Never Let Your Hookup Overhear Her Mom Having Sex

Illustration for article titled Never Let Your Hookup Overhear Her Mom Having Sex

Welcome to Great Moments in Drunken Hookup Failure, where we showcase three heartwarming true stories of drunken love gone horribly awry. Off we go.


Time to throw up the Batsignal and call for new DHF entries. Email them to me, please. As always, your entries should be brief, and our only interest is in your personal humiliation, and not the degradation of your companion for the evening. Time for the stories:


Back in the spring of '97 my alma mater, the University of Arizona, improbably won the basketball national championship by beating three #1 seeds. As such, the 40,000 students decided to celebrate (read: "riot"). When the cops started to pepper spray the crowd, me and my buddy Rich decided to ditch the overturned cars and bonfires to find our own party.

At that time in Tucson, all liquor sales ended at 1am, so we were determined to pick up a couple of bottles of whatever we could lay our hands on before that time. So we headed over to the closest liquor store that wasn't completely packed with people with the same idea as ours. Finally, with literally minutes to spare, we got in line at a liquor store with two bottles of vodka and three twenty four packs of beer (yes, it was just for us, but we figured we'd find our friends as the night wore on and we'd be heroes for having the foresight to pick up beer and liquor while they were busy running from the cops in riot gear). I then noticed that the girl ahead of me in line was this hottie from my astronomy class. I didn't know her name, but that didn't stop me from chatting her up as we waited to ring up our purchases.

She was in line by herself, so I asked where her friends were. She told me that her mom was in town so her friends had basically ditched her to go hang out with the crowd and get wasted outside the judging eye of an adult. She then said, "But I swear, my mom is really cool!" So I asked what her plan was and she basically said that she was headed back to her mom's hotel room to watch the kids partying/rioting on the local news. It was then that Rich piped up and invited them to our place to wait on our friends and the inevitable party that would break out once the cops broke up everything. She agreed quickly and introduced herself to Rich as "Ashley" (not her real name since I can't remember it).

When Ashley got done buying her Zima or whatever girlie drinks she had got she told us she was going to grab her mom and meet us outside. After she exited the store I looked at Rich and said "dibs on Ashley . . . you can have the mom". We chuckled and he said we would just have to see where the night took us.

We met up with Ashley and her mom outside, who has in her mid to late 40's and wasn't all that bad looking. I could see where Ashley got her good looks from. Fast foward to our place and it turns out that Ashley's mom WAS cool. She even took a couple of bong rips and the four of us were in full-on party mode.

I proceeded to get hammered, as did Ashley. By this time it was about 3 in the morning and our friends hadn't yet shown up, but I didn't care because I could tell things were going great with Ashley and that I was probably going to bang her. Rich was a good friend and had taken Ashley's mom on a tour of the house (which is hilarious since it was a total typical off-campus dump). So I went to make my move and Ashley was receptive. After about ten minutes of making out I suggested we go to my room. Ashley quickly said yes and we got up to go. As we were walking down the hallway though we could hear the unmistakable sound of Rich banging the ever-loving crap out of Ashley's mom. She was literally screaming, telling Rich "HARDER! HARDER!"

Ashley got this awful look on her face and I knew at that moment that not only was I not getting laid that night, but that I would probably have to drop that easy-A astronomy class just so we would never have to see each other again. Ashley then started knocking loudly on Rich's door, trying to yell over her mom's screaming, telling her that they had to leave. Ashley's mom either didn't hear or didn't care because they kept going at it for another 20 minutes while we stood outside the door to Rich's bedroom listening to him defile that cougar in what I could only imagine was every way possible.

When the screaming and squeaking bedsprings died down to just some heavy breathing, Ashley knocked again and tried the door handle. The door opened right up (of course he didn't lock it - that would have been the smart thing to do) and there was Ashley's mom, naked, wiping her vag with a handtowel while Rich laid on the bed, equally naked, laughing to himself. Ashley told her mom to get dressed and that she would meet her outside because she wanted to go home.

As Ashley's mom walked out she told us thanks for the good time and then said to Rich, "I hope Ash isn't too pissed. If she tells my husband I'm so screwed."

