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Punch Fucking An 18yo Surfer Boy

I’m going to try and put into words the session I had last night. Even as I commence to write I know the chances of capturing the intensity of the session in a blog post is an impossible task. Which is kind of disheartening. It was quite simply one of the hottest sessions I’ve ever done and I wish I could do it justice.

I think I’ve described Riley, the hot eighteen year old beach boy before. He’s physically perfect. What makes it even better is that he is a really nice guy as well.

He’s a very sexual person. He’s taken the time to stretch his teenage hole so that getting fucked is pure pleasure for him. This involved him siting on a bowling pin for years until he was finally able to slide it into him.

The first time we played he had come so close to taking a fist that I thought that it was pretty likely that in his next session we would pop his fist cherry so I was really looking forward to playing again.

When he arrived just after lunch we chatted for a while, and then I showed him some of the previous sessions I had done. I showed him a session I had done with Mitch, a hot nineteen year old that he had been talking to online but never met. Also an amazing punch fuck video I filmed with a hot early twenties guy. It’s often hard to find good fisting porn with young guys and I think he appreciated directorial my efforts. We also looked at some of my favorite commercial fisting videos – including one of Amerifist from Studfist working the hole of a hot French boy whose eyes roll back in his head with pleasure as he gets punched.

As we watched my computer screen he kept on taking off more and more clothes. Being a regular beach boy he only really feels comfortable when totally naked. It’s totally endearing – and very hot.

By the time we were ready to start playing he was wearing nothing but his jocks and socks. His hard cock looks absolutely perfect in his boxer briefs. It sticks straight up – aiming perfectly for his belly button. It’s an awesome cock – good sized, tapered head.  And so rigid you could engrave things with it.

I quickly popped the blindfold on him, pulled him to his feet and started running my hands over his body. His perfectly tanned skin became covered in goosebumps as I teased his skin. I like to play with boys after I blindfold them – it establishes trust and also establishes that I’m in control. It gives them time to relax and adopt a peaceful, submissive mindset.

With such an amazing body to play with I probably amused myself for longer than was strictly necessary to reassure him. His body is like a work of art – worthy of close inspection and extended contemplation. I didn’t want to stop exploring it with my hands, and occasionally my tounge.

I removed his underwear and amused myself by teasing his cock, balls and ass, before running my tounge from the base of his spine up to the base of his neck. Because I’m ludicrioudly tall I was able to get him in a head lock while resting my chin on the top of his head. My cock was straining against my underwear as I ground it against his ass while reaching around to tease his cock.

 
I wrapped his arms around my neck, reached under his legs and lifted him into the air. He clung to me as my fingers delved into his crack and teased his tight hole. I’m sure that anyone else exploring his butt with their tounge or fingers would have assumed that it was a normal tight teen butt – but I knew from previous experience it would quickly open up.
 
I considered carrying him to the sling, he is certainly light enough and I’m definitely strong enough, but thought better of it given the detritus covering the floor in preparation for the session.

 
I gently guided him to the bedroom. He sucessfully navigated the miriyad of obstacles, including boxes of toys, cables for the lights and cameras and other things in order to end up on my bed.

On my last trip to New York I bought a harness that holds the boy’s arms securely to his side. He looked amazing in it – his perfectly tanned skin contrasting with the black leather strap across his stomach and around his thighs, wrists and elbows.

Once he was helpless it was time for the real fun to begin. Lots more touching of his cock, balls and every other square inch of his body….before the nipple play started. A range of nipple clips on his sensitive, small, twink nipples.

It was then time to take things up a notch. I’m pretty sure he worked out from the sound of the cigarette lighter that he was about to experience wax. The wax dripped over his nipples, first onto the nipple clips and then after they were removed, just on the nipples themselves. The wax then wandered across his balls.

To give him something to distract from the sensations I rested a dildo next to each of his legs near his hands so he could fondle them while lying helpless. He had the massive toy Victor in his left hand and Black Ball in the right. He gripped them with his fingers as the wax rained down.

I then got out my electro wand, and the violet wand wandered all over his body. He loved it on his nipples, but he really loved it on his balls and cock. His cock was leaking pretty freely by this point and I bent down to lick up his clear, sweet, teenage precum.


