Boys in their
Underwear
Underwear
Boys in their underwear boysintheirunderwear.com
All our boys are 18+ years of age!
All our boys are 18+ years of age!
Insane swimwear design photos
Courtesy of
www.koalaswim.com
makers of the world’s
most extreme swimwear, bikinis, thongs,
g-strings, fetish wear, sex wear, sheer wear
and playwear for men.
Boys In Their Underwear.
I’ve always had a thing for boys, and underwear. Ok, let me clarify – when I say boys, I don’t mean school kids. There is something about an older guy that has retained his boyish looks and can still pass for a school kid. Who wants a boy with no experience? Give me a boy, about 19 or 20, 24 at the outside, in a great pair of underwear, huge cock and smooth balls but with a bit of knowledge under his belt. Someone who can seduce me, and turn me on, and knows how to please a guy.
Who’ll look great in underwear, I should have said. He needs to be able to fill them – preferably with a hard-on that can bust rocks. Then again, if he has a smaller cock that’s okay too. I’m not too fussy in the cock department (after all, they all rise to the occasion and if you’ve seen one erect cock, you’ve seen them all). And a smaller cock plays into my young boy fantasy. So I suppose a pair of socks in their jocks would still get a reaction from me. It’s mainly about the underwear. Cocks in underwear, and boys with experience.
Anyway, I digress. Sticking with boys in their underwear. I think it started when I saw my older brother in his white jocks. He was well packaged, and by the time I was old enough to know about that kind of stuff I already knew I was into guys. My brother brought home girlfriends and I’d hear them in his bedroom – and sneaking a peak I’d see his hand up their t-shirts and all over their tits. As he got to know the girl better, the hand would move to under their skirts, fingering their cunts, and then pretty soon they were fucking – albeit quietly. But watching my brother fuck his girlfriends never did it for me. I got hard, but from watching him, not the girl. His white jocks, perfectly packaging his cock and balls. And when he began playing football, he and his team-mates would come back to our home, shower and change. I’d be surrounded by guys, all my brother’s age, wearing underwear and not much else. When they were older and began drinking, I was in heaven – they’d sit on the lounge, in their underwear, getting drunk and rearranging their cocks all night. I’d hide and jerk off to the delightful vision of these boys-almost-men in their underwear, or sometimes I’d fondle myself through my own underwear. If I came, I’d catch it in my pants and play with them for the rest of the night, sniffing them and feeling the dampness in the cotton.
Later I’d find myself watching other guys at the urinal, their beautiful cocks held nicely in check by underwear I longed to try on or play with. They’d take out their cocks and I’d almost start jerking off in front of them - and once I practically pissed on my shirt I was so hard from staring at this one guy. But they had to be about my brother’s age when he started college: 19, 20, give or take. It didn’t matter how old I was. That’s the image I had of my brother in his jocks, his mates changing at our place after football practice. And the memories of watching them in their underwear never left me.
When I started work I befriended the guys who looked most like the boys in my fantasy. And I made sure I was always in the bathroom when they went to take a leak. I’d watch them from the stall, as they took their cocks out of their underwear. I’d masturbate quietly, and as they put themselves away and flushed I’d cum, watching them place their cocks in their underwear and zip themselves up. Later on, as I moved up in the company, I’d offer to take the younger boys under my wing and mentor them. My first stop in the office tour was always the bathroom, and we’d take a leak together and I’d see what underwear the new boy was wearing. If it was white jocks I almost got hard then and there. Sometimes it was boxers, and they’d take their cocks out through the buttoned opening. Other times it was the fancy kind with loud patterns and colours. Every so often I’d come across someone who didn’t wear underwear at all. But it was always exciting – like having someone else unwrap a Christmas present, and you didn’t know what it held. I never made a move on these boys – my job and position in the company required discreetness – but once I had one come onto me. He was a work experience boy, still in college, and eager to learn about the business. I had taken him on the tour, and of course made the obligatory stop at the men’s room. I saw the boy was wearing white jocks, and he was smooth – exactly as I liked them. We finished up and completely by accident, bumped into each other as we both reached for the same tap. I took a step backwards and apologised – he didn’t move though, and instead put his hand on mine so we turned the tap on together. It was a moment from Ghost as we washed hands together – looking back on it now, it was pretty corny – and then as we left the bathroom his hand brushed my cock and there was no mistake. As everyone left the office at the end of the day, he hung back and knocked on the door to my corner office.
I looked up, and nodded for him to enter. I glanced at the door and he locked it behind himself, and then turned to close the blinds on my window. Neither of us spoke as we silently undressed and I saw him standing in front of me; white jocks and hairless crotch. Packaged neatly in his underwear was his cock – large, uncircumcised and not yet hard. It hung loosely inside his underwear. I wanted so badly to feel it inside me, to pull it hard as I fucked his tight ass. But for the moment I savoured the sight of him in his underwear, standing there waiting to be approved. I smiled, and beckoned him closer.
