The first time I enjoyed anal was with a bisexual man [MF]

By popular demand, you filthy animals. Here goes nothing…

I’ve mentioned briefly in stories that I’ve partaken in this particular act but I’ve held off on writing about it. Why? Anal is vulnerable and riddled with certain aspects that are inherently unsexy and kind of hard to write about accurately.

*Trust me, don’t skip those parts when trying this out. Preparation and aftercare are important.*

The first time I had anal was with the guy I lost my virginity to. I’ve never written about him. There’s not much to write unless someone on here has a fetish for missionary and unrealistic expectations of vaginal penetration.

The dude never went down on me once, hated experimenting, and told me using toys to get off while we were together was “cheating.” He’d get weirdly offended if I got myself off with or without him too.

*Men, please don’t be like this. Clit orgasms are a dream. I can orgasm through penetration and I still beg for this.*

So yeah, the first time I tried anal was not enjoyable. He made me feel selfish for asking for lube (so we did not) and he came inside me without us discussing it.

*Oh sweet, younger self. My heart goes out to you and your un-lubricated ass. Stay strong, little one.*

Years later, I am with someone far more experienced. He also happens to fuck men. We have fantastic sex and he introduces me to BDSM and a lot of sexual acts I did not know I loved.

He brings up anal early on and I immediately turn him down. Hard pass. No discussion.

He doesn’t push me but I can tell he’s a little taken aback. We’ve done fucking weird shit in bed so I’m sure this seems like an odd line. Still, he’s really good about boundaries and let’s it drop quickly.

After we’ve been sleeping together for a while, experimentations naturally move to that part of the body. I give him a rim job once while I’m sucking his dick in the shower and he double fingers me a few times to get me off. It feels pretty damn good actually.

I let him put a butt plug in and fuck me like that. I find I do really, really enjoy the fullness of double penetration and start asking for it.

Finally, one day as we’re in postcoital haze on the floor of my kitchen (*yes… we fucked in my kitchen quite regularly so he could incorporate “tools”*), he’s very gently circling my lower back with his hand and playing with my hair. He’s good at aftercare. It’s a nice moment. Im feeling open and amiable.

“Can I ask a question?” He finally says.

“No, we cannot go again for at least ten minutes.”

“I’ll give you another seven at most… but I’m legitimately just curious why you don’t like anal. It’s not a big deal but is it a degradation thing or something?”

“It’s actually a pain thing.”

“V… you just let me spank you with a wooden spoon and put ice on your nipples.”

“How would you like to be fucked in the ass?”

He starts laughing. “Dude, I’ve been fucked in the ass.”

“What?”

“Yeah… a few times actually.”

I knew he had been with men, but this is new… I don’t care that he takes dick, I just can’t really imagine this guy in any position that’s not 100% dominating.

“You didn’t hate it?”

He shakes his head. “You can fuck me in the ass if you want with a toy. I don’t mind.”

“It’s not extremely painful for you?”

“Wait what? Why would it be extremely painful? How big of dick did this dude have?”

“Idk, average?”

“Well what kind of prep did you try?”

I blink at him. I don’t understand the question.

“Omg V, you didn’t prep at all?”

I shrug.

“Did you loosen up with foreplay at least?”

I shake my head. “We just kind of went for it.”

“Aright…” he buries his head in his hands. “I’m almost afraid to ask. What kind of lube did you use?”

“His spit,” I throw up my hands. “But not too much because he said that would defeat the purpose if there wasn’t friction.”

Bro looks *horrified.* I’ve never actually seen him speechless but his mouth is wide open as he stares at me.

“Is it really that weird?” I finally ask. He’s not generally a jerk when talking about my inexperience but I’m starting to think I’ve said something stupid. “Why are you upset?”

“Because I’m kind of pissed of someone did that.”

“Ok well how is it supposed to feel?”

“Maybe slightly uncomfortable to start and then good.”

*Well this is news.*

“Aright,” I finally say. “Tell me everything.”

He explains in impressive detail the ins-and-outs (*lol*) of anal sex. It’s actually quite educational.

We have to take a break halfway through because he gets hard when he’s describing the feeling of railing someone like that. I make fun of him for it and he bets me an orgasm I’m wet too. He checks with his fingers. I am. We fuck again before he finishes his speech.

“Ok… so theoretically if I wanted to try this, you’d go slow right?”

“Obviously.”

“What if I wanted to stop halfway.”

He shrugs. “I’ve had to stop someone when they were halfway through fucking me like that. It’s no big deal.”

This makes me feel better. “And you’d walk me through it?”

“Yes, but I don’t want to unless you actually want to try.”

And damn it, I do. He tells me too think about it for a day and then if I still want to we can try the following evening.

*End scene and cut to another. I am not going into some of the preparation for anal. I’ve bared enough of my damn soul on here.*

After all of that, he actually does make
Me ask for it a few times to make sure I *really* want it. After the third time I finally just call him out for wanting to see me beg and he shrugs and says he can’t help it.

