Kimmy's Discovery Ch. 04

Story Info
The continuing story of young Kimmy and her self-discovery.
7.2k words
4.63
9.9k
8

Part 4 of the 6 part series

Updated 06/08/2023
Created 03/14/2017
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
Deviana
Deviana
90 Followers

We left off (sorry for the delay!) with Kimmy facing the challenge of calling home to let her parents know she wasn't going to be home...

Let your parents know you will not be coming home tonight."

i felt nervous- how to tell them, what to tell them. But i was not going home. Shaking, sitting to calm my voice and my hands, Dougie sat next to me. Dougie handed me the hands-free phone and whispered in my ear- "Go on, sweetie. Let your mother know your boss asked you to help out in an emergency and because you're such a hard worker, you were chosen to go to another store to cover a critical shift and that you will be working a swing shift with managers to prepare it for its new opening. Tell her how this is a real big honor and that they are also paying for your travel costs to the Valley."

"Hello, mom? Hi... i stopped by work and the regional manager said I'm a great worker! Yeah, they like that I work really hard" (Dougie caressed me as i said that word) Whispering... "stop!"

"Yeah, mom- so, they chose me to help out with a store remodel and that it's a great chance for me to get noticed. i watch as Dougie takes the lipstick and moves the pink tip to my lips. i purse my lips, feeling so sexy. "Yeah, so- he said i'll probably work 8 hours, maybe 10, as the people they had doing this were too slow and they're now behind schedule. So, probably be like 3 or 4am...- hold on... yes? Mom, they want me to work a second shift on top tomorrow morning, so it will be even later- i'll just take a long nap and rake in the big bucks! Gotta go, boss is calling to get going! Yes, i'll stay in touch and let you know when i'm coming ... home. Love you, bi!!"

Dougie smiled wickedly. Kimmy has lied and also given himself hours more time to fully immerse himself into his new being. No rush, no interference and no going back. Kim the teenage boy drifted off into the sunset. Kimmy the cute new femmey gurl swished from the fog of confusion to welcome the evening's awakening.

-----

Dougie called me into the bedroom; I was still on the couch, staring at the phone, thinking about the call I had just made. I had lied to my mother and I was to spend the evening- the night, with Dougie ... and who knows what.

I felt wonderful, for certain. The way the tights felt and the silky panty, my bra and inserts. And the feel of lipstick on my lips. The scent of perfume on me. The warm glow I felt all over my body- a little from the drinks, and a ... LOT from the intimacy and discovery of the morning. I ran my toe over my other leg, the tight sheer material accentuating my legs, glimmery- so pretty, so feminine. I touched my finger to my ear- my earrings.. Dougie's earrings, how they dangled on my neck. Nothing like the boring pearl earrings that mother wore- these were long, silvery, slutty.

For a moment, I felt the fear- to escape. If I was to run, to go back to Kim, this was the moment. Sure, I had felt a man- his cock. I had kissed him and touched him. And I let him put makeup on me. This- all of this- who is this? And I ran my fingers over my tight top. My nipples hardened. I looked at my VS120, sitting in the ash tray. Maybe a little bit of the ciggie will help me make the right decision. I picked it up and then the lighter. The rhinestones rubbed against my flesh. I flicked the lighter on and touched the flame to the tip. Inhaling slowly, I felt my lipstick coating the white tip. I stared at my ciggie- the skinniness and the length and the whisper of smoke drifting up. I slowly exhaled, through my nose, the smoke filling the air around me, it seemed like the room was full with it. I took another puff, slowly, my lips holding onto the tip with jealousy. As I touched it, I held it elegantly.

I pursed my lips as I exhaled, closing my eyes, I thought I could still see the smoke around me. My- no, Dougie's wig was the perfect length- I could feel the long hair caressing my neck, almost reaching my cleavage. I looked down- at my cleavage. My titties had always been big, always teased, always hated them. Now- I felt- wonderful. I felt sexy. The taste of my ciggie on my breath- along with the taste of COCK.

Omg- I knew. A shiver of cold- or was it heat- raced over my body. I pressed my arms together slightly and my cleavage grew, my breasts looking so full, round, pressing out, showing off. I loved it! I took another long puff on my ciggie. My fingers extended out, stretched, holding my ciggie, my wrist went naturally limp. I giggled, loving how I felt, how I saw myself. I was seeing my true self, emerging. I sensed a struggle- like each part of me was fighting another- go forward, no- run, hide, escape. Hide, Kim. Hide and go back.

And I shrugged- what to do? I was never really assertive, I don't think. I was about certain things but not about myself. I had my moments, but as I reached teen age, I felt less and less ... something. I saw other- boys, become leaders and standing out. I tried but it was comical, I knew.

