The Sissy Hotel

"Hi, you're Melissa aren't you?" asked Chuck

"Yes," she confirmed.

"My friend Emily here would like to date you but she's incredibly shy," he straight-forwardly declared. "Would you like to date her?"

"Yes, I'd really like to date you," she answered without a moment's hesitation, looking at me. "I was kind of trying to tell you in there, but I fumbled it because I'm hopeless at this sort of thing."

"Awesome. She's got a photo shoot session next, would you like to join her?" I wasn't asked to be part of this conversation at all. I just stood there in socially anxious silence while my confident friend arranged my life for me.

"I'd love to."

I managed a smile, but couldn't speak.

"I now pronounce you dating," Chuck announced with some gusto, like a priest officiating at a wedding. "Be in the big conference room at 1pm, other end of the hall."

"Sure I'll be there." This was all a little awkward. Melissa just looked at me and smiled. "I'll see you soon Emily, I promise." She nodded at Chuck and went back inside. I heard a thump as if she had just fallen against the back of the door.

Did I have a date?

"What are you two girls doing! No talking!" Oh god, Consuela was just everywhere.

...

It only took until the end of lunch for my relentless and merciless internal monologue to convince me that I definitely did not have a date. I was an undatable screw-up and that was a fact. Chuck must have confused Melissa into it and this was all some kind of massive mistake. She probably wouldn't even show.

We had moved onto the photo shoot session. The hotel conference space was set up with several photography and film sets depicting different scenes. Girls were changing into costumes and spending a few minutes on each set for a short scene to be filmed or some photos to be taken before then moving on to the next set. We'd get all the images when we checked out as a memento of our stay.

I now had all the tools at my disposal to ruthlessly sabotage the date that I was certain I didn't have anyway because I didn't deserve it. Just in case she turned up I had better demonstrate to her just how far from the masculine ideal I was and surely not dating material. I was standing on a photography backdrop in a costume I had specially selected to debase myself. I was wearing a pink frilly tutu with white pantyhose in pink heels. I had a pair of lilac wings on my back and was holding a golden wand with a star on top.

Two very bright lights were trained on me as I smiled for the photos. To my astonishment I saw Melissa arrive. I could see her in shadow only and the lights were so bright I couldn't make out her expression. She stood about ten feet behind the camera with her arms folded. I imagined her scowling as she gazed with complete disgust upon the total fag in front of her. The photographer gave me instructions. I blew a kiss to the camera and pointed my wand. I tottered around and bent over, displaying my ass under the tutu and turned around to pout.

I was done in about twenty minutes and was encouraged to move on directly. One of the ladies from the salon helped me out of my fairy costume and I was left naked aside from a pair of pink panties and matching bra. I was quickly escorted on to the next set. I glanced at Melissa, I thought she waved but I wasn't sure. I couldn't quite make her out.

This experience was a classic porn scene. I'd agreed to some additional participation that would be sure to remove any remaining shred of masculinity, as if I had any left. I was stood on a bedroom set together with a stark naked muscled bodybuilder, who briefly introduced himself with a firm handshake. He asked me to bend over the edge of the bed, facing into the camera which was at a low height directed straight at my face. He pulled off my panties and positioned my legs apart a little, then he proceeded to lube me up and put on a condom.

He placed his hand on my back to keep me pressed against the bed and slid into me. Without ceremony, my second virginity had been taken in an instant. It was painful at first but got better. The camera operator told me to lift my head, look at the camera, smile and to pant hard in time to his thrusts. I could see Melissa in the distance. I pretended I was enjoying myself. I opened my mouth, closed my eyes and moaned loudly liked I'd seen women do in porn. The camera operator approved and thought it was great, but it was all for Melissa. I darkly imagined her thoughts, seeing her potential date being pounded by a man, imagining how pathetic I must look to her. He was twice as strong as I could ever hope to be, I couldn't have moved if I had wanted to. His powerful hold over me fed into my fantasies. I couldn't help that I was leaking from my cage.

The camera operator shouted cut and my partner pulled out. I got up and he shook hands with me again in a oddly professional way. I guess it was just his regular day job and he thought nothing of it. I could barely move, my ass was so sore. I pulled on my panties and tentatively wandered off the set towards Melissa. I anticipated her glowering expression and maybe that she would storm off but instead she ran towards me.

