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Upstairs at Jeff’s

Category: Gay Male
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I surf the web quite a bit. I particularly enjoy reading stories about guys (gay and straight) who find themselves exploring their m2m needs/curiosities, especially when it’s a first time experience. I get pretty horny reading the stories. I’ve handled two other cocks in my life so far and each was a very different type of experience, but here’s the story (true) of my first introduction to other guy’s cocks. If you like it, and/or want to hear more, and/or want to know more (about the story or me), let me know.

It all started in the late 70s while I was at high school in the US. My best friend at the time, Joe, had two brothers – one younger and one older (Jeff). I was always over at Joe’s house watching TV, playing video games or football or whatever; and it included the odd wank or blow-job. Not on my own, or with Joe or my other friends, but with his brother Jeff.

It all started one day after swimming at the local pool during summer hols. We’d been playing ‘sardines’: one guy or girl in the middle of the diving pool and everyone else on one side. You all swim from one side to the other and back, and anyone tagged has to stay in the middle of the pool, and tag everyone else until you end up with one untagged winner. We always used the diving pool coz you could swim along the bottom (about 12 feet) to avoid getting tagged.

I digress. Anyway, Jeff was in the middle for this particular game of sardines and when everyone dived in, I went straight to the bottom and started swimming across, but as usual Jeff tagged me first, right on my tightly Speedo’d ass, but this time it was more of a grab than a tag. I used to get pissed off that he always picked on me; but I soon came to realise why.

When we got home from swimming, still with our Speedo’s on (Joe’s folks were out; both his parents worked) Jeff disappeared up stairs saying something about a shower, while the rest of us (me, Joe, his younger brother Lee, and Steve and John) got some drinks and went into the basement to play cards and cool off (it was 97F outside).

Jeff was always acting like the aloof older brother. He was in the local college football team, he was good friends with most of the local girls, but he was also a little geeky. He always made an effort to talk to me and whenever we would have wrestling contests, Jeff would always join in and being much bigger than the rest of us he would always end up winning by pinning one of the young guys to the floor (usually me).

After a while, and with it being such a great day out, the guys decided to go biking in the woods, and then go to Steve’s house. Everyone needed to go home to get their bikes and we arranged to meet up at a particular spot in the woods where there was a rope swing and you could swing out over the creek and jump into the water. Everyone went out the basement door, but I headed up stairs to grab my stuff.

The house was one of those 3 floor types: bedrooms up stairs, main rooms at ground level and some rooms in the basement, which with the sloping landscape actually became the ground floor at the back. Anyway, I shouted up to Jeff to say we were going out and did he want to come.

He shouted down ‘Where ya’ goin?’

‘The rope swing.’

‘Ok, I’ll catch you up.’

‘Cool, but the guys have already gone and we’re then going to Steve’s so you’ll have to hurry if you’re going to catch us at the swing.’

‘Everyone’s gone?’

‘Yeah.’ I replied.

After a slight pause Jeff said, ‘Well before you go why don’t you come check this out?’

‘Check what out?’

‘Come and see. You’ll like it.’

Curiosity got the better of me. ‘Ok’, and I grabbed my stuff (towel, shorts and t-shirt) which I had dumped by the front door on my way in and I headed up the stairs.

I arrived at his room knocked on the closed door (Jeff’s folks had this rule that if anyone had their bedroom door shut, you had to knock and wait to be allowed in; it was their ‘that’s your private space and we won’t invade it’ thing, so the room’s were always a mess). He said ‘Come on in’. So in I went, still wearing just my tight blue Speedos. Jeff was sitting on the bed naked except for a towel.

‘What ya doin?’ I asked.

‘Looking at some magazines’. He looked at me, top to bottom, and said ‘Do you want to go join the others or would you rather look at some mags?’

‘What sort?’ I asked, getting excited at the thought that it may be some of Jeff’s legendary porn collection.

‘I’ve got a Penthouse. Here have a look.’ He reached under his bed and produced a pristine copy of a Penthouse.

I could hardly contain myself ‘Wow, where do you get this?’ I said as he handed it to me. I stared gleefully at the front cover.

‘Still want to go meet up with the guys?’

‘Have you got anymore?’ I stammered.

‘A couple.’

