Assgina for Angie

She searched my eyes for a moment before turning around to head back down. "Don't worry, I won't bother you two in the kitchen. I'll be in the gardening shed if you need me.

I found Angelica in the kitchen as promised, looking quite bored. "Well, it's about time, you're as bad as any girl."

"Sorry, I lost track of time," I lied.

She gave me a long look, her eyes narrowed. "I very much doubt that. How many times did you change your clothes before settling for shorts and a t-shirt?"

"None."

"Now I know that's bullshit, Timmy," Angelica said, directing a vicious grin my way. "You were wearing a different t-shirt and shorts at my house."

"Oh yeah, but they got dirty so I changed," I replied.

Her amusement was almost savage. "So you came home, beat off and made a huge mess."

I shrugged. I didn't want to admit it but I also knew that Angelica would see right through any lie.

"So, yes," she said when it was obvious I wasn't going to say anything. "Well, don't you worry, the only mess I'll make will be right down your throat. No clean up needed."

So we had a date after all. The usual date my mouth had with her cock.

***

"So, where do you wanna go tonight?" I asked as Angelica backed the car out of the driveway. I was sure that I'd be sucking her cock soon enough but she wouldn't pick me up just for that. She had other plans as well or else she would have just told me to come over on my bike to suck her off in her room again.

She looked over at me, giving me a smoky look. "Tonight is a special occasion, Timmy. I just happen to have a bottle of something good. So, tonight we're going someplace private. Just the two of us."

A bottle of something good? I immediately thought of the wet bar her dad kept in their basement with its stock of bourbon. Chances were her dad would never notice a single bottle missing. I wasn't wild about having her drive her car after polishing off a bottle of bourbon but I didn't say anything for fear of her thinking I wasn't fun to hang out with.

"So, where is this private place you mentioned?"

"The clearing up on the overlook."

"That's private?" The overlook was a common spot for people to park and fuck. In fact, it was so locally famous that it had become cliche.

"Private enough," she said. "No one is going to bother us as long as we're in the car."

"Okay, that's cool," I said, resigning myself to a belly full of bourbon and cum.

***

I heaved a sigh of relief when Angelica pulled the car into the clearing overlooking the valley. We were the only ones at the overlook although I was sure other couple would show up eventually.

"So, what's the bottle of something special?" I asked when she finally killed the ignition.

"Hold on," she said as she leaned over in front of me to open the car's glove box. She pulled out a small plastic bag before closing the glove box and sitting up in her seat. She pulled a small jar out of the bag and held it up for me to see. "So, what do you think?"

"K-Y jelly?" I said, nonplussed.

"Smart boy," Angelica said with a grin.

"I don't get it," I said. "This is your bottle of something good?"

"Yeah, it's actually a jar of something good," she said, "but I didn't want to ruin the surprise."

"We came here to fuck," I said. There was no question. There couldn't possibly be another reason for Angelica to bring me to the overlook with a jar of K-Y stashed away in the glove box.

"Is that a problem?"

"Not at all," I answered, shaking my head. "I wasn't expecting it, that's all. You've never let me touch you except for the occasional blow job before. And now you bring me out here to fuck you. I'm actually thrilled, or I will be as soon as I wrap my head around it."

Angelica laughed, throwing her head back in mirth. "Oh, god, too funny! You think you're gonna- oh, fuck that's funny!"

I was more lost than ever. "Mind sharing the joke?"

"There's no way I'm gonna let you put your tiny little penor in me," Angelica said, wiping her eyes. "The K-Y is for you. Specifically, for your ass."

"You think I'm gonna let you fuck me up the ass?"

Angelica smiled. "I know you are."

"No way!"

"Timmy Woodard, take off your pants and get in the back seat or I'll take you back home right now and you can spend the rest of the night at home with Mommy."

I knew she was serious. A minute later I was naked from the waist down and in the back seat on my hands and knees with my ass up in the air.

"Good boy," Angelica crooned as she knelt behind me, her hands on my ass. "Now just hold still for a bit, this will probably feel weird at first but I promise it will feel really good soon. For me at least."

I groaned as I felt a slick finger probe my asshole, spreading the slick lubricant around my anus before easing into the hole itself.

Once she had her finger all the way into my ass she swirled it around, getting my rectum good and slick. The feeling of her finger all the way inside of me was a strange one but I had to admit it didn't feel bad. In fact, I almost liked it once I got used to it.

"There, you should be good and lubed up now," Angelica said as she pulled her finger from my ass and wiped it off on my back. She put her hands on my hips a moment before I felt the tip of her erection probing for my slick asshole. "Fucky fucky time," she said with a laugh as she pushed her stiff cock against my anus, using main force to open it up.

