Tracy – Finale

By Pamela

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My wondering what the future would bring next was answered the following day. I awoke amongst the girls that were sleeping in Tracy’s bedroom. I felt like I was one of them. Clearly not a girl who was a friend of Tracy’s but a girl, nonetheless. I had to wait until the girls had peed before I was allowed to. Some of them took advantage of my availability for licking their vaginas clean. A couple were on their periods and I helped them with their tampons and pads. I knew I’d be having a full day ahead of me doing the laundry for everyone, cleaning and cooking the meals. I hoped that there might be some time when the girls wanted me for their pleasure. I wouldn’t even allow myself to imagine that Tracy would want to fuck me again. If I knew that she wanted to, then I wouldn’t complain at all if she tied me up like she had done the day before.

By the time I was done peeing and washing up, the girls were heading downstairs to await the breakfast that I would make for them. Coffee, juice, whatever style egg they wanted, cereal or English muffins. I had slept in my bra and before Tracy joined the others she said, put on your pretty dress and petticoat and pantyhose. "Then I want you to run over to your house to see if there have been any messages from our parents that we ought to know about. When you come back you can make us breakfast."

I was not surprised that Tracy would have me go to my house wearing a dress. If I was seen by someone, would that matter to Tracy? After I had dressed I walked quickly to my house holding my skirts and was pretty sure no one had seen me. All was quiet inside except for the beeping of the answering machine that indicated that it had one message. I pushed the button to listen. The message had come in at midnight which seemed odd to me. A gruff man’s voice said, "This message is for Greg from Officer Scanlon of the Felt County police department. There's been a car accident involving your parents and another couple. You need to call us as soon as possible." A number was given that was the area code of the ski resort.

My first reaction was to not believe what I heard. Could it be a prank? I listened to it again and wrote down the number on a piece of paper. It definitely did not seem phony and a rising fear began filtering into my mind as I imagined that some terrible tragedy had happened. My parents were injured? How badly? Would they be in a hospital somewhere? What should I do? What can I do? The more I thought about the call the more terror gripped me. It would have to be Tracy's parents that were the other couple. I’ll have to get her to call. She’ll know what to do. She always knows everything. Tears began to stream down my cheeks and now I ran in my dress back to Tracy’s house.

I burst in on her and the girls and they turned to look at me. I desperately tried to speak coherently but with my sobbing and wailing the words came out in fragments. Tracy got up and had me sit next to her on the sofa. Julie sat down on my other side and Laurie, Jody, Alicia, and Abby came over. For the first time ever Tracy talked to me plainly. She said, "Sit down Greg. What's happened? Take a deep breath. Calm down."

"There’s a message on the answering machine. Call this number." I handed the paper with the number to Tracy. "I can't call. I'm too scared. It's the police. There's been an accident. Our parents were in the car!"

A telephone was on the table next to Tracy and she dialed the phone number. Julie put her arm across my back. I was shaking and she squeezed me gently to help calm me down. We listened as someone answered the phone and Tracy asked to be connected to the person who had left the message at my house. After a minute of waiting, we could hear a voice greeting Tracy. She listened for a long time. Every so often she said, “I see” or “Oh my God.” I felt I was near to panicking. Tracy's face got sadder and wearier during the conversation. At one point she reached out an arm and put it around me and pulled me tight against her. Her eyes were glistening as if she were about to cry. I knew that whatever had happened it was beyond terrible. I continued to sob and Tracy held me even tighter. Tracy said, “I understand. Greg’s to be responsible. Yes, that should be fine. I know you are. Goodbye.” She hung up the phone. She sat silently holding me now with both of her arms. She cried and sobbed and tears ran down her face. I felt Tracy’s chest pushed against mine. Any second I knew that she was going to say something that was too horrible to hear. I cringed as she pulled back to look at me in the eyes. Her face was contorted in grief and tears. It seemed unimaginable that I could ever see Tracy like this.

"My grandma died and when the message arrived with my parents, they had to pack up and come home. There was fresh snow on the road and their car swerved to avoid a deer and slid over an embankment. It fell fifty feet onto a rocky ledge."

"Oh, my God! How are they?"

Tracy spent some time trying to get control of her voice in between her sobs. "Both our dad's died in the accident.”

“No! No!” I cried out and covered my ears with my hands. “Don’t tell me!”

“I’m sorry Greg. I have to. Our moms were taken to the hospital in very bad condition and then they both died also."

Now everyone was crying. Tracy and I were sobbing with unimaginable grief. Abby, Jody, Julie, Laurie, and Alicia were crowded around Tracy and me crying and sobbing.

Abby fetched a box of tissues and one by one we took some and blew our noses. After what seemed an eternity, Tracy said, “I’ve got to finish saying what the policeman said. Our mom's before they died told the doctors that they wanted Greg and me to take care of each other in case they died and we became orphans. We're old enough to live as adults according to state law. Since Greg is now seventeen and older than me, our mom’s thought that he should be declared the primary responsible adult.” Tracy looked at me and said, “Ordinarily, Greg, I’d want to go along with their wishes, but clearly that’s not feasible. Our moms were unaware of the dominant role I’ve played in your life. The only realistic way to proceed is for me to be responsible for you. I’ll take care of you. I’ll make sure that you’re fed and clothed and housed. I’ll protect you and provide for your happiness. You’ll be my little charge, my baby, my little daughter. Do you understand?”

“Yes, Tracy,” I said.

“Good. You’ve accepted the fact that you’re my bitch so now I want you to think of yourself as being both my daughter and my bitch. Rest assured I’ll always have your best interests at heart.”

“Thank you, Tracy.”

“We’re going to be crying a lot more in the days and weeks to come. Grieving is a process that takes time. We both loved our parents. They were good people. So we’ll just have to let our emotions come when they come. But my little one, if you’re ever very sad or scared then you can always count on getting comfort from me.”

“Thank you, Tracy.”

“And we too,” Abby said. “Both of you should know that we’ll do anything for you girls.”

“You’re the greatest friends a girl ever had,” Tracy said.

Laurie and Jody squeezed onto the sofa so I was snugly sitting between Julie and Tracy. Abby and Alicia sat on the floor in front of us. I alternately cried and blew my nose as the reality of my situation increasingly fell upon me. At one point I said, “I’m so thankful Tracy that you’ll take care of me. I don’t know what I would do without you. I would be so scared. I love you Tracy and all of you girls, I love you all so much.” I completely broke down and wailed with pain and anguish.

“We all love you to,” Tracy said.

Hearing those words after all I had experienced as her bitch put my mind into a surreal zone of hope for the future. I could not be happy now, for sure, but knowing that I was loved by Tracy and the other girls gave me a path forward that would one day help me out of my grief.

***

After a while, a couple of the girls got up and made coffee and poured some orange juice. Tracy said, “Good idea. We need to eat if we’re to stay strong in the next days and weeks. Come Greg, you need to have some breakfast. We all do.”

When breakfast was over I resumed my place on the sofa and the girls made sure that they surrounded me with their love and affection. Tracy had numerous phone calls to make in order to begin the process of straightening out our lives. First order of business was arranging for the bodies of our parents to be sent back to our town and to be cremated. We picked a date for a memorial service to be held at the funeral home.

Tracy contacted our parent’s friends and the sparse, distant relatives of both of our families. Tracy spoke to a lawyer to arrange for our acquiring official custody of ourselves and for collecting the estates we inherited from our respective parents. Tracy had occasional lapses into grief and I had a steady simpering sadness and crushing hurt that stayed with me all day and into the evening.

The girls shopped for Tracy and me providing food for a week. They made us lunch and then later dinner. When dinner was over and the kitchen cleaned we gathered in Tracy’s bedroom and put on our nighties. I lay next to Tracy who put her arms around me again and held me. Whenever I cried, she’d get a lace hanky and dab at my eyes. She and I were surrounded and enveloped by the other girls. The girls talked in soft tones with Tracy and I slowly drifted off to sleep. I caught some fragments of conversation in which they talked about my future. Apart from some reference to me moving into Tracy’s parent’s bedroom and selling my house I was too drowsy to understand anything.

***

Over the next few days, Tracy and I came to grips with our mutual tragedy so that aftershocks in which we spontaneously wept became less and less frequent. The first few nights after we had gotten the news about our parents Tracy had me sleep in the bed with her. She was amazingly tender with me. She was a new Tracy. Not the stern and sometimes cruel dominatrix that had shaped me into her subservient and loving bitch. I felt like I was her daughter and she sincerely wanted to take care of me and keep me safe. On the fifth day, Tracy said it was time for me to move into the bedroom next to hers as I had been anticipating. “If you’re ever going to grow up to be a big girl, then you have to learn to sleep in your own bed and have your own room. I’m not saying that some nights I won’t let you sleep with me. We’ll keep that possibility open – and certainly on the nights when you’re scared and need to be comforted.”

