The next morning, I lay in bed longer than usual, not wanting to disturb Olly who was still wrapped around me. It felt so good to wake up in his arms, it was a small slice of normality that I could never have. When he started stirring, I looked down and saw those beautiful eyes open, “Morning sleepyhead,” I spoke gently as I ran a finger through his curls.

“Morning,” Olly replied as he started to uncurl himself from my body. I missed the warmth of his body instantly, but I tried not to let him see that. I wanted him to remember our night together as the happy and magical time it was, and not the loss that I knew I was going to feel never seeing this beautiful boy again.

“What’s the time?” Olly asked as he gradually woke up from his slumber. I looked at the clock on the table beside me, “9:30,” I replied as I turned back to look at him.

“Shit,” he said, “I’ve got class in an hour. Mind if I grab a quick shower?”

“Sure, it’s just through there,” I said pointing to the door of my en-suite. I watched his ass as he walked away, knowing I was going to have many nights finishing myself off to thoughts of what it felt like to be inside him. Once I heard the shower start running inside and the tell-tale sign he was under the water, I picked up my phone to check the details for my first client.

There weren’t very many details in the app, but it seems I was to dress up as a ‘sexy pirate’ and go to a London hotel tonight that actually wasn’t very far from my apartment. At least I wouldn’t have all the odd looks at my outfit while I was travelling. I mentally thought through my costume collection to see if I needed to pick anything up this afternoon ahead of the session.

I was pretty sure I had a couple of pirate costumes in my collection, not from client requests surprisingly, this would be a first, but from Halloween costumes from parties Miles and I attended. I’m sure I had a Captain Hook outfit, from the year I went with Miles dressed as Peter Pan, he looked amazing in green tights. Better yet, last year I’d gone as Captain Jack Sparrow, with that outfit I wouldn’t have to worry about the hook getting caught during anything. Yes, that would be a lot safer.

I heard the water shut off and a few minutes later Olly came out, wrapped in just a towel, and all I wanted was to pull him back into my bed and have my way with him all over again. “You look so sexy when you’re all wet,” I called from my spot on the bed where I was still lying naked, much to his appreciation if the tent growing under his towel was any indication. “Looks like you like what you see too,” I teased.

Olly glanced at the clock behind me, “No time for that, I’ve got to get to class. But I’d love to do this again,” he stated, and I felt my heart drop at the reminder that I couldn’t allow this to be more than a one-time thing. When I didn’t reply he asked, “Can I get your number?”

I sighed, “I don’t do that. I had a great time but,” I sighed again, “this was a one-time thing.” I saw a brief glimpse of something that looked like disappointment flash across his face before he put up that confident persona that he approached me with last night.

“Sure, it’s been great,” he said with a bravado that I’m sure was false as he dropped his towel to the floor and bent over to pick up those obscene skinny jeans, giving me another view of the amazing ass that I wish I could be inside again and again. Clearly, trying to tempt me to give in and exchange numbers with him and I wished that I could more than I had wished for anything before.

Once he was back in his jeans, he picked up his sheer top from the night before. It seemed that he was about to slip it back on but he held it out and with that confident smile said, “I can hardly wear this to class can I? Do you have something I could borrow?”

I rolled my eyes but couldn’t fight the grin that was forming on my face as I got up out of bed and walked naked across the room to my chest of drawers. I opened them up and pulled out a black t-shirt that was tight on me. It would still be too big on him, but I’m sure he could make anything look good, “Here, you can keep this, it’s too small for me.” A little pout appeared on his lips but it disappeared just as quickly. Thanking me, he pulled the tee over his head and gathered up his own top. I saw him out and let out a huge sigh to myself as I closed the door. It was fun while it lasted, I thought to myself.

I spent the rest of the day preparing for my client. It had been a few weeks since I met any clients, so I had a bit more grooming to do than I normally would. I didn’t need to worry about waxing or trimming when I wasn’t working. But now things were back to normal, I waxed most of my body, with the exception of under my arms and above the base of my cock. There I only trimmed so that I didn’t look like a ken doll.

After that, I showered to ensure any excess hair was washed off, discovering that Olly had used almost all of a practically new bottle of my fancy shower gel. Towelling dry, I styled my hair to fix it in place. Even though my costume came with a wig, I knew at some point it would likely be removed so it was always best to make sure my own hair looked the part underneath.

I had half an hour before I needed to leave to be at the hotel on time, so I needed to start getting ready. I pulled together all the parts of my costume, checking I had everything that the character wore in the film. My version of the costume consisted of brown trousers, knee length brown leather boots, a billowy white shirt that showed off the top of my pecs, a long brown coat that reached the top of my boots and a thick brown belt with a huge buckle. The whole thing was topped off with a tricorn hat and a wig of long black braids to complete the Jack Sparrow look.

To minimise any suspicion from hotel staff that I was working, I put a long plain coat over the top of my costume, and carried my hat and wig in a small duffle bag. At 6:45, I left my apartment and set off for the hotel, thankfully it wasn’t raining and I made it in good time.

From years of seeing clients in their hotels, I’d learned the trick was to act confident as soon as you walked in and head straight for the lifts to take you to the client’s room without drawing any unwanted attention to yourself from the hotel staff. That was straight forward if the hotel didn’t require a key card to access the other floors, which thankfully this one didn’t. Back in Glasgow, Miles and I had worked out which hotels were like this so that we could make arrangements with some of the staff. Although no hotels would admit to letting escorts in, if you tipped the right people, it could open many doors, literally. But I’d yet to make those connections down here.

When I got to the client’s floor, I located room 714 as shown on the booking request. Before I knocked on the door, I pulled the wig and hat out of my bag and put them on. The plain coat went back inside and slipped it to the side of the door so that the client could get the full effect of the costume on first sight without the duffel bag breaking the illusion.

Taking a deep breath to prepare myself, I puffed out my chest to make my pecs stand out, struck a pose and knocked on the door. I heard a noise that sounded like a crash from the inside, perhaps this was the first time for the client too. It took a few moments for him to reach the door, presumably while he picked up whatever he’d knocked over, and when the door swung open my jaw dropped. The client was looking down at my feet, his eyes slowly roaming up my body. I could tell the moment he realised what I already had as his jaw dropped matching mine.

“Hi Nicky,” I finally managed to say.

