Benefits – Chapter 3

Benefits Ch. 3

First Time’s A Charm

By. Mr. Fantastic

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.”


“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…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…..”



“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.

I had been beating it for about five minutes when I got the feeling I was on the verge. I know that doesn’t sound all that great, but when you’re sixteen and a virgin, you’re only concern isn’t time length, it’s getting off. I was getting there. But right when I felt it arriving, the door opened, and on instinct I turned around, my cock in my hand, ready to burst. And of course, there was Charisma, in her bathrobe, looking me right in my own face, which was covered in a look of shock, fear, and embarrassment.

“Well”, she said, taking her eyes from my face to my still painfully hard dick, “You on your lunch break Jake?”

“Er..uh…,” I struggled to find some words to possibly explain my current situation. “I am so sorry about this Ms. Carpenter, PLEASE don’t get me in any kind of trouble, please…..”

“Please Jake, you act like this is the first time I’ve seen something like this. I mean sure, not from a teenager, but still, I am a bit aware of the affect I can have on people. You’re in no trouble. I’d be lying if I said I wasn’t a little bit weirded out, I mean, I did just catch someone I don’t even know jacking off in my bathroom.”

“Listen, I’m sorry..” I got out before she walked over to me and pressed her finger to my lips, shushing me.

“Like I said, just calm down Jake,” she said as she looked down at my cock, still making me look like a tool by staying hard. “Looks like you’re brain isn’t the only thing not calming down.” She smirked at me and reached down for my cock. “Would you like me to finish this? Then you can get back to work?” I simply nodded, befuddled at the current situation. She looked me in the eyes as she grabbed my cock. She started to jack me, slowly at first. “I bet you like this. Sexy woman jacking you off, wanting you to shoot your cum for her….mmmm….I bet you love just the thought don’t you?” Once again, all I could do was nod. She flashed me that amazing smile of hers and started to jerk me faster, now moving her other hand down to massage my balls, squeezing and kneading them, tugging on the sack. My breathing was getting heavier. I was already close when she walked in, and I was amazed I didn’t cum when her hand was a centimeter away, but I was ready to now. She looked at the expression on my face, and began to urge me on. “Cum for me, cum for Charisma. Give me all you have, come one Jakey…..” I couldn’t take it anymore. With a loud gasp, I let my cum fly, covering the area of her robe closest to my crotch. She let my cock free once every thing had been emptied out. She took her hand to the cum covered area of her robe, and took some cum and massaged it into her breasts. She then took me by the hand and took me to her bed room.

“Uh..” I was attempting to get some words out, but failing.

“What is it Jake?” she asked, removing her robe, showing me her naked body completely. Her breasts were amazing, the first pair I had actually seen in person, as opposed to a magazine. The nipples were hard, and nickel shaped. A light shade of brown, though a bit darker than the rest of her tan body. Her legs were just as amazing as I’d always known, and her pubic hair was shaved into a triangular shape, the lips bare however. I was still struggling for words as she started to walk towards me. She grabbed me by the face and kissed me. “You’re really nervous Jake. Didn’t think you’d be. Hot guy like you. Must have had lots of women, despite your age.” I was a bit flabbergasted, and could only shake my head at her assumption. “Really? How many women then?”

“Um,” I said, finally getting the energy to form a few words. “More like zero.” She was visibly taken aback by this bit of knowledge.

“You’re a virgin?” she asked me, to which I could only reply with an embarrassed nod. “Oh honey, there’s nothing to be embarrassed about. This could be kind of fun. Never got to deflower a guy before.” she said with a smile. “I guess this little situation’s gonna make me a teacher of sorts.” She laid herself down on the bed. “Take off your clothes.” I nervously complied stripping myself naked. My cock once again completely hard. She signaled with her finger for me to come join her on the bed. “So you’ve never been with anyone before?” she said as I crawled on the bed towards her. I shook my head. “Well, looks like I’ll be breaking you in.” She grabbed me by the head and pulled me up to her face for a kiss. “I want you to put your cock in me. I want you to fuck me. Can you do that Jake?” I nodded nervously. “Good.” She took my cock in her hand and guided me to her opening. “Thrust in Jake.” I did as she asked and thrust my cock into her pussy. I let out a loud gasp at this new feeling. I savored it. It was amazing. The wet heat of it. Her pussy fit my inexperienced cock like a velvet glove. I must have been savoring it too long, because Charisma propped herself on her elbows and looked me in the eyes. “Jake, I know its your first time and all, but please, could you continue? I’d like to enjoy this to.”

