A Look Into My Mind: Uncle Sissyboy Ch. 02

I was sitting in my office working. It was very quiet and I was getting a lot of paperwork done. My intercom went off ... "Rich, your sister in law and niece are here. They are asking to see you. Should I send them back," Liz, my secretary asked.

My heart began to race and my cock began to stir. "Uh, yea, sure ... Liz ... tell them to come right back here." It had been two weeks since I had seen them. That was the most unbelievable turning point in my life. Things have not been the same since, and I was wondering where they have been, what was going on. I head my door knob and the door opened. Standing in the doorway was Arlene and Lauren. As I looked up, they smiled. They were both wearing short white denim skirts. Arlene had a thin blouse and her bra was visible beneath it. Lauren had on a tank top and the coolness of my office, made her nipples poke out at the material. They both had on flip-flops.

As they walked in, their perfume permeated the room. I saw their red nail polish on their toes that matched the nail polish on their fingers. They were both tan and looked great. "Mom and I were at the gym earlier, and we decided to come see you ... to make sure that you were following our orders" Lauren said very nonchalantly.

Arlene pushed the lock on the door immediately as it closed. "Stand up and drop your pants, sissyboy" barked Arlene. I stood up from my desk and walked around it, towards them. "Stop right there and do as I ordered, sissyboy" Arlene said in a disgusted tone.

I unbuckled my belt and unsnapped my pants. I let them fall down my legs. There I stood, in Arlene's panties that were given to me to wear. I was told to wear either her pair of soiled panties or Lauren's every day. I was told that they would pop in on me and make sure I was obeying them. I was told not to launder them and I was told to make sure that I came in them and let little squirts of pee in them from time to time. I was further told that I must always have them against my body, that I could wear other panties on top of them, like latex or something else, but that their panties must always be directly against my skin, and they must not be laundered unless instructed to do so.

Lauren and Arlene looked me up and down. "Pull those panties down, we want to inspect them, sissyboy" continued Lauren. I pulled them down and Lauren approached me. She bent over and looked at them. "Yep, mommy ... they are quite ripe smelling and I can see that uncle sissyboy has added to your soil. Good job, uncle sissyboy. It appears you can follow some instructions, very well."

Lauren and Arlene sat down on my sofa, making sure that their flashed their panties at me as they sat down. "Go ahead, and pull them back up, sissyboy" said Lauren.

My cock was beginning to get hard, especially since I saw the crotch of their panties as they sat there in a very unlady-like and provoking manner. "Pull them up over that disgusting clittie cock of yours and pull your pants back up." Arlene said smugly. "You don't think we are going to do anything here, do you ... you disgusting pig? she added.

"Uhm, no ... Mistress Arlene. I wouldn't expect that to happen" I muttered.

"I don't need or expect an explanation from you, why you followed my directions or what you expect! What we do or don't do is up to us, and has nothing to do with your pig expectations."

I looked down at the floor. "Yes, Ma'am"

"Now this is what is going to happen. Tomorrow is Saturday and we arranged for your wife to go to NYC to spend the weekend with our mutual friend, Grace. She is going to spend Saturday and Sunday night there and go shopping and see a play with Grace. There will be a few other girls with them, and it's a "girls weekend" so you won't be invited. Instead, I asked Debbie if you could come and do some work at the house, and she said she would ask you."

"The Limousine will pick her up at 8:30 a.m. Immediately after she departs, you are to get in your car and ride to my house. I mean, immediately. Do you understand?" Arlene said in a very demeaning manner.

"Yes, Mistress ... I understand." "The answer of 'Yes Mistress', would be more than enough to hear from you. Are you fucking stupid? The only words to be muttered from your cock-sucking mouth, is "Yes Mistress" or "No Mistress". "Ok, you pathetic asshole?"

I learned quickly, or at least try to. "Yes Mistress."

Lauren and Arlene stood up, opened the door and left. No goodbye, no nothing ... just got up and left. I could feel my clittie leaking in the panties. I guess now would be a good time to cum in the panties. I need it bad, and I don't know how long it will be before I am permitted to, again.

My phone rang, it was Lauren. "Uncle sissyboy, mom and I decided that we want you to cum in the panties you're wearing. So, do whatever perverted stuff you do, and make that clittie cock of yours spurt your hot cum in mommy's panties."

