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From Stripper to Hooker

Category: Group Sex
02.07.2017
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I’d been stripping for about 6 months. It wasn’t my first choice, but I’d been unable to find a job since graduating with an engineering degree – it seems people just couldn’t handle the idea of a pretty, female engineer.

It was an ok gig, and it more than paid the bills. I certainly didn’t get off on it like I hear about with some girls – it was just a job.

One evening after my shift, the club manager called me into his office. He told me there was a message on the office answering machine the day before asking about hiring a stripper for a private party. He said they didn’t do that (something about insurance), but I could have the number for $50 if I wanted a little side work. I’d heard other girls mention this arrangement, so I was pretty sure he wasn’t scamming me, and I figured I could probably make good money doing the party in less than an hour, then still make my shift at the club, so I handed over the cash, and he gave me a torn piece of paper with the name “Mike” and a number.

I called the number from the club payphone and arranged to meet Mike at a coffee shop the next morning.

Next morning at 10, I walked into the coffee shop, and immediately spotted the baseball cap Mike said he’d be wearing. I got myself a coffee, and hung around a while. Once I was comfortable there wasn’t anything weird going on, I went and sat down opposite him. He made to stand up (like a well-mannered gentleman), but I waved him down again.

I smiled and said, “Hi Mike, I’m Candy – how are you?”

He smiled back and said, “I’m good – nice to meet you!” He seemed like a normal guy – my creep-detector hadn’t gone off.

“So tell me about the party,” I asked.

“Well, it’s for my friend Dan’s 21st, and it’s this Saturday. it’s just going to be small – only 5 of us – we’re the only ones from college still in town, and he’s flying home Monday for a big party back home. We’re not really into clubs or anything, so we told him we’d just stay in and give him his first legal drink and play video games – then we’ll surprise him with, well, you!”

It sounded good to me, so we made arrangements – price, address, time etc.

I was about to get up and leave when he said, “There’s one more thing”

“Yes?”

“Well, um, this is really awkward, but, um,” he lowered his voice, “would you be willing to have sex with him?”

My jaw dropped.

“I’m sorry,” he stumbled. “I didn’t mean to offend you! I wasn’t implying that you would because of what you do! I’m so sorry! Please forget I asked! It’s just that he’s a virgin,and he’s gonna be 21, and that just isn’t right, and he dated this girl for years, and she wouldn’t because she was religious, and then she cheated on him and did it with someone else, and well…” he petered out.

I composed myself. I’d always considered prostitution a perfectly acceptable career choice for a woman, (as long as it was really a choice), but of course I was better than that. Well, here was a chance to put my principles where my mouth was.

I said, “Ok – it’ll cost -” and I was going to say that same again as the dance, but my scumbag brain jumped in and figured that if I named an outrageous price, I could kid myself that I would’ve done it, but they weren’t willing to pay what a girl like me was worth. My mouth said 5 times what I charged for the dance.

“That’s great.” he said without blinking.

Well, shit.

That saturday, since I was going to make so much in the evening, I decided to treat my best friend, and we went and got manicures, had lunch, and – most importantly – went underwear shopping. She knew I stripped, of course, but I didn’t tell her about the other thing. Maybe afterwards, if it went well…

I went home and took a long shower and shaved my pussy even more carefully than I do most days (and I do shave every day I dance.)

Then I put on my new underwear – dark red silk g-string and bra with little black bows in front and black hold-up stockings with beautiful lacy tops. I was going as the “severe school-mistress”, so I put on a pearl necklace, and dressed in a tight black skirt to just above the knee and a severe, crisp white blouse buttoned all the way up to the neck. I finished off with stilettos in the same color as the panties, and lipstick to match. I put my long black hair in a tight ponytail. I made a mental note to try to find a cane and horn-rimmed glasses for next time. (but you can imagine I have them if it makes this better for you 😉

—————————-

I knocked at the apartment door – suddenly I was really nervous – this was happening!

Mike opened the door almost immediately – “I’m really glad you came,” he whispered. “We only let him have one drink so far, so it should work. He’s the guy sitting on the couch.” He handed me a thick envelope, and while I counted the cash, he went back into the living room and started the first song we’d agreed.

