Winky 01

Winky Winters 01

Hi there. They call me Winky and they call me that because my eyes blink about twice that of a normal person and I have dealt with it for my entire 21 years. Other people haven't dealt with it so well, but most folks are kind about it once they realize I can't control it, but it's understandable how it might freak a few people out. Needless to say, I wear a lot of sunglasses. Oh, also needless to say, LOL, I am a master at batting my eyes when eye batting is the way to go to get what I want or need.

By the way, I go by Winky in my fem life too. It always seemed easier to simply identify as one name and Winky seemed to fit me no matter what I was going to wear on any particular day because my eyes blink like crazy anyways. LOL, needless to say, eye lash extensions don't work for me in my fem mode. They come off like a factory slicing machine or something and even freak me out. And forget about the one time I tried to combine eye lashes and those stick-on crystal eye studs. I looked like a landing strip on a Navy ship.

As I mentioned, most people can handle my issue, a few are freaked out by it, but most became used to it and moved on. The problem was that sometimes there wasn't enough time available to allow people to get over it or used to it. One example of that was the roommate selection process. It took me longer to find a suitable roommate then it did my master my cross dressing and makeup skills.

And then I came across the perfect roommate candidate, Dale. Dale seemed reliable and actually came with a recommendation. Given what seemed like a good interview, I determined that Dale would be a suitable roommate because Dale does five things. He works, he eats, he sleeps, he gets lost inside of his interactive video challenges and he smokes blunts a lot and I mean a lot.

To Dale, my eye blinking probably seems normal, LOL. And I promise you that my role playing came up during our interview. I mean, I don't know what he heard, but I did mention that he should expect to catch me dressed from time to time. Either he heard me and understood or his heads bobbles back and forth naturally or because of the blunts. Whatever, I came clean and that was that.

Now, for both of our benefits, I gave up the small den close to his bedroom as his gaming and smoking room, but he had to keep a fan in the window that blew out at all times. A problem for the neighbors for sure, but better for me and the rest of the house. And yes, in all fairness to the story, I jacked up his rent to account for the extra den room and yes, Dale is aware of that and is "cool, cool" happy to have his own space.

Oh, by the way, when you see the City Street Sweeper truck coming down the street, it's Dale, so give him plenty of room on the street and keep your small pets inside. Unless you find his "cool, cool" response acceptable as you explained to him that "Rover" was swept up inside of his truck.

And away we went as roommates. Whether I wore sunglasses or not, it wasn't unusual to catch me at the Microwave in my standard double panties of hugger briefs and bikini brief undies and it wasn't unusual for Dale to stare blankly into space and say "cool, cool" and return to his fantasy land den.

I remember that he rarely remembered much. Unfortunately, as I remember it, he had more friends stop by occasionally that I did, but mostly because my nerd friends were afraid of the way Dale seemed on the surface. His mindless stares did take a little getting used to, just like my eye blinking issue took getting used to. It just took longer my geek friends to realize that he was not in a slasher movie last year.

Fortunately, I think, I remember Dale's friend, Stan, had an eye out for me. Stan was the first guy to pay attention to me as the fem Winky in person. And I remember that being very refreshing over the lurker attention that my Chang homepage offered. I think it's safe to say that it didn't take long for me to fall into the attention appreciation trap that Stan presented to me. And I was happy to present Stan my role playing Winky as much as possible in return. The attention was worth the risk.

As I remember it, it all started out slowly and by that, I mean in sneaky ways. I was never going to plop down in the arm chair in the den dressed in PJ shorts, a small t-shirt and my hair selection of the day, but I would mill around my side of the house or the kitchen in the manner of my choice. If I got caught, then so be it and if Stan got close to me to acknowledge that he caught me, then so be that too.

I remember all that being a cat and mouse game for a few months, which was alright because even though I liked the attention that Stan's eyes paid me, hell, I didn't know what to do about it. I think it was in June when I remember the cat and the mouse agreeing to disagree, as they say. Play, catch and release to play the game again a few days later.