“Sorry,” I said sheepishly. I began to pull out and thrust back in slowly, knowing good and well with this being my first time, I would have zero stamina if I went hard and fast. I moved my face down to her neck and started to kiss and suck on it, hoping I would add to her enjoyment. She let out a soft moan, which I hoped was real. I moved my mouth down to her bountiful breasts. I licked them and caressed them with my hands. I pinched and sucked on her hard nipples, occasionally nibbling on them, eliciting more moans of encouragement from her mouth as I thrusted into her pussy.

“Fuck Jake, do it harder….fuck me,” Charisma moaned. Though I was nervous about speeding up and popping early, she was the boss in this situation. I put my arms by her shoulders to steady myself and I began to thrust into her harder, the sound of our skin slapping together now very audible. Luckily no one else was in the house, because I was fairly sure this would have been a crime for her. Whatever I was doing, I must have been doing a fairly good job at it. Every thrust elicited a moan from her. Then again, she could just been acting. That was her profession after all. I continued to thrust into with abandon, thrusting harder and faster as time went on, not even realizing it myself. I stared at her face as it contorted with pleasure.

“Please don’t be faking it,” I thought to myself. Then I felt the tingling in my balls. “I’m gonna cum soon,” I managed to get out”

“Pull out of me Jake,” she said. I complied, and she promptly held my cock she sat up to face me. I felt I needed to cum, but nothing came out, not even a drop. I was fucking hurting. “You need to learn to pace yourself babe. Mix the hard and fast with the slow and sweet to make it last longer.” She looked down at my painfully hard cock licked the precum that had managed to ooze out off my cockhead. “Lay down.” I did as she asked, lying my head against her pillow. My cock was still in her grasp as she moved over me, her wet cunt hovering over my cock. She slowly lowered herself onto me, causing me to let out a long moan until she had completely covered my prick. She leaned over me and pressed her arms on my chest, steadying herself as she began to ride me. She began to ride me hard and fast, letting out low grunts every time our skin slapped together. I grabbed her by the hips to force her down on me faster and faster. She looked me in the eyes and said to me , “Oooh yeah, you like this don’t you Jake. You like fucking me don’t you? Not bad for a first time is it?” I could barely reply. I let out a grunt and hoped it would suffice. She then proceeded to slow down her thrusts, stopping occasionally to grind against my crotch. She was driving me wild. So wild in fact I decided to take a bit of initiative. I rolled her off of me, making her lie on her stomach. She looked at me with a wicked grin as I entered her pussy from behind. I knew I was going to cum soon, so I might as well do it in the position of my choosing for my first time. I began to thrust into her hard and fast, bringing pleasureful moans from her mouth. I knew I wasn’t going to last long, I could already feel the orgasm building up in my balls. I stared at the tattoo on the small of her back, slapped her firm ass a few times. I looked up, her face buried in her pillow, moaning into it loudly. The sweat from my forehead began to bead and drop onto her tanned back. I finally felt the orgasm reach me. I pulled out of her incredible pussy, and shot my cum all over her back, some of it going up far enough to reach her neck, a few stands in her hair. I leaned back a bit, attempting to relax, forgetting how far down I was on the bed, and ended up falling off the bed. Charisma turned around and laughed a bit. She then got off the bed to help me up.

“Looks like we both need a shower.” She took me by the hand and brought me to the bathroom. She opened up the sliding glass door of the shower and turned it on. She steeped in first, guiding mein behind her. “Wash my hair Jake. You got it dirty after all.” She wet her hair and handed me the shampoo. I squirted some in my hand and began to run it into her hair, massaging her scalp, spreading it around as much as I could. “Mmmm, that feels good. Keep going babe.”

“Uh, Charisma,” I got out sheepishly.


“Not that I haven’t enjoyed myself immensely, but why did this happen exactly?”, I asked.

“Well, if you need to know, I have a bit of a fetish,” she replied. “Not for teenagers, no offense, but for masturbation. It really turns me on watching guys do it. Don’t know why. So when I walked into the bathroom, and so you stroking, I got turned on. Add that to the fact that you’re quite the good-looking guy, I just kind of decided on the spot to have you. Finding you were a virgin actually turned me on a bit more.”

“You think I’m good-looking?” I asked sheepishly.

“Well, yeah. Not too bulky, not to scrawny. Nice mid-way between the two. I like that build. Face is cute too. You have some self confidence issues or something?” she asked, helping me rinse the shampoo from her hair.

