Bottoms. Just how painful was penetration for you when you first first bottomed for a guy?

[barenekkid]

Not at all. I’d been playing with my ass for years and I knew how to get ready so he just slid right into me and it felt soooooo good

[Cutedelicategay]

Mine was almost 8in. My stepfather. However he made love to my hole. The first breach was like filling me. I was 13 yrs. Had just started Cumming and that too very little. I never knew that he was grooming me into a submissive bottom. By the time I reached 18 I was fucked by him, my stepbrother, my stepfather's trucker and other friends and my stepbrother's jock friends. 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

[Bbpally]

Almost unbearably painful.  

 

He jammed it in me in one fel swoop. He wasn't large but he wasn't exactly small either.  Thick.  We were being quiet and we were trying to be sneaky in a friend's house.   It was not fun. I didn't get off.  I bled for a day or two after.   

 

Honestly I wish I had waited for another person.  It's not a regret persay.   But I do wish I had waited.  

[Daddyslut4use]

Yeah, my first was at a bathhouse.  I had been wanting to try anal for a while but was kinda scared. 
Decided to go for it in a slutty way. Got on all fours on a mattress in the big dark room. Pre lubed. 
I think the fact that I presented my ass made people think I was an experienced cum dump. 
First guy who approached was black and hung. He basically mounted me with no foreplay, fingers, nothing.  One fell swoop. 
I could literally hear pop in my head and then the most searing, pulsating pain as my anal ring screamed in pain. 
I tried to call forward so I could slide off his cock but he followed me down to my stomach and started rutting in my ass. 
The initial sphincter pain eased but the burning as he stroked my hole quickly replaced it. 
Probably 5 minutes in, it started to be more pain than pleasure. Another 5 minutes and he was nutting. 
I tried to raise to my knees to get off the mattress and another top quickly grabbed my hips and slid in. This time, it was almost all pleasure although still a bit sore. 
Took a couple more cocks one after another and my hole was now gaping. I finally got up and went to the showers to rinse off. 
Pushed out and lots of pink colored cum flowed down my legs. 
After that first time, I prepped with butt plugs and dildoes and never met a cock I couldn’t take with pleasure
 

[Guest]

8 hours ago, Bbpally said:

Almost unbearably painful.  

 

He jammed it in me in one fel swoop. He wasn't large but he wasn't exactly small either.  Thick.  We were being quiet and we were trying to be sneaky in a friend's house.   It was not fun. I didn't get off.  I bled for a day or two after.   

 

Honestly I wish I had waited for another person.  It's not a regret persay.   But I do wish I had waited.  

 My first time was also painful.

He was gentle and used lots of lube but because of his size and my inability to relax it hurt alot.

He kept asking if I wanted him to stop and I told him no the pain might fade.

It didn't.

He apologized after.

I think he was surprised when I told him"It'll get better the more we do it".

[Tanbbottom]

He was very careful, using lots of lube and took it very slowly. I  can't say I remember the pain, just the adrenaline rush of finally getting fucked. I knew I'd found my true sex role. 

[Devtylor]

My first time bottoming just happened to be with a Brazilian black guy. I told him that I've never bottomed before so he was extra careful. I can't remember if he got all that dick in me, but I remember it being uncomfortable but hot at the same time. 

[guy4funwaco]

It fucking felt like he was ripping me open. I screamed and fought. I couldn't understand how he could have fun seeing me hurt. But, the fourth time it hurt less and he gave me advice on taking it. 

[BritneyFUCKslut]

No pain I wnated to bottom more

[Guest]

F’ing painful. I screamed into the pillow

[Guest]

13 minutes ago, Bbbtmwsfun said:

F’ing painful. I screamed into the pillow

I didn't have to scream into the pillow.

We were alone with no one around and he was pounding my doggystyle while I was screaming.

But I was a good little bottom and didn't beg him to pull out.

My ass was so sore after.I was walking bow legged like I had been ride horseback all day.

Sitting wasn't easy either.I had to sit on one cheek or the other.

[VistaCaBB]

Mine was quite painful but I so wanted to financially have sex.  I was just a stupid teenager and he was a guy in his 30s who did not take his time, probably because he thought I would back out.  He railed me over the back of his couch and I came back for more later. 

[Guest]

5 hours ago, VistaCaBB said:

Mine was quite painful but I so wanted to financially have sex.  I was just a stupid teenager and he was a guy in his 30s who did not take his time, probably because he thought I would back out.  He railed me over the back of his couch and I came back for more later. 

Yes my friend. Been there got that  great to read all these events in the guys lives 

[Njn0mc]

My 1st was not planned kinda forced I was passed out drunk and woke up to to him fucking me deep. It hurt at times as he was thrusting in me. I was bloody a little when i wiped.  My real 1st time he was gentle and well lubed and was very pleasant and painless.

[Ilovetoswallowcum]

There was zero pain, omg it felt so good, like my body was made for this.  I had been a long time toy user but the real thing is 10x better!