We all know there are straight boys out there who think about cock. Usually they have acted on their impulses at some time in the past – a fumbled jerk off with a friend in high school or experimenting with a mate while drunk. Many of the ‘straight’ boys I play with are attempting to recreate or relive a previous experience they have fond memories of – blowing a mate in a tent on school camp or watching porn with a friend until something mutual occurred. I love playing with inexperienced guys but it’s rare to find a guy in his mid twenties with practically no experience. Normally by that age they have at least done something timid and experimental.
Michael was one of the exceptions. I started talking with him on Craig’s List. He was 26, married, two young kids, and had never touched another cock before. However, it was clearly something he had been thinking about for sometime. We had agreed to meet up a few weeks before but at the last minute he cancelled. When we made a new time I wasn’t entirely convinced that he would turn up. He could have been one of those straight boys who love the idea of cock but for whom the reality of a pre-cumming cock head waving in front of them waiting to be serviced is a bit much to swallow.
As it turned out, not only did he turn up but on the night asked if he could come earlier than the scheduled time. He found my apartment building and I buzzed him up.
He wasn’t what I expected. He was better. Some ‘straight’ boys who come to play put on a macho front – just to make it clear that while there are there to suck cock, it doesn’t mean they are gay or anything. What I found was an adorable guy, a little under six foot, with an impish grin, small well kept beard who was a little stocky but with a good shape. In other words, a total DILF. He was a tradey, and how he held himself reflected that – with the slight swagger that tradey guys seem to learn during their apprenticeship.
He admitted he was nervous, which I found incredibly endearing. There’s nothing more boring than a “she’ll be right, mate” attitude to sex. It should be passionate, scary, exciting and thrilling.
We talked and I found out that while he had never sucked cock, or even touched one, he had recently been blown by a guy – and liked it. But he wanted to go further.
I offered to show him some porn and asked him what he wanted to see. He said he loved amateur so I showed him some of the stuff that I had filmed myself. I got him a bottle of cider (1.6 standard drinks – the perfect amount to relax him) and I talked about the various guys he was watching on the screen. Twenty minutes later, drinks finished, he was more relaxed and it was time for me to make the first move.
I pulled him to his feet and started to undress him. His boxer briefs weren’t yet revealing a hard cock but as I ran my hands over his chest and teased his balls through the fabric, a very respectable bulge started to grow as his horniness took over from his nervousness.
He was cut – and I took some time to show him how to play with my uncut cock. He watched fascinated as he pulled my foreskin up and down over my cock head. My cock is thick and I think he was genuinely impressed with this new toy to play with.
I stripped him naked and he did the same to me. His chest was almost entirely smooth with milky white skin. After overcoming that traditional moment of awkwardness when you have to get the pants past your ankles without falling over, we stood chest to chest with our hard cocks in each other’s hands.
I sat down on the couch and guided him down onto his knees so his face was right next to my cock – right up close and personal. He played with it as he studied every inch (and there are quite a few of those) before he gave it a tentative lick and took it into his mouth.
When teaching boys how to suck cock for the first time, or offering refresher lessons for those who are just awful at it, I’ve found it useful to break it down into four stages.
The first is how to treat the cock and balls. The various techniques and games. Learning how to lick the head, run your tongue round the rim, gently chew the foreskin, nibble the shaft, get their balls wet with saliva and gently blow on them to cool them and then apply your hot, wet mouth to warm them again. Lots of fun stuff.
The second lesson is what to do with your hands. Tease the balls, tickle their butt, hold the base of the shaft tight to push the blood to the head you are sucking, run fingers down the inside of their legs, and other techniques to really turn someone on.
The third is variety, learning to move from one technique to the other. A cock can get bored with repetitive actions. Think of a cock as an eighteen year old with attention deficit disorder. It gets bored easily. Mix it up. Go from cock to balls to shaft to head to foreskin and back again.
