Natalie Jaye 01

Natalie Jaye 01

It wasn't unusual for my roommate, Joey, to have a friend or two over to play a few games of pool in basement and last week was no different, sort of. What was different about last week was that it was a Friday and that wasn't Joey's usual game night. They normally played on Thursday nights so they could drink their beer at the Sports Bar on Friday's. But here they were, Joey and his friend Wesley, starting their weekends out a little differently

But not for me. I dress as Natalie Jaye every Friday night and nothing was going to change that now. I don't hide it when Joey gets home late on Friday evenings, but I do make my trips to the kitchen as quick as possible. Joey knows all about my secret life, he deals with it just fine and I don't parade around in front of him. And guess what? Joey pays Nate his share of the rent on time and we talk about who will take the garbage out that week and life goes on. Oh, and speaking of that, I will occasionally dress as Natalie on Monday evenings so I can watch my dance competition show in drag and then flash my painted nails at Joey so, you know, he'll take the trash can out to the curb.

Until that fateful day last Friday. Joey and his friend Wesley were playing pool in the basement, the noise level was normal and I was going about my business at my vanity table half dressed as Natalie in my bedroom and updating my Chang homepage. It felt like everything was good.

And things felt even better when Joey sent me a text to give me advance warning that Wesley was on his way up the steps to use the bathroom. I mean, what better living arrangements could one ask for, right? I made sure my bedroom door was mostly closed and went about asking for opinions on Chang about my new long hair brunette wig. And when I say long hair, I mean my new wig covered my boy nipples as long as I leaned forward towards the camera on my laptop, which I did. And by that, I mean my Chang followers will get a topless hair bra selfie before the night is over. LOL, maybe two because you know, there has to be a nip slip selfie somewhere, right?

What I didn't notice was that Wesley was peeking at me through the crack in my bedroom door. LOL, and then I did notice his peering eye and I stood up and casually walked to the door and closed it shut. I didn't slam it nor did I call him out, I just closed it. So, Wesley got an eyeful, but he didn't get away with it and he knew it because I gave him a wink as I softly closed the door.

And neither did I get away with it for very long. It was mere minutes after I posted on Chang on that I had just gotten peeped on when I received another text from Joey asking me to bring him and Wesley a couple of beers downstairs. I was going to reply that the refrigerator in the basement was probably full of beer because that's where he keeps the majority of his beer, but instead I replied that I would be right down.

I quickly slipped on a pair of Denim shorts, fixed my wig, applied a new coat of Raspberry Red lip gloss on and headed towards the basement to make my point and my point was that I didn't need to take any beer from the kitchen refrigerator. I made a big point out of walking down the steps emptied handed, spun around the corner to the laundry area, bent over to take two beers from the bottom shelf and casually walked to the pool table and handed Joey a beer, with a smile, of course.

Joey gave me a little look, but that might be because I did not have leggings on under my shorts. Like I said, I don't flaunt it around my roommate and for all he knew, I didn't have any skin on my legs. Well, now he does and he also knows that I have painted toenails and an ankle bracelet.

Wesley, on the other hand, received his beer differently. I stepped into him a little, plastered a huge smile across my face and slowly raised my arm to hand him his beer and handed off his beer much more deliberately with one of those tug of war things. And by that, I mean I was definitely flirting and I didn't care that Joey was embarrassed or not. Wesley is having a Luau party soon and I haven't been invited and that's going to change!

Oh, and by the other way, Joey could learn a few things by paying attention to the look that Wesley was giving. I mean, that's how you look at a roleplaying girl who just delivered you a beer! Wesley's look was so intense and piercing. I'm not saying he absolutely liked what he was looking at, but he enjoyed looking me over and I mean up, down, back up again with a brief pause in the middle. In other words, he liked what he was looking at, although I was also positive that I was his first up close and personal cross dresser, but still, right? I mean, I know I had his beer, but I had his full attention in other ways too.

And then I hoped that he wasn't too disappointed with my chest, but I did every thing I could with my eyes to let him know that my chest is 100% adjustable, which sounds funny to say, but so true, LOL.

In other words, I'm going to his party, one way or the other.

"Here you go Wesley, a cold beer from the refrigerator that is right over there. So, are you kicking Joey's ass or have you fallen victim to his pool playing skills? Joey plays hard, doesn't he? Natalie Jaye, by the way, you know, at your service."

"Ah, well, I'm not winning. Oh, thanks for the beer and for the long walk you made."

"No problem. It's hard for me to keep my butt in shape and stair steps are good for that. So, listen, I'd twist your cap off, but I just put these fingernails on, so you're going to have to twist your own cap off."

"Hey, I never get that offer and we're roomies!"

"Shut it, Joey. Wesley is company. Play on boys. I'll be upstairs in my bedroom if you need another beer."

"Wait Natalie Jaye, why don't you hang out down here with us?"