The woman on the magazine cover was stunning: tall, long smooth legs and blonde hair, wearing a black bra (the balconette kind, which I have always loved), black sussy and stockings, and a black g-string. Oh to die for! I was beginning to feel a stirring in my Speedos. ‘Can I borrow this?’ I asked hopefully; wanting to take it, head straight for the bathroom and have a quick wank.

‘No way! I’m not having you splatter cum all over my magazine!’

‘Oh please Jeff!’ I pleaded. ‘I promise I won’t mess it up, I just want to have a …. proper look.’

‘Go on then. But you have to look at it here.’


‘I tell you what: you look at that one and I’ll look at this one.’ He reached under his bed and produced another magazine: a Playboy. ‘Sit down and get stuck in.’

What the hell, I thought. So I did. I sat at the bottom of his bed, with the Penthouse on my lap and started reading (or looking, to be factually correct).

After what seemed like ages, but was probably only a minute or two, Jeff seemed to become restless, and he moved up his bed so that he was sitting on his pillow with his back against the wall. I looked at him and noticed the marquee that his towel had become. I was putting my own Speedos through a stretch test, and trying desperately to hide it, but Jeff didn’t seem to care that I could see his hard-on. After about another minute, Jeff said ‘I, um, need to do something about my boner. Do you mind?’

‘No.’ I replied, not really thinking about what was going to happen.

Jeff pulled his towel off, threw it on the floor and then lay down on the bed. His cock was longish (well only about 6 in, but that seemed long to me at the time), and quite fat (as you’ll find out later I could only just get my hand round it), and it had an enormous dark purple head that looked fit to explode, and no foreskin (which meant nothing to me at the time).

He was looking straight at me as he grabbed his cock and started fisting himself, slowly at first, then a few quick strokes, then slowly again. I couldn’t stop looking at him: his legs, his arms, his chest, his face, and his hand, and what he was doing! My eyes settled on his cock and his fist. He closed his eyes for a moment and when they reopened, they were rigidly focused on my Speedos. I was sitting side on to him, watching him over my left shoulder, and he couldn’t help but see my boner.

He broke the silence, making me jump, ‘Listen, you’re obviously seriously horny too. I can tell. If you were any more horny those Speedos would burst. Why don’t you take them off; it’ll be more comfortable. And hey I’m already naked, no-ones around; they won’t be back for a couple of hours, so no-one will know. It’ll be our secret.’

I was scared and excited. A secret with Jeff. Wow, here I was doing really grown up stuff with Joe’s older a brother, who’s on the football team, who has access to lots of porn and knows loads of shit and stuff. And he wants to spend time with me! Great! But I wasn’t sure about taking off the Speedos.

‘Come on. Look, you see my dick? Yeah. It’s kind of neat isn’t it? What’s different about my dick from yours? You’re probably a bit smaller, but you jerk off don’t you. (It wasn’t a question.) What’s the problem: two guys sharing porn and jerking off. It’s no different than if you were on your own. But, well, I can, you know, show you stuff, make you better at it, teach you how to make it feel really good.’

And with that he sat up, crossed his legs, and reached out to me. He took my hand and pulled me up the bed toward him. ‘Stand up, on the bed.’ I did so, not really sure why I was doing it. He undid the tie at the front of my swim suit, lifted the top over my hard-on and pulled them down to my knees. I remember looking straight ahead at a poster on Jeff’s wall of the rock band Kiss and thinking ‘guys wearing make up in thigh high boots’. I guess at that moment I decided to go with the flow.

Jeff gently rubbed my legs (which were hairless at that age) and then my stomach, all the time staring at my dick. He then said ‘Sit down’ which I did, and he pulled the Speedos over my ankles and threw them on the floor. ‘Lie down’ which I did. All this time I hadn’t said a word. He sat cross legged beside me and started gently caressing my stomach, my chest, my nipples (which went rock hard), my neck, my face. He bent down and kissed my neck, then my chest and then licked my nipples. My cock was like steel and I just closed my eyes and went with the flow.

I felt his hand touch my leg, then move to my thigh and round to the inside of my leg. Then onto my other leg, but this time carried on until his fingers traced over my cock, which jumped about 2 inches at the touch. He laughed, ‘You like it then.’

‘Yes.’ I whispered.