I put on a porn movie on my computer screen and masturbated myself through the panties. I came very quickly and my panties were filled with cum. I stood up to make sure it wouldn't make my pants wet, and I could feel the cum leak down and wet my balls.

Saturday morning couldn't come quick enough. I kissed Debbie goodbye and told her to have fun and buy some nice things. I watched as the limousine drove off down the street. I quickly jumped in my car and drove to their house.

There was a note on the front door. It said, "Rich, come in and go up to my bedroom. There is work to be done in there." It was signed, Arlene. I walked in and headed up the stairs. Noone was in sight. I couldn't hear anything and didn't see anyone. I walked into the bedroom and there were clothes on the bed with instruction to put them on. I looked at the clothes. There was the black hood, a black latex bra with little holes cut out where my nipples would be a black pair of latex panties with a sheath that I figured was to hold my cock. The panties had a full back but there was a hole cut to give access to my asshole. There were black latex stockings and a black latex garter belt. Where should I start, I wondered.

I heard the door open and in came Lauren. "Uncle sissyboy, I thought I should be here to make sure you do it all right." First, put on the garter belt"

I put the garter belt on and felt my cock begin to harden. Lauren laughed, "You're excited already and we haven't even begun yet. Pull the stockings on first, they may be difficult to get on, but you can do it if you try."

I pulled them on, it was difficult, but I figured it was easier to roll them up and put my foot in then roll them on my legs. I finally got them up and fumbled with the garter hooks to hold them up. I've seen them before on my wife, so I knew how to do it. "Very good, sissyboy, or should I say, sissygirl?" Now, take some of that baby oil on the dresser and smear some on your clittie. It will make it easier to slide that worthless cock into the sheath. It will also make it nice and slippery and exciting. It will be hard for you not to cum. AND YOU'RE NOT TO CUM!!!!"

I pulled the latex panties up and pushed my slippery clittie cock into it, then pulled them up the remainder of the way. "Now put on the bra. Have you watched your wife do it? Put it on backwards, snap the snap, slide it around so it's the right way, and put your arms through". Lauren laughed as she said it.

I did as she instructed and positioned the bra so the cut-outs nicely framed my semi-hard nipples. I glanced across the room at a mirror and saw myself in it. I think I looked pretty good. I liked the way I looked. WOW ... they totally owned me, I thought to myself. My clittie cock was sticking out hard and it wanted to be played with. I could feel it leaking.

"Ok, uncle sissyboy, just go sit in the middle of the room ... kneel on your knees in the position that we instructed you to get into" Lauren quickly instructed.

I quickly did as she instructed and watched her leave the room. When she returned, Arlene walked in with her. "Sissyboy, I see Lauren got you dressed properly. You look very sexy and I'm sure the people coming to see you will be very impressed with what we have to offer them" Arlene laughed

People coming to see me, I wondered. Who, what ... when .... WHY? My clittie jumped in its latex sheath. I could feel my nipples harden. "Sissyboy, you had better put that hood on, or they will see who you are. Get up and put it on, immediately." She spit in my face ..."that will make it slide on easier" she quipped. I slipped it on and got back into my position.

Arlene told Lauren to "have them enter."

Eight people entered, four were women and four were men. Then men each had hoods on. The women did not. The women all wore latex skirts, tops and high heels. The men all had on outfits identical to mine.

"Sissyboy, for the last 15 years, I have been a Domme. I have been paid by people to do things to them ... things that they wanted and couldn't get elsewhere. It all started when my dearly departed husband, the sick bastard that he was, decided he wanted to be submissive. We played with it and I learned. One day he wanted to "experience" another man, as he put it. So I found another sniveling man who was submissive and wanted to be Dommed. He paid us a lot of money and that is how I learned to make money doing these things."

"The people who have joined us today ... the women at least ...are all like me. Professional Domme's. With them are the pathetic submissive men who pay them to dominate them. So today and tomorrow, you will treat them to your body and allow them to do anything and everything they desire. I would ask you if it's ok, but it really doesn't matter, does it? If I say so, it's done."

