First Time For Everything
A story of firsts.
It was known around school that I was the only senior dating an older girl but I didn’t mind the attention; I actually accepted it as a compliment. Although I was confident in dating Amy from my part time job at a grocery store, I was embarrassed telling her I was still a virgin. Amy always joked around and picked on me, saying she robbed the cradle and all that nonsense, but I didn’t pay any attention to it really because, even though we hadn’t had sex yet, I knew it was coming.
Amy was a 21-year-old single mother who worked in the photo center of our store, and I was a stock boy who had the slightly humiliating duty of filling up the women’s hygiene items in the aisle directly across from her department. One night she decided to pay me a visit while refilling holes in the shelves with products and, after talking for almost an hour, she left and I ended my shift with the hormones of my youth just raging for the sake of her appearance. Although she had recently become a mother, Amy was still only about 115 pounds and tight-bodied (except for her motherhood-induced large breasts). I had often been caught staring at her while stocking and she knew I was paying full attention to her as if my eyes were burning holes through her shirt.
Being a late bloomer, I was only 17 when I met Amy in March and my birthday wasn’t until May. I played in sports like soccer and ran cross-country so I was built fairly well, in my opinion, and my summers working out on the farms kept my skin bronzed from the days in the sun without a shirt. Although I rarely worked out, I had a significant six-pack and, having high metabolism, I only had around 3% body fat, making my body toned and my arms clean and cut.
After dating Amy for about a month, I was never to be found at my house as I was constantly over at her house, anxiously anticipating our every minute together. One day when I was at her house, we were watching TV and I dozed off, lying on the floor. After almost an hour napping, I was suddenly awakened to a pain in my rib cage and I immediately jumped up to see what had happened when I saw Amy standing in front of me with a grin on her face. Without a moment to spare, she started pulling me by the arm back to her bedroom, busting doors open like we were escaping a fire. Once in her room, she immediately grabbed my clothes and started to undress me, starting with my shirt. Since I had just woken up I was unable to hide the enormous erection beneath my jeans and Amy grabbed my cock through them and squeezed it with pleasure. I let out a moan in disbelief at what was happening to me and realizing I was about to have my first sexual encounter.
After she unzipped my pants, my blood-engorged cock sprang up to meet Amy’s chin and she just smiled up at me, grabbing it with both hands and shoving her mouth down over my hard shaft, engulfing all of me without hesitation. I grabbed her by two handfuls of hair and just laid my head back in satisfaction as she slurped up and down my member with one of her hands fondling my balls. Amy kept sucking on my cock while looking into my eyes greedily with plans of what to do to me next. After several minutes she pulled her mouth off my rigid dick and threw me down to the bed. I obliged and took my pants all the way off while watching her undress in front me, taking all the little steps to draw her thong off over her ass while bending over in front of the bed.
After climbing onto the bed naked, she lifted up her leg a little and grabbed my cock to direct it where it had been longing to enter for some time. I curled my toes as the tip of my dick parted her surprisingly tight lips and, with one motion, she sat all the way down until her clit was rubbing below my waist. First, Amy started with smooth, fluid rocks back and forth, letting me feel the entire depths of her pussy as my cock slid in and out of her with a warm wetness.
Almost failing to speak, she said, “Oh, my god; I didn’t know you were THIS big!” and, being a virgin I couldn’t really tell if I was a good size or not, but if she said it then I believed it. Amy then leaned back and began bouncing her pussy up and down on my cock, letting me see every inch of it go in and out of her juicy, wet lips. Just the sight of it alone almost made me orgasm, but I managed to contain myself.
Not wanting to do all the work, Amy got off my cock and said, “Do me from behind so you can pull my hair,” to which I had no trouble responding. I turned her over to her hands and knees to await my throbbing cock. I lined up behind her and, before I could get a hand on my dick to help guide it into her pussy, she once again reached down and grabbed it first, stroking it a few times before rubbing the tip up between her pussy lips, taking a second to rub circles with it around her clit.
Then I took control. Grasping her hips, I shoved my cock inside her as far as I could go, to which she answered with, “Oh fuck, Taylor! Fuck me! Fuck my brains out!" The feeling of my cock stretching her pussy with every plunge I made my dick swell even more and, before long, I could feel the massive eruption coming on.
Panicking I told her, “Oh, god; I’m gonna cum, what-"
She finished my sentence with, “Cum inside me, baby; I want it all inside me!”
Not being able to help myself, I plunged deeper into her pussy one last time before grabbing her by the shoulders and releasing my load of hot semen in the depths of her pussy. Without even completely understanding the achievement I had just made, I leaned over to rest on her back a moment before pulling out of her, my cock dripping cum onto the bed. As if in a porn movie I’d seen, Amy abruptly turned around and took my dick in her mouth, sucking all the last few drops of cum still inside, and cleaning up all the cum around my groin.
With a smile from ear to ear, Amy looked up at me and said, “I couldn’t help myself; I just knew you were a virgin and I wanted to help you out.” I believe I couldn’t have been more pleased in her wish to steal my virginity.