Friendship Found and Lost

Friendship found and lost Steve5511

The call from my service had come in a couple of hours ago but even so I'd only just picked up the message as I got into my car and checked my phone.

The appointment wasn't too far and I knew the hotel - knew the concierge even - and I could get something to eat and a coffee on the way.

I checked my face in the vanity mirror for any marks. My previous client had been a little rougher than I liked but there were no marks that I could see as I craned my neck from side to side.

In the diner I ordered a sandwich and coffee and called my baby sitter.

"Hi, everything ok?" I paused while she spoke. "No, I'll be a little later than planned so just use the pull-out bed. Sure, I'll pay the extra. Thanks. G'night."

I freshened up in the diner rest room and checked my makeup, making sure my lips were good and red and then went out to the car. Five blocks later I was in the parking lot of the hotel and I called the front desk.

This was a standard precaution; I didn't want to walk into some room and find a weirdo, or worse.

"Hi, could I speak with Mr Morgan, Mr Jim Morgan staying in room 1423?" While the operator connected me to the room I glanced at my watch: 10:56.

With any luck I'd be home by half-past midnight.

"Hi Jim? This is Anna. Just wanted to check it's ok to come up."

His voice sounded a little breathy, a little nervous perhaps and it was often this way; perhaps it was his first time or perhaps he was just excited but so long as he paid that was all that mattered.

I locked the car and walked into the hotel, crossing the lobby straight to the elevator bank, pressing the button for the 14th floor.

Another two years, another two years.

I'd been saying that to myself for the past four years but I was still short on the money I needed to put my daughter through college.

On the 14th I stepped out of the elevator and checked myself in the mirror on the wall opposite. I looked good, a simple black dress and high heels, not too high, just enough to add an elegance to my calves and ankles.

Most people would be checking themselves on the way down to the bar or perhaps to meet a date but me? I was headed in the other direction. I checked my lipstick one last time and walked to the room, knocking twice.

Two steps back, another precaution against being dragged into the room, and a smile switched on.

Here we go again.

The door was opened by a good-looking man and I walked in.

"Hi there.. I'm Jim.. come on in."

He stepped aside to let me into the room and I noticed that he glanced up and down the corridor before closing the door, checking to see if anyone had seen me enter his room.

This wasn't unusual, probably feeling nervous about being seen inviting a woman into his room although if he was from out of town or one of my regular clients using their 'safe room' then I couldn't imagine who they thought might see them.

So first impressions? OK I'd say, kind of cute and polite.

I took his hand and held onto it as he closed the door.

"Hi Jim," I said turning to him. I made sure I was close enough to him for him to feel the warmth of me "I'm Anna, it's good to meet you. Do you have something for me?"

As I said this I glanced around the room and then spotted the envelope on the dresser. This was standard, money first, fun and games afterwards; he'd have been told about this by my agency.

"Oh, that's fine, always good to do this so we can concentrate on enjoying ourselves."

I walked to the dresser and opened the envelope, counting the bills and then placing them in my pocket book.

"So Jim" I said, walking back to him, placing my hands flat on his chest. "Are you from out of town, just visiting or...?"

It was odd I thought. There was something about him that seemed familiar but I was sure I would have remembered if I'd had business with him before.

I picked at the buttons on his shirt. He was in good shape, mid-thirties I'd guess, the same age as me. I flicked my shoes off and stood on tiptoe to kiss him, just lightly on the lips. I could smell whiskey on his breath.

"So what do you do Jim? What brings you to town?"

Hi voice was pleasant when he replied.

"I'm a lawyer and I actually just won a big case so I figured I was going to.... um well treat myself."

"A lawyer hey and a successful one and you just won a big case? Well then it's my job to treat you don't you think?"

I laughed lightly and kissed him again. He was pulling me into him, his hands on my ass, not unpleasant but perhaps a little over eager so soon. I like to start off slowly, as if my client and I are on a date, so that my clients get the real girlfriend experience.

I reached behind me and eased his hands from my ass, leading him to the bed.

"I'll have to remember you if I ever get into trouble."

We were standing at the foot of the bed and I ran my hand up the inside of his thigh but stopped short of his crotch.