Leaning on the edge of my desk, I opened my legs slightly and he stood between them. We kissed for some time, our cocks just touching through our underwear, and I felt him grow hard as I ran my hand along his arms and trailed them down his back. He then put his hands on my cock, and I melted. Without a word he turned away from me and pulled his underwear down just enough so his ass was exposed, and he pulled his cheeks apart. I pulled down my own underwear and placed my wet cock at his hole. He was clean there as well, his hairless asshole like a tight bud waiting for me to plunder it. I rubbed the head of my cock and felt my balls against his underwear through mine, and spat on his hole, regretting the lube I had left in my car’s glovebox. Normally it was in my briefcase so I could jerk off in the bathrooms but I stupidly forgot it today. I pushed slightly and felt his hole open to me, and the boy sighed. He wasn’t a virgin but still fresh, and he leaned back on me gently, easing my cock inside him. My balls were still nestled in my underwear and I freed them so that when I started to fuck him, they could slap against his underwear. As his ass swallowed my cock, he stood up and lay against me so I could reach around and cup his balls. I ran my hand along his cock and pulled back the foreskin, rubbing my thumb at his cock hole and feeling the precum. He moved against me, rubbing his ass in my crotch. I was completely inside him, and it felt fucking awesome. His chest was smooth and taut, the muscles hard and flexing as he breathed in time to my fucking him.
We fucked for what seemed like forever, and I could feel by balls tighten and pretty soon I was breathing even heavier, my load working its way to my cock. He moved perfectly in time with me so I didn’t have to do much of the work as I neared orgasm, and finally I shuddered, my cock spasmed and I shot my cum deep into his asshole. Then he pulled away from me gently and quickly slipped his underwear up so he wouldn’t drip on my carpet. I still remember that. That, and what he said next.
In a little-boy voice, he politely asked me “Please, Sir, may I cum?”
“Ye.. yes.” I huffed, and he began to jerk off in front of me, his foreskin sliding over his head and back again with each stroke. I watched, mesmerised, his white jocks holding my attention more than the young apprentice masturbating before me. As he came he slouched forward, knees trembling. I grabbed a tissue to catch it and he mouthed a silent “Thankyou.”
I never saw him again after that afternoon – he moved to another department the next day, and I heard he now works for my company’s main rival on the other side of town. But the young boy in his underwear, offering his ass to me and pulling his underwear up so my cum wouldn’t stain the carpet is one of my other favourite memories. That, and my brother’s mates in their white underwear.
I found out in time that my secret desire for boys in their underwear was a legitimate fetish. I was not weird or abnormal, it was the same as any other fetish – be it boots, latex, spanking or watersports. I even discovered a website during my research that had people shitting on each other. Each to their own I suppose, but my ‘fetish’ (I was now proud to be able to give it a name) was boys in their underwear, and I was pleased to know it wasn’t wrong or dirty.
I found websites that advocated my fetish; some were paid, whereas others had free photos or short videos I could watch. I kept returning to the sites that had young-looking guys in underwear, their hands innocently holding cocks that were sometimes hard, sometimes not. There were videos of guys masturbating, their underwear only just pulled down so you could still see them in the shots. There were websites featuring guys that looked more like boys – young, clean shaved or waved, smooth crotches and cocks, hairless asses and come-to-bed eyes. They’d jerk off to the camera, and I’d sit at my computer with my own cock in my hands, wanking to their video. I’d cum like a rocket, shooting my load in my underwear so I could walk around and feel my cock and balls sliding around in it. And later, I’d always take the underwear off and play with it; the cotton soaked in my cum would find me playing with my stiffening cock again and again.
There were other sites, of dominated guys in latex and rubber underwear. These tended to be more on the sadism side of things and I was more fascinated than turned on by them. A site I opened out of curiosity inundated me with pictures of guys being ass fucked with massive dildos, and another page in the same website showed a guy being fisted – something I was not really exposed to before. The underwear was nice though – tight, riding high in their cracks and holding cocks tightly in place. Some were designed to hurt and I couldn’t fathom why a guy would want their cock bound, tied or strangled. Again, each to their own. But there was the odd shot of cocks in underwear that were made to ‘present’ the cock – holding it up and out, ready to be sucked or fucked. And one pair of underwear I discovered online had a metal ring in the strap that ran between the ass cheeks. The ring sat over the hole (like I needed any help to find it!) but the visual was incredible. I jerked off to the photo alone, then found a video of a guy being spanked while wearing one. It was more the anal ring (it was called an ‘anal spreader’) than the spanking that got to me, and it provided a week or so of masturbation material. I had a series of one-night-stands after meeting guys in bars, but I was always too shy to mention my fetish to them. So, I usually felt unfulfilled, despite having cum. It was the internet that provided me with my most satisfying experiences – even if I was alone.
I found and remembered my favourite sites, of (naturally) boys in their underwear, and as I explored further I found online groups where I could discuss my desires with others that had them. We traded photos and videos, or swapped stories and websites. Some guys were a little disturbing, but I made sure I only associated with legal sites and found a plethora of places where I could find people that fulfilled my prerequisites. Guys that still looked like young boys, who dressed in their underwear for the enjoyment of others. I made a few friends, tentatively. Mostly they were guys who, like me, loved boyish blokes in underwear. Some guys were a lot older, in their 50s and 60s, some were my age. I met up and had a drink with one of the older guys I’d befriended, who wanted me to wear my favourite underwear. I have no idea why I did it, as I had no intention of letting him see them. But a lack of common sense – and one too many beers – got the better of me and we ended up at a hotel. However I was pleasantly surprised – the fucking was brilliant. To be on the other side of the coin – a younger guy desired by an older guy with a fetish for underwear – was nice. He fucked me and sucked me until I had to ask him to stop. For an older bloke he had a huge hard cock that filled me like no other. And to be wanted as much as I had wanted boys… Well, it was a turn on. We only met the once, but we still talk online and he sends me photos of cocks in underwear that I always cum to.