“D-d-David, you…you…you’re a…a…” Nick stammered so I finished his sentence for him, “An escort?”

“Yeah,” was all he managed to say, clearly still shocked.

“Can I come in?” I asked, knowing if I stayed out here dressed as a pirate too long that the hotel staff might start kicking up a fuss. Wordlessly, Nick moved aside to let me inside the room. The hotel room wasn’t much more than a bed and an armchair, when Nick collapsed on the bed staring up at the ceiling, I thought it best to take the armchair.

Nick took a few minutes to just stare at the ceiling, I gave him time to recover from the shock, as I sat  there waiting patiently. Still laying down, the first thing he managed to groan was, “I can’t believe I just got hard checking out my own brother.” I couldn’t help it, I let out an involuntary “Ha,” at this, startling Nick into sitting up right.

When it seemed like he wasn’t going to say anything more, I thought I’d try and steer the topic clear of the fact that he’d accidentally just hired his own brother for sex. “So…Nicky, you’re gay then?” I asked.

He folded his arms across his chest, and with a pout he declared, “I’m Bi, actually.”

Feeling my younger self bubbling up inside me, I mimicked him saying, “I’m Bi, actually,” before adding, “No need to get defensive, it’s not like it’s something we’ve ever talked about before.”

When he didn’t say anything further, I thought it only fair to share too, “I’m Bi, too, actually,” causing Nick’s posture to soften. “How long have you known?” I asked.

“Since year 11. I never really acted on it, but there was this cute guy in my form and he was sort of my bi-awakening,” Nick replied, “How about you?”

“Since university. Do you remember my roommate, Miles?” Nick nodded. “Yeah, well he was my bi-awakening.” I replied before adding, “And the one who got me into this job.” I thought I might as well get the truth out there, seeing as he knew exactly what I did as he’d booked me.

“Listen David, do you think you could lose the wig? Captain Jack is a massive turn on for me and it’s really confusing me right now to see you,” he gestured in my direction before continuing, “like that.”

Laughing, I removed the hat and wig and put them on the small table next to me, “Haha, yeah I’m sure you would much rather have gone to the grave without me knowing that little fact,” he joined me in laughing now, easing the tension in the room.

“I have to ask though, why this?” Nick asked me, and it was a fair question, one I’d asked myself a few times over the years.

“It all started when I was at uni, short of cash and needed something I could do around my studies.”

“But that was years ago!” Nick exclaimed, so I continued, “Well, I’m good at what I do, and I enjoy it. It’s good pay, even with the agency’s cut, and I’m pretty much my own boss.”

Nick took a moment to contemplate this, “I assume we can keep this between us?”

I laughed again, “Of course little bro, I don’t really fancy our friends and family finding out what I do, and I’m sure neither of us will ever speak of the fact that you found me irresistible again.” He rolled his eyes at this.

“How did you find me?” I asked.

“Google,” he said matter of factly.

“Of course, Google’s always your solution, isn’t it,” I replied, both of us bursting into laughter.

“You’re still going to charge me for this aren’t you?” Nick grumbled.

“Oh yeah,” I smiled.

“Fair.”

We got back to my place and as soon as we were in through the door, our hands and lips were all over each other again. Mentally I was now cursing his skin-tight clothes. It was impossible to get them off him while we were kissing and I didn’t want to stop kissing him. Without breaking our kiss, I carefully walked him backwards to my room before lifting him up and throwing him down on my bed as if he were a rag doll.

I crawled on top of him and my lips found his again, drawn together like magnets, teasing his lips between my teeth in between twirling our tongues around each other, not knowing where his mouth ended and mine began. Panting for air, I decided to try again at peeling his shirt off his body and with a bit of help from Olly, I finally had it up and over his head. I leaned into his neck and started sucking on the side of his smooth neck, as I had wanted to when he first exposed it back in the bar. The moans and groans coming out of this cute boy as I did so were going straight to my cock which was now fully hard and straining at my trousers.

Out of nowhere, Olly surprised me by flipping me on my back. I’m a pretty big guy and had quite a few pounds on him, so I was stunned with how effortlessly he managed to move us. He started unbuttoning my shirt as I ran my hands up and down his bare back, before moving down to cup his firm ass, squeezing his cheeks tightly. Once he had the buttons undone, I leaned up just enough for him to help me out of the shirt, our lips connecting once more. I pulled him down on top of me again, this time the bare skin of our chests finally touching each other.

But it wasn’t enough, we both needed more. I could feel his cock throbbing inside his skinny jeans as he ground his body against me, while my own wasn’t fairing much better inside my trousers. It was my turn to flip him over as I started kissing my way down his body, twisting my tongue around his nipple bars and gently pulling on them with my teeth causing Olly to growl in delight as he thrust his hips up towards me. I continued south towards the top of his jeans, peppering his body with marks to leave him with a reminder of this night for weeks to come.

Finally ready to reveal my prize, I popped the buttons of his jeans and started to pull them down. It wasn’t easy, they really were practically painted on. Perfect for attracting but not designed for easy access. As I got them down slightly it revealed Olly’s trimmed pubes, “No underwear? You naughty boy,” I teased.

“Less words, more naked,” Olly panted. I pulled tightly on his jeans, finally getting them down and off revealing his full naked body to me for the first time. Forgetting the fact that I was still in my jeans, I dived in and started teasing the tip of his cock, slowly taking more and more, not because I needed to, but because I knew it would drive him crazy. This is where I could truly shine, I was excellent at my job and my clients came back because I could make them feel good. When my nose was finally in his fine pubes, it still didn’t seem enough for Olly. His hips were thrusting up to meet my mouth, desperate to get as deep into my throat as he could. 

I picked up the pace, bobbing up and down on his dick, his thrusts meeting me each time as he chased his orgasm. I felt his fingers in my hair, clinging on, trying to last as long as he could. But I knew exactly what I was doing. With a few key swipes of my tongue at the underside of his sensitive head, and a teasing finger circling the entrance of his hole, it wasn’t much longer before he was spilling his seed deep into my throat. As I felt his orgasm subside, I slowly eased off of him, feeling very satisfied with myself.

I climbed back onto the bed next to him and we lazily kissed. Time no longer seemed to have any meaning. All that mattered was Olly and me at that moment. When we came up for air, Olly was hard again. “You’re wearing too many clothes,” he teased as he slid down the bed to reach for the top of my trousers.

