Sissy Friends Forever Ch. 02

"If you could cum from a hypnotic trigger without touching yourself at all I'd be very impressed."

"Would you believe in my hypnosis and start listening more regularly?"

"If you can cum on command, you got me sold."

"It's a deal then. I'll start thinking about how to do it."

I nodded and sprung to my feet. "I got to go to work and you got packages to mail." Cindy had been running a small web store selling products to other sissies. Originally we'd started it to give her something to do, but it was taking off and she was now shipping dozens of packages every day all over the country. We didn't know any of her customers, they were just a name stuck on a box but it was comforting to know there were more people just like us out there in the world, even if they were silent and private.

"Love the bra," Cindy said.

"You can see it?" I asked self consciously looking down at my blouse.

"Kind of, not really, I knew it was there, I saw you putting it on. Glad to see you're a little more confident. Good sissy."

We kissed and I started to walk away. "Purse!" Cindy shouted after me. I had asked her to remind me I was going to try taking a purse to work. Since I was escalating my femininity today, I might as well add that. I went into the closet and pulled out a black leather mini shoulder bag held by a gold chain. It was not a very masculine bag.

"Good choice," she said. "New house rule, you must never use your pockets again. All your stuff goes in a purse from now on."

I transferred my keys, wallet, and phone into my bag. "Done." I kissed her again. "Don't forget we're going out tonight. Your legs need waxing."

"Oh Christ no, that's worse than my period."

...

We'd been in a bar for about two hours. As often happened these days, Cindy got hit on. It was only to be expected as unlike me she was a good looking girl. I remembered how less than six months ago she had been barely able to take a step out of the apartment wearing the most conservative of women's clothes but now she was no shrinking violet. She was wearing her favorite tight hot pink dress with her new boobs on full display. She was in her element, a confident, sexy vixen hunting her prey. It was a case of practice makes perfect. We'd been out in bars so many times she'd heard every line and seen every play. With her looks and experience she'd perfected her art and could wrap any man she pointed at around her finger. Her only problem was holding onto them once she'd hooked them. When it came to maintaining the interest of a man she had an Achilles' heel, but it was in her panties.

I wanted to give Cindy space to play and enjoy her newfound femininity to the fullest so I had quietly drifted away and moved to sit at a table by myself. I was wearing a short, black, satin slip dress that fully exposed my crossed legs. My expensive high heeled shoe had partially slipped off and was idly dangling from my foot. I'd often stare at my phone when I was on my own but I was enjoying watching Cindy from afar, she was working her magic and I was rooting for her to take her chosen man home. The fact I appeared to be staring into space probably made me seem more open and available at that moment.

"Excuse me." I looked up to see a fresh-faced man wearing a casual shirt and jeans. He was young, perhaps not more than 22, with a lean build and mop of curly brown hair.

"Did I steal your seat?" I wasn't sure what he wanted. I started to get up. "I'm sorry, I can move."

"No, no, erm, it's not that. I was just ..." he stumbled over his words and looked down for a second to compose himself. "I was just wondering if ... if I could buy you another drink?"

I was in shock for a moment. A man had just asked me if I wanted a drink for the first time in my life. "Sure you can," I said enthusiastically and started to form a smile. "Thank you so much. I'll have another one of these." He flagged down a waitress and got me another glass of wine.

"I'm not interrupting am I?" He stood there hesitantly, very unsure of himself, waiting to be invited to sit. "I guess you must be waiting for someone."

"No, I'd love some company." I gestured at the empty chair opposite me. My inner critic was telling me it was impossible, but was there an outside chance I was being picked up? The hope gave me a warm glow.

He finally sat down but didn't say anything for a few seconds. "Hi," he said to fill the space.

"Hi," I replied.

"Erm ... hi," he awkwardly repeated again before pausing and running his finger through his hair. "Can I level with you?"

"Sure."

"I've been watching you for the last hour and I really wanted to come over and talk to you, but I have no idea what I'm doing." I couldn't believe it, he was trying to hit on me. I felt so happy.

"First time trying to pick up a girl huh?"

