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I became familiar with the Plumrose Dossier one cool February morning when it was read to me in the private rooms of Madame H at the Clinic.

***

I'd arrived that morning for my weekly 'therapy' and had only enough time to hang up my outer clothes in the Sissies' cloakroom and don my Eva Gabor wig before a facilitator poked her head in and told me I was wanted in Madame H’s office immediately. Even at that point I knew this couldn't be good so I shrugged into a nylon dressing gown and followed her down the corridor in my bare feet.

"What's it about, Dorcas?" I asked while simultaneously waving at another sissy who was being wheeled in opposite direction in a gurney. He was strapped ankle and wrist to the side rails and to judge by the tent in his negligee, loving it.

"Don't know sweetie, just know she wanted me to hustle you to her pronto. Probably about money."

"No probably about it," I thought. I turned my attention towards the facilitator's appearance.

"And what on earth are YOU wearing this morning?"

She had on a floor-length grey gingham dress that featured a tight bodice and a crisp white apron that ended a few inches above her hem. She was wearing her hair up, tucked under a cap.

"Because it looks like a Civil War reenactment!"

Dorcas laughed, "You're close, honey, it's a Simon Legree scenario I'm featured in later this morning.”

I noticed that although her apron was freshly laundered my acute eye could spot a faint straw-colored archipelago of stains from bygone escapades.

We passed one of the ward doors and Dorcas nodded toward it.

"Sissy Pulver is in there, waiting for me."

"I won't even try to imagine," I said.

We arrived at a heavy, richly varnished door labelled DIRECTOR in a gilt font. Dorcas knocked, we heard a mumbled reply and she prodded me through the entryway into a large quiet chamber carpeted in a deep blue pile and tastefully furnished in the same shade of oak as the door.

Madame H was looking down at two files on her desk top, her hand was to her forehead and her blue and white chalk-stripe suit jacket hung off the back of her chair. The silk blouse she wore was a burgundy high-collared invention. She looked up from her papers.

"Thanks for stopping by, Blane. But tell me, where are your slippers?"

"I was given no time to dress properly," I replied. "What’s the the emergency?"

She ignored the question, "Well, never mind the slippers, you won't be playing dress-up today anyway, I'm afraid."

She looked at me quizzically, "What are you wearing under that robe?"

"I told you I have only just arrived..."

She waved away my words impatiently and with the same hand beckoned me forward. I stepped up to the desk and she placed her hand into the teal nylon gown I was wearing and slipped her fingers into the leg-opening of my underwear and pulled the material away from my hip, (I should say here that I was still wearing the men's jockey bikini briefs I had arrived in.) I started to tell her this.

"Men's?" she chuckled, and turning me around with her left hand while her right was still inside my briefs she pulled down the waistband in back to peek at the label.

"Oh, quite right, men's -- nonetheless I saw them on you, Blane and they reminded me of the cotton knickers they made us wear at St. Anne's. Ours weren't, um, 'hipsters' like these though, we wore them right up above our navels. Those are a chic lightweight weave aren't they? They must make you feel very breezy when you wear them -- does your boyfriend approve?"

"You know I don't have boyfriends!" I protested.

"Well not yet,” she said quietly. “But we're not here to discuss your drawers, Betty."

She had used my sissy name. "We're here to discuss your money, or my money as the case actually stands. You are six months in arrears with your clinic fees."

She looked up at me over her lunettes. “At four visits a month, sometimes five... it's around seventy-five hundred dollars, a little more actually."

"What? It's only one-fifty a visit!" I protested.

"That was the introductory fee, first month only."

"That you've extended to me for a two and half years," I reminded her.

"True. Because you seemed to be good for business -- but those days are over now. How are you going to pay this?"

"I'm not, I can't. I just have unemployment insurance and what my sister can send me."

Madame H smiled, "You could get another job?"

"Get a wot?"

She leaned back in mirth, "I was kidding. You've got your house, Betty."

"Please! Anyway it already has a second mortgage."

She leaned forward across her desk and looked at one of the files on her desktop.

"A very modest one, plenty of equity here to get you clear with the Clinic, I've looked into it, you see."

I was behind in all my payments and another mortgage would reduce me to beggary. I'd join the rest of the homeless on Santa Monica's south side. Madame saw my distress and shifted the paper on her desk.

"There is another answer, Betty. We have a special friend of the Clinic, Harold Plumrose. I've been working with him recently. He is looking for someone like you -- a sissy, I mean -- you and I could make your financial problem go away and make him very happy."