“A bit.”

“No need for it,” she said, turning around to face me. “You’re a good catch. And not half bad in the sack, considering this was your first time and all. Almost came myself.”

“You didn’t cum?” I asked embarrassed, leaning my head against the shower wall.

“Don’t feel bad,” she said, taking my face in her hands. “It was your first time.”

“I feel like a dirtbag though.”

Charisma thought about this for a second, then looked at me and said, “You want another shot?”

“Yeah,” I said, nodding a bit nervously.

“Get on you knees then.” I did as she said and kneeled before her. She lifted her left leg onto my shoulder. “Eat me.” I leaned into her. I hoped I would not fuck this up. The only ideas I had about this was what I saw in some of Dyl’s dad’s porn tapes Dyl lifted. I figured I’d start out a bit slowly, so I slowly kissed and licked her inner thigh, working my way up to her aroused pussy. I nibbled on the sensitive skin where her leg met her crotch. I felt her shiver a bit at this. I hoped I was at least doing something right. I moved my hand to her snatch and started to finger fuck her, circling my fingers as I thrusted my two fingers in and out of her. She started to moan. “Good boy, keep going….” I brought mouth to her pussy and breathed in her musk. I moved my hands to cup her firm ass and began to lick her aroused lips, nibbling on them occasionally. I slid my tongue into her opening and licked her inside, hitting everything I could reach. I found her clit and started to drag my tongue across it slowly, while bringing my right hand back to her cunt to finger her while I attacked her clit. I started to suck on her clit hard, nibbling it and darting across it with my tongue, writing out her name, my name, anything I could come up with, on it with my tongue. Her hips started bucking now. She reached her hands down to my head, driving my face further into her crotch. I figured I must have been doing this right. Her hands clamped hard around my head, making it impossible to hear even the water cascading off the shower walls. Despite all that, I still heard he moan out loudly, signaling her orgasm. I felt it to, as the rush of her love juices covered my face and fingers. She released her grip from my ears and brought me up to her, kissing me deeply, tasting herself on my lips. “Not bad at all Jake, not bad at all.”

“Really?” I asked.

“Fuck yeah. Hard to believe you’re, or at least were, a virgin,” she said, moving her hand down, stroking my once again hard cock. “Oooh, look at this. Did I make you all hard again Jake? Need a bit of relief?”

All I could do was simply nod as I watched her descend to her knees. She started on me by gently kissing my sack, she took her tongue and lightly licked the area where my sack met my ass, sending a shiver up my spine. She took her hand to my balls and started to tug and knead on them, sucking them into her mouth, tickling them with her tongue. She slowly licked her way to my cock, licking and kissing my inner thighs, before she finally got to it. She slowly jacked me first, then brought her mouth to the tip, licking slowly to the base, then back again. She looked at me with a smile, then quickly took my cock in her mouth. I let out a loud moan. She looked up and smiled at me as best she could with my cock in her mouth. She took my hands and placed them on the sides of her head.

“You can thrust into my face if you want babe,” she said. “First time bonus.” She put my cock back in her mouth. I took the chance given and started to thrust my cock into her mouth, not even causing her to gag as it went down her throat. I started to thrust harder into her mouth, my balls slapping against her chin, her moans resonating through my cock, causing me to feel insane sensations. We continued like this for a god 10 minutes a t least, with her stopping occasionally to catch her breath and to suckle on my sack a bit more. I was reaching to point of no return at a rapid pace.

“I’m gonna cum Charisma!!!” I exclaimed.

“You can cum in my mouth baby, its okay,” she replied. She took me back into her mouth to the hilt, and soon after that I let loose, letting my seed shoot once again that day, shooting straight down her throat. Even as I began to pull out of her mouth, cum continued to shoot, covering her tongue in my seed. Even as it was out, a few more drops came out, dropping on her chin. She opened her mouth wide to me, showing me her mouth full of cum. She stared back me, my jaw agape, and she swallowed my load down with a smile. The she simply stood up and turned around, finishing her shower. She handed me some soap as well. After we finished bathing, I put my clothes back on and went backstairs to finish the job, and she went back to her bedroom.


“So let me get this straight,” said Laura, trying to hold in laughter. “You want me to believe that for your first time, you fucked Charisma Carpenter, a former cheerleader, and object of lust for thousands. SHE broke you in?”

