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Jack walks with purpose down a city street. He is of moderate height with a slight build. His skin is fair and he is clean shaven. He is dressed in business casual, looking like he just finished his casual Friday working day. Behind him, Jack pulls a good sized suitcase on wheels. He strides into the lobby of a hotel and checks in at the front desk. Key in hand, he rides up the elevator to his third floor room. Stepping off the elevator Jack sees that his room is down the hall to the right.

After a quick look around the room, Jack opens his suitcase to unpack. His clothing all comes out of the suitcase and is either hung in the closet or is neatly placed in drawers. He stashes the suitcase in a corner, and then begins to remove his clothes. Off come the shoes and socks, the slacks, and the shirt. All are neatly put away.

Jack steps in front of the mirror. He admires the way he looks in his sexy red panties. They are cut high on the sides and he likes the way they show off his shaved legs. The tight, smooth nylon material clearly shows the outline of his growing cock. He watches himself in the mirror as he teases himself through the panties. He turns to see the way the thong is firmly nestled into his ass and nicely showing his smooth cheeks. He checks to make sure that his red toenail polish is still looking good.

He moves to the bathroom and runs water for a bath, adding a bit of fragrant bath oil. Jack carefully shaves the small amount of five o’clock shadow he has accumulated during the day, then stripping off the panties, he steps into the tub. Closing his eyes, the work week fades away, and Jack contemplates the evening ahead. After soaking for a time, he runs a razor over his legs, arms and chest. Climbing out of the tub, Jack gently dries his skin, then slips on a short, red, silk komono.

At the mirror, Jack looks at his face critically, and plucks a stray eyebrow hair with a pair of tweezers. He then begins to apply his makeup. He stops short of the hooker look, but he makes his eyes dramatic and finishes his lips with a wet-look, red lipstick.

In the bedroom, he opens the drawer that holds his lingerie. He removes a black, satin, corset; a matching pair of thong panties; and a pair of sheer, tan stockings. Jack wraps himself in the corset and rather awkwardly tightens the drawstrings in the back. He inserts breast forms into the top of the corset, and then he pulls on the small panties and settles his cock and balls into the confined space. Sitting on the bed, he rolls the stockings up his smooth legs and attaches them to the corset garters.

From the closet, Jack slips into a black, sleeveless turtleneck sweater. He then pulls on a very short, red skirt made of a lightweight stretch material. He selects shoes with a four inch heel, open toe, and a wide ankle strap. After putting on the shoes, he adds a silver necklace, then goes into the bathroom for his wig. The wig is auburn in color, shoulder length with gentle waves. Finally, he puts on silver earrings and bracelets.

Jack pulls a chair in front of the bedroom mirror. He watches in the mirror as he sits down and crosses his legs. He notes with satisfaction that his stocking tops are just covered when he sits and smooths his short skirt carefully. With equal satisfaction, he notes that with just a bit of squirming he can expose his stocking tops and garters. He smiles to see that when he uncrosses his legs, his panties can be easily seen when viewed from the right angle.

Jack closes his eyes and gently runs his hand up his stocking-clad thigh. His hand dips under his skirt and over his stockings. He caresses himself through his panties for a moment, then he pulls the panty to the side and releases his cock and balls through the leg hole of the panties. He strokes his hard cock a few times before tucking himself back into the panties.

As a final touch, Jack applies two coats of red fingernail polish, and sits quietly while waiting for the polish to dry. When it’s dry, Jack transfers his lipstick, cash and room key to his black purse. He verifies that the purse already contains a brush, compact, condoms and lubricant. He then takes another look at himself in the full-length mirror. He looks good. If he were more plainly dressed, most people would accept him as a woman without a second thought. His sexy outfit will draw attention, and some will spot him as a man in drag, but that’s OK. He looks sexy and he feels sexy, and that’s what’s important.

Jack puts his purse over his shoulder, takes a deep breath, and steps out the door and into the hallway. There is no one in the hallway as he walks toward the elevator. Waiting for the doors to open, he looks at himself in a mirror and smiles. A small breeze touches his legs and moves up his skirt. He thinks about the very small bit of thin, nylon panty that separates his genitals from the world, and about the little skirt that just barely hides his panties. He realizes that he feels nearly naked from the waist down. As he contemplates this delicious thought, the elevator doors open. Jack smiles at the middle-aged couple that occupy the elevator. He steps in, and sees the smile grow on the man’s face as his eyes travel down Jack’s body. He turns to the front of the elevator, but he can feel the man’s eyes on his legs and his short skirt.

The elevator doors open. Jack steps out and walks across the lobby. He puts special effort into ensuring that his ass sways as he walks. He looks back over his shoulder to find the man watching, so he gives him a wink and an air kiss. Jack leaves the hotel and turns right at the sidewalk. The sky is dark, and the street is brightly lit. His destination is just a block away, but while he walks, he savors the feeling of being outside dressed as he is.

Arriving at the nightclub, Jack opens the door and walks in. He stops and scans the room. The place isn’t overly crowded, but there is a good mix of people. On the dance floor he sees couples of all types, straight, gay and lesbian. The bar area contain a similar mix, and there are a number of stools available. Jack heads for a pair of open stools.

Jack’s arrival has been noted by a man and a woman sitting at a table in the shadows. They watch quietly as he crosses the room.

Jack can’t help but expose himself a bit as swings his butt onto the bar stool. He gives his skirt a little tug to cover his garters while he crosses his legs at the knee. The stool to his right is unoccupied. On the left is a man engaged in quiet conversation with another man on his left. The bartender gives Jack a friendly smile, takes his order, and quickly brings him a glass of wine.