It was so satisfying to hear his moans. The wax and electro elicited some pretty awesome moans – especially when the glowing electrostatic rod was applied directly to his ass.
 
He was under strong lights but in the shadow between his legs I could watch the sparks jump from the end of the glowing orange tube directly onto his hole. He loved the electricity flowing onto his hole and everywhere up to his balls. The sparks look awesome – accompanied by the sound of buzzing voltage and the smell of ozone being created. 

Trying to combine different sensations became my game. Applying electro to his balls while I sucked his cock. Kissing him while I tweaked his nipples. Working his ass while massaged the top of head. We played for ages and I loved every second of it.

It was time to get him into the sling. I started slowly, working his ass with my fingers. I had decided to use Crisco for this session. His hot teen ass opened up beautifully for my hands in the black latex gloves. He was in a hood, but without a blindfold, so he could watch the screen of the video camera mounted overhead capturing my domination of his ass. The video is so fucking cute – he looks like he looking right into your eyes as I work his hole – but he is actually watching the video screen pointed towards him.

 
The overhead camera was attached to a special stand that positions it right above the bed. A second camera was level with his ass with a light attached to capture every move. 

He took a variety of toys and his ass just kept getting looser and looser. He took the toy Bam with ease. He took Blackball with a little difficulty but soon loosened up. I decided to try Victor – a fucking massive toy.

He had to really work for this one. His ass stretched around the toy approaching the edge of the massive head. For about five minutes his ass ring was stretched around the toy just before the ridge. Finally, and with a slow push, the toy stretched his ass and it popped in. His first instinct was to ask me to take it out, but I convince him to leave it there…which he did.

 
He was really stretched wide. Wider than he had ever been. His teen ring was resting past the massive head of the toy. The feeling must have been incredible as I twisted the toy and teased his ring with my fingers. Finally I gripped the toy and firmly pulled. There was an audible pop as his surfer boy ring stretched over the head and the toy slid out. 

When he took Victor I was pretty confident that he would be able to take my fist. It wasn’t very long before it was time to try. I slowly pushed my hand into his ass. The hand reached the widest point and while the pressure increased, it was very clear that it was going to happen. My hand slid into his ass and locked into place with only the slightest resistance.

I loved his reaction – it was something that he had been working towards for ages. I kept it in for a few minutes before gently withdrawing it, and a few minutes later easing it back in.

Beach boy has been talking with the same interstate teen that I’ve been teasing and we decided to snap some photos and send them to him. It was pretty awesome to be able to show someone that we had popped the fist cherry.

I asked our teenage remote viewer for his thoughts on that night:

Once again Andrew face timed me and was having a session with Beach Boy who is a hot fucker! At first he teased me by showing off Beach Boy’s body in the sling and then slowly went down to his cock and ass hole, he hung up then teased me with pictures of Beach Boy putting a thumbs up and smiling, so hot! Then we face timed again, Andrew slowly fingered Beach Boy’s hole, then I think Beach Boy grabbed the phone and started mucking around – seeing his cute smile through that hood made me so hard, Andrew hung up and proceeded to send me pictures, thanks to both of them I shot a massive load 😉 It looked so easy when Andrew’s fist slid in, like not a struggle at all, made me extra horny knowing one day I’ll have that fist up me  😉 Beach Boy loved it as well which made me that much hornier he was so relaxed!

I thought that would be it for the session, but it turned out we were just beginning.

His ass just kept relaxing…and his ass got looser and looser. It was just such a fun session – the ethos was clearly one of pleasure. It definitely didnt have a “take it bitch” kind of vibe. It was fun and playful – in a teacher/student kind of way.

I had actually told him before we started that once you can take a fist it’s actually pretty easy to get to punch fucking – once you know you can take it you can relax and just let it happen.

Exploring his ass it was clear that he was having more problem with depth than width, so after his ass relaxed even more, I formed a closed fist and eased it into his ass. This blew me away – to be able to take a closed fist his first time was pretty extraordinary.

The amazing thing was that as soon as I started using a closed fist his ass relaxed even more. By not going deep his ass seemed to suck my hand inside even faster…and I was able to push my closed fist in and out of his teen ass.

