u/trish_runs

So my friend and I are still on our trip across the country, being in Alberta where we had planned to stay for a couple of days before renting a car and driving through to the west coast. I've dropped a story earlier in the trip here in case somebody wants to read the first part. This is the same friend, same trip, just later.

Prior to us beginning this trip, I had reached out to a former FWB to let him know we were planning to visit and had asked if he wanted to do drinks at some point. We both knew what the plan was but we liked to dance around the topic, just to keep at least some element of suspense. We talked a bit and eventually, he offered us a guest room at his place. He said he would be working during the day and was happy to share his space. I knew him well, my friend trusted me and it made sense to cut costs. At the time, we thought hey, we'd treat him to a nice meal and everybody wins!

So back to this current trip, after our very enjoyable threesome, we realized that if the opportunity came up again, we wouldn't say no. The thrill of it, the taboo of it and all that, it was almost like we were looking for every opportunity to just try it again. I won't lie, my mind went to my FWB but I didn't dare bring it up. Luckily, my friend had the same thought and she brought it up, subtly suggesting that she would be interested if I was ok. Now, I had obvious ulterior motives when I messaged FWB, as I mentioned before. So yes, even though I was ready to fuck his brains out, sharing him with my friend never really crossed my mind as a realistic possibility until very recently. And yes, it seemed like a fun idea so I told her we should see if the opportunity comes up because I would be very happy to.

We joked about what we could do and what we could say. We wanted to make sure he would be comfortable and that we didn't put him in an awkward position but also wanted it to be direct enough so that there was no misinterpretation. We talked about how even though alcohol played a big factor in our first threesome, we still wanted to make sure he consented correctly and that we didn't feel like we would pressure him in anyway. I know, so many guys messaged me saying how lucky the first guy was and how it was their biggest fantasy. I'm just saying, people like different things and might just not be comfortable and I like to make sure everybody is happy and having fun! DONT BLAME ME. So we drew up a plan and decided to enact it when we all were comfortable and settled at his place.

We landed in the city and took an uber to his place. It had been a while since I had last seen him so it was definitely awkward and funny. A lingering hug, some subtle eye contact here and there. He had to do a few work things so my friend and I settled in the guest room and unpacked a little bit of what we had. She gave me a look and we both laughed knowing full well she was still interested in our plan.

We ordered food and ate at the dining table while he finished a few late calls and finished some work while eating at his desk. His apartment isn't huge, so his desk was in the living room which meant we had to whisper and stay quiet as to not bother him. When he did finish, he joined us to eat. My friend and him started to talk, asking typical questions about what they do, how my friend and I met and how our trip was so far. We didn't mention our sexual adventures but talked about some of the sights we saw, some of the food we ate and what we really liked.

Eventually, she asked him how he knew me (already knowing what the answer is) and my old FWB and I gave each other a look that said it all. My friend laughed and said don't worry, she's told me everything.

"Everything? I hope not" my old FWB said.

"Don't worry, we share everything" I joked, gave her a look and then gave him a look before putting some dishes away. A little too much on the nose but it was fun to tease and it was a good test to see exactly how interested he would be. We weren't just going to throw ourselves at him without really confirming he wanted to do it.

It was still early on in the night so we just put on a background movie and just kept talking and watching. Nothing really happened, we talked about places to see, where we should eat. He said he had work the next day so he couldn't stay up too late which was disappointing. Eventually, we hit a bit of a lull and my friend started to pry a bit about my history with my old FWB. He looked at me, I nodded and he just started to spill the beans. A bit about how we met and how things started. I talked a little bit about how fun it was and we started to talk a little more about the details. It was like testing the waters. Once he realized I was serious about how I do share everything with my friend, he was a lot less shy about what he could talk about and it just became a talk about our past adventures, what we enjoyed and some of our favourite moments. My friend would ask clarifying questions and he would answer and they started to get a sense of what both of them liked. He would ask her things like what she liked and naturally, the conversation went to fantasies that we've always wanted to try.

