Benefits Ch. 03

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Flashback to Jake's first time.
7.8k words
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Part 3 of the 10 part series

Updated 11/01/2022
Created 10/15/2004
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None of the events in this story happened. It's all fiction folks.

"And when I woke up, he was gone. Never saw the guy again," Laura said. We were sitting in her bathtub, winding down after another grand night . "And that's how I lost my virginity."

"Wait a tic," I said, "You're telling me that you just boned some random guy in Jersey?"

"What, were you expecting some thing more grand and romantic from the chick who had your cum on her face within thirty minutes of meeting you? It's not like I'm a slut. I'm choosy about who I fuck. I was choosy with him."

"Okay then. What else can we talk about till we're ready for another round?"

"Well Jake, you could always tell me about your first time. I tried digging it out of Mila and Dyl, but neither know. What's the deal?"

"They don't know because I didn't tell them. I've never actually told anyone about it."

"Why? Embarrassed?"

"Hell no Laura. But the story is a bit hard to swallow."

"Spill it to me," she said with a smirk. "You know I'm good when it comes to swallowing."

"Okay then. But remember, you asked for it, and you have to PROMISE not to tell a soul."

******** THEN

"Wake up Jake, time for work," my father said to me.

"Errr......no wakey.....Jake go sleepy," I mumbled back.

"Come on now Jake," he said. "Get out of bed. You're the one who wanted to work for the family company for the summer, and we've got a big day."

"All right," I said.

"Good boy," My dad said, exiting my room. I slowly rose from my bed and gathered my clothes for the day. I picked up my DX t-shirt, boxers, jeans, and my black Chucks, and headed for the bathroom for a morning shower. In about 15 minutes I was out of the shower and dressed, but still very groggy.

"Hungry....breakfast," I managed to mumble.

"We'll get something from the McDonald's drive through. Now let's go Boy Wonder," said my Dad.

"Please, don't call me that."

"Oh yeah, I forgot, only your girlfriend can say it. I'm sorry," he said with a grin.

"Oh, that's a good one. I'll never understand why you didn't make it as a stand-up.....and she's not my girlfriend. My best friend that happens to be a girl, but not girlfriend."

He opened the door and I walked through it. "Whatever you say son," he said as he closed the door behind us. I hopped in the passenger seat of our van , and he in the driver's seat. He started the car and we were off. My Dad was in construction, and we sometimes did renovations for the city. Today we were beginning a job doing some renovations to a school. The place was called Torrance High School. It was the month of August, so no students would be there, but it wasn't empty. See, Torrance High School was where the high school sequences of my favorite show, "Buffy The Vampire Slayer", were filmed. So, I was a little perked about that. But not much, since I had only gotten about five hours of sleep. We eventually arrived to do some work on the interior of the school. Adding new lockers, building a new room, general stuff. Now, my dad's company also handled painting, which was where I was assigned occasionally, since my dad knew from experience I was a total dipshit when it came to actual construction. But painting for some reason I was okay at.

"Hey there loser," a familiar voice said as I walked to one of the building to help set up station.

"Hey Dyl," I replied. "What are you doing here, and how did you arrive?"

"Got a ride from your Mom. Remember? Your Dad offered to pay me to help you get this job done."

"Hnh, never told me. Well, how about you help me set up, so we can get this done with?"

"Yeah yeah, sure," he replied, picking up some paint cans and supplies. "Now, where are the babes?"

"The Hell? What are you talking about?"

"You know, the BABES. Sarah Michelle Gellar, Alyson Hannigan, Charisma Carpenter?"

"Oh. I always figured you for Nicholas Brendon man."

"Ha. Shut the fuck up. Now where are they?"

"Jesus Christ Dyl," I said, "is that the only reason you decided to do this?"

"No, I just LOOOOOVE to paint buildings. Fuck yeah that's why. You've met them before, right?"

"No dude. Never have. Probably won't dude. I don't even think shooting is starting today."

"WHAT THE FUCK?" he yelled. "You've gotta be shitting me!"

"'Fraid not, but my rude awakening this morning is more than worth it to see that look on your face. If only I had a camera."

"Oh fuck you," he said setting up the ladder near a building wall. "I'll tell you one thing though, no women, I ain't climbing that piece of shit."

"Yes you are, or I tell my dad, and no money for you. And honestly, you know all you'd do is ogle the chicks then go home and jerk it in the shower. We're only 16 dude."

"Damn it."

"Yeah yeah. Now pop open that can, pour some paint in the bin, and hand me that roller, so we can get this horseshit over with."

**********NOW

"Wait," Laura said sitting up and turning around as best she could in the tub, "what does some fucking school paint job with Dyl have to do with anything? Unless you two get in some zany 'Three Stooges'-like fight, tell me something else."

