You’d be surprised how many people have embarrassing hookup stories. From having one too many drinks to acting out of spite, some people just act in the heat of the moment and live to either regret or cherish what lead soon after. A close friend is like a sibling. In a way, their mom and dad become part of the family. Despite this, some people have violated this unspoken boundary by doing the unthinkable: Hooking Up With Them. In this segment, people share anonymous stories about the time they got to bang their friend’s parent and lived to tell the tale.
Dinner And A Show
“I slept with my friend’s aunt.
At the time, my friend was like a brother to me. I was always over at his house. I knew his family for about ten years but I barely spoke at length with his aunt.
At some point, the secret came out about her husband cheating on her with their kids’ friend’s parents. Once she found out, my friend’s aunt kept it secret because she didn’t want to ruin the family. She pretended nothing happened while sleeping in the same bed as her cheating husband for about four years.
After twenty years of marriage, my friend’s aunt finally divorced his uncle. Out of spite, his uncle told his cousins they were divorcing because she just didn’t want a family anymore. My friend’s aunt didn’t want to tell them he had cheated because she didn’t want them to think of their father like that. She held true for quite a few years, but the kids were brainwashed by her ex. She was alienated from her kids as a result.
I visited my friend’s house on and off during my late teens and early twenties. He lived right down the road so we would hang out there most of the time.
I was about twenty-three, and his aunt was forty-two when we started chatting at the table one day. Every couple of weeks after that, we would find ourselves chatting away somewhere in or around the house or in the pool. Often when people were around we kept conversations short.
Eventually, we started texting after exchanging numbers concerning a party she was planning for the extended family. Soon, intermittent texting turned flirtatious.
When we saw each other, she and I started hugging each other goodbye. Each time we did, my friend’s aunt would hug a little bit longer than friendly. One night, I was housesitting for someone and told her I was free if she wanted to come over to hang out.
She accepted and I definitely experienced a type of anxiety that you could taste. We ordered Italian food but she didn’t even want to be seen by the delivery driver.
That was when I knew she had some bad intentions too.
After eating, we ended up in front of the tv and snuggled up. I don’t think thirty seconds went by before we started kissing.
It was the hottest sex I’d ever had. I remember it vividly.
We ended up hooking up about five more times over the course of a year. I would go to her house a few towns over and she would make us a full dinner, we’d chat over wine, and have such amazing and fulfilling lovemaking.
We both ended up dating other people but would stay in touch. We hooked up once again when we were single once more. I still see her a couple of times a year when I visit for family BBQs and pool parties at my friend’s house.
No one has a clue.
A Nice Workout
“My friend’s dad was a gym owner. Growing up I always thought he was really good-looking and charming.
At the time, my friend’s dad and I both had toddlers going to the same daycare and we chatted briefly on the couple occasions we dropped off and picked up our kids at the same time. One time during our conversation, we talked about my his gym and how business was going for him.
I casually mentioned how I wanted to lose some weight, so he invited me to take some free classes. Delighted, I took him up on it.
One night after a workout, my friend’s father and I ran into each other again in the parking lot as I was walking home. He was kind enough to offer me a ride home because it was after dark.
Once we made it, I invited him in. He hung around for a while until I could put my kid to bed.
Not much was said before we started making out and had casual sex.
I never went back to his gym after that because it was too awkward. I didn’t know how he felt about our hookup and I knew I didn’t want to actually date him since he was forty-three and I dread awkward conversations.
Occasionally, I still saw him a few times at my kid’s daycare. Things aren’t awkward at all with my friend, but that’s because she still doesn’t know.”
Two Lonely People
“My battle buddy and I were discharged from the Army at the same time and didn’t really have anywhere to go.
We floated around the country for a while before settling on moving to his home state until we got back on our feet. With no money to our names, we crashed at his mom’s apartment.
My friend had a network of people, so he spent a lot of time out and about. I, on the other hand, had no one. All of my family and friends were nearly two thousand miles away, and I had never been the social butterfly type. So instead of hanging out with his friends, I would just go back to the apartment after work and drink myself to sleep, the way a lot of guys fresh out of the military do.
