Sissy Friends Forever

I received a message on my phone just as I was leaving work: 'Get your ass over here. Usual hotel. Room 212. 9pm'. I'd had to work late and he hadn't left me with much time. It was just typical he would choose today, but it wasn't his fault, he had only done exactly what I had asked him to do. I drove to my apartment and quickly picked up a suitcase I kept specially prepared that contained everything I needed, then immediately drove to the hotel.

As I expected, I had a reservation. I checked in, picked up my key and went straight to my room. I took off my work suit and tie and tossed them roughly on the bed. I examined myself naked in front of the mirror. I hadn't shaved my legs in a few days but this would have to do as I didn't have much time. I opened the suitcase and pulled out my make-up kit. I got my beard area covered, put on some red lipstick, a light eyeshadow and did my eyebrows. Ideally I would have liked to have had more time to do some contouring but it wouldn't matter.

I had a choice of three wigs, I picked a blonde hairpiece and fitted it, checking myself out in the mirror. I was always amazed how something as simple as a change of hairstyle suddenly unleashed femininity. It never got old. I didn't have time to hang around admiring myself though. I retrieved my intended outfit and laid it all out on the bed.

I tucked my genitals, it wasn't comfortable but it was better than any unsightly bulges. I pulled on my panties and ran my hands down between my legs. I loved the weird feeling of my cock seeming to disappear, the way you put your hand down there and it was just smooth, there was suddenly nothing of any significance between my legs any more. I put on a bra and filled it out with a couple of gel breast forms. They were an appropriate size for my frame, nothing too outrageous. I found a pair a of scrunched up thigh-highs, the feeling against my legs was just divine as I slipped into them. I picked up my black form-fitting dress and stepped into it, zipping myself up and smoothing it down. I wished I had real cleavage to put on display. I got into my heels, picked up my purse and was ready to go. I only had five minutes left. Just in time.

Now for the part I both dreaded but at the same time found exhilarating. I pulled open the hotel door just a crack and checked if I could hear anything. It sounded silent except for the hum of the elevator in the distance. I nervously poked my head out and looked in both directions. The coast was clear. I stepped out and the sudden slam of the door automatically closing behind me made me jump. Feeling exposed and vulnerable, I quickly made my may to another room nearby and knocked on the door. I glanced around nervously, hoping no one would see me. "Come on, hurry up," I whispered to myself.

After a few moments, exactly who I expected answered the door. Matteo was a flawlessly groomed Italian in his 30s with a stylish closely cropped beard. He had a well defined physique and clearly spent a lot of his life in the gym. His tailored suit exuded an impeccable sense of style and gave him an air of sophistication. Even a straight man could see he was someone who could effortlessly command attention from the opposite sex, should he so choose.

"Inside." He snapped his fingers.

"Yes Sir," I replied, tottering in on my heels. He silently handed me an envelope, it contained fifty dollars in cash, I wasn't high class. I slipped it into my purse and put it down on the bed. "What would you like Sir?"

He didn't answer immediately. Instead he slumped in the chair in the corner of the room next to the desk.

"Lift your dress, let me see you." I stood in front of him and hitched up my skirt revealing my underwear and stocking tops. He made a circling motion with his finger and I turned around at his instruction, showing him my ass. I looked back and smiled at him.

He snapped his fingers and pointed at the floor before looking away dismissively.

"Yes Sir."

I sank down on my knees in front of him. I pulled out his eight inches, masturbating him to erect and got to work. I slid my ruby red lips down his shaft and took him into my mouth as far as I could. I started sucking and got a rhythm going. He picked up a whiskey from the desk and sipped it while I worked away. He placed his hand on the back of my head and tried to push me deeper. I gagged slightly but kept going.

After a few minutes he came in my mouth and I gladly swallowed it down. I withdrew from his shaft and licked up the remaining cum like it was precious to me. For the final touch, I kissed the tip of his cock. I had enjoyed every moment of it. I felt so feminine, I wished it had only lasted longer. I looked up at him and he smiled.

"So, when do you want to do this again?" he asked, his voice in a more friendly tone.

"Message me sometime in the evening, no longer than two weeks," I replied getting to my feet. "How much?"

