He was nice. Easy to talk to, not at all boastful and seemingly more interested in me than in talking about himself. I did though, as advised by Mike in my 'training sessions,' keep turning the conversation back to him; after all that is everyone's favourite topic isn't it? I mean no one is really interested in other people's holiday photos are they?
A large glass of simply superb Chablis later and we were walking through Mayfair towards the restaurant. He was clearly well-known and we were shown to a corner table where we sat almost side by side with a view across the elegant room; in my limited knowledge it seemed to be the best table.
He told me he owned an tech company based in Illinois. By the advice from Mike and for discretion I didn't ask its name or the town where he lived or worked. "Be interested, but not inquisitive" Mike had explained adding. "If he wants you to know, he'll tell you, just don't ask intrusive questions."
He said he was married with three children, one of whom needed special care and that had caused problems in the marriage. Although it was surviving and on the surface was fine, and he thought they still loved each other, their sex life had diminished considerably in the past few years. "Hence Christina I need the buzz of girls like you."
"I understand," I said turning leaning forward a little and placing my fingertips on the back of his hand.
"It keeps me young Chrissy, and stops me straying," he explained rather illogically, but who was I to disagree?
My nerves reduced as I got to know him and as the bottle of wine was finished. I declined a cognac, but had a double expresso to overcome the alcohol.
"Undress for me," he asked politely, pouring us both a glass of champagne when we were in his sumptuous suite.
Does this make me a slut, a woman of easy virtue, a natural hooker or just a girl who lives on the edge, wants to push out the boundaries of her sexuality and loves to experiment, but I found undressing myself, having extensive foreplay and sex with a virtual stranger so easy.
It was flattering to see and hear his admiration and desire for me as I stood before him in the sitting room of the lounge and dropped the jacket on the floor. I ran my hands up and down my body a few times before lifting the lacy hem of the silky, cerise camisole up to my breasts. I stroked them through the material enjoying that feeling and liking the look on his face as I touched my tits. I pulled the camisole up and over my head and handed it to him: where the hell that idea came from I have no idea, perhaps I am a natural, born stripper!
"Oh Chrissy, you have lovely breasts," he said quietly, his eyes riveted on my little B cup fried eggs. I liked him saying that so I took my bra off and showed them to him in all their naked glory.
With lovers and when now posing with clients I adore being half undressed, either half actually, while the other party is fully clothed. I have no idea why, but it is such a massive turn on for me and that was the case with Derek. I think it was that turn on that made being with my first escort client so relatively easy.
"Come here," he said huskily.
I stood in front of him. He undid the brass button on the zip of my posh jeans. He put his hands on my hips, I leaned forward, my tits dangling invitingly for his mouth, and he gently sucked each nipple. He was good, just the right pressure, nothing too hard or aggressive. Nice. He turned me round.
"And you have a gorgeous butt, baby," he sighed running his hands over it. His fingers went into the waist band and he tried easing them down, but the zip was still done up. I didn't know whether he would want me to undo it or not, so I turned back to face him, thrusting my hips forward as I did. He smiled as he found the zip and slid it down. He turned me round again, then peeled the almost skin tight jeans down my bum revealing the white lacy thong that plunged between the mounds of my 'gorgeous butt.'
"Now where do nice young ladies like you get such great all over tans?" He asked running his fingers over each mound.
I was feeling relaxed and confident enough to try a jokey retort.
"Ah a trick of the trade Derek, and I can't reveal that."
"No I suppose not," he replied stroking my bum so wonderfully gently. He went on. "And you are revealing other, more important things to me aren't you?"
I smiled at that and muttered. "Yes Derek."
He left the waist band of my jeans round my upper thighs so that both cheeks in the thong were bare, but my thighs and legs were still covered. I bent forward a little, this time offering him my bum in place of my tits. He accepted the invitation. He kissed it and licked both cheeks. That was also very nice. He slid one hand round to my front his fingers slipping down and probing in the silk of my thong. He quickly found what he was looking for, and as he did, my entire body shuddered, so strong was the sensation in my clit.
"Oh God," I groaned not at all acting as Mike had told me some girls do, but you must not. "Men can always tell," he had said.
I half stumbled and was half pulled backwards so that my bum pressed against his face. One hand rubbing my clit, the other holding my hip, Derek rubbed his face all over my bum and got his tongue between my cheeks.
"Lean forward more."
"I can't," I replied "The jeans are in the way and I will lose my balance."
"Ok," he replied sounding disappointed.
"Like this then," I said moving away from him, sliding the jeans down round my knees and bending over a table so that my arms were resting on it and my head on them.
"Oh fuck, yes," he groaned, moving over to me and kneeling behind me.
Derek kissed, licked, sucked and gently nibbled both cheeks for some time. He alternated his fingers between rubbing my clit, by putting his arm round me, and stroking my pussy, by slipping his hand between my legs from behind. He was obviously something of a bum fan. His enthusiasm, the time he spent and the low moans and expressions of pleasure told me that; and that was fine by me for I really am sensitive down there.
