Give The Man His Money’s Worth Gay Male

“One hundred dollars each. No cameras and you don’t touch us, right?” demanded Silas. He was still a little skeptical about the arrangement. It was one thing to agree to this and it was another to show up and do it and now Silas was looking for any reason to back out, but Steve was as cool as could be. He just sat down in a chair in the middle of the bedroom. Other than a large oak dresser and a side table there was no other furniture.

“That’s the deal. I’ll just sit in my chair and watch.”

“And how long are we supposed to do this?”

“As long as you need.”

“And are you going to touch yourself or anything?” Silas wanted to know.

“Perhaps, but not at the beginning. To start with I just want to watch.”

“Let’s have the money. I want it now.”

“I’ll tell you what.” Said Steve calmly, pulling a long elegant brown leather wallet out of the breast pocket of his tailored suit jacket. “I’ll place the money on the dresser so you can see it and you can pick it up when you’re done. Fair?”

Silas looked my way. “Jonas?” He asked me and I answered with a shrug.

“OK.” Silas said, sounding a little defeated.

Steve took two one hundred dollar bills out of his wallet and placed them on the dresser, then returned to his chair, elegantly folding his hands on his lap. He had a pleasant, nondescript look on his face. I thought he could have been sitting at the opera instead of waiting for two 18 year old high school kids to jerk off in front of him.

I looked over at Silas. He was nervous. The money was on the table, he’d run out of objections and he was realizing he’d actually have to go through with this. Steve was seated facing the bed and I now saw that a towel had been laid out on each of the near corners. Taking my cue I left Silas at one corner, walked over to mine and with my back to him I pulled off my shirt as matter of factly as I could. I was doing my best to avoid eye contact, but when I sat down I glanced over at Steve who I saw was watching us intently, but he hadn’t moved an inch in his chair.

I’d met Steve at a formal dinner about a week ago. I had an afterschool job as a waiter. Usually it was weddings, but this time it was some kind of fashion event. Everyone was extremely well dressed, but I thought that Steve looked especially dapper. His salt and pepper hair was stylishly cut and his classic tailored suit sat perfectly on his slim 5’10” frame. He was seated with 3 other men who I guessed were all in their late 40s or early 50s and all obviously gay. I considered myself straight, but I didn’t have a problem with gay men, in fact I preferred them because they usually tipped me really well.

Steve was extremely polite with me, complemented me on my looks and kept chatting with me whenever I came over to their table. He asked me my name and where I studied. Towards the end of the evening when I was just about off shift he found me and asked if I’d like to come to his place some time. I told him I wasn’t gay and that’s when he asked if I’d consider coming over and giving him a show some time for money. I said I wouldn’t feel comfortable going to his place alone so he suggested I bring a friend. I needed the money so I said I’d think about it and took his number.

My friend was now sitting naked on a towel on one corner of the bed, staring at the ceiling and stroking himself. I knew Silas from school. I’d asked him because he was constantly talking about jerking off, usually after describing the tight body one of our classmates, Mary Sanders. I waited until it was just the two of us and brought it up like I was just telling a about this weird rich guy I’d met. As expected he was a little weirded out, but the more we talked about it the more I could tell he was thinking about it. I pointed out that he masturbated all the time for free and he could close his eyes and pretend he was alone, so he agreed to try it.

We weren’t best friends or anything, but we’d shared some of classes and we hung with the same group. If you’d asked I’d have said he was handsome. He had straight brown hair that he kept mediumlength, prominent cheek bones and a square jaw, but he was also just “one of the guys” and I’d never really thought about his body or anything like that before. Now that we were here I was really curious what he looked like. I acted like my neck was stiff and rolled my head as an excuse to sneak a glance at Silas. I saw that his head was back and his eyes were closed tight so I felt it was safe to check him out a little.

He was around 6’1″ and had a nice, slim, athletic body with defined pecks, a flat stomach and for some reason I remember thinking he had really nice thighs. His legs were spread and his cock was only semihard, maybe 6 inches long and kind of thin. He kept pulling at it, but couldn’t get fully hard. I guess he was distracted. I guess I was distracted too because I lost track of time as my eyes poured over every nook and cranny of his naked body. When I realized I’d been staring I first double checked that Silas’ eyes were still closed, then I looked over to Steve. He’d obviously noticed me checking out Silas and if I wasn’t mistaken he had a little wry smile on his face.

