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I’d never used the services of an escort agency before, but since Dave had dumped me, I’d grown tired of pay-per-view porn and jerking off. Besides, it was the connection I was missing, too – not just the fucking. Although Dave had quite a large cock, it wasn’t everything.
So, I opened my local paper and told myself ‘It’ll just be a one-off. Won’t hurt to try…’ The ad stood out, and my cock soon followed. Panty Land.
Panty. Land.
The guys were all stereotypically bronzed and oiled, bulges in a panty hiding what the censors still had heart attacks – and secret fantasies – about. But one guy grabbed my attention. I rubbed my cock as I memorised his face, and his name – Jason. I pictured his sweet young-boy face and his wet mouth lowering over my cock, his g-string panty pulling slightly between his ass cheeks, the anal spreader ring giving me a perfect view of his tight hole. As his tongue landed on my member, I shuddered and grabbed the phone.
The man on the other end was pleasant, and said that Jason was not one of their most popular choices yet as he was still relatively new. He added that yes, he was available tonight. The vision of Jason, standing before me in his panty, his cock tightly packaged in the Nasty Bitch bikini, and the fact he could be mine tonight was almost too much to bear. I landed back in reality when the man on the phone confirmed my credit card number, and I pulled at my cock, still straining in the confines on my own panty.
Later that night, I fussed about and cleaned my already tidy apartment, and reorganised my cock several times as it ebbed and flowed in anticipation. I had chosen my favourite panty, one that showed off my cock in its eight-inch glory. It wrapped itself around my shaft several times, so even when it wasn’t hard it was well propped up and on display. The head, already shiny with moisture, rubbed against my zipper in a delicious mix of pleasure and the beginnings of pain. It seemed like forever before my door chimed and I had to force myself to walk to the door, not run like a schoolgirl on her first date.
When I opened it, before me stood Jason. He was dressed casually in a pair of jeans and a loose shirt. His dark hair hung loosely over his forehead, almost hiding his eyes. A duffel bag was slung over one shoulder. I let my eyes roam down to his crotch, and smiled when I saw that his cock was not visible – I knew he was wearing the panty from the picture. I imagined it in the Nasty Bitch panty, flattened down, and almost fainted when I thought of the things I was going to get this young little bitch to do. And when he smiled and spoke to me, I actually had to hold the doorframe as my cock throbbed so hard the room spun.
“Hey. I’m Jason – you’re Michael?” he spoke softly, eyes demurely lowered.
“Uh, yeah. Come in, sorry about the mess.” I added lamely. Jason crossed my threshold and it was all I could do to not grab him as he brushed against me. He took off his shoes just inside the door. He was not wearing socks, and he had the most delectable toes and feet. A small tattoo decorated his left ankle. The hair I could see just above it was light and soft, like he had waxed.
“I’ve never done this before. My boyfriend dumped me, and, well…” I began, but Jason turned towards me and smiled again. “It’s ok, relax. We have all night.” He put down his bag and then I did grab him.
The air whoofed out of him and as I felt his chest land on mine, I held his face in my hands and brought it close to me. I kissed him, roughly, and inside I melted. I figured he was young, barely above legal age, and clean-shaven – sometime in the last hour or so. I pictured his cock, panty-clad, and hoped he was hairless there too. I wasn’t, and the image of his face buried in my hairy crotch, sucking at me, spurned me on. I kissed him long and deeply, inhaling his youth and not wanting to let go. It had been a while since I had felt wanted, and Jason’s tongue flicking against mine let me know he found me attractive, even if I was a paying client. I felt like crying when his hands moved from his side and landed on my arms – tentative at first – then pulling me closer to him. I felt the urgency, and responded in kind. I could fuck him then and there, I was so hard and needy. I almost forgot what I had paid for. I had harboured a secret fantasy about a young man in a panty, which is why I gravitated towards that particular ad. Panty Land practically screamed at me, and the sight of Jason in the panty that made him look so young and inviting… even though Dave was young, it had been some time since we had been intimate and we’d grown apart over several months, before he decided to move away and start a new career. It took me some time to get over and now I felt ready – not for a relationship, but for sex, at least. A good quick fuck, something to break the ice. The panty was just the icing on the cake. Panty Land.
I had pre-arranged the details with the man on the phone so there was little I had to explain; Jason knew his role and what I wanted. I kissed him harder, and we walked to the lounge – me pushing him and him walking backwards, his hands resting gently on my hips.
