Life in a Whorehouse Pt. 06

Hello, this is Julie. Becca and I are sharing this series since we both worked in the same whore house together. Becca is a genetic woman, I am a sissy that was raised as a woman by my Mum and sister since I was a little girl.

This story is different from almost all our other stories in that it is all fiction. In this story I am going to be a young woman again in my 20's. Also 2 women that are very important who recently passed will be alive again (Oh how I wish I could do that for real!). My mum, Linda, will be a key part of this story as will a dear family friend, Patricia. Like my mum she will be in her mid to late 40's. Though her name is Patricia, most people call her "Grammy." I am dedicating this story to the memory of both my mother and Grammy.

It is morning, my sister (Becca) and I are just waking up. As soon as we woke up we remembered what happened last night. Both of us stink of cum, piss and shit and we have cum oozing from our holes. Becca is leaking from her cunt and asshole and I am leaking from my sissy cunt (asshole).

We turn to look and laugh at each other. I live in the brothel 24/7 because I am the property of one of the brothel's owners, Annie. Whenever my sister works in the brothel, she sleeps with me in my room. It is not unusual for us to entertain clients together as we did last night.

As we are having our morning coffee, the phone rings, it is Mistress Nancy, the other owner of the brothel. Becca answers, "I want you and Julie to come to my office immediately."

Never daring to disobey her, both of us walk bare assed naked to her office. As soon as we walk in we curtsy to Mistress Nancy and then we see our mum is there with another woman her own age.

We both run to our mother and hug her tightly. She laughed at the sight of us and said, "You both stink like well used whores."

Always the smart ass Becca said, "You should know Mum, you have been a whore a lot longer than us." Mum playfully slapped her ass.

Mum then introduced the other woman. "Girls this is my friend, Patricia, but most people called her Grammy. I asked Mistress Nancy if she would mind if I used her office to introduce you girls to Grammy since it might involve the Mistress as well."

Not caring that we were naked we both curtsy respectfully and sat down, but used a towel that Mistress gave us to sit on. I looked at Grammy and said, "Please excuse our appearance Ma'am and I am sure we both smell awful."

Grammy was gracious, "Not to worry. Your mother warned me about how you might look ladies. Besides, I think you both look lovely and I find your smells arousing."

Mistress said to our mother, "Explain what this is all about Linda."

Mum looked at Becca and I and said, "Grammy has a grandson that she adores and she realizes, like Julie, he was never meant to be a boy or man. She has been helping "her" transition from living and dressing as a man to living and dressing as a woman. She reached a point where she felt she needed help and reached out to me knowing all about Julie as she does."

Mistress said, "I do not mind helping you Grammy, but you know this is a whore house. Are my girls the kinds of women you want you new granddaughter to use as role models?"

Grammy was prepared for that question. "They are exactly what my 'granddaughter' needs Mistress. She needs to learn not just how to be a woman, but how to be a sensual woman."

Mistress looked at all of us and then said to Becca and I. Girls go shower and get yourselves clean and presentable. Julie, come back here in your yellow sun dress. Becca help her get dressed, but I want you to come back naked with your wrists tied behind your back. Be back here in 1 hour or you will be punished."

We both curtsied and left to obey Mistress' commands. Once in the bathroom, I sat on the bowl to do my morning pee and shit, while Becca used the shower. Once she was done showering we switched. I smiled as I thought we always had our best conversations while one of us was on the bowl like this.

I asked, "Why do you think Mum wants us to do this?"

Becca thought and said, "I think Mum realizes that she saved you from a frustrating situation of living a life you were never meant to be. I mean both Mum and I can see how happy you are as a woman. I think Mum just wants to help someone in the same way she helped you."

Before Becca could dry herself, I took her in my arms and kissed her. "You were just as responsible for making me a woman as Mum was and I can never thank you enough."

I sank to my knees and put my face by Becca's cunt. The night after tending to a lot of clients, Becca's cunt tends to be raw and sensitive. I know how much she likes oral done to her then. I let my tongue slide along the outer folds of her labia and took my time arousing her. Once I knew she was at the point of no return, I slide the tip of my tongue along her swollen clit and pressed upwards. As my tongue slid up, I could feel her body shudder.

She used my wet head to lean on as she recovered from her orgasm. Then she looked down at me, "How is it you always know what I need girl?"

I smiled and said, "I was taught by the best."

