What was your first anal sex experience like? Is there any way to make it feel less painful the first couple of times?

It was brutal. I was thirteen, and I had just finished sucking off three older boys in the woods near my house, when, without warning, one of them just pushed me down on my back on a flat rock, put my legs over his shoulders, and plunged his cock deep into me with all his weight, no lube.

He held his cock there for about two or three minutes, gloating that he had popped my cherry. The pain was unbearable, and I begged him to take it out, but he and his friends just laughed.

Then he started fucking me hard and deep. Every thrust took my breath away, and I thought I was going to pass out. All I could do was wimper and beg for mercy. I finally gave up resisting, and tried to ease the pain by being cooperative, but to no avail. He was determined to make it as painful and humiliating as possible.

He lasted a long time because I had just sucked him off, but as he was cumming, I heard one of the other boys say, "I'm next". Then I realized that all three of them were going to fuck me. The second boy was even more brutal, and so was the third.

After they were finished, they got me dressed, took me to one of their houses, and got me washed up. They patted me on the head and told me I had been a good faggot, and that they would be using my ass a lot in the future.

They fucked me two or three times a week for the next few months. After a couple of weeks, I started getting some pleasure out of it, but the initial penetration was always incredibly painful because they never used lube. Sometimes they would invite a friend or two to join them.

terrible!! OW!! Try using a small dildo by your self for a while until you get use to it. You can also try the desensitizing cream/gel

Not too shabby.

Start with smaller stuffs like a finger, and work your way up in sizes.

It hurt like hell. Now after while the pain became pleasure but it still hurt. That why I dont do it often.

To Scotty S. I have so many fantasies about what you wrote. Only I would love to be wearing panties, a jog bra a nylons. I've yet to be penetrated by someone butt I want to feel that and to walk and squat ackward for a few days just to remind me that someone was inside me and treated me like a c....

My first experience was awesome. Everyone says lot's of lube, and I agree. But I lubed up with capt Morgan's first, and he used lots of lube on his cock. I did feel some pain, but I was too horny to care.

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