The couple at the table are behind Jack, and not too close. But, they are close enough to see him easily. They talk quietly, looking frequently in Jack’s direction. After a few minutes, they seem to reach an agreement. The man stands and walks toward Jack. The woman looks in Jack’s direction and smiles.

Jack enjoys his wine and takes in more of the activity around him. He notes that there are a couple of other t-girls in the club, but he decides that none of them look as sexy as he does. He turns on his stool to continue his scan of the room, and a man steps up and asks if the stool to Jack’s right is available. Jack smiles, gestures at the empty stool, and says that it is indeed available. The man is moderately tall, his body seems to be trim, and he has a ruggedly handsome face.

The man orders a drink, then turns to look at Jack. He introduces himself as Mark. Jack says his name as Jackie, and they launch into some pleasant small talk. Jack works at keeping her voice as feminine as possible. She’s fairly certain that Mark knows she’s a t-girl, but the voice is part of the sexy illusion. When Jack’s wine glass is about empty, Mark ask’s if he can buy her another. Jack agrees, but as always, she is very careful to keep an eye on the glass. A girl can’t be too careful.

They chat about the mix of people in the club that night. Mark turns on his stool and quite deliberately looks Jack up and down. He looks Jack in the eye and says that she is one very sexy lady. He then asks if she would like to join him on the dance floor. Jack agrees. Mark stands and offers his hand. Jack takes his hand and slides off the stool. Naturally, her skirt rides up a bit and shows her garters. Mark has seen this and gives Jack a wink before turning and leading her by the hand to the floor.

The rock music is much louder on the dance floor, and conversation isn’t possible without yelling. Mark is a confident dancer, but he remains very attentive and focused on Jack. For her part, Jack is taken away by the dancing. She loves the way it feels to dance in a skirt. She is very aware of her stocking-covered thighs rubbing together, and of that delightful feeling of being nearly naked and vulnerable. Her eyes are closed when she feels Mark’s hands on her hips. She opens her eyes, smiles up at him, and moves her hands to his hips. They sway and gyrate together in time to the beat of the music. Mark takes her hand and spins her out. When he pulls her back, her back is to him. His hands go again to her hips, and he gently pulls her against him. Jack can feel Mark’s cock pressing against his butt with a gentle but firm pressure. Smiling over his shoulder at Mark, Jack slowly grinds his ass against Mark’s crotch. The music transitions to a somewhat slower song. Mark turns Jack around and pulls her close. He puts Jack’s arms on his shoulders, and moves his hands back to Jack’s hips. As they move together to the music, Mark’s hands quickly find their way to Jack’s ass. He cups her cheeks and pulls her against him. Jack is again very aware of Mark’s cock pushing against his belly, and also of her own cock against Mark’s leg, straining against the tight fabric of her panties. When the music changes back to a faster tempo, Mark suggests they return to their drinks. Jack leads the way, so he doesn’t see the gestures exchanged by Mark and the woman as they pass.

Jack and Mark return to their bar stools. With their drinks refreshed, and in the quieter environment of the bar, they resume their talk, but now with a more intimate feeling. Jack is facing the bar, but Mark has turned on his stool and has his back to the bar, and he is able to look directly into Jack’s face. The people to either side are turned toward their partners and totally absorbed in their own conversations. Mark asks her about her fantasies. She laughs and gestures at herself. Mark laughs with her, then gently lays his hand on her knee. They talk about fantasies while looking into each others faces. At the same time, Mark’s hand begins to roam. He moves up her thigh, then encountering the hem of her skirt, brushes his fingertips back along the length of her thigh to her knee and back to her hem. Mark is now talking about some of his fantasies, and Jack struggles to focus on what he is saying and to continue to meet Mark’s gaze. He looses that struggle momentarily as Mark’s hand eases under her skirt. She momentarily closes her eyes as she feels Mark’s hand on her bare thigh above her stockings. She opens her eyes and smiles up at Mark, having lost the thread of the conversation.

Mark slides his hand back down Jack’s thigh to her knee. Gently, but firmly, he grips her knee and forces her to uncross her legs. Very excited, but also a bit apprehensive, Jack glances around to ensure that no one is paying them any attention. With the exception of a woman seated alone at a table nearby, everyone else seems engrossed in their own lives. Turning back to Mark, Jack attempts to pick up the conversation again. Mark’s hand has moved to mid-thigh, and it now slides over her leg and between her thighs, gently urging them apart. Jack complies and parts his legs a couple of inches. Mark’s hand very slowly moves up Jack’s thigh and under her skirt. He pauses to finger a garter holding Jack’s stockings. At that moment, Mark is talking about how he likes the look of garter belts and stockings so much more than pantyhose. He gives the garter a little snap, and Jack lowers his eyes as he feels himself blush.

Jack now feels a finger slowly trace a wandering path across his bare thigh above his stockings. After a seeming eternity, the finger encounters her panties. The single finger becomes a full hand as it explores across the front of her panties. The hand lightly grips Jack’s cock through the panties. Mark smiles, and again the blush comes to Jack’s cheeks. As Mark strokes his hand back and forth along Jack’s cock, she gives up trying to carry on a conversation, but she hears him say that he’d like to have a French maid give him head. Now Mark’s hand moves to the side of Jack’s panties. He carefully slides his fingers under the leg band of the panties, and now his hand is resting directly on Jack’s cock. With a quick move of his hand, Mark manuvers the panties aside and now Jack’s cock and balls are out through the leg opening and free of the panties. Mark begins to stroke Jack’s hard cock. Jack’s eyes are again struggling to stay open as he enjoys the wonderful feelings. Mark whispers in her ear. He asks if she likes what he’s doing or if he should stop. Jack manages to convey that she likes it and that Mark shouldn’t stop. Mark asks if Jack thinks anyone is paying attention to them. This causes Jack to again scan the room while Mark continues to stroke. As before, no one seems to be paying any attention to them, although the woman at the table seems to turn away just as their eyes meet. Mark senses that Jack is about to loose control, and he stops the stroking. He asks if Jack would be interested in moving to a move private location. Jack nods his agreement. Mark carefully places Jack’s cock and balls back into the confines of the panties and removes his hand from under Jack’s skirt.

