Escort Surprise

To really have you understand what happened, the first thing I have to tell you is that I was surprised as anybody. I just managed to make the most of it.

It was a cold February in Chicago a year or so ago. My name is John, and I was in town for a week long sales meeting in the Four Seasons Hotel downtown. The Bulls were playing a series at home, so a number of their players were staying in the hotel too.

Dennis Rodman and I shared an elevator as I went to my room early one night. I'd been feeling a bit under the weather and wanted no part of the partying in the bar. A good book was going to be my night, or so I thought.

Around eleven there was a knock on my door. No one knew my room number, I told myself as I got up from the chair to answer it. I opened the door to find a beautiful woman in a full length fur coat. She was smiling at me as she said, "Stephen?"

I realized that she didn't know what Stephen looked like. Escort service, my mind said immediately. I smiled back at her as I decided what to do next.

***

I held the door open wide, welcoming her into the room, noting her long blond hair. "How are you tonight?" I asked in response to her question. She smiled at me again, beautiful lips.

Dropping the fur off her shoulders and onto the couch, she said, "Quite well, don't you think?" All I could do was stare, at first, thanking Stephen for not being able to get his hotel room number right.

"Quite well, indeed," I was finally able to say. Curvy shape, long legs, full breasts - obviously no bra under her black tank top, and no panty lines in evidence under the black silk knit hip-huggers as she turned for my inspection.

Then I noticed the fuck-me red nail polish on her pretty feet. Strappy black high heel sandals, and fuck-me red nail polish. Mmmmmm, I thought.

"They said you mentioned a fresh pedicure. Will this do?" she asked.

I nodded, smiling, and took advantage of the question to find out exactly what I was getting into. "What else did they tell you? And I'm sorry, but I was so pleasantly surprised by the rest of you that I forgot to ask your name."

"I'm Lilly," she purred, "And thank you for asking. They said your credit card is authorized for your two-hour initial visit, plus up to our maximum, and additional arrangements are at your request and my discretion. They said you were a first-time client of ours and that I was to be especially thoughtful. They said you mentioned a long, stressful meeting, and that I ought to put my massage therapy classes to use."

As I was trying to figure out my next move, she pointed to the desk, where I had a mini-bar set up courtesy of one of our distributors. "May I?" she asked.

"Forgive me for forgetting my manners," I said. "What can I get you?"

"Bourbon. On ice, thanks. No reason to ruin good liquor pouring soda in it, Stephen." She sat down on the couch, crossed her long legs, and asked, "Join me?"

I poured two drinks, sat in the chair across from her, and said, "So how do we spend the next two hours, Lilly? What are you up for this evening?"

"Anything that doesn't involve touching privates, to put it bluntly," she said. She downed half her drink and kicked off her sandal, looked me straight in the eye, and ran her foot up the inside of my calf. "Beyond that, it's up to you. I'm just here to help you relax."

I caught her ankle, stroked the arch of her foot lightly, and said, "Well then, you go right ahead and give it your best shot. I'm open to suggestions."

She giggled and jerked her foot away, and said, "Hey now, I don't know about the tickling. I have sensitive feet." Somehow it made her seem more impish than I had expected, not the stereotype of a call girl. It made me start seriously considering maxing out Stephen's credit limit.

She reached down and slid her other sandal off and picked up her bag, pulling out a bottle of mineral oil. She stood up and polished off her drink, held out her hand, and smiled with those lush lips. "Why don't we start with a little rub down. Take off your shirt and lay down on the floor."

"The floor?" I asked. "Why the floor and not the bed?"

"These beds are way too soft for a serious deep-muscle massage. You need to be on a hard surface so I'm not just bouncing you up and down."

"But sometimes I like bouncing up and down." With Stephen's financing, I was starting to feel a little more bold.

"Bouncing is extra, Stephen," she said as she smirked. "Bouncing involves things your two hours don't cover. Now lay down."

I was not one to argue at this point. I shucked off my sweater and shirt, pulled off everything but my boxers, and laid down on the floor on my stomach. Lilly walked around to my head, and I got another glimpse of those gorgeous feet, those screaming red toe nails, before she knelt down, a knee to either side of my head. She sat on her haunches, then I heard her uncap the oil, squirt some in her hands, and rub them together. She leaned forward, her hands on my neck, my shoulders, down my spine, coating my back with the oil, lightly rubbing it in.

