The events of this story all happened about a year ago. I'm just sharing this now because I just found this sub and thought it would be fun to share.

A couple years ago, my (m26) girlfriend's (f25) best friend (f27) and her boyfriend at the time broke up. It was a pretty messy breakup and took a few months for her to recover and start dating again. The problem was that as soon as she did start dating, she found it difficult to meet somebody that excited her or met her needs. Fast forward a year, and she still hadn't met a single person that she wanted to become serious with, is increasingly jaded about the options (she has very high standards, to be fair to the options), and she just kind of wants to give up dating for a while.

Eventually, she reveals to my girlfriend that she hasn't gone past kissing anybody she has met since the breakup and is sexually frustrated beyond relief. She said the problem isn't necessarily the men, but completely about her - she felt inexperienced and vanilla with sex, as well as insecure about having sex with people she wasn't 100% comfortable with. She met her ex when they were in highschool and I guess their sexual exploration stagnated early, and of course the breakup still left her feeling bad about herself in that way.

It was after this conversation that my girlfriend, we will call her Abby, had the idea for us and her friend, Hanna, to have a threesome and get her sexual frustration out of her system. She thought it would help Hanna get more comfortable with having sex with other men other than her ex (her only sexual partner), and I think Abby also had this fantasy of showing Hanna how to perform, like it would be an educational experience. She told me at this time that Hanna was insecure about oral sex and she thought it would be fun to teach her.

I wasn't really sure about the idea at first. I mean, of course I thought it would be hot to have a threesome with my girlfriend and I did find Hanna attractive, but I never really thought of her sexually and felt it was kind of weird because they were best friends. I also didn't want to admit that I liked the idea, because I felt uncomfortable telling my girlfriend I was excited about fucking with her innocent friend. Abby assured me that she trusts Hanna and me more than anybody in the world and that it would just be a fun, one time experience to help her regain some confidence. I told her that I would do it, but I doubted Hanna would be down.

The next day, Abby texts me screenshots of her conversation with Hanna with a caption saying "shes in 😉". The screenshots showed their texts back and forth about the thresome idea. In short Hanna was very surprised that Abby asked her and felt embarrased. Abby was insistent that she was allowed to say no, but said that it would just be relaxing and fun to help her get off, and maybe encourage her to explore sex more as she continues to date. Hanna was still reluctant, but she did say that if she were to imagine having a threesome with anybody it would be me and Abby, because we are her best friends and she feels safe with us.

I remember my heart poundinng a little bit as I read the last two messages Hanna sent. The first was "i'm not saying yes or no... can I think about it and get back to you?" And the following message, which was sent 10 minutes later before Abby even responded, "omg i can't believe I'm saying this but what the hell yes I would be down"

They kept discussing it and agreed we should all hangout that weekend at her place. The plan was to have a few drinks, order food, and see where the night went, no pressure if she decided she didn't want to go through with it.

Saturday night came and we grabbed a bottle of wine and went to Hanna's apartment. Abby was excited and spent most of that day talking about it, wondering how it would go. Walking up to her building I was feeling a little nervous. When we got to her unit we were all a little giggly and awkward. At first we didn't discuss the reason we were there at all. My own nerves were calmed when I noticed that Hanna was all smiles and clearly the most nervous of the three of us, which I thought was really cute and kind of turned me on.

It was starting to really hit me I was actually going to have sex with my girlfriends best friend. Like I don't think I was convinced up until this point that it would really happen. But once I was in her apartment and drinking wine and turned on, I started realizing just how attracted to her I really was. She has wavy blonde hair, petite but a really nice ass. Her breasts are pretty small, probably B cup, which was something I didn't even know I thought was sexy until I started anticipating seeing her naked. She was wearing a lower cut shirt that showed off the skin of her shoulders and chest, and tight jeans. The outfit was a bit conservative in my opinion, but it still made her ass and boobs look so hot. Part of the turn on for me was this forbidden element, I think.

