The Awakening of a Sissy Pt. 01

A little background about me. My name is/was Joe and I grew up in a small rural area, without a father figure around. There was just mom and 3 older sisters. As such, i ended up picking up a number of slightly femmie traits. It didn't help that i was also small and kind of wimpy. i was forever being harassed by the boys as i was walking home from school. I'm sure you can understand why i say, i had No dating life growing up. I was 19 before i dated my first girl and that came to a screaming halt the moment she saw how small i was, left laughing and never spoke to me again. Jump ahead, I was now barely 19 years old.

I was in a bar sitting alone at a small table, having few drinks, while watching some people play pool. There was a group of young ladies not far from where i was seated. They seemed to be having a fun time chatting and laughing it up. I noticed that there was this one of the young woman that every so often would look my way. I began to wonder if the laughing was coming at my expense.

A while later, as I slowly worked on my second drink, i saw the same young woman get up and walk past me on the way to the ladies room. She looked beautiful and was wearing a small black dress, a little above mid thigh. Her shapely legs were covered in black stockings and she was wearing some very high black spiked heels with double ankle straps. I took notice her lovely figure, nice full breasts, and how her hips swayed from side to side as she slowly strolled past me. A short time later I again watched her as she returned to the table.

While sipping on my drink, I watched the guys at the pool table betting on various shots. At one point one of the guys place a $100.00 bill. betting the other he could not make some kind of crazy bank shot. Soon there was so much money sitting out on the table for both yes and no I felt bad for the guy having to make the shot. I glanced away for a moment to find her smiling and looking at me once again. When she saw me looking she raised her glass as if toasting me. I smiled, raised my glass in response, while wondering what her interest in me seemed to be, and took a sip.

Shortly after doing a cheers with her i noticed the ladies laughing once again. i assumed it was at my expense some how. All of a sudden there was this load cheer, the guy made the shot and soon a fight broke out. I just shook my head wondering Why?

I have to say, I enjoyed watching this beautiful woman, who seemed to have some type of interest in me. Once again there some loud laughter coming from the table, attracting my attention. Moments later she rose, smiling and looking my way.

I watched as she slowly strolled her way over toward me, drink in hand. When she approached my table i attempted to introduced myself, telling her I was Joe. She looked at me for a few moments before saying with a smile on her lovely face "hi Joe, I hear you have a tiny little dick, I like that, and want to get to know you better." Hearing those words, I felt the blood rush to my face.

Embarrassed, humiliated, and upset, I began to rise from my seat to leave. In a soft yet firm voice she said, "Sit Down Joe, I want to get to know you better." While part of me was saying, get the hell out of here, another part was drawn toward the way she spoke to me. Knowing I could leave at any time and curious to hear what she had to say, i sat back down.

She sat down at the opposite side of the table, directly facing me. "My name is Dianna, most people know me as Di," she told me. Di told me how she was somewhat new to the area and recently purchased a house. I learned her and the others at the table had stopped to have a few drinks before going to a club to do some dancing.

After some time, the conversation shifted toward me. Di informed me that the girls at the table had told her stories about me. She seemed especially interested in talking about things that were done to embarrass and humiliate me. "Is it true that they would toss your cloths in the tree and make you climb up there naked to retrieve them, with your little thing dangling in front of the girls?"

We must have chatted for almost 40 minutes before Di told me she needed to get going very soon. "I'm really interested to getting to know you better she said. Under the right conditions, I'd like to see you again Joe, how does that sound to you?"

I could not believe what i was hearing. Here was this beautiful woman, not just talking with me but wanting to get to know me better. I told Di that I too would like to see her again. She smiled and said "that's great but as i said there are conditions she added."

"So here is the deal Joe if you really want to see me: 1) you must shave your whole body smooth for me, All hair below your eyebrows needs to go; 2) I control where things will go from here; and 3) you will be at my house promptly at 1100 tomorrow, if you are late I will not answer the door. If you can't meet each of those conditions don't bother showing up." She handed me a piece of paper with her address again adding, "don't show up if you are not meeting each of my conditions," and she walked away.

