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It was a dark and stormy night…

Stories of Feminization sissy Training It was a dark and stormy night…
Dark and Stormy

by stephanie

It was a Dark and Stormy Night…

…and Cold! The sleet was pounding across the deserted highway, and the wind seemed to zero in and seek me out. i was wet and cold enough after changing the first tire about 5 miles back – when the spare blew, i knew i was going to get much colder…

The thought of walking to Appalacha or Owego made me shiver – still, i was closer to Appalacha (I think). I put on my ex-wife’s pink baseball hat, (a souvenir from a Lake Placid hiking trip), turned the truck off, and stepped out onto the ice-covered macadam.

i could feel the wet cold of the night seeping through my clothes after the first quarter mile, and began to notice ice forming on my jeans and the brim of my hat after a half mile. The village’s lights still eluded me, but i pressed on. i looked back, and the truck had disappeared around a bend in the road, but i thought i saw a flicker of light. i turned and walked on. i could’ve sworn i heard an approaching car, but things went black…

i was warm and cozy – and the blackness of the night had given way to sunshine and the next day. i opened my eyes to a place i had never seen before, obviously a guest bedroom of sorts, as i sat up i felt the sensual feel of satin against my skin. Where was i? i pushed away the soft, floral comforter and swung my legs over the edge of the bed. i was dressed in a pretty, pink baby doll with a matching thong. my legs were rubbery and my head spun as i tried to stand, but somehow i managed. The door into the room was locked, but there was a small bathroom. i never needed to “go” so badly in my life. i made it back to the bed, put my head down, and I was asleep again.

The next sound I heard was a woman’s voice. “Hi, sweetheart, are you awake?” She couldn’t be talking to me, could She? As my eyelids fluttered open, there was a figure sitting beside me framed in the warm glow of electric light. “Hi!” She smiled at me. “Hi,” i said rather drowsily. “Where am i?”

“We saw you pass out on the road last night, you didn’t look good and we couldn’t find any ID, so we brought you to our place. Our next door neighbor, who is a doctor, said you were suffering from hypothermia, to keep you warm, and to call Her when you woke up. Would you like some tea?”

As i sat up i noticed that i still had the baby doll on and i reached for the comforter to cover up. She waved my had away saying “Its okay, relax, dear. When we peeled your wet and frozen clothes off of you, we couldn’t help but notice your peach colored thong. i thought you’d be more comfortable this way.”

She was still smiling as She handed me my tea. i thought i would gag on the first sip, but then the warmth seemed to seep all through my body. “Careful, I put a little brandy in that.” i managed a weak smile back. “So what is your name?” “stephanie…i mean Steve and Yours? “I’m Yvonne, but you may call me Kyssi. My slut’s name is Bill, and you may call him billi.” “Thank you for picking me up, i would probably be dead if you hadn’t stopped.” “That’s pretty much what the Doctor said…”

i took another sip of tea – it tasted and felt so good. “stephanie? May I call you that?” i nodded. “Are you a cross-dresser or a sissy?” …i almost spit out my tea! “i guess there’s no reason to lie – i consider myself a “would-be” sissy.” “Well, sissy stephanie, you owe us your life, and when you’re feeling better we’ll talk about that. Get some rest now. i brought in a portable TV if you want to watch a little. Finish your tea and get some sleep. We’ll talk some more later…”

Daylight was prying at the cracks of my eyelids when i awoke. i felt more myself, less scrambled – and i carefully made my way to the bathroom. Something in the room was different – but i couldn’t put my finger on it. On the counter in the bathroom there was a butt plug and a new woman’s razor. A post-it note on the mirror read, “you know what to do with these…Ms K”.

i looked at myself in the mirror and noticed that i was very pale – even through the two days worth of beard on my face. The tub looked very inviting…But first, i was hungry, and craving that first cup of coffee that i hadn’t had. i went back into the room and looked around. Just to the right of the bathroom was a beautifully organized vanity with one straight mirror and two angled ones. Everything a girl could want was there, from perfumes to makeup and deodorant to nail polish. There was a short dresser next to the vanity, with a coffee maker and a toaster on top. Off to the side was a small refrigerator. There was food in the fridge, but not just food, my favorites. A fresh package of English muffins, a loaf of Italian bread, cheese, butter, a quart of milk, some cold cuts, even my brand of orange juice. The coffee maker was loaded and ready to go so i flipped the switch, and to the smell of fresh coffee i checked out the rest of the room.

