Sissy Friends Forever Ch. 02

I gave up on that and tried to pick up some sissy points by striking up a conversation about make-up with Naomi. I wanted to try and persuade her that I had no classically male interests at all anymore and I was solely interested in stereotypically girly things. I encouraged her to go through my purse, ostensibly to see what she thought of my lipsticks but really it was to show her the collection of items I had in there. I had some spare stockings, some sanitary napkins I obviously didn't need and perfume among a collection of expensive brand name lipsticks, foundation, mascara and eyeshadow. Right at the bottom though was a vibrator I had 'forgotten' about. When Naomi dug down to it, she stopped, looked up at me and smiled, widening her eyes, then continued fishing out a particular lipstick she was interested in. I got a little thrill of embarrassment from knowing she'd seen that.

Matteo placed his hands on the table while he was making an emphatic point about an Italian soccer team. He often needed to use his hands as a complement to fully expressing himself verbally, especially when he became more impassioned. However, I was surprised to see Colton reach across and take his hand. Matteo didn't flinch, he was of course used to being touched by men. Colton hardly seemed to notice he had done it. I started to wonder about him.

The evening finished and I hugged Naomi as we were parting. We exchanged numbers and said we'd keep in touch. I asked if I could take a selfie with her. I didn't particularly want one but I hoped that would prompt her to ask for the same in exchange and she did indeed decide to take her own. With any luck that photo would find its way around my former social network. Either way it was another challenge passed.

I went in for a hug with Colton, hoping to sneak a kiss on the cheek for a final sissy point but he backed away and just shook my hand. I wasn't going to get anywhere. When Matteo went in though, the opposite happened. Matteo offered only a polite handshake from a distance but was firmly pulled in by Colton who turned it into a hug, which he readily accepted.

Cindy drove us both home. "So how'd I do?" I asked.

"Better than I ever expected, but you failed on one. I didn't see any flirting with Colton."

"I tried, I really did," I sulked. "I so wanted my shoes."

"Rules are rules."

"It was never going to happen," interrupted Matteo from the back seat. "He's gay."

"Yeah, I was starting to think that too," I added. "He seemed really touchy-feely with you."

"Can't blame a man for loving the Matteo," he said, referring to himself in the third person. I laughed. He was so full of himself. "I give that marriage one year tops."

I turned to Cindy. "So since Colton was gay, as the unfailing walking gaydar just testified, that means the challenge was void. A hot girl like me was never going to turn him."

"Hmmm ... alright then, you get your shoes."

"Yay! I won!" I shouted. "Thank you, babe."

"I already ordered them anyway. I could never deny my girl anything." She put her hand on my knee.

"Awww, thanks, babe."

"You did absolutely incredible today. I mean look how hot you are and how you carried it off and all of those challenges you did so brilliantly."

"Thanks sweetie. I'm kind of proud of myself too. And Matteo did an awesome job as straight boyfriend."

"I will assume my Oscar in the mail," he said modestly.

"This was fun. We need to do this again," said Cindy. "How many more ex-girlfriends you got?"

"Three," I said. "We're not seriously doing all of them are we?"

"You bet we are. We can't leave anyone in the world not knowing you're a sissy now."

...

We'd been riding the subway for just over an hour. Cindy was sat next to me with her earbuds in. She's been listening to her latest hypnosis track one last time before we tested it. She was resting on my shoulder and seemed almost asleep. We were in the suburbs and had reached the end of the line. The train was about to turn around and go back into the city. All of the remaining passengers exited the car at the final station but we stayed on board. "Wake up sleepy. It's time." I nudged Cindy and she took the headphones out before stretching.

"We're there?"

"Yep, end of the line. Are you ready?"

"Let's get it done." She stood up on her heels and grabbed onto a pole. She was wearing one of her most ridiculous outfits. She had a very tight and very short pink skirt paired with black fishnet pantyhose. Her huge cleavage was on display, barely covered by a white crop top with a big red lipstick kiss motif.