"Emily! Emily! That was incredible. You were just like a real porn star." She threw her arms around me. I couldn't believe she wasn't angry. She squeezed me tightly, I couldn't have ever imagined she would hug me. I was taken aback and my mood turned to joy. "I can't believe I know a porn star. How did you do that? Your expression was so realistic."

We were interrupted by one of the ladies from the salon. She handed me a couple of sanitary pads. "Emily, you're leaking a bit, put these in your panties to catch it until you can take a shower." For a final humiliation I slipped sanitary pads into my pink panties in front of the girl I liked.

"Oh, did you come?" asked Melissa. "So, you enjoyed him inside you?"

"I guess I must have," I said, bright red with embarrassment.

Gisèle joined us. "Hello Melissa, do you need me for something?"

"What? Oh! No. I'm just hear to support Emily. I'm almost done with the accounts I swear, it'll be finished right up by tomorrow boss, first thing."

"No problem, stay, enjoy yourself. All work makes Melissa a dull girl." She looked at a clipboard. "In fact why don't you join in. Emily here needs to move onto the next set. Would you like to participate?" Gisèle pointed at the next filming area. Melissa's face dropped.

"Oh, I don't know." She looked worried by what she saw.

"Nonsense. Lets get you dressed up." Gisèle shouted to attract the attention of an assistant.

In the next scene I was wearing a black lingerie set with heels. I was on my knees in a cage in a mock dungeon with chains hanging on the walls. Melissa towered over me wearing a black leather fetish catsuit and was brandishing a whip. Her blonde hair was scraped back into a ponytail and she had bright red lips. She was wearing spiked heeled boots and had her right foot on the cage with her weight on it as she stared at me menacingly, baring her teeth. She was a hot as hell devil. I looked at the camera with a terrified expression.

"That was perfect," said the camera operator. "This will turn out great."

"Wow, that was fun! So shall we just leave her in there then?" Melissa joked, pointing at me in the cage while laughing at the camera. I was helped out of my imprisonment and stood up on my heels.

"I enjoyed that a lot," I joined in. Melissa was chatty and alive. She'd seemed a little reserved before but participating in a sex scene seemed to have brought her right out of her shell with a new found confidence. Maybe she was always this way but just held it inside.

"I could get used to dominating you. You better watch out girl." Melissa opened her mouth, struck a sexy pose and looked at me alluringly. She tried to crack her whip for emphasis but it bounced back off the floor and hit her in the ankle causing her to stumble in pain.

"Ouch! Oh, baby! You OK?" I fussed and flapped around her, slightly panicked.

"Yeah, yeah, it's fine. Just a bruise I think. Geeze that hurt. Do people seriously actually enjoy being flogged with this thing?" She straightened out her leg.

Gisèle saw the commotion and rushed over. "Melissa are you all right? What's going on?" she asked.

"Dominatrix problems. I'm fine, really."

"I'll kiss it better," I said with a smile and got on my knees and kissed her boot.

"Good slave," laughed Melissa, patting me on the head.

"I love being on my knees for you Mistress."

"Perfect! Because that's exactly what I need right now," interrupted Gisèle. "Can you do me a big favor?"

"Can I take a break?" I asked. "My ass is still pretty sore from before."

"Well that's no problem because I only need your mouth. I've had some nice gentlemen arrive unexpectedly looking for service and almost all the girls are still playing in here." She put her hands together as if praying. "Please can you help? I'm really short and I need to set a good impression to keep the guys coming in or there will be no more cocks for you girls to play with."

"I don't know if I can. I'm no good at it."

"You suck dick like like a vacuum darling, you'll be great."

"Does she now?" Melissa shot me a wide eyed look of surprise.

"Sure, I'll help."

"Oh thank you darling. It means everything to me" Gisèle kissed me on each cheek. "Just go as you are, your lingerie is fabulous. Move it."

"I guess I have work to do then," I said, downbeat at leaving Melissa. "Can I catch up with you later?"

"No. I'm coming with you," she declared grabbing my arm. "This I need to see."