"Yeah," he admitted, avoiding eye contact and looking at the table. He seemed so nervous. I was loving the idea that just through my presence I could turn a man to jelly. I'd never even considered that could be a possibility before. It made me feel so validated as a woman, it made me feel attractive for the first time. As much as he was lifting my confidence though, I was conscious that I shouldn't crush his. I remembered being in his place, with butterflies in my stomach, in a well of anxiety, building up the courage to talk to a girl. I had deep empathy for him.

"The hard part's done now. You came over and talked to me. Just relax." I put my hand on his. "Can I level with you too?" He nodded. "No one has ever tried to pick me up before."

"I can't believe that," he said.

"Awesome compliment." He smiled. I narrowed my eyebrows "Are you certain you've never done this before?"

He shook his head. "Maybe you're a natural." He became embarrassed and glanced away. "Why don't you tell me your name?"

"It's Eric," he stumbled out. "Sorry, I should have asked by now, what's your name?"

Out of the corner of my eye I saw Cindy leave the man she was talking to and start walking towards me. She had almost certainly got to the part where she told him she was a trans girl and had struck out. She had a decent amount of success but she ultimately got rejected maybe four out of five times. She was honest and didn't want to lead them on for too long and she paid dearly for her scruples. I predicted I was going to strike out now in exactly the same way.

"I'm Aaron." I'd never got around to thinking of a girl's name. I didn't actually think I wanted one.

"That's ... interesting. I've never heard a woman called that before."

"It's possible I might not be one hundred percent female."

He sat back in his chair and studied me. "I'd never have guessed. You look incredible."

"A girl could get to like you." He was making me feel so good but I thought in fairness I should offer him an easy escape route, especially as he was so anxious. "You know, if you want to back out. I completely understand. There's no problem at all. A girl like me isn't for every man."

He pondered for a moment and I assumed he would take the opportunity to make a polite exit with no hard feelings but he surprised me. "Well, I'm not every man." The line was a little corny, but so sweet to my ears.

Cindy had stopped ten feet short of the table when she saw I was engaged in conversation and was standing behind Eric. She put her hands in the air like she was cheering for me and gave me a wide eyed, open mouthed look of sheer delight at my apparent success. Then she started miming reeling in a fish. I was trying not to laugh. It was her way of showing support and telling me she didn't mind me playing with him.

"Do you like trans girls?"

"I've never even thought about it before." He sat back and looked away thoughtfully. There was a pause of several seconds. I waited patiently. "Do you mind if I find out?"

I smiled at him and put my hand on his knee. "You are one in a million Eric."

"Thanks," he said bashfully. "Erm ..." he glanced away and then back. "what do I do now?"

I leaned back in my chair. "Why don't you try complimenting something about me and see how it goes."

He opened his mouth and tried to speak but nothing came out. "My mind has gone blank."

"Nothing you're going to say will ever be wrong Eric. Maybe say how much you admire my dress, or earrings, or even better... " I pointed down. "I'll tell you a secret, if you let me bore you to death about my shoes, you got me."

"I love your shoes," he said instantly. "Are they designer?"

"Why thank you, Eric. I'm glad you asked ..." I gave him a full run-down of my extensive shoe collection and what I liked about each pair. I can't imagine he was very excited about that but he intently listened and even asked intelligent questions. It was like he was taking a class and was scared there was going to be a test. I remembered listening to girls I was trying to date rambling on and on and desperately trying to feign interest, not daring to interrupt or change the subject. I could drone on forever about my shoes but eventually I showed the poor boy some mercy and asked him what he was into.

The table next to us became free and Cindy had protectively taken up residence. She pretended to be engrossed in her phone but I could tell she was listening. I saw Eric sneak a quick glance at her, I presumed he thought she was attractive, as many men did, but there was no lingering stare. His eyes darted straight back to me. Another bar patron tried to approach Cindy but she quickly rebuffed him. She was waiting for me to make a decision.

Eric gradually became more comfortable and we chatted for about an hour. He was fresh out of college at a new job and just striking out in the world on his own for the first time. He didn't really know anyone in the area and thought he'd try a bar when he noticed me. We were getting along well. He was very keen, trying to throw compliments at me as best he could and I was lapping it up. I was completely entranced with the experience of this side of the fence. I'd never had someone so intent on impressing me before. He was clumsy with his small talk and obviously inexperienced, but that didn't matter, he had somehow become fixated on me and his unconditional attention was absolutely intoxicating. "Eric, I think I'd like a change of scene." I leaned forward and put my hand on his thigh. "Perhaps we could go to your place for one more drink?" I'd never had the power before to control how the evening was going to turn out, to be the one who decided whether I would be getting lucky. He wasn't going to say no to anything I said.

