Unintentional meeting with a shemale

So I figure this might be an interesting true story to tell here. Ive been a guest on these forums for a while, mostly out of curiosity Ive never been into ladyboys/shemale, but i do find them interesting to look at, especially that ones that are very convinvingly female looking but then are packing decent sized dick down there, its such a odd combination that it does definately play on my mind.

Anyway, I have a girlfriend from Thailand and we have been seeing each other for a while. Shes great and very open minded and I really like her. Shes a cis woman and a very beautiful one at that. Now she's not what i want to talk about, what i want to talk about is the day i met some people she used to work with, her friends.
So one night i get a call to come meet her and her friends (all Thai) for drinks at some fancy expensive tapas joint, i had finished work already so im like "sure".

I get there and they are already all tipsy so i sit down with my GF and just listen in. Theres like 4 other girls there, some are really beautiful and amazing bodies and they are dressed really nice, but one of them kinda looks slightly odd facially, but has a banging body, super toned legs, abs an arms plus nice big D size silicone tits and a perfect tan, all easily noticeable since shes wearing like this faux black leather sling like boob top and shiny body hugging leggings.
Now just a little about me which might help the story, i used to do amateur bodybuilding (natural no roids), im 5'7, stocky and im in pretty good shape still even though i dont do competition training anymore. Ive always been attracted to slightly muscular woman, ive dated a few fitness "influencers" in the past, even now my thai GF is also quite well built but i wouldnt call her ripped, maybe slightly athletic with decent muscle on her arms and legs.

So this fit girl starts talking to me, shes a bit tipsy but not drunk, shes like holding and gripping my biceps a lot, feeling my abs through my shirt and complementing me. My GF isnt really bothered too much by stuff like this, we have been to strip clubs together, naked with other girls in hot tubs, and shes cool with it as long as it doesnt go too far, we dont have an open relationship or anything but shes not overly protective or jealous as long as we are together.
Anyway later in the night my GF and her friends are now quite drunk, im not since i arrived later than them. They are constantly going either to the toilets together or outside to chat leaving me alone with the fit girl quite often.
At this point im fairly certain shes a ladyboy, the voice is not very femine but gravely and the hands are kinda too veiny for a biological woman but again maybe not unusual for fitness woman. So theres a small chance shes a woman but im leaning towards not.

She was asking me stuff about how i train, what exercises I do and is continously complementing me (i know somethings up because i wasnt really in the best shape ever here).
So i return the favour and tell her she has great abs and asked what exercises she does, to which she laughs and says "You need to fuck A LOT to get abs like this". She then put her hand on my crotch and asked "you like to fuck ? How bigs your cock ?"
Now i wasnt really interested in her at all sexually, i was just having some conversation and i did legitamitely respect the effort she put in to look as good as she did, but i wanted to put an end to the now obvious flirting so i bluntly tell her, "Look you know I have a girl lets not go down this road"

This lit a fuse in her and she started going off angrily, "Are you brushing me off cause im a shemale ?" and "I bet if i was some pretty white girl you would be into me" blah blah.
I didnt even ask he if she was trans or not but she was irate about it.
Now i just sat back kept quiet sipping my drink and kept waiting for the rest to return so i could pay the bill and leave but this woman just wouldnt stop with the tantrum.
Eventually to try get a reaction out of me she says something like "I bet you have a small dick, thats why you are afraid of me because i have a bigger dick than you, youre not a REAL man, because real men can handle me".

Im usually good at ignoring shit like this, ive had my fair share of crazy ex's but that statement just annoyed me deeply. While i was thiking of how to react to the statement, my GF and her friends arrive, so i decide to call the waiter, and pay the entire bill so i can take my GF and leave.

Next I drop my boozed up GF at her place then go home, and when im home i cant sleep because i was so angry about what just happened. So i get my phone check my social media and find her and look at and read her profile etc, nothing too crazy other than shes obviously very slutty. Shes showing as online so I let my ego get the better of me and I message her, and i say "Yeah, im pretty sure my cock is bigger than yours..."
FYI my penis is a decent size, just under 7" normally and a full 7 if very hard (not often) and about 5.5" in girth. I often get told by girls ive been with its a good size. Not massive but adequate.
She messages me back predictably "prove it..."

Now im no stranger to sending dick pics (in my youth i did a lot lol), but now im older and I also dont trust this chick with the picture since she could use it to blackmail me or something.
So i tell her that she made the claim, so she should prove it and then ill do the same, she refuses.
So i leave it at that and get back to bed, but a while later another message comes through and shes tells me "to come meet her tomorrow" and that she'll "SHOW me on one condition", if she is bigger than me i need to "suck her bigger cock". I think she was trying to get me to chicken out but i was confident she couldnt be that big, especially being shorter than me and probably on female hormones, so i call her bluff and say sure "but if im bigger you suck my cock and i want to take a photo of you sucking it". Unexpectedly she agrees.

