Surprise hookup with young twink.

[Tanbbottom]

I've been chatting a little with a young guy for the last few months. It didn't look like we could make a hookup work. He couldn't host and neither can I. 

At my noon break today there was a message that he could host  but needed to be finished by 2. I was free, got his address, and was on my way. 

He had me park down the street and warned me about the barking dog.

When I got to the door it was clear he's about 19 and this is his parents house. 

He hustles me up to his bedroom and we start kissing. Deep passionate kissing. This twink has natural talent. 

He keeps apologizing for being nervous. I reassure him it's only natural. 

As we make out my hands slide up inside his sweat shirt and down to cup his hairy ass cheeks inside his sweat pants. 

He asks if it's ok to take off his shirt and apologizes. I assure him there's nothing to apologize for and we are soon both shirtless, hugging and making out. 

My hand moves around under the front of his sweats and finds a slim hardening 5 or 6 inch cock. 

You guessed it,  he apologized 'it isn't hard yet.'

More reassurance from me. 

I wonder out loud what he's hoping for. 

"Maybe I could try to have you fuck me?" Tentative and apologetic voice. 

I confess, "I 'm not a very good top really. "

"Oh. Never? Then I could try to fuck you. "

"I'd like that. "

"But I'm not hard."

"Can I suck you hard?" I offer .

"If you like. "

"Oh I like!" I assure him and drop my pants as I crouch and take him in my mouth. 

After a bit I ask, "Do you like that, do you like your dick in my mouth?"

"Oh yeah!" His smiling face is in agreement with his words. 

Then we switch places and he's very tentative about taking my thick eight inches into his mouth. I assure him he doesn't have to do anything he doesn't want to do. He agrees, not this time. 

I assure him I'm ok with that and go back to work on his twink cock with my expert mouth and throat. 

He's hyper hard and I'd prefer his nervous young load in my ass. "Do you want to fuck me now?"

"Is that what you want?"

"Oh yeah!"

"Then I will try. "

As I lie on my back on his bed he goes to his desk and tells me he has a condom. 

I tell him he doesn't need that for me. He says he wants it anyway. I  ask if he has lube. He points to the bottle of Vaseline and says, sorry this is all I have. 

I  reasure him that's fine with me. I don't tell him why. I know I'm a deceptive old pervert taking advantage of a naive young man. 😜

He crawls in between my legs. Works to get the condom on as I grease my hole with Vaseline. 

He tries to enter me but has lost his erection. Apologizing he pulls it off and lays it aside. 

I pull his lovely naked body in on top of me and we are passionately making out once again. 

My hand is jerking his young cock and it is hard once again. I suggest he might want to try again and aim his raw cock at my greased hole. 

On his first try he penetrates me with half his raw erection. My ass contracts with pain. And he apologizes. I assure him it's OK,  breath deep and ease the rest of him into the hilt. It now feels great for me and I check with him. 

"It feels great!" he assures me. 

So the fucking begins. I ask if he's less anxious if we talk. He responds, "Yes please, keep us talking. "

I learn he's only fucked a couple other guys. Always with condoms. He's never been fucked. This is the first time he's been in an ass bareback. He loves the feeling of his raw cock in my hole. 

I have to work to get him to look at my face. He relaxes and smiles when I succeed. 

'Can he tell I'm enjoying myself?' He smiles and tells me he can. And yes he's enjoying himself,  but he anxiously looks down to check his cock and he starts to retch. 

'Damn' I think to myself,  'I must not be squeaky clean.' I hadn't had time to do a careful clean out. 

He apologizes and asks if he can go clean up. While he's gone I pull out my wet whipes.  Everything is clean. I stick a finger in deep. Still clean and passing the sniff test. I lie back on the bed and without getting my hopes up, apply more Vaseline to my hole. 

He's very apologetic when he comes back and anxiously tells me he's not sure he can continue, maybe another time. I assure him that's okay,  I understand and I ask him if he wants to cuddle for a bit. 

