That Craigslist Advert 01

"Yeah I'm doing fine." I said.

"So how would you feel about anal now?" said Jason.

"I'm ok with trying it. But start with Rob, and we stop if it's too sore." I said.

"Of course, I was going to suggest the same thing. Usually bent over in doggystyle is a good position to begin. Focus on relaxing and breathing, like you've been doing so well while sucking cock. And don't be afraid to use your safe words, or to verbalise if you're finding it hard to take the cock in your ass, our audience really like that stuff for some reason. How does that sound?" said Jason

"Yeah sounds ok to me." I said.

Dave leaned over and whispered something in Jason's ear, with Jason nodding as he spoke.

"So we were just discussing, and maybe it would be good if we used some bondage for the anal scene. And maybe you should try loosen up a little bit with a butt plug before the scene." said Jason.

"I'm fine with the bondage, I kinda expected it honestly. And yes I think the butt plug would help, do you want the butt plug stuff to be on camera?" I asked.

"No that's ok. Even though we all know it's not really possible, our audience loves the thought of a cock being forced up a completely virgin asshole." said Jason.

"Sounds good, have you got a plug?" I asked.

Jason fetched a black medium sized plug and handed it to me. I was just about to start using it when Rob came over and asked if he could insert the plug for me, which I yes to.

So I lay on the carpet, face down and ass up like during my photoshoot, trying to perfect it as I'd guessed this was one of the positions that Jason would want later.

"So you're not really a straight virgin boy are you?" asked Rob.

"I certainly am. Why wouldn't you think I was" I said.

"Because you suck and swallow like a champion, you wear sissy lingerie without protest, and you even volunteer to lick ass when not asked to." said Rob laughing.

"Maybe I have a hidden talent, but push that butt plug in me and you'll see how new my ass is to things being in it." I responded.

Rob laughed as he applied more lube, and pushed hard against my ass stretching it.

"Wow you weren't lying about your ass anyway, here try this." said Rob, and with that he removed the plug and instead stuck his tongue in my ass. Wow! I can see why Budda liked it when I was licking his ass. It felt wet, warm, and amazing at the same time. After a few minutes I felt Rob withdraw and the plug back at my anal entrance. This time as he pushed so did I, this time trying to enjoy the stretching feeling instead of being scared by it. I pushed and pushed until I felt the plug pass through, it was in. Wow that felt huge and tight at the same time. Slowly I felt Rob pull on the plug until it was out again. He then pushed it back in. It was still tough, but it was a little easier than the first time around. Rob continued to probe me, pausing when the plug was at it's widest to help stretch me out.

"You have an amazing ass, I could play with it all day." said Rob. "Hey during the scene would you be willing to wear a garter belt and stockings by any chance?" he continued.

"Yeah sure, I've kinda gotten used to the lingerie to be honest." I said.

"That's so hot." said Rob.

We continued with the plug for about another 5 minutes. The pausing while the plug was at its widest really seemed like it helped. Then after that Jason found a garter belt and stockings, helped to put them on, and reapplied more lipstick just for good measure (In my mind I looked like such a whore now), and I wasn't completely annoyed about that I had to admit.

We returned to the carpet in front of the bed to set up for the next scene. Jason showed me two hooks in the floor that my hands would be tied to by a study rope, along with a spreader bar for my ankles. I got in position, and I'd be lying if I wasn't just a little tiny bit curiously excited about what was to come, I'd put in so much work up to this point, I wanted to know what it was like to have another man's cock in my ass.

I was helped into position. My ass was lubed up and some still photos were taken with Rob's cock at my entrance. Then I was gagged and we took some more photos, and then the gag was removed and I saw Jason appear in front of me and silently do his 3...2...1 and...

Smack! I felt Rob's big hand on my ass.

"Know what's coming next fag? said Rob

"You're going to shove your cock up my tight sissy ass? I replied.

"You learn fast fag." said Rob.

