Roommate Rules Ch. 01

My name is Terry. Terry by day and Terri by night, well some nights. I just turned 22 and own my own home thanks to a large family inheritance a couple of years ago. I didn't buy a really big house, but it's big enough to share with a roommate. My roommate, Jacob, is a super nerd and someone I have known since high school. You might know us. We were the last two guys who got picked to play on a baseball or football game.

Jacob is my 2nd best friend. Mother Nature is my first best friend. She gave me softer features, decent legs and a nice butt. The only thing she made me work for is my waist. It seemed like a fair trade off to me so I set up a small work area in basement. I was willing to put in the time to keep my fem figure and features.

I had lived alone for almost a year when Jacob approached me about becoming my roommate. I told him that I would think about it and if I agreed then there would be rules. Simple rules, but some rules. I have never been a hard partier and didn't want that type of life style in my house. Pay the bills on time and keep the place clean. Knowing Jacob, these would not be a big problem and knowing Jacob's circle of geek friends, there would be no wild parties. Unless you consider a TV watch party for a science program as wild.

Jacob and I sat down and agreed to the rules without any concerns. Before we finished our discussion, I had to drop the bombshell rule.

"The last rule, or thing that you should know and accept, is that I like to dress in female clothing from time to time. That's not something I will parade around in, but you might catch me someday. I don't want you freaking out and I don't want to spread it around."

"That doesn't really surprise me Terry. You have always been, well, a little softer than everyone else. Do I get that bedroom with the little deck outside the sliding doors?"

"Yes. Is that important?"

"The backyard points towards the plains and foothills of the mountain range. No street lights and no city lights. It will be perfect for our telescopes."

"Our?"

"My star gazing friends, or as you might say, my geeky friends."

I laughed and waved it off as no problem. He was actually right as it would be a great place for nerds to hang out and get hyped up on soda pop. To my advantage, that put him on the other side of the house. A little space between us won't hurt. I also told him that he could use the small Den Room as a Greek Cave. It was on his side of the house and it was just big enough for a few chairs and a flat screen. He was excited about that. That a left a common Living Room, Dining Room and Kitchen between us. It also left me with my large Master Bedroom with attached Bathroom and a private Deck of my own. It also left the hallway bathroom for him alone. If it's clean, it's clean. If it's dirty, that's on him and his dudes.

"OK Terry, you know I have to ask, are you gay?"

"I don't feel gay and I have never been with anyone, other than dating Jules a while back. I'm fine in my street clothes and I feel good in my fem clothes. You might catch me in panties, but you won't catch underneath some nasty smelling guy."

"Is this a trannie thing or a sissy thing or what? And how often?"

"Let's go with a cross dressing thing. Maybe once or twice a week. I suspect you will get a glimpse of me in fem wear sooner or later. I am careful at all times, even while I lived alone. I may panties under my jeans once in a while, but I have never been out in public dressed."

I re-assured him that he and his friends would be safe. I also brought it his attention that one of his geek friends, Billy, may have the same traits.

"Billy is the quiet one of the crew, but I never thought about him like that. How long have you been cross dressing and how far do you go?"

"It's been a while. It started when I still lived at home. Not much, but that's where it started. Once I bought this house I went into over drive. I have different levels of dress. Anything from a single pair of panties to full on head to toe."

"You mean you wear make-up and dresses?"

"It took a while to master make up, but I managed. Kevin's Sister taught me how. And I have more skirts than dresses. I need to make it perfectly clear that a lot of deep secrets have been revealed her tonight."

"Relax, we have been dudes for years. Oh shit, do you know how many times I have playfully slapped you on the butt?"

"Relax, we have been dudes for years."

We agreed that my business is my business and that the same goes for him. He also announced that he was going to have a house warming nerd party next weekend. I agreed and said that we better get busy on the Nerd Cave. He laughed and went to pick up more of his belongings. I offered to help, but he said that he had a full nerd crew lined up and ready to go.

"My friends don't have very exciting Saturday's. I'll be back with the team in a while."

"I'll order some Pizza's or something later. Be careful, I don't think Billy is strongest of dudes."

When they returned, I acted as the director and made sure they knew which way to go with the boxes they were carrying. It was a pretty steady line of nerd boys going in and out. I don't know what came over me, but when I caught Billy alone, I took him by the arm and pulled him aside.