“Well I was a little distracted by a certain little minx,” I replied as he undid my fly and made quick work of removing my trousers.

“Briefs, David? I wasn’t expecting that,” he teased.

“Got to keep the mystery going that little bit longer.” Olly made quick work of removing them too so that I was just as naked as him. “Wow, you’re big,” Olly declared before his mouth wrapped around my cock making me moan in delight. I wasn’t expecting how good he’d be at sucking cock, using the stud in his tongue to expertly caress around the head of my cock. It was a whole new experience for me, and I thought I’d experienced most things in my work.

He didn’t seem to struggle with my larger-than-average length, which had often been a struggle for my clients, although never too much for Miles. Olly just kept going, working as much of my length as he could manage with expert skill. I was cumming down his throat in an embarrassingly quick time from how good the blowjob was, but the way he kissed me after I could tell he didn’t mind.

Feeling our naked bodies pressed tightly together as we passionately made out with one another soon had us both hardening again. “Fuck me, David,” he breathed between kisses, “need you inside me.” I groaned at how good that sounded. I flipped him over so he was face down, causing Olly to laugh in surprise. I kissed my way down his back until I reached the most gorgeous ass I’d ever seen. I spread his cheeks to reveal my goal, dipping my head between them and swiping my tongue over his entrance. I swirled my tongue around the edge before tentatively pressing it inside, once I felt him relax around my tongue, I pulled out causing him to whine at the loss.

“Don’t worry baby, I’ll be inside you very soon,” I cooed while reaching for the lube I kept in my bedside table. I made quick work of coating my fingers before pushing inside him to open him up and prepare him for me. I wanted this experience to be as memorable for him as it already was for me. After circling inside him with one, two and then three fingers, I knew he was ready for me when he started bucking up to try and pull them into him even more.

When I pulled my fingers out, his pert ass reared up some more, desperate to be filled. I reached for the drawer again, pulled out a condom and slipped it on, coating it in more lube before lining myself up with his hole. “Ready, baby?” I asked.

“Yes…need…you…fuck,” he managed between ragged breaths. Now I had his consent, I pressed forward, easing myself gently inside him. Even with all the work I’d done to prepare him, he was so tight. “More,” was all Olly cooed each time I stopped to allow him time to get used to my size. Not wanting to hurt him, I took my time, moving in just an inch at a time. Once I was all the way in, I gave him time to get used to my cock filling him up.

Feeling him relax a little I started to slowly pull out, just a bit, then pushing back in. Repeating the motion over and over, each time a little bit faster until I was truly pounding him into the bed below us, spurred on by the delicious sounds he was making. Wanting to take in everything about Olly before this beautiful night was over, without removing my cock from inside him, I flipped him over with ease so that I could look into his beautiful chocolate-coloured eyes.

While I thrust into him again and again, I was taking in every detail of him. The way his curls looked when they were all sweaty, the way his lips were already starting to look bruised from our intense kissing and the way his balls bounced each time I slammed into him. I wanted a distraction and there was no one more distracting than Olly. I bent down, bending Olly with me so that I could kiss him as I was fucking him. With this new angle, I was hitting his prostate each time, feeling him moan straight into my mouth.

With a few more thrusts hitting that spot inside him, he was cumming hands-free and painting both our bodies between us. As his release spilt out over us, I felt his ass contracting around my cock and I was done. With one last deep push, I was filling the condom with my second load of the evening before collapsing on top of Olly’s now sticky body. When I started going soft inside him, I eased myself up and carefully pulled myself and the condom out. I went to the bathroom, disposing of the condom en route and grabbed a damp flannel before returning to Olly to wipe down the mess we’d made of his body.

If he’d been a client, I’d have normally kicked him out at this point, but tonight was different. He was different. As we both lay in the bed, Olly’s body wrapped around mine, an alert sounded on my phone. I picked it up off the side table, careful not to disturb Olly as he started to drift off to sleep. It was the agency’s app, my profile had been approved and I had my first booking. I clicked to open the request, ‘Please arrive dressed as a pirate’, it said in the special requests section. That was a sharp reminder that our lives were too different for anything more to happen between me and Olly. In the morning I’d have to say goodbye, but for now, for now I could enjoy this feeling and pretend that Olly was mine.

My new apartment in London is so much smaller than the home Miles and I built for ourselves in Glasgow. Everything is just so much more expensive down here. I’ve had to join a new agency for work, my old one only covered the Glasgow area, and now I’m waiting for them to approve my profile.

When setting up the account, I was much more conscious that there was a greater risk of being found by people who knew me on the app. I had friends and family who didn’t really know what I did for work but would be within the area that I’d potentially be working in. So, rather than using my real name, my account was now set up under the name Liam and no longer included a face pic. It was a risk, but I hoped the artistic shot I’d taken of my bare chest would still entice a few clients.

That was a week ago and when I checked the agency’s app, my account was still showing as ‘Pending approval’. Sitting in my new home, alone with my thoughts and no opportunity to be distracted by work wasn’t doing me any good. I missed having Miles around, he was my best friend and we’d spent almost every day together for 8 years. I also missed Dorothy and Nathan. They played such a big part in my life, sure they were clients, but the intimate bonds we built, especially with Dorothy, took our connection to another level.

I needed to get out of my tiny apartment and find a distraction. Without an agency, I couldn’t work, Miles’ voice ringing in my head, reminding me it wouldn’t be safe. But maybe I could find some fun; aside from Miles, it had been years since I met anyone just for fun rather than work. Dating in my line of work would never be fair to my partner, and with Miles also around, I never really needed to find anyone for a one-night stand.

Looking in my wardrobe, trying to decide what to wear, so many items inside brought back memories of my years in Glasgow. The sports kit I first wore when I worked with Miles, the suits I wore on dates with Dorothy, the uniforms some of my clients requested I wear, I’d built up quite the collection over the years and I’d been lucky that I’d managed to keep the same size as I was back when I was still a student. I picked out a pair of dark trousers and a black silk shirt that clung nicely to my biceps, styled my hair and grabbed my keys before heading out to find some fun.