He talked about some of his and not so subtly mentioned threesomes with two women while awkwardly doing his best to not look at us. It was cute and my friend and I instantly looked at each other as if to say "ok, he's interested" before my friend dropped that we had a threesome together earlier this trip. His eyes lit up instantly and questions started pouring in on how was it, what happened, had we planned it, was it our first time together. It was GAME OVER at that point and we just kept talking until finally I dropped it.

"So, would you be interested in exploring that fantasy tonight?"

There was an awkward pause and I almost felt like maybe this was a huge huge mistake. I had this awkward moment of looking at my friend and back at him and wanted to throw in a quick "it's ok if you don't! Please don't feel awkward about this" but before I could, he said:

"yes"

And from there, things picked up. There was a split second of hesitation before I moved myself towards him on the couch and we started to make out. I sat on one side while he sat on the end of the couch. My friend did her best to position herself and we awkwardly shimmied our way closer to the middle to give her space on his left before our kiss broke. He looked at her and she pulled his face in and started to kiss him. I remember watching them kiss and thinking that this felt much more surreal than the first time. Maybe it was because I was sober or because this time I was watching a guy I knew kissing my friend. Or maybe because this was actually planned and now there were expectations about it? It's hard to really describe but it was dream like and I just had this weird obsession to just devour him.

I started kissing his neck and fumbling with his pants as he kept kissing her until finally his cock was out and I was stroking it. Hard as a rock, exactly as I remembered it. And before long, I started to wrap my lips around his cock. Hearing his moan while he kissed my friend. 10/10 experience and honestly one of my new favourite moments. Eventually they would stop kissing and I could feel her eyes just staring at me and his cock and it felt like it was an appropriate time to switch.

Switching, by the way, is a weird thing. Not to derail and ramble but how do you know how to split your focus and time and effort between two people? We talked about this after and even he felt the pressure of knowing who to play with, if he was spending enough time with both and if everybody was enjoying it. I felt it too (and so did my friend). So just want to throw that out there for those who fantasize about this. It is an awkward thing!

Anyways, watching her blow him was so hot and I started to strip off his clothes more before kissing his bare chest, neck and back to his lips. Not long after, he pulled away and said he was cumming. And to my surprise, my friend didn't stop and instead sped up, using her hands and in scientific terms, extracted his cum out of him. I don't really know how else to describe it and honestly, I did not know she even liked to do that. But seeing it, hearing him cum and for it all to end, it was very very fun.

We rehydrated, we debriefed and just talked. He just stayed naked while we laughed at what just took place. He apologized for finishing so quickly but we told him it was fine, we have all night. We smiled and he knew we weren't joking. So.. he did the bad thing of giving his boss a heads up that he was starting to come down with a bad cough and fever and was going to work from home tomorrow.

And the night just kept going. He asked if we could watch us play and we said yes. We moved to the bedroom and just started kissing. We'd stripped down and things started to pick up. He would tell me to suck on her nipple or for her to grab my ass and we obliged. Her hands reached down to my clit and things kept escalating. Our kissing was messy and my old FWB positioned himself on the bed and all three of us were naked, mouths everywhere, touching everything and doing our best to just feel good and make each other feel good. Even though we were sober, it's hard to describe everything given how it just felt like a constantly evolving experience. Our mouths were on each other, lips and tongues everywhere until finally he pulled out the condom and told me to turn around. He positioned himself over me and pushed himself inside and it felt intimate for a split second. We moaned about how we missed this, we'd tell each other how good we felt and I admit, I completely forgot my friend was there watching. But she respectfully gave us a moment until joining back in.

And then again, a blur. He fucked her for the first time and watching that was incredible. When things finished, we would just cuddle on the bed and just touch and kiss and feel each other. We would end up in the shower to finally clean ourselves up and get ready for bed but that ended up as another place where we'd play.

