Ericka Made Over Ch. 06

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Ericka has a Sugar Momma and some red pills for the party.
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Part 6 of the 7 part series

Updated 06/10/2023
Created 06/05/2021
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Ericka made over 06

My days with Charlie at the end of last summer were the best and left me with a lot of good memories. If you didn't read Chapter 05, you can trust me when I tell you that I seduced him the first time I put on a custom fit two-piece swim suit. If you did read Chapter 05, well, it was ridiculous, but it worked.

But that was so many months ago. My cross dressing has been bumped up a few a notch's since then. I mean, look at me. Everybody loves capri leggings, right? And I'm walking my well-dressed self over to the Kindle's this morning. I look nice, but I still suck at makeup. And I can only poke myself in the eye so many times. So, it's time to make a favor trade with Mrs. Kindle. The icing on the cake is that I can see Charlie's lawn service truck and trailer in front of the house. I could handle watching my old flame cutting the grass shirtless and bending over to pick up the fallen branches. Ah, the good old days.

I entered the Kindle's property from around the side and found Mr. Kindle on the back porch swing. Because it's just barely 11 am, he is passed out, but still holding onto his Long Island Ice Tea. How he never drops his glass is unknown to science. Known to everyone is Mrs. Kindle standing in her kitchen in the nude. This has nothing to do with science. Mrs. K has a freaky side to her.

"Hey Mrs. K, can I come in and can you please put a robe on?"

"Shut it sissy and get in here. You're blocking the view and the 11:07 am train is about to roll by. What can I do for you and your sissy ass? There's still nine hours before the party starts. Be quick."

"Please Mrs. K, Tranny, not sissy. Oh, look at that. You tried to shave down there and failed. Are you still competing with Mrs. Thomas? She always wins because she has been shaving for years and you don't know jack. OMG, is that the proper way to wave at a train?"

"Shut it and tell me why you're here Tranny."

"Well, I have some free time and I really need your help with my eyes and my eyebrows. Nothing too much, just enough so I can flirt with Charlie. I'll trim that up for you in trade."

"Hah, with an ass like that, no one is ever going to look you in the eyes. Mine used to be that tight too, you know. So, we're talking about a favor trade? Ok, but we need to step it up. An Eye makeover for a real shave sounds good. But interrupting my hired help will cost you a trip to that secret sex club you get your clothes from."

"It's not a sex club and it's not a secret. It's right on the corner of Peckerwood and Pepperwood in Hillsdale. But I do have a Gold Membership. So, I fix that train wreck you created and you drive us to Hillsdale, right? And I get time with Charlie while you take a morning shower, right? And I know your tricks, the visit to Gary's Sex Clothing store is a round trip. You can't take off and leave me in Hillsdale."

"Ugh, fine. Agreed. Let's gets started sissy, sorry, I mean Tranny."

"And?"

"OMG, are you needy much child? Fine. You're cute, you're young, you have a shapely ass and you look good in tights. Yada, yad, yada, blah, blah, blah."

I wish I could do this blind folded, but I would really make a mess out of her mess. I accidently nicked her three or four times so she would jump back and yelp.

"Watch it fem boy. Hey, that looks pretty good. I think we'll work out a regular deal, maybe. I want a MBDS outfit and a collar and leash today from your secret sex slave store."

"You mean a BDSM outfit? Maybe a leather strapped leather body suit or something? No problem there, you might be able to pull one off, but the dog collar and leash thing? I don't see that for Mr. Kindle or for you. Can I go flirt now?"

"Yeah, a sexy body suit. I like that. And the collar is for future considerations. I've been lurking on some sex boards and it seems to be popular for a hot MILF to have a pet. Go get your flirt on with Charlie while I take a shower. 30 minutes and no more. And don't wake up my lousy husband."

Well, the good news is that she will need to get dressed if we're going for a drive. OK, it's old flame Charlie time.

"Hey Charlie. Are you getting everything ready for tonight's big show? Hey, you weren't spying on Dottie in the nude, were you?"

"OMG no, but there is really no spying about it. This is pretty normal for her. I don't mind because she pays me well. She likes the way keep the grounds groomed."

"And she sucks your cock a little?" Which I don't care about. So, how is Sonya and the Twins? Are her boobs sagging down to here from all that milking?"

"Oh yeah, and she's bloated like a wet sponge. But enough about that ball and chain. Let's talk about how good you look."