In the morning she sends me the address and room number of the hotel she was staying in (she is from out of town and here on holiday). I thought hard about going or not, but i was feeling so amped up from the challenge, i felt like my manhood was on the line and i was really ready to go.
I get in the car and start heading to the place, its not far and now my dick is getting hard just from the sort of wierd excitement of probably being bigger than her.

Get to the hotel, go to the room, she opens the door wearing almost the same stuff from the previous night, shes not angry anymore, rather she has a guilty and naughty look on her face.
I walk in, she offers me a drink, starts appologising for her behaviour. I say "cool but you said I had a small dick and yours is bigger than mine, so lets see if thats true or not".
She laughs and starts undressing and takes her top off first...

The boobs drop out and they look very nice, very obviously fake like pornstar style implants but very nice.
My dick is quite hard at this point so i take my jeans off but keep the underwear on. At this point im getting nervous, what if shes actually bigger ? I had no intention of sucking a dick, never have and honestly I dont plan to...i was being driven mostly by my male ego.

She takes her leatherette pants off next and shes wearing silky looking black panties. Theres NO bulge showing. Im like relieved at this point and im fairly confident i was right that it was a bluff.
I take my underwear off, its got a wet spot on it from precum and my dick pops out and its almost at its full size, her eyes go big and she lets out a small giggle. I feel like she honestly did think i had a small dick.

Next the panties come off, and i still cant see any penis but it eventually swings out from her thighs, its not that hard yet, sort of a semi and its about say 4 inches at this point. I tell her to make it hard so we can compare, so she lies next to me on the bed and starts wanking it (i think she was on hormones because she was clearly turned on but was having some difficulty getting fully hard). Her body looked really great fully naked, honestly like a female fitness model but with a penis.

Takes her some time to get hard and she has to grip the base of her cock firmly and it gets to a good size, maybe around 6". Bigger than i expected but smaller than me noticeably, girth is around the same.

So i move mine next to hers and tell her "see im bigger" and she is desperately trying to stay hard or get harder, i can see the strain in her face. She isnt saying anything and while my dick is next to hers i tell her i want to take a photo as proof that im bigger. As im doing that she cums while trying to stay hard.
I moved away a little bit cause i dont really want any cum that isnt mine on me (yeah yeah i know thats probably not what you want to hear :D).
She came properly hard, the cum was thick white ropes and she lets out about 9-10 spurts that dont go very far because of how thick it was.

I was actually taken aback by that, while i had a bigger dick, i cant cum like that, and i was actually a bit jealous. I cum about the same amount but its waterly and sort of clear, her cum was like what you see in porn videos.
While she is spurting out cum she tries to grab my chest and it caught me offguard so i gently pushed her hand way. In retrospect i felt bad for doing that, she seemed a bit embarrassed when i rejected her touch. It wouldnt have really hurt to let her touch my chest i probably ruined a good orgasm for her.

While I start dressing up and she reminds me about the deal, that whoever was bigger gets their dick sucked. I tell her that its okay, i dont really want to degrade her like that i proved my point and that was enough. So im getting dressed and getting second thoughts because i was still rocking a hardon since i left home and I needed to cum bad myself and she seemed like she was eager to do it.
So now im waiting for any opportunity for her to offer again, she then pulls out condom from her purse and says "How about i just suck it with a condom on ? Thats not so bad right?"

I was like "okay sure" internally im thinking "thank fuck she asked a 2nd time".
She puts it on, starts sucking and it was good, even with the condom on. I just relax and enjoy the view, like i said her bod was absolutely A class if you like fit bods.
I cum soon, and its also a big load but my usual watery consistency so i quickly take the condom off myself cause i was a bit embarrased to let her see it after seeing how hers looked.

I wash up and change quickly, appologise to her as well saying that i didnt mean to be a douchebag or disrepectful to ladyboys, she seems happy and comfortable so I give her a small hug and leave.

It was really an exhilarating experience, going there and not knowing for sure if id be bigger or not but coming out the "winner". Im sure some of you will say that i got played and it was just her plan all along to get me to do sexual stuff with her, but honestly i dont feel that way, i feel like it was just an odd situation that escalated to that point.

Believe it or not, its a true story, it actually happened, and I dont actually feel embarassed or anything about it. I actually feel good that I did it, i learned a lot about myself. I actualy do have pics and proof but im not willing to share it for now.
There also a part 2 to this story (no it doesnt involve me having sex with her) but still might be worth hearing. I might add it if theres any desire to hear about that part.
Hope this was worth the read.

