Creative Writing

"I may have missed out telling you a little detail about my fantasy." she gestured to her outfit.

"You look amazing." I replied honestly.

"Thanks. You don't mind playing along, do you?" I shook my head, trying not to grin like an idiot.

She slipped off her coat and struck a pose. One foot off to one side and cocking her hip. In a slightly deeper breath voice, she said.

"It's £50 if you just want oral. £100 for vaginal. £150 if you want to stick it up the pooper. However, as it's a slack time of the year, you can get all that and have me all night for £500."

Just for an instant I wondered if this was all a set up. Was I expected to actually pay? My brain ran away with the connotations trying to join the dots. Chloe gave me a wink, and I relaxed.

"I think I'll take advantage of your special offer. I should warn you I intend to make you work for your money. Although I think I should get to see what I'm buying."

A grin flashed across her face as I was playing along to her role play.

"Sounds reasonable. Sit on the bed, I think you can do the honours."

She moved to stand between my open legs and added. "Starting with my panties."

Running my hands up the back of her thighs, they slid under her skirt and encountered her naked bum. She must be wearing a 'g' string or a thong. However, I was distracted by having my hands on her firm young buttocks. After seeing her lying on my bed the other night, I'd become a little obsessed about them. Yes, I'd managed to touch them earlier in the day, though it wasn't in the flesh, as it were.

Chloe shifted slightly, and I realised I'd gotten distracted. Pushing my hands higher, but I encountered no sign of her underwear.

"Oops!" She said, trying to sound innocent. "It seems I might have forgotten to put them on."

She lifted one foot and wobbled a bit before placing her foot on the edge of the bed. In doing so, it exposed her crotch. I noticed in passing that the pubes I'd seen last night were gone.

"That looks tasty." I commented.

"I've had no complaints." She replied, trying to sound as if this was all run-of-the-mill stuff.

I pulled her skirt up, so it was just a band around her waist. Reach out, I ran my fingertips over her freshly shaved mons. Dipping lower to brush the hood of her clit. Chloe let out a little gasp, which was out of character with her role play, she forced herself to adopt a slightly bored tone.

"You approve?"

"I've not seen the whole package yet. However, from what I've seen I think you're undervaluing herself."

I pushed her back a step and stood up, pulled her top up and off in a single sweep. That morning I'd got a glimpse of her tits when she put her bra on but seeing them like this was far more impressive.

Her areola were a strong pink and topped with hard pencil eraser nipples. Just begging to be touched and sucked on. There was a hint of uncertainty in Chloe's expression, a woman's natural insecurity about exposing herself to her lover for the first time.

"Outstanding!" I whispered, and she seemed to relax.

As she started to push her skirt off, I stopped her.

"Leave it like that for now."

"OK, you've seen what I'm working with. Why don't I see what you have to work with."

She dropped to her knees and went to unzip me. I was tempted to help, but it was probably part of her roleplay. As she undid my belt and pulled my trousers down, and my hard cock sprang free, nearly hitting her in the face.

"Fuck me, Ian. That's an impressive cock." She'd forgotten to keep in character. But I wasn't about to call her out on it.

I stepped out of my trousers and slipped off my shirt. Chloe looked up at my hairy chest and I hoped she liked what she saw.

"Nice!" She added, back in her breathy voice. "I think we're going to enjoy this evening. May I?"

She asked, holding her hand next to my shaft. I nodded, and she wrapped her fingers around it. Slowly peeling the foreskin back as she wanked it. I'm sure she didn't realise she licked her lips as she saw the purple head emerge.

She glanced up at me and I could tell that this was where the roleplay and her own desires merged. Opening her mouth, she slipped the tip inside her mouth and wrapped her deep red lips around it. Teasing the opening with the tip of her tongue. Fuck! She knew what she was doing.

However, unlike a true escort who would probably try to get me to cum quickly, Chloe was taking her time. It appeared she wanted to enjoy it as much as I did. Gradually, she took more of my inside her mouth as her head bobbed up and down.

"Sit down." She ordered, and she shuffled on her knees to keep her mouth on my cock as I sat.

Releasing me, she pushed my cock back up against my abdomen and ran her tongue from the base all the way to the tip. Then went lower and tongued my balls. Something I always like in a situation like this. Alternating between licking, sucking and tonguing Chloe was working me towards climax, no matter how I tried to hold off.

