I usually don’t talk about this, but my girlfriend, Candie, has been pressuring me to share secrets about my sexual history and I feel the need to vent in a private forum first, just to get comfortable with it. It’s not that I’m ashamed, or that I even have a long history to share. Honestly, Candie is my first serious girlfriend and only the second girl I’ve ever been with. But I have a dirty secret about how I lost my virginity. And when I say dirty, I mean dirty in the best possible way.
Many guys my age would say their high school years were some of the best times of their lives. My high school was composed of cliques: either you were in a group or you weren’t. The jocks fucked the cheerleaders, the party animals fucked the drunk girls, the cowboys fucked the redneck girls, class presidents fucked the class secretaries, and the sensitive guys fucked the good girls. I was shy and really had no life outside of academia, besides the chess club and the debate team, which I knew would look great on my college applications. Getting a full-ride scholarship to a good university was my top priority – not socializing. I didn’t belong to any group, so I was shit out of luck. No fucking for me.
Not that I wasn’t interested in fucking. Once I hit sixteen, I was like a walking hard-on. Hot, unattainable cunt was an obsession to me. The conversations I overheard in the guys’ locker room every day after phys ed were ripe with material for my fantasies: talk of Gwen’s round ass and the sounds she made as she came, of Tara’s pink nipples and tight pussy, and of the way Laura rubbed Tom’s balls as she sucked on his cock made me so horny that it was not unusual for me to have to lock myself in the bathroom to rub one out before the next class. To this day, the mental image of Jane losing her virginity in the school parking lot on the hood of John’s car is still etched into my memory. John had agreed to ride her home after their Saturday morning detention class, and he had given her some ride. Sweet Jane.
Locker room talk and girlie magazines fueled countless jack-off sessions throughout my freshman and sophomore years. My erotic fantasy world really opened up when I discovered internet porn as a junior, once my mom decided she trusted me enough to uninstall the spyware she’d been using to monitor my web use. (Did I mention my mom was VERY strict?) Once I had access to all the gang-banging, anal-probing, lesbian clit-licking, pussy-pounding, dick-sucking scenery I could get my hands on, masturbating to pornography became my career, second only to my school obligations. I couldn’t get enough of the porn, and probably because I couldn’t get any in real life. I walked through the school hallways eyeing every hot little thing I saw, envisioning her pink pussy, wondering what her cum smelled and tasted like, and imagining how she might squeal with delight if I ever got the chance to pound my dick into her fresh, hot cunt. I got very good at tucking my erections into my waistband, and made frequent trips to the bathroom.
Come senior year, in spite of my lack of physical experience, I was a regular sex-aficionado . . . or so I thought. It was a guy in my physics lab – Lance was his name – who introduced me to the land of MILF: Moms I’d Like to Fuck. Up to that point, my mental conquests had been limited to tight, tiny and perky barely-legals. I thought that was where it was at. From what Lance said, I was wrong. He was banging his next-door neighbor, a forty-something woman whose older husband had passed away the year prior.
I still remember the sex-crazed look in Lance’s eyes as he spilled the beans: “Sure, Jacob, there’s nothing like breaking in a new twat, but most of these high school girls lay there like a cadaver until it’s over, ya know?”
I had no idea, but nodded in agreement.
“But my neighbor, Evelyn, she knows some tricks. She rides my cock like it’s God. I can’t even put it into words. It’s like she’s sucking my dick with that cunt of hers.”
Again, I had no idea. But it sounded good. I assured Lance I’d mount a MILF the next chance I got. Until then, my trusty friend internet was there to help fill the void.
I searched the web for cougar and MILF porn as soon as I got home, and I liked what I found. The fully grown women on the sites made the girls at my high school look like teenaged boys. And there was something very tempting about the look in their eyes: a look of confidence, knowledge and skill. The soft curves of their hips and the fullness of their breasts and asses turned me on, and I wanted to bury my face in some thick, untamed bush. In school, it was no longer my female classmates that I gave a good mental fucking to, but rather my teachers . . . and especially the librarian. Ms. Winters had a fuck-me body if I ever did see one. I imagined putting my bookworm in that juicy ass and sucking on those pert Dewey decimals every time I visited the library.
Unfortunately, when I graduated high school as the valedictorian, I earned a degree in virginity. I was determined not to enter college as a masturbation major and made it my goal to get some pussy that summer, one way or another. When my mom announced that my Aunt Nancy’s husband had left her and that she was coming to stay with us until she could get on her feet, I was more than a little pissed. It meant having to give up my room, which threw a wrench in my plan to bring a girl home for a good pounding. Little did I know that Aunt Nancy coming to live with us would be the best thing that could’ve happened that summer.
The anxiety on my mom’s face was unmistakable as she spoke: “I’m working a double shift today. Your Aunt Nancy will be here around noon. Please do your best to make her feel comfortable. Keep in mind that she’s going through a hard time . . . and that she’s not too stable.”
I knew what my mom meant by “not too stable.” She and Aunt Nancy were polar opposites. My mom had struggled for my entire life to raise me single-handedly, often working two jobs and taking on the role of both mother and father. She was the pinnacle of responsibility and stability. Aunt Nancy, on the other hand, had married a very rich man at a very young age and never had any children. At forty-three, she was still known for her wild antics and outspoken nature. I hadn’t seen her since I was fifteen, when she came to visit for a cousin’s wedding and snuck me liquor from the bar all night.