Mark and Jack begin to discuss options, and they realize that they both have rooms at the same hotel. As Mark has a suite, they decide to use his room rather than Jack’s. Once again, Mark helps Jack from the bar stool, giving her a sly wink as her skirt rides up. As they walk through the club, Mark places a proprietary arm around Jack’s waist. He opens the door for jack. Just before going outside himself, he waves a final time to the woman at the table.

On the sidewalk, Mark and Jack walk toward the hotel, with Mark holding her firmly around the waist. Partway to the hotel, Mark pulls Jack into a darkened doorway that is set back from the street. He moves her against the door and bends down to kiss her passionately. With his tongue exploring her mouth, his hands explore her body. In turn she moves her hands from his back, down to his butt. She then runs one hand around to his front and along his cock. His cock is very hard, and she can feel it pulsing through his pants. She works his zipper down and puts her hand into his fly. Moving down through the waistband of his silky bikini underwear, she grasps his cock and elicits a little gasp from him. While she is stroking his cock, his hands have moved under her skirt in the back and are feeling her bare ass. He runs a finger down the strip of thong and into her crack. He teases the area of her pussy, and now it’s her turn to gasp.

Coming up for air, Jack asks if Mark would really like to get that blow job from a French maid. Mark tells her that he would like that very much. Jack says that she would like to freshen up in her room, and will come to Mark’s room in about 15 minutes. They straighten themselves up and walk on to the hotel. In the elevator, they push the buttons for their rooms on the third and fourth floors, and move to the rear of the car. At the second floor, a man gets on, pushes the button for a higher floor, and turns to face the front of the car. Mark slides his hand from Jack’s waist, down his butt, and back up under his skirt in the back. His finger is just finding Jack’s pussy when the doors slide open on three. She gives him a quick peck on the cheek and says she’ll be up in a few minutes. She is sure that the eyes of both men are on her ass as she walks out of the elevator and down the hall to her room.

Back in her room, Jack looks at herself in the mirror. She pauses for a moment to lightly stroke her hard clit while thinking about the fun she has already had, as well as the fun still to come. She then strips off her necklace, shoes, skirt, sweater, stockings and panties. From the dresser, she pulls out new stockings and panties. The stockings are sheer black with a black seam up the back. Jack pulls these up her legs and attaches the black garters. She twists around to see and adjust the seams so that they run straight up her legs. She then pulls on the panties. They are white, cut in a bikini style, and the material is thin enough to see through. On the front, they have some lace designs, and they have three rows of ruffles that run horizontally across the bottom. From the closet she takes out a petticoat and a dress. The petticoat is very full and very short. Over this she dons the dress. This is a black, French maid’s dress. The skirt of the dress lies almost horizontally atop the petticoat. The petticoat stops just short of fully concealing Jack’s panties, so the bottom of her crotch can be easily seen when she stands up straight. She needs to only bend forward slightly for her ass to show clearly through the see-through material and the ruffles of her panties. Jack wraps a black choker around her neck, a small white apron around her waist, and places a small black and white maids cap on her head. Her shoes are strappy sandals with a 4 inch heel and an ankle strap. Looking in the mirror, Jack is pleased with how she looks, and she hopes that Mark will like it too.

Jack fastens a long, black cloak around her shoulders, grabs her purse, and heads out the door. She is a bit nervous about being in the hall and the elevator in this outfit, so she walks toward the stairs at the end of the hall. Unfortunately, a sign announces that reentry is only possible on the ground floor, so she turns around and walks to the elevator. Luckily, she doesn’t encounter anyone on the way to the elevator, or during her ride to the fourth floor. Her luck holds, and no one is in the hallway on four. She taps on Mark’s door, and he opens the door for her. Mark steps back and waves Jack into the room. While looking quizically at Jack’s hat, he asks if he can take her cloak. She watches Mark’s eyes as she opens the cloak to reveal his French maid outfit. Pleasure shows in his eyes as he takes the cloak, and Jack confirms this by brushing a hand across the front of his pants where a sizable erection is unsuccessfully attempting to hide. Returning from the closet, Mark insists that Jack pose for him. She gives him her best supermodel imitation. Mark is impressed and says so. He then instructs Jack to bring him a glass of wine. Jack is a bit surprised at the commanding tone, but quickly realizes that Mark is slipping into character to accompany her choice of outfit. Realizing the fun is just starting, she goes to the bar to fetch the wine.

