u/RosenbeggayoureIN

https://www.reddit.com/r/BiStoriesGoneWild/s/BzsDO7yOPt

https://www.reddit.com/r/BiStoriesGoneWild/s/p6oAk5Hkge

Final follow up to my short lived adventures with Matt and Jane…

Matt, Jane and I met up a couple more times over the following weeks, same kind of set up but Jane definitely got in her dom groove, commanding the both of us as she became more of a director than participant. Telling Matt how to suck me, encouraging him to finger my ass as he expertly throated my cock, and still kind of joining in on the action or pleasuring herself as she watched…it was all very hot and I was getting more comfortable in my sexuality.

It came to a head one weekend, drunk and meeting back at her place as things started out like usual. Jane and I kinda fooling around as Matt got my cock in his mouth as soon as he could. Jane was topless again, her magnificent breasts in my face and mouth as Matt rimmed me.

“Fuck you’ve turned into such a slut” she whispered in my ear

“You love getting that ass played with don’t you?” As I just nod in pleasure as Matt continues to devour my hole. Now moving on to my balls as I feel that familiar finger slide in.

“Mmm good boy, that finger feels so good doesn’t it?” I get out an mmhmm of sorts and she continues

“That ass needs something more doesn’t it?”

Matt takes me all the way down his throat as I moan out, grunting a half hearted yes as he works his finger in and out of my aching hole.

“You want a cock in that ass don’t you?” She says

I don’t really respond at first

“No, you need a cock in your ass, right?” She says now in a more commanding tone. I’m now putty in their hands as i nod my head and Matt slides a 2nd finger in.

“Say it” she says again in her now dom tone

“Yes” I moan out

“No, say it” she commands

“I need a cock in my ass” i get out, not really thinking straight (no pun intended)

“Good boy” she says with smile and as if they coordinated, which looking back they might have, Matt then stands up and drops his shorts, the first time i had even really seen his cock. It was a pretty one, cut and somewhat long, and fortunately not too thick. He’s got a big smile on his face as I soak in his cock.

“Suck it first” I hear as I snap out of my trance

Matt walks up as I sit on the futon, basically already eye level with his cock, as he gets close. I reach out and grab what is the first cock other than mine I had ever touched (but not the last!). I remember most just how soft and warm it was, as i slowly squeezed and inspected it. I pulled the tip to my lips and tried to do my best on how i like my cock sucked.

“Mmm good boy” I hear, my mind more focused on Matt’s sexy cock in my mouth, my tongue swirling around his head.

“Harder” I then hear, as I feel Jane’s hand push on the back of my head. Shoving my Matt’s cock deeper and deeper as I gagged a lot and had to pull off. Jane pushed me back on the futon as i lifted my legs up, giving Matt his prize.

Jane crawled over me, sliding me back a bit as she then reached to grab my ass and spread my cheeks, giving Matt the perfect access. Matt already had a condom on as I feel him press the head against me and push until I feel it pop in as a wave of pain and pleasure flowed over me. Matt continued to push slowly, working his cock deeper into my ass, pausing and pumping gently as he went.

“Mmmm that feels so good doesn’t it” Jane purrs, still laying over me holding my ass as Matt finally bottoms out inside me. Matt pulls his cock back out slowly and slides it right back in, doing it several times before adding more lube and begins to pick up speed. Deep stroking me harder and harder as I start to moan and swear.

“God you take cock so good”, fuck him harder. Fuck that’s so hot.” Jane cheers on. Getting more and more into it, even giving my cock a little kiss as she got her front row seat of Matt destroying my ass. She gets off me and takes off her shorts, quickly rubbing her clit next to me as she reaches over and starts stroking me as my cock starts to somehow get hard. I’m in heaven, feeling Matt slide in and out of my ass as Jane fondles my cock when i look to see Jane leaning over and taking me in her mouth. I moan out as she works my shaft up and down with her lips.

“Up” she commands as Matt pulls out, leaving me desperate to be filled again. She pulls me up and pushes me down on the bed, my legs over the edge still and climbs on top. I’m too cock drunk to even realize I don’t have a condom in on but grabs my cock and lowers herself down and lets out a moan of almost relief. She starts riding me as she looks over her shoulder.