I soon found out that my friend’s mom was just as lonely as me. She saw this young guy pounding back drinks and decided it was a good opportunity to shoot her shot.
We shagged up a few times, and eventually, the inevitable uncomfortable truth of the situation settled in for both of us. When it got too awkward, I moved back across the country to my shitty hometown.
She kept our dirty little secret even though I was sure she wanted to come clean.
Unfortunately, my battle buddy disappeared into a world of drug abuse.
I came clean to him about it some years later, after a lot of things had transpired in both our lives. I honestly just wanted to get the past off my chest.
It didn’t go well.
It’s been nearly fifteen years and we’re only now starting to talk again.”
“Wanna Show You Something…”
“I befriended one of the regulars at the shop I worked for. We weren’t all that close, but we would hang out from time to time after we both got off.
His mom was also a regular customer.
She came in one morning as soon as we opened. I learned that her husband had died of cancer about a year prior. My friend’s mom had been complaining about how poorly her dates were going ever since she decided to get back into the dating scene.
She came behind the counter to ask me a question, which was against policy. However one of my coworkers was in the kitchen and she knew I was pretty easygoing about the rules.
She had a rather coy smile on her face before she said, ‘I’m gonna show you something, but it stays between us, okay?’
‘Sure,’ I said, not knowing what to expect.
My friend’s mom then whipped out her phone and shamelessly showed me a picture of her topless and posing in a flirtatious way. She smirked at me as she watched my reaction before she turned around and left from behind the counter.
At this point, it was pretty obvious to me what she wanted. I was contemplating how I was going to go about it when she decided to come back behind the counter and carry on a conversation with me.
After a few moments, my friend’s mom announced she was going to give me another ‘peek’ and pulled her blouse to her chin revealing herself to me. We had customers in the store while this was going on, but it was so early in the morning that it was pretty dead and business was slow.
I was in so much disbelief that I couldn’t look away. My friend’s mother giggled at my reaction before she pulled her shirt down and walked away from the counter again.
About ten minutes went by before I finally said, ‘What the hell,’ and made a decision.
I walked over and tell her to meet me in the employee restroom in five minutes.
I took my break early that day. We had fun there for the duration of my break.
And that is the story of how I lost my virginity to my friend’s mother.”
Way Too Carried Away
“I’ve known my best friend since grade school. We ended up going to the same college right after graduating from high school. We didn’t get the same dorm, but this gave us the opportunity to venture out and meet new people.
About a month in, my roommate dropped out of nowhere. Because it was the middle of the semester, I ended up with a room to myself. Around this time, my best friend’s father also came to visit her at school.
The first day he was there, my best friend spent time with him during the day. After they were done hanging out, he went back to his hotel before we went out and partied that night.
As the end of the night came, my best friend went back to her room and passed out drunk. I was under the influence as well, so I had to stumble to my dorm. As I walked up to the building, her father got out of a car that was parked in a nearby parking lot. He met me at the front door and told me there was something he wanted to talk to me about. Her father then asked if we could go to my room.
Thinking someone was wrong, I told him yes. Once we got to my room, we sat on the edge of my bed and had a normal conversation. My best friend’s father asked me how I thought his daughter was adapting to college life and other basic questions a parent would ask.
I was still very drunk, so my contributions to the conversation were rather minimum. This went on for several minutes before I noticed him inching closer and closer to me.
Gradually, his hand started snaking its way up my leg. I froze, unsure of what to do.
Then my best friend’s dad started saying things like, ‘You’ve really grown up, you know that?’ He then started commenting on how I looked in my outfit. We ended up kissing and got carried away.
After we finished, both of us passed out for a couple of hours before he woke me up for a second round of lovemaking before he went back to his hotel for the rest of the morning until he met up with his daughter.
The next night, as I was heading over to see my friend, her father stopped me and handed me a fat wad of cash.
When he saw the look on my face, he casually told me to get Plan B and a birth control prescription for the future. I was already on birth control, so I pocketed the money. I did this every month he gave me money for two years.
