Student Life Pt. 06

I knocked, and then, quietly, asked to speak to him privately after he opened his room to me, still just dressed in some of his pyjamas, bottoms only. He looked over my shoulder and must have seen Dionne watching as well, but then stood back so that I could enter. Presumably thinking that she might overhear us in this private matter if he questioned me at the entrance.

"David, I'm... a little mixed up. I have some desires, secret sexual desires, that I'm hoping that you can help me with. Something with no strings attached, just as a one-off" I'd put the laptop on his desk and, being unable to check it as that would draw extra attention to what I was doing, hoped that it was pointing in the correct direction and angle to capture us both.

"Connor is so cocky and full of himself, while Scott is too much of a boy yet to make me think I can trust him to keep quiet if I'd asked him. I don't know many others in the city as yet and thought that as you are a really nice guy you would be the right one to help. Basically, well, what I want is, just to try something. To try anal sex for the first time. Could you help me with this? Please?"

I was trying to smile winningly at him while I spoke to make sure that I looked my best. Although, as I was still naked, I didn't suppose that many guys would care too much about the smile while the rest of me was on full display. A little shorter than the average, with not large boobs, I was still surely enough of a woman to attract the attention of most blokes in this situation, especially after just announcing that I wanted no strings attached anal!

David was clearly not most blokes. He stood there in his pyjama bottoms, looking pretty good in all honesty. He wasn't overly muscled but had enough to keep me interested if I'd been on an actual date with him. Hairless chest, clean-shaven, fair hair cut short. Generally well-groomed and attractive.

He wasn't reacting to me in the way I'd expected though, which puzzled me. Which worried me. I wasn't sure what should have been happening, other than a strong likelihood of being kissed and played a little with before he stuck himself up my bum, but this wasn't it. I asked if he had a girlfriend and didn't want to cheat on her -- if so, I'd never tell anyone, honest, so that would be fine. But that clearly wasn't the right direction to go in.

"Look, Amy, you are a really nice girl," he started, which was clearly a bad way for the chat to develop. "But, look, you say you have secret sexual desires, and so do I. I'll kill you if you say this to the others, but I think I'm probably gay. I'm working through a whole bunch of things about my sexuality and don't know where that will go, but, for now... thank you for your offer and for speaking so nicely about me. But no. Sorry."

My first thought was that I was doomed. My family was doomed. I'd failed, and that email would be going out shortly. Bloody well gay, or close enough! I'd not seen that coming, and neither had my blackmailer when setting this task. I might have been expected to get a little resistance from a bloke who was in a relationship, or wanting to be celibate or something because of religion. Fine, those I could have worked with -- but gay! Crap!

I turned back to the laptop to pick it back up and exit the room, then paused. Would he accept failure under these conditions? I had no way of telling, but thought that he might. Otherwise, I would no longer be his to play with, and I was sure that he had a lot more for me in mind, especially as he'd said he'd need to punish me for my act of attempted rebellion this morning. I didn't want to risk it though if I had any other option.

However, there was one more thing that I could try here. I paused while running the wording of this through my head. I'd not get a do-over, so I needed to get this right the first time. I wasn't doing well mentally, so I knew that I needed to be clear in what I said, and how I phrased it. Logical me to the fore!

"David, this could work out fine for the both of us. I would know that you will truly treat this as a one-off -- something that Connor and Scott would be unlikely to do -- and as for you, well, it would give you a chance to practise something with a willing participant before needing to do it in real life, so to speak."

At least he was still listening and hadn't bundled me back out of his room. Back to the watching eyes of Dionne. And what the heck did she think was going on in here? David was studying computing, so that seemed an innocent enough reason for needing to talk with him in private if she asked. Computer issues. They happen to us all.

"Here's my proposal. All guys, straight, gay, whatever, surely like getting their cocks sucked. I'll do that for you, get you hard. I'll then bend over the bed, kneeling down, and..." And what exactly? "I'll stick my head and torso under the quilt. That way you'll just have my backside to play with. It could be anyone's. Screwing me then will give you some indication of what it will be like to do anal with a bloke. With anyone. Then when it comes up for you in future, you can act as if you know what you are doing."