I felt my thong pulled aside once again and this time felt the head of Rob's cock push against my ass. The butt plug certainly helped, the stretching didn't scare me as much as it would have. I breathed out, tried to keep my ass relaxed, and in some way, enjoy what was happening to me.

"Ahh you're so huge for my ass, don't stop stretching me." I said loudly.

I felt more lube being poured on Rob's cock as he pushed. And with one final push his head was in. Inch by inch he pushed in, his cock felt like it went on forever, until after an eternity I felt Rob's pelvis up against my ass.

"Ok hold that position, we'll do some photos, Mike how are doing there?" said Jason.

"I'm good, It's tight but not awful, think I've got a bit of an erection too, make sure and photo that." I said through slow deep breaths.

"Ooh very nice, great shot." said Jason Then after a few more chicks "Ok Rob do your thing once you both feel up to it." continued Jason.

Slowly Rob withdrew from my ass, there was only about an inch of him left inside me when he stopped and started to go back in. I really had to focus here on my body and staying relaxed. The rhythm was slow and consistent, the feeling of Rob's cock pushing through my entrance, I had to admit I was starting to kinda enjoy the feeling of the feeling of the little bounce Rob's body would do off my ass cheeks when he reached full penetration.

"Say fuck my sissy ass." said Rob.

"Ahhh, fuck, my sissy, ass." I replied eventually.

"Say I'm a fag boy now." said Rob.

"I'm a, fag bottom, a fag boy now." I replied, my brain was a mess, not even able to get a simple sentence correct.

Rob continued in a slow consistent rhythm. After a couple minutes I felt Rob's hand on the back of my head, pushing it down. Ah yes this was the position Jason was practicing during the photoshoot, face down and ass up. It was a little easier on my knees, and the soft carpet was comfortable on my face. The angle was also much more comfortable for getting fucked too. Much less pain, and now and again some thrusts was sending a funny bolt of electricity through my body.

Smack, smack! Rob lay a could of good smacks on my ass. The camera guy, who had been focused on my face during the assfucking, was barely a foot from my face now.

"Ahh I'm so going to get my ass fucked again after this." I said to the camera.

"Aww yeah we're going to fuck you so many times, and you're going to fucking love it." said Rob.

"And cut." said Jason. "Mike you take cock like a champion, how are you doing?" said Jason.

"I'm doing fine, the last bit when my head was down, that angle felt kinda nice to be honest." I said.

"Ok, well we were going to move positions, how about we try find that angle again. Here we'll help you up." said Jason.

He loosened my restraints and helped me up.

"So yes we were thinking for this last scene we'd try something we don't normally do with our virgin shoots. How would you feel about having a cock in your ass and mouth at the same time?" said Jason.

"No promises, but I'll give it a go anyway" I said.

We discussed a few possible positions to shoot in, settling for me standing at the edge of the bed, so one guy could fuck me from behind, and another could lay on the bed for me to suck them off. I would be able to support my myself with my hands.

"So we're ready to go Mike, any preference of who goes where?" said Jason half laughing.

Eh yeah, I'd rather Dave in my ass, as his cock is the next smallest, and Rob in my mouth so I could swallow his cum next. Budda is huge so I'd need my ass opened up as much as possible before trying him there." I said.

We all agreed and got in position, took a few more still photos, and soon we were ready.

"Ok Dave, pull down Mike's panties a bit, I want a good shot of his cock aroused while getting filled. All good, everyone lubed up? Ok here we go, 3..2..1.. action.

I felt Dave pushing into my ass first. It felt about the same size as Rob, and this time I was better able to relax as he entered. At the other side I kinda let Rob do his own thing, using my mouth as he saw fit, the cock trying to invade my ass was commanding much more of my attention. Dave had managed to get his head in, and in one quick motion was all the way inside me. If Rob wasn't in my mouth at the same time I think I would have been screaming.

Dave then started fucking my ass a reasonable amount quicker than Rob had been, he also had a much tighter grip on my hips than Rob too. It was certainly more difficult to keep relaxed, though that angle of penetration certainly helped. Rob was properly mouth fucking me, but with relaxing my throat being so much easier than relaxing my ass, this felt easy enough to deal with. Budda on the other hand was basically narrating what was happening, which was really hot.

