[M]y [f]irst time cumming inside of a woman (and it was during anal!) | 2016

Two years ago I was studying abroad in London and saw all the sights lived in another country for a whole month. My university and another university (both State schools in the US) joined together so we could have enough resources to affordably live in a beautiful part of West London.

While the trip itself was a life-changing experience, I also met this girl who opened up my eyes sexually. She was 24, about 5'3" with long curly brown hair, dark brown eyes, a tight firm ass, and DD sized breasts. I know what you're thinking, there's no way that a girl with those measurements has tits that big. I can assure you, these were real and she even told me they used to be perfectly perky Fs. She said it was such a shame I didn't see them in their prime. I thought they were amazing as they were.

At the time I was a 21 year old who had just gotten heartbroken from a longterm relationship. I'm about 6' tall with light brown hair, hazel eyes, and an average build. I saw this girl on the plane and I was smitten by how beautiful she was and I started flirting with her almost immediately. While we did hook up the first night and began this pseudo-relationship for the weeks to follow, this is still one of the most memorable moments of our sexual escapades.

It started out like any of the other sex sessions we had had, her lying on the bed, me on top. I was much less experienced than she was, as she was a self-proclaimed nymphomaniac who struck me as insatiable. Long story short, her pussy could do some incredible tightening and flexing motions that sometimes turned me into a bottle of lotion, squirting after just a few pumps.

For some reason, this time was different. She was on the verge of cumming and was soaked because of it. I was pumping away as valiantly as I could, trying to climb her orgasm mountain, watching her enormous tits bounce with each thrust when I all of a sudden over-estimated my length and slipped out (come on gentlemen, who hasn't done this?). In my haste to once again enter her I gently pressed against her wet skin. She made the "no" face, like I was about to go into her ass and I readjusted. Or, so I thought.

Now, I would not say I'm well hung. I don't have anything to brag about, but I have also never heard any complaints. That being said, she gasped as my cock entered her asshole using nothing but her juices and my rambunctious stupidity. My jaw half-dropped and I stopped mid-thrust.

She said it was fine but did not seem like she was ecstatic about it, and I don't blame her. But we both knew I couldn't go back to her pussy and I knew this was too great of an opportunity to miss, so I didn't want to fuck it up.

I had never successfully had anal sex before. Even though it doesn't usually turn me on in porn, I was pretty turned on at this point. After she got used to it, she was pretty turned on too. She told me before she has a creampie fetish, and loves having cum inside of her. She pulled me down to her level, stared me right in the eye and told me she wanted me to cum inside of her ass. I agreed, but I was too busy enjoying the different sensations of anal sex to think about cumming.

My favorite part was watching my cock disappear inside of her, but seeing her pussy completely untouched. It was such a surreal part of the whole thing. The most unexpected part was how it actually felt. I'm used to the way a vagina feels; like soft, wet, velvet continually vacuum sealing around my cock. Anal sex was a tight entrance and a much more open space beyond it. I could feel ridges and other areas. I even slid my fingers into her pussy so I could feel myself sliding in and out.

She told me to go slowly so that it wouldn't hurt her, but before too long I came anyway. The build up happened suddenly. Before I knew it I was pumping quicker and began shooting warm cum into her ass. I could feel it on my head and shaft all along the tunnel, hot and sticky. She was extremely turned on in that minute and began to whimper when I started cumming.

Completely blown away by that experience, I lay back. We talk for a while about a couple different things (what just happened included) and then passed out.

That was the only time I've ever had anal sex. And while it was an incredible experience, it is only one of several excellent sex stories I have with this woman. We parted ways after the trip and haven't seen each other since. She's actually gotten married in the past couple of months and I started dating this amazing girl a year ago. But I had a lot of fun writing this story. If you liked this and want to hear more (or possibly have any requests) just let me know!

TL;DR: Accidental anal --> creampie.

EDIT: Formatting.