I made sure he landed on the lounge hard, emphasising his part in the night. He whimpered slightly as I landed on top of him, and forced my knee between his legs. My hand followed, and I felt his panty through the jeans, his cock confined smoothly and neatly inside. We continued kissing. It was magic, a young guy in my apartment again, mine to toy with. Even if it was just for a night. I moved from his mouth to his ear.
“I am going to fuck you up, Jason. Did you put on your panty?” I asked needlessly.
Jason nodded, swallowed, and whispered “Yes Sir.”
It had begun.

I stood up, and indicated that he should do likewise. “Undress me.” I instructed, my panty’s bindings beginning to feel a bit too tight as my cock stiffened more than I had bargained for. Jason stood, and started on the buttons on my shirt. When he was done I shucked the top half of my clothing, and it landed on the floor at my feet. I moved it out of the way, and brought his hands to my zipper. He pulled it down, and then I took out my cock. The panty I had put on earlier in relative comfort now felt as though it was strangling my cock, and I placed my hands on Jason’s shoulders, silently telling him to kneel in front of me. As his mouth levelled with my cock, I pulled it close and saw him lick his lips. My cock wobbled, and dripped. As he took the head in his mouth, I ran my hands through his hair and then lightly grabbed a handful. I let him suck me and run his tongue over my head, and guided his hands to my balls – I loved them being fondled as I was sucked off. Jason took them in his hands, and massaged them gently. His palms were smooth and dry, not like my older hands now wet with nervous perspiration. He tugged them a little, and I sighed – he was good. I could get used to this! I took my cock from his mouth, and quickly untied the leather bindings keeping it erect. He then placed his mouth over it again, and I slid it in a little further.
His mouth was wet and smooth, unlike Dave’s bearded face, and I could help but force the length of my shaft in. As he gagged a little, I withdrew. He was a good bitch, I knew I was going to enjoy my night. We were going to take each other to a land neither had been before. I giggled to myself at the thought – Panty Land.
Jason’s eyes watered and eventually spittle formed at the corners of his mouth as I fucked it. I wasn’t gentle at all, and my hands in his hair prevented him from pulling away. I slowly inched my cock in until Jason’s nose was buried in my pubes, just as I had imagined before. I held him there, feeling him cough around my cock, and breath haphazardly through his nose. I took my cock from his dripping hole and slapped him lightly on his cheek – I imagined it land with a wet plop, and was satisfied when it did indeed land with such a noise. Jason dropped his eyes and I slapped his other cheek, my gaze wandering down to his hands, lying in his lap. With each slap, a wet plop; slap, land, plop, slap land plop. Again, the thought of his cock bound in the panty I wanted him to wear made me shudder and swoon. I saw the ad in the paper again – Panty Land – and felt my shaft twitch.
“Take off your shirt.” I ordered, and Jason hurried to comply. His nimble fingers deftly slipped each button through its hole, and I watched intently as he slowly slipped it from his shoulders. His bare chest immediately formed goose pimples, the dark skin matching his eyes and hair. Again I prayed that his crotch was bare, to complete the boyish charm he oozed. The image of his cock in that panty was almost too much for me to bear, but I forced myself to wait. The shirt landed on the carpet, and I kicked it away. He began to breath a little more regularly, and I waited until he had recovered from the mouth fucking I had administered.
“Wait here.” I said quietly, and went to fetch some of my toys from the bedroom. When I returned, I squatted in front of him, my cock poking out from the undone zipper and dangling in front of his chest, my panty only just keeping it in check. Gently, I attached two nipple clamps to him, and he took a sharp breath with each one.
“That’s my boy.” I soothed, and began to pull on them, pretending to check that they were tight enough. Jason shuddered, and his nipples stretched as the cold metal bit onto them and dragged them slowly. His shoulders buckled inward, and his breathing increased slightly. My cock throbbed in its panty. I leaned into his ear, my breath on his neck carrying my words: “Stand up, and take off your jeans. Slowly.”
Jason nodded his understanding, and gradually made it to his feet. The chain between the nipple clamps swayed gently, tapping his chest on the land of bare skin formed by the triangle of his nipples and belly button. He undid the button fly slowly, and as the jeans landed on the floor and he stepped out of them, I realised he was naked. That the thought struck me so suddenly was odd; I was still in my trousers – albeit with a raging hard-on bobbing from my zipper. But I liked the way it felt, and the fact he was completed undressed and I wasn’t added to my excitement.
