I looked down in awe as my rock hard cock pulled back out of Rebecca’s asshole. Her low moan was a cross between pleasure and pain. So erotic. The entire length of my cock was coated in lube, the same thick lube which was smeared around the bottom of her ass crack, her pussy and some of her muscled buttocks.
“Are-are you sure this is okay?” I gasped, trying my hardest to concentrate and not just cum straight away.
“Mmhmmm,” Rebecca said beneath me.
“Have you done this before?” I asked again, still slowly withdrawing my glistening length from her ass.
“Once or twice, I’m not sure. Never on a first date, though,” she said looking back at me with an expectant smile. The smile was so pretty, even given her prominent nose, that I had to lean forward to kiss her. The motion of leaning forward pushed my wide cock further into her asshole, and she closed her eyes as pain flashed across her face. I kissed her anyway, and after a moment of delay her tongue met mine.
“Oh, was this a date?” I asked, with my teasing smile.
“I-I guess not,” she said, looking forward. Then she added, “Maybe next time,” and rested her head down on the pillow.
“Next time? Are you asking me out on a date?”
“Mmhmmm,” she said, her eyes closed, her face impassive.
“I thought freebies were supposed to be one-offs?”
“Do you always talk this much? And, what happened to not kissing me?” Rebecca asked, in almost a whisper.
“You looked too pretty not to kiss.”
She smiled, then winced and hissed out, “Fuck, you are way too big for this. Your girlfriend was right.”
“I know! Nobody lets me do this,” I said.
“I can see why,” she groaned.
“Ready to go again?” I asked softly.
She nodded, then hissed, “Fuuck,” through gritted teeth as I pressed myself inside her bowels once more. “Oh fuck, fuck, fuck, fuck!”
Rebbeca’s hands gripped the pillow, digging her long fingers into the soft material and clenching. Then she reached for the small tube of lube that I’d bought. She squeezed a huge dollop onto her hand and reached back to her ass.
“Pull out?” she asked, looking back at me with her beautiful blue eyes.
I did as she asked, slowly. Not wanting to overload myself and cum too soon. Her hand found my shaft and wrapped itself around me.
“All the way?” I asked.
“No, keep the tip in, I can’t wanna go through the first bit again.” She closed her eyes again. “Shit, I can’t believe I’m doing this.” she said, as she worked her lubed hand up and down my exposed length.
“What? Fucking a fan?” I said, before I could catch myself.
She smiled weakly, then her eyes became distant and then looked forward at the pillow. “You aren’t a fan. What do you know about swimming?” Her voice was unfocused. “My ex-husband was a fan, and that was a disaster.”
“What am I then?” I asked.
Despite her detached body language, her hand was still working up and down my length. “Not sure.” she said. Then looking back at me she smiled. “Very lucky.”
“Lucky?” I repeated, with a laugh.
“Who gets to fuck the number one on their freebie list?” Rebecca asked.
“Ass fuck, you mean,” I corrected.
She closed her eyes and moaned. “I want to taste you.”
“Lets see if you can take it all the way in first.”
Rebecca moaned, and when her hand slid away she brought it to her mouth and sucked her index finger into her mouth. Then her middle finger. Then she must have realised I was watching and stopped.
“I’m not like this normally,” she said looking back at me, the finger no longer by her mouth.
“I’m in no position to judge,” I said softly, as I started pushing myself back inside Rebecca’s anus.
It was so hard to keep control of myself, she was so fucking tight. It was as if she was crushing me in her lubed fist. Despite that tightness, my cock was sliding in steadily thanks to the vast amounts of lube Rebecca was putting on me. But it wasn’t just about the sensations, this was proper anal sex, with a proper beautiful woman, with the lights on. The kind of sex that only exists in porn. There was also the fact that this was Rebecca Harringdon, an Olympic Medalist, and we’d only met three hours ago.
Yet it was real. Rebecca wasn’t perfect. The bottom of her whole ass crack had already been an angry red before I’d even touched her. She must have been sore, but she didn’t comment or mention it. Perhaps she always got that way after a night of dancing. Her pussy was pink, puffy and messy. Before it had looked so much bigger than her ass, but now it seemed to have shrunk. The inner lips of her labia formed a messy hole that seemed to be begging to be fucked in place of her ass.
