First Time Heat

The call had come in pretty late in the week for a Saturday night. I'd had a regular client cancel his Saturday evening spot due to him having the flu, so I just happened to have an opening.

My regular client who was sick was in his mid fifties, divorced, and a wealthy sugar daddy of sorts, but at 29 I was a little too old to figure myself a sugar baby.

This wealthy client liked to buy me little presents and things, though. While that was kind, I didn't really feel comfortable accepting his more expensive gifts that he'd given me in the past. So now he only purchased me little inexpensive items like stockings and body oils. Mostly I liked this client because he was an older, dominant, confident man, a great fuck, and if he could have power fucked me through the mattress and down through the floor I would have gladly let him.

"This will be a new client for you," my boss had told me over the phone.

"Oh?" I asked. I had a pretty decent list of regulars that always requested me when they called in. Usually the younger girls took on the newbies.

"Yes. Everybody else was booked for this Saturday evening. And just so you know, the voice on the phone sounded pretty...young," she said.

I paused a few seconds. "Young? How young?" I asked, a little worriedly.

I was mildly concerned because a different local high-end escort service had gotten into some trouble a little while back because they hadn't been selective enough with their clients. Let's just say the underclassmen of a local high school lacrosse team thought they were going to have a much better evening than they had ended up having, spending the night at the local police precinct.

"No, no! Not that young!" My boss said. "But...young enough," she added.

"We are talking about someone legal?" I asked, just to be sure.

"Yes. Legal, but just barely," she said.

"Is it a first time?" I had asked warily.

I really preferred experienced gentlemen because I liked for them to take the lead in the bedroom and to simply fuck my brains out. I could probably do a first timer but I'd never done one before and it wasn't really what I was used to.

My boss giggled. "It is a first timer. I know you've never done an inexperienced newbie before, but I have faith that you'll do great. So, good luck to you!" She said, and she hung up before I could protest.

Great, I thought. I'll be fucking a man-child on Saturday night instead of my experienced power fucker. I sighed, feeling rather disappointed. This new guy probably wouldn't bring me any gifts, either.

The knowledge that I was going to be showing a newbie the ropes swirled around in my head all Saturday afternoon. I usually liked to meet new clients in a safe place such as a restaurant, and then we'd go on to a nice hotel from there. But this client had assured my boss that the only place he could meet me was at a house. If he was that young he probably couldn't reserve a hotel room anyway.

I got decked out for the date like I normally did. I wore a slinky red sparkly top, a short, tight black leather skirt, and stockings and high heels. I was shaved and waxed as normal and I'd put on some of my favorite perfume. It was called "Dangerous" and it made me feel quite dangerous when I wore it.

Later that evening my Uber dropped me off at a two-story suburban house in a nice neighborhood. The houses around me were one and two-story brick, with decent sized yards. It was a great place to raise a family, probably.

This house had one twenty-ish year old red car parked on the driveway and another equally old white car parked outside on the street. The outside of the house was otherwise dark and quiet but the house had warm-looking lights on the inside that shone out into the dark night.

I double checked the address on the wooden mailbox post and I walked up the driveway and onto the sidewalk that led to the front door. I smoothed down my wavy golden-brown hair and I rang the doorbell.

Several seconds passed and nobody answered, so I rang the doorbell again. I heard arguing on the other side of the door just as it opened.

"Would you calm down? It'll all be alright!" A young male voice said as the door opened.

There stood two individuals just looking at me.

"Hello! I'm Claire," I said.

I looked back and forth from the two "men" who were inside the house. One was tall and pretty nicely built with a shock of short, blonde hair. He grinned at me immediately. The other one was shorter, thinner, with shoulder length straight brown hair and wouldn't look at me for anything. They both were in their stockinged feet.

"Welcome, welcome, Claire! Come on in!" The taller one said. Boy, he was charismatic to a fault. "I'm Chad, by the way," he said.

I was a little confused because I didn't usually do two guys at a time, and I certainly hadn't been warned there would be two men here.

But still I was curious and so I walked inside and Chad closed the door behind me.

"You're Chad?" I said. "I didn't think -" I began, because that was not the name I had been given.

"Yeah, I'm Chad. This here is Oliver," Chad said, pointing to his shorter friend.

I glanced from Chad to Oliver and I smiled widely at the smaller guy.

Oliver was my client.

"Oliver?" I said.

He was looking down at the floor but at his name he glanced up at me and he blushed. "It's nice to meet you," I said.