I looked at the clock, "Shit we are almost out of time. We have to hurry."

Becca went into the closet and got my yellow sun dress, while I started to put on my lacy yellow knickers and bra, stockings and garter belt. Becca gave me the dress. Before I put it on, we blow dried each other's hair. Then I slipped on the dress, stepped into my matching heels. I tied Becca and we hurried to Mistress' office.

As I was afraid we were about 5 minutes late. Mistress was not happy. "You're late ladies."

Knowing it was my fault, I said, "I am sorry Mistress, the time just got away from us."

Mistress smiled and said, "Yes it does, especially when you are licking your sister's cunt." Mistress pointed to the screen. All of the rooms are monitored by CCTV for the safety of the girls when they are with clients.

"That was quite a performance you girls put on. I suppose all three of us should thank you. As we watched you, your Mum, Grammy and I played with ourselves and had nice orgasms.. Thank you very much."

Thinking we dodged a bullet, Becca said "You are welcome."

"You were late, Becca. You first. Bend over." Mistress looked at Grammy and explained. "If you decide that you would like us to train your granddaughter, this is what will happen to her when she does not obey the rules."

Mistress reached into her desk and used her wide leather strap and gave Becca's ass a severe whipping. Poor Becca could just squirm helplessly because her wrists were still tied behind her back. After Becca's ass cheeks were a bright red. Mistress put the strap down.

As Becca was having her ass beaten, I could not help but notice that both my Mum and Grammy were squirming in their chairs. I always knew Mum was a pain slut, but I suspected the same was true of Grammy.

Mistress sensed something about Grammy. "Did that upset you seeing Becca having her ass strapped like that Grammy."

Grammy was obviously flustered by her sexual arousal. "I really don't know what to say Mistress. I understand why you beat her, but I feel bad for that poor girl being beaten."

Mistress smiled, "Poor girl? Go over and touch her cunt Grammy. Tell me what you feel?"

It became obvious that Grammy had never touched another woman in such an intimate way, but knew she had to obey Mistress so she did as she was told. I remember how her hand trembled as she reached for Becca's cunt. As soon as she touched it, they both sighed.

Mistress said, "Does Becca feel or sound like a woman in distress?"

"No Mistress, she is soaked, she must have enjoyed it."

Mistress smiled, "She did. Now would you please be a dear and finish helping Becca orgasm sweetie. Finger her for me."

It was obvious that Grammy was confused, terrified and sexually aroused. As always, sexual arousal wins out and she fingered Becca's wet cunt. For a novice, Grammy did quite well and soon Becca had a really wonderful orgasm.

When Becca settled down she thanked Grammy and Mistress said to Grammy, "Lick your fingers clean dear." Grammy was obviously embarrassed, but obeyed. Mistress asked, "How does Becca taste.?"

Blushing a bright red, Grammy answered in a whisper, "Delicious."

Becca's ass was far too sore for her to sit, so Mistress allowed her to stand. Then Mistress turned to me. "You will be punished too, but first I want Grammy to take a close look at you girl. I stood up and assumed the submissive position; thighs spread wide and hands behind my neck."

As I did, my sundress hiked up, exposing the tops of my stockings and garters.

Mistress said, "Look at her Grammy, would you ever think she is anything but a woman?"

Grammy looked in awe, "She is stunning. I wish my legs looked as good as hers."

Mistress said, "Julie, take off your dress."

I turned around so my Mum could unzip my dress. As she did, I noticed her hands tremble. I knew she was sexually aroused now as well. Once she unzipped my dress, it puddled at my feet and I stepped out of it. I noticed that Grammy went to pick up my dress without being told to and hung it up. I wondered if she was a submissive as well.

Mistress said, "What do you notice Grammy?"

Grammy voice trembled a bit. "Not only does she radiate femininity, she radiates sexuality as well. She is stunning!"

I smiled and curtsied as I accepted her compliment graciously and Mistress explained, "All my girls are trained to be prostitutes dear, not just whores. The difference is that a whore is just concerned about getting their 'John' to cum and then moving on. My girls are trained to give pleasure. That pleasure begins with how they dress and conduct themselves at all times."

"All of my girls wear stockings and garters 24/7. Our clients, both male and female, love how they look like that. Normally Becca would be wearing her stockings and garters as well, but I wanted her completely naked."

Grammy said, "You mean you have women coming to this whor....I mean brothel as well?"

