Boyfriend Meets My Parents. Again.

The premise of this story was based on a reddit post from May 28, 2020. The post has since been removed and it may have been fictional to begin with. Without giving away the whole story, the post mentioned her boyfriend meeting her parents, finding out that he already knew them, and just how he knew them. The debauchery that follows is from my deviant mind.

Note: I don't often want to point out what sexual acts occur in a story beforehand because I feel it gives away the surprise, but because this will be in the Taboo/Incest genre, you should know that this story also includes male-on-male sex. It will not include only male-on-male relations, but it will be a key part of the story. If that is the sort of thing you don't like to read, I ask that you enjoy another story.

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Closing the passenger door behind me, I ran to the other side of the car to join Will, who had just emerged from the driver's side of his Lexus IS. For nearly seven months now, we had been dating and I was practically living at his posh apartment. Though I still had my own place with my roommate, Hannah. For all intents and purposes, however, I was living with Will now. Little Rory Brown had snagged an older man. Sure, we still got a few questionable looks as we went to dinner and I can't say all of my friends have been quite as supportive as I expected they would be when I told them I had found love. I was in my final semester of law school and had already accepted a position with Brinkman, Smith, and Powers as a junior associate - pending my successful bar exam, of course. Still only 24, I was one of the younger members of my graduating class, but age has always been an arbitrary barometer in my view.

Maybe that's why, while I understood why people gave us looks, I didn't care that Will was 35 and we had an age gap of eleven years. To be quite frank, age really is just a number. We attach value to it, but we don't all live the same life at 16 or 20 or 24. Hence why I've always been described by people as "very mature" and "wise beyond her years."

I didn't expect to land in a long-term relationship when I met Will. To be honest, I met Will for one reason - to have sex. My schedule was incredibly busy. Until the last few months, in addition to law school, it also included working at one of those sports bars where the girls wear shorts that cover just a bit more than your average pair of panties. I have a nice ass and can turn on the flirty demeanor so giving the guys a tease in order for them to drop a big tip didn't bother me. But that's not where I met Will. I wanted sex, but not with the complications. I didn't want to fuck a customer because it could get worrisome. I would have zero control whether he continued to frequent my establishment and I don't need that kind of drama. Instead, I sought out a random hookup on Hush Flings, a website that often sets up younger women and older men. It doesn't advertise itself like that, but the best men you find on that site, at least in my opinion, are the older ones. They don't just send you dick pics. They try to get to know you first. You're able to find out if there is some kind of connection - at least enough to warrant a hookup.

Will was the first guy on there I felt like I might want to meet in public. Not planning to fuck him the first time we met, we made plans for coffee. I had another class in a few hours and I didn't even bother to shave my pussy. In no way did I expect to end up in bed with Will.

You're probably not surprised to find out within the hour, I was bent over a hotel bed that he hastily paid for as he fucked me with his thick cock. I missed class that day - something that never happened. Later, as I stroked him while he played with and sucked my nipples, I called out from work despite it being half-price wings night with a baseball playoff game. I texted my roommate, Hannah, to tell her I was staying with a friend as he brought me to orgasm with his mouth. The next morning, we had sex in the shower before I had to leave in a hurry to make it to class. My pussy was still humming during a discussion of negligence-related claims.

Again, my plan when I signed up to use that site was to find someone to take out some sexual frustration with and then move on. Instead, the connection with Will was undeniable. We met a few more times as just friends with benefits, including spending a Saturday at his house where I sucked his cock on the balcony. Eventually, though, we started to transition from just sex to spending time together as well. We went to the movies and museums together, spent a weekend at a cabin retreat where he held me tightly until we fell asleep watching the snow fall, and I even met his twelve-year-old son from his previous marriage.

But I think the moment I realized I truly loved him was when he sat through, gave me advice, and then sat through again my mock final arguments for a court case. A busy man himself, Will was a hedge fund manager. Yet, he made the time to listen to me bumble my way through an assignment for class. In the end, I got an A. It wouldn't have happened if not for Will.

