Kimmy's Discovery Ch. 02

Ch 2 of sweet young Kimmy. With the help of his co-worker, he opens the door to self-discovery and embrace of his true effeminate being.

NOTE- I use the "i" in Kimmy's description, a grammatical faux pas, perhaps, to reinforce the sense of Kimmy's submissive nature.

i laid there, the couch was actually very comfortable, especially given its sleek lines and formal style. i looked at the two magazines and the images of sexy women depicted on both. Quite honestly, i couldn't really tell which one was which. The music filled the room- Dougie had put on some really nice instrumental R&B music which was very soothing.

i felt ... good. While i had been a bit light headed earlier, i felt ... good, very good. i reached for my glass of wine and took another sip. "Do you need a lighter, Kimmy? Its right on the side, it has rhinestones all over it, isn't it cute?"

i looked behind me- the cigarettes were elegantly housed in a very neat cut crystal container. i remember seeing something similar to this when i went with Mother to visit one of her friends- that woman smoked quite a bit and even got Mother to try a cigarette. It was quite hypnotic to see Mother smoking- she seemed so prim and proper, and i considered smoking something... invigorating, emancipating, sexy. All those ads of sexy women smoking- having the long white cigarette on their lips, definitely seemed sexy to me.

i had not had a cigarette in quite some time- i used to sneak some from that woman's house when Mother and the woman would go off into another room to chat and such. i always wondered how many i could actually take (steal) without it being too obvious.

"Are you sure its ok to smoke, Dougie?" i took one of the long sleak white VS120s and put it to my lip. The smell of the menthol and tobacco was delightful. i took the lighter, the rhinestones adorning it catching the sunlight and flashing pretty colors all around me- i giggled, and lit my ciggie. i held it just like the women in the magazine, my fingers extended long and sleak, taking a deep puff and then another. i slowly exhaled and felt the smoke intoxicating. i leaned over the couch to pick up the ash tray and suddenly felt...

"WHACK" a playful but firm smack on my tush, Dougie's hand lingering and then his soft laugh. "My my, sweetie, you present me with that view and i don't know what i'll do!" He then caressed my bottom and asked if that was too hard. I said no, it wasn't, then wiggled my tush to tease him a bit; i felt playful. i gyrated my round bottom for him and then looked over my shoulder at him. "No honey, it wasn't hard at all... do you want to try again? Maybe a little harder?"

i couldn't believe i said that but i loved saying it. Dougie smiled and said... "oh, really... honey, you want it harder, you are making it very hard, in case you didn't know." Then he spanked me several times on both ass cheeks. i giggled and took another deep puff, looking at him and then slowly pursed my lips, blowing the smoke out.

"Hi there" i said. He smiled, and sat close to me... "hi there baby" and then reached across me, brushing his crotch against me as he took his wine glass. He looked at me- "that ciggie looks so lovely in your hands. Have you smoked for very long?" i then told him about Mother; dad didn't smoke or really drink either. Mother had smoked a few cigarettes when visiting that lady and one other- each time, i watched and saw the red lipstick marks left by her and her friend on their cigarette tips. i shared the details with him explicitly, each image and thought that had raced through my young mind. He was enjoying each bit, getting to know me more and more. i felt like i had finally found a true friend who i could share any and all of my closest secrets with.

"And what else, Kimmy- when you saw that red lipstick mark on the cigarette, and you had yours to enjoy in private, did you want to put lipstick on too?"

And here, i knew was that point- do i keep my young exploration of trying on Mother's lingerie and makeup to myself?

"Well..." and i looked him in the eyes. He offered me my wine glass and then took a ciggie for himself. i was holding the lighter still; he took my hand and brought the lighter to him and i lit the flame. He took a deep drag and then put his lips together and blew the smoke off to the side. "i never liked the other cigarettes, Marlboro or Kent or Kool. They just seemed too rough, i sure don't want to walk a mile for a Camel!" i giggled.

"O me neither Dougie. i used to ... omg.. i used to... (looking off to the side), i'd find ciggies in ash trays and the like that weren't finished. Nice restaurants and such, often just discarded by some elegant woman who just wanted a small break. And i'd sneak those home to enjoy later. But i hated the harshness of Marlboro and the Camels had no filter.. eww!"

"So... tell me, honey"

Dougie looked me straight in the eyes. No other words, he ordered me to tell him. And i did. And i shared about looking at Mother's Cosmopolitan- she bought the magazine now and then, and i would buy one every now and then as well- and i would be alone in the backyard and i would put her lipstick on. It felt wonderful gliding onto my lips and i loved seeing my lipstick marks on the ciggie tip. It just felt wonderful! i felt so relieved sharing that with Dougie. i had never ever told anyone about this before.

Dougie smiled and touched my hand. "Honey, i was the same way. My mother used to own a bar- it was a nice enough bar, she was the bartender at times and i would come in and sit off in the back when i was young, do my homework and watch the customers. There were several really glamorous women who worked in Hollywood- they lived right up the street from her bar, and they would be so fashionable, so stunning. I would watch them, how they sat and walked and talked and, when they met men, how they would talk and move their hands."

