Oh Jack 1

"Oh Jack! Can you come over and help me a minute?"

I stopped in my tracks and looked over. Samantha lived in the condo next to mine and was very friendly. I'd introduced myself when she was moving in and ended up helping her all afternoon. We talked easily and I'd started thinking of asking her out. We'd even been flirting a little bit here and there. She was a little short but had a body with all the right curves.

The only thing that made me pause was that the waist string on my shorts had broken so I was having trouble keeping them up. Perfect excuse for more flirtation, right? Well, my situation is a little more complicated. Let's just say I was wearing something I didn't want her to see under my shorts.

"Can I come over in a minute?"

"It'll just take a sec. Please?" she asked and gave me an exaggerated pout. Of course it was a sexy pout that happened to push her large breasts together to tease me.

I smiled and walked over, keeping a hand on my shorts, feeling my cock already stirring.

"What can I do for you?"

"I really appreciate this. Nothing like good neighbors, right? Can you help me get that stuff down from the attic?"

She had a ladder set up to the small door hatch to the upper storage. I could see a couple boxes up there and recognized them from her moving day.

"I told you you'd want those sooner than you'd think," I admonished her playfully. Then I looked at the ladder again and blushed a little. I really didn't want her to find out what I was, well at least not right then. Maybe I could do it quick.

"Here, let me hold the ladder," she urged and I climbed the ladder until I could reach the boxes. I positioned my legs to help hold up my shorts.

"Yep, that one. Okay just one more..."

I had to reach further for the other one and pulled on my shorts.

"Are you okay? You keep fussing with your shorts. You're fine. Here I'll take that box."

I tried to get down off the ladder but she blocked my way.

"Hold up a second. Jaaack."

"Yes?"

"Jack, are you wearing... panties?"

"What? I... I..."

"Well, your shorts sort of slipped down and I can see them a little," she said with a highly amused tone.

'Oh great, she's going to make fun of me,' I thought, my heart sinking. 'There goes my chance at asking her out.'

"Here, let me tug your shorts down," she blurted and yanked my shorts.

"What?!? No!" I yelped but it was way too late.

"Ahh ha ha I was right! Holy crap, Jack! Pink satin panties with, what's that written on your butt? 'I'm a sissy. Fuck me'? Oh... my... god!"

My face burned red and I felt humiliated. Surprisingly my cock was raging hard! I felt every inch of the specially ordered panties I was wearing, stretched taut across my bottom now that my cock was tenting the front.

"Wow, I mean, I knew there was something different about you," she began, still not letting me move or reach to pull up my shorts. "This explains so much! No, don't get down yet. This is too good! I was wondering how to thank you for your help. Wait right there and don't you move!"

With that she ran into her bedroom. I had full opportunity to yank up my shorts, get off the ladder and go back to my apartment to hide. Well, and to stroke and cum because the humiliation of this beautiful woman seeing my sissy side like this had me very worked up.

I didn't move.

"Okaaay, just getting him prepped for you."

She wasn't letting me see what she had. "What do you have?" I asked nervously.

"This?" she answered flourishing the object in her hand. It was an anatomically accurate cock-shaped dildo and a fairly large one. "Oh he's just my favorite dildo! Such a beautiful cock isn't he? This is what you want, isn't it?"

"Samantha, I'm not gay!" I blurted, my face burning even more.

"Oh, right," she said quietly as her hand began to massage my ass through my panties. "So you don't want to feel this beautiful cock? You don't want me to give you a little taste of him?"

I opened my mouth but couldn't speak. I desperately wanted to feel her fucking me with it.

"Yea, I thought so. You wish this was pounding your sissy ass, don't you. God, you're so hard right now of course you do."

Her hand felt great on my ass and her finger would rub the satin against my asshole.

"I've played with lots of kinky people, Jack, so I'm only a little surprised and very intrigued. I was wondering how I'd find someone 'interesting' in this town."

"Now, if you want me to put this cock in you, pull your panties down to your ankles, squat a little so your legs can spread against the ladder."

My hands were shaking, but I did as I was told, pulling the panties down and then lowering myself. My cock was hot pressed against a cold step of the ladder.

"Mmmmm, such a smooth pretty tushie!" she mused, noticing I was shaved smooth all over. She rolled a condom tight over the dildo and then coated it with lube. She ran the head around my bottom and finally began to head for my 'sissy pussy'.

"Like how he feels nudging between your cheeks? Mmm yea you want it, don't you! Ask me to fuck you. Tell me what a sissy you are and ask me to fuck your pussy!" she said in a firm, pushy tone.

"Yes..." I croaked out. I cleared my throat and tried again. "Yes, please fuck me..." It was still barely a whisper.

"I didn't hear you," she stated and waited.

"Yes, Samantha, I'm a sissy. Please fuck my pussy," I blurted loud this time, desperate to feel that beautiful cock pushed in me by this lovely woman.

"Well, your panties didn't lie, did they?" she laughed though not in a harsh way. It warmed my heart a little and calmed down the terrors on the edge of my frantic mind. "Well, let me push him in a little bit... God, you're so ready for it there's almost no resistance!"

She was right. I felt the thick cock pushing gently and I felt my ass relax quickly to accommodate it. My ring opened up and the shaft began to slide in. I whimpered in pleasure.

"How often do you fuck your ass with dildos, Jack, seriously? There! Damn, all the way in, all 8 inches!" she said with a big smile. She turned the cock inside me this way and that and the precum was flowing from my tip. "You are a fucking sissy whore, aren't you Jack? or should I call you Jacqueline from now on?"

I couldn't speak. I just clung to the ladder and enjoyed every second of the sensations. I'd never been a sissy with anyone and being indulged this way better than I could have dreamed.

"Okay, here he comes out."

"What, wait no," I complained softly.

"No, that's it. That's your reward." The dildo slipped out. "You want to cum? Well, maybe I can think of another favor you can do me this weekend, but you'd have to come over only wearing sissiest stuff. And you can't jerk off before then, deal?"

"Oh god, yes, yes!" I carefully got down off the ladder and pulled up my panties. She took my shorts so I'd have to brave our common hallway in just the slutty panties.

"Well, Jacqueline, thanks for helping with the boxes," she grinned. "I'm so glad I got to meet the real you. I think we're going to have lots of fun!"

It took all my willpower to walk back to my condo and not blow my cum all over my panties.