An Unusual Bachelorette Party Pt. 01

I never wanted a typical bachelorette party. This was going to be my second marriage, I'm in my 30's, and I'd long since grown out of my hard partying.

I'd met Sir at a local street fair when we were both perusing the vintage record booth. I'd felt a hand graze my ass under my sundress and turned around ready to start yelling, but then I'd gotten a look at him and decided to see where this would go. He was tall and muscular, easily in his 50's, and was smirking at my reaction. He jerked his head towards the bar on the corner and I went without a word. I was so shocked at myself, I never did things like this. But here I was, following this stranger who'd groped me.

He led me to a booth in the back corner, and only once we sat down did he start to speak.

"Well aren't you the sexiest looking thing here... what's your name kitten?"

I just stared for a minute, once again dumbfounded this was actually happening to me. And trying to ignore the way my nipples hardened when he called me kitten. "Uh.. h-hi, I'm Sara. What do you want?" As if I wasn't already sitting with him. Stupid.

His hand landed on my thigh then, under the table. "Hi Sara, I want to get to know you... intimately." He slowly brushed his fingers along the inside of my thigh, and my legs parted slightly more without me consciously choosing to do so... I think.

"I'm engaged!!" I managed to sputter out, hoping that would convince him AND me to get up and leave. I wasn't looking to be unfaithful, and there was no way he'd missed the giant rock on my finger. He chuckled at me, shaking his head a little bit, clearly amused.

"I can see that kitten. The thing is, I don't really care. I'm married, myself. But I knew the second I saw you in that booth none of it mattered, and I had to have you. You haven't tried to pull away, you even parted your legs for my hand, so clearly you want a little something too. I bet that pussy is drenching your panties right now, isn't it?"

I flushed at his words, because he wasn't wrong. I was dripping wet at this man's touch, and both eager and ashamed that I wanted him to touch me more. A little whimper slipped out, and he grinned as he slid his hand further up my thigh... right as his fingertips were about to graze my core, the waitress showed up. I jumped and tried to close my legs, but he just clamped his hand down holding me in place.

"Good afternoon folks! What can I get y'all to drink?" She didn't see what he was doing to me, the table blessedly in the way.

"I'll have a whisky sour, and she'll have a vodka cranberry. Thanks!" The waitress nodded, and walked off to the bartop to put our order in. My first reaction was to be indignant. "I don't like vodka, actually. I won't drink it."

"Yes you will kitten, trust me." He growled a little, loosening his grip on my leg.

I wasn't entirely sure what to say to that, so I just nodded. He went back to rubbing the inside of my thigh, not quite getting close enough to graze my core, and smirked as I shifted in my seat.

"So kitten, I can see that there's a naughty little thing inside you, just waiting for the right man to bring it out. And I think you want that too, don't you?"

God help me, but I actually thought about it for a minute. Maybe... maybe just this once. I could be wild and free again, just for a day, then go back to my normal life and pretend this never happened. I'd been so good for so long... and I admitted to myself that I was bored. I loved my man but... he couldn't treat me like the naughty slut I wanted to be. Okay, fine. I'd call it a bachelorette party. Crazy things happened on those trips right?

"Yes... yes I do want that. Just this once. Just for today."

"Answer me with 'yes Sir', kitten. And we'll see about what you want after today."

The waitress came up with our drinks and he stared me down until I took a big gulp.

"Good girl, kitten."

"Thank you... Sir." Saying it that first time made me ache, and I spread my legs just a little wider for him. He pretended everything was normal and started chatting at me while he slipped his fingers all the way up my dress and into my panties. Moving the sodden lace aside, I moaned quietly as his fingers slowly circled my swollen clit. He inhaled sharply when he felt how wet I truly was, and I saw his eyes darken and his cock harden in his jeans. He slipped a finger into my tight hole, leaning in to whisper in my ear, "I knew this pussy would be perfect for me. I bet you want to cum already, don't you?"