The taxi pulled into the driveway at exactly twelve thirty. Aunt Nancy emerged from the cab looking exactly as she did the last time I’d seen her: like a well-aged version of Betty Boop. Her eyes lit up as she gestured for me to give her a hug. Her voice was girlish: “Look at you, Jacob! All grown up! And look at those muscles. Mmmmmmmmm. Now be a lovey and help me with my bags.”
It was cool having Aunt Nancy around. For the first few days, she paced around the house looking lost and a little sad. But after a while she seemed to start coming to life. We spent our days playing cards, drinking cocktails, and swimming in the pool. One day, I stepped outside to find her sunbathing in the nude. I was stunned – not with fear, but with excitement. I couldn’t tear my eyes away from the curves of her hourglass figure. I watched as her sweat trickled around her full breasts, down her soft belly and into her healthy bush, and had to fight an almost uncontrollable urge to pounce on her right then and there. I was embarrassed by my sexual desire and hoped she hadn’t heard me come out. Just as I realized I had a raging hard-on, Aunt Nancy sat up and pushed her sunglasses off her face. She turned to examine the horny monster protruding from my swim trunks and giggled, “Well, I’m happy to see you, too, Jacob.”
My face flushed and I wanted to run, but I could not move. There was something about the way she was eyeing me. She said she thought I’d gone out for the day and apologized for being naked, but she made no effort to cover up: “It’s nothing you haven’t seen before, right?”
When I couldn’t answer her, she stood from the lounger and walked toward me. She stood right in front of me, within an inch of my boner, and cupped my face in her hands. “Look at how red-faced you are! Aw, what’s the matter, honey? You’re not scared of me are you? Your dick is telling me you’re not scared at all. He says he wants to play.”
And she was right. My dick wanted to play, explore, dig for treasure, mine for gold, you name it. But I still couldn’t speak, other than to say, “You’re my Aunt . . .”
“Well, Jakey, it’s not like we’re getting married. It’s just sex. It’s just a dick getting some good pussy and a cunt getting a good fucking. Whaddya say?”
She had a point. I could not argue, nor did I want to. At that point I wanted nothing more than to ram my dick into every soft, wet place in Nancy’s built-for-sex body. And she knew it, because her hands immediately grabbed my cock and started rubbing. Then she got on her knees and started sucking my balls before moving on to my penis, which she took deep into her throat as she bobbed her head every which way. It felt better than I’d been able to imagine and I came almost immediately. I would’ve been embarrassed if not for the fact that Nancy wasn’t even fazed. “Don’t worry,” she said, “we have plenty of time.”
With that, she took my hand and led me to the lounger by the pool, where she laid down on her back and opened her legs to straddle either side of the chair. I watched as she spread her pussy open and began to massage her clit. Her cunt was wet and creamy. I wanted to taste it.
“Jacob, come over here and help me out. Let me show you how to make a woman cum.”
She guided my fingers into her throbbing hole and pulled my head into her lap, where my tongue searched out her swollen clit. Nancy guided my movements with her hands and, before I knew it, she was moaning like a cat in heat, telling me she was about to cum. And, man, did she cum! It was exquisite.
Round two, she stood from the lounger and had me take her place. Then she straddled me and took what had to be the biggest, hardest erection I’d ever had deep into her warm, welcoming pussy. She fucked me furiously, as if possessed, as if she couldn’t get enough of me in her. We were both slippery with sweat and cum. Her heavy tits bounced up and down as she rode my cock, grinding her warm clit against my body. It was so much hotter than any porn film I’d ever seen. The entire neighborhood must’ve heard our uncontrollable moaning, and neither of us cared.
After we came, we took a skinny-dip in the pool to cool off. There was nothing awkward between us. We shared a secret, a secret that we reenacted throughout the rest of the summer, until it was time for fall classes to begin. When I entered my freshman year at Virginia Tech, I had the swagger of a genuine ladies man. I knew how to rub, suck, and fuck like nobody’s business, and had no problem approaching girls.
I met Candie in economics and knew right away that I had to bang her. She was a cute little blond, tiny but curvy, and stacked front and back. We hit it off right away and got serious quickly.
Candie loves that I’m smart and funny, and thinks I’m cute. But mostly she loves that I can fuck her mindless. And I love the way she purrs like a kitten as I pump her full of my meat.
Candie was popular in high school and worked her way through most of the varsity jocks. She had a lot of experience, but it was the wrong kind. She wasn’t used to being with a guy who knew how to probe at her most sensitive spot long enough to make her squirt. She’d never cum so hard that her toes went numb. Not until me.
Naturally, Candie assumes I slept around in high school, and she wants to know how many pussies I’ve tamed. I don’t know how to break it to her that she’s far off base. I’m not sure which would shock her more: that she’s the second of only two . . . or that she has my Aunt Nancy to thank for her mind-blowing orgasms. For now, I think I’ll just keep my dirty little secret between me and Nancy.