She wasn't gentle by any means and I gasped in pain as she sank her hard length into me. "Fuck, take it a bit slower!"

"No way," she replied as she shoved herself in deeper. "You're as tight as any virgin. I'm gonna wreck your asshole before I'm done." She punctuated the statement by punching her dick all the way in until my asshole was wrapped tightly around the root of her cock.

"God, you don't need to rip my asshole apart," I said, snarling from the agony of having my asshole stretched out by Angelica's thick cock.

"Quit bitching, you little cunt," she said as she pulled her cock out before slamming it back in. "Just take my cock like the little cock hungry whore you know you are." I bit my lower lip bloody as she held onto my hips and pounded away on my asshole. "Hey, Timmy, did you know that you actually have a nicer ass than Wendy?"

"That's great," I grunted. "Would you mind not completely destroying it?"

"What a baby," Angelica sneered. "I fucked Wendy in the ass a lot harder than this and she didn't complain. If you can't take even this much it means you're even weaker than a girl. How's it feel being such a sissy boy?"

I didn't answer, instead I merely gritted my teeth and took it. For her part, Angelica didn't let up at all, forcing her cock deep into my rectum with each punishing thrust. I couldn't help gasping in pain as she stretched my asshole to the point of nearly being torn in half as she used me for her own pleasure just as hard as she could manage.

Eventually the pain eased and the feeling of her thick prong sliding inside me started to feel good. Moreover, I realized that she had draped herself onto my back and I could feel her tits pressed against me, her nipples hard points against my skin.

I couldn't help myself, I reached between my legs and fondled my own growing erection.

Angelica realized instantly what I was up to. "Knock it off," she snarled. "I swear, if you jizz all over the seat I'll fucking kill you."

I jerked my hand away from my cock but my erection never went away. I knew I'd be jerking off as soon as I got home.

It didn't take long before Angelica's moan of pleasure took on a desperate edge and I knew her orgasm was imminent. "Oh yes, I'm almost there. Your tight little ass is gonna make me fucking spurt! I'm gonna cum buckets deep in your guts. Your asshole will be leaking spooge for a week."

She crudely laughed at her own wit before roughly thrusting deep into my ass. I felt her cock twitching deep inside me and then a wet warm feeling spreading throughout my bowels. "Fuck yes, oh god, oh fuck...."

Her cock seemed throb in my ass forever as she flooded my guts with her seed. For a moment I had the thought that if it were possible to get a guy pregnant through his ass I would have gotten pregnant with triplets.

Angelica hissed as she pulled her wilting cock from my ass. "Make sure you don't drip cum onto my car seat, you little cum slut," she said as she pulled her jeans back on. "Just lie down in the back seat with your ass up to keep the jizz from leaking out. You can put your pants back on when I drop you off at your house."

I looked up at her from where I lie on the backseat. "We're not going to hang out tonight?"

She shook her head. "Naw, I'm gonna go play some Mario Kart, maybe go cruising for chicks if I feel horny later."

"Oh," I said, pondering my latest dismissal. "Well, maybe we can hang out tomorrow?"

"Yeah, sure, maybe."

***

The next day I was hanging around my house hoping for a phone call from Angelica and pondering whether I should just head over to her house. I did want to see her, of course. However, I didn't want to look clingy or desperate.

So instead, I spent the whole day beside the phone waffling over what to do.

When the phone rang I jumped at it and had the receiver to my ear in less than a second. "Hello?"

"Hey, Timmy. How's it hanging?"

"Oh, hi, Angelica," I said, hoping my voice didn't betray just how much I was trembling. "So, what's up? Did you want to hang out today?"

"Naw dude, I'm kinda busy right now," she said. "Last night I crashed Terry's party and man I found this... fuck, hold on...." -her voice came from far away and I knew she had pulled the phone away from her mouth, "shit, how many times to I need to tell you to watch the teeth, I don't want bite marks all up and down my cock," her voice came back to the phone- "sorry about that, this bitch uses her teeth so much that she gives bite jobs, not blow jobs. Anyway, she's just like a bicycle, you can ride her all night long and she's still ready to go come morning."

"Um...so...."

"Yeah, kinda busy today," Angelica said. "But she's gotta take off later so if you wanna get together tonight we can hang out and, y'know, have some fun."

I knew exactly what she meant by 'have some fun' and I knew she'd be the one having all the fun. But still, she was Angelica and that was everything. "Okay, sounds like a plan."