Chapter 91 - Best Friend's DILF

My best friend's dad, Dan Jacobs, is my kryptonite. Not only is he handsome, intelligent, athletic and rich, he's f.u.c.k.i.n.g hot as hell. And he knows it. And he knows I know it too.

How can he not know? The first few times I used to come over and hang with Zac, he always seemed to turn up. Whether it's by the pool, the game room, watching tv, he always showed up. So what? For a horny 17-year-old whose life revolves around nothing but football, ESPN and video games, this dude makes it hard to concentrate on any of those things. I'm also a very closeted 17-year-old. And this guy, this guy turns me the f.u.c.k on. I couldn't get enough of him. I could not stop staring at his face when he isn't looking, his square jaw, five o'clock shadow, blue eyes, neatly styled hair. He caught me so many times and all I could do was just look away as quick as I could.

Mr. Jacobs has the most incredible a.s.s I've ever seen on a man his age. At 40, he's in better shape than most 20-year-olds I know. The first time I saw him in a suit I was instantly hard. It fit him like a glove. And the man can fill out a pair of jeans like no other. Sometimes I would stand out of sight watching Mr. Jacobs go about his day, mowing the lawn, sitting by the pool, cleaning the house. I couldn't get enough of him or that a.s.s.

Soon I think I was just hanging out with my buddy to get off on his dad. No, I know I was. Zac? Zac who?

He started to make intense eye contact one day. It was intimidating and it made me blush. I stuttered when he spoke to me. I began getting the shakes and sweats when he was close to me. God forbid he touch me or brush up against me. A shiver would shoot down my spine and my heart would beat like it was trying to break through my c.h.e.s.t.

I noticed he was staring at me through a reflection in a wall mirror. Then I saw it in a window reflection while we were hanging out by the pool. He watched me walk away and cross the deck to the house. He pulled down his sunglasses, peaking over them to get a better look at my a.s.s. I couldn't believe what I was witnessing. My heart jumped in my c.h.e.s.t and I started to wonder, "Is my best friend's dad…into me?"

I don't know why, and I don't know how but I got the courage up to buy a speedo. I needed to test the waters, not the pool waters but the DILF waters. I slid that small tight material up my football player quads and pulled it up over my bowling ball a.s.s. I looked in the mirror and f.u.c.k, did I look hot. Tall, muscular, ripped from summer football training camp, tan and an a.s.s that stuck out like a shelf. This was the true test. No more dating girls and pretending I like them. No more awkward moments f.u.c.k.i.n.g a chic but really thinking about my best friend's dad or one of my other buddies from school. No more hours and hours of jacking off to gay p.o.r.n. I want some DILF d.i.c.k.

I picked a day when I was sure he was home and Zac wasn't, his mom at work. I showed up, went to the pool, peeled off my tight football pants, the ones I cut up into shorts, and revealed all I had to offer. Like I planned, he came out to the pool within like two-minutes.

"Hey, Chris," he greeted me with a dazzling smile. I could tell he had been to the gym that morning. He is body was pumped.

Acting surprised to see him, "Oh, hey, Mr. Jacobs," I replied.

"You know, you really don't have to call me that," Dan chuckled. "I appreciate the respect but it's just you and me. Deal?"

He sat down on the lounge chair next to me. His shorts are snug, his t-shirt form fitting. F.u.c.k, I love an older guy with a hot body.

"Alright, cool, Dan," I smiled. "I hope you don't mind but Zac said I could hang out by the pool today while he was at work." Lie.

"Oh…Oh, god, no," Dan said with a shrug. His tone telling me I was crazy for thinking otherwise. "You're welcome anytime. You know that. You're like a second son to me." He patted me on the t.h.i.g.h, his hand lingering a little too long.

I decided to put the second part of my scheme into action. "Oh, damn. Where's my phone?" I pretended to search for it under my lounger then glanced over my shoulder towards the house. "Oh, I know where I put it. I left it inside on the dining room table, I'll run in and get it."

I stood up and walked towards the sliding glass door, adjusting the back of my speedo, pulling it down over the bottom of my exposed a.s.s cheeks. I walked with a c.o.c.ky stride, marveling at my reflection in the glass door as I walked towards it. My ripped six-pack, my granite quads, my hip bone muscles sinking into the front of my tiny suit. My football player body looked s.e.xy and tantalizing, my teenage body looking more like a man's.

