That Craigslist Advert 01

I wish I was better with my finances. If I had been then none of this would have happened, but alas that wasn't to be.

I was 19 at the time. I was in college, and thanks to my ability to take out buy now pay later loans and credit cards, I found myself in a lot of debt. I had a part time job at a local cinema, but that just wasn't going to cut it.

So to help add some extra income, I decided to put an advert up on Craigslist. "Young guy looking for quick cash jobs. I'm 19, fit, and strong. I'm well able to weed, mow grass, and carry whatever you need moved. No job too big or small. Thanks."

I got the usual spam and scam responses, I had one person who wanted me to build her an extension on the back of her house (which was above my skillset just a little), and then I received this odd message.

"Hi, just saw your advert. I might have some work for you, might not be the most fun thing in the world for you, but it pays very well. Message me back if interested and we can talk more. Jason."

I immediately wrote back. "Hi Jason, Yes I would be interested to know more what would be involved. Thanks,"

About ten minutes later I got another email from Jason. "So we pay $2,000 per assignment. Usually all able to be done in one day."

That sounded amazing, but I still didn't know what he wanted me to do. Sensing maybe this might be something to do with drugs or crime I replied. "Cool so what exactly do you want me to do? Are you a drug dealer or something?"

Again I soon got a reply. "Haha no I'm not a drug dealer. I'm a specialist video producer. We make videos of young guys being intimidate with another guy for the first time in their lives."

I should have known it, gay porn. No thanks, I'll stay broke. I found no other promising leads from the advert and quickly forgot about it.

About two days later I ran into my landlord in the hall. I was behind on my rent, and he informed me that I was being evicted in 7 days if I didn't come up with the money owed before then.

I was in trouble. I was alone in the city, and had nowhere else to go. I was laying in bed that night wondering what was I going to do when suddenly I remembered that perverted email about getting $2,000 to do gay porn. So I retrieved the email, and decided to at least see what I'd have to do.

"Hi Jason, If I was to do this, what exactly would I have to do?"

It took maybe half an hour to get a reply.

"Hi, here's a link to what we do here, let me know what you think."

I clicked on the link which took me to a website and read the intro on top of the site. "Welcome to the biggest library of videos of straight boys getting fucked for the first time. We tie them up, humiliate them, stretch their tight assholes and make them take load after load of cum in their mouths. Watch them grimace in anal pain, recoil from tasting cum, and protest being tied up and humiliated, but they never ask us to stop. Click below to see our trailer." The trailer showed clips of guy like him being tied up, spanked, whipped, toys shoved up their asses, cocks in their asses, cum in their mouths, it was all pretty graphic.

I wrote back to Jason."Sorry I think that's a bit too intense for me, I just don't think I could do that."

Jason wrote back in less than 5 minutes. "I can pay you $3,000 just to show up, an extra $200 for each cock you can take anally, and $200 for each time someone cums in your mouth. We're a very niche business so unlikely anyone who knows you will ever see you, you can use a fake name, and nothing will happen against your will. We will stop as soon as you ask us to. One afternoon and you could have enough money to afford whatever you need. What do you say?"

Wow that was a lot of money, and as he said, nobody would ever need to know. It was all very tempting financially. Biting the bullet, I replied "Ok I guess I could meet up with you, no promises of anything more though."

Again Jason replied quickly. "That's great, Meet me at the studio at 2pm tomorrow. Bring an I.D., and if you can, use an enema before coming over so we can shoot tomorrow if you're up for it."

I actually did have enemas in the house thanks to a recent medical issue, so I figured what the heck and replied "Yes I can do that. See you tomorrow."

And with that I logged off, amazed at what I'd just agreed to, provisionally at least.

The following day I got up, I skipped breakfast, I was too nervous to be hungry anyway. I did my enema as requested and headed out to meet Jason at the address he gave me.

I arrived at a large non descript building at the back of an industrial estate on the far side of town. I poked my head inside to find nothing more than an office door and a hallway leading off it. Heart pounding, I knocked on the door.

"Come in." said a Man's voice.

"Hi I'm Tom, I'm here to meet Jason." I said nervously.

"Ah, I'm Jason, we were talking online last night right? Glad you came in, have a seat please. I sat down nervously and waited, not knowing what to say.

