Nightime adventures

I had a girl friend name Jill. Jill was almost my hight and built and she was into classes for Beautcain/Fasion. One day she was having a hard time with her make up class doing the super model work and such.

She walked over to me one night ask very embarrassed and quite "Micheal can you help me out with someting please". I looked at her abit worryed because of the tone in her voice "I supose, how much you need?" saying jokingly and laughing "Your an ******* shutup lol". I knew I broke the tension abit she started the question again "Umm....I'm realy having a hard time at school at the moment and was wondering if I can practice my make up on you?" her voice quicken "I promise I'll keep it a secret and just a few times a week I'll try not to take up ..." I put my hands up and said "wait dont you have a face dummy or something?" My word said that but my mind was like OH MY GOD THIS IS GOING TO BE SOOO MUCH FUN!!!. I had to keep it cool becuse she didnt know about me and my past getting into my moms outfits and makeup even when I was in high school I use to every once in awhile.

She was stading there looking like I killed her dreams and I felt realy bad about it so I told her "sure what the hell." Her face lite up "Oh thank you thank you I love you so much." She ran out into the bedroom and got out her makeup kit right away "right now?" I said but realy going yay inside.

She did me up to look just like Drew Barrymore on the Covergirl comerals and I don't know much about terms for diffrent looks and such but I looked sexy hot and my pants got abit tigher that night. She looked at me and almost cryed covering her mouth with her hands and gasping admiring her work "your so preaty, How wasn't you born a women?." If I didn't have blush on she would see me blushing. "Ok i'm done you've been a real sport, heres some make up remover thank you so much for letting me do this. It's got to be killing you inside." She said laughing. "Nah it's not that bad realy not like your making me go outside or your taking pictures." laughing back at her. "how long are you going to need to do this for again tho?" I asked her. "My test is in 3 weeks why your not getting second toughts about this now?". "no no im ok." I said to her.

I walked to the bathroom to remove the makeup and saw myself in proper light and was lost for words. I've never seen my face looking that preaty and sexy before. I lost myself in my own eyes. Women all know the most powerful part of there body is there eyes. I dont care what anyone says lock eyes into a womens eyes and tell me you dont get lost and tranced and I will call you a lier. At that moment I was hooked again the Fem in me awoke and I wanted more and more. I must of stayed in there for like a half hour just staring. I hear a knock on the door and snaped out of it " you ok in there" Jill asked. "yes im taking a dump and got into a mag i'll be out in a min" I told her. I quickly washed up and came out.

The next day she was off to class and I got off work. I went into our apt. and yelled "hello anyone home?". No one was home my mind started to think about how I looked yesterday. I went into her closet, my god the wardobe she had and most of it fit me like a glove as well. I pick out one of her sexest dresses and stockings, pantys and bra. I felt amazing puting it on and almost cumed in her pantys. Her grandma passed on 2 years ago and had aton of wigs that was worth aton of cash I kinda felt bad for wearing one of them but I would be a bald lady if I didn't. I was thinking this would look great with Jill doing my makeup and I hid the outfit in the bathroom.

Full of giddyness I waited for her to come home for 3 hours. Her car pulled into the driveway and my heart raced and I almost fiented with excitment. "I'm home and learnd a new look You busy?". I walked over and gave her a huge hug and kiss like she never had or i've done before. "well that was nice what was that about?" she asked me. "nothing I just love you thats all". We sat down and she begain going to work again.

My body trembled abit as the brush hit my face and I knew what my outcome would be and how that dress felt. She finished and looked over her work and told me I could go clean up, I almost ran into the bathroom. I tryed very hard not to look at my face in the mirror as I got dressed and I turned on the proper lighting and stared at how I looked in the full mirror and giggled like alittle school girl I was so happy I cryed with tears of enjoyment. My body siverd as I twist and twirled. I knew my time was sort like this and I didnt want her to repete yesterdays event of her coming to get me so I washed up and rehid the outfit till I knew I could put it away when she wasnt looking or home.

Couple of days pasted and she needed to pratice again. She got out her makeup kit and went right to work again this time she stayed abit longer looking over her work. I think she stated to like the way I looked she pinched my chin and said "Your so sexy as a women you know that, I can just eat you alive". "haha your so funny" I said in a sarcasic way not to blow my cover "your not turning into a lezzy on me are you?". Thats when she said somting that floored me abit. "Well I always wondered what that could be like. I love
watching Lez porn and such and when the one chick would tell the other what to do I was think could be fun". Well she got my attention with that and I had a way to tell her about how her makeup and dresses made me feel alive.

