Frankie with a Roommate Ch. 13

You have heard me say many times that I am good at making plans when it comes to seducing people. Last night was no different. Master Plan 314 was a complete success. After Brie and I realized that we were not going anywhere as a Tranny couple I proposed a plan to get double sex dates with Zack and Timmy. And the best part of the plan was that we were able to turn the tables on the guys. We worked it out so that there was only enough time available for Brie and I get our sex and then time ran out and the guys had to leave. To my surprise, the plan worked.

It wasn't flawless though. After Brie and I took care of the guys, she went to use the bathroom and Timmy left the bedroom to get dressed. That's when I cheated on Timmy by giving Zack a quick blow job while we were alone in the master bedroom. I thought I was being sneaky with Zack, but Timmy was peeking on us through the bedroom door. Zack wasn't trying to be sneaky at all. He could care less about anything other than getting a blow job. And I wasn't aware of it, but Brie could see me on my knees in front of her precious Zack from her seat on the toilet. She couldn't do anything about it because of that Tranny Issues meme photo op thing. And yes, I just like to say the words over and over, Brie was draining her butt.

From there, I think it goes like this. Brie broke it off with Zack because he didn't stop me from sucking his limp dick. I broke it off with Timmy because I felt guilty about cheating on him 5 minutes after we had sex. Timmy decided to not to break up with me because I'm the only who jacks and sucks him off. He said he would rather take on the cuckhold role and hold out for my cherry someday. And Zack doesn't care about any of this silly relationship stuff as long as he gets another piece of ass soon.

I tried to claim Zack as my rebound boyfriend and he told me to take a number. His ticket dispenser showed that the next ticket was 33. I gave up hope when Brie confirmed that her ticket number was 19 last night.

It was a messy night and it was a successful night at the same time. And I'm not sure today will be much better. Not because of Tori's big press release for her sex doll Tonya Spells and how busy it will be at the store. That will be fine for two reasons. One, because it's Tori and things just work out for her. And two, because I'm in charge of the TV News media crews that will be there to cover the press release.

My concern for today is our cashier, Lizzie. I think Lizzie may have an evil sinister plan because she asked for a ride to work today. Lizzie and I are not best friends. We're just two Tranny types who have to work together and make the best of it. If Lizzie would stop trying to set my dresses on fire when I walk by her cash register counter, we might get along better. And no, I don't retaliate because she wears dresses and skirts made from burlap and I could burn the store down.

However, because I am the nicest Tranny in Middleton, I agreed that we could ride together to work together today. I knew this meant that I was stuck with her all day, but I grit my teeth and drove to her house. Lizzie greeted me at the door and told me that she was almost ready to go. She gave me a quick 2 minutes tour of the house and grabbed her back pack and announced that she was about ready to go.

Lizzie told me how she recently remodeled her house and it showed. It was a little empty, but very clean and new looking. And knowing what my sister just spent remodeling just her kitchen I would say that Lizzie spent quite a bit of money finishing her house. At a later time, I will ask her about where she got all the money to afford such a remodeling job, but for now I will assume that importing raw burlap pays better than one would think.

"And finally, this is the spare bedroom that I may rent out once I find the right roommate. Maybe a roommate like you. OK, I'm ready."

"Let's go. I have to stop by the Pizza shop to make sure the guys have all the food ready for the press release party and to break up with Timmy. I did him wrong last night and he deserves an explanation. An then you might tell me just why you wanted a ride to work today."

"Hey, I'm to be nicer to you. Plus, I thought it might give us a few minutes to chat about things. Things like how you got here."

"Duh, I have your GPS in my phone."

"No silly, I meant how you got here as a cross dresser. But I will remind you that it only a 20 minute to work, so if your story starts with "and let there be light" like most of your stories, we won't be able to finish our conversation. Maybe you could skip a few things and start in 1800's when the first gasoline engine was invented."

"Shut it, Lizzie. I know all about your lunch date with my ex-rebound boyfriend Zack today. You just want to be able to post that you got together with him and that I drove you. I know your tricks and history is important, so the best I can do is start with the bronze age. We're here."

