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After college I had moved to New York City and got a pretty nice apartment for not so much money. The place had two bedrooms and since all my friends had moved to other places, I was left searching for a roommate. Luckily, I had a friend from high school, Dan, who had always wanted to live in the city and we had kept in touch. Unluckily however, he had never gotten a job and I needed someone to help me pay the rent. I knew Dan could make the money though. He had always found ways to get some cash, whether it was selling old shoes, jewelry, and electronics or some more illegal things that I wasn’t so sure about. Either way I needed a roommate fast, Dan had been a good friend, and he was the only one interested.

When he moved in I asked him how he was going to get the money. "Don't worry," he said. "I have my way of getting the rent." I didn’t want to push him to tell me but I was curious as to how he was so financially stable without barely leaving the apartment. Finally one day I forced him to tell me. "Alright," he said. "I’m not proud of this but it’s the only way I can get by until I get a job."

"What is it?" I asked. "I...have a website...where I use a webcam...to...to..."

"To what?"

"To...get naked for the gay guys who watch me. They pay me a good amount and I do what they tell me to do while naked. I hope that’s ok?"

I honestly had no problem with it. I had always thought Dan was hot, in a bad boy, built up sort of way. I told him it was fine as long as he gets the rent.

A couple months went by and Dan approached me timidly and said, "Hey lemme ask you something, and you can totally say no, no pressure, but I’ve been losing some customers because they say they’re getting bored of just me...they want to see me with another dude. So would you do it with me? We wouldn’t have to fuck or anything, just get naked together and show off."

I wasn’t sure what to say. I didn’t want to seem too eager so I said yes for the rent’s sake. Later that night, I couldn’t control my excitement to not only see my long-time crush get butt naked but also for me to be nude with him, doing things with each other. I went into his bedroom and waited for a customer with him. Finally, one guy asked us to get naked, so we did. I couldn’t take my eyes off Dan, his rock hard chest, abs, and arms, his muscular legs and thighs. When he was down to his underwear, I could see his cock's outline, bigger than I had ever imagined. He stripped down, his semi hard cock resting on top of his juicy balls in between his perfect thighs. I sat down next to him naked too, brushing my thigh against his ever so gently. At the request of his customers, we danced around, jerked ourselves, spread our asses, and fondled our balls. The whole time my eyes were fixed on Dan.

When it was over, I said I figured we’d have to do it again in order to keep his customers and he agreed and thanked me. Thanked me! He just gave me the biggest boner of my life and he’s thanking me! This could not get any better...but it didn't
 
If youd like some pictures to go along with this story, i can post some pics of dan (who is a real person) and you can see a bunch of pics of me on my thread, "Slim, Sexy, and 18"
 
OMG, that would be a dream come true for most of us. I certainly hope more has happened other than dancing, jerking, etc......lol Would love to hear more.

Craiger
 
That is a great start to a different kind of story, thanks for sharing it with us. There is a hint of more to come in your final sentence, don't keep us waiting.

So long as you have Dan's permission to show him, we would love the chance to assess his assets for ourselves.
 
YES! Please show pics of Dan and share more stories too!!!
 
Ok Here are pics of dan. I think hes pretty hot. And there is more story to come soon. I just havent gotten around to typing it
 

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Wait I’m so sorry. I just realized that I ended my first par with "but it didn’t" when I meant to say "but it did". I hope that makes it clearer. Ok here’s more:

Dan continued to "work" and only asked me to join him one or two times a month. Although I wouldn’t liked to do more those sessions gave me enough material to jack off for a lifetime. Eventually however, Dan realized that his customers had gotten a taste of the two of us together and wanted more. So those two times a month turned into about once a week.

I had to keep pretending that I felt a little uncomfortable and that it was only for the money. Dan was straight and I was bi I guess. I say I guess because even though I jacked off to men more than women, I only dated women and never really wanted a gay relationship. So while two seemingly straight guys getting naked together on a weekly basis doesn’t sound so heterosexual, Dan and I kept going, assured that it was only for the money which, in this economy, was needed. After all, beggars can’t be choosers.