Abby was dressed much more hot and sexually. She is a brunette with straight hair. She wore a tight black crop top to show off her stomach and the form of her larger c cups. She also had a tan skirt to show off her legs and wore necklaces and rings, as she likes her accessories.

Eventually we finished the bottle of wine that we brought and half of one that Hanna had. I could feel that we were all kind of wondering when someone would make a move and get things started. Given that Abby was the one who was leading this whole event, she was the first one to broach the topic. She said something like, "sooooo... what do we think about hanging out on Hanna's bed?"

Hanna and I were tipsy and laughed. She got a little red in the face and smiled really large. She is shy and was trying not to talk about it, but we were finally at that point in the night where we had to decide if we were going to do this threesome or not, and it was her call at the end of the day. Finally she just bit her lip and nodded her head yes. We all got up from the couch and when to her bedroom.

Abby jumped on the bed and layed on her side watching us. Hanna was smiling sheepishly at me as she walked past and sat down on her side of the bed. I sort of stood there, feeling a little uncomfortable about just getting on her bed... I can't explain it but I just couldnt get out of my head the feeling of crossing boundaries with friends - a bed is a private space and I just didn't know her that privately. I think she could sense my own nerves and hesitation, which made her feel better and more emboldened. Finally she said to me, "you can totally get in the bed, make yourself comfortable."

I sat down closer to the end of the bed, Hanna was sitting up leaning against a pillow and the headboard, and Abby was laying down sort of cuddly to Hanna and getting pretty handsy. Seeing Abby initiating this, and the way she looked at me got me really hard. Abby said, "are we ready to get started," in the devious tone she does when she is horny... Hanna said, "I think I'm ready but I don't know what to do."

Abby got up and went to the other room. She came back with her purse and pulled out two vibrators. She gave one to Hanna and said it was clean and was her favorite one before saying to her, "You sit back and use this. We will start and you can join whenever you're ready."

Finally Abby told me to kneel on the bed with her. We started making out and Hanna was watching us quietly. I started kissing her neck and grabbing her tits through her shirt, then she started grabbing my cock through my jeans. Then she unbuttoned my pants and took it out, and I heard Hanna moan a little when she saw my erection. We kept kissing as Abby gave me a light handjob. Eventually Abby signaled to take off my pants, so I did so as she asked Hanna if she was enjoying the show. Hanna just kept watching me as she replied that she was.

I took my shirt off too and got back in the bed. Abby got down on all fours and began sucking my dick. She has this posture that I love where she arches her back a bit, and makes her ass look incredible as she gives me head. Not long after this, Hanna took off her pants and began touching herself as she watched Abby suck me off. Abby gives the best head I've ever had, she loves to suck my dick and is intentional about everything as she does it, working me up and then calming me down. As Abby was working on me, I watched Hanna play with her pussy. Every once and a while she would look up to me and make eye contact, but then break it off pretty quickly and keep watching Abby. After a little while she turned on the vibrator, and she began moaning as she masturbated to Abby and me. I got carried away with how good Abbey's mouth felt and how hot the situation was and started to fuck Abby's mouth. Hanna was getting more and more turned on watching and finally decided to join in.

Hanna got up and sat closer to me, and immediately Abby stopped and nudged me to move to her. Hanna started to suck my cock and stroke me at the same time. Abby watched and exclaimed how hot it was to watch this, which made Hanna smile and laugh. She continued and I asked if she was comfortable with me touching her, which she answered by silently nodding yes with me still in her mouth. I began to play with her tits as she gave me head which made her moan as she sucked. It felt good, but Hanna was definitely not as good as Abby. I think Abby felt that too because she asked her if she still wanted tips for giving head, Hanna said yes she would want advice.

Abby got closer and told her to use her tongue and tease me more. I turned to her and she demonstrated licking my shaft and head, as she made eye contact with me, occasionally wrapping my head with her lips before going back to licking. She told Hanna it is all about dynamics, before letting her try.