I’m ashamed to say it, but I even arranged for a guy to come to my place once. I met him online, through an escort agency. He had to charge me for that occasion as it was booked and they had my credit card details, but we met again ‘off the books’ soon afterwards, and eventually we developed a relationship. He introduced me to places on the internet where I could purchase underwear that was, shall we say, a little unconventional. My favourite was the G-force, which was basically a sheath for my hard rod suspended on a few bits of skimpy straps. It showed every vein and bulge. Definitely not every-day-underwear but something we used with sex and role-playing.
He loved the female range, and with his soft little-boy cock held in check he looked exactly like a girl, pussy and all. It was nice to experiment and pretend to be straight, but my love was still young-looking guys in underwear – particularly white jocks. We’d fuck, and I always made him wear the white jocks just so I could see his package, neatly tucked away before and after. I’d always find myself going back to the images of my brother’s mates sitting and drinking beer on the lounge, and sometimes I’d make my boyfriends pretend I wasn’t there just so I could ‘secretly’ jerk off while I watched them. I’d save the underwear for later, playing with them while they were still wet, before washing them so they’d be fresh for the next time.
My relationship with the (for want of a better term) prostitute ran its course, and we both moved on. Even though I was now in my 30s, I still maintained a love of guys in their late teens and early 20s.
And one day I began an affair with a guy at work.
He was young, maybe 22 when we started, and not long married. His wife sounded like a right bitch, and we built a friendship based on mutual dislike for his new bride. He knew I was gay, and one day confided in me that he had experimented a little when he was at school. His best mate had seduced him in the showers and introduced him to anal fucking. They had moved very quickly to fisting, and he had even dabbled in bondage. He told me how great it felt having a hand in his ass, and asked me if I had tried it before. I kinda fobbed him off – fancy a straight guy asking me about being fisted!
Although he found he liked it, he never admitted to it and suppressed his feelings – marrying the girl he had dated at college after she fell pregnant. Later he found the child wasn’t his, but of course it was too late and like a good Catholic boy, he stayed with her. After a particularly nasty fight at home, I found myself driving to a bar in one of the seedier areas of town to pick him up.
When I got there I found out it was a gay bar I had never known about. God knows how he ended up there, but I marched up to the bar and discovered him talking to a guy who was obviously intent on taking him home.
“So there you are, Ben. Did you think I wouldn’t come after you? Sheesh, I’m sorry,” I said to the other guy. “He gets so worked up sometimes and just up and leaves – I’m sorry to have caused you so much trouble. Come on,” I said, turning back to Ben. “Let’s go home, baby.” I put my arms under his and escorted him from the bar, drunk.
In the car he looked miserable and dejected. “Thanks, Peter. She kicked me out, I didn’t know what to do.” He offered.
I shook my head. “It’s ok, let’s get you cleaned up and you can sleep it off and come to work with me in the morning.” Fucking Ben was the furthest thing from my mind, and our little role-play didn’t even turn me on. I honestly wanted him to sleep off the drink and have a decent rest. Having him so depressed and helpless brought out the nurturing side of me, and when we got home I helped him from the car and inside, holding his head and telling him how he’d be okay in the morning. I nursed him while he threw up and cleaned his face, making him coffee and a few sandwiches to soak up the drink. I helped him back to the lounge room, where I had intended to make up the spare bed for him. When we got there, he took his head from where it was resting on my shoulder and turned his face to me. He planted a gentle kiss on my neck.
“Thanks again, Peter.” He murmured and I felt his hand slide from my waist to my ass and rest there. He turned to face me more and met my eyes, moving towards my mouth. I’d known Ben for a year or so, and I’m telling the truth when I say I had never thought about sleeping with him. As far as I was concerned, he was married – and straight, despite his youthful experimenting. But here he was, making a move on me in my home, and I found myself wanting him. But I knew better.
“Hey, listen, you’re drunk. I wouldn’t take advantage of anyone in that condition, let alone you.” I eased him onto the lounge. His hand grabbed mine and he forced me to bend down to him. I felt his warm alcohol-soaked breath on my chest, coffee and peanut butter thankfully drowning out the smell of vomit.
“Aren’t I good enough to fuck?” He asked plaintively. “It’s okay, Dee Dee doesn’t think I’m good enough either.” A tear slid down his cheek and I softened. Kneeling in front of him, I took both his hands.
“Ben, you’re drunk. We’d do something you’d regret and you’re too good a friend to lose over that.” I was being candid. I did value his friendship. I didn’t have many friends, even less straight friends, and none I could call a good mate. Ben was one, and I valued that.
In response, though, Ben leaned in and kissed me. Open-mouthed and wanting, he pulled me closer and I let him, and kissed him back. He felt good, and it had been a while since I’d had any attention in my own home. But when he took my hand and placed it on his cock, I pulled away and shook my head.
“Ben, I can’t.” I said.
“Then let me.” He replied, and unzipped his trousers. I saw a flash of underwear and my cock stiffened in response. They were white y-fronts. But I felt so uncomfortable. “Please. I know what I’m doing, Peter. I’m not that drunk.” He explained, and I relented. I let him put my hand inside his pants, and I felt his cock. He was right – he was not too drunk, as his erection testified. I took his cock from the underwear and stroked it gently. He wasn’t too big – but as I’ve already said, smaller cocks don’t worry me too much. Less to fit in my mouth.
I lowered myself so I could take his dick, and as I sucked hard he fucked my mouth, grunting with each thrust. I enjoyed it – being smaller meant I didn’t gag, and Ben supported his weight on my lounge so he could raise his hips. His balls slapped my chin, and I took my free hand to fondle his underwear. It was cotton, simple, and plain. Without him knowing I rubbed them on my cheek, inhaling his scent, and as I sucked him I imagined him as a young boy, in the shower, being ass-fucked and fisted by his young mate. My cock dripped precum on the floor, and I didn’t care. I suddenly wanted Ben, to hell with the friendship. I wanted to fuck him every which way and back again, and do it over and over.