"Really? Thanks. So, do you want to pick up where we left off or are you still afraid to get with me? You can close your eyes. I promise to not to fall off of your lap or the tractor mower. If it helps, I will talk dirty to you by telling you that everyone knows you're tapping Mrs. Kindle on the side and from the back and sometimes from the top."

Damn, that woman is fast in the shower. There is no way I have been grinding on leggings covered butt on Charlie for 30 minutes. But there she was, screaming at me from the back door.

"Hey, faggot, I mean Tranny, I'm ready, let's go."

"Oops, time to go Charlie. Have fun cutting the grass shirtless and it won't bother me at all if you think of my hot mouth when you jack off in 3 minutes. I'll make a fake swallow when we turn at the light. I hope I see you here tonight, if your wife lets you out of the house."

"Hey, it wasn't that I didn't want you, I just didn't know what to do. I was scared and unsure of what to do. I was afraid that you would scream and call me faggot names if I tried to make a move."

"OMG, I gave you a lap dance while we were in our bathing suits and I placed your hands on my absolutely amazing boyish bare chest. Didn't you hear me moaning when you leaned up and sucked on my irresistible nipples?"

"I felt you trying to clamp up and prevent me from dry humping your backside."

"OMG Charlie, I was squeezing your hard cock with my cheeks. You were supposed to take the hint and do something. And by do something, I mean other than cum in your swimming trunks. As I was leaving, you were supposed to stop me so we talk about what just happened, behind the garage, in private. Look, I don't want to fight about the past right now. Find me tonight. I'll be wearing something special just for you and they will be purple."

"So, you don't have time to hear my apology for jacking off on your feet once when you fell asleep in the sun next to the pool?"

"I wasn't asleep. You should have known that because I actually finished you off with a foot job. There's no such thing as "sleep foot sex" and I know you still sneak into my backyard and peek at me through the window."

"Sorry. I'll find you tonight"

"It looks like Mrs. Kindle is almost properly dressed and it's time to go. If you pull me away tonight, I will pretend to be at your mercy or whatever fetish you have going on. See you tonight."

"What does that mean?"

"You can steal me away and have your way with me. It's my catch phrase. But do not trash my outfit or you will be out of the baby making business."

"Hah, I might need a good kick to the nuts. I have Twins at home and Tina is 3 months along and Sylvia is due in September. See you tonight Ericka."

OMG, guys and their side pieces. And OMG, doesn't Mrs. K own anything appropriate? And just for the record, I did not pull Mr. Kindle's cock out of his pants. He must have been "sleep solo sexing" while I was flirting with and twerking on Charlie.

However, during our drive to the Hillsdale store I managed to learn a few things about Mrs. K. One, she's actually pretty cool and she did well to maintain a nice figure after 20 years of marriage. Two, she clearly thinks that the painted lane lines and the traffic light colors are just suggestions. I would be less nervous if I was surrounded in Middleton Park by horny studs after dark than I am while riding as her passenger. I will be driving home.

"Is this it, Ericka?"

"Yes, park in the rear and push your sun dress down."

"Listen sweetie. I was watching you and Charlie earlier. I'm open minded and I'm wondering if I might see some sissy sex, sorry, I mean Tranny sex tonight? I wouldn't mind finding out how that works."

"LOL, we'll see Dottie. I'll give you a secret hand signal when Karla is taking it and giving it at the picnic table. Now remember, these people in the store are my friends, so behave yourself. And again, a sun dress is meant to be worn pushed down."

We approached the front doors and I opened them like I worked there. Yes, I filled out an application just like every other Tranny in Middleton.

"Hey Ericka. We weren't expecting to see you today, but we knew you would show up. Cute leggings and skirt, but who told you that your white V-neck was cute?"

"Well, it wasn't me child. This one should be kicked out of the Tranny faggot club."

"OK then. So, who is your friend and should I run and hide in the back?"

"Hi Frankie. This my neighbor Dottie. She is a horny middle-aged old hag housewife who is pissed off at the hand life dealt her. She and her arch enemy, Maggie Thomas, always have a bald beaver contest just before the firework show starts. It's ridiculous, but Dottie has a good chance of winning this year. So, maybe a strapped body suit that hides nothing and a sheer cover up? And don't forget the sheer cover up."

"That's too easy. What else do you need?"

"Dottie has expressed in interest in pet situation, so a cute dog collar and a chain leash maybe. Not the pink sissy collar, pick out one with spikes and a thick chain. Allie Kat is more of a skater girl Tranny then a pink sissy. We're asking for a friend."

