Carmen's Roommate Issues 01

I don't think there was ever a question while growing up that I was a little different than the other guys in the neighborhood. No one shunned me and I always received invites to events and games, but I was the one standing in back or the last to get picked for a team. Sure, there was a certain amount of teasing from time to time, but no one asked me to leave. That was my life growing up as Charlie. Not the best, but it could have worse.

And then, Life 2.0 happened. We all hit our twenties and started to go this way and that way to find our own lives. Or in other words, get jobs and leave those stupid Middleton High issues behind. I think about half of my class stayed in Middleton, which is probably close to normal for a city the size of Middleton.

Also, probably like most other places, backyard baseball games were replaced with city league softball games, nightclubs and house parties.

I never played Short Stop, but they elected me as the league's bookkeeper in a heartbeat. I never grilled the hamburgers, but I was sent to store when the party host figured out that they forgot to pick up a bottle of mustard. The reasons I was always on the invitee list kind of sucked, but at least I was invited.

My dating life was great as long as you ignore the fact that most of my dates with were with groups of girls at the malt shop. It wasn't the best situation, but I was getting my double chocolate milkshakes, so I didn't complain too much.

Life was just moving along until one day of my friends, Jack, threw me a curve ball. Jack was a good guy, he was one of the more popular guys in our crew, but he had a problem. It seemed that his parents were ready to retire and move further south. Jack had a job and didn't want to leave Middleton just yet and he needed a place to live. He had a few months to figure out his move.

Why he asked to rent a room from me wasn't clear to me. His response was that all the other guys had full houses or families and he couldn't find a place to fit in. His response to my suggestion of leasing an apartment was almost acceptable. He has been approved for an apartment at the Middleton Commons, but it wouldn't be available until September 1st. Ugh, I did not want a roommate for three months or even one month for that matter.

What am I supposed to do? Allowing him to rent my back bedroom wouldn't automatically make me the good guy, but turning him down would certainly make me the bad guy. And his argument that the rent would be on time didn't help. He had a decent job and worked five days a week. I almost wish that Billy would have asked me to rent him a room because I could have shut that down immediately. Billy doesn't believe in taking showers very often and he is convinced that getting close to toilet is good enough. But Jack, well, Jack is clean and neat. Actually, Jack would make a good roommate for a clean freak like me.

Why am I so reluctant to make a sacrifice for three months? Unlike most other New Year's Resolutions, mine was to let my inner self emerge and dress in fem as much as I could. Which is exactly what I have been doing for the last six months. I have been out in public dressed a few times, but I parade around my house dressed several days a week and I'm not exactly ready to give that up. And I'm pretty sure that I can't have that conversation with Jack. I wouldn't know how to talk with Jack as Charlie three days a week and as Carmen four days a week. That has to be an impossible conversation.

I'm happy now that I have come out, LOL, to myself, as a crossdresser, but I'm only comfortable doing it in secret. I am not ready to be called within the crew. I may not be invited to another house party again if my secret was revealed and then who would go pick up the hamburger buns?

I wasn't ignoring Jack's request, but I needed more time to think things over. I also needed to know if I could handle an accidental exposure just in case I got caught. What I mean by that is, if Jack catches me in a pair of shorts and a wig, does he freak out and scream or does he stare me down and remain silent. And what I mean by that is, will he punch me out or get a boner?

When I look at myself in the mirror, I'm happy with what I see, but that's me checking me out and it may not be a fair assessment. I'm not doing this to give anyone a boner, but I need a second opinion on how I look. No, it can't come from Jack because that would be too late. So, I took caution, wadded it up into a ball and threw it into the wind.

I contacted my friend Brandi and asked her to come over to give me some advice tonight about 6 pm. And because I'm not totally stupid, I asked her to bring me a cheeseburger and a milkshake too. I chose Brandi to be my second opinion and advice guru because she already knows some stuff anyways.

I think this where I should insert something about two birds and one stone, but I'm not going to. Just in case the she isn't happy with my little surprise I didn't want any stones laying around. Jack could take a hit, but I struggle when the wind blows hard.

I spent an hour getting ready for her arrival. I did the best I could with what I had to work with. I don't have a lot to work with, but I think I can dress three days in a row without looking the same. Maybe four days in a row with some cleaver mix and matching. I selected simple work out shorts, a sheer pullover that I should never wear, a choker, my dirty blonde short wig and a hoodie. I will admit that I have spent a fair amount of time watching "how to" videos, so I'm not too bad at facial makeup. No, you wouldn't agree with what I said, but that's my story and I'm sticking to it.

