56harrisond

A perspective from someone who first bottomed just after his 18th birthday and has been mostly a bottom since then:
It's mostly mental.  Does the dick feel good inside?  To me, yes.  It's difficult to describe what the actual physical sensation is like.  As I think about it, most words to describe it just don't quite convey the sensation.  Pressure.  Fullness.  Definitely the incredible feeling of pleasure if someone is able to stimulate my prostate, but that doesn't always happen.  I think for me the main pleasure is the sense of connection.  I just enjoy having someone inside of me.
I've never understood the discussions about how it takes time to "train" oneself to like it.  Or that it takes an incredible amount of lube.  My first time bottoming (with my first real boyfriend when we were both 18), we didn't have any lubricant other than spit but we both wanted to try it so we did.  I enjoyed it.  A lot of the time he fucked me after that, we didn't use lube.  I was just hot for him and had no problem relaxing and letting him in.  Surely since then I've had partners where lube was required, particularly when using condoms because that changes the feeling of friction for the bottom.  And guys with very large cocks definitely need to have skill in terms of knowing how to enter at the right speed.  Attempt to thrust too fast too soon and I will feel pain, not pleasure.  With the right foreplay, though, even a big dick can enter me with me feeling like I'm finally getting what I've been waiting for.  A rush of pleasure, with me thinking, "ahhhhh."

1000% Facts right here👆
The position you're in makes a big difference too. Some positions give the bottom more/less control, or allow for maximum depth for balls deep fun.

Even now that I am a more experienced bottom, I would say that anal still hurts some. It almost always hurts for me right at the first penetration I think because my sphincter has to relax and get used to the dick. After that it's more pleasure than pain though sometimes it can still hurt a bit...almost in a pleasurable way actually.
The biggest difference between an actual dick and a dildo is the human being involved. I actually really enjoy seeing someone enjoying my hole and love watching their sexy body on top of mine and hearing their moans. The way another guy fucks is also more unpredictable and not controlled by you, so that makes it hotter than a dildo that you are controlling. 

It's not a weird question, but it's very hard to give anything more than a general answer.  It's highly dependent on the guy who is topping you.  Skill, in my experience, is more important than size, but a big guy is going to feel a lot different than an average guy.
You've taken dildos before, so penetration isn't going to be new for you, but a real cock does feel different because flesh can flex and squeeze in ways silicone won't. 
The best advice is find a guy who you can trust to be your first, it's important for him to be patient and responsive to you when he pushes in.  Use plenty of lube and take it slow.  It is probably going to hurt at first since you're inexperienced, but a good top will let you get used to him inside you before he starts thrusting.
Size is mostly going to affect how "full" you feel.  Guys with longer cocks can actually feel better since they're less likely to accidently pull out all the way and re-enter unexpectedly (that can hurt).  Guys with thicker cocks may be a bigger challenge, even if they're not particularly long.  If they're curved they can feel different than a guy with a straight cock, just because they may hit your prostate differently.  
You should probably give more thought to who would be your first top.  It's probably best to avoid a first time hookup, find someone who you can take your time with.  

I have two regulars that I engage with pretty often that are unpaid. I’ve written about the straight 21 year old kid who’s virginity I took underwhelmingly. We’ve been hanging out regularly since then. It’s always the same. He comes over. Sucks my dick. Swallows a load and goes home. It’s not exciting or spontaneous, but it’s nice. He identifies as straight. Last time he was over, he mentioned that he wanted to suck two dicks at once. 
 
My other buddy is into every kink and fetish you can think of. We explore everything together. Toys, choking, objects in every orifice, groups, pool and hot tub sex you name it. He’s a once in a lifetime sex partner that we just have that chemistry and open attitude that leaves so much room for exploration and pleasure. 
 
He was over tonight and I told him about the other boy and what he wanted to do. He said have him come over. I texted the younger guy and he said he’d be right over. We had poppers lube toys harnesses scattered all over the bed and nasty porn playing on the big screen. My buddy also had hardened candle wax dried to his back. It was a scene. 
 
So the 21 year old walks in and is immediately in shock. He goes “what is all this?” We giggle a bit, clear the bed, and lay together so he can suck us both off at once. He starts to go down on us, and then I notice his eyes lighting up. He stops, looks at the toys and goes what are all these?  We do a little lesson, he’s curious but not ready to partake. He does ask if we’d go down on him at once. We do. He hangs his head off the bed and won’t make eye contact with us but is loving it. 
 
My buddy says to him. What do you want to see us do?  The kid got flabbergasted and couldn’t put a sentence together.  After some coaxing,  he settled on asking me to fuck my buddy while the kid sucked his dick. We obliged. All the while, the kid’s phone is going nuts. Calls, texts, beeps, vibrating on the dresser, all of it. We’re trying to ignore it but it keeps happening. He tells us to just ignore it, but won’t silence it. 
 
After 20 minutes of this I said dude, I think there’s an emergency. He said no, it’s my girlfriend, we share location and she knows I’m here but doesn’t recognize the address. She’s a jealous Latina. 
 
I said is she gunna show up at my house? 
 
He said no. 
 
She continues calling. 
 
I said you have to pick up. I don’t need her at my house. 
 
So he answers the phone. She says where are you. He says I’m at my coke dealers trying to score. 
 
I bust out laughing. She says he better bring some over to her. I hardcore don’t do drugs except occasionally hallucinogenics. I have no coke in my house. He said I need something or she’ll kill me. So the best we could come up with is Metamucil in a ziploc bag lol
He texts her a pic of our “drugs” and she says she’s tired and going to bed, but that they’ll party tomorrow when he goes to see her.
We go back to playing around. He swallows my buddies load and ate my load out of his ass. We cracked his sexual world view wide open. 

 

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