Her test was coming up so I got a misstress outfit from online store and a strap on dildo with a vibrating clit stimulator. Had it all rushed order so it would make it here on time. When it all arived I tryed it on and felt a powerful feminine feeling rushed over me I stayed in it for so long I almost got busted. I took it all off and hid it away till she got home after her test she practice on me more and I spilled the beans on my plan 3 times I wanted her to get her test over with so bad.

Finaly test night I knew she was ready because she practice very hard everyday some on me other time with the head and I was smoking hot or cute. Yet again she took forever to get home. I got a phone call and it was her crying badly "I.....I.....I failed, I realy did bad. I dont know what happen I lost all my skills and froze badly!!!". I started to cry myself cuz I know how hard she worked on making my ugly mug beautiful. "thats ok honey you'll get em next time, I'll see you at home".

I was so heartbroke and was thinking do I realy want to do this and come out on her like this. She got home and walked into the apartment. "What did I do wrong, I have no clue how I faild?". I looked deep into her eyes and asked her "do you want to do my makeup again, make me a whore or something could be fun?". She laughed and got out her makeup did me up very sexy. We laughed about it but I know she still hurt inside about failing. "Why dont you go sit in the message chair for abit and relax" I told her. She did and the chair was right behind the hallway to the bathroom where my misstress outfit was.

Once agian I felt that shiver and trance when I looked at my eyes while I panted my nails as well. I came out the door abit nervose but giddy. With a sexy walk I got right behind her with out her looking back and started to rub her shoulders sexuly. "OHHHH thats feels so good right now" she said as eyes shut abit. Perfect I was thinking. I got in abit deeper rubing her face.................neck.................and when I went back to her shoulders she notice my sexy red nails. "WHAT TH........!".... "SHHHHHH" as I put my finger to her lip to shut her up. "You don't need to say athing Micheal told me you wanted a lezzy fun time and I Michele am here to give it to you. From now on your in my control, you do what I say for all you are is a little prissy girl that failed her test and needs to learn what it is to disapoint me. Now I want you to go into your room, strip, and wait for me like a good girl. You dont want to disappoint me do you?". "no Mich.....", "ah ah ah It's MISTRESS and nothing else!" I intruped. "Yes Mistress" she replied with a shocked look on her face as if she seen a ghost and started to head to the room. "STOP!!!" I yell " Curtsie before you leave yer mistress, Im going to have to punish you twice as hard now go!!" Jill Curtsied as told and went on to the bedroom.

Five minuts later I came in noticing her naked and holding the strapon. "you dont desive that yet do you missy?" "ok whats going on here?" replied Jill. "get on the all fours you need to take yer punishment!". I pushed her to the bed and spanked her hard with a riding crop across her ass. Thwack, left a small red strap mark on her ass and again and again!!. "you need disapline little missy, you lack focuse that I can teach you" THWACK again. I see this was kinda turning her off abit and a man is disapline her in Fem and calling her missy prob didnt help much but she keep going.

I grabed her and fliped her to her back and started kissing her in ruby red lips to her bubblegum pink lips that turn her on. She kissed back harder as her nails dug into my back. She never did that before. "now that u know I can give you a leason in pain it's time for the leason in pleasure. Do you want me to pleasure you my little missy?". "yes Mistess! Yes!". "good cus Misstress knows how to please her little missy and her pleasure is mine and mine to control".

My hand went down her arm to her ass, down her leg real gently and softly. I slid it to her clit and put alittle pressure and rubed. Her lower lip quivered like she was cold. All of this was new and I know she was realy enjoying it now. Her pussy was wet to start off and with the simple touch that I gave her it became ever wetter.

I thrusted a finger deep into her pussy and felt her hips buck hard. Pulled it out and thrusted two deep into her pussy. "you like when Mistress playing with her pussy". a soft "yes" came out of her mouth and I trusted harder and deeper into her pussy yelling "Speak up Misstress don't want strain to hear you scream!" and yet another thrust "YES!!" she screamed. "Goooood Missy likes to scream dont she?". "YES!!!" another scream comes out.

Her hips bucked realy hard now and her pussy became even wetter and wetter as she was about to climax "your going to cum, are you going to cum?" "yes, yeS, yES," More screams "I'm going to let you this time but next time you need to wait for me to say you can, I must give you permission to cum you got that?". "Yes misstress" Replied My little missy. "ok sweety go ahead" as I rubed her clit fast and hard and a stream of her pussy honey came pouring out. "I've see you seen my strapon, I think it's time to fuck you hard with that does that sound good missy?". "yes" she replied.

I did buy a removeable dildo one and I had it apart at this time I sliped my cock in the dildo holder and put on the same color condum to make it look it like the dildo. My missy notice this as a slaped her in the face with it. "Suck my cock!" I told her and she did. She was abit wierded out by me asking her to suck my cock with a condum on but it make it more like a real dildo with the latex. She sucked nice and slow and sent shivers down my cock to my spine.