Ben whimpered, and in a few seconds my mouth was filled with his cum. He continued to move softly, pushing his cock in and slowly pulling it out again. His pubes ticked my nose but they were relatively short so I didn’t mind. The surprise came when, before I had a chance to swallow, Ben ducked down and kissed me again, sucking his load from my mouth. Then he slid down onto the floor and underneath me, kissing me all the while. I lay on top of him for some time, kissing him deeply and tasting his cum on both our breaths. His tongue moved expertly, his hands cupping my ass and lightly fingering my hole. He kissed my neck again and I shivered. My cock felt like it was going to burst, and Ben could sense it too.
“Fuck me, Pete. I want your cock in my ass. I’ve wanted it since we started working together. Please.” He needn’t have added the last word, as I was already pulling my underwear off, and tugging at his. Tossing my underwear side, I held his in my hand and jumped up.
“I’ll be right back, don’t go anywhere.” I raced into my bedroom and grabbed the lube from my briefcase. Spreading it on my cock as I made my way back to the lounge room, I again smelled his underwear. They were surprisingly fresh, and I held onto them as I lowered myself on him and he raised his legs over my shoulders. I’d shucked my shirt on the way to the bedroom and Ben had stripped his so we were both still in our socks, but nothing else.
“I figured you were an underwear guy.” Ben smiled as I rubbed my slippery dick at his hole. His boyish grin, little cock and plain underwear almost sent me over the edge then, but I waited and gradually eased myself into him. He raised his ass off the floor to give me better access and I took him in one move. I saw his arm stretch out next to him, and I almost died when his fingers found my underwear and brought them to his face. He rubbed them on his mouth, and as I fucked his ass he moved them from his own cock to his mouth so he could taste the precum forming there again. His ass was so incredibly tight, I instantly understood the attraction of the underwear that strangled your cock and pondered (briefly) about buying a pair.
I let go of Ben’s ankles at my ears and put my hands either side of his head, riding him hard, and squashing his cock between us. My balls slapped him in a beautiful rhythm I can still hear today. Ben just managed to get his hand down there, and began to jerk off using my underwear. That did it then, and I exploded in his ass with a cry. He came too, and brought my underwear to his mouth and then to mine. I felt the familiar pungent dampness on the fabric.
Ben slept in my bed that night and we fucked again in the morning before showering and heading off to work. The affair continued for three years and in that time he divorced Dee Dee and moved in with me – and no-one ever found out. We kept on using underwear in our sex life, and I introduced him to the range of underwear I purchased while I was fucking the prostitute. Ben’s favourite was the Pinnacle Bikini – a little offering that held his cock nicely in a small pouch poking out from his crotch. I showed him how to use creams to get rid of his short pubes, so when he wore his underwear he looked for all the world like a little boy. Our best-loved game was re-enacting the shower scene, which I relished. I was his mate, seducing him in the shower (I had a double shower so there was always plenty of room). We start off watching telly, and Ben’s signal was when he told me he had to go take a leak. I’d follow him to the bathroom, and ‘decide’ to have a shower. Once inside, I’d convince him to join me and soon we’d be kissing, me telling him it was alright and all good mates did it. I’d lather his smooth body, slowly making my way to his ass, and begin to finger it. His tight hole wrapped around my digit got me hard, and when he was opened enough to take a couple of fingers I’d fuck him. It soon got to the stage where I felt comfortable enough to fist him, and trust me, that was magic. Watching my hand disappear into his ass, seeing his hole stretched so far… I finally knew what the attraction was there, too. We graduated to huge dildos, and experimented with light sadistic play. Ben found that he enjoyed being dominated by me, and some pain turned him on. I wasn’t really into it, but if Ben enjoyed it then I did it for him. But we always came back to the underwear.
During the stress of the court case where Dee Dee tried to get alimony from Ben for the child that wasn’t his, our relationship fell apart and we decided to call it quits. We’re still the best of friends and I exchange a pair of white underwear with him every Christmas. On Christmas morning I jerk off with them, and send the underwear back to him, cum-soaked and gift-wrapped. He does the same for me.
Nowadays I am in my 40s, and in a relationship with a gorgeous 19 year old (although he looks about 17). Dan is blonde, smooth and buff. I’m in pretty good condition myself – I have to be, to look good in my G-force bikini (if I were chatting online I’d put one of those little smiley faces in here). Dan loves wearing a piece of underwear called the Nasty Bitch – complete with a built in anal spreader and a tiny pouch that holds his little cock nice and flat. When I first met Dan he told me he had a small penis. He wasn’t too worried about it, and it is a little small, but I love it. It fits well in the Nasty Bitch and I love sucking it – it reminds me of Ben’s little cock. And the anal spreader just tops it all off. When he wears the underwear and bends over to present his ass to me for fucking, I can’t help but fuck him harder than I probably should. I guess I like the dominating bit more than I let on. Maybe Ben was onto something there, too.
We have a great sex life, and Dan moved in a month or so ago. I suppose you could say we’re in love. I certainly love fucking him. And I know he loves me.
Dan showed me the joys of being fisted, as opposed to fisting someone else. It took some time, but as I get older I like to think of myself as being more open to experimentation. So when Dan mentioned it casually one night I thought ‘Why not?’ After a few weeks my ass was more accommodating and Dan’s young fist felt right at home there. With his hand in my ass and me jerking off, and him in a pair of white jocks, life is wonderful.