I wanted to give Tracy a hug but was afraid to touch her. I said, “Can I hug you, Tracy?”

She looked at me slightly surprised and then said, “Yes, you may.”

I couldn’t get over how nice the new Tracy was to me. I would have gladly been her bitch forever, but being her daughter was even better. It was ironic that it took my becoming an orphan and Tracy my mom, for her to show some kindness towards me.

“All of my mom’s clothing will be yours together with your mom’s clothing. Together you’ll have a formidable collection of bras, panties, girdles, slips, stockings, pantyhose, corsets, body suits. Really, anything you can think of in the lingerie department. There are also many filmy and sexy nightgowns of different colors. I can’t count the number of dresses, skirts, and blouses you now have to choose from. You also have the two beautiful wedding dresses that our moms were married in. There are dozens of pairs of shoes from flats to stiletto heels. There are many perfumes to wear, make-up, handbags, and everything else.”

I was especially happy that I could wear my own mom’s clothing. It would make me feel closer to her spirit. Especially wearing her bras and girdles would allow me to enter into the most intimate part of her being. I hoped that she was up in heaven and could look down and see me in her clothes. It might bring her joy.

Tracy continued, “We’ll hold onto some of your boy outfits if for some reason you need them. For example, you’ll have to meet the social worker as Greg, and until that happens you’ll be going to school dressed as Greg.”

“So later I’ll be wearing a dress to school?”

“I’m sorry. I wasn’t clear. After the social worker approves our living arrangement you’ll drop out of school. There’s no point in you going since your life will be devoted to taking care of me, my friends, the house, and anything else I need done. You’re old enough to legally quit school. I suppose you can take the GED exam if you’d like.”

I thought about what Tracy said. “What do I have to say to the social worker?”

“Make it clear that you’re the responsible adult around here. You’re 17 now. At 18 you’re legally an adult, but the state will tolerate our living arrangement for a year to keep us out of the foster care system. Just don’t mess up.”

“What would happen?”

“Probably take you away from me!”

“That’s terrible! Will you help me prepare?”

“Yes. Once we know when they’re coming. I’ll coach you.”

***

My first night in my new bedroom the girls joined Tracy at my bedside as she was putting me to sleep. Tracy came over and kissed me on the forehead and sat down next to me on the bed. “Are you ready for nighty-night?”

“Yes, Tracy,” I said.

“That’s a very pretty gown you’re wearing,” Tracy said. “It was a favorite of my mom’s.” I could hear Tracy’s voice choking up.

“It’s the prettiest gown I have. It has the loveliest shade of pink and the fabric is so soft. The ruffles on the shoulders are a favorite of mine.”

Tracy collected herself and showed me a book that she had been holding. It had a funny picture of a young girl on the cover. The title suggested that the book was sort of a guide for young girls that are growing up and into puberty. “I want to read to you every night before you go to sleep, Greg, now that we’re going to be living together. Would you like that?”

“You know I’ll love that Tracy!”

“Good. I picked out a book that’s good for moms and their daughters to read together. It tells about the changes that go on in a girl’s body when she enters puberty. I know that you know a lot already about bras and periods and lots of things that girls do, but it’ll be good for you to relearn these things the way girls normally do. This also serves as a useful way for me to fully get into the role of your mother and you into the role of my little girl.”

“But I’m still your bitch?”

“Yes, as I said. You’re always going to be my bitch. But now when it suits me you’re going to also be my daughter.”

“I understand.”

Tracy began reading the story to me. The other girls sat around me on the bed. The story was about a nine-year old girl, Debra, who was dreading the changes to her body that would soon be coming. After some puzzling about what could be bothering her daughter, Debra’s mom realized that she must be seeing the changes in other girls in her class and the time had come for her to tell her about what to expect. I found the story mesmerizing. I wished that I could be Debra and then I realized that I already was Debra in a sense. We both had moms that wanted to teach us about what happens to girls as they become women.

When Tracy was changing pages, I said, “I’m like Debra, aren’t I?”

“Yes, Greg, you are.”

“Can you call me Debra? Can you change my name to Debra? Or do I always have to be Greg?”

Tracy looked at me for a minute thinking and said, “What do you think girls? Should we call Greg ‘Debra’ from now on?”

“I think it’s a great idea,” Abby said.

“If she wants to be called Debra, then I think we should,” Laurie said.

“She’s like a little niece to all of us,” Jody said, “so calling her Debra makes perfect sense.”

“Then it’s settled,” Tracy said. “From now on you’ll be Debra.”

I was so excited and happy that I clapped my hands together and thanked everyone! Tracy resumed reading the story. Debra asked questions of her mommy. “When will I need a bra? Do I wear it every day? What kind of bra will I have to buy? Will my breasts grow to be big? Is it bad if boys see my bra? Will milk come out of my breasts? What is a period? Why will I have a period? Do boys have periods? Do periods hurt? What are tampons? What is pubic hair? Will I have hair in my arm pits?” Debra asked lots and lots of questions, and Tracy made a joke at one point about putting tape over her mouth. But Debra’s mother patiently answered all her questions. By the end of the book, Debra had grown more and more confident that she understood the changes that were coming to her and that she’d be able to deal with them without being afraid. I was very sleepy by then and Tracy kissed me on the forehead again and turned out the light. She then said, “One minute” and she left and then came back holding a soft doll in a pretty dress that was about a foot and a half high. “Take my old dolly for comfort,” she said and helped me tuck it against my chest with my arm around it. “I’ll leave the door open an inch so you won’t be afraid.”

“I love you mommy.”

“I love you Debra.”

Then she and the girls left the room. I held the dolly tightly against me and noticed that it had a faint perfumy smell.

Lying in bed I let the thought that I was Debra percolate through my mind. It was nice to have a name that fit my identity. Tracy’s daughter. My mom had been replaced by Tracy. I felt sorry that now that I had a mom, Tracy didn’t. That was terribly sad. On the other hand, if there was anyone I knew who was strong and independent and very smart, it was Tracy. I felt inspired by her self-confidence, by her seeming to always know what to do in any situation. It’s amazing how Tracy knew me inside and out from the moment I went to fetch her panty that the wind had blown out of her laundry basket. She could see my need for her to control me, especially to fulfill my need to be useful for girls. She was so generous with her time to allow me to lick on her pussy and that of her friends. To allow me to help them with their periods and to help make their lives easier by doing the chores for them. In all of these things, Tracy always knew to do the right thing for me. And then the party where she somehow knew that I could be the lynchpin in keeping the boys satisfied after the girls had gotten tired of their inexperienced love making.

I remembered back to how she had tied me down knowing that it was the perfect preamble to having my body to ravish for her own pleasure. She understood how to get the biggest boners out of me and to keep them hard for the longest time. And now, finally, she saw how I would make the perfect daughter to her. Here I’ve gone from the greatest sadness in my life, to the greatest happiness!

***

When I returned to school after the holiday break, my teachers and classmates had heard about the tragedy that had befallen me and Tracy. They bent over backwards to be helpful to me. The few times I felt a need to cry everyone was respectful of me. The truth was that all during classes I longed to be Debra. That was who I was now, for good or bad. I became anxious for the visit of the social worker to be over so I could begin my new life. I wanted to be Tracy’s daughter Debra and take care of Tracy’s needs. My ambition was to become a homemaker of sorts. Tracy would provide for me the way a husband might and I would take care of the domestic chores. If she were ever to give me a baby to take care of, then I’d be glad to do that for her.

A few weeks later we received a letter concerning the visit of the social worker. It was to be in the late afternoon on a school day. Tracy had me put boy clothes on top of the girl clothes in my dresser so they would be hidden. In a portion of the closet we put some boy clothes, and if I was asked about the many dresses hanging there I was to say that they were our mom’s. We will donate them to a charity when we are fully done with our grieving..

When the social worker showed up, she asked me just a few perfunctory questions. Her main interest was in convincing herself that Tracy was comfortable with the arrangement. Tracy dressed in an uncharacteristically prim dress with a high collar and acted as if she were a chaste and modest young lady. The house was immaculate and I’m sure we both made a great impression on the social worker. A few weeks later we received a letter announcing that I was now Tracy’s official guardian until she turned eighteen. It outlined resources we could take advantage of financially and otherwise if we ran into economic or other difficulties. In fact, with the sale of my parent’s house and some modest life insurance policies, we had a cushion against hardship for a couple of years. After that, we’d have to come up with a plan.

