Roommate Rules Ch. 02

I had wonderful Sunday afternoon, but now it's a few days later and I haven't done anything else to plan out my Roommates nerd party this Friday. I have all of the party favors, thanks to Brie, but that's about I have accomplished. Oh well, it's a beautiful Wednesday and a nice day to sit on my Deck. That's when my phone buzzed. It was Billy.

"I want to wear something Friday"

"We'll see."

My phone buzzed again a few minutes later. It was Brie.

"Can I borrow something?"

"Sure. When?"

"I'm in your driveway."

I ran around to the front of the house and sure enough, there she was.

"I'll be quick and I won't borrow much. I just like to wear different themed outfits on the weekends at work."

"Go ahead. Take your time and borrow anything you want to. Do you need help? Otherwise, I will be out on my Deck. It's right outside my Bedroom sliding doors."

"Yeah, I seen your Deck on Sunday. That's nice. So, I can a go at it alone?"

"I'll be out there. Holla if you need anything."

I could actually see Brie through the sliding door windows as she looked through my closet. I think she knew what she was doing. Not about looking through clothes, but the effect she had on me. Her bare legs and her short skirt had to be meant for me. If this was her way of getting her way, then she can have her way.

"I'm going try a few things on. No peeping."

"Whatever you need to do. Are you working tonight?"

"No, but I am going to stop the shop for a visit, but I only work there on the weekends. Do I have any limits in here?"

"Nope."

"Is this a Saloon Girl outfit?"

"It's a Poker Party costume. You would be the poker chip girl. But I don't know where the thigh high black and white socks are. Look in that top dresser drawer and you should find the arm garters that go with it."

"Found them, right on top of neatly folder thigh high socks. Oh, and they have small decks of cards attached to them. How cute. I'm going to take this for Halloween. My birthday is day before Halloween, by the way. Hey, wait a minute, Terry, why do you have a candy bra and panties set?"

"They came as an extra gift when I made a large order from a website. I haven't even opened the box. They seem like a college dorm room party thing. It also doesn't seem to be something one should wear more than once."

"All true, but you can wear a bra and panties under them. Can I have them?"

"Enjoy your candy. So, you're a Halloween baby huh?"

She took a few more things and asked me to enter the room so she could show me. It was actually a smaller pile than I expected so I approved her findings.

"That's less then I expected. Are sure you looked at everything?"

"I plan on coming back. If I leave now and we don't do anything, will you be mad?"

"No. You can go visit your friends at your work. Just don't forget where I live."

"Ha, like you're going to get rid of me now. Thanks for these outfits. I'll be here Friday at Noon, as promised."

"OK, do you need cash for anything?"

"Thank you, but no. I have a side job as a Party Planner and my Boss pays very well. He even pays better when you bat your eyes at him."

"Funny."

"I don't know how to ask you this, but is money not much of a problem for you?"

"Not so much. I'll see you Friday."

Her arms were full of clothes, but she managed to spin around a give me a little twerk.

I need to get dressed and go do something. Brie goes out in public dressed all the time, why can't I? Maybe a casual outfit and a drive around town. I don't even need to get out of the car. Maybe I'll dress and go visit Billy for a few minutes. It's Wednesday and his folks and Sister should be at work. I can show him how nylons work. It's getting late though, I better hurry.

I selected a simple pair of black tights, like Brie, a skirt, a tan v neck and my brunette wig. Add a little make up, grab a mask and I'm ready. I'll take some flesh toned nylons with me and demonstrate how to put them on. I sent him a fair warning text.

"Are you home alone?"

"Yes, are you coming over?"

"On my way."

I was quite excited to leave the house dressed. It was the first time Terri has seen the light of day. However, I was so nervous that I thought I might pee my pants. This would not be the time to get pulled over or get in a fender bender.

Whew, I made it. Now I need to make that mad dash to the front door. Check that, a mad dash would draw attention. A slow normal walk would look better, like a female visitor. I knocked on the door and surprised Billy. He was expecting Terry and he got Terri.

"Hello. Wait, Terry?"

"It's Terri when I'm like this. Can we go inside before someone spots us?"

"Yes, of course. Let's go upstairs to my room. What's in the bag?"

"Something for me and a demo for you. Which room is yours?"