"I'd like that," he said with a smile. "I'm pretty sure my roommate is out tonight."

"Even better. Now where's your car?"

I proudly strode out of the bar with Eric, glancing in the direction of Cindy as I left. She put her closed fist to her open mouth, pressed her tongue into her cheek, and mimed a blowjob with a longing look in her eyes. I loved that girl. Unfortunately, a man in her line of sight didn't realize the gesture was intended as encouragement for me and thought she was making him a suggestive offer. I wasn't worried, she was a resourceful woman, I'm sure she'd resolve the matter to his satisfaction one way or another.

As we rolled up to Eric's home, I discreetly messaged Cindy the address. I had every confidence that he was perfectly decent but she'd have my back, just in case. She'd be along soon and wait outside. I'd always done the same for her.

Eric took me inside. There were two gaming PCs set up at the back of the living room, plates of half eaten food on the floor and clothes covering the couch. It looked like he was still living the college lifestyle and slowly discovering all the things he'd never noticed his Mom did for him. "Sorry about the mess. I should have cleaned up. I didn't realize someone would be coming by." He made an attempt to make some space and collected up the clothes, throwing them on the floor.

"No problem, it reminds me of my first place."

He was uncertain what to do now and looked around for something to talk about. "Want to see the new game I just started? It's really great." He pointed at one of the PCs.

"Could I have that drink please?"

"Oh, sure. Sorry. Er, yeah." He completely forgot to ask me what kind of drink I would like and went straight through to the kitchen. I heard him rummage in the fridge and he came back a moment later. "I'm really sorry, we're out of beer. Can I get you something else? I might have coffee." He looked distressed at his lack of hospitality.

"Don't worry about the drink Eric." I stepped forward, put my hands on his cheeks, and kissed him to his enormous surprise. "Eric, now if I do anything you don't like, you tell me, OK?" I was worried about his naivety and inexperience, that I might push him further than he wanted to go and he'd be too scared to mention.

He smiled. "Well, I liked that."

I touched his lips. "Now why don't we sit on the couch." He just nodded, looking extremely anxious. I was exhilarated by being in total control. He was putty in my hands, ready to take my lead and do whatever I asked. I felt like a goddess.

Eric sat down but I didn't. I got on my knees in front of him. He started breathing heavily. I unbuckled his belt and pulled down his pants and underwear. He was already erect. I looked up at him sexily. "Good boy," I whispered. I adored the idea that he'd had a hard-on just from the mere anticipation of me. He made me feel like a girl, but more than that, a truly sexual woman. On one hand, I hoped he wouldn't prematurely ejaculate all over my expensive dress, but on the other I hoped he would. I'd consider it the biggest compliment he could ever pay me.

I licked his shaft from base to tip. I wanted to use all the power I had to tease him. He had a sudden, sharp intake of breath like electricity had just run through his body. "I've never seen one so big before," I assured him in a sultry voice. It was a pretty average five inches but I wanted to build up his confidence. "I'm not even sure I can take it all." I kissed the tip and then licked up all his pre-cum with my tongue. He tensed up. I wondered if that was going to be enough to make him explode but he managed to hold back. I put my lips around him and easily got it all into my mouth, sliding down him right to the base. Then I started sucking him with a regular rhythm, moaning as I did, showing him my enjoyment. He came in thirty seconds, pumping into my mouth three times.

I looked up at him, closed my eyes and swallowed. "Delicious," I said before cleaning him up. He sank back into the couch with a huge smile on his face. I was in awe that I had the power to make a man so happy.

"Thank you," he whimpered.

"You don't need to say thank you Eric. I enjoy it." That I did. I pulled up his underwear and pants. "Can you help me up?" He outstretched his right hand to lift me and I offered him my left. I was intending to kiss him some more but he noticed my ring. I had forgotten to take it off.

"Are you married?" he asked.

"Engaged," I said automatically. I should have lied.