I took my drink- maybe something cool would help calm me. I heard Dougie puttering around, singing along with the music that was playing. He had such a calm, smooth voice. Sipping a little bit, I tried to gather my thoughts. I did know that the actions I took, what I did, right now, would shape me for years to come. As I thought of the word 'shape', I realized I was moving my body, swaying, isolating and moving my chest to the sound of the music. I looked at the breast forms, how real they looked. I crossed my legs, tight, my toes pointed.

Sit like a boy, you sissy. I giggled as I heard that word, from my own mind, reference me. You sissy. You are such a sissy, such a fag. Look at you- dressed totally feminine. Look at the lipstick marks- your lipstick marks, on the ciggie and the glass. You're a crossdresser and a sissy. Kimmy- you're a sissy fag crossdresser. Is that how you want to be known and seen? You want to suck cock all the time, Kim... Kimmy? Is that what you want?

Omg- I stood up and walked.

And I swished my ass, crossing over step to sway my ass. My ciggie dangled from my hand, so elegantly. I walked around Dougie's apartment, the click of my heels sounding off. I loved how I felt. Yes... Kim- say hello to the new you, KIMMY. That's right- Kim. Yes, I LOVE to SUCK COCK. It was the most amazing and erotic thing I ever did, I could imagine. And Kim- Kimmy LOVES to be sexy and dressed, and absolutely ADORES makeup. Look Kim- Kimmy is putting more lipstick on. Mmmmmmm it feels so luscious, delicious. Kim- you KNOW you loved doing that for years. Kim, you can't deny it any more. Its not fair to you- the real you. Look at how you feel swishing around, swaying your round gurly ass. And your breasts- just imagine those as really yours. Mmm yes Kim- Kimmy can feel that arousal. Say it Kim- how you love having full breasts and wearing makeup and looking so feminine and sexy.

Kimmy- ... I... yesss... Kimmy, you're right. This IS who and what we.. i.. am. Inhaling on my ciggie, looking at my lipstick mark on the tip- images of Dougie's cock, my lipstick marks on it, as well. I feel a rousing passion in me. I smile, waving bi bi to Kim as I set my ciggie down. "Dougie... what's next?"

Dougie's voice became louder as he approached out of his bedroom into the hallway, his view of me now front & center. "Well now, Kimmy. You look so...so, vibrant! Glowing even." Dougie stepped forward and softly embraced me. Pulling me closer, he looked into my eyes. "Are you ok? Do you want to talk? I know this was a lot to take in." Dougie then giggled a little as he rubbed his crotch against me.

I blushed, the feel of his cock felt good. I didn't move away. Dougie kissed my neck softly, whispering in my ear. "Darling, don't worry. I'm here for you, want you to enjoy and explore, to not feel afraid, that you don't have to hide or deny who you are, what you love and how you want to look and think and desire. I know you're trying to figure this all out by yourself. I'm here for you, always." Dougie touched my hands, holding them. I felt so special and so cared for. I felt wonderful and natural and finally, at home. I looked into Dougie's eyes, smiling.

"Yes Dougie, I... I was almost ready to run away. I was afraid, unsure. Just what was I doing?" But I sat there and thought and remembered and realized and knew. I know what I want. I know what I need. I cannot go back. "Dougie, I don't want to go back. I want to know this- who I really am. Kimmy must be the real me, the ONLY me!" I shivered and a tear came to my eye. Dougie touched it softly with his finger, wiping it away.

"My pet, let me hold you. Yes, Kimmy, you WILL never go back. I will do all I can so that you adore and enjoy being the real you. This really is who you are... just like this is who I am. Now, let's get you ready, shall we?" And with that, Dougie leaned forward and kissed me softly- then fully. I felt his tongue moving into my mouth. I felt it become long, hard, probing me. It felt sexy and erotic and wicked. And I loved it. Dougie caressed my ass and pulled me to him. I could feel him becoming hard. I felt.. hungry.

Dougie pulled away slightly. "You are such a bad gurl! Look at what you've done! Touch it. See? You made me so hard. You're really such a slut, you sissy bitch." Running my fingers over the outline of his cock, I felt pure pleasure.

"Not now- there's too much to do before OUR friends get here. Don't think I don't want you sucking my cock. Honey, you did it so well, you're a natural!" I blushed as he said that. Dougie took my hand and led me back into his bedroom. "Lets freshen your makeup some and, here, I laid out your outfit for this evening. Try these things on, Kimmy."