Sure - would like to hear what happens next

Okay so ill oblige with the second part of the story :)
Like I said above this is true...

So after the first encounter some time goes by and i find myself thinking about the encounter and how exciting it was. I never thought id have any interest in something like that but i did and there was this feeling that i needed to do it again, but the excitement came from not knowing who had the bigger dick, now that i knew the result it obviously wasnt going to be such a thrill anymore so i didnt really want to try meet up again with the girl, even though she did message me a couple times.
I think she could sense that i was not into her and one day she just casually mentioned that she had a friend that was in my area that did massage and that i might be interested in seeing her. I asked why ? and all she said was "heavy cock" and gave one of those grinning emoticons.

Now again, that wierd excitement got into me, i had the number so i pondered wheter to message her or not. I didnt do it immediately because unlike before, i wasnt really going to get a chance to see her first and get an idea of the type of person she was, nor could i just message her and start a dick measuring contest.
One day during a break i just sent a message saying i got the number from her friend and asked about the massage service. She was very professional over the phone and this worried me a little thinking that this wasnt really going to be what i was looking for but i took a gamble and at some point in the chat i complemented her on her profile picture. She was wearing some kind of black dress, not much was really visible and the face was obscured so i couldnt really tell but i took a shot at it.
Thankfully she recieved the complement positively and we started chatting more casually and a bit flirty. At some point she said to me "You know im a ladyboy right" and i was like "yeah xxx told me, it doesnt bother me".
She then insisted that i come for the massage and promised i would really enjoy it and that it would be "special".
Now i knew i wanted to do the cock compare thing again, so i didnt really want to beat around the bush too much, so risking coming accross as a wierdo i said "Well im not looking for sex or anything..." to which she replied "sure of course thats not what i was offering anyway".
I asked "So what were you going to offer ?"
she said "Erotic massage, body to body, i also do fetishes, role play..."
Bingo! That was my opportunity so i cut to the chase and asked "Have you ever done the penis compare fetish ?"
She giggled and replied "Yeah once before...it was interesting, i can do that sure"

That really got me excited, and in my excitment i jumped the gun a bit and started asking questions i probably shouldnt have such as if she thought she had a big cock or not. She answered that she was not sure, but nobody has ever complained to her about having a small dick. She then asked me if i thought if i had a big one to which i replied "Yeah i think so, but not huge or anything".
She then out of the blue offered to send me a picture of her cock, but on the condition that i send her a picture of mine. I agreed even though this potentially would ruin the surprise factor but i wasnt thinking all that clearly at this point. My thought was as long as there was nothing to judge the size against in the picture it wouldnt matter you still wouldnt know who was bigger until we were next to each other in person.

I send pretty much my best angle picture, to which she replies "wow thats a nice size!" so now im waiting, its taking some time for her to send a return picture but she does eventually. I get it and im not sure what to think, im not exactly an expert on judging what a "nice" cock looks like, and the picture i got looked kinda generic, i dont know how else to describe. Sure, it was normal looking, maybe a bit stubby by otherwise i guess pretty normal looking.
The excitement started to wane and I started to wind down the conversation but i still made the booking because i felt like i went this far, i didnt want to bail now.

Day of the booking, and im not that amped, sharing the photos was probably a bad idea in this context as i expected since it took some of the surprise factor away, i didnt have that strong urge and throbbing dick like i did last time. Oh well might as well just go, get the massage and try enjoy myself as much as i can.
I head towards the place, its a really nice area and the place she is staying in is a large house thats kinda been converted to like a getaway spa. Its got a pool, a outside mini bar and a bunch of nice things around. I head to the room she told me, now its important to note at this time while i did see a picture of her cock, i saw nothing else, no face no body, boobs etc. That fact hits me and i start to get some level of excitment again.
I get to the door and she opens it....
She is standing there in front of me, long silky black hair, fairly cute asian face, big fake boobs but not as big as the fit girl i met with before....but heres the real kicker, this bitch was like almost 6ft tall with legs like tree trunks and rounded calves like one of those "thicc" instagram influencers !

Now...this started to worry me, why ? Well something i didnt mention yet from the above initial chat was that i copy pasted the similar stakes from the first girls meetup. If i was bigger she had to give me a blowjob...and if she was bigger i had to. Like i said before, i actually dont want to suck a dick, its just that having some stakes makes the excitment level high but i always felt confident i could win.
But considering the size of this woman and the general dimensions of her, it starts to dawn on me that that picture of the stubby cock i saw, could in fact be a fat monster.
I keep my cool and get into the room and she asks if i want to be massaged on the bed or table, i say bed.

