A rough draft – I’ll come back and fix it up later – think of this as a preview.
Over the years I’ve been lucky enough to fuck a number of cherry boys. Some of them had fooled around with other guys. Some had sucked a lot of cock. Some had even topped before. But I’m talking about that first time a boy finds himself with a hard cock deep in his butt.
Every boy has a different reaction to their first fuck. For some guys it hurts. For some it is pleasure and pain. For all of them it is a big step that they are taking with me – and it’s an honour.
This particular cherry boy was mid twenties and had sucked his fair share of cock but had never been fucked. He was interested in BDSM as a submissive but I also wanted him to have a first fuck that involved eye contact and trust. He bravely left how his first session was going to go entirely up to me. Smart boy. A responsibility I took seriously.
I buzzed him into my building and he came up to my floor. As instructed he knocked at my front door, turned and stood with his back to the door. I made sure he was in position using the spy hole before opening the door and popping a fur lined blindfold over his head. At least that’s what I tried to do – turned out he had quite a large head and it took a few seconds to slide it over his head into position. I dragged him backwards into the apartment, closed the door and spun him around – pushing his back into the door. He had dressed up. Stylish burgundy wing-tip shoes. Black jacket with a high collar buttoned up tight.
I started touching him all over – confirming a tight bulge in his pants – before starting to strip him. Jacket off. Shirt off. Pants undone. Touching the naked skin. I have learnt over the years that taking off shoes during sex is probably one of the least sexy things you can do. There is no way to do it gracefully so I get the boys to do it themselves. He slipped them off quite easily. In one smooth movement, that he later said impressed him, I slid off each trouser leg collecting his sock with my fingers on the way through. I left him wearing just his blue Nasty Pig jock strap that we had picked out while shopping the previous weekend. I spun him around, pressed my front to his back, and wrapped my arm around his neck, holding him in a tight choke hold while running my other hand over his body.
I fitted him with a collar, leather wrist cuffs and a leather harness. The collar was fur lined and comfortable. The harness designed to let me throw him around.
We ended up my leather couch, me learning back while he pleasured me orally. His technique had improved a lot since the last session. No longer did he just try to cram it into his mouth, but he took his time in getting to know my cock. Licking the shaft. Teasing the head. Gently chewing the foreskin. Tonguing my balls. Definitely an eight out of ten blow job. I told him to go lower. Lower and lower he licked until he was approaching my ass. I knew that he hadn’t rimmed anyone before – but it was time to see exactly how obedient he was.
He followed my orders, and his tongue reached my butt. He never really went in, but rimmed the outside. As his confidence grew, his tongue grew more active. He said afterwards that he really enjoyed rimming me – something he never intended to do.
After enjoying his mouth on my cock, ass and balls it was time to move onto other things.
At our last session he reacted really well to be spanked. I went to the cupboard and selected a particularly vicious steel studded thin paddle. I started spanking him, gently at first and then getting harder.
I lay down on the couch and positioned myself so that I could spank him while he sucked my cock. The paddle was really vicious and his ass was quickly red.
After I had my fun it was time to take him into the bedroom. He led the blindfolded, helpless boy into the bedroom and pushed him into the sling. I put his legs into the padded leather ankle straps and clipped his arms onto the sling.
If he been able to see, he would have been blinded by the overhead lights that were focused down onto his crotch and ass. The HD video camera on the tripod. The light mounted below the camera. The purple LED accent lights in the corner of the room. I hit record on the camera which was focused on his ass and cock.
I reached down the side of his jockstrap, and pulled out his balls. I put an silicone nut lock onto his balls – orange in the shape of a metal nut – to slow him down and ensure he didn’t blow his load too soon. The front of his jockstrap was now glistening with pre-cum. Not just wet with pre-cum – the clear liquid had seeped through in such quantities that it was sopping wet. If he had been on all fours there would have been a dangling trail of pre-cum from his jock to the floor.
I got down on my knees and pulled his ass cheeks apart. He had a nice smooth hairless hole with an ass that was a little bit more crinkled than a teenagers’ but still fresh and cute. I left him helpless in my sling and went to the bathroom. I grabbed a fresh brown washcloth and ran the hot water tap until the water was scalding. I wet half the cloth and went back to the bedroom. He moaned as I ran the hot wet cloth up and his crack. His ass wasn’t dirty before but I wanted to make sure it was totally clean – so that it was lickable and so that he could relax knowing it was clean. The hot cloth cooled as I ran it over his ass. I turned it over and used the dry half to towel him off. Back on my knees I pulled his cheeks apart. He lay there quietly and helpless. His ass was pink and hot – and rapidly cooling. I spread his cheeks wide and gently touched my tongue to his ass. He moans appreciatively. I start with short flicking licks and his ass clenches and spasms in pleasure. I pick up the pace and work his boy butt with my tongue. Long licks up and down his crack, trying to push my tongue into his virgin ass. Rapid lapping, teasing. I pull out his iPhone and snap a few photos of his wet virgin hole – the last ones that will ever be taken.
I gloved up and lubed up his ass. I poured lube over his cock, balls and ass. With beginners it is important for them to be reassured that there is a lot of lube. They can’t feel dry at all or they will tense up. That can be fun but not for a first fuck. I slowly pushed my fingers into his ass and started working his butt to loosen him up. When he was nice and loose I pushed a medium purple silicone butt plug slowly into his ass. He winced as it reached the widest part and was about to ask me to slow it down when it passed the widest part and locked into place. I teased his hole with the butt plug. And slowly eased it out. I reached for a larger dildo. Not a massive toy, but definitely something with some width.
This one hurt. He winced as I pushed into him. I left it in to stretch him out. It was then time to take off his blindfold – so I could watch his face.
