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 eyeshadow 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 it's 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 headspace. 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 hair pins 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, it's 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 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 of 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 a 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 throes 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 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, and 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.”
I was absolutely throbbing with excitement at her words. Why did her teasing me get me so excited? She kept poking my skin with her other heel, eventually digging the heel into my nipple. That was really uncomfortable, but she seemed to be enjoying it.
“Oh, I bet your little fuckhole is lonely. Turn around and show me your ass,” she hissed.
I turned around and put my face to the floor, I hesitantly opened my cheeks a little, but she growled to open up. So, I pulled my cheeks wider and she laughed heartily.
“You look like such a fucking whore,” she laughed. She then said, “Your slut hole looks lonely.”
I wondered what she meant by that when I felt something cold and wet on my ass. A moment later I felt something pushing into my ass. At first, I thought it was her finger, but then I realized it was a toy, maybe a dildo? She did say something about a strap-on.
I moaned as the toy got bigger and began to stretch me out. She began working it in and out of me, adding a bit more lube until she gave a big push and my ass really stretched, then closed around a tapered part. Did she just put a butt plug in me?
She laughed, “Oh yes, your hole looks less lonely now. Back to licking, my little sissy whore.”
I turned and went back to licking her boots, very aware of how full my ass was. It took a few minutes before I adjusted and was able to move normally again. She was now punctuating my licking with shots from her crop. Nothing real powerful, just enough to sting a bit.
“I can't decide which I want more, to beat your ass or to get you all sissified,” she looked at me while pursing her lips. “Maybe we'll do both.”
“I don't understand, Mistress. Did I do something wrong?” I asked hesitantly.
“Are you questioning me?” her eyes flashed with anger. Her mouth was drawn into a thin line. She looked pissed, and I was scared for a moment.
My heart hammered as I stammered, “N-n-o, Mistress. I just... I mean, uhhh... I didn't, I just...”
“Understand this, my little slut,” she tucked the crop into my chin forcing me to look up into her bright eyes. I gulped nervously as she said, “We're doing what I want to do, and I want to beat your ass until it's bright red and you're begging for anything to make it stop. Bonus points if I can make you cry.” She smiled a toothy, evil grin and chuckled. “Understand, cunt?”
I nodded a reply. She brought the crop down hard on my ass. “Ouch!” I cried.
“You fucking answer me!”
“Y-y-yes, Mistress,” I nodded and bowed slightly.
“Good, then into the Living Room,” she turned on her heel and stalked into the other room, grabbing her glass of wine along the way.
I crawled after her and into the Living Room. She gestured to some lingerie sitting on a small leather footstool. “Get dressed, sissy girl. I'm going to put on something more comfortable.”
She stepped off into a side room as I slid the white stockings up my legs. My clit throbbed as the silky material wrapped around my shaven legs. I was still amazed at how incredible stockings still felt sliding up my legs. I briefly considered playing with myself, but I wasn't sure how long she was going to be, or how much she was getting changed.
I dug through the rest of the stuff. There was a lacy garter belt, a corselette, a small thong, a pair of pumps with 4” heels, a dirty blonde wig and some leather cuffs. All the clothes were in a pure white, while the cuffs were in a soft pink faux leather. The outfit looked a bit like a bridal lingerie set. A slutty bridal lingerie set, but that seemed appropriate for me.
I slid the garter belt on and hooked the tabs to the tops of the stockings. I slid the lacy panties and put them on as best I could. My rock hard clit was making a tent in the front of them, but there wasn't much I could do for that. I slid my now stockinged feet into the pumps, suddenly glad I'd been practicing more with the heels Nora gave me.
I then wrapped the corselette around, but wasn't able to do the hook and eyes from the front. So, I spun it around and hooked it up, then spun it back around. I looked down a little disappointed at the empty cups. I wondered if Nora would let me run up and get some falsies to put in. I took a few quick moments to secure the cuffs on my wrists and ankles as well. There were cuffs for my thighs as well. It seemed I was going to be well secured.
As I checked myself out, I realized the dirty blonde wig was sitting off to the side. I pulled that on and checked myself out in a long slim mirror. I looked like a bride ready to consummate her vows. I was so wrapped up staring at myself, I only heard Nora's heels clicking when she was a few feet from me.
I was about to turn, when a swish and a sharp crack left a stinging mark on my asscheek. “Ow!”
