A New Spin on Role Playing Games Ch. 03

(M/t, F/t, M+/t -- sissy, oral, anal, boot-worship, strap-on, CBT, corporal, cream-pie, water-sports)

I woke up a bit sore and slightly confused about where I was. I realized I was in my apartment, still dressed in part of my outfit from the LARP earlier. The dried cum all over my face, neck, arms, ass and crotch were a testament to just how wild things had gotten.

I started getting aroused when I remembered that I was the 'prize' for the winner. My winner was going to be over in less than an hour, so I needed to get ready. I decided to soak in the tub to see if that would let some of the soreness ease. Especially the soreness in my mouth and ass.

I only had a little bit of time to get ready before he was supposed to arrive. My nails were already done, so it was mostly about getting my make-up done. I wasn't sure what he wanted to do, so I figured I should go subtle, but still sexy.

I started with shaving again. My facial and body hair don't really grow in very fast, so it was easy to keep up with shaving. I applied moisturizer to most of my body. That helped me get a bit worked up, and also gave me a nice floral scent all over.

I found a nice neutral set of make-up and did a quick application of that. Just some powder, a little tan eye shadow and a nice brown lipstick. This gave me a fairly mild look that still looked nice. I was a little surprised how nice I looked in the mirror. I realized that wild, over the top was fun, but something a little subtler could look good in the right circumstances. I briefly wondered what it would be like going out? I wasn't sure I was ready for that, but it was an exciting thought.

I made my way over to the bag of clothes Nora had sent and started pulling everything out. To her credit, she had tried to find a pretty good mix of everything. I had several skirts and dresses in different colors and styles, several different types of tops, a few pairs of pantyhose and stockings, not to mention some other lingerie, shoes, boots, wigs, jewelry, a robe and several different make-up kits. It was a lot of stuff, especially since my previous collection consisted of some panties and bras, two pairs of pantyhose and one pair of 2" heels. This was a huge step-up.

There was also a selection of some costumes. Apparently one of the sisters was almost my exact size, so I was able to get a bunch of her old stuff. There was a cheerleader costume, a French maid costume, a sexy cop costume, plus things I couldn't recognize that might have been slips and such, but I wasn't sure. They were in a bit of a bundle, so, I just set them aside to go through them later.

It was almost 6pm, so I wanted to get something on. Not that it really mattered my gentleman caller probably had his cock in my ass or mouth, or both, earlier, so its not like he didn't know what kind of girl I was.

I still felt having something femme on would get me in the right head space. So, I pulled on a pair of red panties and a red bra. I then slid up a red garter belt and attached some black opaque stockings. Now, I was starting to feel femme and sexy. I grabbed the robe and wrapped that around myself.

I pulled out a fairly subtle brown wig that looked almost to be the same color as my natural hair. I slid that on and I dug around, finding some hairpins to attach the wig to my hair. I sat down and pulled a pair of the shoes over. Just a nice pair of pumps, nothing too fancy but they were at least 4" heels. I was looking through the jewelry when there was a knock at my door.

Gee, who could that be?

I giggled a little, feeling a little nervous about this. Thankfully the guy... Dwight? Yeah, Dwight was his name. He seemed pretty nervous about this, too. Hopefully we'd be able to relax and enjoy.

I walked over and opened the door in my robe, heels and soft make-up. The look on Dwight's face was priceless. He just stood there for a moment with a small bouquet of flowers in his hands. I smiled and looked at him expectantly, letting the robe peek open so he had a nice glimpse of my lingerie.

He didn't move or speak. He stood there staring, so I asked, "Are those for me? That's sweet."

My voice seemed to wake him up, "Y-y-yes!" He sputtered, "They're for you."

I took the flowers and waved him into my apartment, "Please come in."

The pile of clothes was pretty obvious, it was a small efficiency apartment with just the one bedroom, bathroom and kitchen/multi-purpose room. I gestured for him to have a seat on the couch.

"So, you wanted me to do a little fashion show?" I asked coquettishly.

This seemed to get Dwight's attention. He grinned like a kid who just got some candy and nodded. I stalked over to him, my heels clicking softly on the floor, and stood next to the couch. Giving him a bright smile, I let the robe fall down and tossed it onto the couch striking a pose to really show off my ass and the stockings. Dwight swallowed nervously, shifting uncomfortably in his seat.