So back to the sessions. There was one session in particular that really changed how the whole thing went. We had just started; Dan had his shirt and jeans off, leaving him in a baseball cap and his plaid boxers which, when he sat in the right position, allowed me to see just a little bit of cock up the leg. I was down to my underwear too and we were waiting to get some customer requests. We were rubbing our crotches; Dan would sometimes go under his boxers and casually stroke his big flaccid cock. While I still found him and the whole experience hot, I had somehow built a tolerance so my dick was soft too.

Finally: "Why don’t you guys get naked and jerk off a little" messaged the first paying viewer. Like clockwork we slid off our last piece of clothing, leaving us both 100% nude. We started stroking our cock and massaging our balls (Dan and I both loved playing with our balls, and his were just as impressive and delectable as his penis). We both started to get hard when I looked over and noticed Dan looking at my crotch. I figured he was just glancing, no big deal, but when I looked again he was still staring at me jerk my dick. He was masturbating to me! I looked right at his face and he gave me a look that told me that my thoughts were right! I mean, Dan and I had gotten extremely close through all of this, who wouldn’t. We often walked around the apartment naked and didn’t mind if the other one of us wanted to come into the bathroom while the other was taking a shower in our glass shower. But I never thought he liked what he saw so much. I decided to return Dan's actions and jack off to him stroking it. I had always wanted to stare but I thought he’d get uncomfortable.

I was so into it and ready to cum when I heard a new message from the computer: "jerk each other off"

We had never done this and always told our customers that we don’t do things to each other, but I knew Dan wanted to and god knows I wanted to jerk Dan off. So after a look from Dan, I reached over, grabbed his semi hard cock which was smooth but had a little bit of hair at the base and on his ball sack which was warm to the touch, perfectly stretchy, and perfectly round where his balls were, and stroked. I could see from the look in his eye that he felt great. Then I took my hand and fondled his balls, giving me a massive erection which was now being grabbed by Dan. With his soft yet muscular hand, Dan jerked me. Just the touch of his hand on my cock made me want to jizz like I’ve never jizzed before but I wanted this to continue and go further so I held back as much as I could. I looked at him again and he looked back with such elation and pleasure and I could tell that he had been wanting to do this too.

I couldn’t believe it, my fantasy was coming true and Dan wanted to get with me. I couldn’t wait for the next customer's request.
 
You can get PAID to do stuff like that? Where can I register?!

Seriously though hot shit. Do you have any naked pics of Dan?
 
Sorry, it’s been a while but here’s some more:

We knew we couldn’t cum on camera because we only did that for the private, higher paying customers and we hadn’t gotten any yet (I say we now because it was rare that only Dan went on camera without me. In fact he changed the profile to both of our names and the profile picture was one of the both of us sitting on his bed in only our boxers with his arm around me so that his armpit hair tickled my shoulder). So we always have to stop either when tips stopped coming in or when we knew we were about to blow our loads.

We were still stroking each other. I had my right hand on his long, hard, juicy cock and my left hand on his lower back, caressing just above his ass. He had his left hand on my rock hard dick and his right hand was going up and down my chest and abs, stopping every once and a while to play with my nipples. I was in heaven! I never knew I could be pleasured so much. This hand job from Dan was 100 times better than anytime I’ve fucked a woman. Every time I looked at Dan I could tell he was loving it too, licking his lips and moaning in ecstasy.

The tips were rolling in but we didn’t care. We had forgotten we were on camera, just locked in each other’s touch. I couldn’t wait any longer. Through my heavy breathing I said, "Dan, oh my god, I’m gonna cum"

"Shit," he said, "ok I'll end the session. Get out of the view of the camera just in case you do blow"

I stepped behind the table the computer was on, throbbing cock in hand, and watched Dan shut down the session.

Dan closed his laptop and we looked at each other. I didn’t know what to do. This was the first time since we acknowledged our sexual attraction for each other that we really were alone. No one was paying us or rubbing one out to us.

We stared at each other for about a minute before we started laughing. At first it was just a chuckle but then we were belly laughing. So much so that Dan laid back in his bed. At this point I stopped laughing and was observing his body. From this angle I could see all the muscles in his chest, abs, and legs, and there was a lot of them. I could see the underside of his hard cock and his magnificent, mouth watering ball sack. I could even see a little bit of his asshole, which I hadn’t really seen much since we were always sitting down.