The girls came over to celebrate Tracy’s and mine official freedom. “Now that no one is going to be looking in on us,” Tracy said to me, “it’s safe for you to settle full time into your new role around the house.”

“Gladly, Tracy. Tomorrow I’ll drop out of school. I’m looking forward to being Debra all the time.”

“Now we can store away your boy clothes. Gather them up tomorrow.”

“As soon as I come home from school.”

***

When I announced that I was dropping out of school the guidance counselor was initially upset, but calmed down when I explained that I’d get my GED. The way I figured it, I’d actually be ahead of my classmates and could start community college a year earlier. I did feel a bit anxious about leaving school, mainly because I doubted that my parents would have approved of that. But Tracy was my mom now, and I wanted to please her, so there was nothing that I could do about it even if I wanted to. Surely my parents would understand why I’m happy to devote my life to Tracy. A girl as beautiful and charismatic as her deserves my devotion.

Now that I was home all the time, I was able to settle into a routine in which I made breakfast and dinner for Tracy and sometimes lunch. I did the laundry and cleaning. With her encouragement I learned how to sew so I could take care of any loose hems or missing buttons. Tracy showed me how to take care of her shoes and I looked forward each month when I could take each of her heels one by one and polish them. I gave the same care to her clothing. Keeping it neat in her drawers and closet. Ironing the clothing that needed it.

To be able to go shopping, Tracy and the girls worked intensively with me on clothing and makeup so that I would readily pass as female. A key part of my outfit was a padded girdle that gave me a woman’s ass along with large silicone breasts. My figure in a tight dress or even with jeans and a tee shirt would never be mistaken for a man’s. My hair had grown out fully by this time so it was a simple matter to create a hairdo that accentuated the girlishness of my face. After some practice around the house and then out into the nearby neighborhood I summoned up my resolve and went to the grocery store to shop. I used the newly installed self-check lane to avoid close attention from the checkers. I wasn’t sure if they could see the Greg lurking behind my girlish persona, but I didn’t want to risk that they could.

About once-a-week Tracy invited me to spend the night in her bed. I think she really enjoyed the role of mother and it was fun for her to pretend that she was giving her little girl a special treat. I treasured these nights because they helped to sate my never-ending desire to be with Tracy and to see and touch her body.

When I was in bed relaxing and looking at Tracy my heart would be filled with love and admiration for her. She might be working on her laptop, and while she did she might reach out with her hand and encircle my penis. The pleasure would be intense and I would quietly close my eyes and let Tracy do what she wanted to do. Once she told me that holding onto my cock helped her to study. I thought that was pretty fortunate for me.

Invariably my cock would develop a boner and Tracy would begin stroking it. She could both stroke my dick and work on her computer at the same time. She’d put some spittle on her palm and work her hand up and down on my cock causing me great pleasure. Like everything Tracy did, her skill in massaging my cock was exceptional. I quickly lost control of myself and moaned and cried out in ecstasy. She knew how to control the speed of her hand so that it systematically brought me up closer and closer to an orgasm until I shrieked and spewed out into her hand.

While cleaning me up, Tracy said, “It’s fun to play with your dick. Especially the jerking off part. I’m going to offer it to the other girls to play with. Some of them could use practice in jerking guys off.”

Tracy wasn’t going to get any complaint from me about that!

“Jerking you off has made me a bit horny, but I’m tired. In the morning we’ll figure out a way for you to pleasure me.” She closed her computer and turned out the light.

“Okay, Tracy,” I said, and whispered, “I love you.”

She didn’t say anything and I spent some time wondering how Tracy would use me for her pleasure in the morning. While I entertained these thoughts I fell into a deep sleep.

***

I woke up the next morning and looked over at Tracy sleeping next to me. Her face exquisitely beautiful and my heart pounded with my love for her. While staring at her she awoke and noticed me. Her eyes locked on mine and she said, “I remember now that I went to bed horny. Playing with your dick is a lot of fun.”

I watched Tracy’s face as she seemed to be thinking. Then she got up out of bed, took her nightgown off over her head and then took off panties that she was wearing. She went to a closet and returned with a large thick beach towel. She pulled the blanket off of me and told me to stay on my back. She arranged the towel underneath my head and shoulders and said, “That should do it.”

I had no idea what she was up to, when she said, “I have to pee badly, Debra. It’s been a whole night. But I’m also terribly horny. I think that before I pee I had better take care of my horniness.”

“Can I help?” I asked even though I knew the answer.

“I think so. I need to rub my vagina and clitoris on your face until I cum. That should do it.”

“I love doing that. I could lick your vagina all day long if you let me.”

“I know.” Tracy got up and straddled me with her legs and slowly brought her vagina to my lips. “Go ahead and lick me. I’ve got to be careful not to pee.” I used my tongue to hungrily lick Tracy’s labia. Almost immediately she pushed her vagina down a bit harder onto my lips and slowly moved her hips up and back. “Damn. I’ve got to pee something awful,” she said as she steadily rubbed her pussy over my mouth. “Oh, God, I really have to pee.” Tracy was getting more and more worked up and excited by sliding her clitoris against my face and pushing down. She moved it a bit faster and said, “It’s so hard to keep the pee in. I’m really trying, Debra. I don’t want to pee. I’ve got to hold it. Hold it. Hold it.” She shoved her vagina even harder onto my face and now flung it up and back dragging her clitoris and vagina over my lips. “My bladder is bursting Debra.” She rubbed herself harder and harder and now loudly called out, “I’m sorry, Debra, it’s hard to keep it in. I’m trying. I’m trying.”

Then while her hips and vagina vibrated up and back over my face, Tracy began peeing on me in small bursts. “I’m sorry! I’m sorry! I’m trying to keep it in! You understand?” Small hot jets of her pee shot out onto my mouth, lips and nose and ran over the side of my face onto the towel. Tracy got further and further wound up in her pleasure and ecstasy in a way that I had never seen before. It was clear that rubbing her pee swollen genitals against me caused an incalculable escalation in her pleasure. She kept at it, squeezing her pussy against my face with her urine soaking me and herself while moaning and apologizing for her lack of bladder control. Then, an extremely powerful orgasm took over her entire body and her loins trembled for a half a minute as she kept yelling “Oh, God, Oh, God, Oh, God.” When she was done she sat over me panting and attempting to catch her breath. I thought she was done, but to my surprise she resumed her use of my face to stoke her pleasure. This time it didn’t take her long to reach a second massive orgasm that was accompanied by a strong stream of pee as her body shook. She grabbed the towel, pulled it out from under me, wiped the pee off my face and tossed it across the room onto the bathroom floor. She collapsed on top of me and rolled to my side. “I couldn’t control myself, Debra.”

“I was thrilled to be able to help you.”

“I’ve wanted to do this for the longest time. It creates impossibly powerful climaxes. Your cute face is so perfect to rub against.”

“I’m happy that I could be of help, Tracy.”

***

In the weeks and months that came, Tracy completed her senior year in high school and applied to college. I enjoyed taking care of the house, cooking, shopping and otherwise being available for Tracy’s needs. Monday through Friday we were together before and after she was at school. Tracy was a straight A student with the ambition of going to law school and most evenings she took care of her homework and studying before she partook of the services I could provide. I learned that her pee fueled cunnilingus was reserved usually for the morning when she woke up. She preferred having a full bladder if she was going to get that pleasure from me. Occasionally if she drank a lot of coffee and just happened to be horny she might call me into the bedroom for an impromptu orgasm. I didn’t mind putting down my vacuum cleaner or mop to lie in her bed and let her use my face as she saw fit.

I continued to miss my parents terribly and every so often an aftershock would roll through my mind and I’d cry. Tracy was astute enough to offer me comfort during these times by holding me and making me feel loved. I also was extraordinarily happy that I could be a big part of Tracy’s life. She did start dating after a few months and even bringing guys back to the house. She introduced me as her roommate Debra on these occasions. Sometimes I’d make a dinner or pack a picnic basket for Tracy and her date. The times that she took her boyfriend into her bedroom and closed the door were the hardest on me. I could hear her muffled screams as she orgasmed and I’d imagine that the guy was having intercourse with her. I knew that my life will always have to fit around hers. Tracy is a free spirit who passes through life living exactly as she wants. I was meant to serve her and to be happy for the times I did get to have intimate contact with her.

