The Freebie

"It's fine." she said. "It was nice in a way to get some attention."

"I'm sorry you are leaving so soon." I said, meaning it.

"You are busy," she said, looking at the queue and the people in the smoking area.

"Not so busy that I can't walk you to your hotel room," I said.

"Mine and Victoria's hotel room," she reminded me.

"That too."

"Sure your girlfriend won't mind?"

"She can't mind! You are on the freebie list."

Rebecca laughed.

X

"Fuck," I moaned, as I plunged all the way inside Rebecca's ass in one move. One hand aiming my cock, the other holding her phone and filming. One of her hands was parting her ass, holding apart one of her firm buttocks and the other was dancing over her unfucked pussy.

Her eyes were closed tight and her head rested on the pillow, ass up in the air. I moved the camera up to cover her face, to see the look of bliss as I plunged down, and then immediately pulled all the way out. I moved the camera to cover her ugly gaping anus. Then, before it could close up, I slammed back down fast.

She looked up at me, deep into my eyes and for a moment I could no longer move.

"This.. is... incredible... I never dreamed I could do this," she said dreamily. As soon as she finished, I plunged all the way in again. "That anyone would want to do that to me."

"Fuuuuck," she exhaled. She closed her eyes and held them tightly shut.

"I think I can go deeper if we move," I gasped, as I remembered something I'd seen on Youporn.

"I'm not sure I want you any deeper," she said, with concern suddenly showing behind her smile.

I ended the recording, quickly hitting airdrop to send the video file to my own phone. Then, before she noticed, hit accept on my apple watch.

"Okay, move on your side," I said moving her back down so that she was flat on the bed and out of the doggy position she'd been in.

"Fuck," she gasped, moving her hand to the small of her back.

"Okay?" I said, with genuine concern.

"Just stiff," she said. "Been a while since I've been in this position."

I grinned, and turned her so that she was on her side. Then I moved up her legs.

"What, what do you want?" she asked.

"Curl up," I said.

"Like fetal?" she asked.

"Like a wounded animal," I grinned.

"That feels about right. Fuck, my ass stings. It feels like it's like burning or something," she said, moving her fingers along the rim of her asshole with their tips becoming coated in the lube.

Rather than sliding in behind her, like she might have imagined, I stayed above her. Moving my knees to either side of her ass. One at the small of her back and one at the back of her thighs.

She was so tall, and broad that she looked big even curled up in a ball. There was such a hot juxtaposition in having such a powerful woman in such an obviously submissive position.

"Curl up tighter," I said.

She looked at me, studied me for a moment, then, confused, did as I asked; hunching her back and pulling her knees up against her chest.

Her shoulders looked even bigger now, her legs even longer. She was almost fully compacted.

"Tighter?" I said.

"Mmmm," she said and pulled her knees in with her arm. "I must look like a little girl. Should I suck my thumb?"

I grinned and pressed down on the top of her ass, twisting her hips and opening her buttocks at the expensive of her lower back.

She rewarded me with a hiss of pain, which made me pick up her phone and hit record as fast as I could. I didn't want to miss any of this. Then I pressed my tip into her ass. One of her hands moved around to press on my thigh, ready to tell me to pause if she needed, while the other reached between her closed legs.

Rebecca looked up at me, saw her phone, and closed her eyes tight.

"MMMM," she moaned emphatically, and then sped up the speed of her finger as it danced it's dance on her clit. "I've got my own sex tape now."

I focused on her hands for a moment and then I moved the camera down to my broad, glistening tip. I filmed it as it pressed against her body, zoomed as I pressed harder, and then captured the moment it popped inside. I sped up my invasion once that moment was passed.

I zoomed out as my cock descended into her, and panned up to capture her face. Her mouth was hanging open, and the hand that had been on my thigh had now moved to cuddle her stomach. As if she was in pain.

"Fuck," I moaned. "We have to do this again. This can't be a one-off."

She closed her eyes even tighter and let out another low moan which sounded like, "Yessss."

I lifted up my hips and began fucking in and out of her ass. I was pressing the top of her ass down so that her hips were at almost right angles to her torso and legs. I kept waiting for her to stop me, but she never did.

I pulled the camera zoom back, to get a full body shot of her all curled up and completely, still and taking as much of my cock as I could force in her. My breath caught at the sight.