"Are you ready, Stephen?"

"Mm hmmm," I answered. With her hands at the top of my spine, she raised herself to her knees, put all her weight into the heels of her palms, and pushed down and forward all the way to my ass, literally pushing the air out of my lungs.

"That's it," she said. "That's rush of air. That's what I want to hear." Her hands were on either side of my waist, gripping, as she pulled all the way back to under my arms, up over my shoulder blades. "When you are completely relaxed, I will practically be doing your breathing for you." She kept working, pushing, rubbing, from the center out, from the top down, mercilessly ignoring my flinches as she ground the kinks out of my muscles.

She was working hard, and I could feel sweat dripping off her face, trickling cool traces down my sides. When I was feeling loose as a jellyfish, my skin hot from the rubbing, she started to lighten up, branch out to my arms. Then she stood up and slipped her pants over her hips, letting them drop to the floor in front of my face. Those red red red toes again. I reached over, trailing a finger across the tops of her toes, up the inside of her ankle, wondering but not looking to see what had been under those pants.

She jerked her foot back and giggled again. Then she stepped over my head, a foot to either side of my head, and knelt down again facing my ass, her knees to either side of my chest. I turned my head to one side and licked the arch of her foot, then nibbled at it, just wondering.

"Mmmmmmm, that's nice," was her answer, and I licked and nibbled again as she recommenced the rub-down, concentrating on the small of my back, and circling farther and farther down, on top of my boxers, over my cheeks, down to my thighs. With the way she was straddling my back, I could the slightest trace of panties between her legs, thongs I guessed, along with an increasing heat and wetness. With all the oil on my back, she was sliding a little, back and forth, as she worked on my lower back and ass, pulling my cheeks apart with each return of her hand, sliding a finger between them, pushing against the fabric. I was hard as a rock, and wondering how far this could go.

"Is this a violation of the "No touching privates" rule?" I asked.

"You've still got your shorts on Stephen, and so do I. But this is as far as it goes without further negotiations. Money gets me to stay all night. But don't forget the back end of the deal - it's all at my discretion. As far as I go, that means I don't touch you until you make me want to, and you don't touch me until you make me want you to. I'm not just in this for the money." With that comment, she gripped both my cheeks and then slowly, slowly, slowly, trailed her fingertips down the inside of my thighs, up the backs, over my ass, and wiggled her hips. "What are you up for?"

"I want the complete work-over. I want you naked. And I want you to do whatever I tell you to do. How much?" I figured I had to ask; Stephen would certainly have asked.

"No pain, no bondage, no cumming in my face - those are the rules. Can you deal with that?"

"That's not my thing," I replied.

"$1,500 on top of the $1,000 you paid to get me here, up to 6:00 in the morning. Deal?" She wiggled again, the lace on her thong scratching against my skin, then sliding over her own juices. But this time it was the red-painted toe I was contemplating.

"Deal," I answered. Then I licked the arch of her foot again to seal it . I started thinking Stephen must have one helluva job to afford Lilly.

Lilly lifted up onto her knees as she reached for my calves, and I decided it was time to prove I was up to her challenge. I quickly turned over onto my back, managing not to knock her off her knees, but she had to put her hands down on the floor to keep her balance. I was staring at her gorgeous, round ass, tan lines and all, split by the black lacy band of her thong. Her ass cheeks and thighs were slick and shiny from the oil, and I could see moisture of another kind around the edges of the panty of her thong. "God, you are lucious," was all I could manage.

She looked back over her shoulder at me and smiled when she said, "Hey now, that's off limits. Look but don't touch until I tell you, remember?"

I sat up sliding backward so as not to bump her beautiful backside and tick her off, saying, "I'm looking, believe me, I'm looking. Now I want to see all of you." I slid a finger up the inside of knee, her thigh, down the back of her thigh, over the bottom of her foot. She sat back on my thighs, her knees outside of mine, and lifted her tank top over her head. As her hair lifted, I saw a small tattoo, a Tiger Lily, at the nape of her neck. After her hair fell back, covering it, I gathered her hair together and pushed it over her should, then pulled her back into my chest, kissing and licking the nape of her neck, the little tattoo, her skin still moist and salty from her hard work.

