My First Fist

(Story is true, names are fictional)

It was not long after a breakup. I had a dating app on my phone and hooked up a few times. This 20 year old guy sent me a message. The usual nonsense info to back and forth. I recognised him. We have had sex before two years before. His name was Dylan. I told him we met before but he could not remember it at first. After telling him where and when we fucked before he suddenly said: "now I remember". I remembered Dylan as very slim, very tall, arrogant and quiet. He has a huge dick of 9 inches, blond hair and is extremely sexual.

I was not home at the time and already came that day, so I was not really in the mood to have sex again. But the guy kept writing.

Dylan: "I'm only five minutes walk from you door."

Me: "Ok, but I'm not really in the mood for sex. You could just come over for a chat."

Dylan: "Sure, but a shame, I'm really horny mate."

Me: "I'm into exposure and have loads of pics and vids of myself on my pc. Why don't you have a look at that here and wank on them?"

Dylan: "Sure, sounds like a plan. I'll be there in 10."

Dylan knocked on the door.

Me: "Hey, come in, how's you?"

Dylan: "Hey, not too bad, long time no see."

Me: "Yea, had a relationship but broke up a few weeks ago."

Dylan: "Sorry to hear that."

Me: "My pc is there, why don't we sit there."

Dylan: "Fuck you have so many pics and vids."

Me: "yea, kinda hot that you're scrolling through all of them now, whilst I'll sit here."

Dylan: "I love the vids, do you mind if I take my cock out?"

Me: "No, do whatever you feel like. What have you been up to?"

Dylan: "I've been working in a shop around the corner and do dragqueen shows in a pub in the city. Never thought I would do that, but I just rolled into it. fuck I'm so hard now."

Me: "Damn, I forgot how big you were, can I touch it?"

Dylan: "Yea, sure, go ahead."

Me: "OMG you are rock hard, feels so nice to slowly stroke your huge cock."

Dylan: "You like that don't you."

Me: "Yea, a shame I already came today."

Dylan: "that's ok, you don't have to do anything."

He sat there right in front of me with his skinny black jeans on. His trousers open and his cock sticking out. He looked at my vids and pics and occasionally at me. It was so hot to have all my clothes on and have a hot super young stud sitting there stroking his member. I thought that it would not take him long to shoot his load and leave.

Dylan: "so tell me, what are you into now."

Me: "have been bottoming mostly, bought some dildos and tried to stretch my ass before. I recently been intrigued with more extrem bottoming, like fisting. But whatever I tried, I cannot stretch it that much."

Dylan: "fuck that's hot. Would you mind at all if I rimmed your ass?"

Me: "Dude, I haven't douched our washed myself since this morning."

Dylan: "I don't mind, it doesn't bother me."

Me: "Are you sure? Really I should freshen up."

Dylan: "Don't, just drop your pants and lift your legs up."

Me: "fuck man, you like it dirty."

Dylan: "ha."

Me: "Oh man, that feels so good to feel your tongue circling around my hole and making me all wet. You make my cock hard man."

Dylan: "yea, I do love to rim a nice tight hole. Can we not go to your bedroom so I can work on your hole more comfortably?"

Me: "sure, over there."

Dylan: "Why don't you lay on your back with your legs up. You probably don't mind if I take all my clothes off!?"

Me: "fuck man, you're seducing me. You're making me so horny."

Dylan: "Ha, as if you were not horny before I arrived."

Me: "Oh fuck your finger feels good on my hole."

Dylan: "got any lube?"

Me: "Yea, top drawer, but I don't wanna be fucked."

Dylan: "sure you horny fag, ha."

Dylans index finger pushed against my hole and slowly slid inside me. It felt a bit awkward at first but I did not resit it. He pushed two fingers in my ass and massaged my hole very gently. I had not idea what his plan was. His cock was rock hard and his cockhead was shiny with precum. His eyes were horny and full of concentration. He pushed now three fingers in and turned the around. He was trying to stretch my hole.

Me: "dude, not sure about this, what's your plan?"

Dylan: "just relax and enjoy. I'm enjoying it ha."

Me: "damn that does feel amazing and it turns me on so much. Wait I take the rest of my clothes off."

Dylan: "fuck, look at you. Your cock is so hard, mind if I suck it a bit?"

I did not have to answer his question. He he pushed now four fingers in my ass and grabbed my solid cock with his other hand to point it in the direction of his lips. He opened his mouth and slid hid lips right to the base. I forgot that I can already that morning and was now so horny and felt so hot. I knew what his plan was. He was going to try to fist me. Four fingers were already in with his wet warm mouth sucking on my cock. He stopped sucking me and pulled his fingers out of my ass to add loads more lube on his hand. He pushed now 5 fingers in.

