WHAT THE HELL CHERLY
- 3 years ago
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Becoming (C)Her free porn video
I remember when I first felt it - silk. It was the most luxurious fabric my hands had ever touched. My fingers handled it with care in the department store. I was a teenager shopping when I noticed the silk nightgowns donned by the mannequins, draped so elegantly over their bodies. My body responded immediately and I had to buy some. That day, I bought a long nightgown and three pairs of panties - my first purchases in ladies' apparel.
In the privacy of my bedroom, I slipped the panties on and modeled them in the mirror. I am not sure which affected me more, the cool feel of the silk on my skin, or the way it hugged my ass. Next, I pulled the nightgown over my head. The one I chose could almost pass for a gown it was so elegant. I saw myself with new eyes; I was beautiful.
My cock grew and stretched the flimsy fabric. Fuck, I was turned on. I reached for another pair of silk panties and moved to the bed. I slid my nightgown up over my hips, slid my panties down, and began rubbing the other silk panties up and down my hard dick. Fuck, it felt good. A few minutes later and I was squirting cum all over my stomach, lifting my nightgown higher just in time to avoid staining it. I lay there panting on the bed. This was the beginning of my love affair with ladies' lingerie. I bought many more silky items and mom never questioned why I suddenly volunteered to start doing my own laundry.
As far as life outside my bedroom, I was very introverted - kind of a loner at school but drawn to musical theatre. I loved to sing but was too shy to be on stage, so I worked behind the scenes in makeup and costumes, just to be a part of it all. I would learn the female role and dress up in my room, singing to my mirror. My mother would hear me singing and tell me I had the voice of an angel. I wasn't sure about my voice though. Mothers always say that stuff, don't they?
When I wasn't singing songs from our productions, I was singing Cher. God, I loved her. Her beautiful dark hair and outlandish, glittery costumes. Add in she was a total badass. I practiced emulating her voice and thought I sounded pretty good. Her distinctive contralto voice matched my own natural range. I was proud of the day I perfected that tongue thing she did. So sexy! This was how I spent my Saturdays - alone in my room pretending to be someone I wasn't.
As you might imagine, I didn't have a lot of friends at school. Kids weren't mean to me, just kind of ignored me. Except for one girl. She wanted to work makeup and costumes with me in theatre. Surprisingly, she took as much pride in these aspects of the productions as I did. One day she invited me over to practice some makeup applications for an upcoming play. We got along so well and had fun learning new techniques and practicing on each other. She didn't seem to find it weird that I enjoyed her making me up. I looked forward to spending my Saturdays with her. She was pretty popular though and always left in the late afternoon, getting ready for a date that night. But, I was grateful for the time she spent with me. We felt comfortable with each other and talked about our future dreams, etc. It was nice. Although we attended separate colleges, we kept in touch - until she met him. I had seen her infatuated with many boys, but this one was different. She was in love. Feelings of jealousy rose up inside me and it hurt, so I lost touch with her.
After college, I started working for larger productions in New York City, interning as a makeup artist. Some of the performers spent hours in my makeup chair. I loved starting with a blank canvas and transforming them. My pride soared when I finished and spun them around to look in the mirror - each one would gasp, exclaiming how beautiful she felt. My confidence and comfort-level grew and I started singing to pass the time while I transformed the different ladies. Cher's songs were my usual choice. I quickly became known as the singing makeup artist among the performers. Then, it happened. I guess you could say I was in the right place at the right time and the right person heard me and the process of "Becoming Cher" began. Being a drag queen satisfied my two great loves - feeling feminine and singing.
~~~
I love this process - of becoming her. My Cher persona gives me the confidence to perform on stage. The artistry, crowds, all of it bring me so much joy. Don't get me wrong, I enjoy being Jason too. That part of me is just different. I am an attractive man, but certainly not one of the attention-grabbing beautiful people, like Cher. I enjoy both sides of my life. One side doesn't want attention - more of a watcher. Another side craves it - but needs the costume and makeup to feel comfortable. Both are me. You might not understand, but becoming Cher exhilarates me in a way Jason can't.
I have another show tonight at the Diva Royale and begin the transformation. Fortunately, I am naturally built long and lean, perfect for her elaborate slinky costumes. God gave me the high cheekbones and chiseled face that women pay big bucks to get. It definitely helps that Cher and I share some physical attributes. Still, it takes me a couple of hours to get into makeup, hair, and costume, but I love every aspect of the process. Well, almost every aspect. Tucking is not my favorite thing. I can't have my cock bulging in my dress, so I pull my penis down between my legs and tape it to my perineum. Oh, and I have to shave from face to feet ... every day ... every damn day.
