2nd May 2001: Another experimental story from Sebastian’s schooldays. No trace of this online from its original submission – I’m not sure what happened to it!

Seducing My Housemaster

Part 1  

In my first year at boarding school, I shared a room with a guy called Toby. He was in the fourth form and was about a year older than me. He had light brown straight hair and was quite a nice guy. A bit serious about his studies, I guess, but not totally dull like a lot of the other guys in the top sets. Anyway, one night during prep (a kind of homework session during which the housemaster or house tutor would come round and check on us) Toby got out a girlie mag – Parade or something – and started playing with his cock at his desk. This was no big deal as we’d wanked in front of each other before and were always at it after lights out. I’d seen the magazine before (it was one of his regular jack off mags) and so I didn’t really pay him much interest. I noticed he’d pulled his trousers down around the tops of his thighs as he was sitting in his chair with the magazine propped on the desk.

As I got on with some Maths prep, Toby jerked away with his magazine in front of him, gradually getting faster and faster. I could smell his cock, even from my desk a few metres away. We weren’t too worried about being caught doing this kind of thing because we lived at the end of a long corridor, at one end of which was an old door which banged loudly. However, there was also a fire escape but no-one ever used that – at least not normally.

So you’ve probably guessed that on this evening the housemaster Mr Johnson, for whatever reason, did come up the fire escape instead of coming through the boarding house like he normally did. So Toby had no warning that we were about to be visited and in fact was tossing away quite frantically as the door opened.

I was really shocked when Johnson walked in. I looked around at Toby who was looking with horror at the door, his hand still beating his cock. At first I thought Toby mustn’t realise who it was in the doorway because he was still going at it really quickly but then I realised from his glazed expression that he was right on the brink of orgasm and just couldn’t stop himself. Johnson, a young Chemistry teacher, probably in his late twenties and with a wife and young daughter, roared “Stop doing that Adams and stand up!”

Toby leapt out of his chair, his school trousers around his knees and stood in front of Johnson, his prick pointing upwards. He looked like a scared rabbit, his eyes and mouth wide open and his cheeks red. He was side-on to me and I saw that his cock was arching upwards, kind of pulsating, as he stood there, and that his hips were jerking a bit, sort of thrusting forwards. In fact his cock looked as if it was straining – his bell end was really purple with his foreskin pulled tightly back. It was covered in clear precum and some oozed out of his piss slit as he stood there in front of Johnson. I was fascinated by all this and stared at his cock, clearly on the verge of an orgasm.

Johnson stared at his for a second then said, “You should be working. Get on. And put that bloody thing away”. On saying the last line he motioned with his hand at Toby’s cock and kind of tweaked the bell end, almost as if by accident. It may have been an accident, I guess, but it looked as if he deliberately rubbed his thumb up and down twice on the exposed moist bell of Toby’s cock. He did it so casually, though, that I wasn’t sure that he’d intended it.

As Johnson moved his hand away, Toby’s cock shot a wad of semen over the front of Johnson’s beige trousers and on the lower part of his shirt. Right around the groin area of his trousers, actually. Toby’s hips thrust forward, his buttocks clenching rhythmically, as his cock spurted wads of thick white cum over his housemasters trousers. After a few seconds, Toby’s body went limp and he stood there dazed, trousers still around his knees and cum hanging in strings from his cock.

Johnson looked at me and then back at Toby. The smell of sperm was thick in the air. Johnson then looked at his trousers which were splattered with quite a substantial amount of cum. He said “Do you have a cloth, Wallace?”

I went to the sink to donate my face cloth to the clean up operation and Toby sat down on his chair, his cock slowly softening. He said, sheepishly, “Sorry Sir”. Johnson said, “Clean yourself up for God’s sake”.

After Johnson had wiped the cum off his trousers as best as he could, he said, “I’m not going to tell anyone about this. If I were you, Adams, I wouldn’t either. Or you, Wallace”. We both said we wouldn’t tell anyone (Toby made me promise later that I really wouldn’t) and then he left. He looked like he’d wet himself because the front of his trousers were soaked. He was in such a hurry to leave that he forgot to confiscate the girlie mag, although Toby threw it away the next day anyway.

