Wingman [F]ails, but it worked out well for [M]e!

So the end of Uni rolls around and I take a trip to Thailand, as everyone seemed to do at the time. I was supposed to go with a friend, but he bailed last minute for personal reasons so I booked myself on to a group tour, save just bumbling around on my own. The tour takes in all the highlights in a fortnight and it turns out was pretty much just for Uni students and grads, everyone being the same age bracket.

On my trip there’s 8 of us, I’m ‘paired’ with Mark and to share hotel rooms and there’s a health 4-4 male to female ratio. Two of the girls, Haley and Emma are old friends, As are Jo and Simeira, The other two guys, Jake and Liam are good laugh and again knew each other from home. We all got on great, the drinks flowed each night and we all chose to travel together as a group in days off from the trip, sight seeing etc. Mark hits it off with Haley early doors and they’re like rampant rabbits the whole trip.

I’ve got my eyes on Jo, but she’s quite reserved and never leaves the side of Simeira. We flirt and chat a little and it turns out her boyfriend dumped her a couple of days before the trip, so her confidence is shot and Simeira is not going to let anyone get too close whilst she’s still hurting. Jo is a curvy girl, lovely ass and big boobs but a tiny waistline. Startling blue eyes against pale skin and a smile that lights up a room, much like Julia Roberts.

The last week comes around and after 4 weeks, we all know each other pretty well and we head out for a few drinks. The girls stick with each other as do the guys. Mark complains his dick is sore, Haley has spent the entire day riding him. Out hearts bleed for him. Apparently it’s quite obvious I’ve got a thing for Jo and the conversation soon moves in that direction. Liam reckons Simeira has one eye on him and offers to keep her “busy” whist I make a move on Jo. Great, now is my chance. Sure enough, Liam pulls Simeira for a drink and they get chatting and flirty. The other girls keep chatting for a while and eventually, I see my opening as the other two head to the loos.

Jo Looks stunning tonight. Keen not to upset the locals, she’s covered when we leave the hostel. But her jeans are those that fit perfectly over her ass. The shaul has been removed to reveal a black corset that’s pushed her boobs up, but not over the top. I buy her a drink and we head out on to the beach in front of the bar, and take a seat on a table out there. The conversation flows and we laugh, flirt and finally, I lean in for a kiss when the moment seems right. She tastes of the coconut cocktail she’s drinking and wow, those lips kiss well. Her tongue stays back at first but as we kiss more, she relaxes in to me, straddles me clearly enjoys the moment as much as I do. “Someone’s happy” she can feel my cock erect through my shorts and gently moves over me, grinding a little, that smile across her face. I ask if she wants to head back to the hostel, her first thought being of Simeira but she sees she’s flirting and happily chatting with Liam and so we leave.

I’m on strict orders not to touch in public, to ensure the locals are not upset and so the pace back to the hostel is noticeably quicker.

Once there we head straight to her room and kiss, wildly. She jumps up and around me, wrapping her legs and begins devouring me. This is not the same Jo, reserved that if got to know on the trip! Before too long I’m out of my shirt, removing it as we kiss and she holds on. My cock is trying to explode out of my shorts. She drops off me and I remove the shorts and boxers in one motion, I’m now completely naked in front of her and fully erect. Jo grabs my cock and begins giving me a hand job as we kiss further. I’m pushed against the wall as we go, and she plants kisses along my neck, torso and drops to her knees. Without hesitation she starts sucking my cock. I’ve not had sex in the last three weeks and I feel an orgasm quickly build. She’s an expert at this. Magical with her tongue on my head and the speed she moves her head as she takes my whole length is just incredible. She breaks and makes eye contact as she goes and as she looks at me, I feel the orgasm filling. “Im gonna cum if you don’t slow down” I offer and so she stops, releases my cock and stands. “Not yet “ I feel the orgasm ebb away, thank god.