"The usual, please. A hundred for me plus give me what I need to cover the rooms," he requested. I reached into my purse and found the fifty he gave me, handing it back to him, then added the remainder he had asked for. As much as I may have hoped otherwise, I wasn't actually a prostitute, however, Matteo most definitely was. He was a gay escort I was paying to give me the experience of being a cheap hooker. I'd have him call me whenever he so wished and pretend to be my dominating client. He wasn't naturally very domineering, he was actually a very sweet guy, but he could role-play what I wanted. He'd demand I suck him off in a hotel room and make me feel weak and small, just like a wanted. The exact timing would be a surprise, he'd be in charge of when he wanted me and I'd have to go and do it at his convenience. I'd made use of his services about a dozen times now, but I was ready for something more.

"Can you surprise me next time in some way?" I asked. "I mean I absolutely love blowing you," I put my hands together as if in prayer to emphasize my point, "but it's all getting a bit predictable now. I really need something to spice it up."

"Like what?"

"I don't know. Just ... something different."

"I'm not sure I really get what you sissies want."

"I don't know what I want either! That's the problem."

He looked at the floor, exhaled and ran his fingers through his hair like I'd caused him some big inconvenience. "OK, let me work on it." He lifted his head, tapped his temple and smiled. "I'll see what the old noodle can come up with."

"Thank you. I know I'm incredibly difficult."

"Hey, no, you're my easiest customer." He opened his arms with a warm, inviting gesture. "I do nothing at all, you give me the greatest blowjob and then you just leave."

"You liked my blowjob?" I was delighted by his compliment.

"I loved your blowjob. You're getting better every time. You'd make any man the happiest in the world." I blushed.

He stood up, took off his jacket and unbuttoned his shirt showing off his toned abs. He probably thought it would inspire me. "Are you sure you don't want to try something else before you go?"

"Matteo, I know you're a really handsome guy but all I want to do is blow you. I'm straight."

He looked at me quizzically. "You keep using that word, I do not think it means what you think it means."

"OK Inigo!" I laughed and pointed squarely at his bare chest. "That don't impress me much."

"OK Shania," he shot back. "But I've got the moves and I've got the touch. Why not have Matteo for the full hour? It's only been ten minutes."

"Well maybe if you didn't come so fast," I said playfully.

His hands became animated, he was incapable of saying anything expressive at all without using his Italian gestures. "With your lips on him Bella, any lesser man would be lucky to last for even ten seconds."

He made me smile. While I wasn't attracted to him physically he definitely held a certain charm, but I wanted to go. "Don't get me wrong Matteo, I think you're alright, but I'm looking for something else to keep me warm in the middle of the night." I picked up my purse and blew him a parting kiss. "Later Romeo."

"Sono pazzo di te!" the incorrigible Matteo shouted after me as I closed the door. I ran back to my own room before anyone saw me. I meticulously took off all my makeup and carefully packed up my clothes before leaving for my apartment wearing the suit and tie I had arrived in. Just another anonymous businessman.

...

The two weeks I had given Matteo to call me were almost up and I was counting off the days. Hath he forsaken his Juliet? The fickle merchant of amore was probably busy ass-fucking some Antonio or Bassanio at this moment. I shouldn't have given him so long. I was getting desperate to have his cock in my mouth. Shylock hungered for his 8 inches of flesh. Matteo was one of the few outlets I had for this side of my sexuality, this hidden side.

I was at work and outwardly very much in male mode but my mind was distracted, wandering deep into fantasy as it often did. I was the main character in my own movie: The Secret Life of Walter Sissy. Elouise, my long-time office crush, had just wandered by my desk leaving a waft of her sweet perfume lingering. She was in her early twenties and absolutely captivating. She had long blonde hair that fell well past her shoulders. She changed her style regularly but currently had it in a vintage glamour look with waves, something straight out of The Great Gatsby. It gave her the aura of a classic movie star ready for the red carpet. She always wore a tight body hugging dress and turned every male head as she glided around on her heels with the walk of a model.

Elouise was the office socialite, she knew everyone and was always at the core of any gossip. She often stopped to chat with me but I gave her only brief answers. I had a strictly cordial and professional relationship with her when I had specific business, nothing more. I spoke to her perhaps every couple of days but knew little of her private life. She was a million miles out of my league and so intimidatingly attractive to me that I could barely hold a conversation with her, let alone ask her anything. All I really knew was she had a boyfriend.

