True Trick: The Virgin Jim
His name was Jim, and I know it was really Jim, because I asked for an ID. Jim had called a week earlier, to set a date. A date to lose his virginity.
I met Jim at his hotel room, a *very* nice hotel, furthering my assumptions about Jim being a rich kid.
The hotel was very nice, posh, not swanky. His suite was not the 'Presidential' but sure was much larger than our hour would require.
I arrived at the door to the suite, and could hear a bit of music through the door. Too muffled to make out the tune, it stopped almost the instant that I knocked. The door was quickly opened, and I had my first glimpse of Jim. A tall, lean, young man, with a bit of acne, large brown eyes, and baby fine, dish-water blond hair.
He was eager to hand me the money, but I gestured to the table near the door, as one *never* takes the money directly from the client's hand. He quickly set it down, his ID was on top of the pile of bills.
I could tell he was nervous, as once he set the cash down he virtually leapt to the other side of the room. Realizing Jim needed a few minutes to re-group himself, I asked where the powder room was, and lifted the cash & my goodie bag and proceeded to the door he pointed to.
While I knew Jim needed a few moments to himself, I also knew if I waited too long, he may bolt. (It happens, even if they have paid.)
I looked at the nighties, gowns & teddies I had packed. I knew that black or red would be too intimidating, and white would be too much irony. So, I took out a shorter, moss green babydoll, and quickly dressed. I noticed the huge spa bath tub, and wished that this was a more experienced client. First times are awkward enough, no need to add water ;) ~~ But the tub was a dream...
I checked myself in the mirror, and quietly opened the door.
Jim was now seated in a chair at the end of the suite. I looked over my options quickly, and decided I should sit casually on the bed. I didn't want to risk being too assertive by joining him on the chair. And anything else would probably make him feel too awkward to join me on.
I asked him what music he had been listening too. He mumbled something, but then moved to the entertainment system (I told you this was a nice hotel!) and put a tape in. The room filled with classic jazz. I was a bit surprised.
I asked him who it was, which turned out to be the gem of all questions as it was his own band, doing a cover of some Turrentine tune, I can't remember exactly which anymore. And it was quite nice.
Talking about music really got Jim comfortable, and soon he joined me on the bed, though he remained at the foot of it. Animatedly talking about his band, Jazz in general , and how the kids in his class were more interested in Rap, which he found ludicrous, as they only thing these white rich kids had in common with rappers was (possibly) a large bank account.
Soon he realized my laughter was genuine, and he relaxed. We began to talk about his gigs, and eventually women.
(I had decided, during my drive to the date, that Jim was likely 1, a nice kid with a huge crush on 'Muffy' or some other country club debutant who had never even noticed him or 2, a guy with a girl he adored, but whom he didn't wish to scare with his sexual advances. It seemed often, these rich kids who waited were really caught up in some 1950's moments & didn't know what to do with themselves...)
Through our talks, I discovered a bit more of a complicted tale...
Jim had been serioulsy dating the same girl since they were both 13. Once he became a dedicated musician, and began to play some clubs, his girl became a bit threatened by some of the attention Jim received. Jim claims most of it was insecurity on her part, as he certainly was never approached by any women at these gigs, but it became a large issue between them. And eventually, her insecurities convinced her that Jim was doing her wrong by doing some other woman, and she decided to get even by giving up her own virginity.
Obviously, this caused them to break up, and Jim to consider his thoughts on sex in general. While he had been waiting for Ms Right & marriage, he now felt betrayed. But he didn't seek a professional as a retaliatory measure.
In fact, this break up was over a year ago. But Jim decided he was no longer going to feel ruled by insecurity, his future girl's or his own. He knew he wasn't ready to date yet, and felt a pro would be more honorable than perhaps misleading some girl, or even himself by being confused afterwards by his own feelings.
Rather mature for 18, huh?