"By doing what?" I asked suspiciously.

"Harold wants some play dates, Betty. He's looked though our 'patient roster'. You know a lot of our sissies actually like this sort of arrangement. He’s very picky but he liked you,” she smiled, "although you weren't his first choice. He'll pay for the privilege of being your friend for the next three months and you won't have to do anything you haven't done before, if my information is correct."

She cocked an eye at Dorcas.

"This is very depressing. My aunt left that house to my sister and to me!"

"And you honor her memory with this lifestyle of yours? Also, Betty, I know that your sister sold you her share back when you were both flush."

It was true. I looked at Dorcas for an answer but she was looking at the bookshelf.

"Listen, we'll split the difference and call it five thousand dollars that you owe the Clinic, Betty. I'll tell Plumrose it will be six dates, no more. It's a good deal for you."

It was. I sighed, "By the way, who did Plumrose like better?"

"Cindy, do you know her?"

"I think I've spoken to her here once or twice.”

(Like Madame, I could never refer to the lovely Cindy as ‘he’.)

"What does Plumrose want?”

"The six dates, as I just mentioned, starting with a house visit, his house."

"But WHAT will he want?"

"Well," Madame H crossed her legs in her tight skirt, "I don't know precisely, but just what YOU would want in his place, Blane, full British breakfast, I should imagine." She cleared her throat, adjusted her glasses and looked down at a document, " I'll give you all the particulars in writing later, but he lives in the Hollywood Hills, pretty far up. Are you driving? "

"I've still got my Karmann Ghia."

"Don't take it out of second gear, you should be alright. This Friday evening, Betty, can you manage that?" She handed over some typescript.

"Yes, I think so. Can I go now?"

"Soon. Dorcas, bring Betty into my study, won't you? And we'll have a look-see."

We went through a door behind Madame's desk and I found myself in a plain, smallish room with a daybed and a tiny sink jutting from the wall, its chrome plumbing covered by a lacy tulle curtain; a rolling tumbrel stood to one side bearing a tray of implements on its flat top. There were white painted cupboards in the walls and a wheeled stool on the terrazzo floor. It was an examination room.

" Slip out of your underpants and lay back on this, please.” Madame H indicated the daybed.

I undid the dressing gown stepped out of the white bikinis and reclined along a smooth black surface that felt cool on my bare legs. I was speculating idly whether the material was leather or pleather when Madame insinuated her hands between my raised knees and parted them. I felt her warm breath as she lowered her head to inspect my genital area.

"Just try and relax, Betty.” There was a long pause and then she stood up.

"Well, for the most part you are decently barbered down there."

"Our sissies usually are," offered Dorcas. And it was true. I had trimmed my bush down to a 'landing strip' -- a short vertical mustache atop my pubic bone, although the only thing that landed there were errant drops of semen during one of my masturbation sessions.

"We're just going to clean up your perineal area, Betty. Dorcas, you should find some shaving cream in that cupboard."

Madame H picked up a zippered bag from the tumbrel and produced a single blade razor which she placed next to me on the daybed. When Dorcas returned with the can she jetted a healthy glob of gel onto her hand and started to rub it onto the patch of skin just below my scrotum. It felt lovely, actually, it was that self-warming brand.

"Dorcas, you're better at this, will you shave Betty’s perineum?"

The Director stepped a little to the side and the facilitrix bent to her work while Madame's right hand hovered above this tight little scrimmage and held my balls up and back, clear of the action.

I should say here that despite the humbling nature of the conversation thus far, and even though I was naked with these two fully dressed women, the apparent disadvantage had not caused me to shrink, I suppose that the proof of a true sissy is that we are aroused by such humiliations and although I was not yet fully erect my cock exhibited an turgid state, standing away from my body a bit, with a downward curve in the middle.

As the magenta nails of Madame's right hand continued to hold my suspended scrotum, my apparatus began to engorge and soon the head, fully inflated and crimson with embarrassment was pressing itself against the tight translucent sleeve that covered Madame's forearm. She seemed not to notice.

"That's it Dorcas," she said, "go all the way between her cheeks. Yes, we want Betty as shiny and bald as Caesar's pate down there. Because that's the way Harry Plumrose likes it." she winked at me.

