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

[Guest]

For me it was very sore.

[twinkasianboi]

I was 17 almost 18 and he was 36. We were taking a walk on a trail at night and he felt very horny. We hide behind a wooden fence and I gave my first bj. I tried to swallow and throat down his big thick white daddy cock, but I kept gagging and choking. All the sudden he lifted me up, turned me around, leaned me against the fence doggy style, and pulled down my pants and boxer briefs. I was excited to finally get fucked because of all the porn I watched as a child. He went down on me and ate, licked, and tongue fucked my hairy virgin hole. He stood up and pressed his fat head of his white man cock against my tiny pussy. He whisper, “you want this man cock to be your first?” Of course I begged him to fucked me, but he knew I was naïve. At that moment, I never felt so much pain! His raw unlubed cock forced its way into me and I kid you not, I collapsed on the floor to get away from his dick. He did a few more thrust to teach me a lesson for trusting a complete stranger over grindr. He pulled out and turned me around to kiss me and gave me this warning, “don’t go bareback with anyone or they might give you aids.” However, after a few more years, that same clueless bottom would turn into a willingly bug chaser and beg for a top to give his neg hole multiple poz loads. 

[Guest]

My first time wasn’t the best. I was 15 or 16 and my boyfriend was in his 40s. We had been dating for several months . We first met online in what was planet out at the time & spoked for couple months before we met face to face. We dated for several months before I lost my virginity. Sex was all oral until I turned 16 as I wasn’t ready. When we finally decided it was time I would say the experience wasn’t enjoyable at all. He was sweet, romantic, and slow to not hurt me however I was just in extreme pain. On top of that I didn’t know wtf being a bottom entailed and since he and more experience than I about sex he coached me throughout and told me what to do. It honestly took to our 4th or 5th time before I finally relaxed and started to enjoy sex. 

[YourNoLimitsBottom]

I wasn't sore the first time. His cock was on the thin side, and I had been fucking myself with average sized dildos for a long time prior to working up my courage for that first real meet. He was enthusiastic, but I didn't hurt after.

[Marlin]

I tried bottoming a few times when i was younger but it hurt so much I had to give up. Frustrated I started playing with my hole and using a candle and vaseline as a dildo. I remember how intense my orgasms were with that candle pressing against my prostate. I soon bought a dildo and learned to relax more and push out a bit as pushed it in. One day I was with a guy I was dating and as we were making out I asked him to fuck me. He had an average dick, I lubed it up, bent over and as he started to slide in I pushed out opening my hole. To my surprise it didnt hurt and obviously felt great. Within a few minutes I hear is breathing getting heavier, his dick expanding and his dick balls deep. Suddenly he stopped and I could feel his dick pulsing in me. He stayed in softened. and slid out with some his cum dripping down my balls......I was now truly versatile 

[tony0040]

Not at all, I'd been trying to tempt him for weeks, the exitement & his pre-cum as lubricant made it intensely pleasurable!

[Rillion]

First time was with a friend when we were both 12. We didn't know about lube so it was very painful and we stopped. Later I learned about lube and dildos so when I tried it next at 23, there wasn't any real pain, just the slight discomfort of a condom.

[bbslutuk]

In short, yes, the first time hurt a little bit, specifically at the beginning. I was 17, limited options on getting lube or a dildo, so before I met up with the guy, I was just using spit and my fingers to prep for taking an actual dick. 

 

However, I was very lucky that my first time was with an older and experienced top, he quite quickly picked up when he slid inside me that it wasn't feeling too great for me, helped me with more foreplay and ate my arse, then once he tried getting inside me again, we took it very, very slow whilst fucking.

 

It did hurt the first couple of times, but after that I found it was pretty much fine. Obviously dick size plays a factor as well, it's easier to take a 6 inch average girth dick compared to a 10 inch, heavy girthy bastard lol! 

 

My personal advice to those who are brand new to bottoming would be: 

1. Practice in advance by yourself, get used to the feeling of your fingers or a dildo inside you 

 

2. Use lots and lots and lots of lube, there's never too much! My personal favourites are called 'Spit' and 'Spunk' and both are affordable (I literally used the 'Spit' lube at a sauna in Blackpool this weekend when receiving anal and it's a great lube)

 

3. If you're able to, get some buttplugs and work up the sizes, you'll find your butt gets way more used to them if you practice semi-regularly 

 

4. Tell the top if it's hurting, be honest with them, take a break, lube up more and use some toys first before they get inside you 

[Bokkierob]

I was 14 and he was late 30s. I knew him well (he was my buddy's dad) and I'd been sucking his cock and swallowing his loads for quite a while. He said I was ready to take his cock up my ass. I really wanted it. He lubed my hole real well with spit and very slowly penetrated me. It wasn't painful - maybe a bit uncomfortable. His cock felt massive going up my ass and when he was Balla deep in me I felt so stretched and full  but he was very careful and fucked me slowly. It wasn't very long before he shot his load. He stayed inside me until he got soft. So, no pain and  a great introduction to fucking

[Bttml00king]

I don't remember how painful it was when I was getting fucked the first time. My buddy and I were both drunk. He fucked me in the middle of the night when we were sleeping. I wish I could remember more than just a cock entering my hole.

[BlindRawFucker1]

Surprisingly, it didn’t hurt at all.

 

He was older, and took his time first using a small, very well lubed dildo, then his fingers, then his tongue.  When he ate me, I felt extremely embarrassed and ashamed.  Then, with the pleasure, I thought to myself that I didn’t aks him to do it, and he seemed to really enjoy it.  After that, I totally relaxed.

 

For my first penetration, he had me sit on his dick so I’d be in complete control.  Once I got used to him, I got on my back and he fucked me.

 

I couldn’t have had a better first time.

[Fillitup57]

put it ths way it was a long  long long time before anyone fucked me again and now I live to be fucked and take cum deep 

[badjujuboy]

For me it was painful at first. It didn’t help we were drunk HS kids and it just happened with no thought to lube and prepping. I realized it’s not like in the movies. Luckily it wasn’t “messy” and the pain subsided but I could feel I had been fucked for a few days after.

I also had a buddy whose first time went badly as his bf was huge and caused some damage the first time… again with no planning. 

[VersGuyAnon]

It was more painful after than during the fucking. The lube used was Vaseline, which wasn't exactly that helpful!

[Guest]

Was a bit painful, we were pretty unexperienced kids, I was standing and my face was against the wall and the top who was about 4 years older than tried to penetrate me without a lube, then used his saliva, he pushed all his dick deep inside me, he didn't take it slowly and lasted only few seconds, we were both scared someone could see us, as we were fucking in a playing ground.