Then I noticed that he had stopped laughing and was just lying there like that, as if he were waiting....for me! So I slowly walked over to him and stood in between his legs, his slightly hairy calves rubbing against mine, and for the first time not on camera, I started jerking off next to Dan. but not for long of course cuz I know that wasn’t what he was waiting for. So I bent over, put both hands on his knees, and slowly slid up his thighs until both hands were on his cock. I was pumping his cock with passion, I wanted him to get loud, and he did. He was moaning, through his deep breaths he’d say, "oh yea!" and "oh my god, fuck". While at first he had his eyes closed, he now was staring me right in the face as he rubbed his body with both hands.

Suddenly he yelled, "Shit I’m gonna cum!" So with my left hand on his cock and my right hand on mine, I pumped both our cocks for about 10 more seconds before we both simultaneously came all over Dan's abs.

That was by far the most amazing sexual moment of my life....that is until the next night ;)
 
I have a feeling the webcam customers would be willing to pay more if only they knew what was happening on that bed. Our guys have pumped it up a notch and sounds like it is about to go higher. Great update, ssssss. I'm fervently waiting for the next night.....

Craiger
 
Thank you Craiger!

I stared down at our mixing jizz on Dan’s abs, both our cocks still hard. I reached over to a box of tissues and pulled a few out. I would’ve loved to bent over and licked all the cum off but I didn’t want to move too fast so I wiped it off with tissues, feeling the heat of our juices through the thin tissue paper. I could’ve came again.

I had finished cleaning his body and was now wiping my cock head clean. Dan propped himself up on his elbows smiling and watching me clean myself and in between sighs of ecstasy he suddenly said, "Wow, I owe you one". "What?" I said. He owes me one? I just blew the biggest load of my life and he thinks that was me doing a favor for him? "What are you talking about?". Then he replied, "Well we were jerking off each other at first and while you finished me off, you had to do yourself as well. Haha I just laid there. So, I owe you a...pleasuring...I guess." I could tell he was getting a little uncomfortable, not so certain of what he was talking about. I understood, I still hadn’t processed this thing either. After a second I said, "Well, if you insist haha, how could I pass up an offer like that?" I could tell that me saying this made him much more comfortable as he was now looking up at me and smiling. He started to get up, "Just let me know when and I’ll be there, hands ready." He showed me his hands and I saw a bit of cum on his palm. Was it mine? Was it his? The mystery of it made me hard again. Do I dare ask him for that hand job now? No, if I do now Ill regret it some night soon when I’m really horny.

As Dan was walking out of the room towards the bathroom, as I watched his firm yet juicy ass bounce up and down, without even looking back at me, he said, "Ok I’m taking a shower, babe". Oh my god he just called me babe! Babe? What does that mean? Are we together now? Are we going to start having sex not on camera? Am I living with my boyfriend? Babe! While I had no offence to any of these things, it just seemed to be happening so fast. Dan...From high school...Jesus this was crazy!

I was weirdly turned on by all this hectic, unexpected confusion. I ran to my room, closed the door, and jerked off. It only took about a minute to cum. I was so tired from everything that I decided to go to bed.

Still nude, I walked into the bathroom to brush my teeth. Dan was still in the shower, and since the shower had a clear, glass door, I could see him rubbing soap over his naked muscular body. I was somehow getting rock hard again! I've seen him naked every day for about 4 months now and never thought much of it after a while but now I couldn't control myself. "Focus" I said to myself under my breath and turned away towards the mirror. The problem was, I could still see Dan in the shower in the mirror's reflection! It was as if the universe was telling me to watch him.

Before I could look away again, Dan saw me looking at him in the mirror. He immediately smiled and started soaping up his cock and balls while playing with his nipple and licking his lips, just like during the cam show. I smiled and looked down at the sink. When I looked back up he had turned around, bent over, and started soaping up his butt cheeks, turning his head to make sure I was looking. Then he showed me something I'd never seen. It’s easy to fantasize about a guy who you see naked every day but since we had never fucked and he’d never used a dildo (at least not on camera), his asshole was still a mystery to me. Well, not anymore. While he was soaping his ass, he pretended to accidentally drop the soap so he could bend over to pick it up. Slowly of course. As his hands were on the ground, his cheeks were spread out so far that I could see his entire hole. It even opened up a little bit, as if it was inviting my cock in, which was now again rock hard.