I later found out that Johnson was not as straight as he liked to seem. It was definately true that he was married (we saw his wife nearly every day), but he was definately interested in younger members of his own sex. So I realised that his making Toby reach orgasm as he had was almost certainly deliberate.


Part 2

The boarding house I was in had about 50 other boys in it. It was surrounded by gardens and trees which were popular with the boys as places to smoke. A few friends and I chose a cluster of bushes around the back of the senior common room which was quite secluded and slightly separate from the house. The common room was a converted barn, I guess, and the older guys in the house would go in there some evenings and watch TV or have a game of pool. The common room had on one side of it a toilet which was a bit draughty and dilapidated but was still used by the sixth form lads because it was right next to the common room. Well our bushes were quite near to this toilet – so near that we could here the sound of the guys pissing or taking dumps sometimes.

One evening in the summer when I was in the fourth form, I went round to the bushes for a quick cigarette just after prep. I guess it was about 8.30 and was starting to get dark. I don’t remember why but I was on my own – usually I smoked with my friends. Anyway, while I was sitting there, I heard the footsteps of someone coming round the back of the common room. This was the only way into this area – the garden had high walls all around it – and the path leading towards the back of the common room was quite long, giving smokers about thirty seconds to conceal themselves in the bushes. I shrank behind a bush and looked out to see who was approaching and saw that it was the Housemaster, Mr Johnson. I quietly put my cig out and watched to see what he would do.

He looked around quite guiltily and then squated down near the wall of the toilet. He took out a packet of cigarettes and started smoking one. I knew he smoked so this didn’t really surprise me but I wondered why he felt he had hide away to have one. I figured he must have told his wife that he’d quit and was having to sneak off for the odd one when he could. I was starting to get cold – night was falling – and wished he’d hurry up. He was taking his time, though – he just sat there staring into space, smoking his cigarette.

Suddenly his head swung around, away from me, and he waited, tense and poised. I wondered if he’d heard someone coming, although I could hear no footsteps. He put out his cigarette, being careful to be quiet, and slowly stood up. He looked around again to check that no-one had come around the corner of the common room without him hearing and then squated down again, this time facing the wall of the toilet. I wondered what he was doing – I couldn’t really see from where I was sitting.

I moved out a bit, being as quiet as I could, and realised he was looking into the toilet through a small ventilation hole positioned at about waist-height in the wall. There was a small dirty frosted window at the top of the wall which showed that the light was on so someone must have gone in there – it was the sound of that that he had been waiting for. But why? At first I thought he must suspect a sixth former was taking crack in the john and was spying in. This seemed a bit unlikely, though – surely there’d be a better way of checking that out. As I watched he changed position so that he was kneeling on the paving slabs, still looking through the vent. Then I noticed that his right arm, which I couldn’t see too well because I was looking at him from behind and to the left, was moving – his right elbow was kind of jerking.

It dawned on me that I was watching Johnson masturbating while he was watching one of the sixth formers taking a shit. Since Johnson had seemed to be straight I wondered if there was a girl in the john, but that was impossible because girls were not allowed in the boys houses in the evenings. So he must be watching a boy. Maybe the boy in the john was tossing off, I don’t know – more likely Johnson could get a good view of his cock through the vent and was getting off on it.

At one stage he got up to look around the corner to see if anyone was coming. Maybe he heard a noise from the path. As he got up I saw his hard cock poking out from the front of his trousers. His cock didn’t look very long, but remember it was quite dark and most of it was inside his trousers. This proved beyond doubt he was having a wank, though. When he’d made sure he was in no danger of being seen (or so he thought!) he got back to it. Once again, he kneeled down in front of the vent and his hand got to work on his dick. After about a minute the light in the john went off and his fun came to an end.

He got up, zipped himself up and walked away.

I was intrigued to know if Johnson really did like to look at boys . I was reminded about the incident with Toby which had happened during the previous year and wanted to know if he swung both ways. He was a very masculine guy, quite fit since he cycled a lot, and I was surprised that he might have gay tendencies. I didn’t tell anyone about seeing him wanking at the wall – I don’t think the guys in the house would have believed me anyway seeing as Johnson was a popular housemaster. Instead, I decided to linger in the shower one evening and see if Johnson would look at me.