I was surprised to see Mr. Rick's hippie van parked near the front door. I was concerned about this because the FBI follows Mr. Rick around in their big black SUV's while wearing dark suits, dark sun glasses and holding two fingers up to their right ear. I told Lizzie to remind me to check the petty cash box once we arrived at the store to make sure we had enough bail money available. I felt a little better when I seen Timmy and Zack loading the van with tons of food.

"Hey guys. Listen, we're running late, but I wanted to make sure the food preparation was going well and I wanted to let Timmy down easy because of what happened last night. As it turns out, I guess I'm also giving Zack a sneak peek of his lunch menu. Lizzie wore her best burlap mini skirt today."

Zack and Lizzie walked off to talk and Timmy approached me with his head down and puppy dog eyes. After I let him down, I will remind him that the puppy dog eyes are meant for girls and not guys.

"Timmy, I will give you your freedom. I know you were jacking off while you were watching me cheat on you with Zack last. I'm just happy that you were able to get back together so quickly with your ex, your right hand. I won't stand in your way and I'm sure you will be able to rekindle your romance again." And I won't be jealous if you have a 3-way by inviting your left hand to the party."

"It's alright Frankie. I appreciate your honestly and I'm sorry that Zack refuses to be your rebound boyfriend. But you're still going to wash my warm suit on Tuesday's, right?"

"Of course, I'm a cheater, not a monster. I can't put you in the position of a cuckhold if I break it off completely with you. But I can only give you hand and mouth action. I'm a cheater, not a butt slut."

"I tried saying cuckhold with a cock ring fast 3 times and I couldn't do it. What about the occasional hand jobs in the Pizza shop restroom?"

"Like I said, I'm not a monster. I might even let you know which nights I will be role playing the maid servant at the Vitale's card games. You can peek through the windows and you cuck yourself in the bushes."

I hand waved Lizzie to get over here and to stop giving Zack a snack before lunch.

"Zack, stop that and get over here. And don't come crying to me if you rub yourself raw by dry humping her burlap bag mini skirt. Lizzie, get in the car, I have something private to say to my two ex-lovers."

I gathered the guys around me and tried to lay out the rules for the day.

"Guys, I just want you both to know that I am uncomfortable with my ex-boyfriend and my ex-rebound lover being at my work at the same time. I can't afford relationship issues at my work. My reputation is at stake and it's squeaky clean."

"Relax Frankie. I will be busy unloading the food and then unloading into Lizzie. And once Timmy gets an eyeful of Tori in person, he will unload inside of the hippie van with his girlfriend. I heard they got back together."

"But I will remind you that even though Lizzie wears those sexy burlap bag dresses, she is fragile and pure as the driven snow."

"Lizzie is not pure and I have driven her snow before. I have told you many times to stop believing everything you read on Chang."

"Whatever Zack. Lizzie knows where to take you for your hot lunch date. You will find condoms and lube on the small table in the corner of the room. They are not paper weights, so use them. And make sure you two position yourselves to the left of the special 2-way mirror window. Bye boys."

I tried to squeal my wheels as I left the parking lot, but it didn't work. I always leave the parking lot at idle with my foot on the brakes.

"Lizzie, are you sure you want to hear about how I became a super cute cross dresser? I mean it starts in 1999 when I was born and ends with us riding to work together. My wonderful story will also end with a question and my question is why do you have a boner for me right now?"

"LOL, it's a short drive, so let's start somewhere closer to when you were 18. And you like my boner because I'm your secret, but we'll talk about later. I can only handle one four-day story at a time."

"Fine, after light covered the planet Earth."

"Frankie!"

"Ugh, my neighbors and I used to play video games a few days a week for a couple of hours. After a while my older sister stopped playing with us and went on to do what young women do. It wasn't long before David, my neighbor to the West, left the group to play more sports. That left Jillian and I to play against each other."

"And Jillian was your first love?"

"Maybe. It was nice to sit on a couch with a girl, but we never really made any moves on each other. Jillian wasn't like the other girls. She was a Skater girl and she was good at video games. The funny part was that we played at my house because we had the best game box set up, but I was never very good at it. I didn't win too many games."

"Oh, so Jillian wore knee and elbow pads so she could stay on her knees longer and suck you off because you can hold out for a long time?"