I took her and fliped her around and slamed it into pussy doggystayle. I ponded hard as she started to buck her hips again "you dont cum with out me saying you can missy remeber that!". she was in tranced and I said "you must realy like my cock huh missy? Missy? MISSY?, Oh you dont want to anwser me when I ask you a question?. You need another punishment!".

I had a tube of lube as well and before she could awser me I had my cock out and in her ass before she could say anything. She never had anal sex before and was alway against it. Not this time she was putty in my arms. She got pissed at first but I didnt care this was a punishment. Now I like ass play myself but remebering the first time I did anything down there it hurt abit. "you see a lesson in pain can turn into a lesson in pleasure right missy?". She awnserd this time "YES!!! OH GOD YES!!!". I was almost into climax and I could tell she was too the bucking started right back up. "go ahead you want to cum I give you permission to."

I grabed her arm and helped move her hand down to her clit. She ruped hard and fast the screams came louder and louder as she came again. I pulled out and held it for abit till my feeling slowed down abit I went back to the kissing took the strapon off reinserting the dildo and told her. "there now Misstress lesson arnt so bad now are they?". "No Misstress" she replied as she kissed me back. "now time for your real pleasure Missy!" as I handed Jill the strapon and said in a deep sexy voice "your turn!"


Part 2 Your Turn

She gazed at the strapon and stared at me abit confused as to what I just asked her "your turn?' she replied. Staring back at her and with the most sincere look on my face said "abloslutly your turn. I saved my cum for you its still brewing waiting to be teased out." "Anything?" she replied again. With a deep sexy voice I could come up with I whispered "Anything".

Her face got real serious now as if she was thinking of something "I want you to get on yer knees with yer hands behind your back." I jumped up quickly "Yes Misstress." Jill went to her dresser and got out her sleeping mask and covered my eyes. With my sight gone and only my hearing left my curiosity kicked in. "Oh I didn't think you where this kinky, what types of movies are you realy watching?" "Who said you could say something?" she replied firmly. "no one Misstress." I said all sexy like getting into the spirt of things. I heard a russeling again in her dresser and before I knew it I was cuffed then shackled. "you stay there my little sissy, Misstress got to go do something real quick." Jill said as the door shut. My mind was quickly racing. What just happened here and why am I hog tied oh my god what the hell does she got instore for me. A long time has past or it could of been short I didn't know and I hear talking in the background. All I heard was "Good..................Head....................oh yes he...................." there was another voice, did she call for a friend to come over as well, is she going to let me have my fantasys three way I jokinly told her about but lets face it we want it right fellas.

A few moments past and the door reopened. "You see Head Misstress nice and sissyed. He did it all by his little self to please me and my little sissy did please me very nicly." Jill said. "Head Misstress!?" I yelled. I deep seductive voice came over and said "Thats right sissy. I am Head Misstress Alex Shadowdancer of the House of Shadowdancer. Tho now your not as submissive as we would like you to be, but in time you will be a proper sissy for your Misstress." she said. "What the hells going on here?" I yelled again. "Go ahead and explain to your sissy Misstress Jill." Said the Head Misstress.

Jill came over and said "The school I was going to was a Misstress training course. I hate to say it like this but, your my final exam. I've been studing you for along time now and seen your sissy side. The way you use hand guesstures, walked sometimes and talked" Jill said. "So I'm just home work for you, I loved you deeply for years" abit hurt by whats going on. "Noooo Noooo." Jill replied, "You needed a push that I can give you i've seen the video of you dressing in my cloths and such. I got a camrea up looking at my dresser all them dresses where for you took you long eough to finaly wanted to wear them. Then I came up with the makeup idea and that got you going and you do like the way you feel all dressed up in makeup and looking girly right?". I was busted and kinda shocked at all of this but in a gentel and soft voice almost a whisper "yes" I said. "What was that sissy?" yelled the Head Misstress. "YES!" I shouted "YES! for years and years I wanted to be a women but I've come to terms with me being a man I sometimes did feel I got the short end of the stick at times". As a tear rolled down my face. Jill took the sleeping mask off of my face and looked deeply into my eyes smiling "now this is the only time I going to ask you, depending your anwser is how we will go from there". I gazed back into her soft blue eyes abit tranced by them. Damn them eyes I was thinking. She stared back at me and asked "do you want me to train you to be a women, to pass as a women, this is a one time offer". Thinking abit about how I loved her and cared for her and now she wanted me to be her I stared back into those eyes and with a grin on my face said whole heartly "yes my Misstress".