We finally got to bed late and when his alarm went off, we were not feeling great. Lack of sleep, us all squishing on his queen size bed. Snoring, kicking. We probably won't choose to sleep in the same bed next time but we were all naked and waking up and freshening up, everybody's mind went back to the exact same thing. He went to his desk to quickly answer emails and the very bad parts of us decided it was the time to tease him. So we did and inevitably, he got hard, distracted and had trouble getting much done while we both played with his cock.

And again, he made the unethical choice of telling his boss that he wasn't feeling great and needed some time to rest. He could answer emails and urgent questions but needed to take it easy. His boss was very understanding and gave him the day off. But he didn't end up resting at all that day. One very distinct moment I remember was going downstairs to bring food back for us and coming back to them fucking and joining them. It was pretty much one of those days where the moment any of us were ready, we just started again.

And now as I write this, I realize we did not explore the city at all. Our two days were spent eating takeout, looking out his apartment window and fucking. I am not complaining but it feels like I just have to come back to genuinely see the city. My friend and I now have the car rental and are driving out to the west coast. Unfortunately, no plans like this just yet but we'll see!

One of my best friends and I recently embarked in a travel across Canada adventure. Yes, it isn't the amazing eurotrip we had hoped for but given our financial circumstances, it was a more affordable and still very fun trip (that I'm still on now as I write this). We've been friends since university and although we don't live in the same city now, we still do our best to make time for each other, which mean this 3 week long trip was exactly what we needed.

We planned out our trip, making plans to stop at a variety of places including seeing friends from different parts of our lives, eventually ending up on the west coast. As we talked about who we wanted to see, it became kind of obvious why we prioritized certain people over others. I've written stories of a few people and although a lot of them have ended up in relationships, married, kids etc etc, some haven't. So this trip has also been an excuse for myself to just reach out and see how people have been and how life has treated them (with potentially some ulterior motives). I am, as a lot of you are, awful with keeping up with old friends so a trip across the country and stopping at major cities? Why not just grab a coffee with old lovers and see!

Now, my friend, she's a little less adventurous but also had a very similar idea. We talked about who we wanted to see in Montreal, in Toronto, Kingston, Ottawa, Calgary etc. She would mention guys she wanted to see and one of them was just a long time crush that has never gotten past a drunken makeout at a party. But now that time has passed, maybe the stars are aligned and they can finally have their moment.

So I'll fast forward to us arriving finally at his city. She goes off to meet him for coffee and I'm left to my own devices. The people I knew were not free that day so I walked around, had a nice lunch on my own and went window shopping. I eventually got a text from my friend saying we were all going out tonight. So we got back to our airbnb, ordered food in and got ready.

I'm very biased but my friend is gorgeous. Amazing skin, hair that I'm jealous of and just so pretty. She's indian but born here for those that do care. And seeing her get ready, I knew that she really liked him and was clearly doing her best to look hot (which she did). I decided to match her energy, knowing that her crush was bringing some friends and who knew what could happen.

We met him at his place first and instantly, I could tell why she liked him. He was hot, really polite but also awkwardly quiet. He didn't say much to me but gave her all the attention in the world. His friends were polite but we didn't click in the way that you may have hoped but that's ok. I was here to support my friend and to get her laid.

Eventually, after a few drinking games, we arrived at the club, just drunk enough to start dancing right away. His friends slowly but surely made their way towards me and we danced but kept it "PG". Danced close, some hands on hips but nothing that I would describe as overly sensual. My friend, however, was the opposite. I'd see her dancing close, tightly against him, his hands on her hips. And I swear, it wasn't long before they were making out like their life depended on it. We all noticed it and just "cheered" in our own way. I mean.. who couldn't be happy for them right?

Not much else happened at the club so I'll fast forward to our uber home. He joined us and honestly, it was probably my first experience as a bystander seeing this kind of sexual tension. Just pure silence but a lot of subtle leg rubbing. In my head, I was just planning the logistics. Drink a ton of water, clean myself up, put on headphones and sleep and be happy she's getting it. It was a simple game plan right?? But as the title suggests, I failed.

