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  #1  
Old 11-19-2016
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princess shawn princess shawn is offline
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A good, hard fucking is what I am in the mood for right now. I look around for the biggest, thickest cock. Male or female, it doesn't matter. Meanwhile, my three partners are clearly eager to expose my breasts and cock. I had initially wanted to keep the sailor costume on for ila's sake, to let him know my naked body is exclusive to him, but I cannot disappoint these people any longer. And so I undo the buttons, one at a time, revealing my fat bouncy boobs for their enjoyment. In no time at all, I feel tongues roaming all over my nipples.

Their hands are reaching under the skirt and to the bulge on my panties. "Not yet." I say to them, then point out a man from the crowd. He is rather average looking, noticeably older than me and quite well-built. Most importantly, his cock is enormous. "You, go pick up some lube. You will have the honour of fucking me."

I hear a mix of annoyed groans and shouts of approval from the rest of the audience. My chosen playmate leaves for a moment and returns with a tube of lubricant which he then squeezes over his cock. Slowly I pull my panties down and bend forward, allowing the other three partners to fondle my cock until it gets hard and play with my breasts for as long as they like. "What is your name?" I ask the well endowed new addition to the group.

"Tim." he replies with a big smile on his face, "You won't regret choosing me, princess. I assure you."

The tip of his cock touches my butt hole. I hold up my hand, telling Tim to pause for now, and ask ila, "May I let this man fuck me, Master?" In actuality, I know I don't need permission. I am just stalling, teasing myself before the entry, trying to think of ways to entertain the entire crowd and not just my playmates.
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  #2  
Old 11-20-2016
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Too late I remembered that I had wanted to say that Princess' playmates were not allowed to remove any of her clothes. Well, we'd both have to live with it as is because it was too late to add any rules.

While Shawn's playmates get to work licking and kissing her boobs, Maggie has me get down on my knees to suck her cock hard. It's a task which I relish. I start by licking the tip of her flaccid cock and then along the underside. My hands roam over her firm bottom as I continue to lick and kiss her cock. She is rapidly getting an erection so I take her fully in my mouth to suck her.

As my head is moving back and forth on Maggie's cock I hear Princess call out to a guest to get some lube. I stop what I'm doing to see who she is talking to. I see a guy head off towards a table. My eyes widen when I get a look at his cock. It is fully engorged and it's huge. I wonder how Princess Shawn is going to take that much.

Maggie brings me back to the task at hand by telling me to suck her cock again. I eagerly return to pleasuring Maggie. Just as I'm really getting into it Maggie pulls her cock out of my mouth and moves behind me. "Get down on all fours, lover. I'm driving now," she said.

I drop down onto my hands and knees. I glance to my right to see that Princess is also on all fours now and facing the same direction as me. I look behind her to see her new playmate lubing his cock. He then tosses the tube to Maggie who squirts some lube onto her fingers. The next thing I feel is Maggie's fingers rubbing the lube over my butt.

Just as Maggie finished lubing me and herself I hear Princess asking permission for her new playmate to fuck her.

"Just a moment, Princess," I answer.

Maggie puts her cock up against my entrance. I can hardly wait to feel her slide into me. I look at Princess again and say, "Permission granted, Princess. Let's see if our partners can make us cum."
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  #3  
Old 11-21-2016
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Out of the shadows walks Jamie with rope marks around her wrists and ankle and sweet cum in her bobbed hair and bangs. She walks slowly because she has encountered it all but the guy that tied her down would not allow her to join in. He wanted her all to himself and she has no idea who he is or was.

I shows up in fishnet stockings with a garter belt and stiletto heels but nothing else. I do want to join the fun but my wrists and ankles are sore from being tied spread eagle on my stomach for so long while trying to please himself and me. I show up with a red ass because of a strict spanking but nothing more than a "Pearl Necklace" and "sticky hair" because the guy could not please me but got pleased and I am horny as hell. But I am shy and still stay in the shadows watching the Orgy that is going on and fingering my small penis. My penis is inside me and soft but hot and leaking smooth and clear " sweet salted honey" enough to giver me lubrication enough to feel really good. I lick it off my fingers and OMG. I wish I had another trans woman and a man.