I walked into the room, and right up to Dan. I pushed his knees apart with my right foot, then planted my stiletto between his thighs, pushing the toe under his crotch. I leaned in close to him and put on my best Marilyn voice: “Happy Birthday, Baby – I’m your present!”. He looked stunned and stared at my stocking top – I wondered if he caught a flash of red panty, and I pushed myself back upright and began dancing.

The other 3 guys were standing, gathered round, grinning – “Hello boys,” I vamped, “ready for the show?”

I gyrated in front of Dan for about a minute, thrusting first my chest, then my ass at him, sometimes with my arms above my head, sometimes pushing my tits up and together so the blouse buttons strained, sometimes pulling my skirt up far enough to show a little bare thigh. Then I stopped, facing him, and slowly unbuttoned my blouse. He was mesmerized.

I tossed the blouse at one of the other guys, then danced some more, shaking my tits in front of each of them. At one point I pulled out the hairband and let my beautiful hair fall to my shoulders.

I moved back over right in front of Dan, with my back to him. I looked over my shoulder down at him.

“Unzip me!” I commanded.

He unzipped my skirt, and I stepped back to the center of the room before letting it drop to the floor, and kicking it aside. One of the guys muttered, “Oh my god, that ass!” I felt a tingle in my pussy that I’d never felt dancing up on a stage – this was amazing!

I danced a little more, stroking my hands over my thighs and my ass, sometimes between my legs and over the top of my boobs…

I sank to my knees, then lowered down until my elbows were on the floor, presenting my ass to Dan – the g-string didn’t really cover anything, and I heard him suck in his breath. I wondered how hard he was.

I got up on my knees again, facing him, and slowly pulled my bra straps off my shoulders, then I rose to my feet and reached behind me to unclasp the bra. I kept my left arm across my tits as I tossed it aside, then I straddled Dan’s lap. With my right hand, I pushed him back, then slowly uncovered the twins. He stared, his mouth hanging open, as I stroked my tits and rolled my nipples with my middle fingers until they were rock hard. I have really nice, firm, pert tits, and I wanted to make sure he got an eyeful!

I pushed up off him again, and danced around the other 3 guys, making sure to brush my boobs against their backs, then turned my attention back to Dan. I slowly moved around in front of him and teasingly ran my thumbs around under the waistband of my panties. I made to pull them down a few times while dancing around the room again, then finally stopped in front of Dan.

“I can’t seem to get these off, Dan – will you help me?” I breathed. In a hurry, he came towards me off the couch, and I pushed him down on his knees in front of me. He tugged the panties down, but I kept my legs closed tight, so he had to work for it. As I stepped out of them, I turned and bent over, so he he got a really good look at my pretty, shaved pussy from behind, and I wanted a cock in there so badly!

I slowly laid back on the floor, then raised my hips up and moved them in time to the music, whilst stroking my pussy. I was wearing just stockings, heels and a string of pearls, and I felt like a goddess, in complete control of these guys!

I turned over a few times, and spread my legs wide, making sure they saw all of me, every intimate, wet little fold. I dipped my fingers inside myself and licked them, and stroked my ass and boobs. I noticed all the guys’ crotches were bulging, and I longed to be filled…

I jumped up and grabbed Dan’s hand – “Come with me, baby, and let’s get you your real present!” I led him into the bedroom…

As he closed the door behind us, I threw myself back on the bed, my legs spread wide, and ordered him, “Fuck me! Now!”

In a flash, his pants were round his ankles, and he was on top of me. It took him a couple of attempts to get inside me, and from the groan he let out when my pussy closed around him, I knew he wouldn’t last long. I pulled his t-shirt off him, and scraped my fingernails up and down his back, and lifted my legs so the heels of my stilettos pressed against his ass.

I began whispering in his ear, “Your cock feels so good! Fuck my tight little cunt! Spray your hot cum inside me!” Well, that was all it took, and with an almighty groan he began shudder as he came. I clenched my snatch as tight as I could to hold him inside as long as possible, but pretty soon he rolled off me, panting.