"So Jim, did you have anything in particular in mind for your treat or would you like me to surprise you? We've got plenty of time to enjoy ourselves..." I stretched up on tiptoe again so I could whisper in his ear. "... but I can stay as long as you like. It would be such a pity to rush things don't you think?"

I nuzzled his ear with my lips and pressed against him before continuing. "... all night if you like."

Again I ran my hand up the inside of his thigh but this time I continued until I could feel his hardness.

"I think we might need all night, don't you?"

Some men would agree to extra time immediately, others could be persuaded during the session and a few would stick with the regular hour they'd booked.

It was always worth a try and the reality is, those who agreed to extra time or the whole night finish up paying me to listen to them snoring but hey, it's their egos and money.

All my words and actions were designed solely to get my client so turned on that not only would they enjoy their time with me, they'd want more. A second hour was always more relaxed than the first, saved driving between appointments and an all-nighter usually meant a good night's sleep after the first session followed by a quicky in the morning before they had to get to work.

But Jim wasn't persuaded, perhaps his lawyer's mentality and caution or perhaps he thought that my $400 fee for the first hour was enough although I was sure he could afford more if he wanted to.

He laughed in a knowing sort of way.

"Well I don't know about all night" he replied. "But I do know that right now I'd like to see more of your body". For a moment he looked as if he was going to say something more, a thoughtful frown flickering across his brow as if he'd remembered something.

I gave his cock another squeeze through the fabric of his chinos and shuddered against him, speaking breathily.

"God Jim, you know how to make a woman feel sexy."

My hand found the buckle of his belt and I tugged it open, the lose end slapping against my hand as I released it.

"Why don't you kiss me Jim."

I stretched up to find his mouth and swirled my tongue against his while I slipped my hand inside his shorts, finding his cock. The smell and taste of scotch was strong on his breath and in his mouth and I guessed that he'd had a couple to steady his nerves before I arrived.

Breaking from the kiss I smiled at him as I fondled his rod, feeling the dampness of his precum.

"I think I'd better get you to help me out of my dress, don't you? And I turned so my back was to him.

"Can you manage the zip for me?"

I held my hair aside so Jim could get to the zipper of my dress and as he slowly pulled it down I pressed my ass against his crotch, moving a little and feeling the hardness of his erection against me. Jim breathed out heavily as I did and feeling his breath on my back I turned my head to smile at him over my shoulder but he wanted more and placing his hands on my shoulders, turned me to face him and then, almost tenderly, held my face in his hands as he kissed me, our tongues finding each other's as they swirled together.

He broke the kiss. "Take off the dress".

Jim is very aroused, both physically and mentally, and there's a powerful, commanding tone to his voice; I suppose he's used to getting his own way in court but I'm not being cross examined.

I could of course just do as he says and take off my dress but most men find it very sexy to see a half dressed woman, apparently vulnerable and partially exposed so I place my fingers to his lips.

"Ssh tiger, not so fast, there's no hurry," and I return to his belt, pulling it from the loops of his chinos, then folding it in half before smacking it against my leg. It makes a good 'thwack' as the two halves smack together.

Then I return to his chinos, easing the zipper down and moving down with it until I'm kneeling before him, pulling his chinos past his knees with my dress half off my shoulder, my breasts pressing against his thighs and my mouth nuzzling and nipping at his erection through his shorts.

I slip my hand up the leg of his shorts, grasping at his butt, pulling him to me until my face is buried in his crotch.

"My god Jim, you are big, strong," I say leaning back a little so that I can slip my fingers into the waistband of his shorts, easing them down until his cock is free and I take him into my mouth briefly, sucking on the head of his rigid member.

I still have his belt in my hand and I loop it behind him, using the leather to pull him to me, sucking again at his cock.

Jim has his hands in my hair, playing with it.

"Oh Anna, that feels so good. Take more of me." he pleads.

Jim starts to move his hips, his cock slipping deeper into my mouth and I have to resist the urge to gag as he pushes towards my throat, so I pull back a little, sucking on him as I do.

The belt is still round his butt and I release the buckle end and grab it between his legs, pulling it through slowly, letting the rough side of the leather graze between his cheeks and past his balls.