“Get back inside him” Jane commands, as Matt quickly tries to lift my legs back up. It was kind of awkward but somehow we made it work as I feel Matt fill me back up to my delight. Matt and Jane fucked me in rhythm for a bit, me bottoming out in Jane as Matt bottomed out in me, all of us groaning and moaning in pleasure together. Jane starts tonight pick up the pace and grinds down on me hard, trying to be quiet but failing as she cums hard on my cock, which then triggers me as I pump what feels like dozens of ropes deep inside Jane. she climbs off as my load spills out on to my crotch a stomach as Matt quickly pulls my hips to him and slams his cock deep inside. My now soft cock, covered in cum is flopping back and forth in a sticky mess as Matt goes all out. Fucking me hard and fast as I start to get tunnel vision as his balls slap into me harder and harder until finally he buries his cock as deep as it can go, wrapping his arms around me as I feel his cock pulse in my ass, filling up the condom.

We all collapse in a cum covered heap, sweaty and exhausted as I crashed shortly there after. We hooked up a couple more times but it was never as hot as those other times, which are still up there as all time greats. I have a straight and a gay experience that are my other tops so holler if you’re interested!

People seem interested so here ya go for a couple more fun times with Matt and Jane

https://www.reddit.com/r/BiStoriesGoneWild/s/TddXnCfHdX

So I had some conflicting feelings after my first encounter…I wasn’t quite sure I was straight anymore but back then it was definitely not as accepted and as it still kind of is today being bi is still misunderstood so I kinda kept everything to myself but as a young horny guy my mind kept going back to that amazing head from Matt…

A week or so later I run into Jane at a party (hadn’t really reached out to her ie the conflicting feelings) and we chat it up and start talking about what happened. I apologize for not texting but said I had a really good time, just wasn’t sure what it all meant.

“Oh relax, you said you had a fun time so why worry about it??” Jane replied and For some reason that kind of put my mind at ease but it may have also been that she was wearing a low cut shirt that made those sexy tits pop and had the classic whale tale thong sticking out of her low rise jeans. She looked sexy AF and once again was on the prowl as a few different guys came up to her while we were chatting. I got called for beer pong but was def thinking about heading back to Jane’s again that night.

Fortunately that ended up being exactly what happened. I learned later one of the guys made some homophobic comments which pissed her off and happened to see me as she was walking out so she asked if I wanted to smoke and I knew it was on. Same set up as the first time as Jane and I start fooling around but Matt wasn’t there this time. I wasn’t going to ask or anything but just my luck as I have my mouth wrapped around those sexy nipples again but I hear the door unlock as Matt walks in.

“Mmmm what a nice surprise, please don’t let me stop you” Matt states as he just walks right in, clearly drunk.

Jane and I continue as she’s a little more handsy than last time but we’re mainly making out semi-naked, both our bottoms on as I feel a hand tug at my boxers and see Matt, on his knees by the futon. I lift my ass and sit in front of him, still playing with Janes now hard nipples as he pulls my boxers off and goes to work again. He’s so sloppy this time, gagging hard and really working my balls and shaft. Working his tongue up and down my big cock moaning and complimenting it which distracts me a bit from Jane as I watch Matt perform and I look back over and Jane is just staring with a slight smile.

I run with it as I grab matts head and start fucking his face, driving Jane wild.

“Fuck…watch him take that cock with ease”

“Mmm yes fuck that mouth”

“He’s such a good little slut”

Jane is now naked, fingering herself next to me enjoying the show, giving us both encouragement. Matt pulls up for air, spit dripping down his chin and my cock as he dives back down on my balls but keeps going lower, flicking my taint with his tongue more regularly and me being in ecstasy, I shift forward and lift my hips up off the futon as I feel his tongue hit my virgin hole. I moan out as punches it in and out for a few seconds.