I looked over her shoulder as I worked my way up her neck, and saw her naked breasts, large brownish-pink nipples erect. She leaned her head back against my shoulder, opening up her neck and throat to my tongue.

"It's my turn now," I said, reaching around her waist, running my hands down and back up the tops of her thighs, her hips, hooking my thumbs into the waist of her thong and pulling it down. She lifted up off my thighs, leaned forward so I work it over her hips, down her knees. "Lay down," I said, gently pushing her onto her stomach. I pulled the thong over her calves and feet, then reached for the oil, coating my hands with it, rubbing all over her legs and back, working it in, but being careful not touch her ass, not to screw up.

I was thinking through every trick I'd ever learned, trying to figure out how to get her to want me, listening to every change in her breath, any sign that I was on the right track. Then, finally, she started to respond, stretching her arms out and up over her head, the round sides of her breasts now barely peeking out.

"Oh, that feels good, Stephen," she whispered. "Harder, please." She sounded like she'd said that before...

My cock was practically throbbing as I worked the oil into her soft, soft skin, stroking over her back, working her shoulders, her thighs and calves, then to her feet. She had been letting out little sighs and whimpers, but when I got to her feet, she moaned, "Yesssssss."

I had been on my knees beside her legs, and moved around to her feet.

"Turn over for me, Lilly."

She rolled onto her back, her arms still up over her head, her hair fanned out on the floor, her breasts falling a bit to the sides, her stomach tight and tan, a small silver navel ring I hadn't noticed before, her mound of light brown hair, trimmed along her tan lines for a high-cut swim suit. I started rubbing oil into her feet, her shins, up onto her thighs, getting as close as I dared, pushing her thighs apart to open her up, expose the thick, wet lips of her pussy. I was massaging the insides of her thighs, pushing her legs further and further apart, opening her up wider. She started to pull her knees back together, but I stopped her.

"The deal was you would do whatever I wanted as long as I didn't touch you, Lilly. Now spread your legs," I said. She smiled, and let her knees fall back to the floor, fully opening herself. And that was when the tables turned.

I smiled back. I thought I might understand now - she liked not having to make all the decisions, but still wanted to be in control. I could handle that.

"That's good. That's perfect," I said. "Now, take some of that oil, and rub it into your breasts for me."

She smiled again, and complied, running her hands over her nipples, circling them with her fingers, then pulling and circling again. I moved up between her legs, continuing to work her inner things, first hard, then with just my fingertips, watching the goosebumps come and go from her skin. I circled onto her stomach, covering it with oil then barely trailing my fingers around in circles, up and down, up to brush her hands - but not her breasts - then all the way down her stomach over her thighs and back to her feet. She moaned again when I got to her feet, and I knew I had her now.

I picked up her foot, lightly running my hands over it, then kissed the top of her toes, licked them, worked my tongue between them. Her hips started to move, like she couldn't get comfortable. I worked my way around her foot and back to the top, then massaged her foot while I sucked and licked her little toe, then the next, then the next. She started making little "ah, ah, ah" noises every time she exhaled, her hips starting to work in circles.

Then her hands came down off her breasts, heading for her wet, wide open cunt, her clit practically standing on end. Before I'd even thought about it, I said, "Lilly, baby, you didn't ask permission. If I don't want you to do it, you can't."

Her eyes opened, and she got a wicked evil grin on her face. She reach around her hips, pulling apart the cheeks of her ass, letting her juices flow down, and said, "Stephen, may I please play with my clit and finger fuck myself while you watch me?"

Now how can a guy turn down a request like that? "Yes, you may," I answered, "But only because you asked so nicely. And you have to watch me, too," I said. She looked confused, so I stood up and dropped my boxers. I'm hung like a horse, and her eyes registered a bit of delight as she looked at my cock, red and rigid. Back down on my knees between her legs, I lifted her left leg up, her foot over my shoulder, and began stroking my cock, slowly so as not to explode.

"Go ahead, Lilly. I want to watch you."

She reached down with both hands, slipping her fingers into her juices, rubbing them over her clit, over her ass hole, up to her mouth to taste.