OMG. So, this is what a nerd's bedroom looks like. He had like four computers, solar system stuff, Robots and his walls were covered with posters. Unfortunately, not one of the posters had a bikini babe on it. A true geek.

"Close the door. Are you wearing them now and how do they fit?"

"I wear them every day. They fit better now that I washed them in hot water a few times. Now what?"

"Are you going to show me or are you getting shy?"

I reached under my skirt and started to pull my tights down. I wiggled them down and threw them on Billy's bed. Next, I removed my skirt and tossed that aside as well. I now had Billy's full attention.

"Why are you taking your clothes off Terri?"

"Relax. I'm just replacing my tights with these nylons. You are going to watch me put them on and learn something. You don't want to show me how you look in panties? No pressure and no homo."

It took a minute, but Billy finally dropped his sweat pants and exposed his hidden secret.

"There, that wasn't so hard, was it? Sit on the bed and watch my what I do. Before I start, you need to keep in mind that wearing fem lingerie could be dangerous when you are with you buddies. Be careful of what you unbutton in front of who and don't ever go pee with one of them. People notice things."

"Got it. Now what are you going to show me?"

I positioned myself in front of him and between his legs. I held the nylons and garter belt up for him to see. While his eyes were drawn to the pieces of lingerie, I extended my right leg up and placed my right foot on his crotch for balance.

"This is a garter belt. These straps attach to the top of the nylons. It goes on like this and snaps together, almost like a bra. Now for the hard part. Nylons are tough to put on. It takes practice and patience. They run easily so you need to go slow. Watch how I do this."

He sat and nervously watched me. I showed him how to roll them up into his hands. Then I lifted my foot off of his crotch and slipped the rolled nylon stocking over my foot. Once I had them over my ankle, I put my foot back down on his crotch and had him watch me slowly pull them up my leg.

"See? You pull up a little and you release a little. Nice and easy. You pull the top over these snaps and press. There, one leg done. I'll do my left leg and the demo will be over."

I extended my leg up and pulled the rolled nylon over my ankle again. I needed my balance so I pressed my left foot on his dick and shuffled it place.

"Do you want to try pulling this up my leg, for practice? Go ahead, give it a try. Nice and slow. Pull and release. Look at you, getting a boner before you even start."

My foot told me that he was hard down there. With the nylon over my ankle, I leaned back a little implying that it was OK for him to finish the process. There was nothing fast about his next moves, but at least he finally started. It's a shame, but my legs might be first legs he has ever touched.

"Keep going, you're doing good. Do you notice how they cover and hide leg hair?"

"You don't have any leg hair. This isn't so tough."

"I know, but imagine how your leg hair would be hidden? Nylons are tight, but they have value in other ways. Believe me, when you put on your first pair and you see how much better your legs look. Go ahead, finish the snaps."

"Do you shave your legs?"

"I do, but I have the good fortune of having very little hair anywhere on my body."

He made it all the up to my thighs and the nylon was in position for attachment to the garter belt. I turned slightly to provide easy access.

"I don't know if I should. I'm already touching you more than I should. No homo, remember?"

"I don't think it's fair to call "no homo" when your dick is rock hard and your hands are on my thighs. Just snap the snaps."

"What do you expect? You have been giving me a foot job for the last 5 minutes. How many snaps are there? Besides, you're hard too. Look at that thing. And I like the panties you're wearing. They look different than mine."

"I'm half naked, behind closed doors and you're massaging my leg. Of course, I'm hard. These are a European cut. I like how my hips look in them."

"I agree with that."

"Snap me up and the demo will be over."

I bent my hips so the snaps were in plain sight. It took a moment but he began fumbling with the snaps and the nylons.

"See? That wasn't so bad, was it? Now, if the time ever comes, you will at least know a little something about the process. You can feel them some more. I want you too. They feel great from my private area down to my toes. Go ahead, see for yourself. Your cock wants you to do it."

"Don't tease me and don't look at me. I guess I should check them while we are here. Wow, these feel amazing, but they are look tight as hell. Will they loosen up?"

"I ruin them before I have a chance to find out, so I don't know. I wear them under my jeans once in a while. Although, if I wear them under my jeans I put on normal socks for coverage. Pants cuffs will pull up when you sit down. Remember that. And just as a reminder, you're still rubbing my legs."

"Am I a faggot now Terri?"

