Sissy Friends Forever Ch. 03

"No." She sounded particularly unconvincing. "I was just annoyed you didn't say you loved me." She positioned her finger and thumb about an inch apart and put her hand in front of my face. "I find your lack of devotion to me disturbing."

"Cindy!"

"Yeah I've seen it. I could never be annoyed at you."

"Whatever. I'll give you ten of my best you con artist."

"Now I'm annoyed."

"A hundred."

"Barely acceptable, but I'll take it."

I leaned on the wall and looked at her. "Cindy, can you give me more of your fantasies please? I just feel I need more to work with to keep you engaged."

"Sure thing. This morning when I was in the shower I was having this wild fantasy that I was being married off to a dude while wearing a slutty bridal outfit."

I grinned. "We did that one."

"I know. It was just so good I wanted to fantasize about it again."

"Sweetie, that's lovely, but come on, I need material. Unleash the filth."

"OK. No problem. While I was sitting on the toilet I was imagining being a restroom attendant."

"So one of those people who tries to sell you cologne?" I was confused. "Is that sexy?"

"Ah, my service is a little special. So first I do this." She stood up and sexily sauntered behind me. She pressed her naked breasts into my back. "Then I take out your dick." She reached around me, lifted my dress, put her hand in my panties and pulled out my clitoris. "Then I hold it for you while you pee, like this." I started to get hard.

"There's your problem with this fantasy." I pointed down. "It's not very practical. All of your customers would have an instant erection when you touched them and wouldn't be able to go."

"It doesn't have to be practical, it's fantasy." She looked down at me. "What's that doing up anyway? You're supposed to be limp for women. Is your hypnosis not working?"

"It's pretty difficult keeping it down for you."

"Well, if it fails my only choice will be to put you in this." She picked up a metal cock cage she was cataloging for her shop that had spikes on the inside. I took one look at it and went instantly floppy causing Cindy to laugh at my reaction.

"Jeez, I don't need to wear that, just looking at it is enough."

"Hmmm... useful information. That's something I can use. Maybe I can make some revisions to your hypnosis training to have you subconsciously believe you are wearing this when you see a hot woman. But be warned sissy, if you don't listen to it then you're getting the real thing." She held up the cage again threateningly.

"I'll be a good girl!" I shouted, crossing my legs. She sat down again. I tucked myself in and smoothed down my dress. "So what else you got in the fantasy department?"

"Where were we?" She pondered for a moment. "When I was finishing up in the bathroom I was thinking... "

"Hold on. We're still in the bathroom at this point and you're already on your third fantasy. How many fantasies do you have in a day?"

"You might want to go get a notebook."

Cindy recounted her endless sequence of sexual daydreams. In one, she wanted to be made to stand naked in a shop window, like one of the girls in the red light district of Amsterdam. The way she described it made me desperately wish I was standing there with her. "That one's amazing. I want that too."

"Still stuck on being a whore, huh?" she said.

"Always." Fantasizing about being a prostitute was a major turn-on for me. It was how we met. It was something that I could never get out of my mind.

"Hmm... now what if there was some way we could turn you into a real hooker?" My dick started to consider coming up again.

...

I was starting to understand what Cindy meant when she said hypnosis worked if you believed in it. It was like being on a subway train. You were not the driver, you couldn't change direction, but you had ultimate control as to whether you continued on the journey. You bought your ticket fully informed, you could see where you were heading with complete clarity, but if you changed your mind, you could freely step off at any station. You were never under a spell as such, you were never a prisoner, unless that was what you truly desired in your heart. If you liked the destination, if you really wanted to go to that place, you could just relax and let yourself be taken there. It took a little effort to take control, nothing significant, but it was just enough to make you feel you were being compelled. The most comfortable thing to do, the thing that felt most natural was just to sit back and enjoy the ride. Right at the moment, my train was headed for Sissyville and there was nothing that could make me want to get off.

I was at work, sat at my desk and I saw Sean appear in the distance. I started to feel butterflies and instinctively bit my lip. I knew what was going to happen and I willingly let myself just fall into it. My back straightened as if I wanted to put my breasts on display. My lips started to part, my hand became limp and drew close to my chest. I was warming inside. Then it started to happen. I was wearing panties and pantyhose but that didn't constrain it under my dress. I pulled my chair under the desk to hide myself. I got a hard-on for Sean.

