I had just turned 16 when Larry Robertson tipped me $100 for carrying his clubs for him. Almost literally. My birthday is April 30 and this was the Saturday before Mother's Day in 2012. The $100 bill was folded twice lengthwise and he held it out between the first and middle finger of his right hand. It was more than most golfers tipped their caddies at this country club, but not that much more. He made it seem like a big deal, though. He watched me as I took it from him and slid it into the front pocket of my khakis before he quietly said, "There are a couple more of those for you if you come by my house tonight around 10:00."
He said it so casually. Like I had a reputation as a rentboy or something. Like he already knew I was going to do it. A lot of people have their preconceived ideas about the only openly gay kid in town, I guess. I shrugged and told him I'd think about it. He looked around shiftily like he'd just bought some crack and nodded, telling me he'd see me around before heading to the clubhouse to shower.
He didn't give me an address. He didn't have to. The Robertsons lived four blocks from me. His son, Scott, was my age and in a few of my classes at school. We didn't travel in the same circles or anything, but we each knew who the other was. But then, almost everyone at school knew who I was.
I'm sure I wasn't really the only openly gay kid in town. It was 2012, after all. But I was the only one where it mattered to Larry Robertson and his clique: the old-money, private-school part of Charleston, South Carolina, at the end of the peninsula. The part that tourist magazines advertising B&Bs call South of Broad, because that side of Broad Street is where the ornate, antebellum houses are concentrated. The antebellum houses and the antebellum families. Like mine and the Robertsons.
In this well-heeled, Republican enclave there had been a lingering feeling of inevitability and dread that one day, one of the sons was going to turn out queer. It turned out to be me. When I'd come out at 14 two Christmases before, I think most of the adults in my parents' social circle were quietly relieved that the faggot fairy had skipped their houses, like some blue-blooded, WASP version of the Passover curse. There was an unspoken effusion of gratitude as if my mother and father had volunteered to take one for the team.
My parents themselves had received the news with dignified resignation. I'm sure they comforted each other that night with pithy comments about how well Dick and Lynne Cheney managed despite their queer daughter. My brother, Trey, home for winter break during his first year at college, blazed the trail of acceptance for them by hugging me and joking in his genial way that I'd be switching from the baseball to the girls' softball team in the spring. But my parents' aloofness was the first fissure in what would become the slowly widening chasm between me and them as we gradually drifted apart—until the earthquake of Trey getting killed by a drunk driver the week before I started tenth grade.
An evening thunderstorm had turned the hot but dry day into an oppressive swamp of humidity that May night in 2012. I could feel rivulets of sweat under my polo shirt and shorts, soaking into my boxer-briefs and the ankle socks I wore under my Reeboks. Larry Robertson had turned his front light off so the stoop was dark until he opened the door and light seeped into the street around his silhouette. He was nervous but not surprised as he hastily stepped aside and I walked in.
"I wasn't sure you would really come," he said. "My wife took the kids up to her mom's for the weekend, so we're all alone. You want something to drink?" I declined and followed him down the hall to what looked like an office. The room was lit only by a desk lamp with a green glass shade, so it was mostly dark. The wooden Venetian blinds were closed and there were bookshelves built into the wood-paneled walls.
"So, I guess you want the money first?" he asked, reaching back for his wallet.
"What exactly are we doing here?" I asked.
The question took him aback. Like having to actually say the words wasn't part of the deal. "I, uh, I..." He was stammering. I looked around his office. The dim light was reflecting off panes of glass around the room. Pictures and diplomas, I guess. It was too dark to make out more.
"What? You wanna fuck me on your desk or something?" I asked. He was standing there like a chastened little boy, holding his wallet loosely in front of his crotch with both hands. Silence hung in the air, marked only by his shallow, ragged breaths. I found myself becoming impatient, even though I didn't know what was coming. After a few minutes, I felt annoyed. "Look, when you asked me to come over here, you must have had something in mind. I'm not a psychic. You offered me two hundred bucks so I figured it's something you thought I wouldn't do without money. We're alone in your house, in your dark little office, so tell me what you want."
There was another long pause and I guess he saw that I was about to turn and leave when he asked softly, "Well, what do you like?"
I thought for a second. I'd never had sex before. There just weren't any opportunities for it. I hadn't even watched much porn because there wasn't much opportunity for that either. Our computer was in our living room. It had been since we first got one when I was like 10. I'd looked a few times after school when my mom was out, sometimes at night when my parents were at parties and shit like that. But I didn't know what I liked. So I told him I didn't know.