Dougie moved his hands in lovely feminine elegance, depicting the women of his youth, and i noticed, himself. "And how the men would buy them drinks and then they would get real close to each other... I guess I should have identified with the men but... well, I didn't!" i watched as Dougie shared his story, how he seemed to look off outside, also looking deeply inside.

"Mom had her fashionable bar attire, she used to be a dancer for the big Hollywood shows when she was younger- and every now and then she would wear one of her evening gowns when she knew some big movie stars would be stopping by. I loved watching her get dressed and she would ask me to zip her up in her tight dresses. I would play around with her slips as she went through what she wanted to wear- she would laugh and have me wear her heels, saying 'let me see my sweet Dougie walk now... that's it honey' and I would parade around in front of her, loving how she watched me, her smile, her full painted lips and bright white smile as she watched me. It seemed so natural, so fun, to step around her bedroom, doing my cross over step just as I had seen her and the other ladies walk. "Oh sweetie, you are such a cutie! Maybe I'll get you done up completely some time and show you off at the club!" She giggled and smiled a bit wickedly.

Now it was Dougie's turn to blush and become quiet.

"Isn't it something then, Dougie? Mother's lingerie, how i was drawn to it. She had some really fancy items, bustieres and corsets and girdles and garters. i would also watch in detail as she would get dressed to go out with dad. How she slid her nylons on and i would go watch as she put her makeup on. i thought about watching dad- i DID love to watch people- but he was boring and i would go back to watching Mother. omg Dougie- (this time it was my turn to touch his hand)- one time, i was sure they had left and were gone and i was ...well, trying on Mother's lingerie and had full makeup on. OMG Dougie- they came back home!! She had forgotten something- i told them i was in the bathroom and couldn't come out! (giggle) i was so petrified that they would find out!"

"They finally left and i was wondering- do i just take it all off or...and i ran and got the pack of VS120s that i had bought from a vending machine and went into the backyard and smoked 4 of them. i had the lipstick in my hand and i was shaking as i put more and more lipstick on, omg honey, i loved that so!"

Dougie took the bottle of wine and poured the remainder into my glass. "Here, have some more." i sipped the wine and reflected back. i licked my lip, thinking of that time. Dougie looked at me. "Well, Kimmy, we're alone here and ... well... would you like to put lipstick on again?

Enjoy your Virginia Slims (he said those words so seductively) like you did then? You know I won't tell anyone. In fact, I would join you... yes?"

i looked at Dougie. The passion and heat i felt from when i was young was back in me, raging. i looked at my ciggie, almost gone. Yes, i wanted another one and i wanted to put lipstick on... "yes Dougie... lets! yes!!" i felt wonderful, alive, free!

"What color would you like, love? I have so many to choose from- come on, lets go pick one or two out to try!" Dougie touched my hand and i held his and we went into his bedroom. On his dresser he had a lovely pink satin-covered makeup case. He opened it and i saw dozens of lipsticks and lip glosses. What do i choose?

"What do you think?" My hands trembled as i touched the frosty pink lipstick. i replied... "This one? What do you think?" He took it from my hand and began to apply to my lips. "You know, honey, i do professional makeup on the side. Mom helped teach me and I used to do makeup for all the cheerleaders and prom night too. I make more money doing that for Hollywood events than at work but I have benefits and stuff there, so that's work.. and this... (putting lipstick on me).. this.. love, is ... fun!"

Dougie took his time, not erratic like me. He outlined my lips and looked, dabbling and using a small brush to apply the lipstick. "You know,... while we're at it... wanna have some real fun? Come on honey... when will you get an offer like this again?"

i smiled. i took a sip from my wine glass that i had brought with me. i felt so wonderful and free and- so happy. "But- i know how i look when i put makeup on. i just don't know... (looking at him)- "yes.. do it!"

"That's a gurl!" Dougie blushed and leaned forward and gave me a warm, close hug. Whispering in my ear- "Honey I'm gonna make you soo pretty! You'll look gorgeous!" i lost track of time as Dougie worked his magic. i sat there, my nipples pressing so hard against my top.

"You know... i don't want to get any makeup accidentally on your nice shirt. Here- let's take it off and you can put on one of my tops." Before i could say anything, he unbuttoned three buttons then pulled it off of me. i sat there, topless, i was embarrassed as though i am very fit, my breasts were very noticeable and the areolae were large and distinct. i realized i was covering my 'chest' with my folded arms, not wanting to seem too self-conscious but he noticed and took my hands. "We'll have none of that. Let me see you." i moved my arms as directed and stood upright; my breasts were pressing out, round, feminine.

"O yes, o you are such a doll! Let me see you more. Stand up, turn around, show me how sexy you are, love." i realized that i loved being called 'love' and that i felt so- alive as i showed myself, my body, my curves, to him. i wiggled my tush even more and walked around, just like he walked, swishing my ass.