I take my clothes out, lie down and the massage starts lights are low so i cant see anything yet, she doesnt bring up the compare fetish at all so im thinking she forgot. Next thing i know shes also naked while doing the massage, and soon i feel something touching the back of my thigh and it feels f*cking heavy.
At this point im actually in state of a bit of panic, like ive bitten off more than i can chew. I want to turn around and look to find out the size but i have to be face down. Out the corner of my eye im trying to catch a glimpse but i cant see and all i can feel is this thing bouncing on my legs and ass as she massages me and it feels big.

Eventually she asks me to turn around and i see it, it was actually BIGGER than i expected and it wasnt even fully hard yet, clearly just a semi. And my chest kinda just went cold and internally im saying to myself "F*CK youre going to have to suck a dick now, why the f*ck did i even do this ? You f*cking deserve it for being such a arrogant fool"
She says next "so how do you want to do this compare fetish again ?" as she grabs her shaft and starts tugging on it.

Im lying down there like a stuttering mess trying to decide wheter i should make an excuse to leave or admit defeat and will have to suck it, or just pay her more to not have to do it.
Shes staring at me still wanking it and its getting harder...but not a lot bigger but its still pretty damn big. Also her balls were huge as well and hanging low, they were maybe two times the size of mine and swaying as if they were made of steel.
I start wanking my cock to try get big, at this point im thinking well this is what you came for so might as well try against somebody who can actually win this time.
I was so worried though that i was not getting as hard as i normally can, so i get to around like 6.5" compared to my maximum 7". This was making things worse and i just couldnt get hard because i was trying too hard and not naturally turned on by the situation. She lies next to me and we are both stroking and shes fully hard now, girth is easily bigger than me, length is closer but shes maybe close to 7 or more.

All of a sudden, she starts moaning and says she wants to cum for me, i see this as an out and say sure. She gets up from the bed crouches down on the floor which has these black marble tiles and she cums. Its a huge load, not as thick as as the previous fit girls load but she came much more, there was a big pool of cum on the tiles afterwards.
I cum soon afterwards, but it was a terrible cumshot, i wasnt fully hard and the cumshot was way smaller than normal, kinda pathetic compared to what i normally can do.
Anyway, to my surprise she never brought up the whole "loser has to suck winners dick". She was actually super nice and polite the whole time, i think she never expected that it was something that either of us were going to actually do and it was just chat for fun. She was just more concentrated on having that fun.

I spoke to her afterwards and asked if she had ever measured her cock and to my surprise she said no. I really had to know for closure so i asked her if i could come back when she was rested and measure to see. She was being super nice and humble and saying that shes not as big as me etc but i didnt buy that.
Measuring day ended up being the next day so im there with her and a measuring tape and we measure. Her cock was just under 7" Girth at the thickest part, which was in the middle, i found that a bit strange cause im thickest at the base and so are most pornstars ive seen in videos. IMO thats properly thick ! Thats like 1" thicker than me.
Length was actually smaller than me ! I was truely shocked by that, i was more relaxed and at ease that day so i came in at my normal 7" length with curve, she was 6.8" but perfectly straight so it made it look much bigger especially with the girth. I also just had to try hold her balls, and as expected they were absolutely heavy, i couldnt believe it, it felt like holding two large marbles, i never thought a trans woman could have balls like that given the treatments a lot of them go through.

You could say i was lucky she didnt take the whole compare thing seriously because for sure i would have lost initially, but if we were both at our A game its probably a draw but id admit just visually she looked far bigger than me.
Anyway that was the last time i tried this whole compare thing. I experienced both the ups and downs and i think i dont really need to explore it any further :P. I did enjoy it overall but i think im done with it for now.
I Hope part 2 of the story was a somewhat exciting read :) , theres no part 3 and i dont think there will be anytime in the near future. Cheers !

Okay so above I said there was no part 3, but there was something that happened again a couple months ago involving the first girl. I figured I add it to this thread since its the same girl involved and youll be able to see the back story.

Right, so this latest encounter started with me wanting to go out and do something exciting, the prior month my girlfriend and I were on vacation, we had a great time but when I got back home and back into the grind at work I was craving to have bit of fun again. I asked my girlfriend if we could go to a club or something with her friends again but she hadnt really been in the mood for it.
A couple days pass and I decided to ask her again, and she says no she still wasnt keen on it, but her friend Jessica was back in town and had been asking her to go out as well so she suggested why don't I go out with Jessica and take her for a few drinks.
Now just to refresh the memory, Jessica is the fit asian ladyboy/shemale that I met before when I went out to meet my girlfriend for drinks that one night. My girlfriend was drunk that night and didnt know about the whole dick compare antics that later happened between me and Jessica.
Anyway like i said, my girlfriend isnt the jealous type and she doesnt mind me being around her friends. So I tell her, "yeah sure im happy to take Jessica out" and she replies "Great so that should get both of you off my back !"