Holy Fuckballs Batman!

I’m actually punch fucking an eighteen year old surfy boy – the first time he has taken a fist!

We decided to continue with him on his hands and knees. His ass looked amazing pointing up in the air.  Normally I only want to rim boys when I know they’re totally clean – but I had to restrain myself from burying my face in his gaping, Crisco covered teen boy hole.  He was just so fucking hot.

He was able to take my fist even more easily on all fours, or all fives as he once mistakenly referred to it (his cock is well above average, but doesn’t actually qualify as a limb).

At one point I pulled my fist out of his ass, and he turned to me, and practically leaped into my arms, pushed his body against my mine and bear hugged me as he thanked me for the experience. It was incredibly moving and the only thing that prevented it from being a totally perfect moment was that I had to hug him carefully to avoid getting my Crisco covered gloves over his body. I’m so glad it was as special for him as it was for me.

Back on all fours, every time I pushed his ass to take it further, it responded. He was taking an incredible pounding. I’ve fisted boys who have been fisting for years and they’ve never gotten as relaxed as this tanned teen was managing his first time.

After punch fucking him with my left hand, I switched to my right hand. His ass actually responded better to my right hand, and his moans became more intense and his ass loosened up even further.

By now I thought I was really pushing my luck.  It takes extraordinary skill for a bottom to be able to take alternate punch fucks from different hands. Because each hand feels different it can be difficult to relax. But I decided it was worth a try.  I started very slowly. One hand slowly in and slowly out, before the other takes its place.

But as his ass loosened up even further, I was able to very slowly increase the pace.

This culminated in me counting as the fists were inserted and removed, and got faster and faster….

I originally was going to give him twenty punch fucks, but he passed that with ease and so I aimed for fifty. It wasn’t a challenge so I picked up the pace, when I hit eighty punches I was doing more than punch a second and he was moaning more than ever. I loved it when he got vocal which encouraged me to abuse his ass even faster….until I reached a hundred. I continued past that but stopped counting so I could enjoy the experience.

Finally it was time to finish and I counted down the final ten punches.

After some recovery time we headed to the lounge room to watch back the session. During the session he was so focused on his ass he went soft. He reassured me he was having a great time. However, watching his own young ass get abused on the screen caused him to bone up to rock hard.

Heading back to the bedroom I lay on my back on the bed and he stood over me, as I pushed my hand up into his ass. We tried it with him pushing his hands up onto the roof, and him squatting down making out with me while my fist twisted around in his butt.

It was an extraordinary experience. It was such a privilege to take his fist cherry. And I’m still in awe of his ability to relax and take it. I like to think that part of the reason the session went so well is that he trusted me and knew I would do everything possible to make it an awesome experience.

About twenty minutes after beach boy left Sissyboy messaged me. He was at a nearby restaurant with his Mistress and was wondering if I was busy.  This was about seven thirty. It was then I realised that I hadn’t actually left the house all day. Beach boy had arrived at one pm and left at seven – six hours of play.

I dressed and met Sissyboy and his Mistress and we had a lovely dinner. His Mistress is gorgeous (well, for a girl), with a bright bubbly personality. An incredibly attractive person. I can well see why Sissyboy is so devoted to her – and rightfully so. Good thing he likes cock so can keep playing with him. 🙂

I described my incredible afternoon and they described theirs.  Sissyboy was glowing. I had seen on fetlife that his Mistress was taking him to a CBT workshop given by a Mistress. Sissyboy was unexpectedly used to demonstrate some of the techniques.

Apparently the highlight was when he was helpless with his balls tied and he was having then whipped while happy birthday was sung to him.
“Happy birthday to you…”
Swoosh….WHACK
“Happy birthday to you…”
Swoosh….WHACK
“Happy birthday dear Sissyboy…”
Swoosh….WHACK
“Happy birthday to you.”
Swoosh….WHACK

Sissyboy’s face glowed as he described the session. Apparently there were only three guys and seventeen girls at the session. Which is great – we need more girls into kink as you can’t expect me to fuck all the straight boys myself – it’s exhausting.  😉

I headed home to clean up my apartment, and Mitch asked if he could drop by when he finished work. We hung out while I used various alcohol soaked wipes to remove Crisco from my cameras and tripods.  You need a lot of them to get it all off. He returned some gear that he had borrowed from me. He had a rough day so we decided to hang out in bed – lots of snuggling, spooning and nuzzling while we talked.

