The Disguise

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Later that week they were to leave for another gig in Orlando the next morning and Jen told Angel he was unhappy with the false breasts. They looked and felt good but his chest was broken out in a bad rash from wearing them. He had made up his mind to look into having breast implants. He could always have them removed. Angel asked if he could afford that. He said he had a savings account that had enough in it to cover it.

They took a cab to the bank and Ted closed out the account and walked out with forty thousand dollars.

Angel said he should have no trouble having the operation done for that amount.

When they arrived in Orlando Ted went to a highly recommended Plastic Surgeon and the operation was scheduled for two days later. The operation went smoothly and Jen was very happy with her new look. She could wear more revealing and sexy clothes. No one would mistake her for a male now. The implants were supposed to be B cups but the hormones increased her own breast size and her breasts stabilized at C cups. She looked gorgeous. She loved to walk into stores and malls and feel all the eyes on her. She liked that men tried to date her all the time. She came close several times to accepting the offers of dinner and dancing. The fact that she had never danced with a man held her back.. She was not comfortable with the idea of a man touching her yet. She often thought about how it would feel to kiss a man. She wasn't ready for that yet either. Jen worked hard to perfect her transformation to a woman. Her disguise was virtually perfect. She became the manager of the act and ran the business effortlessly. The only thing she didn't handle was the booking and after eight months of running the act Angel wanted her to take that over gradually. Angel asked her to accompany her when they met with the agents. The agent's office was in Miami and Jen was impressed by the size of the operation and the manner in which they were treated. They were shown into a very large office and seated before a large desk by a very handsome gentleman. He appeared to be a young fifty years old. He was introduced to Jen as Bill Taggert, the agent. He told Angel they were getting wonderful reviews and that they had requests for them to book as opening acts for several big name acts. It would mean much more money but more travel. They would have to buy their own tour bus. He asked if Jen were part of the act. Angel said she wasn't but was the manager. The agent grinned at the two of them, "She has to be the most beautiful manager in the business."

"Thank you, kind Sir. But I can't sing or dance and I love being with my sister."

"She should let you introduce the act and be the mistress of ceremonies. No one would take their eyes off you when you were on the stage." They were given the information and details of the gigs that were in the future. The agent hugged and kissed them both and Jen hid a shiver that she felt when he held and kissed her. When they were outside she looked at Angel and said "He really turned me on. How could that be?"

Angel looked at her, "Sugar, you are almost a woman now and you are having a woman's feelings, you want a man."

"Oh! I think you are right. But I still love having sex with you and the girls."

"Right, but have you noticed that it is almost never intercourse any more, it is always oral sex."

"Really, I haven't noticed, but come to think of it, I don't remember screwing anyone for along time."

"Jen, I think it is time for you to think about going all the way with this sex change. You really love being a woman, will you ever want to go back to being a man?"

"What? I am a man."

"Are you? Look in the mirror." Jen walked to a bench and sat down. She stared off into the distance. After a few minutes she looked at her sister, "I can not imagine going back now. I love this. I can't give it up, ever. I will call the surgeon in Orlando and fly up there when they can schedule me."

A voice said, "Ladies, Jen I couldn't stand to see you walk out of my life. Jen, would you do me the honor of accompanying me to dinner tonight?"

"Why, Bill, I would love to, but."

"Yes she will, Bill, She is not busy tonight. We are at the Biltmore in the Grove. Room 246."

"Wonderful, I'll make reservations and call you. I am looking forward to this evening."

Jen stood and watched him walk away. She looked at Angel, "Can I do this?"

"Hell, yes you can, you will have a good time, he won't expect to get in your panties on the first date. Just be a woman who won't jump in the sack with just anyone."

Jen worried about what to wear all the way home. Angel grinned and said, "Now I know you are a woman, when you say you don't have anything to wear. You just bought that deep blue cocktail dress last week. It hasn't been off the hanger since you bought it. You bought shoes and lingerie to go with it. You will make him drool and trip all over himself in that outfit."

Jen's hair had grown to shoulder length and she didn't wear the wig any more. She often used a fall to wear a bun or long ponytail.