X

"Are you coming up to my room as well?" Rebecca asked as we reached the lobby of her hotel. The hotel was an old Victorian one, with ornate tile floors, and a high ceiling. I was surprised she hadn't been booked into a more expensive hotel, but then she was also sharing so clearly cost had been an issue for someone.

"Is that an invitation?" I said with a smile.

She looked at me for a moment, saying nothing but clearly thinking about something. "No," she said finally. "I was just wondering why you didn't leave me outside."

"Well I had to make sure you were safe, big famous star like yourself." I teased.

She punched my arm playfully, then looked at the lift and back at me. She bit her lip. "What time does your club close?" she asked.

"Three," I asked, confused. I looked at my watch. "So... two hours from now."

"How long can you be away from work?"

"Do you need me to keep you safe until your friend gets back?" I asked, with a smile.

"Yeah. Maybe?" she said. "Yeah, I think so."

"Isn't that a bit like asking the wolf to guard the sheep?" I asked.

She tilted her head, not following.

I grinned. "Don't worry."

The elevator pinged open. We stepped in, and it closed behind us.

"So, like, did you agree on things you could do with me when you agreed your freebie list? Is that something you even thought about?" she asked suddenly, her eyes more alive than I'd ever seen them.

She caught me by surprise and I stammered for a moment, which made her smile.

"Anal. Lots of anal sex." I said.

She seemed shocked for a moment, then smiled. "Anal?" she repeated. "Wow! Just anal?"

"Is that a problem?"

"Did you and your girlfriend think I was the kind of girl that would be okay with anal sex?"

"That's not a no." I said with a playful grin.

She sighed, a long sigh and looked at me with a long look. "Why anal?"

"Cause apparently if I want to do that, then I've got to do it with someone else." I said.

"You mean your girlfriend won't let you have anal sex?"

"Nope," I said with a grin, "She says I'm too big."

"How big are you?"

"I don't want to boast." I said.

"And what makes you think I can take it?" she asked, tilting her head again.

I almost said it was because of how big she was, but I managed to stop myself just in time. "We can only try," I said instead.

"I'm not much of an expert at anal sex," she said with a little embarresement.

"It's okay, neither am I," I said honestly.

"Fuck," she said running her hand through her hair. The lift door opened. She looked at me, smiled, took my hand and then led me into the corridor.

X

"Oh my fucking god," Rebecca gasped. "Fuck, I'm going to cum. I'm going to fucking cum. I'm going to cum from anal." She was getting louder. "Fuck, shit, oh my god. I've got a stranger's cock in my ass and I'm going to cum!"

I groaned deep. I moved the camera so it was on her face. Getting ready. Her body began to spasm, and I wanted to be ready.

"Choke me," she suddenly said. "Grab my throat."

I did as she asked, quickly, with my free hand.

"Harder," she croaked. "I'm your anal whore. Fucking choke me."

I could feel her orgasm coming, so I tightened my grip on her throat and I increased my thrusts in her ass. They were deep, fast thrusts, pistoning into her asshole. More and more of the lube seemed to bubble around my cock as I pumped in and back out of her ass.

Then I felt her tense, and her teeth clench and I knew she was cuming. A real nasty dirty anal come.

"Oh fuck," she squeaked, obviously trying to be loud but muffled by my grip.

That was when I moved.

As she was clenching tight I switched the phone into selfie mode, then held it in front of her face at the same time as I lay down on the bed spooning her. That meant I could go deeper.

With Rebecca lost in a world of her dirty orgasm, her body locked down tight around the half of my cock I already had in her. Without mercy, I pressed my whole length deep into her guts.

The noise she made almost made me cum there and then.

"Ohhhh... ohhhhhhhh..."

It was a deep guttural noise, like a dying animal, but it came from deep within her. Her arms wrapped around her stomach protecting herself. Her face was distorted by the ravaging ecstasy. Rebecca's orgasm seemed to hit a second level, as if for a moment she became a quivering zombie, blank eyes seeing nothing. Her body quivering around my invading cock, and I captured it all on the camera. When she started lying still, I stopped the recording and hit airdrop to send this second, longer video to myself.

"Fuck," she said, finally coming alive. My length was still impaled in her, but staying completely still.

"Fuck, that was... intense," she said, and rubbed her neck. She looked embarrassed, and avoided looking at me for a moment, as if I'd seen part of her she didn't want me to have seen. She slowly stretched out ,moving off me. Then she noticed I was still hard.