“Mmmm someone likes that!” Jane exclaims and all the sudden Jane begins to get dominant. Matt is back to throating me but Jane kisses up my neck and whispers

“You want that tongue back on your asshole don’t you” as I just nod between moans and groans. Matt pulls off and for the first time Jane touches my cock. She grabs it and pulls it toward my stomach and proceeds to force Matt’s head down to my ass. This time he devours my hole, licking, tongue fucking, enjoying his meal as Jane pushes his head up and down on my hole holding my cock up to give him access. I’m going wild, squirming and moaning as Jane gently strokes my big cock with Matt tongue fucking me into bliss.

Matt takes my cock back from Jane and slides me back down my throat as you can tell he is ready to finish me. Jane pulls her tits into my face as I feel my load building when I feel a finger making its way back to my now sloppy wet hole and slide in. I start seeing stars as Matt does not start gently, finger fucking my ass from the start as I feel a second finger pop in. I yelp out but it feels so fucking good and quickly I’m over the tipping point as I let Matt and Jane know I’m about to cum. This time Matt pulls off, two fingers in my ass as he strokes out my load all over his waiting mouth and face as my ass clenches down on his fingers. Jane furiously brings herself to orgasm right after with her own hand as we again all collapse on the futon catching our breath.

We ended up doing this a couple more times in similar variations but there is one more where I finally fuck Jane but Matt also fucks me and is probably one of my hotter experiences.

This was way back when in college so everyone’s at least 18 (20+ years ago)

I had dated girls in high school, played with my ass a bit but never really considered myself not straight until a few months into freshman year… smoking outside as one normally does back then I strike up a convo with a sexy little thing…we will call her Jane. Maybe 5 ft tall, wavy brown hair with nice curves.

Jane and I smoke a little green and end up heading back to her dorm where we start making out etc. she does give me a heads up that her friend may be there but he usually goes to bed early…she tells me he is gay and having problems with his roommate so he stays in her room a lot as she didn’t have a roommate at the time. I don’t care bc I’m hoping to get laid lol.

We come in and he’s in the top bunk sleeping and we start making out on the futon but when I start getting handsy she basically flat out tells me that she will fool around but don’t expect her to reciprocate. I’m thinking fine, she will probably change her mind in the heat of the moment but she’s not budging…I have her top off, sucking on and playing with her sexy tits, kissing the nape of her neck and driving her wild but her hands are moving no where lol.

I ask if I can eat her out and she agrees, but says again she’s basically not going to touch my cock lol. Undeterred I dive in to her full bush pussy, lapping her up, working her clit and sliding a finger in until she cums. A sexy little whimper as she tries to keep it down but you could tell she loved it. I figure she would change her mind but basically just says sorry again as we kinda catch our breath when I hear something from up in the bed:

“Cmon Jane at least suck his cock or something”

It was Matt her friend peeking down from the bunk as Jane then laughs and says something along the lines of “I warned him”

“What a tease” he quips back “not even the tip??”

“Why don’t you come suck it then??” Jane says wryly with a smirk on her face. He laughs “don’t tempt me”

As they both kind of turn to me…now I am still pants on, rock hard and riled up as I laugh too but don’t really respond. There is kind of an awkward silence as Jane then speaks up “I bet he actually would if you want” as I kind of short circuit…unsure of what to do as a “straight” 18 year old. What I came up with was from a recent Chappelle show lol…”hey a mouth is a mouth”

Matt gets a big smile on his face as he climbs down as I kind of freeze, not sure what to do when Jane, fully naked leans over and starts kissing me again. We start making out as my hands get back on those sexy tits as I feel a hand start unbuckling my belt and pulling my jeans down.

“Fuck” is all I hear before I feel that familiar feeling of a warm mouth envelop my cock. Now I’m pretty big (feel free to DM) but really thick so the handful of blowjobs I had gotten in my short life were not the best…until Matt. He worshipped my cock, taking me all the way down right off the bat as I could hear him gag, Gluck and slurp on my cock, all without me ever really looking down as I tried to focus on Jane and her beautiful tits while Matt did his work…

He pulls my cock out of his throat and works my balls, flicking his tongue on my taint just slightly as if he’s testing the waters but then licks back up my shaft as he takes me all the way down again. I’m getting close and let him know with my moans and grunts as he gets the cue and starts throating me without abandon…I have Jane’s tit in my mouth as I feel it coming as I get out a “fuck, fuck” as Matt buries his nose in my pubes as I unload. Shooting rope after rope straight down as Matt pumps my cock with his throat until I finish as he then pulls off squeezing the last bit of cum out with his hands and sucks it off the tip.

