My Sissy Awakening 01

So there I was, 19 years old, at college, and living on my own for the first time. Life was pretty sweet. I'd made new friends, and felt like I was really having the time of my life.

Unfortunately, like a lot of other students, I was also broke. Between tuition and other costs, I was permanently in the red. To make ends meet I'd given private lessons to high school kids, done a few odd jobs, and even sold my blood on one desperate occasion.

So one evening, as was often the case, I was browsing through the college notice board looking for something that might earn me a bit of extra cash. It was amazing to see how many different groups and societies there were at this college, groups for just about everything imaginable. Poker? Yep. Korean? Yep. Pick up truck enthusiasts? You betcha.

I was skimming through the notices when I saw something that caught my eye, It had a big caption "Like anal sex?". I read on. "If so, then we're looking for some anal "virgin" guys for a new start up video producing company. Easy work. Cash paid. All "uniforms" provided by the us. CIM necessary. All models must be D&D free. Contact below for details."

Wow, getting paid to have anal sex? That'd be awesome. While it wasn't for a lack of trying, I was still a virgin. I guess maybe it was because I was a little slight in my build. I was white, about 5ft9, slim toned build, brown hair. Unfortunately it seemed that most girls were into footballers and bodybuilders, and I was neither.

I noted down the email address, along with a few other adverts that looked possibly promising, and continued on my way to the library to do some class work.

I was about half an hour into my assigned reading, and the boredom was overwhelming. I couldn't take it any longer, so I went for a walk to clear my head. Taking out my phone, and curiosity getting the better of me, I decided to message that anal porn company. "Hi, I'm enquiring about the advert looking for models you put up round college, just wondering what the physical requirements are? I'm 5ft9 and a slim build. And how much is being paid? Thanks, Joey."

I finished out my reading material with great effort, and was on my way back to me dorm when my phone beaped. I opened it automatically, and to my surprise that porn company had replied

"Yes those physical measurements sound fine. We pay $200 for a photoshoot, and $500 for a full video, with chances for a bonus if the video does well commercially. We're actually having a casting day tomorrow to meet with potential models. We have a space at 11am, I could book you in then for an obligation free chat if you like? Regards, Tina."

That sounded intriguing. And good money. I had a little reservation about losing my virginity on camera, but I knew that I wanted to lose it anyway so why not now? And I'd heard stories from friends about losing their virginity's awkwardly in the back seats of cars, or in tents at music festivals. So at least I'd have an original story to tell about losing mine.

Maybe I'd have to fuck a fat person, or maybe it was a granny or someone else gross, but I figured it was worth a visit anyway, so I replied "Great, I can make it in tomorrow no problem."

Tina got back and gave me the address. So the following morning I found myself outside a non descript building near an industrial estate on the outskirts of the City.

I pressed a buzzer and the door opened. I stepped into an almost silent lobby, there was a lady sitting at a desk in front of me, rapidly typing something I presumed important based on her level of focus.

"You must be Joey, we've been expecting you. Have a seat, Mr Aikan will be with with you soon." said the lady politely, though she hardly took her eyes off her screen.

I took a seat on the nearby couch, but it was there less than a minute before I saw a door open, and a man approached me, hand outstretched. "Harry Aikan please to meet you, you must be Joey. Come on through this way and we can have a chat." Harry looked to be the talent or boss guy by the looks of things. He was a black guy, maybe 6ft2, kinda rangy, like an old safety in football. He was about 45 with short greying hair and an easy smile.

He led me back to what looked like a half office and half photo shoot area. It being a start up company I guessed working space must be limited.

"So Joey, what brought you in here today? asked Harry.

"Well I saw your flyer on my college notice board and thought I'd see what's up, see if it was for me. The prospect of being paid to have anal sex was something I had to enquire about" I said.

"Good stuff. And tell me Joey, do you have much experience of stuff like this from your personal life?" asked Harry.

"Honestly no, I'm a complete virgin." I said.

"Really?" said Harry "You don't have to lie, the whole being a virgin bit is only for selling video clicks normally." laughed Harry.

"No I really am a virgin, is that ok with you?" I asked nervously.

"Of course yeah no problem, write your first video is going to do some serious clicks, could be a good bonus in it for you." said Harry. "Do you have any preference for the uniform types we use round here for your first time, I think a school uniform would look great on you, really help the scene come together." advised Harry

"Yeah whatever you think is fine with me regarding that stuff. When would I meet the person I'd be working with?" I asked.

"Well once all the formalities and paperwork is done we'd pick someone for you. I think you'd benefit from working with an older pro who's done this before, it'd take the pressure off you, they could guide you through your first time." said Harry.