"Huh? What's the deal? Is it not going well?" He now thought I was cheating on my partner.

"It's all good. We have a very understanding relationship." But now I made a colossal mistake. "You know, my fiancée is probably outside right now."

"What?!?" He jumped to his feet and his still unbuckled pants fell down. He picked them up and quickly ran to the window trying to do up the belt as he went. He peeked through the blinds. "What's going on?" I suddenly realized he was panicked that this was all some kind of set-up and he was terrified a very angry man was going to burst in and beat the crap out of him.

I stood up and chased after him. "It's alright Eric, it's all OK." I put my hands on either side of his face and twisted his head towards me. "No one is going to hurt you," I reassured him. "You're fine, you're alright. Anyway, my fiancée is a girl. She's tiny and wouldn't hurt a fly." She was taller than Eric and probably could easily take him on in a fair fight but it sounded more reassuring if she couldn't. "She's totally happy about all of this. Really."

"What?" he was still very confused.

I quickly went and got my phone out of my purse and dialed Cindy. "Babe, I've been a complete dumbass and got this poor boy in a panic. I told him you were here and he thinks you're a jealous six-foot-five dude who's going to beat him up. Could you just get out of the car please?"

Cindy stepped out and started waving wildly. I pointed her out in the darkness to Eric. "That's her there, the blonde bimbo waving in the wrong direction."

"Oh," Eric seemed a little calmer now he wasn't facing down some huge gym bro intent on murdering him.

"Can she come in?" I thought again. "Or maybe actually I should leave now. I've probably done enough damage for one night."

I thought he'd want me gone. "She's really fine with it? You know, doing what we did?"

"Absolutely one hundred and ten percent. Let me call her in, she can tell you herself."

I got back on the phone and invited Cindy to the door. Eric went to answer it and looked surprised at the hot girl in pink he found on the other side. "Oh! It's you. You were at the bar."

"Yeah. Just looking out for my girl. Can I come in?"

"Er, sure," Eric said.

"I'm really sorry, did we scare you?"

"No, no, it's fine." He had been quite rattled.

"My name's Cindy. I'm engaged to that moron over there." She pointed at me.

"My bad," I apologized, putting my hands in the air to emphasize the point. Maybe he was due an explanation. "Eric, did you say you had some coffee?"

We sat on the couch with Eric between myself and Cindy, sipping our coffee and started trying to explain our relationship.

"Have you ever heard of a sissy before Eric?" I asked him.

"No."

"A sissy is just like a woman but ten times the fun," said Cindy. I wasn't sure that adequately covered it.

"I am very much in love with Cindy here and we're going to get married," I reached my hand across to her and we held hands in his lap. "But you see we both like to play with men. Neither of us gets jealous about it, neither of us minds, it's just part of what we do."

Cindy turned to Eric. "So did she suck you off yet or can I do it while she blathers on?"

Eric looked at Cindy and swallowed. He was very intimidated by her. "Erm ..."

"It's OK honey, I did him already," I clarified.

"Good girl," said Cindy.

Eric turned to me. "I was kinda hoping I could date you," he said with a sincere sadness in his eyes.

"I'm really sorry Eric. I was just looking for a one night thing." I hugged him. "I'm really flattered, truly I am. You're an amazing guy. You did so well tonight. If I wasn't engaged, you'd be the one."

"Oh." He looked despondent. I felt so guilty. He'd made me feel so good and I had just led him on. I wondered if I could find some way to make it all right.

"Look, why don't we help you find someone Eric?" I looked at Cindy.

"Yeah, we could do that," said Cindy enthusiastically. "A nice girl. We'll get you someone perfect."

He turned to me. "But I wanted you." I kissed him.

Cindy leaned on his shoulder. "I feel for you dude. She's really special. I just got in there first and there's only one Aaron to go around."

"I'm just a crush Eric. You'll have ten of those before you find the right one. Let me set you up with someone."

He wasn't totally convinced but eventually he accepted the idea that I wasn't available and agreed that maybe he'd think about dating someone else. I thought I'd leave him a parting gift. I straddled him on the sofa with my knees either side like I was screwing him, my ass was partially visible under my dress. "Cindy, can you take a photo please?" She got up. I turned to Eric and gave him a passionate kiss as Cindy took some pictures.