The knock on the door brought Joe/Josephine back in to the present. Mike was yelling "What's taking so long?" Josephine was just finishing up. She stood up and inspected herself in the mirror. She looked like...A TV whore! Well that's what she was now. Her makeup was poorly done. Her wig was crooked. Other than that she looked pretty good. Her/his slight build looked hot in the mini skirt combined with stockings and a garter belt. "I would look so much better if I had some tits." She thought. She grabbed her socks and stuffed them in her bra. "That's better". She then opened the door and returned to her pimp.
Mike looked her up and down and nodded signaling that he liked what he saw. "Now get on your knees and suck me off!" he told her. She dropped, unbuckled his pants and took out his cock. She eagerly went to work on getting him off. It took a while but he finally grabbed her by the back of her head, thrust deep into her mouth and shot his load. She swallowed as much of his sperm as she could but some of it rolled down her cheek. "You will learn to swallow all of my jism or I will send those pictures to your wife!"
Mike pulled up his pants and said, "It's time for you to go to work". He then left the room. Josephine went into the bathroom and cleaned herself up. A few minutes later there was a knock at the door. Josephine opened the door and let the man in. He stepped into the hotel room. She dropped to the floor and unzipped his pants. She took out his cock and began to suck on it. He stayed limp for quite some time. She experimented and tried many different things to get him hard. She licked the tip of his cock like she did to Mike, but this didn't seem to work. She ran her tongue up and down his shaft but he remained limp. She took the whole cock in her mouth and sucked...still limp. She started to rub his balls with one hand while stroking his shaft with the other. Finally she was getting a reaction. His cock started to grow hard. She continued to stroke and rub. Licking the tip of his cock. The harder he became the more turned on Josephine became. She was getting hard as hell as she pleasured this man. After about 20 minutes of this he deposited his load in her mouth. He pulled up his pants and left. When he left so did her hard on.
Josephine again went into the bathroom to clean up. Just as she got to the sink and started to run the water, there was another knock at the door. She turned and answered the door. Another man entered. She dropped to her knees once again and took out his cock. She started this time by rubbing his balls and stroking his cock. No luck. This is not as easy as it looks. She went to licking the head of his dick. No luck. She moved her lips to his ball sack and took it into her mouth. BINGO! He was hard in a second and she wasn't far behind. He blew his load a few minutes later and was gone. So was Josephine's hard on.
The day continued in a similar fashion. One guy after another. Josephine trying to figure out what turned them on. Eventually she would and he would soon blow his load. She would get excited only to have him blow his load and leave her unsatisfied. As the day went on she got better and better. She was a fast learner. She was quickly becoming good at sucking cock.
Around 2:30 or so Mike entered the room and told Josephine that she pretty good for a beginner. He then told her to lose the panties and get on the bed doggie style. She did. He quickly mounted her from behind and began to fuck the shit out of her. Once again, at the beginning it hurt her like hell. After a while the pain turned to pleasure. Josephine was now hard as a rock again. Mike then flipped her over, put her legs over his shoulders and slid his cock deep in her ass. As he fucked her his belly rubbed up against Josephine's cock. It didn't take long for her to blow her load. She was amazed though, as her hot jism shot all the way up to her face. She opened her mouth and tried to catch her own cum in her mouth. When she was done cumming she quickly scooped up the rest with her hand and fed it to herself. Mike told her, "You are really becoming quite a whore. You love the taste of cum don't you?'
Josephine replied, "Of course I do and it's all you're fault!"
At that moment Mike knew he had her hooked. A few moments later Mike pulled out and gave Josephine some more of her favorite drink.
He got up and got dressed. He took a business card out of his pocket and told Josephine that instead of coming to the hotel tomorrow that she was to go to the address on the card and ask for Mistress Jasmine. He ordered Josephine to do exactly what Mistress Jasmine ordered. He told her that Mistress Jasmine will teach you how to be a woman. He then left.
Josephine then cleaned herself up, changed back into Joe and went home. Once home, he had a nice dinner with his wife. She asked him again if he would grow his hair long, reminding him how she was turned on by her business colleague. Joe realized that if he had long hair he wouldn't need to wear that awful wig he had on today. He made it seem as if he was doing Alexa a favor and agreed.
The next day Joe woke and was apprehensive about going to meet Mistress Jasmine. He took a cab to the address on the card. He got out of the cab and entered the store. It was a high class sex shop. One that had all sorts of clothing, equipment, toys, etc. But not the trashy type. He was looking around some when one of the sales girls asked if he needed help.