"You didn't cum?" she said.

"Not yet." I said with a grin.

"Fuck.." she moaned. "I thought you came when I did."

"Why?" I grinned.

"The way you pushed in, I just, assumed, you know." she said, losing confidence.

"I'm not done yet." I said lifting her head and kissing her, trying to let her know it was all okay.

"How long do we have left?" she asked.

"Thirty minutes," I said, looking at my apple watch and marvelling at how low my heart rate was already. That was some good recovery.

"Lie back," she said.

I looked at her for a moment, then did as she said.

"So, I took you all, didn't I?" she said. "And I came. Big time. And your girlfriend won't even let you do this."

"Yeah, you did," I said looking up at her, "Fuck, there is no way this can just be a one-off."

She grinned at me, picking up her phone and turning it on me. "I'll give you my number," she said. "Isn't a freebie just a one-off thing."

"Yeah, this so isn't going to be okay with her next time." I said.

"Is that okay with you," she asked quietly.

"Fuck yeah," I said, grinning up at her. "I just ass fucked Rebecca Harringdon and watched her cum."

She smiled and moved so she was sitting astride me. She put herself up on her powerful legs, and then used her hand to move my cock head past her unfucked pussy and to the slippery entrance to her bowels.

"Ready?" she said and started to lower herself on my cock. Her face was partially obscured by the phone, but for the first time I could see her magnificent body; her perfect little breasts, with their neat nipples, and her toned stomach. I would never have guessed it had been five years since her Olympic peak.

"Fuck," I moaned.

"Let me know when you are close to cumming," she said.

"What makes you think you can make me cum," I said, in as steady a voice as I could manage.

She smiled. "I'm pretty sure."

"Why?" I asked.

"This," she said, then she bit her lip and in one fast motion, she sat down fully on me and impaled her ass on my cock. Her jaw hung open.

"Fuckk," I hissed.

"Just let me know," she moaned.

X

"Are we really going to do this?" Rebecca asked as she closed the door to her room behind us. The room was not much past the two double beds. One was neat, and one had a messy pile of clothes on it. When Rebecca swept the pile of clothes on to the floor I knew that her's was the messy one.

"Can you think of a good reason not to?" I said quickly.

"I can think of more good reasons not to than to actually do it." she replied.

"Yeah, but I don't think that is going to stop us," I said, not feeling anywhere as sure as my words made me sound.

"Does it have to be anal?" she asked.

"Are you Rebecca Harringdon? The Olympic swimmer?" I asked.

She nodded clearly confused. "You know I am."

"Then it has to be anal sex." I said.

"But why?" she almost whined.

"Those are the rules," I teased.

"What rules?"

"My list, my rules." I said, knowing I was running out of talk and would soon be walking back to work.

Rebecca looked at me for a moment as she worked something out, and then she nodded. "Okay, give me a second." she said, and then she left me as she went into the small bathroom and locked the door.

She was gone just over ten minutes, not the one second she had claimed. The first couple of minutes had been fine, but then I started to think she was hiding in the bathroom, and I sat on the edge of her bed, thumbing through my phone and checking out how things were going back in the club. By the time she reappeared, I'd just about convinced myself that she was going to come out and tell me to leave. It would have been disappointing, but I wasn't going to complain.

"You need to go and buy some lube," she said, sticking her head out of the door, and as if she'd read my thoughts she added, "Take the key card thingy."

I ran to the small corner shop, and the asian man behind the counter smiled at me when I grabbed the bottle. I assumed he thought I was gay. That was a fair assumption, in my smart three-piece suit. It was much more likely I was gay rather than the truth. Who would have guessed that I was going back to the hotel to ass fuck an Olympic medalist, especially a female one. I wasn't even sure I believed it myself.

I found Rebecca lying on her bed, completely naked apart from her high, jeweled heels. It was an incredibly slutty touch.

She blushed when she saw me. I held up the lube.

"I'm so glad you came back," she said, "I was worried you wouldn't. I'd have felt so stupid lying here and waiting. So much for feeling sexy."

She sat up on her elbows, slightly awkwardly, looking all long legs and arms. She looked too big for the bed, and it crossed my mind, looking at her, that the bed might have been smaller than a normal hotel bed.

"You look incredible," I said, tactfully. "Very sexy." I sat down on the bed next to her.

