Frankie with a Roommate Ch. 01

You don't know me yet, but I hope we become good friends. I go by Frankie and I identify as a simple cross dresser. I have the good fortune to have the slender body and soft features for my hobby and I plan on dressing for the next few years. I think you would agree that I do pretty well with my hobby. Just check me out some day, you'll see. The bad news is that I have to refer to my cross dressing as a hobby because I live with a roommate who doesn't know about my secret, so my dressing time has limits. But, rest assured, I do the best I can and as often as I can.

Because I don't have the freedom to dress and hang around a lot, I made a decision to grow my hair out a bit and utilize my dark locks instead of wearing a bunch of different wigs. I do not identify as goth, but my hair makes it easier to dress that way. I do have a blonde wig and an auburn wig, but it's nice to just fluff and go with my own hair.

So, I have a hobby that I love and a roommate that I keep secrets from. What I don't have, yet anyway, is a desire to be a boy toy. I think about sex when I'm surfing the Chang boards, but I don't know to cross that hurdle. Plus, no one asked or seriously hit on me. My most daring public appearance was last Fall when I went fake shopping in downtown Middleton in a short pair of blue jean shorts. I walked the boardwalk 2 or 3 times and pretended to window shop. I used the reflections in the store windows to see who was checking me out and how were they reacting. The results were inconclusive. I think the guys who were checking me out spent just as much time checking out other people. No one approached me to say hello or flirt, which may have been a blessing. I don't know if I created any boners on those guys, but I had one from the excitement of being in public. This is why you always carry a bag with you, in case you need to hide anything.

I might as well move on to the reason I'm writing to you today. It's late Friday afternoon and I have been invited by my trap friend, Lizzie, to spend the night at her place tonight. That might sound more exciting than it will actually be. I think it's more of a house warming night in with a trap and a CD who are friends. No big deal.

I decided to show up fully dressed, so I had to do that and leave the house before my roommate got home from his usual Friday after work socializing. That shouldn't be a problem because my roommate, James, usually hangs out his buds at the local sports bar until at least 9 pm every Friday night. I had plenty of time so I decided to dress, run up to the department store for a few things, come back home and grab my over-night back pack. I would say easy as pie, but I've never made a pie, so what the hell do I know.

I bought want I needed at the store and took the long way home. I have no problem pulling along side of other cars while driving. If nothing else, you might notice my mask has lightning bolts on it, LOL. My problem started when I got home, seemingly in plenty of time, and ducked into my bedroom. I always feel safe when I close the door behind me. Only this time, as I closed my bedroom door, my eye caught my desk and noticed that my laptop was open. I was actually horrified because I never leave it open. I am careful about the files I keep on my laptop and protect them with my life. The hell with my banking information folders, I'm more worried about my CD folders. Because I don't have a lot of opportunities to dress, I have a habit of taking a lot of selfies in various stages of dress whenever I have the chance.

If I could go out more dressed, I might take less selfies. But for now, getting dressed in the safety of my bedroom and taking selfies is my sex life. It's not that bad, I do look good from a high angle.

And guys, I want you to follow me on Chang at Frankie128, but don't expect too much. I crop my face out of the photos that show a lot of bare skin. I'm telling you this so you're not too disappointed.

But right now, I need to figure out why my laptop is open and why the search feature identifies my CD Selfies 2021 04 Full folder as the last opened folder. I remember looking at my photos, but my April folder is too new to have photos where I cropped my face out.

There are two obvious answers. Me because I forgot to close my laptop before I left for the store or James, who is not home. But maybe James slipped home before heading to K-Sports for a beer and he happened to notice my laptop. For the moment, I will blame myself. I've never known James to snoop around my bedroom and he is not exactly a computer whiz. I breathed a sigh of relief and took another 8 selfies.

Check me out on Chang later tonight and leave a comment if you like my hair. But be nice, short and sassy is all I can do right now. And, by the way, one of you should DM me and tell me why it's so important for me to spread my butt cheeks and expose my rosebud. I know what you want, but, come on, my butt cheeks are very shapely. Why isn't a backside pose on my tippy toes good enough for you?

Sorry, back to my fears. I'm sure it was me who forgot to close my laptop, but just in case, I might avoid direct conversations with James for a few days. If I pretend it never happened, then he may be too shy to ask any uncomfortable questions.