Despite how tall and broad she was, the width of my cock dwarfed the size of her ass. I reached down and parted her buttocks. I couldn’t see her asshole or her ring, just the angry red of the depths of her ass crack and then the glorious glistening length of my cock.
X
“You’re Rebecca Harringdon!” I said, as she approached the VIP rope at the entrance to the club. She was teetering on jeweled high heels, the tops of which were just covered by the flared legs of her white jumpsuit. The jumpsuit, with its lace panels covering her upper body, made her look enormous. Not in any way fat but tall and broad-shouldered, looking every bit the Olympic-caliber athlete that she was.
Rebecca turned to her three friends, one older woman and one younger along with a handsome young man with a very of-the-moment haircut. All three were much shorter, and far more traditionally beautiful than her, with her famously prominent nose and features. Her friends looked impressed that I’d recognised Rebecca, and then there was something else; a look in their eyes that said they were both annoyed and relieved that I hadn’t recognised them.
My head doorman leaned over my shoulder and whispered, “He plays for city.” I looked at my doorman, then at the boy, and then back at Rebecca who’d moved closer to me ahead of the other three, and I realised she was a good two inches taller than me, which made her around six foot two.
“I never get recognised,” Rebbeca said, with a huge giggly smile. “Are you a swimming fan?” Her eyes moved over me, I assumed to see if I had the distinctive swimmers physique.
I smiled and let her look. In my dark, three-piece, pinstripe suit, I knew I was well dressed, though in that moment I regretted not ironing my shirt. “No, you were top of my freebie list,” I said, directly to her. Wondering how she’d react. Wondering if she’d slap me, or turn and leave, or laugh.
“What?” she said, looking at me her head tilted to one side as she tried to think. Her three friends broke into smiles and brief laughter, which caused Rebecca to look back at them and repeat, “What?”
I laughed. “You’ve never heard of a freebie list?” I said. I looked at my doorman. “She’s never heard of a freebie list.”
The head doorman chucked playfully, as this was the kind of customer interaction that we both lived for. “I thought everyone knew what a freebie list was. It was on Friends and everything,” he said. “Anyway, I can’t believe you had her on there.”
I grinned. “Top of the list,” I said to him, at the same time as I made eye contact with her.
“What’s a freebie list, then?” she said, smiling and putting her hands on her hips. “What am I top of?”
“I can’t believe you’ve never heard of one,” I said with a grin, “Its a list of celebrities that you are allowed to sleep with, and your girlfriend can’t get mad.”
“Oh god,” she said, and then folded down into herself in an embarrassed giggle.
The older woman, a beautiful brunette, who was at least a foot shorter than Rebecca came up and smiled at me. “Seeing as you have Rebecca as top of your fuck list,” she said, “how about you get us all in for free?”
I looked at Rebecca, whose blushes seemed to be even deeper, and she giggled again.
“Sure. You can have a booth, and some drinks.” I said.
“And champagne?” the brunette asked.
I grinned.
“I said she used to be on my freebie list,” I fired back.
“What changed?” the brunette added.
I laughed. “The London Olympics were a long time ago.” Rebecca looked slightly offended by that, so I added, “Seeing you in that outfit puts you back in the running, though… do you count as a celebrity anymore?” My smile and my eye contact let her know I was teasing playfully with her.
“I do TV commentary,” she said, standing taller again.
“There you go! That counts! Back to the top!”
“Champagne then?” the brunette interrupted.
“I’d need a kiss off Rebecca first before we could do champagne.” I teased.
Rebecca turned bright red again and giggled.
“How about a kiss from me?” the brunette asked.
“I’m afraid you aren’t on my list,” I said, playfully.
Before I could say anything else, Rebecca stepped forward and kissed me full on the mouth. Her hands cupping both of my cheeks, and her tongue forced itself into mine hungrily. I was shocked, and it took me a moment to respond, but as soon as my tongue found hers she pulled away.
I was almost blushing as Rebecca looked at me. She had an almost-fearful look on her face. Her big blue eyes seemed to be looking for any sign of rejection or revulsion, but I just smiled.
“Champagne it is,” I said to the brunette.
I keyed my radio, “Laura, could you come to the front door and take some VIPs through to booth five? They haven’t booked.”
X
“Oh fuck, is it all the way in?” Rebecca said through gritted teeth. She looked back at me, with those big eyes almost pleading for the answer to be yes.
“About half way,” I said, honestly.