"Sorry Wesley, but I'm in a mood to vent on Chang. There's a Luau party coming up soon and I can't seem to get an invite. I mean, I know the crowd will be a few years older than me and I know I won't know everyone there, but you know, invites are important just the same. However, I suppose the party host doesn't think I would look good in a grass skirt, you know, behind the Tiki Bar. Which is a shame because Joey has taught me many times how to squeeze the handle on a keg. So, I'll go vent and you guys continue to stroke your wood sticks between your fingers. Oh, Joey, should I expect Derek at the door soon?"

"Yeah, he's on his way, but I swear, if you talk to him about twisting his cap off, well, it will be your turn to take the trash out."

I flashed my nails at him and walked up the steps. I went straight to my bedroom and smiled at myself because OMG, that conversation exchange with Wesley really had me worked up and when I say I smiled at myself, I mean in front of the mirror as I took a few selfies to post. I am not ashamed or embarrassed to post a selfie or two of me in these short shorts, especially when my brass ring is clearly visible. LOL, I wish I could have taken a quick photo of Wesley and his hard brass ring too, but I didn't take my phone with me to the basement.

And then, of course, I started to search the internet for a grass skirt and hopefully a novelty T-Shirt of a girl wearing a coconut bikini top. I mean, I would wear a coconut or sea shell bikini top over my natural chest to Wesley's party, but that might be pushing the envelope for now. Besides, I have two things going for me in that area. There is a T-Shirt store in the Middleton Mall and I know just the girl who would be more than happy to let me plaster her chest in a coconut bikini across my chest. And by that, I mean I already sent Bibi a DM with my request.

Oh, and as a kicker, I started to research how to pour keg beer because Joey has never had a keg party and I don't know jack about squeezing those little handles!

However, before I finish that research, I heard the knock at the door and I knew it would be Derek. Derek is pretty cool, for the most, so I greeted him at the door with another one of my famous smiles. Although, it started to seem a little suspicious that these guys were here on a Friday night, but I put that out of my mind and opened the front door.

"Hello Derek. The guys are in basement sliding their sticks between their fingers. Would you like me to escort you downstairs and serve you a beer? You're looking good by the way. Oh, sorry, Natalie Jaye, but you knew that already, didn't you Derek?"

"Hey Natalie Jaye, listen, you are mad at me?"

"No, I'm not mad at you. It was actually nice of you to point out that my undies were riding above my cargo shorts. You didn't need to help me push them back inside of my shorts, but it's all good and we don't need to say anything else about that. Come in. Oh, by the way, if it comes up alter, I'm an expert at squeezing nozzles. And if it doesn't come up, then bring it up."

"Whoa, I have a nozzle! Let's stay up here and watch some TV, you know, on the couch."

"Hah, follow me sir and keep your eye on the bouncing ball."

LOL, as all real girls knows, if the guy is behind them, then the guys are watching the bouncing ball, right? It's a guy thing.

"Joey, your next victim has arrived. I'll serve up another round and leave you boys to your wooden sticks."

Oh, I see, now they all want to watch the bouncing ball, huh? Even my roommate! By the way, before tonight I never really liked my old refrigerator in the basement, but maybe I feel differently now. It's really not all that bad.

"Thanks Natalie. Are you going to hang out with us now?"

"Sorry guys, but I'm in a Chat Room and a cute little Tranny named Brie said she might have a perfect costume for me to borrow, but I have to stand in front of the laptop camera and measure myself with a fabric tape measure, you know, in front of the camera and Chat Room guests. And she's at work, so I can't keep her waiting for too much longer. Text me when you want another round of beer."

"What? What are you measuring?"

"My hips. She has a novelty skirt that she thinks might fit me and she only wore it once last summer. So, you know, I need to drop these thick Denim shorts and wrap a soft tape measure around my hips and give the camera a closeup so she read it. Text me when you're empty."

Hah, that was a lie. Not about Brie being at work, but about the measurement part. I already did that and that's why I was late opening the door for Derek. As soon as I let everyone know that I was back in the Chat Room, I received a great idea from Angela Jaye. Her idea sounded good to me, it sounded workable and I knew that Wesley had the money. So, I went back to working my thigh muscles and headed back downstairs.

"Don't mind me boys, but it felt like it might be time for another round of cold ones. And oh, by the way Wesley, my friend Angela Jaye just mentioned to me that all party stores have professional keg tappers that are in a shiny box with two fixed nozzles and it sits on top of the bar so guests can serve themselves and all the bartender has to do is keep the air pressure and guests up. I'm just saying. Oh, I'm also saying that I have the perfect pair of exercise THOT shorts to wear under the grass skirt that Brie just promised me, in case too much exposure is something that someone would worry about. OK, I'll leave you guys to your game and thoughts. Oh, and light up that blunt too and hit it a bunch of times."

Damn, I held my pose for a few moments like Didi Freckles told me to do, which they noticed, but the words didn't come. Damn! I figured that I put myself out there enough for the night, so I decided to give it a rest and go to bed. Right after I spent 20 minutes changing out of my shorts and into my PJ's that is. Oh, and after I served up one last round for the night. I mean, you remember what I said about how running up and down the steps is good exercise, right? And what better way to say good night to the guys than serving up my last call in PJ's, right?

