I’m going to start by saying I don’t like myself in this story. There are very few stories I regret about my past, but this is one of them.
I had pretty intense sexual tension with a friend back in the day. It was one of those situations where we almost certainly would have dated if the timing had been right, but I was with someone else when we met and then he got a girlfriend.
*I really don’t like this part of the story. His girlfriend was a really sweet person.*
One night we were studying together at my place and went over a piece of caselaw with a very weird sexual story embedded in the narrative. He made a comment about how no one would actually do that in bed and apparently I got noticeably quiet. Finally I just started giggling and was like, “Who wouldn’t do that in bed?”
*I’m going to be totally honest, I don’t even remember the act in question. I think it was actually something pretty tame.*
Well, that sparked his interest.
I had actually hooked up with his friend the year before who apparently hinted I was good in bed but wouldn’t give specifics. My friend said he had always been curious about what he meant.
At this point, I did actually bring up his girlfriend and pointed out that she probably wouldn’t appreciate us talking about my sex life. He told me she had cheated on him two months earlier and they were likely going to break up.
*Side note: they did not. Again, I really liked his girlfriend and hate that aspect of this story.*
After that, it was really hard to stop.
He asked me about the weirdest thing I’ve ever done in bed. I answered honestly that I wasn’t even sure what would constitute my “weirdest” act. I explained that I generally liked being dominated and that alone has led to some interesting situations.
*In the words of my ex, there is VERY little I will not do in bed.*
So I told him a few stories…
I told him how I once accidentally broke my nose during sex when my partner and I were drunk. I also once got so loud with a partner my neighbor called the cops. I had to explain to a very shy police officer that the rope burn on my wrists were, in fact, consensual. I told him about how I had made eye contact with a very hot girl while we both fucked our boyfriends in a frat house.
We were laughing, but also getting dangerously closer to each other with every story I divulged. His questions were also so vanilla it was almost cute.
*Yes, friend. I have indeed swallowed cum.*
Finally, we got on the subject of why we never dated.
He told me I should have called him after I broke up with the guy I had been seeing and I told him he should have made a move. He asked if I ever thought about him that way, and we both admitted our attraction towards each other.
I’m not really sure who kissed whom. Fuck me, it was a great kiss though.
We immediately rolled back on the floor and he climbed on top of me as we made out. He kept grinding his hips into me so I could feel how hard he was and I whispered how badly I wanted to fuck him.
I told him to pull my hair as he moved to kiss around my neck, and I let my nails dig into his back as we rocked back and forth like that.
When he asked if I had ever gotten myself off to the thought of him, I answered honestly that I did all the damn time.
*That was true btw. I thought of him a lot. I think that’s why this was so hard.*
Apparently the first time we had ever hung out I told him I love giving head and he had gone home and immediately got off to the thought of it. He told me it had become a regular habit.
That’s when I kind of snapped out of the magic.
I pushed him off and put a book in between us as I reminded him he had a girlfriend. He reminded me they were “practically” broken up.
I told him to fuck off.
*I have been cheated on. I really take it seriously.*
I pushed myself to the opposite wall and told him we couldn’t touch each other. I was sincerely afraid if we kissed again we would end up fucking. We had that level of chemistry.
He asked if we could keep talking, and I told him only if he agreed to stay on opposite sides of the room.
He very reluctantly agreed to my terms.
“Can I know what you think about when you get off to me?” He finally asked.
I got off to the thought of him bending me over. In fact, we were in my room and I explained I often fantasized about him bending me over the desk he was up against.
He closed his eyes and took a couple of deep breaths to calm down which honestly made me laugh a little. The man looked like he was in pain.
I asked what he thought about and he told me he fantasized about me giving him head.
“Did I look you in the eyes while I did it?” I asked.
“No, but I’m adding that to the bank of fantasies.”
“Did you come on my face?”
“You’d let me come on your face?”
“No because that would count as touching.”
