Go Gently the First Time

I really wasn’t sure why my boyfriend Kyle was so set on having anal sex with me. I’m young, tight and very pretty. And I have a hot body too. Not being arrogant, I’m telling the truth. But he kept insisting and finally I decided if it means that much to him, I’ll try it.

“Ok, Angie, be really still,” he said.

“I will,” I replied. What else could I do? I was on my hands and knees in the middle of the bed, my ass and pussy were up in the air. I could feel my knees trembling, so I guess he thought I would panic.

“I just don’t want this gel getting all over you. You won’t be able to feel anything, not even your pussy. And you don’t want your ass cheeks to sag, do you?”

I started to giggle and we both laughed. He was being really cool about it all. The joke was funnier, because the first website we found about the gel was this Russian one, and instead of a good translation, it warned “Caution, can cause anus cheeks to numb.”

Must’ve been the funniest thing we read about the stuff. And I walked around the bedroom naked, pretending I couldn’t feel my ass, knees bent like a monkey, and saying I couldn’t feel them anyway. We both had a good laugh about it.

“Here goes,” he said and slid his finger in and sort of finger fucked my ass for a minute or two. “Shit works,” he said, “I can’t feel my finger.”

“Want me to pull it?” I asked and we both cracked up. “Seriously, I can still feel my ass, though.”

“Do you feel me bending my finger?” he asked.

“Yes,” I said.

“It isn’t in your ass, Angie,” he said, laughing. “You’re anally paranoid!”

“Really?” I asked. “You really pulled it out?”

“Yes,” he replied. “The only thing in there right now is air.”

“Cool,” I said.

I readjusted my knees to get in a better position. I wiggled my ass at him to tease him and lowered the front of my body to give him a better target. I could feel him rubbing my ass cheeks and admiring them. Then I could “feel” him applying lube when he said he was.

We’d been playing with small butt plugs and even a medium sized one once. This was the big event. He was going to fuck me up the ass, real anal sex. And I was still nervous, but so horny I could pop, because he had already fucked me twice that morning.

He started fingering my pussy and tweaking my clit. I asked him what he was doing and he said that he had to wait a while, or the stuff numbing my ass would numb his cock and we’d be there all day. Then he laughed, but I was concentrating on my swollen clit and the orgasm he was about to give me. He kept going for what seemed forever and when I came, it was a long, total body orgasm.

But before I could catch my senses, he was behind me. “Tell me if it hurts, ok?”

“Ok,” I mumbled.

I could feel his rock hard cock slapping on my tailbone, and then he pressed it against my anus. When he entered, it did hurt just a little. But no way in hell was I going to stop him. We’d come this far and I was dead set on seeing if it was as good as my girlfriends said it was.

His shaft was sliding deep inside me, and I could feel his balls slapping against my pussy. It was weird because I was expecting to feel something totally different, but his balls slapping me and the internal massage made me come again and all I could do was moan.

That drove him insane with excitement and the next thing I knew, he was pounding my ass like a pile driver. Every thrust was powerful and manly. I felt so vulnerable and happy at the same time. I felt like a lucky woman.

When he was ready, he pulled out and rammed his hot bone into my soaking wet and hot pussy, which made us both come at the same time. I don’t know what sounds I made because I was too exhausted and happy to think about anything except my orgasm. And we laid down side by side and kissed until we were both exhausted and fell asleep.

We’re anal pros now, but that first time will always be the one I remember.