And now, almost seven months to the day of that first evening in a hotel room, I was about to introduce him to my parents during a weekend away near the end of the semester. I didn't want the added pressure of waiting for my graduation to introduce Will to Mom and Dad. That was already going to be stressful especially with extended family expected to fly in, including my much older sister, Samantha.

Obviously, we were worried. Yes, they knew that Will was older. But I stressed how strongly I felt for him and asked for them to keep an open-mind, confident that Dad and Will would bond over a shared love of the Ravens while Mom would appreciate his manners and charming personality.

My parents are, for a lack of a better word, typical. They met in high school, married after finding out Mom was pregnant with Samantha, and eventually moved into the same house they've lived in for slightly over twenty-five years. Dad started as a floor worker at a furniture factory and now manages the plant. Mom returned to school when I was a child and now manages her own insurance office. Unlike Samantha, I was a planned baby after Dad was promoted to a department manager. She's six years older than me and has her own family now with Capt. Harold Phillips of the United States Air Force.

Meanwhile, Dad and Mom are both nearing the Big 5-0. Even before that, they'll celebrate their 30th Anniversary - Samantha and I, with some quiet financial help from Will, are sending them on a cruise. Many of the couples they used to be friends with are no more, choosing divorce. Yet, my parents still love one another. In a way, I was in awe of them. I knew just how privileged I was to be born into such a loving family that stuck together. Samantha once told me that Mom and Dad were like a quick reference on how to make a marriage work. When you have trouble, call them. They knew all the tips and secrets.

The early spring weather was a bit cool as we got to the front door. I was going to barge right in like I always do when I come home, but Will stopped me. He shifted the bottle of red wine to his other hand and pressed the doorbell. I rolled my eyes at him, but I understood he wanted to be respectful.

In this era of social media, Will was different. He rarely used any of them besides LinkedIn. It took months for him to accept my Instagram request. Not because he was hiding me, but because he never logged in. So, when Mom asked about his Facebook page so she could add him, I wasn't surprised to find out he deactivated his years ago. Since Mom and Dad were old school and only had Facebook in order to connect to friends-and-family, this wasn't only the first time Will met my parents, but the first time he had even seen them.

We waited for the door to open and when it did, both Mom and Dad were there to welcome us. There was a lot of awkwardness after we got the hugs and handshake introductions out of the way before they finally invited us in. But that's to be expected anytime you bring home a stranger to meet your parents, right? That's probably especially true when he's a bit older than you.

When I told Mom I was dating a man eleven years my senior, she was a bit worried. "That's a big age gap," she told me in her mother-knows-best tone. "I'm sure you are smitten by him, but do you really see this relationship going somewhere?" I explained to her that I did, telling her that Will and I haven't avoided talking about our differences in age, but we have a connection that goes well beyond the days we were born. I told Mom that I had never felt this close to another man.

Finally, we came inside and made small talk about the drive.

"Well, I hope you guys are hungry because Linda is putting together a feast that could feed the entire town," Dad said with a laugh.

"Oh, hush your mouth, Daniel," she replied, slapping his arm. "It's not that much food, I swear."

She went off to the kitchen and I stayed around to talk to Dad with Will. Things still felt a bit off as we talked about Will's work and how things were going at the plant for Dad, but I was comforted by the fact that we were at least talking and sharing a few jokes, even if they often were not nearly as funny as our laughter made it seem.

Will held my hand and occasionally gave me a rough squeeze. I could feel his anxiety. As Dad went to check on Mom for a few moments, I looked up at him. "You're doing great. They love you. Just relax."

He gave me an unsure face and I kissed him, sneaking my tongue inside of his mouth for a moment before pulling away as I heard Dad's footsteps.

Mom joined us a few minutes later, explaining dinner would be ready in a few moments. After a particularly awkward pause in the conversation, Will asked where the restroom was. I showed him to the first-floor bathroom and when I returned to the living room, Dad had disappeared.

