I got what only I assumed was an accidental text from my son Blake’s best friend, Skylar, a few weeks back. A common mistake. I’ve done it. He had texted me the day before asking if I could help fix his car. He must have still had the text window up and thought he was texting someone else because until now, I didn't even know he was gay. The picture was of him on all fours, on a bed, wearing nothing but black, thigh-high stockings and black, thong panties. He was looking at the camera over his shoulder with a smirk on his face. It shocked me.
Skylar was 18, almost 19, confident, obnoxious, cocky, and he knew he was hot, but I liked him. He was a good kid. He was charming when he wanted something. He was so attractive that all he had to was flash those white teeth, He was definitely not the type anyone suspected of being a sissy.
I had some experience with guys like him, jock sissy types. I was closeted, hooking up with guys on Grinder. The guys I hooked up with skewed young, and always athletic, masculine types. I liked the closeted ones because I know they would be discreet. I love being a hot daddy type. I love it when a hot dude called me daddy while I fucked him. I loved seeing a young, athletic guy who could be butch one minute, but then spin the bill of his ball cap around and suck my dick. I also found I attracted a certain subset of jock. They were jocks who had daddy issues, and they wanted to make me happy; they wanted my approval. So when I made them wear panties, they did it, no questions asked. I get off on turning a jacked guy into a sexy bitch. Seeing that pic made me suspect Skylar was wearing lingerie even without needing a daddy’s approval.
I noticed a couple of years back that Skylar was filling out, he looked amazing in his baseball uniform, those stretch polyester pants molding to his round, bubbled ass. The tight uniform shirt molded to his chest and biceps. He was boy-next-door cute. But he was my son’s best friend since they were 12. And at the time, he was only 17, so I instantly scolded myself for having those kinds of thoughts.
I didn't text back. I was in total shock and wouldn't even know what to say anyway. I didn't want to embarrass him. And I didn't want to out him to my son. But I didn't delete the picture. The more I looked at it, the more aroused it made me. The way the stockings looked on him, so feminine but his legs were so masculine. I started to imagine him dressed like this and getting fucked by men. Enough of these kinds of thoughts and soon I was jacking it to that pic every night, and cumming gallons. In the days that followed I felt a little guilty every time I saw him which was all the time since he hung out with my kid, playing video games, swimming in the pool, whatever. I saw him almost every day and I kept picturing him in the sexy lingerie. Then I would start to catch him staring at me sometimes, as if he knew that I knew about him. I would look away but there was some kind of tension in the air. He was acting like he had a secret that he wanted to tell.
One day, when I was working from home, Skylar showed up to hang by the pool. It was just me, the family wasn't home, but he was welcome to use the pool anytime he wanted, even if my son wasn’t around. That day Skylar whipped down his shorts by the pool and revealed that he was wearing a speedo, which he had never done before. Sexy as fuck. It was red, skintight, molded to his baseball jock ass, high cut on his thighs. He must had come from the gym because his muscles were pumped, and his body was shaved smooth. The red speedo could have been a red pair of panties if I squinted.
I took a deep breath and made my way outside. I tried to act nonchalant as I came outside to the pool. He was standing there scrolling on his phone, his back to me. I salivated at his wide back, narrow waist, bubble ass, and developed hamstrings. I considered standing there and watching him for a while longer. All I kept seeing was those stockings on his jock legs.
“Hey, Skylar,” I said with a nod and a smile.
“Sup, Mr. F.” There was that huge white smile. “I didn’t know you were going to be here. Working from home today?”
“Yeah. I’ve been doing that a lot more often lately. No one’s here so I usually get a lot done.”
He looked embarrassed. “Oh! Is it ok that I came over today? I can leave if you want me to.” I could tell that he didn’t mean what he was saying. He was being polite, but insincere.
“No, no. You’re fine. You’re welcome to use the pool whenever. I trust you.” I had to try and mentally shut off the images of him I was seeing in my head.
“Thanks, Mr. F. I have nothing to do today, and I’m bored. Thought I would work on my tan,” he said while holding his arm out to show me his skin. But he was tan already. He had silky, smooth skin, tan, and his biceps and triceps bulged. I swallowed hard trying to act like he wasn’t going to make my dick hard. He had the cockiest crocked smile as he tensed the muscle on his arm. The tension in the air grew thicker.
