Author: eatsmostthings

[MT] First time anal with my college girlfriend. :)

My last post was a bit too kinky for some of you, so I thought I’d do something a little more vanilla – one of the earlier times we tried anal.

So my college girlfriend was a transwoman, and you can read more about her in my previous posts – she was gorgeous, with small supple breasts, big doe eyes, and an average sized, slim cock (5 inches long, ~4 inches circumference). In my first gonewildstories post, I described our first sexual encounter, and in the second, a kinkier cum-saving adventure. What I’m about to describe happened somewhere in the middle.

So after our third or so 69-cum swap adventure, we were laying in bed, cuddling, and Meg asked if I had ever considered anal. I told her my experience was pretty light – I’d tried sliding a finger or two inside myself a few times in the shower, but nothing really routine or anything. She responded, “Oh! Wow. How did you like it?” And I very quickly realized at that moment that what she really wanted was for me to top her, not for her to top me. I told her I’d liked it, but I didn’t really have the flexibility to do it comfortably with my hands. She giggled and told me she’d actually never done anything anal before, and hadn’t even considered topping a man. I think at this point I looked pretty embarrassed, but she was encouraging about it. Read more »

[MT] Some kinky cum swapping & frozen loads w/my college trans-girlfriend Meg. [kink]

You guys gave me such good feedback on my first post, so I thought I’d post one more. It’s a bit kinkier than last time, but what the hell.

So I dated a transwoman in college named Meg, and as I mentioned in the last story, and our first time doing anything sexual together, we 69’d, came in each other’s mouths, and cum swapped our loads.

We quickly got pretty nasty, trying basically everything there was to do. We took turns fucking each other, giving each other handjobs in a public park, blowjobs in a public bathroom, and because neither of us are that big, we started using butt plugs sometimes. Whenever I think back to it, it’s a little surprising to me how quickly I went from 0 to 100. I had only had one sexual encounter with a cisgirl – just vanilla PIV, and now here I was, basically sucking the cum out of Meg’s dick every time we fooled around. We actually both came in each other’s mouths almost every time we messed around. Maybe because it was such a special part of our first time together, we both grew sort of addicted to it. Read more »

[MT] Cum swapping with my girlfriend in college.

Sorry this is a bit long…

Back in college, I was a nerdy computer science major, and roughly dressed the part – I wore graphic tees with excruciatingly pedantic designs, wore a mop of messy unkempt black hair, and walked around in flip flops until the weather made it unbearable. My only redeeming quality was that I was not terrible-looking, and I was in fantastic shape at that point – I wasn’t the most athletic guy, but I spent a lot of time at the gym. And so, I’d had girlfriends before, but as you might have expected, I was about as smooth as your typical computer science major and so aside from one awkward, messy night of sex, they never really went anywhere.

So when college hit, I felt this was my chance to come out of my shell, sleep with some girls, and explore (not unlike most nerdy college freshman). But I went to my first party, and, having not had any alcohol before, drank something like 1/6th of a handle of vodka and got absolutely black out drunk and woke up on the floor of the communal bathroom (not even of my own dorm). My friend later told me I’d stripped down to my boxers, began yelling something about love, I then proceeded to start biting things and flirting with random strangers. Read more »