[M]y night of [F]irsts

So, I was a late bloomer, sort of.

I did fine talking to girls and all, but as a somewhat overweight kid from pretty much birth up through, well, now, I had a MAJOR confidence problem when it came to actually thinking girls were into me. All through high school and college, up until I was probably 27 or 28, I just defaulted to thinking girls weren’t into me.

When high school ended, I was still a virgin. I’d made out, had a girl topless a few times, fingered a girl. But I’d never had my pants off, and I had certainly never gone down on a girl. I made it through my first semester of college with little more than that, not even getting what I’d managed once every six or so months back in high school.

Then came second semester, January weather, and a gift from god in the form of a six foot redhead with a tendency to decide she wanted someone at random and then Take. Fucking. Charge.

I ran into her as I was walking into my dorm building at something like eight o’clock one random Wednesday evening. She was hanging with a couple of friends, having a cigarette outside. I’d seen her around at a couple of parties, knew her name, she knew mine.

We started talking and I went to my usual of cracking jokes and keeping the conversation mostly about her, smoking a couple with her before she invited me back to her friends’ room for a beer. I went, sat with her friends (all dudes, all upperclassmen) and joked, drank a little, and just kind of enjoyed having this chick sitting next to me.

Before long, she decided she wanted to go home, asked me if I’d walk her home. I said sure, grabbed my coat and we headed out.

I assumed, as usual, that she just wanted to feel safe as she walked home (I’m a fairly big dude, extra padding aside).

We got to her building and she started talking about how she had what she was pretty sure was the smallest single on campus. Like, closet sized, for real. I laughed, said that sounded like it would either be super uncomfortable or super cozy, depending. She said I should come see it and decide for myself.

I assumed she just wanted to prove she wasn’t lying.

I followed her up and we sat down on the tiny, tiny loveseat that she had managed to squeeze in at the foot of her bed and talks for a few minutes before I turned my head to say something and she just kissed me.

I was totally down for making out!

We made out for a few minutes and she broke away, saying she was going to turn off the light. Came back and her shirt had disappeared, claiming it was hot in there, a lacy black bra and some large, soft, warm looking tits held proudly before her as she walked up and straddled me.

At this point, even I wasn’t stupid enough to not at least do SOMETHING for myself, so while we made out I reached behind her and immediately failed to undo the clasp on her bra. I’d done it before, but this was new and I was nervous and FUCK it had been a long time since I actually got to DO that, so my fingers and my brain combined were too stupid to get it done.

She was great about it, though. She laughed, asked if I needed some help, and laughed again in a giggly, cute sort of way when I gasped out, “Yes, please!”

She reached back, undid the clasp, and tossed the bra aside, revealing her rather fantastic breasts and offering them to me happily. I started to suck on them, kissing and caressing them, really enjoying the soft warmth of them against my face and sort of quietly glad that she was raised up and couldn’t feel the raging boner I had trying to ram itself into a more comfortable position in my jeans.

When she stood up, I still hadn’t figured it out. I didn’t figure it out when she started to unbuckle my pants and knelt in front of me. It WAS kind of hot in there, maybe she just figured I’d be too warm with them on?

I didn’t figure it out until, in one smooth motion, she hooked the waist band of my boxers, yanked them down, and deftly caught my dick with her lips. Ho. Lee. Fuck.

My first blowjob. I was stunned. It was warmer, wetter, more unbelievable than anything I’d ever imagined before. I’d seen a LOT of porn, but had never in my wildest dreams come close to picturing the real thing correctly. She slowly and gently swallowed every inch of my dick, and I thought I would faint when my tip touched her throat and she just swallowed.

I ran my fingers through her hair, down her arms, gasping “Holy shit” every time I felt a new sensation, which was pretty much constantly. In retrospect, and after a decade or so of other experiences, she wasn’t great at giving head. But right then, at that moment, she was the fucking queen of blowjobs, and I was her lowly, happy subject.

I stopped her before I came.

I didn’t want things to end, and I wanted to go down on her. I’d never done it before, but I had wanted to for as long as I’d known what the hell that meant. She was more than happy to comply, sliding out of her pants and panties and laying back on the bed, long, silky white legs spread, her pussy covered in a thin down of fire red hair, lips plump and open and so incredibly inviting.

I had no fucking clue what I was doing. I didn’t tease, didn’t build up, didn’t work my way up to it. I just dove in tongue first, running my tongue between her lips and finding her clit pretty easily. I latched on, sucking gently and running my tongue over and around and back over again. I had no pattern, no plan, just a desire to find out what pussy tasted like and to try and make her feel as good as she had me. I reached forward and slipped a finger into her, curling it up and stroking along her g-spot, never even slowing down with my tongue.

She kept moaning and squirming under my mouth, telling me how good I was at it. My ego exploded, my pride grew to epic proportions, and I was hard as a fucking rock the whole time. She came twice on my tongue, the second coming after I sort of accidentally settled into a rhythm that worked for her, and as soon as she recovered she pushed me away, grabbed my hair and pulled me up.

“You HAVE to fuck me. Now.”

I didn’t have a condom, but she handed me one that, to my perception, she had conjured from some elemental plane of horniness because it just fucking appeared in her hand. I managed to fumble it on, scooted forward, had a false start or two, and then sank forward into what was the warmest, most incredible glove of softness and wonder I’d ever had my dick anywhere near.

I held off, somehow. I don’t know how long I lasted, but I know it was longer than I expected. I tried out different motions, different rhythms, different angles. She was either enjoying herself or a good actress, and encouraged me when I hit the right places or speeds. I came hard, and filled the condom up with a sort of shaking, blissful happiness.

I wasn’t a virgin!

Then I looked down and went for it. I think she was surprised when I dropped down and drove my tongue back into her, but she wasn’t upset about it.

I went down on her until I was hard again, sliding my fingers into her pussy as she finally gave me the first actual instruction she’d uttered the entire time.

“Put a finger in my ass!”

So I did! I learned immediately that if your hands are at all wide, the classic “Shocker” just doesn’t work unless you want to snap off your pinky. I figured it out, though, and she came again. I’ll never forget the way that looked, my fingers pumping in and out of her as her pale pussy pulsed around my first two fingers and her perfectly white, perfectly hairless asshole clenched around my third.

After she came she pulled me up again and guided my dick right back into her pussy. Same condom (stupid, I know) and I was more than happy to go again. I ducked her for a few minutes before she pushed me back, grabbed my cock, and pressed the tip against her asshole.

“Here!”

I pushed against her, felt the ring of her ass relax, and suddenly I popped inside, sinking deep with that first thrust.

First anal!

We went at it, slowly and more or less gently for a while before I finally came again in her ass, her fingers rubbing her clit while I toyed with her nipples.

We chatted for a bit as I slowly softened inside her ass and both laughed when I finally plopped out, the wrinkled condom still trapped in her ring. I gently pulled it out, threw it away, and kissed her.

She asked me to spend the night, but I couldn’t. I lived with a guy in a wheelchair and taking care of him was my job, so I had to be there in a few minutes to put him to bed, and would have to be there through the night. She smiled, kissed me, and handed me my clothes one piece at a time as I got dressed, then walked me naked to the door.

I never slept with her or really saw her again, but I’ll always remember that night in vivid detail.

Source: reddit.com/r/gonewildstories/comments/77iebo/my_night_of_firsts