JBL Prologue | Jay buys his first sex toys

Everyone is over the age of 18. 

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I don’t know if anyone can ever be fully prepared for the first experience on Grindr. Being a 19-year-old, barely out of the closet, doesn’t help either. Needless to say, I was faceless for a big part of when I first started to check the app out, and it didn’t lead to very good results. 

Namely, I found out people could be really blunt and mean. 

“Hi” I would type out 

“Pics” 

If I was horny enough, I would send them. If I wasn’t, I would move on to the next guy I was interested in to see if I could have better luck getting away without sharing pics. 

The next question was almost always “Top or bottom?” 

I would answer vers, although to be completely honest I didn't really know. I mean, can anybody really know what position they enjoy without trying it in real life? 

I think I would prefer bottoming just based on what my fantasies revolve around, but I would be interested in at least trying topping a couple times before deciding. 

“You look like a bottom” 

What does a bottom look like? I spin around in my chair to face the long-length mirror in my room. My slim and boyish frame reflects back at me. 

Fine. 

“I'm a bottom too, so probably not going to work” the guy continues. I flip back to his profile to check him out again. He says he's 6’2 and he's a pretty scruffy-looking guy, with chest hair and a beard. Surely, looks don't determine your sexual position. 

“You don't look like a bottom 😅” I message him, knowing full well I messaged and sent pics to him thinking that he was definitely a top. 

“That's what they say, but as soon as I put something in the ass that first time, I found my calling” 

Fair enough. I haven’t done …. that yet, so I don't know. I just fantasize about it when jerking off. 

“I wouldn't know 🤷🏻‍♂️” I message back. It's nice to talk to another gay man, even though he doesn't seem interested anymore in having a hookup. 

“You don't have toys?” 

“Nope.”

“You haven't fingered yourself?” 

“Nope” 

“Get to it. Go figure out what you like” 

I mean, he's not wrong. I have thought about fingering myself before but haven't gone through it yet. A toy does seem kind of fun… 

I close the app and flip over to a local sex store's website. The amount of dildos is overwhelming and most of them look pretty unpleasant to try to fit in. I mean… surely I will not be able to take something so grotesquely large. 

Can I? 

I end up selecting a medium-sized one that has a suction cup on the end of it. I liked the way it's shaped and it reminds me of one of the pornstars I follow online. I also get a fleshlight and lube, so I can see which one I prefer. I select pick up in store, just in case someone else intercepts my package if it's delivered. 

As soon as I pick my items up, I go back home and lock my door. Deciding that it isn't quite secure enough, I push a small cabinet in front of the door too, in case my roommate interrupts me. I open up the packages in a hurry, and hold each toy in one of my hands. 

Which one do I try first? 

The dildo looks pretty… enticing… but for someone who hasn't even fingered themselves it still seems a little big. The fleshlight seems pretty harmless, and I like the clear sleeve look. I had been extra careful to not select something that looked like any specific body part. 

The excitement of having these toys in my hand was already making me pretty hard so I got undressed and laid a towel down on the bed. Squeezing some lube into the opening of the fleshlight, I use my fingers to feel the material and spread the liquid. 

The supple and cold feeling on my fingers turns me on even more. This won't hurt… so … here we go. I push my hard cock into it in one go. 

“Whoa…” I whisper to myself as my cock is completely surrounded by fleshy material for the first time in my life. The head of it pushes gently into my pubes as I get used to the feeling of it wrapping around my cock. 

This is way better than a hand. 

I experiment with moving it up and down, closing my eyes in concentration at the incredible feeling of the material hugging my hard shaft as I slide in and out of it. 

I can't wait for my first blowjob. 

I pull my slick cock out and it slaps against my skin with a wet smack. I'm harder than I usually am, and I know for sure I'm going to cum into this hole by the end of this experiment. But I should try some other things while I'm here. I get on my knees and place one hand on the towel on top of the bedsheets. With my left hand, I position the toy and thrust back into it. 

“Ah!” I let out loudly. It's never taken me a long time to cum by jerking off, but being in a tight wet space is making me feel more on edge than ever. I practice the deep breathing I've seen online, and once I've calmed down a bit, I thrust gently into the toy. 

The moist sound of me entering the toy repeatedly is hot, and I imagine that it's a cute guy that I'm fucking. 

Nope. Nope nope nope nope nope. Going to cum. I pull out again and feel my cock throb in the open air. I'm going to need a lot more practice if I want to top.

Throb 

In my position, I turn my head to look at the dildo sitting on my desk.

Ok

I get up with my lubed-up member swinging a bit. I grab the dildo and lube it up, sliding my hand up and down the rigid shaft. I look around my room for some free wall space and finally decide on the mirror that is the closet door. 

Playing around with the height, I think I finally figured it out. I back myself up on it while looking at my messy room as I try to push a bit of the lubed-up toy in.

Nothing. I have to push harder. 

I reach back and hold the base of the dildo in case it falls off, but it seems pretty sturdy. Taking a deep breath, I push myself on it again. 

“OH!” I cry out fairly loudly as it penetrates me. It doesn't … hurt… but it's not exactly comfortable either. I hold myself there and place my hands on my knees. When I feel ready I continue pushing.

Nope. It's not going any further in. 

Ok. Not going exactly to plan but I guess this will do. I grind back gently on the part that I do have inside me. It doesn't feel like much at the moment, and my dick is getting soft. I pull it out fully and grab the fleshlight off my bed. I get back in position against the mirror and this time it goes in smoother, although I'm not sure if I'm taking any more than the first time. 

Putting my half-hard cock in the fleshlight, I stroke a couple times to bring myself back to a full erection. Oh my god, I love the feeling of my cock being surrounded completely. I can never do this with my hand. 

As I pump the toy over my cock, experimenting with the different pleasures I can have, I naturally grind into the dildo that's just barely inside me. I slide the fleshlight off and slide it over the underside of my shaft. 

“Oh fuck…” I whisper at the pleasurable sensation. My ass takes a bit more of the toy as I slide my shaft inside the inviting hole again. Fuck it feels so good. 

As I play with myself, my hole takes in more and more of the toy. More and more until it hits a spot that makes me gasp.

This spot makes my cock throb.

I'm close! 

I slide the fleshlight off me in a hurry, fighting the urge to cum. I still want to have some fun

I still want to enjoy it a little more 

I replant my feet to get a stable stance, and it pushes the dildo further into me. The urge of needing to cum overtakes me and I know I've gone past the point of no return. 

I jam my cock back into the fleshlight and immediately start cumming. 

“Ahh!!! ahhHHh!” I moan out loud as I feel my hole contract rapidly for the first time around something. 

“Ahh!...ah!!!” The overwhelming feeling of orgasming into a wet hole is sending my body into spasms, which makes me push into the dildo. The dildo pushes something inside me that makes me want to keep cumming and keep stroking

It makes me thrash. 

And I impale myself 

And I cum

It makes me thrash 

I impale myself

And I cum

And I cum

“MmmMm” The aftershocks rip through my body and make my knees wobble. 

When I feel ready to open my eyes, I am aware that I've taken the whole dildo inside me and my dick is softening in the fleshlight sleeve. I slide the fleshlight off first with another little moan and look at my semi-deflated and sticky cock. 

The dildo feels huge inside me, and for some reason, I feel even more worried about taking it out now than I was to put it in. 

God this is going to feel weird.