I looked at the bright blue spandex dress, it looked divine. Silver high heels covered in sparkles, sheer nylons and white satin push up bra and matching bikini panty. They all looked divine. I touched the dress gently. It really was real. I was not dreaming- this wasn't a fantasy. I looked at Dougie- there was no need for words. I don't think I could have said how wonderful this all was. And I could tell that he knew it.

Off with my tights and top, into the shower to freshen up. The warm water pulsing over my body, onto my clitty and ass; it was divine. I bathed thoroughly and the bubbles and sponge slid over my flesh, the sweet floral perfume of the bath soap encompassing me. My desire to have the moment last for hours was disrupted by Dougie. "Honey, unless you want to have the guys come in here, you better swish that sexy ass out and get ready!" I took a few minutes to thoroughly wash my tush; I took the liberty to use his razor to remove the few soft hairs that were on my body...

Good riddance.

Dougie left a large, fluffy towel for me; as I dried myself, I realized it was spritzed with a floral scent which transferred to my flesh. I inhaled deeply- mmm delightful. Fully dried, I stepped back into his bedroom, my clitty soft and non-descript. I sat on the bed and slid the panties on, and loved how the tight fabric gripped and shaped my round ass. "Go on, sweetie. The boys are about 10 minutes out. And here, lets try this." He reached to my hips and pulled the panties up high, the fabric sliding up between my ass cheeks. He smiled. I loved the feeling of tightness there. "Lets get your ready... here, this.. and then these." In 5 minutes, I was sitting at Dougie's dressing table and he was fully refreshing my makeup. "Lets get you ready for this evening, honey. Its glam time!"

He wouldn't let me look in the mirror. "You'll know how you look when they arrive. Here, your hands are small like mine. Put these rings on and here, this bracelet too. Now, do a slow pirouette for me, siss." I slowly gave Dougie a full view of me from every angle, moving my hips and my hands to pose for him. I felt so sexy.

"Those heels feel ok? Aside from you wearing your mother's heels, you haven't had much practice." I wanted to show Dougie that I was able and began to swish and sway my ass around his apartment. "Shall we have another drink?" Now in the kitchen bar area, I looked at the options. Dougie came up behind me, pressing up against my back. "Honey, we still have our Strega to finish. And I'm casting another spell on you." With that, he caressed my ass cheek, and I moved back to make the moment last longer.

Dougie turned me around and slid his Strega-coated finger into my mouth. His finger was soaking and I licked his finger fully, looking him in the eyes. He then took my finger and dipped it into the glass. He brought it to his lips and began to suck on it- then moved and had it between our mouths, both of us licking it together. Our lips and tongues melted together around my finger, and then his, as well, redipped and wet, one sliding into his mouth and then mine, intertwining over and over. And then the buzzer interrupted, we lingered one last kiss and then Dougie buzzed them in. He walked over to me, holding my hand. "Ready, siss? The evening has only just begun." He then ran into his bedroom and returned with our lipsticks, refreshing mine. And as he ran his finger over the outline of my lips, the door opened and his friends walked in- smiling, giggling, carrying several bags and bottles, and then looked at Dougie.. and then me. Dougie continued to run his finger over my lips. I kissed and licked it. I had no idea how sensuous or flirtatious I may have looked, I just knew I wanted to do that.

"So, this is Kimmy! My god, she's adorable. Don't you all think?" The four looked me over, and one reached to caress and fondle my breasts while another caressed my round ass. "Honey, this is really you? You have the sexiest gurly ass!" I softly said thank you and then introductions commenced over a variety of cocktails. Rob, Kyle, Jerome and Lanny have been Dougie's friends for over 8 years.

"Boys, this is Kimmy. You remember me telling you that I had a hint that Kimmy might be one of our new friends? Well, just look at her. And this is her first time out, first time to... well, maybe I'll let Kimmy tell you that. But first, treat time! And I do want to be sure we sneak in about 30 minutes- Kimmy wants to get her ears pierced, isn't that right sweetie? Maybe we can get your nails done really quickly too. Mira at the salon does owe us some favors. And omg- Kimmy is such a lil liar! You should have heard her tell her mother about not coming home tonight. Maybe we can get her to spend Friday AND Saturday night here." I blushed. The reality that, now, four other people knew about me. They all were very nice looking men, smiling and making me feel one of them- but was there something I was missing?