I am wishing someone else would tie her up on my stomach and please me anally and orally multiple times. A guy from the rear and orally and another trans woman orally with an outie like I have.

Then release the restraints and roll me on my back with my legs tied to the head board and my knees tied wide open with my ass in the air. Open to anyone and lubed up nicely. My mouth is open game to anyone trans woman or man that loves an active tounge as well as a vacuum. I scream harder and faster with tears of joy in my eyes but no one can understand because I have a line of cocks waiting for my tounge and lips and my mouth is always full. All the while another sexy trans woman is styling my hair with her hand and licking the previous cum off of her fingers left over from the other guy that was left in my hair.
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  #4  
Old 11-21-2016
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I smile at ila's reply. Tim begins penetrating me. Despite all the lube he has applied on his cock and my hole, he has to move slowly. Very, very slowly to test how far my hole can stretch. My other three partners, upon hearing ila's words, slide their hands over my cock to milk me. Their fingers tightening, they squeeze and stroke my ladycock. I try to hold in my cum, at least until Tim has fully entered me, so that everyone gets equal credit for who makes me cum. My cock fully stiffens in seconds.

At halfway along Tim's shaft, I scream in ecstasy, "Aaaahh..." The others had to hold me in position with their other hands so that he will not bring me to my knees. I look up at the eager faces of people wishing they are next to fuck me. That is when I notice a lovely lady in fishnet stockings among the crowd of naked bodies. Either she is a latecomer or, from the rope marks, she had been kept busy during the party. Unlike the rest of my audience, she seems distracted, not focusing on the action as much as the lusty spectators. More importantly, she is flaccid.

I feel Tim's balls touching my opening. Keeping myself bent forward until he pulls out, I call out to Jamie, "You there, in the fishnets. Come over here." The other playmates pause to see who I am talking to but I immediately say to them, "Don't stop. My Master wants to see me cum."
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  #5  
Old 11-22-2016
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Maggie slid her cock into me in one long, slow push that let me feel every inch of her beautiful, firm hardness. Of all the cocks that I’ve had in me none felt as good as Maggie’s. She paused momentarily when she was fully inside me and then she started to slowly stroke in and out. I was soon moaning and groaning with pleasure.

I look over at Princess. Tim is still pushing his monster cock into her. Shawn’s other two playmates have started running their hands over her cock. From the look of bliss on Shawn’s face I can see that she is getting a lot of pleasure from all the attention.

It looks like Shawn’s playmates may just get her to cum very soon and long before me. I’m not concerned at the moment though because Maggie’s cock feels too good fucking me. I don’t want her to stop any time soon. If she does cum I’m hoping that someone replaces her; male or female, it doesn’t matter to me. Now if only I had a cock to suck too.

A couple seconds later I again look over at Princess. Someone in the group seems to have her attention and then she calls out for that person to join her. I look around and see a beautiful woman in fishnet stockings, a garter belt, and heels. She is looking around tentatively, perhaps even timidly. She seems both eager and reluctant at the same time.

The woman turns slightly towards me. I can just make out a tiny flaccid cock. For some reason I’m more turned on than ever. I watch her approach Shawn. I get the sudden desire to have this new woman suck my cock. I look directly into Shawn’s eyes hoping that she can see my lust for her newly selected playmate. It would be too easy to tell Princess to send her new partner to me, but I want her to get the idea on her own even if it’s after Princess Shawn has had her own enjoyment with this lovely new woman.
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  #6  
Old 11-24-2016
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My tiny flaccid cock is starting to leak a little. I have a sweet salty slimy ring hanging down to my knees.

I am looking forward to what may come next with this new girl that is wild and submissive. I am fingering my tiny head and all it is like is fingering an XL clit but want a hard cock in my mouth and one in my ass making me scream in ecstasy but all that come out is garbles because my mouth is so full. That cock is tickling my tonsils and I am tasting the sweet saltiness of pre cum sliding down my throat. I am secretly waiting for the sweet explosion that may be soon to come. Or cum. So I can swallow it all.