I couldn't take my eyes off him. The longer my gaze lingered, the firmer my erection seemed to become and the more I felt enchanted by him. I basked in this strange feeling of detachment. My body experienced pure lust but my mind felt almost the opposite. I had no attraction to him at all, or any man, but anyone who was watching me at this moment would never have believed it. Cindy had worked her magic for me and I loved how it made me feel. At least in body, I was now a besotted girl.

Sean was heading towards me. He sat on the end of my desk. "Hey Aaron, how's it going?"

"Great," I said dreamily. "Even better now you're here."

"Sorry, but they need some more help with the Beacon account upstairs."

"Sure thing. When?"

"Ten minutes?"

"I think I can do that."

"Thanks buddy." He patted me on the shoulder and abruptly left. I stepped off the train, but not for long.

Sean had just given me an invitation in our private code. Over a couple of weeks, our relationship had blossomed into a little more than just professional. We had a special meeting place on the fifth floor. I had noticed an executive office that had been unoccupied for some time and we were making use of it. I got there before him and closed the blinds. There was a desk in the middle but I didn't take the seat. That wouldn't be for me. I stood leaning against the wall and waited for him.

Sean arrived after a few minutes and I took up position standing in front of the desk. He locked the door and then walked up behind me, fondling my ass. We kissed each other and he unzipped my dress, pulling it to the floor. He sat on the edge of the desk and unbuttoned his fly, pulling out his dick. I let myself go completely and stepped wholeheartedly back on the train. I suddenly felt a wave of desire for him and my involuntary reactions for him emerged. I felt gooey inside and salivated in expectation of his cock. My own erection came up instantly and made a very visible bulge in my underwear.

"You want my cock don't you Aaron?" I'd been trying to teach him to dominate me and had given him some ideas about how to behave. I think he was starting to enjoy the power rush.

"Yes, Sir," I said. I'd decided to start calling him that, he didn't object.

He looked down. "Why have you got a hard-on Aaron? Do you like cock?"

"Yes, Sir."

"I don't believe you."

"I love cock, Sir. I need it."

"Well don't just stand there." I got on my knees, took him in my mouth and started working away. Due to how good I was feeling from allowing myself to be taken on a hypnotic ride, after a minute I zoned out and slowed my rhythm down. "I'm not feeling enough enthusiasm," he said. I picked up the pace, working away more vigorously at him. I started moaning with enjoyment. "That's better."

He came in my mouth, I pulled away from him, swallowed and looked up at him from my position on all fours.

"Tell me how much I own you."

I turned my head away in shyness. "I'm your cock slave, Sir."

He put his hand under my chin and twisted my head to force me to look at him. "Yes, you are, Aaron. Never forget that." He stood up and left without another word leaving me in my underwear, on my knees. It was where I belonged.

...

Cindy was making dinner as I came home. I snuggled up behind her and put my arms around her waist, kissing her on the back of the neck as she stirred the bolognese at the stove. I put my hand in her skirt and started rubbing her. She liked it when I touched her without warning.

"Can I take over making dinner? You end up doing so much around the place. I'm feeling guilty."

"I like doing the housework and it's practical as I'm home all the time."

"Maybe one day your business will be able to support us both. Then I'll quit my job and be your tradwife. I'll get a 1950s dress, put my hair in a vintage style and do everything for you. You won't have to lift a finger."

"In your dreams. I already called the domestic chores."

"I want to do something."

"Well, I guess I could let you put the laundry on, but you owe me."

"Thanks. I'll do that like the good little housewife I am."

"You might find a pair of my panties at the top of the hamper with some of my freshly leaked cum for you to lick."

"I live in hope." I kissed Cindy again and started to slide both my hands inside her bra. Through the never ending evolution of her hypnosis practice, she'd been working on trying to make her nipples extremely sensitive. As soon as I touched them, she gasped and dropped the spoon she was holding into the pot. "That's improving."

"Yeah it's starting to get pretty good. Still not quite there yet." She fished the spoon out of the pot. "How's your affair going?"

"Wonderfully. You're being cheated on like you wouldn't believe."

"Glad to hear it." She twisted around and kissed me on the lips. "So, details please, what happened today?"

