My Best Friend & I Used to Masturbate to Each Other [MF]

Yeah this story is a little weird.

I used to date a guy in law school and we had REALLY good sex. I was really inexperienced at the time and he definitely awakened my kinky side and subsequently ignited a very fun slut stage that lasted for several years.

Years later he moved back to my city, but we were both in relationships so the romantic aspect of our relationship faded and we became best friends. I realize that sounds shady, but our romantic relationship had been pretty tumultuous and we both knew it would never be a healthy long term thing. I think sometimes we’d both feel a bit of a spark and then remember the roller coaster that had been our courtship and quickly shut things down. Plus, we were both in very happy relationships and didn’t want to risk our friendship because at the time we honestly did understand each other really well and were important to each other.

Anyway, one day we were at brunch of all places and had had far too many mimosas when he brought up that his girlfriend was mad at him because she caught him touching himself in the shower and was offended he hadn’t offered to fool around. I laughed at that because I get myself off at least several times a day and I’m pretty sure I would have killed my boyfriend by now if I demanded sex at every impulse. He then informed me that he did the same, which is why he was confused at her anger because no one could have that much sex. We both stared at each other for half a second and then burst out laughing because we did, in fact, have that much sex when we were together.

The conversation turned a little…

So he asked if I still had that one vibrator and I told him I had upgraded years ago. He said he needed a judge’s ruling on whether it counted as an “upgrade” so I showed him a photo of the one I had bought. He asked me where the weirdest place I had ever gotten myself off to was and I told him under the table at a bar prep course. He told me the weirdest place for him was in the bathroom of a fast food restaurant. We went on like this for a while, laughing at the lengths we had gone to orgasm and how often we got the impulse.

*Side note: Upon reading this I’m questioning if perhaps we both had some underlying addiction here… but I digress.*

So, he asks if I watch porn. I tell him honestly not usually because my imagination tends to beat what I find on Porn Hub, and he says he agrees. I laugh and say maybe porn is for people who don’t have an adequate bank of memories.

And we both go silent. Finally he studies me for a bit and asks if I ever think about him.

**This dude once tied me up and ate me out for an hour straight until I literally had to beg him stop. He used to put me over his knee and spank me every time I got a question wrong when I was studying for a law school exam. He used to make me wear vibrating underwear when I cooked for him and would turn up the intensity with the remote when I was trying to concentrate, and then make me get on my knees to and feed me. He once fucked me in the ass and fingered me so well during that I was the one begging him not to stop.*
*Of course I fucking thought of him from time-to-time when I was in the moment**

All that is to say, I adamantly denied it and then proceeded to turn bright red. When I asked him the same question he just gave me a sheepish smile and we both burst out laughing.

Finally, he admitted he had “on occasion” but only with one experience. I asked him which time and he went into detail about one of our sexual experiences where I told him he couldn’t catch me and ran around our entire apartment before he grabbed me and slammed me down over the table. He held me there for what felt like hours as he got hard and rubbed himself against my ass. I started begging him to fuck me but he refused. I started bargaining, and got more and more desperate as he just laughed at my frustration. At one point I apparently turned to him and said the words “You can spank my ass until it’s raw so long as your dick goes inside me in the end.” I did not remember this. I say weird things in the moment.

He asked me what I thought about and I told him I sometimes fantasized about the way he would withhold orgasms. He told me I wasn’t allowed to come without his permission and when I wanted to get myself off I’d have to text him and he’d tell me what I was allowed to think about while I did it. Sometimes he’d let me come in seconds, but other times it would be hours of agony as he teased me and made me play with him. Once in bed he was fingering me and I was getting close and he yelled, “Don’t you dare enjoy it. This is for me, you little slut.”

Our poor waitress kept coming back to fill our mimosas in the midst of these stories.

This opened up the floodgates a little as we both discussed our favorite sexual experiences with each other and in what ways we had enhanced them in our minds during self-pleasure.

It was flattering, unbelievably hot, and entirely inappropriate. We both agreed to never have a conversation like that again, but have sadly grown apart due to the inability to untangle the past.

Still… Memories are a beautiful thing.

Source: reddit.com/r/gonewildstories/comments/qb15ac/my_best_friend_i_used_to_masturbate_to_each_other

6 comments

  1. Always depressing, when you know there’s a connection but fate’s just like “fuck you”

  2. Broo this was so beautiful written. I also loved kind of a different approach to story telling and instead of explaining the incident directly you were reminiscing about it with your parents. Your excellent chemistry added a hell lot to the fun in this story.

  3. In my opinion, our minds and bodies weren’t built for monogamy. Some partners are not supposed to be lifelong companions, but they were meant to be in your life for some specific periods of time. This story is a quality example of that.

  4. Oh. This was kinda wholesome. Had a smiliar experience last year with an ex-partner. We wrote a bit back and forth, then somehow talked about our shared past experiences. It all ended in a well heated phone call.

Comments are closed.