“Admiring your sexy little self, sissy girl?” Nora asked, smiling.
I nodded, “Yes, Mistress.”
“Good, you can see the effect you've had on me,” she reached down and began stroking the rather large black strap-on she was wearing. “You've got me all hard you little slut.”
I eyed this monster cock nervously. She saw my hesitation and asked, “What's the matter, sissy? Don't you want to suck my cock?”
“Yes, Mistress, but it's very... big,” I stammered.
“Certainly compared to your little nub,” she then put her strap-on next to my clitty. It was at least twice the size of my little dicklet and much thicker. “What's the matter, slut? Aren't any of the boys that have been fucking your brains out this big?”
I shook my head, “No, Mistress.”
“Well, then good thing you've got that big plug in. Now, get on your knees and suck my dick,” she pushed my shoulders and forced me to my knees. I nervously licked her cock head and she purred. I looked up and saw the hunger in her eyes. She was super turned on. I could even smell her arousal being this close to her. The mix of her scent and the smell of the leather from the harness had me even more turned on than I was before.
As I began working on getting this monster cock wet, she took several opportunities to crack her crop against my back and ass. The little stings fading into lines that just further inflamed my arousal.
“You're dripping, slut,” she pointed to her boots and I could see a bunch of my pre-cum was dripping from my clit onto her boots. “Remember, you have to lick up all the cum.”
As I leaned down and licked the drips from her boots, she really went to town on my ass. I looked up as I finished, breathing rapidly from my excitement.
“Look at you, you're enjoying this, aren't you my little sissy? You like being treated like a piece of fuck meat, don't you?” she was grinning toothily and from this angle looked like she was possessed by something evil. It was a scary visage, and help me, it was one of the most arousing things I'd ever seen.
“Yes, Mistress. I love being a worthless little sissy whore,” I blubbered, biting my lip.
“Good, then you'll love this part,” she pulled my mouth back to her strap-on and shoved hard. Her cock hit the back of my throat making me gag. “Oh yeah, gag and on my monster cock, bitch.”
She kept pulling out for a moment, giving me a moment to recover before ramming her cock back down my mouth. On the third try, she slipped into my throat and drove my face into her crotch holding the back of my head tight into her. My nose pressed against her pelvis, I could really smell her arousal now. She started grinding the strap-on in my mouth, and I wondered if she was grinding her clit or pussy against the strap-on.
After several seconds, I needed to breathe but she kept holding me. I pushed softly on her, trying to get through that I couldn't breath. Finally, I was getting desperate and pushed hard. I came up coughing and panting for air.
“Did you push me, slut? I don't care if you can't fucking breathe. I'll let your stupid cunt hole up for air before you pass out, you dumb bitch, now come here,” she grabbed my head and rammed her giant dick down my throat again.
She was grinding again, pounding the cock deeper in my throat and I tried to not gag. I was also trying to not panic since I couldn't breathe again. We went like that for several minutes with me gagging on her huge dick and her grinding this beast down my throat. We hit a point where she just grabbed the back of my head and was grinding so hard, I thought she was going to break my nose. Finally she threw her head back and groaned while her whole body shook.
She held me there until she came down, then she smiled down, “Good girl.”
She let go of my head and I sat back gasping for air. She just stood towering over me, her eyes slitted as she ran her fingers over my head.
“Now, its time to torture your little sissy bits,” she nudged my rock hard clit with the toe of her boot, making me gasp. That made her eyes light up. So, she started kicking my clit with her toe, nudging it pretty hard. Then she kicked me in the balls, hard.
I groaned and fell forward, the pain surging through me. Yet, I was still incredibly turned on.
Her mocking laughter added to both my shame and my arousal. Why was I getting off on her kicking me in the balls? I started to get back up when she pulled her foot back and kicked me in the balls again. Not hard enough to damage anything, but hard enough for me to double over and see stars.
She then leaned down and began smacking my clitty with her riding crop. The leather smacked lightly, but still made my sensitive skin twitch reflexively. She kept tormenting me with her boot and crop and I didn't know which way the attack was coming from next.
Then suddenly, she loomed over me and said, “Get your ass over that stool. I want you face down and ass up, just like the slut you are.”
I obediently crawled over and climbed onto the hassock. I was able to drape my head over one side and my ass was up for easy access. I felt very vulnerable, but I was also rock hard.