"Enough!" I cried, and she sat back looking rather pleased with herself.

"Up." I ordered and helped her to her feet, then pushed her onto her back on the bed.

She lay there trying to suppress a smile of anticipation. I lifted one leg up and removed her high heel, then repeated it. Careful when I put her legs down, I could clearly see her shaved pussy.

The labia were thick and swollen, a clear sign of moisture showed at her opening, and it was my turn to lick my lips in anticipation. Dropping to my knees, I pulled her down the bed until her bum was almost at the bottom of the bed.

I wanted to impress Chloe, and I wanted to take my time. However, within moments of my oral administrations, it was obvious Chloe was far closer to her climax than I'd expected. Switching gears to match up with her needs. My fingers and tongue worked her to her peak and over it with a squeal and body quivering as the tremors robbed her from self-control.

"So good. Oh, fuck that was so good."

She tapped the bed for me to lay next to her and I wiped my face before lying next to her. She rolled over and hugged me and I felt more aftershocks as she recovered. Chloe moved up to kiss me. "Thanks" she said in her usual tone. Then switched to her escort voice.

"Think you deserve a reward for that."

Moving me into the middle of the bed, she squatted over me and lined up my cock at her opening. Lowering herself, we both let out a gasp as she pressed down. The tip resisted for a moment, but then slipped inside.

Her expression is one of intense concentration, as she worked me all the way in. When I bottomed out with her weight on my pubic bone, she looked me in the eye and gave me a very intense smile. Like she'd performed some great sexual feat. Regrettably I'm only average size, but perhaps a little thicker than some.

Reaching for my hands, she pulled them to her breasts then put hers on my ribs to lift herself up and down again. It felt great, especially when she worked into a rhythm. Luckily, I'd calmed down whilst eating her out. So, I'd not pop quickly, but I'd not last long.

Chloe seemed to sense this and suddenly lifted off me. Getting off her knees and standing above me. She took my hands to steady herself as she lowered herself. With no hands free to aim, it took a couple of goes to line up and slip back inside. With the tension in her legs as she squatted over me, she felt tighter.

Looking me in the eye, she bounced up and down and I was reminded for a moment of a jockey in the saddle. I say for a moment, as the sensations were too intense to ignore.

"I'm not going to last much longer."

Chloe nodded, she was panting with the effort, and I was very much appreciating it. Her face was very red and getting sweaty and I realised I'd better finish before she ran out of steam.

"Shit!" I managed as I exploded inside her.

She arched her back and sank all the way down, taking me as deep as it could go. I felt her pussy spasm around my cock as she climaxed again.

After a few moments, she collapsed against my chest.

"Good?" She asked.

"Very."

"Me too. Shit! I never expected that one. It just crept up on me."

We lay there a little longer until Chloe had her breath back, she slipped off me letting my semi hard cock fall from her. Then slid down the bed.

"I'll just clean up a little." She commented, then licked my cock clean from our combined juices. Careful to avoid the most sensitive areas.

She slipped from the bed and grabbed her bag and entered the bathroom. I hear her peeing, then flush. She came out from the bathroom with a toothbrush in her mouth.

"You might want to have a look in the bag. It might give you some ideas." She tossed the bag on the bed and returned to the bathroom.

Inside the bag were a bottle of lotion and another of lube, a regular sized vibrator and a smaller one, hardly bigger than my little finger.

"That's for; back there." Chloe said as she saw my holding it up.

She's a little flushed at admitting it was for anal play.

"However, now I see what you're packing, I'm thinking I might be undercharging for that."

"Why not grab some towels?"

When she returned, I got her to remove the skirt around her waist and lie on her stomach on the towels. Then I massaged the lotion onto her skin. I'll admit I took a long time working on her bum and toying with, but not penetrating her pussy.

When she rolled over, I spent even longer on her chest, teasing her nipples until they almost looked painfully hard. Working lower, I avoided touching her pussy directly, and when I took up the regular vibrator. She groaned in annoyance, when I touched everywhere else, but her breasts and pussy. Tickling the soles of her feet resulted in me nearly getting kicked off the bed.