“Fuck, I am going to be ruined!” She moaned and put her head back into the pillow. I reached up, grabbed one of her hands, and moved it under herself to her pussy.
She got the idea and rubbed over herself.
“My pussy feels totally different, like so much smaller,” she said to herself as her fingers explored her folds. “Like you’ve crushed my pussy.” She moaned. “How can some girls take a cock in their ass and pussy at the same time?”
She slid one finger along the entrance of her pussy. It looked as if she was going to sink it in, but she resisted.
“I can’t believe you are doing this,” I moaned, running my hands up her back. It was amazing how toned her body still was. How much muscle was on her shoulders. Her femininity forever exchanged for her olympic medals.
“Neither can I,” she said, and looked back at me. “Kiss me again.”
I leaned forward and did as she asked. The act of leaning forward pushed me deeper inside her. She winced and then closed her eyes for a moment. When she opened them again, they were bright and sparkling.
“We can’t have long left,” she said, just before my lips met hers and our tongues encircled each other. She broke the kiss after a moment and pressed her forehead against mine. “Push all the way in.”
“Seriously?” I asked, looking her in the eyes trying to see if she was serious.
She smiled and nodded. “I’m a big girl.”
So I did. Her reaction was every bit as good as the sensations of pressing in. She managed to kiss me for maybe the first inch, then her mouth sort of hung open in a silent cry of pain. I thought about stopping, but I brought up my hand and turned her head back to me and kissed her instead.
“Owww,” she said, in a weak wimper.
I touched her cheek gently, “Shhh,” I said soothing her. Then kissed her again.
“Ow,” she said, in that same wimper.
“It’s okay,” I said. “Almost there.”
She arched her back, taking her head away from me, and then she came back and kissed me hard, then biting my lip hard until I was fully inside her.
X
“Hey, where are you going? I said, with a playful tilt of my head at Rebecca. “Surely you don’t smoke.”
The entrance to the smoking area was the same as the entrance to the club, and the queue ran along the edge of the smoking enclosure. Whilst my doorman and I were standing on the front door, we were also able to manage both the smoking area and the queue.
“Nah, just fresh air. It’s hot in there.” Rebecca smiled, and she looked fairly red-faced to back it up.
“Yeah, the aircon is due a clean next week,” I said with a grin, still not quite believing Rebecca Harringdon was in my nightclub.
I saw people coming towards me from the corner of my eye, so I turned my back on her as I greeted them. They had come to the VIP entry and, finding out that they didn’t have any booking, I sent them around to the queue, which by now was across our unit and the next frontage as well.
I turned around and she was still standing there, taller than me, maybe even broader; a vision in white.
“Having fun?” I asked. “You seem more sober than when you came in.”
“Yeah, champagne isn’t my thing, and Chris took the vodka. I danced until my feet hurt, then I was going to take my shoes off when one of your bouncers came over and said I couldn’t.”
I smiled. “Yeah, it’s a health and safety thing.”
She smiled. “No I get it. It’s just my feet are really starting to hurt.”
“Worth it though. Those are some pretty sexy shoes.” I said.
Her smile brightened and she stuck out her leg. The flared end of her jumpsuit fell away to reveal the four inch spike of her jeweled heels.
“Yep, that is some pretty good shoe porn right there.”
She blushed again and giggled, but kept her foot pointed out. “I don’t normally wear shoes this high, but these were stunning.”
I smiled. “They look great, but you know where they’d look better?”
She looked at me, her foot down, her grin ready. “Go on,” she said, playfully.
“On my bedroom floor,,” I said with a laugh. This was a lot of fun.
“Ha,” Rebecca snorted,” You don’t think your girlfriend would mind?”
“You are number one on the freebie list! She can’t mind.”
“You said I was on the list but not any more,” she reminded me.
“The list can be updated.” I said with a smile.
“I can’t see your girlfriend being happy with you claiming your freebie in your bedroom.” Rebecca teased.
“Well, yeah, good point.” I said with a grin. “Okay, they’d look better on your hotel room floor.”
“Ha,” she laughed, clearly enjoying my flirting, “I’m sharing with Victoria, and I don’t think she’d want to share our room with you especially seeing as you didn’t know who she was.”
“Victoria? Your brunette friend? Was she put out about that?”
“Yeah, just a bit. She’s always the one people know,” Rebecca said.
“And you aren’t?” I asked. “I’m not sure I believe that.”
