Wendy Wilds 01

Story Info
Wendy Wilds gets help from roommate to get exposed.
3.1k words
4.32
3.9k
4
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I suppose that after a while people just get used to things, right? It used to bother me when my roommate, Brent, would kick his shoes off in the front foyer and leave the laying how ever they landed and now I'm used to following behind him to make sure his shoes are perfectly aligned, side by side. It's just another household chore. It used to bother how often he would "accidently" bump against me and now I run into his bedroom with a thermometer if he isn't looking over my shoulder in the kitchen to see what I'm cooking while he pats my butt. I mean, I used to it.

LOL, it never bothered me that he never even flinched once no matter what I lounged around the house in, but it did bother me when he asked me why I never wear a stuffed bra around the house. His eyes told me that my explanation disappointed him, but I decided from the beginning that my flat chest would be my crossdressing signature. I mean, I have a couple of bras, you know, just in case, but I pretty much leave them in my dresser drawer.

Hi folks, I'm Wendy Wilds and I'm still trying to figure if I fell for my roommate's trick or was I able to turn the tables on everyone and finally find out what Wendy Wilds can do.

Brent's trick had two parts to it.

First, he explained to me about how his motorcycle buddies would be at our house all morning this Friday getting ready for a long weekend bike trip to some biker camp out event. Which was fine until he started to drop hint after hint that I should help load up the trailing van with coolers of beverages and food. His reasoning was that the guys would be busy shining up their motorcycles and giving their bikes a mechanical once over. That didn't sound too bad, so I nodded my head at him.

Secondly, and this is where his trick really kicked in, he handed me a small box and told me to open it. When I opened the box, I found two nipples looking back at me, which could only mean two things. LOL, Brent has been to the sex clothes store and he must have been embarrassed as hell, but apparently, he wanted something else to gawk at other than my flat chest, I guess. I knew immediately that he wanted me to wear a full bra this Friday morning as I worked in the back of the van while they, you know, were off to the side of the driveway gawking at bumps.

I wasn't so quick to nod my head this time and let him know that I would need a few days to think about it. Allowing Brent to see me dressed as Wendy Wilds is one thing, but running around the garage and driveway in front of his biker friends is a whole different thing. My objections were well demonstrated with my facial expressions and hand gestures.

I don't mind telling you that even though the breast forms had a certain appeal to them, you know, looking right back at me in the specialized box, I reminded myself that Wendy Wilds doesn't think about wearing falsies when getting dressed. To me, my smooth chest and boyish nipples were all that I needed. Besides, there are things you can do with shirts and hoodies to make that area confusing and I think I was doing just fine with that. However, as Brent has presented me with fairly expensive set of bra cup fillers and because his embarrassment must have been priceless, so I suppose that I could at least consider wearing them from time to time.

So, I grabbed the box and ran to my bedroom and made it clear that I would still need a few days to think about exposing myself to his friends, not only for the first time, but with an enhanced chest. LOL, he smiled, admitted that going inside of Gary's Sex Clothes store was very embarrassing and asked me if I was making us dinner tonight. Hah, we'll have carryout dinner tonight, Mr. Breast Forms Guy.

And then I got really pissed off because for one, SOB, they really worked and two, damn, they were very light and easy to install and three, SOB, wow, they really enhanced my chest. However, I'm still holding onto my original dressing method of a flat boyish chest, you know, most of the time.

I made Brent wait for my answer until the last possible moment. Mostly because I had to spend a few days to find a bra that the breast forms fit in better and because I needed a few other things too and that included a couple of special things for Tommy G, his best biker buddy.

And by the way, I was only even considering all of this because Brent might be right about how it might be time to let Wendy Wilds out of the closet. I'm not saying he is right. I'm just saying that he might be right.

Besides, if I get a few photos of me straddling a big bike for my Chang homepage, then I should be captured in new Denim shorts, right? And in this wig, which I can't figure out if it's dark with blonde feather points or if it's blonde with dark spike points. And what I mean by that is, leave me a comment on Chang and give me your color scheme opinion and if you say it's stuck in the middle, well, that is perfectly acceptable.

As the 10 am hour approached, I made myself ready and I started to internally laughed my ass off because as the female role player, I think it's expected for me to have the sore ass, LOL. And here are these boys, getting to ride half way across the State to attend a biker camp out event on those small seats and that vroom, vroom engine under them.

Wait, hey, that's at least six hours each way of a vibrating motorcycle engine under their asses, so maybe they something I don't. OMG, I think I may know why Tommy G set this damn weekend up now. I mean, I'm pretty sure that he loves a little vibration on his backside. Hah, I know your game Tommy G and I picked up a few things special, just for you and your ride, hah!

