A Working Boy

Today’s client was my own personal cowboy, a big Texan rancher. He wasn’t in town often, but he always stopped by when he was here. He had a wife and three daughters, so you might think he liked a little male company from time to time. 

You’d be wrong. 

Which is why I answered the door wearing a frilly white blouse, a very short pleated skirt, and powder blue cotton panties. I usually bought expensive stuff to wear for my clients, but all of this was cheap and disposable. You see, with my big cowboy I only got one use out of this stuff. 

My man came in and cupped my face in his big, warm hand, kicking the door closed behind him. I loved the feel of his skin on my face. I was smooth and soft, while his hand was rough and calloused. 

My cowboy was perfectly in touch with his sexuality. He was mostly straight, but he loved to stray from the pasture from time to time and get with his favourite femboy. He was a big rock of a man standing at six feet and six inches tall, with muscular arms, a broad chest and shoulders, toned pecks and midriff and chiselled facial features. His hair was the gray of steel, clipped short so it didn’t get in the way of his Stetson. 

“How’s my baby?” He asked in his deep southern drawl. It always sent a shiver up my spine. It was like being in some John Wayne movie. Screwed by a cowboy.  It gave me goosebumps. 

“I’m fine, thank you daddy” I said with a coy smile.  He let his thumb drift over my cheek and onto my lips. My mouth went slack and he pushed his thumb along my tongue. 

“Good.” He said.  “You ready to please daddy, baby? Because daddy needs some lovin’”

I loved how this guy started off. It made me want to fall to my knees and beg for it. The deep voice, the older working man’s body, and confidence. Around the thumb in mouth I said “Yes daddy, I’m ready for you. Will you be gentle with me?”

He liked that. He wouldn’t be gentle, of course. We both knew it. But this was part of the game, part of his particular thing, part of what got him off.  He was paying, so I wasn’t arguing.  

“Well, I’ll try, sweet thing” he said, his thumb exploring the inside of my mouth. “But you’re so darn cute that I sometimes get carried away. But you don’t mind, do you baby?”  

“Okay daddy” I said as I sank down to my knees and reached up to unfasten his Texas star belt buckle.  

I remembered getting down on my knees for my first client in this apartment. Well, the first after Stefano of course.  

To begin with Stefano had bought the apartment and said I should use it in place of my old one, the one Danny had organised for me. He said I couldn’t entertain serious clients in “that horrible room”. A couple of months in, as we lay in bed talking after he’d made love to me, I confided in him that I was desperate to move out of of my parents place. He seemed to understand my situation completely. He didn’t question anything, never told me I was wrong or advise me unless I asked. In fact he simply said I should move in here, free of charge. He said it was pointless leaving it standing empty between clients. 

I was thrilled, like I’d succeeded in my main ambition.  Neither mom nor dad seemed to care enough to try and stop me, so I dropped out of school as soon as I could and I moved in. I loved the place, somewhere of my own, where I could do whatever I wanted. Somewhere I could make my home. 

When that first client came through the door, into my place, I had a renewed energy and desire to please.  I hadn’t even said hello and I was down on my knees, unbuckling his belt, yanking his pants down. I was gobbling down his dick almost before the front door closed. I had bounced on that guy’s cock like he was a trampoline. The guy’s eyes had rolled back into his head and they didn’t come back until he’d shot a load of cum into my guts. 

Another month or two in and Max asked me why I still worked with Danny and Ladd Logistics. I asked what he meant and he said, “He only takes a small cut, but it’s still a cut. And he no longer does anything for you. Mister Valentini has recommended clients for you and that’s snowballed. You have your own place. I’m just wondering if there’s a reason you still go through Danny?”  

I was perplexed.  I didn’t know. I guess I was loyal and I guess I still wasn’t sure what Danny’s brother was to me, so I stuck around. “How else would I do it?” I asked, suddenly curious. 

“You’re organised enough. You’re not seeing multiple clients in a day, so it’s easy enough to keep track your appointments anyway. And these customers come to you. Just give them your number and let them schedule direct with you. If it gets to much we’ll find you an assistant.”