We take a couple of shots. This is actually rare because he usually doesn’t let me drink before we fuck.

*We get rough and he’s terrified of hurting me so he likes me sober.*

We make out for a bit on my bed before he pulls me over his lap and bunches my skirt up. He starts fondling my ass and I prepare to get spanked as usual. He feels me tense and whispers, “Not tonight, my dear.”

Instead, he licks his fingers and inserts them into me very, very slowly. My body tightens and he asks me if I want to stop. I shake my head and tell him to keep going.

He does.

It is not too bad. It doesn’t feel great, but it doesn’t hurt. He then pulls out a butt plug, puts lube on it, and slides it in. We’ve done this before so the sensation is familiar and easy to take.

“Do you want to fuck me like this first?” I ask.

“So… I’ve gotten off like six times today on my own.”

I turn to gape at him. “What?”

“I was afraid I’d come too fast! Plus… I got really turned on thinking about it.”

This actually turns me on quite a bit.

He continues. “I’m going to get you off first though… so pick my tongue or your vibrator.”

Oh, good lord it’s hard to pick. I finally pick vibrator because I’m nervous and want to come fast. He lays me back and plays with my breasts as he puts it right on my clit. He makes me look him in the eye as he gently moves it back and forth until I come.

He smiles as he sits back and asks if I’m feeling more relaxed. I nod. He pulls his pants down and asks if I’m ready.

“Well I was until seeing that thing again,” I say.

*Its a rarity to wish a dick was smaller.*

“I can get you off again,” he offers.

“No, no. We’re doing this.”

He turns me around and very, very gently removes the plug from me. He fingers me for a bit more and then puts lube on his fingers and goes deep. When he finally lubes himself up, I’m actually pretty turned on.

“Are you ready?” He asks.

I nod and feel him behind me. With one deep breath he pushes in and I brace myself for pain. However, he stays like that for a while and strokes my hair as I adjust.

“How does it feel?”

“Slightly uncomfortable but not too bad actually.”

He pushes in deeper. “And now?”

“This is fine.”

“I’m going all the way.”

I give him a nod and feel him thrust. I let out a moan, but it’s not terribly painful, just foreign. He stays inside me for a while like that. He reaches around to play with my breasts and rubs his hand over my clit a few times which is still sensitive from earlier.

“You’re so fucking tight,” he whispers in my ear. “I’ve been wondering for a while what’d it feel like to have every hole of yours.”

“Fuck me,” I whisper. I want him like this. I’m surprised by how much I want him like this but I do. It feels animalistic. I need it.

He goes in and out of me slowly, carefully. He takes his time to make sure I adjust to the feel of him and keeps checking in. He also keeps telling me how good I feel and how beautiful I am. Not only is it not hurting, it’s actually kind of feeling pleasurable.

*This is not how we normally fuck btw. We become different people in bed where I like being degraded and he likes doing the degrading. We usually get very rough, very quickly.*

Finally after the third “you’re beautiful,” I can’t take it.

“Do me one favor?” I ask.

“Anything.”

“Call me a whore.”

He pauses only for a moment and I hear a hint of a laughter before that magical switch. Suddenly, he grabs a fistful of my hair and whispers into my ear that I’m a whore. More specifically he says:

“You’re a whore who likes it in the ass right?”

“You’d take my dick any way I’d give it to you, huh?”

“You’re going to take this from me without complaining.”

*Yes! We’re back.*

I finally ask him for it harder.

“Im actually going to need you to beg for it.”

“Please fuck me harder.”

“That’s it?”

“Please fuck my ass harder? I want your dick so bad. Please be rough.”

He goes harder. He doesn’t exactly slam into me like our normal fuckery, but his thrusts become deeper and more intense.

He breaks for just a moment as he says, “Fuck this feels so fucking good,” but then snaps back to dominating mode. “You’d take it any way I wanted you to, huh? Even like this? Even this hard?”

“Yes!” I cry. Because I would. “Can I get myself off?”

“Only because it will feel better for me.”

He slams my head into the mattress as I reach my hands to touch myself. He tells me to go fast because he wants to get off soon and needs to feel my orgasm while he’s in me.

I don’t have to try for very long. Between my fingers and him behind me, I climax in about thirty seconds as he calls me a slut and slaps my ass.

“I’m going to come inside you now,” he tells me. “And you’re going to take it like that.”

My god it feels good.

The moment he’s out of me, he pulls me into the shower and holds me. I find this part important to include because you actually don’t know how your partner is going to respond to new sexual experiences. It’s confusing which is why aftercare is important.

As it turns out, my response is that I love anal. Not constantly, but it’s a very fun thing to occasionally throw into the sexual mix.

So a couple of morals here (1) lube (2) communication and (3) may your foreplay be as long and thorough as this damn novel I just made you read about ass fucking.

Source: reddit.com/r/gonewildstories/comments/rg1zmb/the_first_time_i_enjoyed_anal_was_with_a_bisexual