I was in a daze, shocked at my own sluttiness, at my body's response to him, and how badly I wanted more. When I didn't answer him, he swiftly pulled his finger out and roughly pinched my clit. I had to bite my lip hard to keep from crying out, and he pulled his hand away. I gasped at the sudden lack of sensation.

"I expect you to answer me when I ask you a question, kitten. Now finish your drink, it's time to go."

"... yes Sir," I all but whispered, and choked down the rest of my cocktail. "That's better," he murmured, throwing a couple bills on the table and dragging me by the hand out of the bar. My pussy still aching, I didn't think to ask where we were going until we got down the block, around the corner, and into a side parking lot. We walked up to a big pickup truck, and he opened the back door. "Get in, kitten. Now." I obeyed quickly.

He closed the door, and once he got behind the wheel, he met my bewildered expression in the rearview mirror. "Buckle up, take off your panties, and spread your legs so I can look at that pussy the whole way home."

"Yes Sir," I breathed. Following his directions earned me a "That's my good girl" and he smiled at me when he saw my pussy gush at his words. "Keep that pussy spread, kitten," he said as he pulled out of the parking lot. I wasn't keeping track of where we were going, but about 10 minutes later he was pulling into a garage. Once the door closed all the way, he turned around in his seat and roughly shoved two fingers into my dripping hole. I cried out at the intrusion, then again louder when his thumb started insistently rubbing my clit. I swiftly reached the point of orgasm but right before I came, he pulled his hand away. I whined in protest.

"Mm what a responsive little cunt. You'll be begging me to cum by the time I'm done with you," he stopped and licked some of my wetness off of his fingers, "Your pussy tastes delicious kitten; lean forward and finish cleaning off my fingers with your mouth." I did like the way my pussy tasted, so this I could do eagerly. He shoved his fingers in my mouth and I licked and sucked all my juices off while he groaned his approval. "You're going to be such a good girl for me aren't you?"

"Yes Sir," I tried to say around his fingers still in my mouth. He nodded his approval, withdrew his fingers, and got out of the truck. He opened the door for me and helped me out, but when I turned to look for the door into the house, he grabbed my hair and pulled my head back, pulling me backwards against his chest. He pulled the front of my dress down, exposing my tits, and he started groping them. As he was rolling a nipple between his fingers, he lowered his mouth to my ear and said, "Once we get in the house, I'm going to use you however I want, and you're going to love it. But I need you to know that you can leave at any time, and if you tell me to stop, I will. Do you understand, kitten?"

I could barely form a coherent thought with what he was doing to my breasts, so I just nodded. He sharply smacked my left tit, making me yelp.

"I need your words, I need to hear that you understand and consent. Now I'll ask again, do you understand?"

"Yes Sir, I understand and consent."

"Good. Now the door is up here on the right. Go inside and kneel next to the couch, and wait for me there." He released me at the last word, and I did as I was told. I knelt there without my panties, with my tits out, my pussy drooling onto the floor beneath me, and still very fucking confused about how I'd let myself get here. Several minutes passed and finally I heard the door open and his footsteps come up behind me.

"What a pretty little slut you are, Doing as you're told. Let's see if your mouth is just as slutty as your cunt. Look at me and open your mouth." As I looked up, I saw a very thick hard cock in front of my face and my mouth dropped open. He grabbed my hair again and swiftly started fucking my mouth. I choked a bit at first, which seemed to excite him because he started thrusting harder. Drool was running down my chin, and I was starting to zone out and just get into the rhythm. "Fuuuuuck your mouth is so good, but I'm not ready to cum just yet. Use your tongue to worship my balls."

His hands still in my hair, I leaned in and started licking and sucking his heavy balls. I looked up at him for approval, and he just nodded as he was groaning. "Oh you're such a talented little slut; I knew you would be. Does it make your cunt drip worshipping me like this?" I whined at his words.