I thought again, but Max knew he was into something and had piqued my interested. He had been keen for me to drop Ladd Logistics for a while. He disliked Johnny. He thought he was bad for business and was only ever going to mess me around. Max was probably right about that. 

“Ok” I said. “But what if my clients dry up and I need to find more?” 

Max threw his head back and laughed loudly for the longest time. He had tears streaming down his face. I didn’t see what was so funny. 

“Oh my dear boy!” He said as soon as he could speak. “I really don’t think that’s a consideration, do you...? They’re queuing up, telling their friends, who are telling their friends. There’s only one of you.”

I smiled at him. “Ok smart ass” I said. “But Danny negotiates and sets prices and collects cash....” 

“You are smarter than you give yourself credit for” Max said. “I can help you with pricing. Right now Danny is only charging the rate Mister Valentini recommends. You’re more than capable of telling people how much. In terms of collecting, well...there are lots of ways we can do that. I’ll have one of my people come to your place and we’ll get you set up to take payments in whatever way suits you.”

“Final point” I said, but I was almost convinced. “What about security. Danny handles all that.”  

“Danny does nothing about security and you know it” Max said. It was one of his annoyances. “But I can put you in touch with people, myself included, who can run a little background on potential clients to give you peace of mind.”  

I thought a while, just long enough to extract Max’s monster cock from his pants and suck him off. By the time I had finished, I had made up my mind. “Ok I’m convinced” I said as I wiped my mouth. 

“I don’t know whether I’m happier from the blow job or that news!” Max had beamed. For the first time ever I was pretty sure it wasn’t the blowjob. 

My Texan client helped unbutton his fly and he pushed his jeans down below his ass.  I pulled them down the rest of the way. I took his penis from his plain white boxers. It was large, not the biggest I’d ever had but it was meaty and big enough. I played with it, toyed with it, and then I tentatively opened wide and began to suck and lick.  

“You been seeing other folks behind my back?” He asked, all part of the game. 

I took his cock from my mouth.  “I’m sorry daddy, but I get so lonely between visits….” I batted my eyelashes at him and he raised an eyebrow at me.  He gently pushed me away and I rolled back on the floor. I looked back to see him removing his boots, pulling his jeans off, and then standing to look down on me, his cock already standing straight up, almost touching his belly. 

Here it comes, I thought….. the anticipation was excruciating. “Well, baby, that means I gotta spank that bottom and you darn well know it!” He said, the beginnings of a smile on his face.  He was trying to hide it, but it was there. 

He went to sit on the sofa and he beckoned me over to him.  I stood in front of him, almost between his knees. He reached up with both hands and he tore my blouse off my sight frame in a single movement. He was so strong, it made my knees go weak. He took hold of me and placed me over his knee and raised the hem of my skirt, tucking it into the waistband to keep it out of the way. Then he grabbed the side seam of my panties.  He wasn’t gentle about it, tearing the fabric from my body. 

I whimpered. Sometimes it was nice to have your clothes literally ripped off. 

He ran that rough, warm hand over my smooth, pale buttocks. I loved the feel of this guy.  This was a man who worked with his hands and it showed. I winced as the first slap sent a thrill of hot energy through me.  It stung, and the noise seemed loud in the quiet of my apartment. 

That first client had been noisy, too.  He moaned loudly as I sucked him, taking his dick all the way to the back of my throat as I fondled his balls. When he could take no more of my tongue and cheek, he picked my up by my shoulders and pushed me backwards into my living room and over the arm of the sofa. He grasped at my ankles and pulled my legs up and apart, looking down at what he’d purchased with lustful longing. 

He was a big guy, hairy, and overweight.  In honesty he was a fat slob, but he had a sexual aptitude to match his love of burgers and big bank account.  He adored my body. He went crazy for me. He would touch me all over, examine every details of my flesh. It was always thrilling, always heightened the experience. This was his first time with me though, and he was keen to get his cock stuck into me as soon as he could. 

He lined up his bulbous dick and pushed it into me, thrusting and poking and driving it further forward with each flex of the hips.  Finally it was all the way in and I sighed with pleasure. He took that as a sign to fuck me, and he did. 

