[MF] She wanted to try anal, so of course I said yes

My girlfriend at the time Audrey wasn't exactly the most adventurous woman I've ever been with when it comes to sex, but she was always a good time. Both in sex and in life, she was incredibly stubborn and knew what she liked and what she didn't like. I respected that, and in a lot of ways to led to better, more reliable sex when we weren't constantly trying new things.

That being said, it certainly caught me by surprise when we were doing it doggystyle one day and she asked me to stick a finger in her ass. I asked if she was sure, and she said yes. I reached a finger down and rubbed the outside a bit before going in. She moaned and asked me to keep doing it. After about a minute of doing this while I was fucking her, she came harder than she had in a while.

After we were finished and were laying in bed together, I asked her what that was all about. She said she had tried it recently while masturbating and thought it felt good so she wanted to try it during sex but had forgotten about it until that moment. I had only one thought on my mind after this, but I knew that I had to choose my words very wisely or else I might risk blowing the whole thing up. I ran through a few possibilities of easing into the conversation, but I'm pretty sure in the end it spilled out of my mouth like one word, "wannadoanal?"

She laughed and looked up at me to say, "Let's ease into it. I trust you to be good about it, but you're also very thick, and that kind of scares me."

We were both 24, but neither of us had ever done it before. My first serious girlfriend had a strict no-butt-stuff policy and I strongly respected that. Audrey had had boyfriends inquire about it in the past, but like I said, she was stubborn, not very adventurous, and I think a little scared. I assured her that I would take it as easy as she wanted, and "do research" on it. That meant us laying in bed together watching amateur anal porn and studying it like we were watching the Discovery Channel or something, which is a fun memory to look back on, especially thinking about how two young people overhyped it in our heads to be some magical thing that had 99% chance of ending in tragedy unless we were super duper careful. There's also this certain mystique to it that works its way into your head from a young age through every sitcom and comedy movie using it as the "special birthday surprise" wives give to their husbands that make them jump with joy and smile ear-to-ear. You start watching porn and see the girls either treat it like it's nothing or act like they're in the worst pain imaginable, with little in between.

It started the next time we had sex. We decided that, as part of our foreplay, we would do some fingering and work our way up to see what she's comfortable with. I gently teased her anus with my finger again, causing her to pucker up. Eventually I stuck my finger back in and she moaned softly.

"Does that feel good?"

"Yes," she said, "keep going."

I went a little deeper with it, taking it very slow and feeling her body for signs. Soon, I was down to my knuckle, lightly stroking the inside.

"Do you think you can try two?" I asked her. She scrunched her face and nodded. I pulled my finger back to the first joint, and tried to slip my middle finger in as well. There was some resistance, but eventually it went in as well. She let out a short, "ow."

"Should I stop?" I asked. She shook her head. I was up to two joints in with both fingers before she tapped out. Still, a good first exercise! We continued having sex as normal and when we were done, I brought out some of her tailor's tape. I don't remember the exact measurements I got then but I can't imagine they're much different from the measurements I'm getting right now: my index and middle finger together are just about 1.25 inches (3.175 cm) wide. My penis at its widest point is roughly 2.1 inches (5.334 cm). I argued that we were already over halfway there! That's ignoring circumference and length, of course, but I wanted to keep her upbeat and motivated.

The training continued both with me and on her own, and she got herself some toys as well to help. After one of her solo training sessions, she texted me:

"I think I'm ready."

The next time I was over at her place, we did our usual routine of drinking a glass or two of wine, watching an episode or two of whatever show we were watching at the time, then getting down to business. Everything started normally with some light-hearted foreplay and laughter, but it was clear that there was a mission this time. We made sure she was fully cleaned/prepared and the lube was at the ready.

"Do you want to just jump right into it?" I asked her.

"Let's do things normal for a bit so I can prepare myself," she said. I think secretly she was hoping I would get carried away fucking her pussy and finish before we had the chance. I made a point of being extra sensual with her, giving her lots of kisses and making slow rocking motions with my pelvis. Everything I knew she liked. I reached a finger down and inserted it in her ass. She moaned, and I stuck the second in. Soon, I had stopped fucking her entirely and was focused just on this.

"Are you ready?" I asked. She was apprehensive, but agreed. I knew that she was a little bit paranoid still, but that she really wanted to do it. She was on her back, so I scooted her a bit to make sure her asshole was at the right angle. I lubed up, and poked the head to it. She puckered up and tensed her muscles.