He said, "I'm here to see Mistress Jasmine."
The sales girl asked, "Mike's girl?"
Joe responded, "Yes"
The sales girl introduced herself as Amy and told Joe to follow her. She led Joe into the back room, up the stairs and into an office. Amy introduced Joe to Mistress Jasmine. She was stunning. Tall, blond with perfect tits. Joe desperately wanted to fuck her. She spoke in a commanding voice. "Mike asked me to teach you how to be a woman. If you listen and do what I tell you, you will learn to behave as a woman. Mike will be able to whore you out at a higher rate and I get a higher commission. Don't listen to me and you will be forever sucking guys off in that seedy hotel. Understand?"
Joe shook his head in the affirmative. "Good", she said. "Now strip!"
Joe quickly stripped off his cloths. He stood naked in front of Mistress Jasmine and her assistant Amy. "First you need to learn how to put on make up. Amy will teach you all of the tricks." Amy motioned for Joe to come and sit down in front of the mirror. Amy took great care in showing Joe how put on the make up. She applied it, showing Joe the techniques. When she was done you would have thought Joe was a woman. She then took off the make up and had Joe apply it. He tried his best but was not nearly as good as Amy. The entire morning they applied the makeup and took off the make up. Each time Joe did a better job. By lunch time he was getting the hang of it.
Mistress Jasmine then picked out an outfit of stockings, garter belt, panties, bra, a wig and a short dress for Josephine to wear. She showed Josephine how to put each item on. Once dressed Mistress Jasmine brought out the high heels. She would start with the 3 inch ones. Josephine slipped them on but could barely stand up. Amy showed her how to walk in heels like a woman. Josephine tried but stumbled all over the place. They kept at it and by late afternoon Josephine was really getting the hang of it.
They packaged up all of Josephine's stuff (stockings, panties, bra, high heals, dress and wig) and sent her on her way. Joe took the bag and began to think, "What am I going to do with these?" He rushed home and beat Alexa home by about 5 minutes. He quickly hid the bag, hopping that Alexa would not find it.
That evening was quite routine. Dinner, fuck Alexa, and go to sleep.
The next morning Joe woke and had breakfast with Alexa. He was hoping she would leave for work early so he could get to the hotel and take his time with his make up. He wanted to show Mike that he learned his lessons well. Alexa came into the kitchen and told Joe that she had to leave early. She had an early meeting with a big client. She apologized and left. Joe quickly went to retrieve his bag. He had hid it his closet. When he got to the closet it was gone! He started to frantically search all over the closet. As he moved through the closet he heard Camille say, "Is this what you are looking for?" He turned and she was holding the bag. She asked who the items where for. Joe didn't know what to say. Camille took the items out of the bag one by one. "Very nice stuff. Who's the lucky girl?"
Joe said, "You wouldn't believe me if I told you."
She said, "Try me!"
Joe came clean with her and told her the stuff was for him. She didn't blink when he told her his story. He told her that he likes to dress as a woman sometimes. That it turns him on. Camille was getting turned on by this and told Joe that she wanted to see him dressed. He told her that he didn't have time to show her right now but would in the future. Camille said, "Dress now or I tell Alexa everything."
Joe put on his make up and his stockings, panties, garter belt, bra, dress, wig and high heels. Camille was impressed on how well he did his make up. She then told Joe, "You make me so horny dressed like that! Fuck my asshole right now!"
Joe pulled off Camille's cloths pulled up his dress, whipped out his cock and started fucking her ass. He pumped her fast and hard. He had to get done quickly. He had to get to the hotel or Mike would be pissed. He quickly came. He apologized to Camille for cumming so quickly and began to undress. He saw the clock and realized he didn't have time to change back to his male clothing. So he decided to sneak out the back door dressed as Josephine and head over to the hotel.
He was relieved to get out of the apartment complex without running into anyone. He took a cab to the hotel. As he sat in the back of the cab with his/her legs crossed he noticed that the cabbie couldn't take his eyes off her. He was constantly looking at her in his mirror. She flirted with him and teased him by running her hand up and down her leg. Raising her dress just above her stockings. Josephine was really having fun with this and was upset when they reached the hotel. She paid for the ride and quickly ran up to the room.
Mike was already there. He was quite surprised when Josephine showed up all dressed up. He said, "I see that you like being a woman. Now get on your knees bitch!"
Josephine dropped to her knees and started sucking his cock.
The start of another beautiful day of sucking cock and swallowing sperm!