After hours

Chapter 29:Lucky Winner



“I’m DJ Mary, and a computer once beat me at chess, but it was no match for me at kick boxing,” Mary said, starting the show.



“A While back, Cynthia announced that the grand prize for Buena\'s Password was a date with her, and tonight’s guest is that lucky winner,” Mary said, sounding slightly jealous. “It’s the very lovely Caroline, the mother of May, who was here just last week.”



“Hi, Mary! I’ve become a really huge fan lately of your show,” Caroline said happily.



“Just one thing I’m wondering about: I thought you were married to Norman?” Mary said.



“Well, I do love him, and I like men in general but I’ve always been bisexual, and we have an open marriage. I know that he’s been with a few of the girls who come to challenge him,” Caroline explained.



“Well, I’m only interested in women, so let\'s hear the details,” Mary said.







I always enter all of Buena\'s Password shows, but I never won one until just a few week ago. I got a phone call telling me that I had won, and of course, like just about everyone else in the world, I’ve got a bit of a crush on Cynthia, so I was super excited for the day of the date. So I bought a new dress just for it, a slinky low-cut strapless red satin one with a slit up the side that stopped just a few inches from my hip, and a pair of shoes, really nice stiletto heels. And just to make everything better, I had a pedicure as well, because I knew how much Cynthia likes feet.



When the time finally came, I went to the hotel Cynthia was staying at and met her in the bar. I was surprised to see that she had dressed up as well. Instead of her usual outfit, she was wearing a black halter-top and matching mini-skirt, and knee-high boots with several large silver buckles. Her hair was done up as well, she had it all pulled back into a long ponytail. She looked so good that I wanted to just take her right there with everyone watching, but I kept myself under control. She was kind of staring off, not looking at anything in particular. I walked up to her.



“Hello, Cynthia,” I said softly. She turned toward me and smiled. It was then that I noticed she was wearing a bit of makeup. Not much, just the faintest trace of eye shadow and lip gloss, which made her even more beautiful than she already was, if that\'s even possible.



“You must be Caroline. It a pleasure to be going out with someone as lovely as you!” she said, taking one of my hands and lifting it up, planting a feather-light kiss on the back of it.



“It’s my pleasure, really,” I told her truthfully.



“I’ve already got a booth ready for us. Come on,” she said, standing up from the bar. She took my hand and led me toward the back of the restaurant to a comfy booth that had large curtains on either side of it. She took her seat and patted the spot next to her, so I sat down. Shortly after our waitress came over, and as we ordered, I noticed that her eyes kept going back and forth between us, clearly admiring us.



Once she was gone, Cynthia and I began to talk, mostly about my days as a trainer. Even though I never accomplished anything major, a lot of interesting things happened back then. Just as I was running out of stories, our meal arrived. Cynthia had a plate of pasta, while I had a salad. Cynthia asked the waitress to close the curtains before she left, and she did. With the curtains closed, things were a lot more intimate. The small lamp on the wall provided just enough light for us to see. We started to eat without saying too much at first, until Cynthia offered me a taste of her pasta, which I accepted. She twirled her fork around and lifted it.



“Open wide,” she said. I felt a little silly, letting her feed me like that, but I liked the idea so I did just as she said, and then she leaned in and kissed me, slipping her tongue in. I was caught completely off-guard, but after just a few seconds I began to kiss back. We parted after only a few moments, and she gave me an actual bite of her meal. We went back to eating for a little bit, until I just couldn’t hold back anymore. I lowered one hand beneath the table and placed it on her leg. Cynthia smiled at me.



“I was wondering how long it would take for you to make a move,” she said, giving me a small kiss on the cheek. I slid my hand up the length of her leg, admiring how smooth her skin was. I ran my hand up farther until I got to her crotch, and rubbed her lightly through her panties. As I did, she reached up and pulled down the front of my dress. I wasn’t wearing a bra, so my breasts were freed right away. She let out a small appreciative sound and cupped one of them. I gasped slightly, doing my best not to make any sound. As Cynthia kept fondling my breasts, I slipped my hand down the front of her panties and started fingering her. She had to bite down on her lip to keep from moaning. After a few minutes, Cynthia stopped fondling me and pulled my hand away from her crotch.



“Let’s get this to go, and head up to my room,” she said, before licking my fingers clean of her own juices.