Courtesy of
www.koalaswim.com
makers of the world’s
most extreme swimwear, bikinis, thongs,
g-strings, fetish wear, sex wear, sheer wear
and playwear for men.
Boys In Their Underwear.
I’ve always had a thing for boys, and underwear. Ok, let me clarify – when I say boys, I don’t mean school kids. There is something about an older guy that has retained his boyish looks and can still pass for a school kid. Who wants a boy with no experience? Give me a boy, about 19 or 20, 24 at the outside, in a great pair of underwear, huge cock and smooth balls but with a bit of knowledge under his belt. Someone who can seduce me, and turn me on, and knows how to please a guy.
Who’ll look great in underwear, I should have said. He needs to be able to fill them – preferably with a hard-on that can bust rocks. Then again, if he has a smaller cock that’s okay too. I’m not too fussy in the cock department (after all, they all rise to the occasion and if you’ve seen one erect cock, you’ve seen them all). And a smaller cock plays into my young boy fantasy. So I suppose a pair of socks in their jocks would still get a reaction from me. It’s mainly about the underwear. Cocks in underwear, and boys with experience.
Anyway, I digress. Sticking with boys in their underwear. I think it started when I saw my older brother in his white jocks. He was well packaged, and by the time I was old enough to know about that kind of stuff I already knew I was into guys. My brother brought home girlfriends and I’d hear them in his bedroom – and sneaking a peak I’d see his hand up their t-shirts and all over their tits. As he got to know the girl better, the hand would move to under their skirts, fingering their cunts, and then pretty soon they were fucking – albeit quietly. But watching my brother fuck his girlfriends never did it for me. I got hard, but from watching him, not the girl. His white jocks, perfectly packaging his cock and balls. And when he began playing football, he and his team-mates would come back to our home, shower and change. I’d be surrounded by guys, all my brother’s age, wearing underwear and not much else. When they were older and began drinking, I was in heaven – they’d sit on the lounge, in their underwear, getting drunk and rearranging their cocks all night. I’d hide and jerk off to the delightful vision of these boys-almost-men in their underwear, or sometimes I’d fondle myself through my own underwear. If I came, I’d catch it in my pants and play with them for the rest of the night, sniffing them and feeling the dampness in the cotton.
Later I’d find myself watching other guys at the urinal, their beautiful cocks held nicely in check by underwear I longed to try on or play with. They’d take out their cocks and I’d almost start jerking off in front of them - and once I practically pissed on my shirt I was so hard from staring at this one guy. But they had to be about my brother’s age when he started college: 19, 20, give or take. It didn’t matter how old I was. That’s the image I had of my brother in his jocks, his mates changing at our place after football practice. And the memories of watching them in their underwear never left me.
When I started work I befriended the guys who looked most like the boys in my fantasy. And I made sure I was always in the bathroom when they went to take a leak. I’d watch them from the stall, as they took their cocks out of their underwear. I’d masturbate quietly, and as they put themselves away and flushed I’d cum, watching them place their cocks in their underwear and zip themselves up. Later on, as I moved up in the company, I’d offer to take the younger boys under my wing and mentor them. My first stop in the office tour was always the bathroom, and we’d take a leak together and I’d see what underwear the new boy was wearing. If it was white jocks I almost got hard then and there. Sometimes it was boxers, and they’d take their cocks out through the buttoned opening. Other times it was the fancy kind with loud patterns and colours. Every so often I’d come across someone who didn’t wear underwear at all. But it was always exciting – like having someone else unwrap a Christmas present, and you didn’t know what it held. I never made a move on these boys – my job and position in the company required discreetness – but once I had one come onto me. He was a work experience boy, still in college, and eager to learn about the business. I had taken him on the tour, and of course made the obligatory stop at the men’s room. I saw the boy was wearing white jocks, and he was smooth – exactly as I liked them. We finished up and completely by accident, bumped into each other as we both reached for the same tap. I took a step backwards and apologised – he didn’t move though, and instead put his hand on mine so we turned the tap on together. It was a moment from Ghost as we washed hands together – looking back on it now, it was pretty corny – and then as we left the bathroom his hand brushed my cock and there was no mistake. As everyone left the office at the end of the day, he hung back and knocked on the door to my corner office.
I looked up, and nodded for him to enter. I glanced at the door and he locked it behind himself, and then turned to close the blinds on my window. Neither of us spoke as we silently undressed and I saw him standing in front of me; white jocks and hairless crotch. Packaged neatly in his underwear was his cock – large, uncircumcised and not yet hard. It hung loosely inside his underwear. I wanted so badly to feel it inside me, to pull it hard as I fucked his tight ass. But for the moment I savoured the sight of him in his underwear, standing there waiting to be approved. I smiled, and beckoned him closer.
Leaning on the edge of my desk, I opened my legs slightly and he stood between them. We kissed for some time, our cocks just touching through our underwear, and I felt him grow hard as I ran my hand along his arms and trailed them down his back. He then put his hands on my cock, and I melted. Without a word he turned away from me and pulled his underwear down just enough so his ass was exposed, and he pulled his cheeks apart. I pulled down my own underwear and placed my wet cock at his hole. He was clean there as well, his hairless asshole like a tight bud waiting for me to plunder it. I rubbed the head of my cock and felt my balls against his underwear through mine, and spat on his hole, regretting the lube I had left in my car’s glovebox. Normally it was in my briefcase so I could jerk off in the bathrooms but I stupidly forgot it today. I pushed slightly and felt his hole open to me, and the boy sighed. He wasn’t a virgin but still fresh, and he leaned back on me gently, easing my cock inside him. My balls were still nestled in my underwear and I freed them so that when I started to fuck him, they could slap against his underwear. As his ass swallowed my cock, he stood up and lay against me so I could reach around and cup his balls. I ran my hand along his cock and pulled back the foreskin, rubbing my thumb at his cock hole and feeling the precum. He moved against me, rubbing his ass in my crotch. I was completely inside him, and it felt fucking awesome. His chest was smooth and taut, the muscles hard and flexing as he breathed in time to my fucking him.
