I (25,M) was on vacation in Vancouver and single as all hell. I was in the city for about a week and I really wanted to share an experience with someone. Shortly after arriving, I went to my airbnb, freshened up and hit the down. I did a bit of a bar crawl. Went to some cool dive bars/grungy performance halls, and met quite a few cool locals.
At one of the bars, I saw this gorgeous brunette standing at the bar waiting to order. I decided to grab myself another drink and shoot my shot.
She was in a stylishly ripped white t-shirt, a red bra that you could see through the rips, tight black leather pants, a tight bubble butt, what appeared to be DD tits, and an overall body type that screamed fitness.
I didn’t really know what to say. So, I just told her if she needs help fixing her shirt I was always pretty good at arts and crafts. She laughed, I’m not sure if she laughed at the awful icebreaker attempt or if she legit thought it was funny. We started chatting and it turned out we actually worked in the same industry. About ten minutes into it, things started to get interesting. She asked when I was leaving Vancouver and if I was single. Just as I started to answer, a guy came up and asked her politely what was going on and if she knew me. She said we just met and he then said to her “where should we go for part two of the date?”. I was stunned. Realizing this was my last shot; I asked if she was still interested in showing me around and if I could grab her number. She was down! I could tell her date was deflated by this, but I couldn’t let this opportunity pass me by.
We agreed to meet the following night at 9pm at a high-end sushi place. I’m not normally one to splurge, but what the hell, I was on vacation.
Now, I’m not the best looking fella, but for whatever reason, women tend to like my nerdy, stoner, skater, sarcastic vibe. The reason why I say this now, is because I remember watching this gorgeous woman walk through the doors of the restaurant and think; I have undoubtedly scored out of my league. She came in wearing red lipstick, a tight black dress, high heels, and fishnets. Her dress was so tight her tits looked like they were ready to pop out, and around back you could tell her perfect ass had swallowed up the g-string with the same ease a fat kid eats candy.
Unfortunately, our table was double booked and it was going to be a 45 minute wait, so we got set-up at the bar. We each ordered a drink and resumed the previous night’s conversation about work. Things were going great, and about half way through our first drink, this visibly stressed jacked Asian fellow sat down next to me. Both my date (we’ll call her Kim) and I noticed how concerned this guy looked, so we decided to engage with him. I asked him how his night was going and he looked over wide-eyed with an incredulous look and said “I just found out my girlfriend of 7 years fucked her boss”.
I did not know how to respond to this, but without missing a beat Kim said jokingly “You should get even with her and fuck her boss too!” It made him laugh which was a relief and he introduced himself to us as Andrew. He told us he didn’t want to interrupt, we said it’s not a problem, and he ordered the three of us a round of shots. One thing led to another and we just kept drinking together. It turns out that Andrew also worked in the same industry as Kim and I. We were all in separate departments, but it was easy conversation.
At this point we were all pretty bombed. We finished a plethora of rolls, and told the staff not to worry about moving us to a table. Kim, Andrew, and I were on one. Kim and I knew it was up to us to keep Andrew in a half decent mood, it was a fun little game. Every now and then he would bring up his now ex and grow teary eyed and morose. But we would just steer the conversation away, make jokes, or Kim would lean over showing off her oh so spectacular cleavage.
It was around 11:30 and the restaurant closed at 12. I looked over a Kim and asked what to do next. Andrew chimed in and said “my apartment is in the next building over if you want to come by for a drink”. Normally, I would not go to a random dude’s house I met at the bar with a date, but, I was pretty hammered, and fuck it I was on vacation.
We exited the restaurant, and a couple doors down from the restaurant there was an entrance to a building. We walked In and I was pretty surprised with how nice it was. Marble looking floors, a gorgeous fountain, a doorman, pretty snazzy stuff!
His place was on the 50-something floor and it had an amazing view of the city. Once we got in, Andrew went to the washroom and left Kim and I in the living room. “Do you want me to be a slut for both of you tonight?” Kim asked. I am no prude, but this was the first time I really had ever considered a threesome. Unsure of what to say I nervously blurted out “Do you want two cocks inside you?”. She grabbed my dick and nodded. As she was stroking it over the pants, we heard Andrew wash his hands and open the bathroom door. She let go of my cock and we sat down on the couch.
