Sissys First Anal
- 3 years ago
- 22
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A Sissy's First Dildo Experience free porn video
Buying a dildo online was a bit nerve-wracking, honestly. Not for any huge reason or anything – I live alone, and the packaging is supposed to be discreet anyway, but there’s just something that made me nervous when I first put in the order.
Sure enough, it wasn’t like it was a fat box labeled, “Tasty Black Dildos for Sissy Whores,” all around it; just a plain box, inside which was some bubble wrap and a plain, pink bag. But inside that bag was an unforgettable package.
After carefully opening it and getting a good look at the contents, I started getting nervous for a very different reason. The pictures online were flattering, but they didn’t really have the same weight as the hefty, chocolate-brown dildo as I lifted it up.
My fingers were tracing the veins when I snapped out of it, swallowing hard as I realized how much my mouth had been watering, and I immediately went to my drawers.
I needed it inside of me, but I wanted it to be right.
Stripping out of my “boy clothes” never felt as liberating as it did then, and the whisper of a touch from the lacy panties as they moved up my thighs almost had me moaning right there; I was biting my lip as I grabbed the sheer nightie I kept reserved for play-time, and I knew I was ready.
Mentally, anyway. I might be practically dripping from my little clitty, but I’m not lucky enough to get wet down there without a little help. One hand got a nice little squirt of lube from the bottle, while the other ran a delicate finger along my tip to pick up my pre-cum.
I wanted to use it as a bit of lube but, as I looked closely, I couldn’t help myself.
My lubed-up fingers started to circle my hole as I put my other finger into my mouth, my tongue lapping at the taste of precum as my chest seemed to throb even harder, and my little clitty even harder than that.
Of course, it wasn’t really fair (or really the point) to focus just on me.
My eyes settled on the thick black dick as I carefully used my free hand to lift it just a little bit – just enough to get it standing upright.
I didn’t expect it to be quite so… Big. I’ve stretched myself out with my fingers before, but I just feel so small compared to this… Hunk. Putting my face next to it, gently touching the balls with my chin, I could feel the tip gently touch my forehead just as I slid a finger all the way in.
I moaned into the shaft as I felt my finger just barely stroke my prostate, every sensation feeling so much stronger as I gently eased it in and out. My other hand moved towards my clitty, picking up more of my precum. It was then, though, that I had a sinfully kinky idea. Instead of swallowing, I reached over to the lube bottle.
I reapplied lube to my fingers as I prepared to push deeper, but also brought the whole bottle to my mouth.
It was a little colder than I expected as I squirted a bit into my mouth, but that only made the precum feel that much warmer as I rolled it around. After a few seconds, it was all nice and warm and mixed together (with another little bit more pre-cum added in), and I was ready.
He was so thick, especially the head, that I was worried that I’d spill the lube as I pressed my lips against the tip – it wasn’t rough, but it wasn’t quite smooth either. I moaned out my nose as I pressed my fingers onto my prostate, as though massaging it, and relished the texture of the faux-skin on my lips.
It slid all the way into my mouth, thick enough to keep me from spilling a drop as my tongue moved from the gently-textured head to the slightly firmer shaft. I tried to trace every vein along it, but there’s no way I could’ve kept my focus while looking at it, let alone with the whole thing in my mouth.
At this point, I was all but finger-fucking my ass, stretching it out and pushing that P-button as fast and as hard as I could, but none of it felt as good as the feeling of the lube sloshing in my mouth, pushed about and displaced by a thick, fat, big black cock.
I hadn’t even realized I’d shut my eyes until I slowly opened them and felt a fluttering in my chest, seeing that I hadn’t even made it halfway down.
I tried going further, but the lube in my mouth was just too much – if I took even one more inch, I’d start spilling.
So, I spilled.
Barely able to control myself, I opened my lips just a bit and pushed deeper, feeling the cock-head press against the opening to my throat in an instant, and the lube splashing wetly against the rest of the shaft and absolutely drenching the balls.
I nearly gagged as I pulled back up, my free hand holding the cock steady and the other stock-still – in the excitement of pushing myself down, I’d completely forgotten my ass.
I debated adding a bit more lube and getting back to it, but finally decided not to.
I lifted the dildo with both hands, now, and carefully aimed it at my mouth before sliding it in, moaning around the body as I felt every vein slide across my tongue. The only thing more arousing than the feeling of it was the sound as it pushed aside the spit and leftover lube, as it pressed further and further back while I pushed it.
