Lonely Man Becomes a Sissy Ch. 02

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Sissy wakes up to a new world with Mistress.
3.5k words
4.28
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Part 2 of the 2 part series

Updated 10/02/2022
Created 09/15/2006
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rebeldoll
rebeldoll
242 Followers

I awoke groggy and confused. I normally wake up in my nice queen size bed. I didn't know where I was. I had had the craziest dreams of me being a woman and getting me ass beat and fucked. Then I realized that it was no dream. I was tied down, my arms in front of me, I was on my stomach, my ass stuck in the air, something holding my feet spread apart, and I still was gagged and had the cb-2000 on. I could tell I was still wearing the false tits, corset, hose and my heels were on my feet again and felt locked in place again. I could see that I was on a bed in a candle lit bedroom that was very nicely decorated and some type of industrial music playing in the background and some rustling noises near me. I began to freak out. Only god and my Mistress knew what time it was. Had I missed work? If so, would I get fired and lose everything? Where am I? And when the fuck am I going home? I wanted this to all end, and I started crying.

"Awake are we cunt?" my Mistress said.

I tried to mumble yes and get me out but no real words come out when you're gagged.

"I had to put your heels back on you, I love fucking a whore while she wears her slutty heels for me. I hope you slept well. It is Sunday afternoon now, and I know you have work tomorrow. So, lets see if you make it through the night. If not, I guess there will be an opening at your office."

She began laughing so hard that I hope she would have a heart attack. I could tell she knew I was angry. That only made her laugh harder WHILE pointing at me and calling me names. I tried to ignore her and turned around. In front of me were the pictures of me dressed up and sucking on the dildo, and some of me standing in front of my house. I could tell she took those from inside of her car when she picked me up. Also in front of me was a TV with a live image of me and my Mistress behind me. She was wearing the biggest strap on dildo I had ever seen and she was stroking what looked like K.Y. all over it. I tried to get out of my bounds and escape only to find out that my feet were also chained down AND spread apart.

"Can you see yourself bitch? Can you see me? I hope so! I want you to see this. Every girl remembers her first time, and god damn it, you fucking will too bitch!"

And with that, she thrust her fake dick into my ass so hard that I couldn't scream. It hurt so bad, nothing but air came out when I tried to scream. She then began fucking my virgin ass with such force, the bed began to shake and the pictures on the bed were falling off. I tried to scream. I tried to fight it, but it only made it worse. IN AND OUT, HARDER AND HARDER. I tried to break free. I tried to say stop. IN AND OUT, HARDER AND HARDER. I began to cry so hard I was balling like a little girl with a skinned knee!

"You FUCKING LITTLE BITCH! ARE YOU CRYING?!! You deserve those panties and those tits. Your male life is OVER!! You are mine and you better learn to live with it. Your man cunt and that mouth of yours are mine and I will do with them WHAT EVER I WANT WITH WHOM EVER I WANT!! YOU GOT THAT BITCH???!!!"

She had a steady pace going now. I could tell she was getting off on the dildo as well, so it must have been double sided. She clawed her nails into my back as she fucked me, and I cried harder! It was so humiliating to have to watch the reaction on my face on the monitor. I could see my fake tits shake with ever hump of my Mistresses dick. The weight of my new breast felt like I had had them for life and moved, as a real woman should. The sad thing is, no matter how much I wanted it to stop, AND I DID, my dick was acing in its cage from being aroused. My body was betraying me.

"I want you to commit to me. I want you to obey. I want you to say OUT LOUD that you loved to get fucked by your Mistress, and that you are MY little girl slut and want more cock. Say it or you'll fucking pay bitch!"

I felt her unlock and undo my ball gag as she kept fucking me. I fixed my jaw and rearrange my mouth.

"Say bitch or I'll fuck you until your ass bleeds!!"

Something shut off in me and I began to say,

"I will obey you Mistress, I promise! I want your cock in me. I want to be your little girl slut. I want to wear panties and pretty undies for you. I want to wear dresses that show off my breast. I want you to use my man cunt and my mouth however you see fit. PLEASE PLEASE MISTRESS, I WILL BE GOOD!! I WILL OBEY!!!"