Switching places, Chloe copied me, except she spent a long time probing my anal area. It felt very weird to have such a greasy feeling in that area. By the time I rolled over, I was hard again, and Chloe straddled me and trapped my cock between my abdomen and her labia. Rocking back and forth, forcing her labia to part and run along the sides of my shaft.

She was using me to masturbate without penetration. Rubbing her clit over the underside of my cock. Making very intense feelings as the cluster of nerves ending below the tip of my cock each time it encountered her clit. If I'd not just cum a short time ago, I could probably have cum like that. It certainly looked like Chloe enjoyed it.

After several minutes she seemed to remember her role play and stopped. Lowering her breasts over my face. I licked her nipples. but the lotion didn't taste very nice.

"What would you like next sir? You've sampled two of my holes. Want to go for the hat trick?"

"You sure?"

"Yes, but go easy."

"Of course."

Grabbing the lube, I got her to lie on her stomach, put some on the smaller vibrator and used it to spread it over her anal area. It wasn't just going to be me feeling weird back there. I was tempted to turn it on, but that might not benefit me. Once there was a lot of lube in place, I pressed the tip gently against her sphincter.

After a few moments it opened a little and I twisted the small toy around to spread the lube effectively. Adding more lube, I repeated it, this time sinking almost an inch.

"OK?"

"Fine, it's just a little cold."

"Sorry."

"It's fine, just feels odd and I'm anxious about this."

"We don't have to, you understand."

"I want to."

Careful not to touch the bottle with the tip of the vibrator to avoid contamination. I did it again until the whole thing slipped up her bum with hardly any pressure. It squelched with some trapped air, but Chloe was pushing back against me now. Obviously getting into it. As I turned on the toy, she jumped at the sudden vibration in such a sensitive place. But then pushed back harder, encouraging me.

For several minutes I was content to pleasure her with the toy, but Chloe had other ideas.

"That's enough." She said and moved to take the toy off me.

She headed to the bathroom, and I heard the water running as she washed it off. When she returned, she was walking funny.

"I thought you only walked like that afterwards?" I joked, and she giggled.

"I always wanted to be a cowgirl."

She had me lie back as she sucked me a moment to make sure I was fully ready, then poured a lot of lube on me. Working it evenly over the entire surface.

"It may seem like too much, but that's not a baby carrot. Ready?"

After wiping her hand on the towel, she got on her hands and knees.

"I'm taking my time and if it's too much, just tell me."

She nodded and braced herself.

"Relax, it's worse if you're too tense."

"I know. But knowing it mentally and putting it into practice are two entirely different things."

I picked up the small vibrator and turned it on, then used it to tease her pussy. Tracing along her lips and near, but not touching her clit. In a minute I could tell she was getting more relaxed, so pressed the tip of my cock against her sphincter. Not pushing hard, but with enough pressure to hold it in place.

After a moment of tension, I felt her relax and open. Again, I waited, not impatiently jabbing it in. She pushed back and gasped.

"We can stop if you want?" I told her.

"No, use that vibrator to distract me."

I slipped it inside her and I felt the indirect vibration against the tip of my cock. She pushed back again, and I matched it, feeling her open up more.

"Shit!" She muttered and paused again.

I was thinking it would not happen when suddenly the sphincter swallowed the tip properly.

"Oh, thank fuck for that. I was a second away from giving up. Give me a second to get used to it then push it in all the way. Doing it slowly is a torture."

After some heavy breathing, she pushed against me, and I took that as my cue. Pressing forward, inch after inch slipped inside her.

"Don't stop." She said grunted.

As my pubes pressed up against her greasy hole, she let out a sign of relief.

"I don't think I've ever felt so full, it's like having a baseball bat up there. And having the toy in my cunt at the same time is driving me insane. Fuck me."

I think her use of the 'C' word was a sign of her not being herself.

I'd love to say we fucked like this for ages, but the tight grip and the vibrations worked for both of us. Chloe had her face buried in the pillow to smother her outcries of pleasure. When she climaxed, I swear she nearly tore my cock off, and it triggered my climax. My hand slipped on holding the vibrator in her pussy and my thumb slid in alongside it.

Chloe cried out a second time and her whole body tensed and then shuddered as if someone was running an electrical charge through her body. She collapsed onto her stomach, and without meaning to, pulled me down on top of her.