So the evening comes and I head off to go pick Jessica up from her place. I hadnt seen her for several months so I was interested to see how she was doing. I park outside and call her and she comes down to my car (its an older model black Porsche 911 for those who care). She gets in and greets me with a smile.
Shes looking great just like last time ! Shes wearing a skin tight black leatherette skirt, black high heels with straps and a white top that kinda looks like a sports bra but its meant for casual wear. Her fake DDs stretched the top such that the cleavage was showing on the top and she wasnt wearing a bra underneath since you could see the nipples poking through. Her black hair was nice a long and full of body and she had her great golden tan again just like last time her makeup looked nice as well, a bit pornstar-ish but i liked that. The main difference i noticed though was she was in even better shape this time, her arms and legs looked really lean and toned and her butt looked rounded as well.

Anyway we start chatting while i drive to the club, the place we decided to go to was kinda like a strip club but...not exactly. Its got 3 floors, has a dining area, and various themed rooms (like a library, a 60s gentlemens room, a zen room, and a jacuzzi room plus some others) and a area with a stage and pole where they do have girls dancing, some are strippers, some are just like entertainers who dance.
Id been there before about 4-5 times and it was always good fun but expensive, sometimes crazy sometimes chilled just depends on the company you have on the day.

We get there, pay the hefty entrance fee and head towards the lounge area for drinks. One of the first things I ask Jessica about is her slightly improved look. She tells me that shes been training really hard. trying to attain that "perfect fitness bikini look", plus she has been seeing a cosmetic surgeon for some procedures to her face and body. She says some nice things about me as well, that Im still looking young for my age etc and various other chit chat. Eventually the topic of our last meeting where she got drunk and we ended up comparing dicks to see who's dick was bigger and we had a great chuckle about that. She then tells me something a bit odd, "We should try that again sometime, maybe ill win this time".
Now im thinking "huh?" how are you magically going to be bigger than me when you clearly werent before ? I figured she was being flirty as usual and didnt bother to ask any questions.

About an hour or so in we have had our cocktails and moved around various areas of the club, we get to the stage area which has these nice round couches and we sit there and watch the shows while having our drinks, we arent drunk, maybe very slightly buzzing but thats it.
So of the performers came to chat to us, have some shooters and then leave, that happened throughout the time there at this side.
Then eventually, this one girl comes and sits by us. A gorgeous black woman, fairly tall maybe 5"9 really great legs, lightish skin color like beyonce and really big breasts, probably DDDs. She's very good looking, cat like facial looks and nice slightly curly black hair that comes down to the middle of her back. Shes wearing a outfit that looks like a evening gown but its got sparkly stuff and various things stitched on to it. Judging by her overall look I assumed she was one of the strippers.

She sits next to me and starts chatting, "Hi Im Leona, nice to meet you !"
For some reason, my friend Jessica seemed a bit uneasy about this girl, she wasnt that welcoming compared to the others than came and she gave her a bit of a cold shoulder.
We engage in some small talk, she asks if we are a couple and I say that we are just friends having a night out, while Jessica grumpily sips on her drink.
She then asks "So why dont you come with me for a private dance, or have some champagne in the jaccuzi area". This confirmed to me that she was one of the strippers.
Jessica looks at her, grins and says "Its okay, we're not interested right now, maybe later"

The stripper looks at her and then looks at me and puts her hand on my shoulder and says "You sure you dont want to come ?"
Jessica looking a bit annoyed looks at her again and says "Not now honey, cant you see we are chatting"
The stripper gets up as she turns she rolls her eyes a bit and walks away. Im not sure what Jess's deal was, maybe she was jealous, but she wasnt like that with the other girls, but this girl and her seemed to visually have a lot of similarities, they both had a very similar makeup style, both had large implants and very toned arms and legs so I thought she felt a bit intimidated by her.

A few more minutes pass and we have racked up a large bill so far, and I think the strippers are noticing we have money to spend. So eventually the girl Leona comes back and sits with me again.
Again she asks if i want to join her for champagne in the jacuzzi room, making a lot of hints about what will be happening in the jacuzzi. Jessica sassily snaps at her and says "Listen here, he is isnt interested babe, can't you take a hint and leave ?"
The girl replies cheekily "He's a grown man, you don't speak for him, let him tell me himself" and she looks at me waiting for a response and puts her hand on my crotch suggestively.
Jessica now is getting a bit riled up (playfully) and noticed the strippers hand on my crotch and says "Girl, he isnt interested, besides his cock will destroy you, so just go away!".
The stripper chuckles a bit and says to Jess "Whats going on here ? You have a bit of penis envy or something ?"