"Do you help with something special Terry?"

"I don't, but you do. Follow me and be quiet."

I led him into my bedroom and closed the door. I motioned for him to sit down at my desk and face the mirror.

"Do you need me to move this desk?"

"No Billy, you need a little color. Keep your face towards the mirror and try not to move too much."

"Color? What does that mean?"

"Just a little concealer. They won't notice the color, but they might notice your skin looks smoother. If they don't notice, then they don't look at you anyway. Look up."

"What makes you think I want color and why do you have color?"

"Concealer Billy. Now hold still, this won't take long. This will be our little secret."

Billy was objecting, without objecting. He tilted his face up and held still. I applied a very light coating of the magic dust to his face and smoothed out the edges. I had him look in the mirror.

"See, you can hardly notice. Do you want a little lip gloss?"

"Wow, I notice it and I like it. Look how smooth my face looks. Why do have this stuff and no, I can't wear lipstick. But I like my face."

"I have a neutral lip gloss. It will give you a little shine. Here, let me just touch your lips with it. See, that's not noticeable. Ok, you better get back to work before they miss you. Try not to make prolonged eye contact, but don't shy away from anyone. Bye Billy and remember, this should be our little secret."

Billy made his way out of my bedroom and rejoined the crew with their unloading duties. I laughed to myself when I noticed how he kept his head lowered.

"Hey guys, I'm ordering a couple of Pizza's. Do you want anything special?

"Anything will do. I think the boys are hungry. Thanks Terry."

I ordered two large Pizza's and four large bottles of soda pop. These guys need their sugar to maintain their geek status, or however that works. I can't have too much sugar. The waist line won't allow it. It's juice for me.

I went back to my room and put a pair of panties under my pillow. I have a pair that are too large for me, but they might fit Billy. Black satin bikini cut.

After a while there was a Pizza delivery person at the door. The door was open due to line of box movers so I could see someone peeking in and holding a couple of Pizza boxes and a bag of soda pop bottles.

"Oh, hey there. Good timing. I have a house full of hungry geeks. How much do I owe you?"

"$27 please. It looks like moving day?"

"I have a roommate effective today. He has been a pain in the ass already LOL."

I knew Jacob was standing behind me so I had to take the jab. He laughed and reached for the boxes and the bag.

"My landlord is buying LOL."

"Go feed the nerd's Jacob. Here, take this and keep the change. What's your name?"

"Brie, my name is Brie. What's yours?"

"Terry. I haven't seen you around here before."

"Order more Pizza's. Thanks for the tip. I better go now. My driver will be beeping his horn in a moment."

"You have a driver?"

"We work together as a team. He drives and I run the orders. It works for us."

"OK Brie, I'll see you again someday."

"Enjoy your dinner and all that moving stuff."

By the time I entered the Dining Room they were elbow deep in Pizza and it looked like they already drank most of the soda pop. No matter, whatever it takes to keep their strength up. It was also funny to watch Billy keep his head down. Come on, Billy, you can make some eye contact for crying out loud.

"That girl was cute. We should order Pizza again, like maybe at next week's wild party."

That was Frank. He was Jacob's closet nerd and geek friend. I busted out laughing first at the thought of his idea of a wild party. I wanted to ask him it he meant that by wild party that he was going to wear his other glasses, but I didn't. However, we were all laughing, so maybe we were all thinking the same thing. Jacob broke the laughter.

"OK, let's get back to work. We're almost finished."

"Slow down. I'll play the medical expert here. Let the food settle for at least 20 minutes before you start flexing your muscles. There must be a Mars landing or something on TV. Take a few minutes."

I was either right or they were just tired. They all went into the Living Room and turned on the TV.

"Billy, will you help me clean up these boxes and bottles please?"

Mission accomplished. Billy grabbed the Pizza boxes and headed into the Kitchen. I grabbed the bottles and followed him. I made sure it was safe to talk.

"Are you doing OK? I don't think anyone noticed. And I just figured out that pizza grease is a good excuse for shiny lips."

"I'm nervous as hell. We still have to ride back together."

"Jacob is staying here, so there will only be three of you in the car. Sit in the back."

"How did you know I would go along with this?"

