Lolli Pop 01

Story Info
Lolli Pop didn't start out as Lolli Pop, but ended that way.
3.5k words
3.47
4k
00

Part 1 of the 2 part series

Updated 06/11/2023
Created 04/14/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Lolli Pop 01

Trust me, Lolli Pop was not my chosen fem name. I actually started out as Lilly Lux, but that didn't last long because the first words out of Jake's mouth when I initially revealed myself to him and the guys were Lolli Pop and the rest was history. Which pissed me off.

Being referred to or seen as Lolli Pop wasn't what pissed me off though and it wasn't even Jake himself that pissed me off. It was the fact that it was right in front of me the whole time and I looked right past it. Silly cross dressers, right?

If you have ever been inside of my house then you know darn well that I have coffee cups full of Lolli Pops literally everywhere in my house and I mean literally everywhere. So, it was right there in front of my face the whole time and I never seen the forest for the trees. This is what happens when you're to engulfed with thoughts of "am I a black Denim CD or a blue Denim CD?" and things like that.

Anyways, hi, I'm Lolli Pop and I'm a silly cross dresser. Prior to my renaming I had established a Chang page for Lilly Lux, but she's retired now. If you're the detective type, you can lurk on Lilly's page and follow the clues from the posted selfies to find my Lolli Pop page. I mean, coffee cups filled with Lolli Pops are literally visible in every single selfie. Also, yup, I used that one coffee cup full of Lolli Pops as a blocker in that frontal selfie in the bathroom and I still didn't see it.

So, hey there, I'm Lolli Pop and Jake pissed me off, for a minute.

All of that was all a while ago and the river of life has continued to flow under the bridge, so everything is good now.

Before I tell you a little about myself, let me just say that, OMG, Lilly Lux was on such a trim and proper path, so I'm glad that cold fish is back in the closet. I mean, her long lost Chang homepage banner said it all, right? I mean, who in the hell boasts about being as fresh as a new blooming Lilly flower?

Anyways, I'm silly enough alright because I like to live free, but I'm not sassy. I'll engage in a fair amount of back and forth with you, but I'll back it down if I detect that you're getting frustrated with me. I don't want you to walk away from me without at least saying that you'll call me another time.

And without being to sassy, I have an answer for everything. Like if we're hanging out and you try a cheesy line on me like "why do you look so good in those jeans?", well my response is probably going to be "because you're horny and I'm 20" and things like that.

I also have absolutely nothing to hide. I mean, I don't flaunt my true gender by walking around in just a pair of tight tights or anything like that, but before the rubber meets the road, I will point a few things out. I would rather have you excuse yourself early in the flirting rather than find yourself in a position to side step me in embarrassment at the last minute. I play fair.

I like hanging out at the multitude of city festivals and I use the evening darkness to my advantage. I've wandered off to the edges of the festival grounds a few times with a guy, but the rubber never met the road there. I do have a favorite spot and I do like the way Danny gets a handful of my bare bottom skin, but I don't consider that as any rubber meeting any portion of the road. It's just a gravel side street. It also just so happens to be a back road that I like to take from time to time and I haven't gotten lost yet because SOB, Danny knows that road like the back of his hand.

Ah, as for my sex life, LOL, re-read above. And then invite Danny out for a beer and grill him with a few questions for me because I'm not convinced that he knows for sure that he splits a boy's butt crack with his fingers at literally every single city festival. And then follow that question up by asking him just how in the hell he got so good at it.

And yeah, yeah, yeah, if I actually played "fair", then I would bring it up, but it's just so easy to get caught up things, right? Besides, there is an off chance that he does know that Lolli Pop is a shy guy dressed as a girl with a crazy nickname and he's actually playing me, so who is not playing fair now? Well, it's still me, but still, right?

Alright then, let me give you my take on the whole Lolli Pop thing came to be.

Without mentioning the name brand, there is a soda company that has a full array of novelty items and I found myself collecting their novelty coffee cups that had a matching ceramic tile and obviously, I place the coffee cup on top of the ceramic tile like it's a matching coaster and I have them spread all over the house, the back deck, the pole barn, the attic, the basement, in the living room on a fancy ladder style shelf unit, on the game console and on and on. And the coffee cups are full of Lolli Pops like a bouquet of flowers. And very colorful flowers too because I only buy the good suckers.

