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I spent the summer after my last year of high school working at a restaurant on the west coast, at a small resort town on the ocean close in Sonoma, California. I had grown up in a smaller town in the middle of nowhere in Ohio, and wanted to see a bit of the country before starting college in the fall. I also wanted to find a way to forget about my last year of high school, which was extremely uneventful. At 5’9″ and 140 lbs, I was definitely not the most athletic kid in school, and was mostly overlooked by everyone, especially the girls. I had long, shoulder length hair, fine features, and could barely grow a beard: not at all the football player type that suburban Ohio girls went for. I thought moving to California for a summer would be a good way to forget about high school before starting college.

While I wasn’t especially athletic, I did really enjoy running, and I took full advantage of the trails outside of the resort town. The scenery was incredible, ranging from dense pacific forests to open ocean views and even took me by a few secluded beaches. I’m pretty introverted, and I wasn’t really making any new friends at work, but I was falling love with the natural landscape and my secluded runs. Every 30 minutes or so I would bump into another jogger, but they generally seemed to be about as engrossed by the landscape as I was and didn’t pay much attention to anything else.

Like any 18 year old with a healthy sex drive, I enjoyed jacking off pretty much every day. I don’t know how or why – maybe it had something to do with being isolated and not having much of an outlet for my sexual fantasies – I started stopping in the middle of my runs to masturbate. At first, I would be extremely careful, going well off the trail and making sure that no one was around before pulling my shorts down a bit as if I was peeing, and jerking off as quickly as possible. But after a few careful sessions I realized that it was super unlikely that anyone would catch me, and that I could take my time, getting to the point where I would stop in the middle of the trail, pull off my tight running shorts completely, and spend a while pleasuring myself.

After a few weeks of this I started to play a new ‘game’ to test myself. I would strip naked, hide my running clothes in the bushes, and run for while wearing nothing but my shoes and socks. After I got too scared and excited, I would run back to where my clothes were and masturbate like crazy. All the running had given me a pretty slim and tight body, and I got into the habit of admiring myself while I was still naked before playing with myself. I was doing some stretches, my dick hard and pointing out, and while I was reaching up with my arms, my back arched and my ass slightly sticking out, I jumped as I heard a man’s voice.

“Very nice” he said, smiling at me lewdly. “Smooth and you’ve got a great ass.” He must have been in his early 40s, about 6’2″ with a strong build and a beard. He was wearing shorts and a plaid shirt, with hiking boots and a backpack.

I immediately covered my front with my hands, facing away from him to hide my ass.

“Don’t be shy now, I’ve been admiring you stretching for a while.”

“Fuck off you pervert!” I yelled at him, finding my voice.

He just laughed at me. “You’ve been running naked on this trail for the past two weeks, jerking off like crazy after you finish because it gets you so horny, and I’m the pervert?”

I was shocked, I thought I had been so careful not to be seen by anyone. “Whatever, you’re the one who’s been spying on me this whole time, you dirty old man!”

I started walking towards the spot where I had left my clothes, careful to keep myself covered. “Oh, are you looking for these?” he said, holding up my shorts and t-shirt in his hand. I was getting worried now – what did this asshole have in mind?

“I’ll give them back to you, but only if you finish what you came here to do” he said, smiling that same dirty smile.

“Definitely not happening!” I said, lunging to try and grab my shorts in his hand, but he pulled away quickly and I missed.

He just looked at me, still smiling. “Then you’d prefer that I send these photos and videos of you to your friends and coworkers, I guess?” He pulled out his phone and scrolled quickly through photos and a few very embarrassing videos he had taken of me masturbating. In one of the videos – it must have been two days ago – I was leaning up on my toes, ass sticking out and hand bracing myself against a tree, as I came, moaning like crazy.

I was wondering what had led me to jerk off like that, with my ass in the air and moaning in not the most masculine way, and, if I have to admit, getting even hornier thinking about it, when his voice brought me back to the current exceedingly awkward moment. “Here’s the deal. I know you’re working at one of the restaurants at the resort. I’m guessing you’re saving up for college or something. If you jerk off right now – like you always do anyway – I’ll give you 500 dollars.”