"Sounds good." I said, a little relieved.

"So at this point I'd like you to strip naked, check for scars, track marks etc. And just make sure body wise you'rea good fit for our site, that ok with you?" said Harry.

"Sure" I said. I knew this point would likely come, but it was still a little nervous getting naked in front of another guy. Yet after a minute there I was bare assed, and Harry walking around me like this was the most normal thing in the world.

"Can you get your body hair waxed before the shoot? I know there's not too much but still nothing hurts sales like ass hair." said Harry and I nodded.

"Very nice, could you bend forward a little?" asked Harry. I did as requested. "That's gonna be a great shot, very tight, nice." continued Harry. "Would you like to do a wardrobe trial, if you don't like the school uniform we can try something else?" said Harry.

"Sure, might as well try it." I said.

"Cool, back in a minute." said Harry.

Harry returned a short while later, a black rectangular box in his hand. "Here you go, if you don't like some of the colours we may be able to change those." said Harry.

I took the box and lifted the lid, and to say what I saw surprised me didn't quite do it justice. Inside was what was clearly a woman's sexy schoolgirl uniform. There was white socks, black shoes, white stockings, garter belt, thong and padded bra. Accompanying these was a short reddish plaid skirt, white shirt, and blonde pigtailed wig.

"What the fuck is this?" I demanded.

"What do you mean, do you not like it?" asked Harry puzzled.

"I mean why are you trying to get me to wear a schoolgirl uniform?" I insisted.

"Because, I wanted to check you looked good in it before we shoot, we discussed this." said Harry.

"We did not. What kind of sick shit are you doing around here!" I demanded.

"What do you mean, what did you think you were going to wear during your first time? said Harry.

"My first time doing what EXACTLY?" I asked suspiciously.

"Eh, your first time dressing up as a sissy, sucking dick, getting fucked in the ass, and swallowing cum. Is that exact enough?" said Harry.

I was in shock. Words failed me momentarily. "Why wouldn't you put that on your flyer that you put out?" I demanded, half in hysterics.

"We did." said Harry bluntly. "I proof read them myself, and I've interviewed two others who responded to our ad, and they knew exactly what we did here." insisted Harry.

"Well it wasn't on the flyer that I saw." I replied.

Harry walked over to his desk, picked up a piece of paper, walked back to me, and handed it to me.

It was the flyer that I'd seen, except on this copy there was a part at the top above the "like anal sex?" part, and this made me read the entire flyer in a different light.

"Attention bottoms, sissys and curious crossdressers. Like anal sex? If so, then we're looking for some anal "virgin" guys for a new start up video producing company. Easy work. Cash paid. All "uniforms" provided by the us. CIM necessary. All models must be D&D free. Contact below for details." Above the wording there was also a small picture of a young twink looking guy with a cock halfway in his ass while wearing some kind of black lingerie.

"Oh wow, I've never seen the top part of the flyer. I must have missed it, or it must have been covered up." I said.

Reading the flyer again Harry kind of laughed. "Yeah I guess I can see how you read something very different. Did you not find the CIM bit odd though?" asked Harry.

""What does that mean?" I said

"Cum in mouth." said Harry.

"I thought it was some kind of irrelevant porn lingo." I said.

"So, you thought you'd be assfucking some mature woman while wearing a boy's school uniform, instead of getting your tight little asshole broken in while dressed as a sissy schoolgirl, do I have it right?" summised Harry.

"I wouldn't have worded it exactly like that, but basically yes." I replied.

"Well, this has been a real waste of time for us all, I don't suppose you've any interest in wearing the uniform so?" asked Harry.

"No, sorry." I said.

"Such a pity. I was going to pick myself for your first shoot, your ass is stuck in my brain, could I just see you wiggle it one time? asked Harry.

Feeling like I owed him, I have him a half hearted butt stick out for a few seconds.

"Such a waste. Look I don't mean to push my luck, but if you tried on the uniform for even a minute, I'd reimburse you as if you did a full photoshoot." said Harry.

"No thanks, not my thing." I insisted.

"$400 to put the uniform on for 1 minute, and I'll take no pictures, just a mental image." pleaded Harry.

"No thanks." I said, although at the same time I thought that did sound like good money.

"$500." said Harry.

I paused. That was a lot of money. More than I could make doing basically anything else in the same amount of time. I pondered for a minute longer, and then said. "Ok, I'll do it. No photos, 1 minute only, and I want cash." I said.

"Sure, thanks I appreciate it." said Harry who'd already put the money on the table.