"I thought this was a nice base outfit. Do you like it?" I smiled and blinked my eyes. I realized the batting eyelashes thing wasn't as effective if you didn't have mascara or fake eyelashes on. Oh well, hopefully it got the point across.

Dwight nodded again, apparently struck mute. I have to say, this was kind of fun. I realized I was his prize, but I was clearly the one in control and it was a lot of fun. I briefly thought about Nora dominating me and wondered if I could play him like that. Maybe, but that didn't feel comfortable. We'd have to see, maybe if I found a 'dominatrix' outfit? I mostly had slutty stuff, so I'd probably go with that.

I went over to the pile of clothes and found a slinky red dress, but I thought I'd save that and try some other stuff first. Dwight was leaning over the arm of the couch, watching expectantly. So, I made a big show of putting in my falsies. Then pulling on a tight black top that hugged my chest and really highlighted my fake tits. I slid on a knee length black skirt and looked myself over. It actually looked pretty nice. I was surprised that this looked sexy, but still nice. Not super slutty, just a little slutty, especially with the red heels.

I strolled back over to Dwight, letting my hips sway exaggeratedly. I stopped just short of him, striking a pose, "So, what do you think?"

"Oh yeah, you look... I mean, its great. You look super sexy!" Dwight stammered.

"You think I'd get some attention like this?" I asked softly, leaning in close.

"Oh wow, yes. They'd be drooling over you," Dwight answered excitedly.

I grinned, "That sounds like fun. Want to see something else?" I asked, purring.

Dwight answered with a nod.

"See if you can find some music for us while I try on something else," I gestured to the corner.

I made my way back to the pile and dug through, finding a black sheath dress. I slipped the skirt and top off, fighting my way into the dress. Getting the zipper up in the back was proving to be more than I could manage. Apparently girls had to be double-jointed to get themselves into clothes? I guess this was why they had friends over to help them dress.

As some classic rock played, I figured Dwight had found something, so I scurried back over to him. As he turned to me, I spun and asked, "Zip me up?"

I could almost hear Dwight's grin as he slid the zipper up to the back of my neck. I turned and let him get a good glimpse of the clingy black dress. I liked the feel of this one. It really hugged my curves, what I had of them anyway.

"How's this one?" I slid up close to Dwight, even with the 4" heels I was an inch or two shorter than him. He leaned in and kissed me softly. Okay, wow. I was not expecting that. It was nice, but felt a little weird. First, he had stubble on his face. I'd never kissed anyone with stubble before, it was an odd sensation. Second, I was expecting this to be a dress up and suck his cock, maybe get fucked kind of night. It hadn't even really occurred to me that kissing and making out might be on the menu.

I broke the kiss and looked at him and pointed out, "You're going to have my lipstick on you."

He just shrugged and pulled me in close, kissing me again. I'll say, feeling his body pressed against me was really nice. It was fun to to feel how excited he was. I was starting to feel randy again, and that got me feeling playful.

I ran my hands over his shoulders, as his hands ran down my back and played with my ass. That was teasing and nice. He started kissing across my cheek and over to my neck. Oh my, that was really nice. Apparently I had a serious erogenous zone on my neck and him hitting that had my clit uncomfortably testing my tuck in no time.

Shortly, I was panting and worked up, my hands ran down his chest to his crotch where I could feel how hard he was. I started opening his fly and within a few moments had his cock out. I kneeled down and started working lightly with my tongue on his cock. This wasn't a group setting, so I was taking my time with this. I started lightly with just my tongue, running it all over getting lots of moans and muttering from him. I looked up at him as I swirled my tongue around his cock head, watching his head tilt back and hearing him groan with pleasure really stroked my ego and made me want more.

I moved down and began tonguing his balls, which also got a lot of moaning and groaning. He also started running his hands through my hair, well, my wig. Which was nice, but would probably feel really nice if it was my real hair. I licked and sucked my way back up to start really sucking his dick.

Looking into his eyes as I wrapped my lips around his head sucking his length into my mouth. He was about average in size and length, probably about 7 or 8 inches. Not huge, but certainly way bigger than my unit. This let me really be able to take him deep and suck his cock into my throat pretty easily.

