To paint a picture, I am a 23 year old woman Who has been intrigued by the thought of men’s buttholes for some time now. My ex, who I was with for five years, didn’t mind if I played with his from the outside but we didn’t experiment much with actual penetration. My new partner-who is a 27 year old furry hunk- and I have been seeing each other for three months. He had a virgin butthole when I met him. Anywho, Here is a true tale of a young couple expanding their sexual horizons.

It started about two months back. We were laying in bed one morning, indulging in some snuggles before starting the day. As he lay on his back, I rested my head on his chest while affectionately caressing his morning hard-on. I lightly ran my fingers across his dick, balls, and taint. We hadn’t spoke about butt stuff yet, and some guys are pretty freaked out by their own anuses, but I wanted so badly to feel his. I decided to introduce his booty to my finger. I was very subtle with my intentions. As I was petting his taint, I allowed a finger to wander a bit farther down and brush against his hole very gently. I could have played it off as an accident if need be, but he didn’t react whatsoever so I did it again. And again. I’d start at his dick and slowly work my way down to his gooch before giving his booty a quick, gentle stroke. Rinse and repeat.

Even though I could tell that my butthole-touching didn’t bother him, his lack of reaction made me unsure if he was actually into it or feeling neutral about it. That is, until we finished our morning snuggle session and he informed me that no one has ever touched him there before and that it felt really nice. Yahtzee!

Fast forward a few hours, we’re in the car on the way to our favorite coney for lunch. He brings up butt stuff and says he wouldn’t mind experimenting with it. The coney was closed due to a broken pipe or something, and the parking lot was completely empty. I tend to give him head in the car quite often, so you can guess what happened next. As I was sucking on him, he wriggled his pants down lower than usual and spread his legs a bit. I took that as my cue to play with his ass. This time though, I wasn’t so subtle. I rubbed and pressed on his hole until it sucked my finger in about a half inch. He was totally into it and erupted into my mouth.

So for the past two months, usually once a week, I’ll put my finger up his ass just a tad, and press on a certain spot while sucking him. It drives him crazy. He once gripped the shower curtain so hard during that he pulled the whole thing off the wall.

Until this past week, he wouldn’t allow me in very far. A few days ago he told me that he doesn’t like things actually UP his ass, and probably wouldn’t like any sex toys or baseball bats up there, but he enjoys the tip of my finger. He spoke to soon. Very soon after that conversation, (literally like twenty minutes later) I wet my hand with my own pussy juice and made my way to his rear end. I kept my hand still as he pumped his penis in and out of me, much slower than usual. When he’d push his dick into me, my finger would slide out of his ass. And when he pulled his dick out, my finger would re enter him. This time however, I couldn’t have penetrated him deeper if I tried. Eventually he stopped fucking me, and instead straddled my stomach while stroking his dick. I continued focusing on fingering him. When I removed my finger to re wet it, he frantically commanded that I “put it back in”. I was in heaven. He eventually orgasmed and we went about our day.

The next day (yesterday) we were doing our usual fooling around before bed. I wasn’t up for sex but didn’t mind lending a helping hand to my horny babe. This time however, I broke the lube out and got his asshole nice and slippery. I vigorously rubbed his asshole until my hand got tired and I had to switch.

“Do you think I could fit two fingers?” I suggested sheepishly. “I don’t know,” he responded. “I feel like two might hurt.” “Okay I’ll just stick with one at a time.” “I didn’t say we couldn’t try it out.”

So I inserted a second finger into his tight little hole. He let out a moan, so I double checked to make sure it wasn’t hurting. He didn’t respond verbally, just more squirming and moaning, so I continued rubbing and fucking his asshole as deep and hard as I could with not one, but TWO fingers, while he stroked his dick. About two minutes later he shot a massive load all over himself and the bed.

I think it’s safe to say that he does in fact, like things UP his ass.

My goal is to master his anus enough to where I can massage his prostate to the point of orgasm without him touching his dick. The only issue is that when I directly stimulate his prostate, it makes him feel like he has to pee, which he finds a bit distracting. The internet says this is normal but I’m stumped on how to get passed the need to pee feeling. Advice is welcome.

Thanks for reading about my recent sexual endeavors.