"If you would wait, I could get to the point. It's about the first time I ever had sex, and you'll have to hear about it tomorrow," I replied. It was 1:00 A.M., and Laura had an early day tomorrow.

"Fuck," she said. "Well, I'll come by your place tomorrow around three, and you'd better fucking finish the story."

"I will, but if Mila's still around, it'll have to wait until she's gone. She's coming by to help me to do some organization."

"Whatever, I just want to hear the fucking story," said Laura, exiting the tub.

********

"I can't quite reach," Mila said. "And remind me again why I'm the one reaching in the back of the top shelf of your closet?" She said while standing on her tip toes on a step-ladder.

"You volunteered short stuff," I replied. "And I know better than to attempt to talk you out of something you're determined to do."

"Can I un-volunteer?"

"No. But don't worry, I'm right behind you, so you're safe, but that's only if you fall backwards. Any other way, and you're pretty much screwed."

"Thank you SO much my Man Of Steel, I feel so much safer," she said sarcastically. "Just what exactly am I looking for up here?"

"Well, a card board box, but it should have a circular handle on it," I replied. "It has a bunch of my old Green Lantern comics."

"Ah, so I'm looking for something of the utmost importance," she said with a humorous tone. "Hey, I think I got it. It's stuck though."

"Give it a good pull. I promise I've got you covered."

"Okay...I think..I've got..it...WHOAAAAAA!" she said, and flew off the stool side ways. I caught her, and we tumbled onto the floor. She landed on top of me, we were face to face.

"See, told you I'd catch you," I said. "A true hero is always there when it counts."

"Once again, you're here, oh hero of mine," she said lightheartedly. "How will I ever repay you?"

"How about 5 bucks? A pizza perhaps?"

She gave me a laugh and started to just look at me deeply.

"What?" I asked. She didn't reply. She simply moved some hair out from my eyes.

"You have beautiful eyes, you know," she said. She leaned down to my face and kissed me deeply. My mind was racing at this point. I of course kissed back, but I was puzzled about what brought this on, because I didn't see it coming. Our tongues intertwined, and I wrapped my arms around her petite form. She signaled for me to lift myself up a bit, and she removed my t-shirt. I replied by slowly removing hers, leaving her in only a black bra. We returned to our heavy kissing. I slowly started to move my right hand to her crotch, which she was grinding against mine. Then, at that moment, a knock at my window came.

"Yo, bookworm, let me in!"

It was Laura, and just as suddenly as she had started, Mila darted off me and hopped onto the couch.

"I'm so sorry about that Jake," she said. "Don't know what came over me." She scrambled to put her shirt back on.

"No need to apologize," I said, putting my shirt back on as well. "We'll talk about it later." I got up and went to the door to let Laura in.

"I should really get going now anyway," said Mila, getting together her things and heading towards the door as I grabbed the nob. "I'll see you later."

"Mila, wait," I said. "We need to talk about this."

"We will, I just need to get my head together."

"Okay," I replied, and opened the door. Mila greeted Laura and rushed out.

"What was that about?" asked Laura.

"Oh nothing," I replied. "She just started to kiss and undress me, and vice versa, then heard you knock and felt very weird about it and rushed out."

"Oh, shit Jake, I'm so sorry," she said. "If I'd known...."

"Don't sweat it Laura," I replied. "It was bound to happen sooner or later. My surprise is it was her that made the move."

"I'm not. You know those eyes you make at her? Well, she makes them right back at you. I'm surprised you never noticed."

"Then why didn't she ever say anything?"]

"Probably the same reason you haven't," she said. "She doesn't want to lose you. She's a bit of chickenshit in that area as well."

"Great, fucking great," I said.

"Hey, just chill Jake. This could actually be a good thing. Something actually happened between you two."

"You think so?"

"Maybe," she said. "Never know unless you go for it."

"Yeah," I replied. "I have to know."

"Well good for you Jake. You seem to have shed the chickenshit skin."

"Yeah, thanks. You are a confidence booster. But I just hope things go well. I'm nervous as all fuck."

"You know what a good stress reliever is? Storytelling."

"I'm not really in the mood for storytelling, all right?"

"Oh come ON," said Laura. "You promised!"

"Jesus Laura, I really don't feel like talking about my first time right now!"

"You promised....."

"Fine."

*********THEN

"Dyl," I said. "I need you to refill the bin. Dyl?" I looked down from the ladder. Dyl had fallen asleep under a tree. "God dammit." I climbed down and smacked him on the head. "Who the fuck are you, Shaggy? WAKE UP!"

"WHA?" he said, sitting up with a jolt.