We all laugh a bit as I complement his skills as he winks and says “anytime” and climbs back into bed, leaving me panting on the couch next to a sexy woman, drunk, not knowing what the hell just happened but also realizing that was the best head I have ever gotten…

Matt, Jane and I ended up hooking up a few times before they had a falling out if anyone’s interested but it turns out Jane had/has? A kink for this lol

Part 1 https://www.reddit.com/r/gonewildstories/s/mZjsTj7ZuR

part 2 https://www.reddit.com/r/gonewildstories/s/74OPCSj4dd

I’ll try not to bore people with the set up but here is the final part (sorry about not sharing part 1!)

So obviously Wednesday was rough but now knowing I was getting a round 3 with Leila and potentially her roommate (I didn’t even know their name or gender at this point) got me through it. I started planting the seeds during the day, didn’t eat much at dinner and then told my director I was feeling a bit off to build up the charade just in case after dinner plans were being made. Sure enough someone suggested a bar near the restaurant (which I made sure wasn’t around her place) and I bowed out gracefully…

I text Leila “should be done with dinner around 9”

“I’ll buzz you up” she replied. Short answers from her so I wasn’t sure what was in store for me but I’m excited. I pop back to the hotel to shower and prep a bit and sneak off to Leila’s.

I buzz up and walk in to see Leila on the couch ripping a vape pen as I see what I can only assume is her roommate sitting by her. They are clearly trans as well, much taller than Leila, probably 5’8 to 5’10 with brown hair and much smaller, more natural looking breasts… they were more masculine than Leila but still sexy as hell

I smile at Leila and get that sexy smirk back, which makes me think I’m in for something fun…

“So here he is in all his glory! I’m Sierra, Leila told me you guys had quite the fun last night!”

“Most definitely” I laugh “too bad I had to say work all day”

“Oh I think we can make up for that” Leila says… “Sierra here is kind of a size queen and would have a lot of fun with what you’re packing”

My ears perk up “oh really??” As I look over at Sierra as I get a Leila esque smirk back from her.

“Hahah I don’t know about size queen, but I’ve been known to enjoy a big cock” Sierra says. “Sounds like you might too”

I laugh as we kind of awkwardly talk a little before I ask if I can hit her pen. We smoke a little and before long Leila says we will be a lot more comfy in her bed. We stand up but not before I pull Leila in for a deep kiss, caressing her sexy torso and ass until we pull off and I see Sierra close staring at us. I turn and pull her in as well, her lips are soft but her tongue is aggressive as we make out for a bit before I pull off

“Nice to officially meet you” I say with a smile as we head to Leila’s room. Leila sits on the end of the bed as I crawl up on top and start kissing Leila again.

“Be right back” Sierra says “don’t have too much fun”

Leila and I continue to make out like teenagers, just like the night before. I kiss down the nape of her neck again but this time I pull down her shirt to reveal her sexy tits as I take her nipple into my mouth. Sucking and swirling with my tongue, giving her gentle bites here and there, driving her wild. I work my hand down her stomach to her pants and feel her already hard cock straining against the fabric. I slide my hand inside her leggings as I slowly stroke, never letting that nipple out of my mouth.

Now I’ve lost track of Sierra but I’m assuming she’s prepping for me so I continue to worship Leila’s beautiful body and cock. She pulls my pants down and starts to stroke me as I slowly move my kisses down from her beautiful breast to her toned stomach, down to the crease of her hips.

I take her back in my mouth naked on all fours on the bed as I work her in and out of my throat, more gentle than the night before, taking my time and savoring her taste as I hear Leila audibly approve of my work.