Heading to Soho, I walked into a bar that seemed popular but not too busy. I wasn’t in the mood for the thumping beat of the clubs. I propped myself up on a stool at the bar and ordered a Tennent’s to which the barman replied, “Never heard of that mate.” I rubbed my neck in frustration, of course, this day was just going to get worse. “I’ll have a lager,” I sigh, resigning myself to having whatever they could offer. Tennent’s had been Miles and my lager of choice whenever we were hanging out in Glasgow.

The barman pulled one of the taps on the bar and passed me an overpriced drink that quite frankly tasted disgusting. I was trying to work out what it tasted like when I heard a voice behind me ask, “What you drinking sexy?” Without looking I replied, “It tastes like cat piss.”

With a hint of a cheeky smile in his voice, he replied, “And how do you know what cat piss tastes like?”

I turned my head to answer, but the second I saw him I lost the power of speech. I looked him up and down, he was wearing the skinniest jeans I had ever seen that looked like they were painted on, while the sheer top he was wearing was clearly designed to show off his lithe body and, are those nipple bars, fuck I’m in trouble. He must have caught me checking him out because he giggled, drawing my attention up to his beautiful lips that I wanted to see wrecked after hours of us kissing and his full head of dark curls that I imagined pulling on as I pounded him into the bed.

“Like what you see?” He wiggled his eyebrows at me as he leaned forward to take a sip of my drink. As he did his face contorted and he said, “God, that does taste like cat’s piss,” returning the monstrosity to the bar where he found it. He called the barman over and ordered, “2 Jameson’s, neat, he’s paying,” gesturing towards me.

“Cheeky fucker,” I replied, nodding for the barman to confirm I was indeed going to pay. This guy was pushing all the right buttons for me right now, and I knew right then I wanted to take him home and fuck him into tomorrow. The barman handed us our drinks and as I reached for the glass nearest me, the sexy guy reached forward for the same one so that our hands would touch. Sparks shot between our hands like electricity running between us, I looked into his gorgeous brown eyes and felt as if they were trying to bury deep into my soul.

Without releasing my hand the sexy guy spoke again, “Hi, I’m Olly,” in such a silky smooth voice that I almost missed it. Suddenly feeling like there was a frog in my throat, I coughed a little to clear it before meekly replying, “David.”

“Nice to meet you, David,” he purred, literally purred my name. Am I dreaming? If I am, nobody wake me up. He released my hand and went for his own glass, making a show of slowly bringing it to his sweet lips and letting it drip slowly into his waiting mouth and down his throat, exposing his smooth neck, almost daring me to lean in and start sucking at the soft skin to mark him and make him my own. I could tell Olly knew exactly what he was doing, he’d clearly set his sights on me and now his efforts to reel me in were working exactly as he planned.

I reached for my own glass, downing the drink in one go. Letting the sharp sting in my throat prove to me that I’m in the land of the living. I gestured to the barman for another and invited Olly to pull up a stool next to me, “Join me?” But instead of taking the vacant stool, the little minx climbed onto my lap, grinding his pert ass against my crotch as he ‘got comfortable’. I wrapped one arm around him to hold him in place, pulling him a little tighter so I could feel his body against mine, two can play at that game, you naughty boy.

“Comfortable?” I asked him.

“Very,” he replied, bringing his glass to his lips again and letting a few more drops of whiskey drip slowly onto his tongue. I leaned forward so that my lips were next to his ear and whispered, “I want to devour you and take you apart slowly for hours,” causing him to shiver in my lap.

Taking that as a good sign, I continued to whisper in his ear, “I want to take you back to my place, pry you out of those skin-tight clothes, and taste every inch of you from top to bottom while you writhe with pleasure underneath me.” He let out a little whimper, “Please,” was all he managed.

I didn’t need to hear any more, I inched my lips round to his face, we were just a breath apart from each other now. He made the final move and closed the gap between us, and those sparks were back. Our lips connected and it wasn’t long before our tongues were tussling for dominance inside each other’s mouths. For the first time, I discovered it wasn’t just his nipples that were pierced, the little slut had a tongue stud too and boy did it make the sensation of his tongue against mine even more electric.

I couldn’t resist biting on his lower lip and the noise he let out was like a jolt to my cock that I’m sure Olly could feel stiffening underneath him. When we finally broke apart it took a moment for me to remember where we were, our foreheads pressed together. “Shall we,” Olly said, but my mind was still hazy from the heat of our kiss.

“What?” I replied confused, causing him to let out the sweetest giggle.

“Go back to yours. If you still want to, that is,” the bold confidence he had before slipping slightly now that he was asking rather than just taking what he wanted. There wasn’t even a doubt in my mind that I wanted this man, no, I needed this man. I helped him off my lap, took hold of his hand and, trying to sound more casual than I felt, said, “Let’s go.”

As I looked around our apartment for one last time, I thought back to all the good times Miles and I shared there over the last few years. After we finished university 6 years ago, we bought a three-bedroom apartment together in the heart of the city in a modern new build complex. We fell in love with it because the ‘guest’ bedroom had its own suite and was located right next to the front door making it perfect if either of us wanted to host any clients. We were able to divide our personal and professional space and ensure privacy for each other if one of us was working.

Neither of us often did calls at home, but it paid to be as flexible as possible in our line of work. So much had changed since I was at university; I’d fully embraced my bisexuality, although I hadn’t yet come out to my family or anyone back home in Kent, and working for both men as well as women had given me some amazing opportunities to try new things that my clients requested that I definitely wouldn’t have considered before I became an escort. It was early on in my career that I learned I enjoyed pleasing my partners, making me especially popular with my clients as it meant I’d focus my efforts on fulfilling their desires to the best of my abilities.

While Dorothy was the first of my clients to introduce me to a little Dom/sub roleplay, she certainly wasn’t the last to expand my experiences into kink. It was odd the first time a client asked me to be dominant instead of submissive, being submissive just came naturally to me as it felt like an extension of giving the client exactly what they wanted.

When I was first asked to dominate a client, it was a complete switch in my thinking from doing what the client told me to telling the client what to do. Of course, they gave me some idea of what they were looking for, but it left the events a lot more open for me to try and interpret my client’s wishes. That first time the client seemed to be satisfied when they left, but I had found it incredibly awkward to take over the control in that way. I’d dominated a few times since then, but being submissive came much more naturally to me and my clients really enjoyed how easily I took to being controlled.