Jess can't help it at this point, I know how flustered she gets when she is challenged and she loses her inibitions (like when she got confrontational with me the last time about who's dick was bigger).
She starts waving her hand around "Penis envy ?! Girl are you being serious right now !? There's no penis envy here, in fact ill shove my fat cock down that big mouth of yours just to shut you up !"
It was getting a bit heated, a mix of playful banter but also some real friction between the two of them.
Leona bursts out laughing in a kind of disbelief, "YOUR cock ? Are you delusional or something ? Maybe lay off the roids love..."
The stripper gets up and leaves and blows a kiss at us sarcastically.

Jessica is really agitated now, jittering and just restless and looking around rapidly. She looks at me and says "I bet she thinks im joking about having a cock, ill show that bitch who I am!"
I tell her to chill, it was just some playful banter and she's not trying to fight her or anything, they are just looking for a payday.
Jessica shuffled closer towards me on the couch and says in my ear "Call her back, Im going to show her my cock and I want to see the look in her face..."
Im like, "Thats silly, and youre just going to create a scene". She then gets grumpy lies back on the couch and refuses to talk to me anymore.
So now im thinking, this was a good night and its ending off poorly.
However the area we where sitting was quite private, lots of silk curtains, fairly dark and the couches arent directly in view from the other seats so I had an idea...

"I have an idea Jess, but don't outright show it to her, try and flash her it unintentionally"
Her eyes light up, she pulls up her already short tight skirt a bit more and pulls out her underwear and untucks her penis. From where im sitting i can see up her skirt easily and after just a few seconds her cock is THROBBING hard and she is looking like she's ready for a fight.
Surprised i say "Jess ?? Erm your dick is rock hard ? And it looks bigger than before ??"
She then explains to me that she had a couple procedures done, she had the ligaments cut to extend the penis out a bit more and also had dermal injections to make it fatter.
I couldnt exactly tell at this point how big, but it looked properly big compared to last time.

I go to call the stripper Leona again, she wasnt so keen to come back, so I tell her ill order champage and book the Jacuzzi room with her. She agrees but says i must book her friend Sammy as well.
Sammy is nearby, a very small cute black girl wearing lingerie, slim, short (maybe 5"0), short black hair that comes down to the shoulders. She had the most gorgeous dark velvety looking skin id ever seen, not a single mark on her, small breasts but the most beautiful toned abs youd ever seen on a women.

I walk them back to our corner couch. Everybody sits down, Jessica now has her legs crossed, smilling cheekily. Sammy introduces herself and we order some light drinks, Sammy is on my right, Leona to my left and Jessica to her left. Jessica uncrosses her legs and slowly opens them while leaning back on the couch. I can see her cock is still rock hard, and is a bit wet now on the tip. The area lighting is dim but has additional lights that change color and move position, every now and then the light hits our couch and illuminates it enough to see clearly. Jessica is waiting for Leona to catch a glimpse of her cock.
Im waiting with great interest to see what happens.

It takes a couple minutes but eventually Leona while sipping her drink notices Jessica's cock showing between her skirt. Her eyes go big, she puts down the drink and starts looking at Jessica's skirt.
I lean over to Sammy and say "Just FYI, Jessica is Transgender" in order to get her to be cool, she just giggles and says "Oh thats cool", she had the cutest girliest voice you can imagine.
Leona looks at Jessica and says "Holy shit! I thought you were just talking shit to me, is that real ?!"
Jessica holding her drink says mockingly "What ? I told you I had a fat cock, he's not the only one packing at this table." Leona leans closer "No way thats real, thats like a dildo or something", Jess puts both her arms on the top of the couch and says "Wanna bet its real ?"
Leona replies "Bet what ?"
Jessica explains "If its a real working cock, you gotta suck it, if you think its not ill pay you the full fee for booking the Jacuzzi area and you can just leave I wont go"
At this point i need to mention, book a jacuzzi room at this place is like $1000 per person per hour. Chilling in that room with drinks and girls adds up to a massive bill really fast.
Leona says confidently "sure!"

Jessica pretends to act like Leona called her bluff and refuses to open her legs and show her. Sammy and I are watching this debacle with much enjoyment. Leona starts asking Jessica to pay up, she then says "okay wait!" pulls up the skirt spreads her legs and shows her cock, still hard, throbbing even more now, the veins are thick and the top is shiny and wet, and her balls are sucked in tight against her body, shes fully waxxed down there too.
Leona looked shocked, she asks if she can hold it and Jessica says yes. She takes one hand and grabs the cock and says "wow this thing's a weapon!". Jessica starts reminding Leona that she needs to suck it now.
At this point I tell them ive already booked the Jacuzzi room and we should go there and not create a scene here.