“Oh damn” I hear Sierra exclaim and before I can even look back I feel her hands on my ass, groping my cheeks as I get spread and feel a nice warm tongue directly on my hole. I let out an audible groan with Leila’s cock in my mouth as Sierra starts tongue fucking my ass. Working it in and out as they reach under and start stroking me from behind. I’m going crazy, trying to still give Leila’s cock the attention it deserves while shocks of pleasure wave through me from all the sensations going on.

“Such a good boy Leila! Where did you find this guy” Sierra says, now playing with my balls as I feel them spit on my hole and work a finger in. Now I love my ass being played with but I guess I was surprised as I thought I’d be fucking Sierra but I roll with it.

Another finger goes in and then a 3rd which has now officially distracted me off Leila’s cock as I get used to the 3 fingers working in and out of my ass. I moan out as Sierra continues her pace as I catch a glimpse of that sexy smirk from Leila, her cock in my hand as I can now multi task again and take her back in my mouth and then I feel a 4th finger try and make its way in….

“Fuuuuck” I let out, pulling off Leila’s cock again as I turn back to see what she is planning here when my stomach drops… I turn to see Sierra, fully naked with her sexy tiny tits, long torso, and one of the bigger cocks I have seen in real life. She was probably a bit longer than me and almost as thick….

“Oh fuck” I get out “ I don’t think that’s going to fit” but Sierra had different plans. No more niceties, as Sierra pushes my head down back onto Leila’s cock and all i get from her is a “shhhh, good boy”

I feel her fingers pull out, leaving an aching void I need filled but nervous of what is going to happen next. I feel her press the tip against my hole, pressing harder and harder as I try and relax. Leila’s cock is pretty much just sitting in my mouth as I slowly get stretched to the max. The head pops in and I immediately see stars as inch by inch I feel Sierras cock slide in. After what feels like an eternity and plenty of moaning and yelling from me, Sierra was balls deep inside my ass and paused, letting me continue to adjust as Sierra slowly made little pumps into me as our balls bounced together.

“Fuck that’s hot” Leila says which kinda snaps me back as I realize I still have Leila’s cock just in my hand without me moving. I begin to stroke her again as I keep getting used to Sierra’s size. Sierra slowly starts to pull out and slide in, smaller strokes as I moan with Leila’s cock back in my mouth. I’m finally starting to get a rhythm as Sierra picks up speed, letting Sierra fuck me right into Leila’s cock, gagging and moaning as I get destroyed from both ends.

I’m almost in a trance as Sierra starts pounding me, spit dripping out of my mouth down Leila’s balls and legs as I take Leila down my throat as Sierra claps my cheeks, pile driving their cock what seems to be deeper into my ass each time.

Leila starts to squirm “mmm fuck I’m going to cum” as I feel that familiar feeling of her cock tensing and pulsing as she erupts in my mouth, cum spilling out as I try and swallow it all while having my insides rearranged by Sierra. Leila pulls herself up and slaps my ass as Sierra pulls out, leaving me gaping and aching, now desperate to be filled back up. Leila rolls me over and takes my soft cock in her mouth as Sierra reenters my now destroyed hole.

Sierra picks up right where they left off, driving into me as I slowly start to get hard from Leila’s mouth. I feel my load building as I feel every inch slide in and out of my ass, firing all my nerve endings as Leila uses Sierras momentum to take me as deep as she can. Sierra goes into full Jack hammer mode as Leila starts gagging from the deepthroat as I start to grunt again. Leila pulls off and strokes me as I cum so fucking hard, shooting watery ropes up my chest, hitting myself in the chin and lips as Sierra pulls off the condom and follows suit, stroking over me and drops one of the biggest loads I’ve ever seen. I take some in my mouth as I want to taste her but most gets all over my face and lips as I grab their cock and pull it in my mouth. I lay there in a daze covered in two beautiful trans women’s cum and my own as Sierra and Leila bend over me and we share a three way cum kiss, all of us tasting each other.

I was absolutely wrecked and drained so we ended up showering and had a little more foreplay but nothing as hot and exciting as what just happened. I ended up not being able to see it them again that trip (Leila had to work) but funny enough I did get to fuck Sierra as she had a work trip in MKE like 7 months later which was also a great time. Still the biggest cock I have ever taken to this day.