Returning with the glass of wine, Jack finds Mark seated in one of two club chairs in the living room of the suite. She hands him the glass, but he waves her away. He tells her the glass is to be properly delivered on a serving tray. When she returns with the glass on a tray, she tries to serve using a bunny dip. Mark again corrects her style. She is told that the bunny dip is fine for some, but in this house she is to keep her knees straight and bend at the waist to serve. This way, others will be able to enjoy the view of her legs and ass. She serves Mark the wine as directed. He sips the wine and tells Jack to stand with her back to him. He then tells her to pretend she is serving someone. As instructed, she keeps her knees straight and bends at the waist. She is very aware that Mark can now see her panty ruffles along with being able to see her ass very clearly through the the thin material of the panties. She is both embarrassed and excited by this. Now Mark tells her to put the tray down and to face him. When she does so, he directs her to lift the front of her dress and petticoat. Feeling suddenly shy, she lowers her eyes and slowly complies. Mark tells her that her panties are very pretty, and that she should stroke herself through her pretty panties. Holding her dress and petticoat up with her left hand, she moves her right hand to her panties. She gently rubs her clit through the panties. She closes her eyes, but he snaps at her to keep them open. He wants her to be looking at him while he is watching her. At his direction, she dips her hand inside her panties and continues to caress herself. He then directs her to pull her panties aside to release her clit. Her clit springs free as she pulls the panties to the side. She feels a very exciting humiliation as she strokes herself for him, all the while watching him watch her. Before she gets to the point of climax, Mark instructs her to stop and to tidy herself up.

After she gets herself arranged back in her panties, she is told to get a small cushion from the sofa. Mark then tells her to put the cushion on the floor in front of his chair, and to get down on her knees. He has a leg on each side of Jack as he slouches down in the chair. He directs her to unzip his pants and to pull out his cock. When she does so, she finds that his cock is of moderate size, but that it is very hard. He orders her to kiss and fondle it. She leans forward and does as instructed. She kisses the tip and gently strokes the shaft with her fingertips. She runs kisses down one side then the other. She kisses the tip again and looks up at Mark. He takes her head between his hands and presses her down so that his cock slides into her mouth. He removes his hands and tells her to suck him off.

Jack is getting more and more excited himself while he uses his mouth and hands to get Mark off. She is pretty much lost to the world when she feels hands on her hips and a female voice saying what pretty panties she has. Jack attempts to pull away from Mark to see what’s happening, but again Mark holds Jack’s head firmly and slowly forces her mouth up and down on his cock. Jack feels the hands move from his hips to his ass. They caress his cheeks for a moment then one hand slips between his legs and finds her clit. She is enjoying the unexpected attention when the female voice comments that this isn’t what one would expect to find inside such pretty panties, and then asks someone else if they would like to see. A deep male voice says that he just might have to dip into that pussy.

Alarmed now, Jack pushes away from Mark and gets up from the floor. He sees a man seated on the sofa across the room, and a familar looking woman sitting on the floor. Mark remains in the club chair, but puts himself back in his pants and zips up. Being quite panicked by the turn of events, Jack runs to the door to the hall. No one gets up or looks at all threatening, but Jack rushes out the door and down the hall to the elevator. It is only when he is riding down to his floor that he calms down enough to remember how he is dressed.

The elevator doors open for his floor, and Jack is confronted by a nightmare; a large group of people is gathered down the hall to the left. Initially, no one notices him as he slips down the hall to the right toward his room. Looking back, he groans when he sees that the crowd is mostly college age males, jocks by the look of them. There are also a few girls in what appear to be cheerleader uniforms. It is the attention being paid to these girls that has allowed Jack to go momentarily unnoticed. Of course, this doesn’t last. Just before reaching his door, he hears one of the jocks give and wolf whistle and comment about the hot number at the other end of the hall. Jack preys that his key will work the first time and allow him to escape. He reaches his door and looks up the hallway to see several of the jocks and cheerleaders coming his way, laughing and shouting comments about his sexy outfit. At that moment, he that his room key is in his purse, and that his purse is still in Mark’s room.

Jack quickly considers his options. He can go move away from the group by going to the stairs, but that will mean walking down to the ground floor and through the lobby. There he can either ask for a key from the busy front desk, or take the elevator to Mark’s floor. Or, he can brave the gauntlet forming between himself and the elevator. He decides to take the shortest route, and he turns to walk down the hallway to the elevator. The jocks and the cheerleaders are now strung along the hallway, but they stand aside as Jack approaches. The jocks make appreciative or lewd sounds as he walks by, but they don’t bother or interfere with him. At least until a cheerleader points out what the jocks haven’t noticed, that the chick in the French maid outfit isn’t a chick at all. Now the comments become more lewd and suggestive. The guys begin to crowd Jack as he continues to make his way to the elevator. He feels hands begin to pluck at his dress and to pinch his legs and his ass. One of the girls steps right in front of him causing Jack to stop short. With a lewd smile on her face, she reaches down to his crotch and grabs his now flaccid cock through his panties. She suggests that maybe he’d like to pull a train for the team. This brings an enthusiastic cheer from the crowd. To the obvious disappointment of the crowd, Jack politely declines and continues to move toward the elevator. While they continue to taunt and tease him, Jack is somewhat relieved to realize that the group doesn’t seem to be a real threat. He reaches the elevator and pushes the up button. At first, he stands facing the doors, embarrassed to face the people, but after having his ass anonomously pinched and fondle a few times. he turns around. The cheerleader who felt him up is now standing right in front him and holding the arm of one of the jocks. The jock is handsome and dressed casually. The cheerleader is cute with shoulder-length brown hair. Jack realizes that the cheerleader’s outfit is very sexy. The top is sleeveless and form fitting. The skirt is tight and apparently made of lycra or some other stretch material. Since she’s not wearing the usual pleated or flared skirt, he wonders if she wears something more sexy than the usual underneath as well. As he’s having these thoughts, she grabs his crotch again. He is now embarrassed to find that his erection has returned. She smiles and tells her boyfriend to check it out. She quickly grabs the bottom of Jack’s petticoat with both hands and pulls it up. The crowd laughs and jokes about the big clit he’s got stuffed in his little panties. Jack feels totally humiliated. Mercifully, the elevator finally arrives. He hurries inside, pushes the button for the fourth floor, and tries to hide in the corner. Much to his dismay, the cheerleader and her boyfriend have also entered the elevator.

