The Entrepreneur by Chris James    The Entrepreneur
by Chris James

  Sexual Situations
  Rated Mature 18+

The Entrepreneur by Chris James

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Author Introduction
    This isn't one of those stories where the kid's parents die in a car crash or the guy was left billions in his uncle's will. The characters in this story are just normal people with the ambition to serve themselves by participating in the American capitalistic system of small business.

I don't know what I expected Florida to be like when I moved here from up North. All us Yankee types seem to slide down here at some point in life, I was here for business. My folks had left me a nice home all to myself. There had been no tragedy, they were off touring the world and planned to do that until the day they dropped dead.

Yeah, the business. It was all mine, courtesy of the partner I saddled myself with eight years ago, he lasted only half of that and I was glad to see him go. He cleaned out the company bank account and fled to Rio with some bimbo, leaving a wife and three kids behind. I closed out his accounts and settled the widow with a generous check. Oh, he wasn't dead yet, but he would be if I ever saw him again.

So sunny Florida, sand, palm trees ... sand, I'd seen it all the first week I moved in. The only people who went to the beach were the tourists and I was determined not to become one of those. The neighborhood was nice, lots of retired couples, some young families, and all pretty well off in our sagging economy.

OK, the business ... I sell stuff, unusual stuff ... the weirder the better. Remember all those junky catalogs you get in the mail? I don't do that, aren't you happy? I have a catalog, but people subscribe to it, it's exclusive. I sold a steam locomotive to an Arab sheik last year, he wanted it as a gift for his young nephew. It came from Utah. I had it dismantled and shipped to him where a team reassembled it in his back yard. His cost, eight million, I got two of them.

I only needed one sale a year like that to live like a king, but most of my stuff was much smaller, consumer products for the bored and wealthy. The new neighborhood was unpretentious so I put my crown away and tried to live a normal life. I got two or three hits a month from the catalog, the rest was online inquiries. All this meant was that I had free time ... entirely too much free time.

My parent's house backed onto the golf course, a game I didn't play. But we were down at the far end, like the tenth hole or something near the lake. My dad had a golf cart so I would occasionally take a spin, doing my best to stay out of the way, and that's where I met Matt.

Matt was about fourteen I imagine, nice kid ... pretty cute too. OK, I don't go for kids, that was just an observation. Yeah, I was gay, but I knew that the bars in Ft. Lauderdale were just up the road, I'd seen some nice beefcake there, but I had yet to bring one home.

Matt was a hustler. Oh for God's sake, I don't mean like that, get your mind out of the gutter. The boy was like me in many ways, he liked wheeling and dealing. I imagine he was quite the little businessman at his middle school. The first week I moved in he sold me a mailbox. I already had one of those but he said it didn't meet the current postal codes.

The Entrepreneur by Chris James

OK, I had no idea what he was talking about, so he took me out and showed me. Dad had probably had the damn thing for thirty years, and Matt said it was not only too high, it was too far off the road. I didn't think it was that big a deal, but I admired him for this salesmanship. He sold me a new one for sixty bucks, installed. I began to pay attention to him after that and he seemed to like the conversations we had. And once he found out what I did for a living he was around all the time.

OK, that worried me. What would his parents think? I mean some guy moves in and within a month their son is hanging around him. I was waiting for the cops to call, but it never happened. After about three weeks I worked up enough nerve to bring it up with the boy. Matt was astonished that I would worry about it.

Seems the parents were split up and he lived with his mom and two sisters. The only man in the house syndrome, I'd been through that myself. A few days later my doorbell rang and Matt was there with his mother. I could see the relationship; the boy looked just like her. She held a casserole in her hand and apologized for not coming to see me sooner.

I took the dish into the kitchen and Matt followed along, towing her behind.

"I told Mom what you said, Jake," The boy said.

"About?" I asked.

"You know, that she might think you're some dirty old man."

I was aghast, and his mother was shocked. "I'm sorry ... " She began.

I chuckled. "One thing I've learned about your son is that he is direct, and he's right, that's what I said."

"Well you're not ... are you?" Matt asked.

I smiled at his question. "No, Matt ... do you want to check my police record, the FBI files, Homeland Security?"

"Wow, do they all know you?"

"I certainly hope not," I said. "I don't have a record, but I guess that proves nothing."

The conversation between the boy and me was amusing his mother, she held up a hand to stop things. "Mrs. Conklin at the association says she's known your parents for a long time, Jake ... may I call you Jake?"

"Certainly, and you already have," I said.

"I'm Susan. I guess you know by now that Matt is not shy like most boys his age. I trust him to make good choices and he's never disappointed me. He told me about you the first day you two met, so there has been nothing secret about your relationship. So you go on being Matt's friend, he likes you and says you can teach him a lot."

Matt smiled. "See, Mom knows ... are we OK now?"

"Yes," I laughed. "I just wonder who's going to protect me from you."

"If he gets to be a bother send him home, that's all I ask," Susan said.

"He's never been a bit of a problem," I said. "I enjoy his company."

"Oh, Jake ... can I show Mom your catalog?"

"Sure ... would you like some tea, Susan?"

We sat at the table with our iced tea as she looked at the pages of my latest catalog with Matt leaning over her shoulder.

"Do people really buy these things?" Susan asked.

"Yes, I do a good business. Most of my regular clients have what you might call ... eclectic tastes, some of them have more money than common sense. For instance, I have two women who seem to be in competition. If Lady A buys something then Lady B must have the exact same thing shortly thereafter. I can't imagine what they think they're doing."

"Some of these things don't have a price on them," Matt said.