"So, you've had a look at our website, and you've still turned up, which means you must at least be open to participating. You must have a lot of questions, ask away." said Jason.

"Eh yeah... well..... eh..... what exactly would I have to do?" I asked.

"So, we tend to to focus more on oral than anal if you're truly an anal virgin which you said you were. We might still try anal if you're up for it, but we do enough oral to still have plenty film to work with. We'd use a few different guys for you to work with so we would get a few different cumshots. One rule is whenever someone cums in your mouth we need to see a shot of it in your mouth before you spit or swallow. It's ok if you don't like it too much, our subscribers are a bit out there, and many quite like the grimaces of our talent if there's cum in your mouth, or something too big in your ass. Regarding safe words, say red to stop at anytime, shake your head no if you're gagged, and say mercy if you want us to slow down but not stop. How's that?" finished Jason.

"Eh that's pretty good detail. I'm just a little scared is all." I said.

"Perfectly understandable. So look here's what would happen next if you decide to follow through and participate. We'll do some paperwork, I.D. checks, and some other bits. Then we'll do a body check for scars, track marks etc. Once that is all passed we'll start with a photoshoot and some still shots, then we do a quick interview for the camera, feel free to use a pseudonym if you wish, then we'd in bring the guys you'd be working with in and start. Bear in mind that we often stop and slow down filming to photograph certain still shots for the teaser reels. Feel you're up to the next step?" said Jason.

"Yes I'm ok with that I guess." I said.

The paperwork was all very straightforward, along with the body check. In fact the whole body check was quite clinical and comfortable, the only slightly sexual being Jason commenting that I had a natural twink body. I was 5ft10, short brown hair, fullish lips, a slim toned body, only a little body hair, peachy perky ass, and a 5 inch cock.

So about a half an hour later I was following Jason down the hall, and into what looked like a movie set of a upmarket bedroom. There was a large Long bed, a straw chair, a large mahogany beside cabinet, and a large area between the wall and bed. I stood there, in my boxers, feeling incredibly vulnerable, and a many other thoughts going through my heads as I waited for Jason's next move.

"So take off your underwear, and relax, have fun, things will go better for everyone this way." said Jason lightly. I did as he requested but couldn't help and feel uncomfortable standing there naked in front of him.

"So get on your knees and we'll start there." said Jason.

I got on my knees, as instructed I stuck out my tongue, had a blindfold put on, and I then had a ball gag in my mouth. I also took some photos with a banana in my mouth after the gag was removed.

"You're doing great, we'll do some butt shots now if you're ok." said Jason.

I was already on my knees, so it felt easy enough to bend over. I spread my ass, I took a photo of me teasing my own ass with my finger, then teasing my ass with a butt plug, and then i did similar photos with me sitting on the edge of the bed with my legs in the air.

"Fantastic, now we'd like you to put on these handcuffs and repeat the photos where possible." said Jason.

Jason put a pair of soft black cuffs on me. They were much more comfortable than I'd expected. We spent 20 minutes going through photos again, with me falling over a few times and needing Jason to help me into the correct positions.

"That's good work. Now let's try again but this time we'll take off the blindfold and put a jockstrap on you." said Jason.

Jason put on a blue jockstrap and we repeated. By this point my nerves were starting to dissipate a little, the repetitive mundane nature of the photos made it feel like just another job, almost. Again we repeated the same photos as before.

"Hmmm, if you don't mind I'd like to try a pair of panties on you instead of a jockstrap, we'll just do the anal photos this time" said Jason.

Jason helped me out of the jockstrap, and replaced it with a frilly black thong. Jason slid the thong slightly to the side to expose my asshole, and then we repeated the same photos as before.

"That was really good, very hot photos. So here's what we're going to do next. Were going to do the pre shoot interview. It's just a kind of teaser for the audience. During the interview, at some point your fellow talent will come in, and when the time is right, the scene will begin proper. Also if you're ok with it I'd like to remove your cuffs, and get you to wear a matching bra with the panties for the shoot. The thong looks great on you, and you have a certain closet sissy type of body, how does that sound to you?" said Jason.

"Eh, well it can't be any more humiliating than what I'm about to do, so yeah go ahead." I said.