Hanna began licking my cock similar to how Abby did, but it felt so much more exciting that it was Hanna. It is hard to explain, but it was in this moment where the whole situation really got hot for me... Hanna had been avoiding eye contact with me most of the night, but now she was teasing me and maintaining this hungry, erotic eye contact with me. It was like she was reading my mind and desire for her to start really sucking, but in her blue eyes I saw her enjoying the suspense she had me in. She would bob her head down for a short time and then go back to licking my frenulum, because Abby told her it is the most sensitive part of my penis.

Abby saw this chemisty and started getting really turned on. She forgot about the lesson and started kissing my flank and my thighs as Hanna kept teasing and finally sucking me more. I wanted to collapse from the pleasure, it was so fucking hot. Abby and I started making out as Hanna got really into sucking my cock. Abby and I were dirty talking and Hanna was moaning and touching herself. Then Abby said she wanted me and Hanna to fuck.

Hanna made no complaints as she quickly removed her shirt and bra and laid down on her back looking at me with the most intense fuck me eyes. Abby took her clothes off and laid next to Hanna with a vibrator. I moved up to Hanna and got into missionary position, as it was just the easiest and I already knew Hanna was really only comfortable with that position. We kissed for a moment before starting and I sort of dissociated because she was really good at kissing. We snapped out of it when Abby laughed and said, "uh hello I'm still here!" Hanna started stroking me again and finally I inserted my cock into her vagina. She was really tight, but she was so wet and turned on... It felt like heaven.

Abby was watching and moaning and talking about how sexy it was to watch Hanna get fucked by her boyfriend. I felt kind of bad because I was really enjoying this moment with Hanna, I didn't expect this chemisty and connection I felt. We were fucking and made out for a while and I finally decided I had to include Abby so I pushed myself up and fucked Hanna harder as I made out with Abby. This seemed to turn Hanna on a lot because she was starting to moan really loud. Then Abby surprised me a little and started kissing Hanna. This almost threw me over the edge so I had to slow down lol. I started giving Hanna's tits more attention and sucked on her nipples for a while as I calmed down.

I started fucking her faster again trying to get her closer to orgasm. Abby got distracted and turned up the vibrator to make herself cum, and when I got Hanna close and felt myself way too close to coming, I pulled out and started fingering her. It didnt take long for Hanna to orgasm and when she did she squirted a little. Abby grabbed my cock and started giving me a handjob as I knelt over Hanna. Abby asked her if she wanted me to come all over her, and Hanna said in a sleepy post orgasm tone "oh my god yes pleeease."

Abby and I made out while she worked me up. Finally she made me cum really hard and I watched my load shoot all over Hanna's stomach and tits. I have to say it was one of the most satisfying and memorable orgasms I've ever had.

We all calmed down that and got pretty quiet for a little as we enjoyed our afterglows lol. We started joking and laughing and talking about how much fun that was. We all cleaned up and Hanna showered, then we all got comfortable and started talking about sex and our experiences. Hanna opened up a lot about her troubles with sex and her frustrations, and said this night was cathartic for her. Abby and I left really late and went home.

I told Abby I felt bad that she and I didn't end up having sex at all and it was just Hanna and I in the end, but Abby was assuring me that it was totally okay and that she really enjoyed just masturbating and watching. She said she could tell we were enjoying ourselves and felt bad asking for her turn, because she gets me all the time. She said she was satisfied with the whole experience and is was all about Hanna in the first place.

Before that night, the three of us agreed to set the boundary that a threesome was a one time thing for us. Logically, none of us wanted to complicate the dynamic at all. But after we had actually done it, I was kind of sad at the thought that we weren't ever going to do it again. In hindsight I regretted hownit went in a way, like I wish Abby got to teach her more like she wanted to and I wished I had gotten to give Hanna oral.

We haven't had a threesome since then, but I will say that wasn't the last time Hanna and I were intimate. Maybe I'll tell that story another day. I wanted to include it now, but this is already way too long because I got carried away in the details lol.