Ok, another fairly pedestrian tale from my not so amazing sex life. Be forewarned there is somewhat of a letdown at the end. As always story is 100% true.
I was 18, a freshman in college and fairly recently lost my virginity to my 21-year old girlfriend. Getting laid almost every day was like a dream come true and I wanted to fuck 2-3 times a day. Pretty early on having sex during my GF’s period came up. She was open to it and I was too horny to skip several days of fucking. I was a bit grossed out of the thought of it, I don’t like blood at at all, but it felt great, always wet and silky. During these times we would lay a towel down, turn off the lights, and fuck missionary. I always wore a condom with her regardless, and when I was finished I would pull the condom off still in the dark, wrap it in some paper towels and toss, wipe around my junk and my hands around with some wet wipes, toss all that, then head to the bathroom to clean up some more. Same for her pretty much. This kept the gross factor to a minimum.
One night I was hanging out with her while it was that time of the month. We started messing around a little and were both naked, I figured we would do our regular routine soon. But before that happened she told me she was sorry, she kind of had bad cramps and she wasn’t up for it tonight. She laid on her stomach on the bed the long way, and I sat perpendicular with my back against he wall, her legs resting across mine. She turned the TV on and started watching. Shame on me I was so horny I could not leave her alone, I started messaging the back of her legs, thighs and eventually her ass, kneading her cheeks and pulling them apart. For the first time in my life, I started to take a close look at her asshole. I had seen anal porn but had zero experience whatsoever, even with her I don’t think I had really touched it or paid much attention to it. We had sex doggy style a few times by then, but usually with the lights pretty dim.
Her asshole was pretty cute all things considered. It was not pink like a pornstar but not too dark and pretty small. I hadn’t ever considered the thought of actual anal sex with a woman, I thought that was just in porn, that it would hurt her and she would be upset and that was not my deal at all. But I was really horny as hell and intrigued to experiment. I took my index finger and gently started rubbing around her asshole. Then I started gently tapping her hole. She said, “Oooh” and looked back over her shoulder at me, a mix of surprise and confusion. First time anything like this had gone down. I asked if she wanted me to stop and she said it’s ok and turned back around. My next move was to wet my finger with spit and gently rub, going back to wet my finger a few more times. I asked her if she liked it and she said it was fine. Eventually I started to slowly poke my finger into that pooper, just a little bit. It was met each time with quite a bit of pressure/resistance. Again I ask if it’s ok, and this time she says it feels “weird”, I ask if I should stop and she says no it’s ok. So I continue wetting, and digging in her ass with my finger. She lets out little grunts from time to time and I tell her stop me at any time, but she never does. After maybe 5-10 minutes, I can’t remember, her asshole seems to loosen up a little bit and my index finger is in knuckle deep, maybe 2, 2 1/2 inches? She is groaning/moaning softly. I ask her if she likes it and she says not really, but somehow her cramps are gone now. I pull my finger out and….surprise….it smells like shit. I think that’s to be expected here right. I just deal with it, don’t say anything, and I inform her I am going to fuck you in the ass now! In truth I’m kidding, this still really has not crossed my mind to actually do, I figure it would just be too painful and not worth the hassle. Not to mention I was pretty clueless about lube or anything like that. To my surprise, she says OK.
Now shit has just got real. I think about it. I am an inexperienced 18 year old who just recently lost his virginity. Was I really going to fuck my first girlfriend in her ass, would I even like it, would she hate it and be mad and make me stop, would it even fit (average), etc. I got up off the bed, stood past the end and pulled her down towards me. Grabbed her hips and lifted her into doggy position. The green light was there. The brown eye was there. Buuuuut…..for whatever reason, I decided against it. I really did not want to hurt her, and I did not want to mess up my daily pussy supply. I put on a condom….and started to slip my cock into her….pussy. All of a sudden she lurches forward and says “WAIT!” She had a tampon in LOL, I was so fucking clueless. She gets up off the bed and tells me to turn around (I’m not supposed to see this), and takes out her tampon and tosses it. She says she wants to use a towel and on her back but I say no, please the other way. So she obliges and gets back on all fours, and I’m standing past the edge of the bed. I slip in, very wet for obvious reasons, and start pounding her pussy. I close my eyes and imagine I am pounding her in the ass like in porn. I was so turned on by all this I came really quick and hard, grunting like an animal. I knew she hadn’t come anywhere close and said sorry. She said she definitely wasn’t going to cum tonight anyway. It was pretty light out that evening, and this time I saw everything, a lot of blood over my cock, crotch, stomach, her crotch, ass, down the back of her thighs etc. We started to clean up and she apologized, I said for what?!?! I harassed you for sex and wanted it this way. It’s totally cool, and really it was no big deal, WELL WORTH IT.
So there it is. Never wound up having anal sex with her, never had that cramping issue again that I can recall, fingered her ass a tiny bit here and there but this is as close at it came.
Source: reddit.com/r/gonewildstories/comments/goo2yt/mf_first_time_anal_play_during_period