Growing up, I read a lot of books about orphans – a staple in British children's literature. One trope was always present: they would daydream that one day their parents would show up and sweep them away into a world so radically different than the one they inhabit. I had no fantasies like that about the father I never knew. Somehow, I always imagined he was just a regular bloke, the kind I saw on the bus every day.
But as it turns out, I was wrong. Dad was nothing like I'd imagined! The day after Thanksgiving, he asked me if I wanted to go spend Christmas with him in California, which after a short conversation with Mum I said yes to. Dad's father and younger brother spent a couple more days in London, and I said goodbye to them knowing I'd see them again in just a few weeks when the term was over.
School kept me busy in December, and Dad spent the time organising our trip. Turns out, he got us first-class tickets, which was sooo far removed from the budget flights I was used to taking to places like Spain. It was a good thing we were in first class, because every flight was crazy busy as we flew out of Heathrow, did a layover in New York, and proceeded to San Francisco.
Another good thing was that I could comfortably sleep on the plane. When I did, I had a recurring dream: my father lying in bed next to me, jacking off. It'd started on Thanksgiving, ever since I masturbated in Dad's bed and came on his used underwear. That night, I dreamt that Dad had come home, lain down next to me, jerked himself off, and used the same underwear to clean up the mess; all the while I was half-asleep next to him. It wasn't the first sex dream I'd had about my father, but it was by far the most realistic one! Ever since it happened, it kept coming back to me, including on the flight from New York to California.
"Time to wake up, Callum. C'mon. You can sleep when we get to Dad's house. He's got one of the guest rooms all ready for you," my father stirred me awake as we started to land. I woke up, and tried my best to hide my boner under the airline-logoed blanket. When I heard "one of the guest rooms" I pictured my grandfather living in some sort of mansion or a palace (which seemed to match his personality, based on the time I spent with him so far). Turns out, Granddad lived in a nice townhouse, which wasn't as large or grandiose as I'd imagined, but probably just as expensive.
Not that I really cared about that; I wanted to spend as much time out of the house as possible! Granddad's house was central enough that I could walk everywhere, and my internal gaydar led me to the Castro the very next day. Here, I marveled at the open display of gayness everywhere that surpassed even what I was used to in Soho back home.
After spending a few months in London, Dad had to go to his office here a few times, giving me ample time to explore the city either on my own or with my uncle Blake (it still felt weird calling someone my exact age my "uncle"). What I hadn't realised in London was that Blake was openly gay as well, giving us even more things to bond over.
"It must've been so much fun growing up here," I said to Blake one afternoon as we strolled through SoMa.
"Yes, everyone's really fun and liberal. I started going our years ago. Josh would take me to all these parties he went to if I begged hard enough."
I felt a pang of jealousy over the fact that Blake got to grow up around my dad and spend time with him. "What was my father like, when you were growing up?" I asked him.
"Oh, great. I mean, since he and Kris are so much older than me we never got in silly fights or anything. They were just the fun older brothers that let me do whatever I wanted when our father wasn't looking."
I also got to meet my other uncle, Kris, who was 24 and seemed busy with work and planning his upcoming wedding. He and his fiancée Mia didn't hang out with us too much, but we were all scheduled to spend Christmas together at Granddad's house.
After a few hours of walking around town and shopping with Blake, he seemed to get tired and said he wanted to head home. Meanwhile, my dad texted to say he was leaving the office and could come meet me, so I said goodbye to Blake and hung out by myself for a while, waiting for Dad.
"See anything you like?" someone snuck up behind me and startled me while I was looking at a shop window. My heart fluttering, I turned around and saw that it was Dad.
I blushed. I was standing in front of a gay sex shop and the thing I'd been looking at in the window was a jockstrap on a well-hung mannequin.
"Just browsing," I replied staring at the ground, and followed Dad to a Thai restaurant around the corner for dinner. On our way back, my eyes involuntarily strayed to the sex shop window again. Dad must've noticed it because he said "C'mon, let's go in." Before I knew what was happening, he had his hand on my back and guided me inside the shop.
"Hi there," Dad said to the person behind the counter as if they were old friends.
"Hey. Welcome back!" the man greeted him. My eyes widened when I saw that the shop assistant was wearing a black leather harness across his chest and was completely shirtless. The harness was matched by a pair of leather shorts on the man, who seemed to be in his 40s. He was rather chunky, and had salt-and-pepper hair covering his chest, arms and shoulders. Comically enough, he was also wearing a Santa hat, making him look just like Santa's kinky, bearish brother.