I stood up beside her and whispered in her ear "Sissy period!" as I snapped my fingers directly in front of her eyes. For a moment I thought nothing had happened, I had strongly suspected nothing would, but then quite suddenly and to my enormous surprise, her eyes widened and she let out a whimper followed by two shorts pants. I looked down at her skirt. A small wet patch had appeared at the front, about the size of a quarter. Within a couple of seconds I noticed a trickle rolling down the inside of her pantyhose and into her shoe.

"No way." She had managed to ejaculate just from hypnosis without touching herself in any way. I was so sure it was impossible. I was so certain it was all just nonsense and role play on her part but I had been proven wrong. She'd had a physical reaction I was sure she couldn't possibly fake.

"Are you convinced now?" She looked stunned herself.

"I am more than convinced." Other passengers were starting to board. "Come and take a seat." I got her sat down next to me. "How are you feeling?"

"Like a man wearing a dumb outfit who's just cum in his panties in a public place." Her voice was lower which I knew meant her sissy side was heavily suppressed. As more people came onto the train she curled up. The straight man stuck in Cindy's mind was trying to hide the very feminine body and hyper-sexual clothing that embarrassed him so much, but it was impossible. Cindy had chosen her outfit especially to be what he would hate the most. I tried to hug her but she recoiled at the touch. The subway train set off for Chris' arduous journey home. He knew there was no escape, he just had to suffer the humiliation.

She stayed silent and unmoving. I made efforts to check on her every five minutes but she didn't want to talk to me, that was until about half an hour had passed. She spontaneously uncurled herself and sat up straight with her breasts confidently pushed forwards, hands on her knees.

"Are you back sweetie?" I said.

"Not yet," she said, her voice still low.

"What's going on in there?" I brushed back her hair as if it revealed her mind. At least she didn't mind me touching her now.

"I still feel like him, but I just don't care about my clothes anymore."

"That's great you're doing better."

"I think this is doing me some good. I've just kind of seen that no one cares what I look like. It's like when we first started out and I was so scared of going outside. Now I've just been going through that whole thing again but through the lens of a different mindset."

"That's awesome." I looked at her with puppy dog eyes. "Ready for a hug?"

"Try and stop me." She wrapped her arms around me and hugged me tight. I think we were having some success.

As we were exiting the train at our stop, some guy felt her ass. She confidently owned the situation and made a kissy face at him. I knew my girl was back.

Back in the apartment, I was rewarding her for the difficult time she'd gone through. I put her over my knee, ripped off her pantyhose and put her cum filled panties to her face. "Cum must never be wasted. Now lick," I ordered. She started lapping up her own mess. When she had cleaned her panties to my satisfaction, I started spanking her. Being spanked was one of her favorite things but after five minutes she picked up her phone and started scrolling. I was worried she was losing enthusiasm for it.

"Everything OK?" I stopped swatting her.

"Why did you stop?"

"I thought you were losing interest."

"I will never get tired of you spanking me. Back to work. I want my ass teaching a lesson." I picked up where I had left off with the 'punishment'.

"What are you doing?"

"I'm multitasking. I'm looking at wedding invitation styles."

I smiled and stroked her hair with my free hand. "Do you ever get worried that after we're married we'll run out of ideas to keep each other excited?"

She turned around to look at me. Seeing my serious expression, she put the phone down and got off my lap. She sat down next to me and hugged me tightly for reassurance. "You excite me by just being here, dumbo." She planted a big kiss on my cheek. "Besides I got enough filth in my brain to keep our panties soaked until the end of time. Don't you worry about that."

I kissed her. "What would I do without you?"

"Jack off in your closet?"

"Probably!" I laughed.

"I've been thinking, we should do something to help other sissies." She took my hand and squeezed it, then started playing with my ring. "All those packages I ship every day from my store. All those anonymous names on anonymous boxes. Not everyone has got an Aaron to play with. We should think about how to reach out and get them to meet up." She put her head on my shoulder. "I just want to make other sissies as happy as I am."

"That's a wonderful idea. You're a beautiful and generous person." I kissed her. "After I get two more rings on your finger, that's what we're going to do."