I made myself maintain contact with his eyes, even though they were still lowered, looking at the ground. “Turn around. I want to see your pretty asshole.” I saved the best for last – his cock flattened and hidden in his panty – and instead made it so I couldn’t be tempted to see it. As Jason turned so his back was to me, I let my gaze travel down his back, eventually landing at the tight buttocks. They were hairless – waxed, I assumed – and very smooth. I wanted so badly to bury my face between them. The g-string of the panty slipped between the cheeks into the crack, and I took a step towards him, slipping my finger under the leather and lifting it away from his body. I walked him towards my lounge, using the pressure from the leather strap between his ass as a guide, so his crotch was forced into the arm of the chair.
I saw the anal spreader neatly positioned over his hole, and I ran my hand up over his back and pushed him down, so he was bending over the arm of the lounge. Then I saw it in all its glory – his tight ass, surrounded by the metal spreader holding it ever so slightly open. Just a bit darker than the surrounding skin of his ass, the hole looked fresh. I believed the man on the phone when he said Jason was still new to the company. He obviously had not been in the business too long.
I placed a hand on either side of his ass, and held it open. I wasn’t going to fuck him yet – I still had much more to do – but I wanted to feel my cock resting against the metal of the panty; I wanted to rub my head on the hole, test its resilience. As I slid myself between the cheeks and let my cock fall against the anal spreader built into the panty, I reached under him and tugged on the chain now hanging across his throat. His butt involuntarily clenched and I immediately let a palm land on his ass. The handprint rose against the flesh, and he murmured softly “Sorry Sir.”
I took my cock away, and spat on his hole, then rubbed myself against him, my panty pulling between my own butt cheeks and the leather binds from the panty creating friction between us both. I held my cock, and placed it at the hole. Pushing gently, I felt the resistance, and knew it was going to be tight. Plenty of lube and not too much force, otherwise he’d be too sore later on. I didn’t want that.
I stepped back, and viewed the hand print on his ass, the anal spreader holding his tight hole ready for me, and the went spot beginning to form in the panty where his cock head lay between his legs, dripping and wanting.
I walked back to my toys, and selected the paddle Dave and I had sometimes used. It was black, studded on one side and made a hell of a whack when it landed on bare skin. I also picked up a ball gag, a pair of wrist cuffs, and a very large butt plug. And a tube of lubricating gel, almost as an afterthought. Walking back to where Jason was draped over my lounge, I reached under his face and brought it up so he was still leaning on the arm but now I could access his face. I sat sideways on the lounge and expertly fitted the ball gag over his face. He was a little smaller than Dave, so it was larger in his mouth – I wondered how long he could cope with it there. Again, I didn’t want him too sore.
“Is that okay?” I asked, concerned. He nodded, but I saw tears forming in his eyes, and made a note of the time. I kissed his forehead, and stood behind him again. Taking his arms from where they were supporting his weight I placed them at his back, and attached the leather cuffs. He now had nothing to support himself and slumped over the arm of the lounge, his legs tightening as he struggled to maintain his balance.
I took the butt plug, and lathered it with lube. It was one of those ones that had five bulges that increased in size, so the ass could stretch over one bulge, rest for a little, then stretch to accommodate the next bulge. I could never get past the third bump so when Dave fucked me, it was still quite uncomfortable with his large penis in my ass.
I placed it at Jason’s hole, and realised I’d need to remove the anal spreader in order for the butt plug to slip inside. So I pulled it to the side and rested it on his ass. It had left an indent around his hole, making it appear outlined like a target. I again placed the plug at his asshole, and began to slip in. The resistance I felt with my own cock was there – but not as strong, as the butt plug had a tapered end and was well lubed. It inched inside him, and I saw with pleasure the first little bump disappear. Four to go, on a nice new hole. I knew it would be hard work – more so for Jason.
I moved it a little from side to side, helping his beautiful little ass to stretch. Jason so far was enjoying it; he pushed back and moaned – I let fly with a well-timed slap to his exposed ass from the paddle, to tell him I was in charge. He would enjoy it only if I let him. The imprint from the paddle swallowed the handprint from where his first reprimand had landed.
I pushed the plug a little more, and even though his hole was now welcoming the first bulge, it firmly fought against the next. I forced it, watching the skin as it grew taught and Jason squirmed. At the bulge’s widest point, Jason whimpered and pulled away. Instead of another smack, I simply popped the plug in, the shock of the sudden pain and then relief making Jason silent. My own cock was now throbbing to the point where I felt my balls turning blue. I made sure the plug would not fall out, and took a step back to survey the scene. I let out a breath when I saw my beautiful boy, gagged, bound and being ass-fucked with a bright yellow butt plug. I could not see his cock, still restrained by the panty, and he looked for all the world like a virgin offering to some sex god. I checked the time, and walked over to him and took his head in my hands, raising it so his eyes met mine for the first time since he arrived.