I sat there for several moments, somewhat shocked over what had just happened. Di was beautiful and she seemed interested in me. There was no question that I was attracted to her but shaving myself smooth in order to see her? I was amazed at how confident she was while laying out her conditions, I somehow found it to be rather appealing.

When the waitress came by I ordered one more drink and paid my tab. I really wanted to see Di but could not get past the shaving myself smooth requirement. I wondered why she would make that a condition for seeing her again. She had said promptly at 1100 or she would not answer the door, what was with that?

After finishing my drink I left and headed toward home. As I drove, my mind was on Di and her conditions. The one good thing about her condition of being smooth was, if I was to do it, I was fortunate to have very little body hair. Smiling, I made the decision to do it. It's just hair, it will grow back, that was the bases of my decision.

When I got home I ran a bath to get ready to shave myself. While the water ran, I used scissors to cut away the bulk of my pubic hair and my armpit hair. Soon after I was in the tub shaving myself. Once my legs were done I began working on my arms. I noted how different it felt having smooth legs. After my arms were done, I began to carefully remove the remaining pubic hair. When that was done I drained the tub and took a quick shower to wash away any loose hair that had stuck to me.

Once I had dried off I walked over to the full length mirror to get a view of my new look. Best I could tell I had got all the hair removed. I found it somewhat humorous when i looked over my pubic region. With the hair gone I actually looked a little bigger.

After having one more drink, I went off to bed without putting anything on. My mind raced with so many thoughts as I tried to fall asleep. I feel asleep picturing Di's beautiful body as well as the instructions she had given me.

When I woke in the morning i made some coffee and then took a quick shower. I decided that I would leave a little early to ensure I could find Di's home and be at her door promptly at 1100. Once I found her house I spent time driving around the area to kill the extra time. A few moments before 1100 I made my way back to her house.

As I was pulling up toward her house, I noticed a car pulling out of her long driveway. I couldn't see who it was due the heavy tint on the cars windows. I parked my car, noted the time and walked to her door. Taking a deep breath at exactly 1100 I knocked on her door. A few moments later she answered the door wearing a black robe and what appeared to be the stockings and heels from the night before.

"Good to see you are on time, I assume you followed my instructions?" When I told her I did she invited me inside. "Let's go to the living room, follow me." Once we were in the living room she had me stand there as she looked me over. After she had walked around me she stood in front of me looking me up and down with a smile on her face.

"Take your shirt off, fold it neatly, and place it on the table Joe." Once that was done she had me remove my shoes and socks. "Now get out of those pants Joe, fold them and put them on the table with your shirt." I nervously began removing my pants while wondering where all this was leading.

As nervous as i was, I was rock hard. While I slipped the pants down, Di started to laugh. "Seriously Joe, you still wear tightie whiteys?"

"That's coming to an end" she added while still laughing. I tried using the pants to shield the tent in my underwear. That effort worked well enough until I had to place the pants on the table.

Almost immediately Di noticed my condition and laughed more. "Looks like someone is a bit excited" she stated. Embarrassed I moved my hands to cover that area. "Oh no you don't Joe, hands at you side, let me look you over." She slowly walked around looking me over. When she was behind me I felt her hands on my butt cheeks. "Very cute and firm Joe, I like that" she stated.

A moment later I heard her open a drawer. Put your arms behind your back Joe and keep them there. I had no idea why but somehow I was finding all of this exciting. As soon as I put my arms behind my back Di place cuffs on me.

"I told you at the bar Joe, I'll control where things go from here. Now, about those underwear, they need to go now." Di took a pair of scissors and cut away the sides of my underwear, letting the material fall to the floor.

There I was butt naked, arms cuffed behind my back, and my tiny cock fully hard. As Di looked at it she began to giggle. "Oh my Joe, the girls told me you were tiny but i thought they might be exaggerating about it. Clearly you were not given a tool that is meant to satisfy a woman, but I do think it is cute. Stand right there, I'll be back in a moment" she stated and walked off.