Oh hell, he wasn't exactly leaping at the prospect. Not that I could blame him, as this was rather out of the blue, and was a pretty bizarre request. 'Hey mate, so you're gay? Well, then how about fucking this pretty girl up the arse -- after all, it is much the same thing as doing a bloke when it comes down to it!' It was the best reasoning I could come up with though, however weak it seemed, even to me.

The only chance I could see of this going any further was a bold one. A risky one. The sort of thing that would get a bloke arrested as assault. However, as the naked girl in his room then I was already on shaky ground. Not giving any prior indication of what I was about to do I pre-empted any further discussion.

I quickly knelt in front of him, pulled down the front of his pyjamas -- and made sure that I would have grasped any boxers or underpants below if they had been there -- and stuck his mostly flaccid cock in my mouth. Before yesterday I'd never done this properly, yet now it was two in two days. My reasoning, such as it was, was simple. A guy getting a blowjob never said, 'that's enough, please stop now.' At least in movies and porn.

It wasn't like I did this every day, although that seemed to be the case just now, but he surprised me by being hairless down there. Very occasionally I'd come across that in porn, but it seemed that the usual man liked his own pubic hair to remain while wanting his women to be trimmed and neatly groomed. Was this a wannabe gay man thing, or just what some men liked these days? Not getting a nose full of pubes certainly got my vote though!

Normally I think I'd have been expected to look up and meet the guy in the eyes, for at least part of the time. Establishing that contact helped the relationship. They could see they were dominating you, if that was needed, while you could know you were in control of their experience, even while you were on your knees in front of them.

This time I kept my head down as far as possible. I was a girl in full make-up, and he'd just said that was pretty much what he didn't want in his life. I hoped to get him aroused (and that at least was happening) without making it obvious that it was a girl doing this. There was every chance that no one had ever done this for him, to him, so I hoped his imagination and dreams would step in and stop him from stopping me.

Getting him semi-hard didn't take long at all. Almost as soon as my mouth closed over the tip of his cock, and my tongue got to work as I moved up and down his shaft, the miracle happened. In a film, this would have been accompanied by a rocket ship taking off in the background, or a bridge being raised. Something highly symbolic to let the audience know what was happening.

Here, there was not even music to go along with what was happening. Just the slurping sounds that I was making. With Connor, I might have overemphasised them for his added pleasure, but I wasn't sure what to do here. I could hardly stop the action to ask if he was alright. I'd basically pulled his clothes down and attacked him in the hope that he would go along with me, and this had to work.

He had a full-blown erection within 30 seconds and, as he'd not pushed me away, I had to assume he was enjoying it. With the doubts over his sexual identity there was a heck of a good chance that he was a virgin -- as was I, although I didn't expect to be for much longer -- and that he'd not experienced this before. Watching porn was great for some things, but, as I'd found out myself last night, real-world experience was something else again.

Once up, he was probably a little smaller than Connor, but about the same size going around. Girth? Thankfully he seemed clean, which was a little bit of a surprise to me, given this that had come as a surprise to him. He obviously showered and looked after his body well though. I didn't go as far as deep-throating him, but close, coming at slightly different angles to make sure I got full coverage. I wanted him to be happy, but not too happy. He still had other work to do here.

For the person giving a blowjob, it can get a bit repetitive. I could see how in the right circumstances it might be nice to do this for your man, and you would focus on that. Here though, I just had the bobbing motion to concentrate on and to remember to keep my tongue in action. His breathing had changed, so I was happy he would stick with this bit -- but as for the next? There was only one way to tell.

I disengaged, grabbed the soap bottle and, in the same motion, nudged the laptop around to face the bed. The angle of the lens was probably still okay and I didn't take the risk of adjusting that and making him wonder what I was doing. If it had caught me on my knees sucking his cock, then it should catch me a little further away and bent over his bed. Probably.