In my mind I was immersed in a strange duality with her, a certain doublethink I was sure was unique to myself that no other man could ever feel. On one hand I desperately wanted to fuck her and I dreamed of sleeping with her as I knew would any man, but on the the other hand I also wanted to be her. I imagined wearing her clothes and the feel of her pantyhose against my legs. I visualized myself inside her body, looking out from her point of view, literally walking a mile in her high heeled shoes. I fantasized I was her, I would smile at my male colleagues, soaking up how I knew they were all deeply attracted to me, reveling in the raw sexual power I knew I held over them.

When the end of the day came I rushed straight home. I went into my bedroom and unlocked my closet. I'd had a lock fitted in case anyone I invited into my apartment ever became curious and snooped around because this was where I kept my 'special' collection. Inside I had a large walk-in dressing room with racks of clothes. I had dresses, skirts, sets of underwear, a substantial designer shoe collection for every occasion and a wide array of make-up. Everything a girl could ever dream of. My choices though were heavily influenced by Elouise. As well as my secret love, she was also my secret mentor. I studied her fashion and wrote down everything I ever saw her wearing. I trawled websites for hours, trying to find her dresses and her shoes. It would have been easier to straight-up ask her where she bought her clothes but that would have been a weird conversation coming from a man. In the end, I figured out the places she liked to shop. Every time I saw her wearing something new, I bought it for myself.

I was just contemplating getting into a dress when I got a message. It was Matteo and he wanted me in two hours. At last. I had plenty of time, I picked out the dress I had seen Elouise wearing today and packed it in my bag. What shoes had she worn though? It was high heeled sandals I was sure. I packed a matching pair. I drove to the hotel and started to get prepared in my room. It was a long drawn out process, but Matteo's whore was ready, a poor pastiche of Elouise. I wished I could look as good as her.

I snuck out into the hallway, furtive as always and knocked on Matteo's door. He invited me inside and slumped in the chair in the corner. He snapped his fingers and I opened my mouth with almost Pavlovian expectation, salivating at his cock, but he didn't point me at the floor as he usually did. He glanced to my right, looking behind me and I heard the distinctive sound of high heels clipping on the floor.

I whipped around, shocked to see someone else emerge from the bathroom. In front of me was another cross-dresser, perhaps in her late twenties. She was very ... pink. She was wearing a short pink skirt, pink heels and a pink off-the-shoulder blouse. Her face was made-up and she had pink eyeshadow and lipstick.

"This is Cindy," said Matteo. He noted my confused expression. "You said you wanted something different."

"Yes Sir," I replied. I had said I wanted something different. "That's right."

"Very good then."

I turned back around to face her and Matteo gestured towards me. "Cindy, this is Aaron." I wasn't sure what I should do now. Should I say hi? I was slightly annoyed he had used my real name in front of this other person I didn't know if I could trust, but I hadn't given him any alternative name.

"Why don't you two ladies get aquatinted." He leaned back in his chair. "I want to see you making out."

"Yes Sir!" We both said it in unison and then laughed at the coincidence. It broke the ice. I approached her. She looked nervous. I started lightly kissing her.

"You can do better than that," encouraged Matteo. I amped it up to a full mouth kiss with tongue. Cindy closed her eyes. "That's much better, now more enthusiasm." I started moaning. I embraced her and fondled her ass, she followed my lead and started doing the same.

"Get on the bed." We both lay down facing each other. "Make-out! Aaron, get your hand between her legs." I started kissing her and slid my hand up her skirt. I slipped my fingers into her panties and came across what felt like a cock cage. I tugged at it a little and tried to tease her. "Kiss her little clitoris."

I rolled her onto her back, hitched up her tight mini-skirt and pulled down her panties. She was completely shaved and totally smooth. I kissed her cage and played with it a little with my tongue. She was leaking pre-cum which I lapped up.

We made out for maybe quarter of an hour, well a little more than just made out, before Matteo moved things along. "OK, now ladies we are going to play a game. Stand up both of you, over here," he ordered and unbuckled his belt. "I want you both to suck me now, but with some competitive fun. Whoever gets my cum in her mouth gets a free session with me next time. Cindy will go first." He snapped his fingers and said assertively "Drop for cock." Cindy instantaneously fell to her knees in front of him with her mouth wide open, a vacant look in her eyes like she was somehow under his spell. I wasn't sure what she was doing. I knelt beside her more slowly and got comfortable. Matteo presented his dick and she worked away enthusiastically with no hesitation. After only ten seconds, he shouted "Swap over!" Cindy withdrew with some reluctance. I took my turn and started sucking him. He continued to make us switch every few seconds, our different shades of lipstick intermingling on his shaft.