I laughed. “You’re tanner than you think you are.”
“You think? Nah, I don’t think so.”
I watched him give himself a once over, his abs tightened as if he were doing it on purpose. I couldn’t keep my eyes off that red speedo. I had to say something. He normally wore some kind of trunk when he swam.
“You’re definitely going to have some interesting tan lines in that suit.” I kept seeing lacy panties.
He looked down at his suit and then back to me. He laughed and shrugged.
“Do you usually wear skimpy suits this this?” I asked hanging on his every word.
He smiled. “When I’m alone. I know I would get shit from my buddies if I wore speedos around them, but I like wearing them. They’re sexy as fuck, yeah?”
I think I blushed. I chuckled nervously. He was being very obvious. What the fuck was his game? I scoffed. “They’re just jealous, Skylar. If they saw you right now... in that suit, they would just feel insecure,” I said and then suddenly wished I hadn’t said that.
He smirked at me. “Thanks! I mean, I don’t want to brag but look at this shit.” He flexed his arms. “Who wouldn’t be jealous?” His cocky smirk was sexy as fuck. “I’m fucking jacked.”
I chuckled at the boy. He was totally bragging, and he knew it. “You are jacked,” I said. “Hot.”
He smiled and held eye contact. I looked down and then back again. He was still smirking and looking at me. He knew I was interested. He knew he had me.
“I’ve always been jealous of Blake,” Skylar said as if changing the subject.
I looked at him confused. “What? Why?”
“Because he has you for a dad.”
“What’s wrong with your dad?”
“Nothing. But having you as a dad would be awesome. You’re nothing like other dads. You’re not bald, you’re not fat. You still look hot. I bet you get that a lot, don’t you?”
I blushed as I shrugged. “I have good genetics. It’s easy for me to pack on muscle.”
“I noticed.” He bit his bottom lip which was sexy.
We were quiet for a while. I think he was waiting for me to say something. But he folded his arms over his chest and leaned back against the wall, crossing his ankles. “Why didn’t you reply to my text?”
I froze and looked at him. His ripped, muscular, jock body glistening from the pool. I just stared at him, and he stared at me, his face was very serious. He lost his signature smirk. I said nothing.
"Mr. F?"
I started and then stopped. That was my confirmation that he sent it on purpose. I looked around to make sure no one was around, knowing there wasn’t but I was paranoid. "I... I thought you sent me that picture accidentally," I said.
"Nope," he simply stated.
I know I looked surprised. “I text back anything because I didn't want to embarrass you if you accidently sent it to me."
"It was for you," he said. “You know it was. If you didn’t know then, you know now.”
I began to sweat. I looked around again. I looked back and swallowed hard. I leaned in and asked, "Skylar, what are you doing?”
“I bet that pic is still on your phone,” he said. He said it like he was reading my mind.
I looked at him and then shook my head, but I wasn’t saying I didn’t have it. I was telling him that I was caught and I knew it.
“How did you know?”
He smirked at me. "You should be more careful with your Grinder profile, Mr. F," he said.
My face turned white. I started to tremble. "Shit.”
He chuckled. “Yeah, ‘daddy4jocksissy’” That was my Grinder handle. I didn’t have a face pic so I’m not sure how he knew it was me.
I tried to remember all the guys I chatted with but never hooked up with. I went through my mental database of descriptions, pictures, anything that would tell me who Skylar was online. Then I saw a mole near his naval. I’d seen that before. Then I felt like an idiot. That mole, his etched abs, the tan skin.
“’Jacked panty boy?’” I said.
“Bingo, Mr. F. That’s me.”
I was embarrassed. “You can't say anything."
He gave me a raised eyebrow. "Dude, why would I tell anyone? Everyone would know I'm on Grinder too. Duh. ‘Jacked panty boy’ isn’t exactly something I want spreading around.”
I was a little relieved. "So Blake doesn't know? About me or you?"
"God, no,” he scowled. “He thinks I'm straight as an arrow."
"Oh," I said sounding relieved. "You and I have chatted a few times. I assumed whomever I was chatting with was on the downlow because we never hooked up.”