We fucked for what seemed like forever, and I could feel by balls tighten and pretty soon I was breathing even heavier, my load working its way to my cock. He moved perfectly in time with me so I didn’t have to do much of the work as I neared orgasm, and finally I shuddered, my cock spasmed and I shot my cum deep into his asshole. Then he pulled away from me gently and quickly slipped his underwear up so he wouldn’t drip on my carpet. I still remember that. That, and what he said next.
In a little-boy voice, he politely asked me “Please, Sir, may I cum?”
“Ye.. yes.” I huffed, and he began to jerk off in front of me, his foreskin sliding over his head and back again with each stroke. I watched, mesmerised, his white jocks holding my attention more than the young apprentice masturbating before me. As he came he slouched forward, knees trembling. I grabbed a tissue to catch it and he mouthed a silent “Thankyou.”
I never saw him again after that afternoon – he moved to another department the next day, and I heard he now works for my company’s main rival on the other side of town. But the young boy in his underwear, offering his ass to me and pulling his underwear up so my cum wouldn’t stain the carpet is one of my other favourite memories. That, and my brother’s mates in their white underwear.
I found out in time that my secret desire for boys in their underwear was a legitimate fetish. I was not weird or abnormal, it was the same as any other fetish – be it boots, latex, spanking or watersports. I even discovered a website during my research that had people shitting on each other. Each to their own I suppose, but my ‘fetish’ (I was now proud to be able to give it a name) was boys in their underwear, and I was pleased to know it wasn’t wrong or dirty.
I found websites that advocated my fetish; some were paid, whereas others had free photos or short videos I could watch. I kept returning to the sites that had young-looking guys in underwear, their hands innocently holding cocks that were sometimes hard, sometimes not. There were videos of guys masturbating, their underwear only just pulled down so you could still see them in the shots. There were websites featuring guys that looked more like boys – young, clean shaved or waved, smooth crotches and cocks, hairless asses and come-to-bed eyes. They’d jerk off to the camera, and I’d sit at my computer with my own cock in my hands, wanking to their video. I’d cum like a rocket, shooting my load in my underwear so I could walk around and feel my cock and balls sliding around in it. And later, I’d always take the underwear off and play with it; the cotton soaked in my cum would find me playing with my stiffening cock again and again.
There were other sites, of dominated guys in latex and rubber underwear. These tended to be more on the sadism side of things and I was more fascinated than turned on by them. A site I opened out of curiosity inundated me with pictures of guys being ass fucked with massive dildos, and another page in the same website showed a guy being fisted – something I was not really exposed to before. The underwear was nice though – tight, riding high in their cracks and holding cocks tightly in place. Some were designed to hurt and I couldn’t fathom why a guy would want their cock bound, tied or strangled. Again, each to their own. But there was the odd shot of cocks in underwear that were made to ‘present’ the cock – holding it up and out, ready to be sucked or fucked. And one pair of underwear I discovered online had a metal ring in the strap that ran between the ass cheeks. The ring sat over the hole (like I needed any help to find it!) but the visual was incredible. I jerked off to the photo alone, then found a video of a guy being spanked while wearing one. It was more the anal ring (it was called an ‘anal spreader’) than the spanking that got to me, and it provided a week or so of masturbation material. I had a series of one-night-stands after meeting guys in bars, but I was always too shy to mention my fetish to them. So, I usually felt unfulfilled, despite having cum. It was the internet that provided me with my most satisfying experiences – even if I was alone.
I found and remembered my favourite sites, of (naturally) boys in their underwear, and as I explored further I found online groups where I could discuss my desires with others that had them. We traded photos and videos, or swapped stories and websites. Some guys were a little disturbing, but I made sure I only associated with legal sites and found a plethora of places where I could find people that fulfilled my prerequisites. Guys that still looked like young boys, who dressed in their underwear for the enjoyment of others. I made a few friends, tentatively. Mostly they were guys who, like me, loved boyish blokes in underwear. Some guys were a lot older, in their 50s and 60s, some were my age. I met up and had a drink with one of the older guys I’d befriended, who wanted me to wear my favourite underwear. I have no idea why I did it, as I had no intention of letting him see them. But a lack of common sense – and one too many beers – got the better of me and we ended up at a hotel. However I was pleasantly surprised – the fucking was brilliant. To be on the other side of the coin – a younger guy desired by an older guy with a fetish for underwear – was nice. He fucked me and sucked me until I had to ask him to stop. For an older bloke he had a huge hard cock that filled me like no other. And to be wanted as much as I had wanted boys… Well, it was a turn on. We only met the once, but we still talk online and he sends me photos of cocks in underwear that I always cum to.
I’m ashamed to say it, but I even arranged for a guy to come to my place once. I met him online, through an escort agency. He had to charge me for that occasion as it was booked and they had my credit card details, but we met again ‘off the books’ soon afterwards, and eventually we developed a relationship. He introduced me to places on the internet where I could purchase underwear that was, shall we say, a little unconventional. My favourite was the G-force, which was basically a sheath for my hard rod suspended on a few bits of skimpy straps. It showed every vein and bulge. Definitely not every-day-underwear but something we used with sex and role-playing.
