The Chaperone (True Story)

So I have this friend.

We’ll call her Mia.

Admittedly, when we first met I made a move on her and got shot down!

I had been honest from the start about me being in an open relationship with my long term partner, Bunny. Mia simply wasn’t comfortable with the idea of playing with a guy who was in any kind of relationship. So I told her I respected that and was happy to just be her friend.

So that’s what we became, good friends chatting all the time, shit talking over drinks and being a dance teacher I would teach her dancing and we would go to dance events together.

Eventually Mia got more and more curious about my Open/Swingers lifestyle and started asking all kinds of questions about it. She told me she had another friend (We’ll call Kat) who really wanted to check out a Swing Club for the first time… Next thing I knew I had made plans with the two women to be their Platonic Chaperone at a Swingers Event!

I told my partner who laughed and said only I could get myself into such a situation and to go have fun.

Honestly it was a weird feeling, I was both excited but also a little wistful… I had no intention of sleeping with either of these beautiful women at the party as I had sworn to be there as their friend and guide and I fully intended to uphold that.

The night arrived, I swung by in an Uber to pick up Mia and Kat.

Mia is standing there her hourglass figure on full display in a long tightly fitting satin gown with a long split from the right hip down showing her slender legs and emphasing her hips and ass… her long dark hair loosely tumbling along the side of her face and her brown eyes sparkling.

Kat is very petite in a tight, short black dress that just covers her upper thighs, her blonde hair is tied up into a bun leaving her piercing blue eyes unobstructed.

The hop in the car and we continue on to the party. Once there I gave them a tour of the club showing them everything that is on offer and explain the social cues and what to expect. We then hit the bar to grab a drink and started to mingle.

They enjoyed talking to people and finding out more about the lifestyle.

Mia was very nervous and kept taking me back to the bar for more drinks.

Kat however had became fascinated by the Kink room and asked if she could try out using the whips on me. While being on the recieving end of a whip isn’t really my thing, I obliged and we had some innocent fun with her trying the whips out for the first time. Mia stayed upstairs to continue mingling.

Some time later Mia came back down, Kat and I had finished playing with the whips and so Mia dragged me up to the bar again where complained that there everyone there was in relationships and the only hot single guy was too busy talking to others.

I had warned her that this would likely be the case as most people come in a pair, but she was still a little disappointed.

Now a few drinks in she turns to me and says “I want to do something crazy. But I don’t want you partner to hate me.”

I assured her that she was well aware of where I was and what I was up to and there was no issues, but I valued her friendship first so I wouldn’t do anything that she wasn’t comfortable with or that would change our friendship.

“Ok…” she whispers, at this point she is looking deep into my eyes resting her hand on my hip while swirling a glass of Whisky in the other.

Suddenly she puts down the glass grabs my hand and leads me upstairs where she points at the Sex Swing “I want to try that! Will you help me?”

Of course I say yes… I lift her up and place her into the swing I grasp the ends of her long dress and slowly lift it up to sit just above her hips so that I could lift her legs up onto either side of the chains… her dressed lifted high and her legs spread wide her black lace panties were on full display, thenlace pattern was very loose and I could clearly see her perfectly inviting lower lips and how wet she was… I started to stroke her legs softly running up her inner thighs when I got to her panties she started to quiver I started to rub her pussy through her underwear and I could feel how hot and wet it was. As I continues she pulled her panties to the side so I slid a finger inside her and then two… she was squirming and moaning on the swing after a few minutes she started to squirt all over the place. She got embarrassed and apologised saying she forgot to want me that she was a big squirter. I just smiled at her, winked and then got down on my knees and started to eat her out from the swing until she squirted again in my mouth. She’s now quivering I stood back up and she wrapped her legs around the small of back and pulled me in closer pressing my now hard cock still in my underwear up against her soaking wet pussy.

She sat up in the swing and started to kiss me while I grinded up on her, I felt her juices soaking through my underwear and I could feel her warmth against my cock. Just as our excitement began to reach a fever pitch Kat walked in… “I got us all a private room why don’t we move there?”

