up and took Mia’s hand.

“Come with me, my love,” said Brandy

Chapter21

A few days later, Mia met Heather for lunch.

“Well, you’ve been rather busy,” said Heather as Mia sat down across from her.

Mia was dressed in a gray dress, black stockings, and knee-high, high heel boots. Her hair was now dyed a dark red with highlights. It had also been restyled so that there was no doubt that she was a woman. Her eyebrows were now very thin and highly arched.

Each ear had additional piercings of several studs to go with the silver hoops.

After the waitress took their order, Heather began to comment about Mia’s appearance.

“Very nice, you look quite lovely,” said Heather. “So, tell me about it.”

Mia told her about how Brandy had transformed her at work and that they were dating.

“How do you feel about the fact that your boss is interested in you?” asked Heather.

“To be honest, I am intrigued,” replied Mia. “I have to admit that the sex we had has opened up my eyes.”

“I’m not surprised. I see you got your tongue pierced, are there any other changes?” asked Heather.

“My naval and clitty are also pierced now,” said Mia. “We also looked at tattoos.”

“What kind?” asked Heather who appeared amused.

“One on the back, just above the panty line, and one on the back of my neck, both are floral patterns of vines and flowers,” replied Mia.

“They sound quite lovely. I also like the piercings, along with the new hairstyle,” said Heather. “I assume the large breasts are her idea too?”

Mia nodded.

“She says that I have the body for them,” said Mia.

“Well, we’re soon going to find out for real,” said Heather. “I suspected that you would lose the bet and have made an appointment for us to see an excellent plastic surgeon this afternoon. And she’s right, you should have large breasts.”

“Can they make them this big?” asked Mia.

“He has a special process that used fat redistribution. I’ve seen his work and he’s very good. In fact, he also wants to do your hips and butt. I think that you should do it. It will give you a very sexy body.

“Okay,” replied Mia.

“So it sounds like you and Brandy are becoming quite close,” said Heather.

“You could say that. I never stood a chance with her as a guy, and now we’re lovers,” said Mia.

“Did she pick out that dress?” asked Heather.

Mia nodded.

“She has replaced my wardrobe. I don’t have any male clothing anymore; she took everything to Goodwill,” said Mia.

“Another bridge crossed,” said Heather.

“Burned is a better choice of words,” said Mia. “Along with other things.”

“So, you told your family. I take it things didn’t go well?”

Mia held out her hand and rocked it back and forth.

“My Dad called me a fucking faggot and hung up on me. Mom called me later and was more open-minded. She even asked for a photo. She said that she would work on Dad,” said Mia.

“And your siblings?”

“My sister won’t answer the phone. However, my brother said that he can’t wait to meet his sister. go figure!” replied Mia.

“Give them time,” said Heather. “Now, I have something that we need to talk about. I will be upfront with this: how would you like to work for me?”

Mia looked around to see if anyone was listening.

“Are you serious?” she asked softly.

“Very much so. I think you have what it takes to make an excellent escort. I have several clients who would love to be with a girl like you,” replied Heather. “The hours are flexible, and the returns are very good.”

“I want to finish college,” said Mia.

“You can do both,” replied Heather. “Honey, you’re going to need money for this transition. Also, I think you would love doing it. Not all the clients want sex. Some just want company.”

“Can I think about it?” asked Mia.

“Of course! You won’t be able to do this until after you heal from the surgery on your breasts anyway,” continued Heather.

“Okay, that makes sense,” said Mia. “Maybe I’m going at all this too fast. Maybe we should put off the breast implants for a while.”

“Maybe, but you can’t undo what you’ve already done. You’re out at work and college, you told your family, you can’t undo this. Getting breast implants will just help you adjust to your new life as a woman,” said Heather. “Besides you won’t have to deal with the pads anymore and that’s a plus.”

Mia nodded.

“Yes, you’re going quickly, but you have people who are supporting you. We’re not doing this to hurt you or humiliate you, but to have you find inner peace. When I saw the way you reacted the first time we had sex, I knew you had a strong feminine side. It’s the real you Mia.”