He loved the female range, and with his soft little-boy cock held in check he looked exactly like a girl, pussy and all. It was nice to experiment and pretend to be straight, but my love was still young-looking guys in underwear – particularly white jocks. We’d fuck, and I always made him wear the white jocks just so I could see his package, neatly tucked away before and after. I’d always find myself going back to the images of my brother’s mates sitting and drinking beer on the lounge, and sometimes I’d make my boyfriends pretend I wasn’t there just so I could ‘secretly’ jerk off while I watched them. I’d save the underwear for later, playing with them while they were still wet, before washing them so they’d be fresh for the next time.
My relationship with the (for want of a better term) prostitute ran its course, and we both moved on. Even though I was now in my 30s, I still maintained a love of guys in their late teens and early 20s.
And one day I began an affair with a guy at work.
He was young, maybe 22 when we started, and not long married. His wife sounded like a right bitch, and we built a friendship based on mutual dislike for his new bride. He knew I was gay, and one day confided in me that he had experimented a little when he was at school. His best mate had seduced him in the showers and introduced him to anal fucking. They had moved very quickly to fisting, and he had even dabbled in bondage. He told me how great it felt having a hand in his ass, and asked me if I had tried it before. I kinda fobbed him off – fancy a straight guy asking me about being fisted!
Although he found he liked it, he never admitted to it and suppressed his feelings – marrying the girl he had dated at college after she fell pregnant. Later he found the child wasn’t his, but of course it was too late and like a good Catholic boy, he stayed with her. After a particularly nasty fight at home, I found myself driving to a bar in one of the seedier areas of town to pick him up.
When I got there I found out it was a gay bar I had never known about. God knows how he ended up there, but I marched up to the bar and discovered him talking to a guy who was obviously intent on taking him home.
“So there you are, Ben. Did you think I wouldn’t come after you? Sheesh, I’m sorry,” I said to the other guy. “He gets so worked up sometimes and just up and leaves – I’m sorry to have caused you so much trouble. Come on,” I said, turning back to Ben. “Let’s go home, baby.” I put my arms under his and escorted him from the bar, drunk.
In the car he looked miserable and dejected. “Thanks, Peter. She kicked me out, I didn’t know what to do.” He offered.
I shook my head. “It’s ok, let’s get you cleaned up and you can sleep it off and come to work with me in the morning.” Fucking Ben was the furthest thing from my mind, and our little role-play didn’t even turn me on. I honestly wanted him to sleep off the drink and have a decent rest. Having him so depressed and helpless brought out the nurturing side of me, and when we got home I helped him from the car and inside, holding his head and telling him how he’d be okay in the morning. I nursed him while he threw up and cleaned his face, making him coffee and a few sandwiches to soak up the drink. I helped him back to the lounge room, where I had intended to make up the spare bed for him. When we got there, he took his head from where it was resting on my shoulder and turned his face to me. He planted a gentle kiss on my neck.
“Thanks again, Peter.” He murmured and I felt his hand slide from my waist to my ass and rest there. He turned to face me more and met my eyes, moving towards my mouth. I’d known Ben for a year or so, and I’m telling the truth when I say I had never thought about sleeping with him. As far as I was concerned, he was married – and straight, despite his youthful experimenting. But here he was, making a move on me in my home, and I found myself wanting him. But I knew better.
“Hey, listen, you’re drunk. I wouldn’t take advantage of anyone in that condition, let alone you.” I eased him onto the lounge. His hand grabbed mine and he forced me to bend down to him. I felt his warm alcohol-soaked breath on my chest, coffee and peanut butter thankfully drowning out the smell of vomit.
“Aren’t I good enough to fuck?” He asked plaintively. “It’s okay, Dee Dee doesn’t think I’m good enough either.” A tear slid down his cheek and I softened. Kneeling in front of him, I took both his hands.
“Ben, you’re drunk. We’d do something you’d regret and you’re too good a friend to lose over that.” I was being candid. I did value his friendship. I didn’t have many friends, even less straight friends, and none I could call a good mate. Ben was one, and I valued that.
In response, though, Ben leaned in and kissed me. Open-mouthed and wanting, he pulled me closer and I let him, and kissed him back. He felt good, and it had been a while since I’d had any attention in my own home. But when he took my hand and placed it on his cock, I pulled away and shook my head.
“Ben, I can’t.” I said.
“Then let me.” He replied, and unzipped his trousers. I saw a flash of underwear and my cock stiffened in response. They were white y-fronts. But I felt so uncomfortable. “Please. I know what I’m doing, Peter. I’m not that drunk.” He explained, and I relented. I let him put my hand inside his pants, and I felt his cock. He was right – he was not too drunk, as his erection testified. I took his cock from the underwear and stroked it gently. He wasn’t too big – but as I’ve already said, smaller cocks don’t worry me too much. Less to fit in my mouth.
I lowered myself so I could take his dick, and as I sucked hard he fucked my mouth, grunting with each thrust. I enjoyed it – being smaller meant I didn’t gag, and Ben supported his weight on my lounge so he could raise his hips. His balls slapped my chin, and I took my free hand to fondle his underwear. It was cotton, simple, and plain. Without him knowing I rubbed them on my cheek, inhaling his scent, and as I sucked him I imagined him as a young boy, in the shower, being ass-fucked and fisted by his young mate. My cock dripped precum on the floor, and I didn’t care. I suddenly wanted Ben, to hell with the friendship. I wanted to fuck him every which way and back again, and do it over and over.