"This is my son," Dad introduced me to the man. "We're just looking around."
"Hi. And I'm gonna assume he is 18, which he needs to be to be in here," the man winked.
"Of course," Dad smiled and led me further into the store, while the man went to look back at his computer screen.
"How do you know this place?" I asked Dad, whispering for some reason.
"I've shopped here before," he replied nonchalantly.
"Nothing. I just assumed... I thought this was like a gay shop."
"What, straight people aren't allowed to buy sex toys?"
"No... Yeah, of course..." I stuttered, browsing around for something to look at so that Dad wouldn't notice me blushing. Unfortunately, what was in front of me was a display full of obscenely oversized dildos, which only made me go redder in the face.
"Is that what you were looking at?" Dad pointed at a rack full of underwear and jockstraps like the ones that were in the window.
"Yeah," I admitted. Either way, it was less embarrassing than staring at dildos that were the size of my entire leg from the knee down.
I'd wanted a jockstrap for YEARS now! I saw them in porn a lot, especially on younger guys such as myself, and the fact that I couldn't easily get one only made me want it more. Apparently, all I had to say was "Dad, can I have one of those?"
"Have a look around. If there's anything you like just get it. I haven't gotten you a Christmas present yet anyway," Dad said as casually as if we were in an ordinary toy store.
I looked around, feeling a tad nervous. Luckily, we were the only people in the shop. With two days to go until Christmas, apparently sex toys weren't high up on many people's shopping lists.
I went to look at some of the colourful briefs first. They were all extremely tight and low-cut. Even just holding them in my hands made my cock stir.
"If there's anything that you like, the fitting rooms are right over there," the harness-clad bear suddenly appeared from behind the register.
"I– I can try these on?" I asked nervously.
"Of course," the hunky man smiled and disappeared again.
I looked at Dad, who was walking around checking out some of the items in the store. I picked a couple of different briefs and went to one of the changing rooms, closing the curtain behind me. The gap between the curtain and the floor was so large that you could see up past my knees, offering little discretion. I wondered if this was done on purpose at a place like this.
I took my trousers and underwear off, and I tried on a red pair of briefs first. To see better, I took off my T-shirt as well. It wasn't every day I got to go underwear shopping in a sex store, after all. Checking myself out in the mirror, I LOVED the way the undies looked on me! As scrawny as I was, I never thought of myself as particularly sexy, but wearing this I felt... hot! It was a feeling I'd never quite felt before.
"Holy shit," I said out loud when I turned around and saw my arse in the mirror. Without a doubt, it was my best feature. Unlike many boys my age I didn't play football or rugby, but even the ones who did would kill to have an arse like mine, especially when I was wearing this.
"Everything okay?" I heard Dad ask and before I had the chance to reply he'd pulled open the curtain. "Looks good," he said and nodded in approval.
"Thanks," I blushed for the umpteenth time today. I was blushing not only because I was standing in front of my father in nothing but a pair of sexy underwear, but also because he actually said I looked good in them. "Let me try the rest of these on."
"Okay," Dad left, only closing the curtain halfway. Moving quickly, I took off the red briefs and tried on a blue pair. These ones made my bulge look extra big in the front. Either that, or my cock was growing because of how hot this all was.
"Let me know if you want me to get you something else off the rack," Dad suddenly reappeared, looking at me through the half-open curtain. I'm not sure if I was imagining things, but I could swear his eyes darted up-and-down as he gave me a once-over in the blue briefs, focusing on the area right between my legs. I tried to flex what muscle I had in order to impress my father.
"Umm," I said, "I was thinking of getting some of the other ones. The other kind."
"You meant the jockstraps? I'll bring you some," Dad said coolly.
Holy shit! Was this really happening?! When I was little, I'd go shopping with Mum; except then we'd shop for sweatshirts and jeans, not underwear that I would try on in the store. And certainly not jockstraps! Now, Dad was acting like this was just another ordinary shopping trip.
Yet somehow, as nervous as I was earlier, the nervousness was slowly starting to fade. I looked at myself in the mirror again, naked except for my socks and the blue briefs with the tag hanging off them, checking out my own bulge. This underwear definitely made me feel sexier, which in turn also seemed to make me braver. I felt more confident, and stood upright as Dad showed up again with a few pairs of jocks in his hands.
"I got you a few different sizes, from extra-small to medium," Dad handed me the jocks.
"Thanks." I waited for him to step back before I closed the curtain again.
The first pair I tried on was fairly basic: a white pouch with a red waistband. I took off the blue briefs and put on the jockstrap slowly, almost ceremoniously.