"Yeah, you too," he said, looking down again at his feet.

"He's real shy," Chad said with an eye roll, being all Mr. Obvious.

I nodded. "I see. But that's okay," I said. "I like shy guys," I lied.

"So...do you just, um, take him upstairs? Or what?" Chad said.

I chuckled. "Well, that's Oliver's decision to make," I said. "Oliver?"

He didn't respond so I decided to take the reins.

"Um...Oliver, what are you drinking?" I asked.

"I just had one of Chad's dad's beers," he offered a little proudly.

I grinned. He was definitely underage for that. "Well, why don't we move on to soda or something like that? Would you want to go into the kitchen first? I'm kind of thirsty," I said.

He flushed again, looking at the wall. "Sure," he said.

But, he didn't move.

Chad finally rolled his eyes. "Come on, Romeo. Let's show her to the kitchen. But I can only hold your hand for so long, you know," he added on a grumble.

Oliver blew out a nervous breath of air and he followed us both into the kitchen.

"Oliver," I said, as he sat down at the table and his friend Chad got three Cokes out of the fridge, "I really like your house," I said.

"Thanks," Chad said. "Actually I live here with my parents. They're on vacation in the Cayman Islands right now," he said.

"Nice!" I said. "How come you didn't go?" I asked.

Chad grinned. "Football practice. Coach would have drawn and quartered me if I had disappeared for two weeks," he said.

"Ugh," Oliver groaned, rubbing his stomach like it hurt.

"And when the cat's away the boys will play?" I asked.

"Something like that," Chad answered with a grin.

"So...where do you guys go to school?" I asked.

"We're both seniors over at Central High. Oliver here just turned eighteen," Chad said. "But I've been eighteen now for a few months," he said, puffing out his chest a little bit.

I grinned. "Aha. I remember being eighteen," I said.

Chad laughed. "Sure! It couldn't have been that long ago for you," he said.

"Um...yeah, let's see...eleven years ago, but thanks," I said with a smile. "What kinds of things do you guys like to do?" I asked Oliver, but Chad answered.

"I play football. And I wrestle," Chad said.

"Nice! Oliver? You?" I asked.

He looked sick. "I have to, um - " and he ran off. I heard a door down the hallway close that I assumed was a bathroom.

"Oh, man. We had tacos earlier for dinner. Maybe that wasn't such a great idea," Chad offered, looking worried.

I smiled. "Poor guy. I'll go check on him. I'll be right back," I said.

I headed down the dark hallway and stopped outside the closed door with the light shining out from the bottom.

"Oliver, are you okay, buddy?" I asked from the outside of the door.

He groaned. "Don't come in! I feel sick. Leave me alone!" He said.

I smiled. "It's okay. Take your time, guy," I said, giving two friendly knocks on the bathroom door.

I came back into the kitchen.

"Is he taking a crap?!" Chad exclaimed in disbelief.

I nodded with a grin.

Chad frowned. "Well, that's gross! And he can't be sick! We only have you for like an hour!" He said. "We can't afford to pay you for any more time!"

I sat back down on a kitchen chair. "Relax. Listen, it's his first time...right?" I asked.

Chad nodded. "Yeah. Poor bastard has never even had a girlfriend. Has never been kissed. I fuck my girlfriend every chance I get. I just wanted him to have the same...you know..."

I waved my hand through the air. "Don't worry about it," I assured him. "I'll make sure Oliver's very happy by the time I leave," I said.

Chad blew out a relieved breath. "Thanks. This took all his Christmas money and some from me for his birthday," he said.

I smiled. "Wow. I think that you're a good friend, Chad."

He beamed.

A few seconds later Oliver came walking slowly into the kitchen.

"Feel better?" I said.

He still had his hand on his stomach. "I don't know," he said.

Chad sent me an alarmed look. He grabbed Oliver and tugged him into the other corner of the kitchen. I pretended not to hear what they were talking about, but words like "man up!" And "don't be a pussy!" Drifted over to me as I sipped my Coke.

I noticed Oliver glancing at me from the corner of my eye. He nodded reluctantly at what Chad was saying.

I turned my head and I looked at Oliver straight on and I smiled at him. I knew that my smile was pretty disarming and I was hoping it would calm his nerves.

"You guys can use my bedroom," Chad said, coming back over to me. "First bedroom at the top of the stairs," he said.

I nodded. "Oliver? Shall we go?" I asked.