She gave me an unconvinced look, but she didn't say anything. I handed her the tube, and she squeezed out a huge dollop of lube on her palm while I started taking off my clothes.

She sat, the lube cuped in her palm and she watched me, staring with no sense of self-consciousness. I decided to leave my shirt on. This whole thing had a feeling of being in a porn, so keeping the shirt on felt right.

"Do your rules allow you to kiss me?" she said.

"Can I say no?" I said smiling at her, standing before her. Pleased that my cock was already rock hard and ready just from the sight of her.

"If you want to make me feel like a prostitute," she said with a smile.

"Okay, no then." I teased.

"Fuck," she said biting her lip and closing her eyes.

I smiled and picked up the tube of lube.

She smiled. "How should I be?"

"I guess on your front, doggy style?"

"Like this?" she asked, moving to the middle of the bed, putting her ass high on the bed, the top of her legs dead straight, her back bent so that her tits were squashed into the bed. She grabbed a pillow for her head.

"Perfect," I said, and it was.

She looked back and smiled and put her hand underneath her stomach and pressed the thick lube between her legs . Most of it went over her pussy. Her ass, perhaps being an unfamiliar play area for her, remained mostly uncoated. I took a moment to look at her most private holes. Her pussy was completely shaved, but her lips were puffy and pink, as was some of the skin around. It crossed my mind that perhaps the ten minutes in the bathroom had been spent shaving herself clean. She'd missed a few dark whisps of hair around her asshole. The sight was real, and erotic.

I smiled and squeezed a load on to my fingers.

"Put your hands like this?" I said putting them one at a time on her muscled buttocks.

"This feels so wrong," she said.

"I think it can only get worse from here," I said.

I reached forward tentatively, not knowing how she'd react. Maybe she'd freak out, or maybe this would all turn out to be a big joke. My fingers touched the red skin at the bottom of her ass, and I began sliding them the short distance to the small indentation that marked her asshole. It was neat, and clean, and perfectly closed.

I smeared the lube over the entrance and I felt it clench tighter in response to my touch.

"Let me do it first," Rebecca said. Her hand moved from her butt cheek while my hand replaced hers, holding the muscled cheeks apart.

She pressed her index finger inside herself. I looked from her ass, up to her face. Her features were lost in concentration and she was biting her lip.

"Okay, this feels...weird."

"I thought you were going to say tight," I commented.

"Yeah, that too. Fuck, I have no idea how we are going to do this."

X

"Oh fuck, oh fuck, oh fuck, I'm cumming," I said as I felt the rising swell of the orgasm sweep through me. I could feel it deep down within me, starting at my testicles as it threatened to explode through me. "I... can't hold it."

Rebecca smiled the biggest, happiest, most un-self-conscious smile that I'd seen from her. It made her look even prettier, as she bounced her ass up and down along my thick shaft.

"Good," she said, then she aimed the camera at her face, at the same time as she tilted the camera down her body and leaned back.

I saw her stomach bulge in the shape of my cock as she bent backwards the opposite direction to my cock. And she forced herself as far onto my cock as she could, impaling herself totally.

"Oh..." she managed, before her face distorted in pain. Then the smile came back, and she moaned, "Mmmm."

And like that I came. I was as deep as I could be inside her ass. My perfect, pure seed vanished deep inside into the dark dirty colon of the olympic medalist. She was so tight that I could feel every spurt as it travelled the whole length of my cock.

"Put down the phone and kiss me, Rebecca," I just managed to gasp.

She did exactly as she was told. The phone left her hands, and she bent forward and kissed me hard on the lips as the last of my cum shot into her.

I wanted to stay locked like that forever, deep inside her, but it wouldn't be long until Victoria came back and so I let myself slide from her asshole. A flood of fluid came out behind my cock, and slid down over my cock and testicals.

Rebecca looked at the mess, and bit her lip without even realising she'd done it

"Go on," I said with a wicked smile on my lips. I was still painfully hard, with cum still oozing out of my tip. It must have been trapped by the tightness of her guts to have stayed inside me.

She looked up at me, seeming momentarily confused. I started to sit up, then moved to my knees bringing my glazed cock towards her mouth.

"I don't even know your name," Rebecca said, as her mouth engulfed my cock without even a brief inspection. It had been as deep as it could possibly go inside her. It was impossible that it could be completely clean. Even without anything else, that amount of lube, flavoured or not, would turn even the strongest of stomach.