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So....about 3 or 4 months ago i met a guy in chatropolis. In the 'showoffs with webcam room' ill call him tom as im not sure he and his friends would want me using real names on the web. We talked and flirted for bout an hour. I have to get pretty horny to cam for a guy. He was totally into the kinda stuff that gets me off (sissy humiliation and cum eating) so eventually i cammed for him he watched me dress up girly, toy my ass and finally blow my sissy load into my cum cup before guzzling it down like a crazed slut. All of the time egging me on, teasing me, humiliating me, abusing me until he too shot his thick load for me. Usually at this point its cam off. Get changed and back to normal, but tom wanted to chat more. We did. He was really cool whereas i was nervous and i hate to say a bit giggly. Eventually we swapped email adresses. And logged off.
Over the next few weeks we swapped messages. Me just sharing more outrageous fantasies with him. And him begging to cam again. He had friends who wanted to watch too! Id never really spoken with anyone who seemed to be openly into crossdressers. Its usually a kinky dark secret.
I cammed for him again. This time i set up a room on quickviseo. I called it christina123. (My sissy name from chatropolis) and waited for them. Tom logged on...said hi...then rang his friend...then another...and again. 10 minutes or so passed where he told me that id like his friends, and again i was giggly. Eventually, one after the other they logged in. I could see each of them. Couple naked, 4 guys logged on to watch me whore myself. Tom took the lead...and again i toyed my ass. Longer this time tho. A good hour i took their orders. Finally, allowing me to cum and drink down a huge load. Each of them then jerked off as i watched...one after the other they came. They thanked me for a wonderful show and rang off. All except tom. We again chatted. He somehow got me all horny again and made me do another show for him. Finally we logged off.
A day or so passed and tom sent an email. The guys had enjoyed my show. Would i consider doing it in person? Several long, kinky, flirty emails followed. I said i wanted them all... i wanted to suck them off....i wanted them inside me. We were both clearly turned on by each others messages.
Finally a message dropped in my inbox. The tone changed now. Would i meet up? For serious.
I thought long and hard....a week passed before i responded. I would do it.
I promised to dress for them, i would give them all blowjobs, but no anal. I just thought 4 guys would be too much. And as id never been fucked i was a little scared by the thought.
Cutting a long story short it was agreed. A hotel room was booked in a travelodge local to tom. We exchanged phone numbers. And in the week leading up, several very kinky text messages.
The day of our meet up arrived and i received a text that one guy couldnt make it. I kinda half expected it to be called of but toms next message was about how excited he was and how his two friends were lookinh forward to it.
I packed a bag. And drove the 90 minutes to our rendezvous.
About 20 minutes away i got a text. I pulled over to read it. Tom had booked into the hotel and they were in the pub next to the hotel. I parked up and with my bag entered the pub. It took a minute or two to find them. But they had a booth near the back of the pub.
Ill call the other two guys dick and harry (see what ive done there) we drank beer for almost an hour. My heary pounding in my chest. ...but eventually i calmed. They were nice, normal funny guys. Not stunning to look at. Dick and harry were in their 50's quite fit. Tom was in his 40's a little short. Slightly overweight if anything. I asked if they had done this before and they explained only with each other. They had often discussed finding a CD or a tranny to join them. But this was the first time they had 'struck gold' (their words, not mine)
I stood up and said that we needed to make a move before i chickened out. So we crossed the road and entered the hotel. We took the lift to the 3rd floor and enterred our room. For a second we stood looking at each other. I realised they were as nervous as me. So taking my bag i headed toward the bathroom. 'Ill get dressed boys' i said. Beginning to get into my slutty webcam persona
As i shut the door behind me they were each stripping off
I stripped naked. I had shaved all over special for today. And i dressed. Black basque. Black lace patterned stockings. Id worn them in our web show and tom had specially requested i wear them. Then my new special treat. Id purchased a pair of dark pink and black stillettos specially for today. A good 6" heel on a 2" platform. Theyre actually a size too small as it seems difficult to get anything sexy in a size 9 but i can squeeze them on. Theyre uncomfortable....but so sexy!
I topped the outfit off with a bright pink bob cut wig. Then i took my cock ring from my bag. I always have a little difficulty getting it on....and i was pretty much fully erect by now. But i love how it looks and feels, so it was going on. I fumbled my balls though it and was struggling to get my cock through too when there was a gentle knock on the door. 'Almost ready' i said....
Finally the ring was in place. Real tight making the veins in my engorged cock bulge. I applied a thick layer of pink lipstick. Took my buttplug from my bag and applied some lube in my ass. I know i wasnt gonna fuck....but i still wanted a toy in my ass. I Took a final deep breath and unlocked the door.
I stepped into the room. To be greeted by 3 naked, fully erect guys. 'Oh fuck yes' one of them said.
I held out my butt plug, 'can one of you boys put this in for me' i purred. Making my way past them i knelt on the bed offering up my glistening lubed rosebud to them. Tom took the plug from my hand and bagan to tease my boipussy with it. Mmmm....please baby...put it in me i said
He obeyed. Sliding it into me. It nestled in position. So snug.
I knelt up. 'Whos first?' I grinned. Harry clambered onto the bed. His back against the headboard. His 7" angry cock aimed at me like a weapon. I looked him in the eyes. Smiled...then swallowed his cock.. 'oh fuck...you filthy slut' he blurted as i bobbed up and down on his cock. Suddenly all of my nerves were gone. I could feel tom fingering at the plug in my asshole. I was in charge now!
Harry came quick. Too quick. Filling my mouth with his thick gloopy load. It was salty and bitter. Once i was content id got it all i knelt up. Showed harry his load on my tongue and swallowed it.