"Very observant," I said. "Some of these things are one of a kind, and not all of them belong to me. So if I get a buyer I have to negotiate a price with the seller."

"Matt knows how that works, he bought six mailboxes at a yard sale last year ... what were they sweetie, three dollars apiece?"

Matt blushed, knowing he'd been busted. But I roared with laughter and he laughed along.

"Your son is an entrepreneur. I might have to make him a partner one of these days," I said.

I asked Susan if she might wish to stay for dinner, after all she had brought food. But she had to go home and feed the girls, she urged me to enjoy the casserole. And then Matt invited himself to stay for dinner, and I agreed. Susan left after admonishing her son to be home early enough to finish his homework. And after she was gone Matt did a most unusual thing, he gave me a hug. His arms around my waist felt so good and I rubbed his back with my hands.

When he let go I looked down at his very green eyes and asked him why. "I like you, Jake ... you don't treat me like a little kid." He said.

I placed my hands on his shoulders. "You are a kid, but I respect the mind you have, that's why we get along so well."

That seemed to please him and he went about microwaving the casserole. Tuna and egg noodles with crumbled potato chips on top, I hadn't had that since I was about Matt's age. This was our first meal together, and that seemed to inspire him towards other firsts, like the questions.

"You ever been married, Jake?"


"Do you have a girlfriend?"


"Does that mean you're gay?"


"Oh ... I think I am too."

I put my fork down and looked in his eyes. "If you are, that doesn't mean anything will happen between us, OK?"

Matt smiled. "I get that, you won't teach me about sex. What will you teach me?"

I reached over and stroked his cheek with my fingers. "That you're a very handsome young man and someday you'll make some nice boy very happy."

Matt blushed and that made me smile, he was adorable. "And what if I want to know about sex?" He asked.

"We can talk about anything ... does your mother know?"

"I think so. When I was ten I had a birthday party, there were girls there but I kissed a boy named Samuel after I blew out the candles. Mom has the whole thing on a disk; I think that's why my dad left."

I was astonished. "Your dad left because you kissed a boy when you were ten? That's crazy."

"Yeah, that's my dad; he left two weeks after my tenth birthday."

"Oh Matt, you don't know that's why he left ... don't feel guilty about that."

"I don't, he was an asshole."

OK, I could see he wasn't upset about the loss of his father, at least not on the surface. It also explained why he hung around with me.

"I'm sorry you feel that way, I don't know how your mother feels," I said.

Matt grinned. "She's the one called him an asshole and threw him out, I love that."

I smiled back. "So my little gay buddy, do you have a boyfriend?"

"Me? Nope ... well maybe," Matt said. "I don't know what he wants from me."

"Does this person have a name?" I asked.

"Yup ... Samuel, now you know why I kissed him. We call him Sam now."

"So, is he gay like you?"

"He doesn't know ... but he wants to find out," Matt said. "He goes to my school. So, you think I should have sex with him?"

I almost choked on my food. I had to say one thing for the boy; he didn't beat around the bush. I had no idea what to tell him, so I said just that.

"I don't know this boy ... Sam, how can I tell you what to do?" I asked.

"Maybe I can tell you what I know and you can fill in the gaps, will that work?"

"OK, that'll be a good start, when should we have this discussion?"

"I have three days, he's coming for a sleepover on Saturday night," Matt said.

"Oh my, what will you do about your mother?" I asked.

"Oh yeah, I forgot about that. Can we sleep over here?"

Oh Lord, I'd walked right into that. Was I prepared to deal with two horny fourteen-year-old boys having sex in my house? I had no idea what they would do, only masturbate I hoped.

"I don't know if your mother will like that," I said.

"I'll tell her it was my idea, a boy's night out kinda thing," Matt said. "Can we?"

"I suppose, but we need to have that talk first," I said. "Now you need to go home, I'm sure you have some homework to do."

If it happened, they would sleep in the guest room, and fortunately there would be a full bathroom between us. I did not need to lie in bed listening to two boys having orgasms. I was pretty sure Matt, and thus his friend Sam, was at the age where all the equipment worked.

I would urge masturbation as a good place to start, mutual if they wanted. If neither of them was experienced I didn't see anything oral happening, and anal was out of the question. I would not provide condoms, which ought to stop any serious fooling around. But I would certainly take it upon myself to explain how condoms were used; Matt needed to know the truth about everything.

Ahh, the idea of two young lovers was so romantic. But the early experiences were often filled with moments of fumbling around. Kenny Terrell, I would never forget that name. My first romance with a boy, and such a willing boy at that. Seventh grade, we were both thirteen.

The dance at the school cafeteria was every boy's nightmare; it was a ladies choice night. Kenny and I stood against the wall close to the door. I was determined that when the first girl approached me I would excuse myself to the Boy's bathroom down the hall. I think Kenny had pretty much the same idea and was more likely to use the excuse. The boy was devastatingly cute, all blonde and glorious looking.

I didn't wait for a girl, I slid out the door. I stood there a moment and realized the gate was locked across the hallway. Well that sucked, the bathroom was on the other side. I went to turn back and Kenny came through the door, bumping right into me.

"If you have to pee, you're shit out of luck," I said.

"Yeah, I do in fact ... I'll have to use the one in the locker room," He said.

"That's probably locked off as well," I said. "They want us to use the bathroom by the office."

"And walk back past all those girls? No way, follow me," Kenny said, and I did.

We walked past the gym and around the corner where I saw that gate was locked as well, but Kenny turned towards the coach's offices and stopped at a small metal door. It wasn't really a door; it was a towel chute into the laundry room.