"I'm not going in just yet, just teasing the outside," I assured her. I rubbed around the outside, and she had her head up watching me the whole time. She started to ease the tension in her body.

"Go," she said. I started to push a little forward, but she reflexively moved herself back. "Sorry, sorry," she said. Each time I poked her, she did the same thing.

"Would it be easier if you faced the other way and couldn't watch?" I asked her. She agreed and flipped over to be on all four, her round little ass up in the air and her face down in the bed. I got behind her and back into position with my cock just outside the gate. I rubbed against it a little bit until she was comfortable again, then poked in. Her ass sucked up my head with surprising ease. She let out a soft yelp and stuffed her face into her pillow. I massaged her back and told her it would be fine. She pulled her head back up and breathed out.

"Oh fuck that feels weird," she said. I had to agree with that.

I can't even tell you if I was actually making any in-and-out motions or if our bodies moved together because the head didn't really get any deeper or shallower, just kind of rocked along with us, but I was trying my best. It was shockingly tight, which I guess I should have already known it would be. Audrey was quite petite and had a very tight pussy as well even when fully aroused, but this was far beyond that. Soon, she gave me the go-ahead to push a little deeper. I held onto her and pushed until I was about halfway in, just before the thickest point of my cock. It was at this point that giving her true strokes became easier. I pulled out until it was just my head inside her, then pushed back in to that halfway point. Her groans turned to moans pretty quickly.

"Does that feel good?" I asked. She nodded.

"Deeper," she said. I pushed past the thickest point and eventually as deep as I could go.

"Okay, that's it. I can't go any further," I said, "feel better about this?"

She nodded.

"Happy you tried this?" I asked.

She nodded again.

I pulled back halfway and pushed back in, then did this a few times before I started making slow full thrusts. She had reached her hand down under her stomach and was rubbing her pussy while I fucked her ass. She said after that it was the strangest feeling she'd ever had, where she could feel me stimulating her pussy from the other side of the wall. That is apparently a common experience, but I'm a dude, so what do I know? I'm just telling you what she told me.

Her ass was so tight I could feel myself getting ready to cum even with my slow strokes. I was going at the pace I would normally go to "slow things down" and "reset," but the grip on my cock was so pleasurable that it didn't matter. I felt incredibly lucky when I felt her tense up and throw her face back down into the pillow and scream as she came. She lifted her head still moaning and I felt every ripple and shake through her body. It was certainly a unique experience. I came almost instantly after, filling her ass with my seed. I apologized for that since we hadn't really discussed where I was going to finish, but she said it was fine and felt great to feel my cock throb and pump in her ass. I slowly pulled myself back and popped out of her hole.

We did some thorough cleaning of the workstation and ourselves, then went off to shower together. After, we laid back down in her bed and discussed it. She said it was probably the most unique and intense orgasm she'd ever felt and that she wanted to do this more often, though, not every time. I tried to put into words to describe how tight it felt, maybe as tight as the firmest grip with my hand but covering my entire cock like a sleeve. All in all, we both had a great time, and she found a new love of anal.

After a break without trying it again to let herself recover, she was back asking to do it again. We started doing it harder and faster until we were practically pros. I've described her as stubborn, but it's kind of hard for me to describe how intense her personality was outside of our relationship. At work, she was the hard-ass boss that everyone was afraid of. She was the bitchy friend that was always speaking her mind and keeping people in their place. With that image in mind, there was something incredibly sexy about the way this girl started actually begging me for anal after this. There was something crazy about walking into our shared workplace and hearing her employees talk about how hard she is on them, knowing that less than 24 hours earlier she was on all fours begging for me to fuck her in the ass.

Now you're probably expecting me to end this story by telling you how much she became an "anal slut" or something of that nature because that's how most of these stories go. Truth is, after the novelty wore off a bit and we were kind of used to it, as with many things, we fell out of doing it so often and went back to our usual routine. That's not to say she didn't love it... she absolutely did! Probably more than I did, if we're being honest. It was just a fair amount of prep work and pain to tolerate on top of the pleasure. Still though, the seal was broken. It wasn't a taboo anymore, and it was something we could do when we were in the mood. That's all that really mattered. This story was still one I figured I'd write up and post. Maybe it will inspire someone else to stick a finger where it doesn't belong and break the taboo.