"Yes Sir," I said with my mouth still full of him.

"Good girl; I'll need to check it then. Kneel in front of the couch and lean over it, resting your chest on the cushions, and spread your legs for me." Once I got in position, I felt him pull the bottom of my dress all the way to my waist, then the drag of his fingertips up the inside of my thighs, just like at the bar. I whimpered with need, wiggling a little to try and encourage him to get there faster and he just chuckled. "Oh my poor little slut is so needy! I can feel your wetness on your thighs. Did you know you were going to be such a good slut for me today?"

"No Sir, I didn't know. Thank you for your praise." I'd been in a few D/s relationships in the past, and started falling back into those habits with the way he was treating me.

"What a polite slut you are now! No more of that brattiness from the bar. Good girl." With that, he finally dragged his fingers through my center and I moaned embarrassingly loudly. "Your pussy is sloppy wet for me. Should I make you cum now?"

"Please... please Sir let me cum for you." He teased my clit slowly with the tip of one finger and I was already so aroused that I nearly came right then.

"Not yet kitten. Not yet." He took his hand away and I nearly screamed in frustration. "Stay right there." I stayed put, seething as he walked away. I heard a door open somewhere in the house, and then his footsteps returning. "Have you ever had that ass played with?"

"Only small toys Sir." He can't be thinking what I think he's thinking... right?

"Good thing I brought the small one, then. Need to get it nice and wet first, though." Before I fully register what he means, I feel his tongue on my ass and something fucking my pussy. I can't help myself, I thrust backwards against him, wanting his tongue and what I now realize is the plug deeper.

"My good little slut, so greedy for more. Now, are you ready for this plug in your ass?"

"Yes please Sir," I moan, and I feel the warm metal start pushing into my tightest hole.

"Good girl, relax. There you go, how does that feel?"

"Um... very full Sir... I think good?" It'd been so long since I'd had a plug in my ass, I was trying to get reacquainted with the sensation. I shivered when I realized I was basically naked in this man's living room, spread out and plugged with a dripping cunt... and all I wanted was for him to fuck me. "Sir... please please may I cum for you?"

"What pretty manners you have now, kitten. I think it is finally time for your first orgasm. Are you ready?" That was all the warning I got before his cock slammed into me, all the way to the hilt. "The only way you're going to get this first orgasm is all over your new Master's cock. That way you know who this pussy is going to belong to from now on." His filthy words and the fullness of being fucked with the buttplug in, couple with all the teasing and edging earlier finally did it. I screamed as my climax tore through me, my body arching and bucking and shaking like I was being exorcised. After what felt like an eternity, I went limp and he slowed his thrusting.

"Thank you Sir," I gasped. I had no idea where this could even go after an orgasm like that. How could that be topped?

"You're so beautiful when you cum for me, kitten. What a good girl." I whimpered when he pulled his cock out of me, and he lifted me up onto the couch, pulling my dress all the way off me. "I know you can cum more for me, and I want to taste my pussy. So give me another, and I may finally let you have my cum." It wasn't a request. My body still felt like jello but I spread my legs and held my thighs to keep myself bared for him.

"This cunt looks delicious; dripping your cum and swollen from my cock." He leaned over and dragged his tongue up my center, and my back arched in response. He hummed his pleasure as he started sucking my clit, and I gasped as he started toying with the plug in my ass. He slid two fingers from his other hand into my free hole, teasing my g-spot. I didn't think I'd be able to cum again. I never have been, I always thought something was wrong with me. But before long, I felt release gathering, and he could feel me clenching around his fingers. He added a third, pushing and twisting the plug, sucking harder on my clit, and I was embarrassed by the sounds leaving my mouth.

"That's right my little slut. Give it to me. Now." And with that, another climax screamed its way through my body. "Open your mouth, clean up my fingers." Sleepily, I sucked and licked at his fingers until all my juices were cleaned off. He leaned up and sucked each nipple, eliciting more gasps and moans.