The door was still locked, which bothered me a little, and then i spied a laptop computer sitting on a small desk by the window. The note on the screen read “Turn me on…Ms K”. The LCD display popped on instantly. Words seemed to dance across the screen until they assembled a message: “Hi stephanie. i hope you are feeling better. There’s food in the fridge and coffee in the pot. Help yourself. When i return i expect you to be bathed, shaved, plugged and dressed. you’ll find whatever you need in the dresser and the closet. you will have put on make-up, perfume and nail polish. Show me what a good sissy you can be. When you’re done with all of that…press ENTER…Ms K.”

i poured myself a cup of coffee, wishing i had a cigarette to go with it, and read the message over and over. Did i have a choice? Probably. But this was the fantasy i’d been dreaming of for a very long time. i decided to go with it. i ate an English muffin and started a warm bubble bath.

i picked up a barrette from the vanity and as i put my hair up i noticed two shiny balls attached to my ear lobes. She had pierced my ears! i stared at the mirror in disbelief. How was i going to explain that? But somehow my fears evaporated as quickly as i realized them. They were pretty, and i liked the way they made me feel – feminine, soft, warm all over…i’d worry about it later, now it was time to start getting ready.

Soaking in the fragrant bubble bath was pure heaven. i thought i’d never felt so worry-free and comfortable. Not only physically, but mentally – everything seemed perfect – and instead of analyzing it and looking for problems, (my usual way), i just flowed with it. i felt perfectly at peace. As i soaked and shaved and washed my hair i couldn’t shake the feeling of belonging – of somehow fulfilling a destiny.

i toweled off, found a short satin dressing gown and began to lotion up. i couldn’t believe the pleasure i received from this simple act. It was as if my body was glowing – shooting sparks and beams of femininity. i picked out a smooth, pink, under-wired bra with a cute little bow on the front, and a matching spandex thong, carefully tucking myself in the process. As i rolled the sheer thigh-highs up my soft, smooth legs i thought i was about to cry. It felt too good! i was much too content. But once again the feelings of doubt passed quickly.

i applied my make-up as best i could, i had had some previous practice, and picked out a short lacy pink dress that showed off what little cleavage i had. The outline of my bra and panties were just visible beneath it’s soft caress. When i tied the ribbon in the back it looked as if i had a waistline. As i rummaged around in the closet for shoes i found a shoulder-length auburn wig, styled softly off to one side. The addition of a pair of 4″ pink pumps completed the new me.

i picked out some matching nail polish and a nail file and sat in front of the laptop. my nails were pretty rough, but in no time i was ready for polish. As i waited for my right hand to dry, i pushed “Enter”. The words broke apart and began to re-assemble again.

“The time is 2:30 pm Hi stephanie! I hope you’re feeling fine about now. you’re expected to be downstairs at 5 pm promptly. Until then you are welcome to follow the links at the bottom of the screen or watch some TV. If you would like to rest, there is an alarm set to go off about 4:30 to give you time to primp before coming downstairs. Enjoy the afternoon, my sweet sissy stephanie – we have much to do tonight…. Ms Kyssi.”

i poured myself another coffee, finished my nails, and sat on the edge of the bed. The remote for the TV was conveniently left on the nightstand. With a push of a button it came to life. A movie was already in progress, and i settled in to watch.

The camera zoomed onto a pair of handcuffs, attached to the wall with a pair of pretty red-nailed hands held fast to them. As it panned back i could tell that the grrl was naked except for a collar, and her lovely breasts swayed ever so slightly. her nipples were hard and excited. As it pulled back even more, i noticed a rope attached to the floor on one end, and fastened to a harness with a cock and a pair of balls at the other. Seconds later a masked woman, dressed in black PVC entered the room. She grabbed the grrl’s breasts roughly in a gloved hand and produced a paddle from a belt that She wore.

“You must show more respect when I have company you little slut” and with that She began methodically paddling Her captive. The grrl counted each stroke a-loud and thanked her Mistress for each stroke. Tears were streaming down her face before the Mistress let up. As She left, the Mistress said “you can hang there for a while, you little whore, until I decide what additional punishment you will require.” The camera zoomed in on her tear- streaked face and followed her body down to a pair of fire-red buns, and pulled back.

“That’s enough of that!” i said out loud, and switched the TV off. “i wouldn’t want to end up like that…” Curious, i went back to the computer and clicked one of the links. “Inside Sissify.com” popped immediately on the screen with the familiar “high-heel” logo that i’d seen before. In the password box was my log-in name, and a “saved” password. i hit “Enter”.