“I guess you’re right,” said Mia.

“I can help you in another area. I’ve talked to my lawyer and she’s laid out what we’ll have to do to get your identity changed legally. She said that it’s pretty routine in this state and she could start processing the paperwork as soon as you’re ready,” said Heather.

“Really?” asked Mia.

“Yes, that’s right. So, are you ready to take the next step?”

“Sure, call her,” said Mia.

Chapter 22

“Wow, this is what you’ll look like?” asked Brandy as she looked at the computer generated images that the plastic surgeon had provided Mia.

They showed her body with large breasts and shapely hips and rear.

“Yes,” replied Mia. “My breasts will be smaller than the pads, but that’s to account for the growth that I’ll get from hormones. I started the treatment today.”

“Cool,” said Brandy. “You’re really becoming a girl. So, are you going to get the full surgery?”

“Not for a while, since I want to adjust to all the other changes,” said Mia.

“Makes sense. So when are you going to get this done?” asked Brandy.

“In two weeks, right after finals,” replied Mia. “The recovery isn’t supposed to take that long, as the surgeon uses new micro-surgery techniques. He also said that there would be minimal scarring.”

“That’s good to hear,” said Brandy. “I can’t wait to play with your new boobies.”

Mia giggled.

“Have you told David?” asked Brandy.

“Yes, he was cool about it. I’ll only miss a week or so of work,” replied Mia.

“He’ll want you even more now,” said Brandy. “Although the way he looks at you, I don’t think he’s willing to wait.”

“So has he really had sex with every girl at the coffee shop?” asked Mia.

“As far as I know. He’s actually fun to be with in bed. I think you’ll like it,” said Brandy.

“And you won’t mind?”

“No, I see it as part of your education in becoming a woman,” said Brandy. “I know from our time in bed that you like being fucked. Have you ever given a blowjob?”

“No,” admitted Mia. “I got a few.”

“I think you’ll like it. And the fact that you have had one will make you pretty good at it, as you’ll know what to do,” said Brandy. “This sort of talk doesn’t bother you does it?”

“It used to,” said Mia.

“Have you ever had sex with a guy?”

“No,” replied Mia.

“Did you think about it? Be honest,” said Brandy.

“I guess I thought about what it would be like, but I never acted on it as Mike,” said Mia.

Well, David will be a good first time for you. He doesn’t want any commitment, just a good time. I think he’s very curious about doing it with a girl like you. It will allow him to see a different side of his own,” said Brandy.

“Makes sense,” said Mia.

“I want you as my girl, but I also want you to explore your sexuality, Mia,” said Brandy

Mia nodded. She almost brought up Heather’s offer, but decided not to. She wanted to talk to Heather first.

Chapter 23

“Are you sure this is a good idea?” asked Mia as she paced in Heather’s living room.

She was dressed in a leather skirt, tights, knee-high boots and a red sweater that looked as if it was poured over her chest.

“Yes, you need to honest and open with her,” said Heather.

Mia looked at her watch.

“She should be here shortly. I hope she understands,” said Mia.

“I’m pleased that you’ve accepted my offer. I think you’ll be quite popular. I also think you have the demeanor to be an escort. You’re open-minded and willing to try new things,” said Heather. “I’m going to look forward to training you. I already have several clients who are interested in you.”

“Really?” asked Mia.

“Yes, and I imagine that you’ll quickly have a list of regular clients. It’s how I do most my business. It’s nice to have clients that you know what to expect,” said Heather.

Just then they heard the doorbell ring.

“That must be Brandy,” said Mia nervously.

“It will be okay,” said Heather.

Together they walked over to the front door.

Brandy was standing on the front step and smiled when she saw Mia.

“Hi Mia,” greeted Brandy as she stepped inside. “You look nice.”

Heather closed the front door.

“Thanks,” replied Mia.

Mia turned to introduce Heather to Mia. However she was shocked when Brandy hugged the older woman.