"Far from it, Billy. You're a nerd who wants to try on lingerie. Your worries should be more about keeping your secret and less about a stupid title. You're really hard. Do you want to show it to me?"

"That seems gay."

"Would you feel better if I took control and peeked at it myself?"

"You have been staring at me for 5 minutes. Are there really any doubts?"

"Fine. I just thought you might like to show it me."

"Are you thinking I might be able to wear something special to the party?"

"Maybe and maybe not. You could get away with lingerie under your street clothes and walk around the party with a hard on all night. On the other hand, if you find one of your nerdy little girl friends who is willing to suck your dick dry, you will have a problem."

"Like that is going to happen. Do you think that might happen?"

"You never know. You're not a bad looking guy and I' sure there will a geek girl at the party who is made, just for you. You know you're still rubbing my legs, right? And you know your dick is pointing right at me, right?"

"Sorry. But your legs feel so good and you're standing between my legs half naked."

"It's OK Billy. Your hands feel good on me. And we are going to keep today's visit a secret, right? Do you want to dry hump me? I know that is weird and sounds gay, but if you need some relief, well, I'm right here and today is a one-time thing. I mean, we are alone and behind closed doors."

"Thank you, but I think I have reached my limit for the day. Plus, I have never done that before."

"No problem. I was just trying to help. I should put my skirt back on and take off. Your family might be home soon anyway."

I pulled away from his grip on my legs and reached for my skirt. I jazzed it up by bending over in his face and took my time grabbing my skirt. I suppose he couldn't help himself when he pulled me down on the bed and rolled me over on my belly. He climbed on top of me and straddled my left leg. For someone who has never dry humped anyone before, he's getting after pretty good.

"Is there something you want to tell me Billy?"

"I've seen it in videos. Shut up and let me do this."

"OK, but for a rookie, you are really hitting your stride. You like rubbing your hard dick on my nylon covered leg, don't you? Don't be afraid to move and hump my buns either. That's my fantasy Billy, having my cheeks split by a big fat cock. Go ahead, move up a little and see if hot dogging is a real thing."

"We shouldn't be doing this."

"You mean you shouldn't continue humping my half naked body because you're about to cum in your panties? Is that what you mean? If you don't cum then this will be failure and who wants a dirty little secret that was a failure? Not me and certainly not you. Your grunting tells me that you are close to releasing. Try to get your fat dick in between my buns. Use my backside and rub me. There, that's better, that's how it's done. Do you like this?"

"I do. It's OK if I cum, right? I'm so close."

"Like I said, this is a one-time thing, so do your thing."

I knew things were about to wet and sticky when Billy squeezed me and grunted loud enough for the neighbors to hear. I felt the wetness on my butt and I was glad he still has panties on. They absorbed most of his nerd fluid.

The next that happened was a total shocker. Neither Billy nor I was prepared for it. Billy's bedroom opened.

"Billy, are you alright? I heard you yelling. OMG, what are doing and who is she? OMG!"

It was his Sister, Lynn. She stood in the door with her hand over her mouth and the largest eyes ever, in shock. The only saving grace for Billy was that he had been dry humping me from the rear and left side. He was somewhat hidden from Lynn in his position. I don't think she could see that he was wearing panties. Me, on the other hand, was fully exposed to her. I am so glad I wore my wig and v neck. I don't think she had time to register that my panties contained a bulge. I was hoping that her brain only registered a ½ naked woman in her Brother's bed. I'm positive she didn't recognize me as me. I was a girl on her Brother's bed.

"Lynn, get out of here!"

She slammed the door and ran down the hall.

"It's OK Billy. She couldn't see what you were wearing and she didn't recognize me. All you have to explain to her is why you had a girl in your bed. Change your underwear first though. You made a mess, a big mess."

"I am so sorry about this."

"Don't be, I'm not, but I better go before everyone else gets home. Can I get a towel please? And I will be expecting an explanation someday on why you were so good at this."

"Here, you can use this towel. Roll back over and I will wipe you off. So, now my dirty little secret is that I used your ass and came on it. It's a very nice ass, by the way. I'm sorry if I'm cleaning you to hard, but I need to thoroughly clean the mess I made on your ass."

"Thanks, I'm glad you like it. My dirty little secret is that I used my ass to rub your nut out. I better go. Do you want me to slip out the front door or what?"