Taking a step back she begins undoing the corset. The first button is snagged and she can’t get it. Realising I need more time to gather myself I stop her, placing my hands on her breasts and kiss her more. My hands head down and unbutton her jeans. I slide them over her ass and down her thighs. No pants. We giggle at this as I push her on to the bed and remove them completely. Completely shaved, in nothing more than the corset. “Did I mention I used to be a gymnast?” She spreads her legs, achingly wide, almost to the full splits. If that isn’t an invitation I don’t know what is. I drop to my knees and devour her in a frenzy. I don’t come up for air, I’m licking, sucking and slurping as fast as I can as she groans and writhes over me. Her legs close around my shoulders and she pushed me in to her, grinding on to my tongue. Before too long everything about her tightens just before she explodes with an orgasm and deep groan.

She lays back breathing hard. “Get me out of this thing” she motions towards the corset. I start the buttons at the bottom, and quickly release them all. The top one is still snagged. “Rip it off” I’m instructed and so I do. She takes two deep breaths, her breasts pushed forward and her rib cage exposed. Her stomach stays as tiny as it has always appeared. Her breasts are full, and her nipples are some of the most erect I’ve ever seen. I take them in my mouth in turn and swirl them, nibbling too. Jo is sensitive and reacts as expected, but I want her more than ever now. I reach for my shorts and retrieve a condom, slipping it on with ease. I lean over her and kiss, deep and hard. She manoeuvres my cock to her pussy and slides me in. God that feels good, we both groan. I begin thrusting gently, rhythmic and her movements match mine.

We both stop as we hear a key in the door lock. It’s Simeira, she’s back. Liam clearly didn’t have any game. I’m over Jo, deep inside her as we look back. Her arms around my neck, my ass pointing straight at Simeira. She takes one look at us and rolls her eyes. “Ok, so got her. Now I’m tired, and slightly turned on, so either you’re done, or I’m joining in”. I look at her, she’s not joking. I look at Jo, she smiles at me, “why not?” “Really?” “Sure, if you want to. We ARE NOT done, so you don’t have much choice” I smile and Jo shouts across to Simeira. “Join us” “Great, I’m really freaking horny now and I want you to do that thing you do with your tongue” I look between the girls as it dawns on me, they’ve been fucking. They both laugh as it becomes obvious I’m catching up.

Simeira takes off her clothes, and wow, great body. Her Asian roots mean she’s a lovely caramel tone to her skin and her perky little tits are finished with dark nipples. She too is shaved.

I pull out of Jo, stand and kiss Simeira, she’s a coconut cocktail drinker too. “ hey, back to work” Jo instructs and points to her pussy. I turn, and pull her down the bed so I can take her standing. Simeira places a hand on Jos breast and leans in for a kiss. They kiss for a while as I re-enter Jo, I thrust gently, enjoying the show. “69” jo says and Simeira hops on over her, sitting on her face. Simeira is not mere inches from my cock as I’m thrusting. “Can we lose the condom Jo?” She asks. “Sure, I hate those things” Simeira pushes me out of Jo, takes off the condom and then pulls me in, swallowing me hole. Jo does that thing with her tongue and Simeira groans uncontrollably, forgetting me. I look down and remember I don’t need to wait for her to suck, instead thrusting back in to Jo, she groans now, happy the condom is gone, clearly. Jo bends in such a way to allow my cock, and Simeira’s tongue access at the same time. I thrust as she licks. This is all too much and before too long, I declare I’m gonna come. Jo shouts up, swallow him Simeira. She opens her mouth and just in the nick of time, I pull out and thrust in to her throat, filling her mouth. A little shocked by the volume, she dribbles some out on to Jos pussy. Like a pro, she swallows, and licks it all back up. As she does she feels the orgasm in her and begins licking Jo faster. Simeira explodes in a loud orgasm a few seconds later. As she breathes out she mouths “finger her” to me, “her turn” I slip my fingers inside Jo and she groans. Rubbing her button with my thumb, making the come hither motion with my finger, Jo too explodes a few moments later.

All now spent, the girls lie side by side and make room for me between them. I drop in and we kiss some more. The sex continued throughout the night and I was well and truly fucked by the morning.

At breakfast, Liam apologised profusely for not keeping Simeira entertained. I game them the basics of what had happened and the apologies soon stopped! Simeira did actually fancy Liam and they hooked up a couple of days later. I became like Mark for the rest of the trip, complaining my dick was sore, Jo never put me down….!

Source: reddit.com/r/gonewildstories/comments/hugyj9/wingman_fails_but_it_worked_out_well_for_me

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