Kenny grinned. "My private entrance, care to join me?"

OK, he wasn't leaving me here alone. The chute opened and Kenny went through head first. Once his legs disappeared I leaned into the opening and followed. On the other side was a table and I pulled myself out onto it, Kenny was sitting there waiting. The room was almost dark except for the glow coming through the window from the emergency light in the locker room.

"I thought you had to pee?" I asked.

"Nope, I lied ... do you?"

"No ... I ... " And that's when he kissed me. It wasn't a long sloppy kiss, just a meeting of lips and then we parted.

"I've wanted to do that for weeks," Kenny said. "Are you mad at me?"

I was struck dumb, so I shook my head and he smiled. He put a hand on my neck and pulled me close, our lips met again, only this time I was prepared. The kiss went on and on, and I thought I would faint. Here I was kissing the most awesome looking boy in school, and he had started it.

Kenny pulled away and looked at me. "I've been looking at you since school started; I think you're so handsome. You won't tell anyone about this, will you?"

My God, he thought I was handsome ... him? Kenny was desired by every girl in school, and at least one boy ... me. I slid my hands across his shoulders and pulled him closer, and again we kissed. Slowly he leaned into me and I gradually fell back on the table with Kenny lying half on top, our lips glued together.

I ran my hands down his back and then up to his neck, my fingers running through his hair and around his ears. I heard him moan and I knew why, his cock was hard as a rock and pressing into my thigh. Our lips parted and we both gasped. I couldn't see his blue eyes in the darkness, but I knew he was staring down at me.

"Are we going to have sex?" I asked quietly.

Kenny nodded. "We can ... I've never done anything before, have you?"

I smiled. "Nope, we should have brought a manual."

He giggled at that and kissed me again. And this time I slid my hands down his back and grasped his butt cheeks. I felt him press that hardness against me. I was in the same condition and felt like I was about to burst out of my jeans.

"Will anyone see us here?" I asked.

"No, it's safe ... can I see your cock?" Kenny asked.

I nodded and unsnapped my jeans; Kenny slid his hands to my waist and began to tug them down. "I want to see yours too," I said. And as I slid my briefs down Kenny unsnapped his jeans and tugged them down, he wore no underwear and I thought that was sexy as hell. I lifted my shirt and he did the same. I looked at his cock and he at mine, they looked exactly alike.

His hand slid down to my tiny patch of pubic growth and I returned the favor. I had more hair down there. His was blonde and barely visible in the darkness, but I felt it. His hand grasped my cock and I did the same to him. We both began a slow stroking and I felt my whole body tingle at his touch.

"I never did this before," Kenny whispered. "Your skin is so smooth."

I leaned up to kiss him and he pressed back. The position was awkward and I lost my grasp on his cock, but I grasped his butt once again and Kenny rolled on top of me. His hand was between us, still gently stroking, but he soon abandoned that completely. Our cocks were pressed between us and we began to rub against each other.

His head was down, face against my neck and I heard him groan, followed by his hot breath on my ear as his tongue began to lick my neck. It was electric and I arched my head back to give him easy access. His lips and tongue kissed and bathed my throat, and now it was my turn to groan. Oh God, he was driving me crazy.

His cock was digging into my belly and it felt so good as he rubbed against me. I sought to pull him ever closer, and he trembled as my hands grasped his butt. The rubbing was stimulating us both and I felt that familiar tingle inside.

"I'm gonna cum," I gasped, and felt his teeth bite my neck.

"Me too," he groaned and our rubbing took on a new urgency.

My cock had never felt like this before, it felt huge and swollen, and then I knew why as it throbbed and I began to spurt. It seemed to go on forever, and then I realized Kenny had cut loose too. I grasped his head and pulled our mouths together, we both moaned as the last of our cum dribbled out and mingled between us.

Kenny collapsed on my chest and I could feel his heart beating a mile a minute, I was sure mine was doing the same thing. But we lay there for several minutes in the silence of that room and it was magical. Kenny slowly raised his head and looked down at me.

"That was incredible," He said, and I nodded. And then out of nowhere came the words that I would remember for the rest of my life. "I love you, Jake ... I really mean that."

I could look back now and realize neither of us knew what that meant. But for two thirteen-year-old boys in the throes of passion it worked, and it did until tenth grade. Kenny's family moved to California and I was devastated. I cried a lot, and became a loner for a while. Kenny was the lucky one, he already had the perfect surfer boy look ... I just looked like a sad gay boy from Connecticut.

But we learned about sex together ... all kinds of sex. That first night had been a revelation of feelings, and with love between us there were no boundaries. Of course I was mortified by the hickey he left on my neck, I had no idea that would happen ... but I saw it as a token of his love.

I had to give Matt a short course on the ins and outs of male Sex ... Oops, maybe that's not a good way to express it. But if he and Sam stayed together for a while it would come to that, the primal urge to mate was in us all. I just wondered who would end up on the bottom.

Of course I had no reason to know any of this, but that didn't stop me from thinking about it. The boy was expecting me to instruct him in words how to get sexy with his friend; it would be a whole lot easier to show him. I had porn, what single gay man didn't? But that would be all wrong, the boy would lose that innocence I so admired. Kissing, masturbation and maybe oral sex was all I was willing to discuss for the moment.

After their first encounter Matt would come tell me what they had done, he'd probably be proud of it. And knowing him he'd want to know what to do next, and I suppose that would be up to Sam. He was the unknown in the equation and I just hoped Matt was honest with me about how Sam felt.