I watched his reflection in the big glass doors as I entered the house. Dan was staring at my a.s.s like it was Thanksgiving dinner. I smiled to myself and unfortunately, started to get a little stiff. His hungry eyes made my think about nothing but getting his c.o.c.k into my a.s.s.

"Shit," I said to myself quietly as I looked down at my spandex covered c.o.c.k. "Calm the f.u.c.k down, dumb f.u.c.k," I mumbled out loud. I grabbed my strategically placed phone, I took a deep breath and waited a few more seconds before joining him back at the pool.

This time he made no attempt to hide his stares. His sunglasses didn't hide the fact that his eyes followed me back to my chair.

"Can't stand being without my phone. Ya know?" I laughed.

He smiled. He pulled up his sunglasses and set them on the top his head, nestled in that thick, black wavy hair. His eyes were traveling down my c.h.e.s.t to my abs and hovering over my speedo. "Uh…yeah. I hate that too. Feels n.a.k.e.d," he commented before he bit his bottom lip. That s.e.xy, plump bottom lip.

"Yeah, exactly." I nodded in agreement. "N.a.k.e.d," I said quietly.

My eyes followed his tan muscular biceps, triceps, thick forearms. His legs, tan and not too much hair.

"You, ah…You…are really looking good these days," he stammered a bit. "Football camp agrees with you. Your body is jacked, dude!" he said as he playfully punched my quad. I could tell he was trying to find the right tone and the appropriate words to come off as a bro and not a dad.

"You know how it is," I shrugged. "Hot days, long workouts. Can't eat enough food, fat just keeps falling off me. Muscle just keeps growing. I had to buy new jeans; my a.s.s got too big,"

I ran my hand over the side of my speedo as I shifted in the chair, tilting my body to the side to expose my a.s.s. I give it a playful slap. His eyes grew large as I flexed my glute. He bit his lip again. This dude was hungry for a.s.s. My a.s.s.

"What's your body fat percentage?" He asked almost too eagerly.

I ran my hand down my 6-pak and pinch a bit of skin near the waistband of my suit. "Oh, probably around seven or eight-percent? Some where around there, not sure," I reply nonchalantly, meeting his eyes.

Nodding his head, "Cool, cool."

I adjusted myself, tugging gently at my c.o.c.k though the front of my speedo.

"So…uh…" he stammered again. I wanted to laugh out loud. He couldn't complete a thought. He leaned forward, elbows on his knees, nervously rubbing his palms together. Looking around, to the left, to the right, back to me as if there would anyone listening. His paranoia was cute.

My heart was racing. He was sweating, his forehead dripping a small drop here and there. I continued to stare at him, never dropping eye contact. He looked down again as if collecting his thoughts. He looked up at me again and let out a small uncomfortable laugh.

"Oh, man…" he said quietly under his breath before taking a deep breath and puffing it out. He continued to rub his palms together, out came another nervous laugh.

"You…uh…where did…where did you get the speedo?" He chickened out asking what he really wanted to ask deep down in his gut. His facial expression said he still was trying to play it safe. I could tell he regretted asking the question before it was done leaving his lips.

I ran my hand from the front, down the side and pinched some fabric and let it snap back. "Online. You like it? Don't think it makes me look too…gay?"

He swallowed hard. "Oh, no, dude. No, not at all. In fact, you're one of the few guys I know who can pull one off. Fits you like a glove."

"Yeah? Right on. Thanks, Dan," I said as I gave him a firm fist bump, bro'in it up with the nervous hot older man.

My eyes were drilling holes through his. I loved making him squirm. It's just like how I love to make girl's squirm with my charm and c.o.c.kiness. Even though I don't like girls, it's a rush to know that I have that affect on them. Dumb bitches. Now I just realized the power I have over this hot older guy. Do I have this power over any guy? Or just gay dudes?

He broke eye contact for a second, quickly scanning my body. "Besides, you could never look gay. Not stereotypical, I mean. You're a big guy, very masculine. Not that gay guys can't be masculine," he said quickly as if he had offended someone. "But I'm sure you would be any gay man's first choice," he smiled. He was quiet for a few seconds and then his eyes turned serious, almost seductive. "I mean, if I were gay, I'd be all over you. That probably doesn't matter, being gay I mean. I bet you could turn any straight guy."