I was as ready as I was going to be and prepared myself to open the door and present Brandi with a weird situation. When Brandi texted me to let me know that she was on her way, I responded with a please keep an open mind and to leave all stones and other weapons in the car.

As I waited for her to pull in the driveway I repeated in my head "soft voice" a thousand times. Not only have I not been outside dressed a lot, but I have spoken even less. Here she is and here is the moment of truth. I took the deepest breath of my life and opened the door.

"Hello Brandi. Thank you for coming over tonight and thanks for the double cheeseburger. Please, come in and let trash talk begin."

"Well, I suppose I'm not all that surprised, but I will say that if this is something you're serious about, then cheeseburgers should be a no-no. Not good for the waistline Charlie."

"Carmen. Carmen Lux. Where shall we start?"

We sat in the living room and talked. Or should I say, we sat in the living room and she eyeballed me all night. I reluctantly thanked her for the cheeseburger tip and she responded with that I needed to view a different "how to" video website. She asked me how I got so good at shaving my legs and I sheepishly told her that I have three legs hairs to contend with anyways. We shared a few other tips and slams before things settled down.

"So, did you invite me over for shaving and makeup tips or is there something else? Like, does this have something to do with those panties you stole me last Summer when we all went camping?"

"Ah, you took 6 minutes slowly sorting through your back pack until you found "my color", remember? Anyways, I suppose we can call that night the beginning of it all. I think you picked out and helped me try on the perfect style and color. I still have them. However, my current problem is this. You may be aware that Jack wants to rent a room from me for the rest of the summer. I've been doing crossdressing for about six months and I'm not sure I can stop. A day will come when he catches me and it would be nice to know if I'm hot or not."

"I would expect you to be further along for six months of effort, but that's just me. However, One, let's not use words like "hot" for now. You need a little work. Two, work on your posture. Walk like a girl, sit like a girl and use your hands like a girl. Three, are you afraid of getting caught or do you want to get caught?"

"I'm not ready to get caught. I'll get the boot and then who would run store to pick up lawn chairs? I just like my fem time and I don't want to be worried about being confused for a girlfriend late at night."

"I will help you, but you need to be honest with me about that camping trip last year. Did you really forget to pack enough undies or did you just want my panties?"

"I always figured that you would be one to wear the sexy stuff. I thought there would be a chance that you would give me a pair and I thought I could get away with it for a day in the campground. You didn't disappoint me, but Danny did catch a glimpse of the bright blue shade color as I was in my tent changing."

"Hmmm, changing or jacking off your boner? Sorry Carmen, I suppose I already know that answer. So, you were saying that you were wearing my panties when you invited Danny into your tent? The tent you set up way in the back of the campsite."

"Shut it, Brandi. I was drunk and passed out. Danny just wanted to check on me. Can we get back to my roommate issues?"

"Hah, you don't drink and Danny left the campfire the very moment he received a text. A text from you I think. But, fine. It doesn't matter because I followed him in the dark and peeked on you guys. I'll give you credit for keeping your face buried in the pillows and I will admit that I copied your action a couple of times. I have had Kenny wrap his cock in panties while he humped my butt cheeks under the panties I was wearing. I call it Camp sex."

"Never mind all that. Any advice for me and my Jack the roommate situation?"

"There are three choices. One, don't get caught. Two, be up front and hope he keeps your secret. Three, be up front and hope he changes his mind about living with you. My other advice is to invest a little in a new bra and inserts. PS, you'll get caught over the course of the summer because I'm sure you like to sleep in your fem undies and everyone gets up for a drink of water sooner or later."

"So, I should play it safe and ask him to look elsewhere?"

"And give up the excitement of getting caught? Don't you want to have someone touch your satin undies or do you prefer staring at yourself in the mirror and keeping all of this to yourself?"

"So, I should dig through the trash and find the caution I threw away."

"Enough with the back and forth. Be the good guy, let him live here for a few months and hope for the best. Give me some money and I'll pick you up a few things from store. And by the way, if you're going to give Danny a foot job under the table at the malt shop, then that's something I would to know about in advance. I have a little freak in mee too. Ah, I'll be needing a little more money than that please. I think you need some real stuff."

"Here. All this stays between us, right? I mean, this is very embarrassing. By the way, foot jobs under a table are only true in memes."

"And this from the guy who takes Claudia to the hamburger shack every Saturday night. OMG, don't worry about me, worry about exposing yourself and your secret life to Jack.