‘Then you’ll really like this.’ And he grabbed my cock with his hand and started to gently wank it. I was in heaven; God it felt good. To be lying there, hands by my side with someone else doing the work. The feel of a hot firm hand working my cock rhythmically up and down. I crossed my hands behind my head and sighed.

‘See. I told you I could make you feel good.’ It didn’t dawn on me at the time, (but it does now) that the way he said it, so softly, yet firmly, was so reassuring that I just gave in. I started to squirm and he started to pump faster, and I warned him that I thought I was going might cum. What he then did just killed me. I felt something wet touch the eye of my cock, and as I opened my eyes and looked, I realised it was his tongue. He was licking my cock; just the head, shoving his tongue into the slit, and then tracing it around the head. That did it. I wasn’t thinking about Miss July anymore; all I could think about was how beautiful this wank was and how beautiful Jeff was for doing it. I could feel my balls tightening.

I wanted to scream, but instead muffled a shout through gritted teeth ‘I’m gonnnaa cummm…’ Jeff quickly moved up onto his knees and leant over me and began to wank my cock really hard and fast. My cock was aimed straight up at him, and as I came it felt like I was shooting a bullet through my cock, I hit him right in the chest with first shot, the next one landed on his wrist, and the rest on my stomach and his hand. Oh Jesus was that incredible! Jeff continued to gently wank me until my dick went completely limp. The wet slippery feel of his hand on my subsiding and cum covered cock was amazing. When he finally removed his hand, I relaxed and it was only then that I realised my entire body had been tensed: my legs thrust out as straight as they could go, my knees locked, my butt squeezed as tight as it would go, my stomach muscles cramped, my hands were in fists behind my head and my jaw ached. I sagged onto the bed and just lay there with my eyes closed. I remember wishing that that precise moment would never end!

When I opened my eyes, Jeff was just kneeling there looking at me, smiling. His cum soaked hand resting on my stomach just above my pubes. ‘See.’ he said. And I did.

I couldn’t take my eyes off him as he lifted his hand from me, brought his wrist up to his face and looked at it for a moment. And then he licked the cum off his wrist. ‘Mmm, nice cum.’ He closed his eyes and smiled. It looked like he was rolling the stuff round in his mouth. Then he swallowed. I couldn’t believe my eyes. Were you supposed to swallow it? I didn’t think so. But then he looked down at his chest and the cum that was slowly running down from the spot where it had hit him. He proceeded to scoop it up with his fingers and licked it into his mouth. ‘Tastes nice.’ He said looking at me, then at my cock, then back at me. He then licked his entire hand clean. After which he said ‘Want to try some. It tastes really good!’

I just nodded my head from side to side. He leaned toward me and said ‘Go on, just a little bit. Tell you what; I’ll just put a drop on your lips.’ Before I could say anything, he leant toward my head. I thought he was going to kiss me and I turned away, but he just stayed there, his head about 6 inches from mine, until I looked back at him. Then he said ‘Trust me, ok.’ And brought his lips toward mine. His tongue came out and he just licked my lips, and then he sat back upright. I didn’t know what to do, but I guess a natural reaction kicked in because without thinking I licked my lips and sucked them into my mouth – as you do when you have something wet on your lips. I recall the strange texture, and the taste: that slightly bitter, salty taste, but mainly I remember a hint of lemon. It was okay, but the idea of cum in my mouth did gross me out a bit. I think I screwed my face up at the thought, coz Jeff laughed.

Without so much as a pause, he then said ‘Hey, do you want to do me?’

But all I had was images of having to lick his cum and I didn’t fancy it. ‘Not really.’ was all I could say.

‘Ok. Maybe next time. For now just watch.’

And he lay down beside me and began to jerk himself off. It only took a minute before he tensed and as he rolled his head to look me straight in the eyes, I saw a glob of cum shoot out of his cock and land on his stomach, followed by another and another and another. It went on for ages. Finally he relaxed and his hand dropped away from his cock. He looked up at the ceiling and closed his eyes.