Andrew asked if we liked tequila, as he had a pretty extensive collection. We said yes. He led us to his liquor cabinet, and my god, he must have had a hundred bottles. He’d tell us about the different kinds, and we’d each take a small shot after he described it. At this point I was sitting down, Kim was on my lap, I was rock hard and squeezing her ass every chance I got. After about 5 or 6 shots (a ton of half shots to taste the different tequilas) we decided to go back to the living room and put on some music. Once I stood up and looked at Kim, I saw that one of her nipples was above her dress. I guess while she was on my lap one of them popped up and I couldn’t notice with her back to me.
Once we sat on the livingroom couch (Kim in the middle) Andrew turned on the tv/sound system. Kim asked if she could put on a youtube video. She grabbed the little portable keyboard and put on this anime type music video about a threesome, pulled a blanket off the back of the couch, and spread it across all three of us. She grabbed my dick immediately as the blanket covered me, and I assume she did the same for Andrew.
She asked why no one said anything about her nipple being out. Andrew started growing a little nervous and blushed, but otherwise seemed to be going along with it, and I said “I didn’t want to ruin the show.”. She then stood up, unzipped her dress and said “well the show must go on ” as she freed her tits completely and brought the dress down past her knees. She had a bright red g-string under her fishnets that matched her lipstick and asked who wanted their dick sucked first. Andrew peeped up and said something along the lines of “can I fuck you first and he can fuck you after?” Kim looked at me, I nodded and Andrew took her into his room and fucked her HARD. I heard the bed rocking and her screaming from the living room which only made me hornier. I sat there stroking my cock, listening to their animalistic moans and pants, trying not to nut. About 20 minutes later, Kim emerged from the room and said “round two”. She got on her knees spit on my cock and wrapped her tits around my cock and started titty fucking me while staring at me with her green eyes. She asked if I liked that she was a slut. It was so fucking hot. I grabbed her by the hair and pulled her up (she told me hair pulling and rough sex was her jam) she climbed on top of me and started riding me on the couch. I was sucking her perky tits and squeezing her ass while she screamed and rode me hard. We switched to doggy after a little bit. As I was fucking her from behind, and she was screaming, Andrew came out of his room, walked right up to Kim and stuck his dick In her mouth. I guess he couldn’t resist getting horny hearing a sex goddess like Kim screaming while getting fucked. I was fucking her from behind with one hand on Kim’s tit, Andrew was getting his dick sucked with a hand on the other. It was pretty wild.
Kim moaned “think you’d both fit In my pussy?” Both Andrew and I stayed silent. Kim stood up and said “if you try to both fit in my pussy at the same time I will forever do whatever you want me to do, whenever, now one of you lies on the ground, I’ll ride you, and the other; go from behind and stick your cock in too.” We were drunk and comfortable enough to comply.
I lied down, Kim hopped on, stuck my cock in her bare pussy, and Andrew went from behind and fit in too. It was crazy tight. Both Andrew and I were in Kim’s pussy and she was screaming at the top of her lungs. “I’ve always wanted two cocks in my pussy!” She started rocking back and forth and then Andrew just started pounding her again. Her facial expression was in one word; ecstasy. I started sucking her tits and she started screaming even louder “Treat me like your little fuck toy!” She started to erupt with wetness. It was like a warm water balloon had bursted inside her, tons of her cum was running down my thighs “I’m cumming!” She screamed. Then I felt it coming on. I had one of my most powerful orgasms ever. I pulled out and maneuvered away as Andrew kept fucking her from behind. I just watched in awe as this gorgeous (literally a 10/10) girl’s tits clapped together as she was getting fcuked from behind. Finally, Andrew pulled out and came on her ass.
“Well that was a fun activity!” Kim said, and we all laughed. We got dressed and decided to call it a night. We left Andrew’s place (who was in a way better mood than before I may add) and Kim and I went back to my airbnb where we cuddled, fucked, and chatted for the rest of the night.
It was a really great experience and Kim and I kept in touch for a while. She ended up getting into a pretty serious relationship with that guy she was with at the dive bar with; which I found pretty hilarious. Neither She nor I ever followed up with Andrew, but I assume this made the break-up a little easier (if at least for that night). It was definitely the experience I didn’t know I was looking for.
Source: reddit.com/r/gonewildstories/comments/o9a2j3/a_threeway_with_two_strangers_while_on_vacation