With some boys all it took was to push the wrong buttons and the game was over, David Brooks had been like that my senior year in high school. We were both on the cusp of adulthood, or what passed for it at eighteen. But my three years with Kenny had taught me a lot about what to do in the bedroom, David was still unsure of himself.

I was already a wheeler and dealer by then, working my way towards college with an eye on a business degree. I had been in the photography club for two years already when David walked in. He wanted an activity, I wanted a friend, and we seemed a pretty good match. It didn't hurt that he carried a high end Nikon camera; it told me he was serious about his art.

I had an eye for the unusual, the forerunner to what I did now. I had talked my way past cops and security guards to get the best shots at a subject, and I had a pretty impressive portfolio by then. David was a people photographer, and when he finally shared his albums with the club I was astounded. Not a single shot was posed; he must have been the invisible man to get such a poignant view of life.

But I saw something in those photos that the other kids in the club did not, I saw what was in David's mind. This one photo he had said it all, a street scene, people walking on the sidewalk downtown. But the shot was really about the guy standing in front of the store display window, his reflection clear and in focus ... he was looking at a nude male mannequin.

The picture seemed erotic and I knew I would have to ask him about it ... privately. They were shooting a film over in Bridgeport and I mentioned that to David. I thought we could get some unusual photos of the on location stuff, he might find a few movie stars to fill his lens. So armed with only our cameras and a couple of press badges from the school newspaper, we set off early on a Saturday morning.

Bridgeport was just up the road, and I found a parking spot downtown once we spotted a couple of production trucks. By then I had spent almost an hour observing David without anyone else around. He was a quiet and somewhat soft spoken guy, and that didn't mean he was gay. But I had the perfect opening statement to check that out.

"I don't want to star gaze all day," I said. "Seeing Michelle and Lance together doing a film is interesting enough. I wonder how a gay guy deals with kissing a woman like her, even if it is an act."

David smiled. "You ever see any porn? That's all an act, most times the couples look so bored it just screams fake at you."

I laughed. "Porn? Why you kinky bastard ... what have you seen?"

"All kinds, but that was a few years ago. I make my own ideas of sex now," He said, holding up the Nikon.

"Subtle, Mr. Brooks ... subtle. I remember your store window photo ... that was almost erotic."

David nodded. "You caught that? Good, I'm glad you did."

"I'm gay, of course I would."

David frowned. "I ... I'm happy for you. Look, Jake ... I know what you think, but I'm not gay ... I can't be. That would cause a whole bunch of issues in my life, stuff I just can't deal with ... "

"Whoa ... slow down," I said. "I just told you that to be honest. If we're going to be friends I think that's important. I don't have any designs on your body ... I just want us to be friends."

David sighed and looked up through the windshield. "My therapist said this would happen some day, he said I would meet a gay boy and face the challenge of friendship. I can't be gay because I'm afraid of the consequences, Jake."

"It's OK, you don't have to tell me anything," I said.

"See ... but I do, therapy does that, it makes you honest about your feelings. I've been in therapy for four years now, once a week on Thursday nights. My uncle raped me dozens of times when I was twelve ... thirteen. My mom found out, it was her brother ... he's in jail."

I know the shock was clearly etched across my face when David turned to look at me. He reached over and patted my arm to reassure me.

"It's OK, I survived," He said. "I have gay feelings too, but I doubt them ... my uncle's fault not mine. I started to enjoy what he did to me, maybe it was the attention. I was too young to see it as anything but pleasure after the pain went away. He used me; it's as simple as that.

"I don't think about girls a lot, and I've never had sex with a boy my age, my therapist says I'm still a virgin, at least emotionally... mentally. My body understands sex, I use a dildo when I masturbate, and it's the only way I can get off now. Sorry, maybe that's too much information."

"David ... has anyone ever kissed you?" I asked quietly.

His brown puppy dog eyes said it all, and he shook his head. His eyes were moist because he knew what I was asking ... I wanted to kiss him. I hesitated and he knew I was holding back for his sake. The hand on my arm squeezed and he turned his body to me as I leaned over and brushed his lips with mine.

I heard him moan deep in his throat and he mashed his lips against mine, he needed that kiss. We never did see Michelle or Lance; instead we saw my bedroom for the rest of the morning. He was soft and sensual ... yielding, and trusting me not to hurt him. It was the finest moment of loving someone I had ever experienced, then and now.

But David was right; he could not orgasm unless I was inside of him. He discussed me with his therapist and they talked it all out. And at some point David decided that it was OK to be gay, and I was his lover. It made senior year seem like a dream, but not all of it was good.

We were out at school; we had fights with other boys. There were unkind words thrown about, and we fought some more. David fought hardest, and yet I was always there beside him giving back whatever someone threw at us. And despite the adversity we graduated, and spent the summer aware that what we had would soon be over.

I went to NYU and David to Stanford, some three thousand miles away. I saw him occasionally when he came home for vacations, but we were still honest with one another. He ended up partnering with a man twenty years older, and I'm sure his therapist would agree, David had found a man to take his uncle's place. And here I was thirty years later, successful in business, unlucky in love.

Matt came over after school the following day and we sat down. "So what do you already know," I asked.

"The biology I understand, I mean how babies are made and stuff, but that doesn't help much does it?"

"What do you know abut your penis?" I asked.

Matt smiled. "We're well acquainted."

"Do you think your sex drive is normal or over the top?"

"Oh ... hmm. I jerk off morning, noon and night whenever I can, you tell me."

"Normal," I said. "When did you first have an orgasm?"