Jen took a long shower and dried off. She dusted with after bath powder and felt her body all over. She felt smooth and clean and she slipped on a pair of new blue hose and garter belt. Jen adjusted the snaps and checked everything was straight. She pulled new pair of matching panties and loved the feel as they slid up her legs. She stepped into her high heeled shoes and walked out where all the girls waited. They all said she was drop dead gorgeous. Angel hugged her and said, "Remember when you were a guy and you told me you saw a girl so beautiful your heart stopped beating for a while?"

"Yes, I remember that."

"That's how you look tonight. Slip into that dress and I'll help you with your hair and make up, God knows, you don't have to do much."

Angel just finished with Jen's makeup and she went to put things in her clutch purse. The phone rang and Angel picked it up. It was Bill he asked for Jen and Angel told him he was a lucky man. She said Jen looked absolutely smashing tonight. Bill said he was tied up with a client and was running late. He said he had decided they would stop for drinks then go to his house for dinner. He was sending a driver for Jen and would meet her at his club for drinks. Bill said the driver would be waiting in front of the hotel in ten minutes and would she please forgive him for not being there himself to pick her up. Angel told him she would pass on the message.

Bill Taggart stood talking to several of his friends in the bar of the Palmetto Woods Country Club when a hush fell over the room. One of the men he was with said "Jesus, Look at that. Another stood with his mouth open. Bill turned and saw Jen standing in the entry way to the bar. He was stunned by her beauty. He shook himself and hurried to her, "Jen, there you are! Wow! You are beautiful tonight. I love your dress. He reached for the short cape she had over her shoulders. As she leaned a little forward he got a glimpse of her perfect breasts when the front of the dress fell forward. It was a dress with shoulder pads and a plunging neckline that went almost to her waist where a belt closed the front of the dress. Her escorted her to a table and held her chair for her. When she was seated he took her hand and pressed it to his lips, "Jen, you are so beautiful it takes my breath away, and I deal with beautiful women every day of my life. They all pale beside you. Jen blushed and looked at him and said, "Bill, you are very handsome too! I am proud to be with you."

"Dear girl would you care for something to drink?"

"Yes, I would like a small glass of white wine, Please."

He raised his hand and a waiter appeared as if by magic." Bill gave him their order. "Dear Lady, I must apologize, I was delayed by a client who is a big pain in the butt. I wanted so badly to meet you myself, I thought this was the quickest way to be with you. She smiled at him and put her hand on his and said, "I forgive you, Bill, your Rolls was quite splendid, but I would rather have had you in person"

He felt a shiver go from her touch deep into his soul. He held her hand to his lips. "Never again will I let that happen."

" It doesn't matter, Bill. I just missed you."

He felt light headed, like a boy on his first date.

"Jen, the meal at the club is not at it's best on a Thursday night like this. I thought, if you don't mind we might go to my house and I could throw a couple steaks on the fire. I cook a mean steak."

She grinned at him, "That is the best offer I have had in a long time. Let's go."

They stood and he put her short cape around her shoulders. She smiled, "Thank you." He felt as if he were walking on clouds as she took his arm and held it tight, her breast against his arm. His car was waiting and they sat in back for the short ride. His house was magnificent, every thing was perfect. He helped her remove her cape and took off his jacket. "Come out on the patio, let me get the gas grill going." The patio was delightful. It was beautifully landscaped and illuminated. He sat her at a nearby table and told her he would get the steaks and things. She got up and followed him to the kitchen and helped him carry things to the patio. She made several trips while he started the fire. They sat and he held her hand while the fire heated up. The steaks were thick and well marbled. He put two foil wrapped potatoes on the grill as it heated. She stood and walked around the patio. "Would you like to see the house?" he asked.

"Oh! Yes it is quite lovely."

"It was just a pile of concrete until you walked in, Jen, You bring it to life."

"Why , thank you, but I feel you strongly here. It is your space. I do feel comfortable here though." They walked into the living room and Jen paused and looked at a large portrait of a lovely woman above the fire place. She looked at him and asked, "Is that your late wife?"

