As I smoothed my pencil skirt down over my hips and thighs, I noticed the tiny bumps in the fabric caused by the clasps of my garter. This won't do, I thought. I'd look too much like a whore walking into the lobby of the Grand Hilton, so I stepped out of my skirt and removed the garter. My thigh-high stockings would have to hold themselves in place. I liked my pencil skirt's sleek, slender look, which hugged my hips seductively. Slipping on black stilettos, I surveyed my reflection in the full-length mirror. It had a classy look, and the black skirt contrasted with my chosen white silk blouse. When I slipped the matching blazer over my shoulders, my appearance changed from classy and sexy to conservative. I was sure I'd impress both the father and his son.
I pulled into the garage at the Hilton and stopped at the valet station. The elderly man who approached offered his hand to help me step out of my Benz. I rewarded him with a glimpse of my creamy thigh above my stockings. "Take care of my baby," I said, handing him a fifty-dollar bill.
"Count on it, ma'am," he answered.
I started walking away from him but didn't hear the driver's door close, so I glanced over my shoulder and saw he was standing there watching me. I smiled and accentuated my steps a little more for his enjoyment.
I shoved the revolving door and stepped along with its speed as I entered the lobby of the Grand Hilton, which was surprisingly relatively empty considering the time of day. I took a few steps inside, surveying the lobby for a lone gentleman. No one approached me, so I continued deeper inside. A young lady behind the counter asked. "Can I help you?"
"I'm waiting for someone," I answered, then walked across the lobby and sat on one of the leather chairs for guests.
As I sat there, several couples walked by, and as almost always happens, I drew the attention of the men. They either gave me a quick smile or let their eyes roam over my form, not caring if the lady they were with noticed.
Nearly ten minutes passed, and I was beginning to feel somewhat uncomfortable about the wait when a middle-aged gentleman came out of the elevator and immediately noticed me sitting patiently waiting. He approached my chair and asked, "Are you Angel?"
"I am," I answered rather bluntly.
He reached out, offering his hand as he spoke. "I'm so sorry about being late; I was upstairs talking with my boy and didn't watch the time."
I accepted his handshake and lied. "It's not a problem."
"My name is Johnathan Westfield." He said.
I smiled and replied. "It's nice to meet you, Johnathan."
As I stood up, Johnathan suggested. "Why don't we go have a drink? I can talk to you about my son."
I wanted to know more about the boy's issues with females, so I agreed. "Good idea."
As we walked toward the lounge, Johnathan offered. "My son's name is James, but we call him Jimmy."
I thought Jimmy sounded so juvenile and immediately decided that when I met him, I'd give him the courtesy of using his given name.
Johnathan led me to the bar and pulled one stool away. I slipped onto the stool and crossed my legs; my pencil skirt rode above my knee as I did. Johnathan took notice of my shapely leg and sat beside me sideways on his stool. I unbuttoned my blazer, giving him something more than my legs to view.
"What'll ya have?" the young barkeep asked as he approached us.
"Angel?" Johnathan asked.
"I'd like a red wine spritzer, please," I told the barkeep.
"Let me have a draft," Johnathan said after I'd ordered.
As we waited for our drinks, Johnathan again apologized for his tartness, "I'm so sorry about not being in the lobby when you arrived."
I placed my hand on his thigh and again said, "It's not a problem; you've asked for the entire evening, so it's your time.
The way he looked at me made me feel like I'd be fucking him tonight instead of his youthful son, and I was sure at some point in the future, I'd be meeting him at a hotel to do just that.
Our drinks arrived, and after tasting my spritzer, I tried to get Johnathan back on point, "So, tell me about your son."
He smiled, realizing I wanted to get on with my task, "First, let me tell you that Jimmy is very shy. He's had several girlfriends, but each one has dumped him."
"Do you know why?" I asked.
Johnathan paused for a moment, then offered, "I did speak to one of the girls, and she told me that he seems to fumble when they get intimate."
"He is twenty, correct," I asked, wanting to make sure I wouldn't have a problem with him being underage.
"Yes, that's correct; he'll be twenty-one next week," Johnathan said.
I needed more details. "I was told that he has a problem with being abusive?" I asked.
"Well, let me put any fears you may have to rest. There is no indication of any physical abuse, but when things don't go well with a girl, he tends to become rather vulgar," He explained.
I leaned closer to Johnathan and whispered so only he could hear, "Vulgar isn't always a bad thing. I am often turned on by a man calling me a fucking slut." I smiled widely as I finished.