“How could She know about this?” i thought to myself as i navigated the familiar page. i clicked on “Talk-to-me”. A pop-up note appeared on the screen stating that i may watch the room, but that Ms Kyssi had temporarily removed my chatting privileges. i clicked okay, and looked at the chat screen. A couple of the girls were discussing some new purchases and a planned trip. i clicked “Home”. i was getting tired; the thought of lying down for a few minutes was overpowering. i made my way to the bed and was sleeping before my head landed on the pillow.

“Ding! Ding! Ding! Ding!” The not-so-gentle voice of the alarm woke me with a start. i got up, shut it off, and went to the vanity. Not too much damage, thank god. i freshened my make-up, combed my wig and smiled at my image in the mirror. “i’m a pretty sissy” just kept running through my head.

At two minutes to five, i heard a metallic click from the door. i tentatively tried the knob; it was open. Peeking out into the hall, i noticed lights and a staircase, behind me was darkness. Floating down the carpeted stairs seemed more than natural to me, and as i reached the bottom i heard heavy breathing and moaning. i turned the corner to see Ms Kyssi lying on the couch with a man pumping away at Her with his rock-hard cock. i turned quickly attempting to make a hasty retreat back up the stairs.

“Hi stephanie, right on time. i want you to watch this, dear. Come closer.” i did as i was told and as i neared the couch it was evident that they were both about to explode. Amidst flush faces, screaming and grunting, they both reached powerful orgasms. i timidly stood next to them with my hands folded in front of me.

“On you knees, stephanie, like a good little sissy.” Ms Kyssi commanded. i did so with no hesitation. My face was within inches of their sex, and i’m quite sure i didn’t need the blush that i was wearing. He slowly pulled out of Her, still hard and covered with slick juices. “Well, what are you waiting for stephanie, clean him up!”

i brought my face next to his manhood, looked up at him as if he were a god, and began licking and gently sucking on him. Swallowing whatever sweet love nectar i could. “stephanie, i want you to meet billi, he is My slut and you belong to him as well as Me.” When he was cleansed, i looked up and asked “Would You like me to continue, billi?”

“No, stephanie, i’ve had enough for now.” “Thank You, billi.” “Now you may clean Me as well, dear,” Ms Kyssi said. “Thank You, Mistress.” i began slowly licking first around Her sacred sex, and gently circling nearer. There seemed to be an endless supply of love juices coming from Her, and i savored every drop. i ran my tongue slowly from the top of Her anus to Her womanly clit, stopping to relish the sweet musk. Her breath quickened, She grabbed me by the back of my neck and pushed my face harder into Her wet sex. Then She was bucking and screaming. i kept my neck and shoulders loose and rode with Her until She pushed me away.

“That was wonderful, stephanie. i guess that membership at the House has taught you a thing or two. We will be having dinner in the dining room and you will be serving. Dinner is on the stove and in the oven. Set two place settings, dear.” “Yes, Ms Kyssi, ” i replied without even thinking, and i started toward the kitchen. “…and stephanie….?” “Yes, Ms Kyssi?” “Clean yourself up and fix your make-up first…” “Yes Ma’am”.

The lacy apron that was hanging in the kitchen looked adorable over my pink dress. i served Them london broil with baked potato, mixed vegetables and red wine. The house smelled delicious, you could almost taste the juicy london broil and the buttery potatoes. Of course, i was not allowed to join Them.

“stephanie, we will take our coffee in the living room”, Mistress said as She was finishing. “Coffee, Mistress?” i asked coyly. “you did remember to make coffee, didn’t you stephanie?” Ms Kyssi asked rather harshly. Turning, She said, “she has to learn, billi. “There’s only one thing she’ll understand, but it’s her first night, Mistress…”

“No, billi. We can’t start spoiling her already. stephaine! Come here now!” “Yes, Mistress, i’ll brew some…” She held up a finger to Her mouth, and motioned me toward the table. As billi stood, i felt my knees getting weak. “Bend over the table, stephanie…do it now!” i could smell the paraffin from the table candles as he roughly pulled up my dress. he was unbuckling his belt. “you’ll thank me for this, stephanie, understand?” “Yes, Mistress.”

The first blow came without warning, a sharp burn across my tender ass. i almost yelled in surprise, but managed to bite it back. After a slight pause there was another and it stung worse then the first. Then billi began raining them down on me, mercilessly. i lost count at thirty. my ass was burning and screaming at me. Tears were running down my cheeks. Then he stopped when Mistress ordered him to.

i had collapsed onto the table sobbing. Suddenly there was another stinging blow. “Thank You, Mistress Kyssi and billi, for taking the time to punish this worthless slut.” “you’re welcome, stephanie,” billi said. “You know, Ms Kyssi, there’s something about a nice red ass that i just can’t resist.” Mistress nodded Her head and winked at him.

i heard billi’s pants drop to the floor. The butt plug that i had inserted earlier was pulled out, and i felt the head of his cock pressing to gain entrance. The sensation intensified, and when He gave a final push he was in me completely. It felt as if someone had pushed the business end of a baseball bat up into me.

