I've had an intense fetish for loose shorts for a very long time. Most guys I know who are into shorts at all, like them tight. From a purely visual turn-on point of view, I agree completely - a nice pair of thighs disappearing into a pair of short, tight shorts is cock-hardeningly sexy, and bulges and buns can look great in them - but for sheer horny vulnerability, I much prefer them loose. Very often, a victim can feel more 'naked' wearing just a pair of loose shorts, than if he's wearing nothing at all. Having experienced this myself many times in the past, I can tell you why: if he's naked, he accepts that his cock, balls, perineum, inner thighs and arse are exposed and accessible - but with shorts on, there is a (largely unconscious) feeling that this area is somehow protected. There is cotton - or silk, leather, PVC, rubber, denim or whatever - covering his most sensitive and private places - and if that protection is intentionally and slowly violated, the effect can be very intense indeed...
Tez loved everything about soccer – especially the kit. And it was the usual story: he was straight, he had a girlfriend, their sex was good, but couldn’t even think of telling her about his fetish. He said his best orgasms were when he was on his own – when he put his footie kit on, played with his cock for a while through the shorts, then pulled them down and wanked himself off. He said he thought he would like a session – he’d always fantasised about being tied up – but he must be wearing the kit all the time, and he didn’t want sex of any kind: he didn’t want another guy even to touch his cock.
I thought there may be potential here, and that it would be fun to educate him. Laughing wickedly and twirling a metaphorical moustache, I agreed.
I’d got him spread-eagled between the vertical posts and for the last two hours I’d been stroking, teasing and tickling his slim body all over – except for the area covered by his yellow and black shorts. That area I had very carefully not touched at all.
His cock had been rock-hard since very soon after I’d fastened the last restraint; it was stuck out horizontally inside his shorts. I looked at the clock – two hours so far. I sat down in the chair and gave him a rest for five minutes and then, starting at his wrists, I worked my way as slowly as I possibly could along his arms, across his shoulders, and down his upper body, stroking and teasing with light fingertips. When I got to the waistband of his shorts I stopped, and began at his feet, working my way up equally slowly as far as the legs of his shorts. I paid particular attention to his legs, especially the insides of them, above his knees.
Occasionally I stroked my hands down his shorts on the outsides of his thighs, and moved the shorts about a little, so he could really feel them.
I’d been systematically working on the boy’s body for about two and a half hours now, and he knew that the area under his shorts was off-limits. Those shorts were his protection, and I’d been very carefully reinforcing that idea since I’d first got Tez restrained.
I’d been teasing my fingertips slowly up the insides of his thighs from his knees repeatedly, stopping each time I got to the leg of his shorts. This time, however, I didn’t stop. He had specified that I wasn’t to touch his cock. However, he had said nothing about his balls...
He gasped urgently as my fingers slid slowly under the leg into his no-go zone, and continued up the increasingly sensitive skin towards his crotch. I thought he was about to object – and I’m sure he started to – but in the end all he did was begin to shake his head.
Very, very slowly I tickled upwards to the very top of his thigh – my fingertips were millimetres from his balls – stroking the hairless skin lightly, teasingly. Having got to the top I turned my hand slightly and tickled the balls themselves.
He began to moan loudly and his head-shaking became more violent. I knew exactly what he was feeling: an intense sense of invasion. The shorts that had been his protection were no longer a barrier to my hands – and not only that, but the fact that these sensitive parts hadn’t been so much as touched for the last few hours had made them super-sensitive and super-erogenous. This was a straight boy – and he felt like he was being raped. I carefully didn’t touch his cock, but confined my fingertips to the insides of his thighs, and his balls.
Just as slowly, my hand began its downward journey. I repeated this sequence first on one leg, then on the other, and then both together – sometimes up the insides of his thighs, sometimes the outsides, fronts or backs. He was fighting a battle in his mind: he was a straight boy and there was a gay guy with his hands up his shorts – that was unthinkable – but at the same time he was as horny as fuck and desperately needed to cum.
Gradually I increased the speed until my hands were disappearing up the legs of his shorts quickly, tickling his balls for a moment, then coming out again. I did it from in front of him, from behind him, and from the side with one hand going up the front and the other between his thighs from the back. Constant, repeated invasion. He was moaning all the time now, and also struggling. His straight-boy reflexes were forcing him to try to close his legs together, to try to get away from my invading hands – but he couldn’t. His cock had been leaking pre-cum for a long time now.
I stopped, and let him rest for a few moments.