As she was walking back into the room she was holding something in her hand. "I think this will work for you, it should be small enough" In her hand was a clear plastic tube that had an odd look about it. "Let's see how this looks on that pretty little clitty of yours," she said to me. I gave her a look of confusion hearing her call it a clitty. Di saw my look and said "well you can't really believe that that pathetic little thing passes as a cock, so from now on it is your clitty." I felt both embarrassed and humiliated hearing her comments, and yet I somehow also felt aroused.

"It's okay, in time you will come to accept it as your clitty," she said as she slipped me into the tube. She reached into the pocket of her robe and removed another piece of clear plastic and some white pins. She slipped the half round plastic piece under my sack and used the pins to hold it in place and slipped another over the top of my now flaccid "clitty" and added it to the pins. "Now comes the best part" she stated, while reaching into her pocket, producing a thin pink lock. She placed the lock in the center pin which had a small hole in it and locked it in place.

She stepped back and took a look at me. "That chastity tube is perfect for you, you look adorable wearing it. In time I am certain you will come to understand that it is fitting for you." She then used her phone and took some pictures of me. "Now lets go over a few things" she stated as she slowly untied her robe.

"First, from now on, you are to refer to me as Mistress or Mistress Di. Second, I am your key holder for now. Third, that pathetic little clitty is never going to be inside me. Forth, you will do as I say and when I say it. Fifth, you will be required to keep yourself shaved totally smooth at all times. Sixth, you will accept that you are the submissive and I the Dominate. Seventh, as a submissive, you accept that you may be punished for various transgressions."

Her robe fell to the floor and in front of me was this beautiful woman. Her body was perfect, firm breasts, lovely figure, great shapely legs, and her pubic area showed just a small landing strip of hair. "Yes, look at your Mistress, let your eyes wonder my body, know that you will worship it as i wish" "Kneel before your Mistress and tell me you accept these terms."

Her confidence stunned and aroused me, I felt drawn to her. Part of my mind was saying run while another was saying stay, you are enjoying and need this role. I looked at Di and let out a sigh as i slowly dropped to my knees.

While i was not certain what I was really getting into the words came out of my mouth, "yes I accept your terms." She looked at me with an odd look and walked behind me and smacked my ass which made me jump a bit.

"That would be yes I accept your terms Mistress, now say it properly."

"Yes I accept your terms Mistress" i stated.

"Very good Joe, now comes the next part. I'm going to uncuff you and allow you to think about what you have just said. I will give you 5 minutes to yourself to come to terms with this arrangement. When I return you will either have left, never to return or you will remain on your knees we will continue your training." She then uncuffed me, grabbed her robe and walked away.

She left me kneeling there, my mind racing in thoughts. I thought about her rules, how hard could they be to follow? I looked down at the chastity tube thinking, no big deal, I don't get to use it anyway. Then my mind pictured her beautiful body and how she might feel. I thought to myself, if I don't like where things are going i just would not come back. The idea of her having a picture of me locked up was a bit of a concern, what might she do with it? In the few moments I had, I decided to stay.

When she returned she was once again wearing her robe. "I see you decided to stay, I was hoping you would." She pulled out a pink collar from her pocket and placed it on me. "When you enter from now on you will immediately place this on in the hallway. This serves as a sign of your submission and obedience to me. Now stand up and put these on."

She reached into her pocket and pulled out a pink lace pantie and handed it to me. It smelled like it had a scent of perfume on it. She saw the look on my face and laughed. In a firm tone she stated, "Yes, you are to wear panties, your a submissive, now get them on."

I'm not sure if it was her firm tone or simply my desire to please her but i took them from her. Once again there was that feeling of embarrassment and humiliation that past over me. I looked at the panties and back at her with a pleading look of don't make me do this. Di saw my look and said "Do as your Mistress tells you and get them on Now!"

Why I don't know but i said "okay, Ill put them on for you." Di moved quickly and before I knew it felt a sound swat on my butt.