Part 2

Well, Leila wasn’t lying…she was a pro. Two hands on my cock, working it up and down like her job, gagging, spitting, and doing her best to take me all the way down her throat. Pulling out for air as a thick stream of spit dangled between that sexy smirk and the tip of my cock. She slaps my cock into her cheek as she then runs her tongue up and down my shaft, down to my balls as she works her way back up…I was in heaven.

I feel it building but I’m not quite close yet until I see it. Leila’s shorts had come off at some point and that sexy little cock of hers was back to rock hard, sticking straight out with her cute little veins bulging out of it. She is back down on my balls and I pull my legs up slightly and she immediately gets my cue…I feel her sloppy wet tongue work its way down to my tight hole as it circles around all while she continues to pump my now aching cock. She tongue fucks my ass as I moan in pleasure, I’m starting to get close…

Sensing this Leila goes into overdrive, taking me back in her mouth with reckless abandon. Bobbing up and down, gagging and glucking as I feel her spit drip down my cock to my balls. I lean my head back enjoying some of the best head of my life as I feel a finger knocking at my door down below. I rock my hips forward as I feel her finger easily slide inside me, working it in and out in tandem with my cock going in and out of her throat. I’m seeing stars as I start to grunt, Leila picks up the pace as that familiar feeling rushes over and my cock explodes. Leila pulls out for me to see one of the sexiest moments (for now) engrained in my memory as I shoot rope after rope across that sexy grin of hers, unloading across her hair, face and lips. She smiles again as she takes me back in her mouth, squeezing out the last drop as my cock makes a pop sound finally pulling out.

I look down and see Leila on her knees, a cum covered mess stroking her little cock.

“Mmm looks like you’re ready for round 2 already” I get out, exhausted from the best nut of my life.

The smirk comes right back as Leila stands up and bends down to kiss me as I eagerly taste myself all over her lips and tongue.

“I’m going to need more than that mouth this time” she says pulling away from our kiss

I knew I was going to get what I was hoping for, that sexy cock deep inside me. Leila reaches into the end table by the couch and pulls out a condom. I have always wanted to try this and only had one person do it to me, but I grabbed the condom from her and pull her close to me, her standing up and me still sitting on the couch as I take her back in my mouth. Working her cock a bit I open the condom and place it on the tip of her cock, and with my best fuck me eyes I wrap my lips back on her tip and take her all the way down my throat, rolling the condom on as I stare into her eyes.

Leila moans…”fuck you’re such a good little slut aren’t you?”

She steps back and takes charge, lifting my legs up as I slide back and offer up my tight little ass as hers to take. She spits straight into my hole as I feel her fingers make their way back inside me. One at first, then 2, slowly fucking me as I moan out. My cock is already getting hard again as I feel her cock press against me, gently pressing harder and harder until I feel that welcome pop of her cock making its way inside me. We both let out a moan as she immediately starts to pump.

At first she was gentle, slow long strokes as I got used to her cock inside me, slowly burying herself all the way inside and slowly pulling alll the way out, then popping right back in. I grab my now hard cock as I start to stroke while Leila builds up a rhythm.

“Fuck you take cock so well baby” Leila whispers under her breath as she picks up speed. Soon she is going full bore, fucking my ass hard as her sexy little balls slap into mine. Leila is clearly a seasoned top, power stroking into my ass as beads of precum start leaking out of my cock.

Leila hits me deep as i let out a loud “fuck!” Which just makes her go even harder. At this point I can’t even focus, my cock back to soft as Leila continues to jack hammer my ass. Soon her moans and grunts get louder and she pulls out of my ass, rips off the condom and jumps over me as I watch her cock erupt for the 2nd time, spraying cum across my sweaty chest as she collapses over me, both of us covered in each others cum and sweat.

We hop in the shower to rinse off and I check the clock… fuck 230am…

We trade numbers and say our goodbyes as my post fuck high wears off and the gravity of tomorrow begins to set in as I hustle back to the hotel to try and get a couple hours of sleep. The next day is rough but I survive, zoning out hearing about everyone’s backgrounds, going on autopilot through the lunches etc when I get a text that afternoon…

“How ya holding up?”

