I’m going back a few years on this one, but wanted to share.
Just got out of a rubbish relationship and was looking for something fun (?), and starred talking more to a lovely girl called Nikki who worked at the local library who I was flirting with off and on. She was a bit of a plain Jane to look at, very prim and proper, the kind of girl who always has a cardigan within 5ft at all times, with mousy brown hair, cute thick framed glasses and green eyes. Very unassuming, and fairly quiet (though that might have just been the setting!), and always went as red a beetroot when flirting. I found her pretty, and loved my time with her.
I asked her out one afternoon and we ended up going out for a few months until I had to move for work. We got along like a house on fire, and the more I got to know her the more I realised she really wasn’t the quiet unassuming girl I thought she was, she was very flirty, kinda forward, and definitely a little bit kinky ;)
I don’t remember the exact details of how it came about, other than we’d been going out for about a month and we’d just came back to her place from the gym (gym buddies, how cute!), and I’d just got out of the shower. She was rubbing my back as I was laying on the couch, pretty innocent but she’d been dropping hints she was horny before the gym and I was hopeful it’d lead to something. She asked me if I wanted a special massage and I shrugged and said sure (figuring/hoping she might have meant a bj), and before I knew it she was wriggling my pants around my ankles and started rubbing in long strokes from my shoulders to my ass. “This feels promising” I thought with a smile on my face.
I closed my eyes and let her continue. After a while the strokes stopped going all the way from my shoulders down, and were slowly focusing into smaller strokes, much lower, until she wasn’t doing much other than rubbing my ass. “You have such a nice ass” she kept saying, as her soft hands were working my cheeks in a circular motion. I could feel what was coming because of her shifting her position, and I felt a kiss, two, three landing all over. First tentative but because I didn’t offer any resistance they became wetter and sloppier and I could feel she was trying to surreptitiously spread my ass cheeks.
I don’t know what came over me but my next words were “don’t be shy” which was an insane thing to say as I’d never done any butt stuff and not only did it sound like I knew what I or she was doing, but that I wanted… something there? It sounded really sexy in my head and I just blurted it out lol
She wasn’t shy and completely took control. She spread my ass cheeks and slowly started licking. I’ll admit to jumping slightly but I relaxed into it and man it felt good. It didn’t phase her and she kept going.
After a while she starts with “Have you ever…?” she trailed off. I didn’t know exactly what she meant .. “What?” .. “Have you ever had anal?”
Wohh there. Stop. She’s asking about anal while rubbing and licking my ass. “No, I’m not into that?” It came out as more of a question that I’d have liked. But because it came out as a question she continued “No haha.. would you like to try though? If you like it, I’ll let you do it to me”
Holy fuck. Did I want to fuck her in the ass? Hell yes. It had been a lifelong fantasy from first looking at porn. Did I want to trade my ass for her’s? Not likely!!
I hadn’t replied so she said “It’s not gay or anything, I have toys. Lots of toys. It’ll be fun.”
I still haven’t said anything and I’m starting to panic. She needs or will expect an answer but I’m so fucking conflicted and I’ve literally lost all power of thought.
“Have you done this kind of thing with guys before?” I asked. I’ll admit it was a bit higher pitched that I would have wanted. I could hear the smile on her voice when she replied “we’ll start off small and see where we go, and I’ll be super gentle.”
And so just like that it was decided.
I’ve just realised this post is super long, I’ll post more in the morning if people are interested:-)
Source: reddit.com/r/gonewildstories/comments/926g6t/mf_surprise_butt_stuff
Absolutely interested! Hoping you said yes, because having a woman do you is incredible! ?
Prostate orgasm is a home run
Not one bit of this is gay, go for it, you’ll probably like it. She sounds like she knows what’s up, so go for it, and go slow… in the beginning ;)
More
My girlfriend and I have add prostate stimulation to our menu of sexual activity.
We started slowly but now she will literally fuck my ass with a strap-on.
Honestly some of the most intense orgasms I’ve ever had.
Shit or get off the pot. Either tell the story or don’t.
“NEXT TIME ON DRAGONBALL Z!” Shit is obnoxious.