As the doors close and the elevator begins to move, the cheerleader asks where he’s going dressed up so cute. Thinking quickly, he says he’s going to a costume party. She replies that that sounds like fun, and that maybe they’ll tag along. At the fourth floor, Jack exits the elevator and hurries toward Mark’s room while the cheerleader and her boyfriend trail behind. At Mark’s door, Jack hurriedly knocks and wonders what he’s going to say. The cheerleader and the jock stand on either side of him. The door is opened by the woman. She is above-average in height, has short blonde hair, and is wearing a very short and sexy black leather dress. Jack remembers why she looked familiar before. She was the woman in the bar who was watching while Mark was fondling him under his skirt. She smiles and announces that Jackie has returned, and that she has brought more guests for the party. She invites them all in, but Jack says that he just needs his purse and cloak. The cheerleader tells him that’s nonsense, and she and the jock take his arms and pull him into the center of the room. The woman tells the newcomers to sit down, but she takes Jack’s arm and keeps him in the center of the room. She explains that he is just ill at ease because everyone hasn’t been introduced.

“My name is Stephanie,” she says. “I am married to Mark over there, and I’m bisexual. We enjoy swinging and picking up cute transvestites to play with. Now, what about you Jackie?”

Jack says nothing, so Stephanie continues. “OK, I would like to introduces Jackie. She, or he if you prefer, is a cute transvestite that we picked up earlier this evening. She is married, bisexual, and was hoping to get well fucked tonight.”

“That’s not true,” Jack protests.

“Oh Jackie dear, of course it’s true. First, you weren’t dressed like a hooker in that bar because you were going to a costume party, so I think it’s fair to identify you as a transvestite, especially since you then made a point of changing into your present sexy ensemble. Next, since I walked in the room to find your cute little pantied ass in the air while you were blowing my husband, I think we can assume you have a thing for men. Of course we had to go through your purse to identify the owner, and we found out about your wife Susan, so we can assume you also like women, thus you are bisexual. Finally, as for your plans to get fucked tonight, we also found the lube and condoms in your purse. By the way, good for you for preparing for safe sex.”

Jack sees that everyone is smiling knowingly about him and his desires, and he feels completely humiliated.

“That takes care of Jackie and me, let’s go around and have everyone else introduce themselves, and tell us how you know Jackie. Let’s start with Mark.”

“I’m Mark. I’m mostly into women, but I also like t-girls and I get off on doing cute sissies. I had a nice evening going with Jackie here, but my blow job was interrupted, and I expect her to finish it properly.”

Stephanie leaves Jack standing by himself for a moment and goes over to whisper in Mark’s ear. He leaves the room without a comment, and Stephanie returns to Jack’s side.

Next up is the man that had snuck into the room with Stephanie. He has a slightly hispanic look, with black hair and dark eyes. “I am Ricardo. I met Stephanie in the bar tonight. She told me that I could make love to her if I would first fuck a sissy that she knew. Stephanie is very beautiful and desireable, so I agreed. I am feeling very amorous now, so I look forward to fucking little Jackie here, at least as a prelude to Stephanie.” The little group applauds and Stephanie smiles and bows her appreciation.

The cheerleader stands to introduce herself. “Hi. My name is Linda. My friend Don and I were downstairs at a victory celebration with the rest of the team when Jackie got off the elevator. At first, we thought it was a girl, probably a hooker because of her outfit. She seemed to have trouble getting into her room and headed back for the elevator. When we got a closer look, we realized that she was a he. Just to be sure, I grabbed his crotch, and I can testify that this is no lady.” After the laughter dies down, Linda continues. “We followed him up here out of curiosity. I’ve never met a transvestite before, and It’s making me kinda horny thinking about seeing Jackie blowing Mark and getting fucked by Ricardo and maybe by Don. Hell, if I had a strap-on, I think I’d get off fucking him too!” Another round of applause and laughter as Linda sits down.

“As Linda said, I’m Don. Linda and I have been seeing each other for a few months. We’re into kinky sex play like bondage and S&M and stuff. I’ve watched Linda with another girl, and she’s said that she’d like to see me with a guy. I’ve never been interested in guys, but it might be fun to have this sissy blow me or to fuck him in the ass. By the way, if this is going to be a real party we can invite some more of the guys from downstairs if you want.”

Before anyone could second that motion, Stephanie said, “thank you Don, but we really don’t want this to turn into a real gang bang. No, I’m sure you’ll all going to get to play with Jackie as you have suggested, but we don’t want anything to be forced. Jackie is going to have fun being our sissy maid and sex toy, aren’t you Jackie?”

Jack was about to protest when Stephanie placed her fingers over his mouth. “No, don’t say anything just yet. I’m sure that if we took a vote now, the majority here would like for you to stay and play. But the decision to stay or to leave will be made by you alone, so think carefully. If you stay, you’ll be treated as our sex toy. In your French maid outfit, you’ll be required to serve us and to service us. Later, we’ll probably have you model some different sexy looks, like the outfit you wore to the bar that made you look like a hooker. As a hooker, we’ll have to pay to fuck you. All in all, I bet you’ll be living many of your own fantasies. So, Jackie think about it for a moment.” Stephanie walks over and sits on the arm of Linda’s chair, she whispers in her ear then returns to Jack’s side. Linda gets up and stands on the other side of him.