I heard Oliver audibly gulp, but he nodded. I stood and held out my hand. "Lead the way," I said.

He stared at my hand for a few seconds.

"Take her hand, dumbass!" Chad said through clenched teeth.

Oliver flushed again. He took my hand in his sweaty palm and led me quickly up the stairs.

Chad's bedroom was indeed the first room at the top of the stairs and it screamed "high school boy". Heavy metal music posters were on the wall along with pro football players and famous pro wrestlers. He had a mirror on one wall with pictures on it of a cute high school girl in a cheerleader outfit which I figured must be his girlfriend. He had some free weights in one corner of his room that I could imagine him using. The bedroom walls were painted dark blue, which complimented the tan carpet nicely. He had a plaid blue bedspread on an unmade queen sized bed with light blue sheets.

I immediately went to the bed and started to make it.

"Do I...um...just take all my clothes off right now?" Oliver asked.

I smiled to myself as I tugged the sheets into place. "Do whatever makes you feel comfortable, Oliver. But we sure don't have to start out triple X rated if you don't want to," I said, glancing over at him.

He waited until I had made the bed, then he loped over and sat down on the comforter.

"This is embarrassing, and it was all Chad's idea. I know I'm going to suck at this," he said, looking down at his long hands with his slender fingers.

"Okay. Stop," I said, sitting on the bed next to him. "Tell me what's worrying you," I said.

He scrunched up his face. "Lots of things. What if I can't come? What if I come too fast? What if I do something embarrassing? What if-"

"Okay," I said, with a gentle chuckle. I put a calming hand on his thigh. "Take a deep breath, Oliver. Here's what we'll do. Let's set some rules at the get-go, okay?"

"Rules? Like what?" He asked dubiously.

"Like...you can come as many times as you want...okay? Don't worry about being too fast or too slow, alright? We both know this isn't a fakey porn shoot. There are no expectations here. You set the rules, got it? If you like what's happening, say so. If you don't like what's happening, say so and we'll change it. Sound good?" I asked.

He blew out a big breath. He looked a little bit more relieved.

Oliver really was a cute, normal-looking, average kid, I thought as I studied him. His friend Chad was probably considered better looking by the girls. Chad had a few pimples on his face but was outgoing as hell so they weren't all that noticeable. It was easy to see why his quiet best friend Oliver got overlooked with Chad around. The smaller kid had no self confidence to speak of. But in direct contrast with Chad, Oliver had beautiful porcelain skin. He had skin that even I envied.

"You know, you're really a cute guy," I blurted out.

He looked up to make sure I wasn't blowing smoke up his ass and then he flushed and smiled.

"And your skin!" I said. "It's absolutely gorgeous!" I said. I reached out and ran a finger down his cheek. His flush intensified.

"Someday, Oliver, you're going to make a girl very, very happy, I just know it," I told him.

He looked away but couldn't hide his half-grin.

"Okay. So what do you want to do first?" I asked. "Let's start easy is my suggestion."

Oliver resembled a deer caught in a pair of bright car headlights. "I don't know," he said, shaking his head.

"Hum," I said. "Well, how about I give you a little backrub?" I suggested. "That will loosen you up a bit," I said.

He hesitantly nodded. "You mean like with essential oils and shit?" He asked.

I laughed. "Nope. Just with my bare hands," I said.

"Oh. Okay. That would probably work," he said.

I climbed behind him on the bed and I put my hands on his shoulders over his gray t-shirt. He felt really tense so I started to massage him. "So, Oliver. Tell me a little bit about yourself. What kinds of things do you like to do for fun?" I asked as my fingers worked.

"Um...well I play a lot of video games. I like geocaching. And I play the saxophone," he said.

"That's cool. But you'll have to tell me, what's geocaching?" I asked.

"Oh. It's when you go to a specific location that you find on a geocaching app. You use coordinates to find the place. Then you usually find a logbook that someone's hidden there and you sign your name on it. It's kind of like a treasure hunt. I do it with my dad or with Chad sometimes," he said.

"Aha! That sounds like fun," I said as I dug my thumb into a particularly stubborn knot on the back of Oliver's neck. "What about your favorite subjects in school?"

"I like anything science, especially space stuff. But I also like band. And I like my shop class. We're making chairs right now," he said.

"Wow, you're really well-rounded, I think. Do you drive?" I asked.

He nodded.

"I've had some really fun experiences in the backseat of cars," I chuckled.

He shrugged. "Man, I have not," he said.