“Ooh, nice and tight.” “billi – show her what it means to be taken, you little slut”, Mistress smirked. There was no hesitation. he began slamming into me, deep, fast and hard. his cock felt as if were trying to get to the white tablecloth beneath me. It hurt like hell! my tessies had fallen out of my thong and were crushed against the table edge with each of his thrusts. i began to breathe and match his rhythm; the pain ebbed away and was replaced by an excitement i’d never felt. i wanted him inside me; i wanted him to fuck me harder, faster. i felt like a tightrope wire that was about to snap. There were tremors inside of me, each growing more powerful than the last. i felt my ass gripping at his cock, trying to pull it deeper within me.


Suddenly, my whole body seemed to spasm. i was flooded with a warm and violent sense of cumming. It wasn’t like ejaculating; it was from the middle of me, from my guts, from his beautiful cock pounding away at me. “Look, billi, the little slut is cumming, she likes this too much…” There were several harder thrusts, and i felt his cock grow bigger, and then we were both cumming. he shot his load of precious love juice deep into me, and i continued to spasm in ecstasy. his cock began to grow soft, and i felt him slowly pull it out. i could feel his cum running out of me and down my stockings.

“Go clean yourself up, and get out of My sight!” Mistress screamed at me. i could hardly move, let alone talk. billi helped me off the table and onto my feet. my legs were all shivers and made out of rubber. He got me to the stairs just as Mistress said: “Go on now, stephanie. Clean yourself up and change. I’ll bring you some tea in a little bit.”

i grabbed the railing for support, and pulled myself up one stair at a time. i got to my bathroom just in time to throw up what little food there was still in my stomach. i slipped out of my heels, took off my clothes, and peeled off my cum stained panties. Reaching into the tub, i managed somehow to turn the water on, flip up the shower catch, and step in. i never realized the pretty auburn wig i was wearing wasn’t my own hair…

i cleaned up the best i could, slipped into the satin robe i had worn earlier and collapsed on the bed. i don’t know how long i lay there, praying for sleep to take me, but when it finally did Ms Kyssi awakened me. “stephanie, dear, how are you feeling?” “Kind of nauseous, Mistress.” She sat me up; my ass was on fire again. “Drink this, you’ll feel much better.” It was more of the tea She had brought me the other night, spicy, warm. my stomach settled almost immediately. “I see you forgot to take your wig off, dear, ” She said as She pulled the combs out of my hair. “We’ll have to deal with that tomorrow…”

A loud “thump” woke me from a rather pleasant dream… Satin surrounded me; the sheets, comforter and the pretty floral chemise i was wearing. i could feel my breasts slowly swinging back and forth. A large callused hand reached around and massaged one of them. My nipples were so hard i could see them through the thin, smooth material. Someone was fucking me, and his rough body hair was rubbing my smooth ass cheeks raw: but i didn’t care. i was in heaven…fully developed breasts and a hard cock inside of me. His breath was hot and heavy on the back of my neck. i wanted to cum….

It was all replaced in a flash by the guestroom, lit by dawn’s first embers. i rolled over and tried to get back into the dream, but to no avail. The door clicked, and soft wispy footsteps seemed to lead right to me. “Good morning, stephanie.” It was Ms Kyssi, with more of Her famous tea – even as the smell filled the room i yearned for it.

“How do we feel this morning, dear?” “Very sore, Mistress, and restless.” “Do you remember that you ruined your wig last night?” “Yes, Mistress, i remember You telling me about it. May i have some tea, please? It smells so good.” “Not just yet, little lady. you have to learn that you must take care of your sissy things.” “Yes, Mistress. How may i do penance?” “you will wear this under your clothes today. you will not be able to take it off without My permission. Do you understand?” “Yes, Mistress. This foolish slut must make amends.”

“Good, now turn around and show me your pretty little ass.” Something smooth was pressing against my sissy cunt. i felt elated and dizzy at once. It slid in ever so slowly, with almost no resistance. She wrapped something cold and metallic around my waist. There was a clicking sound. “Stand up stephanie” She brought two thin metal straps from behind me, one on either side of my sissy clit and tessies, and clipped them to the waistband. A curved metal plate with a metal strap on the end was attached and placed over my sex. The strap went between my legs. When she cinched it to the waistband in the back my tessies were crushed against my body, and the dildo was driven into me even deeper – there was another click.