At the end of the school year Tracy was valedictorian of the high school. She had been accepted in the local university on a scholarship. Tracy handled all of our money and she said that for the summer we should have a swimming pool with a privacy fence around it put in the backyard. She envisioned that it would be fun for her and our friends to lie about the pool sunning themselves and cooling off in the water during the long hot summer days. I’d be welcome to join them in either my bikini or my one-piece bathing suits.

Tracy said that to afford the pool, I would have to get a job. Otherwise we’d be in danger of running out of money. The one obvious marketable skill I had was being a maid, but Tracy thought that that would not provide enough income to live the way she wanted to.

Tracy brought the girls over one night to brainstorm solutions. One idea was to rent out some rooms. That might take care of the mortgage but Tracy wasn’t enthusiastic for sharing our lives with strangers. I was just returning from the kitchen to deliver beers to the girls when I saw they were looking at me. Tracy said, “Debra, after some thought, we realized that you have a marketable skill that could solve our financial problems. A skill that should more than enough pay our expenses and allow us to stay living here.”

“That’s great news. What’s my skill, Tracy?” I said, not having any idea what she was referring to.

“You’re gifted in pleasuring women and men. Do you remember the party just before our parents died? You gave a blowjob to Tom that he talked about for months afterwards. Also the hand job you gave John changed his whole life. The girls and I will find you customers that will pay you to do whatever they prefer. It could be fucking, or blowjobs or hand jobs. Really anything.”

“You really think I’m skilled enough to do that?”

“Absolutely. The girls and I have even brainstormed a pricelist for your services.”

“Pricelist?”

“Yes. For example, a simple hand job on a boy will be $50. A hand job with some licking of the penis would be $75. Complete blow jobs start at $100. Addons raise the price. For example, sucking the balls also, add $15. Cumming into your mouth add $20. To have you restrained generally doubles the price. Blindfolding you is extra. Treating you roughly triples the price, though no marks are to be left on you. We’ll also entertain special requests and figure out the price when we hear what the customer would like to do.”

“Can I wear my pretty dresses while I work on the boys?”

“Of course. You’re Debra! They might want you wearing just a bra and panty or have on a garter belt and stockings. You never know. Some boys might want you to pretend that you’re a boy and even have you dress as a boy.”

“Will there be girls who pay for me too?”

“I was getting to that. We’re not expecting a lot of business with traditional fucking. Except perhaps with married women looking for a little diversion. They’d pay $150 for a fuck if they’re on top and extra for you on top. Licking on their pussies will be $50, but if they want you to make them cum then we charge $25 per orgasm additional. Probably we’ll have to have a time limit. Some women are harder to please than others. You don’t want one that’ll take all day.”

I imagined how tired my jaw might become. “I hope I can please the women.”

“A good part of the business is likely to be fantasy reenactments. Girls and boys will pay for an experience that they can’t get with their regular partner. Guys might want a blow job because their girlfriend refuses to do it. Girls might want to tie you up, whip you and otherwise dominate you. These are things that many guys would not let their girlfriends or husbands do to them. In the same way, some girls might want to pee on you. We’ll have to charge a lot for that. The thing is, for a price, we’ll have you do kinky things that couples are reluctant to do for each other.”

“How much money do we need to make?”

“A few thousand a month. Of course it’s tax free.”

“Girls who refer customers get a 10 percent kickback. You’re liable to get tips which you’ll give to me. This has a great chance of solving our problems. It’ll pay for my tuition at law school and keep a roof over our heads besides keeping us well fed. When I graduate law school and land a job, we can think of shutting down the business, unless you want to keep it up.”

“When will this start?”

“As soon as possible. I’ll manage your calendar to set up your schedule. It’ll vary day to day by what the customers want. You’ll also have to change sheets after each customer. There will be quite a bit of extra laundry. Do you have any questions or concerns?”

I thought a minute and said, “What if one of the boys or girls wants to hurt me?”

“They’ll be told what the limits of their fantasies may be. If one of them gets overzealous we’ll take care of them. There will always be someone in the house while you’re working so you’re not alone. Having said that, some customers might get off watching you suffer psychologically. For example if you’re tied up and so forth. In those cases I expect you to allow yourself to be swept up in their fantasy so they get the fun they’re seeking. Physical pain is only allowed within reason. Playful whipping, nipple tweaking, that kind of thing.”

The girls talked long into the night plotting how they would set up the business and find customers. I went to my room to sleep. On the one hand I was quite pleased that I’d be the one to enable Tracy to go through college and law school. On the other hand I was terribly scared that I wouldn’t be very good at what Tracy thought I was good at.

***

I didn’t have to wait long to find out if my skill was up to the level that Tracy thought it was. Two days later I got my first customer. It was a shy college student named Ernie who had never had a woman touch his penis. For fifty bucks he was desperate to get past this bugaboo. He elected also to pay extra to cum into my mouth. He thought that it would be a step toward getting his first blowjob. His only preference in how I should dress was that I should be as pretty as possible, so I made sure to have on a party dress with my full crinolines.

It was a bit awkward when Tracy ushered Ernie into my bedroom. We both knew what he was there for but we initially acted like we were on a blind date and had to introduce ourselves to each other. I realized that it was my job to make him feel comfortable so I said, “Sit on the bed Ernie and relax. Let me help you take off your pants.” I undid his belt, button and zipper and he stepped out of his pants. He was wearing black boxers underneath and I could see that he was already excited in anticipation of what I was about to do. I pulled down his boxers to his ankles and he kicked them off and sat on the bed. “You can sit up or lie down, whatever you like.”

“I’ll sit up so I can watch you do it. That excites me.”

I sat back next to him and tucked my skirts away from his penis. It was about half erect now with a downward bend in it. “Can I put my arm around you?” Ernie asked.

“Sure Ernie.”

“Thanks.” He reached his arm across my shoulders and held me. I’m pretty sure that his touching me caused his penis to stiffen a bit more. It was now almost straight and pointing up. He had his legs spread so that it wasn’t hard to lift up his cock and see his balls. I held them in one hand while grasping his penis with my other.

“Damn that feels good. I wish Carol could do this. She’s my girlfriend but she won’t touch my penis. I’ve asked her many times to beat me off but she just won’t do it. I’m glad that you don’t mind touching my dick. You really understand what to do. Right now I’m jumping out of my skin with pleasure.”

Ernie’s cock had reached its longest and straightest extension and it was a relatively easy matter to slide my lubricated hand up and back making sure the sensitive areas got some nice attention. I even put in a little twist of my hand which invariably caused Ernie to moan in pleasure.

“What do you think of my cock?” Ernie asked me.

“It’s a very nice one,” I said.

“No really. What do you think?”

“It’s pretty big and kind of thick also. That probably sets it apart from other dicks.”

“Is it beautiful?”

“Definitely, Ernie. The first time I saw it I knew that you had an especially attractive penis. Your balls are very impressive. They’re nice balls. You’ve got nice balls. You should be proud of them. I like touching them and holding them. Letting them gently fall through and around my fingers.”

Ernie gasped at the pleasure I was giving him. “Keep talking. I’m desperately trying not to cum this quickly. You’re so good you’re driving me to the edge. Your talking helps distract me so I won’t cum just yet.”

“Like I said, Ernie, you’ve got great balls, but your penis is the best. Holding your penis is really holding a significant cock. I mean it’s so long it’s like I wonder if I’ll ever reach the end when I stroke it with my hand.”

Ernie laughed. “You’re humoring me.”

“No. You’ve got the kind of cock that girls absolutely hunger for. Imagine how they’ll feel when you slide that big, straight thing of yours up their pussies?”

“I wish you would tell Carol that.”

“But you still see her even though she frustrates you?”

“Oh, yes. I’m crazy about her, but she doesn’t want to be rushed.”

“I don’t know how she can resist this beautiful cock of yours.”

“Thank you, Debra. You’re the best. Now I think you better finish me off. It’s so fucking great the way it feels.”

“OK, Ernie. You want to cum into my mouth, so I’ll scoot down and get my face ready to receive your effluent.” I slid down and positioned my face a few inches from his cock and returned to rubbing on it. I picked up the pace establishing a rhythm in which the pleasure continued to grow from one stroke of my hand to the next. I could see that Ernie was seriously leaking pre-cum. I slid my hand faster and faster to capture the wave of pleasure as it ran toward a climax. I don’t really know why I sensed exactly when Ernie was about to cum, but I did and was able to open my mouth and move it directly in line with his rigid and swollen cock just as a large jet of bright-white semen shot directly into my mouth followed by a half dozen more.

“That’s so great!” Ernie said, “Don’t swallow yet. I need to get a picture.” He got his phone and took a picture of my open mouth filled with cum. “I’m going to show this to Carol. It might convince her to go the next step with me.”

