I once had sex with my girlfriend’s sister [MF]

My name is Jake. This happened when I was in college in the early 1990s. I was a sophomore. I met my roommate’s girlfriend’s roommate and we hit it off. It was an improbably match because I was a pretty standard suburban kid and she was a full-on hippy. Like a hippy-hippy. As in her parents named her and her siblings things like Creek, Gaia, and Luna (not their real names but not far off).

To that point, Gaia was easily the most attractive girl I had dated. She was average height, thin with brown eyes and long brown hair. She had about B-cup breasts and never wore a bra. She was a freshman.

At first we got along because we had similar senses of humor. Later we discovered we had great sexual chemistry. When you’re in college, that’s about all you need as the foundation of a solid longterm relationship.

One of the key things to know about her was that she had zero hang ups about sex. She was all onboard with free love even though that fad passed on 20 years prior. If she thought she’d enjoy something sexual and was interested in it, she had no qualms about pursuing it or talking about or anything. She didn’t care what anyone else said about it which annoyed the shit out of most of the other girls in her hall which was an added bonus for me.

We experiment with a lot of stuff sexually (well, I experimented. She already run most of the tests, analyzed the results and had them published in a peer reviewed journal, so to speak). Remember this was pre-internet and pre-internet porn, so our knowledge of most sexual acts came from either shit one of our friends saw on a badly beaten up porno they got from their older brother, from first hand experience or locker room rumors.

She was the second girl to blow me and the first girl I ate out. She showed me to almost all the sexual positions I know and the pleasure of having a finger shoved up your butt.

When Spring Break rolled around, I didn’t have anything to do. My family lived across the country and I didn’t want to shell out for a flight home. She invited me to stay with her family. I asked if her parents would be ok with that and she told me they would.

On the day we showed up, I made sure to look like a presentable and upstanding young man (I gave great parent back then). I had gotten a haircut. I was wearing a clean polo and khakis. I used my “Sir” and “Ma’am”s and a firm handshake. When her parents saw me, they were pleasant but I got a distinct “Who invited the narc?” vibe from them.

Her parents were even more of hippies than she was. They were OG hippies from the 1960s. It’s hard to describe. If you put them in a movie, people would roll their eyes at how stereotypically over the top they were.

I remember two things about their house: 1.) there was a jar of pot on the kitchen counter like how most people might have a jar of sugar. 2.) it smelled of stale farts which is too be expected when the inhabitants live on a diet of beans and lentils.

In addition to her parents, her younger brother and older sister Luna (a senior in college) were also home. One night, her brother was gone and the rest of us had a wholesome evening in the kitchen of baking pot brownies. It was a scene straight out of the Brady Bunch.

Eventually her parents went to bed since they had to get up early. I stayed up with my girlfriend and her sister watching a movie. Near the end of the movie, my girlfriend had fallen asleep. I was super high. I was a relative lightweight. I also made the rookie mistake of eating one brownie, not feeling anything right away then eating a second brownie. Both brownies teamed up to knock me on my ass.

Her sister and I started talking. She started laughing at me because of how high I was. She told me there was a test to see if you were OD’ing on pot (I was not smart enough to know you couldn’t OD on pot).

The test was to hold your palm up to your nose and hold it there for 5 seconds. If you could, you were ok. When I held my hand up to my nose, she hit my hand causing me to hit myself in the face. (It’s similar to the “If your hand is bigger than your face you have cancer” prank).

She thought this was hysterical. When she stopped laughing, she asked if I was ok. Then she asked if she needed to kiss it to make it better. She then kissed me on the nose. Then she gave me a peck on the lips followed by a real kiss on the lips.

At this point, I was sure I was dreaming. It’s like when you start flying in a dream and you realize you are dreaming because you know the laws of the real world don’t operate like that.

Then she straddled me and started rubbing her body against mine. That felt more real than dreams usually do. I made her stop and said I couldn’t because of her sister.

She said, “She doesn’t care.”

I was like, “What do you mean she doesn’t care?”

“Gaia wake up and tell your boyfriend it’s not the 1950s anymore.”

Gaia woke up and groggily asked, “What’s happening?”

I thought I was dead. I started trying to come up with excuses for why her sister was on top of me. Before I could Luna said, “Do you mind if I fool around with Jake?”

Then responding as if her sister had just asked if she could borrow her sweater, “Yeah, sure. I am going to bed. See you guys in the morning.”

I was flabbergasted and a little offended. I remember back to a couple of time when she caught me checking out other girls and said I should go talk to them. I thought he was joking or sarcastic but maybe she wasn’t. Early in our relationship she said she didn’t believe in old fashioned idea about monogamy and marriage. I thought she was trying to sound cool and maybe signaling she was open to a three-way. I was wrong. She walked the walk.

At this point, Luna starts kissing me again. I am still only 50-50 on whether I was dreaming. But either way, I was like “Fuck it. This is a pretty cool dream.”

I pulled off Luna’s shirt. Unlike Gaia and her mom, Luna wore a bra. I assume out of necessity because her boobs with a couple sizes bigger than either of them. On her short / petite frame, they looked huge.

Between the pot and the three decades that have passed, the details are fuzzy. I know we both went down on each other. We at least did missionary, her riding me while I sat on the sofa and me doing her from behind while she was bent over the sofa. The only thing I remember clearly was getting my hand stuck in her very thick hair went I tried to run my hand through it.

Afterwards, I went to bed next to my girlfriend. In the morning, I was awkwardly dancing around the elephant in the room. She asked me if I was still high or something. I said no I was just nervous about what happened last night. She just said, “Dude, grow up.”

And that was that.

Source: reddit.com/r/gonewildstories/comments/bpw5h9/i_once_had_sex_with_my_girlfriends_sister_mf