Me: "Oh dude, not sure about that. Have you ever done that before?"

Dylan: "yea, once. Trust me, just relax. It will be fine."

Dylans' hands were not to big. He pushed five fingers in and then I felt the pressure of his knuckles. He pushed rather hard and I felt my ass stretching.

Me: "oh, fuck stop stop, that hurts too much."

Dylan: "ok, relax. I'll use more lube, don't worry."

For some reason this 20 year old twink could comfort and calm me instantly even though he could be my son.

Me: "damn, I'm nervous man. Do be careful."

Dylan: "you just have to let it happen, I won't stop now."

Me: "fuck man, I'm both horny and scared."

Dylan: "keep breathing."

He pushed five fingers in again and turned them slowly to stretch me more. He then pushed again and I felt my ass stretch way too much. He looked at me and saw it was uncomfortable and withdrew again. He added more lube on his fingers, hand and on my ass. He slowly entered his five fingers again and started pushing.

Dylan: "you're opening up. I'm quite far in already."

Me: "oh man, this feels so weird but my cock is throbbing and I'm so horny now. Look at my cock dripping man."

Dylan: "I'll lube up one more time and then you'll have to take it all. It will stretch a lot, but just let me push my hand in."

Me: "fuck, fuck, fuck."

I was breathing loudly now. I felt his slippery hand pushing against my first sphincter and stretching it open. He pushed slowly but did not stop. He went on and I felt my second sphincter overstretching. His knuckles were scratching my skin around my hole and my skin was pushed away opening up my sphincter to his knuckles and forcing me open. I felt pain, but the horny feelings overpowered and although I felt scared of hurting myself, I now only wanted to feel his fist in me. I felt my sphincter stretching more and more.

Dylan: "relax, I will keep pushing. I will not stop. Just let it go in. Fuck man that is so hot."

He pushed slowly but hard and suddenly I my hole stretched over his knuckles and sucking his hand into my ass closing my sphincter around his wrist.

Dylan: "Oh my god, that is so hot, fuck I'll have to take a pic."

I could not speak at first. I was so horny as if I was in a trance.

Dylan: "Fuck man, your first fist."

It now started to feel uncomfortable and I asked him to pull his hand out of my ass. He slowly pulled and I felt my ass stretching again. It felt so tight. He kept pulling and my ass pushed his hand out. Loads of slime came out ass well.

Me: "fuck that was so hot."

Dylan: "wait, I'll go back in and film it."

Dylan switched on his recording and pushed his hand against my hole once again. He pushed, but this time he did not stop he just pushed it all the way in. I cried out loud with excitement mixed with pain and horny feelings. His cock was throbbing. I started wanking myself, looking into the lens of his phone.

Me: "oooooh, I could come any second."

Dylan: "Don't, I want to have some more fun."

Dylan pulled his fist out of me and laid himself next to me.

Dylan: "sit on my cock."

Me: "I have to get a condom first."

I knew that Dylan had lots of unprotected sex and I did not want to jinx it. I opened a Durex and held the tip between my fingers. I dropped over him, my legs spread on my knees and held his cock with one hand and rolled the condom over with the other. Fuck his cock was so hard. I squirted some lube on his dick and and sat on it. I rode him like that for a while. It felt so good and he hit my prostate in just the right place. I squirted some precum mixed with piss in his belly button.

Dylan: "fuck man, is that piss!?"

Me: "euhm, yes."

Dylan: "that is sooooo hot!"

I let his cock slide out of my ass and sucked his belly button empty. It tasted so good. I could see in his eyes that he loved it. He then turned me on my back and pushed his cock aggressively in my ass. It felt so good. I was in total submission of a bloke that was 17 years younger than me. He fucked me hard and long. We were both sweating and breathing and moaning loudly. We did not kiss once. He pulled his cock out of my ass, slid the condom off and grabbed both our cocks wanking the two with one hand. Our cocks were wet and slimy of precum, sweat and lube. We then grabbed or own member and started wanking whilst looking in each other eyes.

Me: "Give me your phone. Mind if your face is in it?"

Dylan: "I don't care."

I switched on the cam and started filming both of us. Seconds later both our cocks started pulsating and shooting our white thick cream all over my face, chest and belly. I shot so far. I was soaked in sex.

He took a towel next to the bed and dried himself up.

Dylan: "give me your email, I'll send you the vids."

Me: "cool, sounds horny. We'll have to do that again."

Dylan: "sure, ha. What do you think of your first fist?"

Me: "damn, that was so much hotter than I expected."

Dylan: "haha!"

Dylan left, leaving me exhausted in my bed. We had met up twice more, but it was never as hot as this time. And although I asked him for the vids of that day multiple times, he never sent them.

And although he never fisted me again, it opened me up literally for a whole new set of sex experiences.