Silas took a little convincing to put on this little show. I think he was worried that jerking off in front of a guy was “gay” so I took great pains to reassure him he jerked off at home all the time and that didn’t make him gay. He wasn’t doing it because it turned him on after all. This was just a way to get some easy money. That’s why I was doing it, I said, just to make some extra money. If truth be told, I wasn’t worried whether this little show was “gay” or not, I was worried Silas would figure out that this did turn me on. I’d turned my back to him as I took off my clothes not out of modesty, but so he wouldn’t see the erection I’d been trying to hide since before we got in the house.

I dated girls and I’d had my crushes, but lately all of my fantasies involved my math teacher Mrs. Chlebek. She was tall with broad shoulders, big breasts, a stern face and a quick temper. The first time I laid eyes on her I immediately realized I really wanted her to punish me. I had this whole scenario in my head where she was mad at me for screwing around and she’d make me stay after class. Once the other students were gone but the door was still unlocked she’d punish me by making me strip naked, bend me over her desk and spank me hard with a paddle until my ass was bright red. Then she’d take a dildo out of her desk and face fuck me with it as punishment for talking in class. The fantasy kept getting more and more elaborate and lately, with the dildo still in my mouth, she’d fuck me with a strap on while telling me in a stern voice that naughty students take it in the ass. It was even hotter when I pictured someone watching. Initially I’d imagined a couple of the cute girls in my class walking in and laughing at me as they watched me get pounded in the ass, but just recently I’d pictured our crusty old 60 year old principal walking in on us. He’d leave the door open and just stand there with folded arms and nod approval to Mrs. Chlebek at her methods and that was the biggest turn on of all.

Of course I didn’t dare tell anyone about this fantasy and outwardly I’d talk with my guy friends, including Silas, about which of the girls in our class we’d like to bang. Back in reality Steve and I were still looking each other right in the eyes as I stroked my rock hard 5″ cock. It seemed like Silas wanted to pretend Steve wasn’t there, but as I stood there, next to the bed, fully exposed, erect penis in hand, seeing Steve seated in front of me, fully clothed, eating up my young fully body with his eyes, it felt silly to pretend this wasn’t turning me on.

“Do you like the show?” I asked Steve. Out of the corner of my eye I could see Silas look at me in surprise as I spoke.

“Yes, very much. You’re both too cute.” Answered Steve.

“Yeah, what’s cute about me?” I asked him. I was a shorter than Silas at 5’9″ and very thin. When girls described me they usually used words like “tiny” and “scrawny,” not “cute.”

“You have a cute face with great dick sucking lips.” he answered.

“Oh really?” I licked my lips. I guess I did have pretty lush lips for a guy. “I bet you’d love to see that.” I teased.

“I would. I’d pay another $200.”

This caught me off guard, but he’d opened a door and I was all in now. I looked over at Silas. He looked confused, but importantly he wasn’t freaking out.

“We don’t get paid until someone cums, right?” I asked Steve.

“That was the deal.”

I slid over on the bed towards Silas.

“Dude, what are you doing?” Silas asked me a little startled.

“Making some money.” I said.

“Dude…” he began, but before he could finish I got down on the carpet and kneeled in front of him. There could be no confusion what I had in mind, I couldn’t play this off as a joke later. I was kneeling in front of him offering to suck his dick. I looked up at him and I couldn’t quite read his expression, but after a slight pause he seemed to make a decision and moved his hand away from his crotch.

“I mean if you want to suck my cock, I’m not going to stop you.” He finally said. He closed his eyes and leaned back on the bed probably thinking about Mary Sanders. OK I thought, I’m really going to do this. I leaned forward between his spread legs until my face was inches away from his flaccid penis. I wasn’t really sure what to do and I was so nervous I was shaking. I finally stuck out my tongue and licked his cock, from the tip up the shaft to the base. After I did it I remember feeling silly for getting so nervous. There really wasn’t anything to it. I continued licking the sides of his shaft and I heard him murmur, but he wasn’t getting noticeably any harder. I figured I might as well go for it, so I put his whole penis in my mouth. I licked around the head and sucked him bobbing gently up and down. At first it felt a little strange having a limp cock in my mouth, but soon I felt him begin to swell and as he did, surprisingly, I kind of liked it. I remember thinking how oddly rubbery the head of his penis felt in my mouth and how I could feel him grow and twitch. He kept growing until I couldn’t get all of him in my mouth anymore and I liked that even more.