"You've never done this before?" he asked.
"What? Gone over to some old guy's house for cash? No."
"No. It's just...I thought...." He trailed off. He took a step forward and dropped the wallet on the desk to our side. He reached out and unbuttoned my shirt. His hands were shaking.
"Is this OK?" he asked.
"Yeah, I guess."
"Can you take it off?"
I reached back and grabbed the collar and pulled my shirt off over my head. "Oh, God," I heard him sigh. He took another step forward and we were basically only a foot apart. His dick tented out his khakis. The back of his right hand gently touched my left pec. "You're so beautiful." He almost whispered it. "You're so smooth and lean."
I was. Even then I was already about 6'1" and weighed only 130. I'm 6'3" now and still only 145, and that's after a lot of fucking time in the gym. Other than my pits and pubes, and a light dusting of thin hair on my lower arms and legs, I have basically no body hair. And it's all copper-colored, like a fresh penny. Unlike a lot of gingers, I don't have freckles, but I sunburn like a son of a bitch so I wear suncreen during the day all year round. I have the complexion of a glass of milk.
He rested his hands on my hips as he leaned in and licked my left nipple. For the first time, I felt a jolt of sexual pleasure. He sucked the nipple into his mouth and started rubbing it between his teeth as I exhaled sharply and pressed my chest out to his face. He gently turned my hips so I was back against his desk and I leaned on it. He slipped one hand between my legs, stroking up the inside of my thighs over my shorts. He kept complimenting how hot I was as he worked my nipple and kissed my pec. At last, his hand found my cock, half-hard in my shorts and angled to my hip.
"Fuck!" He pulled his head away from my chest and looked down at my crotch. "Jesus fuck, is that you?" he asked. He watched his hand trace along my dick, which was still swelling. He looked up and asked how big I was and I told him over eight. It's almost ten now, but what I had then was more than enough to impress him. "Can I see it?" he asked.
I shrugged but he wasn't looking up. "You're paying for it." I said. He dropped to his knees and unbuttoned my shorts. He tugged them down and gaped at the bulge in my boxer-briefs. He pressed his nose in tight and breathed in hard.
"Oh fuck," he said. "You're so fucking hot, Jeff." I hate being called Jeff. I hate most references to my first name, which is neither Jeff nor Jeffrey. My parents call me Pen, shortened from my middle name. My brother always called me J.P., and that's still what I prefer. But most people who don't know me don't know better. Larry Robertson didn't know better, but since he had just pulled the waistband of my underwear down and wrapped his lips around my cock, I didn't care.
I was leaning back with my palms flat on his desk as I started moaning "fuck." His tongue was probing under my foreskin and his lips clenching around my shaft. He had wrapped one hand around the base of my dick and the other gently cupped my balls. I kept rolling my hips up at him and the muscles between my navel and the hand around my dick were twitching uncontrollably. I couldn't stop saying "fuck." He sucked more of my cock into his mouth and my body reflexively curled around his head. I sat up on the desk and my hips and knees folded; my hands clutched the back of his head. I felt his throat clench tightly as he gagged. He tried to push back with his hands but at that moment I couldn't have been pried off with a crowbar. I was completely overwhelmed, shoving more cock in his throat as I surrendered to the primal instinct to embed myself completely. And then I came.
Every muscle in my body clenched as lava erupted from my balls and exploded deep in his throat. My dick spasmed for what felt like ten minutes, unleashing more and more cream. I was shouting but the words were unintelligible. When it was over, I simply collapsed, panting. I was utterly spent. I fell back on the desk and my legs dangled limply over the edge. The air conditioning felt cold and I realized distantly that I was covered in sweat again. I shivered, partly from chill and partly from Larry Robertson's mouth, slowly sucking the cum off my cock as he slid his face off me. He took each of my wrists in one of his hands, holding tightly. He laid one pair of our arms across my waist and pinned me down. He then wrapped his lips around the head of my cock again and started sucking hard, as hard as he could, like a calf on a teat, all while running his tongue relentlessly between my foreskin and cockhead. I struggled weakly against the intense sensation but there was nothing I could do. It felt like he was going to suck my balls out through my dick.
Eventually, he stopped and just started licking my balls.
"Oh shit," I basically whimpered.
"You liked that I guess," he said.
"Oh shit," I repeated.
"You taste so sweet, Jeff," he said. "Your cum but even your ball sweat."
"Gross," I said.