I was crying so hard by that point that I couldn't say anymore. I just kept crying as she kept fucking me, and fucking me. Then, it started to slowly feel good and I actually wanted it. Dear god! What's happening to me?!

"That's a good girl Lilly. You will get what you want and I will get what I want out of you, OR, this tape you are watch will go out to everyone you know. It would make a great stocking stuffer for Christmas, don't you think?"

As I tried to respond, she slapped my face so hard I bit my tongue, and it was bleeding.

"You will speak only when I tell you to, and I didn't FUCKING SAY SPEAK YOU BITCH!!"

With that, she shoved some clothe in my mouth, followed by that ball gag and locked it once again behind my head.

"D o you like that taste of my panties bitch? I hope so! They are what I cleaned up yours and my cum from last nights little fuck session. Get use to that taste too. You will have so much cum in you, that I think you will get "Cum Dumpster" tattooed on your ass."

She began to trust her dick into me harder and deeper. BANG BANG!! She began to scream from her orgasm as she dug her nails into my back again. I tried to scream from my orgasm but nothing was heard through my gag. We came at the same time! My body went limp, as did hers. She lie on my back breathing heavy and moaning and repeating "oh my god" over and over. I tried to breath and wipe the tears from my eyes on the bed. Then suddenly, PLOP, she pulled out of me and I was left there in my shame, trying to recover.

WHACK WHACK!!

She was beating me again, only this time, with A WHIP!! She cracked it against my ass, my back and my thighs. I began crying again.

"I DIDN'T SAY YOU COULD CUM YOU FUCKING WHORE!! And all over my bed spread too!! YOU BITCH!!"

I counted 10 strikes, and then she stopped. I was crying so hard from the pain, that couldn't see through all of my tears. She grabbed my chin, lifting my head and slapped me across the face. I just kept crying. I could feel here start to untie me. First my feet were unchained and the spread bar undone. Then, my arms undone and I dropped to the floor. I had no more strength. I just kept crying.

My Mistress leaned over me and smiled.

"You are such a sight to see. You are such a little sissy bitch. Aren't you??!"

She then flipped me over onto my stomach and hand cuffed my arms behind my back. Then placed the blindfold over my eyes. I could feel her start to lift me up and she said, "Get up NOW!" I helped her pick me up. I could feel he put a leash onto my cb-2000 AND my collar and start to drag me by my "clit" and my neck. She pulled me down till I was on my knees. She pulled my blindfold off only for me to see her dildo, right in front of my mouth. She undid my gag and pulled the panties out of my mouth and shoved them down my cleavage and just said "SUCK IT!" I closed my eyes, and began to suck her fake dick like it was the last thing I would ever do. I wanted her to be proud of me, AND I wanted to do it right so that I wouldn't get beat again. She started to face fuck me slowly. Her cock slowly going deeper and deeper down my throat. It got so far down that I could smell her pussy right in front of my nose.

" That's a good girl. A girl must know how to suck a good dick. Especially a big black dick like this one. Can you taste yourself on it whore? HAHAHA! You better get use to sucking dick and become a fucking pro at it too. I have to be hard on you the first time like this, or you bitches never learn right. I have to break you in the first night so I know you won't run away from me. You are my new dog. And this is your training."

She pulled her dick out of my mouth and stepped back. She undid her strap-on, pulling the other end of it out of you cunt and let it drop to the floor. She stepped backup to me and shoved my face into her pussy. I knew what exactly what to do. I lick and licked. I sucked on her little clit and shoved my tongue as deep into her as I could. She just rode my face, face fucking my tongue so hard I couldn't breath. All I could taste and smell was her pussy. She began to convulse and pulled my hair, shoving my head into her crotch as she came right into my mouth. I swallowed every bit and even licked my lips clean.

"VERY GOOD! You are so good at that, that I don't need your little clit anymore; I will just use your mouth and fuck that ass. Now I'm sure you are tired and hungry, so I will allow you to eat, and you will be PUT AWAY until I need you again."

