Room 100

My wife Holly, and I were away visiting her family. Before we left she had suggested I take a few days for myself and get away to do some vision planning and relax. "You have been working hard and taking care of me and everyone else. Go take care of yourself for a bit."

I eagerly agreed and sheepishly asked "One or two nights?" she responded whatever I needed. I reserved a rental car and booked two nights in a Hilton Home2 about an hour away from where we were going to be.

I gathered some of my special clothing items, but just the basics as I didn't want her to find them in my luggage. A few years ago, she had asked me to stop dressing up, I could not. A few pair of satiny panties, one of my slinky camisoles and a bit of extra padding. Oh, and some thigh high stay-up stockings. Unfortunately, no heels, too bulky. I thought I could easily find a pair of clearance heels that would suffice for the brief foray.

So, after the family business was completed, I gathered my stuff and my wife dropped me at the Enterprise office and I kissed her good bye. My first stop was a big shoe warehouse and found a cheap pair of heels. With summer winding down strappy sandals were clearance. I found a pair with 1" thick soles and 5" stiletto heels with a wide ankle strap. Next, I grabbed some snacks and beverages and headed to the Hotel.

I had checked in on line and gotten my digital room key. Upon arrival I went straight to my room, room 100. It was a corner room on the first floor right by the back door. I settled in and quickly shed myself of my male clothes and donned my feminine attire. Once dressed up with a heavy coat of bright red lipstick, I was reading Literotica stories and began playing when suddenly the door opens quickly and in walks a sexy guy, a bit feminine, struggling with several suitcases. He turns and drops them upon realizing someone was in the room already. We stare at each other for a moment before I blurt out "What are you doing in my room?"

And he responds "What are you doing in my room?"

We banter back and forth a bit and realize a clerical error was made, a double booking, before he says "You are quite pretty, why don't we share the room, I am here for the same reason as you, to dress up and have some fun. My name is Marcus and when dressed, Marci."

"I go by La'nette when dressed, or Lane when not." I paused "I don't know, it is a little tempting. I have fantasized about things like this. I am curious about sharing, trying different things, but I am afraid... Oh, hell, I think I would like to meet Marci."

I stand and stammer a bit as he steps up to me and leans in and kisses me tenderly before saying "Submit to me baby, I can help you take your dressing to another level. Introduce you to another level of pleasure. We can have some serious fun girlfriend." His hands cupped my satin covered ass and pulled me tight to him.

I found myself returning the kiss and tingling all over. What was I doing? I had never been with anybody in any sexual way other than my wife. Let alone dressed up, this was amazing. I was kinda thinking, I wish my wife could join us then he kissed me again and I melted into him.

"I will take that as a yes my new little sissy girlfriend." He then helps me dress at a different level, first by helping me shave from the waist down. He says smooth stocking clad legs are for everyone's benefit, but he wants me to maintain some masculine features, a bit of the 'bi' nature. Next, he pulls out a garter and black seamed stockings. Marcus helps roll them up my now smooth legs. It feels exquisite, nothing like I ever felt before. Then a pair of satin panties with lace trim, so sexy so feminine.

After that he asks "How experienced are you with CFM heels?"

I answered "Quite."

"Excellent," he said as he retrieved a very sexy pair of slutty high heels with 2" platforms, 6" stiletto heels and a wide ankle strap. He kneels down and caresses my feet one at a time as he slips them into the heels and secures the strap and then adds a small heart shaped lock to each and adds "Not that you will want to take them off, but, it makes you a little beholding to me as I have the key."

Next, he gives me a black satin and red lace corset and helps me into it and cinches me real tight and pushes my little man breasts up and together giving me a bit of cleavage. I gasp for breath and reassures me I will get used to it.

Marcus has me sit and affixes some rather long acrylic nails in bright red. Then some extreme false eye lashes following an opaque foundation and then a touch of blush accenting my high cheeks. Following that he applies some intense eye shadow and mascara. He won't let me see his progress yet saying "I must complete my masterpiece with my favorite part, lips." Next my new lover outlines my quivering lips with a dark red liner and fills that in with bright red lip stain telling me that this will keep the sexy color all night long. Then finishes that off with a thick layer of glittery gloss. He steps back and pauses before saying "Oh my gosh, you are absolutely gorgeous."