He grinned and replied, "I'm sure you are, but a college-age girl might find that kind of remark offensive."
I was beginning to get a clearer picture of my challenge with him. I'd quickly deal with his shyness and show him that any woman, regardless of age, wants to be treated with kindness, gentle caresses, and a slow, straightforward approach to intimacy.
"He has no physical challenges, does he?" I asked.
Johnathan instantly replied, "Not a one."
"Okay, can you give me about three hours?" I asked, figuring I could spend an hour talking to him and two showing him how to please a woman.
Johnathan looked at his watch and answered, "I'll call his cell around eleven o'clock."
I finished my spritzer and replied, "If a woman answers, give us another hour."
Johnathan laughed.
"What's the room number?" I asked.
"It's 1104," he replied.
"Okay, I'm going to go meet your son; I'm certain there will be some changes in the boy when I'm finished," I assured him.
I slipped off the stool, not bothering to keep my skirt from riding even higher on my thigh, and gave Johnathan a healthy look at the milky white flesh above my stocking tops. After all, Daddy said he was a very good client and had already proven to be an excellent tipper.
While the elevator rose to the eleventh floor, I smoothed my skirt along my legs and buttoned my blazer. It was a short walk from the elevator to the room. I knocked lightly on the door.
A few seconds later, I heard the deadbolt turn, and the door slowly opened.
I smiled widely and asked, "Are you James?"
He sheepishly replied, "Yes."
"Can I come in?" I asked since he didn't invite me in.
"Oh, I'm sorry; please come in," he replied.
James is about five feet ten inches tall, reasonably thin, and has curly red hair. I assumed that had something to do with his shyness since boys with red hair get called ginger and other unflattering things. He wore a pair of dark slacks and a blue pullover knit shirt.
I walked past him, then stopped and turned around.
"I'm Angel," I said, extending my hand toward him.
He took my hand and lightly shook it; I could feel the moisture in his palm.
"Please don't be nervous," I said.
He avoided eye contact with me as much as possible, and I knew I'd have to get him out of his shell initially, or it would be a long night.
"Are you in school?" I asked.
He replied, "Yes, I'm a sophomore at state." His eyes still didn't look at me.
I decided to take the bull by the horns and stepped forward until I was close to him. I placed one finger under his chin and lifted his face. "I want you to look at me, James," I sternly said.
He looked at me, and I could see fear in his eyes.
"I'm very shy," James offered.
I smiled at him and answered, "I'm here to help you get past that."
"I hope you can," he admitted.
I took a step back, and his eyes stayed fixed on mine.
"Do you think I'm pretty?" I asked.
"You're the most beautiful lady I've ever seen," James replied.
I smiled at him and gave him his first lesson, "You know, James, women like it when you tell them they are pretty. Have you ever told one of your girlfriends that they are pretty?" I asked.
He thought for a moment, then replied, "I don't think so."
"Well, remember that tip," I answered.
He wasn't yet showing signs of overcoming his shyness, but at least he kept 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 as he replied, "Of course, I think you're very sexy."
"Good, I'm glad you think that," I answered.
He was 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, it's 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, slowly slipping it off my shoulders and tossing 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 told me he'd understood my second lesson.
I shook my head, causing my hair to fly around and then fall haphazardly on my shoulders, covering 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 that 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 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. Instead, 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 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 sure he'd never done that before, and James confirmed my thoughts when he said that, "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 and held the bar in place.
"Very nice," I complimented 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 gentle 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 lace 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, 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 lust for his soft, gentle 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 before 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, and 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 complimented him by saying, "You're making me very wet, James."
"I am?" he replied, almost sounding surprised that I was getting wet.
"Would you like to feel how wet my pussy is?" I asked the apparent 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 waistband of my skirt, rocking my hips back and forth as I slowly peeled the snug-fitting garment off my hips.
"Oh, my God, Angel!" he exclaimed, quickly adding, "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, which 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 and then 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 compliment 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 been so playful with a 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 the 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 this young man's last shards of shyness were gone.
"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, lifting 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 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 at first. I assumed he lacked the experience to know how to kiss a lustful woman properly.
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 broad 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 over his head. His chest was hairless, and his nipples were a light, 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 slide 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, "So you know I'm as red down there as I am up top."
I smiled and reassured him, "I don't give a damn 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 was 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 needed to teach, and as I stood up before him, I spoke. "Are you ready to eat my hot, sopping-wet cunt?"