“Good to see you again, Aunt Heather,” greeted Brandy.

“Thank you my dear,” replied Heather.

“What? What’s going on?” stammered Mia.

She felt very weak, as if she was going to pass out.

“Brandy is my niece,” said Heather.

A panicked look appeared on Mia’s face.

“So, this was all a set up?” she gasped.

Brandy took Mia’s hands.

“No, it wasn’t,” said Brandy. “It was all my idea.”

“What?” asked Mia as she wiped tears away from her eyes.

“Come let’s sit down and talk this out,” said Heather. “Everything will be clear in a moment.”

The three women walked together into the living room. Mia sat down and nervously waited to hear what was going on.

“Please tell me that you haven’t been using me,” begged Mia.

“What I said about suspecting you were hiding something is true, Mia. I talked to Aunt Heather, and she offered to help,” said Brandy. “I guess we should have told you sooner, I apologize for that.”

“I’m also sorry. We never intended to hurt you. I truly was looking for someone to help test the device. When Brandy talked to me about you, it seemed like the perfect match,” said Heather. “The more I worked with you, the more I saw that Brandy was right, and I did my best to help you see the real you. I truly see potential in you as an escort.”

“I don’t have any problems with you being an escort, Mia; in fact I agree with Aunt Heather: it would be a great opportunity for you to fund your transition,” said Brandy. “I also know that she’s very good at screening her clients, as I have worked a couple of times for her to help pay for tuition.”

“Really?” asked Mia.

Brandy nodded and took Mia by the hands.

“Honey, the last thing I want to do is hurt you. I love the woman that you have become, and I want to help you grow into your new life,” said Brandy.

“You really mean that?” asked Mia softly.

“Of course,” replied Brandy. “I wouldn’t lie to you. Yes, I love controlling you, but I want our relationship to be mutual.”

“I don’t know what to say, this is all happening so quickly. But it also feels so right,” said Mia.

“Mia, I know this must be overwhelming, but we really do care about you. We planned on telling you all this eventually,” added Heather.

Brandy reached over and ran her hand gently across Mia’s Cheek.

“I truly love you Mia,” said Brandy. “I want to help you blossom in all ways.”

“Okay, I believe you,” said Mia as she took out a tissue and began to wipe her eyes.

“Are we okay?” asked Brandy.

Mia nodded.

Brandy leaned close and gave Mia a long hug.

Chapter 24

“What time are you going out with him?” asked Brandy.

They were at work on their shift together.

“Right after work,” replied Mia. “I brought an outfit to change into.”

“Excited?” asked Brandy.

“I have to admit that I am. I mean, this is another big step,” said Mia.

“David is pretty cool, and I know he won’t hurt you. If he does, every woman who works here will beat the crap out of him,” said Brandy.

“That’s good to know,” said Mia.

“So what are you going to wear?” asked Brandy.

“Gray skirt, black sweater, stockings, garter belt, and high heels,” said Mia. “We’re going to dinner.”

“And then?” asked Brandy with a wink.

“I’ll let you know,” replied Mia. “I would have preferred to wait until after I get my breasts, but now I plan on leaving this job to work for Heather.”

“I doubt that David will mind,” said Brandy. “He can’t keep his eyes off you.”

Mia smiled back at Brandy.

“I thought it was my imagination,” she said.

“No, he definitely wants you,” said Brandy. “I suppose that it’s sexist and all, but he doesn’t force anyone to have sex. If a girl says no, he’s cool with that. But we‘re also using him, and he’s really good in bed. I know you’ll have a great time.”

“I’m so glad that you’re so open-minded about all this,” said Mia.

“I love you; it goes with the territory,” replied Brandy. “I’m glad that you’ve agreed to move in with me.”

Mia had moved in with Brandy the previous weekend. They were presently looking for a larger place.

“I like it. I hated living alone, and now I’m with the woman of my dreams,” replied Mia.

Brandy winked at her.

“And so am I,” said Brandy.