Dorcas stepped away when she was finished and Madame came back to the fore. She reached in to test the finish with the edge of her hand which she drew from the bony nub of my coccyx, between my cheeks, across the taupe pucker of my anus, up across my smooth perineum to the base of my scrotum. I was fully inflamed by now, my rod twitching helplessly.

"Yes," she went on, "we want anyone exploring this particular area to be unable to tell you apart from a blowup doll. Touch it, Betty."

I obeyed and was appalled to find such a strange, synthetically smooth, pleasure patch on my own body!

She let me pat myself and primp for a moment. I heard her open a cupboard and then Madame pulled out a shiny chrome appliance and plugged it into a wall socket. The device was the size of mango, although as I've said, metallic. She handed it over to Dorcas who wove her right hand through two coiled-spring straps so the exposed motor of the thing rode on the top of her hand.

"Stand over here, sweetie” the facilitrix said, as she positioned me in front of a kidney-shaped enamel surgical bowl sitting on the cart. She flipped a switch and her hand came alive amid the sexy electric hum of the machine which I now recognized as an old-school scalp invigorator.

Madame H read my thoughts. "Very popular in the fifties," She said. She was sitting on the stool and between her knees, at the hem of her skirt I caught a glimpse of the lace border of her slip, it was mint green. I gulped and felt my urethra spasm in agreement.

"Uh huh," I croaked, my eyes wide in horror, anticipation and delight.

Dorcas started moving the whirring device along my delighted shaft. The feeling was, as you might guess, electric, but more than that, because the vibrating connections with my flesh were the girl's fingers! I felt pleasure along with a ravishing sense of separation, my penis seemed to exist as a separate entity for a moment, not just with a mind of its own -- as the joke goes -- but a will of its own.

"Are you ready?" Dorcas whispered, then she moved her hand down over my testicles and I only had time to gasp before I gave up my load in three massive heaves and series of tapering shudders. Tilting the metal pan deftly, Dorcas caught my ejaculate in its hollow and presented it to Madame, who was seated on the wheeled stool watching the show.

Together they bent to examine this potage, and panting, I joined them. Madame H withdrew a green handkerchief from a taut pocket in her skirt front and handed it over.

"Wipe yourself darling, that was very good."

I was still leaking sissy juice down my right thigh so I dabbed with the cloth and then absently slipped it into the little pocket of the teal dressing gown I had doffed again in the chilly examination room.

I looked down into the bowl, what had been three silver-dollar sized dollops and perhaps six or eight M&M-sized sparkles of jism were starting to deliquesce into a single mass.

"The volume is fine," Madame opined, "and we can fix the texture."

She took the bowl over to the sink and tilted the evidence into it while running the tap. "Now Plumrose," she went on, "he likes thin, hot jets, and plenty of them. Follow me, children."

Back in her office she removed a white letter envelope from the desk drawer and handed it over. It contained a handful of pills.

"Guaifenesen," she said.

"Gwhy what?"

"Guaifenesen, the active ingredient in Mucinex and any number of drugstore-brand expectorants; it loosens and liquifies mucus so it can be expelled more easily. Relief for the common cold but in your case, Betty, it will produce a thinner ejaculate and more of it. You will empty out more thoroughly and refill more rapidly. Two a day, twelve hours apart. Now put on your bikinis and leave. Believe it or not I'm quite busy today."

I returned down the hall to the cloakroom with Dorcas who finally knocked on poor Pulver’s door. While hanging the dressing gown back on my hook I saw Madame H's handkerchief bulging in the small transparent pocket of the garment. I thought I might run it back to her office but it seemed a trivial reason to disturb the Director. Anyway I wanted to leave the clinic quickly and use my cell phone in the car.

What no one knew was that Cindy and I were a little more than Clinic chums, we had actually played together. Just once. We'd had fun but neither of us had followed up, I think we were too much alike, meaning selfish, both of us princesses needing to be adored.

Nevertheless we had gotten together at Cindy's townhouse, over on San Vicente, and spent a couple of hours trying on each other's lingerie (Cindy had a drawer full of the most delicious knickers, mostly vintage, some reproduction, but many real collector's pieces.) We each took about a million pictures of ourselves, inspired by mid-century girlie mags.

When it came time to consummate the date it was lovely because it was panty-play but it lacked the intimate connection I for one need to explore new erotic frontiers. Cindy seemed haughty around me after that but we were still friendly enough I suppose, so I sent her a text, " need to call u about Plumrose", and received the reply, "Ok after 6."