The new girl loves an explosion in her mouth and ass form two simultaneous partners. Please don't keep her waiting for too long. We have all night so many times we can go.
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  #7  
Old 11-24-2016
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(I try not to nitpick but Jamie, please stick to writing in first person. In your latest post, is "the new girl" you, me or someone else?)

My goodness, what has this new arrival been through? Even as Tim starts to pull out, not squirting yet as he is being slow and gentle with his giant cock's re-entry into my tight butthole, I am wondering if Jamie has been neglected all this time. Unlike everyone else, she is shy, far from rushing to the front row to catch a glimpse of the action. I can see a tiny bit of cum on the tip of her cock; maybe someone played with her a while ago but left without properly satisfying her.

This will not happen, not in my party. "Everyone, stop for now." I order my playmates to back off. They do so reluctantly including Tim, all of them looking quite annoyed by the interruption. I walk over to Jamie, stopping as far as I can go with the leash still in ila's hand. I look at Jamie from head to toe. A fully submissive lady with no one to dominate her, with cum on her hair that she has not wiped off. My first guess is that she desires a strict dom willing to punish her if necessary, though I find myself hesitant to adopt this attitude in case that is not what she wants.

I say to her, "I will be your Mistress for the rest of the party, but first you have to show me what you can do." I point at my cock that my partners had pleasured into its lovely, fully swollen form. "Suck me. Do it well and I will let someone fuck you. But if you fail to satisfy me, I will find ways to humiliate you."
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  #8  
Old 12-16-2016
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I watch while Princess prepares to enter slave. I enjoy watching the slow deliberate measures. I’m so involved that I forget to do anything until Shawn says that slave wants to taste my cum.

I scramble into position so that my cock is within tongue flicking distance of Jamie’s mouth. I give her cheeks two quick, sharp, stinging slaps with palms of my hands. “Listen up, slave,” I say gratingly. “You need a more appropriate name than slave. From now on you’ll be call cock slut or cum slut. Both names fit you.”

I look at Shawn and see her smiling at the new names. I have a feeling that she may come up with some names of her own. It will be interesting to see what happens.

I turn my attention back to Jamie. I slap her three times with my cock. “Suck it, cock slut. Suck it good.”

I have already cum more times tonight than I ever thought possible so I’m curious to find out how our slave is going to get me hard once more. As cum slut takes my flaccid cock in her mouth I look back at Princess Shawn to see that she is slowly fucking slave’s ass. “That’s it, Princess, fuck cum slut real good. Fill her with your hot cream and then we’ll switch around.”
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  #9  
Old 12-18-2016
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(I'm waiting for Jamie's reply.)
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  #10  
Old 01-07-2017
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(After discussing with ila, I've decided to end this roleplay. Not because of Jamie's absence, but because cybersex will get boring if it drags for too long.)

After fucking Jamie's asshole, and squirting one final load into her, I pull out visibly fatigued by the night's events. There was a lot of fucking and cumming for a single party. I cannot get enough of that, but I have to stop at some point. "I think we can call it a night here." I say to ila, somewhat hesitantly as I know he will be disappointed by my decision despite his own exhaustion.

As for Jamie, I untie her from the bed. "And you are still a slut who can't obey your mistress." Very gently I remove the chastity cage from her cock. It is now free to cum and swell, but I make sure she knows I still disapprove of it. "The next time you see flyers announcing my next party, I expect you to show up. You need more training. Believe me, the punishment will be as severe as tonight's if not more so if you still refuse to follow orders. You may go home now."

She gives me a shy glance. I cannot tell if it is fear or eagerness on her face. Then she heads out of ila's house without putting any clothes on; the humiliation from walking home naked will be a bonus to her. I put my costume and shoes back on, making sure ila gets one last look at my cock and boobs. "My dear ila, you've earned this." I whisper, and kiss him on the lips. "Be sure to keep a lookout for my next party. I'll be waiting for you."

With that, I head back to my mansion. The mess will be cleaned up tomorrow morning. Back in my bedroom, I slip off the costume and into my nightie. Climbing onto my bed, I fall into a deep sleep.
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