What happens to horny sissies

[Computergeek94]

Well that went in a different direction than what I was expecting 0_o

[Dirty_Slut]

I love this story

[Petite_Devil]

Haha, wish I had my own sissy, while studying at school.
My grades would be excellent for a few years ahead.
Thanks.

[Alcd87]

This story just keeps getting hotter, you realy are doing a good job with it

[tiger777]

I really think that this is a great story and hope that you have fun writing it and I'm looking forward to the next part.

[subDanni]

Peter drove me to his place. When we walked from the parking lot to his house he held his arm around my waist. I felt like I was a prostitute, walking with a rich man to his home. He had a nice house. We went in and when we got into the living room I saw a woman sitting there reading a book. They had a very classy home. Old fashion. She was wearing a red shirt and a black skirt. Over knee length. I figured she had pantyhose underneath, and she had her hair up in a bun and was wearing glasses. She looked like a strict teacher. I stood beside Peter looking down. I was very humiliated in front of this woman.

Peter: This is Margaret, slave. She will take care of you now.
Me: Yes, Sir.
Margaret: Is this the troubled school-girl?
Peter: Yes, she need some strict teaching.
Margaret: Right. Look at me, Jenna, is it?
I looked up at her. So shy and careful.
Margaret: You will address as Ma'am. And you will listen and do as I tell you. Do you understand, Jenna?
Me: Yes, Ma'am.
Margaret: Good. Peter, we'll go upstairs. I assume you're done with her for now.
Peter: Yes.

Peter handed Margaret the keys to the chastity before we went upstairs and into their bathroom. I was stripped completely naked, except for the chastity. That stayed on. Margaret washed off my slutty make-up and applied new. Not slutty looking, the new make-up was pretty. And placed a cute bow on my head and let my hair innocently rest to the left side of my forehead. I looked so innocent.

Margaret: Now this is how a proper school-girl should look. Don't you agree, Jenna?
Me: Yes, Ma'am.
Margaret: Tell me, why do you dress like, frankly, a hooker?
I looked down, in shame.
Me: I-I'm not sure, Ma'am.
Margaret: Is it because you are insecure? And want acceptance from the boys?
Me: I guess so, Ma'am.
Margaret: That's a shame. You need to dress and act properly. Now, put your hands behind your back.
Me: Yes, Ma'am.

She unlocked the chastity and I became erect immediately. She looked up at me with a very judging and strict look on her face. I felt so embarrassed and tried to look away.

Margaret: Look at me, Jenna!
I looked at her, shameful.
Margaret: This is not acceptable. We will have to do something about that clit you have.
Me: Yes, Ma'am.

I was crazy horny. First time out of the cage for over two weeks. She put a blindfold on me and led me out of the bathroom and into another room. I just stood there in the new room, and could hear her walking around there, with her heels. Suddenly she stopped. I could feel her standing close to me. My cock was still erect. Then I felt it. She slapped my hard cock hard with a ruler. I moaned and buckled my knees a bit.

Margaret: We are going to whip that clit into it's rightful position.
She slapped it again and started to walk around me as she asked me questions.
Margaret: Why are you so aroused, Jenna?
Me: It-It's just been so long since it's been free.
She slapped it again.
Margaret: When did you last ejaculate?
Me: I came with the cage on ten days ago, Ma'am.
Slapped it again.
Margaret: And how long have you been locked?
Me: Two and a half weeks, Ma'am.
Slapped it again.

She slapped it so hard that the erection went down. Then I could hear her walking around me one more time, before she took a grip around me balls and slapped them too, five times. I fell down to my knees, but she told me strictly to get back up. Then she just gently touched my flaccid cock. She was taking some sort of measurements of the length of my soft cock and of my balls. I felt so small and pathetic in front of her. Naked in front of a fully dressed and mature woman. After a while she walked away again and came back with a chastity. A spiked chastity. She put it on my cock and removed the blindfold. There was a TV in the room. She told to sit down on my knees, with my bum resting on my feet, and to fold my hands and place them in my lap.

Margaret: This will hurt, but it's for your own good, Jenna.
Me: Yes, Ma'am. I understand.
Margaret: Good.

She turned the TV on and showed me porn. It was videos of slutty girls giving blow jobs and being fucked by a lot of men. I became very horny watching it and my cock hurt so much in the spiked chastity. Margaret just sat in a chair beside me, with her legs crossed. Judging me. She made me watch for almost an hour. Every time my cock became painfully erect it got soft, but it never took long before it became excited again. It was such torture. After we were done she left the room for a bit. When she returned she had someone else with her. It was another sissy!