When I got home, after I had undressed, (stripping off my newly eroticized men's bikinis) and showered, I looked at the printout Madame H had given me. It told me I would be need to be outfitted for my date sometime on Thursday and that the date itself should commence at 9 PM Friday; until then I was to keep myself chaste, take the Guaifenesen as instructed and keep myself depilitated, "as of course behooves a proper sissy."
I wondered about the 'outfitting' but the rest of the instructions were as I'd expected.

I had some time to kill before the 6 PM call to Cindy, so I thought it would be a nice gesture to return a clean hanky to Madame. It would be gross, I thought, to hand over this handkerchief which I had dripped on earlier today.

I brought it over to the sink in the master bedroom's attached bathroom and flattened it on the counter. I admired the thing, stains and all, it was about eight inches on a side and of a substantial thickness of mint green silk, the exact color I realized of that slip hem I had glimpsed. The lacy border matched the one on her slip too, I guessed. At Madame H's level of deportment the well-dressed lady might actually buy slips, bras and panties that were all of a piece; in color, in cut and in lacework.

What I now held in my hand was a component of that trousseau. I sniffed the wondrous swatch -- there was something there, was it Chanel No. 5? Possibly.

An impulse struck me. I took the hanky with me to the bedroom and leaned back on the padded headboard with my right leg extended before me on the duvet while my left foot lolled over the side. I flopped the handkerchief across my thigh and drew it up to my hip and I loved the drag of it over my bare skin, the whisper of the fabric speaking of what it could do to my bare flesh.

Now I lay back fully across the queen bed with my eyes closed and my lips parted. I sashayed the cloth onto my belly and down. I let it rest there awhile. I caught my breath and rearranged my grip to the middle of the handkerchief and lifted it again, now it was a little 'tutu' which I danced lightly over my swollen organ. The feeling was exquisite and the accompanying sensations of the lacy border on my thighs and balls was intoxicating.

I was, I knew, just seconds away from releasing a devastating spray of semen so I backed gingerly away from that edge. It had been terribly tempting but my self-respect and my promise to Madame H prevented me from going further. I felt pleased with myself for my self-discipline. I told myself I was aloof from such antics. I also felt thoroughly girly.

I slid my long, Lili St Cyr negligee over my shoulders and my feet into my marabou mules. I put on a short perky wig and sat down on the bed to call Cindy. My erection, still assertive was pushing past the sash of my peignoir and though I may have been able to contain it with an undergarment I dursn't put on panties, as the act of opening that top bureau drawer might still push me over the edge.

It was 6:05. I called Cindy. When she answered she said "Hello, Betty" and I'll admit to being flattered that I was still in her contacts. I gave her the short version of the events that had just transpired. I was even more flattered when Cindy invited me to come right over. We shared the same zip code so it was nothing to motor the few blocks.

"What happened with you and Plumrose? Did you actually meet him?" Were my first questions.

"Oh sure, I saw him twice."

"And what's he like?"

"He's disgusting!"

"In what way?"

"In all ways, Betty. He's overweight, he's practically bald, breath smells of cigarettes, his face is like sandpaper when he kisses you, or goes down between your legs. And he's old, Betty, old!"

"He kissed you?" I was appalled, taking this all in at a gulp as I was. "How old?" I wanted to know.

"Oh God, I don't know, fifty-five maybe."

"That's only twenty-odd years older than you, Cindy."

"Tell me about it. I'm a hag."

"No you're not and you know it. Why'd you date him TWICE then?"

"Two reasons, first -- money, not because I need it," She lifted her slim arm ironically to indicate the well embellished townhouse around us, "but because getting paid would make me a call girl. I liked the idea, it's sexy, don't you think?"

It WAS sexy. To have that on your resume. I wasn't jealous of Cindy's wealth, nor of her lithe figure, but I was sure jealous of that.

"What was the second reason?"

"It was hot. Hot because it was disgusting. It made me feel so feminine when I was with him, a beauty and the beast thing, I guess." She grinned at a memory and went on, "Haven't you ever stuck your dick in something gross and loved it?"

"Just into your Vanity Fair granny panties. Seriously, what does he like to do? Madame was vague, just said he wanted everything, full British breakfast was her phrase."

"I know what you're worried about, Cindy, relax, he won't bend you over 'til the second date," she smiled sadistically "and then, close your eyes and think of England."

After that I decided to take the date as it came and I relaxed in the knowledge that I would be getting my 'whore' card stamped a full seven years earlier in my sissy career than Cindy had.

