I tend to be very long winded, so fair warning at the start. As we started our sexual exploration, we weren’t really sure where to start looking for other like minded couples. The obvious answer was posting an ad in the Casual Encounters section on Craigs List. We tried a handful of times but always received very curt one liners or gratuitous dick pics. Even from the beginning, we were looking for other couples that we were compatible with on a personality level before even thinking about jumping into the bedroom.
Anyways, several summers ago, we put an ad up on Craigs List looking for another couple to grab a drink with on a random Friday night. We received an actual thoughtful reply from another couple wondering if we might be interested in getting drinks later that night. After a handful of email exchanges, we decided to meet them at a local bar around 9pm.
My girlfriend, Olivia, and I got there first and ordered a drink and staked out some seating for the four of us. As a refresher, Olivia is about 5’2″ and 105 lbs. She’s very athletic and fit with a toned body. As I’ve mentioned before, she has very perky 32B cups with nipples that never seem to stay soft. I’m just your average fit, athletic guy and together we’re just another unassuming, average attractive couple, next door types if you will.
We were texting back and forth with the other couple, Sarah and Ian, and ordered them a drink while we waited for them to show up. We honestly didn’t know too much about them aside from the fact that they were an educated, working professional couple like us. We only had a grainy black and white photo of them, so we weren’t really even sure what to expect when they showed up.
Fortunately, they were easy on the eyes. Sarah was a college hockey player and in grad school at the moment. She was about 5’8″ and 125 lbs, thick in a good way with short brown hair and maybe small 34C cups. Ian was about 6’0″ and your average ex-military guy, short hair and very stocky build.
We hit it off very quickly after the first round of drinks. I was chatting with Ian and Olivia had hit it off with Sarah. In case you readers are every interested in meeting up with another couple, having separate conversations with almost random strangers is one key indicator that things are going well.
Things quickly progressed and we decided to head back to their place. We were sitting in their kitchen around an island, where Olivia and I were on one side, and Sarah and Ian were on the other. During our first round of drinks at their place, Sarah quickly became very friendly and we started playing footsies. Underneath the table, I was massaging her foot a bit and at this point, I knew things were a go. Olivia looked over and saw what was going on and gave me a very sly smile.
Ian orchestrated the next set of events and the girls soon started getting topless and making out with each other. I clearly remember Ian staring at Olivia’s breasts and commenting about her hard her nipples had become. After some kissing and wandering hands, we decided to move things to the bedroom.
Ian and I just stood back as the two girls continued to kiss and start to undress each other further on the bed. The two of them shimmied their way out of their jeans. Olivia was wearing a lacey black thong and Sarah had on a purple g-string with a pink bow on the front. From all of the hockey and skating, Sarah’s ass swallowed the small thong and right away I was hard and amazed at what was happening in front of my eyes.
The two girls were now laying on the bed kissing each other, intertwining their arms their hands were slowly wandering and doing some very heavy petting. After watching them a bit, I decided to join on the bed and started caressing Olivia’s ass and started to move my hands down to her pussy. I could feel her thong a bit damp and slid it down a off her body. She was completely shaved down below and I rubbed my fingers up and down her slit a little bit while kissing her nipples.
At things point, Ian came and joined us as well and started to kiss Olivia while now I was focusing all my attention on Sarah. I kissed Sarah for the first time and there’s always something sharp and electric about kissing someone new, learning out how they use their tongue and finding the right cadence. After some gentle play, I spread her pussy lips apart and slid a finger deep inside. I eased in and began finger fucking her and using my thumb on her clit to massage it. Her moans became loud and audible and after a couple of minutes of teasing and playing, she yells out that she feel like she’s about to squirt. This for me, is a big turn-on and now I continue to finger her harder and try to get deeper inside to touch her g-spot and soon Sarah had a great first orgasm of the evening.
Shortly after, Olivia joined the two of us on the bed. Olivia has always had a fascination with being with another woman and this was her first time experiencing this. Not skipping a beat, she went straight down on Sarah and started licking her pussy. Sarah seemed to be enjoying it and moaning and I moved further up, now rock hard and standing full attention. Sarah grabbed my cock and began to stroke me. I moved my body further and positioned myself right by Sarah’s face and she obliged by taking the tip of my cock into her mouth. She used her tongue to lick the head and I could feel her moans vibrated along the shaft as I watched Olivia going down on another woman for the first time.
Throughout all of this, I clearly remember Sarah yelling, “You’re such a dirty girl.” directly entirely at Olivia, and commanding her to keep licking her pussy. Ian at this point is kind of MIA, but I’m not complaining one bit as I have the attention of two beautiful woman to myself. As Sarah still continues to suck and stroke me, Ian at this point finally decides to join us.
He hadn’t really been participating until now, but pulls out a handful of sexy toys and lays them all out on the bed. He pulls out this long 18″ double ended dildo, gets behind Olivia, and slowly starts to slide it in her. Olivia moans slightly as the toy starts to glisten as it goes in and out of her. I reach back and help spread Olivia’s ass and watch the toy go deeper and deeper inside her. This was quite the eyeful for me, watching my beautiful girlfriend get fucked with this toy while she continues to lick Sarah. Ian again disappears at this point and I take control of the dildo, pull it out and then start to make my way behind my girlfriend.
As I’m positioned behind her, I start to kiss her ass and play with her breasts as she’s still going down on Sarah. I think it’s time for me to have some real fun so I lift up Olivia’s hip and gently place the head of my cock at the entrance of her pussy. I slowly enter her and she is dripping wet. I look down in front of me, see my girlfriend’s beautiful ass and see her head buried in-between another woman’s legs and Sarah reaching down and playing with Olivia’s nipples. With each thrust into Olivia, I could hear her start to moan and the whole scene of the night is finally building up in me and I quickly feel myself about to cum. After a couple more thrusts, I finally cum inside Olivia and that kind of ends everything as I collapse next to the two women and we just giggle and laugh about everything.
Olivia jumps to the bathroom to go cleanup and Sarah goes to check on Ian and see how he’s doing. Ian at this point is clearly a drunk wreck and had been popping some pills all night. He keeps on talking about his whiskey dick and then starts to yell at me and Olivia that we need to get out. Sarah is doing the best she can to keep everything in control, but at this point, we toss all of our clothes on real quick, give Sarah a quick kiss good-bye and leave their apartment right away.
We haven’t met up with Sarah and Ian again and don’t plan to. But this was our first real experience with another couple and the start of many more sexual escapades for me and Olivia.
Source: reddit.com/r/gonewildstories/comments/5e1k8a/mostly_mff_craigslist_encounters_of_the_strangest
Hot… And awkward AF!
Ian had performance anxiety lucky you got two beautiful women