Chapter 25

Dinner was very nice. David took her to a small local bistro. He was the perfect gentleman. In many ways, it was the way that Mia had always wanted to act when she was on a date as Mike. It just confirmed that she was doing the right thing in becoming a woman.

“I have to admit that I can’t imagine that you were ever Mike,” said David. “You seem so comfortable as a woman.”

“Thank you,” replied Mia. “I guess it’s because I was trying to hold it in for so long.”

“That makes sense,” he replied. “I was very pleased when you accepted my invitation to dinner.”

He then reached over and took her hands into his.

“I find you very sexy,” he said as he leaned closer to her.

Mia smiled back.

“I suppose you know my reputation,” he said.

“Yes, the other girls have talked to me about you,” she replied. “Very nice things.”

He smiled back at her.

“I would love to take you home with me,” he said. “I know this is rather blunt, but I don’t see any reason to hide my intentions.”

“I would love to be with you tonight,” replied Mia.

A short time later they were in David’s BMW and heading to his home.

Chapter 26

“Make yourself comfortable,” said David as he hung up their coats. “Can I get you a drink? A glass of wine?”

“That would be nice,” replied Mia as she walked into his small, but nicely furnished living room.

It was a very masculine living room. There was a leather couch and a matching love seat. There was also a reclining leather chair. A large HD TV was mounted on the wall. She sat down on the couch and waited for David.

He walked in carrying two glasses of wine. He handed her one of the glasses and then sat down next to her.

“To tonight,” he said as he touched his glass to hers.

Mia had to admit that he was very smooth.

The wine was good and felt nice and warm as it entered her body.

She looked into David’s eyes and without a word; he took the glass out of her hand and set it down on the coffee table. He then caressed her face with his hand before pulling her close. He was forceful without being harsh, thought Mia, as his lips pressed against hers. She then felt his tongue slip into her mouth.

It then hit her that she was kissing a man and that it felt so right. It was even better than she had fantasized about.

“I’m not being too forceful for you,” he whispered.

“No,” replied Mia. “In fact, I like it this way.”

“Really?” he replied. “Are you submissive?”

Mia nodded.

“Very nice,” he replied. “Please stand up.”

Mia did as she was told.

“Stand in front of me,” he ordered, “and slowly undress. Stop when I tell you.”

Mia nodded and slowly took off her sweater.

David sipped his wine and nodded as he watched.

“Take off your skirt next,” he ordered.

Mia slipped her skirt down her legs and then stepped out of it.

“Take the bra off,” he stated.

She reached around and undid her bra, and as she covered her chest with one arm, she slipped her bra and pads off. She stood in front of him with her crossed arms over her chest.

“Nice,” he said. “Move your arms.”

Mia did as she was told.

Even though she had only been on the hormones for two weeks, her nipples were now larger and darker in color. The doctor said that this was due to the new process that he was using.

“Very sexy,” he said. “Are they sensitive?”

“Very,” she replied.

“I can’t wait to play with them,” he replied. “Now, slip off your panties.”

Mia did as he ordered.

“I like the piercings,” he stated. “Do you plan on getting your nipples done too?”

“Eventually,” she replied. “But after I get the implants.”

“Of course,” he replied. “Come sit down next to me.”

Mia walked over and sat down next to David. He immediately slipped his arm around her and pulled her close. As he kissed her, he began to run her nipples through his fingers.

Mia began to squirm as waves of pleasure began to run through her body. He was more physical than the way Brandy had played with her nipples, yet she found it very erotic.

“You like that?” he whispered.

“Oh yes,” she moaned.

“Very good,” he replied as he moved one of her hands to his crotch.

Mia could feel David’s hard cock, and she instinctively began to rub it.

“Take it out,” ordered David

Mia undid David’s belt and then undid his trousers. She could feel her heart beating faster, as she took his cock into her hand. Without hesitation, she began to gently stroke it.

“Hmm, you know what feels good, don’t you,” he moaned.

