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More fantasies about Alan

More fantasies about Alan

Alan and I used to play chess occasionally. Whilst I always rated myself smarter than him, he usually beat me at first. It took me a long time and a lot of effort to even things up a bit.

However, always on the lookout for new ways of engineering a bit of action I came up with the idea of 'strip chess'. My wanking fantasies were always that really - thoughts about how I might engineer some sex action with Alan. I spent quite a lot of time thinking through how this might proceed.

So how in my fantasy world would we actually embark on a game of strip chess? Well it would usually start with us challenging each other to a game. 'Do you reckon you could beat me now?' Alan would ask. 'Yes. You're due a blow to your ego'. 'Well how much do you rate your chances? A pound to the winner? A fiver?'. 'No chance, I've lost enough to you already.' 'Come on you've got to make it interesting for me. What will you risk Chris? How about a forfeit?' 'OK what?' I'd ask suspiciously. 'Well you know you played strip poker with those girls from school. How about whenever you lose a piece you remove an item of clothing?' 'Go on then, seems harmless', I'd stupidly reply.

Pretty soon I'd find myself minus quite a few items of clothing as well as some pawns and him maybe losing just a jumper. 'Check!' he'd declare with a wicked glint in his eye. By then I'm already down to shirt, and underpants. I'd remove my shirt and then prepare to take my move. I take his knight checking my king, so off come Alan's trousers. Naturally he'd foreseen this and my bishop is taken by a pawn. 'I've only got my pants left. I'm not taking them off,' I declare. 'Come on. Off. Stick to the rules.' Eventually my pants come off and I'm stark naked. Because I'm a bit cold my own personal 'bishop' is not showing signs of excitement (I'm relieved to think. I don't want him thinking I'm that way inclined). My back to the wall (metaphorically speaking) my brain clicks into gear and I start to even things up a bit and Alan I successive turns strips off his shirt, then his jeans. 'Is that a gun or are you pleased to see me,' I joke. He really does look like he's getting pleased and that starts me off. I try to hide it by keeping my legs crossed!

A few more turns and I'm in check again. We hadn't planned for this in the rules. What happens once someone has lost all their clothes? 'You have to do another forfeit', Alan declares. 'What?' I enquire with a tone of dread. 'Go and stand at the window.' 'No chance!' "or something else then. You do something for me.' "Err, what?' I reply. My protagonist pauses before saying, 'Well, this is just as a punishment for you for being bad at this, not because it's what I want, but you've got to touch my cock because I know you won't like it.' Seeing I didn't immediately object (I said nothing because I was taken aback) Alan continued, for ten seconds you've got to hold it. And move your hand up and down.' More excited than I want to admit, I made a play of refusal. 'You really mean it don't you.' 'Yes. Come on. Get on with it. Get it over with. It'll teach you to play chess better. You're always asking me for advice on how to improve. This will give you the motivation!', Alan suggests. I gingerly approach him and checking to make sure it isn't a joke, I slip my hand down the waistband of his pants and feel his cock. He's got a semi on. I wrap my fingers round his shaft. It's thinner than mine, as I'd noticed before in the changing rooms. 'Ten strokes. And not too fast. I'll count out seconds.' And I begin to wank his cock. Ten slow strokes. He's not just got a semi on by the end. And I respond too. My cock grows and by the finish I'm sporting a good hard on. Back to the game!

I don't think this has helped my concentration, and I'm not sure it's helped my motivation to do better, and I make an error and I'm in check again. 'Ten more strokes!' OK ten more strokes'. I'm eying the bulge in Alan's pants as I approach him. My hand goes down the waistband. "oh pull them down a bit. There's more room'. I obey. His full erection is on display. The tip of his glans is peaking out of the foreskin. I reach round his shaft and start ten more strokes. The downstrokes reveal more and more of his knob. It looks inviting. 'Did he notice me staring at it?' I wonder. I think he did. Back to the game. 'I think you want to lose, don't you!' he taunts as I lose a piece defending my king, and Alan nods to my erection. I'm a bit quicker to start the ten strokes this time. And ten doesn't seem enough to me, but 'better not seem too keen' I try to fool myself.