"He's starting to dominate me a little, like I asked him to, and I told him I was his cock slave."

"Good girl."

"The thing is, it's almost true. The feeling I get from that hypnosis track you made for me is wild. It enhances the experience exquisitely. When I just let myself go and let it take over me, I get a sort of tunnel vision and my body just feels desire all on its own, like it's disassociated from my mind and I'm just a passenger."

"And to think you doubted me." She smiled.

"I will never doubt you again. I think it's almost too intense."

"Too intense? What are you? Some kind of sissy?"

"Yes."

"I'll notch it up a little more then."

"That would be impossible." Challenging her would make her more determined. I started stroking her ass.

"Are you doubting me?"

"What could you possibly do?"

"So you told him you were his cock slave huh? I think it's time you started living up to your wedding vows." She found my hand and played with my third ring. "I think it's time you were truly addicted to cock."

"Yes please."

"You know when you're on your sissy period? When the sexual frustration builds up. You know how you feel you desperately need a release and the feeling starts to consume you?"

"Yeah"

"I'm going to make you imagine that feeling, but instead of jacking off, it can only be satiated with the feeling of cum sliding down your throat."

"How often will I have these terrible cravings?"

"Whenever I want you to." She snapped her fingers as a demonstration of her control, just like I did with her.

"What if there's no dick to suck when I'm in need?"

"Too bad. Maybe you'll have to go beg your little boyfriend."

"You're evil."

"Yes I am."

I started kissing her neck again.

....

I was sat in the passenger seat of the car wearing a tight black dress that ended a little above the knee with matching black heels. I was very nervous and I alternated between tightly clutching my purse and playing with the curls of my brown wig, but it didn't soothe me.

"You'll do fine," reassured Cindy, noting my anxiety as she drove us. "You look gorgeous babe, he's going to love you."

"Thanks." I smiled at her. "So how much did you get for me?"

"I got a hundred and fifty. I was scammed."

"I'm pretty content with that."

"You're at least a thousand dollars a night girl."

"Thanks, sweetie."

"I'm more of a five dollar, me love you long time, kind of girl."

I laughed. "Your priceless to me."

She smiled. "Do you like my earrings?" Cindy played with her trashy, big gold hoops that complemented her carefully selected ensemble. We were both dressed for the same job, I was being more realistic, she was being a cartoon. She was wearing a tight pink miniskirt with fishnet stockings and over-the-knee spiked leather boots. I wasn't sure how she was managing to drive in them.

"They go just right with your outfit." I put my hand on her leg. "You know you didn't have to dress up."

"I wanted to show support in my own special way." She glanced at me. "Besides, any excuse, right?"

"You don't need an excuse. Promise me you'll always wear whatever makes you happy whenever you want. There's no limits."

"Thanks, babe." Cindy's phone interrupted us, announcing we had reached our destination. "Ooo, I guess it's this building on the right." She parked the car in a convenient spot.

"So, here we are." I breathed deeply and closed my eyes for a moment. Cindy had advertised me on a site for escorts and I'd got my first client. It was a fantasy that had become real, now I'd have to go and deliver the goods.

"It's apartment 36 and it's David."

I turned to Cindy with a grimace on my face. "I'm not sure I can do this. I feel like I want to back out."

"Come here." She leaned across and we kissed. "Just enjoy yourself." She gestured for me to get out of the car.

I breathed deeply. "OK." I built up the courage and went for the door handle but Cindy grabbed my arm. "What?"

"Oh! Nearly forgot." She snapped her fingers in front of my eyes. "Cum addiction!" she ordered. I looked at her confused. "It might help with the anxiety."

"I don't feel any different."

"You will when you relax and fall into it. Now go, go, or you'll be late." She wafted her hand, encouraging me to leave. "You don't want a bad review do you?"

"Let's do this." I opened the car door and walked into the building. I made my way up to the third floor in the elevator and found the apartment. I paused outside the door to check my make-up, as much out of procrastination as to ensure I looked good. I breathed deeply to calm my nerves and then went to bang on the door but my hand froze before I knocked. I took one more breath and then tapped more gently than I should have, but someone heard me anyway.