Cindy got up and poured us some Pinot Gris and she suggested we try on some of her things. I told her that I knew where that would lead and that I wanted to be able to look Madame in the eye when I saw her on Thursday.

"Okay," she said, "we can play another time. Now I have a question for you; you just said you owed six months of fees at the Clinic, how long have you been a member?"

"Two and a half years," I replied.

"Jesus Christ! You were already fooling around in the Clinic during your senior year at college? No wonder you didn't get into graduate school."

She wished me well at the end of the evening and I promised to call her with the details of my date with Harold Plumrose.

On the Thursday I presented myself at the Clinic and was shown to Madame H right away. She was at her desk dressed in the same suit, it seemed, but this time in a maroon iteration with a cream blouse and with nude hose and a brown suede pumps. She had a silver tray before her with a carafe and two cups.

"Good morning, Blane, would you like some coffee? Sit over here," she, patted the chair next to her and poured a cup out for me, then she swiveled to her left to face me, balancing her cup on her knee, " are you getting excited about meeting our benefactor?"

"I'll admit I'm curious."

The hem of her slip, where it rested on her chain's seat was champagne colored, the sole of her shoe as it rocked back and forth on her flexing ankle was buff and barely scuffed.

"Well, all questions will be answered tomorrow. Now, unlike your last visit you WILL be dressing today, Betty. I need to see you in a wardrobe item that Mr. P requested for you. To see if it fits."

"Can't you just check it against my sizes? You have them on file."

"No, not possible. Just change over by the mirror, and don't mind me I won't see anything your mother hasn't."

Too true, I thought, Madame was trim and healthy but she must be at least sixty.

Arranged on an oak valet next to a handsome cheval mirror were the items for me to model, whether for Madame's approval or her mere amusement I wasn't sure.

I picked up a white babydoll nightie by its narrow satin ribbon straps and lay it on the daybed. There was a pair of grey hose, heavy and expensive by feel of them; these I laid across the frothy heap of the nightie. Next, and quite interesting to me was a linen garter belt with four straps ending in sturdy stainless tabs; the garter belt was high-waisted and the linen was machine embroidered in a diamond pattern surrounding small eyelets. The accessory was white like the baby doll but while the nightie was a bright, synthetic, snow globe white, the garter belt was a matte, natural hue; its modest decoration made it seem as chaste as a maiden's apron. The accompanying shoes I recognized as my own white patent leather pumps which a facilitator must have brought up from my locker.

I sat upon the daybed and took up the first stocking. There is no way to don full-fashioned garter hose which is not lewd to behold, I looked up to see if Madame was watching but she had her face in some papers on her desk.

"These are VERY nice," I said, running my hands over the delicious friction of a stocking as I slid the hose down over my left calf which I was holding aloft, my toes a-point.

Madame H peered up only briefly and said, "They're very dear, don't go walking over uncarpeted floors in them if you want to wear them again. All that is yours to keep afterwards, you know. Lagniappe, you lucky boy. Oh, and do put on the wig, Betty, I hate it when some of you sissies like to parade around in your crew cuts while you're cross dressed. It's NOT sexy."

I finished pushing the last of the rubber tabs through nylon stocking-top. I fished out pair of sheer, white Nancy King full coverage panties from where they had been tucked inside one of the shoes. Arranging the tag into a neat flat flag below my right pelvis, I arose and pushed my feet into the rather tight and rather steep heels and posed before the mirror checking the hosiery and general fit of my rig.

"Anyone who sees you like that this tonight will be riveted, my dearest!" Madame H beamed at me from across the room. I had never known her to sound so benign.

"Come here and let's see you up close."

As I stepped toward the desk Madame H removed a hanky from below the desktop and wiped her lenses. It was my turn to be riveted - the handkerchief was a match for the champagne slip I had spied earlier. I was suddenly only too aware of the elastic waist and leg-holes of the scabrous panties, the feather-weight almost-not-there baby doll that clad me in a lurid cloud from my shoulders to my hips, of the garter-straps stretched tautly across my thighs and buttocks, the whole pornographic assemblage swaying across the room on those white, ironic/iconic high-heel pumps, inspired by some Elmer Batters wet dream.

I stopped before Madame and she reached to gently grasp my wrists to pull me closer so the frilly hem of the nightie was six or eight inches from her nose.