I got up and finished pulling his pants off, then lay down next to him.

“Well, how was that?” I asked.

“Fucking unbelievable! Sorry I was so quick… did you know that was my first time?”

“I think someone mentioned it…” I smiled.

“You’re fucking incredible – all I could think about while you were dancing was how much I wanted to fuck you – thank you!”

“You’re very welcome!”

We chatted a little more – he told me about college, his plans for his career, that kind of thing. While we were talking, his hand wandered to my breasts and gently fondled them. I moved up so they were in his face, and he began kissing and sucking my nipples.

I asked him, “What’s the furthest you’ve been before this?”

“My ex used to let me feel her tits, but that’s as far as it went – hers were nowhere near as nice as yours.”

“So you’ve never touched a pussy?”

“No…”

“Wanna explore…?”

I opened my stocking-clad legs, and he moved down between them. I could feel his breath on me as he parted my lips with his fingers. He ran them up and down a few times, gently squeezing and tugging on my labia. I reached down and pinched around my clit so it stood out.

“That’s the magic button,” I said. “Mine normally hides under that little hood, unless I’m turned on like this.”

He brushed his fingers slowly across it. “Yes…” I said, “Take it gently, it’s incredibly sensitive… now slip your fingers inside me.”

He did, and felt around inside my pussy.

“Now, curl them up towards the front – feel that firm, rough patch?”

He nodded.

“That’s the g-spot – you can massage that while you’re licking a girl’s clit.”

He took the hint, and ran his tongue across my clit, then sucked on it tentatively.

“Like that?” he asked.

“Yeah, that’s good, but remember, every girl is different, so try different things and feel her reactions.”

He practised a little more, sucking and licking and stroking, then I sat up and pushed him back down – “Ok, time for your first blow-job!”

“But I’m not hard again yet…”

I straddled him, pushed my tits against his chest, and kissed him full on the mouth, deeply, hungrily, biting his lips and sucking on his tongue.

I felt his cock stiffen between us.

“There you go!” I laughed.

I slid down his body, giving one of his nipples a quick bite on the way, and began kissing around the base of his cock. I gently took hold of his balls and rolled them around with my fingers. He moaned. I quickly unsnapped my pearl necklace, and wrapped it around his cock, then gripped it firmly and moved it up and down, while pressing my fingertips into the base of his cock under his balls.

“Oh my god!” he groaned.

“Good, huh?” I said, “And you haven’t felt anything yet!” And with that, I took the head of his cock between my lips, and ran my tongue across his frenulum.

“Oh my fucking god!!” he cried out, and gripped my head with his hands, “oh god, that’s incredible!!”

I slowly pulled the pearls off his cock, then licked up and down the shaft and took one of his balls in my mouth and sucked for a while, and rolled it around with my tongue, while stroking him up and down with my hand. I could feel he was close to cumming, so I backed off and took a firm grip of the base of his shaft until he got it back under control, then I started sucking again. I scraped a fingernail down the seam of his ballsack, then across his taint, and he started making funny little high-pitched sounds, so I slowed down again, and instead enveloped his cock with my tits, resting one of them on his balls, and then rubbing my nipple across the tip.

“I wanna taste your pussy again,” he panted, so I turned round and straddled his head, and he grabbed my ass and buried his tongue in my cunt, and licked up and down, even swirling my asshole. I pressed my fingers against the underside of his cock and massaged upwards, forcing a big drop of precum into my mouth.

I circled the head of his cock with my tongue, probing inside a little, running my lips up and down, whilst stroking the full length with one hand and massaging his taint with the other…

I felt him building again, and decided to let him cum. I speeded up my stroking, then felt his balls clench tight, so I pressed my fingertips into his urethra at the base of his cock, and held the cum back for a second. He cried out, and I let go, and was rewarded with a gush of cum into my throat. He dug his fingers into my ass in ecstasy and his hips bucked up against me, as I sucked and swallowed for all I was worth, until I felt his grip on my cheeks relax, and I let go his exhausted cock.