Also, the guy at the candy store likes it when I come around, but Henry is a total basket case story that his wife needs to submit, not me.

Anyways, that's my side of the Lolli Pop and coffee cup array story and I started out my story with how Jake identified me as Lolli Pop, so there it is folks.

I can't clutter this story up with the entire business venture I entered with Teddy, Jake and Frank, but let me just say that whatever I say, my good friend Teddy is not involved. We have been friends for a long time, we have been that way and he doesn't mind how I live my life, so where ever I go with this, well, Teddy is innocent. Teddy likes the girl's and I like my girl's undies and everybody is happy.

But a while back, Teddy introduced two of his co-workers into my life, Jake and Frank. The three of them came to me with a small business proposal and it didn't sound half bad. They would do this and that and I never had to break or chip a fingernail and all four of us would make a few extra bucks along the way. I mean, that's gold, right?

To make a long story short, the three of them work at one of the local shops and they figured out that the shop scraps perfect wood pieces that could be repurposed into something else with minimal reworking and finishing. I call them ladder shelfs and they can be ordered in variety of wood shades. They are actually pretty cool and I'm sure you have seen similar products before. I mean, is it ladder in the living room that doubles as a shelf or is it a shelf unit that looks like a ladder, right?

And what did they need from me? LOL, two things. One, my pole barn and two, LOL, I direct the pizza delivery guy towards the pole barn by pointing my finger. I mean, once in a while I have to use my middle finger to direct the pizza delivery guy because he's such a little freak, but I was making a few bucks and not one single broken or chipped nail. Gold, right?

Well, that's when Jake tagged me as Lolli Pop. On the day that I had them over to finalize exactly how little work was expected of me, I decided to show them how they should expect me to dress. Well, I greeted them as Lilly Lux and that was the Lilly's last day on the job, thanks to Jake.

Before I go on, let me address Frank. Ah, Frank is basically out my story just the same as Teddy is because I can't figure out Frank's deal. He doesn't talk about girls and he doesn't talk about boys. As a matter of fact, the only reaction I got out of Frank was when I expressed my concerns over the legality of our business. They said that the shop was cool with them taking the scrap material for profit, but still, right? I mean, just how popular would I be in the prison showers, right? LOL, he almost laughed.

With all of that out of the way, there I was. Freshly tagged as Lolli Pop with two invisible guys to the right and Jake with his wandering eyes to left. Well, hells bells, right?

I don't know if it was Jake himself or the thrill of having a pet name, but I engaged with Jake over the next several weeks. It was fun, it was somewhat harmless, it was exciting, it made me think of the good old days with Danny behind the tree lines and it felt safe. I certainly hesitate to call it a relationship at any level, but it probably was at some level. Also, I totally fell for the "pet name" thing.

Needless to say, that fateful day when the four of us met to finalize our business agreement, was a very fateful day. Not only did we agree on profit sharing and appropriate working hours out back in the pole barn, we all agreed that my orange jumpsuit would include my inmate number, a name tag and my cell block number. I mean, "oh, so you 10 prisoners are looking for Lolli Pop? Cell block D", right?

Well, at the end of our business finalization meeting, LOL, I followed Jake towards the bathroom as the guys prepared to leave. And no, we were in my house, so that can't be stalking, but yes, I snuck up on him.

"Damn Lolli Pop, you startled me here in the hallway. What's up?"

"Well, for starters, I wanted to thank you for my new name. I really like it and I still can't believe I didn't think of it. I mean, duh, right? Anyways, I just wanted to ask you one last time if your boss is alright with all of this because just imagine what I will be mopping up in the prison lunch room when they assign me to mopping duty. Also, are you saying that you like the way I look in these jeans?"

"LOL, relax, we'll tell the police that we drugged you and stole the key to your barn, you know, four or five times a week. Besides, what makes you so sure that I like the way you wear those jeans, Lolli Pop?"

"Ah, this, Jake."

(Point, stab, poke, point). Oh, you want the truth, do you? (Point, poke, poke, press, trace, poke).