"Well, wait. Take some more cash. I found out that I have to wear two pairs of panties at a time."

"Does it pop out when you only wear hip huggers?"

"Crossdressing issues are real."

After Brandi took my money and left, I sat on the couch and pondered my options. It didn't take too long for me to decide against allowing Jack to move in for three months. Not so much because I was afraid of his reaction if he caught me dressed, but the trickle-down effect within our circle of friends. It's one thing to have one person pissed off at you and another thing to be kicked out of the circle by all the others. Sure, I'll be the bad guy for a minute, but I should be able to recover before to long. And who knows, some of our friends may actually agree my decision.

It was still early evening in the evening, so I called Jack to give him the bad news. However, before I could lay it out for him, he chimed in with his news first. Another apartment will be opening up in one month and it's actually a better apartment. Ugh, he sounded quite happy and here I was, ready to tell him that he would have to reserve a corner on 7th Street and Elm Street to sleep at night.

I needed a minute to think, so I let him ramble on and on and on. The only thing I could come up with is to accept him as a renter for one month and one month only. I don't think he heard me say one month and one only even though I said it eight times, but I said it. Over and over.

Jack even sweetened the deal by letting me know that a large majority of his stuff would go straight into storage instead of dragging it into my house for one month. That was a big factor in what I did next. I took advantage of the situation by reminding him that I'm the good guy here and that he could bring his bed over this Saturday.

And I was quite pleased on Saturday morning. He had one truck load of stuff and two extra guys to help carry it all inside. I had my fake arm cast on as I welcomed them and pointed towards his bedroom. I suppose that the next time this happens, if it ever happens again, I will put away the shopping bags that Brandi dropped off for me last night. I'm sure all three of the guys knew I had no business shopping at the "Big Brown Bag" store. I will also remind Brandi that there are other stores that sell lingerie much cheaper than that store. And then I will remind myself to not wear exercise shorts in front of the guys when I have my fake arm cast on. It probably doesn't look good for me right now.

Unfortunately, one of the guys with Jack was Joey. Joey is a good guy as well, but he likes to supervise much more than carry stuff. He also happens to have a habit of cornering me when he tells me what he forgot from the store.

"Hey Charlie. It's really nice of you to do this for Jack. He was kind of in a bind and you really came through. I have a whole new respect for you."

"Thanks Joey. Should I pick up paper plates tomorrow on my way over?"

"Nah, let's wait until you get there and get settled in before we send you on an errand. It's a tradition, you know."

"And because you like to corner me in the kitchen alone as you explain to me what it is you need?"

"Again, it's a tradition. And who knows, maybe one of these days you will ask me what I want after I tell you what I need."

"That will not be a tradition. Enough of being naughty, Joey. Here come the other guys."

What the hell am I doing engaging with Joey? I have no idea, other than I guess I like it when someone gives my thighs the attention they deserve. Besides, I can fend him off my fake cast if I need to.

"Almost finished. Greg and I will grab the last two suitcases and I'll get you guys back home."

Oops, with Jack and Greg making one last trip to the truck, that gave Joey one last chance to do something stupid. Or maybe it gave me one more chance to do something stupid.

"Well Joey, if you were to tell me what you wanted, what would that be? And I'm only asking to be nice because I'm the good guy here. In other words, be nice and polite with your response and by polite I don't mean it's alright for us to lock our legs together."

"Hey, you're the one who didn't back away. And by the way, nice work out shorts."

"And I still haven't heard what you want. By the way back at you, is that for me or are you thinking of Cassandra? Surely her thighs are so much better than mine. I suppose I should make a note that you're not drunk yet, we're not a party and you're hard. Stop being so naughty Joey. They will be right back."

"By the way to the fifth power, can you stay late tomorrow? Like until everyone leaves or passes out?"

"To the 15th power, tell me what you want and say it out loud, in words, Joey."

Whew, saved by the bell. Jack and Greg rounded the corner just in the nick of time. I think Joey was almost ready to tell me that he's tired of his pristine girlfriend Cassandra being such a prude. Cassandra is nice enough, but we all get the feeling that she thinks certain sex acts are the devil's work. Plus, all the girls talk about her behind her back and they all say that nothing but food and beverage touch her lips.

"Let's go Joey. I'll have home just in time to go to work. I'll be home later roomie."

"Bye guys. And Jack, don't ever expect dinner. Bye Greg. Later Joey."

End Carmen's Roommate Issues 01