Madame H placed the fingers of each hand onto the knob of nylon and rubber where the garter tab held fast to the stocking top. She gave the front two a trial tug and then reached around to test the two that secured the back of my stockings. This movement placed her face even closer to the sheer white nylon covering my groin and there are no aesthetically correct or poetically apt words for it, my hardon raged! It jutted straight up and I found that the elastic waist-band of the panties was bisecting the mouth of my penis painfully, forcing it agape while the gusset was pulled up tight against my smooth, rubber-dolly perineum forcing my testicles to almost pop through the leg openings.

Madame's cheek gently rubbed against the entire inflamed mass as she continued to test the straps until finally, blessedly, she left off to compliment me, "You always knew how to wear your garters properly, Betty, and look how the belt gives you a tiny waist. Be sure to keep it tightly adjusted when you visit Mr. Plumrose."

Trembling, I moaned an appropriate response and returned to my clothing to re-insert my swollen self into my civvies, utterly knackered by the roller coaster ride of excitation and deflation I had suffered for the last two days.

As I changed back into boy-mode, a facilitator, Penelope, this time, arranged my new kit in one of the Clinic's white and green garment bags. I poked a finger through a hanger's hook, slung the bag over my shoulder and staggered away like a debauched rat-packer heading for McCarran after a Vegas bender. But MY weekend hadn't even begun.

I drove the few blocks to my home -- it was still in the forenoon -- drank a pint of Gatorade and dropped back on my bed. I was exhausted but my head was reeling with images. Finally I decided I didn't care if the Plumrose date was a success or not. The anticipation and the preparation were killing me. And so, with this attitude, I was able to drop off for a few hours desperately needed sleep.

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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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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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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...

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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Sissy Rules Reads like a proper job description

(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows...

1 year ago
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Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

3 years ago
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Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl outfits, super swishy behavior and a little sex, not to mention dominant women, are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fictional fantasy work. No references...

2 years ago
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Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

4 years ago
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Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
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Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

4 years ago
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Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
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Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve 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 brother.) James: AKA....

4 years ago
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Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

3 years ago
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Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

3 years ago
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Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

2 years ago
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Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

4 years ago
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Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

2 years ago
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sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
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Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

4 years ago
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Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

4 years ago
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Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - 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; 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...

3 years ago
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Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
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Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

3 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - 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 in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

4 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

2 years ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - 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 brother.) James: AKA. Auntie Jamie, ...

2 years ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
2 years ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

4 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

4 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

3 years ago
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Sissy Fantasy

I waited for what seemed like hours and was probably minutes when I heard Masters voice. "Silly me I forgot to open it, better hurry sissy I don't think Jenny would be too pleased if the neighbors saw you dressed that way," he smirked. The car lights flashed and the boot unlocked. I grabbed the cases and hurried inside. As I was passing Master he handed me a package. "A present from Jenny....put it on when you change... and put my case somewhere safe but don't open it," he...

3 years ago
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Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine 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 brother.) James: AKA. Auntie...

2 years ago
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Sissy Gets A Black Master

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

2 years ago
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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

3 years ago
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Sissy Stepson Part 6 Carolines Sissification

Part 6 - Caroline's Sissification Mrs. Monet was now going to really put the spurs to her sissy stepson and force him to live a life of sissified faggot. With Carl still lying on the floor with sissy cream stains all over his pantyhose and panties she began taking pictures of sissy stepson. "What are you doing, I want to change," said Carl. "Oh, no just because you popped your cookies doesn't mean its over, you pathetic faggot. I now have evidence what a pervert you are and I...

3 years ago
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Sissy Therapy

Sissy Therapy by Kate "Great practice, guys! If we keep working hard, we have a real shot at the conference title," Coach Jones addressed the thirty or so high school boys gathered around him. The boys were sweaty and tired, but the coach's praise momentarily raised their spirits. "Smith nice passing out there. Keep up the good work." Fifteen year old Billy Smith grinned cockily. "Sure, Coach. After all, I am the greatest!" The other boys moaned at Billy's arrogance. Coach...

4 years ago
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Sissy Stepson 8 Carolines Milking

Part 8 - Milking Caroline "Our sissy is going to get ready for milking, I have enough knee highs for everyone to participate" said Mrs. Monet excitedly. She gave everyone three knee high's, sissy Caroline was going to get the milking of her life! Caroline came back to the group with here outfit on and was instructed to sit next to Regina for milking. Regina encased the Caroline's sissy stick with the nylon and instead of using her hand. She took off her high heel and stuck the toe...

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