Lauren walked in; she was dressed in nylon panties, stockings that didn't need a garter belt, and high heels. Her little pert titties were magnificent and held in place with a sheer tight bra. It looked like a training bra, since it didn't appear to have any cups. Her thick black pubic bush could be seen thru the very sheer material of the panties. There were hairs that escaped the confines of the panties and curled forward. Her long, tanned legs were enticing. My cock got harder. I always had a thing for my niece, and it was obvious to all, that I did.

Lauren walked over to me and stood in front of my face. Her panties were directly in front of my face and I looked at them with great interest. My cock got harder and she lifted her foot and touched it with the toe of her shoe. "I bet that pathetic cock of yours is leaking in that sheath, huh sissyboy?"

Lauren turned around and faced the visitors. Her ass, now in front of my face. I could see the crack of her little ass thru the sheer panties and the trail of dark pubic hair that lined it. I looked down her magnificent legs and then back up. "You see, this sissyboy behind me has always had a thing for me. As I grew up, I would frequently notice him trying to look up my skirt or trying to see up the leg of my shorts. He would glance at my bare feet whenever possible. I would feel him undressing me with his eyes, and it always made me feel uncomfortable. Being younger, I wasn't sure what it was all about, but it did make me feel uneasy. I just wasn't sure why."

Lauren continued, "It seems he also had a thing for my mom and would frequently steal her panties from the hamper in our bathroom. She didn't know at the time what was happening to them, but she did wonder why her panties were missing. She always suspected it was probably the friends of my brother who got interested in them and took them."

Lauren turned and holding my face said ... "isn't that true, sissyboy?" "Yes Mistress" I obediently replied. I could see the Domme's shaking their heads in a disapproving manner. Lauren continued, "sissyboy admitted to me a few weeks ago that he would have stolen my panties too, but they were too small and when I was younger, they were always cotton and he doesn't have a fetish for cotton panties." A short time ago, I found on his computer, a link to a site that he maintains that has pictures of him in panties and talks about his desire to be a transvestite. More specifically, a submissive transvestite. He had notes for readers about his stealing panties from my mom among others. About his lecherous desires toward me and my mommy. In short, it's a site dedicated to showing what a sick fuck he truly is."

Lauren turned to look at me again. This time she spit on my face and kicked me in the balls. I leaned forward in pain and she pushed me back up. "No one gave you permission to lean forward, sissyboy. So sit the fuck up and stop being a baby" she growled at me.

Turning back to the audience, she backed closer to my face ... her nylon covered ass barely an inch from my face. "Mommy and I confronted him about this a few weeks ago and began to initiate him into his new life ... a life of being a subbie to mommy and me. Mommy and me hope you will be able to help us move him along this path and that you use him in any way you desire."

Lauren knew that her attire had the attention of the other submissive men in the room as well. She knows full well that her young, thin body is the desire of many men in the world today. Most men love the look of younger females, especially teenagers. I'm sure that her presence in the room today was very exciting for the male attendees.

"Uncle sissyboy, I want to give you a special cleaning today. One of the ongoing requirements that the Domme's have of their subs, is that they drink a lot of water before a session and not piss until told to. So I am sure, that by now ... their bladders are quite full and need release. "

"Mistress', would you please allow your subs to pee into this large enema bag so that I can give sissyboy here, a nice piss enema to clean him out for your use?" With that, a simple gaze at each sub by their Domme made them stand and walk over to Lauren. "Ok, I want each of you to pee into this bag, so that your hot piss can flow into uncle sissyboys ass" They each obediently pulled their latex panties down and, one by one, pee'd into the bag. The bag was quite full of hot yellow piss when they finished. Lauren hooked the bag up to a pole on wheels that she had and walked over to me.

"Kneel down, sissyboy and present your ass for all to see" Lauren snapped. I did as instructed and moved me legs apart so that my asshole was visible. Lauren reached into a bag that she had and pulled out a black rubber nozzle type thing with a hose attached to it and what looked like a rubber pump. She kneeled behind me and worked the nozzle into my asshole. She wasn't very gentle. After she pushed it in, I felt it begin to expand inside my asshole. That's what that pump thing was for. It made it inflate in my asshole. It was quite uncomfortable.

She moved the pole in front of me and I could tell that the tube was already connected from the enema bag. I saw her unclasp the clasp and saw the piss flow rapidly thru the tube and then into my ass. I could feel the warmth of the piss and it flowed in and it excited my prostate. I could feel my cock respond to it.