Seeing Mom's look, I knew something was up. During family game nights, Mom had proven one thing with amazing consistency: she couldn't bluff. It was comical to see her even try. Dad and I would often share a look and try not to laugh. But that lack of a poker face also was evident when she had bad news. Within only a few seconds after returning home from school one day, I knew something was wrong. She wanted to wait until Dad came home to tell me, but it was too evident that something was up. That was the day I found out Grandma passed away.

I was seeing the same look of dread on her face now. I closed the distance between us and asked, "what's wrong, Mom? Is it Will? Dad? What's going on?"

She opened her mouth, but Dad came back to the living room. Looking his way, she told him she needed my help in the kitchen.

"You're going to leave me alone...with...?"

I felt irrationally angry at his response and wanted to say something, but Mom took me by the arm and led me away, explaining that he'd be fine. Seconds later, she whisked me away into the kitchen. She took a moment to stir the gravy and take it off the burner before looking my way. The silence was deafening as she stared at me. I flashed back to that day she couldn't hide the fact that something horrible had happened. This was big.

My mind rushed through possibilities. Divorce? No way. That can't be it. Was one of them sick? Dying? Was I about to learn that one of my parents had an inoperable cancer and had only weeks to live? What in the hell was going on?

Finally, I couldn't take her stalling anymore. "I'm a big girl, Mom. Tell me what's going on. I can't help you deal with this unless you talk."

Releasing a breath, she said, "It's about Will."

"Will? What about Will?" My voice was much higher than hers as I tried to figure out what was wrong.

She nervously looked toward the hallway that led to the living room. "Please keep your voice down, okay?"

"Fine," I whispered back. "Just tell me what's up with Will."

"Well," she said with a light shrug. "This isn't the first time we met Will, honey. Only when we met him, his name was John."

I shook my head as if waking up from a dream. But no, I was still in the kitchen. "What do you mean? His name is Will. I know his name is Will. I've seen the yearbooks." I still kid him about his long hair from when he was in a garage rock band.

"I'm sure that his name is actually Will, honey. It's just when we met him, he used the name, John."

"What do you mean you met him? How did you meet him?"

"It's a long story, honey," she said. "But the key points are this: we met Will about ten years ago on a website. We met him...for sex."

It seemed like time came to a halt. I honestly don't remember much of what happened over the next few minutes. At some point, I left the house via the back door. At the end of the yard, I climbed the fence and fell in the Peters' backyard. Their dog, Sadie, barked at me and I saw Mr. Peters once he checked what the racket was. I didn't answer him when he called my name. Instead, I opened their front gate to reach Francis Street. Taking a right, I soon came to the cul-de-sac at the end of the road where my friend Callie used to live before her family moved to Florida. There's a patch of woods behind the houses there and I walked through them.

From there, I ended up behind one of the dollar stores that they put up in the last few years on Route 29. Walking on the side of the highway, I reached the bridge that goes over some train tracks. Ducking down a path that was now overgrown, I slipped under the bridge with the sound of cars speeding in excess of 55 mph overhead.

It used to be a spot to hang out back in the day. I smoked my first joint here. As dumb kids, we used to throw rocks at the trains that passed with their cargo. I made out with Felix Carson a few times down here before he tried to push me to have sex before I wanted to. One swift kick to his nuts ended that.

My phone buzzed. It was the first time I noticed. I already had seven missed calls - five from Will and two from Mom. Both had texted me asking me to return and talk about things like an adult. But honestly, I didn't think I was throwing a fit. What do you do when you find out that your parents not only had previously met your boyfriend, but sex was involved? And Mom hadn't said, "when I met him, his name was John." She said, "we." This wasn't some quiet affair. That was bad enough. No, they knew Will.

I had no clue what to do. Or where to go. And as the sun set, the late April-weather turned cooler. My thin long-sleeve yellow blouse suddenly seemed like a really bad idea.

After shivering for another thirty minutes, I decided that I couldn't run from this forever. Maybe my relationship with Will was over, but it's a little harder to avoid your family. I pulled out my phone that had continued to buzz. I sent Mom a text of where to come get me and to come alone. Making my way back up the road as the sun disappeared from view for the last time that evening, I waited until Mom pulled over. I hopped into the car and was a little grateful that she had put the heat on.