“Really?” I said.

“It shows that she’s missing out on all the fun.”

“She might get jealous.”

“I don’t think so. She encouraged me to come here.”

I gave Ernie a ratings sheet to fill out. Tracy said that this would be a way of making sure that I tried my best with the clients.

***

After Ernie had left, Tracy came in to find out how it went. “Ernie said he’s very pleased and gave you five stars. You seem to be off to a great start.”

“Thank you, Tracy.”

“Your next appointment is in an hour. Remember to change the sheets. If you need to change your outfit I’ll let you know.”

And then all of a sudden I realized what was happening. I don’t know why I didn’t fully realize sooner what Tracy’s moneymaking scheme was all about. I guess it was the starkness of how I had to stay in my bedroom and have random people come in and have sex with me. The truth was that I had become a whore and Tracy was my pimp. I debated whether I should say anything to Tracy. I was scared of getting her angry with me. Finally I knew that I had to say something, so I said, “I’m a prostitute, right?”

Tracy stared at me for a long time. It seemed like she was thinking what to say. Finally she said, “You’re right. I don’t feel great about it, but there’s no other option here is there? Either you earn us some money, or I lose my future. When I’m a lawyer, I’ll make enough money for you and me to live luxuriously. So, eventually your sacrifice will pay off.”

“I think you misunderstood me. I didn’t mean to imply that it’s bad that you’ve made me a whore. If that’s what it takes to pay for you to go to college and law school, then I’m more than happy to do it. I just hadn’t fully realized that I was becoming a prostitute. As long as my experiences are good, like they were with Ernie, then it’s actually kind of interesting to have different sexual encounters with men and women.”

“I’m glad you said that. You’re a wonderfully sexy and responsive girl. I do believe that you can give our customers a lot of pleasure. Why shouldn’t you have the opportunity to do that? Of course, I hope that you allow yourself to take pleasure from your experiences. Did you enjoy playing with Ernie’s cock? If so, take full advantage of that. You have my permission and blessing.”

As always, Tracy could see further than I could. While I was now a whore, I should try and get pleasure from each of my encounters. That was an interesting proposition. Maybe for some of them it would be easy to take pleasure. For others, I had doubts. I didn’t mind rubbing on Ernie’s cock for example, and I even felt a sense of pride in my skill. But was it pleasure? It would never be as pleasurable as when Tracy used my body to fuck me or to rub her pussy on my face or even just to hold me. It was those moments that made it all worthwhile.

***

An hour later a girl named Molly who had been in some of my classes in high school entered my room through the open door. She was a bit thicker boned than Tracy’s friends and she was not especially attractive, though she was very well endowed.

She looked me over and said, “You used to be a boy, didn’t you? We went to school together.”

“Yeah.”

“I remember. You dropped out.”

“I got my GED.”

“You quit school to be a whore? That’s weird, but to each his own, I guess. Tracy says that I can have access to your penis for an hour.”

“What would you like me to do?”

“It’s really kind of cute the way that Tracy dresses you. It’s like you’re her little sister? Am I right?”

“Yeah. Tracy wants me to be pretty and I like being pretty.”

“I dressed the way you are and had tea parties and played with my dollies when I was about four or five years old.”

“Tracy and her friends like me being a little girl. I’m happy to do as they wish.”

“I guess as long as you like being a little girl it’s cool. Anyway I’m really curious to see what’s inside your panties. How do we get to them inside your skirts?”

“I’ll take off my girdle and stockings and then I can pull down my panties.” I unhooked my stockings and carefully took them off. Then I undid my girdle and wiggled out of it.

Then Molly said, “Hold up your skirts and I’ll pull down your panties.”

I gathered up my skirts and held them while Molly carefully pulled down my panties. “Oh my God,” Molly said and laughed. “So that’s what a penis looks like. It’s a funny looking thing, isn’t it?”

“I don’t know about funny. I admit they do look kind of odd.”

“I guess it’s limp now right? I mean that’s not it’s full size, is it?”

“Yes, it’s kind of limp right now. It will get bigger when it gets stimulated.”

“You mean a boner?”

“Yeah.”

“How can I get you to have a boner?”

“There’s different ways. You can touch it in the right spots, or you could do something sexy. When I see girls in their underwear or naked I can often get a boner from just looking at them.”

“Really? Boys are that simple?”

“I’m afraid so.”

“What else gives boys boners?”

“Some boys get boners when girls are tough on them. Order them around, tie them up, hit them. Things like that.”

“What about you?”

“I guess maybe.”

“That’s interesting. Maybe in the future I’ll try that. For now, I’ll take my skirt and top off and see if that gives you a boner.” Molly stripped down to her bra and panties. Both were white and rather plain. Her large bosoms were pretty exciting to look at. I liked the way her bra had to contend with keeping them up. She stared at my penis which grew a little because it was erotic to see her in her underwear, but it wasn’t exactly the kind of view that would arouse me to a boner.

“I think you got a bit bigger, but that’s not a boner is it?”

“You’ll know a boner when you see it. It’s quite rigid.”

“Why doesn’t my underwear give you a boner?”

“There’s no lace. It’s kind of plain. I respond strongly to lace. Look at my bra and panty. They’re much prettier than yours.”

“Interesting. So if I go out with a boy I should wear pretty underwear?”

“Yeah. It could help a lot if you take your clothes off. I also think girls can feel good about their bodies when they wear pretty underwear. I think boys can feel the same way in nice boxers.”

“I’ll try and get you a boner using my hand.”

Molly proceeded to touch my penis in a variety of ways. I talked her through what would make me feel good and she turned out to be a good listener. She worked on my shaft assiduously bringing it ever closer to cumming. Tracy had reminded me that Molly was paying 50 dollars per hour for giving me a hand job. If I was to cum, then she’d owe another 20 dollars.

“You’re getting me close to cumming, Molly. It’s kind of amazing what a fast learner you are.”

“Thanks, Debra. It’s just that I’ve been psyched to learn about penises. If I make you cum, then I have to pay an extra twenty dollars?”

“Yeah. I think that’s what Tracy wants.”

“I’d like to stay the full hour, but won’t get you to orgasm. Could you let me know when to stop?”

“Sure. Actually, you better stop now at least for a few minutes.”

Molly stopped sliding her hand on my cock and I felt myself returning from the brink of cumming.

“Can I keep touching it?”

“Yes. If you don’t want it to get close to cumming again, then avoid the end of my penis. You can play with the rest of it. That feels good. You can play with my balls if you like, though you should be gentle with them.”

“What about your prostate?”

“Yeah that’s a source of pleasure, but you know where the access is?”

“Is it up your asshole?”

“Yeah.”

Molly opened up her purse and took out a long relatively thin, white plastic vibrator. “I’ve got my vibrator with me. Can I put it up your asshole and see what it does to you? What does that cost?”

“Tracy never mentioned a charge for that. I guess it’s free.”

“Good. I’ll turn the vibrator on your prostrate and hold your penis at the same time.”

“You probably ought to lubricate your vibrator.”

“Of course. I have some lotion with me.”

“It might make me lose control of my cumming.”

“Do I still have to pay if I don’t want you to cum but you cum anyway?”

“I don’t know.”

“We’ll sort that out later. Right now I’m anxious to see what the vibrator does to you.”

Molly covered her vibrator with a lotion and turned it on. It made a low buzzing sound and she felt around with it until she hit my rear hole and then gently began working it inside me. I just about leapt out of my skin. The pleasure was new and intense and Molly laughed seeing what a powerful effect it had on me. Then with her free hand she grabbed a hold of my boner and began stroking me. The two complimentary pleasures caused my hips to rock back and forth as waves of pleasure ran through me from both sides.

“How’s that? Molly said.

I made some strange gagging sounds as I battled to not immediately cum.

“Does that mean it feels good?”

I nodded my head.

“Go ahead and hold my breasts, Greg,” Molly said.

I put my hands over the cups of her bra and felt her large boobs. It was too much for me. I closed my eyes and felt myself squirting semen everywhere as my entire body shook with pleasure. I had to worry about my heart, my spasming was so intense.

“My God, Greg, you’ve got your stuff everywhere.”

“I’m sorry, Molly.”

“I still have ten minutes left.”

She took her vibrator out of me and turned it off. Then she held my now exhausted and shriveled penis in her two hands.

“It’s such a sad little thing now.”

“That’s what happens.”

“How long until it revives?”

“Probably a few hours. By tomorrow it’ll be in good shape.”

“What happens if you have a customer after me who wants to play with your dick like I did?”

“I guess they’d have to get a raincheck. I’ll ask Tracy about that.”