I was about to turn around and run back to my apartment as quickly casino siteleri as I could, but I had to admit that this was kind of interesting. Sure, he was a pervert, but if it was only jerking off quickly, maybe it wasn’t such a bad deal.

“Let’s say I do that – will you delete the photos and videos you took of me?” I asked him.

“Sure, I’ll even delete them right now” he said, showing me as he erased them from his phone and pulling out five 100 dollar bills. “And I promise I don’t have any backups.”

Was I really going to do this? I could definitely use the money, and he had already seen me masturbate so maybe it wasn’t quite so bad. Also, I couldn’t deny that I was even harder than usual, and was leaking precum all over my hands and arm.

I slowly pulled my hands away and started to do what this older man wanted. The thought of someone – anyone – watching me masturbate was incredibly arousing, and I knew I wasn’t going to last very long. After only about a minute I was moaning softly, and when I looked up at him he was rubbing his crotch, still smiling at me. I blushed and looked away quickly.

He must have noticed that I was getting close to cumming. I was standing up straight and picturing a hot blonde girl bent over in front of me, grunting as I imagined thrusting into her from behind. “No, not like that” he said. “Do it like you did last time.”

For whatever reason – maybe because I liked the idea of showing of for and pleasing an audience, even if it was just a dirty older man – I leaned up against a tree and got up on my toes, my ass out in the air. I closed my eyes and the picture of the hot blonde disappeared, as my moans became softer and higher pitched. I came harder than ever, my ass exposed, moaning through each spasm of cum.

I was embarrassed and filled with regret. The man clapped and whistled. “Lovely performance, glad I could capture it all for posterity” he said.

My eyes snapped open to see him standing there with his phone. He had taken another video of me cumming!

“You said you’d delete all the photos and videos!” I protested.

“I said I’d delete the ones I had already taken” he said smiling that same dirty smile. “Listen, you obviously need the money. Let’s make this a regular deal. You like to show off, and I like to watch. I’ll keep paying you to put on a show, and at the end of the summer I’ll delete all the videos. My name is Peter, by the way”

I bit my lip. Was I really going to play this game with him? I did need the money, and if it was just between the two of us and all he wanted to do was watch…

“Okay” I said, not believing what I was saying, “But you have to delete everything at the end and you can’t touch me. I’m not gay, okay? I’m Steve.”

“Fine by me” he said, smiling and handing me my clothes. “I’ll see you tomorrow, Steve.”

I got dressed and got out of there as quickly as I could. By the time I got home I was horny again – typical 19 year old – and I jerked off again thinking about that imaginary hot blonde girl. Only this time, I couldn’t stop thinking about how exciting it was to have someone watch while I played with myself. The image of Peter rubbing his crotch and smiling at me popped into my head, and the realization that I was able to turn someone on by showing off pushed me over the edge. I came hard, collapsing onto my bed. I was worried and nervous about tomorrow, but a small part of me that I hadn’t even acknowledged yet was also very excited.

—–

The next morning I had pretty much resolved not to see Peter again. I started looking online for different places to run, deciding then and there that I’d never be able to go near my old running trail. After about 30 minutes of searching, I found a trail that looked great, and would take me by the ocean as well. I was putting on my shoes when my phone beeped with a message.

“You’d better not be thinking of blowing me off today. Peter ;)” A screen capture from yesterday was attached.

My first thought was how did he have number, and then I realized I had left my phone in my shorts when I went off for my exhibitionist run yesterday. As if to confirm, I got a second message from Peter: “You should really put a passcode on your phone by the way. I managed to get a bunch of your contacts. Maybe they’d like to see your video? Make sure you’re on time.”

I was upset, but resigned. It wouldn’t be that bad – I’d be jerking off naked on another trail anyway – and I could make some extra money. When I got to the spot we met yesterday, Peter was already there. Now that I got another look at him, I had to admit that he was pretty muscular and quite handsome: if he had been at all interested in girls he wouldn’t have had any trouble picking up attractive women, even ones around my age.

“Hi Steve. Good to see you” he said smiling. “I’ve got a deal for you. You can either do your normal run naked and come back and jerk off, and I’ll give you 500 dollars like we agreed, or you can wear the outfit I have in this bag and do the same thing, and I’ll give canlı casino 250 extra. What do you say?”