I have long suspected that Tommy G might like things a little differently and his motorcycle is sparkly blue, so my special purchase for Tommy G was a medium sized blue bejeweled butt plug and a blue one leotard to wear under his hard ass motorcycle gear. And you know, a small tube of lube and a small bottle of sanitizer. Hah!

I let all three of the bikers and Kenny with his trailing cargo van pull in and park before I made my first appearance outside. I even waited for them to busy themselves with checking their tire air pressure and for Kenny to prop the rear doors of his van open. That's when I made my casual walk to the van.

And holy train wreck snap, the back of the van was a mess with backpacks, tool boxes, tents and empty coolers, which means I will be working harder than I expected too. And better yet, holy Denim shorts snap, yup, the guys like these shorts alright. LOL, they are confused as hell, but they like the shorts and my bare legs.

However, I had work to do in the back of this train wreck van and I'm on the clock meaning if I don't finish up quickly, the guys won't go vroom, vroom any time soon. What I forgot about was that even the biker guys were busy dusting off their machines, Kenny the trailing van driver had less to do, you know, other than to bother me.

"Hey baby, the word from Brent is that you're roleplaying Wendy Wilds and that you're going to make enough room back here for all of our stuff, the coolers and for me and you to sleep in."

"Kenny!"

"Look, I have a nice air mattress that should fit between the coolers and the tents, so what do you say? Hey, we should test out the warranty on the air mattress. You're riding my shotgun this weekend, right?"

"Kenny!"

"Go pack some purple sleepwear for me Wendy Wilds. The van could use a splash of color."

"That's enough Kenny. You go help the guys. I have cooler packing duties to finish. And from what I heard from literally everyone, Amber rides your shotgun just fine. And just what is so funny now?"

"LOL, what happens if I hook up battery jumper cables to your nipples? You know, tonight after we recover from our first time. I mean, is it zap or yikes?"

"Ha, ha, butthead. Get out of here. Besides, I favor black and I only have a few things in purple. So, go and send Tommy G over here for a minute. I have something for his trip and don't even say it, it's obvious that you have something for my, well, my trip."

I will admit I was a little flustered as I went back to work in the back of the van and I will admit that for my first time being propositioned, I think I handled well. I mean, not everyone is that direct, right? However, as I pushed the tents to one side and positioned the coolers to the other side, I could clearly see that an air mattress would slide right up the middle. And then I shook my head from side to side and told myself that nothing was going right up the middle.

"Hey, ah, Wendy Wilds, were you looking for me?"

"Yes, Tommy G, I wanted to tell you something. However, if you have lewd comments about my manner of dress, let's get through those first. So???"

"Whoa, I'm cool Wendy, it's just that you have better legs than I would have imagined. Now, what did you need?"

"Well Tommy G, and I don't mean for any of this to be embarrassing, but there may be a few things for you in the cabinet under the bathroom sink. There is butt plug with a blue head piece, a blue one-piece leotard with snaps, a small travel size tube of lube and a bottle of sanitizer, if that's something you're interested in. The plug is bejeweled in sparkly blue, just like your fuel tank. Anyways, it's just a thought, you know, if you're interested in something like that. And you don't have to tell me your decision, but if you decide in favor of the secret items, just be sure to keep your heavy metal concert T-Shirt on and tucked in. The leotard is a little shiny. You'll also need a few minutes in the bathroom, so plan for that. OK, bye now."

Hah, his body language says "hey, that's gay" but eyes are as wide as a pie and I'll keep my eye on his comings and goings between the driveway and the house until they leave.

I suppose I should admit that it was a little disappointing that the guys were keeping their distance, but I kept up with my work. I even packed the pre packaged Sub Sandwiches in layers and with a note between each layer so they would know what the consumption order was. LOL, I just filled the beer and ice tea coolers all willy-nilly and covered it all with ice. And for some damn reason, I hooked up the portable air pump to the air mattress, you know, just to see if it actually fit, you know, just to see. And that trance was interrupted by a text from Tommy G.

"A forever secret, right?"

"Forever. Enjoy the ride."

And SOB, with a little maneuvering, the damn air mattress did fit, kind of. And why the hell I kept moving things around is beyond me, but I did until the back of the van looked like a small bedroom with walls made out of backpacks and boxes.

"Hah, I knew it. See? It does fit and just imagine how cozy it would be. So, did you pack a few things yet, Wendy Wilds? I packed a fully loaded 12 Gauge and I want you to hold my shotgun, baby."

"Shut it, Kenny. I was just checking it out because you need someone to take of you like I take care of Brent. Are those two blankets on the van's rear bench seat what you going to sleep under or do want to sleep on the raw rubber surface? And don't you dare say anything about liking it raw mister. We both know I'm not your type. I mean, wet works better for you than tight, right?"

