The Time My Mom (and My Girlfriend’s Mom) Caught Me Having Wild, Weird Sex With My Girlfriend

By 05.07.10


Editor’s Note: Today we’ve already annouced the four runners-up of our “The Time My Mother Caught Me…” Mother’s Day contest. And the grand-prize winner, who will receive a pair of Liquid Flow shorts and a bouquet flowers for his mom, is Cassius Clay! For more embarrassing Mother’s Day stories, click here.


Being the proverbial jock that I was in high school, I never really had any difficulty finding girlfriends. I typically fell for tall, ditsy, long-legged girls with huge tits and an ass to match. Come the start of senior year, I was single and was very much looking for a change of pace.


As my fellow jock friends and I sat down to lunch on the first day of that infamous senior year, we each commented on every girl that walked by. Primarily, the comments ranged from, “Yeah, I’d bang her,”  to “Eh, I’d have to be pretty drunk.” No one thought much of who was walking by or what was being said until this cute, innocent, short little choirgirl priss named Samantha walked by. Normally when the question of “bangable” or even “paperbagable” arose, my friends were quick to the thumbs down and fart noise. However, this time one of my friends chimed in, claiming he heard this goody two-shoes, overachieving angel was in fact a freak behind closed doors. No one believed him, but I knew it was true.


From that moment on, I made it my goal to go out with Samantha, or to at least get a sampling of some of her freakiness. Given that I was the captain of our state championship soccer team, asking her to hang out was a walk in the park and she excitedly accepted my offer. I got a lot of shit from my friends, who felt that she wasn’t up to my standards, but I didn’t care. I knew that in the end I’d be able to prove to them it was all worth it and soon after they’d label me a genius or better yet, “the man” (whatever that means).


If I wanted to get this show on the road, I knew we’d better hang out alone. I invited her over on a Friday after school when no one was home at my house. In an attempt to avoid an awkward situation of her coming home and walking in on something we were doing, I had forewarned my mom on Wednesday that I was doing so. Regrettably, I told her I was helping Samantha with homework, so my mom didn’t exactly get my subliminal memo. On Thursday night I reminded my mom again and she exclaimed that she had been good friends with Samantha’s mom for a while. She said she would actually be out to lunch with her while Samantha and I were at the house alone. I figured this was perfect.


Since this was our first time hanging out, I didn’t expect much to happen, given her squeaky clean reputation. Boy was I wrong. As soon as I closed the back door she was all over me. We began passionately making out and undressing in the kitchen until eventually we made it up to my room. She violently threw me onto the bed. Next thing I know, boxers are off, panties and bra come off, and she’s riding me like I’m the last guy on earth she’ll ever f*ck. No condom, no talking, no nothing. Just pure, aggressive, hormonal sex. I was very shocked by all this and, for the most part, impressed, but I knew she had way more freakiness left in the tank, I just needed to get it out somehow.


After the first time I came, I asked her what the freakiest thing she had ever done was. She named 4 or 5 things that I had never even heard of, things that I was fairly certain were not legal in the United States. She then brought up something her old boyfriend always wanted to try but she never let him attempt. It was called a “donkey punch.” If there was one story I definitely needed to tell all the boys at lunch, this was it. When she asked me if I wanted to do it, I said, “yes,” without hesitating. 


For those of you who don’t know what a “donkey punch” is, it’s when you’re banging your lady friend from behind — in the ass nonetheless — and right before you finish you punch her in the back of the head, knocking her unconscious which supposedly causes her ass cheeks to involuntarily tighten, which then sucks the c*m right out of you. An indescribable feeling and perhaps, potentially, the best sex story of all time (note the word potentially).


So, as I’m nailing her from behind, she starts moaning like you wouldn’t believe. She’s flat out loving it and so am I, but the noise was just too much. I put on some loud music to conceal it. Unbeknownst to me, my mom and Samantha ’s mom changed their reservation to an earlier time. They had just gotten home to come check on Samantha and I as we study. My mom thought this would be a perfect opportunity for me to meet Samantha ’s mom and hopefully get on her good side if I ever planned to make Samantha my legit girlfriend.


Of course, right as I’m about to c*m, my mom and Samantha’s mom walk into my room. I am unaware of this given that the door to my room is directly behind us. The scream from Samantha’s mom startles the f*ck out of me and I accidentially land a huge haymaker straight to Samantha’s nose when she turns around.


Blood starts flying everywhere, Samantha’s crying, both our moms are standing there screaming, jaws to the floor, and I’m just kneeling down, butt nekked, with the worst blue balls ever, wondering if this could get any more embarrassing. Once I snap out of this state of embarrassment-induced shock, I rush to put on my clothes. So does Samantha. As soon as she’s fully clothed, her mom grabs her by the wrist and basically drags her from my room out to the car all while Samantha is still crying and pinching her nose to stop some of the blood flow, which by now has thoroughly ruined the sheets and pillows on my bed and even the carpet on the floor.


My mom, who is also in shock, runs away from my room hysterically crying and slams the door behind her.


As I sit there speechless, hoping that this is just a nightmare sent straight from hell and that I’ll be waking up any minute now, I get a text from Samantha saying that her extremely over-protective mom is pressing charges against me for assault. She tells me this is “good news” because she wanted to try me for rape, seeing as we weren’t using a condom, I was being a little uncharacteristically aggressive from behind given the unusual circ*mstances, and I also might have been saying some not so G-rated things right as she walked in. 


Samantha’s mom eventually dropped the charges but only after she made us agree to pay Samantha’s tuition at the new private school she’d be attending. She was so humiliated and embarrassed about the incident that her mom forced her to transfer.


My mom ended up grounding me for practically all of senior year. Our relationship was ruined and family dinners became extinct. I haven’t had a non-awkward conversation with her since. Being 18 with a babysitter kind of sucked, too.

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