Diary of a High Price Escort Ch. 15

He thought for a moment then replied. "I don't think so."

"Well remember that tip." I answered.

He wasn't yet showing any signs of overcoming his shyness but at least he was keeping eye contact with me. That was about to change.

I unbuttoned my blazer and slipped it off tossing it on the bed beside me. "Do you think I'm sexy?"

His eyes dropped to the floor and I detected a faint blush on his cheeks.

"Look at me James. Do you think I'm sexy?" I repeated my question.

His eyes rose up as he replied. "Of course I think you're very sexy."

"Good I'm glad you think that." I answered.

He was kind of fidgeting as he looked at me. His hands moved up to his belt and he tugged on it, I assumed in an attempt to adjust his growing cock.

I slowly moved my fingers to the top button of my blouse and undid it. James eyes stayed fixed on my chest. When I opened the next one I pulled the fabric wider and leaned toward him letting this young man get his first glimpse of my lush soft cleavage.

He yanked on his belt again but that didn't help hide the growing bulge in his pants. "Are you going to undress right here in front of me?" He asked.

"Do you want me to?" I answered.

"Oh yes please." He instantly replied.

As I moved my fingers to the third button; the one that would expose all of my warm succulent cleavage, I said. "You know James its okay to touch yourself while you watch me undress."

After exposing my cleavage and the top of my bra I slid my hands down and pulled my blouse from the waistband of my tight pencil skirt.

As I undid another button I asked. "When other girls undress for you James; do you tell them how lovely they are?"

"I haven't in the past." He answered.

I smiled and gave him a second lesson. "You should start."

He smiled at me for the first time and I could see the veil of shyness beginning to lift.

My blouse fell open as I undid the last button and I slowly slipped it off my shoulders and tossed it to join my blazer on the bed.

His eyes were fixed on my cleavage as firmly as his hand was grasping his hard cock.

"I have big beautiful tits; don't you agree James." I asked.

He smiled again and replied. "Yes they are lovely." His answer telling me he'd understood my second lesson.

I shook my head causing my hair to fly around then fall haphazardly on my shoulders and cover part of my face.

I moved one finger up to the satin strap of my bra and slipped it off my shoulder letting it dangle against my upper arm.

"Have you ever helped a girl undress?" I asked.

He let his eyes drop again as he admitted. "No I haven't."

"Women love when their lover helps them undress." I said.

His eyes returned to mine as he began to speak. "Do you want me?" I interrupted. "Yes I want you to help me with my bra."

I turned to face away from him as I spoke. "Come close to me James."

I let my arms dangle at my sides as I sensed him approach from behind. He didn't touch me; I assumed he was waiting for my instruction.

"Do I smell good?" I asked knowing he was close enough to enjoy my perfume.

"Yes you smell wonderful." He answered.

"Make sure you tell a girl how wonderful she smells." I remarked giving him another lesson.

What I really wanted to do was move backward and press my ass against what I knew was a rock hard youthful cock, but I resisted the urge for now.

"James I want you to use your left index finger to slip the other strap off my shoulder." I said.

I could sense his finger trembling as he reached for my naked shoulder. At first he tried to push it aside but realized he'd have to hook his fingertip under the strap to have it move.

I tilted my head back as James succeeded with my bra strap which now dangled seductively just like its twin.

"Would you like to feel the lacy material of my bra?" I asked.

James replied softly. "Yes."

"Good I want you to reach around and touch my soft tits." I said.

I felt him move closer to me as his trembling hands circled my body. His hands crushed against my chest.

"Oh no James; girls like gentle first caresses." I remarked.

"My sorry Angel." He said as he removed his hands from my tits.

"Try again; but with a gentle light touch." I said.

His hands circled me again but this time his fingers barely touched the lacy material of my bra. I moaned softly; not because his soft caress excited me; but to show him the kind of reaction a gentle caress can invoke from a woman. I moved my hands up to cover his and pressed them a little firmer against my big soft tits and as I did I arched my back and pressed my ass against his loins.

James moved back, but quickly realized that I wanted to feel his erection against my ass and pressed his loins firmer against me.

I moved his hands up above the lacy bra covering my tits and let him feel the soft warm flesh of my chest. His hands no longer trembled rather they moved slowly as his fingertips absorbed the feeling of my naked skin.