One client, a slender guy called Nathan, he’d really expanded my experience of being dominated more than any other. Our sessions would always start in the same way; As soon as I walked in and we’d dealt with the money, he would order me to strip while he watched and then get into what he called the ‘present position’ where I was down on my knees with my hands behind my back. He’d then circle around me to inspect me before ordering me to crawl into another room.

After that, it would depend on what mood he was in. Sometimes, he would get me to go on all fours so he could use me as a footrest, or he might get me to strip off his shoes and socks so that I could suck on his toes and worship his large size 10 feet, which I was worried about when he first told me but they actually tasted pretty good.

The first time he bent me over his knee to spank me though, that’s when I knew I was born to be submissive. It was like electric shocks ran from the point his palm connected with my ass to radiate all throughout my body in a way that was both painful and pleasurable at the same time.

Nathan was the first client who didn’t care, or even want, me to get off during our sessions. He took great pleasure in sending me home horny and needy for more. When I got home that night, I was so desperate for release that Miles and I fucked for the first time without another client being with us. It wasn’t anything romantic, it was more animalistic, two guys fucking the cum out of each other and releasing all of our pent-up frustrations. 

It was the first of many nights that either I or Miles would come home in need of release and we’d help each other out. It was always hot and horny, and it was never awkward afterwards. In our job, we knew that sex was just sex, and we knew not to get attached to our clients. But knowing it, and doing it, were two different things.

It was hard when Nathan’s bookings started to slow down and eventually stopped altogether. There’s a unique bond of trust between a Master and his sub that transcends the normal escort/client relationship and with what followed just a day later, it felt like it was time for a change.

Dorothy had remained a loyal and regular client of mine right from the start. Most of the time our meets would be for dinner and a catch-up, we’d grown to be very close friends over the years. Occasionally, she’d book me for a more sexual session, always saying that “even us old birds need a good rogering sometimes.” And I valued each and every time that we spent together. So  when, the day after Nathan told me he would no longer require my services, I got a letter from her solicitor informing me she had passed away in her sleep, I just felt lost.

I was asked to attend the reading of her will, which was a shock in itself, but what was the most surprising was that I was the only one that had been asked to attend. Once I was seated the solicitor handed me a handwritten letter.

My dearest David,

Thank you so much for making an old girl so happy in her final years. I have loved every minute of the time we shared together and cherished your company more than you could ever possibly know.

After my Edgar passed on, I never thought I would find happiness or joy again, but despite our age difference you always made me feel like a teenager again, just as he used to.

I hope you know you meant so much more to me than just a companion, I felt you truly cared what I had to say and listened even when I rambled on about my youth. 

I have no family left of my own except for you, my precious boy. I hope you will be lucky enough to find someone who will make every day worth waking up and that you live every day to the fullest as I always have. It’s been a good life and I’m so very happy that you were a part of it.

Be happy David, and please don’t make a fuss when my fuddy-duddy lawyer tells you what I’ve left you. 

All my love,

Dorothy x

I don’t know when I started crying, the solicitor told me something once I finished reading the letter but I didn’t really take it in. Everything after that was a bit hazy, I remember getting home and Miles holding me as I cried. Mourning the loss of not only Dorothy, but also Nathan too. Miles had warned me when I first started this job not to get too attached, and normally I was pretty good at that, but Dorothy was not just my client, she was my friend too.

Besides Miles and our apartment, there wasn’t anything really tying me to Glasgow, so after a couple of days I decided to do something that was long overdue. With the money Dorothy left me I decided it was time to go home.

It only took a couple of weeks to pack up my life in Glasgow, and after one last fuck for the road last night with Miles, today was the day I set off on my next adventure.

“David, are you home?” called my roommate Miles as he rushed into our flat late one evening, clearly out of breath from running. He barged into my room without knocking.

“Dude, I could have been naked in here,” I responded even though I didn’t really care about him seeing me naked, I wasn’t shy about my body. Since I started working for the agency I had decided to join the university gym. I hadn’t really done anything to stay in shape since coming to university, but as my body is one of my most important assets as an escort, I thought I best do what I could to maintain the strong physique that years of playing rugby had earned me.

“Like you care, I’ve seen you walk naked across the hall after your shower when you could have covered up,” Miles joked. He wasn’t wrong I liked to show off.

“Listen, are you doing anything tonight?” he asked.

“Tonight? Erm, no I don’t think so, why?”

“I need a massive, and I mean MASSIVE, favour from you, but it’s kind of a lot to ask,” he sounded nervous.

“Miles, as you just pointed out, you’ve literally seen me naked, ask away, I won’t be offended.” I was curious as to what sort of favour would make him seem so apprehensive to ask me.

Miles took a breath before he replied while looking down at his feet instead of at me. “So I have this regular client, and we’d arranged to meet tonight,” he paused. When it didn’t seem like he was going to start again, I asked the first thing I thought might be the reason he was hesitant to ask. “Right, so…what? Did you need me to clear out of here for the night?”

He looked up at me, “What? No…no it’s not that,” he took another deep breath and finally let out, “I need you to come with me.” I had no idea what he meant though, at first I thought he might need a lift because his car had broken down or something but the confusion must have been evident on my face because he sighed and clarified, “I had arranged for another guy to join us, my client wanted a meet with two guys, but the other guy just pulled out and I’m supposed to meet her in an hour. So…”

It didn’t seem like he was going to finish the sentence so I finished it for him in slight disbelief at what I was hearing, “So, you need me to…be…there…with…her, and y-you.”

“I know it sounds crazy, and if there was anyone else I could ask I would, but I’m begging you, David, please! You’ll be paid of course, and you’ll earn more than a normal 1 on 1 session,” he begged.

I rubbed my hand over my face as I tried to take in what he was saying. He wanted me to join him with a woman, the three of us, together. My mouth started to speak before my brain could catch up, “How would that work?”

Looking even more nervous now, Miles continued, “Well she wants us to both have sex with her, like one at each end and switching round so we take it in turns.” Thinking he was finished I replied, “That sounds doable,” but that wasn’t all that the client wanted. 

“Erm…she also…she wants to see us…together,” and with that, my jaw dropped to the floor just like it did when I first found out that Miles was an escort. “I know, it’s a lot to ask, I know you’re straight, but I wouldn’t ask if I wasn’t desperate. She makes regular bookings and she’s a really great tipper, I can’t afford to lose her David,” he begged. 

“What would we have to do?” my mouth running away from me again.