“Are you ok?” I asked. He nodded, tears from the gag streaming down his face and his nipples pressing against the fabric of the lounge – I knew how uncomfortable they must have been. I kissed his forehead again and resumed my work at his rear. The plug wobbled as his legs twitched, the muscles growing tired from attempting to keep his balance as he lay over the arm of the lounge. I took hold of the plug and began to work on the third bulge. His ass, although stretched to accommodate the second, was going to resist the next. But I was patient and we did have all night.
I slowly pushed, and bit-by-bit, the plug disappeared almost to the widest point again. Jason shivered, and I paused. I could see the skin turning white and Jason’s hole clenching. I couldn’t resist, I bent over and kissed him, just above where the plug disappeared inside him. Then I plunged it suddenly and forcefully, and Jason yelped against the ball gag in his mouth. I raised the paddle again, and delighted in the slap as it landed. Just because I could, I slapped him several times, watching the butt plug spasm and Jason’s legs kick out. He was my little bitch from Panty Land, and he’d learn who was in charge. It seemed to be taking some time, though – not that I minded too much. I still held the thought of his cock in the panty he wore, smooth and flattened against his body, and prided myself in the restraint I had to have not seen it yet. I did sneak a quick peak between his legs, and saw the damp spot on his panty had grown. I didn’t know if he was just really excited, or whether the pain I was causing had made him wet himself. I didn’t care either way. As long as he was enjoying it – and he had not given me any indication to the contrary – then I intended to continue.
I pulled myself out of my reverie and looked down to the plug, still lodged in Jason’s hole, but looking as though it might fall out and land on my carpet. He had now gone as far as I could – the third bump – and I wanted more than ever to see it engulfed in his tight butt. As I had done for the first bump, I wiggled it around in his ass, and soon enough it began to loosen. I smeared some more lube over the next bulge and massaged a little more into Jason’s hole. He relaxed visibly when I did this, and I realised how much it must be hurting him. I smiled.
The second last bulge took a little longer, although when it eventually plopped inside Jason’s ass I don’t know who was more relieved – him or I. The fifth, I almost gave up on. Jason started to shake his head, and I had to stop several times. At one stage I asked him again if he was alright, and he mumbled from behind the gag that he just needed a rest. I eased it in right up to the widest point, only to have him shake his head – and land a series of blows to his trembling cheeks. But we were almost done, and I was not about to stop now. I massaged some more lube around the plug, and put my hand on his back. The leather from his panty was soaked in sweat, and I knew that between his legs the dampness would be all over the part that held his cock confined. His back was slippery and I whispered that we were just about finished. Edging the butt plug in, I praised Jason for his marathon effort, and when it slipped inside his ass it took us both by surprise. I stood back, and saw the butt plug totally swallowed by Jason’s hole. There was a good 25 inches inside him, and his ass was wider than I could ever have achieved. And rightly so, Jason was breathing heavily, his legs shaking and dripping sweat. It landed on the floor and soaked into my carpet.
I walked around to Jason’s shoulders and helped him stand. He was red-faced and puffing around the ball gag, more sweat stinging his eyes and running down his chest, landing on the chain between his nipple clamps. The clamps themselves had held fast, and his poor battered nipples looked miserable. I took the clamps off, and began kissing the bruised flesh. Jason’s knees buckled, and I helped him turn around so he could sit on the arm of the lounge he had just been bent over. This forced the butt plug in even further, and he groaned. I had contemplated doing more, but this was our first time and I wanted him to want to come back willingly. So, I decided I’d done enough to him for tonight. The rest of our time together – in Panty Land – would be pain free for him.
I gently took off the cuffs, and massaged his wrists. So worried was I about making him comfortable I had forgotten about the panty he wore, that I had especially requested and was so desperate to see. I slipped the buckle of the ball gag, and slowly took it from his mouth. The butt pug I decided to leave for the time being. I stood directly in front of him, and placed my hands on his face.
“Are you okay?” I asked him for the fourth and last time tonight. He nodded, and I brought his mouth to mine. I kissed him softly, moving between his legs so he could feel my huge cock, straining and dripping. After I had treated a partner poorly I loved the after-part: the tender kisses and the slow fucking. If I didn’t cum when I was paddling or mouth fucking someone, or at some other stage while I was delivering pain, then I loved spending time making it up. If I did cum earlier on, I either came again or did it just for them.