Jason took the cuffs off me, and had to help me with the bra clips to get it in place, but we got there. I then sat on the edge of the bed and Jason mimed 3..2..1 and...

"Hi, how old are you and what's your name?" asked Jason.

"Hi, I'm Mike and I'm 18 years old." I said, I decided to use both a fake name and age for privacy reasons.

"Welcome here today Mike. So what is it you're here to do?" asked Jason.

""Eh I'm here to suck dick, swallow cum, and take a cock in my ass." I said.

"Very nice, and have you done any of those things before?" asked Jason.

"Never, so I'm quite nervous." I replied. At this point the door behind Jason opened, and in walked 3 tall, naked, or semi naked young men. Two of them were white, and one was black. They all had erections, they all looked very well hung, and they were all looking at me and smiling and winking.

"I can see you're new friends have arrived, what do you think looking at them?" said Jason.

"That their cocks look enormous." I said honestly.

"They are, but don't worry they're very friendly, you'll have loads of fun. I can see you're wearing a bra and panties, how do you feel about that?" said Jason.

"It's fine, I guess it does make my ass stick out a bit." I said.

"It does, have you ever crossdressed before? I think you'd look great in full sissy uniform." said Jason.

"No, this is my first time for this too." I said.

"Well we're glad to have you here. We've gone over your safe words and you know you can stop things at any time, which we encourage." said Jason, and I nodded. "So why don't you bend over and show these lovely young men what their prize will be today." continued Jason.

I knelt down and bent over, face down, ass up and pointed towards where the guys were. I pulled the thong aside and rubbed my finger around my anus. Honestly, this did feel kinda cool to think these guys were lusting after me.

As I got up and turned around I didn't notice one of the white guys coming towards me, cock in hand. Internally sighing, I closed my eyes, opened my mouth, and waited for the inevitable to come.

But nothing came, maybe he had decided against putting his cock my mouth. After about 2 minutes I opened my eyes just in time to see that same guy furiously jacking his cock only a few feet from me. And almost immediately after I opened my eyes he advanced on me again, this time thrusting the head of his cock into my mouth. I was just getting ready for the oral penetration to come when I heard a series of moans coming from the guy in my mouth, and felt a series of thick shots of cum flow in.

Slowly the guy withdrew from my mouth and moved back. Jason was standing behind him with a series of placards in his hand. ""open mouth" and "don't spit/swallow yet". I looked over and there was someone else on the video camera now.

Still a little dumbstruck, doing as instructed I opened my mouth and heard a few photo clicks, sticking out my tongue a little to make the photos quicker to take. After a minute Jason took down the "open your mouth" and covered the "don't" part of the other card. So while staring into the camera I tilted my head back and swallowed the cum in one go, sticking my tongue out to show the camera that I'd actually swallowed. The cum didn't taste that bad, like kinda warmish mayonnaise, and I liked mayonnaise so it wasn't as nauseating as I'd expected actually.

"And cut. That was amazing "Mike". You'd think that you'd been swallowing cum for years. Sorry about the surprise cumshot, Dave sometimes likes to haze the new guy, don't you Dave?" said Jason.

"Yeah sorry, but very impressive kid." said Dave smiling.

"So you've already met Dave, and the other two gentlemen here are Rob and Budda." said Jason pointing to the other two men. All three were 6ft-6ft2 and muscled. Dave's cock was about 8 inches, Rob's was about 7 inches, and Budda's big black cock measured at least 10 inches, and thick too, the thought of that in my ass certainly scared me a little.

"So we're going to start the camera running for the next scene which is you sucking them all off. And listen I don't normally say this, but if you can even pretend to like this, it would look great. I've been looking for a straight boy who suddenly converts to gay when faced with cock, and the way you swallowed that cum, you could be that guy." continued Jason.

"What do you need me to do?" I said half curious.

"Act enthusiastic, like you really want cock inside you. Dirty talk would be great, say if you're sucking cock then saying yeah I love this, or if the guys are saying something dirty to you then agree with them, like you're eager to be used. How does that sound?" said Jason.

"I could give it a go I guess." I said

"Great, do what you can, but there could be a bonus in it for you. Now, for the next scene the guys are going to circle around you and get you to suck them off. And I'd like to try something, we're going to put lipstick on you and see how deep you can go with the guys, and we'll do something with whoever you go most or least deep on as a fun forfeit, how does that sound?" asked Jason.