“Wait…you’re not horrified? You’re actually considering this?” Miles seemed taken aback and honestly, I was a little surprised that I was considering it. 

“Look, we’re friends, Miles. You need help, and I want to help you if I can. So, as time is running out and it seems you have no options, tell me what you need me to do.”

That’s how an hour later I found myself in the passenger seat of Miles’ car, pulling up outside a house wearing my England rugby shirt, gym shorts and my best friend’s underwear. It turned out this client had very specific instructions about what she wanted.

Part of her request was for both the men she booked to be in sports kit, which I had managed to cobble together, but she also wanted both men wearing jockstraps underneath. I’d never even worn, let alone owned, a jockstrap, so Miles had to lend me one of his to fulfil his client’s fantasy. When I was getting dressed, I struggled with getting the straps to sit comfortably and not dig into my ass, so Miles had to get very friendly, very quickly to help me get them seated just right. As we stepped out into the evening breeze, it was an odd sensation to feel the wind through the thin material of my shorts, reaching my bare ass underneath, but it wasn’t an unpleasant one. 

Miles came round to my side of the car and we walked side by side up to the front door of the old Victorian house, “you ready?” Miles asked me before ringing the doorbell. “Ha, we’re about to find out,” I scoffed just before the door opened to reveal a beautiful woman with long, dark, curls hanging down past her shoulders. She was maybe in her 40s and was wearing a dress that clearly was designed to show off her huge tits. 

Coughing to clear his throat, clearly, he’d caught me staring, Miles made the introductions, “Nancy, this is David. David, Nancy.”

“Nice to meet you,” I hoped I sounded calm because I certainly didn’t feel it. Sure this wasn’t my first time meeting a client, or my first time having sex with one, but it was my first threesome of any sort, let alone with another guy, and my best friend of all people. 

Nancy clearly had no such nerves as she looked me up and down, practically devouring me with her eyes. “Very nice pick Miles, I like him,” she cooed as she reached out and caressed my bicep. She waved for us to walk inside and as I walked past her Nancy squeezed my ass, just the fabric of the shorts between her hand and my otherwise bare cheeks.

Once the door was shut, Nancy discretely handed an envelope to Miles and announced, “Give me a few minutes and then meet me upstairs. Miles knows the way,” she winked at me before disappearing up the stairs.

I turned to look at Miles, my jaw dropped in shock causing Miles to quietly giggle. He came close to me and whispered in my ear, “She’s a lot, but she’s fun.” It felt odd feeling Miles breath on my ear, the anticipation of what could happen this evening amplified the innocent sensation. There wasn’t time to discuss the specifics of tonight, but Miles and I agreed to check in as things heated up to make sure I didn’t get overwhelmed by anything I wasn’t ready for. 

“I’m ready boys,” Nancy called seductively from upstairs. Miles gave me a look to confirm I was good to go, I nodded and he led the way up the stairs. I took the opportunity to check out Miles from behind, he didn’t have the same build as me that I’d built up through years of rugby, but he was nicely toned with just a hint of definition in his arms and legs. He was wearing white shorts through which I could clearly make out the straps of his jock as they tightly framed his sexy ass. I felt my cock starting to stir the more I looked, I feel like I should probably be concerned about that but it wasn’t my head that was doing the thinking any more. 

When we got to the bedroom, Nancy had changed out of her dress and was now lying on the bed wearing just her red lace lingerie. She looked so “hot”.

“Hee hee, thank you, David,” shit I didn’t mean to say that out loud. “Come up on the bed and kiss me, David,” she said in a sultry voice while patting the bed beside her. I crawled up the bed beside her and leaned in to kiss her, she kissed back with fire nipping at my lips and teasing me with her tongue. I felt the mattress dip towards the other side as Miles came up and joined us. She released my lips and pulled Miles down to make out with him too. Seeing the two of them kiss was so hot, if there was room in the jock for my cock to tent it I would be just from watching them together.

When they came up for air Nancy looked at the two of us, “Will you kiss Miles for me, David?” Miles was about to reply, probably about to say something like I’m not sure if David would be up for that, but I don’t give him the chance, I reach for the back of his neck and pull his lips to mine, I kiss him hard and passionately and it feels incredible. It takes Miles a moment to realise what’s happening but then he’s kissing me back just as fiercely. He’s moaning into my mouth, I’m moaning into his and Nancy is moaning below us just from the sight. 

Eventually, we had to break up for air, his lips looked swollen and red from the intensity of the kiss, I’m sure mine must look the same. We stare at each other, lost in the moment before we remember we aren’t alone and we’re here to do a job. We both look down at Nancy, “that was fucking hot boys,” she panted causing Miles to chuckle, “you’re telling me.”

I lean down to kiss Nancy some more, and it feels different from kissing Miles, not bad, just different. I have an idea, without breaking from my kiss with Nancy, I pull Miles in, encouraging him to slip his tongue in too so that the 3 of us are now all kissing together. Tongues darting in and out of each other’s mouths, not knowing or caring who was who’s.

We were shaking and breathless when the three of us came up for air. Miles and I both collapsed alongside Nancy to grab a moment to recover. Nancy sat up, “I think you two are both far too overdressed, why don’t you help each other out of those sexy kits,” she teased. Miles and I stepped off the bed and came round to the end to put on a good show for Nancy.

Miles pressed a button on his phone and some sexy music started playing, he grabbed my hips and started guiding me to move with him. As we were getting started, Miles pulled me in close so our bodies were pressed together and leaned forward to whisper close in my ear, “She loves a sexy strip tease, just down to our jocks.” He moved his head back and winked at me. I had an overwhelming desire to press my lips to his neck, to taste more of his skin. I resisted the urge for the moment, knowing what we were supposed to be doing. I reached for the bottom of his football shirt and lifted it slowly up his body, giving Nancy a teasing reveal before slipping it up and over his head.

I’d seen Miles naked before around the flat, but I’d never really allowed myself to truly look before. He was stunning, his chest was smooth with the only visible hairs leading a trail down into his shorts that I wanted to trace with my tongue. His pecs were nicely defined but still managed to look natural. But I couldn’t stop to enjoy the view for too long, maybe I’d have a chance to do that when we are back home. Miles was now reaching for the bottom of my rugby shirt and mimicked my moments of teasingly lifting it up and off my body.

