My friend Jim approached me at school Monday morning. He leaned against the lockers and asked, “Hey, how did everything go after the party?”
My heart fluttered briefly as I wondered if he’d heard something, but then I realized if he‘d heard that I’d probably be hearing all about it from everyone! So, I relaxed and shrugged it off, “Yeah, it was fine, no big deal.” That was a lie, but what was going to say, I blew two guys on my way home? Oh and they were going to make me into their personal sissy slut, too? I planned to keep that secret for a while.
“Cool, glad you made it okay. El says you can just drop the clothes off any time,” Jim said casually as he was looking over his shoulder at someone who was waiting for him.
Oh man, I hadn’t thought about having to give the stuff back, I hoped to keep them! “Oh, okay. I was pretty drunk when I got home, so I’m not sure where they are. I’ll have to check with my mom.”
“Okay, no rush, I don’t think it’s a big deal, she just mentioned it when I gave her my stuff back. I gotta run,” he said, turning away.
Well, that would be a problem, especially since the panties had been absolutely soaked when I came while sucking off Don and Chuck. I had washed the panties and the stockings, so I think they were okay. The rest of the outfit I was sure couldn’t be machine washed, so I wiped everything down, hoping that would be enough.
As I was thinking about care of my femme clothes and how to tell Don that I might not have the clothes any more on Friday, Chuck leaned out of the bathroom door and waved me in.
I sighed and my shoulders slumped. Did they seriously want something now? I was scared what was going to happen in the bathroom! I stood up straight and headed in. I might as well meet it head on, so to speak.
In the bathroom, Don was leaning against the sink smoking a cigarette. Chuck kept watch by the door.
Don could tell I was nervous, “Don’t worry, slut. I don’t want anything right now, I’m only interested in you when you’re dressed appropriately.” He took a drag and grabbed a small bag next to him and handed it to me. I looked up confused. “It’s a present for you.”
I opened it and looked in. I saw some kind of colored squares and brushes in a whole big kit. There was also a tube of something and a pink plastic… thing.
“There’s a make-up kit so you can practice and get yourself nice and done up when we get to my place Friday night,” Don explained, “the other is a butt plug and some lube. You better practice with those, unless you want to be walking funny all weekend.”
I looked up confused, “A butt plug? But… why?”
“You really are a dumb cunt sometimes. That should be obvious, we’re gonna fuck you, and while I like a nice tight ass, I figured I’d be nice and let you get a bit broken in first. Ain’t I sweet?” Don grinned like the cat who ate the canary.
“Yeah, you’re a peach,” I replied, unsure what else to say.
“I’d suggest hiding that away before anyone else sees it, but it ain’t my sissy ass. Later,” he put out his cigarette and headed out.
After he headed out, Chuck leaned back in the door, “By the way, Don says you better wear the plug to school, too. He wants to check on you.”
“What? I can’t do that, what about gym?” I asked my eyes wide. This was getting out of control!
“Good point, I’ll check with Don. Maybe he can get you out of gym or something,” he shrugged and before I could reply, he left.
The rest of the day was a blur. I was both excited and a bit scared about playing with my new toys!
I got home in a rush and immediately went up and dumped out the bag on my bed. I was surprised at the kit. It was fairly sizable and seemed to have all kinds of different make-ups for the eyes, lips, cheeks, plus brushes and applicators for everything. It wasn’t huge, but definitely too big for my purse! At least I had the couple things El had included in the purse.
Thinking about that made me remember that I was supposed to give the clothes back, I’d have to let Don know. After all, if he got this make-up kit, so maybe he could get some more clothes? And the plug. I checked out my new “toy”. Well, it wasn’t too long, but it was pretty wide toward the bottom. It also had some kind of lip at the bottom. I guessed that was to keep it from sliding all the way up your ass!
I wasn’t sure I could fit it, but I guess that’s what the tube of lube was for! Well, I was going to be in, so I might as well, give it a try. I was both scared and excited!