[tiger777]

Yet another great update to this story I like where this is going and I don't know if I want her back with her sister and Denies (when they are done with her) but I like this.

[subDanni]

The sissy she had brought was wearing a very sexy maid outfit. She had a bit longer hair than me and had it up in a bum, like Margaret. With cute short heels on her feet.

Margaret: This pretty girl is Brenda. Say hello, Jenna.
Me: Hello, Brenda.
Brenda: Hello.
Margaret: Brenda is a very good sissy, and have been especially good this last week. So I have decided I want to reward her.
Me: Yes, Ma'am.
Margaret: We usually only let her out of the chastity once a month, but I will let her out tonight, a week earlier than scheduled. And if she is very good, I will let her have an orgasm.

Margaret unlocked the cage on my cock, but put the normal chastity back on. Then she unlocked Brenda's chaste cock and told her to get naked. She told us both to sit on our knees beside each other and in front of Margaret, with our hands behind our backs.

Margaret: Look at my pretty girls. Why don't you start kissing each other?

I looked at Brenda. This was so humiliating, but Brenda took the initiative and started to kiss me. We still had our hands behind our backs.

Margaret: You are allowed to get excited, Brenda. And you can both use your hands.
Brenda: Thank you, Ma'am.

Brenda got closer to me and I could feel her cock become hard against my chaste cock. He, or she, held her hands around me and gently squeezed my ass. Her lips against mine felt so good. After a while Margaret told us to stop and get back into kneeling position in front of her. We did as commanded. She held a Hitachi vibrator in each hand.

Margaret: Now that I have your attention, girls. We will have a little competition. The one of you that cum from me vibrating your clits will be punished. The one that don't will be rewarded. And Jenna, you really have an advantage with that locked clit. Brenda is free and erect. And have even been denied longer than you.
Me: Yes, Ma'am.

She started the vibs and placed them on our clits. I became very horny. Looking at this strict woman rubbing a vibrator against my chaste cock, and at the sissy beside me struggling and grinding against that vibrator. Brenda was good at this, I could not handle the strong vibration even when my cock was locked up. After a little while it started to leak and I had a ruined orgasm in my chastity. The cum squirted on the floor in front of me, and I gave a feminine moan as I came. Margaret gave me a strict look and shook her head. She looked disappointed.

Margaret: Good girl, Brenda. This other girl obviously need a lot more training. You should be ashamed of yourself, Jenna.
I looked down in shame.
Me: I'm sorry, Ma'am.
Margaret: Lick up that mess, Jenna. And Brenda, you won, so I'll let you have some fun with Jenna.
Brenda: Thank you mommy. Can I use toys on her?
Margaret: Some toys, yes. Don't get too excited.
Brenda: Thank you.

Brenda went to get some toys. She came back with anal beeds. Four big ones on it. I nervously gulped when I saw them. Brenda put me in a doggy position and lubed up my asshole before she started to put then inside me. The first one went in smoothly, the second one a bit painful and the third Brenda had to use some force to get inside. I moaned as she forced it inside me. Suddenly someone came in. It was Peter, with another man.

Peter: Oh, both the sissies are here. We would like to have Brenda for a little while, Margaret.
Margaret: Hmm, this could be interesting. I like having them compete. How about you two come in here for a blowjob?
Peter: Oh, yes. We would like that.
Margaret: Brenda will pleasure you, Peter. And you, Jenna, you will pleasure this nice gentelman. His name is Christopher.
Brenda: Yes, Ma'am.

The guys walked over to us. We were on our knees beside each other, I still had three of the beeds inside me. They got their cocks out and Brenda eagerly started to suck Peter's cock. I was a bit more hesitant, but looked up at Christopher and started to masturbate his cock before I started to suck it.

Margaret: The first one to gag lose. And the loser will be their toilet this evening.

The guys seemed to get excited by that and started to fuck our mouths. Brenda was very skilled, so I lost again with Christopher's cock deep down my throat.

Margaret: Oh, my. Loser again, Jenna. You really have a lot to learn, Jenna. When you cum, Peter, I want you to cum on Jenna's face.
Peter: With pleasure.

Peter fucked Brenda's mouth hard. Getting deep down her throat. Christopher did the same with me and I got tears in my eyes. I eagerly looked up at him while I sucked him. My cock was so horny in this position. With both my mouth and ass filled. I could feel that he was going to cum soon, and Peter also moved towards me. He masturbated right above my face. Christopher pulled out his cock and started to cum on my face and in my mouth. Peter also started to cum. Their cumloads filled my mouth and covered my pretty face and at the same time Brenda forced the forth beed up my ass. I felt so used and abused. And loved it. I smiled at Peter and Christopher, thanking them for their cum.