Passing him my soap, I turned and burrowed under the edge of his bedding. My arms reached all the way to the other side of the mattress and I took a good grip there. I wasn't sure how this was going to go -- assuming it did go -- and wanted to make myself as stable as possible so that my accidentally slipping off the bed wasn't likely.

While I'd not mentioned this to him -- for obvious reasons -- I thought this a weak point, well, an even weaker point, in the plan. If he'd considered this from the start, then my smaller than average, slightly skinny frame was unlikely to match up to whatever bloke he'd been picturing doing this with. My hope had been that by the time we got to this point in the arrangements he'd have raging hormones and not be overly critical of my butt's appearance, or that my legs were thinner than his mind's desire.

I realised I'd not said what the soap was for, and hoped that he didn't need to be told. If there was anything of a doubt about this in his head, his being with a woman, then I didn't want to compound that by popping out of my small burrow for a chat. My bum was sticking out, and I tried to angle that so that my pussy would be as out of sight as it could be. It was hard to picture how this looked to him, so I hoped it would do for this one occasion. If it was likely to become a regular feature of life, then I'd maybe need to practise in front of a mirror!

I laughed, internally, at that for a second, but then stopped as it hit me that I had no idea what was going to become a regular feature of my life from this point onwards. Any arousal I'd been feeling at this situation disappeared. And there had been some, despite the oddity of where I was. Being naked, and sucking a cock, did something for me in that respect, even though it was not exactly a feature of my sex thought life.

With that video, attached to that email, I was totally in the hands of my blackmailer. He could tell me to screw, or be screwed by, every man in a gay night club and I'd be bound to give it a try. Or a regular nightclub. Or a bus station for that matter. My sex life, hell my entire life, was now his to direct as he saw fit.

The only thing, or at least the main thing, puzzling me right now was why had� he� not come forward to take me for his own? He was giving me to first Connor, and now David -- with Scott to follow for sure. Why had he not told me to come to, not his home as I'd then be able to act against him if I knew where that was, but a hotel when he could fuck me. Or a park, to do it outside. Or... anywhere really.

Where was he, and why had he not put in an appearance? Possibilities seemed to be that he was married, or had other family engagements? He was travelling when he found my phone and wasn't local? In which case he could order me to come to a location convenient to him. Or? I wasn't sure, and my immediate situation suddenly overtook my musing.

David had worked out what the soap was for but, rather than applying some to a finger and working his way in, had taken a different approach. Even just coating his cock and just going for it made more sense than this. As best as I could work it out from my position, he'd unscrewed the pump from the bottle and inserted the stem of that inside me. Sure, it would be coated in the soap from the inside of the bottle and was one way of getting a lot inside me at once, but that was real lateral thinking.

The thing can only have been about five or six inches long, given the size of the bottle, and quite thin, but it felt bloody weird. He swished it around, withdrew it, and then I could hear him shaking the bottle. He'd clearly put it back in and then mixed things up to reapply the gooey mixture. A few moments later it was back inside me about as deeply as it could go.

David did this once more, and then I could hear him putting the stem of the pump back inside the bottle and screwing it up again. Great. Just great. Now it wouldn't leak if it was knocked over or as I took it back to my room, but the entire bottle of soap was now contaminated by that part having been right up inside my bum. Was I going to be using that bottle to clean my face ever again? Not sodding likely!

One day I was going to have to talk to him about this behaviour. I certainly didn't appreciate this way of applying the stand-in lube and didn't think anyone else would either. Boys were just plain weird! Why would he have thought that a good idea! Use a finger man, like any normal person would!

The moment finally arrived when I could feel the pressure pushing against my ring. He had one hand on my hip, and presumably was using the other trying to guide himself into the target area. His tip went in relatively easily and was quickly followed by most of the rest of him. He was bigger, for sure, than what had previously gone up, but the large amount of soap must have helped. As should my having played with my own arse from time to time.

As he hit his limit, I could feel his hips pressing closely against me, squashing up against my buttocks. Anal cherry -- gone. While you were always supposed to remember your first fuck, I figured this would also count. Not quite done with a stranger, but pretty close, and in almost as meaningless a fashion. This would hopefully keep my family safe a little longer though, and so would be worth it.