"All I did was to bring your deep dark secret to the surface. I think it's something you have thought about for a while. You can wipe it off anytime you want."

"No, I like it. But why now? This could have waited until we were more alone."

"It was the first opportunity. I've never seen you without your crew of nerds. Plus, if we were more alone, you would be in nylons and a mini skirt. You want to come back later this week when Jacob is at work?"

"Slow down. This is enough for now, but really?"

"Well, not next week. I don't have anything that will fit you. Your hips are different than mine."

"You have other stuff?"

"Be quiet. This is our little secret, remember? Now, I left you a present under my pillow. I suggest that you sneak back to my bedroom, close the door and find your prize. Put them on under your underwear and feel how wonderful it is to have soft satin around your groin. They are new, but they are not my size. You can keep them. And no snooping around my room. I'll keep the nerds distracted for a few minutes. Now go and be quick."

You could see the wheels turning inside his head. To do or not to do, that was the question and his decision.

All I had to do was to walk into the Living Room, point at the TV and say "how does work? Nerds love to explain the workings of everything. Getting them to shut up is another thing. I noticed Josh coming back our way and gave me a thumbs up. I turned my back to the crowd, smiled and whipped my hand back in forth.

"OK guys, the food has settled. Let's finish this and give Jacob some time to settle into his new home. Frank, I'm putting you in charge of the wild house warming party next weekend. Make me a list of things we need and I will get them. It's on me. Go crazy LOL."

The first thing that belongs on his list is a film crew. This event should be captured on video and submitted to one of those funny video TV shows, like Nerds Gone Wild If Nerds Could Go Wild.

"Billy, how are you feeling?"

"Like a neutron center with an equal number of electrons and protons."

Jacob noticed that I was puzzled.

"That means perfect. A perfect match. And no, I have no idea what he's talking about. Alright guys, I think we're done here for the day. I can handle it from here. I'll see you all later."

Jacob walked his crew out to Henry's car. Frank took the front seat, so that left the rear seat open for Billy. He needed the privacy. I walked him towards the car.

"Don't get caught with those. You will have to wash them yourself in the sink and hide them in your bedroom."

"Thank you. I love them. I got a hard on in 10 seconds."

"I know, now go sit in the back seat. And don't forget you're wearing a little make up when you walk into your Parents house. Whatever you do, avoid your Sister until you can wash your face."

I didn't see much of Jacob for the rest of the evening. He was busy straightening out his belongings in his room. That's OK, Roommates don't need to spend a lot of time together. I have a week to help my friend set up a wild party. I laugh in my head every time I think of "wild party". Where do I start?

"Jacob, I'm going out for a while. I'll be back later."

I had an idea. A very strange idea, but an idea. I drove uptown to the Pizza shop and knocked on the door.

"Brie, will you let that customer know that we are not serving indoor dining right now?

"Got it Sal. Oh, hey there, Terry. Was something wrong with your order?"

"No, not at all. It was perfect. But I have a problem and you appear to be trendy enough to help me out. I will pay for your services and all expenses. I know this sounds strange, but I don't have the type of skills required to put a party together. Are you interested? I will pay you like a party planner."

"A party? For you or for those science geeks? I like to think I'm trendy in the clothes department, but I don't know squat about NASA."

"It's for the nerd crew, this Friday night. It's a house warming party for my new roommate, the super nerd, Jacob. All I'm asking for is ideas on party favors and help setting up the house. I will pay you for services rendered and all of the supplies. I can even pick them up from the stores. Please tell me that you have some interest? I have no idea how to set up a party for nerds."

"And you think I do?"

"No, but you will probably do a lot better than me. We just need a lot of soda pop and nerd wall hangings. I know of least 2 party supply stores in the area."

"Well, I have a few hours tomorrow and I'm sure they are open on Sunday's. Tell you what. Why don't you meet at the "We Be Parties" store tomorrow around Noon and we'll see what they have to offer. If we have enough time, we can go the "Parties Be Us" store as well. Deal?"

"I'll take it. Noon tomorrow. I'll be there."

"My services don't come cheap Terry, but I'm worth every penny."

"My senses told me that. That is why I'm here. See you tomorrow."