She then fastened my cuffs to some hooks she had already secured to the legs of the large footstool. Apparently she had prepared for this! My wrists, thighs and ankles were quickly secured and I was unable to move even if I wanted to. My heart was absolutely hammering as she stalked behind me.
A soft whoosh was followed by a loud smack. A moment later pain flashed in my ass. A soft chuckle let me know that Mistress Nora was enjoying beating my ass. She gave me several more swats with her gloved hand before switching to the riding crop. She then mixed the fast, stinging strikes of the crop with the heavy thuds from her hand. I was squirming, moaning and trying to breathe deeply to help process the pain. She was only giving me a few moments between hits before she'd strike again, so I had little time to process. As the pain was building, I was gasping for air while my brain moved into overload.
The smacking while being plugged was even more of a mind-fuck to add in. Since each hit I'd tense and pull the plug deeper, but then I'd relax a moment and the plug would slide to the flared part. It was only an inch or two, but it was enough to make it feel like I was fucking myself in the ass. So, while the pain was making me go limp, the plug was keeping my libido at a high level.
Soon, Mistress Nora was just laying into my ass, continuously hitting my ass over and over. I could feel the spots that had been hit multiple times, and those flared with even more pain. Somewhere in the back of my mind, I realized I was probably going to have some welts or marks of some kind.
Then as suddenly as the assault started, it stopped. Nora breathlessly stepped in front of me. Her chest was heaving and her face was flushed with excitement.
“Damn slut, that was fun! I hope you enjoyed it too,” she leaned in close, waving her strap-on in my face. “You see how hard I am? Before I make you my bitch, I want to make sure you stay my bitch.”
She then stepped around behind me. I was expecting her to pull out my plug, so when she started messing with my clit and balls, I was a little confused.
“M-m-m-mistress?” I stammered.
She smacked my balls in response, “Shut up, slut. You're to speak only when spoken to.”
She began pulling hard on my balls, then it felt like she was squishing them. Then she folded my now soft clitty down and did something with it that was a bit painful. It took me a moment to realize she'd put me in some kind of cock ring or something.
She stepped back around in front of me and held something in front of my face. I could see it was a small plastic piece of some kind. It looked vaguely phallic shaped. I thought it was a gag and she was going to silence me, then I saw it had a small lock and I realized it was a chastity cage.
Nora... I mean Mistress Nora, saw the realization in my eyes. Biting her lip and nodding, she said, “Yes, that little nub of yours is going to be under lock and key. And you get out when I decide you do.”
As she stepped around me and messed with the cage and my clit, she continued. “Of course, a little slut like you should have no problem getting lots of cock to get you off.”
The ominous click of a lock made me realize I was now hers. The idea both scared and thrilled me. On the one hand being under her control meant I'd get to serve her even more, but I had no control over a part of my own body.
“Oh, yes, you really are a little slut,” she said as she pulled out my butt plug. “Oh yeah, you're going to love this. Oh and put this in your little whore mouth.”
She pushed the butt plug into my mouth. I recoiled for a moment at the taste. But there really wasn't much I could do. Nora then pushed her strapon up to my asshole, letting the head slide in very slowly. I moaned as her head pushed past my ring and then slid most of the way in.
“Oh yeah, you fucking dirty whore. Look at your hungry little hole. Oh, and if you drop that plug out of your nasty mouth, I'm going to spank your balls hard,” she then thrust hard and the rest of the cock buried in me.
I moaned into the plug, feeling my clit try to swell with my arousal, but the cage prevented that. She pulled back and then thrust hard again, picking up the pace and finding a nice rhythm that was really hitting my prostate. I was feeling even more worked up than before thanks to the cage. My chastity mistress began really pounding my ass, I could hear her breathing heavily, then she thrust deep and grunted, grinding on my ass with her plastic cock. I guessed from her ragged breathing she was cumming. She pulled out a moment later, then reached around, took the plug from my mouth and slid back into my now well-opened ass. The plug slid in easily.
“You are such a fucking sissy slut,” she laughed. “What a hungry little ass.”
She stepped around in front of me, and shoved her cock in my mouth. “Clean your nasty ass off my gorgeous black cock.”
I sucked on her cock as she pumped it in and out of my mouth. After several strokes she grabbed the back of my head and shoved the cock all the way into my throat. I gagged as she held my nose to her stomach.