Here I was, in the middle of the room with eight people I have never seen before. I was kneeling with an enema of piss flowing into my asshole. My cock was hard and dripping within the confines of the latex sheath that was covering it. One of the Mistress' said "I would like to clamp his nipples" Arlene said, "please feel free to do as you wish, darling."

The youngest and thinnest of the Domme's approached me. I would learn that her name was Mistress Janine. She was drop dead gorgeous. She was thin and tall. Her legs were long and fit. Her entire body was very fit and she had long black hair that was pulled back taught into a ponytail. She was beautiful and she smelled magnificent. She approached me and knelt in front of me. "You are really a pathetic sissyboy. You should be honored that someone like me would even look at you, let alone touch you." She had two clamps in her hands. "Kiss these clamps. In a moment they will be latched onto your nipples." I kissed each one as it was presented to my lips and then she clamped them onto my nipples. I wanted to scream. They hurt like hell. I could feel my stomach begin to cramp and my nipples were aching. My clittie was leaking into my sheath. Mistress Janine reached down and examined my clittie. "Look at that ... he actually is enjoying all of this ... there is quite a lot of precum that has oozed into that sheath."

I looked up and the enema bag had emptied. I needed to expel it into the toilet, but the plug in my ass prevented anything from leaving ... only entering. Arlene walked over and told me to stand. It was difficult since standing up only made the pain in my stomach worse. She didn't care and pulled me into the bathroom. "Sit on that toilet and clean out that worthless ass of yours. You're lucky that I'm not making you shit in a bucket and make you eat it."

I sat on the toilet and immediately the piss expelled from my ass in a strong hard stream. I could feel the water from the toilet splash up and cover my ass. The enema piss would start to squirt out and stop, start and stop ... over and over and over again until it no longer came out. "Wipe yourself clean with these wipes and stand up" barked Arlene. I did as I was instructed.

Mistress Jennifer, the older of the other Domme's walked in. "Sissyboy, we want to make sure you are totally cleaned out, so the other Domme's and I have pissed into the enema bag with our golden hot piss and have decided to give you an enema with our glorious golden liquid. You should be honored to get an enema with our special piss. With any luck, you'll get some of our estrogen from it, and it will make you more of a girl."

Mistress Jennifer was thin and tall like the others. She had a look about her that made it very clear that she would love to hurt me and would love to inflict as much pain as possible. She looked very cold and hard. She was also beautiful, her hair also pulled back hard into a ponytail. She was a stunning woman, but one I knew could be very cruel. "Get on your knees and push your ass up towards me. That means, get on your knees, then your chest should touch the ground."

She took the enema, now known to me as a bardex, and with one hard thrust, shoved it into my ass. I was glad that I had been stretched already, because it would have hurt a lot more than it did, it I hadn't been. "Now follow me into the bedroom. I want the others to witness this" Snapped Mistress Jennifer

All the talk of piss made me realize I hadn't relieved myself when I was on the toilet. I needed to go bad. I knew better than to ask. Mistress Jennifer reached down and continued to pull me into the bedroom by grabbing my semi-hard cock and pulling me like it was a handle. When I got into the room, Lauren walked up to me and said, "I'm going to pull the clips off your nipples, uncle sissyboy." Instantly, she opened them both and took them off. I wasn't prepared for the pain that followed. As the blood rushed into my nipples, the pain was intense. It was a burning pain followed by a bad ache. My god did it hurt. My cock went totally limp. "Aww look, his pathetic cock went limp from the pain ... what a shame" Lauren teased.

"What good is hard cock unless it's fucking you? It should be limp" said Mistress Janine. "I told him not to have a hard cock unless ordered to do so. Now I know what to do, to make him limp ... if he doesn't obey in the future." She giggled a cruel giggle.

Mistress Jennifer took the very full bag of the Domme's piss and attached it to the hose coming out of my ass. She made sure the bulb was totally inflated ... and it hurt when she did. Then she opened the clasp on the tubing and the piss flowed into my ass. It was already getting cool and the sharp contrast of my warm rectum and the cool piss gave me an instant erection. I could feel precum ooze out again. That sheath must really be getting a lot of precum in it. I wanted to reach down and stroke myself, but knew that wouldn't be allowed.