He quickly moves his naked body into mine and I offer soothing sounds and gentle kisses to his forehead. 

Soon his mouth moves to mine and once again we are passionately making out. 

My hand finds his cock and he is rock hard. 

I ask if he wants to 69. He looks confused. I ask if he knows what 69 is and has he ever done it. 

He knows but never has.

Does he want me to suck his cock?

Yes. 

So I have him move it up to my mouth. 

He's soon straddling my chest and I'm working his super hard dick with my mouth and throat. 

I  stop long enough to ask if he likes this. 

"Oh, yeah!"

I help him adjust so he can fuck my face. 

'I'm sorry, you're going to make me cum."

"Don't be sorry,  give it to me", and I took him deep again. 

His first shot hit my tounge leaving a bit of a bitter taste. The rest shoot deep down my throat. 

Not exactly what I had hoped for, but good enough. 

"Sorry " a deeply concerned look on his face. 

'There is nothing to be sorry about. That was fantastic ." I reassured and meant it. 

Once again his naked body was on top of mine and we were passionately kissing. Once again he was super hard. 

I gently asked if he wanted to try getting into my ass again. 

"I can try, but I want the condom if that's okay?"

"Whatever you need. "

We retrieved the condom he had set aside and he hastily pulled it back on. There was a huge air bubble trapped in it. I  liked the look of that.  I helped him line it up with my hole and he was inside me lickity split. 

He was clearly enjoying this fuck until he felt something and feared he had slipped out. 

He checked,  saw he was still inside and reassured himself he could see the condom. 

Back to a great fuck during which he apologetically asked me to keep the noise down for fear of the neighbors hearing. It was my turn to apologize and assure him I was loving this and too enthusiastic with my voiced pleasure .

He agreed and soon confessed I was about to make him cum again. 

"Great!" I joyfully assured him. 

He pushed in deep and there were subtle signs he was ejaculating into the condom deep in my ass. 

We deep kissed some more and I thanked him. 

When he pulled out I saw what I was hoping for. The condom had broken and was only around the base of his young cock. I moved a finger to my ass and sure enough he had bred me his young naive load.

I had him check his cock. He was horrified. I  assured him I couldn't be more satisfied. I'd wanted his cum in my mouth.  He looked concerned.  And in my  ... He finished my sentence  "Ass" and a big smile broke out on his face. 

He then hurriedly ran off to the bathroom. I was almost dressed when he got back and quickly slipped into his sweats. He kept the dog quiet and called thanks as I scurried out the door and down the street to my car, taking care every step to keep as much of his prize virgin load in my ass as I could. 

And yes, it is still in me every bit as much as the one in my stomach. 

I stopped on my drive home to send him a thank you note, "Amazing, amazing, amazing!"

He sent a note back, assuring me he had enjoyed himself. 

Literally fucking fantastic! Stealthed his first load deposit into my cum dump ass. 

Now I wonder if I'll get another chance with him,  and if he'll ever want to use a condom with me again?

Further, might I be the first to claim his twink virgin ass ? Might I be the first to breed his beautiful young hairy ass?

Mmmmm, mmmmm. I couldn't be happier. 

[Nowwhat007]

Please keep us posted. This is so hot 🥵 

[str8mature5]

Yes please contuine with this twink

[Tanbbottom]

Thanks guys. Actually he ended up blocking me. I guess his nerves just got in the way of proceeding. I was a little disappointed but it's not worth stressing over. Bottom line, it's a hot unique memory,  and I really do wish him well. His nerves will calm down someday. 

[fuckyouraw777]

1 hour ago, Tanbbottom said:

Thanks guys. Actually he ended up blocking me. I guess his nerves just got in the way of proceeding. I was a little disappointed but it's not worth stressing over. Bottom line, it's a hot unique memory,  and I really do wish him well. His nerves will calm down someday. 

Maybe he's not quite as naive as he seems, was meaning for the condom to break, and got nerves because of that.