Fourth is pacing. This is what turns a good cock sucker into a great one. Anyone can master changing between styles – they key is to vary the tempo so it looks like there has been a lot more variety. The first time you lick someone’s balls do it slowly and sensually – long licks that warm them. Go onto other things – when you come back to it, lick them like a thirsty puppy with rapid flicks of the tongue (putting a collar on the boy can help with this). Changing the pace and tempo adds the wow factor and avoids looking like you are going between actions or following a script. It adds unpredictability and passion.
He was a very good student. Within twenty minutes he was sucking cock better than seventy percent of the guys I’ve ever had down there. We moved to the bedroom and after he graduated from cock sucking school I started to reciprocate. His first 69. First time time having someone do back to him what was being done to him.
I started tickling his balls with my fingers and made my way towards his ass. Teasing under his balls, then finding his tight hole with my fingers.
While he was sucking more precum out of my cock I positioned him so I could spread his cheeks and inspect his ass hole.
His ass was pink and tight. It looked newer and tighter than most teenagers. Only a light fuzz of hair around it. When I teased it with my fingers it only puckered tighter. This was one fucking adorable cherry hole that I wanted to pop. But first I had to teach him to relax his throat. I rolled him onto his back and positioned him so his head was hanging over the bed – at the perfect height and angle to slide my cock into his mouth and down his throat.
Throat fucking is an art form but even giving it a go can be intense. I supported his head and neck with both hands as I slowly pushed my cock into his throat. Initially when he gagged I pulled out immediately. We did it a few times – the amount of time before he gagged very slowly increasing. I then told him to take it for as long as he could before he tapped my leg and I slid it out again. Having a straight boy gag on your cock is pretty damn good – throat spasms plus cock equals awesome.
By the end he had learned to keep his throat open for a few seconds before gagging – and then tolerate the gagging for about three seconds. Not the best record but he now knows how it feels – and understands the gag reaction he has to overcome. Even a few seconds of deep throat with a cock as thick as mine is an achievement.
He lay in bed leaking precum and watched as I pulled the sling out from under the bed and quickly attached it to the hooks bolted into the roof. I pulled him off the bed and we stood chest to chest with our hard cocks threatening to skewer each other. I think he liked the fact I was taller than him. I positioned him at the base of the sling and he lay back into it. I pushed his feet through the stirrups until his ankles were supported by the two inch wide leather straps. He instinctively put his hands over his head – in a classic submissive pose but it was so natural I’m sure it was unconscious. I moved between his legs and mashed my crotch into his ass that was now at the perfect height. It is normally at this point that boys understand the power of the sling and exactly how well they can get fucked.
I put a towel on the floor and positioned my stool so his ass was at my eye level. I laid out my tools and began to work his butt. After gloving up, I began with a single finger – and located his prostate. He was a bit unsure about the intense feelings. I moved onto more and more fingers – moving slowly and carefully but stretching all the time knowing his inexperienced ass might not have the stamina for a longer session. I asked him how many fingers were up his butt – and he was genuinely surprised and a bit amazed when I told him I had all five up there – only to the first knuckle but not bad for a beginner.
I moved onto my diamond shaped stainless steel probe. “cold” was his initial reaction when I pushed it against his virgin ass. The probe starts small and gets to about the size if a twenty cent piece before narrowing again. The sensation is one of pressure increasing and increasing before passing the widest point and it pops into your ass. I went slowly but he gasped as it pushed through and ended up in his ass. Pulling it out is the same sensation. After it had been slowly pushed in and out a few times he realised what all boys realise – if it’s already been in and it fits and it didnt cause massive pain, then I should just lie here and enjoy it. When this happens the boy begins to relax – his ass stops clamping down and he learns that keeping your ass open is more pleasurable. When he learns this – learns to stay relaxed – the fun can really begin. The next toy was a silicone one with five pink balls in a row. While larger than the stainless steel it feels warmer and fleshlike and it rapidly disappeared into his ass. When I started fucking with the balls I knew he was loose enough to get fucked and probably enjoy it.