The Head Misstress never understood why Jill was so nice to her sissys while training in the house but it did get results and Jill did get a A+ in punishment class. She was used to the firm but fare method and told Jill to kneel at her feet. "As Head Misstress of the House of Showdancer I hear by grant you your last name. At my feet you are Misstress Jill". She motioned Jill to raise "But as you stand you are now Misstress Jill Shadowdancer one of my sisters rise my sister and take charge of your sissy. You'll have 4 years to make him into a proper lady and the best Misstress with the most proper one takes my chair" She said firmly. Jill had tears in her eye and I'll have to admit I was proud of her as well.

The Head Misstres turn her attention to me now and said "your lucky with this one. Other Misstresses are not so nice". She made a motion to Jill to come over to me and ask "well whats IT'S name?". she asked. Thinking in the back on my mind oh great now im a it what did I get into? Jill looked at me and smiled and said "It actuly named it's self Michele Head Misstress" Jill said proudly. The head Misstress was abit shocked on how far I took this and how much I had planed to make her feel better. Head Misstress motioned me over to her and I walked my my knees to her. "As Head Misstress to the House of Shadowdancer I hearby name you sissy michele. It's now up to you to learn from your Misstress, she is in complete control of you and your life now. You will be punished and rewarded by her and other Misstresses in the house when on House grounds. Do you understand!" "yes Head Misstress" I replied. She turn her attention to Jill again and said "It's time I leave you two alone you have alot of explaining to do to her. Good night to you sister and good work". Jill curtiesd and thanked her as she left our apartment.

Jill came back and told me everything rules of the house rules of this house and what I should do if this happens thing like that. I looked at her as my brain kicked back on and said "Ok pause for a sec time out what the hell did I get myself into here?" Jill replied back "im sorry for tricking you like this and baiting you into this but it was the only way I knew I could get you into doing this for me and not just for me damn it for your self. I seen how unhappy you are at times or the way you hold back crying at sad parts in moives trying to be that mahco man that you are but with that little girl screaming to get out. It killed me to see you like this and I do love you very much but now I feel a deeper conection with you because I can make you fully happy. It needed to be done and as Head Misstress said your lucky it wasn't another Misstress that profiled you. I gave you the choies of this life, you took it. Not many Misstress gives choices, there is a forced side to this world that I dont agree with but I love my life and the power I feel when I'm training. We don't have to be Misstress and sissy all the time but when I do ask a sissy question or give a task it must be anwsered or completed you got that my sissy" "yes Misstress" I repailed.

Things starting to turn normal I grabed at my balls and they remined me that I wasn't done yet. "Oh my god!" Jill screamed "I almost forgot on how you held back so I could make you cum". She stared deeple into my eyes and grabed my cock and said "now my little sissy its abit of training time for you". She grabed onto my cock in my panties and asked me "do you like it when Misstress playes with your cock? humm" I told her "yes Misstress" as I growned abit. "No you don't like it when I play with yer cock becuse you don't have one. Do you sissy?". I was abit confused on this and asked "I don't Misstress?". "No What does a women have down there?" she said with a smile. "A pussy" I replied. Misstress Jill tightins her grip on me and made it hurt abit "Once again What does a women have down there?" said abit more firm. "A pussy Misstress" I repiled. Her grip losens abit "Thats right but lets remeber class in session and you dont want to disrespect the teacher now do you little sissy?". "No Misstress" abit turned on by the way she handled this. "Now sissy what part of a pussy does women like to have played with the most?" "A clit Misstress" saying it happy that I knew a anwser. "Very good sissy this is your sissy clitty. Do you like your new sissy clitty?" She said prodly that I knew an answer. "Yes I do Misstress I like my new sissy clitty cuz it makes me feel so good" geting into the sprit of things.

Misstress Jill let go and grabed my hand and placed it on my new found clitty. I'll have to admit I liked calling it that abit more than a cock or penis it had a cute ring to it. Misstress Jill voice came off slutty this time "Play with yer new clitty till it makes milk for Misstress". Now i've jerked off before and i'll have to admit this was 1000 times better I could swear the feeling was diffrent as I rubed it like it was a clit and till I was there. I reached for a towle or a rag or something and Misstress Jill grabed my hand and tossed any and all items that I could use to catch my cum aside saying fermly "Ah Ah AHH, your milk goes on sissys tummy then in yer tummy" said with a smile. I've never tasted cum before and with this new found life I did not diagree with what she said.

I rubed my clitty abit harder and fast till I shot my milk all over my tummy and I cam so hard I shot some on my face and near my mouth. Misstress Jill seen this and was shocked on how well I enjoyed this and said "Good sissy clean it up all in yer tummy not one drop can be wasted". I took my hand wiped up abig handful off my tummy and placed it my mouth. My cum tasted realy good which I was shocked and feeling abit slutty like a porn star. Misstress Jill came over and kissed the cum off my chin herself "See Misstress like sissy milk too, lesson over".