He was telling me about a night quite recently when he stayed over at his mate’s house and ended up in the spa with his mate’s 28 year old older brother.  His mate was making out with his girlfriend so they were being left alone. The brother then let his hands wander under water…

After lots of underwater play Mitch decided to not continue – until he discovered he was expected to share a bedroom with the brother. Mitch valiantly resisted for as long as he could – and then went for it. I wish I could have seen it. Mitch is a hung teen who really knows how to fuck. I imagine that the older brother thought that he might have gotten a bit of fun with a younger guy – never imagining that he was probably in for one hell of a pounding.

We started talking about ways he could tactfully let his best mate know that he had fucked his older brother. The ideas got more and more inappropriate. For example:

“Your brother is a size queen.” “How do you know that?” “Because he loved my massive cock in his ass”

“Your brother really loves you – when I was ploughing his ass he kept screaming your name”.

That last one cracked us up for a few minutes – ah, inappropriate humour. Love it.

I messaged beach boy this morning and we did the following interview for my soxster.com readers:

Congratulations on taking your first fist. How long has this been a goal of yours?
Uuhm since i was 17 
Did you watch much fisting porn? Do you remember what your initial reaction to it was?
Yeah i did , my initial reaction to it was wholly fuck how loose is that guy 
And you wanted to be like that yourself?
Not at first 
I thought it was a bit too extreme, but over the space of about 3 months i came around to the idea as a learn more about it
Have you always enjoyed putting things up your ass?
Yes
I started with a pen ( i don’t think i ever told you that) 
We all have to start somewhere. And you went from there until you reached the now infamous bowling pin. Did all that ass play make it easier to get fucked?
Yes defiantly because my ass getting used i could get past the pain stage of getting fucked faster and just skip straight to enjoying it
🙂
Some boys take years to get past that stage – and yet you got to the point where you could go to an orgy with hot energetic boys under 22 and get fucked by eight of them and still want more. Good memories?
Yeah awesome memories 
So we first played some time ago and your ass was so close to taking a fist. I remember thinking that you were SO close when your ass had enough. A less honourable master would have just pushed it in. What training did you do between that first session we did and last night?
I got a proper dildo and some times used it 4 out of 7 days a week 
and also lots of sex 
Can’t forget that
Hehe…how much sex? You were just finishing high school when we first played and now you’re at uni – more opportunities?
I dunno i stopped counting and hells yeah more opportunities
There is good research that the more education you have, the more sex you have over your life. Do you have any messages for any high school guys? Perhaps Study Hard, get into uni and Stay Hard?
yeah its defiantly worth going to uni or collage the lifestyle is great and you get so much more sex 🙂
Well that’s a good community service announcement. So at what point yesterday did you know it was going to happen? That today was the day?
Probably when i took that big ass black dildo of yours with the massive head
That’s Victor – how did that feel when it locked into place? That’s a fucking huge toy.
I felt full and stretched such a weird feeling 
but most of all it felt awesome 
Did the Crisco help?
Yes i don’t think it would have gone in so easy if we didn’t use it 
So when my hand slid into your ass could you feel it lock into place?
Yeah it was amazing but it also felt weird cause it was a totally new experience for  
It does feel weird because someone has just PUT A HAND INSIDE YOU! It’s a real trust exercise and the feelings are intense. Normally that’s it for a first session – but your ass just kept on relaxing and opening up.  Did you expect that?
Nope i thought i would only just be able to take the fist 
So did I – but obviously it felt good because we continued. How would you describe the feeling to someone who is used to having big toys in their hole but who has never taken a fist?
It’s very different in my opinion the fist can move on its own and change its shape hole still in the your hole its a mind-blowing experience something that big toy just cant match
(don’t get me wrong i luuuuuuve big toys 😛 ) 
So did it feel better than you expected?
Yes it was out of this world when i got punched fuck by you 100 times I’ve never had so much pleasure in my life