“Yeah,” I replied. “And this is exactly why I never told Dyl. I knew the fucker would never believe me and just fucking rip on me. And even if he did, he wouldn’t be able to keep his trap shut.”

“Okay, so why didn’t you ever tell Mila smart guy?”

“Because, she was already pissed I ditched her to work, how happy do you think she’d be if I fucked one of the hottest women in the planet in addition? I didn’t want to lose any more of my chance with her.”

“Fair enough. You two were all right after that though obviously.”

“Yeah, but not completely. She was mad for a good month afterwards.”

“Really? Man, maybe she’s felt this way about you for as long as you for her.”

“Yeah. But either way, I blew it. Sure, I got laid for the first time by an insanely hot woman, but to be honest, if I could, I would have gotten out of it and gone to the movie with Mila. Just for the possibility of being in a better place with her than I am now.”

“You’ll get there Jake,” Laura said, pulling herself closer to me, putting an arm around me. “She just needs time to come around. And if what you told me today is true, she might be ready to.”

“Thanks Laura,” I said. “I have an early day tomorrow, sale at the shop. But I’m open for lunch.”

“Cool. I’ll see you then Jake.” She gave me a kiss on the cheek and a hug, and then walked out the door.

My sleep that night was troubled. I kept tossing and turning, fearing the talk with Mila, but also looking forward to it slightly. Maybe Laura was right. Maybe she did feel the same. Then again…..


It was around 8:30 in the morning, and the store was open. We had a lot of business, surprising, even for a sale. But I wasn’t complaining. Busy store meant mucho dinero. I was halfway though a sale when Mila walked in, a serious look on her usually cheerful face. She walked to the side of the line.

“Jake, can I see you when you’re done ringing that up?” she asked in a stern tone.

“Yeah, sure, meet me in my office,” I replied. She walked past the counter right into my office. I rung up my customer and walked towards Dyl. “Hey, could you ring some of these folks up Dyl, I need to do something very important.”

“Sure thing man,” he replied, walking towards the cash register. I walked bac k to my office to see Mila half-sitting, half-leaning on my desk.

“We need to talk,” she said, looking me straight in the eyes.

“Yeah, I know,” I said. “And I want to start it off. What happened between us yesterday?”

“I’m gonna lay it out right here for you Jake. I have feelings for you. SERIOUS ones. But I don’t know what to do about them, and they just rose to the surface yesterday.”

“You have feelings for me?” I couldn’t believe it. I hoped to God I wasn’t smiling the big toothy grin of doom.

“Yes. And I really want to start something with you, take what we have to the next level. But there’s only two things stopping me.”

Holy fucking shit, Laura was right. My mind was racing with thoughts, trying to form a response. “What’s stopping you”?

“Well, first and foremost, its our friendship. I don’t want to lose 14 years of friendship on something that may or may not work out.”

“We can cross that bridge when we come to it. Its worth the risk I think. What’s the other thing?”

“Well, it’s the fact that I’d only be your second girlfriend. You’ve kind of shut yourself off from serious relationships since….”

“Please Mila, don’t even mention her name. Of anyone, you should know that.”

“Well, you know who I mean. Ever since what went down between you and her, you’ve only had flings at best. I don’t want to be just another fling to you because some blonde bimbo burned you.”

“You wouldn’t,” I said, taking her by the shoulders. “I’d never hurt you. You mean too much to me to do that.”

“Still Jake, I worry about it. That’s why I think I have a solution.”

“Really, what st it?”

“Well hero, we wait a year. If in a year, you haven’t found anyone, and neither have I, then we’ll give us a shot. But we both have to actively look, just to see if there’s anyone else out there.”

“A year?” I asked. I sat down in my chair and thought about it. This was a big risk, at least to me. What if she actually met someone? Then again, she might not. The prize was too big not to risk it. “A year it is. If we don’t find anyone, we look to each other. But we can still hang out, right?”

“Of course,” she said, giving me a hug. “I don’t want anything to get in the way of what we already have. In fact, you wanna catch a movie tonight?”

“Sure,” I said with a smile.

“Cool, I’ll call you at around 7:00 with times.”

“I’m there.”

“Okay then,” she said with a smile and a turn. “I’ll talk to you then. Bye.”

“Bye,” I said. Wow. If things went the way I wanted, she’d be mine. Then again, how often have things gone exactly right for me? However, this is probably the best chance I’ve had. Ever. I would just have to hope thing would work out for the best, because I, at least in my head, had everything to lose.

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