"Alright my sissy slut, go get us a drink while I change into Marci." He firmly directs. I turn in and look in the mirror. Holy crap I look fabulous. I faux kiss him and go out to the kitchenette and prepare a couple of drinks. When I go back he is already in a garter and stockings, satin panties, crotchless, and a bra with large gel breast forms. He is at the mirror and applying foundation. Next extreme lashes followed by long pink nails furthering the transformation into Marci. Wow, she is so sexy and beautiful. I step up behind her and press my very hard 'clitty' onto her ass as she applies a heavy layer of hot pink lipstick. We both don long lacy robes and opera length satin gloves. We strut out to the living area and get cozy.

We hang out a bit, talking about our fetishes, our passion for women's clothes as we watch some CD porn. We make out a bit, kissing, caressing, and flirting intently. Then there is a knock at the door. I freak out a bit and Marci, calms me some and goes to answer the door. She returns with a tall dark and handsome stranger. She introduces him as John. I am freaking out first Marcus invades my world and now some 'John' enters what was my private world. Is this what I think it might be. Marci is now pimping me out? What would my wife think?

I hope she would think I am a sexy sissy slut and join in. John draws me back to this new reality by helping me to my feet and pulling me tight to his firm body. Marci chimes in "You slut, he was my date, are you at least going to share him?"

John kissed me passionately before I could reply. Then I said "Well, I don't know. Your kisses are fabulous Marci but, I really liked being kissed by a man."

Marci laughed and answered "Well, if you liked being kissed, wait till he takes that sweet cherry sissy pussy of yours." That thought both scared me and aroused me greatly. Yesterday this was supposed to be just a private little CDer getaway, now I am extremely dressed with another CDer and a very handsome stranger.

Just then my phone rings and Marci grabs it and says it's your wife. I think how does she know it's my wife, my phone just says 'Holly'? That thought quickly fades as she says "Ask her for another day." My lover hits answer and hand me the phone.

I say "Hi Babe. What'ch ya doing?" She asks how I am doing and I ask for another day. She replies "Sure babe, I know you need this time. Have fun, relieve that stress. I will see ya soon." She weirdly emphasized 'soon' I thought but Marci grabbed me and pulled me back between her and John and into the present. She was kissing me passionately as John caressed me all over before spinning me around and kissing me as well. I spend the evening with Marci & John.

Wow, I am so aroused, being dressed all sexy and sharing it with someone (I wish Holly would share this part of me). From nearly the beginning of my dressing, I have fantasized about being with another sissy but recently I have been fantasizing about being with a man, here I am with both. We kissed and fondled each other for 30 minutes or so before Marci helped John out of his clothes and was licking and sucking his magnificent cock. Shit, it was much bigger than mine.

I freshen my lipstick as I absorb this erotic scene before me. After a few minutes of watching Marci hungerly devouring John's hard cock, she suggested I do the same for her. I hesitated a bit and she said "Come on slut you know you want to suck on my clitty cock and I want to be your first."

John chimes in "I want to be your first real cock." I reach out and touch her crotch feeling her hardness. As he adds "I would love to be the first to pound that sweet sissy ass of yours."

"Right behind me big boy." Marci claims.

I ternately kiss the tip of her clitty leaving a bold lip print on it. She moans around the big shaft in her mouth. This encourages me to lick and suck it more eagerly. After about ten minutes Marci is squirming under my attention and I hear John's moas getting louder. He comments on how hot it is watch us two babes together.

Soon Marci is working her hard shaft in and out of my mouth as John does the same to her. She moans loudly and starts cumming in my mouth. I panic a bit but she encourages me and lets loose and I struggle to keep it all in my mouth. I am not completely successful as a lot escapes and some drips down my chin and splatters on my face as her softening cock slips out of my mouth.