"Alright, so if you're asking for a friend, then you need a bottle of red pills, right?"

"The small bottle of red pills will do. We will also need a small bottle of blue pills to spike the Yellow Smoothies tonight."

"Hey, what are the red pills for?"

"Oh, never mind all that Miss Dirty Dottie. I'll explain everything while we find you something to wear. Meanwhile, Ericka, we love you, but you need to stop choosing your own clothes to wear. Your cuteness and the fine clothes that Karla gave you are meant to be additives. You need a refresher course on mathematical symbols. Go to the back and find your new locker. Tori made it for you. Please, Dirty D, this way."

"Ah, why did Tori make me a locker? I don't work here, yet."

"Tori made a locker for you in back because she stole your Pixie friend. She almost feels bad about that and she almost plays fair. Right this way Dottie. Oh, well, we usually wait until we get our customers in the dressing room before we have them strip naked, but OK."

I left them to shop around and went into the back to find this locker. Locker #1, skull and cross bones, that's Karla's. Locker #2, flashing Neon Lights flashing Tori and Barbie. Moving on to Locker #3, "Frankie" surrounded by pucker kisses and glitter. Locker #4, I think that's a weapon, so Lizzie.

Oh, look at that, Locker #5 had my name on it. It was written in crayon by a 4th grader and they missed two of the six letters. That was a little upsetting until I opened it and found a bunch of matched clothing sets on hangers and a note from Tori. I swear, I cannot figure out if she loves me or hates me, but the note said something to the effect that if I dressed myself today, then I was probably so-so and I should change right now. It felt like love with a hateful body slam.

However, I took the hint and changed. There was another bike shorts combo. Blue with red stripes. The shorts, the pull over and the skirt are all matched. Cool, I am back to being cute and I guess I have a new look.

I hung my other clothes in the locker, used a sharpie to fix my name and headed out into the store to find Mrs. Kindle. I found them at the Lizzie's Cash Register.

"So, Mrs. K, did Frankie help you find anything totally inappropriate?"

"Be nice Ericka. Miss Dirty D is so happy that she added money to your account. We love our new customer, Dirty Dottie Kindle, but I'm putting the red and blue pills in your bag for safe keeping. And I promise that whatever vixen you provide to her for that fake "held against her will" thing will look good in the collar and leash I selected. She will also look good in photos you post on Chang, so have at it."

"Cool. Dottie, did you get everything you wanted today? Will you look ridiculous and make a fool out of yourself?"

"Oh yeah, Look at this Tranny boy. I'm winning tonight."

"Oh, I see. So, you bought panties made with four straps of leather?"

"Hah, I have Peek a Boo everything. That old hag Maggie Thomas is going down tonight. Hey, you're looking cute in that. Can we pick up some guys on the way home and pull over in one of roadside Parks?"

"Hmmm, maybe, but it's getting late and we should go. But do tell, why did you completely remove your sun dress?"

"It's not illegal to drive in panties, so shut it."

"OK, were you going to put on some panties or are we peeking the world on the way home?"

"Excuse me Tranny, didn't you just hear this hottie tell you how much cash I dumped in your account?"

"Sorry, my bad. But I'm driving home. You can let your boobs out and flash the big rig truckers. If we do pull over somewhere, I'll explain to you how many red pills to should feed to Allie Kat per day. Let's go."

"Who is this Allie Kat you keep mentioning, Ericka?"

"We'll talk about her on Monday, when you can walk again. Remember, I'm bringing enough guys tonight to totally wear you out. I'll bring you a cup of spiked tea on Sunday morning. And don't think for a moment that I don't know what's in those little boxes. Just remember that you can't have butt sex if you're wearing a butt plug."

"Shut it. I told you I'm opened minded. I'm not judging you for not even trying to hide your boner in those tight shorts. I suppose it was an accident that your skirt is caught in the waist band like that. Let's hit the road and pick up some guys."

"We can go, but I have to tell Lizzie something first. Lizzie, your pretend ex-boyfriend Pepper Jack was a gentleman last night at the mall and he knows he let a good one get away. His prepared statement from the bottom of his heart was four pages long."

"OMG, that SOB left off three pages? Well, whatever, I am the one who got away and he unblocked me, so he may come back."

"Damn Ericka, why haven't you invited these two to the party. I like them."

"They are both working tonight, but the August event for sure. I have another plan. Bye guys."

"Bye Ericka. Tori does love you and she will see you tonight about midnight."