Ben whimpered, and in a few seconds my mouth was filled with his cum. He continued to move softly, pushing his cock in and slowly pulling it out again. His pubes ticked my nose but they were relatively short so I didn’t mind. The surprise came when, before I had a chance to swallow, Ben ducked down and kissed me again, sucking his load from my mouth. Then he slid down onto the floor and underneath me, kissing me all the while. I lay on top of him for some time, kissing him deeply and tasting his cum on both our breaths. His tongue moved expertly, his hands cupping my ass and lightly fingering my hole. He kissed my neck again and I shivered. My cock felt like it was going to burst, and Ben could sense it too.
“Fuck me, Pete. I want your cock in my ass. I’ve wanted it since we started working together. Please.” He needn’t have added the last word, as I was already pulling my underwear off, and tugging at his. Tossing my underwear side, I held his in my hand and jumped up.
“I’ll be right back, don’t go anywhere.” I raced into my bedroom and grabbed the lube from my briefcase. Spreading it on my cock as I made my way back to the lounge room, I again smelled his underwear. They were surprisingly fresh, and I held onto them as I lowered myself on him and he raised his legs over my shoulders. I’d shucked my shirt on the way to the bedroom and Ben had stripped his so we were both still in our socks, but nothing else.
“I figured you were an underwear guy.” Ben smiled as I rubbed my slippery dick at his hole. His boyish grin, little cock and plain underwear almost sent me over the edge then, but I waited and gradually eased myself into him. He raised his ass off the floor to give me better access and I took him in one move. I saw his arm stretch out next to him, and I almost died when his fingers found my underwear and brought them to his face. He rubbed them on his mouth, and as I fucked his ass he moved them from his own cock to his mouth so he could taste the precum forming there again. His ass was so incredibly tight, I instantly understood the attraction of the underwear that strangled your cock and pondered (briefly) about buying a pair.
I let go of Ben’s ankles at my ears and put my hands either side of his head, riding him hard, and squashing his cock between us. My balls slapped him in a beautiful rhythm I can still hear today. Ben just managed to get his hand down there, and began to jerk off using my underwear. That did it then, and I exploded in his ass with a cry. He came too, and brought my underwear to his mouth and then to mine. I felt the familiar pungent dampness on the fabric.
Ben slept in my bed that night and we fucked again in the morning before showering and heading off to work. The affair continued for three years and in that time he divorced Dee Dee and moved in with me – and no-one ever found out. We kept on using underwear in our sex life, and I introduced him to the range of underwear I purchased while I was fucking the prostitute. Ben’s favourite was the Pinnacle Bikini – a little offering that held his cock nicely in a small pouch poking out from his crotch. I showed him how to use creams to get rid of his short pubes, so when he wore his underwear he looked for all the world like a little boy. Our best-loved game was re-enacting the shower scene, which I relished. I was his mate, seducing him in the shower (I had a double shower so there was always plenty of room). We start off watching telly, and Ben’s signal was when he told me he had to go take a leak. I’d follow him to the bathroom, and ‘decide’ to have a shower. Once inside, I’d convince him to join me and soon we’d be kissing, me telling him it was alright and all good mates did it. I’d lather his smooth body, slowly making my way to his ass, and begin to finger it. His tight hole wrapped around my digit got me hard, and when he was opened enough to take a couple of fingers I’d fuck him. It soon got to the stage where I felt comfortable enough to fist him, and trust me, that was magic. Watching my hand disappear into his ass, seeing his hole stretched so far… I finally knew what the attraction was there, too. We graduated to huge dildos, and experimented with light sadistic play. Ben found that he enjoyed being dominated by me, and some pain turned him on. I wasn’t really into it, but if Ben enjoyed it then I did it for him. But we always came back to the underwear.
During the stress of the court case where Dee Dee tried to get alimony from Ben for the child that wasn’t his, our relationship fell apart and we decided to call it quits. We’re still the best of friends and I exchange a pair of white underwear with him every Christmas. On Christmas morning I jerk off with them, and send the underwear back to him, cum-soaked and gift-wrapped. He does the same for me.
Nowadays I am in my 40s, and in a relationship with a gorgeous 19 year old (although he looks about 17). Dan is blonde, smooth and buff. I’m in pretty good condition myself – I have to be, to look good in my G-force bikini (if I were chatting online I’d put one of those little smiley faces in here). Dan loves wearing a piece of underwear called the Nasty Bitch – complete with a built in anal spreader and a tiny pouch that holds his little cock nice and flat. When I first met Dan he told me he had a small penis. He wasn’t too worried about it, and it is a little small, but I love it. It fits well in the Nasty Bitch and I love sucking it – it reminds me of Ben’s little cock. And the anal spreader just tops it all off. When he wears the underwear and bends over to present his ass to me for fucking, I can’t help but fuck him harder than I probably should. I guess I like the dominating bit more than I let on. Maybe Ben was onto something there, too.
We have a great sex life, and Dan moved in a month or so ago. I suppose you could say we’re in love. I certainly love fucking him. And I know he loves me.
Dan showed me the joys of being fisted, as opposed to fisting someone else. It took some time, but as I get older I like to think of myself as being more open to experimentation. So when Dan mentioned it casually one night I thought ‘Why not?’ After a few weeks my ass was more accommodating and Dan’s young fist felt right at home there. With his hand in my ass and me jerking off, and him in a pair of white jocks, life is wonderful.