On most evenings the prefects in the house made sure we were all tucked up by lights out. However on Saturday evening, the prefects could stay out until midnight and Johnson would come around and see that we were all present and correct. So at 10.30 I deliberately started having a shower, knowing that Johnson would come in and tell me to go to bed. I was risking a week of early morning wake-up duties, but I figured that when he saw the show I would put on for him he might kind of forget about punishments.

I was in the shower for ages as it took him a while to come up to my floor. I guess he was talking to someone on the ground floor for a while about something. So it was actually close to 11 o’clock by the time he came into the shower room and said, “Who’s in there?” I was quite relieved to hear him as the water was by this stage getting cold and I was turning into a prune. I got out of the shower cubicle, reached for my towel, but instead of wrapping it around me, I dried my hair with it. My cock was quite well developed for a boy of 14 and it was semi-erect (but not overtly so) in anticipation of my exhibition.

He said, “Why are you showering so late Wallace?” I jumped as if I hadn’t realised he was there and then said “Oh I was talking to my mother on the phone and I lost track of time”. I dried my hair, letting the rest of my body stay wet, and made no effort to hide my cock from his gaze. I didn’t really want to make it obvious that I was looking at him to see how much he was looking at me, but I was aware that he was really eyeing me up. I waited to be told I was in trouble, but he just stood there looking at me.

I started drying my chest. At 14 I played a lot of basketball and was well toned. I was also (and still am) blond, and have quite an attractive, albeit slightly angular, face. In fact, I must have made quite a pretty sight to any guy looking at me getting dried. So it wasn’t totally weird of Johnson to linger in the doorway to get a look at me. What he did next, though, proved that he was enjoying the view more than a regular straight guy would.

He asked me about the school basketball team. This was totally unlike Johnson as he wasn’t really interested in sports of any kind. But he asked me and kept asking me questions about the sport to give himself an excuse to stand and watch me. I kept talking to him, drying my armpits, around my cock, turning my bum towards him as I dried that, then bending over to dry my feet. In fact, as I did that, his voice started to waiver in mid-question. I really got between each toe, pointing my anus up towards him. Then I turned around again, started drying my back and let him get a really good look at my cock. By this stage it was quite heavy, not giving the game away by standing up, but looking as thick and long as it could while staying limp. Maybe it stood out a little from my ball sac, I don’t know, but he really stared at it, nestling in my blond pubic hair.

I noticed he had his hand in the pocket of his jogging pants. He wasn’t playing with himself – that would have been a bit too overt for Johnson – but he cupped his crotch, probably to hide the hardon that was developing within.

When I’d finished answering his latest bullshit question, I turned to the urinal and started peeing. This was unplanned but I needed to go and wanted to give him another look at my butt. He started another question and it kind of tailed off. I said, “Pardon, Sir?” and he started it again. Then I scratched my ass, right in the crack around my hole, and he lost the thread again. I guess he wanted to see me take a piss because he came right into the room, saying he needed to check that the windows were properly closed. He walked up to the window and I took my time shaking my cock and then made masturbatory movements with it as if squeezing every last drop of piss out of it. Again he stared but by now he was past even attempting to ask me a question. Pulling my foreskin right back at the urinal, I looked up at him. He was staring at my cock and then, realising I was looking at him, looked away and said “Well you’d better get straight to bed”. He visibly pulled himself together, took a deep breath and shook his head, and looked at the steamed up window. He took his hand out of his pocket to go through with his pretend check of the window, and I saw that his jogging pants were tenting outwards in the area of his cock. Proof at last!!

Then he put his hand back in his pocket and left the room. Strange thing was that he didn’t check the rest of the house – he went straight back to his own quarters. Wonder why!!?


Part 3

I was kind of fascinated by all this and when I was masturbating I found my thoughts returning to what might happen if I tried to seduce him in private. Within a couple of weeks I’d gone from fanticising about us having a wank together to imagining myself being bent over his desk being fucked by him. All this from a guy who claims to be straight! I wasn’t as fucked up about it as you might think – I just kind of accepted that having a crush on an older authority was just something most guys go through. Of course, I didn’t mention it to any of my mates.