"Last call boys, for me at least. I'll be turning in now, so have fun playing with your balls. Clean up when you're done. Good night."

And again, plenty of staring, but no party offer, yet. I logged off of Chang and crawled under my covers and did my best to drift off to sleep, which is a lie because I kept my wig on, just in case there was a back up at the bathroom and one of them needed to use my private bathroom.

Huh, listen to that, will you? It wasn't a request to use my private bathroom, but it was a soft voice at my bedroom door.

"Natalie? Natalie? Are you awake? It's Wesley. Natalie? Can I come in? Natalie?"

"What is it, Wesley? Do you need to use my bathroom? You can come in. I'm under the covers, so close the door behind you and push the little lock button."

Again, look at that, will you? I have never ever seen Wesley lower his head and shuffle. I mean, who was that stranger entering my bedroom at this time of night, right?

"I just wanted to talk to you before I leave for the night."

"Sit down on my bed and talk then. But talk slowly, I'm still half asleep and a little groggy."

Hah, he was going to be gentleman as he sat on my bed, but I beat him to it! As his butt was coming down, I lifted the blanket and provided him with a more inviting place to sit. And no, I don't sleep in just panties. I prefer a crop top and my fem boxers and I might I say, so did Wesley. And by that, I mean he spun his body around all by himself and lifted his feet up on the bed and dare I say, was almost laying with me in bed, although he was sort of sitting up in the bed. Hah, all that did was give me a chance to snuggle up his middle section because you know, I was all groggy and stuff.

"Listen Natalie, I know you're all groggy and stuff and I'll talk to you again about this tomorrow, but I'm afraid that you might get harassed at my party. I mean, I want you to come and it would be great if you worked the Tiki Bar, but you know, right?"

"Well, I'm too groggy to respond right now Wesley, but are you afraid because you're hard for me right now? You don't have to tell people that. But it's your party, so whatever you think is best."

Oh, now I know why guy's cargo shorts are so baggy! It's so you can run your hand right up the pant leg with ease, you know, when you're all sleep groggy and stuff. LOL, you can't stroke it, but you sure can push and pull on it.

"I don't mind Wesley. Just close your eyes and relax. Oh, and I'm not afraid if you just so happened to unbutton your shorts. I mean, my other arm is trapped under your legs and we should try to contain the mess you're going to make."

Guys, right? They will do anything for a gooey conclusion on any given night. And let me tell you, for a cross dresser who has yet to be involved in any kind of sexual activity, I seemed to figure a few things quickly and not just because I had his hard rod in my hand either. I mean, somehow my body seemed to find it's way on top of his legs and I guess I was humping him. I think. The geometry was a little fuzzy, but there I was, on top of Wesley and acting like I knew what I was doing.

"Ooh, ugh, that feels so good Natalie. Just between us, right?"

"Just between us Wesley. And this doesn't mean you have to invite me to your party. I've always found you to be attractive and I was hoping my first sexual experience would be with you, so, just relax. OMG, it's not easy to jack off someone else and I'm so glad that you are man enough to enjoy sharing my bed."

Well, he took the wind right out of my sails, didn't he? I was going to play it cool and slowly move my inexperienced mouth over his thick cock, but no, he had to beat me to the punch this time and pushed himself into my mouth. Which I really don't understand how he did that so effortlessly, but he did. I guess I'll work that geometry problem later, you know, after he is finished wrecking my jaws! And then I will work on the other geometry problem which is just how in the hell did I manage to contain it all? I mean, he absolutely erupted in my mouth and it came out a lot faster than I could swallow, but I held my own, kind of.

Oh, I can't wait to post about this on Chang! And here I thought my first Tranny sexual experience would be some kind of sissy rubbing or something and what I mean by that is OMG ladies, how the hell do you practice for that? It was like a damn fire hose or something! And no, I'm not posting the photo he snuck in while I was trying to clean my face and lips off.

"Holy hot stuff snap Wesley, you wrecked me!"

"Yeah, I did! Anyways, thanks, that was great, but just between us, right?"

"A solid secret. You're all macho safe and stuff. Are you leaving now?"

"Well, it's a guy thing, so yeah. Besides, the guys think I went home already, so you know, right? I can't get caught sneaking out of your bedroom."

"I know. Anyways, you can knock on my bedroom door again sometime. Good night, Wesley."

Well, SOB, he left! And he left without offering me a party invite! In other words, SOB! Or in more other words, hey, I'm going to his Luau party, one way or the other!

And what I mean by that is Bibi already forwarded me a picture of her in a sea shell bikini top, which was close enough for me and it should look pretty on a black T-shirt.

So, my goal of getting a proper invite is still open and I have time to work on that and my new other goal is to make sure Bibi is invited too! I mean, I know people fear getting caught at a party wearing the same clothes, but what happens when the same pair of boobs show up in the same sea shell bikini, right?

End Natalie Jaye 01