"Slow your roll and let me tell my story. I won't be mad if you pull your burlap bag up a little."

"Hmmm, like this?"

"Perfect. Well, as time went on, Jillian and I did get a closer and by that, I mean we would sit shoulder to shoulder and play touchy feely. And then, one day out of the blue, she claimed that the cost of losing to her was that she had the right to put eye liner and lipstick on me."

"And you didn't want to lose your one and only woman, so you agreed?"

"Pretty close. The issue was that it progressed from a few face paintings where we would giggle and laugh to the point of where I wouldn't wash it off for a few hours."

"OK, so a couple of friends goofing off. But as time went on, were you a willing participant or were you being bullied a little?"

"Well, I will leave it up to you to keep count, but then there were three bombshells. But it's fair to say I was a very willing participant."

"Explosion #1?"

"It wasn't long before I started to ignore the game box. It was over for me the first day I took my seat on the couch and leaned in towards her as to say she could do her work. I had learned when to close my eyes and when to turn and tilt my head. One could call me out for begging for it."

"Wow, but OK. Bomb drop #2?"

"Before I get to that I insist that you reach into my back pack and find my spare panties if you're going to sit there and stroke yourself while I tell my story. Now, where was I? Oh, yeah, some dude named Ben thought it would be good idea to fly a kite in a thunder storm."

"Frankie!"

"Sorry. One day I went online and searched for lingerie. I didn't know anything about styles and sizes, but all of the stores had sizing charts on their pages. I measured my hips and my chest and hit the send button. I didn't buy the best in case I made a major sizing and look error, but the bra and panties were a matched set. As it turns out, my selection wasn't that bad. They were a little tight, but I figured out how to let the bra straps out. It was a big moment for me."

"Alright. Not judging. When did the 3rd bomb find its target?"

"It was an atomic bomb. After I spent a few days figuring how to wear the undies, I set up a video play date with Jillian when I knew no one would be home for several hours. I made sure I was clean and shaven before she arrived. When she showed up, I had her take a seat and excused myself for a few minutes and went to my bedroom. While I was in my bedroom, I changed into my special undies, stuffed the bra full of Kleenex and slipped on a T-shirt and gym shorts. I admired my chest bumps in the mirror, felt myself up and casually walked back to the couch and took a seat."

"OMG, what did Jillian do?"

"When I first sat down, she was distracted by the video screen and didn't notice my secret. As I was leaning in for my make over, she was putting the controller down and reaching for her make-up kit in her purse. That's when I got the "OMG, why are there bumps on your chest" questions. I totally forgot about how I was going to explain this, but I muddled through it. Once I got to part where I was willing to crank it up a notch and that I was wearing a matched set, it was over for me. She told me to remove my T-shirt. When I stood to comply, she jerked my gym shorts down."

"Holy moly. What happened next? Did she run out of your house screaming while calling you names?"

"Oh no. She checked me out for a few minutes and pushed me down to the couch. She picked up her make-up kit and straddled my lap while facing me. I was so scared and nervous that all I could do was to lean forward and close my eyes and let the games begin."

"I guess you're right about that being a big moment for you. Do you mind if I ask if the touchy and feely stuff got bumped up a notch?"

"Hmmm, yes and no. I was too afraid to even move a muscle, but I think it's fair to say that I was getting my first lap dance. I cannot confirm if her hip movements were on purpose or just the result of her make-over work. Either way, my boner looked a lot like yours does now. And I would prefer that you make a mess in my spare panties as opposed to my car seat, if that's what it comes to."

"I will. Did you take another bombing run?"

"Jillian was flying the bomber jet. As Halloween approached, she took the lead and took us to one of those Halloween pop stores. Who knew, that for less than $40, you could get a complete slutty school girl uniform, including a cheap wig. She also knew that they were cheap and wouldn't last long, so she had me buy two uniforms. At this point I owned two cheap wigs. A long hair dark one and a short hair blonde one."

"Alright, so she found herself a pet project. I assume the dress up play dates continued?"