"You're doing so well for me, kitten. Thank you."

"Thank you, Sir." I all but whispered it, already spent but somehow needing more.

"You can't be falling asleep on me, we have so much more to do. Let's wake you up some, shall we?"

I struggled to sit up, wrung out as I was. He dropped onto the couch next to me, and pulled me over his knees.

"I think a spanking should do it, and it'll chase away any ideas of bringing back that bratty attitude. I'll say...20. And you'll need to count. If you lose track, we have to start over." He gave the plug a little twist and tap, then smoothed his palm over my backside. There was a brief moment of stillness and then whack!

"One!", I gasped out, my ass stinging. I felt the plug shift at the impact, my core clenching in response to the sensations. I felt his fingers trailing back down to my pussy, spreading it wide open.

"Well, I didn't think you could get any more drenched for me, kitten... but look at you. I bet this needy little hole will be drooling all down your thighs by the time your spanking is up." And with that proclamation, smacks 2-20 came. Alternating sides each time, sometimes taking a moment to toy with the plug, sometimes to spread my pussy open to see just how my juices were flowing. I was half out of my mind with need by the time he was done, my ass burning and my core clenched and aching for release yet again.

"You did so well for me, what a good little slut you are." He praised me while running a soothing hand over my hot skin.

"Thank you, Sir. Glad to have pleased you." I felt his hard cock pressing into my side as I responded, and got an idea. I wasn't just going to lay around and wait for him to decide what to do with me. His fingers were very slowly and shallowly teasing my hole, laid over his lap as I still was, so I wanted to find a way to get what I needed now.

"Sir... I was wondering..."

"What's on your mind? I'm dying to know."

"I was hoping... maybe I could ride your cock now? Let you sit back and have me do the work?" I desperately needed to be filled again and if I could get him to relent enough to let me take over, I knew I could find a way to climax. Then maybe I could think straight again.

"I think you've earned it, for a bit. Take my pants all the way off, first."

He helped me slowly get up, and I did as he asked. He held his cock straight up as I straddled him, making it easier for me to slide all the down. When he was fully inside me, he reached around and pushed on the plug, making me gasp and writhe.

"Thank you, Sir", I choked out.

"Good girl, now ride your new Master's cock," he grinned. As I started to slowly find my rhythm, he tilted his head forward and started to suck on my nipples, grazing them with his teeth. His left arm stayed wrapped around me, playing with the plug. I instantly clenched around his cock, and I saw the look in his eyes when he realized that I would cum from all of the stimulation... and that that was exactly what I was after.

"Oh no no. Now I thought that spanking would help clear all those naughty thoughts out of your head. Guess you need a bit more of a lesson. You're not going to get to orgasm until I tell you to, I thought you understood me. Now we're really going to have to do this the hard way... but at least I'll be having fun."

With that, he grabbed my hips and set a new, more aggressive pace. Once I picked it up, he smirked at me and went right back to toying with the plug and sucking and biting my nipples... but then he slid his right hand between us, where my clit could rub against it as I was riding him. When I started whimpering and moaning louder, he removed both hands and leaned back. The loss of sensation made me cry out.

"Sir... please I need..." I couldn't bring myself to fully say it, hoping maybe this wouldn't last too long and he would give me the release I was desperate for. He just laughed at me, watching me bounce on his cock, and then went right back to it. Off and on, teasing and taunting, stimulation then withholding. I lost track of how many times he went back and forth, but I was incoherent by the point he decided it was enough. I was sweating and panting, my thighs burned, and I was fully in subspace.

"Do you understand now, kitten? You're just a pretty little slutty toy for me. And that's exactly what you need, isn't it?"

"... yes... Sir", I managed to say, mumbling.

"I think that greedy little pussy has had enough for now, hasn't it? Let's see how that ass is doing." I could only nod as he helped lift me off his lap, then led me through to the kitchen.