"Last year, nothing much came out, now it shoots across the room every time. Last weekend I did it twice in a row," Matt said.

"So your reactions are normal, what do you think about when you jerk off?"

Matt blushed. "Guys ... and sometimes you."

I smiled. "Thank you, I'm flattered. So what do you think about Sam's body?"

"He's so thin, so sexy," Matt said.

"Have you ever thought about oral sex?" I asked.

"Yeah ... what does it taste like? I mean when a guy makes cum, does it taste bad?"

"No, not really ... it's just different. It changes with age and what you eat, but overall it isn't nasty. Have you tasted your own?"

"No ... I never thought of that, I should though, shouldn't I?"

"If you want an idea of what we're talking about, yeah. Some guys can suck their own cocks."

"Really ... awesome ... how is that possible?" Matt asked.

"Either it's really long or they just bend in the middle, I sure can't do it," I said. "I saw a video once, the guy lay on his back and curled his legs up and over his head until his cock was pointed straight at his mouth when he let go, got a real taste of himself that way."

"Damn, that sounds hot ... I'm hard just thinking about it," Matt said.

"The bathroom is down the hall if you need it," I said.

Matt went home later on and tried the position on his back, feet braced on the wall over his headboard. He said most of it went in his mouth; the taste was just OK ... he was sure Sam would taste better.

"Just remember if you blow him he'll feel like he has to do it back, and he may not be ready for the challenge," I said when we resumed the conversation.

"He sat in English class today with a big old hard on just for me," Matt said with a smile.

"So he's ready for something, good. I don't want you engaging in anal sex but you need to think about it," I said.

"OK ... I hear it hurts the first time."

"It'll hurt every time if you don't prepare yourself, are you going to pitch or catch?" I asked.

"Oh ... well, if he wants, Sam can fuck me, but I sure wanna fuck him."

I frowned. "Such a crude expression for something so tender and wonderful," I said. "It shouldn't happen right away, Sam needs to feel like he's giving you something special, it needs to be romantic."

"I guess that's the really big question, what does it feel like?" Matt said.

"It feels like heaven on Earth, the best thing you'll ever learn. That fullness inside will make you feel connected to him like nothing else. Nature was kind by putting our prostate just where it is, stimulating that will drive you up the wall. I never had a greater orgasm of my own."

"Oh ... it sounds wonderful, so what does this prostate thing do?" Matt asked.

"If you were four years older I would show you, but I can't. Have you ever placed anything in your rear end?"

"I rubbed it with my finger once, it feels good down there."

"There's a spot, about three inches up inside you. It feels like a little nub, a bump, and that's where your prostate is. Your finger can reach it, so next time you jerk off give it a try. But you'll need to lubricate first."

I smiled. "I'm going to give you something to use for that, please don't tell anyone."

"Can't you just show me, I won't tell," Matt said.

"It would break the rules ... the law. I'm not even sure us talking about this isn't illegal, there are so many rules to follow. But I won't lie to you; these are things you need to know."

He followed me down the hall to my bedroom. I gave him a small bottle of lubricant and explained how it could be used to ease that finger up inside. I could see his cock was hard from just thinking about it. Matt squirmed and adjusted the equipment right there in front of me. Then he looked at my bed and smiled.

"So, if we got it on, this is where it would happen?"

"In your dreams, come back in a few years," I said.

"And if I did, would you have me?" Matt asked.

I slid my hands around his head and leaned down to kiss him. The first time our lips had ever touched and I felt him melt. I quickly pulled away and saw the passion in his eyes.

"Yes ... I'd enjoy having you," I said.

Matt went home with this silly look on his face, tomorrow was Saturday, Sam was due over at three. I would order pizza, and I had snacks and drinks enough for an army. I had movies, Matt had movies and said Sam was sure to bring along some DVD's of his own. It only remained to be seen how many of them they watched before retiring to the bedroom.

I went in and looked at the guest room. I slept in my parent's king sized bed now, the queen mattress had been moved in here. More than enough room for two boys to play. I lay two bath towels and several small hand towels on the bureau, it might get messy. I just wish I knew what they might get around to doing.

Yeah, it was a perverse thought ... I would love to watch. The memories their inexperience would conjure up, Kenny and me...our nights of exploration and wonder. I would gaze upon their bodies and just wish for one last time I could be that innocent. It wouldn't be pornographic at all, just a trip down memory lane.

I sat on the bed and stared at the bureau which faced the bed. I had the means, why not use it? It would be wrong, but the boys would never know unless I told them. It would violate Matt's confidence in me, spying on them would be all wrong. But I knew I was going to do it.

The HK-1000, the perfect spying tool, I had two of them in the garage. The updated version of the Nanny-cam, that spying device from the early nineties. Parents who suspected their nanny might be abusing the kids while they were away had bought these devices. They secretly recorded what might be happening for later playback.

The newest version was a good home security tool. Motion activated, it would record someone in the room, a burglar, a neighbor with a key. HK-1000 was wireless, broadcasting a picture in color, high resolution, even sound ... all for the low, low cost of eighteen hundred dollars.

I had one in the living room, but Matt never noticed it. It looked like just an ordinary clock radio, which it was. I could plug the receiving module into my laptop and view the boys in real time as I recorded what they were doing. It was wrong, so wrong...I walked out to the garage to get one.

All of Saturday morning I told myself I wasn't going to turn it on and watch, but that was a lie. Even if Matt turned out all the lights the damn thing would switch to infra-red. The lens was the most expensive part; under normal light I would be able to count his pubic hairs. OK, I would watch, and if something went wrong Matt would tell me. Then I would already know what to say in return. I would not keep the file; it had to be erased ... didn't it?