The Texan spanked me hard, a regular thwack every ten or fifteen seconds. In between he’d caress my sore skin, occasionally allowing his fingers to drift deeper into my crack. 

My bottom was red and I cried out the last few times, adding a little drama that I knew he’d like.  He was breathing deeply and heavily, a manly sexual sound that drove me nuts. 

He rubbed my sore cheeks with his big hand, moving in circles that came ever closer to my crack and my hole.  This was the part he seemed to like the most.  I knew he’d be watching intently. 

He ran his thumb across my entrance, pushing slightly. The pushing got harder and harder until he popped it inside me to the first knuckle.  He began to move his thumb around, probing me, pulling at the wall of my anal ring, opening me up. 

Then the second thumb. He pushed that inside too and ran them both around. He loved to pull me open, to see how much he could stretch me out before it became too much to bear. 

His hands settled on me, one on each cheek, his two thumbs now deep inside me. He pulled me open, gaping me, stretching me. It started to sting and then to hurt, but I embraced it, seeing how far I could go. 

His fingers gripped hard on my buttocks, providing the anchor for his hands. His strong thumbs pulled in opposite directions. I breathed deeply and I arched my back. I was almost at the point where I would need him to stop. 

He huffed and puffed, pulling and probing he dribbled saliva right into my open hole. Then, as he gripped hard and really pulled, I moaned out loud. 

His thumbs relaxed immediately and he very gently withdrew them. My hole remained gaping. That was as far as i’d ever let him go and it felt oddly satisfying. 

He picked me up off his lap, turned me to face away from him, holding me tight by my buttocks. He lowered me down to sit on his large hard dick. It was sleek but meaty, not much head but a broad and long shaft. It was like a little space rocket. 

He impaled me easily, my anus still stretched out. I dropped all the way down his shaft until I was full and sitting in his lap. I whimpered for him. 

“Now baby, let me show you how a real cowboy fucks” he said, his drawl reverberating through my body. 

He lifted me up, then let me drop. Then again. And again and again and again. It knocked the breath from my lungs each time forcing me to make breathy sounds every time he filled me up. 

The fucking was terrific. It was a real, manly fuck. He liked to take what he wanted and while I trusted him and knew he’d never hurt me, he liked to skirt the edge of that trust. Personally I loved it. It was closest thing to rape fantasy that I had.  

He lifted me off his twitching shaft and literally threw me onto my stomach on the sofa. He climbed up behind me and thrust his hips down, taking me in my ass once more and grinding himself down on me. I moaned, this time completely involuntary. 

He fucked me like that for a while, screwing and grinding and stabbing me with his big member. He shoved my face into the sofa and took me, hard. 

When that first customer had run out of steam, his overweight body out of stamina, I’d rolled him onto his back and hung my legs over.  I wanted it rough, hard and fast and as long as he could keep it up, I was going to get what I wanted. 

He had loved it. It hadn’t taken very long, but I’d got enough out of him.  He came deep in my guts and when he’d finished, he had spent the longest time touching my hole and looking at me, watching the cum leak out of me.  He came back often after that. It was always a delight to let him touch me and examine every part of me.  

The Texan gave a little yee-haw as he sawed his dick in my hole. I arched my back and pushed up to meet him, delighting in how roughly he went at me.  I felt so small and insignificant underneath his body of steel. He could snap me in half, of that I had little doubt, but he knew his own strength and only ever went so far. 

He took my perspiring body and flipped me onto my back. He lifted one leg and held it close to his body while he stuffed his duck back inside me. He pulled my leg, massaging the sole of my foot. He pulled my leg so much it lifted my ass off the ground, and that was how he would finish.  

He pushed and shoved and bucked and then, eventually, he shouted out loud and surged forward. I felt his cock spasm and he emptied his balls in me.   It felt so good.  

Finally he lay me back down, spread my legs open, and then he lay beside me playing with my cock.  He always jerked me off before he finished and not all clients did that.  I came over my belly, and he scooped up the goo and fed it to me, delighting as I grasped his hand and sucked on his fingers. 