"They did. She even showed me how to run through the Ladies section at the department store and grab three packs of panties and a bra and then use the self-service lanes. After that, she suggested that my new fetish become my sleepwear and she even taught me how to wash them in the bathroom sink."

"I actually like this story. But, now that you became hooked on cross dressing, who found you out? Your sister? David? Anybody? And did you and Jillian ever have sex?"

"It's fair to say that Jillian liked popping my nut with her lap dances, but that's all that ever happened. If you ever meet her, I would appreciate it if you didn't bring that up. I don't think my sister ever found out or she never let on about it."

"Hmmm, so that leaves David."

"It does. Jillian set me up or should I say she set David up for a thrill. Jillian tricked me into a Truth or Dare video game bet and I lost, as usual. And just to be clear, her Truth or Dare bet never had anything to do with Truth. She forced it into a Dare and a Dare only."

"So, Jillian was having her fun and playing her little games. What kind of Dare did she trick you into and were you really tricked? Be honest."

"I did allow the "trick" to occur. I trusted Jillian and put faith in her ability to whoop David's butt in the video game. Her Dare was that I would expose myself fully dressed to David, if David won the game. The real trick on me was that she had no intention on winning. I should have thought about that when she decked me out a half hour before David was to arrive."

"So, you sat in your bedroom for 30 minutes fully dressed while those two played the game?"

"Well, yes, but Jillian said I needed the extra time for selfies. And once I started snapping selfies, I couldn't stop. I have always had a girl's butt and I have never had leg hair. The selfies were another big moment for me."

"OK, I got this. Jillian threw the game, had David kick back in the couch to enjoy his victory and then called you out of the bedroom so you could strike a pose and reveal your true inner self."

"Well, I would accuse you of peeping on us, but you left out a few important details. After David's eyes came back to almost normal, Jillian switched hats and became the coach. She put a whistle around her neck and started barking out instructions."

"OMG, she didn't make you strip down to your undies, did she?"

"No, she knew David wasn't ready for that. However, she did have David drop his skater shorts and sit back down. Then she had me face away from him and sit on his lap. Her instructions on how I should grind my butt on his crotch were very clear. She showed me by moving my thighs her with hands and blowing her whistle is my ear."

"And David was OK with his neighbor boy who is now his neighbor girl playing bump and grind on his dick, which I assume was hard by now."

"David was clearly in shock at first, but relaxed after a few minutes of my wonderful ass on his cock. Did I mentioned that I have always had a girl's butt? Anyways, once Jillian noticed that David was more than "relaxed" she instructed me to lift a little and told David to pull it out. I lifted, took a quick peek at him and sat back down. I no longer needed Jillian to work my gyrations."

"OMG, you were rubbing his raw cock? Was he trying to find home plate?"

"I still had my panties on and he was more than happy to have someone working on his cock. It's possible I was the first to touch him in any manner whatsoever. Jillian made it clear to David that it wouldn't be over until he made a mess on my panties. I didn't quite understand his grunts and mumbles, but his sounds didn't sound angry."

"Not bad. You revealed yourself, Jillian was blowing her whistle and you and David had a somewhat harmless sexual experience. It actually sounds like a nice way to start your new lifestyle. But, is this part where David blows his nut, freaks out when he realizes what just happened and ran like hell?"

"Not quite. This is the part where Jillian grabbed David's cock and pushed it under the back of my undies and told him to thrust and leave his nut between my butt cheeks. I was the one freaking out until I felt my cheeks being split by a very warm and very hard hunk of meat. This was the exact moment I knew where I was head in life."

"Hmmm, so you pulled his nut between those sweet cheeks of yours and then it ruined your friendship forever. The three of you never played video games together again?"

"Thank you for recognizing a sweet pair of sweet cheeks when you see them and I seen you peeking at me in the restroom. I didn't take me long to figure out that every time I used the restroom that you would be right behind me. And I will admit that today isn't the first time I seen your dick. But it was by accident rather than like today when you just whipped it out."

"Hey, you said I could push my dress up while we drive to work."

"Only because I was afraid your burlap thong would leave rub marks on you. I never asked you to shift sideways in the seat and stroke it in my direction. Anyways, back to my story, it turns out that the Vikings arrived in the America's way before Columbus did."