What a Night

It all started out innocent enough...here I was laying in bed next to my wife on this cold winters night, just two nights before Christmas. We had arrived on time to her parent’s house with nothing unusual happening on the way. It had been a pretty dull night and with her parents having gone to bed the two of us and her younger sister had decided to get comfortable and talk. In hardly any time at all the two of them had drifted off to sleep leaving me to stay up waiting for the middle sister to arrive to complete the family for Christmas.

I grabbed my laptop and decided to jump online to see what was happening in all my favorite chat rooms. While online I got an private message from someone named Princess^Perfect telling me "kneel and prepare to serve me" Not really being in the cyber scene I laughed it off and ignored it going back to chatting with my peers about our daily lives and the Christmas time. After about two minutes had passed my screen flickered with another private message from the Princess; berating me and telling me to prepare for my punishment if I did not follow her commands. Again I chuckled and this time copied and pasted the message to the channel I was in so we could all get a chuckle out of it. When my screen flashed to alert me to my third message from the Princess I started to get a little irate and without reading it I simply responded "Listen I don't know who you are, but I'm not into the whole cyber scene and especially being someone's slave, so please leave me alone." and then closed it without even reading her message. Within seconds my screen flashed with her response and I thought oh great now I got to report this person just so I can get some peace on here. As I opened her message and began to highlight it to send it to the Operators my eyes got caught on her second word "Michael" which is my name. I immediately thought oh shit my computer has been hacked into and this person has my name, but then I remember I don't use my real name anywhere...this has to be someone who knows me. I thought I better play along to see if I could figure out who this person was so I decided to read her message. "Princess^Perfect - Look Michael, you little shit, I know who you are and where you are at...either kneel now or pay the penalty!" I responded "ok fine, I am now kneeling..." I flipped back to room I was in and told them I had to take care of something and would be back shortly.

I returned my attention to my mystery Princess and found another response from her telling me it was too late and that I was to be punished for my disobedience. I thought back to my single days and replied "yes Ma'am, whatever you wish." I was then told to go into my sister-in-laws room and quietly find her sexiest pair of panties and get them." Trying to play along I responded that she was asleep in her room and that it would wake her up. I got an immediate response back telling me the lying would only get me punished further, that she knew my sister-in-law was asleep in the same room as my wife. I quickly became nervous knowing that my laptop was the only computer in the house and that meant that this person had to be watching the inside of this house someway. I quickly and quietly got up and started to close all the curtains and look to see if I could see any miniature cameras anywhere. When I came back to my laptop I saw she had sent a couple lines of "LOL" and that closing the curtains would not get me out of this. I was then told that due to my disobedience of not retrieving her panties, lying about her, and closing the curtains I was to now to not only get her panties, but also a bra, and a sexy piece of lingerie. With a warning, that if there were any further actions of disobedience I would be getting her punishment first hand. Not knowing who this person was or how they knew what was happening inside this house I responded "yes Ma'am please forgive me" and then went and got what was I told to.

When I came back she instructed me to describe what clothing I got in as most detail as I could. I told her I found a pair of pink satin thong panties, matching bra which was a 40D, and a pink see thru Baby Doll outfit with fur on the cuffs, around the neck line, and the bottom of the outfit. I was then told to strip and put on the outfit I picked out for her. I pleaded with her that I am not made to do this as I was expecting company and that anyone could wake up at any time. Calling me a little sissy cock slave she told me I should have thought about that before I disobeyed her and that if I did not do as told she would make sure that everyone was up before I had a chance to return the clothes. Without knowing what I could do I weighed my options this stranger on the net that knew so much about me and what was happening in this house gave me; I knew I couldn't risk her waking up everyone to catch me with my 18 year old sister-in-laws lingerie I gave in and submitted to her. Stripping out my clothes I carefully looked all around to make sure no one was awake and then put on the outfit. The thong was a little snug, but overall the clothes fit. I should take a moment to describe myself to you.