I was actually really getting into the blowjob, but it occurred to me that something was wrong. Steve was probably staring at the back of my head and that wouldn’t do. I needed to know he could see what I was doing so I reluctantly pulled my mouth off of Silas’ now fully erect cock and stood up. Silas opened his eyes and looked at me.

“What’s the matter?” He asked.

“Nothing.” I said, “just turn sideways, I want to get on the bed.” He did as I asked and turned so that he was now laying perpendicular to Steve with one leg hanging off the end of the bed. “Ok,” I said, “Close your eyes again.” After I was sure he wasn’t looking anymore I looked Steve directly in the eyes as I stroked my own cock. I saw him lick his lips in approval, but he stayed in the same position, hands folded in his lap. His hungry eyes egging me on I got on the bed stuck my head back between Silas’ legs and gave his now very erect cock a big sloppy lick from balls to tip before taking him back in my mouth. As I bobbed slowly up and down I tried to take more and more of him in my mouth until I felt him hitting the back of my throat and I came up coughing.

“Are you OK?” Silas asked.

“I’m fine.”

Undeterred I tried again and again, gagging and sputtering until I finally felt his cock slip down my throat. I felt the strong urge to cough again, but I fought it down. This was my fantasy coming to life and there was no way I was going to stop now. I felt more and more of him slide down my throat until my lips were wrapped around the base of his cock. I bobbed up and down loving the feeling of his cock sliding in my throat. My eyes were watering and my mouth was salivating making the blowjob sloppier and sloppier. I kept trying to press more and more of him in until my nose was squished against his pubic mound. I heard Silas groaning and I pictured Steve staring at me, my friend’s cock down my throat. I tried to turn on my side so Steve could see my own cock sticking out, red and excited. I was hooked and I wanted more. Silas was groaning loudly now and I was worried he was going to cum and it would all be over. Before he could cum I reluctantly pulled all the way off of him.

He tried to grab his cock, but I pulled his hand away.

“I’ll finish.” I said, “I just need a second. You’re so big my jaw is sore.” Strictly speaking that was the truth, my jaw was killing me. I looked at Steve, who still hadn’t moved.

“Do you have any lubricant?” I asked Steve.

“In the dresser, top right.” He answered evenly.

I got up, my erection bobbing around as I walked and practically threw open the drawer. I didn’t have to look long. The whole drawer was full of condoms, lube and assorted toys. I resisted the urge to look through the toys and just grabbed the first tube of lube I found.

“What’s that for?” Asked Silas.

“Don’t worry, it’s for me.” I answered and resumed my place on the bed. I didn’t even wait for Silas to close his eyes. With him still looking at me I looked him right in the eyes while I put his cock back in my mouth.

“Oh god that’s good!” He exclaimed and leaned back again.

With his cock in my mouth I opened the tube and drizzled a big glob of lube on my hand, then awkwardly propped myself up on one arm as I got up on my knees then reached through my legs with my other hand and began rubbing my fingers around my hole. It felt great just running my finger over my sensitive sphincter, but I was impatient and I thrust a finger inside as far as I could and began massaging my prostate. I’d fingered myself before while thinking about Mrs. Chlebek, but it had never felt this good before. Instead of imagining my 35 year old teacher there was a real 50 something man watching me and instead of a strap on there was a real cock in my mouth and instead of feeling weird, that was somehow hotter, naughtier and even more of a turn on. I deep throated Silas again and stayed there, my nose pressed hard against his crotch, my nostrils filled with his scent. All I could think of was Steve sitting fully dressed, just a couple feet away, staring at me while my throat was so full of cock so that I could barely breath, propped awkwardly on one arm as I frantically fingered my prostate. I must have stayed like that for a couple minutes, tears running down my nose and my face turning blue. I was in heaven, but it wasn’t enough. Again I reluctantly pulled off of Silas’ cock.

“Silas?” I said, two fingers still buried in my ass.

“What?” He asked looking up at me.

“Silas. Let’s give the man his money’s worth. I want you to fuck me.”

“What. Are you serious?”

“Come on. You said you always wanted to try anal. Please. I need you to fuck me. Please.”

“Fuck. Sure. OK.”

