A Sissy's Tale - Part 2 By Tasting Jenny
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This story is a work of fiction and contains descriptions of explicit sexual acts between men and women. If this type of content offends you or you are under the age of 18 do not read it.
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Copyright Nov 2023. All Rights Reserved.
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Becoming a sissy MF, bi, cd
"I'll be home late. Try to behave."
Kris' sarcastic admonishment combined with her smirk made me smile. How much trouble could I get into firmly locked in the chastity cage? And I'd already done the things that usually made my Friday special, wearing lingerie and masterbating. The only thing left was to call for pizza delivery.
The first thing that I learned after Kris left for her Friday Night out was that there would be no standing to pee with the chastity cage in place. Even as small as I was, the shape of the cage guaranteed a mess. I don't know why I just didn't sit to start with but my standard approach was to slide my junk through the leg hole and go from there. I peed all over my knees and thighs and a little on my panties. Now I had cum on my bra and pee on my panties. I managed to wipe off my legs and clean up the floor but taking a leak was a much bigger deal than I expected.
I loved the yellow bra and panties even more than I thought I would and there were just a few drops of pee on my panties. A little cum and pee wouldn't hurt. I put my jeans and t-shirt back on to be dressed when the delivery man arrived.
After cleaning up my mess and getting dressed I was curious about my collection of clothes that Kris had clearly found. I'd thought that having it in the basement storage closet hidden behind other boxes would make it fit in. The only thing that made it stand out was that there was a light logo of Shelley's Cafe. I'd found the box several years ago and while I'd been through several purge cycles of getting rid of all my feminine clothes, I'd kept the box. I loved the name Shelley and used it as my fem name.
My hidden box was now right up front and clearly visible. Opening it up, the clothes looked like they were all there but I needed to know if she'd found it. Running my hand around the bottom of the box I was hopeful that the dildo and lube I knew was buried beneath was still there. Nothing. It was only about 6" long but not something you'd miss. Now with a bit of panic I took the box to our room and dumped the contents on our bed. There were the black and pink bras, two camis, four pairs of panties, a pair of stay-up stockings, and a pair of 3" slingback pumps with a pretty bow on the toe. The right stocking has a big run because I'd snagged it on my toenail when taking them off. Really need a pedicure. I didn't have much but all of my clothes were there. But no dildo.
What did Kris think when she found my box? She hadn't asked about the dildo but she'd definitely found it. We were well past my being able to casually explain or deny. She knew. I heard the doorbell ring with the pizza and had to get him his $40 for the pizza and tip.
"Hi Steve. Thanks for the delivery. It's much easier than me going and getting it." Steve worked most Friday nights and I'd gotten used to having him stop by since I ordered pizza most Friday's. We were friendly enough that he'd step into the foyer while we traded pizza for money. I usually had to go find cash and the tip was just less than the pizza so there was lots of incentive for him to chat me up. He also knew Kris liked to go out and party on Friday's.
"Happy to. I appreciate your business. What happened to your standard Meat Lovers order. You threw me off going for Taco?"
"Thought I'd change things up tonight just to try something different."
"Makes sense but you seem like a serious Meat Lover. Thanks again and see you next week." Steve said as he stepped out the door. I wasn't sure if we were talking about pizza or something else. Could he tell I was wearing a bra and panties? Was he hitting on me? I couldn't tell.
The Taco pizza was a nice change up but it wasn't going to be as good for leftovers in the morning. No sloppy seconds there. But I did manage to make a huge mess getting lettuce and cheese all over as I sat on the couch and watched a game show on TV. There was a woman that was absolutely killing it and when I looked her up to see how many times she'd won, she was number two in the history of the show. She was also trans. She looked pretty passable to me as I wouldn't have known if I didn't look her up. Totally unexpected.
It took a bit of work to clean up my Taco pizza remains from the couch when my phone pinged. Seemed like everything needed extra cleaning tonight. Based on the ping, I expected Jill was posting the first pics from the evening out. I'd customized her "ding tone" because I was always curious where they were and what they were doing. Grabbing my phone, I saw the share link from Jill and couldn't resist opening it.
They were at the dance club tonight. I'd said Kris looked good enough to eat but that wasn't really doing her justice. She looked fuckably hot when she left. She was wearing so little that she was a guaranteed tease to any one that danced with her. The rest of the girls were showing lots of skin as well and there were men all around them.
My channel surfing moved on to Friday night football where two teams nobody had ever heard of were playing. The score was 24 -10 and they were panning the sidelines when they came across a player with a HUGE penis. It was one of those times where the announcers are talking and then there's an uncomfortable silence when you see something this unexpected. I'd seen it with pretty women in low cut blouses where they go totally silent for the shot but this was the first time I'd seen it with a guy. His cock was totally outlined in his uniform.
What the fuck? Was it a full moon or something? Usually I spent Friday evenings surfing the web and looking at porn and reading stories that didn't have this much real action. Was it that I was caged and wearing a bra and panties? How is this happening?
At 10:00 I received a text from Kris "Having a blast, hope you are too ;-). There is a yellow nighty in your dresser. It's not cheating if you want me to cuckold you, right? Hugs and kisses."
I read her text over and over. Did she want me to put the nightgown on? Was she coming home tonight? Was she asking my permission to cheat? My mouth went dry and I was scared and excited at the same time. I fantasized about her with other men every Friday night and thought about it almost every day. Imagining her pussy lips being stretched around a fat cock and then smashed vs barely feeling my 3" clit, Knowing that she couldn't help but cum with a real cock. But I wanted her to just do it and tell me how much she loved it, not ask me. I responded "Right" to her text.
"Say it!" came back immediately.
The text just sat there looking at me. My cock couldn't get hard in the cage but I was as excited as I've ever been. I wanted this so badly even though I was afraid she'd actually do it. "Please cuckold me."
And silence. It was 11:00 before I gave up. I thought about texting her again but I knew the answer. She was already fucking him.