“This has been fun Debra. I think I’ve learned so much that I didn’t know before.”

“Thank you. I’d love for you to come again!”

Molly hesitated and asked me, “Does Tracy allow you to have a girlfriend?”

“I don’t think so. She wants me to always be available for the clients. But I also love her and I don’t think there’s any room in my heart for someone else.”

The hour was up and Molly got dressed, gave me a hug, thanked me again and left. I cleaned up my semen and changed the sheets. Tracy came up to my room to get a debriefing. “Molly put a vibrator up my bottom,” I said.

“How did that go?”

“It felt good. I mean it felt very good.”

“I’m glad. You have to expect that some women may want to use your bottom as if it was a vagina.”

“They will?”

“Yes. They tie a penis on themselves and force it into your bottom as if they were fucking a girl. When the time comes you’ll see. Any other issues?”

“Molly made me cum. We were wondering what would happen if another customer wanted me to cum on the same day?”

“Good point. We’ll schedule just one orgasm a day for you. Anything else?”

“Molly asked me if I’m allowed to have a girlfriend. I said that I didn’t think so. That’s right, isn’t it?”

“Obviously, you can’t. You have to always be available if someone wants to pay for your services. Besides that, we can’t give away for free what others are paying for.”

“That’s what I thought, too.”

Tracy looked at me as if having a second thought and said, “I can say this much to you, Debra. I’ll make a greater effort to take advantage of you myself. I’ll get you in my bed more often and I’ll find more occasions where I can tie you down and fuck you. How’s that?”

“That would be wonderful, Tracy!”

“Good. I do appreciate your devotion. It’s going to get me through college and law school.”

***

The next client that Tracy scheduled was two days later. It was a middle-aged woman who wanted me to play the role of her sixteen-year-old nephew. I was to refer to her as Aunt Charlotte. “I’m not sure what she’s got in mind, though she intends to fuck you by the end of the hour. She asked me if that was okay.”

“I’ll do my best,” I said. Then I added, “Can an aunt have sex with her nephew?”

“It’s the woman’s fantasy. It’s not real. You’re not her nephew, are you? Just remember to act the part that she wants you to be. It’s important in a fantasy to be just right. Any deviation from what the customer needs can reduce the quality of their experience.”

By the time the woman showed up I was nervous. Would I be able to act and improvise so as to make the woman happy? I was lying on the bed when precisely on time, a woman wearing an expensive form-fitting tailored black dress, stockings, and high spike heels strode into the bedroom. Her fingers were perfectly manicured with red nail polish and I couldn’t help but notice her extraordinary figure, from the swell of her breasts down to her beautifully arching butt and onto her gorgeous stockinged legs. She closed the door behind her and stared at me smiling. As per her instructions I was dressed as a boy.

“So Eric, which of my bras do you want to wear today?”

“What bras to you have?”

“I packed four bras in my suitcase for the trip. Two white, one black and one pink. I’m wearing the blue bra now. Which bra would you like?”

“The pink bra.”

“That means you get my pink panties to wear.”

“Thank you, Aunt Charlotte. You’re the best aunt a boy ever had!”

“That’s sweet of you to say. What kind of aunt would I be to not help you out? Your parents will be away for four days and you’re entitled to have some fun during that time.”

Aunt Charlotte handed me the matching pink bra and panty. “You have the prettiest lingerie, Aunt Charlotte. I think we have the same taste.”

Charlotte laughed. “I know we do.”

“You’re the only woman I know that doesn’t get haughty when she finds out I want to wear a bra and panty.”

“What women act haughty?”

“I went to the bra section in the department store and I saw a pretty bodysuit and when I brought it up to the desk to pay for it, the saleswoman who was about the same age as you are, gave me a scary look. I said the bodysuit is a present and she said, “No, it’s not. You’re planning to wear it. You should be ashamed of yourself. A young man buying himself a woman’s bodysuit.” I left the bodysuit that I wanted so much on the counter, and ran away. I began crying and felt ashamed of myself.”

“You tell me what bodysuit and I’ll buy it for you.”

“You’re so special, Aunt Charlotte.”

“Now put on the bra and panty. I want to see how you look in them.”

I took my clothes off and put on the bra and panty.

“My oh my, Eric. You are pretty. What a wonderful lithe figure you have. Your skin is blemish free, smooth, and hairless. You’re all girl. If the truth be told, you remind me of one of those very pretty young women that appear in porno films that I’ve seen. You’ve got that bouncy, sweet energy. You’re the kind of girl that enjoys a dick. Sucking them, sucking the balls, licking them, taking them inside your pussy. Am I right?”

I laughed and said, “You’re making me laugh Aunt Charlotte. I love being pretty. I can’t stop men from desiring me.”

“I’ve got a tartan skirt for you to wear also.” Aunt Charlotte handed it to me and I put it on.

“You’re so pretty that women will also find you irresistible.”

“What about you, Aunt Charlotte?” I giggled. “Do you find me irresistible?”

“I do.”

Aunt Charlotte reached behind her neck and undid the zipper of her dress. “I’ll take off my dress. I want you to get up close and personal with a woman who finds you adorable and sexy.” She slid the dress over her head revealing her blue bra, matching blue panties and pantyhose. Her bra was working overtime to hold up her substantial breasts. Charlotte stood in front of me and put her arms around me and pulled me in close to her. She was a few inches taller and her body was much more substantial than mine. Between her large breasts and womanly butt I felt almost small next to her.

“How do you feel?” Charlotte asked me.

“I feel a bit overwhelmed by you!”

“Would you like to have sex like a lady?”

“What do you mean? How can I do that?”

“I’ll be the man, which makes sense since I’m larger and stronger than you. That frees you up to be the girl. How’s that?”

“I think I would adore being made love to by you in which I’m the woman.”

“Good. So give me a moment.” Charlotte took off her pantyhose and went into the bathroom and a few minutes later she came out with what looked to be a penis having a lifelike boner emerging from where her vagina sat. Whatever was holding the penis up was hidden by her panties.

“Your boner and balls look just like that of a man,” I said.

“Duh,” Charlotte said and laughed. Before I could say anything she added, “Turn around and bend over the bed.”

“What’s going to happen?” I asked.

“I’m going to fuck you from behind. It’s one of the basic sex positions. Do you watch nature shows? Now face the bed and bend over. I’m going to give your pussy a treat.”

I wasn’t exactly sure what Charlotte was up to until I felt her hand feeling around in my crack. There was a sound like sputtering from a tube and I glanced backwards and saw that Charlotte had covered her penis with a lubricant. I looked down at the bed and nervously awaited what Charlotte was going to do. I felt her place a leather belt around my neck and then pull back on it slightly choking me.

“Okay, Eric. Since you’re a virgin and not used to this, relax. We’ll go slow. My dick will easily slide in. It’s flexible and not as thick as you might think. Relax and you’ll enjoy it. Don’t fight me.”

“I won’t Aunt Charlotte,” I said in a tiny voice. I felt Charlotte pull down my panties to my knees. Then I let out a kind of squeaky sound as the end of Charlotte’s dildo pushed into my asshole.

“Here we go, my darling. You’ve got the prettiest vagina and ass. God, it’s so hot. I want to fuck you all day long my pretty Eric.”

After my experience with Molly’s vibrator I had some sense of the sensations that were about to rain down on my prostate during Charlotte’s conquest of me. She pushed the slippery dildo up into me slowly so that there wasn’t any pain and my butt relaxed and adjusted quickly to the onslaught. As she bore down on me, she steadied herself by pulling on the belt that was around my neck. I had never felt so helpless in my life. I had no way of resisting my neck being choked and my bottom being attacked. I had lost all control of the situation. Charlotte had turned me into a receptacle for her fantasy. Once she had put the dildo in as far as she wanted to go, she released her choke hold and pulled back part way. A second later she pushed her penis back in. She continued the motion until a degree of fluidity developed and a rhythm was established. I felt her hand on my shoulder pushing me down into the bed. The force shoved my face into the bedding with my butt up in the air. While she worked her penis in and out of me I heard her moaning. Though I didn’t know the details, her device obviously included a mechanism for rubbing on her own clitoris so that not only was she overwhelming my prostrate with intense feeling, but she was getting herself excited and heading to orgasm.

My own cock was pushed against the bed and rigid. Pleasure pulsated through my whole genital area. I became comfortably relaxed with the pounding that Aunt Charlotte was doing to me. It was a nice feeling to think that she was using me to pleasure herself. I enjoyed my feeling of helplessness. The thought of her control over me was exciting. Suddenly my mind jumped out of the fantasy and realized that what I was feeling here I often felt with Tracy. I loved being her receptacle. I loved my helplessness around her. I loved my dependency on her.