Sam and Matt walked over around three-thirty, and my heart flopped when I saw the object of Matt's desire. Sam was a beautiful blonde creature, immediately bringing Kenny to mind. He shook my hand shyly, and that endeared him even more. They flopped on the couch and Matt grinned as if to say 'see, isn't he awesome?'

Matt showed Sam my catalog of products and I told them about some of the weird stuff I had moved in the past year or so. Sam laughed and suggested some people were crazy enough to buy anything, I could only agree. His face was adorable, his smile lit up the room...and if I had been Matt's age I would have been instantly in love with him.

At one point Sam went to use the bathroom and Matt gave me a look.

"So?" He asked.

I smiled. "Lucky bastard."

Matt nodded. "I want it to be special."

"Sweetie, you're already special ... that means you're halfway there."

Matt gave me a hug and a kiss, witnessed by Sam as he quietly walked back in the room. Matt looked up and laughed at the expression on Sam's face.

"Jake isn't fourteen otherwise you'd be out of luck," He said.

Sam sat back down and appraised me; I had a different dimension now.

"What Matt means is that I'm his only gay friend who's an adult. He knows I won't touch him and he teases me constantly about that," I said.

Sam smiled and I saw him visibly relax. "You ... you don't like boys?"

"Of course I do, I could eat two or three. But Matt doesn't need anything but affection from me and whatever else his sick little mind can conjure up." I started tickling Matt and he giggled with delight.

Sam laughed, enjoying the sight and eventually he came over to the couch and began to tickle Matt as well. Matt turned from me and attacked Sam, pressing the boy back on the couch as I sat watching. Their faces came closer and I knew what Matt was after. His lips met Sam's and they held them that way for a good long while.

Sam pushed Matt off and sat up, adjusting the bulge in his shorts. He glanced at me to see if I noticed and I smiled in return causing him to blush. Matt slid to the floor and started to look through the DVD's. I motioned to Sam who slid over beside me.

I kissed his forehead and he leaned against my shoulder. "Never be embarrassed by honest feelings, Sam. Every day life will give you new and different experiences ... enjoy each and every one of them. Share the best things in life with your friends. And someday one of those friends will love you in return."

Sam was quiet for a moment, and then he spoke. "I think I'm gay too ... I just don't know anything about it."

Matt had scooted over now, paying attention to Sam's words. Their eyes held steady on one another, I could see the adoration on Matt's face.

"Both of you have so much to learn about these feelings. Gay is not a choice, it's an understanding. If you are then it's always been there and with time you come to terms with it. Just having sex with another boy doesn't mean you're gay, only your heart knows the truth.

"For now it's enough that the both of you want to explore those feelings, and I agree, this is the right way to go about it. Enjoy the physical feelings you can give one another, leave all the heavy thinking for later on when your cock isn't hard, OK?"

Matt shifted his gaze to me and I realized both boys were looking at me. "That's the smartest thing anyone has ever told me," Sam said.

Matt patted my knee. "Jake is like that, he's gonna be our best friend, Sammy."

"You don't think sex will tell me if I'm gay?" Sam asked.

"It will tell you what you like, and that will help you decide. Do you need an answer right away?" I asked.

"No ... like you said, I don't need to think about it with a hard on in my pants." And then Sam giggled. "But it's like that all the time."

"Ahh, then you have to sneak up on it when Matt's not around," I said. "I think he made it happen."

"Yeah, I popped wood in English class the other day just by looking at him," Sam said.

"So you both share the feelings, and that's good, a great place to start," I said.

Matt shifted his hand to Sam's leg and squeezed. I almost laughed when Sam groaned; he would stay stiff all night at this rate. Sex and a little romance was in the air, Matt was a very lucky boy.

The afternoon turned into evening. A movie, a pizza or two and another movie. Sam lay in Matt's arms, their bodies side by side on the couch. I got mine when both boys lay their feet in my lap. Sam had the proverbial large feet, maybe a size eleven, Matt's were shorter. If what they say held true my Matty boy was in for a surprise tonight, I hope he didn't choke.

The movie ended at nine-thirty and I knew they were ready to move on. Matt had been stroking Sam's hair for almost an hour, and the bulges I saw on both of them said they needed to do something about it.

"Go to bed, guys," I said. "I'm sure you won't get to sleep for hours."

Matt gave me a grin as he and Sam stood up. First Matt and then Sam gave me a hug and a kiss good night, it was a sweet gesture. I let them wander back to the guest room and shut the door. I didn't need to watch, they were both so turned on, and whatever it was they did now was going to happen fast.

Did I really want to watch? Would I feel bad about it? Hell...there was only one way to find out. I walked down the hall to my room. I had a desk in one corner and the laptop was already on, just awaiting my command to link to the HK module. I moved the mouse and activated it.

Matt was sitting on the bed looking around the room, Sam was not in sight and then I heard the toilet flush. Sam walked back in view and I smiled, he was wearing only briefs.

"Your turn," Sam said.

Matt stood up and faced Sam, his backside to the camera, and then he began to remove his shorts. They fell revealing his briefs and a tight little ass. He was standing in front of Sam and I saw Matt wiggle his butt.

"Turn around and do that," Sam said. Matt faced the camera and shook his butt at Sam; I could already see the swelling at the front of those briefs. Slowly Matt slid his fingers into the waistband and began to ease them down. Sam giggled as Matt's ass came in view, what I got was a full on view of Matt's erection. A good five inches of erect cock.

"Nice ass, Matty."