So fisting beginners is definitely a team exercise – we quickly worked out that you could take the fist being pushed in and out. In fact a closed fist actually worked better for you as your ass is pretty shallow at the moment. So before I started punch fucking you, what did it feel like as my hand was going in and out slowly?
I could feel every inch of your fist as it slid in and every inch was pleasure and pain(in a good way) combined 
Now your ass was cooperating amazingly well – and I started fisting you faster and faster until I was punch fucking you. What do you say to people who don’t believe it’s possible for a newbie to be punch fucked their first time?
Tell them its bullshit and send them to you 😛
Haha…so am I good at this?
Yes Sir you are pro 
What can I say? I like to give to the community and help young people. 😉  We switched from the sling to you on all fours – was that much easier for you?
Yeah it was a world of difference for me it seemed to go in much quicker 
You looked so fucking cute with your amazing ass up in the air. I punch fucked you for a while with my left hand and then alternated between left and right. How did that feel? Does each hand feel different? 
Yeah one of the hands went in easier then the other but the difference felt good when you picked up the pace of the fisting 🙂
And I really picked up the pace – that was some of the fastest punching I’ve done – how did it make you feel?
Well i went to what my friend calls nirvana it was so amazing i can’t even explain it look up nirvana its the best description i can think of
Pure pleasure and almost ceasing to exist? Out of body experience?
Pretty much
Before we played we watched a video of Amerifist playing with a young French guy – when the boy is being fisted his eyes rolled back and he is in total ecstasy – do you know now what he was feeling?
And I presume you want to feel it again? 
I think i do yeah 🙂 
and fuck yes i do 
Have you ever been double fucked? Two cocks in your ass at the same time? 
No not really 
I want to try it 
I’ve sucked 2 cocks at once
well it was 3 
You were soft for quite a bit of the session – which isn’t uncommon for fisting. Did that worry you? You had to reassure me you were having a good time, didn’t you?
Nup didn’t worry me just thought it might worry you i was totally concentrating on my ass i didn’t need my dick lol
Having a hard cock is one way of telling your fister that you are having a good time. If you aren’t hard then you just need to stay vocal and reassure him you are liking it.  😉
I’m sure that as you get used to it you will get hard during some fisting sessions
And blowing a load with a hand in your butt I’m sure you will find mind blowing
I’m used to having to be quiet so the other boys mum or my mum for that matter doesn’t hear me:P
But you already know that 😛
We pretty much tried every position: on your back in the sling, on all fours, on your back in the bed, you lowering yourself onto my arm, you standing….I think you liked all fours the best?
Yup all fours is definantly my position of choice for fisting at the moment but i like normal fucking in missionary 
You like to watch your top when he pounds you or you like to make out?
Make out, plus it is hot seeing another teenage boys face when they cum 
I’ve always thought so 😉
So it looks like we are catching up on Sunday along with another teen who likes to be fisted. Have you ever fisted anyone before?
Nope ive used multiple fingers 
Never a full fist 
Well we might need to change that on Sunday – looking forward to it ?
Yes i am very much
So how does your teenage surfer boy hole feel today? You took a real pounding
Good, not sore 
I would imagine if somebody tried putting anything in there it would though 😛
Rest up your ass for next Sunday – no cocks over eight inches 😉
Will do 
What did you think as we watched the video of you being punch fucked?
I thought i need to start tanning nude 
Also i thought it was pretty hot 
I kinda like the contrast between your ass and body 😉
And did you like seeing your hole gape open?
Fuck yeah 
I was hot as 
I looked in the mirror when i got home too lol
What did it look like? All closed up tight again?
For the most part 
Any advice for other young guys who want to try fisting?
And why did you decide on me to pop your fist cherry? 
Cause i trust you you respect peoples limits. I say if you haven’t tried fisting its defiantly something to work toward
Well congratulations on your first fist and I’m sure soxster’s readers will love to see some pics from the session in the near future
They will be 🙂 

I showed the video to another Soxster boy and told him what happened. His comment was “Does putting a bowling pin up your ass count as a strike or a spare?”. We both agreed that so long it wasn’t a Split then it was ok – you don’t want to split your ass!  😛