I couldn't breathe. I thought I was going to pass out. I found myself staring into my mirror, slowly pumping my dick as Dan showed off in the shower. Before I knew it, he was done and as he stepped out of the shower, I stared down at the sink, as if he had somehow not noticed me staring at him and jerking off to his hole. Dan walked over to me, wet and butt naked, pressed his entire front body against my entire back body, both of us naked, looked at me in the mirror and softly said, "Why don't we finish that show from before?". Then he gently grabbed my balls, and gave a little tug. He smelled like soap and sex. He smelled like my fantasy. But no, this was better than any fantasy I’ve ever had before.

I watched his ass as he left the bathroom. As soon as he closed the door behind him after one last look back, I dashed to the toilet and instantly came in it. Wow...three loads in under an hour! And now I was going for a forth with Dan on camera?
 
Wow, ssssss, you are prolific tonight. Again a hot chapter. Either Dan is teasing, or he is giving out subtle messages. Can't let those go by, must take advantage...... Thanks!

Craiger
 
Very hot and nice writing. Can we get a link to your shows or is the story all fantasy? Thanks.
 
Its been a while but heres another installment:

I walk out of the bathroom slowly in shock, not even caring that my entire back side was wet after Dan pressed up against me. I turned to see Dan drying off with a towel as he set up a cam session. He sat on the bed and placed the towel over his crotch. That image alone was so hot. It reminded me of when I watched these types of cam shows and saw other models so scantily covered, fantasizing about lifting up that towel and doing God knows what to their junk. But now, I wasnt separated by a computer screen. I didnt have to pay or plead to see a peak. I didnt have to type messages along with dozens of other horned up guys to get the attention of the model. I was six feet away from Dan. I had him all to myself. And now, I could do God knows what to his junk...in fact, I had! I was living my fantasy and that moment watching Dan on the computer was when I realized how amazing it felt.

Well, that moment ended when Dan looked at me and sensually patted the place on the bed right next to him, telling me to come over. So I did. I sat and put a pillow in front of my crotch so there was still something left to pay to see. My cock was soft which seemed odd to me, as I could not think of a more arousing situation, but after cumming a personal record of three times in under an hour, I guess it made sense. While before we sat close enough to each other so our thighs only grazed, now our thighs pressed against each other, we played footsie, and when Dan wasn't caressing my lower back he was resting his hand on my knee. I reciprocated by lightly grabbing the inside of his thigh which was still warm and a bit wet from his shower.

I looked at the computer and seen that Dan started a special session that customers have to pay to enter. You'd think we would always do this as it guarantees money. But customers pay for these shows because they want to see solo models cum and use toys and couples fuck. We had never even discussed fucking. It always just seemed like an obvious no. But Dan now made it seem like an obvious yes.

I got so nervous. I had never gone all the way with a guy. I mean, who would top? Who would bottom? Did Dan signal to me before that he was a bottom when he flashed me his hole? Did we have condoms or lube? All of this internal confusion was cut short when the first customer messaged us.

"You guys are so hot! Would luv to see all of you...;)"
"*25 credits*"

Without skipping a beat I moved my pillow and Dan dropped his towel. "Whatsup, man?" said Dan, in his usual cool way. The same voice I heard all throughout high school I now heard from a naked guy sitting almost on top of me. Surreal.

"My cock, that's what's up! And urs should too. Dont leave me hangin you two"
"*25 credits"

We starting playing with ourselves, pulling on our soft cocks and rubbing our balls. Dan got rock hard pretty quickly to the delight of our now 14 customers.

"Looks like you might need to help him, Dan"
"*15 credits*"

Dan looked down and saw my only semi-hard dick. "Haha yea I guess I could use a hand" I said, putting my hand on his back. With his left hand stroking himself, he reached over with his right and slowly rubbed. I leaned back and propped myself up with my elbows. Either he thought I wanted more, he wanted me to get hard faster, or a customer paid for it, but all of a sudden his hand got warmer, wetter...I looked down... it wasnt his hand. Dan was blowing me!!! I could see messages and tips coming in rapidly but i couldnt give a shit. I got so hard so fast that Dan started gagging. I couldve cum easily but I guess I had gained some control so I kept my juices in. I put my hand on his head, rubbing his hair as he went up and down.

Like I said, the customers were the last thing i was thinking about at that time. But it was the next message that made me more thankful than ever that they were still there...
 