"Yes it is, perhaps I should have removed the picture before I brought you here." She turned and looked at him. "Why in the world would you do that? She was your beloved wife, she was part of you. I would feel terrible if you did that."

He looked at her with new respect. "Come on girl, lets check the fire." They went back on the patio and he put the meat on the grill. She walked to him and reached up and loosened his tie, "There you look better now. He walked to a stand and pressed a button and soft music filled the area. He held his arms out to her and she stepped in to them. They glided smoothly across the patio. She put her head on his chest and he buried his face in her hair." He stopped by the fire and turned the meat over. She moved back into his arms. He stopped again and she stepped back. Her belt buckle caught on his pocket and popped open. Her dress flew open revealing her in her garter belt, panties and hose. She pulled the dress together and turned away from him. He found the belt and took it to her. She looked at him with tears in her eyes, "I am so embarrassed, how can I face you?"

"Jen, you were the sexiest thing I have ever seen. I will carry that picture of you in my mind forever."

"Oh! No! Don't say that." she wept. "I am so sorry."

"Please don't cry, please stop. Let me hold you girl. You did nothing wrong. He held her in his arms then gently pressed his lips to hers. She pressed against him then pulled back.

She looked at him and put her hand to her mouth. "I think I had better go. That felt way too good."

"No! You haven't eaten yet. Please stay."

"All right. Feed me then, kiss me again, then you can take me home."

"You want me to kiss you again?"

"I really do. I wanted to be prim and proper for you. I don't kiss on the first date. But I liked it, it scared me I liked it so much. Oh! Please don't think I am being forward. I sound like a school girl. I don't know what you did to me."

"Sit down, the meat and potatoes are ready, I'll get the salad." He sliced strips off the steak and put them on plates and put the potatoes beside them. They ate dinner, his eyes never left her. She looked at him, "Why are you looking at me like that, Bill."

"Because you are beautiful, and I am praying your dress will fall open again." She stared at him, then a tiny smile started at the corner of her mouth. Then she giggled, "Was I funny?"

"Jen, you were delicious, just gorgeous. If you are finished let's move in on the couch where it is more comfortable. I'll get us an after dinner drink." Jen moved to the couch and he brought small liqueur glasses. They talked about the things they liked and didn't like, foods, music, TV, everything. He put his arm around her and she moved close to him. He smelled her hair, he forgot what he was saying. She said "you say you like purple cows?"

"Yes, I do."

"Bill Taggert, you are not paying any attention to me at all."

"I am paying attention to how your hair smells and to how much I want to kiss you again."

"Then please do it." The kiss started as a gentle soft kiss, then her tongue brushed his lips. Both mouths opened and their tongues met and rubbed together. Her arms went around his neck. His hands moved down her back. She pushed him away and said, "we must stop now. Please."

"Why?"

"Because of this." She put her hand on his throbbing erection. "I want it but I can't have it right now."

"I don't understand?"

"Dear Bill, I am deeply attracted to you. I have never felt an attraction this strong in my whole life. I want you too. But we just met today. There are two things that say no. One, the short time we have known each other, I could easily ignore. The second, which is a physical problem I am cursed with, I can not ignore. I am scheduled for surgery in two days. If it is successful and when I am healed, I will be pounding on your door and I will drag you kicking and screaming to the nearest bed where I WILL have my way with you. If it doesn't work, you will never see me again." Tears coursed down her cheeks. "I know this is not fair to you, I just don't know what to do."

"Let me help you, let me be by your side. I can't stand the idea of never seeing you again. I won't have it."

"Bill, something else I must tell you is that I will never be able to have children. I will understand if that changes how you feel."

"It changes nothing in the way I feel. You are not just trying to get rid of me are you? I know I am way too old for you."

"No, No, don't say that, I don't know how old you are, I have never even thought about it, I don't care how young you are. Oh! No. You are not too old."

"Where are you going for your operation?"

"Orlando."

"When do you have to be there?"

"It is scheduled for Saturday morning at 6."

