Volunteering my boyfriend to help my friend to get off

NSFWNo Regrets

My friend got out of a very long relationship 2 months ago and honestly been having a very hard time, the guy broke up with her and she been slowly loosing her mind. One minute she complains about missing him, then hating him, then saying she missed the sex, then saying sex wasn’t even that good, then contradicting herself again. I tired to be as supportive as I can be, but it’s obvious she is just going in circles refusing to move on. First I tried to nudge her to maybe go and try to see other ppl, but she’s like if I go on a date I’ll just start talking about my ex and random hook ups are so iky.

Thats the context now let’s get into the actual story. Before their break up, we rented a cottage to go with friends for a long weekend. That was before own couple broke up and other dropped out, so now we had only myself, my boyfriend going and this girl. Both of them wanted to just cancel but I was like fuck that we going just 3 of us and they agreed. I had already something brewing in my mind and told my boyfriend to be nice to my friend, like really nice and winked at him.

As we got there my friend was usually whinny but I didn’t pay much attention to it, the girl is hurting, instead I started volunteering my boyfriend to do shit for us, he’s smart I think he caught on what I was planning. First I was like can you please make me and my friend drinks, then I’d hype him up infront of her. He brought us things, made us food, gave us massages. During the massages I don’t think she realized but my friend started moaning a bit, that’s where I knew I got her ass.

Evening comes and goes and we all ready to go to sleep, I go to my friends room and crawl into her bed and hug her from behind, we chat while cuddling for a bit and then I go, “I’d like for [my boyfriend] to sleep here with you tonight” she frantically turns to me and replies “what do you mean?” I stare at her for a while, fuck she is so pretty, then I kiss her lips and reply “what’s mine is yours” then I get up and go and as I’m about to leave I ask “so should I sent him” few moments of silence and then a single “yes.”

I quickly go and tell my boyfriend he has a mission and needs to take care of my friend, make her feel like the only woman to ever been loved, I know he can be good at that. So he did, and not only that night but next two night too, I was honestly quite jealous, however it was me who pushed for it each time and it clearly worked, my friend stoped whining about her ex for the first time like ever.

Bellow is the retelling of the first night from my boyfriend as I was giving him a blowjob. He got to her room and it was awkward as fuck, they both exchanged an awkward hi and then my boyfriend asked to he could lie down, which my friend said yes to. Then in bed my boyfriend asked if she wanted a massage, my friend agreed and layed on her back, after lowering the covers he realized she was fully naked, which I noted she very much wasn’t when I left her. He gave her a full body massage which eventually turned into fingering and my friend cuming. Then he turned her onto her back and asked if he can kiss her, she nodded and they kissed, then made out for a bit, she was cupping his cock in his shorts. He asked if he should take the shorts off, she said yes. They contributed making out and she was slowly stroking him. Then he asks if she wants to go farther, she again said yes, so he spread her legs and pushed his cock against her pussy, again asking if this is okay, she said yes so he went in. They were in missionary for a while, i knew this myself as I heard them. First it was just quite bed movement, then there were moans, mostly my friends but also my boyfriends. He said she started to cry mid sex which scared the hell out of him, but she begged him to keep going once he stopped and apologized for the tiers, said that she was overwhelmed but felt good and wanted to keep going. So they did, no position switch of anything, just slow missionary with a lot of making out and ties from her side, allegedly she came few times and then ended up sucking him off dry. Part I didn’t expect is that he stayed with her the whole night, she asked him, was guilty about it the next day but I didn’t mind, I knew she needed company and I knew my men is the best kind of company.

This went on for two more nights, I wanted to join them, but felt it would be wrong, and my boyfriend would always come to me in the morning and fuck me so it’s not like I was not getting my attention. It’s been two weeks and my friend is doing way better now, she thanks us both for helping her out of her head and says that she actually feels like she’s moving on now.

Posted Aug 12, 2026, 2:11 PM UTC

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