After pulling my dress back into place, we got everything packed up and headed back to her room. But we couldn’t hold back, and once we were in the elevator, Cynthia pressed me against the back wall and kissed me deeply. I lifted one leg and wrapped it around her. She put her hand on my ass, holding me steady as she began to grind hard against me. I wrapped my arms around her, sliding my hands under her skirt and cupping her ass, pulling her tighter against myself.



Just as we were getting into it, the elevator stopped and the door began to open. We broke away instantly just as a couple walked in. Right away the guy began staring at Cynthia, than he switched over to me and began to drool a little. Then his girlfriend smacked him in the back of the head and pulled him down by the ear, and began cussing him out. Thankfully it was just a short time before we got to the floor with Cynthia’s room, because it was a pretty awkward ride with Cynthia and I standing there watching him get berated, especially since he couldn\'t stop staring at us, and even she seemed to sneak a few glances at Cynthia while she was yelling at him.



We got out as fast as we could, and rushed to her room, leaving the couple behind. It was pretty clear to me that the guy was most likely going to be spending the night outside his room. Once we got into her room, Cynthia let out a sigh.



“Looks like we’re finally going to get to have some real fun,” she said with a grin. She guided me to the bed and had me sit down.



“Just enjoy the show,” she said. She began to dance a little, shaking her hips seductively, running her hands all over her body. She started by undoing her hair, letting it cascade like a golden waterfall. Then she walked over, lifting one leg up and resting it on my shoulder. She began to unsnap the buckles one at a time, leaning in closer, until right as she got to the last one our faces were nearly touching. I leaned forward to kiss her, but she pulled back.



“I told you, just watch for now,” she said as she bent over and gripped her boot, pulling her leg out of it extremely slowly. As soon as it was free, she pulled out the chair that sat in front of the vanity mirror and she unbuckled the other boot, throwing it away. She spread her legs widely, giving me a good look at the large wet spot that had formed in the middle of her panties. But just as soon she closed her legs again, and stood up. She quickly spun around and bent over, and started to lift her skirt. But just as I caught a glimpse of her ass, she lifted her hands up and instead pulled her shirt off, still facing away from me. But I could see her perfectly well in the mirror. She reached up and cupped her breasts. She walked over to me, keeping her hand over her chest, and lowered herself so that her rear was resting on my lap. She then wrapped her arms around me and pulled me face-first into her breasts. She began to slowly rock her hips, and after just a few seconds she let go of me, but kept grinding. She reached back and unzipped my dress, and pulled it down. She pushed me onto my back and kissed me, and started working her way down, kissing my neck before she started on my breasts, tracing her tongue around my nipples in very slow circles before finally taking one of the hardened nubs between her lips. She swirled around it very gently, giving a tiny nip before moving over to the other one, giving it the same treatment.



After she was done with my breasts, she began to kiss farther down, pulling my dress away as she went. Once it got to my waist, she stood up and pulled it off, and lifted my leg up.



“You have fantastic legs, Caroline," she said, running her hands along my calves. I couldn’t help but blush slightly at being complimented like that. She took hold of one of my shoes and pulled it off. She cradled my foot gently, caressing it softly. She lifted it up and gently traced my big toe around her lips, before moving on to the next. Once she had done that, she began to lick each one very slowly and softly. Then she licked the sole of my foot. I was already turned on, and couldn’t hold back any more, so I reached down and began to finger myself as Cynthia kept licking all over my foot. Once she was done with it, she lifted my other foot and began to do the same for it, and shortly after she took my toe between her lips. I came with a loud gasp. Cynthia kept licking my foot for several moments, before letting it go.



She than pulled her skirt and underwear off at the same time, and crawled on top of me so that we could sixty-nine. She pulled my panties away and began licking me. I shoved a few fingers into her pussy and started licking all around her cunny, making her moan loudly. As I did, I reached up with my free hand and began to trace my fingers along the sole of her foot, while I hummed. It didn’t take very long for me to make her cum, following just a few seconds later.







“After that, we got dressed and went to a strip club and...” Caroline drifted off for a few seconds.



“Let’s just say if you ever get the chance to go to the VIP room with Cynthia, you’ll never forget it,” she said, ending her story.



“I’ll keep that in mind,” Mary said, puffing her cheeks slightly, not trying to hide the jealousy this time around. “Anyway, remember to tune in next time for more of DJ Mary’s Sexy Stories.”