Now, if you talk to Stan in person, I guarantee you that he doesn't remember our first one on one time correctly. I did not send him a text while he was in den with Dale and provide him with the GPS location of my bedroom. As I remember it, he took a wrong turn in the hallway when he exited the bathroom. He remembers it as me standing there is jammies pointing towards my bedroom, but my memory has it as he popped his head into my bedroom and with some lame "oops, excuse me, Winky" excuse.

My proof of Stan's faulty memory is that he will tell you that he caught me waiting for him in the hallway in striped jammies that peeked the bottom of my globes. As I remember it, none of my jammies were striped.

However, in all fairness, I'm sure we both remember how long we stood in my bedroom doorway as we discussed his accidental wrong turn. I remember that my fem Winky never went looking for a boyfriend, but I also remember how nice it felt to be in his embrace. I may or may not remember locking my leg around his to keep him close to me, but I absolutely remember him massaging my chest. It makes for fond memories when your surprise visitor doesn't care that he his pinching and rolling boy nipples. I don't remember a lot after that and I can't for the life of me remember who humped who, but I clearly remember his groans of pleasure as he made a mess in his cargo shorts.

I remember that moment being so embarrassing for both of us and I remember his precious expression as he covered himself and left the house suddenly. I even remember the series of texts we shared as he drove home with wet shorts and I remember them because I saved them. I even screen shot them because I wanted to remember fem Winky's first sexual experience (with another person).

LOL, I definitely remember posting on Chang that Winky doesn't need to wear sunglasses at night. And then I remember my roomie wandering around the house looking for his friend.

"Hey Winky, have you seen Stan? It's his turn."

"Stan had to leave Dale. He spilled his soup in his cargo shorts. It was hot soup and stuff."

"Cool, cool, hey are you decent Winky?"

"Not really Dale. Stan spilled his soup on me too. It was hot soup and stuff."

"Cool, cool. Hey Winky, are you decent?"

"Not really, Dale. Good night."

"Cool, cool."

I remember reminding myself that any further cat and mouse games could result in me finding myself in a deeper sexual situation than I was ready for, but I kept remembering how amazing it felt to be appreciated. Unfortunately, as I remember it, my choices were slim. Stay in the closet, reveal myself and end up in the Cottonwood Street alley with the other Tranny's who don't have regular boyfriends, hang out near the Men's Rooms in the clubs or carry on with Stan for a while and come up with better codes to kick off the cat and mouse games.

I remember Stan being the clear front runner and head master cat. LOL, I remember making great efforts to make my tail as attractive to him as possible, without advertising it as for the taking. Fem Winky had her limits, but Winky had a nice tail to sway back and forth to set the trap.

Wow, I remember laying in wait for Stan to use the bathroom by peeking through the crack in my bedroom door. I don't remember being as quick as a Cheetah, but I was inside of the bathroom before he knew it and I laid out my list of codes as fast as I could. Listen for the beeping of the Microwave, the rustling of plates or cans, read your texts, just open my bedroom door and things like that. I remember that he liked my Denim shorts and I remember promising him that we would find a solution to the wet spot issue. LMAO, and I really remember how he couldn't "go" with a boner!

And then I remember wiping up the floor and bowl rim because I didn't know how to aim his thick rod at the toilet bowl very well, but I remember it as my second sexual experience. I remember posting my Winky code for by reminding my followers that I didn't wear my sunglasses that night.

Stan refuses to remember that I kissed him, but I remember flicking the tip of my tongue on his lips at least once and by that, I mean it was probably twice. I also remember reminding him that it was the kiss that helped him recover so quickly, but, as I remember it, he was a little freaked out by that, so I backed off and saved his macho status.

I wish I could remember who had who hooked, but the games continued and the game level increased with each visit. By the way, he was hooked on me because as I remember it, he increased his visits from a few times a month to every Thursday and I remember him asking me to wear a certain outfit to make the popcorn for the video guys that night. I remember that was very naughty of Stan to ask that of me, but I absolutely remember doing it.

