Lessons Learned

This is the first chapter of a series of stories based on some real-life experiences of mine. The names of those involved have been changed for a number of reasons, but the events themselves are unaltered. I hope you enjoy these pieces, and feel free to comment as you see fit.

*

Lizzy and I met on Halloween. My friend Joe and I had decided to celebrate All Hallow's Eve by dressing up as Jay and Silent Bob. As the taller and decidedly more slender of the two, I was going to be Jay. This meant shaving off my brown goatee and buying a blonde wig, while all my portly friend had to do to play Silent Bob was buy a mullet wig and borrow my trenchcoat.

Joe and I were taking a break from our daily rounds. We'd been touring the local college campus in our costumes all day, posing with interested students for pictures and spending an hour or so actually hanging outside a convenience store (in which a man actually asked me to perform the Jay rap from the beginning of

Jay and Silent Bob Strike Back

; I gladly obliged).

When Lizzy walked through the door, while I was in the middle of a round of

Guitar Hero III

, I was instantly struck by how tall she was. I stand a little over 6-foot-1, and without the black high-heel leather boots she fancied, Lizzy matched that height.

Her black hair flowed well below her shoulders, and as she stood at the door in her white and purple medieval dress, I was drawn to her considerable cleavage. It was obvious Lizzy had a rack on her, and even though I was trying not to look at her breasts as they nestled together in her top, I couldn't really help it.

Lizzy noticed immediately, smiling at me before sitting on the couch next to Joe. She'd been friends with Joe for roughly three years, but this was the first I'd seen her. Lizzy wasn't on the skinny side, but she wasn't really fat, either. She had nice curves – even in that dress – and sported a spread-wings tattoo across her shoulder blades. Her green eyes were striking in their intensity, and at that moment, in the middle of fucking up "My Name is Jonas" on expert, I knew I had to fuck this girl.

Nothing happened for much of the night outside of flirting. She was spending most of the night catching up with Joe, whom she hadn't seen in a few months, and talking to me. Still a smoker back then, I coaxed her outside whenever I wanted to take a smoke break, trying to gauge her interest through our conversations.

The second time we went outside for my cigarette break, I didn't even light up. We were so engrossed in whatever it was we were talking about that I'd simply forgotten to strike one. And though I never once made a conscious decision to give up cigarettes, I never had another one after that instant.

"One thing I absolutely love," Lizzy told me matter-of-factly, "is when a guy stands behind me and kisses along the side of my neck. Just drives me up the wall."

"Like this?" I asked with a grin, taking off my blond wig before standing directly behind Lizzy. Pressing my chest to her back, I rest my right hand on her hip as my tongue softly glided along her pulse line. With a soft groan, my left hand grabbed and squeezed her left breast, and as I felt the firmness and the weight in my palm, I felt her hips swivel against my crotch.

Lizzy was moaning, my lips wrapping around the spot I just licked to suck lightly. I was throbbing in my sweatpants, silently cursing the fact that we couldn't duck into the back seat of my Pontiac for a good fuck. We'd have to be quick, and I wanted desperately to take my time.

By the time I broke the embrace to go back inside, Lizzy's face was flushed, and the smile she gave me told me I'd already hit the right buttons. We talked and flirted for the rest of the night, which included an en masse trip to IHOP, which ultimately included roughly 10 people. We ate, talked and laughed – and I performed Jay's rap again before leaving the restaurant.

Before heading home for the night, and watching Lizzy leave so she could make it to her job delivering newspapers, she gave me her number. I started driving the 30 minutes it took for me to get from Joe's apartment to my place, and Lizzy called.

"Pleasant surprise," was my greeting.

"You missed out," the husky voice replied on the other end. "I was getting changed. You could've seen me in my bra and panties."

I laughed a little. "Doesn't mean I won't get the chance again."

Lizzy chuckled before letting out a soft moan. "The way you made me feel outside earlier?" she shot back. "Most definitely. I'm still wet from that, you know."

I choked back a groan as I felt my cock lurch in my pants. "Really now …"

"It's all I can do not to shove my hand down my pants while I'm driving."

Again, I laughed. "That … doesn't sound like it'd be too safe." Never mind the fact that I was starting to fight that very temptation myself.

"Oh, I've done it before."

My mouth hung open in stunned silence. I could feel the head of my cock throbbing against my seatbelt at this point, and I wanted to pull over and whip it out right at that moment. I heard Lizzy laugh at my silence. "What's the matter?" she asked coyly. "Was it something I said?"

I cleared my throat before speaking again. "If I was over there, you wouldn't need to take such dangerous measures."

"Really. And what would you be doing?"

"Well," I began, wishing I had a hands-free set for my phone. This hard-on was almost getting unbearable and I still had about 20 minutes to go before I got home. "I'd start with that neck thing. You seemed to like that.

"Then, while I'm doing the neck thing, I'd slowly take off all your clothes … that way, when I'm fondling those tits of yours, I can pinch the nipple and my other hand can slide between your legs and play with your hot pussy. Make you cum before I ever fuck you."

There was a silence on the other end for a split second before I heard Lizzy moan softly. The noise sent another jolt to my rigid shaft and even if I couldn't stroke it right at this moment, I at least had to free it. So I undid the tie on the front of my sweatpants and pulled them down to let my cock free, glancing down to see precum dotting the head as I sat at a red light.

"Mmmm, do that and I might have to reward you. Push you onto the couch before getting on my knees and swallowing your shaft. Take you all the way in … I wondered how you tasted when you were pressed against me."

Pulling onto the interstate, I licked my lips and groaned. I'd been wondering nearly the same thing, only on my end it was how my shaft would feel surrounded by her warm, moist lips. And what her tits would look like covered in my release.