“OK Jackie, have you thought about how much fun it will be to parade around for us in your cute little outfits, to suck some cock and have some up your little ass pussy?” Again, before he can answer or protest, Linda pulls up his petticoat and skirt and Stephanie pulls down his panties. To his ever growing humiliation, his cock springs out, fully erect and pulsing with excitement.

“Well, the vote is in and it looks like you raised your hand to stay and play Jackie!” While the group applauds and laughs, Stephanie turns to face him, and reaches down and gently caresses his cock and balls before returning them to his panties. Softly she says to him, “relax and enjoy sweetie, it’s obviously what you really want, so savor the moment.”

Jack’s head drops. She’s right of course. He’s more turned on than he’s ever been. True, he’s humiliated and embarrased beyond belief, but that’s part of the turn on. He has had fantasies about being a sex toy in his sexy clothes, about being a serving maid, and about being made to be a hooker, and especially about being fucked in his pussy, but he never thought they would actually happen. He could probably still walk out now, but wasn’t this what he was looking for when he went out tonight? He looks up at Stephanie, “may I get you a drink mistress?”

“Yes Jackie, and check with our guests to see what they want. Oh, and don’t forget the proper way to serve.”

“Yes mistress,” Jackie says and curtsies to Stephanie. Jackie circles around the room and takes drink orders. After taking each order, she curtsies before moving on to the next guest. After taking all the orders, she goes to the bar area to pour wine and mix drinks. Carrying the drinks out on a tray, she goes to where Linda is sitting. She bends over from the waist to give Linda her drink.

“Nice ass!” and “Love your ruffles” are the first comments made by those watching her from the rear. These continue as she makes her way around the room with the drinks. Just before reaching Stephanie, Mark returns and whispers in Stephanies ear and Stephanie nods. When everyone has a drink, except Jackie of course, Stephanie proposes a toast, “here’s to play time with Jackie!” She then says, “put your serving tray away and come back out here. It’s time for you to take care of unfinished business.”

Jackie does as she’s told, and returns to stand in front of Stephanie. “You will now unzip Mark’s pants and finish the blowjob you were giving him earlier. I’m sure we will all enjoy watching you.”

“What!” Jackie exclaimed. “You expect me to do that in front of everyone? I can’t do it in private?”

“Of course you will you little sissy. Your only purpose now is to serve and entertain us. Your feelings of humiliation and shame are not our concern. Now do as you’re told before I decide that punishment is in order. And get a pillow first, I don’t want your knees to become an unsightly red color.”

All eyes are on Jackie as she crosses the room to get a pillow and then puts it down in front of Mark’s chair. He situates himself and Jackie gets on her knees between his legs. She reaches forward and pulls down his zipper. She then reaches in his fly and pulls out his hard cock. Linda yells out her appreciation, “nice cock Mark.”

Mark smiles. “Go ahead sissy, suck my cock.” Feeling ashamed but so excited she could burst, Jackie bends forward and slips her mouth around Mark’s cock. Mark groans and puts his hands on the side of Jackie’s head.

Jackie hear’s Linda shout encouragement, “you go girl!” As it happened the first time, Jackie now feels hands on her hips. But this time, she realizes there are more than just Stephanies hands involved. Without removing Mark’s cock from her mouth, she looks around and sees the leering Ricardo next to his ass.

“I believe it’s time for me to dip my cock into the pussy of this sexy little sissy,” Ricardo says. With that, Jackie feels as four hands pull her panties down around her knees, and then off one leg. She struggles to protest, but Mark holds her firmly by the head and Stephanie holds her hips.

“You will use a condom and plenty of lube Ricardo, I want Jackie to enjoy this. By the way, are you a virgin dear?” Stephanie asks. Jackie’s mouth is full so she can’t respond, but she manages a little nod of her head. “In that case, you will also be very slow and gentle Ricardo.”

To the encouragement of the others, Jackie hears Ricardo unzip and remove his pants, then the sound of a condom being torn open. “Here, let me do this”, Stephanie says as she begins to apply lubricant to Jackie’s pussy.

Wanting to get in on the action, Linda says, “hey, I want to help too.” Jackie now feels one hand on each ass cheek, and two hands lubricating her pussy. First one then the other dip gently inside. Then they begin a steady in and out motion. One hand leaves his ass and reaches around to his clit. Linda exclaims, “wow! He must really be liking this, his cock, or rather her clit is really rock hard!”

“It is now my turn,” Ricardo orders. He positions himself between Jackies knees, and then pushes them further apart. Jackie feels Ricardo’s hands on her hips and the head of his cock press gently against her pussy.

Stephanie has moved up by her head and whispers in her ear to relax and enjoy it. She moans quietly and momentarily forgets about sucking Mark’s cock. Stephanie now holds Jackie’s head still, so she is forced to keep Mark’s cock in her mouth, but allowing her to focus on what is happening at her ass.

Unable to do anything more than moan around Mark’s cock, Jackie feels Ricardo’s well lubricated cock begin to slide into her pussy. When he feels resistance, he pauses for a moment before pushing on. While Jackie has never had a man’s cock in her pussy, she has practiced with a dildo, so she knows how to relax to avoid any real pain. Ricardo’s cock keeps going in slowly. Jackie moans and wonders if she will be able to take it all in. It seems to go on and on, when suddenly Jackie feels Ricardo’s balls push against his ass. There is a pause and the others in the room cheer. Now Jackie feels Ricardo begin to pull slowly out of him. There is another pause just before it feels like he will pull all the way out, then he pushes forward again. Jackie feels the tempo begin to speed up a bit, and she thinks about how she is getting truly fucked, by a stranger, right in front of a bunch of other strangers, all the while with yet another stranger’s cock in her mouth. Oh, this is so very good!