The spell was broken and the moment gone, Mia suddenly flushed and embarrassment took over. “Ok I’ll go find another guy to join us wait for me in the room!”

So Kat and I took the room, some time passed and no sign of Mia, Kat said she’d hold the room while I find Mia.

Mia was nowhere to be found but another couple was keen to join us so they came back with me to the room they were a young Filipino couple he was tall and fit and she was a tiny petite little thing with huge breasts. Kat decided she just wanted to watch from the corner. And the young man also wanted to see me take his girlfriend while giving instructions.

She was a firecracker! We started with some foreplay fingering her until she came before I put on a condom as she was begging to be fucked while panting she breathes to me “please with my pussy but don’t you dare finish before you destroy my ass too…”

Yes ma’am! Her pussy was dripping wet and super hot after a time I flipped her over to doggy positing on the end of the bed changed condoms and then pushed myself slowly deep into her tight ass she gasped and moaned… her boyfriend calling out “oooh your in trouble now!” He slapped her ass once kissed her and then decided to give us some time alone. Kat meanwhile was still watching from the corner.

After a while of good hard fucking we both lay there panting she gave me a deep passionate kiss, thanked me and left to find her boyfriend.

Kat was told me she loved the show and said it was so interesting to watch… at this point we realised we hadn’t seen Mia in a long time so we went to find her.

We finally tracked her down, she had gone off to play with the hot guy she had mentioned earlier. But she was disappointed “he was such a let down” she moaned “he was so selfish, he barely touched me and then he just shoved his dick in mouth and finished…”

I lamented that it was a shame that she’d had such an experience, but Kat just laughed “Well you should have come to the room with us! You really missed out not getting to see Jay in action!” I awkwardly laughed and shrugged.

At this point the party was finished and it was time to leave. We were all agreed that we weren’t ready to go home just yet so instead we got an Uber back to Mia’s place to have a few more drinks and debrief on the night.

While we are walking up the stairs to Mia’s appartment Kat whispers to me “Mia really wants to fuck you but she’s too embarrassed to admit it… I’ll get things rolling upstairs”

We all sit on the coach, chatting laughing and drinking after a time Kat just outright asks “why don’t we all just have a threesome right now? We can’t end the night with the Mia’s lame guy”

Mia and I looked at each other and we both said ok.

What transpired next was an amazingly long play session I’ll never forget… the girls both being straight didn’t want to interact with each other, so it was up to me to pleasure them both hours of fingering, licking and sucking…

Kat’s style was a bit more reserved, no kissing allowed and I could tell she was pushing Mia and I together more… but she didn’t hesitate to play, strocking, sucking and enjoying what came her way.

Mia started off shy but as we started kissing more and playing more she squirted another few times, next thing I knew she pushed me back and got on her knees and with me standing at the end of the bed she gave me one of the longest and sloppiest blowjobs I’ve ever had… I was in heaven.

After a time I lay back down between the two girls, Mia and I started pashing again while I went back to to fingering Kat. Meanwhile Kat opened up a condom and started to roll it onto my cock and then started jerking me off for a while, she then pushed Mia and I into a spooning position and whispered in my ear “Fuck her.”

Mia reached down and took hold of my throbbing cock she started grinding her ass up against my hard tip as she rythmically stroked the shaft it. Finally as we are both panting and moaning she pushed her lips hard up against my throbbing tip and and it slid right into her soaking wet pussy… I lost track of time as she grinded up on me rotating her hips sending waves of pleasure down my cock… she squirted again while I was inside her and I felt the hot gush of fluids at which point I came hard, my cock throbbing and pulsating from the intensity…

The three of us then lay there toghether, strocking and fondling and kissing for another few hours until the sun came up…

What started out as a night that I thought was me going as a friend, a platonic Chaperone to ensure these two ladies just had a safe fun experience turned out to be one of the most amazing threesomes I’ve ever experienced.

Sorry for the long read, but thank you for those who made it to the end!

It’s my first story on here so I hope you guys liked it!