“There, there now my sweet stephanie, you will grow to love it. From now on you belong to Us. You must ask permission even to go to the bathroom. This chastity belt is impossible to remove with out this key. You will be locked in your room when one of Us is not here, and you shall wear this chastity belt, as punishment for ruining your wig.”

She held up a small chrome key. “Today, my delightful little sissy, we shall spend the day together. Here’s a little surprise…” She held up a small plastic box with a button on it. When She pushed the button the dildo in me became alive…vibrating, squirming, twisting and pumping into me. Within seconds i was cumming just like last night – from deep within me. my mind and body turned into mush as spasm after spasm of pure pleasure wracked me, each one more powerful than the one before. i was on my knees, i thought i would pass out…

Suddenly it stopped. “This remote has a half-mile radius. If i call and you don’t answer – i won’t hesitate to use it. You may think it’s very pleasurable now – but if i leave it on long enough you will wish to hell you were dead…understood?” “Yes, Mistress.” “Now clean yourself up, get dressed and come downstairs when your ready, and I’ll pick you out something pretty – we’re going shopping…”

While i was in the shower, Mistress Kyssi had laid out the outfit She wanted me to wear. It was a pinstripe pattern suit with a knee-length skirt, a white blouse and a jacket that looked as if it were tailored just for me. i slipped on a pair of black pumps and rushed down the stairs. “Well, don’t we look pretty today, ” She smiled as She inspected me. “But those shoes won’t due; I have some special ones for our little trip.”

Out of a shoebox She produced a pair of 5″ strap, black pumps with little locks on each. i thought the locks were ornamental, but as i snapped them into place She produced a key and smiled wickedly. “Those are on for the duration, honey, ” she quipped. “And what to do about your hair…” i stared numbly at the shiny padlocks on my pumps.

“Hmmmm…let’s just see if blondes have more fun, shall we?” She disappeared for a moment and returned with a long blonde wig. “Put this on, and if something happens to it….” The dildo inside of me began twisting and pumping again, my knees got weak. “Yes, Mistress Kyssi” i said weakly. It stopped.

Carefully, i smoothed it over my head and attached the small combs to my hair. As i walked down the hall i caught my reflection in the hall mirror. i was a woman. As i rearranged my blonde locks, i couldn’t believe what i saw. Staring back at me was a woman ready to go shopping. i couldn’t break myself away. “You look great as a blonde,” She said as She patted my behind.

We walked together into the crisp, sunlit day. i couldn’t believe how great it felt to be outside – especially dressed as i was. i had been out of the house before dressed, but usually at night or at a club, never during the day. The feeling of old man winter sneaking a peek at my garters just sent me into giggles. The heels were higher than i was used to, but i managed to maintain my balance.

Our first stop was a caterer. Mistress quickly and succinctly placed Her order. The staff seemed very friendly and familiar with Her. She was making arrangements for a party of sorts, but i stayed out of the way for the most part. She introduced me as stephanie, the new housemaid, and told them that i would be taking care of the arrangements in the future. i smiled and tried to remember their names – but I’ve never been very good at that.

The next stop was a uniform shop, where two seamstresses fit me for a classic French maid’s uniform, complete with apron, ruffles and even a duster. As one of them tried to attach the headpiece to my hair, the wig slipped, and Mistress commented how it was so hard to find good-looking help these days. They all laughed and straightened my wig. One of them, while attaching a garter, slid her hand all the way up my thigh, and seemed disappointed to find the smooth metal plate under my panties.

“This is Patti and Her assistant is Joy, stephanie. And how shall we thank these wonderful ladies for fitting you so well?” i curtseyed as prettily as i could and smiled a thank you to both of them. “That’s not exactly what We had in mind, steph,” Joy said. i was led into the back room, told to kneel between Patti’s legs. “I’m sure you don’t need instructions, stephanie, pleasure Her,” Mistress said grinning.

She lifted the folds of her dress, and as i reached for Her panties She said: “No stephanie, take them off with your sissy teeth; work for it, bitch.” She lifted Her dress and guided my head toward Her special place, and as i worked to remove Her panties, She threw Her dress back over me. i heard Patti lifting my dress and commenting on how nicely exposed the chastity belt left my sissy little butt. Just as i managed to pull Joy’s panties to Her knees i heard muffled talking.