"How's it look?"
This time, my father completely startled me when he pulled the curtain open! I mean, it was one thing for him to see me trying on underwear, but another thing to see me in a jockstrap, with my bare arse on display. Yet, he seemed just as cool and casual as earlier.
"F– Fine," I struggled not to stutter too hard as I turned around. Whichever way I turned, Dad could see my arse either directly or in the mirror behind me. Besides, my bulge was now growing even bigger, my cock almost half-hard. Fuck!
"Here, let me fix that for you," my father suddenly reached in and adjusted one of the straps in the back, right under my right arsecheek. I felt the back of Dad's finger graze my skin as it moved downwards and inwards, and when I felt the band snap back against my arse I almost shot my load right there and then.
"I think I'm gonna try something else on," I quickly said, hoping that would get him to leave. I was feeling more confident, but NOT confident enough to let him see me with a full-blown boner.
"Okay," he said, retreating again and closing the curtain.
Alone in the changing room, I took a few deep breaths in an attempt to make my cock go softer. It worked to a certain degree, but I just couldn't get it to go all the way down. Instead, I tried on another jock, this one with a wider waistband that said Trophy Boy on it.
"Hubba hubba," my dad chimed in again after reopening the curtain. "Niiice."
"Thanks," I responded, this time turning around more confidently, even arching my back a little bit, poking my bum out.
"Damn, your ass looks amazing in those! I wish I could say you got it from me, but you got your mom to thank for that."
"Haha," I laughed politely, my head positively spinning. Did he really just say that??!!
"Let me see..." he said and knelt down, so my arse was basically in his face. I could almost feel his breath on my bare cheeks. This time, he reached up with both hands and adjusted both straps of my jock simultaneously. When he was done, he even cupped my cheeks with his large hands for a second, making sure everything fit properly.
"This place will be closed for Christmas, so just get whatever you want now. I'm not sure if we'll be able to come back," Dad continued as if this was the most normal father-son moment we were sharing.
"Okay," I nodded and watched him disappear behind the curtain again.
I turned to the mirror, my blood rushing all through my body. Before I could help myself, I put my right hand on my crotch, feeling my growing cock. Within a second, it was fully fucking hard.
"Damn, your ass looks amazing in those!" replayed over and over in my head as I closed my eyes. I never wanted to let this moment go. I could still feel my father's hands cupping my naked cheeks. My hand squeezed my erection and before I knew what was going on, I was cumming right inside the pouch of the underwear. A large load spurted out of my cock, seeping through the cotton material until I could feel it with my hand.
"Shit, shit, shit," I said softly. That orgasm felt amazing ("Damn, your ass looks amazing in those!" still replayed in my head) but as soon as it was done I started to panic. I'd cum inside the jockstrap. What the fuck do I do now?! I couldn't just put my trousers on over it and walk away; the security tag would make the sensors go off on our way out (besides, that would be stealing, of course). I could take it off and hide it somewhere in the store, but that felt... wrong. Running out of options, I got an idea.
"Dad? Can you ask the shop assistant to come here, please," I popped my head out the curtain and asked my father.
"Um, sure," he said, looking slightly confused. A short moment later, the leather bear came back, with a jolly smile on his face that matched his Santa hat.
"I have a question," I said as he walked into my changing room. Thankfully, he was alone. I covered up my crotch with both hands, still only wearing the jockstrap. "Could you take the security tag off here? In the changing room?"
"No, sorry honey, I have to do it at the register. Why?"
FUCK! Well, I had no choice but to admit the truth.
"I... had a little accident in them," I said, lifting my hands. By now my boner had gone away, but my jizz was still very much visible on the jock.
"Haha, oh, don't worry about that!" the man laughed. "You're not the first person to do that. Hell, you're not even the first person TODAY."
"So it's fine? You sure? Thank you," I said and slipped off the jock, handing it to the man. He didn't seem grossed out at all to take it in his hand. I quickly put on the boxer briefs I'd come here in, and gave the man the rest of the underwear I'd tried on. "I'll take all these."
"No prob. And by the way, they look great on you," the bear winked on his way out.
I put the rest of my clothes on and met Dad back at the register. He had already paid for everything and was holding three different bags. We thanked the friendly assistant and walked out into the street.
"This one's mine," Dad said upon checking the inside of one of the bags. It piqued my interest what he might've bought for himself. "And these two are for you. He put the... dirty ones in a separate bag," Dad said with a shit-eating smirk on his face as he handed me the bags.