I was determined to find out, too.

"Bet you're hard, aren't you?" she asked with a little bit of a smirk in her voice, almost like she knew what she was doing to me. I heard her let out a soft moan, telling me she did indeed have a hand down her pants while she was driving. "Can't wait to grab that shaft and tug on it, jack off thinking of fucking me until you blow?"

"You'd like that, wouldn't you?" was honestly the only thing I could say at this point.

Lizzy chuckled, her laugh darker than before. It wasn't a dangerous laugh, just one that told me the right buttons were being pushed. I could tell without seeing her she was wet, and somehow I just knew that as she flew down the interstate, she had one hand working her sweet little clit.

"I would," she finally said with a sharp gasp. She was getting closer. "I want you lying on your bed tonight, completely naked. I want that shaft throbbing in your hand, I want you spitting on it, making it nice and wet – but not nearly as wet as my pussy would make it. Stroke, stroke, just stroke that fucking cock until you blow your load.

"I want you pasted in your own cum … all because of me."

I was speechless. I was glad I decided not to touch my throbbing member yet, because if I had, I would've likely lost control and swerved a bit. And considering I passed a state trooper on the side of the road at that moment, I was thankful for my restraint – even if it was becoming almost impossible.

"I think I'd like it better if your tits were pasted in my cum," I managed through a husky voice. Breathing was difficult and I could feel it getting warmer in my car. My body was on fire, all from the mere words she spoke. If it was this intense now, what would the real thing be like?

"Mmmmmm," I heard her coo. "We might have to try that."

"What do you mean 'might'?" I quipped, just in time to hear another soft moan on the other end. This one dragged out a bit, with a sharp increase in pitch at the end, and if sound were any indication, Lizzy was writhing in the seat of her car.

It was almost like something out of a porn movie, and certainly kinkier than anything I'd ever experienced outside a chat room. I'd had my fair share of sex, but nothing anywhere near this raw.

Honestly, I wasn't sure how long I would make it – and I wasn't even touching myself yet.

I could feel the precum leaking down my shaft as I reached my exit, pulling off to the right with the phone stuck to my ear. Again, I cursed my lack of hands-free set, listening to the moans and sighs on the other end. Lizzy moaned my name once, telling me she had two fingers buried in her warm slit before apparently lowering her phone for me to hear.

I could tell because for about 15 seconds I could hear nothing but soft slurping sounds. One moan was audible in the background, but that wet pussy was all I could hear. My cock jumped in excitement, and I thought I was gonna blow right then.

But I didn't, and Lizzy brought the phone back to her ear. "Now imagine your cock in there instead of my fingers … I'd push you down onto the bed, get on top and show you a world you could only dream of … mmmmmmmmmmmmm."

"Flip you over," I began, my voice showing obvious signs of struggle as I fought with my arousal – or rather, my inability to act on it at the moment, "fuck your warm snatch, pound that hot little pussy and pull on your hair … you'd like that, wouldn't you?

"You'd like being my cumslut."

"Yes I would," she whispered before another gasp filled my head. She moaned long and low in her throat, the sound building until she let out a yelp. "Oh god! I'm gonna cum!"

Pulling off into a dark parking lot, empty and with no lights, I undid my seat belt and put Lizzy on speaker phone. I groaned with release once I was finally able to wrap my hand fully around my cock, my thumb coated in precum.

"Cum for me, Lizzy … tell me how bad you want it."

I'd worked my shirt over my head, so when I finally blew, I wouldn't make a mess all over my clothes. I panted with each furious stroke of my wrist, my ears hanging on every word and moan coming from my phone.

Lizzy never really got to speaking any coherent words; rather, she filled my phone with unintelligible groans and heavy breathing before she screamed in a crescendo, and I could've sworn as my hand worked furiously over my shaft that I could hear the contractions in her pussy muscles.

It was one thing to hear Lizzy cum, but I almost felt as if I could feel her orgasm, even as she caught her breath, groaned and begged for me to cum next.

"Cum for me," she cooed. "Cum for me and you get to lick my fingers clean."

I licked my lips at the thought of what her juices tasted like, and before I knew it, the moment had finally arrived. I didn't even get to announce it, but my release finally took over. My thighs quivered and with a groan so loud it surprised even me, my cock shot all its juices. My chest and the steering wheel took the brunt of my load as I came, my body shaking as I slowed my strokes, eventually just sitting in the seat trying to catch my breath.

As my breathing returned to normal, so did my sense of hearing. I heard Lizzy chuckle to herself over the phone before she added a "Mmmmmmmmmmm" to it.

"Bet you made quite the mess," she said as I turned off speaker phone.

"My poor steering wheel," I whispered into the phone, still struggling to find oxygen.

"Well," Lizzy answered in her husky voice, "tomorrow night you can cum all over my tits. When you get off work, come to my place."

I was again left speechless. Did Lizzy just tell me to go to her place to fuck her? And ask me to cum on those considerable tits, to boot? It took me a moment to realize it was real – one of the side effects of a four-year dry spell – but once I came to, I hastily agreed.

"We'll have all night, too," she offered. "But for now, I need to let you go, cause I just got to work.

"Get your rest, okay?"

Before I could answer the line went dead, and I was left by myself in the car with no shirt on and a steering wheel covered in jizz. I grabbed a napkin out of the glove box to clean up the mess before driving the five minutes I had left to get home, where I was sure I would promptly fall asleep.

How could I not after an orgasm that intense?

But when I got home and into bed, I realized I couldn't sleep; I was too busy thinking of the night ahead, what it would be like to slide into Lizzy's moist cavern for the first time. Before I knew it, I was hard again, and I tugged one last shot out before finally drifting off to sleep.

The first day of November was going to be one hell of a ride.