I turn up an eyebrow at that comment.

"Really? A straight guy, huh? Maybe even a married guy?" I smirk. "One with a kid?" I licked my bottom lip, slowly, s.e.xy. "If you were gay, you'd be all over me?"

He looked down. Contemplating his next answer. Then as if he was injected with a burst of courage, his head snapped up to look at me. He knew it was time to pounce. The kid before him was ready. He's wanted his son's best friend since they first met, and I was giving all the right signals. His posture took on a dominant air.

"Oh, yeah. I would be all over your shit." His eyes looked devious, almost evil. His mouth closed, no smile.

I lean forward. "Well, Dan. If I were into dudes…I would make you my bitch." I hissed. I smiled a white toothy grin and gave him a slap on his knee and a squeeze.

He gulped. Both of us quiet, just staring at each other. He looks at his watch and then back at me.

"Your bitch, huh?" he asks in a challenging tone telling me I was crazy to think that.

"Well, Danny Boy, one of us has to be" I said in a low quiet voice. I bite my lower lip.

"What if I were to make you MY bitch, huh? F.u.c.k the c.o.c.ky right out of you," Dan said, straight faced, letting me know who was in control.

I shrug my muscular shoulders. "We could always…take turns?" I looked down at his stiffening bulge. "F.u.c.k.i.n.g the c.o.c.ky out of each other."

He swallows hard again.

I continued, enjoying the flirtatious seduction. "Unless, you're the type who likes to take control. You seem like the type. I'm sure a man like you could take on, say, a guy my size."

He looks around again as if someone might be listening. He checked his watch. We stared into each other's eyes for what seemed like forever. I licked my lips and reached out and squeezed his knee.

"We're thinking…the same thing…right?" he said more of a statement than a question.

I shrug again. "Well, Danny Boy, only if you're thinking about ripping my tight, little suit off and boning me. Then, yes, we're thinking the same thing."

"Thought so," he replied. "Um…Zac…"

"F.u.c.k Zac! Who cares about him?" I said with irritation in my expression.

I scoot to the edge of the lounge chair, my knee touching his. His bulge is full on erect.

"He'll never find out…MR. JACOBS," I say with a naughty tone to my voice.

"Please, MR. JACOBS," I say mockingly in my best schoolboy voice. "I've waited so long for this. You're all I can think about, MR. JACOBS."

"STOP calling me Mr. Jacobs," he says with a smile.

"But why, MR. JACOBS? Why won't you let me call you that?" I tease. "You're my best friend's dad. You're almost like a dad to me. I'm showing you respect, MR.…"

He cuts me off by grabbing the back of my neck, slamming our lips together and thrusting his tongue down my throat. He pushes me on to my back and slides on top of me, grinding his c.o.c.k against my t.h.i.g.h and then against my rock-hard c.o.c.k.

"F.u.c.k yeah." I hiss as we break our lip lock. "About f.u.c.k.i.n.g time, old man."

He jumps up off the chair, grabs my hand and pulls me up. Without stopping he pulls be through the glass doors, up the stairs and into the master bedroom.

He spins me around and kisses me again before he shoves me hard onto the bed. My big muscular body bouncing on the mattress.

"Get those f.u.c.k.i.n.g speedos off or I WILL rip them off." He says as he starts furiously taking off his own clothes.

I get a c.o.c.ky look on my face, eyebrow c.o.c.ked, challenging him. I want him as aggressive as I can get him.

"Try it…old man," I say like I'm pissed that he would even dare to test me. Really though, I want him to want to take me down.

He stops and looks down at me like he can't believe what I just said. There is no smile. I have disrespected him. "What did you just say to me? Not even my kid talks to me like that."

"I'm not your kid, Danny-Boy. But then if I was, I have a feeling this would still be happing. Maybe you wish I was your kid? Afterall, Zac is a hot piece of a.s.s. I wouldn't mind taking it for a spin."

Once again, he looks at me with a slightly surprised expression. He jumps on me and rolls me over on my stomach. Dude is strong! But then I'm not fighting back.

He grabs with both hands the tight material over my a.s.s and tears the back seam that runs down between my muscular globes. My hole is now exposed through the rip.