I climbed off and stood by the bed. He lay there, spreadeagled, his eyes closed, his spent cock laying back on his stomach.

“That’s definitely best bj I’ve ever given,” I thought.

I went in the bathroom and cleaned myself up. All my clothes were in the living room, so I wrapped myself in a large towel and went out there, leaving Dan apparently asleep.

Someone new had arrived – a pretty blonde was sitting on the couch. I sat down next to her and said, “Hi”.

“Hi yourself, I’m Stacey,” she said – she nodded towards the bedroom door – “did he enjoy himself?”

“I think so,” I smiled, “nice guy”.

“Yes,” she said. “I suppose Mike told you his ex treated him like shit, so we decided to get him something special.”

There was a pause.

“So,” she said, “can I see what he got, since I missed the show?” She gestured towards my boobs.

I was a little surprised, but I figured I had nothing left to hide from these guys, so I let the towel drop away from my chest. Before I knew it, she had leaned over and taken my nipple in her mouth!

“Hey!” I exclaimed.

She looked up at me – “What, did he make you cum already?”.

“Well no,” I said, “but…”

“Well then, let me…” She carried on licking my nipple, and stroked the other one with her hand.

Kissing boobs was the furthest I’d ever been with another girl, and I was curious to see how it felt. If her work on a clit was anything like her work on a nipple, I was in for a good time, and my cunt certainly had some unfinished business!

I leant back on the couch and let my arms drop to my side. She opened the towel up completely and moved down between my legs. She started slowly kissing up my inner thighs, working teasingly towards my pussy, and pulled me down to the edge of the couch for better access. She licked all the way around my pussy, over my thighs again, and even flicked her tongue across my asshole, she was so soft and slow and sensuous, it was killing me – I just wanted her to touch my clit! She began to work her lips and tongue up and down my labia, and she swirled around my clit, but never close enough…

“Please…” I murmured, “please…”

Finally, she put her lips over my clit and sucked it in – I moaned loudly, and started stroking my nipples… She licked and sucked, and pressed hard and soft with her tongue, sometimes running up and down and into my pussy, then she worked two fingers inside me and found my G spot – this was the best head I’d ever had!

I’d had my eyes closed all this time, but when I opened them, I saw the three other guys standing around, watching, almost drooling.

“Hey!” I laughed, “No watching for free! I want to see cocks!”

Within seconds, I was surrounded by hard cocks being stroked – what a turn-on, I was nearly there!

“I want you guys to cum on my tits,” I said, pushing them together and pinching my nipples. The guys all got up on the couch and started pumping even harder. Stacey was working my pussy like there might be gold in there, and as the first splash of jizz hit my tits I went over the edge. I clenched her fingers so hard I thought I might break them, and let the tidal wave of orgasm wash over me, electrifying me from head to toe. It just kept coming, and Stacey sucked my clit even harder, and I felt the next splash of cum across my tits, and the wave rose again and I grabbed her hair and pulled her into my cunt as hard as I could and wrapped my legs around her, and she licked and sucked faster and faster, until I thought I might die and I pushed her head away and she pulled her fingers out and gently stroked my pussy lips as the orgasm subsided…

I laid back in a trance as she gently started kissing all over my belly, and then moved up and started licking the cum off my tits. Even after all that my clit still responded when she gently bit my nipples, and I thought I might actually be able to go again…

When she had finished cleaning up my tits, she came all the way up and kissed me full on the lips – the mingled flavors of her sweet breath, her strawberry lip gloss, the cum and my pussy juices seemed like the greatest thing I had ever tasted. I kissed her back hard, and our tongues explored each others mouths. I slid my hands up under the back of her t-shirt and unsnapped her bra, and felt her breasts drop onto me, larger than mine. She broke the kiss and pulled her t-shirt off, then leaned back in with her tits in my face. Her nipples were darker than mine, and rock hard, but her boobs were so soft and delicious, and I lost myself in them, kissing and licking.