Hah, that was a bold move for someone who just took the slutty name of Lolli Pop merely 30 minutes ago, right?

"Hey, just remember that you're starting something. I mean, let's put that in meeting minutes, Lolli Pop."

"Whatever Jake, just try to keep me out of prison. But listen, you guys gave me three weeks to think about our business venture and I used that time wisely to you know, check you out. So, I know you have a girlfriend and I'm happy for you, so if you're thinking that your pet Lolli Pop is going to go all Lolli Pop crazy on you so your Lolli Pop can Lolli Pop off, well, that's not happening."

"Geez, all of a sudden, I miss that frigid cold fish Lilly Lux, but I'm glad that I struck a nerve within you by giving you a pet name. But listen, girlfriend or not, why don't you review the meeting minutes with me one more time before I leave tonight. And please, include all hand gestures and don't forget how I get to Lolli Pop off in your sweet mouth."

"Do you mean my hand gestures like this where I poke and press while I try to settle in my mind how I can become your personal little Lolli Pop so I can go all Lolli Pop crazy on your fat Lolli Pop until your Lolli Pop goes all Lolli Pop popping off? I mean, the girlfriend, right? I play fair, Jake."

Oh, meeting adjourned, I guess.

Wait, did he say mouth? I never said anything about Lolli Popping off in my mouth, right? Did you hear me say mouth because I don't remember saying anything about him doing anything in my Ripe Red Raspberry glossed mouth. Well, I never heard me say any such thing, but I did hear Jake screaming and not a moment too soon

"JAKE? Are you using the bathroom or rebuilding the bathroom? Let's go. We need to steal our scrap pieces after hours or we're all going to prison and your precious little Lolli Pop isn't going to do well in the laundry service room. I'm not saying that I check my friend out from time to time, but seriously, add a belt to her orange jumpsuit and watch out Cell Block B, right?"

Hah, I knew it! I'll be the only one in belted orange jumpsuit that has a name tag on it as I dish out the lunch room hash and the ass a little later. Hah, I knew it!

"You better go, Jake. I mean, we're business partners now and you have a girlfriend, so you know, no private meetings. Say hey to the girlfriend for me. Also, never say hey to girlfriend for me."

"Yeah, well, as an equal shareholder, I'll call a private meeting whenever I want to. Also, if Shelia ever stops by to check up on me, well, you still own some "Lenny" clothes, right?"

So, that's basically how Lolli Pop stuck her foot in her mouthful. I had no idea how all that Lolli Popping stuff came out of my mouth, but it did and Jake liked it and that started a new path of adventures.

Over the next several weeks, the guys had the operation up and running and they actually producing some nice shelf units. They were working, they were having fun, I directed that little freak towards the barn to keep them fed, we were all making a few bucks and I even started to sass back to Timmy the little delivery guy freak. Oh, and everyone was happy.

Well, Jake's trips up to house during working hours started to increase. I mean, they are guys and guys have no problem going behind the barn, but Jake insisted on interrupting me while I was kicked back on the couch in my leisurewear (work uniform) as I watched Chef G throw pork chops around the kitchen.

I suppose it fair to say that he started to wear me down and it's only fair to say that I looked forward to his need to pee in private visits. I mean, it gave us a chance to talk in private, which was the best way for me to keep up with us committed relationship with his girlfriend, Shelia. And fine, to be even more fair, I lurked her on social media, so I knew when Jake was lying.

"Jake, you know I play fair, so I kept one pair of your boxer shorts from the laundry and put them in my bedroom. I mean, just in case you ever need to take a shower or something."

"Cool Lolli Pop, but it wouldn't kill you to fill one of these coffee cups with lubricated condoms instead of Lolli Pop suckers! It just wouldn't kill you, I say."

"But Shelia might kill me. Besides, how do you know that one of the novelty coffee cups in my bedroom isn't filled with premium condoms?"

"OMG, did you fill a cup with "When You Need It Really Wet" condoms?"

"Ah, no, but I've never purchased condoms before, so I hoping you would throw a name out there. Also, seriously, "When You Need It Really Wet" condoms? Sounds like maybe you have been down to the Cottonwood Street alley before."