"For fuck's sake Dyl, my dad's paying you to help us paint, not sleep under a fucking tree."

"Dammit......can't I help with something else?"

"And leave me to paint here alone?"

"Glad you like the idea. I'm gonna go talk to your dad about what else I can do." And with that, he bolted off towards the building's inside, where my dad was handling some of the renovations with his crew.

"Ah fuck," I muttered. I couldn't do anything about it now though. I shrugged to myself and refilled the bin. It was also a bit hot as well, so I removed my DX shirt and sat it to the side of the ladder. I climbed back up and resumed painting.

I had been doing this for about half an hour when I first started noticing some voices behind me, though when I turned around to look, the people talking had been seemingly sitting their for a bit. From what I had heard, they had been commenting on me, actually complementing how I looked sans shirt. They all started to giggle like school girls when I turned around to notice. I blushed a bit I guess. Then again, what 16 year old guy wouldn't blush a bit if women like Charisma Carpenter, Sarah Michelle Gellar, and Alyson Hannigan were making rather nice comments on their appearance. Apparently they were doing some shooting today, exterior shots. And Dyl ran inside. I smiled to myself. Then I looked at them again and saw one coming towards me. It was Charisma. I started my way down the ladder. I had to fill the bin back up again anyhow, so if I could squeeze in some idle chit-hat with this beauty, why the Hell not?

"Hi there," she said, with me kneeling down at a paint can, pouring some into the bin.

"Uh, hi," I replied.

"You're doing a pretty good job, being here all by yourself, Mr....."

"Oh, um, I'm Jake Parker. You can just call me Jake if you want."

"Okay Jake. Like I was saying, you seem to be doing a fairly quick and good job on this wall here, doing it all alone." And technically she was right. All Dyl had been doing was filling the bin with paint.

"Oh, its nothing. About the only thing I'm good at in my dad's company."

"Oh, you work for your dad? Where would he happen to be?" she asked me.

"Oh, well he's inside, overseeing some of the minor renovations being made to the school."

"Oh, well thank you very much Jake," she said. "Could you please give me the company number? I have some renovations on my place I'd like to be done. Small stuff really, but I'm shopping around, trying to find the best price."

I reached into my back pocket and handed her a business card from a pack my dad always made me keep handy.

"Well, thank you very much Jake Parker," she said with a smile. "See you around." she said with a wave and another smile, and she walked back to her co-stars. I turned around and smiled to myself once again. Dyl missed the one thing he came to see, though it served him right.

Hours passed, and I had finished my job, with basically zero help from Dyl. I put my shirt back on and walked into the school, the area where the renovations were being done. I saw Dyl, looking completely and totally exhausted, carrying around some lumber.

"Havin' fun there Dyl?" I asked, and simply got a stern look as a reply. I walked over to my father, who was simply sitting down on a crate, talking on his cell phone. He hung up as I sat down with him.

"So, how much longer we gonna be here for Dad?"

"To tell you the truth, we could go right now. I just thought it'd be fun to watch Dyl squirm a bit."

"You are my hero Dad."

"I try." he replied with a shrug.

"So, everyone but Dyl is basically ready to head out?"

"Yep. You think we should tell him to wrap it up?"

"Sure," I said, just waiting for the moment I could tell Dyl what happened to me.

*********

It was around 8:00 in the evening. I was in my room, watching some TV and talking to Mila over the phone.

"So I'll see you at the movies this weekend?" I asked. This was finally my big chance. I had gotten a date out of her. Sure, it wasn't a "DATE" date, but it was just her and I. Alone. In a movie theater. Boo yah.

""Yeah, I'll see you at around 6:00."

"Cool. See you tomorrow Mila."

"I'm there. Bye Jake." I hung up the phone. I jumped on my bed in celebration. I had done it! FINALLY!! I was halfway through my happy dance that my dad came into my room.

"Hey son," he said perplexed, "Am I interrupting anything?"

"Er....no?" I replied, a tad bit embarrassed.

"Yeah right. Anyhow, I have some good news for you. You're gonna be making a bit more cash before schools starts up again. Overtime money for you."

"Great dad, now what's the catch?"

"Smart one aren't you," he said. "Well, I'm sending you do some painting at a house. Nothing big, just a couple of rooms. Two day job max."

"Okay, no big deal. Now let's hear the catch."

"It's tomorrow and Sunday."

"WHAT?" I asked in a yell. "Please tell me you're joking. Come on, PLEASE tell me this is just one of your really bad jokes."

"No joke sone. Why did you have something planned?"

"Well, I was going to go catch a flick with Mila at around six. But I guess I could be back here in time." When I said this, my dad winced a bit. "What is it now?"