"Here, honey. You haven't smoked pot before, I bet. Am I right?" Once again, Dougie sized me up correctly. I shook my head no. He put the joint to his lips and lit it up, inhaled and then brought it to my lips. "Nice and slow, Kimmy. Nice and slow. You know how to suck nice and slow, don't you?" Dougie giggled and looked at his friends. I inhaled and let the smoke flow into my body. A second inhale, the smoke drifting and engulfing my body and my mind. I passed the joint to one of the guys and he touched my hand softly, caressing my fingers as he took it from me. I smiled, slowly, wide, and then licked my lips. The joint was passed among them, then back to Dougie to finish. He set it aside and brought out another joint. He lit it and inhaled then leaned next to me. I waited for him to pass it to me. Instead, he moved and kissed me fully. He opened his mouth and I felt the smoke enter me. My wet lips melted to his. As he slowly stopped, he passed the joint and the next guy took a deep hit. He (Rob) then stepped to me and kissed me the same way. I felt him place his hand on my back, holding me to him. Kyle watched, and I knew that I would be kissed intensely, both as their sexy welcomes and to assure I felt the buzz from the pot.

After the fourth kiss, we all went to sit on the couch. I suddenly was surrounded by Rob and Lanny, while Kyle, the most petite of the group, sat gently on the end of the coffee table, facing me. Dougie called to me and tossed my lipstick, telling me to put more lipstick on. I did and looked at the four as I coated my lips. I felt Rob and Lanny sliding their hands on my legs, and between being totally femme, I felt high and each touch of their hands made me feel beyond sexy and feminine. I began to think of sucking cock and my eyes drifted to looking at their pants. They must have noticed as they each took my arm and guided it to their crotch. I began to feel their erections- warm, becoming hard. Hard, from my touch. I smiled. I looked over and saw Dougie watching from his bedroom door. He smiled at me and blew me a kiss. I wanted their cocks. All of them.

1000s of images skirted through my mind as I sat there, surrounded by sexy men who kept telling me how sexy and feminine I was. I found it hard to believe I was there and that their admiration was directed towards me. As I felt quite high, I avoided closing my eyes to avoid getting dizzy. But with eyes open, I saw the look of these 4 men as they caressed and touched my body. Though I wasn't paralyzed, I wasn't sure what to do, who to touch. I guess my concerns were seen as they brought me to my feet, each taking a few moments to dance with me. Each, I enjoyed finding, placed their hands on my round tush. I moved my body to the sultry music and welcomed their kisses.

I looked over to the bedroom door and there was Dougie, watching. I blushed. I felt like I had betrayed him, enjoying the touch of these men. I smiled and mouthed... "Hi, is this ok?" Dougie smiled back warmly, licking his lips. He blew me a kiss and then pointed to his rhinestone-encrusted watch. I placed my hands on Jerome's tush; his Cock felt massive, so much bigger than his friends.

Little did I know that earlier, when Dougie had called his friends to enjoy my coming out, he also plotted with them to make this an extra special evening. Dougie thought it would be essential for me to be fully engulfed in what he knew was my burning desire to explore and enjoy and accept and desire more of any and everything feminine. He told them that he knew my older brother who had been a friend for a while but shied away after a few nights out at some of the more wild LA clubs of the late 70s. Dougie had no intention of having someone tiptoe forward just to run away in fear. Dougie felt he had failed Kimmy's brother and tried to help him- to not feel guilt or remorse for his true desires. Kimmy's brother, instead, sought shelter in the church and a faith-based dating group. Dougie, who knew Kimmy's brother for several years as schoolmates, saw him with women who were abusive, demanding and lacking the passion & love and kindness so painfully desired.

Dougie would NOT let that happen again. He wanted to be sure that my inquiries and exploration were not just hints but complete immersion and embrace. Kimmy was to tested and challenged, again and again, if she really wanted to be so totally femme and without question, the effeminate, sexy, slutty crossdresser that he initially saw. The few hours Kimmy spent with Dougie this early afternoon could have been just exploration and then denial- a blip like an errant kiss that leads to nothing else. Or it could be the kindling that creates a raging fire of pleasure and acceptance- of erotic transformation into a lifestyle that Kimmy seemed so destined for.

As Jerome and I danced, I was taken by what felt to be more sensations. Jerome's hands were on my tush, that was for certain. I felt him becoming so hard, pressing against me. But I felt something else. Hands, on my breasts, moving and caressing me. I looked into Jerome's eyes, his lustful smile brimming with delight. He leaned to me and kissed my neck, his lips toying with my ear and dangly earring. I felt a rush of warmth race over my body, tingling sensations of pleasure, of arousal. I moaned, wanting more. And then I felt lips on my other ear. I turned slightly and then felt a mouth meeting up with mine. I kissed, not sure who it was and not caring. I wanted to kiss, deeply. I felt my dress being removed and lifted my arms to allow it be drift off my body. I felt their mouths- four mouths, warm, moving over every inch of my soft, bare flesh.

Deviana
Deviana
90 Followers
12