“Oh yeah, you little cock sucker. Can you smell me?” she asked, looking deep into my watering eyes. “Can you smell what abusing your pathetic ass has done to me?”
She took her cock out of my mouth and quickly pulled the strap-on harness off. She turned back and sat on the footstool right in front of me. She starting running her fingers over her clit and pussy lips just inches from my face. Her scent was overwhelming this close.
As she toyed with her womanhood, her other hand lifted my chin as high as I could go it in this position. She smiled down at me. “Of course, my new jewelry has me pretty excited, too.” She held up a small key she had on a chain around her neck.
“Oh yeah,” she closed her eyes and leaned her head back as she proceeded to cum, as she stroked lightly over her clit repeatedly.
As she calmed down, she smiled down at me. “That was fun, my little pet. You do understand, your sissy ass is mine now, right? I'm not kidding around here.”
I nodded, “Yes, Mistress. I understand.”
She reached down and undid my wrist cuffs, “Good, we can have lots of fun, you and I. Unhook yourself and come kneel at my feet.”
She stalked over to a large overstuffed armchair and sat down, sipping on her wine. I got myself unhooked and made my way over to her, kneeling down. I looked up at her expectantly.
She nudged my caged clitty with the toe of her boot. “Oh that looks like its going to get uncomfortable for you, and soon. That is so fucking hot. Do you like being caged, sissy girl?”
I blushed crimson as I realized I'd go through way worse to have the chance to kneel before a woman like this. “Yes, Mistress. Its a bit tight now, but I like being yours.”
She smiled brightly, “Good girl.” She ran her hand gently over my face. “Of course, seeing that big cock taking your ass has made me horny for some cock. Some real cock. So, go up into the bathroom and put on the outfit hanging there and then do your make-up. I want you looking like a proper slut.”
“I... wait, Mistress. What do you mean?” I stammered.
She glared down as she stood up, “Are you questioning me again?”
“No, Mistress! I just don't understand,” I answered quickly.
“I know, but you're just a sissy, you don't have to understand. Just do as you're told,” she stalked off. Then looked back, “And be quick. I don't want to be waiting on your dumb ass.”
“Yes, Mistress,” I answered, my head swirling a little. What was going on now?
After she left, I made my way to the bathroom. There was a white dress hanging on a hook in the bathroom. It looked like it was going to be clingy. It had a low-cut neckline and the hem was probably about mid-thigh. So, it was a short dress that still managed to look like a slutty bridal dress.
I donned the dress then I turned to the set of cosmetics sitting by the sink. Thankfully, I'd been practicing with my make-up, but I was worried if I did it too fast, I'd look like a clown. I just needed to look like a slut, but that was much more work than you'd think it is.
I worked on getting the make-up right, but I also tried to go quick. I did up the eyes starting with some blue eye shadow. It was a nice look. I had read about doing blended and smoky looks. I didn't really want to practice with that now. Instead I focused on getting the mascara on and even. I debated trying some eye liner, but I still wasn't very good at that. I did some powder and blush on my cheeks, just to accent the highlights and give a little color. I then made sure to get a nice coat of red on my lips. They just looked bright and glowing red when Nora leaned into the bathroom.
She was grinning, “Ready to go?”
She had changed as well. She was wearing a black version of my outfit. We looked like some kind of slutty sisters or something. It was a little disconcerting, especially when she walked behind me and had me pull my hair up. She buckled a small pink choker on my neck. It took me a moment to realize it also had glittery letters on the front that said, 'SISSY'.
“Just to make sure,” she chuckled evilly. “Come on.”
She led me outside and handed me the keys, “Have you driven in heels before, sissy girl?”
“No, Mistress,” I replied.
“Well, this will be a good chance for you to practice,” she laughed and we were on our way.
She gave me directions to drive a few minutes down the road. Fortunately, I was so busy focusing on driving that I didn't really pay much attention to where we were going, or how I was dressed. We parked and Nora led the way up to an apartment building.
She knocked on a door and I was more than a little nervous about where we were and what was happening. I was so excited about what might happen that I was steadily dripping into my panties. I was also more than a little scared about where this was going. Just being out publicly dressed had my heart hammering.
A tall, handsome man opened the door, looking like he'd just stepped out a magazine ad or something. He smiled at Nora, “Hey girl! You made it.”
“Of course, I did Todd,” she responded by kissing him deeply.