"Um... i, am i ok?" "O sweetie, you're more than OK. Here, take those silly boi pants off, okay? Your body is just way to sexy and pretty to be hidden by pants that don't show off your sexy shape. Here... try these on." And Dougie tossed to me a pair of tights. i turned as i became naked aside from my undies.

"Oh no! Those are no longer in your wardrobe... OFF WITH THOSE!! NOW!!"

i slid the briefs off and i was now naked before him. "Here, these are just your size and style." And he tossed me a pair of very delicate red lacey bikini-style panties. i had worn Mother's panties a number of times but those were all boring nylon, no lace, aside from her fancy fancy lingerie. These, the red panties, felt wonderful. As i slid them on, i felt so different, and as i slid them all the way up, i turned and gave Dougie a seductive smile.

"Nice... very nice, now come over here so i can see you up close." i swished over to him and then turned so he could see how they melted to my ass. He ran his hand over the sheer material, touching me. i felt so sexy. "And the front?" i turned and my erection was impossible to hide. "O my, that is ... nice!" He whispered that last word and then ran his hand over me. my clitty jerked, the first time that anyone else had ever touched it. His hand ran along the length and i felt a rush of heat over me.

"Put those leggings on now, for now, sweetie. You know, all the dancers wear those, they're comfy, aren't they?" i slid the sheer black material up and yes, it felt wonderful and yes, they were very comfortable. i tried to adjust myself... and Dougie giggled. "Sweetie, don't worry about that for now. Come on, lets finish your makeup, you sexy gurl." He then slid a tight tight top over me, which also molded to my upper body and breasts. it didn't help that it was white and my nipples were very visible.

i walked back and sat down and over the next 30 minutes, Dougie did this and applied that and smiled and bumped his crotch against me and touched me so softly.

Every now and then, Dougie would dabble a bit of makeup over his own face. He would look in the mirror and see me, smile and blow me a kiss. i blushed and smiled. "Ok, you ready?" What do i dare say? Yes? No?? Help???

"yes, i am..." And he had me stand up to look in the full length mirror. i couldn't believe my eyes. My eyes, full and glam and my long eyelashes and eyebrows and eyeshadow. And my lips- i looked, turned, not able to believe it was really me. "Go ahead, honey, blow yourself a kiss" and i did. i looked at me and puckered my lips and then Dougie leaned over and kissed me.

And i melted. And i returned his kiss. And felt his lips on me, his hands on me, his crotch.. .his Cock, pressing against me, and i loved it. His tongue slowly slid into my mouth and i gladly opened my lips, yes... His hands on my ass felt amazing. i stood there, feeling all of his attention. Then i saw as he undid his pants, sliding them down. His long legs bare and his pink panties barely containing his Cock.

i moaned. He pressed against me and i met him, feeling my clitty press back against him. He kissed me more and i felt my lips melting onto his. "Don't worry about your lipstick, sweetie, I'll fix up your lips just like the women do".

And then i felt him take my hand and place it on his ass. And i began to caress him, his round ass soft,... He moaned and i fondled his ass with both hands, our lips fully engulfed in a long deep passionate kiss.

i loved how i felt, how i looked, how i saw myself- the new me, and how i turned him on. "My o my~ sis, i would love to show you off, you're such a doll! I have a couple more things to do- we can't just stop here now, can we?" Before i could even answer, he said, "Of course we can't stop here." As he caressed my clitty, he took my hand- "here, lets help your budding breasts look their best. You've worn your mother's bras, lets see if she had anything like this!" And he reached into one of his dresser drawers and extracted a bra that had life-like breasts. "Here, take that top off and put this on. And i have a few other things too, you're going to be such a living doll!"

i felt like it was Christmas, better than any of the days where i had hours to dress as a 6 - 9 year old. i was with someone who understood me and enjoyed helping me and was really sexy. i stood there, watching, moving from foot to foot, trying to look sexy. A moment later, Dougie emerged with a sexy sequin top, high heels and a wig. "Now, this will complete the new you, just as we know you should look, right?" i nodded yes.

With the wig on and high heels in place, i felt so perfect an sexy. "Wait!" And Dougie reached into his jewelry case and brought out a pair of stunning dangly clip on earrings and a necklace. "Now... NOW... you are done, perfect, sexy and omg... you have me so turned on! You're such a gorgeous princess, i don't know if i will be able to keep you to myself, all the sexy guys are going to get to know you, you know."

i looked in the mirror- who is this? omg, my eyes, my hair, my ... breasts! and i walked slowly- and quickly caught on, slow, small steps, heel to toe. And i looked at Dougie... "omg

Dougie, i just love it! Thank you soo much! Its amazing, i feel so sexy, so perfect!" And i reached over and gave him such a long hug. Whispering "thank you darling"

"Now, go on out and get yourself a ciggie, sis. And pour us both another snifter of Stregga. The night is just starting. "Yes love, i will." And i swished my ass out to the living room.