I figured I might as well get dressed up since I knew my mom wouldn’t be home until late, so I had plenty of time. I got out the stash of clothes I had, which included a few other things I had managed to sneak over the years. There were three pairs of panties, a pair of pantyhose and a bra. They were pretty tame compared to the new outfit I had. I decided I was going to enjoy this outfit while I still had it. I hoped I could get away with keeping it, but I was going to enjoy it either way.
I pulled out the PVC miniskirt, the PVC bustier top, the garter belt, the fishnet stockings and of course, the stripper heels and the heavy duty corset! I quickly pulled panties on and tucked so I wouldn’t make too unsightly a bulge!
I then took my time dressing, enjoying each piece as I put it on. The cool, slick PVC feeling so clingy as I wrapped it on, the almost bondage-like feeling of the corset and of course the stockings! I slipped on the heels figuring I’d better practice walking in them, too!
I took out the make-up kit and figured I might as well go the whole hog and see how well I could do. I was going to probably need practice since I’d have to do it myself on Friday! Thankfully there was a small instruction book in this kit. It gave tips and tricks for dramatic looks and color combinations. I was really looking for some kind of basics. So, I decided to start simple. I knew I could manage lipstick, so I got out one of the basic colors, a nice pink and tried it on. It was fairly easy to put on, but I figured out quickly that if I went outside my lips it looked more like clown make-up!
So, I also practiced cleaning it off, and started again. The second time I managed to fill in and get a nice full look. I figured the guys would want a really bright vivid red, but I figured I could practice with several of the colors this week and see what worked. I figured the blush was probably pretty easy, so I experimented with that. Again, I learned that subtlety was key. Too much could look really odd, too little and there was almost no point!
I tried the mascara then, too since that also seemed pretty straightforward, it just goes on your lashes, right? Easier said than done! I kept getting it on my skin around my eyes, then trying to clean it off would get me black streaks across my face. I think I was finally able to find a decent look with it, but it wasn’t great. Well, that’s why I was practicing!
I decided to hold on the eye shadow and eye liner since that seemed pretty complicated. So, I instead took to my other ‘present’. I pulled out the butt plug and the tube of lube. On the one hand, I was really excited about the idea of being fucked, on the other hand I was really scared what it was going to be like. I kind of wished I had a vibrator or dildo to try it out first, but I figured that’s what this was for.
It was pretty wide at the base, so I figured I should ‘warm up’ some first. So, I hiked my skirt, pulled my panties aside and started running my hand over my ass cheeks. I was already pretty excited, so I was making a bit of a bulge in the front. I ran my finger down my crack and began teasing my hole. I was surprised how good and erotic it felt. Then I remembered Don fingering me when I came before, so I guessed I should go for it. I licked my finger and began siding it into myself.
The rush from penetrating myself was amazing, it was a bit overshadowed by the slight twinge of pain as I pushed most of my finger in. I slid my finger in and out slowly, surprised that it both hurt and felt good. Things began stretching after a moment and the pain gave way to pleasure. Now, I was getting really horny. The amazing thing at the back of my mind was I now WANTED to get fucked. And not like, soft gentle lovemaking, I wanted animal fucking.
I was getting a little crazy with lust, so I knew I needed to get the plug in or I was going to jerk off and that would be it. So, grabbed the lube, then pulled out my finger and began greasing myself up, both outside and in. I really began diddling myself at that point. My finger slid all the way in nice and easy, with the lube. I added a second finger and that hurt for a moment at first, but then the lust overrode that. I bent over and was heavily fingering myself. My breathing was ragged and I was out of my mind with lust.
I pulled the plug over with my left hand while still fingering my ass with my other hand. I lubed it up and then reached back, pulling my fingers out and lining the tip up with my ass. I pushed and I could feel the cold lubed plastic slide right into my hole. I got several inches in before it hit some resistance. Stretching again hurt a bit, so I backed off then pushed some more.
Basically I started fucking myself with the plug, taking in more and more with each stroke. Finally one last push and the plug slid all the way in. The base seating itself against my cheeks as my ass stretched to accommodate. I had a very weird pleasure and pain mix. I couldn’t resist and had to reach down and untuck my clitty from my panties, I was rock hard in a few moments and began stroking away.
I was so worked up I knew I was going to cum pretty fast, but it was going to be intense!