The long wait has been more than adequately worthwhile - don't be too long with the follow on;)
 
Great update, ssssss! Those are the shows really worth watching and Dan obviously knows how to please. Can't wait to see what that next message is.

Craiger
 
Thanks you two!

As my fingers rubbed the short hair on his head going up and down on my now rock hard cock, I put my head back and moaned in ecstasy. Having cum already so many times that day, I could tell that although this felt incredible, I'd be able to last for much more before blowing yet another load.

By now he was on his knees on the couch, perpendicular to me, so the camera and all our customers (whenever I glanced at the computer, I saw our number of viewers increase) could see the whole left side of his magnificent body. I decided to heighten the situation but remembered to do so in the name of making money. I know it sounds a bit sleezy but hey, it turned both of us on, it gave us a reason to play with each other (although after the whole bathroom scenario maybe we didnt need this anymore), and we needed rent money. So after composing myself after the moaning, I said to the camera, "hey guys, I'll finger Dan's gorgeous asshole for seventy-five credits!" Dan looked up with an approving and excited smile while jerking my cock before putting his mouth on it again. I watched the computer:
"*25 credits*"
"*10 credits*"
"*25 credits*"
Each from different people. "C'mon guys, I really want to finger fuck him. I just need fifteen more cred-"
"*50 credits*"
"Wow! Thank you dude! Since you went above and beyond, I'll go above and beyond with Dan's hole." Dan looked at the camera and thanked the user again and said something about how much he wanted it or something. I wasn't really paying attention because I was thinking too much about being able to play with Dan's ass. The ass I had just been flashed in the bathroom a few moments earlier and had been so close to yet so far away from for months.

I grabbed his ass with my left hand, squeezing each cheek and running my middle finger up and down his crack, poking at his hole. Firm yet with a give. Muscular. He didnt have a lot of hair anywhere on his ass, even around his hole, besides some short, soft, blond hairs so it seemed naturally slightly furry. It's hard to describe in detail so I'll just say it was as perfect an ass as I've ever seen on a man, by my tastes anyway. And by our customers tastes apparently too since we had even more tips come in. I put my left middle finger in my mouth and started slobbering all over it to get it wet. I tried sucking on it at first to make it look sexy but it wasnt getting wet to the point of lubrication. So while slobbering isnt exactly smooth or beautiful, I did what I could. After all, who would remember my finger in my mouth after it entered that asshole. Once I got it wet enough, I reached back to his hole and poked at it again. I assumed, with as much certainty as one can assume, that he had probably not done any fingering and definitely had not been fucked up the ass before. Neither had I, though I had fingered myself on occasion at my horniest moments. I wanted to go slow and easy so it would feel good rather than painful.

I got my finger in up to the first knuckle while I slowly went in and out. Dan had stopped blowing me, though his hand was firmly still around the base of my cock, and started moaning and breathing heavy. He turned to the camera and said, "Anyone want to give some encouragement to a guy getting his virgin ass' cherry popped right now?" I assumed right. Dan was always smart and smooth like that, to guilt people into giving tips and giving a sexy pout to the cam whenever he did. And it worked! Within three minutes, by the time I had worked my finger half way to the second knuckle, we got over a hundred credits in tips! After each one, Dan would thank them and then go back to moaning. He had gotten used to the finger enough eventually that he went back to stroking my cock and getting it super hard again.

After having to ease in my finger so slowly just to get less than halfway down it while getting so much money in tips, I figured we wouldnt have to do any more to get more than enough money and that Dan wasn't ready for much more. We had talked in the beginning that we would never fuck, that fucking would take things too far and mean that we were both actually gay. Same with kissing weirdly enough, though I guess that's kind of personal and relationship-y too. I know it doesnt make sense at all but we, two self assured straight friends about to start getting naked together for other people's enjoyment and our financial gain without any experience doing so, thought it was a good rule. But after that day, after cumming together and what happened in the bathroom, I didn't know what was good or what rules still existed.
 
What's a little butt contact just between friends......nothing other than driving someone completely mad... It sounds as though Dan is pushing the envelop a bit and the rules are fading into the background. Why not? I'm sure I wouldn't be able to handle it as far as it has gone. Awesome update, ssssss. More please!

Craiger
 
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