First time cumming in my GF [MF] [21/20] [Anal] [Long]

Juliet and I have been dating for almost six months now, and the sex we have is definitely the best of my life. I’ve thought of submitting some of our sexual stories in the past, maybe if this gets enough attention I’ll write a few more. She is 20, about 5’6, 125 pounds, and wears a 32D. She takes excellent care of herself, and we go to the gym 3 or 4 times a week (her ab workout alone is more than most can handle). She has curly blonde hair that’s just past her shoulders, and bright blue eyes. I am 21, 6’3, and 195 pounds with wavy auburn hair and hazel eyes. We started out as roommates in the same university apartment with two other male roommates, and we began dating almost immediately.

I have had anal sex in the past with a couple previous partners, but it was something Juliet has been reluctant to attempt for reasons I consider perfectly reasonable. I’ve made it clear that it’s not something I need by any means, just something I like fantasizing about sometimes, and something I would happily do again. She once tried with a previous partner but says he never even got inside, and the furthest anything has been in her ass have been my fingers on occasion while we’re having sex.

Today was a fairly normal Saturday for us, and we had some lovely afternoon sex when I got off work at 4. About an hour later we were still in bed, she in a blue lace thong and myself wearing only boxer briefs. She brought up starting on homework, so I countered by suggesting that we get high and watch Cosmos (the Neil deGrasse Tyson series, which she’s never seen). She didn’t take much convincing, and I went to my room to load my vape while she brought up Netflix on her TV.

We watched most of the first episode and about halfway through we were spooning and I was absentmindedly fondling her ass, when I started rubbing her asshole through her panties. She wasn’t stopping me so I continued a bit, and then pulled the thong to the side when she stopped me. “Don’t put it in my ass,” she said. I told her I was just going to keep playing with it from the outside, which she said she was fine with. She pulled her underwear down about halfway and laid fully on her stomach to grant me better access, and I dared to get some lube from the bedside table to make things more slippery. As I was gently rubbing and occasionally pressing lightly on her asshole, she was mostly engrossed in the documentary but also made no complaints about what I was doing, and my middle finger found its way deeper and deeper on occasion. This was turning me on and I became hard, eventually transitioning to rubbing her asshole with the tip of my cock while she was still in a prone position. This is as far as I’ve been allowed to go in the past, and I am perfectly content stopping at any point if she tells me to. But she doesn’t, and when the first episode ends she has just the head of my cock tentatively in her ass. With occasional setbacks and restarts, she is telling me to be slow and careful. “You can keep doing that, but you’re not fucking my ass” she said. I asked her to reach back and spread her ass for me, something I request a lot while we’re having sex, and she complied.

By now I had added lube several times, and was basically thrusting the extreme tip in and out of her while she spread for me. She still maintained that I was not allowed to fuck her ass, but then she said “If you want you can cum on my ass,” and I asked “Where?” to which she replied, “You can cum into it if you want, just don’t go too deep.” This was a huge turn-on for me because I, like most people I’m sure, am very turned on by cumming inside a girl (in any hole) and Juliet is firm on saving having cum in her pussy for marriage (which I admire and hope one day to fulfill). So apart from her mouth, this would be my first time cumming inside her. As I’m thrusting slowly still, my cock occasionally makes a little progress into her ass. I’m watching her face and seeing that as long as the advance is very, very slow, she was allowing it. “How far is that?” “Past the head, I’m pretty sure that’s the worst part.” She nodded, “Alright, now cum in my ass? Please baby?”

I continue thrusting, slowly making headway and concentrating on trying to reach orgasm quickly (as a courtesy) and without hurting her. Apart from the occasional gasp, she’s giving me the green light and spreading her ass with one hand while putting the other on my thigh to occasionally push me back for a moment before I can continue. I’m watching the first third, then half, then almost two thirds of my cock slide into her ass and it’s one of the hottest things I’ve ever seen. Something about a good Catholic girl taking a cock in her ass really turns me on, what can I say. She’s begging me to cum, saying she wants to feel it inside her and she wants me to have her in a way nobody has before, “Please cum for me, I need you to cum for me, cum in my asshole baby please,” and finally I feel myself come to the brink and cross it, and my cum pours into her asshole. She moans and wriggles her hips as my cock pulses inside her, and when my orgasm subsides I slowly pull out. As I sit back and admire her ass, which really looks just as tight as before but with the addition of some of my cum leaking out of it, she looks back at me and spreads, saying “Take a picture, I know you’re thinking it.” I love this girl.

Source: reddit.com/r/gonewildstories/comments/5r2wbf/first_time_cumming_in_my_gf_mf_2120_anal_long