Stephanie now begins to move Jackie’s head up and down. Jackie picks up the beat and starts to match the rhythm of Ricardo’s thrusts into her pussy. Both start getting faster. Jackie can see Mark lean his head back and close his eyes as his breathing speeds up. She can feel Ricardo’s hands grip her hips harder and increase the power in his thrusts into her pussy. Mark grips her head tightly and forces his cock deeper into her mouth and his whole body seems to be going into a spasm. Suddenly, her mouth and throat are filled with his come, and he continues to fuck her face. Now Ricardo pounds into her ass, and she can feel that he too is coming.

After a few moments, Mark is pulling Jackie’s mouth off of his now shrinking cock. Ricardo likewise is pulling out of Jackie’s pussy and collapsing on the floor.

“I think you better freshen yourself up dear, then we’ll need another round of drinks,” directs Stephanie.

Jackie sees that Don and Linda are watching her every move as she stands and pulls her panties back on. She begins to walk toward the bar when Linda calls her over. “Please lift your petticoat Jackie.” She does so, and Linda runs her hand over Jackie’s panties and her throbing clit. “Still excited I see, you nasty little slut. Now turn around and bend over.” Jackie does as she is directed, and she feels Linda’s hands on her ass. “I really liked sticking my finger in your pussy sweetie, and apparently you liked it too. I think we’ll have to improve on that in a little while. For now, I’ll have a glass of wine.”

Jackie fetches drinks and serves them. With this completed, Stephanie calls her over. “Mark brought your other clothes up from your room. Go into the bedroom and change into the hooker look you had on earlier.”

Disturbed that Mark had been in her room and going through her things, Jackie goes into the bedroom and closes the door behind her. She finds her earlier outfit laid out on the bed. She also finds the pink babydoll nightie and panties that she was going to wear to bed that night. She picks up the nightie and feels embarrassed because Mark has seen these, when they were intended only for her private pleasure. She takes off her apron, hat, French maid dress and petticoat and lays them on the bed. She hides the nightie and panties under the dress. Dressed only in her corset, stockings, heels and the ruffle panties, she walks to a full-length mirror. She poses and admires the way she looks, she turns and looks over her shoulder at her butt as she bends over. She removes the panties and puts them on the bed. Her clit is rock hard and she sighs and closes her eyes as she begins to stroke it, slowly at first but then speeding up. Suddently, Stephanie opens the door and walks into the room. “None of that now! You hurry and get dressed. I have guests that are waiting for their entertainment.” Jackie is humiliated to be caught so and she grabs her dress up to cover herself until Stephanie leaves, but Stephanie walks to the bed and sits down, obviously intending to watch. So Jackie puts the dress back and proceeds to get dressed. First the small, black, thong panties to cover her exposed clit. Then the black, sleeveless turtleneck, and finally, the short, red skirt.

“Walk over this way dear, let me look at you,” Stephanie directs. “You must swing your hips more suggestively to attract you clients. Now turn and walk out and back again.” Jackie puts more emphasis into swinging her hips as she walks this time and Stephanie is satisfied. “Now we just need to fix your makeup. Here, sit on this chair.” Jackie sits down and Stephanie gathers makeup. “Now scoot forward so I can reach your face easily.” Jackie scoots forward on the chair and Stephanie then forces Jackies knees apart with her own legs as she moves close to apply the makeup. Jackie finds very erotic to have Stephanie’s nylons rubbing against her own nylon-clad thighs. She begins to run her hands up Stephanie’s legs. “Now stop that. Are you a lesbian too? There, that should do it. What do you think?”

Jackie turned to look in the mirror. Stephanie had added considerable additional mascara and shadow. “I look like a whore!”

Stephanie’s only comment was, “well, duh!” She then directed her to the other room with instructions to be seductive and accommodating.

“Before Jackie entertains us some more, I have a little movie clip I’d like to play for you all,” Mark announces.

Linda pats the cushion beside her. “Here, sit next to me Jackie”. A wide-screen TV comes on, and Jackie sees herself in the bedroom. She is mortified as she and the others watch her posing and admiring herself. She thinks she’ll die of shame as she sees herself begin to stroke herself and the others laugh and jeer. When Stephanie asks if she is a lesbian, the others laugh, but Linda runs a hand up her thigh and looks serious when she says, “well, are you?” Before Jackie can react, Stephanie pulls her to her feet and orders her to model and pose for the group. Stripper music starts playing and she strolls around the room, posing in every sexy way she can think of. She is surprised to realize that all eyes are glued to her body. She begins to sway and dance to the music and she sees first Ricardo, then both Don and Mark begin to rub their crotches. Linda is squirming in her seat, and Stephanie moves next to Ricardo where she takes over the stroking.

Linda calls to Jackie to come back and sit by her. To her boyfriend she says, “OK Don, get those pants off.” Don needs no further encouragement as he quickly strips out of his jeans and underwear. His large cock is very hard and obviously very excited. “Jackie, I want to kiss Don and play with his cock and balls. And no sister kisses now, I want lots of tongue action.” Jackie is surprised to find how excited she is about carrying out this assignment. She kisses Don passionately and uses both hands to stroke and knead his cock and balls. She is really enjoying it when Linda orders her to stop and to go down on Don’s cock. Jackie finds that she is even more excited about this action and she does her very best at first teasing and then engulfing Don’s cock with her hungry mouth. She is now on her hands and knees on a couch, with Don sitting on one end and Linda sitting on the floor watching. Now Linda’s hands are on Jackie’s ass. She teases Jackie’s pussy, then pushes a finger in. With the finger moving in and out of her pussy, she hears Linda whisper in her ear, “you like that don’t you sissy. You like being fucked in the ass. You finish Don, and I’ll try you out.” The finger continues to move in and out of her pussy while Jackie continues to suck Don’s cock. Don begins to shudder. He grabs Jackie’s head as he explodes come into her mouth. He fucks her face until he is done, then he collapses back on the sofa.