“No, go ahead – it’s what i keep the little whore around for; enjoy Yourself” There were muffled footsteps, first away and then closing. i licked gently and carefully around my prize, and when i neared Her little nub She squeezed tightly on my head. There was a whistling sound and a sharp stab of pain across my already sore buns. A smooth hand gently massaged the rising welt. There was another, and another. It felt as if Patti was drawing a pattern on me. Joy was ordering me to stop teasing and get down to business, which i did with a passion. Patti continued alternating strokes of gentle hands and a sharp crop. Mistress Kyssi joined in by pushing Her remote control every so often, only adding to my humiliation and pain.

Joy mashed Her pussy into my face and Patti smacked me with 7 consecutive strokes. Joy was cumming. At first there were only tremors, but then She wrapped Her legs around my neck and dug Her heels into my back. My face was locked to Her sweet sex as She bucked and moaned. Patti continued Her straping, leaving welts halfway down the back of my thigh. Joy let me loose and pushed me away. i fell backwards and landed with my head on the carpeted floor between Patti’s legs. She squatted immediately on my mouth and suddenly i was filled with warm salty liquid.

“Don’t spill a drop, stephanie, or there will be hell to pay,” Mistress commanded. i swallowed the stream of liquid as quickly as i could, with only a drop or two seeping from the corners of my mouth. When Patti was through with me, She stood and walked to stand next to Joy. They embraced and kissed tenderly. “Not bad at all for a novice, Kyssi,” Patti smiled. “Come see us anytime.” i was excused to the bathroom to “primp”, as Mistress puts it. The packages were waiting for me by the counter as i walked out. “Nice butt, stephanie, i may just have to borrow you sometime,” Joy said.

The cool leather of the car seat never felt quite as good as when i got back into the car. “you did well back there stephanie, you will make a fine sissy,” Mistress said smilin. “Thank You, Mistress,” i smiled back. There was a couple more stops. The first was a wig and hat store, where Mistress removed my wig in front of several customers and had me try on several to replace the one i ruined.

The second was a fetish shop, where She picked up a new cat-o-nine tails and a riding crop. She had the sales person demonstrate them on me with my skirt raised. He seemed to take great delight in adding a few more stripes to my tender bottom. As we were leaving, i noticed that i really had to “go”. “Well, dear, you’ll just have to wait ’til we get home. I left the key to your belt, there.”

She stopped at the bank on the way, made me accompany Her, and chatted extensively with the bank teller while i stood with my hands folded in front of me. When i felt as if i couldn’t hold it another second She smiled a good-bye and we went back to the car. After another twenty minutes on the road, we were finally home. She casually slipped out of Her coat. “Mistress Kyssi? May i please have permission to go to the little girl’s room?”

“I suppose you do have to go, don’t you.” “Yes Mistress, very badly.” “Boil some water for tea, first, then I’ll unlock you.” i don’t think it ever seemed so long to wait for a pot of water to boil, but somehow i managed not to think about “going”. i brought Her the service and She pulled the key out of Her purse. “Bend over, stephanie, i can’t unlock this otherwise.” Finally i heard the lock click and the metal sheath dropped to the floor. i stood there until She nodded at me and i literally ran up the stairs to the bathroom. “While you’re up there – start getting ready for tonight.”

Mistress Kyssi was only a few minutes behind me. She brought a tray with sandwiches and some of Her wonderful tea. i could lose myself in the smell of it…warm, spicy, somehow so feminine. We laughed and talked like two old girlfriends for over an hour. “you have been a delightful sissy, today, stephanie. For your reward I’m going to remove the rest of the chastity belt; and i have something special planned for later. For now, though, it’s getting late, and you have to be ready, so pretty yourself up, put on your new outfit, and i shall see you downstairs in an hour.” As the lock clicked the metal band and straps fell to the floor. She couldn’t resist teasing me with the dildo for a while as She removed it. i felt empty inside with it gone. Tonight will be very special, indeed,” She smiled.

i showered and shaved again, wanting to be perfect for the evening’s festivities. The maid’s dress fit me like a glove, and the ruffles in the skirt made me feel so pretty. She had decided that i should wear the blonde wig, pulled back up in a bun, with the headpiece on top. i found myself daydreaming, fantasizing really, about my sissy bottom being filled. i got so wet i could feel a cold spot on my virginal white panties. As i made my way downstairs, i felt proud to be able to serve such a wonderful Mistress.

