**Note:** …just mind that english is my second language so the grammer and what not may suck at some points and futher stories as I’m also not the best of writer for those type of stories or in general, so please go easy on me.
“It’s not gay to try it once…right?” I muttered to myself while walking away from the corner store. The bag in my hands swished from side to side while I playfully started skipping. The awkward tension of buying lube from people I knew was over and now I could get to the fun part! Just a quick hop, skip, and drive home later-
I sat down on my bed.. Terrified. I’ve never done anything like this before- How was it supposed to feel? Should I try watching something to get in the mood? What if it’s not what I expected it to be?
Flustered and nervous, I threw myself down and stared at the ceiling. Phone in one hand, bottle in the other.
Mmnnnn~
Groaning, I flicked through my phone looking for something as a distraction.. Maybe I could just jerk off and sleep on-
A part of me was up and ready for that kind of fun as my skirt turned to a tent. Succumbing to the comfort of a regular start, I started edging my tip against the light fabric. My hips shifted while I was stifling my own moans, imagining what I was about to experience with a slight grin.
I slid a hand down my body and under the skirt to the base of my exited friend. Rolling over, I couldn’t help but to grind against my hand and clothes feeling my own heat bring me comfort.
Getting into the mood went quickly after I took the lube I had set out for plugging myself and began treating my hand like a slut-
The wet plaps of masturbation were music to my ears while I felt myself slowly edging to peak. THEN SUDDENLY-
I paused looking down on myself…
My dick was still glistening with a mixture of lube and precum making it oh so fun to keep stroking~ but then I remembered the reason I wanted to buy lube in the first place.
With the sole thought of cumming on my mind and wet fingers ready for the plunge, I felt them enter myself from behind.
At first I shuddered.. It was foreign. Weird even. Trying to move felt a bit strange, but I picked up pace anyway. Moments later and I was thrusting myself, still pent at the edge of my orgasm.
I didn’t even noticed my legs lifting in the air as I was going, but I rolled back around almost like I was trying to mating press myself. My sex-crazed stare was spoiled by the skirt hiding it from my view as I kept going.
Despite furiously masturbating at this point, I didn’t felt any closer to that wondrous climax I was expecting. It felt good, but being at the cusp just wasn’t enough.
Then reaching a bit further I almost felt something squish~
Immediately arcing my back in response, I learned the meaning of ‘the cum button’ while my mind went blanked. Almost like a primal command was given, I shot hot ropes of white through my clothes while feeling my first ever anal orgasm.
Nothing compared to the mess I just made out of myself my eyes rolled up and I collapsed on my back. It was still twitching while I tried to catch my breath to no avail.
“holy…shit” i panted before passing out for a bit with a quite surprised but satisfing smile on my face and on the thought of doing a second time later on.
Source: reddit.com/r/eroticliterature/comments/10celph/curiosity_nsfw_solo_m20_femboy_crossdressing_anal