“I’d say I’d have to see what’s in the bag first” I said, a little apprehensively.

He pulled out a pair of tight black shorts and a sports bra. Both had pink stripes down the middle. It was basically what female volleyball players would wear at their matches, and looked at least a size too small for me, as slim as I was. That being said, it was an extra 250 dollars to wear clothes instead of run naked.

“Sure, why not” I said, thinking that he was an idiot for even proposing it, but hey, it’s his money.

I walked off the path out of sight to strip down and put on the bikini bottom and a padded sports bra. The bottom was embarrassing enough, as my ass was hanging out and you could clearly see the oultine of my cock, which was getting harder by the second. But what was even worse was the top. It felt very weird to put it on, but strangely exciting. I figured with my longer hair and smooth face, I might even be able to pass for a girl with small breasts, because of the pads.

As I emerged from the woods Peter smiled in approval. “I knew you’d look great, very sexy Steve.” He gestured towards the path. “Now all you have to do is run 20 minutes out and then back, and do your thing back here for me to watch.”

I blushed when he complimented me, which was odd, and started running. At this time of the day there wouldn’t be anyone on the trail anyway, so no one would see me dressed up like a slutty beach volleyball player. I was about to reach the halfway point when I realized that two runners were coming my way, and I was going to have to pass them. They had seen me from a distance so it was too late to jump off the trail. As they came closer I realized they were both young guys, a little bit older than me. Would they laugh at me, or make fun of me? I thought I must have looked pretty stupid with what I was wearing.

As they got closer I braced for an insult or two, or at least a dirty look, but they both barely looked at me, as if it was totally normal to see a guy dressed up in a girl’s beach volleyball outfit. As I ran by them, I looked back and I could see one of them was staring approvingly at my ass cheeks poking out of the bikini bottom. He looked up at me and smiled. I blushed and ran even faster in the other direction, but I was even harder then before. Why was I getting turned on by another guy staring at my ass?

When I got back to Peter he saw immediately how hard I was, and knew that I had passed by the guys. He told me that he had asked the two guys if they had seen his girlfriend up ahead, and they said yes. They both thought they had ran by a girl!

Peter had another surprise for me. “Okay, so you’ve definitely earned your 750 dollars today Steve. But I’ll double that if you let me give you a massage before you jerk off for me – you must pretty sore having run so hard to get away from those guys!”

1,500 dollars was a lot of money, just for going for a run and getting a massage, so I said nodded and said “Deal. As long as you keep your hands away from my cock.”

We went back to his car to grab some massage oil. “We’ll do this with you standing up, if you don’t mind” he said “I don’t really have a table here.”

He started by rubbing the massage oil up and down my legs, going slightly under the bikini bottom to cover my ass as well. The oil was fresh and made my skin tingle a bit, but in a good, relaxing way, which wasn’t at all helping with my hard on. He knew exactly how to give a great massage, and his strong, large hands worked my lower and upper legs as I sighed in relief. He started to work on my ass a bit more, and it felt so good to feel my muscles relax that I didn’t even protest.

“Why don’t we go sit down on that bench over there so I can work your glutes a bit better?”

The tingling feeling of the massage oil combined with his skilled hands was amazing, so I just nodded and followed him. And anyway, I was getting paid to get massaged!

He gestured for me to lie down across his lap. “Ugh, do I really need to be in that position?” I said, very aware that I was still rock hard and getting even harder, and not wanting to give him any more satisfaction than necessary.

“If you don’t mind” he said “It’s much better for the angle and the pressure, and you’re pretty tight!”

Well, I thought, he was paying me 750 dollars.

I got into position across his lap and he really went to work on my ass. I have to admit it was amazing, and I was sighing and moaning from the feeling of relaxation almost immediately. I barely even noticed when he pulled the bikini into my ass like a thong, and – very much against my will – even moaned softly when his fingers brushed my hole.

I also had another problem – each time he massaged my ass, my cock would grind into his muscular leg. I think some of the massage oil had gotten up on my dick as well, as it was really tingling and twitching.

I was having trouble keeping myself under control, and managed to whisper kaçak casino “Don’t you think this enough?”