Anyway, I decided to go to his office with a spurious problem which would enable me to show him my cock again. This time we’d be in a place where it was unlikely that we’d be caught (his wife usually took their daughter over to her mother’s or something when he was on duty in the boarding house) and I could see how far he’d be prepared to go. I don’t know what I wanted to happen – I was just curious, I guess.

I went into Johnson’s study and told him that I wanted to talk to him about something important. He was behind his desk, at his computer, and he told me to come in and sit down on the sofa. He came over and sat on one of the armchairs near it. He said, “What’s the problem, Wallace?”

I said, “Well, it’s kind of embarrassing, but I don’t know who else I can tell.” He nodded. I continued, “Erm… when I, er, masturbate it… well it really hurts.” He shifted in his seat and I thought he might be too embarrassed for me to continue. After about ten seconds he said, “Where does it hurt?” I said, “On the back of my cock. Um, I mean, on the back of my penis”. He said, “You can call it your cock. Sounds less, er, scientific”. He was clearly feeling quite uncomfortable by this and I was wondering whether it had been such a good idea.

I went on, “I’m worried that maybe I’m not doing it right. I’ve asked a few of the other guys, in a round about way, you know, but I haven’t been able to find out what I’m doing wrong.” He started to look less freaked out and more interested. Again I continued, “I enjoy it – it’s not like agony or anything. It’s just – well, sometimes it bleeds”.

He said, “Well that’s not right. Thanks for having the guts to talk to me, Sebastian”. Now he looked more relaxed and actually smiled. He probably thought it would make him look as if he was cool with all this. He said, “Maybe I should make an appointment for you to see Dr Craddock”. I nodded and said, “If you think so, Sir. I was kind of hoping it wouldn’t be such a big deal, though. I’d feel really embarrassed talking to some old guy about this”.

He nodded and smiled. He went on, “Well, it’s probably just a matter of using lubrication.” I looked deliberately dumb. He said, “Does your, er, cock feel dry when you masturbate?” I said, “How do you mean?” “Well, do you have to spit on it?” I decided I couldn’t play the innocent for too long or he’d suspect I was setting him up. So I said, “Oh you mean precum? I produce a bit, I guess, but it does feel a bit dry”. I spoke openly by now hoping this would help him relax. It seemed to be working.

He considered, then said abstractly, as if still thinking, “Well, since you’re not circumcised…” I looked at him. Clearly he’d remembered my cock from seeing it in the showers a couple of weeks earlier. He looked a bit startled when he realised his mistake. He added, “… are you?” To make it look as if I hadn’t noticed I looked away and said casually, “No it’s not the foreskin. It’s that bit kind of under the head – well, it’s hard to describe.”

He didn’t know what to say this. He looked a bit scared but at the same time he was breathing quite quickly. Maybe he was intrigued by the discussion: I wasn’t fully sure. As he was sitting down I couldn’t tell if he was hardening up. After a few seconds he said, “Well, if you’re too embarrassed to talk to the doctor…” He left his sentence annoyingly incomplete. I thought I should say something so I said, “Well it’s a matter of feeling comfortable with someone, Sir.” He seemed to like hearing that. Again, however, he wouldn’t say anything and we sat for a few seconds in silence.

Eventually he said, “Well, if you want to show me…” This is what I’d been waiting for. My original plan had been to see if he would say that and then back off if he did. However, I was now feeling quite excited by the idea of wanking in front of him and seeing his response. So I said, again trying to sound casual, “Yeah, okay.”

I stood up and he looked away. Maybe he was wondering about the consequences of being caught: he definitely looked as if some serious stuff was going through his mind. I loosened my belt, unzipped my fly and pulled down my black school trousers to the top of my thighs. I had my Joe Boxer briefs on, and I noticed that I was filling the front of them quite nicely. He looked at my underwear with a fairly neutral expression.

