It was a dark and stormy night…

Dark and Stormy

“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.”

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It has only been a week but what a week this site is awesome and the Staff is so wonderful to deal with i am an older sissy and sadly my wife could never know. that’s sad because our life… Read more “lola”

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