He just smiled at me and massaged even harder, rolling the bikini bottom down so my ass was fully exposed. He was pushing up with his finger against my hole now, and I was shocked to feel myself uncontrollably pushing back against him! As his finger slid inside and started to explore, he reassured me, saying that it was just part of the massage and a way to really work my glutes through my prostate. His finger kept brushing up against something inside me that sent shockwaves through my body, and I was trying my best not to moan each time.

The excitement of the run in a girl’s outfit, the oil massage, the grinding up against him, and now him massaging my insides was just too much. All of a sudden he pressed down harder on ‘that spot’, and I gasped and moaned “Peter, stop…” but it was too late, as I came hard in the front of the bikini bottom, moaning and shaking through each burst.

I could feel my cum running down my leg onto his legs, feeling waves of pleasure running over me. I had never cum so hard in my life. After what must have been a minute I calmed down and realized that I had made a pretty big mess all over his legs. “Wow Steve, I’ve never seen someone cum like that from having their ass explored for the first time” he said.

Hearing his voice brought me back to reality, and I realized I was dressed in a girl’s volleyball outfit, lying across an older man’s lap with my ass exposed and my own cum running down my legs.

I was upset and embarrassed, not wanting to show him how much I had enjoyed myself. “Screw you, I came because your leg was rubbing against my cock you old pervert” I said.

I got up a bit too quickly and lost my balance. I fell backwards towards the bench, straight into Peter’s strong arms, my bare ass on his lap and my head on his shoulder. It felt so comfortable and I was so tired and relaxed from the run and the massage, although I did feel how hard (and big, much bigger than me!) he was, pressing up against my ass through his pants.

When I finally managed to get up, Peter handed me my normal running clothes and the money for today.

He winked at me and said “Thanks Steve, that was great. Looking forward to seeing you tomorrow.”

I just nodded and started getting dressed, handing him the girl’s outfit. “No, you keep it” he said smiling “it does look great on you.”

Part of me was thinking that today went a bit further than I was expecting, but I had to admit that he kept his promise. Having his hands all over my ass was a bit weird, but it was all part of the massage so I didn’t think too much about it. And anyway I felt horrible about cumming with his finger in my ass and didn’t want him to know how embarrassed I was. In any case, so far this wasn’t so bad, and I had made a month’s salary in two days of ‘work.’ As I got home and showered it never even crossed my mind that this would go further, or that I would start to slowly give in to Peter as the summer went on…

—–

Our ‘games’ went on in a similar fashion for the next few weeks, always ending with him ‘massaging’ me on his lap until I came, and of course me calling him a dirty old man, promising him I was only doing it for the money. The only difference was that he had me try on new outfits to go running each time. One time it was a thong bikini, another time it was see-through gymnastics tights, and another he brought a white one-piece girl’s swimsuit that seemed innocent enough, until I started sweating and it became transparent. Eventually, he added an extra finger to his ‘internal massage’ as I loosened up, and gave me what looked suspiciously like a butt plug for ‘therapeutic massage purposes’ to insert during my runs.

As he made me moan and cum again and again while massaging my prostate, I started to feel new sensations in my ass and even started to miss feeling his fingers afterwards, but I didn’t think twice about it as I was making a ton of money while doing what seemed to be at worst harmless fun. I hadn’t even noticed how my own masturbating routine at home had slowly changed. Instead of just jerking off like normal, I would explore my ass with my fingers like Peter did when he massaged me. It felt good, but I couldn’t quite get the same angle and I couldn’t make myself cum. It would just make me more and more frustrated until I saw him again for those mind numbing orgasms, although of course I’d never admit this is why I wanted to see him.

All of a sudden, after one particularly intense massage session, he stopped messaging me. As the days went by, I was getting more and more pent up, unable to cum using my own fingers and desperately needing release. Finally, after seven long days, he sent me a message inviting me over to his place for dinner tomorrow, saying he would send a car to pick me up at around 6pm. Just after lunch on the day of our dinner, my doorbell rang and when I went to go answer it there was a young, attractive woman with a bag. “Hello, I’m here for your home spa appointment” she said. Seeing my confusion, she smiled and added “Don’t worry, the bill has already been taken care of by Peter. He told me that he would triple your normal day rate. He must really like you, this is the full package.”

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