"Do you ever think about it? Taking a special girl wherever kids go to make out?" I asked.

He shrugged and then shook his head. "Nobody would want to go with me," he said.

"Oh, now that's not true!" I said emphatically. "Have you ever asked anyone?"

He just shook his head.

"Hum. Tell me: What kind of fantasies do you have?" I asked him.

He paused, but he shrugged again.

"Well, what do you like to think about when you beat off?" I asked.

He looked back at me in horror.

I chuckled. "Come on. Everybody does it, I guarantee you. What kind of things do you think about?" I asked him in a whisper, my lips in his hair just right next to his ear.

He shuddered from my closeness. "Um...well..."

"Can you tell me? Odds are we can make it happen tonight," I whispered.

"Well, I...I sometimes think about this girl Stacey at school. She's a cheerleader friend of Tanya's, Chad's girlfriend. She has these really full lips. I guess I often think about her lips around my..."

"Gotcha!" I said. "That's a great fantasy!" I added.

"You don't think it's pervy?" He asked.

"What? No! I mean everybody has fantasies. I'd imagine lots of kids at your school star in other kids' fantasies."

He grinned a bit at that. "I guess," he admitted.

"Since you like Stacey's mouth...why don't we make tonight all about lips? Would you like for me to kiss you?" I asked him.

He shrugged. "I've never been kissed. I don't know what I'm doing," he said.

I took my hands off his shoulders and I moved so that I was sitting in front of him. I took his hands in mine.

"Aww, Oliver, kissing is pretty easy. Here," I said, scooting a little bit closer to him. "You just start out like this..." I said. I started to lean in. "Look into the other person's eyes. Move in a little closer...and I'll tilt my head so our noses don't bump..."

Truth be told he looked absolutely terrified, but he managed to pucker his lips a bit and when mine touched his, his lips were soft and trembling.

The knowledge of his sweet nervousness hit me in my chest and then zinged straight down to my pussy. What was happening right now? Kissing this boy's unsure lips was shockingly quite possibly one of the most arousing moments of my life.

I let my lips linger on his until I felt his tongue peek out. I met his tongue with mine and I opened my mouth and then I really kissed him.

He moved right along with me until he suddenly nipped very gently at my bottom lip. It was then my turn to shiver.

I smiled, breathing a bit heavy. "That was wonderful, Oliver," I murmured.

"R-really?" He asked.

I nodded. "Let's do it again," I said.

This time Oliver was a bit more fearless as he kissed me, his young mouth begging for more from me. I extended my tongue and lightly licked his bottom lip. He chuckled and continued the kiss.

It was astounding. It was like I was watching the boy bloom right before my eyes.

I reached my hands up to clasp them behind his neck and he scooted in even closer.

We kissed like that for several minutes, our tongues playing together wildly.

When I finally pulled away he looked a little bit kiss-drunk.

And I felt that way.

"I think you're really getting the hang of kissing!" I praised.

"Yeah?" He asked.

I nodded. "Yeah. How about we lie down on the bed now?" I said.

I kicked my high heeled shoes off and urged him to lie down on his side. I did the same. I leaned in closer and kissed him again, but this time I really allowed myself to get lost in the kiss. When I felt the urge to moan I didn't hold back, and when the kiss ended, his lips were swollen and cherry-frosted.

"God, your moans are going straight to my...you know," he said.

"Your cock?" I suggested.

He nodded.

I grinned. "Why don't we take off your shirt?" I suggested.

Oliver sat up a little and grabbed his T-shirt at the nape of his neck and in one motion tugged it off of his body.

I paused. "God, I really love it when a man takes his shirt off like that," I chuckled, surprised to see him do it that way.

How was this young kid so different than what I usually liked, yet he was somehow pushing all of my buttons?

I leaned in to kiss him again. "Touch me," I begged as I ran my hand over his absolutely hairless chest.

He put his hand on my shoulder and I chuckled. "You can touch me anywhere you like," I said to him. "Not just on my shoulder," I said.

His hand slid down until he was tentatively cupping my breast.

"Congrats! You've made it to second base, Oliver," I teased.

He chuckled. "Looks like it," he agreed.

I sat up and took off my dressy sparkly red tank top. Oliver's very prominent Adam's apple jumped in his throat as he took in my black lacy bra.

He traced the lace along the tops of my cups and my nipples hardened just from that indirect touch.

"Oliver," I whispered. "Can I undo your jeans?" I asked.