The next two hours were spent running around straightening and arranging. Apparently, She was expecting a lot of guests. The caterers came and gave me many tips on how to serve and preserve the fine goodies that they had brought. i felt ready and excited about the prospect of serving Her wonderful friends. billi came home a little after six, and Mistress instructed him on what to wear. A half-hour later he appeared with a collar, leather g-string, and a shear black dressing robe that did little to hide his best parts. his face was made up heavily, in dramatic, dark purples and reds, and i felt a tinge of jealousy when i saw the high-heeled fetish stompers he was wearing. he pranced about doing Mistress’ bidding much the same as me, but when we made eye contact i could feel a haughty snobbery in his look. It made me shiver.

The guests began to arrive at 8 pm. billi and i met them at the door, bid them welcome and hung their coats in the hall closet. The variety of people and clothing caught me completely off guard. There were men wearing nothing but crotchless panties with their clitties and tessies slapping their thighs with every move. Others appeared to be completely encased in rubber. Most of the submissives wore collars with leashes attached; the rest stood motionless and respectfully awaited orders. There were three or four sissies in cute little party dresses. They giggled a lot and seemed to enjoy the attention they were getting. i learned very quickly not to speak to the subs, and only to address the Mistress’ when They spoke to me.

The Mistress’ were awe-inspiring. They wore everything from simple black cocktail dresses to elaborate vinyl, rubber and leather costumes. Some had whips and cuffs attached to the belts they wore; others smiled and fondled Mistress’ collection of toys. All seemed genuinely happy to be here. i was very busy, but couldn’t help but catch the excitement in the room. Where was Mistress Kyssi? i hadn’t seen Her in quite a while. Just then, one of the subs put his hand up my dress and grabbed my ass. A Mistress in white leather cropped him one across the shoulder.

“you can look but don’t touch you filthy maggot!” She stated matter-of -factly. i curtseyed and said, “thank You, Mistress”. “So you are Kyssi’s new maid, huh? i assume you are a sissy under all that?” “Yes, Mistress.” “you are very lucky to have a Mistress like Kyssi to train you correctly. She trained my most recent acquisition, pointing: “in the blue, satin cocktail dress. her name is lois.” “she’s very pretty, Mistress.” “Thank you, dear.”

She turned and began conversing with the other Mistress’s, and i retreated into the kitchen to get another tray of hors’ devours. i returned just in time to see Mistress Kyssi’s entrance. She wore a tight leather bustier laced up the front, and a pair of skin tight black leather pants that were so tight they appeared painted on. She also wore a pair of thigh high spike heeled boots with silver buckles and chains…i had to stop and catch my breath. Her smile brightened the room, and the excitement went up a notch. As She turned toward me i noticed a long thick bulge down the inside of one of Her legs.

The party continued, and Mistress Diane demonstrated a new bondage corset that had rings and clips down the side. Her subby, damien, was rendered immobile and each of the Mistresses took a turn inspecting him, and allowing him to pay Them tribute. Some slashed a whip or crop savagely across his rear end – Others allowed him to kiss their shoes. It was getting, late; my calves were beginning to ache. Mistress called both billi and me to the center of the room.

“I would like you all to meet stephanie, my new sissy maid. she has only been here a few days, but has proven to be an excellent servant. And of course you all know billi – my favorite slut.” billi came over to me, stuck his tongue out and languidly licked my cheek. Mistress reached out and slapped him hard; he stumbled back – completely shocked.

“You will never touch stephanie again without permission, billi. Is that understood?” “Yes Mistress,” he bowed his head. “You will make amends NOW! ON yOUR KNEES!” billy complied immediately, there was an uncertain look in his eyes, and i think She really frightened him. “Pull down stephanie’s panties and make her hard with your slut mouth.” billi stared at Her in disbelief, but as She raised Her hand he reached under my dress. My panties fell to my ankles and i felt his lipstick covered mouth engulf my sissy clit. i became hard almost immediately, filling his mouth.

“Hold your dress up, stephanie, show off that pretty clitty of yours…” “Yes, Mistress.” i shyly pulled my dress up. “stop, billi, don’t move. stephanie, take your other hand and jerk off on his face.” We both stared at Her. “NOW!” She commanded. i grabbed my sissy clit and began to stroke it. “Slap him with it a couple of times, stephanie, enjoy yourself.”

i did as i was told, and just as i felt my sissy cum begin to boil she stopped me. “Get up, slut, and bend over that chair.” “stephanie, fuck him till you cum!” i tried to push my hard clitty into his puckered hole, but couldn’t penetrate. She backed me up a step, spat on Her hand, and rubbed it over me. She pushed me forward. This time i did enter, and as i felt him open to accept me, the room began to spin. i pushed deep and slow, fascinated by the look of my naked clitty sliding in and out of him.