John says "That is fucking hot as hell you sluts." I lay back a bit to watch. He his now holding her head and thrusting in and out boldly and yells "Here it comes my sweet slut Marci." And thrusts in deep one more time and shutters releasing his big load into her mouth. She manages to keep it all in.

We all rest for a few moments Marci and I freshen our lipstick before John grabs me and guides me between his thighs and says "Hey sissy slut, wrap those pretty lips around my cock. Get me hard again so I can fuck Marci's tight ass. I will get yours next time."

I sheepishly kiss the head of his already growing and hardening cock leaving a lip print there. I admire my mark and then begin to lick and suck it eagerly thinking if Holly could see me now. How hot it would be to be getting a stud aroused and hard to fuck her.

Back to the present. Marci got on all fours and John said "That's good slut, go fed her your clitty as I pound her sissy ass." I did as directed, and Marci took me into her mouth. What an exotic sight. A sexy cross dresser sucking my little clitty as a big handsome stud fucks her long and hard. Soon I was cumming in her mouth and shortly John was filling Marci's ass with his second load tonight. Oh my gosh, I have never felt things like what they did with me and to me. I am hooked.

Next day: Marci and I wake up and make love for an hour before we dress sexy and shop all afternoon and get our nails done and an extreme make over and were quite dressed up with party / rave wear, new slutty heels, and head out to dinner. We are all over each other, caressing, and kissing. A gorgeous couple walk up. A tall dark and handsome gentleman and a sexy goth babe approach our table. Marci introduces me to them and I immediately think she is doing it again, pimping me out. My fear escalates but so does my arousal. She introduces them to me. They are Josh and Sasha. Sasha is a CDer like me and Josh is obviously bi.

Marci invites them to join us. Sasha slides in next to me. Sasha and I start out kissing as do Marci and Josh. We enjoy the evening out before returning to Room 100 and really enjoy the rest of the night in. Sasha and I spend much of the evening in a hot 69 while Josh pounds Marci long and hard. We end the evening with me on all fours devouring Josh' hard cock and Marci pounding my sissy pussy. Oh my gosh this is fabulous fantasies coming true. In two days, I have had two tasted cum from two sissy clitties and two handsome hunk's cocks and now losing my anal cherry. After Marci filled my ass with her cum and Josh my mouth with his. We all collapse and rest. Josh and Sasha leave and Marci and I change into some sexy lingerie and snuggling into bed.

The next day similar activities ensue. More shopping and new sexy clothes and good food at dinner out with Marci. We are even more dressed up than yesterday with elegant evening gowns and gloves, new slutty heels, and head out to dinner. They seat the two of us at a table for 6 a bit odd I thought but we are enjoying great food and wine and I look up and there is Holly standing at our table. She is dressed to the nines in a sexy evening gown with long fingerless gloves that present her long sexy nails. There is a long slit in the dress and her stocking clad leg is sexily protruding. I scan her leg from her thigh down to her foot clad in a CFM heels. Her face is exquisitely made up like those glamor shots. Long fluttery lashes and full pouty lips heavily painted in bright red shiny lipstick.

Holly says "Holy shit look at you baby! You look amazing." Turning to Marci she adds, "You did a remarkable job with her as promised."

After I finish ogling my sultry wife, I realize there is a tall dark and handsome hunk with his hand on her back. Holly introduces him as Miguel. And behind them is a cute, obviously a crossdresser, sheepishly avoiding eye contact as she is introduced as Missy the Sissy.

Is this whole thing a set up? my head is spinning in confusion as my little clitty is harder than ever. They join us at the table for 6. Marci is on my left and Missy sits on my right while Holly and Miguel sit across from us, very close together, it appears his hand is on her thigh and then when Holly knows I am watching she kisses the handsome man quite passionately. Right in front of me.

"That's right baby Miguel and I are lovers, have been for a while." She says matter of factly and then adds "He introduced me to Marci and she convinced me to allow her to transform you." She kisses Miguel again before adding "If you're gonna be a sissy husband I am gonna be a hot wife. Marci showed me what a sissy slut you have been. Wait until you see what a slut I have become."