"Turn over," he said. I rolled my eyes. So here it is, I thought to myself. Time to get fucked. And it was going to be with this flabby, balding guy literally old enough to be my father. I almost said no, but he had taken my hips in his hands and was rolling me over the edge of the desk. I went with it, then felt his palms on my flat ass cheeks. He was pushing them apart.
"Oh my God," he murmured. "It's so beautiful. And it's totally smooth. Do you shave it?"
I felt myself grimace at the thought and was about to tell him no but instead of waiting for an answer, he put his mouth on my hole and started licking. "Oh, fuck!" I was starting to chant again. My back arched as I put my weight down on my forearms. My cock surged, despite having cum only minutes before.
"Mmm," I heard him moan. He was going to town eating my ass, wet slurping noises filling the air as his tongue swept against my hole over and over. And when it eventually pressed inside me, I had to close my eyes because I couldn't see straight anymore. And I couldn't talk, either. I mean, syllables were spilling out of my mouth but they didn't connect up into words. I had a vague awareness of him spreading my legs apart with his hands and then planting his knees between my ankles to keep them that way. A minute later, I had an acute awareness of him rubbing his fingertip against my hole while his tongue was still inside it, because that's when I started spasming on top of his desk like a fish landed on the deck of a boat.
His tongue slipped out and his finger slipped in. It didn't hurt, but it didn't feel right either. I stopped flopping around and started biting my lower lip. He was probing for something and then he hit it. My prostate. It felt like he'd rubbed it with sandpaper. I grimaced again and gritted my teeth. "No, stop," I said.
"No, you'll like it," he answered. I felt him trying to work a second finger in as he stood and fumbled with his belt buckle with his free hand.
"No, I said stop!" I looked over my shoulder. His pants were open now and a hard, stubby, circumcised cock poked out of the fly of his boxers. He hit my prostate again with his finger and it felt like someone stabbed it with an ice pick through my urethra. I bucked reflexively, then started to push myself up from the desk. But the hand he'd been using to get his dick out pushed down on my back. I felt his finger slide out of my ass and could see him starting to line his dick up with my hole.
This wasn't going to happen. Larry Robertson was not going to fuck me with his gross, cut little old-man dick. He had at least a hundred pounds on me, bulk that had probably been muscle when he was a college jock or something but that had dilapidated with age into flab, but it was still more weight than I could shift in my present position, as I learned after a few seconds of struggling. Finally, I went limp and felt the heat from his crotch on my ass. And that's when I deployed the nuclear option.
"Is this the way Scotty likes it?" I asked.
He froze. "What?" he asked softly.
I doubled-down on my bluff. "You heard me. Does he say 'Fuck me, daddy' when you pin him down here? Do you do it in the middle of the night when Mirabella's asleep upstairs?" I asked, naming his wife. "Or on the weekend, when she's out shopping?" He dropped his hands and staggered back.
"I...no...I...that's sick," he stammered.
I turned to face him. My dick had gone soft again. "What's sick? Raping a 16-year-old? Or only if he's your son?"
His face was ashen, like a stale corpse. His dick was soft, too, flopping out through the fly. But the look in his eyes wasn't disgust or outrage. It was guilt and fear. "No! I'd never touch Scott!"
And I knew. It was instantly clear. "No, you haven't touched him. You've just thought about it," I smirked. "Do you watch his ass from behind these blinds when he's marching back and forth mowing the lawn? Do you hide your eyes behind sunglasses as they move up and down his body at the pool?" He was backing slowly away as I stepped closer, but then he tripped on the pants around his ankles and fell heavily on his ass. "Do you..." I paused to let his dread grow, "...sneak his dirty underwear from the laundry and smell them?"
His eyes were already wide but when I said this, I saw the tears well up. "Oh God," he said. "How did you know? God, please don't tell him! Don't tell anyone!"
I had moved so close that I was straddling his twisted legs now. My cock was in his face again. "Put it back in your mouth and get it hard again," I said coldly.
"Oh God, please, Jeff?" he said, looking up at me.
"Don't call me Jeff. And suck my fucking cock," I said.
He leaned forward and put in his mouth. I closed my eyes and tilted my head back as he caressed it with his tongue. He seemed to love playing with my foreskin with the tip, and I loved it too. I took his head between my hands and began thrusting as I hardened. He started gagging but I didn't care. I felt his hands on my hips again, trying to control my pace and depth, and I shoved them away. When my balls began to churn, I pushed his forehead back.
"Get up," I said. "Bend over your desk."
He blinked stupidly. I slapped him.