I spent the rest of the evening thinking about two things. Billy jacking off in his new panties and getting Jacob a new flat screen TV for his Nerd Cave. I'm not bragging about my financial situation, but flat screens are much cheaper nowadays and another TV might prevent conflicts in the future. I like my true crime channels and he can watch all Robots Rule programs he wants. He gets a gift and we avoid conflicts. It should be a win-win situation. It's been several hours since the nerds left so this might be a good time to text Billy.

"Do you need to clean them already?"

"Do you always ask questions you know the answer to?"

I always sleep in on Sunday's and today was no different. It appeared that Jacob had been up for a while.

"What day is Trash pick-up? I'll take that responsibility."

"Monday, so the containers go out today, on Sunday night."

"I own it. I'll be at my Parents most of today. Do you need any help today?"

"Nope. I have a few errands to run. I'll probably be home by 3 or 4. Tell your Mom and Dad I said hello."

"I will. I should be back by 7 or 8. See you later."

We went about our ways. I headed to the "We Be Parties" store right at Noon. I looked around for Brie. Maybe she was late. Oh, there she is, just pulling in now. Mental note, Brie drives a mid-sized silver sedan. A four door, what is she, in her thirties? Not that I would ask that. Maybe she just the extra room a four door offers.

"Hey Brie. Thanks for doing this. Are you ready to generate some ideas?"

"Hi Terry. Yes, I am. Let's do this. But before we start, I think you should know that I'm going to need $50 per store, as my services rendered."

"This must be my lucky day because I was going to propose $100 per store."

"Perfect, then we agree on $150 per store and we plan on visiting two stores. That's $300. Agree?"

"I like your style. Agreed, but you better deliver on the ideas. The worse thing in the world is a handful of dis-appointed geeks. It's funny how I just happen to have 3 crisp hundo's. right here."

"And you pay for all the supplies?"

"And you help me set up the house?"

"That will be services provided and an additional charge."

"Will another $100 do?"

"Agreed, another $150 and I will be at house next Friday about Noon."

"$200 if you show up on time."

"Got it, another $250. I'll be on time and pretty. You're not a pervert or something, are you?"

"No, but are you keeping tracking of this because I'm getting lost? We better get inside and start the process."

"Your wallet, I mean our agreed upon financial agreements are in good hands, my hands. Let's go."

I was delightfully surprised once we were inside. If even Brie never met a geek in her life, she knew how to pick out party favors. I was hoping for more adult geeky stuff, but it seemed to be geared more towards younger kids. However, we managed to fill a cart with items. Brie found these LED light kits that hung on the wall or on the ceiling. I thought they were pretty cool. We also got some streamers and plates and stuff like that.

"What's the next store? It should be quicker. We got a lot here."

"Parties Be Us. I'll meet you there."

"I can leave my car here and ride with you, if you want."

"What if your boyfriend sees us together?"

"I don't owe anyone anything."

"Sounds good. Get in."

We went to the other store and looked around. We picked up a few more things, but it was basically the same as the other store. The rear of my SUV was full of stuff. It should to be enough.

"OK, that I think that should do for the day. Thanks for all your help. Here's another $300."

"I'm trying to fair with you, we agreed on $250."

"I was thinking that you could prove to yourself that I'm not a pervert and I was thinking that when you show up on Friday, you could be, well, extra pretty or something. And then you will see that nothing bad will happen."

"I'll take that chance. $400 and I'll have bare legs, but no peeking up my skirt. You got another hundred?"

"Fine, here are two more hundo's, just in case there is an accident. I Mean, you might be on a step ladder or something when you're hanging those LED lights strings."

"Thanks. I'm almost late for work. Any chance I might get an order from you tonight? I only work until 6 pm."

"There is a better chance that you make me a European salad as you last order and bring it to me on your way home. Is my house on your way home?"

"Expect me before 7 pm. What about your roommate?"

"He's eating with his Mom and dad. See you tonight. Do you need more money for the salad?"

"I'm buying, tonight."

I took her back to her car and headed home and un-loaded all of these party supplies into the garage and basement. We bought more than I thought we did. Whatever, we shouldn't need anything else. After un-loading, I ran up to the electronics store and picked up a new flat screen. Not a real big one, just big enough for the Nerd Cave. I'm really glad these are so easy to hook up these days. Even the cable company makes it easy to add another TV.