I was a little surprised how quickly he agreed, but I wasn’t going to question a good thing. I poured a ton of lube on my hand and stroked his cock with it. It felt so good lubed up in my hand I didn’t want to let go. My face was close to Silas’ and we looked at one another while my hand slowly stroked his hard cock. Our lips were so close for a second I thought we were going to kiss, but maybe I was just getting caught up in the moment. I let go of his erection and got on all fours, trembling with anticipation. Fortunately I didn’t have to wait long as he immediately drove his cock into my prestreched hole.

“Jesus Christ!” I yelled.

“Are you OK?” Silas asked.

“Yes, fuck me!” It felt so good to be filled up and stretched like that, I needed more.

“Oh god your ass feels good.” I heard him say as he began to thrust. I moved in motion with him, shoving my ass back against his hips as he thrust.

“Slap me.” I commanded.

“What?”

“Slap me. Slap my ass!”

“What? Fuck you!” He yelled back and then crack! I felt and heard him violently slap my left cheek. I winced from the wonderful pain. I could feel the sting and the heat from my ass.

“You like that?” He asked.

“Yes! Slap my ass! Call me naughty!”

Crack! I felt another slap.

“You like that you naughty bitch?!” he yelled.

“Yes! Yes!”

I loved how he called me a naughty bitch and I couldn’t get enough. I felt one more slap and then without warning Silas flipped me onto my back, pinned my knees up to my chest and drove back into my ass.

“You like that? You like me your naughty little bitch ass?!” He yelled at me. Something unexpected had awoken in Silas. He wasn’t thinking of Mary Saunders, he was looking straight at me, while pressing my knees hard into the chest. I felt totally in his power and I loved it.

“Yes, I like it!”

“Say you liked sucking my dick!”

“I loved sucking your dick!”

“Say you like getting fucked in the ass!”

“I love getting fucked in the ass by your hard cock sir!”

“Only bitches like getting fucked in the ass. Say you’re my bitch!”

“I’m your naughty little bitch. Just keep me!”

I turned my head to see Steve in his chair, a smirk on his face as Silas pounded into my ass. That look and Silas’ cock rubbing against my prostate sent me over the edge and I came. The first rope landed on my chest with more coming painting my stomach. The whole time I couldn’t take my eyes off of Steve.

“You like being covered in cum?” Asked Silas. He didn’t wait for an answer, he just pulled out and straddled my chest while jerking off. I looked up to see his cock above me looking dominant and powerful. It only took a few strokes for him to come. The first spurt came out like a rocked hitting my forehead before he aimed his cock down so that the rest of his jizz landed on on my cheek and mouth. He kept stroking until the last drop trickled out on my chin. When he was done he leaned back and collapsed on the bed panting as I stared at the ceiling, cum slowly trickling down my face.

“Fuck!” I heard Silas yell.

After what felt like an eternity I heard a slight creak as Steve got up. I looked over to see him take out his wallet again and without comment count out another $400 and place it on the dresser.

“Very enjoyable.” I heard him say. “You know, if you’re interested in earning some more money, I have friends who would pay to see a show like that. Think about it. Feel free to use the shower. I’ll be downstairs making myself a drink.” And with that he walked out leaving us alone.

Silas and I leaned up and looked at one another, his cum still sliding off my face. I could taste it on my lips.

“That was a hell of a show we just put on, right?” he said finally

“Yeah.”

“Look, we already said we don’t talk about this to anyone. Agreed?”

“Agreed. Totally.” I said and then after another small pause. “But we can do it again, right?”

There was another small pause before Silas answered. “Sure.” He said. “I mean, it’s good money.”

“Yeah, of course, it’s good money.”

“Yeah, I mean that’s why we’re here, right? But,” he paused for a second as though he was considering something. “But I mean, if, if you wanted to suck my dick again sometime, I mean that would be OK. I mean I’d be OK with that.”

“Maybe.” I said carefully. “I mean if you get bored jerking off, I could, you know, do it as like a favor. I know how frustrating it can be.”

“Yeah. Yeah. Thanks. Sure. You mind if I shower first?”

“Go for it.”

He hopped off of the bed and as I watched his toned ass walk out of the bedroom. I realized he hadn’t even looked at the money on the way out. I knew this was only the beginning for me. In my mind I was already rewriting my fantasy. Now it was Silas me in a classroom after school as Mrs. Chlebek watched.

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