Tom was sat on the edge of the bed. Swinging my legs around i dropped to the floor between his legs. Kneeling, looking up into his face as he slowly jerked of inches from my face. Dick sat next to him. His cock was shaved smooth and cut...i was saving him till last. Toms cock tasted sweaty, filthy in fact. It didn't matter. In fact it was better. I worked on him more slowly...id rushed harry...and now felt a little guilty. His hands were at the back of my head. I knew he wouldnt let me stop. I didnt want to. Minutes past as i slurped and licked at his hardon. All the time hes calling me names...slut, faggot, whore, sissy..,all the stuff id told him that i liked in our messages
Eventually he pushed me off his cock...and repositioned himself on the bed. Similar to where harry had been. I walked to the foot of the bed. Gently fingering dicks cock as i passed him and smiling to him. I crawled up the bed, slowly toward toms beautiful hard cock. He was wanking it again. I was transfixed. I went to take him back into my mouth... but he forced me down....further south, moving his cock above me. 'Come on baby....a nasty fuckin slut like you needs to earn my cock' i licked at his balls but still he eased me down, 'go on slut you know what i want' i licked at his arsehole. "Thats it sweetie...eat my fuckin ass like the filthy pig you are"
At that second i almost came
I did as i had been told....a new experience for me....oh fuck this was wrong yet i was more turned on than ever. I worked my hand up between my legs and found my buttplug. I bagan pushing at it...just to feel it a little deeper in me. At first my tongue just flicked at his hole....but somehow that wasnt degrading enough for me...my tongue slid into his asshole. Dick was on the bed next to me, he wanted a close up. "Fucking hell tom...the fuckin slut is eating your asshole" he said
Again i almost came. I swear....it was only the cock ring saved me.
Tom....who had been wanking the whole time i was eating his ass...suddenly spat "fuck im cumming"
Letting me up from his ass....my lipstick smeared all over my face his asshole a smeared mess of spit and lipstick he sprayed his hot load into my face. Shot after shot. One huge drop into my eye temporarily blinding me. Finally he was spent.
I knelt up and began wiping toms cum from my face with my fingers. Each time licking them clean.
Tom was breathing heavy. Harry was sat next to him at the top of the bed grinning ear to ear, tom said 'jesus baby....i think im in love with you"
'Well tough' i said 'dick...where do you want me"
"On your knees bitch" he said
Dick stood witn his back to the wall. That perfect cock of his dripping precum. I walked to him. Grabbed a tissue from the dressing table and cleaned my face. Dick smiled. Pulled me to him and kissed me. "You dirty bastard...said tom....didnt you see her eating my ass"
Dick broke off kissing me and i slid to my knees and took him in my mouth.
"Oh fuck thats it baby ....suck it...suck it good....suck it slut" he was fucking my face. He had two fistfulls of my pink hair.
My cock was harder than ever before as he pumped my mouth full of his semen. His orgasm was huge. His legs almost gave out on him. I swallowed all of his precious jizz. 'Oh god baby that was amazing he offered by way of thanks.
I stood. Glanced at myself in the mirror. Lipstick smeared everywhere. Lips puffy and swolen. I excused myself to the bathroom. Washed my face, straightened my wig and reapplied my makeup.
I re entered the room. All 3 guys were lying on the bed and beamed at me as i entered. I tottered to the bed in my heels and jumped onto the bed with them. They made room for me to sit in the middle between them all. I sat up between them. All 4 of us staring at my rigid veiny cock.
'Fuck boys that was so hot'
Tom grasped my cock....i shuddered and moaned
Dick took a clear plastic cup from the table next to the bed and rejoined us...
I bit my lip and gave him the cutest look i could
Harry positioned himself between my legs and took hold of my buttplug...and began to fuck me with it.
Tom loosed my cock
"Shall we see if you can cum like a slut too" he said
Harry continued to push the plug in and out of me. Oh god....i was just so hard...so turned on...the taste of cum and ass in my mouth it was all just too much. My whole body spasmed, my breathing deepened. Dick bought the cup to my cock.
I actually cried out as if in pain as the first shot of my jizz finally forced its way past my cockring
I heard it hit the plastic cup....quckly following by 3,4,5 more thick blasts. I was writhing in ecstasy, our bodies a heaving mass of sex on this hotel bed.
"Finished?" Dick said
I nodded.
He bought the cup to my lips to drink. I eagerly gobbled down my own load.
I looked down the bed....all 3 of my suiters were rock hard again

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Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

2 years ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

3 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

2 years ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

2 years ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

2 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

1 year ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

3 years ago
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The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

2 years ago
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Classroom Sissy

Classroom Sissy By Cassandra Morgan I did it! I got in! Me! Geeky Brad Hollins. I'm one of the 10! I'm finally accepted! I'm finally one of the chosen few! I never thought I had a chance. After all, more than 200 students apply for the 10 every year, and 190 of them go away disappointed. Only the finest minds at Calvin Coolidge Community College (CCCC) get a Golden Ticket. And I'm Willie Wonka! Whee! You've heard of the 10, haven't you? It's a secret honor society at CCCC,...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

3 years ago
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A Submissive Sissy

A Submissive SissyMy sissy slave husband, Princess, was in the process of paying his usual obeisance to my feet on a recent morning. It's always good to see Princess applying his tongue to my high heels and on this particular morning he was working extra hard to please me since he was about to beg me to not take him to the beauty parlor. He knew that it was unlikely that I would relent, nevertheless, the outings I arrange are so excruciatingly humiliating for the poor dear that he is ever...

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