I am a 29 year old happily married man, standing at 6'1" tall and weighing 135 pounds. I'm not super skinny but obviously not overweight or very muscular at all. But anyways back my tale here...after putting the clothes on I sat back down and got ready to tell her that I had done it, and saw she had typed "There now that is a good lil sissy panty boy...don't you feel better wearing girly clothes? I know you do since you are not a real man, but actually just a little sissified slut that loves wearing women’s clothes. I told her no that I did not enjoy it, and that I was only doing it since I was left with no other choices except to get caught with her clothes and be in deep shit with my in-laws. Immediately I got a response back that simply said "SMACK!" Followed by another response that said if I did not want that to smack to really happen I had better learn some manners. I was to address her only as My’ Princess, and that I had better admit to being in love with wearing these clothes. Again I submitted and said yes My’ Princess please forgive me, I do so love wearing this outfit. It was at that time that I noticed my other sister-in-law pulling up and begged that I bet let go so that I may change before she came in and saw me. I was quickly told no, however she would allow me to go into the bathroom with my laptop and clothes so that we may continue this in lesson of life, if I would tell her that I would submit to her, and become her sissy cock slave. Desperately just wanting to get this over with I quickly respond yes My' Princess I would be her sissy cock slave. With that she said go...and I quickly grabbed everything and made a mad dash to bathroom, just as I shut the door I heard my newly arriving sister-in-law open the door and quietly come into the house trying not to wake those sleeping.

Once inside with the door locked I thanked her, and asked what it was that she was going to require of me. She responded telling me that I was to use tissue paper to stuff the bra full. When I had finished she asked me if I had a hard-on yet caused by the outfit. I noticed then that the soft feel of the satin thong against my cock and balls, and the ruffling of the fur against my stomach, ass, and neck, combined with the feeling of having fake tits did in fact excite me and had caused my cock to come to full attention and strain against the flimsy pink thong. I shamefully admitted yes and told her that my cock was in fact at full erection and straining to be released as it was the hardest it had ever been at 9 1/2".

She just laughed and then without notice my sister-in-law opened the door and came in. I stood up to try and keep her from screaming and waking everyone else up and to try and explain. She just simply looked at me and asked did I give you permission to stand up. Shocked I looked at her and she just smiled and then walked over to me pushing me down to my knees. Now you should know that she is about 5'9 125 lbs with long strawberry blonde hair, a trim and fit tanned body, with about 38d tits. She looked me over and told me what a complete sissy slut I looked like and how I should be ashamed that she walked in on me wearing her baby sister’s panties and lingerie, with a bra stuffed full of fake tits. She then looked at my cock and said my is that...is this little sissy slut girl all excited? Laughing she took hold of my cock through the satin thong panties and gripped it stroking it up and down and then asked if like having my precious little clit fingered. Lost in the feelings of it all I could only murmur yes that I liked having my clit fingered. She then asked me if I wanted a good fucking with her, which I quickly responded yes. She just giggled and said ok...then stopped stroking and stood back up stepping out of her dress I saw she had nothing on underneath.

She reached up and starting playing with her breasts and told me that if I wanted her I was to do the same with mine...so I started fondling my fake tits. As she was fondling her tits my eyes gazed over her beautiful body and saw that she was clean shaven...this made my cock drip its first drop of precum. When she saw that she said that my pussy was good and wet now and told me to keep playing with my tits while she walked behind me. She then told me to get on my knees doggy style and stepped back around into my view wearing now a strap on that had to be at least 9 inches long. She could see the fear in my eyes as she quickly grabbed my head and pushed the monster past my lips and deep into my mouth. Forcing me to suck on her fake cock she laughingly told me that all good sluts suck a cock before they fuck it.

With tears now streaming down my face in humiliation she pulled the monster from my mouth and walked around behind me. I begged her not to use it anymore but she only slapped my pantied ass hard and told me that I was her sissy slut and she would do as she pleased. She pulled the thong panties aside and grabbed my balls in her hand massaging them while she lowered herself and took my cock into her mouth. She licked my shaft up and down both sides then pushed herself onto my cock taking almost all of into her mouth giving me a killer blowjob. When she could sense I was getting close to cumming she pulled off my cock and started licking and tongue fucking my ass.