I was still taking my time, slowly working every inch up and down as I massaged his length with my lips mouth and tongue. A few strokes later, I paused all the way down to suck on him while he was buried in my throat. He then put his hands on the back on my head, holding me down, I stayed like that while he bucked slightly in my throat, eventually letting me up for a quick breath. I caught my breath and then slid my mouth back down on him, starting a nice steady pace.

He then got more aggressive, holding my head and basically fucking my throat. I couldn't believe how much that turned me on. I'm not sure if it was the rough play, the control or what, but something about being taken and used like that had me uncomfortably tenting my panties since I was tucked down.

It only took a few minutes before Dwight grabbed the back of my head, jamming his cock deep in my throat. He groaned and pumped his cock, I could feel his cum shooting straight down my throat as he bucked and grunted through his orgasm. He eventually let go and I gasped deep for air. I was also panting with how horny I was.

Dwight had his eyes closed. He opened them and looked down at me with a wide grin, "Holy shit, that was hot as hell."

I bit my lip and smiled, "Oh fuck yes! You want to play some more?"

Dwight nodded, "Oh yeah, but I'm going to need some time to recover after that. You want to show me some more outfits?"

So, I continued with my fashion show, running through several different combinations of outfits, I finally tried that slinky red dress. I paired some black leggings with a blue crop top. I also went through several costumes. The cheerleader outfit was fun since it even had some pom poms. I tried doing an quick cheer routine that was more comedy than sexy, but it was fun, so that was the important part.

Dwight apparently also liked the cheerleader costume since he pulled me onto his lap and started making out with me again. That led to me straddling him and grinding on his cock, until he eventually pulled my panties aside and slid slowly inside me.

I groaned and he slid deep in my well-stretched hole. I was still a little uncomfortable from all the fucking earlier, but it only took a moment before I was riding the full length and loving being filled up again. The nice thing with being on top was it let me control the speed and also let us keep making out while I was riding him.

We went for quite a while before he reached into the front of my skirt and pulled my cock out of my panties and started stroking me. The intensity of that sensation had me bouncing wildly on him while I moaned deep and long.

Dwight pumped hard on my cock while I rode on him and within a few moments I was grunting and finally came with a scream. All of my spasming must have set Dwight off since he grabbed my waist pulled me tight and proceeded to cum hard up my ass. I was deep in the throws of my orgasm, so I didn't realize he was cumming until I came down and realized he had his head thrown back in post-orgasmic haze. He fell back onto the couch, and I leaned forward on his chest, both of us panting hard.

We had a few drinks, but I think Dwight was spent and before too long he headed home. I was both disappointed and somewhat relieved. I'd have to talk with the group about maybe doing the 'winning' on another night, since I was also beat. I cleaned up a bit and basically passed out in bed.

I was a bit surprised when I got a message from Nora a few days later. It said, "Love the videos of you being used, sissy girl. So hot, mmmm. Come to my house on Friday night. Be fully shaved and ready to serve."

I replied to let her know I'd be there and asked how she got a video, but she her only response was, "Be here at 7pm. Do NOT be late."

The threat had me both scared and excited.

Friday night found me at Nora's. I got there about 6:50pm since I didn't want to be late. I just hung out for a few minutes before I knocked just before 7pm. I waited for a few minutes, and then knocked again.

Nora answered the door at 7pm. She was clearly in vamp mode. She had on a heavy-duty boned leather corset, a leather skirt, thigh high boots and elbow length gloves. It took me a moment to realize she was also wielding a riding crop. I could really only stand and stare at her. I was trying to say hello, but my brain wasn't quite working.

"Are you okay?" she asked slyly, almost purring.

I nodded, but that was the most I could manage. She let the crop fall lightly on my chest and ran it up to my chin, before pressing it up and forcing my chin up. I gasped in surprise and fear. With the heels she was slightly taller than me, so I was looking up into her eyes. It was very intimidating.

"I asked you a question," she stated slowly, menacingly.

I shivered in fear, "Yes, Ma'am. Sorry, I'm just, I mean, you are... wow, you look so powerful and fierce."

"Hmmm, powerful and fierce, I like that," she growled. "Does that mean you're scared?"

I nodded and swallowed nervously, "Yes, Ma'am."