I would never wear my Capri tights without a skirt in front of anyone due to the lack of coverage, but I remember asking him which pair he would like me to wear. And oh yeah, I remember him whipping off an entire outfit and suggesting that I rub myself up a little to increase my visibility. The nerve of him, right? However, I also remember whispering in his ear that I didn't need to rub anything when he was around. I was surprised that he never considered that I get turned on too, but I remember being pleasantly surprised when he made the extra effort right there and then to make sure my small package was as exposed as much as it was going to get. LOL, I remember those naughty selfies!

I remember posting on Chang that not only does Winky not wear her sunglasses at night, her un-named partner does have a care in the world that Winky has a weenie. I may have worded it funny, but it's what every Tranny wanted. I remember one of the most popular memes on Chang went something like "So what if I have a dick? I'm still cute and you're still horny." LOL, I remember having it as a screen saver for about three days. I still remember what folder that meme is saved in too.

Unfortunately, I remember responding to Stan's "ready" text and delivering the three bowls of popcorn to the den in my Capri tights. Oh, I remember being very grateful for the lack of comments, but I remember the stares. I mean, Dale stared at the screen and didn't notice me and Stan made a point of showing me off to the other guest, Hank, but I remember Hank's jaw drop and Stan smiling. LOL, I remember the glare Stan gave me when he figured out that I was about to lean over and kiss him on the cheek, which I saved by picking up the empty beer bottles. That's when I reminded myself that bending over in yoga pants isn't much better than showing in the front. LOL, Hank will remember me! Hank could probably read the size tag on my undies through the stretched out thin material of my tights.

It was only a few minutes later when Stan made his way to my bedroom. As he remembers it, he was the aggressor and basically ripped my tights off and pinned me to the wall with my arms held high. That time, Stan's memory was correct and he remembered it well. I don't what it's called or if it even has a sex position name, but he had his way with my exposed buns and the crack between them. I don't know how I knew how to help things out, but I remember pushing back and rocking my backside to match thrusting his actions. I remember the moment when I knew it was over and I remember not caring about the mess that was about to be everywhere. Stan may not remember it, but he showed his fondness again for my chest again. As he pinned me to the wall, he used my chest as his holding point.

Oh, I remember him saying that he wanted it to be on the inside next time and he probably doesn't remember me saying that I wasn't ready for that, but I promised to level up the game again soon. I made my promise of a next level game to him by turning around and seeing his completely nude body for the very first time. OMG, that was very easy to remember.

I remember thinking that it would be an easy promise to remember and I may or may not have thought to myself "damn", this is how a couple should look when side by side. One taller than the other and one softer than the other.

Most of all, LOL, I remember Dale's voice in the hallway as Stan scrambled to get his clothes back on. I also remembered his ability to recover so quickly (and I'm trying to forget that he has no control and pops off even quicker). I remember being ashamed and amazed at the same time. My tool has never stood out like that, let alone bounce like that. I remember that being very hypnotic. And damn it, I remember being snapped out of that trance!

"Hey Winky, have you seen Stan? It's his turn."

"Stan had to leave Dale. A dam broke outside of town and he's trying to plug the hole."

"Cool, cool, hey are you decent Winky?"

"Not really Dale. I'm trying to keep my water dam hole from being plugged."

"Cool, cool. Hey Winky, are you decent?"

"Not really, Dale. Good night."

"Cool, cool."

I remember carefully planning my "surprise, you caught me" evening when I knew there would a video challenge going on in the den room (Duh, almost any day of the week). I thought I would surprise Stan by letting him "catch" me taking a nap in skimpy sleepwear. I felt confident that it would work because he is the only one who has ever entered my bedroom, door open or door closed.

My plan was to look too irresistible when he lifted the blanket and spied my mostly naked body laying there fast asleep. The buns he liked to work over so much would be pointing right at him, but I would have to be manhandled a little to expose my charming boy nipples. Either that or he goes with his standard reach around.