She drove for a few minutes in silence before I couldn't take it much longer. "Tell me how you met him. Tell me...tell me everything."

I saw her look my way for a couple of seconds before she asked, "Are you sure you want to know?"

"No," I replied. "But I need to. Otherwise, I'll never be able to move on. Give me the whole damn story."

She pulled over in the parking lot of the old K-Mart. It was empty now. Looking forward, she started her story.

"Let me start off by saying that I trust that everything I tell you stays between you, me, and your father. Not a word to Sam and please don't tell anyone else." I told her that she had my word. "One day, I hope that you are in a relationship long enough to understand that no matter how much you love someone and wish to spend the rest of your life with them, that underneath the exterior of an amazing relationship, there are cracks. Most of these cracks won't lead to anything too serious, but all of them make the foundation a little weaker. You can either ignore them and hope they go away or try to fix them. Your father and I have always tried to fix the cracks. It's not always easy and we don't always fix them so much as we plaster over them, but the effort we put into our marriage is why we've stayed together while other couples failed."

"About ten years ago, we became aware of a crack. Our sex life was beginning to...become unsatisfying. I know that nobody wants to hear that about their parents because nobody wants to imagine their parents as sexual creatures, but your father and I like to have sex with one another."

"I know," I said in a low voice. "You're not always quiet about it."

"Nor do I want to be sometimes. Your father had sex with two other women before we got together. He was the first man I had ever had sex with and up until about ten years ago, he was the only man I ever had sex with. Just to be clear, our sex life had evolved from those first few years when we knew almost nothing about sex besides that it felt good. We had tried new positions and...new sex acts." She made a noise out of frustration and turned to me. "Listen - there's no way I can talk about this without being very frank about it so I hope that you will forgive the language your mother will use."

"I'm 24," I replied. "You're not going to shock me into therapy because you guys like to get a little nasty in the bedroom."

"Fair enough, sweetie. So, like I said, we tried new things. We found out that I like anal. He found out that he, too, liked to test the waters anally. We watched porn together, had sex in public places, and he particularly enjoyed what we called a 'Highway 29 Release.' That's when I'd blow your father while he drove. Occasionally, we'd get honks as truckers saw me going down on your father. It was fun and it added excitement to our sex life. We tried roleplaying, we'd sext one another while at work, and really...we just kept trying to push for something new and invigorating."

"Mom, can you get to Will?"

She frowned at me. "I'm getting there. Just please let me provide context. After a particular long stretch where we kind of didn't know what else to do to change things up, we started to get frustrated with one another. And one night, I pointed out that he had been the only other person I had ever been with. I didn't mean to hurt his feelings and I wanted him to know I wasn't looking to cheat on him or I was bored with him, but I couldn't shake these fantasies about what it would be like to be with someone else. Truth is I had long wanted threesomes, foursomes, and more. It really excited me."

She shrugged her shoulders.

"So, we talked it out. Watched porn with threesomes and more. Your dad was a little hesitant so I suggested a compromise. I knew that his ultimate fantasy was a threesome with another woman. Honestly, it had become one of mine, too. I told him that let's have a threesome with another woman and then we'll have a threesome with another man. He was still a little iffy so I put on a scene with two girls going down on one guy. At the same time, I gave him a blowjob. After he came, he agreed. And if you ever need to convince a man to do anything, that's a secret that's going to work 99% of the time.

"This was back when you would go onto Craig's List for this sort of thing. We eventually met Lana. After a few weeks of trading emails and pictures and talking on the phone, we decided to meet up at a local hotel. Your sister watched you while we went out for a 'date night.' But we didn't go out to eat. We had sex with Lana."

Looking her way, I asked, "we?"

She chuckled. "Yes, we. Like I said, I was interested, too. Lana is a beautiful woman and very sexual. We'd meet up a few more times - including once without your father, though I took pictures and video for him."