I felt his tongue licking across one of my cheeks right along the curve of my crease. Then it slid down the 'cliff wall' deep into that musky crevice. It was almost as if he was exploring, no enquiring is a better term. Yes, he seemed to be asking my permission, how gentlemanly! A little wiggle and a low groan told him that I was giving him that. He quickly pulled the thin gusset to one side. His tongue then slid right into my crease and it licked along the bottom of it. It was absolutely, bloody gorgeous, particularly when he got the tip of it inside me a little. He did that by grasping each cheek, pulling them apart and stretching the puckered skin surrounding that hole. That opened it a little, which enabled him to give me that most sensational of sensations, anal, oral sex.
Odd isn't it, I adore my bum being fucked by a tongue, quite enjoy a finger's exploration, but am shit scared of having a cock up there? I was pleased that he did not ask and it was not until later that I recalled I had not ticked the box marked anal penetration on the online questionnaire I had completed. They must tell the customers of the girl's likes and dislikes I realised alter that evening.
"Lay on the bed for me," he said.
"Front or back?"
"Front please I have not finished with that glorious butt yet."
And he hadn't. He played with it for ages. Stroking, rubbing, pinching and caressing my inner thighs, each cheek and in the crease between them and then round the front onto my clit he took me very near to an orgasm rather more quickly than I preferred, but I fought it and managed to resist, for a while that is.
I was wondering just what was going on as he still had not undressed.
"Just stay right like that Chrissy I won't be a moment," he said as I felt his weight moving off the bed. He returned pretty quickly. "Is this ok?" He asked very considerately.
"What's that?" I replied turning my head and looking at him. He was holding a bottle of baby oil, but had not as I had suspected he might undressed.
"On your butt Chrissy," he said by way of explanation.
"Just open your legs for me," he said pulling gently on my ankle. He opened my legs pretty much as far as they would go and then just ran his fingertips up and down the inside of them up and over the cheeks of my bum and along the crease for a while. The feeling of the oil being poured onto and then running along the crease in my bum was lovely. As were his fingertips that followed its route up and down that sensitive valley. He fiddled one hand along my side obviously trying to get to my breast so I lifted myself up a little to give him full access to it. He cupped it and squeezed it nicely.
"Thanks Christina," he whispered.
"My pleasure," I replied without thinking, but suddenly realising it was precisely that.
His hand felt nice on my breast and nipple, but then so did the other one that was gliding all over the cheeks of my bum and up and down my thighs. Slowly, though, that one began to focus on my pussy and the crease in my bum. He would slip between my widely, probably almost lewdly, spreaded legs and gently run his fingertips along my lips. Sometimes slightly inside me, but then at other times just on the lips they would run from my clit at the front, along my sodden pussy across the perineum and into the gulf between the cheeks of my bottom. In there they would glide up and down slowly pausing each time right on my anus. Each time they paused he would press right on it and each time it was a little firmer. He removed his hand from my breast and started to use both between my legs and on my pussy and bum.
It was actually quite amazing and I found that my nervousness and apprehension had almost gone; I was beginning to enjoy having sex as an escort with my first client.
"You have a great ass, Chrissy," he whispered running one of his hands over both cheeks as the fingers on the other lingered in the crevice between them.
"Thanks," was all I could muster as a reply.
"Is it ok?"
"And this?" He asked as he pressed his fingertip on my clit then ran it along my pussy and the crease in my ass, as I now thought of it.
"Mmmm yes, again," I sighed.
He slid one hand between my legs and rubbed my clit and pressed the forefinger, I think, of the other hand right on my hole.
"Yes," I gasped as the combination of the sensations rushing from my clit collided with the anticipation of what I thought he was suggesting. 'He wants to finger fuck my bum,' I thought wondering why he did not seem to want to fuck me, well not yet at least.
"Yes Derek if that's what you want," I sighed.
"It is what I want Chrissy, I want your ass."
I panicked a little. "They told you I don't do anal penetration didn't they?"
"Yes don't worry my lovely I do not want to fuck your ass and in fact I do not want to fuck you at all," was his surprising reply.
'What the fuck did he want?' I asked myself.
"So what do you want?"
"I told you that I am relatively happily married and I do not want to be totally unfaithful to my wife. I know it's illogical, but if I just enjoy you with my mouth and fingers and we kiss, I will be happy."
He then went on to make the most beautiful and exciting finger love to me. He caressed my bum he stroked in the crease at the same time as which he ran his fingers along my pussy lips. His fingers slid inside my pussy and he pumped them a little causing my body to react and to hump back at the pleasure giving finger. He poured more oil on me and rubbed that into the crease paying particular attention to loosening and lubricating the puckered skin of my anus. He would press on that then move away only to return to it and press more firmly even slipping his fingertip and nail in a little way. Each time he pressed on it he waited. I didn't get what that was about at first, but then it hit me, he was asking my permission; he was seeking my agreement, but did not want to ask in words. The next time he ran his finger along the slit between my pussy lips, across my perineum and into the crease in my ass he kept going until his finger reached my anal hole. This time he pressed with increased pressure and held it there. I had to do something I knew that, after all he had bought me hadn't he? So as I felt his finger pressing more firmly I grunted then wiggled my bottom a little. I was saying yes, I was agreeing, I was giving my client the permission to push his finger up my ass and fuck me like that.
And that is what went on in my first experience as an escort.