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Extremely Painful Anal Sex

SilverRRCloud

I'd rather be a Sexgod:)
Joined
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I met this 'Joe' on a professional function couple of months ago.

He is in his late 20's, nicely-shaped but not buff. Smart, pretty successful, friendly kinda guy. My gaydar went into overdrive and we soon agreed, we were playing on the same team, as the saying goes.

Towards the end of the following day, he accepted my invitation for private drinks in my suite. (Yeah, I was putting all the moves and sure, I was looking forward to getting into his pants. He was more than responsive and willing, too.)

You probably know the score: one thing led to another and we were soon going at it.

Frankly, I was hoping for a good BJ but he offered more. He even came pre-lubed.

I took it nice and easy with him, as he was rather tight and claimed he was rather 'new' to all this anal thing, though, he liked it very much, etc..

K, so, I took my time and gave him a slow break-in. Judging by his facial expression, he was going through some serious pain and yeah, he was slightly tearing up.

I stayed on the course and wanted to grant him a little break once I got in. Suddenly, he grabbed my hips and impaled himself in one swift move onto my dick. It looked like he had passed out for a few seconds. His breath intake was sharp and irregular, he was tearing up profusely (something I have never seen before) and his facial expression was indicating that he was going through some serious torment.

I decided to stay deep in for a moment, for him to readjust to the intrusion, when he started the slight rocking motion. I took his hint and was soon pounding him with all I could give. He was actively encouraging me both verbally and by meeting my thrusts...

Yet, he never stopped crying and tears were going down his cheeks freely. Again, his facial expression was that of an awesome pain.

For all his obvious pain and suffering, he was more than just a good sport and took it really like a man.

I was pretty sure that he would not wish to repeat such a painful experience again.

I was wrong. He is now in town and he just phoned in. He obviously wants more of the same.

---
I have never encountered the extreme pain+tears situation and am slightly off balance here. I have no intention of turning this dude down either. If he gets off on massive pain, let this be his problem.

I am wondering, if anyone else has experienced anything similar, and what would be your take on this?

Thanks:)

SC
 
Some people seem to have the belief that if they are going to get fucked, it has gotta hurt. Something like no pain, no gain...or "If I am going to be fucked, I'm going to know about it." The pain is the pleasure.

In your situation, I would do as you have done. Take it slowly and be considerate but if you get messages that he wants to be really fucked, then satisfy his needs. Please just make sure that you do not do any physical injury.
 
Yup. He likes it hard and rough. The tears meant you were doing good!

Don't worry about it. If you were too rough and he wanted you to stop, he can always say so.

If he called for a re-match, then you were doing very good! ..|
 
Wow, your story got me all horny but...

If he was all that teary but still was hesitant, I guess he did enjoyed some of it at the end. He wanted to have another rematch that meant he really enjoyed YOU. hehehe. After the second time with him, will you tell us the story?
 
yeh...your recap of the encounter rather turned me on a bit too....:lol:

The song lyrics "Hurts so good, come on baby make it hurt so good..." came to mind.

Perhaps, to ease your concerns, discuss a safe/code word to use in case it gets too rough for him.
 
Thanks, guys. Good advice as usual here.

I am slightly off-center here, to say in the least as I have never had a bottom willingly experience pain during your usual vanilla anal sex throughout the action. I felt slightly weirded out by his massive tearing up and all.

I agree that he must have liked it, now that he is asking for a re-match...

I'll definitely think about the safe word, though we have communicated quite well during our first steamy encounter.

Thanks, again, guys...

SC
 
I'm a bottom. No one's ever told me that I "tear" or what not.

For any tops, I'm just curious what's that like.
 
I'm a bottom. No one's ever told me that I "tear" or what not.

For any tops, I'm just curious what's that like.

Dude,

I did not tell him to tear up. He did it on his own and once the tears started flowing down, they would not stop for as long as I was in...

SC
 
I understood your story plain and clear...

In case you hadn't thought of this, it sounds like this guy might like to wrestle and be handcuffed and fucked this next time.
 
I understood your story plain and clear...

In case you hadn't thought of this, it sounds like this guy might like to wrestle and be handcuffed and fucked this next time.


Thanks...

Nope, I don't think so. He never indicated, he'd offer any resistance whatsoever, even for the sake of a roleplay... He is showing sufficient submissive traits that I see no point in handcuffing him at all...

What would be the point in 'forcing' someone, who is more than willing? Play is fine, but even play has to bear some correlation with reality...

SC
 
Again, you understand 0% of my post.

You don't HAVE to handcuff him. If you HAVE to handcuff him to fuck him, then ... you might want to reconsider your life plans. I am just saying ... the type of guy this person sounds like, he might enjoy being handcuffed ... and fucked hard.
 
Reminds me of Janet Jackson's song, "That's The Way Love Goes". The lyrics are: "Oh baby, don't stop , don't stop. Go deeper, baby deeper. You feel so good I'm gonna cry!" Sounds like he's loving it to me.
 
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