Jackie looks around the room. Stephanie and Ricardo are kissing passionately. She has her hand in his pants and he has his up her dress. Mark has his cock out and is sitting quietly watching Ricardo and his wife make out. Don is out cold. Linda is still moving her finger in and out of Jackie’s pussy. “OK sissy, now it’s my turn. I want you on the bed.” She pulls her finger out and points to the bedroom. “After you.”

Jackie gets up and begins to walk to the bedroom, Linda follows and rubs Jackie’s ass. “All mine,” she purrs. In the bedroom, Linda tells her to sit on the bed and wait. Linda goes into the bathroom. When she returns, Jackie sees that Linda has removed her skirt and donned a harness holding a large, realistic looking cock dildo. “That’s right you little sissy slut, it’s time for me to fuck your ass. Do you like my new cock? Stephanie gave it to me because she knew I wanted to fuck you. Take off your little panties and lay back on the bed.” Though a bit apprehensive, Jackie does as she is told. “Pull up that little skirt now. Oh look! You’re all excited about this aren’t you. What should we think if you come while I’m fucking you? That would show you really like it wouldn’t it?” Linda spreads lube all over the dildo. She then kneels between Jackie’s legs and spreads more on Jackie’s pussy. She presses a finger in and wiggles it around. “Hmm, I think you’re ready. Now spread your legs real wide, cause here it comes.” Supporting herself on her hands and knees, Linda eases her cock against Jackie’s pussy. Jackie closes her eyes. “Open those eyes sissy, I want you to see me fucking you.” Linda then slides her cock into Jackie while being sure to keep eye contact. “Does that feel good sissy? I always love the feeling of being fucked by a man, but it does feel great to be the one doing the fucking.” She picks up the pace and slides in and out of Jackie’s pussy over and over. Jackie’s clit is being rubbed by Linda’s belly and she can feel herself getting more and more excited. She thinks that she might actually come while Linda fucks her. But before that happens, Jackie realizes that someone else has entered the room. She looks over and sees that everyone has now come in to watch. Yet again, she is terribly embarrassed, but she can do nothing about it while Linda continues to pound into her pussy. Suddenly Linda stops. She pulls out and moves off the bed. “That was fun, but I’m still horny,” Linda says. Mark offers to help and they go to the living room together. Jackie scrambles to cover herself while everyone looks on and laughs.

“It’s about time for the finale sweetcheeks,” Stephanie says. “Get out of all of those clothes and into that adorable babydoll. We’ll expect you in the living room in 5 minutes. Oh, remember we’re watching, so no playing with yourself. By the way, we’ll save the film of Linda fucking you, it’s pretty good.

Jackie hurrys to do as she was told. She takes off all of her clothes, including the corset, breast forms and stockings, but she keeps her wig on. She puts on the babydoll she had hoped no one would see. Looking in the mirror, Jackie confirms what she already knew, the babydoll conceals absolutely nothing. Her clit can be clearly seen through the gauzy material, and since it is very hard, it is only partially restrained by the little thong panties. Likewise, her little nipples are hard and erect and clearly visible through the nightie. Neither the nightie nor the thong panty covers her ass, so a look in the mirror confirms that she is entirely exposed back there. Swallowing any pride she might have left, Jackie steps out into the living room.

Jackie finds that everyone is sitting down around a futon that has been positioned in the middle of the floor. Lamps have been positioned so that the futon is in bright light while the surrounding room is in dim, half-light. “And now, for your viewing pleasure,” Stephanie announces, “our little Jackie will perform again for us. Since everyone has now gotten off except our little sissy, she is going to show us how she can do it herself. Please lie down on the futon Jackie. Knowing that you might need some current visual stimulation, we’ll turn on the TV for you.” Once again the big screen comes to life showing her in the bedroom. But this time, it’s showing her about to get fucked by Linda. “Go ahead dear, fire when ready.” Jackie looks at the screen and sees herself taking off her panties. Almost involuntarily, her hand moves down to her clit. The group murmurs it’s enthsiastic approval. She gently strokes herself through the panties as she watches Linda preparing to fuck her on the screen. She sees Linda enter her pussy with the cock, and she pulls the panties aside and begins to stroke her clit rapidly. She forgets all about these people watching her. All she can see is Linda fucking her. She explodes in a wracking orgasm and spews come all over herself and the futon.

The next morning, it’s quiet when he wakes up. Jack finds he is still wearing the babydoll nightie with dried come on it in several places. There is no one in the bedroom except him. Not wanting to be seen like this, he quickly looks around for his clothes. Not finding anything in the closet or the drawers, he pads quietly to the living room. There is no one there either, likewise in the bathroom. Returning to the living room, he notices a pile of things on the bar. He finds what he now thought of as his hooker clothes, along with his purse and a note.

“Dear Jackie, you had such a good time last night, we thought it shouldn’t end too soon. So, we’ve checked you out of your room and taken your other clothes and your wallet. You shouldn’t have any trouble getting a ride in this outfit, and since we left your purse, you’ll be able to lube up and practice safe sex. We’ll send all of your other stuff to your home. Have fun. Love, Stephanie and the gang. P.S. Since we’ve got your work and home information, we’ll contact you one of these days for another party.”

With a sigh, Jackie changed into her hooker clothes and went out the door.