I saw Ashley every once in a while on campus after that, but we made it a point to never make eye-contact. I couldn't be pissed at Rich though. I did tell him that he had to take the mom.


Approximately 5 years ago, a girl that I know named Jenn visited my city for a party. By word of mouth, I was aware that Jenn was going to attend the party; however, we never actually spoke on the phone or made plans to meet. Fast forward through the pre-game of hard liquor, gravity bongs, and multiple beer funnels. My taxi cab arrives at a posh night club for the birthday party and I venture into the night.

I drink a couple drinks walking around looking to interject myself into conversation with Jenn. I find Jenn drinking at the bar with a few guys. Being the gentleman that I am, I introduced myself to the individuals around her then focused my attention back on Jenn. She and I eventually establish common ground and a mutual enjoyment for shots. After an hour of conversation and talking about nothing that I recall, we decide to leave the party and go back to my house.

We go back to my room and have enjoyable drunken sex.

The failure rears its ugly head during the before breakfast and departure sex. I wake up with a blinding headache and leave my bedroom for water. I drink probably 2 or 3 glasses of water then return to bed with a glass for Jenn. Jenn is still under the covers and trying to collect her thoughts from last night's debauchery. She finally collects her thoughts and has a wonderful idea to give me a blow job to ease my hangover. I am extremely grateful for this idea and allow her to commence fellatio.

Blow jobs are a tremendous way to start the day, and during all the enjoyment along with my mind shattering hangover I forgot her last words before started. Those words being, "make sure you tap my head before you come, I can't stand the taste". Obviously, I forgot her instructions immediately and before she knew it I discover my eyes moving towards the back of my brain and my toes pointing towards the ceiling fan.

I let loose a few strings of baby batter that pass directly into Jenn's mouth. I immediately notice that she detaches her mouth from my penis and violently slings her head upwards. Before I have time to react, Jenn's innate response was to puke my freshly expelled baby batter along with whatever else she had in your stomach directly on my naked chest. I am instantly horrified once I realized what had transpired all before 9AM. We stare at each other with amazement, shame, and disgust for what felt like minutes. Then Jenn leaves the room and grabs a wet towel. We both sit down on the other edge of the bed (the side that isn't covered with jizz/puke) and laugh about the awkward situation.


I had the fortune/misfortune of going to school near two women's colleges. These places were harder to crack than Fort Knox unless you had an "in" with one of the girls. After trying for a year, my friend finally started dating a girl from one of them and we were slowly starting to integrate into her group of friends. My buddy's girlfriend had one particularly attractive friend who I immediately became interested in. We hung out as a group a few times and she was always friendly, but reserved. One night their whole house had a big party and I ended up in a room talking with the girl I was into, who I'll call Stephanie. Things are going well, we find out we have a lot in common, same musical tastes, the whole deal. It unfortunately also comes out that she has a boyfriend back home in Idaho. The whole time we're talking I'm also drinking of course, though, so I can't quite bring myself to give up on this girl despite the boyfriend situation. That all comes to an end however, when a fire alarm goes off. Everyone evacuates the building and as we're standing around outside, I lose track of Stephanie.

After a moment however, a random drunk girl, whose name I can't tell you because I never got it, comes and starts basically groping me in the yard outside the dorm. Being drunk and figuring I have nothing to lose with Stephanie anyway, I go with this new random girl and she leads me back into the house and into a stairway. We start making out there but are interrupted (unsurprisingly) so she brings me back up to her bedroom. Thinking I'm golden, I get her on the bed and continue the make-out session. Sadly, that's when the unfortunate part of women's colleges comes in. Militant lesbians start knocking on the door, screaming at this girl to let them in. When we open the door, there are six or seven pissed off looking girls, half of whom could take me in a fair fight. The lesbian in charge informs me that the girl I'm hooking up with is too drunk and therefore I'm not allowed to be there with her. The girls then literally take out pink Saran wrap and roll it out the door to the stairs as if it's a red carpet and basically march me and my blue balls out of the house. To top it off, my friend's girlfriend later told me that Stephanie was interested in me and went looking for me that night after the fire alarm and couldn't figure out where I'd gone.