Mia felt the precum against her hand, as she stroked his cock. She was really pleasuring a man; it was no longer a forbidden fantasy.

“Mia, get on your knees,” ordered David.

Without hesitation, she got off the couch and positioned herself on her knees between his legs. She looked up at him and he nodded. Lowering her head she leaned down and began to kiss and lick his cock.

Mia knew that this was another step in becoming a woman and leaving her old life behind her. It would also soon become her job once she started work as an escort. Heather was right; the idea of being a professional escort truly excited Mia.

As she took David’s cock into her mouth she knew that she wanted to give him the best blowjob that he had even had. She was now a professional and even though she wasn’t going to be paid, she would use this night as practice. Brandy was her love, and all others would be clients.

David leaned back and moaned as Mia worked his cock. He was amazed by how good she was. The sensation of her pierced tongue only added to the pleasure. He reached over and took her head in his hands and guided her as she began to suck him off.

Mia struggled, at first, not to gag as she took his cock all the way into her mouth, but with each passing moment, she relaxed. She found that she was actually enjoying herself. Her nipples were very hard, and she found herself playing with them as she sucked his cock.

“Damn, you’re good,” moaned David.

She began to pick up pace and sucked him faster. She could tell by his moaning and breathing rate that he was getting close to an orgasm. This only made her work his cock faster. She wasn’t sure how she’d react when she came, but when he did, she found herself eagerly taking his seed.

David gasped and moaned as Mia slowly brought him down from his orgasm.

“My god, Mia, that was incredible,” he sighed.

Looking up, she smiled at him.

“I’m pleased to her that,” she replied as she licked her lips.

She then reached over and picked up her glass and took a long drink of wine.

“Please come back up on the couch,” he said.

Mia did as she was asked and sat down close to him.

“You were wonderful,” he said as he pulled her closer.

“Thank you,” she replied. “I’m glad you enjoyed it.”

“So what now?” he asked.

“Do you want to make love to me?” she asked.

“Really?” he asked.

Mia nodded.

“I’ve never done that before, I mean with a girl like you,” he said.

“And you’ll be my first man,” she countered. “I’m anxious to know what it’s like.”

“Okay, but let me get my strength back first,” he said as he pulled her close.

Chapter 27

“So how was it?” asked Brandy when Mia came into their home.

“I enjoyed it,” she replied as she gave Brandy a hug.

“That’s good to hear. You want some tea?” asked Brandy. “And we can talk about it if you desire.”

“I’d like that. Let me grab a bath first and change into my PJs,” replied Mia.

Thirty minutes later they were cuddling together on the couch sipping tea.

“I’m glad to hear that David was nice with you,” said Brandy.

“I think he wanted to give me oral, but couldn’t get the nerve to try it,” said Mia. “He did stroke me when we made love.”

“And how do you feel about all this?” asked Brandy.

“The whole evening confirmed that I have made the right decision to transition. I mean, from the beginning of the date to when he kissed me goodbye when he dropped me off her, it all felt very natural,” admitted Mia. “There’s something else.”

“What’s that?” asked Brandy.

“I kinda used this night as a test to see if I could actually be an escort. I guess I passed it, as I’m not ashamed of what I did,” she explained. “The sex I had with him, while enjoyable, didn’t have an emotional connection like it does with you. Does that make sense? I mean, I enjoyed myself, but knowing there was no attachment made it very freeing. With you, it’s very different.”

“It makes sense. I know what you mean about the lack of emotional connection. I went through that, when I worked for Aunt Heather.”

Mia let out a big yawn.

“I think we should go to bed,” said Brandy.

“I’d like that,” replied Mia. “Thank you again for everything.”

“My pleasure,” replied Brandy as she gave Mia a kiss.

Chapter 28

Two months later, Mia stood in front of the full length mirror in the bedroom. She was naked and inspecting her body.

She was pleased with what she was seeing. Her breasts were large and full. Her present bra size was 34-DD. Her doctor said that she might get larger due to the hormones. Her nipples were large and very sensitive.