"Good," she replied. She dropped the crop, turned and started walking in the house, paused and looked back, "Oh and you will call me Mistress from now on. Clear?"

"Y-y-y-es, M-m-mistress," I replied quickly.

"Follow me," she ordered. I followed her into the house. I thought we'd be heading to the attic again, but she went to the kitchen. So, I followed her there.

She turned and looked at me, beckoning me over with a finger. I approached, my heart hammering in my chest, a little scared about what was going to happen. She pointed to the floor in front of her. I quickly knelt down, looking up at her. She looked like a goddess looming over me like that. Her pale skin accented by all the black leather, the boots making her look even taller, like some kind of amazon warrior.

As I knelt, she smiled, clearly enjoying her power. "Good girl," she said smiling down at me, tapping the crop on her other hand. "Now, here's how things are going to work tonight."

She then laid out the ground rules. I was to only speak when spoken to. I was to address her as Mistress. If anything made me uncomfortable, I was to say the words 'Yellow' or 'Red'. Yellow if I just needed a moment to catch my breath or pause for a moment. Red if I was freaking out and needed to stop. I was to follow her orders to the letter and any failure meant I would be punished. I was definitely not allowed to play with my clit, and if I came without permission, I would be severely punished. If there was any cum, I was to clean it all up with my tongue. There was a whole list of instructions that I was to follow. My head was kind of swimming with the intensity of it all.

After she laid out the orders, she asked me very simply, "Is there anything you absolutely wouldn't want to do?"

"I'm sorry, Mistress. I don't understand," I replied, still a little thrown off.

"Well, sissy," she smiled like she was explaining something to a child. "I'm going to use you as my little sissy sex toy tonight. I'm going to dress you up and I'm going to make you into my little slut with my strap-on. I'm also going to tie you up and beat your ass raw. I'll also be smacking your little sissy clit and balls around, too. Is there anything there that sounds like too much?"

I shook my head, "I don't think so, Mistress. That sounds... exciting... and a little scary."

"Good, how about worshiping me?" she gestured to her leather clad body.

"Oh yes, Mistress. I'd happily worship you," I smiled.

"Good, then start by licking my boots," she pointed to her sexy boots.

I leaned down and laid on the floor, then began kissing and licking her boots. I was unbelievably excited at debasing myself before this gorgeous vision of a woman.

She stopped me after a few minutes, "This is nice, but I want to be entertained. Take off your clothes, now!"

I obediently stripped off my jeans, shirt and socks. She laughed slightly when she saw my pink panties. I blushed softly.

"Those are cute, slut," she chuckled. "But I want you naked, get 'em off."

I hurriedly dropped the pink panties.

"Good girl. Now, go to the fridge, get me a glass of wine and get some water for yourself," she smiled and winked.

I scurried to the fridge and found a bottle of wine, but it wasn't open. Thankfully there was a corkscrew sitting in an organizer near the fridge. I opened the bottle, found a glass and poured it out for her. I grabbed a bottle of water and hurried back to her. I had heard her moving around and she had moved to a chair next to the kitchen table.

I sat the glass of wine down on the table. I took a quick sip of the water. Then she simply pointed to the ground and her boots. I got back on the ground and began licking and worshiping her boots again.

She sipped her wine and laughed at me, which just made me even more excited. I was a little embarrassed at how much her laughing turned me on. I think she realized that too since she started nudging my clitty with the toe of her boot, "Does it excite you when I laugh at your little nub, slut?"

I nodded and said, "Yes, Mistress," as I continued licking away at her boots. She alternated between lightly kicking my clit with her boots and digging the heels into my skin. She really focused on my ass for digging into. My breathing was quite ragged with how worked up I was, and my clit was dripping pretty steadily. She kicked the underside and my dripping got all over her boot.

"Oh my slut, your clit juices got all over my pretty boots, lick them clean," she ordered.

I switched to licking the other boot, cleaning all the pre-cum off of her shiny boots. She was clearly enjoying tormenting me as she was playing with her nipples, "Good slut, now suck on my heel."

She lifted the boot up and held the soft leather on the calf as I sucked on the heel. She continued playing with herself while mocking me, "Oh yeah, suck my heel, slut. Suck it like a little cock. Of course, my heel is bigger than your little clit."