We head to the room, everybody strips down and jumps into the Jacuzzi, its a really nice place, paintings and murals on the wall, drinks on call etc. Im wearing a speedo as underwear so i just keep that on (what can i say ? I came prepared).

...Anyway this post was quite long so ill continue the story in the next post...

...continued from above...

So, now we are all in the jacuzzi. Its a bit awkward because theres a remote which you use to call someone when you want fresh drinks and a guy comes in dressed as a butler and all the girls are sitting there naked in the jacuzzi. Anyway it doesnt bother them but it just seems like such a wierd thing to me.

The girls start chatting, the current hot topic is Jessica and the fact that she has a cock, and she is LOVING the attention now. Before she and Leona were at each others throats but now they are naked in the tub together sipping champagne and laughing.
Leona has one hand holding her champagne glass and the other underwater holding Jessica's cock. Im sitting with Sammy and we are just chilling with random chit chat now and then.
After the first glasses of champagne go down, Jess tells Leona "Hey remember our bet ?" and gets up and sits on the top corner of the top and points at her still hard cock.

This was the first time I got a look at her newly enhanced cock under good lighting. I honestly was quite shocked at the results of whatever procedures she had done. Before she was about 6 inches long and 5.5 inches girth, Im about 7 inches long, and 5.7 inches thick, when we compared those months ago i was noticeably bigger.
Now she was also about 7" long, and maybe 6 inches thick at least! And on top of that she was getting rock hard erections with pumping veins, whereas before she struggled to get hard. The only thing i could notice from the procedure was two very small scars above the top of the penis on the pubic area, which were barely noticeable due to the tan.

Leona now looked a bit nervous the mood changed a bit. She goes up to Jess and says "Yeah okay, deals a deal, get ready". She gets up slightly above the water, her boobs showing and they are monsters, they look very nice but the skin is streched from the sheer size of those things. They made Jessica's DDs look small.
She opens her mouth and starts sucking Jess's cock, Jess throws her head back and moans a bit. Sammy looks at me and then puts her hand on my crotch, she seemed to be in the mood now as well.
Leona starts sucking faster and harder and Jess's face starts to get more and more strained, her balls where sucked up right into her body you couldnt even see them !
All of a sudden, Leona lets go and stops sucking and lowers herself back into the tub. Jessica initially looked a bit relieved at first but then started to look confused.
"Why did you stop babe ?"

With a cunning look on her face Leona replies "The bet was just to suck it, you didnt say how long or that i had to make you cum". Jess had a smile on her face but looked baffled and just said "Ah ! You bitch ! What the fuck girl ?!"
Leona then explains "The fee is just for booking the room and drinks, im not obliged to do anything sexual here, and officially nothings supposed to happen here".

Now having been here before, I immediately knew what was happening. Like she said, officially the room is just to chill drink champage etc and chill with the girls, but the reality is rich guys book in here and do all kinds of sexual stuff...for a price. She goes on to explain to Jess that she will continue the fun will let her fuck her for $1200.
Jess looks at her like "WTF" and then just blurts out "This dick does not fuck pussy, only ass". Sammy and I just laughed when she said that, it was so off the cuff we couldnt help it.
Leona looks at her and says "Normally i wouldnt, but I think youre hot, and if you promise to take it easy on me then yeah you can fuck my ass".

Suprisingly Jess agreed, and I thought she was going to ask me to pay it, to which the answer was going to be "HELL NO!" i already paid for everything so far, but she pulled out her card from her handbag, the stripper presses the button on the remote and the damn butler looking guy arrives again with a card machine this time!
She pays the fee, the guy leaves and before you know it Leona is sucking that cock again and Jess looks like her soul is being sucked out.

Now ive seen Jessica cum before and I thinking to myself that the stripper has no idea what shes in for, Jess cums like as if a can of whipped cream exploded !
Though everytime i think she's going to bust her nut some how she manages to hold on and keep going. Its obvious the stripper is trying to make her cum fast.
About after 4~5 more min of very hard and fast sucking, Jess just moans like she's about to die pushes back Leona's head and starts cumming on her. First couple of shots go straight into the strippers mouth, and then she fires off about five more on her face and tits. The cum is really thick and white like i remember it before, and as I expected Leona is surprised by it. She tells Jess "Holy shit, your cum is crazy thick, its literally like cream"