As the last of the belt slips past his balls I come up for air and kiss his belly.

"Do you like that Jim, the leather on your skin? Why don't you let me make you feel as if you've been really naughty because I think you are being naughty tonight aren't you?"

I stand up, my dress still hanging off my shoulder and I reach behind me to undo the clasp of my bra, letting my breasts tumble free.

"Tell me how you're being naughty tonight and we'll keep it our little secret shall we, just between you and me huh?"

I sit on the bed and pat the space beside me.

"Come and sit next to me Jim and tell me all about how naughty you're being. It will feel so much better when you do."

"Oh I want to be very naughty with you" he says sitting next to me, his erection twitching slightly. He reaches out and cups my breast, rubbing my nipple with his thumb and he's surprisingly gentle as he cups my breast and that's good, even pleasant. Some of the men I meet act like they've bought my body and can do whatever they like to me but this one isn't like that, at least, not yet and I put my hand over his, pressing his fingers against my nipple which hardens at the touch.

"See what you've done already, you've got me all excited." With my other hand I start to unbutton his shirt, grazing my nails against his nipples as I do.

"So tell me Jim, is there a Mrs Jim somewhere, a Mrs Jim that you're not going to tell about tonight?"

"No, no woman in my life right now. None but you."

I smile at him "That's very flattering, I like that."

I push his shirt off his shoulders. He's well built, fit, and I guess that he keeps in shape.

"You're very fit, very strong, I think you're going to make me very happy tonight."

I break from him and stand, pushing him back onto the bed and tugging at his chinos.

"If you let me undress you, I'll let you undress me."

He laughs. "Well you can undress me but if you don't mind, I'd rather watch you undress for me and could you put on those heels again? I love a woman in high heels." He propped himself up on his elbow to watch.

I retrieve my shoes and step into them, leaning forward a little as I do to make sure Jim has a good view of my breasts.

My dress and bra are already undone and all I have to do is let the dress slip off my shoulder and slide to the floor over my hips, taking my bra with it.

There's a bead of precum on his cock, glinting in the soft light of the room, and I bend forward to lick it with the tip of my tongue, allowing my breasts to hang down with my nipples brushing against his thighs and then I stand again, cradling my breasts with my hands, tweaking at my nipples which are still hard from Jim's earlier attention.

I smile and lick my lips, tasting his precum. There's no need to say anything and I turn so my back is towards him and hook my thumbs into the top of my panties glancing over my shoulder as I start to ease them towards my hips.

"Ready?" and saying this I bend forward so my butt is close to him as I slip my panties off, sliding them down my legs and stepping backward to free them from my shoes.

My ass is now only inches from him and I give a little wiggle.

"All yours Jim, help yourself."

He accepts my invitation and grabs my ass, his fingers digging into my cheeks as he runs his tongue up my thigh and over my butt and then he turns me round. With Jim sitting on the end of the bed I only have to lean over a little so he can take one of my breasts into his mouth, licking and sucking on my already hard nipple and then moving to my other breast he licks and sucks again as if wanting to give equal treatment. Jim's mouth on my nipples feels good, not rough but arousing and although I know what I'm doing is my job, at heart I'm just a girl and some men have it and some don't and this one has it; like the memory of someone that I was close to long ago Jim makes me feel good and for the moment I'm happy to drop the professional front and just enjoy what he's doing.

I have my hands on his shoulders to steady myself and again I'm struck again by the feeling that I've met Jim somewhere but I know he's never been a client of mine before tonight.

My thought is broken by his hand running up the inside of my thigh and I spread my legs a little, inviting him, sending him the message that he's exciting me and he is, when his hand moves between my legs, cupping my pussy so that the heel of his hand is on my mons and his fingers resting on my labia.

"Oh that feels good, don't stop, you have such clever hands."

The words come out like they do with every client but somehow, right now, I mean them.

I wonder if he'll notice the birthmark at the back of my left knee and then think 'well what if he does'. I was teased for that as a child but that was long ago.