My intention was not to interfere at all. She liked him, he liked her and they obviously deserved their moment. But I swear, they set me up for failure. I entered my room and I instantly heard shuffling and kissing. I couldn't even get to the washroom because they were right in the common area on the couch. My mind was thinking ok, maybe I can just sleep, accept that I'll be hungover, dehydrated and that I didn't get to clean up before sleeping (all of which are things I hate) but I'm doing it for her. Maybe I'll just sneak out, pretend I'm not looking and they'll be distracted enough to not notice me or not care.

So.. I tried it and the moment I opened the door, they both looked at me and there they were stripped down, his cock in her hand as she was stroking him off mid kiss. We awkwardly made eye contact but.. they kept going. She kept stroking him and they turned back to keep kissing and I kind of just watched. I didn't want to but it was hot to see her eventually pull his cock to her mouth and to hear him moan. I'm obviously a sexual person and given the alcohol and the sexual tension, I just stayed at the door. It felt very porn like, like the walk in on your friend, stare at them, touch yourself and then just join. I didn't touch myself or anything but I awkwardly found myself grabbing water in the kitchen but not in a hurried way. In a way where I clearly was still seeing everything and they knew it.

Eventually, my friend pulled away and said she needed water and I guess we just all sat there, rehydrating while they both were naked. And again, they had that look in their eyes and just went back at it as if I wasn't there. I must give off this non threatening energy or something because I felt invisible as they found themself on the couch again, this time fucking with her on top of him. And I again awkwardly sat there, sipping my glass of water slowly but just kind of captivated by it all. Two hot people fucking in front of me, I was horny, who can blame me really.

Like I said before, he had this calm quiet energy so it was a shock to me when he looked over to me and said come here. I made eye contact with my friend and in her eyes, there was nothing that said no I listened. I walked over and he said kiss me and I lowered myself and positioned myself and started to kiss him as she continued to be on top. When my friend and I eventually talked about it afterwards, I described it like hypnosis. Like I didn't have really self control and that it felt like it was all that I wanted to do. And I will say, kissing somebody who was fucking somebody else (especially in this awkward position)? Very weird but very very hot.

I felt his tongue enter my mouth and I reciprocated. It was what I'd describe as an overly passionate kiss and I couldn't help but match his energy. And then he pulled away and said to kiss [my friend] and I obliged. And again, kissing somebody that's fucking somebody else? kissing a woman? and also my best friend? Very very weird but also very very hot. And again, she just went for it and I just couldn't help but match her energy. All the while, he started to grab my ass and I really started to get into it.

I stripped down finally and we somehow found ourselves in one of the bedrooms, both of us laying on our backs naked as he stood over us. And he'd start to eat one of us out while fingering the other, kind of going back and forth a bit until he started to fuck her again. I remembered kissing his neck and telling him to fuck her harder and to fuck her brains out until finally he came and we all just collapsed.

The reality hit quickly and I remember distinctly all of us just laughing at how ridiculous that was. He went to the washroom to throw out the condom and clean himself up while my friend and I just laid there naked laughing at what happened. I remember apologizing so much for interrupting her moment and she said that she had fun and told me not to apologize. By the time he was back, the sexual energy was different and we were all exhausted from what just happened and from the alcohol so I went back to my room and he stayed for the night with her.

Nothing else happened in the morning. He was back to his quiet self, we said goodbye to him and my friend and I debriefed on what was a crazy night. I told her again how apologetic I was and she said that he wasn't exactly how she remembered him to be but still wanted to get him out of her system and that did it. She said the crush kind of disappeared at their coffee date but she's thought about him enough to the point where she physically wanted to make it happen. And for me joining? None of it was planned but she said it was fun and wouldn't say no to it again if the moment came up. I said the same thing. If it feels right and it just happens to work out, why not.

We have just two weeks left and plenty more people to see so who knows what we might get up to. I have at least one "date" lined up so if they click, I'm not going to say no to another fun night.