Mistress smiled, "It is okay Sweetie, I do not mind you calling it a whorehouse and yes, about half of our clients are women dear. They come here out of sexual frustration or to experiment. Some come here so we can train them how to be better lovers. So when you asked us to train your granddaughter how to be a woman, that did not surprise me. Linda knows we do kinky things like that. What is the name you use on your granddaughter when she is dressed pretty."

"I call her 'Tricia' Mistress. She chose that name to honor me and I love her for that."

Mistress turned to me, "Unhook your bra Sissy." I did as she told me though I thought it odd that she called me "Sissy."

When I took off my bra, my 36D tits tumbled out. They stood firm and my nipples were like diamonds now. I was obviously excited.

Mistress explained "Sissy has been on hormones since she was a teen. Her tits are natural. Go ahead Grammy, feel them."

Grammy's hand trembled as she reached out and started to rub my tits. I smiled and said, "They are not made of glass Grammy, they won't break if you squeeze them. In fact, I would love for you to slap them please."

Grammy did as I asked and slapped them once gently, then slapped them harder, over and over again. She asked, "Doesn't that hurt?"

I smiled, "It does and thank you. I am a pain slut, I love being slapped like that."

Before I could say anything else, Mistress pulled my hair back and spit in my face.

Mistress said, Slip your knickers down Julie." I did as commanded and then Mistress went on to explain. "So her cock Grammy? We do not call it a cock, we call it her clitty. Jiggle her balls Grammy."

Grammy did and I could feel her warm hands on my tiny balls. Mistress said, "We call those her 'lady parts' Grammy. See how tiny her clitty is? She is hard now and she is not quite 4 inches. That is because of the hormones dear. The same hormones that gave her such nice tits also made her clitty small as well as her lady parts. But on the plus side, when she cums she cums a lot. Watch."

Mistress then looked at my mum. "Take off your clothes dear." Mum quickly obeyed and then stood naked, except for her stockings and garters, in front of Mistress in a submissive position, thighs spread wide and hands behind her head.

Mistress said to Grammy. "Watch this. I am going to have Linda suck her daughter. When Julie cums Linda will open her mouth and show you how much cum Julie produced."

Grammy said in shock, "You mean Linda will suck her own daughter?"

Mistress asked, "Does that bother you Grammy?"

Grammy shook her head, "No it is just so new to me and so exciting."

It was obvious that Grammy was sexually aroused by the way she was squirming in her chair. Mistress said, "You are imagining yourself sucking your granddaughter now, aren't you?"

The blush on Grammy's face as all we needed to know Mistress was correct.

Mum got on her knees in front of me and kissed the tip of my clitty and then put the tip of her tongue on my pee hole. She looked up at me and said "No matter how often I suck you dear, it still excites me."

Normally Mum would take her time and bring me off slowly, but she knew that Mistress was waiting impatiently, so she dipped her finger into her wet cunt and then reached around and pushed her wet finger into my sensitive asshole. Just as she pressed into my prostate, my clitty exploded in her talented mouth.

I came hard. I was already excited, but to have my clitty being sucked by my mother, in front of a woman I just met, really sent me over the edge. I came so much harder than usual. After I was done cumming, I could feel Mum sucking me one last time.

Mistress said to Mum, "Look at Grammy and then open your mouth dear."

Mum obeyed and as she opened her mouth, cum started to drip from her lips on to her tits. Mistress smiled and looked at me, "Very impressive dear."

Mistress asked Grammy, "Have you ever kissed another woman girl?"

Grammy shook her head no.

Mistress had an evil smile when she said, "This would be a good time to start dear. Kiss Linda's mouth."

Grammy never hesitated and kissed my mum and the both of them shared my cum as they kissed passionately. When they were finally done Mistress asked, "How was that Grammy?"

Grammy's face was flushed, "I can't explain it Mistress. I have never dreamed of doing this, yet I loved it."

Mistress said, "Be honest dear, you can't wait to suck your granddaughter."

Grammy never hesitated, "I won't lie to you Mistress. The thought of that excites me."

Becca remained standing as Mistress explained her plans. The sight in the room was so erotic. Two beautiful women seated as they discussed Tricia's future, while 3 other woman stood naked and listened quietly.

Mistress explained her thoughts. "You can have Tricia brought her to live for a month. During that time, Linda and her girls will train Tricia on being a woman. During that month, you and Tricia will have no contact with her whatsoever. At the end of the month, you will come and see how Tricia looks and acts and based on the results we will decide what to do next."