We went on like this for a while until Charlotte gasped, grunted, and shook with an orgasm. She pulled back leaving me folded over the bed and said, “Wait here.” She went to the bathroom and came back without her penis. “Lie on your back,” she said. She climbed over me and fed my boner into her pussy and leaned forward pinning my hands to the bed. She began fucking me slowly. “Here’s pretty Eric getting herself fucked.”

Even before I came close to cumming Charlotte had gone into another orgasm and groaned loudly. She stopped for a second and then resumed slowly. “Okay. Give me one more orgasm. We’ll cum together.”

Her hips worked herself up and back on my cock at a furious pace. “Cum now, Eric. Now! Now!” she ordered me. I felt myself getting closer and closer to cumming while at the same time I was worried that I would fail Charlotte. Her demand for my orgasm was not helping me get one and then Charlotte smacked me on the cheek yelling “Cum now!” Her slap had the effect of forcing me to concentrate on the intense pleasure in my penis and a second later an orgasm burst out of me. Charlotte rode my spasming cock until it collapsed and fell out of her.

Charlotte got off me and sat on the edge of the bed. “Look at that Eric.” She pointed to a prodigious amount of whitish cum leaking out of her vagina. “Get over here and clean me up. I don’t want this wetting my panties.”

I got up and kneeled in front of the bed and slurped up the cum that was leaking out of Charlotte’s vagina. “Good girl, Eric.”

“Thank you, Aunt Charlotte.”

***

Tracy was especially interested in my debriefing of Charlotte’s time with me. On her way out of the house, Charlotte had told Tracy that she was quite impressed by my ability to adlib the part of her nephew. “He’s a natural,” she told her. “Without missing a beat he was an adorable submissive teenage nephew. I can’t tell you the thrill I felt having my way with him. I’m going to become a regular customer around here.”

“Charlotte said that she’s entirely pleased with her time with you and will be coming back regularly.”

“I tried my best.”

“It paid off. She loved your ability to improvise the role of her nephew.”

“I just followed her lead.”

“Did she fuck you like she said she was going to?”

“Yes, at the end. First she put on a penis and had sex with me through my bottom hole.”

“Really? Did that hurt?”

“Not really. She was pretty gentle with me. She made it slippery and was very slow at first. I guess I have to say that it felt very good. Like Molly used her vibrator up my bottom hole and that felt good. It’s sort of the same thing.”

“Well, I guess we’re off to a great start with our business. I’ve got a blow job for you in a couple of hours. In fact, next week I’ve got a half-dozen blowjob bookings. Even Ernie wants to come back with a friend. You’ll give Ernie a hand job while he gets to watch you give his friend a blow job. Can you do that?”

“I guess I can.”

“We’ll have to charge a supplement for all the extra effort. I think the hard part will be for you to concentrate on both at the same time, instead of focusing on them one at a time – which would lead to a lot of frustration.”

“I’ll do my best, Tracy.”

“I know you will. My first tuition payment is due in a month, and I think that we’ll have the money by then.”

“That’s great.”

***

The man, Leo, who had booked a blowjob for that afternoon was in his fifties. To greet him I was once again wearing my dress and otherwise returned to my usual feminine state. When he entered the room, he looked it over and then examined me. “You’re pretty enough. Debra? I think Tracy referred to you as Debra.”

“Yes, I’m Debra.”

“Good. My dear departed wife loved to give me blow jobs until she ran away with a college student twenty years younger than her.”

“So she’s not dead?”

“I’m sorry. I keep saying she’s departed when I mean she left me. Divorced me. Anyway, you’re much prettier than she is. It’ll be nice to have a pretty girl give me a blow job.”

“I hope I’m as good as she was.”

“I’m sure you are. I’ll just pull down my trousers, sit in this easy chair and kick back. Tracy says that you have a half-hour to get me to cum.”

“True. First thing I’m supposed to do is wash your penis in the sink. Is that okay?”

“Sure. That makes sense.”

We went into the bathroom and Leo lowered his trousers and stood in front of the sink. I turned on the hot water, soaped up my hands and washed Leo’s dick and balls. The cock in front of me was a lot older than John’s, Tom’s and Ernie’s, the only ones I had ever seen up close previously. The pubies had some gray in them and the skin looked more aged. It lacked the smooth complexion of a young dick. I rinsed off the soap and dried his cock and balls with a hand towel and we went back into the bedroom.

“Do you want me to swallow your cum?” I asked.

“You can if you want to. I don’t mind if it just squirts over your face. You probably don’t want it in your carpet or on the chair. I hope you remember that during the cumming you must continue to stroke my dick until the last drop is out.”

“Of course. I know that’s important.”

With that I got down to the business at hand. Considering the blowjob I did at Tracy’s party, this would be my second attempt. Nonetheless I felt a degree of confidence that I’d be able to get Leo to shoot off in a reasonable amount of time.

While I worked on Leo’s cock I thought about my future. I’d clearly be giving many blowjobs, which meant that I’d be meeting many men. Lots of penises one after another. No two would look identical as far as I knew. I suppose that eventually I wouldn’t even notice or think about the particular cock I was having to suck on. Focusing back on Leo, his dick had gotten hard and he was moaning in pleasure. I varied my rhythmic sucking to stir him up a bit more and massaged his balls for a few minutes. He was in good shape for an early orgasm and my mind drifted off now thinking about the many women that will hire my services. Old and young, thin, and curvy. I can’t begin to imagine the range of sexual desires that they will have and use me to achieve. Many vaginas and breasts. All the different outfits they’ll be wearing. Each new woman would be like a Christmas present to be unwrapped so as to see what’s inside. Same with the men. You have no idea what someone’s penis looks like until it’s revealed. What about the physiques of the men? Some might be musclebound. Others might be undeveloped. Tracy has three years of law school that I’ll pay for through my sex work. After that, what will happen? Once Tracy gets a job will she still want me to be a whore?

Leo’s loud moaning distracted me from my thoughts. He was getting close to cumming. I studied his penis while I again sucked on his balls. It was a red, stiff rod now and somewhat fatter. It had the special look that penises have when they’re at their most aroused state. There’s a kind of raw, biological power as if one is watching the essence of evolution in real time. This is mating the way nature intended it. The entire universe focused on this hot, obsessed cock ready to unleash a torrent of wiggling sperms within a vagina to begin a stampede for the magical egg. Only in this case the sperms would be finding the mouth that surrounded and sucked Leo’s erstwhile cock. I knew that Leo was now about to shoot off and I sucked his dick carefully hitting all the right spots and attempting to get it as far inside my mouth as I could. I was making a gagging sound punctuated by gasps of air when Leo shoved my head all the way up to the base of his penis. I could tell that his cock had found a place partially down my throat. While I was struggling to breathe, Leo let out a whoop and what seemed like an unending gallon of cum filled up my throat and the insides of my mouth. When the spasms were over and before I suffocated I pulled his rigid organ back out of the opening he had found for it.

“Oh, good golly in heaven!” Leo said. “My wife could never do that. You’re amazing Debra.”

I enjoyed receiving the complement as I preoccupied myself with swallowing the cum that was filling my mouth.

“Five minutes left,” Leo said.

“You’re very responsive,” I said.

“Perhaps, but you have a gift for blowjobs.”

“Thank you.”

“Would you mind if I felt you up for a minute. Your chest is so enticing to me. My wife wasn’t a big fan of me touching her boobs.”

“Sure Leo. I don’t mind.”

Leo put his hands over my boobs and felt them. He sighed with contentment. Then he snuck his hand inside my dress to feel my boobs over my bra. “I better stop here. Believe it or not I can feel a little rise in my penis. You’re such a pretty girl, Debra. I hope to see you again.”

“Please do come back. You’ve got a nice penis. I think he and I can become good friends.”

Leo laughed as he left.

***

The next day was quiet and at dinner Tracy said, “You must have really done a great blowjob for Leo. He was raving about you when he left. How did it go?”

“He sat in the chair and I sucked on his penis. He’s a nice guy and I was happy to have given him some pleasure.”

“I think you’ve shown beyond any doubt that you are quite talented in pleasing both men and women. Your improvisational skill is amazing. We’ve quite a few reservations coming in now. I’m sure that’s by word of mouth. We’re going to easily earn enough to pay our bills. In fact, I’ll be putting some of the surplus money into a fund to pay for my law school.”

“I’m so happy that I can help you, Tracy.”