He checked me out as they broke the kiss, “That's the sissy girl you mentioned?”
Nora smiled and nodded, “Yup, and she'll do whatever I want. What do you think?”
Todd looked me up and down, “She's cute. Kind of slutty, but I guess that's appropriate for a sissy. I think Tyrone is going to love her.”
We made our way over to a nearby bedroom. As we did, Nora pointed to the floor in front of the bed. I felt like an obedient pet kneeling in front of them while they made out. Todd had her top pulled down and was playing with her tits. She moaned, but also looked at me, smiling mischievously. She pulled Todd's cock out of his pants and was stroking it gently.
She then looked at me, “Well, it's not going to suck itself.”
I looked up at Todd, but he just shrugged and went back to kissing Nora's neck and playing with her tits. I knelt down and crawled over. I started working my tongue slowly up and down his cock. Hearing him moan, I kept teasing around with my mouth and tongue, but Nora had other ideas. She grabbed the back of my head, pushed my mouth to the tip of his cock and shoved me down. I gagged roughly at first, trying to open my mouth and throat, but Nora was relentless. I'm pretty sure she was getting off by making me gag.
Apparently, Todd was, too. Since he was moaning and groaning loudly, so was Nora. She grabbed Todd's hand and put it up her skirt, forcing my head down even harder. By this time I'd adjusted my angle, and opened my throat up, so his pretty sizable cock slid down my throat. I still gagged and choked on it, but not as bad.
Nora shoved me up and down several more times on Todd's dick before she pushed me back and out of the way. She then slid over to straddle his lap, guiding his cock into her. She grunted deeply, clearly overtaken with lust at this point. His cock slid all the way into her.
I felt an odd twinge of jealousy as she mounted him. I don't know why, she clearly didn't want me as her boyfriend, for obvious reasons, but the idea of her fucking another guy just inches from my face had my head swimming. The sight of them intertwined and the sounds they were making overwhelmed any slight jealousy I might have felt.
I could see both of them locked in their passion. I was just a few feet from them and I could smell her arousal. I could hear the wet squelching as she bounced on his cock. They both grunted in animal passion, the sounds of their lovemaking filling my ears. I wasn't sure what to do other than watch their fornicating.
They went for a good long time and the excitement of watching them had me straining my cage and leaking into my panties. It was better than watching a porn since I could smell them as well. After several minutes, she climbed off and went to her hands and knees. Todd climbed up behind her and took her from behind.
She purred excitedly as he grabbed her hips and really began pounding away. She beckoned me over and pulled my mouth to her tits. I began sucking on them for all I was worth. I worshiped her tits like they were my last meal and she ground my face into her chest. I could feel her heart beating as I listened to Todd hammering away at her, the sound of flesh on flesh only overtaken by her moans and my sucking on her.
They went for what seemed like hours. It was probably more like 30 or 40 minutes with Nora screaming and quivering her way through at least three different orgasms. Finally, Todd sped up and with a loud groan and grunt, drove deep into Nora. She shivered her way through a last climax as Todd came deep inside her. They sat panting for several minutes until Todd pulled out and flopped on the bed.
Todd was about to stand up when Nora sat up and said, “Hang on, babe. Sissy will clean you up. Won't you slut?”
I nodded and slid over to Todd and began sucking the cum and Nora's juices off his now shrinking cock. Once I had him completely clean, he laid on the bed and pulled Nora in close to him. Nora beckoned me over and guided my head between her legs, “Lick his cum out of me, slut. I want to cum all over your face, while you swallow his cum.”
So, for several minutes I worshiped her well-fucked pussy, his thick load of cum pouring out of her and into my mouth. I swallowed as much as I could, while still licking away at her. Apparently, she was really into it, because after I swallowed the last of his manhood in her, she grabbed the back of my head, squeezed her thighs around my face and came once again.
She sat catching her breath as I softly licked her back down. She ran her hands over my face and purred, “Very good, sissy girl. That was awesome, but you look like you're all worked up and could use some relief.” She turned to Todd, “Is your roommate still in?”
Todd nodded, “Oh yeah, he's going to love her.”
Todd threw a shirt and shorts on. Nora pulled her dress back on, then she pulled me up and we walked into the living room. We went to the kitchen and Nora said, “Get me something to drink.”
I went into the fridge, and it was mostly beer, but there was an opened wine bottle. I got that out and poured her a wine. I got myself some water and sipped that as she sipped her wine. We heard Todd coming back talking with another guy.