"I don't see much other choice. Lynn is probably crying in her room. Don't forget your shoes."

I put my skirt on and straightened myself up. Should I sneak down the stairs or just walk normally? I have nothing to hide at this point. I'm just another girl coming out of Billy's Bedroom. OK, fine, I'm the first girl to come out of Billy's Bedroom. OMG whatever, I'm the first cross dresser to come out of Billy's Bedroom, happy now? You readers are so fickle.

I checked myself out in the mirror, smiled at Billy and waved good bye.

"Remember, say whatever you have too, but having sex with a girl is normal, as far as Lynn is concerned. Besides, a dirty little secret is only something dirty if it's not a secret. See you Friday."

I tip toed down the steps and looked around the corner towards the Kitchen area. I knew Lynn would be in there and she was. She was sitting at the table looking directly at me. I offered a very faint and shy wave. I did not want to push the issue. She had a glare in her eyes, but she surprised me.

"I didn't think he was ever going to have someone. I'm glad he did, but keep it down next time. You're not a hooker, are you?"

My fem voice still needs work so I did not say anything. I gave her a gentle look over my mask and held my hand up and shook my head in a 'No" fashion. I wanted to run to the door, but I managed to keep my composure and walked. If nothing else, I practiced my hip swing. I also had to consider if Lynn thinks I'm a tramp if I'm a hooker. Hmmm, not yet.

Once I was in my car, I sent Billy a text.

"Lynn was cooler than I expected."

The event left me with a question, a question for the world and you guys. If my fantasy was to be dry humped and a guy dry humped me, do I still have a fantasy? It's a good thing I have another fantasy to fall back on.

The drive home was nerve racking. I'm dressed in a skirt and nylons and I might look like a hooker. I also may have dried nerd cum on my butt. I pulled my mask up and held my head down and drove home at the speed limit.

Once I arrived at home I parked in the garage and closed the door. I sat in the garage and called my Party Planner Brie and let her know that some girls were expected as guests. I explained the situation to her and laughed at her reaction.

"Let's see, a house full of horny nerd virgin guys and a handful of geeky desperate virgin girls huh? You just need more alcohol and their car keys. And no, I'm sorry but I cannot stop by tonight. Don't be mad. See you Friday."

She is funny person and probably right about the nerd and geeks. Now, my next task is to get inside the house. Jacob is home and I'm in the garage, dressed like a hooker. Sorry, I meant dressed like a tramp. If Jacob was in the Living Room, I would have to walk right behind him. If he is in his Bedroom or the Nerd Cave, I would be alright. And there is no way I can peek through the windows of my own house. The neighbors could see a female burglar and call the cops. I fixed my clothing and headed through the side door. Whatever happens, happens. It's a good thing we already had the "talk".

I threw my shoulders back, took a deep breath, reached for the door knob and prepared myself for whatever was about to happen.

It figures that Jacob was sitting on the Living Room couch watching Nerd TV. I had two choices. I could slip behind him and get into my room while he was fixated on the TV or I could just get this over with. I took another deep breath and walked right over to the couch and sat right next to him.

"What's on? Giga Robot vs Mega Robot? What's the matter, robot got your tongue? Say something Jacob or at least put your tongue back in your mouth. Or just keep staring at me. Don't be so shocked, we had this conversation. Hello, Earth to Jacob. Are you alright?"

It seemed like we needed something to break the ice so I slipped up onto his lap and wrapped my arm around the back of the couch. I was hoping to shock him back to life without that gay thing getting in the way.

"I'm Sorry Jacob, but I was dressed and went for a drive. I didn't realize I was gone so long and I wasn't going to sneak around. Are you mad or upset?"

"It shocked me for a moment, but I knew it was coming. Does it make you mad that I think you're hot dressed like a hooker? Where did you get those legs from?"

"No, I'm not mad that I can turn you on when I'm dressed like tramp. I'm still a rookie at dressing in public and could use all of the compliments I can get. You can touch my legs if you want to."

"Alright, but is this going a little too far? Catching you dressed and touching you while dressed are two different things. Maybe we should leave well enough alone?"

"We can do that, but I want to be fair and give you every opportunity to express your feelings. And I feel something underneath me. Is that another compliment? Do I get a bigger compliment if I move around a little, like this? Oh, yes I do."