After a moment or two this kneeled behind me and put the head of her dildo against my virgin asshole. I begged her again not to do it, but was answered with a harsh squeeze of my balls and her saying..."what you little sissy cock sucker...you want me to eat your pussy and suck your clit, but not want me to fuck your pussy? Are you nothing but a little cock tease? With that she laughed and pushed the head of her monster into my ass. I felt blinding pain as my as tight ass was punished and stretched wide. She just reached around and grabbed my padded tits pulling me back against her until she had completely sunk her cock into my ass. I was now sobbing and whimpering in pain and she just laughed as she began to slowly fuck my ass and pull me into her by my tits. As the pain started to lessen I began to beg her to stop, she just laughed and told me since I couldn't keep my pretty cock sucking mouth closed she would just have to fill it. She paused fucking my ass long enough to reach behind her and pull something out of her bag, then put another dildo about 6 inches in front my mouth again. I closed my lips tight, but she forced it into my mouth completely gagging me on the tip of it causing me to push it out. She fastened a harness onto my head that held the dildo in my mouth continuously pulling it in all the way while I kept instantly trying to force it out. She just laughed at me saying that I was truly a natural cock sucker with the way I was keeping that cock sliding in and out and then went back to fucking my ass again. After about 10 minutes she started to pump my ass harder and faster and grab my bra tighter as she neared her orgasm. When she finally came down, she pulled out of my ass, and removed the harness from now sore mouth.

She looked at me and laughed an evil laugh telling me that from now on I was her slutty lil girl, and that she was going to call me Michelle. She told me that I was to start wearing a pair of panties every day and whenever I was alone I was to be fully dressed. She told me to make plans the day after to Christmas to go shopping with her, as we would be going out to buy me several pieces of lingerie, and panties, bras, and dresses, and to be ready to try on each one asking for the opinion of the clerk. She looked down at my panties and saw where I cummed while she was fucking me, and just grinned saying that she knew I would get off sucking a cock and being fucked. She told me to stand and remove my soiled panties. As I did she told me that I was to take them in the most seductive way I could rubbing my swollen clit and dripping pussy, sliding them slowly off my body. When I had finished taking them off my cock was again at full attention. She looked at me as said, just like a true slut...you can never get enough can you...you little pussy.

She told me to take my cock and jack off in front of her, but to make sure I did not cum without her permission. As I took my cock into my hand and began to jerk off for her, she picked up the cum filled panties and told me to clean them by shoving them in my mouth. I felt sick from my first taste of cum, but she just laughed and told me to get used to it. Every time I was to cum I would be punished to eat every drop. As I stood there wearing only the flimsy baby doll outfit, and the stuffed bra, with my cock in my hand madly jerking it off and my own cum soaked panties in my mouth I could tell I was getting close. I spit the panties out of my mouth and begged for her permission to cum. She knelt down in front of me and took my cock into her hands and said I could cum only when she had me in her mouth and then quickly took my cock into her mouth and began sucking it. I could feel her sucking every last drop out my mouth and since I hadn't seen her spit or dribble any I only thought I was saved as surely she had to be swallowing it all. When I was finished she took her mouth off my cock and began to spit out my cum into her hands. When she was done she had what looked like a gallon in her hands and told me to open my mouth and stick out my tongue. She started by taking a large glob of my sperm and placing it on my tongue and telling me to sallow which almost made me puke right there. She warned me not to and that I should enjoy it...as it was a privilege to be able to sallow a man's cum. After several mouthfuls I had finally eaten all my cum, she told me to undress and put on my clothes and follow her.

We walked back into her sister's room where she looked through the drawers and pulled out another pair of white silk thong panties, with several little pink hearts all over them, and told me I was to wear these until we got me some of my own. With that she made me strip again and put on the panties. The feel of the new clean silk panties against my cock had it hard again before I was able to get my pants up. She just looked at me and smiled and said that I would be a good sissy girl for her. She kissed me deep and then patted my silk panties and said I should go to sleep; tomorrow was going to be one fun filled day.

If you like this and would like to see a further degradation into this life please email me at the link below and let me know. Or if you think Michelle should claim her manhood back and turn his Princess into a submissive slut let me know that as well.