Losing My Anal Virginity [MF]

All right everyone, let me tell you about the time I lost my anal virginity. This happened just over 24 hours ago with my [22/F] boyfriend [29/M] of a few months. For some background, he has had anal sex before but I hadn’t ever – only some light anal play, maybe a finger on occasion, that sort of thing. For some of the cute background on our relationship because I’m sappy and have an emotional approach towards sex, we’ve both said one of the main things that attracted us to the other is that we’re both equally goofy and silly. We joke around a lot and have a lot of fun teasing each other. I have a tendency to be a tad bit high strung while he’s very mellow, so we balance each other out nicely. All in all, he’s fantastic and last night only proved this more.

Getting to the interesting part, we spent the whole day together yesterday. We went out canoeing early in the morning, headed out to browse some of the festivals going on in a large city about an hour away from us, took a nap, and just generally enjoyed letting the day take us where it may. We had been discussing the idea of anal after playing around with a bullet vibrator we had used on my ass a few times, but last night I could feel that the timing was right. So we grabbed some silicone lube and hopped in the shower (for easier cleanup just in case).

Now, I’ve previously been in a relationship with an almost germaphobe, so I was absolutely PETRIFIED at the thought of accidentally… well, y’know, during anal. So, being the silly girlfriend I am, I say this as soon as I hop in the shower: “I have a very serious question that I hope you’ll answer honestly. Are you still going to love me if I poop all over your dick?!” We had a good little laugh and started hugging and kissing really slowly and sensually. Our bullet vibrator was waterproof, so I had the idea of bringing it into the shower with us to get me “prepared in steps”, so to speak. He gently lubed up my ass and slid the bullet in. Since we hadn’t played around with it too many times, this was still a fun and exciting new sensation, and knowing that he had control of how/when/with what intensity it was going to vibrate turned me on so much. I turned away from him and got on my tiptoes with my ass out and let him slowly begin to fuck me (vaginally). Things are getting hot and heavy while he’s changing up the mode on the vibrator at just the right times, fucking me harder and faster while I’m rubbing all over my clit. I can’t help but moan out and I feel myself getting wetter and more turned on every minute. After a bit, I decided it was time to do this thing for real. I took out the bullet and wrapped him up in a wet, slippery hug while we started making out again.

Now, normally my boyfriend likes to be a little rough with me in terms of biting, which I love. Having leftover bruises that remind me of just when he was biting my shoulder or tit at the right moment is a sexy little treat every time I see myself naked in the mirror. But this time, he was ever so gentle. I’m not sure if it was what felt right to him in the moment or the fact that I had been telling him he’d have to be gentle for my first time, but this man was sensually brushing his mouth against my neck and nipples and body in all the right ways, kissing all the right places. He starts rubbing circles around my clit while I’m basically incapacitated and dripping wet. I start begging him to fuck me at this point.

So there I am, body soaking wet from the warm, steamy shower, pussy soaking wet from this fantastic man and the things he’s been doing to me. I’m turned away from him, on my tip toes due to our height difference, legs spread with my tight little virgin asshole exposed, completely and utterly vulnerable. Because of the trust I have for him, I know I’m in good hands and I’m *so* turned on, yet I’m still nervous (obviously!). After applying some more lube, he starts to slowly slip the head inside of me. For a split second, I didn’t think I was going to be able to take it all. My confidence was a little shaken by how big he felt inside of my ass already, but I was so turned on and ready to keep going, so we pushed forward. After a few gentle and slow thrusts, we gradually started working up the pace more and he slowly slipped all the way inside of me, hips straight pressed against my ass. I couldn’t believe he had already gotten all the way in! It was FANTASTIC. He was so deep and it was so incredibly hot! Albeit a little uncomfortable at times, I communicated what felt okay and what didn’t, let him know when to ease up and when to go faster, etc. and he listened and responded so wonderfully.

As the slight discomfort faded, I found myself getting more and more into it. He was sliding his hands all over my ass and clit and tits, holding my hips while he fucked my ass harder and harder. I kept moaning and gasping, totally wrapped up in pleasure. At his suggestion, I started playing with myself. I was rubbing myself faster and faster while he fucked me, sliding my wet, lubed fingers over my throbbing clit. I felt myself coming to the edge pretty quickly, and when I came… Oh man. It was an amazing sensation! I have very intense orgasms with PIV and clitoral stimulation, and this one was almost more intense. It was different to come that hard while he wasn’t inside of me “like normal”, but super sexy. My legs were shaking and I kept gasping and moaning his name, oh god, fuck, etc. the whole time. I had the biggest, dumbest grin on my face after that and we kissed while he was still inside of me.

From that point on, I got even more into it. My arms and face were pressed up against the shower wall while he all but rammed my ass as I started bouncing back onto his dick, begging him to “Fuck me, fuck me, FUCK me!” Watching him getting so into it got me going so much that I almost came again without even touching myself! I loved the feeling of his sexy, strong hands grabbing my hips and tits while he fucked my ass faster and harder.

I did reach my limit after a while, but we thoroughly cleaned off and finished things regularly outside of the shower. (Well, a slight mishap occurred there. Long story short, wait for your ass to go back to normal before riding your boyfriend too hard after anal. Thankfully he wasn’t bothered and claims to still love me, so that’s good! Lesson learned though!) I’m not going to lie, I did have the sensation of being right on the edge of using the bathroom while I was getting “accommodated” to his size, but that obviously passed as we got more into things.

Overall, I had an absolutely incredible experience losing my anal virginity. I was interested in trying anal before this, but only just recently – and I definitely did not expect to enjoy it as much as I did! If anyone out there is on the fence, I’d encourage you to give it a try. With the right partner, good communication, and plenty of lube, it can definitely be done right the first time, as I learned. And now I feel even closer to my wonderful boyfriend and have found a new favorite sextivity as well! ;)

Source: reddit.com/r/gonewildstories/comments/67jsgq/losing_my_anal_virginity_mf