Sighing to myself, I started getting dressed. I started with the thong (it felt flimsy but light on my skin), then I put on the stockings, that took a while. Almost as long as clipping the garter belt took. The bra was easy enough as I was quite flexible. then I put on the skirt, shirt, and shoes. I thought I was done but then I saw there was the wig, and some red lipstick hiding under it, sighing again to myself, I put them on.

"Wow, you're so hot, here look at the mirror." said Harry.

I took the hand mirror and wow, I was stunned. I did look hot, the lips, the legs the was only one word to describe me: fuckable.

"Just before you take it off, could you please bend over a little and lift your skirt? I would love to see it." asked Harry.

I'll be honest, at this point even I was curious about what that looked like. The heeled shoes made it very easy to bend over while still standing, I slowly lifted my skirt and even moved my thong a little to the side, revealing my asshole.

I remained there for a minute or so, wondering when should I stand back up. I was just about to stand back up when I felt Harry's hands on my hips. They were big and rough, one hand was then cupping my ass, while the other was wandering around to my..... rock hard cock! I hadn't even noticed that. I just remained there, no idea what to do next.

"Mmm, that's so nice." said Harry. He got much closer to me, I could feel his erection up against my ass, it was quite big.

On Hay went his hand was caressing my ass again, even giving it a light smack at one point. He moved his hand around until it stopped around my asshole. I heard a small pop and a squeezing sound and suddenly I felt Harry's lubed finger around my anus. He was rubbing around the edge before I felt the pressure as he pushed his finger inside me. Wow, even just one finger felt huge, I really had to control my breathing to try and relax. I wasn't sure weather I wanted him to stop, or try get a second finger in. After another minute of poking and probing Harry slowly withdrew from me. I just remained there, bent over with my back to Harry, waiting on his next move.

"I'm going to jack off, and I would love to jack off on your face, if that's something you've any desire at all to do, please get on your knees." said Harry.

I was on my knees without even thinking. I had become completely lost in the moment. Suddenly I was at eye level with his large cock, barely covered by his underwear. Harry then lowered his boxers to reveal his beast, it was easily 8 inches I guessed.

Harry grasped his chick, and began furiously jacking himself, inches from my face. "oh yeah, I'm gonna cum on your face bitch, make you a real sissy, oh yeah you'd like that wouldn't you?" He muttered.

His pace was picking up, he kept saying he was getting close. Then he says "get in position, here it comes."

I don't know why I did it, I had lost all control. Because with being asked to, I closed my eyes, stuck out my tongue, and moved forward, clamping my lips around the head of Harry's cock. It only took about ten seconds for the first drop to arrive. It was followed soon by squirt after squirt of thick warm cum. I kept as much it as I could in my mouth, though I think a little came out.

Once Harry had finished cumming, his cock stayed in my mouth for another minute, until I slowly withdrew. I didn't really know what to do with the cum but figured I'd give swallowing a go. So, hoping I wasn't about to vomit, I gulped. Honestly, it wasn't as bad as I expected. Yes it was thick, and the taste sort of stayed in my mouth afterwards, it was also more sweet and less salty than feared.

"That was pretty amazing, especially for someone who 15 minutes ago never had any intention of doing anything like this" breathed Harry after a while.

"Eh thanks I guess." I mumbled, I stood up not really knowing where to look.

"So, does anything that happened here make you reconsider appearing in a video for us here?" said Harry nonchalantly.

"Well, honestly no I don't think I could do that. But, and I can't believe I'm even saying this, but if you wanted to meet up again in a personal capacity for activities sort of like this, well I think I'd be open to doing that." I said.

"I could work with that for sure. As long as you're good with dressing provocatively like this, sucking and swallowing like you just did, and eventually you'll have to let me get my big cock all up in that tight virgin ass of yours, it really is the tightest ass I've ever seen." said Harry.

"Thanks I guess, it was all definitely more exciting than I'd expected." I blushed.

."And you're up for doing the other things I requested?" said Harry.

"Yeah I think I am." I replied half laughing.

"Well, in that case you should come over to my house this weekend, day Saturday? It's up in the hills, big spacious place, you'd love it. We can take our time and have fun." said Harry smiling. "I'd also like to you take this and practice with it, watch some porn or something and make a night of it thinking about what you'll be getting up to." said Harry as he handed me a small to medium glass butt plug.

"Here's your money Joey, you've earned it, spend it on something nice. And here's my number, message me later so I get yours." said Harry as he put the piece of paper down my top and into my bra, rubbing his other hand on my crotch as he leaned in and kissed me on the lips.

"I have to go, I have more work to do, so I'll leave you to get changed, Tina will let you out. You can keep the uniform if you want, I still have many lessons to teach you so it might come in handy later." smiled Harry as he headed out the door. I stared after him, wondering what I might get up to the next time I saw him.