“No stephanie, this is how you Fuck!” i heard a zipper behind me, and i knew immediately that Her strap-on pushing its way inside of me, i breathed in and accepted Her gift. i pinned between them, She thrust deep and hard into me, and i in turn into him. It was as if one long cock was fucking us both. Then, i began trembling inside again; my tessies seemed to suck up inside of me. i was cumming – both ways – all ways – my whole being sucked up into that one colossal moment. Everything went black…

“stephanie, wake up, dear.” It was Mistress Kyssi. i was warm and sleepy under the covers of my bed. “I brought you some tea, honey.” i opened my eyes. Mistress Kyssi was sitting on the bed next to me, a steamy cup of tea in Her hand. “Did you enjoy last night, stephanie?” “Yes Mistress, very much, ” i said reaching for the tea as i sat up. “i’m sorry i passed…” She put Her finger to my mouth. “It’s okay, you were fabulous last night.” i was beaming, i’d never felt so much a part of anything in my life. “We have to talk, stephen-andrew…”

Suddenly i was dizzy, when my vision cleared i felt different. i was no longer stephanie, stephen andrew had returned. And with his coming, my other life crashed down on me like a tidal wave. “i….” “I know you have a lot of questions, stephen. Let me try to explain before you ask, okay?” i nodded “Do you remember the night we first talked?” “Yes, i remember everything.”

“That first cup of tea had more than a little brandy in it. There were several feminizing agents and a mild hypnotic drug. That’s how i found out all about you. I called your boss, and told him you were interviewing for a job on the West Coast, and that he’d be hearing from you in the next few days. i found out your likes, dislikes and sizes simply by asking. Then i placed a mild hypnotic suggestion that freed stephanie from where you had been keeping her hidden. When I said your given name just now, the suggestion was removed.”

“You have a choice to make, stephen, ” She went on. “You can go back to your old life today if you wish. Or you can choose to stay and become stephanie permanently.” She paused, as if waiting for this to sink in. “If you go back to your old life, you won’t ever see us again and in time you will look back at this and remember it as a dream. If you choose to stay, however, i will continue your feminization. Eventually, your breasts will grow and your body will become more feminine. i will not allow you to have SRS, however, i want your male equipment to remain functional.”

“billy and I own a small chain of beauty parlors across the Northwest. We were here to visit friends and relatives. You will be required to attend beauty school, and to work at one of the local ones. If you’re very good, and believe me, dear, you will be, i have an opening for an executive secretary/personal assistant. You will live with billy and me in Washington while you train. i will arrange to have your personal belongings packed and brought out.”

“The choice is yours, stephen. Sip your tea and think about it. We leave tomorrow. The clothes you were wearing when we found you are on the dresser, and a darling, new outfit that i would love to see you in is on the closet door. Your truck has been fixed and is in the driveway.” “I’ll be waiting downstairs and will know your answer by the clothes you choose…”

The End

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i have only been a member for a few short days and have found myself wondering why i hadnt joined much earlier. Truth is i was very scared and worried to face my sissy desires. Now i find those fears… Read more “sissy cindy”

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The House is there like a beacon in the darkness.  You have done, and are doing, so much for the community and this sissy is very grateful.

It so comforting to be a member of this community, (you are all my sweet sisters) to know this sissy is not alone, in my exploration into what it is to be a sweet pathetic sissy, who’s only desire is… Read more “sally”

The House of Sissify has encouraged me to be the real me and experiment with all sorts of idea’s. Before I started I would rarely dress up, now I can’t go a day without wearing at least panties. I would… Read more “Jess”

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The House of Sissify is the best site that this sissy has found. she has spent hours in it just reading and learning. This sissy humbly thanks all the Sissify Staff

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i just wanted to express my gratitude for accepting me in Your sissy training and hope i can learn how to be a better sissy for my Wife.

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This sissy is infinitely grateful that you have welcomed her into the House and given her a safe haven among like-minded people. Although she has only been here for a short time, she has made tremendous progress in her deep… Read more “sissy fraenzi”

…and i must say that Madame Stewart is right, even in a distance of 3000 km, She made it possible to make me impotent.

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This sissy wishes to thank her Superiors for providing the opportunity for learning. This sissy is so happy at being able to learn how to be a better sissy.Thank you for providing such great insight, and for allowing this sissy… Read more “sissy michelle”

It seems the House of Sissify has loosened the ground up beneath me and im descending, in free fall, accelerating by the vast gravitational attraction of Femininity.

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I just wanted to thank you for having such a wonderful service. I have been looking for years to find someone to help me make this transformation. Again, let me say thank you.

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