It was Leila, I quickly text back and we go back and forth on how much fun we had, how tired I am etc when she sends this:

“So i know you probably have a bunch of stuff tonight or whatever, but i told my roommate about you and they want to meet this mysterious man slut from Wisconsin”

“Just meet?” I quickly reply

“lol” was all I got back

“Let me see what I can do” I reply as I start planning out my future excuses for round 3 that night.

Let me know if yall want to hear the grand finale

This was a couple years ago, but still always fresh in my mind. There’s probably a few more parts worth if people are interested!

It was going to be a long week…I had meetings in Boston all day Wednesday, Thursday, and Friday as we were opening a new office and they needed some boots on the ground to get the new team up to speed. Since most of the team was new, this also meant LOTS of networking. Normally I’m a social little butterfly and fine with all that but this was gonna be a long one…breakfast, lunch and dinner with meetings in between each day, happy hours, dinners with senior leaders (which almost always led to a night cap of some sort) and then do it all over again at 8am the next day. Of course since they’re starting bright and early that meant a Tuesday night flight so I check in to my hotel and Google some local bars to see what they have on tap.

I end up at a small little divey bar with a good selection of local stuff not too far away and belly up to the bar with maybe 7-10 other people there in total. Around the corner comes the bartender and immediately she checks all my boxes…she’s petite, maybe 5’3” at best, wearing a black tank top and shorts showing off her tatted up arms and legs with dark black hair pulled up in a simple ponytail. While not revealing cleavage wise, the tank top was definitely accentuating her perky tits which tbh looked a little fake but we’re definitely not too big or anything. For me, I’m kinda a big Midwest dude lol, 6’2” brown hair and eyes and rocking a solid dad bod. I also happen to be pretty blessed below the waist… (I know I know) a little over 7 long but almost 6 thick and cut.

Anywho so I’m overall playing it cool, not laying it on thick by any means but chatting with her frequently over the next couple hours…work, what to do in Boston (if I could swing any down time) where she was from (somewhere in Pennsylvania) where I’m from (wisco) etc. let’s call her Leila. I wasn’t really trying to pick her up or anything despite her sexy self but mostly bc she was the bartender and probably just being nice and I had a brutal schedule ahead. It’s getting close to close so I asked if she had any good food recommendations on a Tuesday at this hour and she gave me a couple. I settled up and gave her a nice tip and said my goodbyes.

I waffle between a few places and finally end up at Bovas (good stuff!) and eat my pizza right outside, smoking my vape, drinking some water and ready to hit the hay after I finish when I hear someone behind me…

“Pretty good right?”
It was Leila, walking home from work but in a more cheerful mood than she was behind the bar.

We chit chat a bit more about the pizza and we kinda end up walking back home the same way. We’re both hitting our nicotine vapes but I pull out my penjamin and offer her a hit. We each take one or two when I’m realizing that my cart is out and it dawns on me that I didn’t bring another…how I’m going to get to a dispo with my schedule?? Fuck

“Shit I’m out! This week is going to suck ass so much” I say as we chat about my conundrum but then I hear music to my ears…

“I’ve actually got a preroll back at my apartment, wanna join?” Leila asks

Don’t have to ask me twice! Turns out she’s just like 3 blocks from my hotel so we head up to her place and I’m of course much more flirty now, going through all the possibilities of what might happen in my head. We head out to her balcony and spark up, chatting about life, dating, etc. she doesn’t have chairs or anything so we’re just kind of standing next to each other as we finish the joint, buzzing from my few beers and the joint when I decide to go for it and just straight asked her:

“Can I kiss you?”

Leila gives me a cute little smirk and she simply nods as our lips embrace. Passionate but not all over each other….yet. I grab her sides above her hip and pull her in close as we end the kiss and look at each other…

“Mmm that was nice” I say, both of us grinning like teenagers “We should probably do that again”

And just like that it was on, we start making out heavily, tongues dancing as my hands slide up and down her sexy torso, grabbing her tight little ass through her shorts right there on the balcony. I move my kisses down the nape of her neck as she moans out and starts rubbing my now semi hard cock over my jeans. I move my hands up, palming her (now confirmed fake) tits as I roll her nipple gently between my fingers giving them a pinch.