“Baby, you’re good as ever.” He said. “I enjoy nothing more than fucking that hole of yours. It gives me something to think about when I go home to satisfy my wife.” He added. I smiled and hugged him. He’d get up soon and ask if you could use the shower. 

I smiled as I realised as I knew all my clients inside and out. I knew what they wanted, what they’d do next, how they’d be when they had finished. I got a little pang of sadness as I realised there was no emotional connection with these people.  I enjoyed the sex, of course, but after they left me I shrugged them off and got on with life. 

I lay there, the taste of my own cum in my mouth and my hole feeling that familiar warm sensation. My cowboy asked politely if he could freshen up and I was on autopilot when I said he was welcome to use the shower.  He got up and disappeared into the bathroom. I lay where I was, turning mixed emotions over in my mind. 

I left Danny’s place feeling mixed emotions. I was sad, feeling like I was leaving a huge part of my life behind. I felt like I was abandoning a friend, at least to some extent. Danny had been good to me. He’d been fair and he’d been honest. I could have ended up with a worse pimp, I guessed, and I was grateful to him.  

But I was also elated. I was free. No more living with parents, no more attachments. It was me, my clients, my apartment, my money, my life. In a lot of ways I thought I’d really made it. 

Danny had been so sweet, too. He’d known it was coming and he was sad, and he grinned when he promised to keep trying to recruit me back. But he was genuinely happy for me and he thanked me for helping to turn his business around. He even apologised for his “idiot of a brother”. We parted on good terms and that meant more to me that I realised.  

The months that followed were sweet. I built up regular clients, started live streaming and selling content via online channels. It wasn’t as highly paid as my client work, but it was very lucrative. And it was fun!  

Then came the day when I guess I really grew up. The day Stefano came to see me for the last time. 

He’d been a little shaky this time, like age had suddenly found him.  That didn’t stop him from enjoying my body, though.  He touched me, spending longer than ever tracing every curve, every crevice, as if memorising me. He was a little calmer than usual, but he spread my legs and screwed me, allowing me the pleasure of swallowing his cum when he was ready.  

Afterward, as we lay together on my bed, my arm draped over his chest, he got all serious.  He gave me all sorts of life advice, told me stories about his own life and finally, when I realised something wasn’t quite right, he took a deep breath. He told me that he was going back home for a serious heart operation.  He wasn’t confident about it. He said his age made it touch and go. I started to cry silently as he spoke.

“You know, I think I’m in love with you. I’m sorry to drop that on you, but in case I don’t come back I wanted you to know. You have made me happier than I have been for many years. And it’s not just the time we spend in bed - although I like that part a lot...” he smiled broadly at me and I giggled even through my tears. “...but you have really gotten into my heart. I enjoy spending time with you. You’re special.”  

I had no words. I had wanted to tell him that I loved him too. I was sure my love wasn’t the same as his, but that didn’t matter right now. But I couldn’t speak. My eyes were full of tears and my throat had a huge emotional lump in it that hurt. I sat up to look at him properly. 

He snapped out of it and got all businesslike. “I told Max to sign the apartment over to you. It’s yours. In case... well, it doesn’t matter. It was always going to be a gift anyway. Just promise me something?”

I nodded and that caused more tears to tumble down my cheeks.  

“Make sure you make time for you, okay?  You’ve achieved your goals. I know you enjoy what you do and I’m not saying you shouldn’t, but everyone needs love in their life and that includes you. And no, sex isn’t the same thing. So when you find it, grab it, and hang onto it!”  

He smiled broadly again and I couldn’t help but grin back. 

“And hang onto it for dear fucking life!” He said with a chuckle. 

My eyes went wide. He never swore, so I was shocked. I grabbed him and held him tightly, hugging him so hard. 

Eventually he peeled me off and stood. He walked gracefully to my door, opened it and stepped through. He looked back just briefly, gave me a smile, and then left. 

I sobbed. Something about that encounter told me it was the last time I’d see him and I was right. 

Stefano Valentini. My father figure. My lover. A true gentleman. 

To be continued one more time...