Within a few moments, a middle-aged man answered. He was shorter than myself, about five feet six tall and while hardly obese, he had a rounded physique and was not especially in shape. His receding salt and pepper hair was neatly combed and he wore a pair of round eyeglasses which slightly magnified his hazel eyes. "Hi, is it David?"

He thought for just a moment too long. "Oh, erm, yes." I could tell from the delay before he responded that he had given a fake name, but that didn't matter. I was about to do the same.

"Please come in," he offered. I stepped passed him and he checked up and down the hallway. He seemed anxious that no one had seen me. Once he was satisfied there was no one around, he took me through to the living room. "What should I call you?"

"I'm Alicia."

"That's not your real name is it?"

"No. David's not your name is it?"

"Not exactly."

"Well, now we're on fake first name terms, I guess we can fuck." That broke the tension and we both laughed.

"Erm, do you want anything before we begin?" he asked. "Coffee? Drink?"

"No, I'm good, thanks."

"Do you want to do it in here or in the bedroom?"

"Erm, bedroom." He led me through and I sat on the bed.

"Before we start, I just wanted to check you were clear I'm a trans girl?" I wanted to make sure Cindy hadn't left anything important out of my profile. I'd never seen it.

"That's what I hoped," he smiled. Everything seemed to be in order.

"Great. I didn't want you to get a surprise." He smiled. "What would you like?" I was starting to feel more in control of the situation and felt more relaxed. He seemed more nervous than I was. As I let my mind go though, I started to board the train. My eyes were drawn to his cock and I couldn't wait to have him in my mouth. I started to imagine him squirting his load into me and cum sliding down my throat. Cindy had taken over my brain.

"Can I take you in the ass?"

"What?" I looked up to meet his eyes. I was so engrossed in the idea of giving him a blowjob, my mind was so fixated on sucking, I hadn't even considered anything else was a possibility.

"Is anal OK?"

I snapped out of it. "Erm, sure." The customer was always right. "Let's just get you prepared." I'd been practicing something special using a dildo, I just hoped I could do it now it was show time. I picked a condom out of my purse and went down on my knees in front of him. I unbuckled his khaki pants and found he was already up for me. I looked up at him. "I like a man who is ready for action." He smiled back. I formed my mouth into an 'O' shape and put the condom between my lips. I slowly took him in my mouth and rolled out the condom as I went, down to the base of his five inches.

With his cock in my mouth I suddenly felt a wave of pleasure. I closed my eyes and by every natural instinct I wanted to suck him, but I resisted and stepped off the train a moment, slowly withdrawing my lips.

"That was wonderful," he said approvingly.

"I was quite pleased with how that went."

"Neat trick." I got on the bed on all fours and found some lube in my purse. I hitched up my skirt and pulled down my panties. I felt him get on the bed behind me. He took the lube and made me ready, then I felt him inside me. He held onto me and started thrusting away. He wasn't hitting the spot but my physical pleasure was only a secondary concern. This was about my mental pleasure. I was now being used by a man. I was no longer just playacting a fantasy, I was a real whore now.

I started moaning in time to his thrusts, pretending he was a master of sex. "You're so good, David." He was no Cindy, but I wanted to encourage him. As he was fucking me, the hypnosis started to sneak up on me again without my even realizing. The thought of a dick in my mouth slowly started to consume me. I opened my lips and started fantasizing there was another man spit-roasting me. I badly needed to swallow.

After a few minutes I heard him start to orgasm. I started to fake having an orgasm too and clenched my butt cheeks around him. As he withdrew, he slid out of the condom and it stayed half inside me, dangling out of my ass. His breathing was heavy, but started to slow and he backed away from me, then collapsed on the bed.

"You can go now," he said brusquely.

"But is that all you want? You've got the full hour." All I could think about was sucking. How was I going to get my lips around him?

"Please go."

He wasn't going to let me blow him, but I was in desperate need of his cum. It was like a thirst that I just couldn't quench, an itch I couldn't scratch. I thought about the condom still in my backside and what might be inside it. I left it in and pulled up my panties. The thought of licking out the condom disgusted me in one sense, but in that moment I was the desperate addict Cindy had turned me into, I needed my fix however it came.

I got off the bed and smoothed down my skirt, picking up my purse. I was about to leave when I looked back at David on the bed and noticed he seemed downcast and frustrated.