Benefits Ch. 03

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.

"Yes?"

"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.

*********NOW

"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.