“That’s one thing about you that I’ve always loved though perhaps never fully appreciated. The fact that you take so much pleasure in pleasing me. I think for a long time I thought that it was because you’re afraid of me. But I now see that your fear comes from worrying that I’ll cast you off. The truth is that you love me so much – even to the point of worshipping me – that there isn’t anything you won’t do in order to be in my life.”

“From the first time …”

“Let me finish. From the first time we met I treated you like my servant. I continuously found new ways to degrade you and humiliate you, yet you never wavered in loving me. I made you my dog on a leash and made you do tricks. Then I made you my bitch, then my girl bitch. I dressed you as a little girl. I made you give a hand job and a blowjob at the party. I made you lick our vaginas clean. I punished you for disobeying me. Yet, through all of this you loved being with me. Then we were orphaned and our shared pain brought us close together – rather I should say it made me develop true feelings for you. I hate the thought that you lost your parents!”

Tracy was overcome by emotion and I went over to her and rested my hand on her shoulder. “May I?” She nodded her head and I held her.

Tracy regained her composure and said, “And now I’m your mom and I’m taking advantage of your love for me by having you be a whore.”

“I really don’t mind. There’s nothing I wouldn’t do for you.”

“Mark my words, Debra: a time will come when I’ll repay you for all your generosity and love!”

Now I wept like a baby and Tracy held me.

***

While Tracy was in college for four years I performed too many blowjobs to count. I had my regular penises to contend with and got to know them and their quirks very well. Then there were the many one and done penises for guys who just seemed to want to have a great orgasm. Most of the men preferred me in my pretty dresses. Some in just lingerie. Some wanted me nude even though it made clear that I had a cock of my own. Some men insisted I beg them to suck their dick. Others pretended like they were forcing me to suck it. Some tied me down and put their dicks in my mouth. Some men insisted on shoving their entire dick down my throat, others didn’t care about that at all. After a while I’d seen every fantasy possible and it would be quite an unusual blowjob it if it deviated from the many scripts I had seen before.

I have to say that I got very good at blowjobs. I’d wash the dicks off in the sink then before they knew it I had them erected and on a steady march to cumming. I can’t remember one man that I couldn’t bring to orgasm with my mouth and tongue. My tongue was a genius at rooting out the exact nerve endings on a cock that were key to triggering it to shoot off. I suppose I’ve swallowed enough cum to gain weight. Some days felt like gallons and gallons of cum. I suppose that was because some men orgasmed with a dozen squirts worth of cum. Others might have just a small trickle. One never knew what was coming until it came.

I gave many hand jobs during this time. This was always easy work except for the occasional man who never would get really hard and could not be coaxed over the edge. This was frustrating to me. Besides my hand getting tired, I couldn’t figure out what I was missing. Some of these men had enough empathy for my plight to take over and do the final rubbing. In a minute I’d have the cum shooting out onto my face and mouth. Others left without an orgasm hoping to get a refund from Tracy. She’d give them a small discount and then lecture them on not properly preparing for me. She bet they had beaten off before coming to the house.

The thousand women who hired me over four years brought with them a thousand vaginas and two thousand breasts. Besides that a thousand bras and panties. I never tired of meeting the women and helping them to get the experience they craved. They fucked me. I fucked them. They put any number of dildos and vibrators up my butt. They dominated me. They demanded that I treat them like sluts. They abused me and loved me. They had me be anywhere from a tiny baby to an old father or grandfather. I could go on and on.

Over four years I’m sure that I heard the orgasmic phrase “Oh God,” ten thousand times. In every octave and key. Sung, yelled, squeaked, blurted, gasped, and whispered. Some days my ears rang from the sound. During orgasms I’ve been grabbed, twisted, hugged, shoved, and tickled. My boobs have been felt up countless times. My ass has been grabbed, pinched, spanked, fondled, and massaged. I could go on and on.

By the time Tracy was a senior in college I had seen a dozen men come and go as her boyfriend. I celebrated when they left and secretly cried when they came. Despite these guys, I’d have to say that Tracy and I became steadily closer to each other. I was more like her daughter/servant than daughter/bitch. I did do all the labor around the house besides my sex work which freed Tracy up to study hard and live as she wished. I never made a peep of a complaint. I loved her and would be her slave if needs be.

In her senior year, Tracy applied to law school and was accepted and we celebrated the good news with Tracy’s best friends. A half-dozen bottles of champagne and merriment. My work had given Tracy sufficient funds to pay for the three years of law school with plenty left over. I had the sense that Tracy was going to announce the end of my need to pleasure me and women but she held back. I had to assume that she knew best!

***

In the spring, a month after our celebration of her law school acceptance Tracy came to my bedroom when I was about to go to sleep. My last customer of the day had been a woman bodybuilder who had screwed me in the rear. I had played the part of her estranged husband, Phil. She had tossed me around the bedroom for an hour finding different ways to prove how she was infinitely stronger than me. The coup de grace was dressing me as a girl, strapping on her dildo and fucking my rear. “How’s this Phil?” she said over and over again as she pushed her dildo into me. I kept on thinking how glad I was that I wasn’t Phil in real life.

I had showered and turned the lights out and Tracy lay down next to me in the dark room. She softly said to me, “We’re rapidly approaching a juncture in our lives. Up to this point we’ve been together because of our parent’s dying wishes. It also made a lot of sense since you needed me to take care of you and protect you. Now you’re 22 and I’m 21. We’re adults as far as age goes. The time has come where we have to think of what our future is going to look like.”

My worst fears seemed to have come true. Tracy was setting the groundwork for telling me that we were going to move on from each other. In the dark, some tears started to come from my eyes.

“Your sex work has allowed me to go to college and get ready for law school. I’m so appreciative of that. During the last four years I’ve dated many men as you well know. I can only imagine how painful it was for you to know that we had sex together and sometimes loved each other. In every case, however, the romance died and we parted ways.”

My tears started flowing in earnest. I wanted to die. I couldn’t take the pain of her leaving me. I tried to brace myself for the inevitable rejection but knew that that was impossible. I was going to be an absolute wreck. I wished I had at least one friend who would pick up my shattered pieces.

“I’ve thought a lot about these failed relationships until it dawned on me that I’m the reason they failed. You see, I love men’s bodies but I don’t like having to fend off their instinct to lord over me, or even to have a relationship as equals. No. No. No. What I need in a man, is you. A man who is so incapable of competing with me that I can be the unquestioned dominant partner. A man who is so in awe of me that he offers no resistance to whatever it is I want to do. A man who has become a girl because of his inability to stand up for himself. The truth is that I love that kind of man and I love you. Yes, Debra, after all these six years together, I have finally realized that I’m crazy in love with you. I get an endless thrill from dominating you and seeing your weakness. So I’ve decided that I don’t want to look for any other man in my life. I want you. I want to marry you and raise a family with you. You’ll be my wife, my daughter, my bitch. You’ll do my bidding in the same worshipful way you’ve always done. So what is it Debra? Will you marry me?”

My tears switched in an instant from tears of pain to tears of joy. I began to sob loudly and between the heaves of my chest I said that of course I would marry her and that I would always be devoted to her. I’d do anything she told me to do. I would take care of our children and do all the chores around the house and always be her pretty Debra for whenever she wanted to have sex with me.”

“I’m so happy Debra!” Tracy said and she rolled on top of me and we kissed for a long time.

***

Our wedding was held in May in a corner of our backyard under a red maple tree just beyond the pool. We had many, many guests. There were Tracy’s girlfriends and their plus ones. There were some neighbors. There were even some of our most loyal clients. Molly, Leo, and a dozen other regulars attended. For them it was bittersweet because they were happy for me but sad that I would no longer be taking care of their sexual needs.

I was dressed in my mom’s wedding dress and I wished that she could have seen how pretty I was. Abby and Laurie had spent an hour with me beforehand helping me with my dress, my nails, my makeup, my hair, and everything else needed to make me beautiful. They gave me a pretty corsage to hold. On cue, a string quartet played Pachelbel’s canon and I came down the stairs and out back to join Tracy in front of the minister. She was wearing a dark blue, short dress and looked radiant. My mom’s beautiful gown swirled around me as I came up to Tracy. I was so overcome with emotion that Tracy reached out to steady me.

The minister talked about love. Talked about what it takes to have a successful marriage. He said that both the happiest and saddest people he knows are married. Tracy and I would have to spend our lives working to make sure that we never lost the happiness we shared this day. We exchanged vows and Tracy put her mother’s gold wedding band on my finger and I put my father’s gold wedding band on her finger. We kissed and I wept uncontrollably. The guests applauded and we celebrated our marriage long into the night.

The End