"She will not see me tonight. I had Brooke banned from the event."

"Hmmm, we'll see, Kiwi Charms, we'll see. Have fun tonight."

I did drive home because I at least tried to stay between the lines and actually stopped at the red lights.

"Pull over into the Ice Cream shop Kiwi Tranny. We can sit on the bench and lure guys into our traps. Plus, we need to talk. If you want me to be your Sugar Momma, you need to start communicating with me and we can start with Allie Kat and your plans for the August event. Hey, do Tranny's have Sugar Momma's or are those just silly memes?"

"I don't know, but it's probably the same as those hot MILF memes where they have Tranny's on a leash. We can tease guys while we eat ice cream in a seductive manner, but Allie Kat is for next week. I cannot deal with her right now. But you have to put your tits back in before we go to the window."

My new Sugar Momma bought us some cups of ice cream and we sat on the bench and forget to sit like ladies.

"Listen Kiwi Charms, I don't think your plan is going to completely work tonight, but I'm giving you full credit for having a plan and for all the effort you have put forth. I didn't want to say anything, but your plan failed to account for the booze and the spiked Smoothies. Rules go out the window when people are all high and stuff. But, again, I'm glad you came up with a plan as opposed to my free for all concepts. So, what's on your mind for August?"

"I haven't given it much thought, but off the top of my head, I was thinking of a dual event. One, it's a Luau party. Grass skirts and sea shell bikini tops all the way. It also includes 100 Tiki torch lights and two Tiki Bars. Tori can modify the costumes to expose maximum skin and we'll need some chain to lock up three or four of the worst husbands. We'll use them as a sacrifice to the Fire Gods. The guys will wear grass skirts below the knees and they can wear loin clothes so they don't poke out between the blades of grass. The ladies will wear mini grass skirts and will be commando. Learning to sit down will be up to each individual female."

"Well, that's quite a lot for right off the top of your head. What will your Tranny friends wear?"

"That's open right now. Every time I start a conversation with "I have a plan" they run away. But, if any of them attend, they would wear knee length grass skirts and a banana sling. Half way in between the guys and the ladies."

"Alright, what's part 2 of your plan?"

"I haven't given it much thought, but if Mr. Kindle could makeover the shed using these blue prints, it would help me out. If he follows the blue prints exactly, the secret project should cost less than $189. My idea for the revised and upgraded shed is a secret for now, but I promise, it won't disappoint."

"Hmmm, 100 Tiki torches, three sizes of grass skirts, Tiki Bars with built in glory holes and a secret shed, huh? So, all of this is off the top of your head, right?"

"Right off the top. And if we're lucky, the store will get the first orders of the new and improved purple pills just in time for the Luau party. I haven't really thought about it, but if I can get more of the Middleton Tranny's to use the purple pills, I will need your approval to extend extra invites to more guys. Everyone should be paired up. I'm nice that way. Should I go wait in the SUV while that guy finger bangs you like that?"

"No, go behind the SUV if you're going to use your ice cream as a lubricant to jack your new friend off. I don't want my seats to be a mess."

"Well, maybe we should get an ice cream station to put along side of the Smoothie machine for tonight."

"Consider it done."

"Be honest with me. Is anyone going to listen to me tonight and do what my secret hand signals mean for them to do?"

"In the interest in our new friendship, I will not be answering that question. Your friend Karla, the boss lady, came into the dressing room while I was trying on things that can't be called clothes. Don't tell her I said this, but she only needs you to get past the sign-in table. Maybe you should bring your other friend Allie Kat along tonight so you not the only person standing around alone."

"Screw it, let's get home. I'll work the ice cream station along side of the geeky guy who runs the Smoothie machine and I already know you give him blue pills before the events."

"Alright then, so tonight is a disaster. Have you already begun thinking about the Halloween event? It's on a Saturday night this year."

"Hmmm, I haven't really thought about it, but maybe a Witches and Warlocks thing. The costumes are dirt cheap and Tori can rework them in 15 different ways. But, it's early still. I'll see you tonight. Thanks for driving today."

Charlie finished the yard work by the time we arrived back home, so I slowly walked the 2 doors down the sidewalk to my house. It's a shame to waste these fine bike shorts for only a few hours of showing off, so a show for the neighbors it was. It was a big surprise to open my front door and find Allie Kat taking a nap on the couch. And you may think I can't match clothes very well, but no Tranny looks good in Tweed Harry Potter Hermione Granger shorts. Especially when they are the real thing and cut below the knees.

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