"My turn," I said, and she scooped up another finger-full and held it out to me, her other hand going to work on her clit. I took her fingers into my mouth, running my tongue over them, sucking them clean.

I let go of her fingers, and they went immediately to push inside her, first two, then three, working in and out, slipping out and down her crack then back up. She was furiously working her clit, watching pre-cum drip off my cock as I smiled at her, and she was about to orgasm, her breaths coming faster and faster. I reached out with my other hand, taking her wrist of the hand that was half-inside her, and said, "Now Lilly, stop." I licked her fingers clean again, sucking on them, watching as she worked her clit until she came, her hips thrusting into the air, her hole gaping, clenching, and dripping juices down her crack and onto the floor. She tried to pull her hand away from her clit then, and I said, "No, you have to keep playing with your clit. You can't stop until I tell you to. "

"Oh, God, you're serious about this, aren't you?" she said as her hand went back to work, a sexy, happy look on her face. I smiled as I turned my attention to her other foot, going to work on her toes, licking and sucking them, kissing and tonguing the arch of her foot, running my hands over her ankles and thighs. She started to breathe hard again, groaning, her hips twitching.

The orgasm rocked her, and again she tried to take her hand away from her clit, and again I told her no. She started to work again, and said, "Stephen, would you please fuck me? Please? I have to feel you inside me, I have to... Please?"

Finally.

I lifted her legs up over my shoulders, stroking her thighs, and asked, "Does this mean I can touch you now? How do you want it, Lilly?"

"Yes, Stephen, please. Do whatever you want, just fuck me."

I almost came before she got the words out of her mouth, but got it under control. I reached around to the front of her thighs and pulled her all the way up between my knees. I leaned over her, pulling her knees up to her shoulders, and said, "I thought you'd never ask," then plunged my cock deep into her cunt over and over again, covering her lips with mine, sucking her tongue into my mouth in time with my thrusts into her. She groaned, and came again, her hot walls gripping me, almost vibrating as she came yet again, and started to pant.

I kissed her deeply again, taking her legs from my shoulders and slipping my arms under her back, then sitting back up onto my haunches and bring her up with me. She was almost limp from the multiple orgasms, leaning into me, and I pushed her back, lifting one of her breasts to my mouth, biting and sucking her nipple as I held her ass in my other hand, still thrusting gently into her and trying to make this last as long as possible. Her recovery took a little longer this time, but her breathing sped up again as stroked up and down the cleft of her ass, circling the already-wet hole with my finger tip, pushing against it, into it as I nibbled at her breasts, licked her throat.

She dropped her head back, thrust her hips back against my finger, gyrating and reaching for her clit at the same time. I stopped her hand, and her head whipped up as her eyes opened.

"Oh, I'm sorry, I'm sorry Stephen. Please may I play with my clit while you finger fuck my ass, please?" she asked.

"No, you may not, Lilly. You may play with your clit while I fuck your ass, though," I answered, staring into her eys and pulling out of her swollen pussy and positioning the head of my cock against her tight hole.

"Thank you, Stephen," she answered, and pushed her ass down over the head of my throbbing cock with a sharp intake of her breath until her cunt was grinding onto my pelvic bone. She was so tight, and so deep, and she continued to stare into my eyes as her hand went back to work on her clit, as I thrust into her, pulling her hips down onto me and working them in circles.

"Oh yes, oh harder please Stephen fuck me harder," she pleaded. She held the back of my neck with her other hand, gyrating her hips, just trying to hang on as I slammed into her faster and faster, the ring of her asshole gripping, slipping as she came again and juices poured out of her cunt down her ass, coating my cock. My balls started to tighten, and I could feel the heat rising from deep in my pelvis, almost shaking as I came, filling her, setting off another orgasm, both of us groaning, staring into each other's eyes.

As my cock slipped out of her, she collapsed against my shoulder, still holding the back of my head. I stroked her back lightly, running my hands up into her hair as we caught our breath. After a while, her hand slipped down between us, finding my cock and stroking it. She giggled a little and said, "It's only 2:30. You've still got three and a half hours on the clock."

As I picked her up and moved us to the bed, all I could do was thank Stephen and Visa.