“When I realized it was you, Mr. F... I wanted to hook up. But you know, kind hard with Blake around. I knew I had to be careful. I had to wait for the best time.”
“Wait, how did you know it was me online?”
He laughed. “A word of advice about hook-up app faceless selfies. If you’re on the downlow, always take your phone case off your phone.”
“Fuck,” I mumbled. I felt like an idiot. I thought I was being discreet.
“Yeah. Not too many guys out there with a phone case like yours. I’ve seen it a million times.”
My phone case looks like a vintage cassette tape. On the label I wrote “Harvard Mix” which was where I went to college. The case reminded me of a real mixed tape I made while at Harvard and that’s what I titled it.
“Harvard Mix.”
He nodded. “Harvard Mix.”
He pushed off the wall with his elbow. He reached up and swiped imaginary lint off the sleeve of my t-shirt, then his hand lingered.
"I...," I stammered. I stepped back. "Skylar...we can't do this."
He was amused at my attempt to thwart his advances. “You never said if you liked that pic. I mean, of course you did, right?”
I looked at him with trepidation. “I did,” I replied quietly but forcefully. He was taking control, and I didn’t like it. He had me where he wanted me. He was silent as he smiled at me. I just looked back at him, taking in his blue eyes, dark wavy hair.
"Well?" he asked.
"Well, what?"
"Are you gonna fuck me or what, Stephen?"
My body went slack, and I was sweating. He used my first name for the first time ever. "You just come over to your best friend's house and ask his dad to fuck you. Ballsy little fucker."
"Well, online we talked about doing it. I've wanted your dick since I was 14; as soon as I knew I was gay. I know you want to fuck me, Stephen.”
“It’s weird when you call me by my first name.”
Skylar ignored the comment. “Let's fuck. I brought some pretty things to wear for you," he said in a sing-song tone.
I perked up. "Wha.... what? You did?" I must have sounded like a fucking moron.
"You bet your hot ass I did." He was grinning now.
"Oh shit," I mumbled. I knew we would be alone for the rest of the day and into the evening. "You're my kid's best friend."
He rolled his eyes and put his hand on my forearm. "And I don't give a flying fuck. He’s not the one I want to fuck. I want his dad." He put his hand on my hard dick that was pushing out my shorts. "I'm going to put on some pretty panties for you, some stockings, and then I want to suck your dick and eat all your fucking daddy cream. Then I'm gonna spread my bitch legs for you and you're gonna smash my jock pussy until you cum again."
"Oh god," I whispered. Then he pulled my arm as he walked back inside. I felt like I was floating above myself as I was being led though my house. I watched his tight, muscular little ass in those tiny speedos. His muscular back flexed. My dick ached to get inside.
He led me to the bedroom. He told me to stay, and he went into my son's room. He came back wearing black nylon thigh high stockings, thong, and garter belt. He told me to sit back and relax. He dropped down to his knees, opened my shorts and dived down onto my cock. Holy shit, he was a good cocksucker. And he stood by his word because he sucked me until I came and then sucked some more.
Then he took off my shorts, laid me back on the bed, and straddled me. That's when he leaned forward and kissed me. And fuck me, he was a great kisser.
After the kissing, I looked up at him. "How are you such a great ki..."
"Lots of experience," he said cutting me off.
He produced a tube of lube. He reached behind him and took my cock. He slathered it with lube and tossed the tube aside. Then he came up on his knees, still reaching behind, he aimed my cock at his hole, and he slowly sat down. His eyes were closed, his teeth clenched as he slowly descended on my cock. I watched his determined face. His muscles flexed, his quads trembled. I grasped the sides of his waist and helped pull him down. We were both moaning and groaning. It was the tightest hole I'd ever been inside of. When he hit bottom, he grunted, took a deep breath, and then looked down at me with a grin.
"Fuck yeah," he said. He was such a bro, and he said it like a bro. “That’s good dick.”
"Oh shit," I whispered.
He pushed down on my chest, using it as leverage as he slowly lifted himself. He gasped and then let himself back down.
"Your dick is so fucking big," he groaned.
"You're doing fine." I watched his stockinged legs, the sexy fabric stretching around his quads and calves.