With that said, she pushed me down, turned me over and undid my handcuffs. I was then instructed to stand on all fours like a dog. She the applied chained handcuffs to my wrist and to my ankles. These allowed me to move but only about a foot at a time. She pulled on my leash and I crawled around on the floor. She pulled me to a dog cage with a bed and two bowls inside. She pulled me inside and pulled my leash through the other side of the cage and locked it. I couldn't now back out of the cage. She smacked my inner thighs so I would spread my legs apart. I fear I would get fucked again. Instead, she shoved a big butt plug into my ass. I tried not to scream to prevent another beating. She then put an adult diaper on me and duck taped in on. She unlocked my ankle chains and pulled something up my legs. They were frilly panties. She pulled up my legs and over my ass covering the diaper. I could feel all the lace from the panties around my thighs. Spanking my ass one last time, she then shut the cage and pad locked it. She came around so I could see her. I watched her put the key hat was on a gold necklace with a bunch of other keys, over her head and resting against her breast.

"Eat up! You'll need your strength later. And I better not hear a peep out of you, or I'll just use the taser!"

She went around to the back of me again. I felt a sharp pain in my ass as if I got a shot, and she just said, " nighty night bitch!"

She covered the cage with a blanket, and walked away. I could only see what was in the cage and the light threw the blanket. I looked down, trying to forget the pain in my ass. I saw in the bowls, one had water; the other had a few pills in some applesauce. I wondered what the pills were and feared what might happen to me. Then I remembered the beatings, the rape, the torture. I didn't want to that again. I knew she now owned me and I better eat this shit or I might get hurt again. Plus, I hadn't eaten anything since before I dressed myself up at home and was picked up by my mistress. I was starving! I ate it all, ignoring the pills and what they might be. I licked up the water like a dog that just ran a marathon. I then tried to cope with what all had happened to me. This was for real. What had I done? Can I ever go back from this? I soon became very sleepy, and curled up in the fetal position and passed out asleep.

I awoke to the sound of a spoon hitting a pot. My Mistress was screaming at me to wake up. She pulled my legs, yanking me out of the cage and orders me to stand. I almost fell from being so out of it and being confined in the cage, AND I was still wearing heels. I looked down to see that I had wet my diaper, and I still had to pee.

"You are pathetic! You wet yourself! Now, go to the restroom to the right, take off you dirty diaper, and sit on the toilet like a good girl and potty. I will be in there in a minute."

I took baby steps, trying not to fall all the way to the bathroom. Once inside, I pulled the frilly panties off and undid my diaper, and sat down on the toilet. I pushed my "clit" in its cage between my legs and peed. I looked up on the wall and saw a clock. It was 5am and I had to be at work at 9am! My Mistress entered.

"Stand up and turn around!"

She un-cuffed me, took off my collar, unlocked and took off my heels, rolled my stocking down my legs, and untied my corset, letting it all fall to the ground. She went to the shower and turned it on for me.

"Get in the shower, shave everything, and wash with the pretty smelling body wash and shampoo and condition your hair. When you get out, rub the baby lotion all over you and apply the rose perfume. By the time you do all that, I will be back with your clothes, and I will take you home."

I almost exploded I was so happy. I jumped in the shower. I was curious to when I would be able to get the false breast off.

When I was finished, my mistress came in with a hand full of clothes and handed them to me. I had a towel around my chest, covering my breast and my hair was also wrapped in a towel. I was ordered to go into the bedroom and get dressed. I walked into the bedroom, wobbling a little from the butt plug still inside me. I went through the clothes to see what I going to wear. There were pink bikini cut panties, pink 36 d size bra, pink garter belt, tan colored thigh high hose, a low cut white sweater, and a pink knee length leather skirt. I looked down to see a pair of pink strappy high heels. I quickly dressed. Trying not to get a run in my hose with my long fake nails. I was half way done putting on my heels when I looked at a clock. It was now 6:30am. I normally get up a t 7am and get ready for work. I was dressed as a woman with glued on nails and fake breast and I knew I was about an hour from home. Plus, I know it would take longer getting home because of traffic, AND I had to change once I got home and speed to work to not be late. My Mistress entered, holding out a pink leather purse.

"You look hot! I bet every guy at you office will want to fuck you when you into work dressed like that! Now, come with me so I can do your hair and make-up. You better learn how to do these things, as I won't do them for you after today."