In the end, it was Cindy who was on him, sucking with vigor, when Matteo released his prize with a grunt. "We have a winner," he declared. "Don't swallow! Now be kind and share my gift to you with Aaron. Good girl." She moved in for a kiss with me and I happily obliged. I scooped some of the cum from her mouth with my tongue and we both got to swallow. I pulled away and saw she had a string of cum dripping from her chin. I licked it off her, then I went down to Matteo's cock and swirled my tongue around the tip to claim the last few drops of his precious seed.

Suddenly there was a knock at the door. "Shit!" said Matteo. He pushed my head away and started buckling up his belt. I sprang to my feet and Matteo rushed to answer the door. He looked through the spy hole and exhaled. "It's my next customer, he's impossibly early. Sorry." He opened the door just enough to show his face. "Mi scusi, aspetti un attimo per favore," he said to whoever was on the other side and closed the door.

"Who is it? Can't you get rid of him?" asked Cindy.

"No, he pays my rent. He's a big spender. My apologies. Sorry. Sorry. Can you leave now? I will do you some kind of discount or something for the inconvenience."

"I don't want him to see me," said Cindy worried.

"And I don't want him to see you either." Matteo scratched his head. "Erm, simple. You ladies go in the bathroom. I invite him in and distract him and you sneak out the door as quick as you can. Go!"

We went into the bathroom. Cindy's male clothes were strewn around and she started rapidly collecting them. "But I got to change? I can't go outside like this."

"No problem, I got the room across the hall. Come with me and you can change there."

"Awesome. Thanks."

The bathroom door was slightly ajar and we heard someone come in. I took off my shoes so I could move more stealthily. Matteo was discussing something in Italian. I peeked my head out of the bathroom door and saw him engaged in conversation with a bald-headed middle-aged man. I snuck out and opened the hotel door quietly. Cindy zipped past me into the hallway at lightning speed and the door closed behind me. I don't know how Matteo explained the slam. Not my problem. I quickly fished out my door key and bundled Cindy into my room.

"Safe!" I exclaimed, leaning against the back of my door with relief.

"Thanks again," Cindy said. She went into the bathroom. "You got eye make-up remover? I forgot to grab it. It's still in his bathroom."

"Yeah sure," I offered. I went into the bathroom to point it out. "It's in my make-up bag, just there." I sat on the edge of the bath. "You know, I never imagined I would ever meet anyone like me."

"How do you mean?" she asked.

"I mean, you get a thrill out of dressing up and sucking dick too? I never saw anyone before who even hinted they were into it."

"I think there's a lot more of us than you think. We're all just extremely private because of the stigma." She started removing her make-up while she spoke. "I love it. I like to imagine I'm a prostitute and he's my John."

"Me too! That's the exact role play I like to do with Matteo." I thought for a moment. "So would you say you're a sissy?"

"Well, that's one thing they call us."

I pondered for a moment. "Can I buy you dinner sissy Cindy?"

She turned to me and smiled. "Sure you can, I'm really hungry. A girl cannot live by cum alone."

"As much as we like to try." We both laughed. "I already made out with you, now I'm offering you dinner. It's kind of the wrong way around."

"I guess, but I'll take it all the same thanks."

I had an idea I wanted to raise with her but wasn't sure how she'd take it. I tried to gently probe how she might feel. "Have you ever been outside dressed before?"

"No way, I'm too scared," she said emphatically.

"I'm terrified by the idea too. Really I am." I looked at her seriously. "But what if we did something crazy?"

"Ohhhh no, no, no. I can't. No way." She understood what I was about to suggest.

"I think I could do it if there were two of us. We would support each other. You know, safety in numbers."

"No."

"Let's get dressed up and go to the hotel restaurant. It's just a ride down in the elevator, we never have to leave the building. Let's say it all goes wrong and we embarrass ourselves. We can just burn this place, never come here again in our lives. Why would you ever need to come here? What's the harm in trying just once?"