Matt let the underwear drop and sat on the bed. Without a word Sam stood up and stripped off his briefs, first presenting Matt with the rear view as his six incher slapped up against his belly. Lord, Matt was going to have a time dealing with that.

It wasn't until they lay on the bed together that I began to feel aroused. Matt climbed on top and then Sam rolled them apart, pulling himself on top. Back and forth, the whole time their lips sealed together, they were playing. Finally they lay on their sides and hands grasped cocks.

"Damn, you're so big," Matt said, his hand clutching and stroking Sam's cock.

"You better stop ... I'm about to shoot," Sam groaned.

"Oh ... not yet, I wanna taste it," Matt said. OK, I had known that was going to happen.

Matt turned himself sideways, pushing Sam on his back and sliding his head down to the boy's crotch. Sam gasped as Matt began to lick the head of his cock.

"Matty ... what are you ... Oh God," Sam groaned and that was all the warning Matt got, the boy erupted in his face. The surprised look on Matt's face made me want to laugh, but the scene was so fucking sexy I couldn't. Sam's cock emptied his balls in short order, big lazy spurts of creamy goo that splattered Matt's cheeks before he got his mouth over the end. I could see he got a few shots in his mouth, enough for a good taste of Sam.

Sam collapsed and Matt withdrew his mouth, I could tell he still had cum in his mouth and then I saw him swallow. Brave warrior, his first almost blow job. The goo was running down his face and Matt slid off the end of the bed and grabbed a face cloth, looking up into the mirror above the camera with a grin. He was quickly out of focus as the HK tried and failed to adjust, too close ... but then he sat back down.

"Jeez, you sure make a lot of cum," Matt said.

"You ... you put it in your mouth," Sam said. "Isn't it gross?"

"No way ... haven't you ever tasted it before?"

"Eww, no way," Sam said. "If I suck you I wanna know before you shoot, OK?"

"Yeah ... long as you jerk me to a finish," Matt said.

He scooted back up on the bed and it was Sam's turn to suck cock. Matt had a taste for cum now, Sam might not ever. But I was surprised when Sam took Matt's cock in his mouth and slid it all the way down his throat. Fuck, he sure wasn't shy about it.

Matt groaned and leaned up to see if Sam really had it all. Yeah the boy had every inch embedded in his throat and then he slid it back out.

"Fuck ... that felt awesome," Matt said.

Sam nodded but never lost contact, and down he went again. Matt's tool was shorter, slender, Sam could handle that ... and I wondered where he had learned the technique. He bobbed and Matt squirmed, it wouldn't take long now.

"Oh God ... pull off ... I'm gonna cum," Matt squealed.

Sam quickly withdrew and his hand went to town. Matt bucked upwards once ... twice and he let go. Three good shots straight up in the air a foot or so and then he was done. Sam looked down at the splatters on Matt's belly and grinned. He sniffed at the goop on the back of his hand and took a tentative lick. OK, at least he was willing to try.

The way things usually worked was that if Matt was willing to suck Sam off, then Sam might just find himself on the bottom. Some guys just couldn't handle the taste or even the thought of it in their mouths. But they often compensated by allowing themselves to be penetrated, equaling things out.

Matt was definite top man material, aggressive and unafraid of anything. Sam had a bigger cock, I had no idea what his butt situation was...but Matt would find out. They kissed and cuddled, all I could hear were moans and sucking noises. I noticed that neither of them completely lost their erections. Mine was drooling in my shorts by now.

Matt pulled away and smiled. "You ever finger yourself up the butt?" He asked.

Sam giggled. "No ... why would I do that? It sounds gross."

"Hardly, it feels awesome. See there's this gland up there, the prostate, and when your finger touches that thing it's like fireworks in your body. Jake says that's why guys like getting fucked."

"Shit, Matt ... he tells you things like that? That's kinda pervy."

"Oh hell no, you did not say that. Jake will tell me anything I ask him, and I want to know it all. Honest, if you stay with me we are gonna do just everything and I am gonna blow your mind."

"Oh shit, you wanna fuck me?" Sam asked.

Matt grinned. "Not now, you aren't ready for it. But you have to let me show you something, and then you'll understand. I did it last night and I'm still freakin about how good it felt."

"You're not gonna hurt me are you?" Sam asked.

Matt leaned over and kissed Sam, pulling their faces together by grasping the boy's head. They pulled apart with a smacking sound.

"I am never going to hurt you, Sammy...but this is gonna feel so good you might think you died and went to heaven."

Sam smiled. "OK...I like the sound of that. What are you gonna do?"

"I'm gonna suck your dick and slide my finger up your butt. And when you cum you'll probably scream, so you better have that pillow ready to cover your face. I damn near woke my mother up last night, and we don't want Jake to think I'm killing you in here."

"That good, huh?"

Matt grinned. "You'll probably blow my head off when you let go, but you'll definitely be begging me to fuck you."

"I can't do that, Matty...I..."

"Shush...don't say you won't until you feel me."

Sam must have thought something good was about to happen because his cock looked terribly stiff and swollen. Matt made him roll onto his stomach and then the little bottle appeared in his hand. Matt knelt between Sam's legs and I saw his hands spread the boy's legs. Damn, he was blocking my view.

Matt was looking down intently at his target. "Wow, you got no hairs down here, just like me," Matt said.

"I can't see back there, how would I even know?" Sam said.

"Well you got a nice clean lookin butt hole, that's for sure."

Matt leaned down for a closer look and I saw his elbows go out to the side; he was spreading Sam's ass cheeks for a better look.

"What are you doing?" Sam asked.