"I...I can't," he said. "I've never...and...I mean, you're too big!"
I acted without thinking. I didn't have time to think. I just saw my hand reach out, grab his nose, and pull.
"Oooww!" he shrieked. I pulled him up and toward me as I reversed back to his desk. He scrambled to his feet and followed. I turned and pushed into his momentum until his chest landed with a thud on the blotter. Then I stepped behind him.
"How big is Scotty's dick, do you think?" I asked.
"What? I don't know," he said. It sounded like he was about to cry. "I've never looked."
"Oh, so you just want his ass then. I guess it doesn't matter. You can pretend this is him if you want. Or not." And with that, I pressed my knob against his hole.
"Oh fuck! No, please! Jeff! At least spit on it or something!"
"I told you not to call me Jeff." And I thrust forward.
He didn't squeal like a schoolgirl. It was more like an animal being slaughtered. His hole was so fucking tight. And hot. Way tighter and hotter than my fist when I jerk off. I was only halfway in when I decided he was right, I needed spit or something because what was left from skull-fucking him just wasn't enough. I cleared my throat and spat on my shaft, then shoved the rest in. I had to stop there because I was seeing stars again. I leaned my hips against his soft butt and flexed my cock hard inside him. I bit my bottom lip again and turned my face to the ceiling.
When he had asked me earlier, I hadn't known what I liked. But I knew now. I ground my hips against him in a counter-clockwise circle, like a pestle grinding in a mortar. Then I slowly pulled back and it felt like his ass was clenching around me, milking me, trying to squeeze the cum out of me. It felt so good I almost pulled all the way out but I stopped and pushed hard back in. He squealed again. I sighed.
Soon, I built up a rhythm. My hips were slapping his ass and my balls were swinging between my thighs like an upside-down metronome. The air began to smell faintly of shit. I looked down and saw he was crying. I wondered if my cock felt wrong inside him like his finger had inside me. Intuitively, I decided against it. My cock was a hell of a lot bigger than his finger, so it probably hurt like hell. I didn't care. He lusted after his own son and had been on the verge of raping me. I scowled and slapped his ass with my palm. He yelped.
"Boy raping son fucker," I hissed down at him without breaking my pace. He sobbed. In the corner of my eye, I saw his wallet, still lying on his desk where he had tossed it earlier. I reached down and picked through it. There were the two $100s, along with a couple $50s and a wad of $20s and smaller bills. I ignored them for now. I found what I was looking for and slid it out.
"Look at this," I said. I bent over, holding it in front of his face. It was his son's yearbook photo. He had been clenching his eyes tightly closed, the tears still squeezing out through them, but I grabbed his thinning hair with one hand and wrenched his head back. "Look!"
His eyes opened. I knew when they'd focused because he cried out and closed them again. "Look!" I repeated. They opened again and he resumed his sobbing. "Do you feel him inside you now? Is this the way you fantasized about it when you were jerking your stubby little cock?"
"Nooooo," he wailed.
"No? You were inside him instead?"
"Nooooo," he said again.
One of them was a lie. I figured it was the second one but I really didn't care. "Kiss him," I said.
He closed his eyes yet again and slowly pursed his trembling lips. I brought the photo to them and he kissed it.
"Say, 'I love you, Scotty,'" I demanded.
He wailed again but sniveled out the words.
"Again!" I said. "Say, 'Daddy loves you, Scotty!'". He said it. I made him say it again every time I thrust into his sloppy ass.
It didn't take much longer to cum. I'd blown once from the blowjob but this was my first fuck and I was still 16. I pumped my load inside him, my hands clutching him hard because my knees buckled and I didn't want to fall. I'm pretty sure I left bruises where my fingers gripped his shoulders through his shirt. I was panting and covered in sweat. I leaned there as my dick softened, Larry Robertson crying and limp below me, his eyes closed, his desk blotter stained with tears, Scott's yearbook photo discarded an inch or so from his nose.
When my dick was mostly soft, it fell from his now well-stretched hole. My cock was streaked with shit and cum and I think some blood. I pulled down the shirttail bunched up at the small of his back to clean it off. As I bent over to pick up my shorts and boxer-briefs, I saw a disgusting smear of colors leaking down the inside of his thighs. I got dressed and emptied his wallet, then I went home.
That's how I found out I love fucking guys who have sons in high school or college. I fuck guys my age, too, and guys in between, but dads are my favorite. If you want me to write about others, or better yet if you live near Charleston or UVA and want to get fucked, send me an email. But don't call me Jeff.