I pulled down the front of my underwear, tucking the waistband beneath my ball sac. This made it look bigger than it was: my balls really stuck out. My semi-hard cock was raised slightly above my scrotum at an angle of about 45 degrees. The pink head and piss slit were visible as the foreskin was slightly pulled back. Again I was pleased with how I looked. My cock was about 6 inches long and looked really good with my blond pubic hair above it. My cock and balls were framed by the white front of my school shirt: the flaps of the shirt were lying on either side of it, with the lowest button being fastened just above the protruding bush of my pubic hair.

Johnson stared at it. He said, in a shaky voice, “So where does it hurt, Wallace?” I moved my hand onto my cock, brushing my tie to one side when the end of it got in the way, and pulled back the foreskin. I said, “Well, it only hurts when it’s hard. I’ll just get it a bit harder.” I made slow jerking movements, pulling my foreskin up and down over the head. It really felt good to do it in front of him: I could feel it getting longer in my hand.

He got up suddenly and I stopped. He said, “I, er, better lock the door. It would be a bit embarrassing for us both if…” He locked the door and came back over, this time sitting on the edge of his armchair with his face closer to my cock. I continued wanking. My cock was by now about eight inches long – it’s full length. I deliberately stopped and took my hand off it, moving slightly so he could see it from the side. I liked looking at it like this myself – it looked quite long for a guy of fourteen.

He kept staring and I started masturbating again. Eventually I said, “Yeah it’s hurting now – under the head.” I pulled my cock upwards and held it at the base, the head pressing into my shirt. He looked at its underside, red and sore-looking where the foreskin joined the shaft of the cock. “Yeah, I can see where the problem is”. He was actually looking at the natural redness of my dick: I wasn’t having any problems at all.

He asked, “Does it hurt when you touch it there?” “Where?” He reached forward and gently rubbed the underside of my cock, his finger making long loops from the bell end down the shaft. “Yeah, a bit,” I replied. “But it’s not really painful.”

“Maybe you’re not holding right when you, er, play with it. Let’s see you do it again.” I moved it further towards his face. My bell-end was now just inches from his nose. I slowly pulled my foreskin up and down. He stared at it, breathing slowly, never taking his eyes from my long erection as I masturbated. “I think it’s your thumb – it’s irritating the back of your foreskin,” he said. I told him that I’d always done it like that. “Since when?” “I dunno, about three years”.

He said, “If you don’t mind, I’ll show you a better way.” I took my hand off my cock and it sprung upwards, even nearer to his face.” He stood up and told me to turn around. Standing behind me, he put his hand around my cock, thumb on the top and fingers underneath. Then he started jerking my cock, really squeezing it as he pulled the foreskin back and forth. It felt really good. He was much faster than I had been and he squeezed so hard that the bell went a deep purple colour. He said, “Is that any better?” I gasped, “I dunno…”

He kept masturbating me. After about thirty seconds he said, “How does it feel?” “Good,” I said, breathlessly. He stopped and told me to turn around again. I was disappointed that he’d stopped, and then even more disappointed when he sat down again. My cock stood out, white marks on it where his tight fingers had been. He stared up at me and then smiled. He said, “You weren’t meant to enjoy it that much”. Feeling a bit embarrassed, I said, “Sorry Sir” Then I added, “But you were very good.” Now he looked a bit pissed off and looked away. Then he turned back to me and said, “Well, you have a try like that and see if it feels better.”

By now, though, I thought I’d gone a bit too far – my intentions seemed obvious, although the truth was that I didn’t really know what I had intended. Pulling my underpants back over my cock and balls, I told him that I’d try it later. “I’ll keep my thumb on the top from now on.” He stood up, looking a bit troubled. Maybe he wanted this to continue but knew that it couldn’t without becoming something potentially very serious. He said, “Well let me know how it goes…” But I guess even that seemed dangerous to him, so he smiled and corrected himself: “No, I guess I’d rather we don’t mention it again if your problem has been solved” I thanked him, being deliberately formal, and then left the room.

I often jerk off, even now, thinking of what might have happened. I think he was close to going further with me – I’m sure he really wanted to. I’m glad I did it, though – at the time I regretted it a bit, especially over the next few days when I had to be around him – and I wish I’d cum all over his coffee table and carpet while he was jerking me off.


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