"Never mind that. So, are you going to tell me the Lolli Popping off story again tonight?"

"Sorry Jake, but Frank is single and he dry humped me last night, so maybe he can watch me suck a Lolli Pop sucker soon."

"Ah, excuse me, he pushed you out of the way when that ladder piece fell because you know, you were looking at your nails instead of paying attention to the shop. And stop coming out to the shop in bare feet and flip flops. Even one of our small wrenches could chip your toenail polish and I saw your post about how you want someone to suck on your cute toes while you suck on a Lolli Pop. Also, Frank still asks questions about the correct way to jack off, so don't get all Lolli Pop involved with that."

"Well, stop lurking on my Chang page and stop making comments about how sad you are because you and Shelia broke up. A spat is not a break up."

Oh, I'd like to tell you that I won because that shut him up, but I think I lost because he shut up, gave up and went back out to the barn to finish up. I mean, I'm all about going back and forth and I was so ready for so much more. But I let him go because Teddy bounced in at one of his perfectly timed moments and presented his next big idea. He said that they reached one hundred units sold and he thought we should celebrate by having a small victory party in the pole barn, you know, after the guys cleaned it up a bit.

"So, what are thinking Teddy, extra beer and us? Like most other Saturday nights?"

"No, a real celebration, like extra beer, us and streamers hanging from the ceiling."

Well, if you're going to throw a celebration party, go big or go home, right? I mean, curly streamer paper from the ceiling, right? I mean, sure, and I would call TV3 News and warn them in advance that Chase Stevenson, live at 6, 7 and 11, will have a blowout story to cover.

I didn't say yes or no because I was still flustered over the fact that Jake couldn't carry on a simple back and forth argument for more than one minute, but I did stop the party supply store on my way to the pharmacy. I mean, what was I going to, let Teddy buy one roll of dark blue streamer paper, two six packs and call it a party? Hah, Chase Stevenson, live at 6, 7 and 11 wouldn't even leave the news room for that.

Anyways, my stop at the pharmacy was quite interesting. I held my head low as I told the young clerk at the pharmacy that I was a little embarrassed, but she didn't hesitate to give me the once over before she handed me a box of "when you really need it wet because he is as tight as a fresh Lilly flower" condoms. Also, I'm not sure if she gave me a smirk or just a quick smile.

Oops, also, the young female clerk at the pharmacy was Shelia because I checked up on her too through social media and figured out where she worked.

On my way home, I did a little clothing shopping too because we were having a party. I bought some new jeans, some new capri jeans, a few tops and a unitard because it looked like it would run up my butt the way Danny used to run his fingers up my butt. LOL, it did, but it was no Danny, but my selfies, right? LOL, no need to ask any questions where my backside starts or ends, even though the lurkers kept acting like they were confused about things and kept insisting on various angles. LOL, I played fair to their requests until I figured out that I was repeating poses and they were repeating their comments. Silly little lurkers, right? Taking advantage of a silly CD who knows he will probably only have this ass for maybe just another year or two and isn't afraid to capture an imagine or 50 of it now.

Anyways, I retired the unitard and placed it near the retired Lilly Lux and informed the guys that the celebration party was a go.

And as for the string and hot glue gun that I bought from the "We Be Parties" supply store, well, some girls braid wood and plastic beads in their hair for that clinking and clacking effect when they walk. I thought I might try and attach some Lolli Pops to my clothes to see if I can go all clinking and clacking as I wandered around the party.

End Lolli Pop 01

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

story TAGS

READ MORE OF THIS SERIES

Lolli Pop Series Info

Similar Stories

Feminization Triggers What makes feminization such a powerful experience?in How To
Conversation with Gabriella Ch. 01 Gabriella explores her sub while all share her wife.in Transgender & Crossdressers
High Heels and Stockings Tryout Trying out his wife's slut clothes.in Transgender & Crossdressers
A Cross Dressing Suck Off Fantasy... Man on business meets sexy cross dresser.in Transgender & Crossdressers
Nicki's First Time Nicki is forced to confront her fantasies.in Transgender & Crossdressers
More Stories