Each nipple had a small steel ring in it.

She ran her hands down her thin waist to her hips and rear. They had been modified at the same time as her breasts.

Just as Heather had said, she had grown to love her body being totally hairless. She had received laser treatments to permanently remove all her hair below her head.

She turned and looked at her tattoos.

In addition to the one above her panty-line and on the back of her neck, she also got one on her ankle, another floral design.

She turned and studied her face. She was becoming very good at doing her makeup, although eyeliner was still a problem. She was debating getting permanent makeup.

She reached up and touched the jeweled stud that was in her nostril. It was Brandy’s idea to further enhance Mia’s alternative look. Heather agreed that it would make Mia more desirable.

She began to get dressed. Tonight she was wearing stockings, a garter belt, short black leather skirt, knee-high spiked high-heeled boots, a sleeveless red silk top, and a leather jacket. Her makeup was heavy and sexy with dark colored eye shadow.

Her top was low cut and showed off her cleavage.

She completed the outfit with silver jewelry and a thin spiked black choker.

“Very nice,” said Brandy as she stood in their bedroom doorway. “If he doesn’t like you he’s crazy.”

“Heather said that he likes his girls wild and sexy,” said Mia.

“Well you’ve got both down. Where are you meeting him?” asked Brandy.

Mia mentioned the name of the bar.

“He’s staying in the downtown Hilton,” said Mia.

“What time do you think you’ll be home?”

“Around two,” she replied. “Heather knows where I’ll be too. She knows this guy and says that he’s very nice.”

“I’m sure he is. Oh, don’t forget that tomorrow we’re going out with the girls from the coffee house; they want to see how you’re doing,” said Brandy.

“I can’t wait,” said Mia. “Well, my ride should be here shortly. I suppose that I’ll need to get a car soon.”

“You can always borrow my Honda,” said Brandy. “Or better still, use your bike.”

Mia giggled.

“Stop! I don’t want to laugh; I’ll mess up my makeup,” she said. “Besides, I don’t think I can ride a bike in heels and a skirt.”

“It would be fun to watch. Anyway, I’ll see you when you get home,” said Brandy.

“You don’t have to wait up,” said Mia.

“I know,” replied Brandy as she smiled at her lover. “I’m so proud of how you’ve accepted the real you.”

Mia blew her lover a kiss.

Chapter 29

A little after two, Mia returned to the apartment. Brandy was waiting for at the front door and gave her a hug and a kiss.

“So, how was it?” asked Brandy. “Oh, I just started the kettle; you want some tea?”

Mia nodded, and she slipped off her heels.

“He was very nice,” replied Mia. “We had drinks, and then went back to his hotel room where we had sex.”

“And was he any good?” asked Brandy as she set out the tea.

“Yes, he was very gentle. He loved the fact that I’m pierced, and he wants to see me again, although he has a request concerning my look,” replied Mia. “He wants me all in black and to look more Goth in makeup and hair.”

“Are you game?” asked Brandy.

Mia nodded.

“Cool! I know just the place to get your outfit. The only thing is that I get you in the same outfit,” said Brandy.

“I’d like that,” replied Mia. “He gave me oral, which was different. It’s the first time that a man has done that to me.”

“And how did it feel?”

“He was very good,” replied Mia. “Heather said that I would be popular while I’m in between. While I want to get SRS, I may put it off until I get tired of this job.”

“So you like being an escort?”

Mia smiled and nodded.

“There’s a thrill about it, it’s hard to explain. I also get to play in different roles,” said Mia. “My next two clients have special requests.”

The kettle went off and Brandy filled the mugs with hot water.

“And what are those?”

“One wants me to play his secretary, and the other wants me to dress and act like a prostitute,” said Mia. “He has a fetish for something out of Pretty Woman.”

Brandy laughed.

“Do you have your outfit picked out?” asked Brandy.

“Heather is getting it for me,” she replied.

“Do I get you in the same thing?” asked Brandy with a smile.

“Of course,” said Mia as she put some honey in her tea.