"F.u.c.k, yeah," he growls, "I WILL f.u.c.k the c.o.c.ky out of your a.s.s, you arrogant, little prick. But then, you want that, don't you?" Again, not a question, it's was a statement.

Well, I wasn't planning on this happening so soon. I thought we would mac on each other for a while before we got to the f.u.c.k.i.n.g. F.u.c.k it. He wanted to get to the deed so let's get to the f.u.c.k.i.n.g deed.

"F.u.c.k yeah, I do, old man. I've wanted you to f.u.c.k me since the day we met. Finally took the f.u.c.k.i.n.g hint, dude."

Again, annoyed at my brazen attitude towards him, accusing him of not being able to see the obvious signs of a hot jock trying to get his attention. "Boy, I'm going to destroy your beautiful a.s.s." He moves over to the side table and produces a bottle of lube. "Don't worry, p.u.s.s.y boy. I'll take it slow…at first," he mocked. "After that, I'm screwing your jock a.s.s until I dump a nice big load inside your gut."

"Mr. Jacobs," I saw with a naughty accusatory tone. "You act like you've done this before." My tone telling him I know he has.

He squirts some lube on to my hole. It's cold. I flinch.

"Not my first rodeo. You guys are a dime a f.u.c.k.i.n.g dozen."

Dan opened me up with his big fingers, getting me prepared for his thick c.o.c.k. Kinky, I thought. He's going to f.u.c.k me through my speedo. He must really like the suit. I'll have to take a note of that. When he slid in, for the first time in my short life, I knew who I was and what I wanted. I wanted c.o.c.k. I want it all the time. He was slow at first like he promised. As soon as he thought I was ready, his onslaught began. I could tell by the determined look on his handsome face, the look of how proud he was that he achieved another jock boy conquest. He took pride in knowing he took control of a thick, solid muscle boy, threw him around and turned that jock into a full on, f.u.c.k.i.n.g p.u.s.s.y boy.

He f.u.c.k.e.d me all afternoon. He f.u.c.k.e.d me in every position he could think of. After that day, we would hook up on the down low. He allowed me to play with his a.s.s from time to time but forbid me to put my d.i.c.k anywhere near that tight hole. I was fine with that. Being this man's f.u.c.k boy was good enough for me.

He eventually shared with me the different jock hook ups he had with other guys my age. It turned me on to picture him balls deep in some other football or baseball player like myself. I asked him to introduce me to a couple. He was hesitant but he relented. Those were encounters to be told at another time.

Whatever we did, he made sure to assure me that I was his main boy.

So now, a year later, as I'm sitting in his secret condo that he bought on the DL for us to f.u.c.k in, he appears from the upstairs. He's wearing a slim, blue sport coat, a crisp white dress shirt and a silky yellow tie. However, he's also wearing a nice tight pair of dark jeans that accentuate his hot bubble b.u.t.t and his muscular t.h.i.g.hs. He takes off his sport coat to tuck in his fitted shirt, highlighting his tiny waist. It's so hot to see him dressed this way. It makes me remember the time he f.u.c.k.e.d me while he was wearing one of his designer suits. He looks amazing in a tailored suit, but oh man, those jeans.

I'm dressed similarly. He bought me one of many custom-made

Armani suits. I have just turned 18 and we've been f.u.c.k.i.n.g for almost a year now. Zac still doesn't know. His mom has no idea either. We were spending a lot of time together; alone and with Zac which was awkward sometimes. We eventually came up with a cover story that Dan is mentoring me and teaching me about his job, whatever that is, and just being a good mentor and father figure. No one is the wiser. It sounds very plausible.

"So, Mr. Jacobs, where are you taking me?" I flirt.

He puts his sport coat back on. "Tonight, I have a special evening planned for my hot football boy," he grinned.

I laugh as I stand up and cup his a.s.s with one hand. I kiss him.

"I'm taking you out for a nice dinner and then to a party. A friend of mine has a house out in the hills."

"Are you showing me off, Mr. Jacobs?" I ask sarcastically. Of course, he is.

"Baby boy, I'm going to show you off, make every dude there jealous and then f.u.c.k the hell out of you."

I smile. A sudden rush of adrenaline shoots up my spine.

"Nice," I hiss.

"You like that, baby boy?" He hugs me and strokes my c.o.c.k over my jeans.

"Yes, Sir. Mr. Jacobs."