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

[Alaric]

First time was with a condom, and apart from a couple of twinges not painful. It was in a private room in a sauna where I'd gone for just give/take BJ's. The anon guy said I should try fucking, I didn't measure but I suppose he was about five inches. The biggest shock was the coldness  of the glob of lube against my anus.. 

[Medwaym]

My first time was really painful, I had to ask him to pull out. This put me off trying for quite a few years sadly.

[Cockdumb&Cute]

It wasn't painful at all - I had already been finger fucking and using dildos since i was young. It felt right and good and natural for me.

[Guest]

My first time, I posted an ad on CL. I was 18, he was in his late 50’s early 60’s, visiting on business and told me to come to his hotel room. His cock was super hard, probably 7.5”. He had me lay down ass up on the bed. He got on top pressed his cock against my tight hole for a couple minutes trying to stick it in. Just when I started thinking it wasn’t going to fit, he pushed his cock in all the way, basically popped my cherry. It fucking hurt, I was frozen in place gasping for air for a few minutes. That didn’t stop him though, he started fucking me, hard. I stuck my face in the pillow to stay quiet. Then he flipped me on my back, pushed my legs up above my head exposing my ass and fucked me rough for a while. He finally asked how my ass felt, I told him it hurts, lol. He had me suck his cock until he came in my mouth and I swallowed. My ass was sore for the next couple days. As soon as it felt better I posted another CL ad and got fucked by another older daddy and my ass didn’t get too sore afterwards.

[Sfmike64]

The first times I bottomed I hated it. I was a teenager and the person doing it wasn't gentle and didn't use lube, just spit. 

So I hated getting fucked and mostly topped and sucked dicks. It wasn't until I was about 20, it was 1984, and met a guy through an old fashioned print personal ad. I took the train into NYC and spent the weeknd with him. His name was Chuck.

Oh god was he hot. Short, furry, a bit muscly, I was SMITTEN. He was SO my type. In an alternate universe I would now be married to a dentist since 1984.

Anyway, we smoked some weed and I was so into him that I finally was able to relax and take his cock. He bred me all weekend (and took me to see Whoopi Goldberg's original one woman show!).  I always wondered what happened to him. 🙂 

[Hottightass4u]

Don’t remember any pain.

[Chastitytom]

Hurt like fucking hell. He was 54, i was 15. Contact pages in an old porn mag. Searched for a strict older man to take me. So it was my own "fault" that it was so painful really. Although he really enjoyed hurting me. Kept going back for more. 

[drm1234]

I was 19 or 20 and he was in his early forties.  This was the mid 1980s so he wore a condom.   It hurt a bit when he first entered me and started to thrust.  It didn't take long for me to relax and start to enjoy it.   That's when I knew that I was born to be a bottom.  When he found out that this was my first time, he said one of the sexiest things anyone has ever said to me:  "A big handome boy like you should get fucked whenever he wants".   

[rockhard801]

My first time was painful for the first few minutes and then feelings of pleasure took over.  However, the next day I was really sore and it took a few days for the pain to go away.  

[Guest]

It hurt in the beginning but he said two things to me. Once my cock goes in it doesn’t come back out until I cum. And the second thing was I don’t ever wear condoms so I hope you like getting knocked up slut. 

[chasingseedinaus]

It didn't hurt at all. The guy wasn't too big and it was with a rubber. Blew in a minute or two. I was 17.

[Pigbear66]

I was quite young and introduced gradually to sex by the next door neighbor. At first it was touching and fondling. He introduced me to being sucked and of course I returned the favor, finding I had an aptitude for it. Lol.  He liked to play with my hole, gently fingering it while I sucked his large veiny uncut cock ( foreskin fascinated me). As my ass got used to being fingered, he used KY jelly to get in 2 fingers. Finally he asked if he could fuck me and wishing to please him I agreed. He had me sit on his cock at first. Praising me as I " took it as a man", I slowly slid down the shaft until I had it all the way in. It hurt like a son of a bitch.  He let me get used to it, then began to gently thrust as my ass loosened up. The pain began to melt into a feeling of warmth and fullness. Turning me on my back he began to fuck me harder, then much harder, finally impaling me to the root of his dick as he filled my ass literally with his cum . He stayed in until he got soft, then carefully cleaned my bum. I had bled a little. I was sore the next a bit, but was proud I had pleased him. He fucked me every day for a week until my boy hole opened easily. I still enjoy the little bit of pain when I take the first cock of the day.

 

[Hunter22]

I started playing with cucumbers and such when I was about 12, I remember applying Vaseline on my hole and fingering it a bit.

The first time I pushed it in I felt a jolt in my hole, it was a combination of pain and excitement but the result was that after a few minutes I was hooked and couldn't stop.

I went through a lot of cucumbers before buying my first dildo when I was 14 and then soon after had my first raw cock up my hole.

It felt huge at that time (about 6") but he fingered my hole with some Vaseline, and was impressed how easily I took his first, the second and third finger before I he started pushing in.
That sensation of fear looking into his eyes and combination of fear and excitement feeling his raw cock head playing with hole before pushing in the head.

I felt the same jolt in my hole just like that first cucumber but the lust I felt took over and soon he was all the way in. 
It was both our first time and we took it slow at the beginning before he started increasing the pace.

he didn't last more than 5-10 minutes but it felt like he was fucking me forever before he busted a load in me.
I was hooked and each cock penetrated me since feels like that very first time.

oh, we ended up flip fucking each other the entire weekend dumping countless loads in both our loads. 

[suolsu]

Not really, my partner was smaller than average. I was 12, he was 17.

[ccmmss]

My first tine taking a real cock inside my hole was in my 30s. I had already been fooling around trading bjs and topping guys but had yet to get fucked. I went to a guys place and we got naked. Layed on his bed watching some porn and of course touching and fooling around. Giving each other bjs and admiring each other. One thing leads to another and I let him rimm me while face down on his bed. Now I really love being rimmed. Had it done several times already. Amazing how much tension we carry each day around our hole. Anyways. I had already used dildos too.... I was clean and looking for more. He knew I wanted him inside.

He lubed us up and made his way inside. I was nervouse of course but wanted it. He took his time. I am sure he could tell I was tight. Of course there was the favorite mome t we all love when they pop inside..... itt felt wonderfull... just slightly uncomfortable. He then fucked me for a good while until he need to unload. Since he was already bare he decide to pull out and shoot up my back. I could feel his thick heavy shots of cum land on me. Felt so warm. He shot alot. After he settleed down he cleaned of my back and I flipped over. My cock was rock hard. So he took care of that issue. He swallowed my cock and sucked me until I shot my globes of cum for him to swallow.

We relaxed for awhile then I went home. I couldnt believe what happened! It felt so damm good! Wanted more!!!!