"Fuck!" She cried out as the impact drove me in a little deeper.

Scared I'd hurt her, I pulled back and got another "Fuck!" as I pulled out. Her rectum looked well and truly plundered. I felt guilty about doing it, even though she'd repeatedly told me to do it.

"Oh shit! I've never cum like that before. I think I even squirted a little. I think that was my first proper anal orgasm. And vaginal almost at the same time. It was almost too much for me."

Suddenly I realised I'd left the vibrator still going in her pussy, so I gently turned it off and took it out. She rolled onto her side and held an arm out to pull me into a hug and kiss. Exhaustedly, her kisses are vague as if she's not quite got control of her body yet.

After a few minutes, she pulled me up and into the bathroom. We showered together and spent a long time making sure we were both fully clean and free of the greasy lube. Her rectum still looked red and a little sore, but it wasn't quite so angry looking.

"I hope you don't mind if we don't do that again tonight. Don't get me wrong, it was amazing. But it was pretty painful."

"Sorry."

"It's not your fault. Well, I suppose it partially is, as it's your big dick that did it. However, I was the one who insisted on it. Perhaps I should have listened to you."

"Perhaps, how about we get something to eat?"

"Room service?" She asked cheekily.

"I was thinking about finding a restaurant. Regrettably that means we'll both have to get dressed. You have some regular clothes?" she nodded.

Two hours later, after a nice meal and a few drinks, we returned to our room and got naked again.

This time we used what we'd learned about each other's bodies earlier to make love instead of simply fucking. We spent time orally pleasing each other before I got on top and we watched each other's faces as we built to our mutual climaxes. She orgasmed moments before me.

Snuggling up against each other, we slipped into a post orgasmic sleep.

It was all too obvious in the morning that Chloe felt awkward about what had happened. She jumped in the shower as soon as we woke, then hurriedly dressed. Against my protestations, she turned down my offers for breakfast and a lift home. Rushing from the room, she barely gave a backwards glance.

Her running out like that was a little upsetting. But I'd spent a long time considering the implications and consequences of fulfilling a fantasy in real life in my writing. The cold light of day can change how you look at things. All I could do is hope last night was not something that would scar her, and she'd get over it.

Rather than get breakfast at the hotel, I hit the road and try to avoid most of the early morning traffic. Arriving home close to noon, I plugged my phone in to charge and headed off to make a coffee.

The phone rang before the kettle had boiled and I answered it to find it was Chloe.

"Ian, I'm so sorry about rushing off like that."

"It's OK."

"No, it's not. It gave you the impression I regretted it."

"You don't have to explain." However, she ignored me.

"I woke up just before you and freaked out. I was in bed with a stranger and after what we'd done. I nearly tried to sneak out without waking you. But that would have been hurtful. Probably thinking you'd done something wrong. You didn't. It's just I've done nothing like that before."

"You don't have to justify yourself..."

"I feel so bad for running off, but my head was all over the place. Inventing wild conspiracy theories, like you'd somehow wired up the room to record us having sex and were going to publish it online. And a lot more stupider than that."

"It's ok to have a bad reaction to fulfilling a fantasy. I just hope it didn't turn out too bad for you. Because I know I'll fondly remember it for a very long time."

"Me too, and that's not just because my bum is sore." She laughed and finally sounded a little more relaxed. "What I meant was it was an amazing experience and far better sex than I'd expected..."

"Thank you."

"You certainly ticked off something from my bucket list as well. You know at one point I nearly thought I'd actually charge you. Not the full amount we talked about, but just a token. Just so I could feel what it would be like to be paid for sex. That was one of the things that freaked me out. That was a pretty big line to cross with a fantasy."

"You weren't the only one to get a little freaked out. When you started talking about money, I wondered if it had been a set up all the time. A beautiful young woman like you, and there's little old me."

"Ha! There's nothing little about you. The fact I'm sitting on a very soft cushion right now, proves that."

"So apart from a sore bum you're, OK? I hope it didn't scar you for life."

"No, I'm fine, and to be honest the memories of those amazing orgasms are blurring out the memory of the pain. A bit like childbirth I'm told, the pleasure and love of the child makes you forget about the bad bits."

"I'm relieved, I was worried you put last night into the 'definitely a mistake' column."