Todd stepped back in with an even bigger guy. The new guy gave Nora a little kiss on the cheek, “Hey Nora, so this has been your pet project?”
“Hey Tyrone, and yup, this is my sissy slut,” she beamed as Tyrone looked me up and down.
“And she's a sissy?” he looked at her disbelievingly.
“That's why she has the collar,” Nora laughed. Then to me she said, “Show him your clitty.”
I blushed scarlet, but I dutifully lifted my dress up and pulled down my wet panties to show off my locked clitty.
Tyrone shook his head and just said, “Damn... So, can I play with her?”
Nora bit her lip and nodded, “Oh hell yes. I thought you might like her. She can play with all your friends if you want, too.”
My heart skipped a beat. What did she just say? Friends?
Tyrone's face broke into a wide grin, “Oh yeah. They'll definitely love her.”
Nora said simply, “Just know, she and I have an appointment tomorrow, so I'll need her back in a few hours. Oh, and don't leave any permanent marks, otherwise she'll do whatever you guys want.”
Tyrone stepped in close to me as Todd and Nora headed back to Todd's room. I looked up nervously. Even in my 4” heels he was a good 6” taller than me. He smiled wide as he pushed me to my knees and pulled out his cock.
He was only semi-hard and was already very big. As I worked on his cock, I saw he was on his phone. He smiled down at me as he put his phone away and his member swelled to full size. He was a bit thicker than Todd, but not quite as long. Here I was becoming a cock connoisseur. Just part of the life of a sissy slut, I guess.
After a few minutes, Tyrone reached down and pulled me back up to my feet, “Come on, baby girl. My friends want to play with you, too.”
He took my hand and led me out of the apartment. Oh my! Where was I off to now? And why did the idea of a strange group of guys using me excite me so damn much?!
“You really are cute as a girl,” said Tyrone. “How long you been dressing up?”
“Well, I've worn panties for years,” I explained. “But I've only been fully dressing a few weeks.”
“Get out of here, really?” Tyrone laughed. “I would have guessed years. Maybe all your life!”
“Well, Nora is quite a teacher,” I explained.
“Yeah, so she's got you all locked up, huh? We've never had a sissy in chastity before. So, we'll see how that goes.” Tyrone explained that his group of friends were all athletes, and even though attitudes were changing about LGBTQ+ lifestyles, big school college sports was still pretty traditional, especially at state schools. So, this group of guys would have some twinks or sissy girls that they would play with quietly. Apparently their previous two play toys had left school. One had graduated and the other had changed to another school. So, they were really excited to have a new play toy. It sounds like they were going to have a party and I was the main attraction. Naturally this both scared and excited me. I was already dripping in my panties.
As we walked, Tyrone held my hand and supported me if I was struggling on my heels. He was very sweet about it actually. We came to another apartment and he knocked. Another very tall and built guy opened the door. He and Tyrone fist bumped and the new guy looked me up and down.
“This is a sissy? No fucking way,” he said to Tyrone.
“Believe it, Ken,” he said, guiding me in. “She's cute and sweet, but also very wild.”
Ken smiled at me, “You want something to drink, cutie?”
I nodded and looked at the room full of guys. They were watching a game, but everyone's eyes were on me. I blushed and got a little shy. Tyrone took my hand again and walked me into the room. He sat on a chair and pulled me onto his lap. I could feel his hard cock, pushing against my plugged ass.
Tyrone pointed around the room, “That's Adam, Lou, Carlos, Tiny and you just met Ken.”
They still couldn't believe I was a sissy girl, so Tyrone had me stand up and show off my locked up clitty. The guys were all super excited for this. They were even more excited to see my plugged ass.
“Oh yeah, I guess you're all ready, then, Sissy?” said Lou.
Tyrone laughed and held up my wrist which still had the leather cuffs on it, “This slut is all ready for anything.”
At that point the guys decided to tie my hands behind my back and tie my ankles to my knees. I was then physically picked up and placed on a futon they had ready to go. Tyrone came up and slid his member back into my mouth.
One of the other guys got behind me and pulled out my plug. He quickly replaced it with his cockhead. Even with how open I was, he pushed slowly because he was well-hung. Even with the plug and the lube it took him some time to get my ass adjusted to his monster cock. Fortunately, I had Tyrone's big cock to keep me focused.