I also decided to bribe him with beer. I have just enough time to run up to the corner party store and buy enough beer to fill the refrigerator. That way he will come home and be very happy when he opens the refrigerator. And if I buy enough beer, I should be able to buy his silence for several days.

Oh, and to the Anon who just messaged me, thanks. I promise that the next time someone releases on my butt cheeks, I will pretend it's you. Of course, I will lick it up for you. I'm sure you taste a lot like my own, right?

I went to the corner store and filled one of their small shopping carts with boxes of beer. I'm not a big drinker so I picked the same kind that James brings home. Blue boxes with the blue and white cans inside. This must be the good stuff.

The cashier was one of the neighborhood housewives who worked here for extra spending cash. She could have kept my secret forever, but apparently did not want to let this moment go by. She figured out that I mostly shop there as Jeff and occasionally as Frankie. I was hoping that she is the only one in Middleton who knew my secrets. Mrs. Conn also knew that I never bought beer as Jeff or as Frankie.

"What's the special occasion Frankie? You know this is a lot of beer, right? Are you having a party that a lonely old housewife should know about? How many guys are going to be there?"

"LOL, Mrs. Conn. I'm not having a party, but I am trying to keep my roommate buzzed for a few days. And from I hear around the neighborhood, you're not really all that lonely."

"Tell you what Frankie, if you don't talk about how much dick I suck, I won't tell the stock boy that you are a boy. I'll sweeten the deal by having Randy load all of this beer in your car for you. Feel free to give him something to look at."

"And send him back in with boner?"

"You know me too well. Randy, car load please."

Randy loaded my car and told me to have a good time at my party. I told him to take a smoke break with Mrs. Conn and gave his boner a few squeezes. Mrs. Conn was watching us and gave me a thumbs up through the window.

Before I go on, let me be clear. That was my biggest sex act as Frankie. Pitiful, I know. But when I add together all my nude selfies and one boner check it almost equals that I'm a whore. Remember, find me at Frankie128 and leave lude comments.

I swung around the corner to my house and filled the refrigerator with of all the boxes of beer. There, James should be quite distracted for a few days. I gave Lizzie a call to let her know I was on my way.

"Hey Lizzie, I have a box of beer and my back pack, so I heading over. What else do we need?"

"You mean a 12 Pack of beer? I hope you got the good stuff."

"The best, the cans are blue and white."

"Oh, that's hot. I'm going to order a Pizza and some salads. Do you mind picking them up from the Pizza shop on your way? What are you wearing?"

"It's simple. Socks, skirt and V-neck. Nothing special. We're staying in, right?"

"Yes, we are staying in. My plans for the night having us staying in and behind closed doors. Just make sure your V-neck is black. The folks at the Pizza shop will appreciate it. You know that we're gong to watch videos and practice our sex moves tonight, right?"

"LOL, I need a sex move before I can practice it LOL. See you soon."

I grabbed a 12 Pack box of beer and headed out. On my way out of the neighborhood I drove down the alley behind the party store. I just wanted to make sure that Mrs. Conn was on her knobby knees. Check. I mean, they say that it's a great source of protein and good for the skin.

Then I drove to the Pizza shop to pick up our food. I walked into the shop and up to the counter.

"May I help you, Miss? Did you have a pick up?"

"Yes. Do you have an order for Lizzie Bloodworth?"

"It's coming right up. Suzie, how's those Greek Salads coming? The Pizza is ready in 3 minutes."

"They're right behind you Sal. And hey you, do you know Lizzie?"

"I do. We're having a night in. We're going to eat Pizza and Salads, drink a box of beer and practice our sex moves. So, I'm guessing you're Suzie because that old guy just called you Suzie?"

"LOL, I am. So, you and Lizzie have a whole box of beer? Don't tell me, the cans are yellow and white. And I like your hair."

"No silly, they're blue and white. We got the good stuff. I'll tell Lizzie you said hello."

"Order for Lizzie Blood Slut. It is prepaid so you're good to go Miss."

"Thank you, sir. It was nice to meet you, Suzie."

"Same here Frankie. Don't drink and drive and don't get to crazy tonight. I'll text Lizzie later."

"We'll be good. And who just ran past me like a lightning bolt? She almost knocked me down."

