[MF] The “lesbian” with red flags and my mother’s convertable

I have several strange hookup stories from my past, and I’m going to start sharing them starting with this one. I was friends with this girl named Ashley for a couple years. She was in the same group of people in the punk/metal scene I used to hang out with. She had red flags all over the place, so I would have never pursued her even she said she wasn’t lesbian (questionable stories of men breaking into her house and assaulting her, off and on heavy drugs, crazy eyes, always had to correct you with “facts” she “knew but everyone else didn’t”). Most people tolerated her, but I had a way of talking around her that kept her comfortable without her reverting to “Red Flag Mode” most of the time. I hung out with a lot of people back then, but I always felt alone. I’d hang out with anyone to fill in that void until they would drag me into their drama, then drop them like a hot potato. We would chill by ourselves from time to time, and I sometimes dropped her off at the house of whatever girl she was dating at the time because she had no car.

This story begins after I had a really bad break up. I was desperate for company and affection at the time. I was still living with my parents, and they went on a cruise. My mom forgot to hide the keys to her convertible, and I decided I was going to enjoy the car all week long. Friend after friend were busy that whole week, so I was just cruising by myself. I did the whole mallrat thing across nearly all the big malls of NJ during the week meeting new people as I walked around and goofed off. I ran into Ashley at the mall I visited the most often. I treated her to some teriyaki chicken at Sarku Japan while I told her about the convertible situation. She laughed with me about it and said she’d happy to cruise around in the car with me for the rest of the week. She had never actually been in a convertible before that.

We drove around at random visiting hot spots for our friends until we landed that evening at a place we went to very often for open mic night. I sometimes read some of my poetry and songwriting there, but I most just went up to do something weird to make people laugh. I had a puppet frog that I named Darth Frog. It was like a ventriloquist act (because nothing makes a woman’s panties drop like a puppet frog /s). I did all of the talking though, and I made the frog answer in head movements and arm movements. I would often roast my friends with Darth Frog’s help or end the act with Darth Frog trying to choke me to death. That night, the host of the open mic night passed my puppet frog around to all the women in the place, and 99% of all the women placed the puppet in their pants as part of a gag.

Ashley was cracking up the entire time until I finally got Darth Frog back. I made the wise crack that my damn puppet frog has been in the pants of more women then I ever will, and Ashley just about lost her sides laughing. I finished the tea I was drinking, and we headed to my place.

I wasn’t really that cold, but she insisted I light up my fireplace because she’s never been in a house with a real fireplace. I kept saying no until I made her agree to cuddling in pajamas in front of the fireplace. I was joking, but she was so happy to agree to that. I just went with it. She called her mom not to wait up for her and that she’d be sleeping over my place. She stole one of my most comfy pajama pants that had a tie strap and one of my old faded band shits. I am a big guy, so they were baggy and comfortable for her. It was kind of odd that I noticed her underwear in her pile of clothes after we changed, but I thought nothing of it. She was lesbian after all.

We were cuddling by the fireplace talking with TV on in the background when my phone rings. Whenever I was home alone, my dad likes to tell my uncle, so my uncle can prank call me. My uncle and I were fucking with each other over the phone when Ashley decided to get in on the call. Then my uncle’s girlfriend at the time got on the call with Ashley, and they started dirty talking about things they could do to each other. Ashley got really into it, but my uncle wanted to get his girlfriend off the phone. I told Ashley about the whole prank call thing we have going on after the call ended, and she said she wished she had someone that did that with her.

We eventually moved into my parents’ bedroom. I had a couch that folded out into a bed; my bed wasn’t that big either. I had a dog then, and he liked sleeping in their bed. It made it easier for my dog to wake me up if he needed to go out in the middle of the night.

Ashley and I continued to cuddle in my parents’ bed. She moved my arms to her breasts at this point. I figured she was more comfortable that way; she was lesbian after all. Yeah, I was that oblivious. I don’t walk much in my sleep, but I talk, sometimes sing, and get handsy in my sleep. It was years later that one of my partners finally told me how handsy I can get in my sleep; I never knew until then. To this day I am sure if I initiated anything in my sleep, and there are more stories I have to tell where I am not sure if I did the initiating because I was unaware of my nocturnal activities.

Ashley and I had fallen asleep cuddling with my arms around her breasts. I only wore some boxers to sleep, but I started to stir realizing I was naked. My cock had a warm, wet feeling, and I realized it was probing Ashley’s slit very slightly… maybe an inch deep back and forth as Ashley was grinding herself backward on my cock. It took me a minute to register that she had no pants on either. My hands were underneath her shirt by this time; her breasts were big enough to fill my hands. I moved my hands to her hips as I whispered in her ear something along the lines of, “You can stop me if this is not want you want.” I pull her ass into me from her hips slowly allowing my cock to penetrate her slit entirely. She moaned as I kissed her neck, kissed behind her ear and occasionally nibbled on her ear lobes as she rocked into me with more force than I was pushing into her.

She never turned to face me, but she would shake a little and nearly straighten out from time to time. Either she was cumming, or she was coming close several times. We literally went on over an hour. We weren’t being aggressive, and the all the movements were lazy in the spooning position. I have trouble cumming unless I get into just that right spot at the right moment and just start pounding until I empty out. Ashley was barely able to move anymore when I finally reached that point. My fingers tightened around her hips as I increased the fury of my thrusts until I emptied myself entirely inside of her. I wasn’t really thinking, and it was out of reflex. My ex that just broke up with me was using an IUD, and we always did bareback with me cumming inside of her. Ashley and I both passed out with me still inside of her.

Ashley seemed happy when we woke up to her alarms. She needed to shower before I was going to drive her to her classes in the morning. She kissed me before she showered, but it seemed friendly instead of passionate. She hugged me tight right before she got out of my mother’s convertible to go to classes. I came back to pick her up from classes. I waited almost an hour, and she wouldn’t answer my calls. I walked around a little while looking for her before I gave up. I was a little depressed until another friend called me to tell me his plans changed and that he was free to hang out.

Ashley never answered my calls or messages. I stopped trying after a couple of days. I gave her space, and I figured she would contact me if she wanted to talk.

It was months and months later the next time I ran into Ashley. I was dating someone else when she came up to me. She hugged me tight, and then the hug was followed by an awkward hello and me introducing her to my new girlfriend. Ashley didn’t stay at open mic night that long after I introduced her to my girlfriend. I never saw Ashley again after that night. I already started going to open mic night less, and I moved a couple years later. I’ve seen her Facebook and other social media after our hook up, but I never added her on anything. It kind of stung that she didn’t even try to be a friend after anything. I would have been fine if she made a mistake and realized she was still lesbian or whatever. I was still hurting from a breakup then and needed friends, so I guess I was still a bit bitter. I’m doing good and practically married these days, but I wish I had more friends to hang out with. I sorry this had a depressing ending. I just think about how few friends I have right now, and I think about nights like this one a lot and how I lost friends.

Source: reddit.com/r/gonewildstories/comments/68c0iq/mf_the_lesbian_with_red_flags_and_my_mothers