"Here is what I want to do, is Angel going with you?" Jen nodded. "OK, I will have my private jet take us to Orlando tomorrow afternoon. I have nice apartment we keep there, we will all stay there, my limo will take us to the hospital. Angel and I will be by your side." He held up his hand, Don't say a word. I WILL be there no matter what you say. My whole life depends on this too!" I have fallen in love with you and until you say you don't want me I will be there for you."

"Oh! Bill, that is the sweetest thing anyone ever said to me. But you don't want to be saddled with a nonfunctional woman. That is not fair to you, I will not do that to you."

"You haven't said you don't want me."

"I can't say that, I am trying, but I just can't say it."

They arrived at Bill's Orlando apartment and it was as impressive as his house. It was a four bedroom penthouse overlooking the city. Jen and Bill had clung to each other on the trip from Miami. Jen wanted to wait on Bill hand and foot and he wanted to do the same for her. Finally Angel put her foot down. "Look you guys, knock off this silly business of seeing who can do the most for each other. It's not going to work. It's not a contest to show who loves the other the most. Bill, just let Jen cater to you now, she needs to do it now because she knows she might never have another chance. After the operation Bill, you will have plenty of time to take care of her. The doctor said she cannot move at all for several days, then she will be restricted as to what she can do for another week or so."

Angel went to her room early and Jen and Bill sat on the patio and looked out over the city lights. They could hear the city traffic below, but found the evening peaceful and warm. He held her close to him and they talked the evening away until Jen said, "Dearest, I must get some sleep. Five o'clock is going to come early."

Bill lay in his room looking at nothing but seeing Jen. He heard his door open and saw her walk to his bed. She stood looking down at him, he smiled and held the covers open, "Come on in, it is warm in here. I saved you a place."

Jen smiled, "I hoped you would, can I hug your back?" He turned his back to her and she slipped in beside him. She moved until she was touching him the length of her body. She put her arm over him and caressed his chest. She loved the curly hair there. He wore only pajama bottoms. She let her hand move down him until she reached his waist band. She found the bow knot closing the draw string to his pajama bottoms and pulled it open. She slipped her hand down his flat corded stomach and reached his pubic hair. He drew a sharp deep breath. Her hand searched for and found his erection. He gasped as her fingers closed around it. She moved down and rubbed it against her cheeks, whimpering softly as she felt the satiny softness of the head. "Will you think I am horrid if I kiss it?" she asked.

"No, I will think you are very sweet. I will love anything you do."

Jen put her lips around the top of his cock and savored the taste of him. She could not believe she was doing this. She was still a man. The desire to please him and to fulfill her own desires was overpowering. She took as much of him in her mouth as she could. She couldn't believe the pleasure she felt from having his member in her mouth. She wanted him inside her. That could not happen now so she was going to have to settle for this.

She ran her tongue over his penis and licked every inch of him. She buried her face below his cock and loved the smell of his balls. She gently pulled one of them into her mouth. He threw his head back and groaned. She stopped what she was doing and asked, "Did I hurt you, Bill."

"Hell No! It was heaven, wonderful." She sucked in the other ball and held it in her mouth running her tongue all over it. Jen caressed his shaft with her hands and lubricated it with her mouth. She licked the spot just below the head where the big tube on the bottom entered the head. He moaned and twitched. She grinned to herself. 'A good spot.' She spread her lips over the head and moved down the shaft with her lips as far as she was comfortable. She loved his cock, it was just the right size, her nose was almost in his pubic hair when the head hit the bottom of her throat. She started a slow up and down motion and felt him stiffen even more. She moved faster, closing her lips tighter around the shaft. She thought he was about to cum so she grasped him with her fingers following her lips with her hands, twisting them back and forth. Bill was moaning constantly now. He jerked and she felt the tube under his cock start to spasm. The first spurt of cum hit the back of her throat and startled her. Spurt after spurt flooded her mouth. She pulled slowly up his pulsing cock and loved the taste of his cum. She didn't let a drop escape. She swallowed it all. She licked ever bit of his cock until it was cleaned of all his juice. She moved up and placed her lips softly against his. After a long sweet kiss she whispered, "Did I please you a little, Bill. I did my best, It was the first time I did that to a man."