A couple of turns later and I seize the opportunity to turn the tables. 'Check!' 'Was that too easy?' I ask myself. 'Or is he getting distracted?' Alan doesn't need much encouragement to grasp my penis, and count out the regulation ten strokes in ten seconds. By now I'm fit to burst and he looks it too. Must return to the game. We're only doing this as a punishment for making mistakes! We're not enjoying it. It's just a reaction to a physical stimulus! I think that's how we would rationalise that. Then.

Pretty soon I realise Alan's mistake was a deliberate. It was part of a strategem. No k**ding! I was set up. He's arranged the position for him to manoeuvre me into a trap. Check. Ten strokes. Check again. Ten more! Then 'Check mate!' 'OK what do we do now?' I ask. 'Well I finished you off so now you finish me off!' And that's how I end up with him spurting spunk over my right hand, chest and chin.

'Play again? Best of three?' Alan asks. 'Yes!!"

'This time when you lose a piece the other person gets to remove your item of clothing' I proffer. This ups the ante a bit. It's quite exciting having someone else unstrap your belt, pull it off, unbutton your waistband and slide your jeans down to you ankles. The first time he's got me in check in the next game, Alan suggest upping the forfeit in someway. 'I know,' I say bending my head down to his crotch. I lick up his shaft, from balls to tip, on the outside of his pants. I put Alan in check a few turns later. I'm already pantless and he licks my flesh directly. I think we're both enjoying this. Next time, he's lost a pawn and his pants when he gets me in check. I pull his foreskin back and lick around the glans. A couple more moves and Alan has lost another piece. We're both naked. Both erect. 'What next? I've nothing left to take off.' I point Alan to my cock and suggest he licks my knob.

The game is losing all semblance of a struggle of wits. We're losing pieces and getting in check left, right and centre. Pretty soon it's stalemate. At least we think so. We don't bother to examine it too closely. The only proper forfeit for stalemate is a 69. We both seem to instinctively know this and without saying anything we're both on the floor, top to tail, sucking and gobbling. It takes only a minute before we're gushing into each other's mouths.

'Play again?' I ask. 'Yes. Let's have a drink and a rest first though!'

The third (and final?) game ends with victory for Alan. Two orgasms down, he takes longer to cum. I don't mind. i'm happy gobbling away. After Alan finally shoots, he lays there with a satisfied glow. The cheeks on his pale skinned face are flushed. 'Best of five?' I offer.
Published by chrisffn099
6 years ago
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chrisffn099
chrisffn099 Publisher 5 years ago
Thanks leerjammer66. There were quite a few more fantasies like that!
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Ailsa_TV
Ailsa_TV 5 years ago
to chrisffn099 : I've been meaning to do that for ages, never seem to find the time but if I do I'll let you know. Thanks again for reviving that memory.
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dirtyoldbiman
to Ailsa_TV : Alisa, rather like your version of the game better. Chris's idea is a good way to get it started. "tasty" story
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chrisffn099
chrisffn099 Publisher 5 years ago
to Ailsa_TV : Thanks Ailsa. I'd love to hear (read?) about your fantasy involving the older guy you mentioned.
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Ailsa_TV
Ailsa_TV 5 years ago
A great read !
My first job after school was in an office where an older guy took a wee fancy to me. Everyone knew he was gay. I just didn’t see any attraction there at all so avoided any situations where things could have developed and he was never a pushy type let alone touchy feely even when we went out in the car together sometimes on business. A few years down the line my fantasies about him were growing and before long they always brought on my best orgasm. Anyway, I tried many times to put a strip chess one together but it never quite worked so I usually just skipped to the bit where I took his cock in my mouth and sucked until he came :smile:
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chrisffn099
chrisffn099 Publisher 6 years ago
to Lingerieboy71 : Me neither. It was all in my head unfortunately.
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Lingerieboy71
Lingerieboy71 6 years ago
I was in the chess club at school, and I don't recall anything like this happening..!
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