So far the boy had had nothing over his eyes, but now I took a leather bag hood and, ignoring his protests and struggling, quickly dropped it over his head. I tightened the neck strap so that the shiny leather clung to his face when he breathed in. I knew that would intensify everything – especially his feeling of being helpless, of being raped. I knelt on the floor behind him, lubed a rubber glove, pulled it onto my right hand and counted to five. Then I suddenly forced my hand up the leg of his shorts between his thighs, enclosed his cock with my smooth, slippery rubber-gloved fingers, and milked it hard and fast.
His body convulsed. He yelled into the hood and the restraints creaked alarmingly as he strained to clamp his thighs together, and I felt his cock bucking madly in my fingers as he came. My rubber-gloved fingers slipped and slid over his cock head as his spunk pumped out helplessly into the smooth, shiny black rubber and dripped down onto the floor between his legs.
That was the start of a long and frequent series of visits from him. He accused me of ruining his sex life with his girl – nothing, he said, came close to the orgasms he had while he was being raped in his shorts.
So sue me, I said.
Shorts did nothing for Geoff, in fact he didn't like them - said he 'hadn't got the legs for them', and that they didn't turn him on at all. I suppose Geoff was the nearest thing I've had to a regular 'slave' - apart from Jamie, who is mentioned in the 'Tickling' section later - (I'm not really into the Master/Slave thing), in that I was the only guy he was seeing (or wanted to), and he needed me to control his sex life as much as possible. An important part of this control was my decision about when he could - or could not - cum. I always made him cum at the end of a session, but expressly forbade him to cum by any means while he was not with me. I know he obeyed me in this and never wanked himself off at home, because it was so important to him that he was under my control in this respect.
He used to come around to my house in Birmingham a couple of times a week, and he called me 'Sir' (in spite of my telling him it wasn't necessary). Being ex-army, he used to wear combats, and he was into many of the 'usual' SM activities: CP, TT, and the like. Now personally I've never really got off on these, but he was a very sexy guy, and he enjoyed them so much that I took pleasure in indulging him. Also, one of his biggest turn-ons was to be tied up tightly in something restrictive, hooded, and left alone for periods of time. This was fine for me as it gave me a chance to get on with other things :)
So - an average session with Geoff would consist of putting him into some tight restraint, leaving him for a while, then getting him out, beating his arse, torturing his tits or his balls, possibly a bit of electro - and then finally putting him back into some kind of bondage, and jacking him off. Being very into shorts myself, I'd tried playing with him in various kinds of shorts at one time or another, but his cock would go soft and he'd lose interest. So one day I decided to conduct an experiment.
We were sitting in the living room one evening before a session - at least I was sitting, he - not being permitted to use the furniture - was on the floor by my booted feet. I produced a pair of white nylon running shorts and handed them to him. "Look after those well, Geoff - because from today on, the only time you are going to cum is in those shorts."
He made a face, and said that he didn't like shorts.
I smiled. "You will, Geoff, you will".
He hadn't been round to see me for three days, and of course he hadn't cum since last time I'd brought him off, so I knew very well that he was extremely horny. I took him upstairs, strapped him into his leather sleepsack (which he kept at my house) with his cock and balls sticking out; hooded him; put headphones with soft white noise in them over his ears; and comfortably suspended him horizontally from bungees. This was one of his favourite positions of all, and he loved the sensory deprivation. We didn't do it very often, as it took a lot of time and effort to set up, but on this occasion it was ideal for what I had in mind. In the past, the longest time I'd left him there like that was about an hour (he got so horny that he needed to cum badly by then) - but this time I left him for three hours, looking in on him frequently to check he was all right. By the end of the second hour he was so horny that he couldn't keep still, and begged me to jack him off there and then. I said, "later, Geoff," and left him again.
When I'd got him down, I spent the next couple of hours doing all the things to him which I knew turned him on most of all. I beat his arse - starting gently and building it up to a level beyond which he'd been able to take before; I put clamps on his nipples, then later took them off and tortured his tits as the blood returned to them, when they are at their most sensitive; I attached electrodes to the cheeks of his arse and to his balls and sent pulsating waves of electricity through them while I made him lick my boots and leather jeans - and all the time while I was doing these things to him I played with his cock: gripping it gently and sliding my rubber-gloved fingers lightly over the shaft and sensitive cock-head. But intentionally, I did not allow him to cum. From the moment I'd put him into the sleepsack until the end of the session, he had a constant, raging hard-on.
Eventually, I told him to get dressed, and that that was it for tonight. He looked at me as if I was out of my mind and asked me if I'd make him cum. I smiled and shook my head. "No," I said. "I want you here at 2.30 tomorrow afternoon (it was Saturday), prepared for a long session. If you're good I might make you cum then."
He pleaded and begged (he was having difficulty keeping his hands off his horny - and still hard - cock), but I was determined.