"Hah, those are my sleeping blankets and I'm posting that I have someone to take care of me whether you like it or not, so you should just like it."

"Hah, you should know that I' always going to tell you to shut it, whether you like it or not. But never mind all that. There are hamburger, potato and onion meals in the small cooler by your front console. They are wrapped in foil and ready to cook. Just throw them on the edge of the camp fire and let them cook for 30 minutes. The potato's may be a little under cooked, but if I were there, I would tell you to shut it and eat them. You won't die. And don't you dare share my little notes with anyone."

"Well now, that sounds like you're taking good care of me, doesn't it?

"Hah, I'm assuming that Amber took good care of your full balls this morning, right? Go back and help the guys. I still have to make up your bed and leave my perfume scent on your front seat. Bye now."

As I stood back behind the van and admired my work, I realized two things. One, LOL, the first big pot hole Kenny hits is going to cause all this stuff to crash down on the air mattress and two, I'm liking the breast forms more and more. However, I am still a flat chested CD, for the most part.

"Hey Cheekbone, how's going with the bikes? Are they mechanically fit to make it to the city line?"

"Oh, that's 50-50, but I'm sure we'll be fine and oh my, doesn't this look cozy back here? Now I see why Kenny is over the bragging about how you're packing a bag and a box of 12 Gauge shells and I'm pretty sure that a box of shells is code for a box of condoms. So, are riding in the van and joining the party?"

"Hah, I am not riding shotgun, at least not this trip. However, I am looking forward to peace and quiet at home, so fill your bald tires with air and get going."

Cheekbone is cool and I think he has the best bike. He has it all decked out with running lights and it looks pretty cool heading down the street. And my peace and quiet was shattered by Kenny, again!

"Oh, Wendy Wilds, you have undone yourself. I mean, it's going to crash down when I hit a pot hole, but until then, wow, what a place for us to do it in. So, are ready to start admitting a few things, Wendy Wilds?"

"Shut it, Kenny. I packed you a special cooler with Miss Bea's Spiked Ice Tea, but not while you're driving. I also put a few blunts in the glove box. I wrapped them in something purple, so be careful when you open the glove box. So, are you going to text me a few times over the weekend?"

"I'd rather roll over and ask you to get me up for another round in person."

"Nice try. And stop looking at me like you want to kiss me good bye. That's not happening. However, these Demin jeans shorts are called Apple Bottoms."

"Ah, good to know and what I mean by that is, huh?"

"I'm just saying that sometimes people squeeze the fruit at the grocery store to make sure it's fresh and what they want."

In other others, two open van doors provide ample coverage if two willing adults want to be a little frisky or something. By the way, if people at the grocery store squeeze that hard and for that long, then the fruit is ruined.

"So, have a safe trip and watch out for the guys. Are you going to hug me so that I know exactly what your condition is or what? But a hug only, mind you, no gyrating."

"Are you always going to play games with me or are you going to cure my condition, Wendy Wilds?"

"I re-arranged your backpack and by the way, did you like my apples?"

"I did and I'm going to check them out deeper next week, you know, for worms."

"Did you fill your gas tank or do I need to run up to the station with you? We may have 17 minutes before the guys are ready to go. By the way, I put your cigarettes and lighter in the center console and cleaned the bugs off of your windshield."

Oh well, it was his loss because the guys had their motorcycles fired up and they were ready to hit the highway. And shame on Amber for not being here to see Kenny off because she would have had a little something to mess with and I don't mean a little something.

All in all, I'll call the morning a success. The guys had visual access to me and didn't freak out. The neighbors couldn't stop looking over and, well, LOL, old Mr. Jenkins may have been freaking out a little, but then again, he probably hasn't seen a pair of bare legs in quite some time. And I think that Kenny might just be that horny most of the time.

Unfortunately for me, I was all dressed up and had very few places to go at this hour on a Friday morning. You know, other than the "Stop & Rob" convenience store, which I might say, I took my time as I walked up and down each aisle.

Fortunately for me, I had three full days to play as Wendy Wilds without interruption.

End Wendy Wilds 01

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousover 2 years ago

There are many attributes found within a flat chested boi-gurl. Have fun trying/testing the breast forms, they are an option.

Who knew . . . You might yet go both ways . . .

Share this Story

story TAGS

Similar Stories

Best Friend's Secret Matt confesses to Cindy, but Cindy has her own confession...in Transgender & Crossdressers
A Halloween Love Story Sam's had a bad week, but the weekend changes everything!in Transgender & Crossdressers
AC Went Out! Turned into a good night!in Transgender & Crossdressers
For a Good Time Call... A man gets a surprise from a lovely woman in a club bathroom.in Transgender & Crossdressers
Taking a Break The start of a holiday takes an unexpected turn.in Transgender & Crossdressers
More Stories