"Looking, that's all." Matt picked up the bottle and I knew he was squeezing out some of the lube on Sam's asshole. He tossed the bottle aside and I figured he was rubbing a finger around in the slime.

"That feels weird," Sam said. "Oh, what are you doing?"

"Relax, you get all tensed up and I won't be able to get in's only a finger."

Matt played a while before Sam responded again. "That doesn't feel bad at all."

"I'm goin slowly, I need to get my whole finger up in there... doesn't it feel good?"

"Uh huh ... kinda weird," Sam replied, but I could tell he was feeling good about it.

And then thank goodness Matt shifted his position, climbing over Sam's thigh until he was kneeling beside the boy. I could see the spread cheeks and Matt's finger embedded in Sam's hole. I watched Matt working it slowly in and out, good work; he was allowing Sam to relax.

He spent five minutes getting that finger all the way in, but the way his wrist was turned he wasn't rubbing the prostate, just filling the space.

"I'm going to roll you over very slowly," Matt said and Sam said, "Yeah."

Matt's left index finger was deep inside, so he pushed Sam on his side with his right hand and then pulled his leg up. Somehow Matt had thought this all through and slid Sam's leg up until he could bring his left arm down and allow the boy to slip through onto his back.

Sam just laid there, legs splayed and his cock sticking straight up. And then I noticed that Matt's wrist was turned as well, he could directly assault the prostate now. Matt leaned down and took Sam's cock in his mouth. The boy gasped at the feeling and then Matt started working that finger.

"Oh God ... Oh My God ... that feels awesome," Sam said.

Matt started sucking up and down as his finger pushed in and out and in no time Sam was thrashing around on the bed. That did it, out came my cock and I began to stroke. Jeez, I was watching something hotter than any porn I had.

Sam groaned loudly and Matt bobbed on. Sam was moving his body all around, his hands clutching the sheets of the bed like he might fly off if he didn't hold on. He started bouncing his body up and down, thrusting into Matt's mouth and at the same time embedding that finger to the fullest. Another loud groan and Sam grabbed the pillow, slapping it over his face.

I could still hear the screams of ecstasy as Sam's body trembled and bucked, Matt suddenly stiffened and I knew Sam had cut loose. I watched Matt gag a bit and then cum started oozing out the corners of his mouth. Sam was out of it, and so was I. My cock throbbed and I shot my wad on the carpet as Sam filled Matt's mouth.

I could see Matt's throat working; he was trying to swallow all he could. Sam had collapsed completely. Matt finally laid his face on Sam's stomach and slowly withdrew that finger. I saw him hold it up to his nose and sniff, kinky kid, and then he stuck it in his mouth.

OK, not even I would have done that ... but this was Matt. He was no longer the innocent kid I had met some weeks ago, no ... he was changed. I could almost see him tongue fucking Sam before sliding his cock in the boy's rear ... that would happen, I was sure of it now.

I suddenly realized that I was responsible for all this. I had told Matt a few facts and he had gone home to experiment, and look at his conclusions. This was no kiddie jerk off session, this was Matt having real sexual experimentation and Sam was his lab rat.

Matt paused in sucking on that finger and smiled as he pulled it out of his mouth. He was looking right at the camera and he puckered his lips in a kiss. Oh My God ... how did he know I was watching?

I shut down the program and closed my laptop, I was totally freaked out. I stumbled in the bathroom and cleaned myself off. Looking in the mirror as I brushed my teeth I realized Matt had known all along I would watch, and yet he put on that show. I shut off the light and slid into bed wondering how I would face him tomorrow. I was thoroughly ashamed of myself.

I don't know how long it was, I had dozed off ... but I felt the covers slide back and Matt slipped into bed with me. I feigned sleep, he wasn't buying it.

"Did you enjoy the show?" Matt asked.

"I--I'm sorry," I said.

"Did the HK-1000 perform as expected?" Matt asked.

Oh Lord, so that's how he knew. "Uh ... very well," I said.

"I saw it in the catalog; I remembered what features it had ... thought that was pretty cool. So when I saw it on the bureau I figured you put it there for a reason. You didn't answer the question ... did you enjoy yourself?"

"Yes ... that was hot ... you were hot. Does Sam know you're in here?"

"Sam doesn't know shit, he passed out after that orgasm," Matt said. "You haven't figured this out yet, have you?"

"No Matt ... figured what out?" I asked.

"I put on that show for you, not Sam. He won't even suck my dick, but I'm sure you will. I don't love him, Jake...never will...I love you."

"Matt we can't ... "

"Aw hell, don't go getting moral on me now after what you did. I don't want Sam, I want you ... I've always wanted you."

"This is all ... why did you even bring Sam over?"

"Just good sales practice. I want to be your partner, but you have all these fuckin rules to follow. Look I'm a good deal, low mileage and even you said it, I'm hot. I'm an entrepreneur, you said it yourself. I just had to find the right sales tactic and you did all the rest."

There was silence in the room and then I began to laugh. Matt joined in and I hugged him, feeling his hard little cock press against my leg. "You little devil ... you tricked me."

"Don't feel bad ... I know how to make you a happy customer," Matt said.

"I bet you do ... what about Sam?"

Let him find his own man, I got mine. So ... when do I get that free sample, partner?"

"The Entrepreneur" Copyright © 2 Jul 2009 by Chris James. All rights reserved.
    This work may not be duplicated in any form (physical, electronic, audio, or otherwise) without the author's written permission. All applicable copyright laws apply. All individuals depicted are fictional with any resemblance to real persons being purely coincidental.

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