I partially rethought that as he mostly withdrew and then shot back in again. His technique was lousy and didn't get any better as this was repeated time and time again. Rather than taking it slowly, which is what I'd want from anyone doing this, going in by increments and letting us both get used to the sensations, he seemed to have learnt from porn videos. Ram the bloody thing in, withdraw and then repeat.

Whatever he did to me was worth it if it kept that email from being sent. So I kept saying to myself anyway, as I started to feel a certain amount of pain and shock from the repeating impact. Soap plainly didn't cut it as a replacement lubricant, and this experience was now bringing tears to my eyes. People liked this sort of thing! Why? This wasn't fun, or sexy!

The noise being created by his fucking me was similar to the sort of sound that is made when you wash soapy hands, rubbing them together -- which made sense in the circumstances. A sort of soft sucking sound, punctuated by his grunting and my making low moans, but not of pleasure, as he went all the way in. I was trying my best to keep quiet, to not remind him that this was Amy underneath him, but was not being totally successful.

While it wasn't comfortable, I was getting used to the pattern of his rhythm, so I was able to anticipate how this was going to be until this situation was over. That helped a little as I could move with him. Calling it a 'situation' made it seem better than 'being anal fucked by a roommate you couldn't even remember the surname of, you knew him so little.'

He never completely withdrew but left at least the tip of his cock inside me, moving back and apart so that his hips no longer touched me. This was then followed by a long, reasonably quick, thrust, jamming his body back into mine. Each time this happened there was a clapping noise as my bum cheeks were flattened, to join the squelch from inside me.

Once all the way in, he'd give a grunt, then a couple of little wiggles of the hips. Presumably this gave him pleasure as he could feel the sensitive bits of his cock getting contracted by my sphincters in there. Flesh on flesh of my buttocks and his hips. Or something. I only felt the discomfort of being stretched and pulled in a part of my body that didn't want to be. Again, again, and once again.

I'd never really done this to myself. While I'd used objects to go in there, any fucking had been done fairly slowly and cautiously. If it hurt, then I stopped and went another way. If he'd been a regular guy, into girls and that, then I might have asked him to change his angle of approach to make it better for me. Would have done so in fact.

If that had happened, and he'd been touching my clit -- or I dared to, which I didn't at the moment in case the movement, the noise, drew attention to me -- and played with my boobs at the same time, then... then I might not object to this happening again. There were brief moments in there where I almost felt pleasure before the pain was back again, taking front and centre.

However, with David not really wanting to be with girls, I dare not talk to him. I didn't want to break his concentration and remind him of who I was. I thought that we were far enough along that he'd not care and keep going, but, if he wasn't, if he stopped, then I was finished. I just had to endure to the end. His happy ending.

All things come to an end, and this did as well. Eventually. His grunting suddenly increased and, with a few more violent, wonky, thrusts as he tightened his grip on my hips, he came. I'd assumed that I would feel something happening inside of me, but I didn't. I guessed that there was quite a mess in there, and his semen was just a small part of the overall gloop.

It was only as he started to back off, to disengage, that I remembered the second part of this. Getting butt fucked wasn't enough in itself, and would be a failure if that was all that I achieved here. I hurriedly got myself untangled from under his quilt, turned, and, catching him in the act of standing, managed to get my hands onto his legs.

He asked me what I was doing, as he fought slightly to regain the balance that I'd disturbed as I bumped into him and turned his body the way I wanted it to face, for the camera, but I didn't answer. I didn't need to, as it was pretty damn obvious. I was putting his now drooping cock into my mouth. Clean it like this or fail the mission was my instruction, and I couldn't afford to fail.

Given that he was a moving target, albeit a slow one, I'd had to go in with my eyes open to make sure that I achieved a lock with my mouth. Using my lips with the pretty cupid's bow. Not so pretty right now though, as I'd seen what I was heading towards, knew what they were wrapped around at this moment.