Of course the heart to heart talk made Jim feel closer to me, and he stood up before me, and began to undress. First his shirt, then his shoes. He bent down to kiss me, his soft brown eyes slowly being covered by his eye lids... Then he stopped, his eyes still closed, and whispered 'Is it alright if I kiss you?' (This was more of the 'Pretty Woman' factor, than an insecure man asking permission. Normally I don't kiss clients, but can you even imagine a 'first-time' without kissing?! ) Without reply, I put my arms around his neck, and slowly, softly, kissed him.
He melted into me, and slowly brought his weight upon me, until I lay on my back on the bed. He began to move his right hand to the side of my face, and slowly up into my hair. His left hand crept to my breast, fondling it above the silk of the gown. He moaned, deep in his throat.
I in return ran my hands down his shoulders to his back, his ass, then after a few rubs, moved them between us, to loosen & remove his pants. Once the pants were removed, it was apparent we didn't have too much more time, and he placed the condom on. He kneeled above me, and I lifted the gown over my head. His eyes were still in soft focus as he absorbed my form. He smiled a shy smile, and began to move my legs open, and he ran his hand along my thigh. There was a small 'jump' from his cock, indicating, again, that we didn't have much time...
I took his hard cock and lead it to my warmth... he entered, with his eyes pressed closed, hard... his brows lifted once, twice, as he sighed... then he bean to thrust.
His thrusts were quick, hard and, to be honest, not many. He shuddered, and lay with his head nestled over my left shoulder, breathing hard. His back still tense.
I lay quietly. I wasn't sure if he was relaxed, sated, embarrassed... He began to laugh, a giant, full bellied laugh, and rolled off me, onto his back. This was a surprise!
"Listen,' he said, "I know my time is probably up, but can you stay awhile?"
I began to mumble something about the hour, when he interrupted "I intend to pay, and I am not love sick -- I am young, and I want to go again!" His voice was full of confidence and strength, his member beginning to rise again... "And I want to learn, learn how you feel... how it feels for you..."
I had to giggle in response. I also had to say 'Yes' -- who could resist? ;)
I went to leave the bed, to get my phone, but Jim was already leaping out of bed & returning with my bag, all smiles. I made my security call, saying I would check back in within an hour...
Jim took the phone from my hand, dropped it casually over his shoulder to the bag on the floor, and raising his eye brow, he gave me a killer smile. You know the kind -- intensely staring into your eyes, soft smile on his lips, with one corner just a bit higher than the other... He took his right hand, gently pushed me on the shoulder, and shoved me playfully onto the bed.
This time, his kisses were more confident, more playful, and more intense. His hands explored, but they were no longer timid. His fingers played with touch, with my response. My mouth, my nipples, my skin, my neck, they were stroked, pinched, sucked, and slowly trailed upon by his tongue...
He slid his hands along both my thighs as he shimmied down my body, kneeling before my spread legs. He took his long fingers, stroked my wetness, then rolled me onto my stomach. His hands felt the contours of my back, my ass, my hips, he slid his hard cock up and down my backside.
Then he slid back to his knees, and gently lifted me up to all fours. Once again he glided his fingers over my wetness, sliding one inside, as he ground himself into my thigh. He removed his finger, turned himself toward my ass, and slowly entered me. He shuddered, but stood his ground, trying to gain control of himself.
I know at this point I groaned, with the pleasure of his work as well as the anticipation of what would come... He shushed me with a soft, but firm whisper.
Then he slowly began to glide in & out of me. Slowly at first, feeling my reactions, measuring his actions to my responses... Then he pressed my head down into the bedding, moaning a little, and then he began to thrust harder... his body at once both in the joy of pleasure and the pain of trying to control himself... He said 'please' just once, whether to me to cum, or himself to hold on, I don't really know... But soon, soon, both were to be true. In a few more strokes, I began to shudder, my hands clenching the sheets, and he once again, with a giant thrust, collapsed onto my back...
Slowly we both sank fully to the bed...
...hot, sated, and covered in a light sweat...
we lay like that until my cell phone rang...
I left that night knowing that he would never need to call me (or another pro) again. But oh-so pleased that I had been the one...