"Sure, why not, I'm in too deep now." I said half laughing to myself.

"Great. Ok guys get in position, and we'll continue the scene in 3...2...1...

All 3 men encircled me, Rob with the lipstick in his hand.

"Hey fag boy, come here, it's time to play a game." said Rob.

"Oh yeah, you gonna use my mouth are you?" I said.

I opened my mouth and Rob applied a thick smear of red lipstick to my waiting mouth. And without pause he aggressively shoved his cock into my mouth. I half gagged on the first push, but I'd expected this to happen, and had read up online yesterday on how best to deep throat. Basically what I was to do was relax as much as I could, focus on breathing through my nose, and just let the guy in my mouth set the pace. So within about 30 seconds I was able to go at least half way down his cock with each suck. After another few minutes of this I took a breath and held it in, trying to go as deep as I could, making it about 7 inches down Rob's cock before I had to stop. Rob withdrew from my mouth, replaced seconds later by Dave's cock, I was impressed that he was able to get hard again so quick.

I had gotten the rhythm of what to do by now, and within a minute I was able to basically go all the way, with Dave helping by pushing my head down until my nose was buried in his pubic bone. I did this a few more times before he also withdrew from my mouth.

"Wow you're a natural cocksucker, but it's time for you to deal with the big boy now, open up bitch." said Budda.

I opened my mouth, thinking I was a pro at this, but wow Budda's cock was thick, and I just wasn't able to relax enough to get him into my throat. After multiple attempts, I had to settle for going up and down his first 4 inches as fast as I could. I did enjoy the feeling of gagging on his cock a little bit, like I was a real whore.

"Well no need to get the measuring tape, couldn't handle the black beast fag boy? What are you gonna do to make it right? asked Budda.

"Whatever you want." I said.

"Ok, get over here and lick my balls bitch." said Budda.

I was just lowering down to comply when something else crossed my mind. Something that I'd wanted to try before with girls, and something I thought would look good for Jason on the camera.

"Please sir, can I lick your ass instead?" I said, keeping eye contact with Budda.

.

"You wanna lick my black ass bitch?" said Budda.

"Yes I do." I said quickly.

Budda turned around, and as I moved forward, I felt a hand on the back of my head, as I stuck out my tongue and aimed it square at Budda's approaching sphincter. I couldn't tell whether it was Rob or Dave forcing my head into Budda's ass, but it felt kind hot. And in all honesty, I kinda liked licking Budda. His ass didn't taste or smell bad, kinda like some fruity shower gel, I'd guessed Budda had washed with this before the shoot. I loved the long licks around his ass, followed by pointing my tongue and trying to go as deep into his asshole as I could. And the moans out of Budda were great, he was certainly enjoying it by all accounts.

While I was doing this I felt something wet being applied to my ass, followed a second later by the unmistakable feeling of a man's finger pushing it's way into my ass for the first time. There I was, my tongue deep in another man's asshole and a different man's finger probing my anal region and a thought came to me, I really need to be better with money in the future.

After maybe another few minutes of this I heard the deep moans out of Budda grow, I knew he must be getting close. I increased the depth and speed of my licking, knowing what was about to come if I continued.

And after only another couple minutes Budda moved away from me and turned back around, I knew what was about to happen. I closed my eyes, stuck out my tongue and looked up at Budda.

"You want to fill my bitch mouth with your thick black cum don't you? Come on, give it to me." I said.

Budda advanced on me, not breaking eye contact with me. I took him eagerly in my mouth and sucked. It took only about 30 seconds for Budda to let out the same moans as Dave before him, followed soon after by thick spurts of warm cum in my mouth. Budda's load was bigger than Dave's, and it was a bit of a challenge to keep it in my mouth for the camera shot without swallowing it by reflex.

After the same few still photo shots as before, I swallowed the cum again, this time finishing it with an "ahh" for the camera. Budda's cum went down easy enough. It was a little less salty and more bland than Dave's, I had no idea there was such a difference between men in terms of cum taste.

"And cut." said Jason. "Mike, you're doing better than I could have ever hoped. How are doing, everything ok?" asked Jason.