She smiled and laughed. “She’s the pretty one. I’m like the ugly giant compared to her.” She grinned. “No one really ever knew me outside of sports circles.”
“What brings you to my little club, anyway?” I asked, changing the subject.
“It was on the way back to the hotel,” she said. Leaning on the barrier and looking up the street.
WIth her eyes distracted, I checked out her small breasts. Her nipples were hardened in the night air, and I could see just how small they were on her breasts. I’d always marvelled at how out-of-proportion her breasts had looked compared to her broad chest and back, and thought it was perhaps a cruel curse. In person, though, she looked perfect.
“Way back from where?” I asked
“Oh, an awards dinner. We were booked as guest speakers.” Rebecca said.
Just then Victoria, the brunette, burst out of the club.
“There you are, flirting with Mr Freebie again?” she said to Rebecca. Then she turned to me and said, “Can we have more champagne, please, Mr Handsome Manager man?”
I smiled at her, and back at Rebecca. “I’d need another kiss.”
Rebecca blushed and then stepped towards me.
“I’m just teasing, one kiss was more than enough,” I said, using my radio to ask Laura to get them more champagne. As I did I saw a brief flash of disappointment, which turned to rejection, on Rebecca’s face. That was a surprise.
“Come on then,” the brunette said.
“Give me a minute,” Rebecca said.
“Oh really,” the brunette said with a laugh, “Okay, then! Have fun you two!”
I was about to turn to Rebecca when one of the doormen came out, red-faced and angry. He came straight up to me and the head doorman moved over.
“That’s it, that shirt-filler is a fucking joke,” the doorman exploded. “He’s on his phone again. You have to sort him out. We can’t have him doing that in there, he’s a liability!”
Both I and the head doorman turned to deal with this new situation, and out of the corner of my eye I saw Rebecca slink back inside the club, trying, despite her height, to be as invisible as it felt like she wished she was.
X
“Fuck, you are gaping!” I gasped in awe as my cock pulled out of her ass all the way, and just for a moment her asshole remained open. It was a pink mess of muscles, surrounded by the darker skin of her ass, and in the middle was an angry red opening into her body. It was dark and deep. Rebecca’s gape had no symmetry, wider than it was longer. Just outside of the muscles were the tiny, wispy dark hairs I’d noticed before. Now there seemed more of them, probably because the wet lube had made them clump together.
“Am I?” she said in surprise, and brought her hand from her pussy around to feel it. By the time she’d gotten her finger in place she’d closed back up.
“Missed it,” I said.
“I never thought I could do that! I thought it was just in porn.”
“Well you did.” I said.
“I’d love to see.”
“I’ll take a picture if you like,” I grinned.
“Give me my handbag.”
I reached for her white handbag, and she found her phone almost instantly, an iPhone XR with a white case. She unlocked it, threw it on the bed, and then lowered her head to my lube-covered cock.
“Did you want me to wipe it first?” I asked down at her.
She looked up at me with those big blue eyes and, holding my attention she lowered her head and sucked my tip into her mouth. Then she moaned and closed her eyes, and took more of me in her mouth at the same time she brought her free hand to the base of my cock and pumped.
For a moment I was stunned, watching Rebecca Harringdon performing ass to mouth.
Then, waking up, I pulled up her phone and hit video, and filmed her sucking me.
When she saw I was filming she instantly closed her eyes again. A long drawn-out moan then came from her very core.
I grinned and filmed as her mouth and hands worked her magic on my length. I was happy to have the filming to concentrate on, as it made it possible to control my coming orgasm. Without that distraction, I’m certain I would have exploded with the force of a fire hose into her mouth as she performed ass to mouth.
I never thought I’d see anyone do this, let alone an Olympic medalist. It was all I could do to stop my free hand from forcing her head down onto my cock and holding it there.
X
“Leaving so soon?” I said as I saw her coming out.
“Well, Victoria is all over some guy,” Rebecca said, with more than a hint of frustration and side eye. “His mates are all getting grabby on me, all of whom are gross, and Chris and his girlfriend are eating each other’s faces off.”
“Do you want me to get them thrown out?”
“Chris and his girlfriend?” Rebecca said.
“No, the grabby guys,” I said.
“Nah, just boys being boys isn’t it,” she said.
“We have a zero tolerance of it, so if you want them out I can get them out right now.” I said seriously.
“Honestly it’s fine, they weren’t that bad.”
“If you are sure,” I asked.