With just my mouth free, Tyrone controlled most of the action, taking his time to slowly drive his cock deep in my mouth and then back out. Once my ass was opened up, my ass man began taking me with long slow strokes as well.
Both guys took their time laying into me while the others watched and commented about how my clitty was dripping in my panties. They also tried to decide what kind of things they wanted to do with me the next time. It occurred to me that I was going to become a complete pleasure tool for these guys, and I already had another group that was ready to take me tomorrow. Oh, the life of a sissy slut!
My moaning and grinding got both guys really pumping into me. They both had pretty impressive stamina and it took them a while to finally finish off but when they did it was a lot. Tyrone pulled out and came all over my face, pretty much covering my eyes and nose with his load.
Once he finished off another guy came in to take his place. Seeing my coated face got my anal lover worked up and he came deep in my ass. It felt like he was flooding my ass with a hose. When he pulled out, the cum was running in streams out of my ass.
However, that just made my next lover have lots of lube to slide right into my ass. Each guy took me once and then I was flipped over, my ankles were untied briefly just to be re-tied to the legs of the futon, spreading my legs wide. It also put my head at the edge of the futon, so the guys were able to really fuck my face like this. Each guy took me another time and I was treated to six more giant loads of cum. And yes, each of them were sporting a very large cock at least nine to ten inches, with Tiny sporting an 11 or 12 inch beast.
After a few hours, the guys were finally sated and Tyrone walked me back to his apartment. He held my hand while several loads of cum dripped out of my ass and dried on the rest of me. It was wild. He just chatted with me the whole way like I hadn't just been fucked every which way by him and his friends. Needless to say, my stretched ass was making me walk with wobbly legs the whole way.
Tyrone told me they'd be more prepared next time, “Some of the boys will have some toys and things they'll want to use on you. Some of the shit will blow your mind.”
“More than I already blew your cocks?” I joked.
He laughed, “You're pretty awesome, girl. You ever want to go out?”
Wait? Was he seriously asking me out? “I-I-I don't know. Would you really want to? I thought you needed to keep things quiet?”
“Ain't nobody going to know you're not a girl. We could go out any time,” Tyrone laughed.
“Well, as long as Nora's okay with it, that sounds like it would be fun,” I smiled.
Back at the apartment Nora had a good laugh at how well-fucked I looked. She made sure to get a few pics, especially of the cum leaking out of my ass and the dried cum still on my face.
She kissed Todd good-bye and Tyrone gave me a very deep kiss before we left. I won't lie, my head was spinning at how everything had gone this night
Nora offered to drive since she assumed I was pretty worn out. She was right.
When we got back, she asked if I made a puddle. When I looked down and saw the puddle of cum on the seat, Nora made me lick it clean. She laughed as I did, “Don't worry, Todd left a couple loads in me, too. So, you'll get to lick those out while I go to sleep.”
Needless to say, I spent quite a bit of time licking her pussy in her bed until she pushed me aside, rolled over and went to sleep. I basically passed out, since I was so tired from everything that happened. The problem with being in the chastity cage meant that when I got aroused through the night, the pulling of the cage would wake me each time. And getting morning wood in a chastity cage is no joke. It's down right painful.
When Nora woke up, she felt me next to her and rolled over. She looked down at me and laughed, “We need to make sure and clean your make-up off and cum off before going to bed in the future. Go clean yourself up. You look like a well used whore... which is accurate, really.”
I went to the bathroom and sure enough, she wasn't kidding. I had make-up and dried cum streaked and smeared all over my face. I washed and scrubbed several times before getting everything off. I also peed, but of course, I had to sit down since the cage wouldn't let me stand and pee.
Nora came in while I was peeing and laughed softly, “So, you have to sit to pee now, like a girl?”
I nodded, “Yes, Mistress.”
She sat and peed when I was done, “Come here, sissy.”
She pulled my face into her crotch and had me lick the piss from her. The acrid taste was bitter and very strong. She slid forward on the seat and had me fully worship her pussy again.
After a few minutes, she pushed me back and said, “Come on slut, you need to worship me more, while I tell you what you're going to wear while the boys ravage you today. I am so going to enjoy seeing you getting used like a cheap whore.” She grinned like the Cheshire Cat. I thought the boys at the LARP might be in more trouble than I was when I heard her plan. It was going to be another wild day.