My friend didn’t find out until a few years later when she was visiting her father during summer break. She found nudes and videos of her father and me together on his computer.
To say she flipped out is putting it lightly. She still hasn’t talked to me to this day…”
One Too Many
“I was working as an intern at a hospital. My friend’s mom was in Public Relations for the healthcare system. My friend and I went to the same high school and kept in touch throughout college.
My friend’s mom reached out to me one day because she knew I was interested in film. She made videos for her company that interviewed doctors and patients. The cool part was that she had been a popular news reporter for the local ABC news channel for decades before she had this position.
What started off as a normal, ‘Hey, let’s go get a drink after work,’ gettogether ended up being a ten gin and tonic marathon which eventually ended back at my parents’ condo on the deck looking over the city.
My parents were away on vacation and I couldn’t take her to my own place because my girlfriend was home. I’m a scumbag. I know. My friend’s mom began drunkenly dancing in the living room and one thing led to another.
I can tell you it was the worst sex of my life.
This mom had a family. Her husband, son that I was friends with, and an older daughter all kept crossing my mind while we did the deed.
Even though it’s been years, our drunken hook-up is still something I regret. I never talked to my friend again after that and I avoided his mother at all costs.
The next day, she sent me an envelope with her panties and suggestive pictures of her. I remember cringing before throwing them in the trash.
The next Monday when I returned to work, my friend’s mother came up to me and asked how my weekend was.
‘Uhhhh, fine,’ I said just wanting the conversation to end.
‘Because I had a great weekend,’ she said with a wink. ‘We could always go to the bathroom for a quickie.’
It was at that point that I truly felt disgusting and not worthy. Luckily as time passed, I emotionally healed and got back to hooking up with people my own age.
I quit drinking after that.”
My Gift To You
“My parents don’t have a lot of money. My best friend’s dad, however, is the Chief Financial Officer of a company and was doing well for himself. He drove a Porsche, had a beautiful house, and was well-dressed.
He and his wife divorced had divorced two years ago. My friend said they split because her dad was hard to live with and her mother was a former beauty queen who used to be very sweet, but she became a real diva. The two of them couldn’t stand to be around each other anymore.
My best friend and some other friends were going to NYC to celebrate New Year’s. We all saved up but I was still low on funds. I had been hanging around my best friend for a few years so I was pretty comfortable with her dad.
I was sitting at the kitchen table at his house asking for options. Suddenly, my best friend’s dad pulled out his phone. Five minutes later I got an email notification about the information for my Delta plane ticket to NYC!
Right then and there, he cashed in his reward miles and bought the ticket on my behalf. I started crying and jumped up and hugged him. He laughed and said I’m a good kid and deserved some happiness with friends.
He then left so I could call my other friends so we could make plans. When I told my dad, he called him to pay him back. My best friend’s dad refused and said it wasn’t necessary because my dad has been so good to my daughter over the years and it was the least he could do for his daughter in return.
After that, all I could think about was making love to him. I had always thought of him as a good-looking man. I began seeing his face in everything I did. So after a few days, I courageously went to his house and baked a dessert for him as a ‘thank you.’
After shaking off my nervousness, I tried to seduce my best friend’s father, but he shot me down. I kept trying but he resisted and asked me to leave before something stupid happened.
I was desperate and wouldn’t take no for an answer. I finally kissed him and that did it. He grabbed me and kissed me back. In a blur, we were entwined together in sensual lovemaking. We had sex on his couch and in his bedroom. It was the best time of my life. My best friend’s father was the best man I had ever been with.
The next morning, he insisted I leave because he didn’t want his daughter to find out. After I left, I texted him about what an amazing time I had.
Within seconds, he replied:
‘No. This was a mistake. We messed up.’
I was concerned my best friend’s father didn’t want to hook up again. At that moment, I wanted to convince him I wasn’t out for his money. I simply wanted his body and was after his affection.
To this day, I have to keep quiet. I can’t let my best friend know because I know she’d go nuts. She knows her mom and dad will never get back together but I know she’d be upset if she knew I slept with her father.
So it’s all secrets now.”