When I take off the blindfold there is something unexpected. He has been having such a good time that he has sweated into the black sheepskin lined blindfold and there are back marks on his face. For a split second I think I’ve bruised his face but it’s only black dye. I rub his face with the towel and the strangely sexy black eyed panda look quickly disappears.
Despite the fact that this boy hasn’t been fucked, he is a bit of an amyl whore. He uses it regularly when jerking off. To make sure that the amyl really helped his first time I loaded up a gas mask with amyl. I had given him a few sniffs during the toys and fingers up his ass but it was now time to give him a serious hit. Breathing amyl through a gas mask gives you a serious rush. Safety tip – never do this by yourself with the gas mask straps attached. You want to just hold it there and have it fall off. If you leave it on and something happens then it could kill you – so play safe! I held it over his face and told him to breathe in. I gave him about ten seconds of amyl and dropped the mask beside the sling.
When I slid my cock into his butt he asked if it was in. As a top with a massively thick cock this surprised me – as I had never had that question before! What he actually meant was “is that your cock or fingers?”. The misunderstanding resolved I started to push deeper into him.
He was moaning in pleasure. No pain. None. None of the usual pleas to go slowly or winces that normally go with a cherry pop. Just pure pleasure. I was expecting to have to push into him slowly – stopping frequently so he could adjust. But there was no need – it was one slow, steady push until balls hit his ass and my cock was buried as far as it could go.
He was having a good time – his eyes kept rolling back into his head. I fucked him slow, fast, hard, long strokes, short strokes. He moved his legs from the ankle straps to rest directly on the sling chains. By putting his feet on the sling chains he really opened his ass up to give great access for the fuck and allowed me to go deeper. I put his hands into the leather wrist straps so he can hang on during the fuck. Every few minutes I hold the gas mask over his face and send him flying on an amyl high.
His face has become flushed – but it makes him look more alive and passionate. He is covered with a fine sheen of sweat as I fuck.
The fuck got rougher and rougher. Part of me wanted to see him gasp and feel a mixture of pleasure and pain. But no matter how hard I fucked, he wasn’t experiencing any pain at all. It was pure pleasure. The only thing that changed was the level of pleasure. The harder I fucked, the more he liked it. This was the longest, most intense cherry fuck ever. I grabbed his harness and used the leverage to pull him onto my cock harder and harder.
At one stage I reached over to the camera and paused it before restarting it. This gave the camera a chance to save the first file. I realised that we has been fucking for 47 minutes. I decided to go for a nice even hour – and fucked on. I grabbed his I-Phone and snapped photos with my cock buried deep in his ass, and took short videos of my pounding him, including his face.
I’m pulled harder and harder on the harness to pull myself into his ass harder and rougher. Suddenly one of the studs on the harness gives way. I knew I should have used one of the buckle harnesses but the stud ones look good too. I reconnect the harness, grab it where all four straps connect over his breastbone and slams my cock back into his ass.
Eventually we reached an hour and it was time for him to cum.
When he finally came his reaction was impressive. I continued to fuck him as hard as I could until he was panting and the last drop of cum had been milked from his cock.
I ripped off the condom, gave him a second to compose himself and stood over the sling and jerked myself off while he tongued my balls. It took me a while to come as I was pretty tired from fucking for an hour. Finally, when I was about to blow, I asked him whether he wanted it on his face or chest – he said to avoid his face so I turned to the side and blew it facing away from him. The first shot travelled about three meters.
I rolled onto the bed and lay there exhausted. Longest, most intense of a cherry boy ever!
When I talked with him afterwards he said that he couldn’t recall another time in his life when he had been so happy. Pure joy. He watched the video I took on his I-Phone again and again – and said he couldn’t get over how ecstatic he was.
I thought you might enjoy some of the SMS between Zakai and myself before and after the session:
Andrew: Every good gay boy dreams of his first time being ploughed into submission. These days it seems most boys are fucked in high school – if sixteen, seventeen and eighteen year olds can take a cock up their butts and love it – so can you. 😉
Zakai: R u trying to drive me insane I’m at work hard and I can’t do anything about it
Andrew: Hehe. As bad as this teasing is, it will be far worse tonight when my cock head is resting against your hole that is wet and open from toys – and I just tease your hole and crack, not knowing when I’m going to push myself into you. That first time you feel my balls hit your ass cheeks and you know I’m in fully.
Zakai: Wow I have no words
And after the session….
Andrew: If you had half as good a time as I did – you had had an amazing first fuck;)
Zakai: I seriously don’t have words. Thanks for the greatest night of my life. X
😉 It was amazing I couldn’t ask for better.
Andrew: How’s your butt feeling?
Zakai: A little sore but not unbearable lol. 🙂 I had a great time. U would not believe how great the time I had was I feel amazing I feel different hard to explain
Andrew: There is a reason why people always remember their first time. Life is never going to be the same – taking a cock up your butt you have proved you can take whatever life throws at you.
Zakai: Lol. You are getting me hard. 😛 It was a very surreal experience. I can’t wait to read it on soxster. I just watched the video of u fucking me and you can really see the ecstasy in feeling its written all over my face. 🙂
Andrew: Haha – yes, you were having a very good time. 🙂
I posted this version of the story I posted a draft – this was his response:
Zakai: Huston. We have a problem. I just read your draft of my first time at work. Lucky I’m sitting down. I’m so fucking hard and my pre cum has leak all the way through my work pants. Clear wetness. If i stand up everyone will see and i finish in 10 min 🙁 Can’t wait to read the final version.:)
A pic of his virgin ass – the last pic ever taken before his cherry was popped!
First cock in his ass.
Jock soaked in precum.
Strapped into the sling…