"I'm beginning to get turned on." I remarked as he explored my upper body with his soft youthful fingers and palms.

He moved even closer and gently kissed my shoulder causing me to shudder lightly.

"I want you to undo the clasp of my bra." I said.

I was fairly certain he'd never done that before and James confirmed my thought when he said. "I'm not sure how to do that."

I wanted to giggle but held it inside. "Just take your time and use your fingertips." I suggested.

His hands moved between us and without too much fumbling he had both clasps undone. I'd dropped my arms to my sides and held the bar in place.

"Very nice." I complemented him on his small victory.

His hands touched my naked back slowly moving from the indentation from my bra up toward my shoulders.

"I want you to reach around and slowly remove my bra." I instructed.

James was a quick learner and rather than reaching around he moved his fingers up to my shoulders tracing along the tiny dents caused by the straps then down over the soft naked flesh of my chest until he finally reached the lacy fabric covering my tits.

"I love how gently you're being." I remarked and rewarded his soft touch by pressing my ass harder against his rock hard cock.

His fingertips toyed with the lacy at the top of my bra slowly inching further down and pulling the chest straps through the hold I had on them with my arms.

The cups loosened some and James moved his fingers deeper under the garment.

My nipples had long since hardened into sensitive nubs and I finally gave in to my own lust for his soft gently touch; lifting my arms and allowing the garment to fall from my chest. The shoulder straps slid down my arms and the bra fell to the floor in front of me.

"Oh my god." James murmured as his fingers slipped down toward my erect nipples.

I wanted to take his hands in mine and crush them against my tits; but this youthful man needed to understand that foreplay when done correctly should take forever.

His arms stretched up over my shoulders and finally he reached my nipples with his fingertips. He moved them side to side sliding each one over the hard nubs one fingertip at a time.

"I think you're getting the idea here James." I commented as he continued caressing and teasing my nipples.

"I like this." He replied.

His shyness had all but disappeared, but I suspected it very well may rear its ugly head again later in the evening.

"I want you to feel the full weight of my big tits." I said as I reached up and pulled his arms down along mine.

His fingers touched my flat belly for a moment then he moved his open hands up to cup my fullness lifting the soft orbs of pleasure and gently squeezing the warm flesh. I moaned as his hands moved over my chest and began grinding my ass up and down against his rock hard cock.

I let him caress and play with my tits for as long as he liked; instructing him to lift one orb while he gently rolled a hard nipple between his thumb and index finger. He followed my instructions and even experimented with lifting both tits and tweaking both nipples at the same time.

My chest tingled from his playful toying of my tits. Had he been an older more experienced man I suspected I'd have turned and dropped to my knees to play with his cock and balls much like he played with my tits.

My glands reacted to his touch and released moisture inside my pussy and I complemented him by saying. "You're making me very wet James."

"I am?" He replied almost sounding like he was surprised that I was getting wet.

"Would you like to feel how wet my pussy is?" I asked the obvious silly question.

"Oh my god YES!" He exclaimed.

I moved my hands up to grasp his and as I drew them from my tingling tits I said. "Unzip my skirt."

He had no problem with the zipper at the back of my skirt and as the tiny tap reached the bottom of its length I stepped forward.

"I want you to watch me as I take my skirt down." I suggested.

I moved my hands up to the waist band of my skirt rocked my hips back and forth as I slowly peeled the snug fitting garment off my hips.

"Oh my god Angel!" He exclaimed then quickly added "You're wearing a thong."

"Are you used to cotton panties?" I asked as I continued squeezing out of my skirt.

"Almost always." He answered.

The fabric finally loosened and to be honest I took more time than usual giving him time to fully appreciate the look of a sexy ass wearing a thong. I let go of the skirt and it fell to the floor in a puddle around my stilettos.

I was slightly bent at the waist and to tease my young client I slid my hands around to cover my ass than spread my fingers wide apart before pulling at my ass cheeks and showing him the spaghetti thin strip of fabric covering my asshole.

"Do you think I have a sexy ass" I questioned.

"I've never seen a sexier ass in my life." He replied.

I suspected he hadn't seen too many asses in his short life but I accepted the complement by shaking that sexy ass for him.