I made my way from his lips to his neck, and sucked a trail to the spot I knew I loved being kissed, at the place where the neck ended and the shoulder began. Landing soft kisses there, I slowly lowered myself to my knees so I was in front of Jason’s cock, making my way down his belly (pausing at his nipples on the way). It was then I remembered his cock, and the Nasty Bitch bikini he wore – the same one he wore in the Panty Land ad in the paper.
I let myself look at it for the first time, and delighted in the fact he was hairless – even more so that he had waxed and there was no stubble for me to content with. His cock was indeed smooth and well confined within the pouch of the panty, although by now it was saturated. I rubbed it slowly, and felt the butt plug protruding from his ass, crammed against the lounge. His cock grew harder and I let it out of its restraint. Jason was large, unbelievably so, and I suddenly wanted it in my ass. The need was so overpowering I could barely bring myself to spend time sucking it – but I did, as by then Jason has his hands lightly resting on my head, almost pleading me to take him in my mouth. I obliged, and found myself reminiscing and daydreaming. I deep-throated him, taking him by surprise. Jason began moaning, and I felt his balls tighten. I looked up and saw he had his eyes closed, his mouth was slightly parted and his tongue touching the top lip. I was a little disappointed – I wanted him to fuck me, and if he came that was less likely. Even still, I continued, and even let him hold my head firmly while he began to fuck my mouth.
But I was absolutely delighted when he blurted “Oh fuck, Michael. I’m gonna cum!” and opened his eyes to look down at me. I saw something I hadn’t seen for a long time, and went to town on his cock. Pretty soon, he shot his load and I swallowed it – actually, I devoured it – and felt his balls soften. I waited for his cock to follow suit in my mouth, but it didn’t. It stayed hard, and I looked back up to Jason. He just winked. He stood up squatted, and I gently took the butt plug from his ass. It came out much easier than it went in, and I pictured his asshole, open and waiting for me. I looked back to him.
We only just made it to my bedroom, kissing hungrily on the way. Jason fell on top of me, landing on my bed, and we desperately stripped off each other’s panty. Jason rubbed his cock against me, and I spread my legs to invite him closer. He grabbed his cock, and rubbed it at my asshole.
“Where’s your lube?” he hissed, and I remembered the spare tube I kept in my bedside chest. I pointed madly, and he spread some over my ass and his cock. Holding his cock again, he lay over me and guided it to my hole. I felt it gradually slide in, and was surprised at how my ass took it so easily. Jason fucked me slowly, all the while looking intently into my eyes. I was suddenly the schoolgirl I dreaded at the beginning of the night – shy and virginal. He leaned on one elbow and smirked. “It’s okay, let me do the work now.” Was all he said, and I gave myself to him.
He fucked me for what seemed like an eternity, until I felt as though I was going to explode. I was amazed at how long he stayed hard. Then he slipped out, and positioned himself so he was squatting, his hole over my cock.

Holding his ass cheeks apart, he lowered himself onto me. I held my cock so it landed in his ass. “Oh God.” I groaned, and raised my hips to fuck him.
Jason sat on me, grinding his ass so my cock was engulfed, and rode it. “I said I’d do all the work.” He reminded me, and I relaxed, enjoying my cock inside him. His hand wandered to his own cock, and he began to jerk off. “Can I cum on your chest?” he asked. I barely managed a nod, I was so close to cumming myself. I pictured the young boy in the Panty Land advert, and compared it to the gorgeous guy now riding my cock, and decided I liked both.
Jason’s breath quickened, and I saw his cock stiffen. He panted “I want you to cum with me.” I was more than happy to accommodate him, and as he bore down on me I could feel my cock harden inside him. “Tell me when you’re going to. I want you to cum in my ass…” Jason whispered and I swallowed. He seemed so in charge now, but still so young. I would have been a little confused if it were another situation.
I met his eyes. “I’m gonna cum, Jason.” I saw him shudder, and then he shot his wad on my chest. At the same time, I filled his ass. “Fuck.” we both exclaimed. Jason fell against me, landing with a soft thud on his cum. It oozed between us, and I felt mine trickle from his ass. He still moved every so often, and my cock eventually slipped out of him. I kissed him, and I had to ask.
“It was my birthday the day the ad was run.” He answered. “You’re my first.”

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