"That would be Yes Mistress, I'll put them on, correct?"

"Yes Mistress, I'll put them on" I replied.

I could not believe how the panties felt as i stepped into them and began sliding them up my now smooth legs. There was also the scent of the flowerly perfume to them. As I put them on, I heard the click of the camera phone, as Di took more pictures of me.

Once they were on she walked around and looked me over. She took a moment and adjusted them a little. "Perfect, they really make your sexy butt look so lovely and femme." I thought to myself, my butt looks femme, what was that about? Di returned and stood in front of me and again removed her robe.

"Okay Joe, you have done well, I think you need a reward. Come over here and kiss each of my nipples, don't touch me, don't suck them, just lean in and kiss each one and then thank me for allowing you to do that."

I looked at her and then her breasts, her nipple were hard and standing proud. I wondered why I was only allowed to kiss them, I wanted to feel them and suck on them. Something in my mind told me to do as I was told so I leaned in and gave each nipple a soft tender kiss and said "thank you Mistress for letting me kiss them."

"How are you at eating pussy Joe?" I could not believe what she had asked and how she asked it. My head kind of went down as i told that I have never done that.

Di laughed at my response. "You have never licked pussy for real?" I just shook my head, not knowing what to say. Yet again there was that embarrassment and humiliation.

"Actually, that is not a bad thing Joe. I can teach you one of your key duties from the start, with no bad habits to break. Get down on your knees and stay there for a moment." Eating pussy is one of my key duties, I thought to myself. This is sounding pretty good to me.

I watched as Di moved over to the sofa and sat down. She spread her legs wide open giving me full view of her beautiful pussy. She began playing with her pussy right in front of my eyes. Her fingers spread the lips open and she inserted a finger. "I'm already so wet Joe and that is because of you. Get down on all 4's and crawl over here between my legs.

I didn't hesitate for a moment, I crawled over between her legs while looking up at her. "Look at it Joe, to you it is my pretty Mistress pussy. To Real Men, those who are hung, it's a pussy, a cunt, a fuck hole, a slit, or anything else they wish to call it. Now, move in closer and ask me nicely if I will allow you to lick and eat my pretty Mistress pussy."

As i moved in closer the scent of her sex really hit my nostrils While looking at her I asked "please may i eat and lick your pretty Mistress pussy?"

She used her fingers to expose her clit, "lick here first, roll your tongue all over my clit." I rolled mu tongue all over her little sex button and soon had her moaning. "Push your tongue in me. Taste me, I'm all wet."

I was amazed at how wet she was as I worked my tongue inside her. I followed her instructions, licking her clit and pushing my tongue inside her, my face was soaked from her juices. I delighted in knowing i was pleasuring her as her moans grew louder.

Her hand grabbed the back of my head pressing me deeper into her sex, "that's it my sweet little sissy bitch, eat me good, lick my clit and make me cum." I was to busy enjoying her to be bothered by being called a little sissy bitch.

After several minutes she exclaimed "Yes, I'm going to cum, lick me good bitch." She pressed herself to me hard and I felt her body spasm. "Lick my juices up, do it now and get your reward" she exclaimed. After several more moments of licking her juices she pushed my head away.

"Okay, enough training for today. Get dressed, keep the panties on and leave my pretty pussy juice on your face so you can enjoy the smell. I want you back promptly at 1100 tomorrow. Make sure you are wearing your panties."

I was somewhat unsure if I had done something wrong as i got up from between her legs. "What about that thing you put on me, are you going to take it off," I asked?

"Did you forget Mistress" she quickly snapped.

I responded, "What about that thing you put on me, are you going to take it off Mistress?"

She looked at me and smiled, "Oh no Joe, that stays on until I decide to remove it."

"I want you to stay in your panties all day and night, they only come off when you take a bath and shave yourself smooth again. I'll have a fresh pair of panties waiting for you tomorrow, then you will have 2 pairs. I also want you to get use to sitting to pee, you'll understand why soon enough. Leave you collar by the table at the doorway."