"I doubt you'd be back by six," he said. "The job's a good mile and a half away, and I told the client you were good until six thirty."

I fell back on my bed, looking up at the ceiling. "I can't believe this."

"I'm sorry son. If I had known about your date, I would have had someone else do it. But it's to late now, everyone's going with me to finish up the renovations on the school, and I can't spare anyone."

"First of all, its not a date. Second of all, its not like you knew. Just give me some time to stew in this, okay?"

"Okay son," he said, walking out the door.

I laid on my bed for a good ten minutes before I worked up the nerve to call Mila to tell her I couldn't make it. She sounded really mad actually, and I could've sworn she hung up the phone with a slam. Needless to say, I got precious little sleep that night.

*********

It was around 11:00 in the morning, and I was on the highway to the house. I barely said a word to anyone as I loaded up my truck to head out to the job. I was actually in a mood not too suited to my traditional band of choice, so popped in something to allow me to further stew. So I was listening to the Cure on my CD player as I hit the exit, and made my way closer to this stupid fucking job that may have just cost me my ONE shot with Mila. I was pissed, depressed, and just generally in a "Fuck The World" state of mind. Towards the stroke of noon, I arrived at the house. I exited my truck and headed for the door to the house. It was a fairly nice one too. Two stories, decent lawn, probably air-conditioned. Probably wouldn't be ALL bad, but still, FTW. I walked to the door. There was a note taped to it.

"Just come on inside and get started. The room you'll be starting today is the second on the right when you climb the stairs."

I shrugged and went back out to my truck and started loading stuff into the room mentioned. I set down some plastic over the floor, and the ladder after. All I needed now was the person who actually hired me to come down. In all the business of being told I had to do this, no one ever gave me one clue on what color I was supposed to use. I had the usual room colors, whites, off-whites, beige, browns, and other, more out their choices in the truck. So I sat and waited. From listening to the sounds of the house, whoever was here was upstairs taking a shower, or something along those lines. Perhaps wash was being done. Never know, some people do have laundry machines on the second floor, when a second floor is to be had. Not many, but still, possibility. SO I just sat there and waited. Not long though, but in the mood I was in, one second was too long of a wait. Soon enough I heard the pipes stop, and a door upstairs open and close.

"Hello? Parker Construction here," I called out. " I was sent to paint some rooms."

"I'll be down in a second," a female voice replied.

"Great," I thought to myself. "This should be fun." Every time I've been on the job, and it's been for painting, or generally any kind of design for a woman, it's always taken twice as long as estimated. I don't mean to come off as judgmental, but from my past dealings, I was already increasing my pisseditude by 50%. I heard footsteps coming down the stairs, then the sound of feet walking on the tile floor towards the room. I couldn't believe my eyes when I saw who walked into the doorway.

"Well, Jake Parker," the woman said, standing there in her bathrobe, her hair still slightly damp. "Didn't think I'd see you here." It was Charisma Carpenter. IN her bathrobe. And nothing else. In front of me. Well, the day got a bit better. "Sorry for coming out like this. Laundry day and all. But anyhow I'll be up in my room if you need anything."

"Well, actually, I could use some info," I told her. "No one told me exactly what color you wanted the rooms painted in." Of course while saying this, it took all my will power to look her in the eyes as I said this, though I know I must have glanced a few shots at her cleavage. I just hope she didn't notice.

"Jake, eyes up here."

Well shit.

"Good boy. Now, I think for this room, beige is okay. It's not a private room or anything, nothing to personal. For the other room, I'll have to think a bit. Now if you need to use the restroom, it's right up the stairs, third door on the left. Any questions, just come to my bedroom, upstairs, straight down the hall, help yourself to something to drink if you get thirsty." With that, she turned quickly, the robe lifting a bit, just enough for me to get a glimpse of her ass, and she walked back up to her room. I opened the can of beige I had brought in, put some into the bin, put my roller in, and got to work. Since I had arrived and began work, half hour had passed by, and the only thing I could think of was Charisma, showering. Her hands running over naked form, caressing her soapy breast, sliding her hands between her legs.......I was getting insanely hard. I was ignoring this as best I could, but the more I tried to block out the thoughts, the more they fought there way to the surface. Eventually, I decided to do the only thing a 16 year old boy in my position would do. I headed up to the bathroom with the intention of whacking the thoughts away. I walked up calmly as possible, headed to the bathroom, and politely shut the door behind me. Then I turned to the toilet, put the seat up, fished out my cock and started to whack furiously, hoping to get it done with as soon as possible so I could hopefully get the job done a bit ahead of schedule. The longer I was at this, the more time it took away from painting, and I didn't want that. Despite the owner, I wanted to be out of this house ASAP.

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