"You were going to feel how wet I am." I said reminding him that I wanted his touch. I pirouetted on my stilettos to face him. His eyes grew to saucer size as he got his first look at the twin orbs of pleasure he'd be so playful with moment earlier.

As I closed the short distance between us his eyes moved from mine down over my big soft tits and flat belly to their final goal; the tiny triangle of black lacy fabric hiding my moist pussy.

James stood motionless the only movement I detected was his eyes roaming up and down my mature sexy body. I reached out and took one hand in mine. "You have me soaking wet James." I remarked as I slipped his fingers under to top of my lacy thong.

I felt his hand tremble as it slid over my clean shaven pubic mound. His eyes were glued to mine until I closed mine when his fingertips touched my pulsing clit. A moment later his middle digit curled and slipped between my cunt lips.

"My cunt is so fucking wet for you." I softly whispered as James seized the moment and probed deeper into my steamy depths.

He didn't speak a word but as he slipped a second finger inside me I knew the last shards of shyness were gone from this young man.

"Oh god I love how you finger me." I exclaimed as his fingers explored every nook and cranny of my sopping wet cunt.

His free hand moved up to cup one soft tit and I moved my hands to the other and lifted the nipple toward his mouth.

"I want you to kiss my nipple, I want you to lick it, suck it and gently bite it." I told him.

His mouth dropped down as I lifted my offering toward it. His soft kiss sent a shiver through my body and when he placed his flattened tongue against the sensitive nub I shuddered. "Now suck it inside your mouth." I demanded. James drew my hard nipple between his teeth and then closed them lightly on the hard tip. "Yes." I exclaimed

"Do the other." I pleaded.

He switched up and began gently fondling the tit he had just been orally pleasing and I lifted the other to his very talented mouth.

I knew that if I allowed him to continue finger fucking my quivering cunt I'd climax standing there before him. I was supposed to be the experienced MILF here and I decided my orgasm could wait. I reached for his hand and pulled his soaking wet fingers from my cunt.

"Taste me." I said as I lifted his fingers toward his lips.

He gladly slipped his fingers between his lips and sucked my wetness from them.

"You taste so..." He paused.

"So what James." I asked.

"You taste so womanly." He said clearly not sure how to describe the taste of my cunt.

I took a half step back and slipped my own fingers inside my wet slit coating them completely. As I smeared my wetness on my own lips I said. "Taste me here."

James moved forward and embraced me my chest crushing against his fabric covered youthful chest. Our mouths met and I pierced his lips with my tongue. Our kiss wasn't passionate at least not a first I assumed he lacked the experience to know how to properly kiss a lustful woman.

I taught him with my lips, my tongue and my hands how to kiss a woman.

I broke our kiss my tongue sliding around his lips as it ended. Looking into his confident eyes I asked. "Have you ever eaten a woman's wet cunt?"

"Oh my gosh no." James replied.

"This is going to be very important James; I'm going to teach you how to drive any girl insane with your mouth." I explained.

"I'm all yours Angel." He replied with a wide smile on his lips.

"But first my dear, I want to remove your clothes." I announced.

"I've never, I always take my clothes off myself." James admitted.

"Not tonight." I replied as my hands grasped his shirt at the bottom and slowly pulled it up over his head. His chest was hairless and his nipples were a lite almost pink color. After tossing his shirt aside I ran my fingers through his curly red locks letting my long sexy nails scrape against his scalp.

"I love your hair." I said.

"You're the first." He replied.

I slowly slid my fingers down over his smooth chest reaching the waistband of his slacks. "I can't wait." James interrupted me. "To see if it's as red down there."

I smiled and corrected him. "No I can't wait to see this rock hard cock." My hand continued down to slid over the head and down the shaft.

He seemed to be somewhat concerned about how I would react to what I knew was a curly patch of red hair surrounding the base of his cock. "Just so you know I'm as red down there as I am up top."

I smiled and reassured him. "I don't give a dam what color your pubic hair is, what I'm most interested in is seeing how far down my throat I can press this hard cock." I gave it a gentle squeeze as I informed him that sometime that evening I'd be swallowing his cock and pressing my nose into his curly red pubic hair.

"Let's just take a look at it." I said as I slowly knelt before him.

