Prom? Ch. 01

Life really does have a strange way of working itself out. Here I was, in my best friend Natalie's bedroom, laying on her bed, getting one of the best blowjobs of my entire life, from Natalie of all people! Natalie, who I had never had the thought of pursuing at all, was giving me a blowjob. And on top of all this, I was made up to look like a slutty blonde! I didn't want to admit it to myself, but the fact that I was getting a blowjob while I looked like a hot blonde girl was turning me on even more.

Natalie was now bobbing on my cock, my entire shaft disappearing in her mouth, before she popped back up again, flicking her tongue back along my head. I became lost in the moment, lost in the pleasure I was feeling from my cock as Natalie worked it with her mouth. I moaned, biting my lip and playing with my nipples. My nipples never usually did much for me sexually, but at that point everything was turning me on.

I was so lost in the moment that I almost didn't notice that there was pressure being applied to my ass. As Natalie had been eating me out/blowing me, she had slowly been moving me into a position where my ass was more exposed. While one of her arms had wrapped around one of my thighs as she blew me, her other arm had now trailed down to my ass. She gave it a soft pat, before rubbing it, eventually moving her hand a little closer to the hole than I had expected. Her hand stayed there for awhile, before moving a little bit closer to the hole. With each bob of her head on my cock, her hand would move closer and closer to my hole, until eventually her fingers were teasing my opening.

She took her head away from my cock and gave me a look, as if she was asking whether she could put a finger in my ass. For a few seconds I considered my options, before really taking my situation into consideration. I was already getting blown while dressed as a girl. Was there really any limit as to how weird this situation could get? Why the hell not? I nodded my head at Natalie, and she smiled in return. Natalie took her hand away from my ass and used her other hand to jerk me off, scooping up precum from my cock and slathering it onto her index finger. For good measure, she stuck her finger in her mouth, wetting it further with her saliva. I folded myself a little more, my knees coming closer to my ears, my hole now more exposed as I lay on my back.

I felt Natalie's finger slowly start to ease into my ass. She teased the rim of my hole as her mouth returned to my cock, engulfing the head between her lips. She looked into my eyes, her mouth full of cock, and gave me a wink. She slowly but firmly pushed her index finger into my ass, making sure to look at me to detect any discomfort or pain. Her finger was quite skinny, maybe a bit on the long side for someone her size, but the girth of her finger certainly wasn't a source of pain. Regardless, it was the first time anything had been up my ass, so there was at least a little discomfort, most of which I was able to ignore given the massive amounts of pleasure I was receiving from the blowjob.

Before long Natalie had plunged her entire finger inside me, and she was now knuckle deep in my ass. She looked at me as she blew me, and I moaned as she slowly started to pull her finger out of me, arching her finger so it brushed up against a particularly sensitive place inside me that gave me an extra wave of pleasure. Natalie slowly moved her finger back into me, brushing against that place again. She started speeding up the pace of her finger in my ass, and after awhile her finger was going at the same pace as her mouth was going on my cock. My moans were becoming louder and louder, almost becoming primal screams as she fingered my tight hole. Natalie withdrew her mouth from my cock.

"Who's my little slut?" she asked, not slowing down the pace of her finger.

"I...I...I am" I said in between moans. Despite her mouth and her hands not being on my cock, my cock continued to throb as if they were. In fact, it was growing harder with each pump of her finger into my hole. I screamed louder as she introduced another finger into my hole.

"Cum for me Anna. Cum for me you little slut," Natalie said, her mouth returning back to the head of my cock. She gave one last flick of her tongue over my bulging cock, and one last plunge of her fingers in my hole, before an explosion occurred inside me. My eyes rolled back in my head as I arched my back, and I screamed as my hole clenched and unclenched repeatedly around Natalie's finger. I felt a warmth growing inside me, radiating from deep down, almost near where Natalie had her fingers. That heat soon spread all over my body, and my hips, thighs and stomach shook in return. It engulfed my legs, and my legs started shaking against Natalie's shoulders. I briefly thought back to earlier today, when I was biking up to Natalie's house, my legs shaking as I climbed up the hill. Well, my legs were certainly shaking again: only this time, I was having the most intense orgasm of my life, cumming like a slutty girl. My back was still arched as the heat kept on flowing through me, now coming in waves from my throbbing insides.

"OH...MY...GOD!" I screamed as a whole new powerful wave hit me, this time radiating outward from my cock. My body convulsed around Natalie's finger, still deep in my hole, a ripple of pleasure and passion crashing through my body. The heat from my cock and the heat from deep in my hole combined, turning into one. It rippled through my body one last time, one last shock through my body as the waves left me through my cock. My position on my back led to my cock facing my stomach, causing me to squirt wave after wave of cum across my smooth, hairless stomach.

My legs fell away from Natalie's shoulder, melting away into the sheets and retaining a jelly-like feeling. For a couple of seconds I couldn't move because aftershocks continued to hit me. Once my body had stopped shaking I turned my head back down, back to looking at my soft, feminine body. I noticed that my soft, feminine stomach was covered in a rather unfeminine amount of cum, with some even pooling into my belly button. A towel landed right in the middle of my stomach.

"I'd dry myself off if I were you," Natalie said. "We have to go to the mall. You need a prom dress sweetie."