We danced closely a little more before Miles reached for the top of my shorts and slowly slid himself down my body along with my shorts which I stepped out of. Once he rose back up to my eye level it was my turn to copy him and slide his shorts down his strong legs which were covered in a fine layer of hair contrasting with the rest of his smooth body.

We were both standing facing each other in our jocks, still touching and grinding to the music while Nancy touched herself on the bed. “Come here boys,” Nancy beckoned to us breathlessly. We climbed back up on the bed and went back to the three of us kissing, and running our hands all over each other. Exploring each other’s bodies now that we were all down to underwear.

As our kisses started to move further south, I worked my way licking and kissing every inch of  Nancy’s body, until my lips reached her crimson panties. With a singular focus, I loop the strings of the bikini around my thumbs swiftly pulling them down and begin to devour her.

That was when I realised what the jocks were for, I suddenly felt a tongue working its way in and out of my hole and it felt amazing. No one had ever rimmed me before and if it always felt this way then I wanted to feel it over and over again. We moved ourselves round so that Nancy could rim Miles too, giving the three of us easy access to explore each other with our tongues.

I guess it’s time to update my Artist’s profile with the agency…again

• Guy: Yes
• Multiple Partners: Open

It took a week for the agency to approve my profile, after which it didn’t take too long to get my very first client. She was an adorable little old lady called Dorothy. Her husband had died and she wanted someone to go out to dinner with her from time to time and keep her company. I remember her once telling me she was ‘too old for all the faffing about that goes with dating’ and that by hiring me she could both enjoy the view and avoid the constant discussions about dentures and her date’s latest ailments that the conversation inevitably descended into when she went out with men that others might deem as ‘age appropriate’. Her and her husband had never done anything appropriate for their age, and she had no intention of starting now.

The very first time we met, I was so nervous. We chatted through the agency a little to set up all the arrangements but I didn’t know what to expect. We met at The Ivy on Buchanan Street, a chic and stylish restaurant which I would never have even considered going to with my budget. Miles had given me some tips beforehand, so I’d dressed up in my best suit, styled my hair just right, and didn’t wear anything that might make me stand out or look out of place. Dorothy certainly appreciated it when she first saw me cooing, “My, my, you’re even more handsome than your profile picture.” I’m sure I was blushing, “You look beautiful yourself,” I replied trying to turn on all my charm.

She giggled as the maître d’ came over and asked for the name of our reservation. Dorothy and I had discussed this in our initial communications through the agency, so trying my hardest to sound confident I replied, “Nelson, table for two.” We were shown to our table and once we were alone with our menus, Dorothy passed me across a small envelope which I tucked into the inside of my jacket. Thankfully, Miles had warned me not to check it at the table where everyone could see as I’m sure would have been my first instinct.

We chatted about the menu while we were deciding and once we’d placed our order I excused myself to go to the toilets. Following Miles’ advice, I slipped into a cubicle and checked the contents of the envelope. Inside was the money Dorothy and I had agreed on for my services, plus money for tonight’s meal. I slipped the money for the meal into my wallet and left the rest in the envelope inside my jacket. Dorothy liked to appear traditional to the outside world so that she could really surprise them on her terms.

After I returned to the table, the dinner went really smoothly. We chatted and laughed, everything just felt easy and much to my surprise there were no awkward moments where neither of us knew what to say. I’d always been one to speak my mind and found this was something Dorothy and I had in common. She told me about all the cool things she’d done during her life, and she genuinely wanted to hear about mine too. I’d tell her about my studies, about my life growing up, even my practically nonexistent dating life which she seemed quite saddened about. As the meal came to an end and I paid the bill, I found myself hoping that Dorothy would want to see me again. Not just for the money, although that was certainly good, but also because I genuinely did have a good time.

A few days went by when I got another notification from the agency of a booking request. When I was between my classes, I logged in to my account and saw that Dorothy had requested a repeat booking, I guess I didn’t do a bad job after all. Bookings from Dorothy went on like this every couple of weeks, she would pick the restaurant, wanting to experience a wide variety of sometimes quite surprising delicacies, and I would show up playing the role of the perfect attentive gentleman.

Each time Dorothy would book my services, my rating on the agency’s website would improve and as it did I started getting requests for more bookings. Mostly, they were older women looking for company for dinners or the theatre. But I still made sure I made time for Dorothy when she would make a booking request, as without her giving me a chance, I don’t know if any of the others would have given my profile a glance. That’s why when Dorothy mentioned one night at dinner that she had a special request, I decided to give it some serious consideration.

When it came to our next booking, instead of a fancy restaurant I found myself in the lobby of a far too nice hotel heading straight for the lift to take me up to the 5th floor where Dorothy had a suite booked. When the lift doors opened, I stepped out, took a deep breath and walked to room 507 where she had told me to meet her. I knew exactly what was planned once I stepped inside this room, yet still, I was nervous. I’d never done anything like this before, and I think back then, if we hadn’t already built up such a great relationship with one another then I probably wouldn’t have considered it.

I knocked on the door and waited, time seemed to slow down in that moment. It felt like I was waiting hours for the door to open, but it was probably only seconds. When the door opened and Dorothy was standing in front of me, I greeted her as she’d requested, “Hello mistress.” 

“Hello my beautiful boy, come on inside,” she replied while making way for me to enter the room. I walked in and stood at the foot of the bed with my hands behind my back looking away from her as she’d instructed. I couldn’t see her from this angle, but I hadn’t heard her move from the door since it closed, so it came as quite a shock when I suddenly felt her whisper into my ear, “You’ve always looked so good in that suit,” which she emphasised by squeezing my ass.

I jumped at the action but it was all part of what we had agreed, so I was more excited than surprised when she next spoke in my ear, “Let’s take off this jacket and get you more comfortable,” after which she helped to slide my suit jacket off my arms and onto the floor at my feet. She took a step back and more firmly this time ordered, “Pick that up.” I quickly moved to comply and felt a sudden sting of her hand spanking my backside. “What do you say when I give you an order boy?”

I was still reeling from the spank to think what the correct answer was, but apparently, my thinking was taking too long because before I knew it I was being spanked again. “You are supposed to acknowledge each order with ‘Yes Mistress’ before you carry it out. Do you remember now boy?”

“Yes Mistress,” I quickly replied, still facing away from Dorothy.