“I’m so happy to see that you’re getting this chance to be the real you,” said Brandy. “I mean, I like that you’re exploring your sexuality.”

Mia smiled back and she stirred her tea. “Well, I guess I’m just making up for lost time.”

“Well, let’s go cuddle on the couch and talk about that,” said Brandy with a wink.

Chapter 30

The next night was a girl’s night out with the women from the coffee house. It started at Brandy and Mia’s apartment, and the plan was to head out for drinks.

In addition to Vanessa and Leslie, there were several other women. All were very curious about Mia’s transformation, especially her breast surgery.

“They look so real,” said Gina, a graduate student.

“The surgeon doesn’t use implants, just fat distribution,” replied Mia. “He used the same process on my hips and butt.”

“Really?” asked Vanessa.

Mia nodded.

“They feel very real,” said Brandy. “Trust me on that.”

There was a round of laughter.

“You want to feel them?” asked Mia.

“Really?” asked Vanessa.

Mia nodded.

Vanessa, followed by the other women all gently touched Mia’s breasts.

“Wow, they really do feel real!” exclaimed Holly, a big breasted African-American.

“I may need to look this guy up,” said Gina.

“I can give you his name. He’s not cheap, but he’s worth it,” replied Mia.

“Cool,” said Gina. “I have to admit that you look great. You really made the right decision to be a girl.”

The others nodded in agreement.

“Are you still in school?” asked Vanessa.

Mia nodded.

“The college has been very accommodating,” said Mia. “My only real issue right now is with my family.”

“How bad?” asked Leslie.

“My Dad still considers me a fucking faggot; I can’t imagine what he’d do if he found out about the rest of my life,” said Mia. “At least my Mom is talking to me. She says that she plans on working on him. We talk once a week or so. She’s also helping me with my sister.”

“At least her brother is cool about it,” said Brandy. “He’s actually coming out this summer to see us.”

“That’s cool, but what about your sister? I mean I would think she’d understand,” said Holly.

“She has even blocked my emails,” said Mia. “It sucks, but I’m so happy now. I can’t believe how I repressed all this for so long. I just wish they’d listen to me and understand that I’m finally content. I’m not asking for their approval, just to try and accept me for who I am.”

“Do you think they’ll ever come around?” asked Holly.

“I think so, but I’m not going back to who I used to be. It wouldn’t matter anyway, because what can I say to them? That this was all a joke?” said Mia.

“Well, it’s their loss,” said Gina. “It’s obvious that you’re much happier than as a woman.”

“Thanks,” replied Mia.

“Well, let’s get going,” said Brandy. “We have some partying to do.”

Chapter 31

Later that evening, Mia and Brandy cuddled together in their bed.

“That was fun!” said Brandy.

“I agree,” said Mia. “I love how they all accepted me for who I’ve become.”

“You’re going to experience all sorts of people, Mia. There will those who accept you as you are, there will be those who will never see you as a woman, and then again, some will change their mind. There are also those who see you as someone exotic and exciting, like your clients. But there’s one thing you can count on, that is that I’ll always be there for you,” said Brandy.

“I truly appreciate that. I don’t think I could have gotten this far without your help and pushing. I also appreciate all the help Heather has given me,” said Mia.

Brandy leaned close and kissed Mia.

“I wish that your whole family could see how happy you are,” said Brandy.

“And I wish they could meet you,” added Mia. “I guess we have to take what life gives us.”

“Yes, but don’t give up, hopefully your family will realize how much you mean to them,” said Brandy.

“I hope so,” replied Mia as she snuggled closer to Brandy.

“Let’s make love,” said Brandy as she kissed Mia again

She reached over into the nightstand and took out the dildo with the attached sleeve. Heather had given them one of the devices as a housewarming gift.

“I’ve been thinking about making love to you all night,” said Brandy.

Mia let out a contented sigh. Her life had changed so drastically in the past few months, yet she couldn’t imagine it any other way now. Her life was far from perfect, but then again whose life was?

The End