She grabbed me by putting her hand up my skirt and pulling me by my cb-2000. I was dragged into another room where there was a vanity with tons of make-up and a chair. She pushed me down into the chair, and quickly went to work on me. First, she pierced my ears with big hoop earrings. She then went to work on my face. Foundation, powder, rouge, eyeliner, eye shadow, mascara, and finally, stay on lipstick. The whole time she was doing this, I was freaking out. Am I to go to work dressed like this? If so, will I get fired? What will happen next? While she was fixing my hair, she started curling it and applying hair spray to make the curls stay. As she worked, she told me to take the jewelry in front of me and put it on. There where 6 rings with diamonds, a gold necklace with a gold heart, and a couple of gold bracelets for my skinny wrists. She finished I all up by squirting a few sprays of more perfume on my neck and wrists.

"You look stunning! I can't believe you USE to be a man. Well, those days are over with. You'll notice when you get home that I made some changes to you apartment. I found you secret little e-bay bank account and bought you a new wardrobe. You now have a closet full of dresses, skirts, blouses, shoes and so on. Your drawers are packed with new panties, bras, a few corsets, slips, nightgowns, garters, hose, pantyhose, teddies, camis, and work out clothes like sports bras and spandex shorts. I also put some bikinis and bathing suits in there. I also fixed you room with some pretty sheets for your bed and some girly decorations. Also, I fixed up your bathroom with feminine products. You have plenty of make-up, shaving gel, body wash, shampoos and conditioners, hair care products, tampons and maxi pads, face scrubs and so on. You also have a little box with jewelry on your new vanity filled with perfume and more make-up and nail polish. You will also find some vitamins in your bathroom. You are to take one of each a day. I want you healthy and in shape. You are to change you diet as well. You will eat salads and drink water till I say other wise. Ad you can only have a slim fast for breakfast. I scheduled you weekly appointments at my beauty shop for your hair, nails, eyebrows and body waxing. I will know if you go or not, so you better not let me down. You seem scared. I did leave SOME of you nasty boy clothes for you. You are to only wear them when I say to. As for you boxers and boy socks, they are burning in the furnace heating up this place. Now, lets go. You don't want to be late for work!"

I was shaking and in tears.

SLAP!!!

"Don't cry!! You'll ruin your make-up. Now LET'S GO BITCH!!"

She threw the pink purse at me and grabbed my wrist and pulled me through the house. She then put sunglasses on me that were completely black, so I could not see. I heard her unlock her door and she pulled me out, lock her door, and dragged me to the car. I heard her open the door for me and help me in. once inside, she pulled my wrist around the back of the seat and handcuffed me. She slammed me door and walk to the other side and got in.

"Don't say a word, or I'll drop you off in Compton, then you'll really get fucked by a big black dick!"

With that, she started the car, blaring heavy metal music, and sped away.

rebeldoll
rebeldoll
242 Followers
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  • COMMENTS
11 Comments
AnonymousAnonymousabout 5 years ago
And that's why

you shouldn't trust strangers you contact on the internet.

But in reality, nutters like this mistress are pretty few and far between, so it's just not a credible story.

cdCindy1cdCindy1about 7 years ago
Just like me and my Mistress

This part of your story is exactly what my Mistress Angelique made me say to her out loud - at a restaurant where I was dressed up for her.

"I will obey you Mistress, I promise! I want your cock in me. I want to be your little girl slut. I want to wear panties and sexy clothes for you. I want to wear dresses that show off my breasts. I want you to use my man cunt and my mouth however you see fit. PLEASE PLEASE MISTRESS, I WILL BE GOOD FOR YOU !! I WILL OBEY YOU!!!" (almost exactly the same words you said).

The other restaurant customers were shocked and a lot of them laughed because they knew I was a man crossdressed for my Mistress. I was embarrassed and humiliated but it was also exciting at the same time - such a turn-on because that's how sissies like me feel.

Please tell more stories like this one. It really hit home with me because it's similar to what has actually happened with me and my Mistress.

NamwanWhiteNamwanWhitealmost 8 years ago
10 years...

and no part 3 :*(

AnonymousAnonymousabout 11 years ago
epic

I really want to be you

AnonymousAnonymousover 11 years ago
slutty

I have been used like that and wish it would never stop great story

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