He posted himself slowly and then sped up. Soon he was bouncing up and down on my dick like it was a fucking stability ball at the gym. His face was staring at me. His teeth clenched. It was like he was on a mission. And that mission was to drain me.
"Fuck yeah," he hissed. "Waited so long for this dick. You’re gonna wreck my pussy, Stephen.”
I nodded. "You're so fucking sexy. Fucking sexy sissy jock boy.”
"Yeah? You like your sissy jock boy pussy?" he said it seductively.
"Oh my god, I fucking love my sissy jock boy’s pussy."
He settled down all the way and gyrated his ass on my dick. He looked down at me. "Fuck my pussy. Fuck my sissy jock pussy."
My heart raced suddenly. "Oh yeah, baby boy. Ride that dick."
"Fuck my pussy... daddy," he said in a breathy, sexy voice.
Something happened inside of me when he called me daddy. I reared up, flipped him on his back and entered him again.
He groaned loudly and then he gasped. "Oh fuck YES!" he yelled. His legs were on my shoulders. "Wreck my pussy, daddy! I'll be a good little muscle girl for you." His voice was low which made what he was saying even sexier.
He was saying all the right things. This gorgeous, cute, athletic, butch jock was calling me daddy and telling me to fuck his pussy, dressed in slutty lingerie. What more could I want?
I kissed him hard. Then I sat back, grabbed his ankles and spread his legs wide. "Do you want to be my little jock girl? My little muscle girl with a sweet jock pussy?"
He nodded quickly a few times. He became serious. His eyes were intense. It was like someone poured gasoline on him and lit him on fire. His low, baritone voice growled. "Fuck yeah I'm your fucking muscle girl. Daddy's gonna fuck his muscle girl's pussy whenever he wants on the down low. Gonna be your mistress. All I want is to be your side pussy."
My eyes got big. "Jesus fucking Christ, kid!" I hollered before I tensed up and exploded in that jock pussy. I came the hardest I ever had.
"Fuck yeah! Cum in your little jock girl's pussy! Get my jock cunt sticky wet."
The shit coming out of his mouth was intoxicating. I now had my own butch little muscle pussy.
I pulled out of him.
"Oh my god, fuck yeah! That was the best dick I've ever had," he said gleefully.
"There's a lot more of that... princess," I growled.
He licked his bottom lip and smiled. "Princess? That’s fucking sexy. Am I your princess?"
"Oh fuck yeah, you are. My little jock princess."
Fuck yeah," he whispered.
"You got more of these pretty things," I asked running my hand over his stockinged thigh.
He shrugged. "Some. Not much. Shit is expensive."
I smiled. "Don't worry then. I'll order some more things for you, princess. Got to keep my little jock girl looking pretty."
“This is hotter than I dreamed it would be.” He wrapped his ankles around my waist.
“You know what’s hot? You walking around here all butch, talking shit with Blake, talking about girls and he doesn’t know that you’re his dad’s little bitch.”
Skylar looked up at me and gasped. “Fuck, that’s hot. Tell me again.”
“You’re my little bitch. I’m gonna fuck your tight jock pussy all the time from now on.”
“Fuck, yeah,” he hissed. “Fucking fuck yeah.”
“You’re my butch little princess, aren’t you?”
“Yes, daddy. I want to be your jacked up cunt.”
“I’ll cunt you,” I said when I inserted back into him.
“Fuuuuuk, daddy,” he moaned as I sank in.
“After I cum inside your pussy again, we’re going shopping.”
“Really?”
“Oh yeah. I’ve got to get my new muscle girl some new things to wear. Would you like that, princess?”
Skylar was feeling my dick his is nut. “Uh huh, daddy,” he whimpered.
“Good girl,” I cooed into his ear. “My little muscled up sissy faggot.”
“Yes, daddy.”
I looked at my watch. “We have until 9:00 tonight. We’ll go shopping. Come back here and I’ll put one more load in your pussy before everyone gets back.”
“Deal.”
“Remember, Skylar. This is real. You keep that big, buff body nice and tight for me. I want my big strong boy to be a big strong bitch for me. You keep it tight. Got it?”
“Yes, daddy.”
“Good girl.”