Mistress then asked Grammy to describe Tricia physically and it was agreed that Trisha was likely going to be a BBW, at least at first. Mistress said, "I am going to have the other co owner of the brothel help as well Grammy. Her name is Annie and she is a BBW. She will help a lot."

Once everything was settled, Mistress said, "It has been about 10 minutes since Julie came in her mother's mouth. Remember I told you that the hormones allow Julie to have multiple orgasms just like a woman does Grammy. Watch this."

Mistress said to me, "Sissy, I did not forget that you were late in getting back here, Now you will be punished as well. Unzip me."

Mistress turned her back and I unzipped her dress and she stepped out of it. Then she took of her bra and knickers. All of us admired her naked body. Both Mistress and I are the same tit size, 36D, and often will share bras and clothes. Then I noticed that Grammy had the same body type as Mistress and I did, lithe with a dancer's body and her tits were about the same size as Mistress and I.

Mistress sat down in a chair and spread here legs wide. I laid across her legs with my clitty between her legs. Once I was in position, Mistress clamped her legs tight on my clit. As she did, I could feel her stockings pressing on to my clit. Mistress knows how much I love that.

Mistress never hesitated or held back in front of Grammy and gave me a vicious spanking. My ass cheeks were bright red in no time and the more I squirmed the more her stockings rubbed along my swollen clit. When she was done, she called Grammy me over.

"Feel Sissy's ass dear, what do you notice?"

Grammy said, "Her ass is bright red and it is really warm."

Mistress smiled, "That is how someone's ass should be if the spanking was done properly. Now watch this Grammy."

Mistress extended her finger to Grammy's face. "Lick my finger dear."

Grammy did as told and then Mistress put her finger by my sissy cunt (asshole). I squirmed as she started to push deep inside me. Mistress looked at Grammy and explained "What I am doing now dear, is I am milking Sissy by playing with her prostate."

Sure enough, In just a moment my clitty exploded and I moaned loudly as I came hard, spurt after spurt. Mistress kept her finger in my sissy cunt until I was completely done. Then she leaned over and lovingly kissed my ass.

Slowly, Mistress pulled her finger out of my asshole and, as Mistress expected, it was covered in shit. She extended her finger to Grammy again. Grammy hesitated for a second and then leaned over and licked Mistress' finger clean.

Mistress smiled at Grammy and said, "Good girl."

Mistress spoke up with me still laying across her lap. Now I was so embarrassed, I am sure my face was as red as my ass. "Remember, Sissy just came a short while ago in her mother's mouth. Remember how much Sissy came dear? Now watch this."

Mistress slapped my ass again, "Get up Sissy." I did as I was told and then Mistress stood up as well. When she did there was a large puddle of cum on the chair.

Mistress looked to Grammy, "Not only can she have multi orgasms Grammy, but each time she cums, she cums a lot."

Looking at Grammy Mistress said, "Be a dear and lick Sissy's cum from the chair please?"

Grammy never hesitated and for the second time in 15 minutes was savoring the taste of my cum. As she was doing that, Linda was licking the cum from Mistress' thighs and stockings.

Once everyone was done, Mistress looked at Grammy and Linda and said. "I am sure you ladies have a lot to discuss. Why not use Julie's room and sort things out between you both and then come back in here and we can iron out the last few details."

Grammy stood up to leave, but Mistress said, "One last thing Grammy, leave all your clothes here."

Grammy started to protest but when Mistress glared at her she backed down and meekly removed her clothes. I remember being impressed with how beautiful Grammy was and being shocked that she wore such sexy underwear. I did notice that Grammy's cunt was not shaven and the pubic auburn hair was quite thick and curly.

Then bare assed naked, Linda and Grammy went into the hall to go to my room. As they walked, Grammy put and arm across her tits and a hand over her cunt for modesty. Linda gently slapped at her hands. "I am sorry Grammy, women are not allowed any shame of modesty in here."

Grammy awkwardly lowered her arms but blushed bright red as men and women passed by her and stared at the new woman they had never seen before.

Once inside Julie's room, Linda looked at Grammy and said, "You must have a dozen questions. Let me make us some tea and we can figure things out. Once the tea was made, they sat down together and Grammy noticed that Linda sat with her thighs slightly parted.