We went downstairs again, and I picked the shorts up off the floor and handed them to him. "Here - I want you to wear these, and nothing else, in bed tonight. You don't like shorts, so they should help you to get some sleep." I went with him to the door. "Oh, and wear a cock ring as well." I knew that cock rings turned him on.
The next afternoon he arrived with a hard-on in his cammos, and said that he hadn't got much sleep at all. I took him upstairs, and did an almost exact repeat of the previous night's session, except that it was longer, more inventive, and more intense. I even used nettles on the cheeks of his arse and the rim of his arsehole.
It was late evening by the time I finished getting him ready for what I wanted to do, and by that time he was beside himself with the need to cum. I had sadistically teased his cock almost continuously since I'd taken him out of the sleepsack all those hours ago, and it had been necessary to keep his hands restrained to stop him from making himself cum when I was moving him from one piece of equipment to another.
I handed him the shorts and ordered him to put them on. He grimaced and said that he'd much rather be naked if I was going to make him cum. "You have a choice:" I replied, "either I make you cum in those shorts or you don't cum today." We both knew that his next visit wouldn't be until Tuesday - another three days. He put them on.
Geoff has a 30" waist, and these shorts were 32", so they were quite loose on him. I nodded approvingly at how he looked, and then made him lie down on the examination table. I cuffed his wrists to the top, beyond his head, and strapped his ankles into stirrups to keep them elevated and wide apart. Once his lower legs were strapped into them, he was unable to close his knees together at all. Three leather straps pulled tightly over his body made it impossible for him to move very far in any direction, and a green canvas ex-army hood made sure he would be concentrating fully on what I was doing to him. Sitting down at his left-hand side, I smiled at the sight of this helpless, horny guy, his hard, precum-dripping cock tenting the loose nylon of his shorts out into a bulge that was simply begging to be gripped firmly and jacked off.
I knew that Geoff was still unbelievably horny - that much was clear from the fact that he was wearing shorts and yet his cock was still as solid as steel - and that his need to cum was just about the only thing he was capable of thinking about; and so, to prolong and intensify the poor boy's suffering, I began to work on him very slowly indeed. With my right hand I began to trace the shape of his rigid cock through the thin nylon - drawing small circles and lines with my fingernails. I avoided the cock-head for the moment. Every time I moved my fingers, his cock involuntarily jerked inside the shorts, and moans of both pleasure and extreme frustration came from beneath the hood.
I kept that up for a while, just tickling and teasing his cock shaft, and then progressed to the sensitive, and thus far untouched, head itself. The first time my fingertip touched it - even through the nylon - he moaned in anguish and begged me to let him cum. Ignoring him, I continued to tickle and tease him, my fingers merely brushing the outline of the engorged head through the precum-wetted white shorts.
I put my other hand slowly up the leg of the shorts, my fingertips teasing the inside of his thigh as they went, and then onto his balls. I began to tickle them.
I was getting seriously turned on doing this, and needed very badly an orgasm myself. When I couldn’t stand it any more, I decided to make him cum. I gripped his cock head between a finger and thumb through the thin shorts, and began to milk him slowly. My other hand grabbed his balls below the cock ring and pulled them gently. The combined stimulus was, as I'd known it would be, too much for him, and - with an animal roar - he started to cum. My fingers began to slide over his cock head as his spunk shot out into the shorts.
His body thrashed under the leather straps, and both of my hands were covered in hot spunk as it erupted faster than the shorts could soak it up, and ran down the inside surfaces and onto his balls.
When he was finished, and his cock had stopped bucking around inside his shorts, I got my own cock out of my leather jeans and shot over his chest.
When he took the shorts off afterwards, they were soaked with spunk all down the front and the left-hand side.
That was the first session with the shorts. Thereafter, every single time I made Geoff cum, it was into them. Sometimes it was slow and frustrating, other times I'd just grab his balls and his cock through the thin nylon and pump it hard and fast until he came. He kept them at home, and was permitted to put them on whenever he wished - but he was absolutely forbidden to wash them - and, over the months, they got stiffer and spunkier.
I gave them a name - the 'Milking Shorts' - and eventually all I had to do was to say to Geoff "put the Milking Shorts on, boy," and his cock would instantly spring to full, rock-hard erection. My experiment had succeeded: he’d developed an intense fetish for those shorts.
A postscript: I lost track of Geoff when I moved up here to Huddersfield, but then about a year ago I got a phone call from him - he'd got my number from a mutual friend. Since the Birmingham days he's got married and had two kids. But he said he's still got the Milking Shorts, and to this day the best orgasms he has are when he's wanking himself off into them.
Ah, the power of the mind :)
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