"Aww yeah use that fag boy, look at his little cock, he fucking loves it. Yeah let's fill this bitch with cum, he ain't gonna be able to sit down for a week after we finish with him. Yeah use use this fag, use him like he wants to be used." said Budda as I worked hard to cope with getting filled from both ends.

"Get ready bitch, I'm about to cum right in your whore mouth." said Rob. He had his hands around my face, his cock thrusting deep into my mouth, faster and faster, until the inevitable happened. Rob's cock swelled and throbbed, followed by the now familiar thick streams of cum in my mouth. I kept the cum in, and opened my mouth for the camera to see my full mouth, all the while Dave was still pounding away in my ass. Rob's cum tasted pretty bland, neither good nor bad, and I felt I gave the camera a good show.

"Oh look at fag boy, he's loving this, let's keep him working." said Budda.

My head was still down when I felt something pushing on my head. I looked up to see Budda's huge cock pushing it's in my mouth. He somehow managed to lie down in front of me, without me even noticing.

"Fuck I'm getting close." said Dave.

"And cut." said Jason. "I have an idea for the finish, Dave can cum in Mike's ass at the same time as Budda cums in his mouth. So off camera we'll get Budda close, then start the camera again for the main shot. Sound ok Mike?" said Jason.

"Yeah." I couldn't say much more, as Budda was still in my mouth.

So for the next few minutes I quietly sucked away at Budda while the others talked away in the background. It was a much different experience to doing it in camera, more natural.

"Kid you're doing so so good. I dunno if you are willing to do porn again, or even be with a guy again. But you've got a real talent. I would love to work with you again, that fine ass of yours especially." said Budda.

I would have said thanks, but my mouth was a little full at the time. I was able to go a little deeper than I could during the earlier sucking game, but still only had about half of him in me at my deepest. After another few minutes Budda signalled to Jason that he was ready for the final scene.

We got in position, just before the scene was about to start I remembered thinking that it was strange not having a cock inside me, I'd been probed so thoroughly already that day.

So after Jason said action Dave and Budda began pumping away in my mouth and ass. I never said it to the guys, or Jason, but I liked the anal sex. The oral was fine, and I felt like I was pretty good at it for my level of experience, but the anal was much nicer. I liked the feeling of my entrance being stretched once it had relaxed enough to not hurt anymore. I liked those pleasant shock sensations when my ass was at a bit of an angle (a later Google search told me this was likely due to my prostate being stimulated). And I liked the lingerie I was wearing. The way the thong pressed up my ass when I bent over excited me, I imagined how my ass must look with the garter and stockings on, and then the guys cocks pounding away, it must have looked a lot like the porn movies of women that I'd jacked off to before this.

I was completely lost in the moment in my own brain that I nearly missed the telltale moans coming from the guys that there was semen incoming. I felt Budda explode first, he had slightly less cum than before, but still a decent amount. And as roughly the second jet of cum entered my mouth I felt the first amount of cum in my ass, it felt like warm lube, and was certainly easier than having to swallow cum over and over again. We did wait and and catch a glimpse of the cum leaking from my ass for the camera but that was easy enough to do.

I also did my usual routine and swallowed like before. We took some still photos and a quick bye to the camera, and before I knew it that was it. I showered, got dressed, and I got paid (I got my appearance fee as a cheque, and my anal/swallow bonus as cash which was quite stunning to look at, I'd never made so much money so quick in my whole life).

Jason said that I could keep the lingerie if I wanted, and that he would likely give me a call in the future to see if I was interested in anymore work (I really wasn't able to answer him when he asked me, the were far too many other thoughts spinning in my head when he asked me).

And just like that, It was all over. I said one final goodbye, and walked back out the door I'd entered only a few hours ago as a virgin to gay sex, wondering to myself if/when I might do that again.