We went on like this for a while, talking in theoretics. I told him I would theoretically like him to go down on me and he told me he would theoretically like to see me climax.
*I want to be clear, this was already cheating.*
“It’s hard to be around you sometimes,” he finally said.
“Because of the tension?”
“Yeah, I just can’t help but think about you naked. It’s an unhealthy obsession.”
And at that, I took my shirt off and let it fall to the floor. Next I took my bra off and threw it away.
For a solid ten seconds, he just studied me with his mouth hanging open. I’m going to be honest, his expression alone was enough to get me wet. Holy shit.
“Can you play with them?” He asked shyly.
I moved my hands to my breasts and started playing with myself. I usually can’t get myself close to orgasm through nipple play, but I was so turned on at this point I was actually pretty close.
The poor man looked like he was about to die. “V… I might have to go.”
“Just get yourself off.”
“Seriously?”
I shrugged. “There’s lube in the drawer behind you if you need it.”
It took him a while to comply. We were both struggling with this. Finally, he unbuckled his belt and pulled his pants down low enough to pull himself out.
*Bro had a really nice dick. I’m still bummed I never got the chance to suck that one.*
“How would you fuck me?” I asked as I started pinching my own breasts.
“I’d start with you on the desk.”
“I’d ask you to bend me over pretty quickly.”
“I’ve thought about your ass so much like that.”
“With me bent over?”
“And in my hands.”
“I’d probably ask you to spank me. I really like being spanked.”
That really put him over the edge. “Fuck,” he groaned. “You have no idea how much I want you.”
I started rubbing myself through my jeans. In another life I would have taken them off as I am not shy about getting myself off in front of others. However, it is VERY hard for me to stop once I get past a certain point and was afraid if additional articles came off we’d end up fucking.
“I really wish I could swallow your cum.”
“Fuck!” He cried as he came.
*He wiped himself off on my damn flash cards which were color-coded btw. That’s a fun detail etched in my memory.*
He told me to get myself off, but I declined and said we’d already gone too far.
We had the award conversation where he told me he’d break up with his girlfriend and I told him I actually thought he should try to make it work.
*I wasn’t being noble btw. I probably would have dated him if they had, but I sincerely liked his girlfriend and thought she probably deserved another chance after cheating. Hell, so did he.*
When we calmed down and clothes came back on, we actually did cuddle for a while before we left.
That was difficult.
The fucking moment he closed the door behind him, I really put that lifetime warranty on my vibrator to the test. I got myself off probably ten times to the thought of his face while he came. I stayed up all night alternating between memorizing crim pro elements and destroying my clit.
As you’ve probably guessed, we never got together or fooled around again.
Weirdly enough, he actually told his girlfriend about us. I went to lunch with her the following month and eventually she forgave us both.
So no, this was not ok. I would not do it today and deeply regretted playing a part in their rough patch. In another life though, this dude and me would have fucked each other silly.
Source: reddit.com/r/gonewildstories/comments/rttk2f/i_watched_my_friend_get_himself_off_mf_cheating
God you are definitely best erotic story writer I have read on this site. So hot and real. Great work and keep it up.
The fact that you were 99.999% there but didn’t cross over just screams law student/lawyer…. As a fellow law school graduate this story was frustrating in more ways than one…
You had so much more fun in law school than I did. Really, more fun than literally anyone I know. Beyond jealous.
But yes, cheating is wrong.
I would go countercurrent and tell that this helped them to stay together, and the reason why he told her.
If you two didn’t hook up you were at least “used” the let him draw with her cheating.
So, did you make mistake? Maybe yes but that mistake turned out for the best.
Wow OP, your story reminds me how many dimensions there are to cheating and how easy it can be in the moment (or after it)to persuade yourself that you can redraw the line. In my experience, cheating is so much more complex than just, like, fucking someone once, regretting it and begging for forgiveness, like in the movies. You are so generous to not only share your sexual triumphs but also the weird and the sad. Please keep it up!!