Peter: You're welcome, slut. We'll go downstairs again.
Margaret: Well, Brenda. Do you want to do something with Jenna as well?
Brenda: Yes, Ma'am.

Brenda ran her finger over my face covering it with cum and made me lick her finger. She did that until my face wasn't covered in cum anymore. Then she stood up and showed me her ass and made me lick her asshole. She loved my tongue on her asshole and moaned like a real sissy.

Brenda: Good girl, Jenna. Now lay down on your back.
Me: Yes, Brenda.

I did as she said and she got on top for me. Sitting on top of me, with her erect cock touching my locked cock. She rubbed her cock against my locked cock. It was so frustrating, and then she used the Hitachi vibrator on her cock as well. She humped and moaned. I did as well. It was so hot watching her pretty face moan in pleasure. And to feel her cock against mine, even if mine was locked. She increased the pace and I could see on her face that she was going to cum. I just grabbed her ass-cheeks and she squirted all over my stomach. It was such a humiliating and arousing feeling. Brenda licked up her cum from my belly, and then she got her face above mine and kissed me. All the cum was swapped into my mouth.

Brenda: Swallow it, Jenna.

I did. It was lovely. I smiled at Brenda and thanked her. Margaret then put me on all fours and made Brenda pull the anal beeds out of my ass. I moaned in pain as she pulled them out.

Margaret: Enough fun for now, Brenda.
Brenda: Thank you so much, Ma'am. Jenna is such a fun girl.
Margaret: Put on your dress again. Don't you have some cleaning to do? I'll let your clit stay free until tomorrow.
Brenda: Yes, Ma'am. Thank you.

Margaret led me to another room. In this room there was a cage. Where it would be room for me to stay on all fours inside. So not very big, but just big enough. Margaret gave me a pair of white frilly panties, not slutty thongs like I usually wore, and a pink nightgown and cute knee high socks with bows, before she put me inside the cage and locked the door to the cage shut. There were bars on the side and on the top of the cage.

Margaret: Sleep well, Jenna.
Me: Thank you, Ma'am.

I tried to find a comfortable position, but after a little bit Peter came in. He told me to get my mouth up between the bars and open up. Then he peed into my mouth. He took it easy so I was able to swallow it all, and he even made me lick the tip of his cock clean before he left.
I tried to sleep again and after a while I finally managed to do so.

[Dirty_Slut]

I am so jealous of jeena...wish I were her

[Petite_Devil]

Finally our Jenny felt her clit free for a moment.
I only hope it was not the last time it was unlocked.
Great chapter as always. Thanks.

[Alcd87]

Oh wow this is good, I so wish I was Jenna in this story

[tiger777]

I can only agree with the others, yet another great chapter

[philmcrakin]

Thanks for the great story. I want to be this Christopher character in the latest part

[subDanni]

Originally Posted by philmcrakin

Thanks for the great story. I want to be this Christopher character in the latest part

Oh really? So you rather want to Fuck Jenna's inexperienced mouth, than Brenda's so well trained mouth?

[subDanni]

I thought I would be allowed to rest now, but a bit into the night Christopher and Peter came into the room. They were like before, handsomely dressed and were drinking whiskey. Very classy look. I was nervous, due to their influenced by alcohol, but luckily they weren't drunk. Just a little tipsy. Christopher unlocked the cage I was in and led me out. He placed me on my knees in the middle of the room. Peter sat back in a chair and looked at me.

Peter: what to do with this slut. Such a fucking tease.
Christopher: I agree. Trying to look innocent in that outfit. We all know you're a whore. Right, slut?
Me: yes.
Christopher: say it out loud, cunt.
Me: I'm a fucking whore.
Christopher: that's right. Offer yourself, whore.

I pulled down the panties and presented my ass. Stayed on all fours.

Christopher: Fuck that asscunt makes me horny!
Peter: well, Fuck it then. Or are you afraid Margaret will get angry?
Christopher: hehe, she don't need to know. Right, whore?
Me: I won't say a word! I promise.
Peter: good girl. She don't like it when I get involved in the training of her new sissies without her knowing.
Me: I understand.

Christopher could not wait any longer and pulled his pants down and started to fuck me in front of Peter. I was put in a position on all fours with my head turned so I was looking at Peter. Forced to stare at him while I was fucked in my ass. After a while he opened his pants and told me to get closer to him and take care of his cock. Christopher let me crawl closer to Peter before he continued to fuck me with his delicious cock.

Peter: I wanted a blowjob from that inexperienced mouth of yours earlier.
Christopher: it was nice. Her mouth feels good.