"Brie, she works here. She either needs to drain her butt or she's jealous of the hot chick with the bare legs inside of her work. Bye."

I sent Lizzie a text to let her know that I needed her help to carry in the beer and the food. She seen me pull into her driveway and made her way to my car. She didn't have a care in the world, but I noticed that some of her neighbors were enjoying a pleasant Friday evening on their front porches. That doesn't seem like a big deal, but yesterday they probably seen Leo cutting the grass and tonight there are two extremely hot girls carrying in beer and food. It made me think that my neighbors may witness the same thing. I made a mental note to be more careful.

"I'll carry the box of beer and you carry the food, Lizzie."

"The 12 Pack Frankie, the 12 Packs of beer, not a box. Ooh, their blue and white, how cute."

Once inside, we hugged, exchanged cheek kisses and groped each other for a moment. Lizzie doesn't have the best ass in town, but it fits well inside a pair of hands. We sat down with a beer and Pizza and chit chatted. I told Lizzie about my concern that my roommate may have been snooping around my computer and how I tried to distract him with beer. Lizzie told me not to get too worried about it and told me to get us another beer.

"I don't know if it's a good idea for us to kill so many beers Lizzie."

"Slam, pound, shoot or guzzle. No one kills a beer, Frankie."

"LOL Lizzie, those are all sex move words. Would you slam me or pound me if we were going to have sex?"

"Well, if you keep acting so dizzy, I might shoot you. But I'd slam you if we were on a secluded beach and pound you every night if we were in a relationship. And I'm not guzzling anything but another one these fine blue and white beers. Oh, Suzie just sent a text. She would like your phone number. Are you OK with that?"

"No problem but send it with a selfie attached. Here, suck on my finger and look directly into the lens. Perfect. Hit send please. OK, let's clean up the kitchen and fire up some videos."

"Sounds good, but the rule for tonight is that video viewing must occur in bed. It's PJ's time."

I just wear panties and a very long T-shirt as my PJ's. Lizzie had an actual PJ set, which were very cute. We walked around the living room for a few minutes in case any of the neighbors were looking and headed into Lizzie's bedroom. We crawled under the covers and fired up her laptop.

"So, what are your goals for tonight Liz?"

"Well, for one thing, I need to actually sleep with another person in a bed for the night. I don't what it's like to share a bed with someone. And I know that sooner or later I'm going to have to put out, so I need to figure something out about doing that. Hey, do you want to fuck me in the butt tonight?"

"LOL, we won't be butt fucking tonight, but I will do my best to give you experience on how to share a bed for a night. But, beware, all of these videos start with everyone naked and the sex starts immediately. You may figure out how to take your Bull, but not how to get there in the first place."

"Point noted, but I want to watch the positions. In my head, I think I want to be a very low doggie position, so I want to see what other tranny's do."

"Whoa Lizzie. You might want to consider hand jobs or blow jobs before you get naked and stick your greased ass up in the air. Baby steps Lizzie."

"Well, I jack off every day, so I know how that works. I also practice with bananas a lot, so I'm at least prepared to have something in my mouth. Besides, the popular opinion on Chang is that I will have to give it up if I want a second date. So, do you want me to grab my lube?"

"Look, you're really cute. You will get dates. Just swipe "up" on Kinder and try it. But, let's click on a few videos and see what your future holds for you. Send another selfie to Suzie of us in bed together. Pucker your lips please."

I snap a selfie and handed her my phone. It's only fair that I have Suzie's phone number if she gets mine. While Lizzie was busy with that, I opened a few tranny sex videos and ran my hand down to Lizzie's crotch. I did this for two reasons. One, so Lizzie had a hard on while viewing videos and two, I have never seen her hard and I wanted to know what was under the covers. I was hoping to find a true monster so I could claim that there was no way I could take such a big dick. What I found was a normal sized dick that would probably fit and maybe rock my world.

"That feels nice Frankie. Do you have a plan that I don't know about?"

"Not exactly, but I did want to verify that you are too big for me to take and to let you know what's going to happen when you share a bed with a Bull. Tranny or straight, sex always involves sex parts. People grab and touch each other all the time under the covers. Hey, look at this video. Is that the position you were trying to explain to me? Mark it as a "favorite" if that's what you meant."