We tottered over to the dressing room and I was sent straight in and down to my knees without delay. Melissa sat on the chair in the corner. A guy came in and started unzipping himself. He was pleasantly surprised to see an attractive woman. "Can I have you instead?" he callously dismissed me, gesturing towards Melissa.

"Sorry dude, it's just not my thing," she shrugged.

"She just likes to watch," I added. He seemed disappointed he was getting the flat-chested cross-dresser instead of the hot, blonde real woman in a leather catsuit but took whatever he could get. I worked away at him enthusiastically, swallowed his cum and he left quickly. I wondered if this would be final straw for Melissa. I was sure that on seeing my eager, hungry display she would have a sudden realization about what little cock sucking bitch I was, that I could never be a man for her.

I turned around hesitantly almost expecting her to be recoiling with revulsion but her legs were apart, she had her hand on her upper thigh near her crotch. She was laid back and relaxed. "You know something Emily? I think that made me a little wet." I hadn't expected her to have that reaction. I hadn't expected any woman would have that reaction. I had shown her everything that I was and yet there was seemingly nothing I could possibly do to disappoint her. She was amazing.

"You suck like a whore," she said completely unfiltered and quickly reconsidered the comment. "Sorry, I just mean, you were like a professional." She thought again and face-palmed. "You were good at it. Sorry. You're an awesome cock sucker. Was that any better?" She grimaced at her inelegant description.

"I loved your first try. Say it again."

"I never heard of anyone who liked being called a whore before. Last person I called a whore was my 11th grade math teacher when she bitched about my homework. It did not go well for me."

She really made me laugh. She effortlessly flipped back into dominatrix role play mode like she was turning on a light switch, her expression turned serious. I composed myself in response. "You know with my job I can see everything that goes on in this place. Did you know those men pay Gisèle to use your mouth? Do you like your mouth being used for money, whore?"

"I love being used for money, Mistress."

"Of course you do, cock sucking whore. You are desperate for that delicious cum in your mouth aren't you, whore?"

She was seriously hitting my buttons and I was getting hard. "Yes Mistress."

"Suck for me, whore," she said with absolute authority and a piercing stare. "Show me how much you love it."

I smiled widely. "Yes Mistress." I pressed the signaling switch by the door. I sucked off the next man to enter the room with wild enthusiasm and swallowed down his cum like the cheap hooker I was.

"Again whore," Melissa ordered brusquely. Was she just role playing because I liked it or was she enjoying the idea of having power over me? Was it the leather suit bringing this side out in her? She was making me feel unbelievable horny.

After the third guy, I'd run out of cocks to suck. I turned around and Melissa's eyes were glazed over, she was openly rubbing between her legs without a care in the world. I don't know what was going on in her head but she was lost in some fantasy as she gently stroked herself.

"Did I tell you to stop sucking, whore?" she said almost like she was hypnotized.

"That's all there is."

She brought herself out of her daze like she was waking up from the happiest, deepest sleep and stretched her arms in the air. "Shame. I think I only needed to watch you do one more and I'd have finished myself off."

She was suddenly back to a bright and energetic mood. She sprung to her feet. "So, I think we both need a shower. I'm sweating like a pig in this catsuit and you've had dick in just about everywhere," she laughed. We went back to the hotel bedrooms hand in hand. I was about to break off in the direction of my room at the other end of the hallway but she wouldn't let go of my hand and dragged me back playfully towards her.

"I'm not letting you go yet slave. You can use my shower. You put all that effort into cleaning it in this morning. Best you get to have use out of it."

"Oh. Sure thing." I said innocently, having absolutely no conception of what she might be implying.

I went into her spotless bathroom. I was busy carefully folding my lingerie onto the counter by the basin and was just about to take my panties off when she burst in. "Can you help me with the zip on the back of this thing please?" She was stuck in her catsuit and couldn't get out of it.

"Sure." I helped get her free. I expected her to go back into the bedroom for some privacy but she turned towards me and wriggled out of the one-piece garment, leaving herself standing in front of me in just a white bra and panties. I was transfixed by her body.

"Let me help you with that," she said looking down at my panties. She got down on her knees and pulled my panties to my ankles but was stopped dead by the sight of my bright pink cock cage. "What's that thing?" she asked.

"It's a chastity cage."

"What's that all about?"