I stroked his cock before moving my hands down to his balls, gently rubbing them. And placed my mouth on his erect cock. His wet cock head was sweet and slippery. Moving deeper down on his cock I began to gag a little. Peter seemed to like it, but pulled out a pair of handcuffs.

Peter: put these handcuffs on her, will you Christopher?
Christopher: sure! This slut is so sexy with her hands restricted!

I tried my best to make them both cum. Sucking hard on Peter's cock and moving my ass against Christopher's cock. But I wanted it to end soom, even though I wanted to please them. I was so tired. And suddenly I could hear someone entering the room.

Margaret: Peter, what are you doing with MY girl?!
Christopher: oh, fuck!
Peter: oh, come on. Let us just use her for a little bit!

Christopher pulled his cock out of my ass. Painfully quick, and put his pants back on and left the room. I didn't know what to do.

Margaret: Jenna needs to rest, Peter! I told you not to bother her after you was here the last time to urinate. And Jenna, stop sucking his cock. He don't deserve your pretty mouth.
Peter: you're so uptight sometimes, Margaret.
Margaret: I don't care. I let you use these girls in exchange for being in charge of them. That's only fair, when I let you spill your seed in all these sluts.
Peter: fine. I'll leave.

Peter pulled his pants up and left.

Margaret: I'm sorry about that Jenna. I should never had let the door stay unlocked. Men can't ever be trusted!
Me: it's OK, ma'am. Thank you.
Margaret: oh my sweet little girl, you don't know if it's OK or not. When I say it's not ok, well, then it's not OK.
Me: yes, ma'am.
Margaret: I want you to feel safe. You are sleeping in my room tonight. Put your panties on and follow me.

I put the cute and frilly panties on and followed her into her room. She had a huge bed. I was placed at the foot of the bed where I could curl up and she put a duvet over me. She gently stirred my hair with her soft hand while she started to hum for a bit. I felt so special and cared for. It was amazing. Then She laid in the middle if the bed, with her feet reaching the mid part of my body, occasionally touching my locked cock with her feet. I was very tired and quickly fell a sleep. And I slept deeply. When I woke up in the morning, Margaret wasn't in the bed. I decided to just keep sleeping because I was still tired. After a bit I could hear someone coming into the room, it was Margaret and Sarah. I pretended to still be sleeping.

Margaret: she is in the bed here, Sarah. Let's be quiet. I let her sleep as long as she wish today. She was so tired after yesterday.
Sarah: awe she looks so cute there, and in that outfit. My poor little Jen.

Sarah actually seemed to have bad conscience about leaving me like she did at school. She whispered while she looked at me "I'm sorry, little Jenna".
They both sat down by a table in the corner of the room. I still pretended to be sleeping, and could barely hear what they said to each other.

Margaret: I will give you some tips on how to discipline your sissy. I understand that you don't want to put her in a lot of pain, but there are many other ways to punish a misbehaved sissy-slave.
Sarah: yes, thank you. I just feel so bad about it when it goes too far.
Margsret: I understand. I would suggest humiliating her. And tease her for punishment, instead of pain. You can unlock her chastity, tie her hands and attach a vibrator to her clitty. After a while she will hate it. But keep her like that for a long period of time. Tease her and lock her back up. She will learn to behave that way.
Sarah: that sounds like something I can manage to do.
Margaret: yes, and make her do humiliating and degrading things while you record her. That way you can show her the vids if she misbehave again. She will hate to watch herself doing those things. And you can say you will make her do it again if she don't get her act together.

After that they moved closer to each other and started to whisper. I could not hear what they were saying.. Suddenly they spoke louder again.

Margaret: feel free to ask for more advice. And even invite me or you can come here again. I would love to train Jenna again. She is a very special girl. Remember that, Sarah.
Sarah: yes I will. Thank you for all your advice.
Margaret: no problem. Special girls like Jenna can be fragile, so be very careful next time you get angry with her. I wouldn't ever want to loose a girl like that.

I turned around in the bed and Sarah could see I was awake. Her eyes lit up when she saw my face. She quickly walked over and sat on the edge of the bed, beside me. Her soft hand gently touched my thigh.

Sarsh: hi Jen! Are you OK? I'm so sorry I overreacted!

I was a bit surprised about the way she felt about this, but happy that she wasn't angry anymore.

Me: hi, mistress. It's OK. I needed to be thought a lesson.
Sarah: will you come home with me, little Jen? I want you to come home.
Me: yes, mistress.

She leaned over and hugged me. It felt very good. Her smell, her arms around me and her chest against me. It was perfect.