I made it as far as I could without gagging, before slowly pulling it back out; each time, the deliciously unique sound drove me to moan before speeding up just a bit.
Stroke after stroke, thrust after thrust, I could barely contain myself as I went from carefully sliding it in to fucking my mouth as roughly as I could; I kept getting to just the brink of gagging but, every time, it was like I could get it in just a little bit deeper, until I felt like I was practically knocking on my throat with every slam.
There was no way I would be taking this delectable chocolate monster any deeper (on my first time, at least), so I finally pulled it all the way out and set it down once again, my breathing labored and face flushed as I did. I could barely even pay attention to the way that the spit and lube had splashed out of my mouth onto my nightie, drenching me from my chest to my panties.
But it wasn’t even close to over.
I could feel my own length pounding with need, desperately begging for attention right alongside my hole. But then, a proper sissy knows exactly which one to give her attention to, doesn’t she?
Lubed up fingers finally went back to stretching myself out, preparing me for what was next. I could feel my ass trying to pull back as I stretched it more and more – the feeling of cool air moving was my first clue to just how wide my gape was getting, but I’d felt this fat black dick in my throat.
It wasn’t enough. Not yet.
I kept poking and pulling, teasing the entrance and every inch of my insides as I pressed everywhere. I got halfway to cumming just from the way I pressed into my prostate; I was dripping pre from the tip of my dick, watching it dribble onto the floor before turning my eyes to my goal.
My face half-slid in the lube as I shifted to look up at the dildo, at how it shined from the light bouncing off the lube, and I knew I was ready.
My hands finally pulled away from my ass as I crawled, hands and knees, towards it. Moving over it, I could feel the just-barely-textured head press up against the part of my own clitty that the panties were just barely too short to cover, and I nearly came as I stopped to grind for just a few seconds.
Finally, I moved just past it and double-checked that the lube hadn’t messed up the suction at the bottom (it did, and I fixed it) before feeling it press against me.
I had to use my feet to angle it, my soles smearing just a little more lube across its length as I slowly leaned back. Even after all that stretching, it still didn’t slide in easily; I slid the tip all along my ass for a second, before pressing it against my hole and sitting back.
Then, I started to count down, promising that, at zero, I’d sit back fast enough to just force the head in.
Ten. I took a slow, deep breath.
Nine. I used one hand to slowly caress my chest.
Eight. The other kept me stable, pressed carefully against the floor.
Seven. The completely soaked nightie clung to my skin, sliding across my chest as I moved my first hand.
Six. Despite the cool air moving through the room, I only felt like I was getting warmer as pressed a little bit harder against the tip.
Five. I could feel the slightest bit of give from the shaft, the warmth of my ass starting to stretch pulling a guttural moan from my throat.
Four. The slow movement of the hand on my chest turned into something more like a pathetic pawing, my clitty throbbing even harder as I tried not to touch it.
Three. The stretching started to feel even more pronounced as I resisted the urge to push down early, moans turning into desperate mewls as I struggled to hold back.
Two. My breathing hitched, and I felt it.
It popped all the way in, even without the extra push.
Every bit of air in my chest surged out at once, leaving not even enough to gasp or groan as the rest of the lube slid the length deeper inside.
It slammed into my prostate and, without even touching it, my hard little clitty started to spurt.
I couldn’t control my body as tremors overtook it, the rapid tightening and relaxing forcing the tip of the dildo to pound into my P-spot over and over and over; even after I finished shooting cum onto the floor, I still kept cumming as a full-body orgasm captured me entirely.
My hips kept bucking long after my upper body collapsed, my face resting in a puddle of drool, lube, and just enough of the furthest-spurting of my cum to taste distinctly salty.
I couldn’t stop the twitching in my ass as minutes (or at least what felt like minutes) passed, and I finally straightened my legs. My stomach flattened against all the rest of my cum and, with a satisfying and resounding little POP, the dildo slid out and wiggled back to an upright position. I couldn’t help but twitch one more time as a bit of the lube was flicked off by the movement, splashing me with just a few drops across my back.
I laid like that for who-knows-how-long, before finally rolling over onto my back and absently wiping up all of the cum, lube, and spit I could.
It never tasted as good as it did right then, and I knew that as much as I loved finger-fucking myself?
After an experience like that, how could I ever go back?
Gigi
- 08.02.2023
- 34
- 0
- Category:
- Crossdressing