By this time, I had pulled her dick out of her panties and I was gently stroking it. It might be Lizzie, but it's the first bare dick I ever touched other than mine. The boner check I gave the stock boy earlier just fell way down the list of sex acts.

"OMG, yes. See how she is scrunched way down on her hands and legs? That's my dream and look how perfect the height is for her guy. He just stepped forward and entered her. That's the dream. But it is funny how they are all ready to go, isn't it? Hey, maybe we can start a new thing. Maybe we should video the foreplay and post that. Do you want to slowly remove my PJ's?"

"No one has time for that Lizzie. No one is going to jack off to silly foreplay. Maybe you should open up a few blow jobs videos. There, hit that one, the one with the two spinning circles attached to it. Oh, I like these. It's a meme about a tranny who tricked his Sister's boyfriend into waiting for her to get home from work. These are the best and they are true stories."

"Oh, you do like these, don't you? You went from gently stroking me to straight up jacking me off and now I like them too. But I think I should grab a wash cloth or something Frankie."

"Hit record and keep my face out of it. It's about time I learned what it's like to have something in my mouth."

No, I have no idea where I got the nerve to dip under the covers and insert Lizzie's dick in my mouth, but I found it. No, I have no idea how to perform oral sex other than what I seen in videos, so I kind of held still and let Lizzie fuck my mouth. I made some suction, but there is no way I can honestly post that I sucked off my hot Friday night date. Ah, screw it, I rarely tell the truth on Chang anyway.

I nodded when Lizzie asked me if I was prepared to swallow. That was so much easier said than done. I have a whole new respect for the women of the world and the rookie Tranny's. I also realized that her load is a lot more than my normal load. But I learned very quickly that you have to take a stream and then swallow. Repeat until it stops.

"You OK down there Frankie?"

"I am now. Lizzie, girl, you blow a huge load. You should post about that. Was I any good?"

"Not really Frankie, but it was your first time. Besides, you sucked the nut right out of me so there is nothing to complain about. Plus, now it would be truthful for you to post that you sucked a full load out of your hot date."

"Oh, I just did and Suzie already left a comment. Unfortunately for Suzie, I already swallowed all of your cum, so I can't post a facial photo."

"LOL, she's so naughty sometimes. But here's the deal. I'm not letting you leave with blue balls tonight and I have some cherry scented lube. So, what do you say? I mean, my PJ bottoms are basically off of me now."

"Where are you going Lizzie?"

"I'm propping my iPad up on my dresser and hitting record silly. Do you mind if I leave my panties on? I have a stupid fantasy that I am taken so fast that there is no time to remove them. Just push them aside and avoid eye contact with the camera."

"Anything else Lizzie? For someone with no sexual moves, you seem to know how to direct traffic."

I didn't receive an answer, but I did receive a small hand job. Lizzie coated my hard dick with the lube in a very slow motion. Then she readjusted her iPad camera and scrunched down on the end of the bed. I found out that there is some truth within the videos. Two steps forward and the head of my dick had a perfect angle to her tight little rosebud and the lube allowed me to just walk forward. This is not what I signed up for tonight, but I suppose sexual excitement has changed many of minds over time.

"This feels wonderful Frankie. So much better than my suction cup dildo. Give me a few slow strokes and then pound me like a slut. I promise no one will know it's you. That's it, Frankie, pick up the pace and treat me like a slam piece you found on Kinder. Hold out babe, don't blow that load too soon, but when you do, I want to fill my butt full with your cum. Are you spreading me out Frankie? Has my hole ever been this wide opened? No, it hasn't babe. Am I tight for you Frankie? You would come back for more, wouldn't you? Are you tensing up now? Do I sense relief coming soon? Let it go Frankie, I'm here for you. I promised you wouldn't go home with blue balls babe. Go ahead, fill me up."

I filled Lizzie alright. My experiences for comparison sucks, but that was the best nut I ever left in my wake. And so much tighter than that slut I hooked up two years ago.

"Was I good Frankie? Was I tight enough for you?"

"That my best ever and nothing should be allowed to be that tight. I hope you don't mind if I come back for more Lizzie."

"LOL, wipe yourself off and get in bed. I'll probably be in the bathroom for a few minutes, so try not to fall asleep on me. And please, feel free to post about that tighter than anything on planet Earth thing."