I rolled down a condom and drizzled lube on his ass. I rubbed my cock up and down his crack a few time – partly to tease him and partly to make sure it was slick with lube. I found his hole, slowly applied pressure and gradually, inch by inch, I popped his cherry. He took it really well. From the look on his face it was a mixture of pleasure and pain. When it was all the way in, I held it there before beginning tiny strokes.
When fucking I like to change angles – so the boy doesnt get used to it too quickly. We quickly worked out that he didn’t like being fucked in a position that pounds his prostate. I suspect in time he will grow to love that but for the moment the sensations were too overwhelming. I changed tempo a number of times, his ass relaxed more and he started to enjoy the sensations more and more. I power fucked him a few times for five seconds just to show him what it felt like – and he shuddered as I counted down from five to zero as I fucked him hard.
After about fifteen minutes, we switched from the sling to the bed. I positioned him on hands and knees on the edge of the bed, so I could stand and rub my cock up and down his crack. I applied more lube and slid in. I think he really appreciated in that moment how easy it is to get fucked in a sling. His ass tensed up and he winced as my thick cock ended up balls deep in his ass. I tried a few experimental strokes but I was hitting his prostate on every stroke. For most boys this is a good thing – and it’s something I pride myself on being able to do. But for this beginner I needed to tone it down a bit. I had him lower his chest to the bed, all the way down so his nipples were on the sheet. In this position his prostate wasn’t getting as much abuse and he was able to take it.
I flipped him onto his back and took him missionary but it also caused some intense sensations. He had already been fucked for longer than most guys – so I put him back in the sling for the finale.
His body was in a bit of shock from his first fuck and he was having difficulty staying hard. He was a bit confused by that but I reassured him that it was pretty common the first time. I slid into his ass again and held my cock perfectly still while he started to jerk off. My hands massaged his cock and balls as he overcame the punishment of his ass to once again be hard and dripping precum. As he got closer I started moving in and out and as his orgasm started to crest I pounded the fuck out of him.
He blew a load any porn star would have been proud of. A truly massive load over his stomach and chest. Impressive for height, number of shots and quantity. I kept pounding as he blew, and even for a few seconds after he finished – before slowly pulling my cock out of his ass.
He lay there while I fetched a towel to clean him up.
I helped him out of the sling and to his feet. I started stroking myself and asked him to play with my balls. He had amazing technique – gently stroking down each time, putting just enough pressure on them. Brushing the inside of my legs. Getting me quickly to the point I could blow and holding me there. I was at that point where I couldn’t tell anymore if I wasn’t blowing my load because I didn’t want to due to the incredible pleasure or because the overload of pleasure was inhibiting my ability to push myself over the edge. I blew a big load and he recoiled slightly as it shot onto his arm and stomach.
We showered together – lots of massage and shower gel.
I hope he enjoyed his first time as much as I enjoyed giving it to him – and I hope he becomes a regular. And there is lots more to teach him. Threeways. Fourways. If he was gay you’ll call him a fit cub – and I know at least three other cubs who would want him to sample their porridge and end up sleeping in their bed. Who needs Goldilocks?
After the session I emailed him:
“Wow – for a first time that was amazing. You are already a better cock sucker than 70% of the boys who have ever blown me. Seriously well done. :)”
And this was his response…
“Why thank you and a huge thankyou for guiding me through it so well.
I had a great time. And I’ll send the pics over the weekend”
Oh, that’s one thing I left out of the story. At every stage of our session I took photos with his iPhone. My cock in his mouth, my cock in his ass, even some short video clips of him demonstrating his new found cock sucking abilities. Hot. He emailed some through – unfortunately but understandably without his face. Enjoy. Check out the cum – that’s all his! His prostate didn’t know what hit it!