"It makes it difficult to get hard, prevents masturbation and keeps me in a permanent state of sexual frustration."

"Really? You like that?"

"I need it to be here. I mean without this you would just jack-off within ten minutes, a wave of shame would wash over you and you'd just leave."

"So how do I get you out of this damn thing?" she said tugging at it.

"You need a key, I think they have it at the front desk."

She looked away in thought for a second. "Just my luck," she whispered more to herself than to me. "Later then."

"Later for what?" I asked naively.

"Let's get you in the shower." I hopped in and turned the water on but through the glass door I saw her take off her bra and panties. I was dazzled by seeing her naked. She opened the door and got in with me. "Surprise!"

Oh my god. I was in a shower with a naked hot girl. This had never happened to me before in my life and I'd given up hope it ever would. I couldn't stop staring at her breasts. She picked up the soap. "Can you wash me please?" I eagerly took her up on the offer and took the soap from her. I shyly avoided her genitals to start with but she grabbed my hand and pulled me all around her breasts. My cock went absolutely wild and strained against my cage painfully. I tried to get it down but it was near impossible.

She took my hand and pushed it between her legs. I started soaping her but she had other ideas. "Finger me!" she demanded. I had zero idea what I was doing but nestled my finger into her labia and stroked, hoping for the best "That's good. Keep doing that and do not stop!"

I kept rubbing her in the same spot for several minutes. She jumped like a wave of electricity went through her. I paused wondering if I was doing something wrong. "Keep going! Don't stop!" I kept fingering her, and a short while later she exhaled sharply twice in quick succession, then pushed my hand away, leaning against the back wall to recover. "Christ, I was desperate for that," she said, catching her breath. She looked at at me with a sultry expression. "You did amazing." She leaned forward and kissed me passionately. I was in love. This morning I had thought I was useless, now I felt like a king, or perhaps queen. I couldn't believe I just made a woman orgasm.

After a few moments she built up her strength and washed me down. We got out of the shower and toweled each other off.

"That was amazing. I loved that," I said.

"Not as much as me," she replied. "I just need you to do one more thing for me," she added sexily.

My mind went wild with ideas about what she might want. "Anything for you."

She picked up a bottle of mouth wash from next to the basin. "Your breath smells like cum." I laughed.

Back in the bedroom, I was lying on the bed and had been mesmerized by watching her putting her clothes on. She folded up the leather catsuit ready to return it.

"Do you should think I should buy this from Gisèle?" she asked. "I think it may have lost some value since I masturbated in it. It does not smell good in there."

"I don't think you know the internet at all. I think it's value just went up."

"Huh?" She looked at me like I was a weirdo, which I probably was. "Screw it. I'll send it back to the laundry."

"But I would like to see you wearing that again. You looked seriously hot."

She smiled. "Well, this is the most ... unique first date I've ever been on in my life but also the most fun. Would you let me round it off by taking you out to dinner in the city?"

"I'd really like that." How could I turn that down.

"Great. We need to find you something to wear."

"My male clothes are in a locker near the front desk. I can just go and grab them and be back in five."

"No!" she said unexpectedly sharply and then moderated her tone. "No, that's OK. What else you got?"

"Well, only things from here. There's dresses and stuff in my room."

"Perfect."

"But I can't go outside, you know, dressed as a girl."

"Sure you can," she smiled. "I do it all the time."

I loved her sense of humor but I wasn't sure about this at all.

"Someone might call me out or something. There might be some kind of trouble"

"A man in a dress is not the weirdest thing to ever happen in Vegas, trust me."

She led me naked through the hallway back to my room and I directed her to the wardrobe of dreams. "So, what do we have here?" She riffled through the racks and pulled out an asymmetric off-shoulder drape midi dress in red. "We have a winner."

"I can't wear that."

"Please. For me?"

Her pleading got me into the dress with some stockings and matching red heels. She did my make-up for me using what I had in the bathroom. "Wow! Cinderella is ready the ball." I blushed.

She took me out to her rental car and took off towards Vegas. It was a new experience for me to be in a vehicle where you didn't need pray before turning the key.

"So what food you like? Italian? I know a good place."

"Sounds great."

"I just realized I don't know your name. I mean it's not actually Emily is it?"