I purchased the smallest pair of sleep shorts I could find and a new pair of undies that I could manipulate by hand. Regular thongs are great and I wanted that disappearing dental floss look, but thongs only work for CD's while posing for selfies and I didn't want my dangling equipment to become the center of attention. So, I twisted and folded a pair of bikini panties and made my own small strap of material. I had my holding power in the front, I had a make shift disappearing rope in the back and a new bushy ponytail wig on top. (LOL, selfies were posted).

Unfortunately, Stan seemed to have a hard time sneaking away from the guys and as I remember it, I actually dozed off. However, I clearly remember being stirred awake by the movements of another body. Fortunately, it was Stan, but unfortunately, I missed the look on his face when he lifted the blanket. Fortunately, I had my laptop recording the event and captured his reactions. Unfortunately, I captured his face so I couldn't share the video and unfortunately, some people are missing out on how well his hard on bounces, points and leaks. I may or may not remember blurring out his face and posting it anyways because that was another reason why Winky doesn't need to wear her sunglasses at night.

Anyways, he did have to wake me up and I was surprised to find him getting quite busy back there, but I remember it was a nice moment to look back over my shoulder at him, which also released my chest from the bed for him. Stan may not last very long, but he crams in a lot of business inside of his 3 minutes window (sorry Stanley).

I remember asking him to be careful back there, but I don't remember telling him to stop, even when I felt his head pressing up against my "exit only" sign. I remember that it felt quite nice, so very nice and then I remember praying for his lack of staying power to beat his pushing forward efforts. I wanted Stan to win, but I was still in a place where the victory needed to be on the outside. Anywhere outside was fine with me, just as long as it was an outside win.

I do remember we both won and got what we both wanted and OMG, I remember his pressure feeling like a fire hose! Damn, I remember that well.

Unfortunately, sex is messy and I remember a huge sticky mess everywhere. And as a volunteer Fireman, Stan had a hose full of foaming fire retardant to put out the flames. My memory may be a little jaded after that, but I remember a small possibility that a small amount of his creamy translucent man juice may have bypassed the "exit only" sign, but I remember not caring at the moment because even though he remembers it differently, he planted a big kiss on my neck. After that, all I remember is doing a lot of laundry the next day.

Unfortunately, we had to deal with Dale's voice on the other side of my door again. Or as I remember it, I had to deal with it because Stan had lips firmly latched onto my nipples as he quickly recovered.

"Hey Winky, have you seen Stan? It's his turn."

"Stan had to leave Dale. He was desperate to claim the last virgin in town."

"Cool, cool, hey are you decent Winky?"

"Not really Dale. I'm still the last virgin in town, but it's only a matter of time, probably."

"Cool, cool. Hey Winky, are you decent?"

"Not really, Dale. Good night."

"Cool, cool."

I remember our cat and mouse games working. Dale didn't suspect anything, Stan couldn't get enough of me, yet respected my desire to keeps where they were and Winky had many more reasons why she didn't need to wear her sunglasses at night to keep from chasing anyone away with her weird blinking eyes.

And to prove that my secret relationship was safe, I had a candid conversation with the roomie, you know, after he smoked a few blunts (Duh, any time of the day).

"Dale, I'm sexually involved with someone and I almost have a boyfriend."

"Cool, cool. Hey Winky, have you seen Stan? It's his turn."

"Damn it, Dale, I'm trying to tell you that I may an overnight guest from time to time."

"Cool, cool. Do I know him?"

"Well, he is a gamer and you know those people, so probably. He and I also play other games."

"Cool, cool. Hey Winky, have you seen Stan? It's his turn."

"Listen, I came clean with you and that's that. You got the 7th of the month rent?"

"Cool, cool, I got that right here, but I might be short for the 14th of the month rent."

"It's cool Dale, just double up for the 21st of the month rent."

"Cool, cool."

Ah, I could go forever with that conversation because that conversation went on forever, but the point is that I came (somewhat) clean with Dale out of respect for his friendship with Stan. And because he pretended to remember what we spoke about I went out and got him some more baggies of smoke. Well, I think I did, I mean, it could have been mountain grass clipping for all I knew.

Talk to you guys soon, xoxo, Winky.

End Winky Winters 01