Original story here https://www.reddit.com/r/gonewildstories/comments/i1u5r5/mf_my_current_gf_and_i_first_time/
If any of you read my last story, I posted about her and my first time. As time went on and as we explored mire of what we were into, we would occasionally push boundaries. As I was eating her, I would occasionally dip down and give her ass a tease with my tongue. That was a first for her, and she loved it – which completely surprised me. She told me she was an anal virgin. One night while she was giving me one of her mind blowing blow jobs she reached for the bottle of lube. I assumed she was going to finish me off with a hand job. As she kept sucking me, she also dipped down and gave my asshole a flick of her tongue. I moaned a little and she kept at it for a minute, then I felt her now lubed up finger slide down off of my cock and a gentle probe and some pressure, then all at once she was in to her first knuckle inside me. Her mouth resumed it’s place om my cock, then she pushed further in and started rubbing my p-spot. I had never in my life experienced this before, and, shockingly to me, it felt awesome. It wasn’t long before I emptied myself into her eager mouth. It was definitely a new thing, and I thought until this point I was pretty sexually experienced.
Fast forward a month or so as we integrated this into a regular part of our play, and we had a vibrator out and I was teasing her with it. Taking turns with her various erogenous spots, I teased her clit and went to put it inside her when she grabbed it from me. “Not tonight, this is for you”, she told me. I laid on my back as her expert lips and tongue started devouring my dick as she began to play with my ass with her free hand. I felt one finger, then two disappear into me, then a small butt plug that we picked up got pushed in. She would tap the end of it with her fingers and it felt great with the pressure hitting me on my prostate gland. As the plug got removed, I felt the vibrator taking its place, and i was surprised that it actually fit. And felt good. Really good. One hand pumping my cock, and the dildo fucking my ass, she turned up the vibrations. At this point I turned into a shaking, moaning, whimpering pile of jello after I exploded with The. Most. Powerful. Orgasm. I’ve ever had in my life. (Pause for the complete William Shatner effect) I have never felt anything this strong, ever! After I recovered, I treated her to at least four orgasms leaving my back and shoulders looking like I lost a fight with a wildcat.
We discussed taking it further and trying some pegging, but sadly the relationship never made it that far.
Source: reddit.com/r/gonewildstories/comments/jql4xl/how_i_m_discovered_i_am_into_prostate_play_with
My gf actually proposed something similar but I was too scared/freaked out lol. I’ve heard good things about it and maybe I’ll build up the courage to try it one day.