I reached down and unsnapped her jeans. She wriggled them off, and I rolled her over so she lay across the couch in just her pink panties, and I kissed her passionately on the mouth and neck, and worked down to her boobs and nibbled and sucked and squeezed and stroked, and I kissed her belly and her hipbones and then gently kissed right between her legs on the damp patch on her panties… her knees were up around me, and I kissed them, and her feet and her thighs, and then back to her panties. I pulled them up tight, so the cotton disappeared between her shaved lips, then slipped a finger under them behind her pussy so I could draw the cotton back and forth across her cunt, pulling side to side so it flicked her clit. She groaned loudly, and I lifted her legs and pulled the panties off, then I kept them taught between my hands and ran the fabric up and down her pussy. I spread her lips with one hand, and pushed my panty-covered fingers into her hole, gradually stuffing the panties in there. Once only a tiny loop was showing, I squeezed her lips together and began to tug on the fabric, pulling her lips back and forth, but not letting any out. I licked up and down her labia, then sucked her clit as deep into my mouth as it would go, flicking it with my tongue.

I was crouched down between these beautiful legs, with a hot cunt in my mouth, but I wanted more.

I looked up.

“Anyone that’s ready can fuck me!” I said to the room in general, and within seconds I felt hands on my ass and between my legs. I hard cock pushed against my pussy, then slipped inside – yes! This is what I needed – I was now the filling in a heaven sandwich! I didn’t look around – it was so sexy not knowing who’s cock was inside me…

“Bite me!” Stacey panted. I scraped her clit with my teeth, and she moaned.

“Oh yes, more!” I kept at it, and slipped my fingers inside her with the panties and massaged her from the inside.

As I licked and sucked, I gradually started to pull the panties out.

“God, your cunt is delicious,” I moaned, as the guy behind me stepped up his pace.

As the panties snapped out, I felt Stacey begin to cum. I licked harder, and rubbed her g-spot faster. She moaned and writhed under me, and I quickly moved backwards and grabbed a hard cock that was right next to my face, and guided the guy into her.

“Oh god yes!” she cried, “fuck me so hard!” He started to pound her, grunting.

I moved backwards until I was over the edge of the couch, still being fucked hard from behind, and I felt his fingernails dig into my ass cheeks as he unloaded with a loud moan. I grabbed his cock as hard as I could with my pussy, and he twitched, trying to keep fucking until he couldn’t take it anymore. He pulled out, and immediately another cock slipped inside me, slightly larger. I settled in, enjoying the feeling of not having to do anything, but then Mike lifted my head and slipped onto the couch under me, guiding his cock into my mouth. I sucked hungrily, realizing that the guy inside me must be the birthday boy – good for him!

Just then I felt pressure on my asshole – I looked up over my shoulder at him.

“Take it slow and gentle – help my hole relax first, ok?” Ha! He’d gone from virgin to trying to fuck a hooker in the ass within an hour!

As I sucked the cock, Dan’s fingers gently worked my asshole, even as his pounding of my pussy didn’t miss a beat. I felt him gradually open me up wider over a couple of minutes, until I twitched my ass up at him to signal I was ready. His fingers pulled out, and were replaced by the head of his cock.

“Now slowly!” I cautioned, returning to the cock in hand, massaging his balls and stroking up and down the shaft.

Dan slowly pushed in, stopping halfway to make sure it was ok. I pushed back against him, and he slid all the way in, until I could feel his balls on my pussy.

“God that feels good!” I moaned, with a mouth full of cock.

The guy I was sucking was clearly watching, and it was too much for him – he grabbed my boob hard and started spraying cum into the back of my throat. I kept sucking until he begged me to stop, and I let his rapidly softening cock slip from my lips. He stayed where he was, and I kept fondling his balls, my head resting in his lap, as my ass was fucked. I wished I had a cock in my pussy too, and I made a mental note to make that happen some day. I imagined it was happening right then and there, and my hand went to my pussy and started working furiously. Of course, I’m the expert on rubbing my clit, so it didn’t take long before I was bucking under Dan’s weight, and he let his third load of the evening go inside me with a groan.

By this time, the guy fucking Stacey had come too, and we just all lay there in a sweaty, exhausted, happy pile.

I never found my silk panties again. I hope Dan got them, but I suspect Stacey.

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