Jessica lies down for a few minutes outside the tub, Leona gets out as well and heads to a basin in the corner to wash her face. Im still still in the tub with a hardon with the cute Sammy next to me.
Now at this point, i think Leona was being sneaky, I think she just wanted the money and didnt really want to do anal and thats why she tried to make sure Jess came early.
After washing up Leona gets back in the tub and starts drinking again, Jess gets up behind Leona, downs one of the shooters on the side table and starts wanking her cock again.
Im thinking "NO WAY!" she barely could stay hard when i first met her, now shes able to get rock hard twice in a row ?
Once shes hard again she taps Leona on the shoulder and says "Hey we arent done yet girl, im still gonna pump that ass!" Leona had a look of disbelief on her face when she saw that her cock was already hard again. Jess carefully pulls her out of the tub and makes her go on all fours on the wooden floor just to the side of the tub. Pulls a blue condom out of her bag, puts it on, wanks a couple more times then starts pushing her cock into the strippers ass. Once its all the way in she smacks Leona's ass cheek and starts slowly pumping. Leona has a slightly uncomfortable look on her face but seems to be relishing it.

While thats happening, Sammy looks at me and says "Well hun do you want to do anything ? Im feeling a bit left out here" she giggled. So I tell her okay, but i ask her if i the damn butler guy needs to come in again since Jess is busy plowing the other strippers ass just right there outside of the tub !
Sammy says "Nah, i trust you, we can sort it out afterwards" and she proceeds to remove my speedo and start tugging my dick.
I also get out of the water now and sit on the edge of the tub, and she gets a good look at me now as well and she says "Hey! looks like both you guys have big cocks, nice!"
She starts licking my dick, and then turns around and starts bouncing her ass on me but I stop her and say "No sex, just a BJ", and she giggles and says "Ah no way!? Trying to save yourself or something ? Like whats the difference ?"
Im thinking like maybe she's right, i should just do it, she was looking utterly fantastic, that body was world class, slim with silky skin and curves in all the right place and a small round ass that you could bounce a quarter off. Though i stuck to my guns and decided to just get a good sucking and she was fine with that.

While im getting my dick sucked by Sammy, Jess and Leona are still going at it on the other side. It was a wild sight, both of their pairs of big wet fake tits bouncing back and forth. Jess had strain showing on her face and her veins and muscles were popping. Every now and then she would smack Leona's ass or tits. Leona started to get a bit annoyed at that after the first few times.
Sammy stops sucking for few seconds turns around looks at Jessica then looks back at me and and says "Damn your friend is a fucking machine!"

Though reality was, I could see Jess was running out of steam, i could see she was struggling to cum a second time but she was still staying hard. So a bit out of character for me I shout at her "Come on Jess ! Pump it !" just to try help her out a bit. She tiredly looks up towards me points and says "Hey quiet down! Your ass is next !"
Within about 30 seconds of saying that i can see shes tensing up like shes finally going to cum, I think Leona could tell as well because she pulled out Jess's cock, put her down back to the floor and legs in the air, pulled off the condom and started jacking off Jess's cock, pointing it towards Jess's own face. Jess was so tired, she just went with it, and after a few tugs, she started cumming, firing only about 3-4 shots of cum onto her own tits, the cum was more watery this second time round.
Jess just lied on the floor afterwards exhausted but still smiling, Leona then comically smacked Jess on the side of her ass and said "How'd you like that workout girl ?". Jess just silently put her hand up and showed her the middle finger and then they both laughed.

I myself was about ready to cum as well, then Leona walks up to me and Sammy and says "So whats going on here with you two hey ?"
She crouches down and starts to massage my shoulders and her huge boobs pressed up against my back. Sammy was still busy sucking my cock. It was an amazing feeling.
So as you can imagine I didnt last too long like this and I had to cum, i tell Sammy im gonna cum and let her decide what she wants to do. She pulls her head away and starts jerking me, then Leona reaches below and grabs my balls. I then shot a big load, about 10 shots straight into Sammys chest and abs. Unlike Jessica's mine is not thick, but i think i have a lot more volume. Leona looks at me and says "Yikes! you just fully glazed my friend", Leona was clearly quite a character, and with that we were done with the Jacuzzi room for the night. There was a lovely shower area next door to the Jacuzzi room so we all washed up and changed and went back to the main area.

We sat and drank some non alcholic drinks to try and refresh ourselves, but it was very late now, well past midnight. Leona and Sammy called over some of the massueses from the hotel side and they gave all of us some head and shoulder massages, but i could see Jess was trashed, the alcohol and sex had taken its toll and i figured i needed to take her home soon.
We left the club, after I settled the massive bill, it was like basically 2 months of my salary, but luckily i had plenty to cover it so I covered it and we left. Though not something i want to pay for again anytime soon !
Jess basically slept the whole drive back to her home, had to wake her up and walk her to her flat, then i drove home by myself.

Was an extremely enjoyable but also outrageously crazy night. Jessica is like a magnet for this kind of nonsense, but i feel lucky that i was able to experience something wild like this.

Damn Jessica sounds like a handful but a great time.

hot story :banana: