First time anal with a girl did not go as expected [MF].

This is the first time I’ve written something like this, and I’m also not great at writing in general, so I apologize if this is hard to follow. Now a bit about myself and the girl in this story; My dick is above average, at 7 inches length & 6 inches girth, and that’s the primary reason this girl and I are FWB. I met her at an orgy last November and we’ve been having sex every so often since. She likes thicker dicks and enjoys it when her cervix gets bumped by a penis during sex. I don’t fully understand how it’s pleasurable but if it works for her it works for me. Now on with the story, sorry it’s a long one:

Yesterday around lunchtime I get a snapchat message from a girl that I’m FWB with and she says “I want that big dick”. Feeling sporty I respond with “where do you want it?” and she then sends me a picture of her asshole. I’ve never done anal with a girl before so she now has 100% of my attention. The rest of the work day was dreadfully slow and boring, cause all I could think about was that booty hole. I’d thoroughly eaten it out before, but now I’d get to fuck it.

She arrives at my place round 7pm and as soon as she’s through the door she’s headed to my shower, throwing off her clothes as she goes. It’s an ok sized shower, enough for 2, but it also has a sauna feature. We both get into the shower, turn on the sauna, and set the timer for 10 minutes. I then turn the shower on and we wash eachother, with hands lingering in certain places for a little longer than a simple wash.

After getting out of the shower and drying off she pulls a metal butt plug out of her purse and asks me to put it in her. The butt plug looks like condensed anal beads, with the tip being a small bead and the next ones keep getting wider til the base, then it has a regular jewel bottom. I put some lube on it and slowly slide the butt plug in, it’s like maybe 4 inches long.

We then lie on my bed and talk about random stuff for a while, as we hadn’t talk much in a week, but eventually my hand finds a breast and her hand finds my penis. I eat her out for a bit, she gives me a BJ for a bit, and then we’re both ready for the main event. I grab a condom, put it on, lube up my dick a bit, and she’s ready and waiting for me, legs spread eagle in missionary. I slide right on inside her easily, mentally noting I might not always need the extra lube. Immediately I notice the difference the butt plug inside her is making, it’s a bit tighter and more sturdy feeling on the under side of my dick.

After a bit of playing with her nipples with my hands we start kissing, but what I didn’t realize was that I was thrusting a bit rougher than usual. This meant that I was hitting her cervix pretty often and it wasn’t long before she had her first climax, she was unusually vocal so I was glad I was home alone. After her orgasm I stopped thrusting but stayed inside her, almost balls deep, and we continued to make out for a while.

When I went mostly soft she stopped kissing me and whispered in my ear “now fuck my ass”. I got up off my bed, sliding out of her, took the condom off and tossed it onto a pile of clothes on the floor, and she then presented me her ass while on all 4s. I carefully pull the butt plug out of her and set it on my night side table. I noticed a bit of brown on the end of it but I didn’t really care. I should have, and taken it as a sign of things to come.

Her asshole had just a slight gape so I poured some lube inside, cause I know for anal lube is key and for the size of my dick I knew a was going to need a good amount. I grabbed another condom and she gave me another BJ to get hard again. I put the condom on, put even more lube on my dick, she then crawled to the end of my bed in set up in doggy position. I got on my bed, aligned myself with her ass, and slowly began to push in.

When I get just the tip in she gaspes “OH MY GOD” and I stopp and let her get used to my size. I then firmly sunk my hands into her ass cheeks and proceeded to slowly thrust inside more. To try and make this more comfortable and more enjoyable for her I slowly thrust in an inch, then slowly pull back to just the tip, but not taking the tip out. Then I slowly go to a couple inches, give or take, and then back to the tip.

It was a fairly slow process, but I was enjoying the hell out of it and I think she was as well the way she was softly moaning. When I got most of my full length in for the first time and then back to the tip, I put more lube on my shaft and repeated going back and forth to that depth a couple more times. Then I leaned over next to her ear and said “enough warm up” and started thrusting at a more moderate pace.

She got more vocal with her moans, and it really started to feel good for me too. I could sense I wasn’t going to last much longer so I reached around and under her hips to start rubbing her clit. That really got her going and she started to buck her hips to meet mine. Just as I’m about to cum she beats me to it and says “oh I’m gonna cum” and starts to have a very intense “shaking orgasm”. As she’s cumming I cum to, but I thrust balls deep while doing so, going further in than I ever have. This might have been a mistake on my part.

She starts to squirt with quite a force but also she might have just been peeing for what happened next. I feel something dense pressing against my dick. Then a warm feeling all around my shaft and I looked down. Brown, and it’s already starting to leak out. I slide my dick out of her (in hindsight I probably shouldn’t have) and she erupts all over my bed. There was diarrhea almost from one end of the bed to the other and a large pile right behind her.

She must have still been orgasming or in bliss as I went to wipe myself off and it wasn’t till I came back with some paper towels that she came around. She was immediately extremely embarrassed and almost started to cry but I hugged her and told her everything was going to alright. I cleaned her up enough so that she could go have another shower while I continued cleaning up the bead. It was pretty obvious at this point the sheets and comforter were way to stained so took them off my bed and put them into a garbage bag.

After her shower and clean up were done and a new set of sheets were put on the bed we started to watch a movie but both fell asleep cuddling shortly after. When we got up this morning and after getting out of bed she starts rubbing her butt cheek and says to me with a smirk on her face “why do you have to have such a big dumb dick”.

Source: reddit.com/r/gonewildstories/comments/bqr773/first_time_anal_with_a_girl_did_not_go_as