At which point all I could think about was the slow slippery wet wank that Jeff had given me after I had cum, so, I reached out and grabbed his subsiding cock and began to slowly wank it. With my hand wrapped round his semi-flaccid cock, the tips of my thumb and forefinger only just touched each other, and I must’ve gripped too tightly because he jumped a bit and said ‘Gently. I get really sensitive afterward.’ So I relaxed my grip and slowly wanked him for about a minute until he got really soft and it all got a bit floppy and uncoordinated. At which point I just started playing with the head, enjoying the slippery feel of it; rubbing the bit under his cock head between my thumb and forefinger. Jeff moaned and said ‘God that feels good. You’ve got really soft hands.’ It slipped out my grasp a couple of times, and on the third occasion Jeff laughed and said ‘Enough already! We’ve got loads of time for that.’

But we didn’t because the front door slammed. It was Joe: ‘Hey Jeff, you here? Have you seen Mickey? We’ve been waiting for him before we head off to the rope swing. You gonna come too?’

‘Oh yeah!’ Jeff shouted back, while he looked at me with a devilish grin, but he then added ‘Mickey’s up here. We were just looking at some stuff.’ Oh shit! I jumped off the bed, grabbed my Speedos and put them on as fast as I could. I could here Joe coming up the stairs!

‘Shit’ I blurted out, as I turned to see Joe playing with his cock. ‘He’ll fucking see us. Put something on!’ I hissed.

‘Don’t panic’ he said as he dropped his cock, jumped off the bed and put on some shorts as he shouted ‘Grab me a Coke from the fridge will ya, we’ll be down in a sec’. The footsteps stopped, and then started again, heading downstairs. ‘Don’t worry about it, it’s cool. Remember though: not a word. Otherwise I’m dead, and so are you! It’s our secret. Pact?’

‘Pact.’ I replied.

Jeff shoved the magazine’s back under his bed and headed out of the room, grabbing a t-shirt on he way out. I just stood there, slightly shell shocked. What had just happened? What had I done? What was I feeling? I liked girls! Okay I’d only ever kissed one girl, but I definitely liked girls! But oh shit what Jeff had done had felt soooo good! And I wanted to do it again!

I sat down on the bed, and picked up my shorts to put them on. As I leant back to pull my shorts up, I leaned on back on the pillow and heard something rustle. I thought ‘another magazine!’, so I reached under the pillow and, yup another magazine, so I pulled it out. But holy shit! It had two naked guys on the front. I opened it and flicked some pages. More naked guys. I turned another page and there was a picture of a young guy naked and tied to a chair (obviously staged), with an older guy standing in front of him, with his dick in the younger guys mouth! I turned some more pages and there was a shot of the same young guy still tied to the chair, with cum on his face and around his lips. The older bloke was standing just in front of him holding his huge cock. It dawned – he’s just cum on the guy’s face! I turned to the next page and the guys cock was back in the young guy’s mouth! Oh shit! My cock twitched; this was horny!

Just then Jeff shouted ‘Come on! Hurry up!’ I quickly shoved the magazine back under the pillow, pulled up my shorts and put on my t-shirt and raced downstairs to find Joe already outside, and Jeff waiting by the front door with a bottle of Mountain Dew, which he handed to me: ‘Thought you might want to wet those lips.’

As Jeff opened the door, he let his hand hang as I walked past, and it brushed against my leg. It was like an electric shock, and I sort of twitched/jumped in response; and then ran across the lawn to where the guys were waiting with their bikes, while Jeff locked the door. Joe had already been to my house to get my bike, and as I grabbed the handlebars from him he asked what we’d been doing. I just looked back at Jeff, not knowing what to say. I couldn’t think of anything apart from ‘your brother’s just jerked me off and swallowed my cum!’

Jeff quickly (and very calmly) said ‘You know those mags I’ve got, well Mickey wanted a good look at them, and so I let him … for a small fee.’ He then looked at me, winked and said ‘You owe me big time!’

Joe looked astonished: ‘You lucky bastard. He never lets us look at them.’ And with that we all jumped on our bikes and headed off into the woods.

I felt great and pretty smug with my new experience. Between the house and the rope swing, I decided I was definitely straight, but I could handle some more sessions with Jeff!

Stay tuned for the next instalment with Jeff.

[I’m now married with kids, living in England, and while I love my life as it is, I still reminisce about being upstairs at Jeffs.]

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ian wrote

Love your story I’m always turned on by teen and early sex stories reminds me of when my older brother me discover wanking and blowjobs I got to love him!!!!!!!