“Good boy, now, pick the jacket up and hang it up nicely.”

“Yes Mistress,” I remembered to say this time before I bent down to retrieve my jacket and hung it in the wardrobe. Once this was done, ensuring it was as neat as possible, I returned back to my previous position at the foot of the bed with my hands behind my back.

“Good boy,” she cooed, before taking a seat in a chair at the side of the room, “Now turn around and face me.”

“Yes Mistress,” the response coming automatically before turning to face her.

“Remove the shirt and hang it up nicely,” she commanded. I acknowledged her order and unbuttoned my shirt while she watched. I hung it up next to my jacket and returned to face her once more. She was clearly looking me up and down to take in all of me. Part of me felt a little embarrassed, but more than that I was feeling horny. It felt nice to be looked at, to be desired and the praise she was showering me with felt good too.

Next to go were my shoes, socks and trousers all of which she had me put neatly in the wardrobe. Once I was standing before her in just my boxers, I’d picked a nice tight black pair that it was impossible to hide my obvious arousal in, she stood from the chair and came over and started running her hands over my arms and chest. I had a pretty good body from my days playing rugby at grammar school, I have my Papa to thank for that, it was something he had encouraged both me and my brother Nick to do because he thought it would make us ‘attractive to women’, it was certainly working for me right now.

Then there was a knock on the door and a man on the other side called “Room Service”. Dorothy called back, “Just a moment,” before she reached for the top of my boxers and gave a swift tug to send them down to the floor, causing my hard cock to spring up and hit my stomach. “Let the man in David,” she said calmly and for a moment I stood there shocked and lost for words. “He’s waiting boy,” she said more firmly this time. Knowing I had to do as I was told, I turned and walked across the suite to the door. That felt like the longest walk I’d ever done.

I took a deep breath and opened the door, completely naked and my hard cock pointing straight out at the man on the other side. I noticed his eyes snapped down to my cock and quickly returned back to my face. Blushing he repeated, “Room service”, almost like it was a question. “Bring it in please,” called Dorothy from inside the suite so I stepped to one side and held the door as the man brought the food Dorothy had ordered before I arrived into the room.

“Tip the nice man, David,” Dorothy said with a hint of a smirk on her face. I walked to the wardrobe and retrieved a £5 note from my jacket to hand to him. As I did this, with no shame at all, Dorothy said, “Good boy,” which caused my cock to twitch. Looking back now, this was definitely where my praise kink started. The man thanked me for the tip and hurriedly left the room. Dorothy picked up the plate she had ordered for me and placed it on the floor by her feet. “Down boy,” she grinned and being the good boy that I am, I did as I was told.

After that day, I updated my Artist’s profile with the agency.

• Sex: Open

My name is David Nelson, and I’m a male escort. A gigolo, a prostitute, whatever you want to call it, it all means the same thing: my job is getting paid to have sex for money…well mostly. It’s not all I do, sometimes I’m hired by lonely people wanting someone to go out to dinner with them, or act as arm candy at some fancy event. In fact, that’s how this all started back when I was a poor university student.

During my second year at Glasgow University, I shared a flat with my friend Miles. Miles was everyone’s friend; he was chatty, interesting and an all-round nice guy. As far as I knew, he didn’t have a job, but he never seemed to be struggling for money in the way I always seemed to be. Sure, I was fortunate that my Papa helped pay for my rent, but with my loans paying for my tuition, what little I had left didn’t really go very far each week. Miles would often spend his evenings out, but he never brought anyone back to the flat; I even told him it was fine with me if he did. It made sense if he was getting laid all the time, he was a good looking guy, even I could see that.

One day Miles came home with a very fancy new watch on his wrist, it literally glistened when the light caught it, so I had to ask, “How can you possibly afford a watch like that? Did you sell a kidney?”

“Ha, something like that,” Miles chuckled.

“Something like that?” I repeat, confused by his response. 

Miles paused, I guess he was considering how much to tell me, and what he told me next truly did shock me.

“It wasn’t my kidney I sold, but it was a part of my body. In fact this little beauty,” referring to his watch, “was paid for by this sexy ass,” at which he literally spanked himself for emphasis. I’m sure I must have looked like a cartoon character at that moment, completely lost for words and it felt as though my jaw dropped to the floor.

After I’d recovered enough to take in what he was telling me, Miles told me how he worked for an online agency that helped connect potential clients with the escorts they represented for dates, company and of course sex.

The pieces all started to fit into place in my head then. Why he never brought any of his ‘dates’ back to the flat. Why he never seemed to be struggling for money. Why he kept some pretty weird hours. He asked me if I wanted him to refer me to be added to his agency’s list of ‘staff’ but although I didn’t judge him for it at all, I didn’t think it was for me.

I didn’t think any more about it for another couple of weeks until a particularly disastrous attempt at dating made me question what was actually stopping me from doing it. I wasn’t a prude when it came to sex, besides Miles had even told me not all of his clients wanted or even expected sex, so I could just do the dinner date-for-hire part if I was really that concerned about it. I could at least look into the agency more before I decided, rather than dismissing it completely as I had when Miles first told me about it.

So I did, Miles referred me to his agency, which apparently got him an extra bonus, and sped up the vetting process they did for all their potential new ‘Artists’ as they called them. I provided them with a few basic details including my ID and a recent picture and within a couple of days, I received a form in my inbox asking me to provide some information for my ‘Artist profile’. It was a lot like a dating profile with sections like ‘About me’, ‘Hobbies’ and ‘Favourites’. It only started to differ when it got to the section titled ‘Do’s and Don’ts’.

I guess the best way to describe this section of the profile is the agency’s way of “managing expectations” and matching the most appropriate artist to a client. It was a list of services that I had to indicate if I was willing to provide them or not, with another option to leave it ‘open to discussion’. I worked my way down the list, which started pretty tamely. 

• Dinner: Yes
• Theatre: Yes
• Cinema: Yes
• Boyfriend Experience: Open
• Events: Yes
• Overnight: No
• Sex: No

With a number of follow-up options that were greyed out once I selected No to Sex. Artists could update their profile at any time, so I figured I’d start without the sex and see if I even liked being an escort first. 

The final section was on preferences:

• Girls: Yes
• Guys: No
• Age: Open
• OF/JFF: No

After completing the form, I hit submit before I thought too much about it. From there I just had to wait for my first client.