Will bottoming always hurt?

[alizia]

I really agrre with the "relax and lube" idea here.

Although I am only be topped by my Mistress-GGf with a strap-on I hope I can soon enjoy a real cock and compare both pleasures and "pains" strapon-real

[kfortune]

My first time was in a rather lust-fueled meeting. He rimmed me to get me wet (he didn't like using lube) and I was too excited / nervous. When he fucked me doggy it really hurt and I had a flash of inspiration and suggested I get on top. I was able to control the speed of penetration and felt more in control. After that, it was awesome.

It got easier and easier the more he fucked me.

[Ryz]

Do lots of coke

[Chase_Mcthirsty]

actually i was topping a client recently (in last week) and i had taken 2 viagra jelly in the morning .. i was sporting some pipe he got his ass destroyed to the point he was crying on the bed lol i just said well you have paid for the hour and i am going to fuck you for the hour mwuahahahaha . alas he only last 10minutes ..

..........Fucking rookies.

[Chase_Mcthirsty]

So true. Adding to that, it also has to do with how concerned she is with your pleasure. I'll give examples.

I've bottomed a grand total of four times.

The first was with a "working girl" (back when I wasn't too proud to trick). When she first started to penetrate, I felt an extremely intense pain, but she did a good job relaxing me. She talked me through it and told me to take a deep breath as it was going in. It felt so damn good after that. However, the pleasure didn't last that long because she couldn't keep it up (not her fault. i understand what comes with hormones). So, I proceeded to fuck the shit out of her for the rest of the session.

The second was with a girl (non-working) that I met on adultspace. That was the best sex I'd had in my life at that point. When I bottomed, I initially felt that same extreme pain, and told her to take it slow. She was really patient with me, and I felt relaxed. Before I knew it, the intensity of that pain had transformed into an intense feeling of bliss and ecstasy. I feel like that fuck really made me understand how girls get pleasure from being fucked. I was moaning like a bitch. I then fucked her, and proceeded to go straight to sleep.

The third was a girl (non-working) I met on CL. She said she wanted someone to bottom for her. I was down. This turned out to be the type of fuck in which I was hoping for her to hurry up and be done. This wasn't even because it hurt. She was just not into trying to make it feel good for me at all. Once again, it made me kinda understand how girls (both GG and TS) feel. As a matter of fact, I think bottoming has made me an exponentially better fucker of GGs, but that's a better story.

The fourth time was with a TS friend of mine who I met years before. Previously, we had done just just about everything short of intercourse. She had a boyfriend, and considered intercourse to be cheating, but not everything else (i.e., oral, frottage, sleeping in the same bed, etc.) Well, long story short, we fucked last year. I topped first. Then when she topped, I didn't get that much pleasure out of it. I don't know if it was because I already came, or if it was because her big dick was continuously hurting me. However, she came pretty quick so it was over soon anyway. I felt relaxed with her, because I knew her. However, I think that "skill" thing that you mentioned (or the lack thereof) may have played a factor.

So the moral of the story is: yes, it does depend on the girl (at least for me, it does).

You should've kept the 2nd girls number.

[TGasMutiny]

son if you pushed back i will just driill in harder and harder until i split you in two

You are awesome Lib!!!!!!!!!!!!

[jm813]

Honestly the bigger the dick the less it hurts. The smaller ones tend to almost pinch as they go in and out.

[Westheangelino]

One word: poppers. Once you pop, you can't stop.

[Lovecox]

I started this thread and I would like to update.
I bottomed for a TS and it was really fucking hot! I think there were three factors that contributed to this being pleasurable and not painful.
1. I've known her for awhile and feel comfortable around her.
2. She licked and sucked my ass for a good long while first.
3. Her cock is not too big or fat.
It happened really naturally. For me getting eaten out first really put me in the mood. When she started rubbing her cock on my ass I felt really ready. She took her time. I was definitely relaxed and was able to enjoy it. It was really great.
She's not as hot as the other one but I definitely want to see her again. Maybe it's all chemistry.

[BeardedOne]

I've been with small, average, and large (Try thinking 10"+) and it's all relative to how receptive you are and how co-operative the gurl is. Don't shake off the gurls that are seriously blessed so long as you can follow the basic rules of 'relaxation, lubrication, and communication'.