His eyes were staring down at me, an excited lustful stair as I undid the clasp of his slacks. In a moment his pants were puddled around his ankles and my fingers were sliding up his naked legs toward the waistband of his white jockey shorts. The bulge in his shorts outlined the hard cock they covered.

I stretched the elastic out from his hips and slowly peeled them down. James didn't lie about being as red down there his thick curly red patch of pubic hair only served to pull my attention to the rock hard cock that stood at attention from the growth.

I didn't touch it but rather studied his youthful cock the light skinned complexion of his chest was duplicated in the color of his cock. His cock head surrounded by folds of uncircumcised flesh poked out from the excess flesh. Below his shaft was rock solid the veins that pumped blood through it buried deep within his shaft giving it a smooth sleek appearance. Dangling evenly below his red pubic mound his scrotum cradled twin cum producing balls. I wanted to touch it, I wanted to stretch his foreskin back and study what I knew would be a very sensitive corona. But I had other lessons I need to teach and as I stood up before him I spoke. "Are you ready to eat my hot sopping wet cunt?"

He smiled and said one word. "Absolutely."

I leaned forward and kissed him deeply then said. "Watch me."

He froze in place stoically standing there but watching every move I made.

I slowly walked between the beds then turned and sat down on the edge of the mattress. I looked at him and smiled then reclined with my head on a pillow and my legs stretched out toward him.

I knew I didn't need to ask, but I did so anyway. "Are you watching me?"

James instantly replied. "Every move."

I kept my legs together as I slid my hands over my tits and up to my neck. Using my long sleek fingers I combed my hair evenly out around my head keeping my eyes in constant contact with his.

As I moved my hands back down over my tits I lifted my hips slightly and hooked four fingers under the thin strips that held my thong to my waist. As the tiny garment slid off my ass I raised my legs straight up above me. From the foot of the bed James had a perfect view of my loins as I exposed them. I slid the thong up my thighs toward my knees then bent my legs and slid the lacy thong down my calves and over my stilettos. As I tossed it aside I slowly began spreading my legs and dropping my heels to the bed cover. Once I had the heels of my stilettos imbedded in the fabric of the cover I dropped my knees and exposed myself completely to James lustful stare.

I moved both hand between my thighs and used matching sleek digits to spread my cunt lips open showing him the pink moist flesh inside. I lifted one hand toward him and turned it palm up signaled with my index finger for him to come to me.

He wasted no time nearly jumping on the bed between my spread legs, his rock hard cock standing straight from his loins. I loved his enthusiasm but wanted him to understand just what I expected from him. "I want you to listen to every word I say and follow my instructions carefully." I said.

"I KNOW what to do." He answered emphasizing the word know. "I've watch tons of porn." He added.

I laughed and said. "Porn is a fantasy. This is the real deal." I said moving one hand to my wet cunt and sliding my fingers side to side massaging the wet lips. James kept his eyes fixed on my loins as I spoke again. "Think of me as the director of our porn movie, I'll tell you what to do when to do it and we won't have the pleasure of a second take. You're the male star and I'm counting on you getting it right from the start."

"I promise." James replied.

"Okay; from my toes to my waist I want you to touch everything, taste everything, kiss and lick everything." I started.

He started to lean down toward my wet cunt. "You don't go for the prize right away." I remarked. "Start with my ankles." I added.

I lifted my right leg up straightening my knee. James grabbed the heel of my stiletto and used his free hand to gently caress my ankle through the fabric of my hosiery. His free hand slid up along my shinbone and he released my shoe and followed with his second hand softly massaging my calf muscles.

"That's very nice." I commented.

His hands lingered on my calf for a while but I wasn't about to tell him to move on. Eventually James moved one hand to the back of my knee and with a gently push from the hand still on my shin he bent my leg and lowered my stiletto back to the bed. One hand slid to the outside of my knee and pulled my leg toward him as he leaned sideways and met my silk covered knee with his lips, planting a soft kiss on the inside of my leg.

He was doing just fine and I told him so. "I love being kissed all over my legs."

His soft kisses continued following his hands that inched closer to the tops of my stockings. This youthful man was quickly learning the art of seduction. His fingertip finally transitioned from silk to smooth naked flesh and as they did he hooked his fingers under the top of my stocking. I thought for a moment he was going to slide my hose down my leg and I prompted him. "Leave my stockings on James."