Jim's cock is rigid and I reach down to stroke his shaft, rubbing my thumb on the slipperiness of his precum. He moans as I stroke the length of his cock and I think he might be going to cum but that would be a pity because I want to keep him on the edge for as long as I can; after all this is my job, I'm a professional and he's paying good money for my skills.

I learned the hard way to keep a guy on the edge in a massage parlour giving guys 'happy endings' for tips. The better I did it the more likely they'd ask for me again and the bigger tip I'd get and of course there was the feeling of control; I got so good I could have them begging for me to make them cum. I taught them the true meaning of sweet agony and used that knowledge to my own advantage when I started to work as an escort.

One of the older women in the massage parlour ran a call agency and for a small cut she'd take punter's enquiries and then pass them onto whoever was free to work. She said I had the looks and skills to be a successful escort just as she'd had when she was my age.

I was terrified the first time but the money was much better than giving guys hand jobs and after the first few it became routine, just as it was tonight with Jim.

But that was all a long time ago and now I'm looking after this guy whose cock is throbbing so I ease off the stroking and squeeze him gently but firmly, pulling him back from the edge.

As I ease off he turns and reaches behind him, grabbing a condom that he has along with a few others on the night stand. He turns back to me, handing me the condom.

"Will you do the honours because I need to have you now." and he slips his finger into me as if to reinforce what he's saying.

I always use condoms with my clients and carry my own supply but Jim has brought his own which adds to the feeling I have that this might be his first time with an escort and I wonder why? Or perhaps that's just the lawyer in him being prepared for any situation.

He might of course just be celebrating as he told me but why not celebrate with his wife or girlfriend? Or he might need to dominate, to use me, bolstering some inadequacy in himself or he might just be looking for some good, uncomplicated sex but why isn't a successful, good looking lawyer getting that at home?

It's a puzzle.

I take the condom from him and tear the foil, pulling the rubber free.

"Lie back." I say, popping the condom into my mouth and I bend to him, taking his cock into my mouth and pushing the condom down his shaft with my lips. I finish the job with my hands, smoothing the rubber onto the length of his rod and then, placing the head of his cock in my entrance, I ease myself onto him.

The punters love this and as an extra bonus the condom is extra slippery with my saliva.

"Feels good huh? I say as I start to ride him, slowly moving up and down. I don't think this phase will last long though; I think he'll want to fuck me, to feel that he's in control.

"Oh god yes." Jim's reply lets me know that he likes what I'm doing. He's playing with my breasts again, squeezing my nipples. I look at him but his eyes are focussed on something else and glancing over my shoulder I can see that he's watching me in the mirror opposite the end of the bed, watching me ride him but also something else, something that's caught his attention and then he's looking at me again, looking at me intently as if he's come to some realisation.

Our eyes lock and again for a moment I'm sure that I know Jim.

But from where?

I've racked my brain and I'm sure that he's never been a client of mine; I'd know anyway as I keep a note of all of them and there's some that I won't do business with again and then there's just the odd one, here or there, that I'd almost go with for free and I'm starting to think that Jim might be one of those.

But I keep reminding myself: just two more years, just two more years for my daughter's college fund.

So even though sometimes I'm tempted, there's no freebies.

I drag my mind back to the present, aware that Jim has been fucking me and enjoying it and I've been totally oblivious to what's happening but after so many clients it's often like this.

"Oh God yes!" Jim is saying as we fuck. I have to concentrate for a while, to let him think that he's the best I've ever had. There's nothing better than repeat business.

"God I love your cock, so strong, stroking my pussy, fucking me."

We continue for a while.

"Oh, you're going to make me cum, cumming...cumming..." and I collapse onto him, hugging him and kissing his neck.

Although for me there was no orgasm, men generally like to feel that they're good lovers so I give a shudder to convince him.

"Jesus you are some lover, that was just massive,"

We lie there for just a moment before Jim kisses the top of my head and then tilts my head up so that we're looking right at each other.

"Well, that was a nice warm up, now let's really fuck." says Jim and he rolls me onto my back driving into me hard, almost viciously. His lust is clear to see and there's a subtle change in Jim's demeanour; he seems suddenly more aggressive now he has me on my back and he's going to give me a 'good fucking' as if I need teaching a lesson or perhaps he wants to be in total control for a while.