She lets out an “ohhh fuck” before she backs away from me a bit. Confused I look back at her and go for more but she stops me…

Now I’ll preface that this woman is beautiful and sexy and very passable but I had an idea she might be trans but I of course never want to make assumptions.

“Im sorry it didn’t come out earlier but just so you know, I’m trans and pre-op” Leila gets out finally, looking nervous.

“Show me yours and I’ll show you mine?” I say back with a grin, as little did Leila know I just so happen to be pan and a complete cock slut lol.

Leila laughs, looking reassured as we immediately pick back up where we left off on the balcony. I move my lips down her ear and neck, hearing her moans of pleasure tell me I’m on the right path. I kiss down her shoulders and chest, hovering my lips over her nipples through her shirt as I pinch the other which seems to be driving her wild but here is where I decide to get bold…

Due to our height difference I’m already basically crouching down with my mouth over her clothed tits so I just say fuck it and drop to my knees on her balcony pulling the front of her shorts down to reveal a sexy, perfect little half hard 4-5 inch cock.

Leila gasps “what are you doi…….Fuuuuuck” she trails off mid sentence as I take her whole cock into my mouth, instantly feeling it get harder and harder as I swirl my tongue around it. I go to work, worshipping her sexy little cock with all my might, burying my nose in her freshly shaved pubic area as I gag a little, pulling off as spit drips down my chin. I look up and see Leila admiring my work with that same sexy smirk on her face as she grabs the back of my head and forces me back on to her now rock hard cock.

“Good boy”

I’m all in as Leila gets more and more aggressive, now with a solid rhythm as she fucked my face right there on her balcony, my head knocking into her railing, clanging and glucking noises echoing in the night. Her cock slides back and forth down my tongue, hitting the back of my throat as she pumps harder and harder each time. I finally tap a little for some air and a break as she pulls out of my desperate mouth, her gorgeous cock glistening in the moon light dripping with my spit and her precum…

“Fuck you’re going to make me cum” Leila panted.

And those words were all I needed as I dove right back on her gorgeous little cock, this time using my hands as I worked her shaft and balls as I bobbed up and down on her cock like my life depended on it. Within just a couple minutes of moaning and “oh fucks” I feel her cock start to tense and pulse as Leila lets out a whimper, barely getting out “ughhhh I’m cumming….”

I take her all the way to the back of my throat as I get my reward, feeling her cock explode directly down my throat as I do small pumps as deep as I can take her, milking out every last drop as I slowly pull her out of my mouth once the spurts subside, savoring the taste of her sweet cum, sweat, and my saliva all mixed together. I take her back in my mouth for a final taste as she starts pulling away her now hyper sensitive cock that just unloaded in my mouth.

“Where the fuck did you come from?” Leila laughs. “Now get the fuck inside before we actually get caught!”

I smile and we jump back inside, Leila pulling me in for a deep kiss, tasting herself on my tongue as her hands quickly reach for my rock hard cock straining against my jeans.

“Let me return the favor for you baby” leila whispers to me as I grab her ass and start reaching for her tight little hole but she pushes me down on her couch before I get there.

“Sorry baby, I don’t bottom but I’ve been told I give excellent head” she smirks again as she pulls her tank top over her head , unhooks her bra and drops to her knees, pulling my thick cock out as her smirk turns to a big smile with her perky tits on display.

“Haha fuck, yeah that is definitely going no where near my ass” as she slowly takes the tip of my cock into her mouth, almost like she’s inspecting it first.

I laugh “oh no worries, I’m pretty vers and usually like to bottom anyway” which pretty much stopped her in her tracks, my cock still in her mouth as she looks up with the most curious face.

“Haha well fuck, you’re just full of surprises aren’t you” Leila gets out before she takes me in her mouth again but this time much deeper, gagging as she almost gets me all the way down, making me squirm in pleasure as she does her best to take me all in.

Getting pretty long so happy to do the other parts here soon if people are interested, as it ended up being a very fun and very long week indeed.

Jorge_gon26