As I meticulously apply each layer of makeup and Cher comes into focus, my excitement builds. I love giving myself her iconic purple smokey eye, topped off with thick fake lashes. It is interesting how my personality transforms with my physical appearance. But the time I am finished, Jason has become Cher inside and out. The last part is my favorite - slipping into my costume. Watching myself in the mirror, I slowly pull up my stockings, marveling at how they show off my lean legs. Next the silk panties - my great love. I twist and turn in the mirror, posing, twirling, admiring. I don't need a bra, but love the femininity of it so I wear one. Lastly, I slip the sparkling dress over my head, careful not to touch my made-up face. I reach for the wig, securing it firmly in place to finish my look. I enjoy quite a bit or mirror-time when my ensemble is complete. Seeing myself. Feeling the elegance adorning my body. All of it fuels my energy for my performance.
Right before I make my way to the stage, my high heels go on ... and they fucking hurt my feet. I'm ready for another performance and adrenaline rushes through my veins. Each night is different, never knowing what kind of audience awaits me. What a rush! The announcer calls my name and the applause quickens my steps.
I notice her in the middle of "Love is a Lonely Place Without You". It can't be? Can it? Jess? I have to know for certain and descend the steps to sing to her table. As I approach, my suspicions are confirmed. I would know those big blue eyes anywhere. Fueled with "Cher" confidence, I take her hand and sing into those eyes I never expected to see again.
As I sing words of love and missing her, she blushes, giggling, looking back at her friends. I kiss her cheek and whisper, "Hi, Jess," in her ear. Then, I see it - the moment she recognizes me. Her mouth drops open and I wink before releasing her hand and resuming my position on the stage.
I purposely look at everyone in the audience, except her - too nervous about her reaction seeing me like this. After I finish my set, I send a stagehand out into the audience to invite her to my dressing room.
My feet are firmly planted on the other side of the door, just praying I hear a knock. When I do, I try not to rip the door off the hinges opening it.
"Hi, Jess," I say, trying to control my beating heart.
"Jason! Sweet Jesus! I can't believe this!" She reaches out to rake her fingers through my long hair. "What? How? I mean you look and sound just like her. You are Cher!" Then, she throws her arms around my body, pulling me into a warm hug.
I am excited by her hug and her compliment. "Thank you, Jess. I worked hard to become her."
"How did you think to do this?" she says, pulling back, wide eyes roaming up and down from my made-up face down to my 5-inch heels.
I know she is shocked by all of this. I can only think to explain it by saying, "I love this quote by Cher - 'All of us invent ourselves. Some of us just have more imagination than others.' I guess I have a pretty big imagination, Jess."
"You are amazing. I mean it. I can't tell you how happy I am to have found you again," she says, hugging me once again. She hasn't changed. Her scent. Her smile. Her eyes. Everything part of her is just as I remembered.
As we pull apart, I keep her hands held in mine, caressing the top of her hand with my thumb. "I have missed you. I wanted to call, but-"
"It's my fault," she cuts me off. "I thought I was in love and got so consumed with him. I should have kept in touch. You were my only friend, you know."
"What? You were popular and had lots of friends, Jess."
"They weren't real friends - not like you. I have missed you," she says, lunging at me again for a hug. "I just moved here and can't believe you are here too!"
I may as well get this over with. "So, how is he?"
"Who the hell cares," she says laughing. "He cheated on me. I think I knew he wasn't the one, somewhere in the back of my mind. I don't know what I was thinking."
"You seemed so in love."
"I think I was in love with being in love. You know what I mean? Young and stupid. In truth, the only one I still think about from back then is you."
I sigh and look away.
"What?" she asks, reaching up to turn my face back to hers.
"It's just that I never stopped thinking about you either. I regret not telling you how I really felt, but I didn't seem your romantic type."
"You were interested in me? But, aren't you gay? I mean ..." she says, gesturing to my costume.
"No, Jess. I'm straight. Everyone always assumes drag queens are gay. Some are, some aren't. I am most definitely not. It is hard to explain why I do this," I say running my hands over my dress. "And I don't want to be a woman. There is no gender identity thing going on with me either."
"I want to know all about it," she says, her eyes pleading with me.
"I will tell you - later. Right now, I have another set. Will you stay and watch?"
"I wouldn't miss it for the world, Jason," she says smiling. Rising up on her toes, she surprises me with a quick kiss on my cheek and then leaves my dressing room.
It takes me a few moments to gather my nerves. Seeing her again has me rattled. I inhale a few deep breaths and head back on stage determined to please the audience and impress a certain lady.
I walk back on stage to thunderous applause. God, it's intoxicating. I open this set with "Real Love" and can't help but seek her out as I sing words of not wanting to lose what I found.
Her smile is radiant as her friends poke her, letting her know they notice she is the object of my focus. She sways in her seat to the beat and mouths the next lines telling what we mean to each other.
I close with "Believe" to a standing audience. No one from my past knows I do this. Seeing her support and seeming pride in what I have become means the world to me.
I hear a knock on my dressing room door.
"Come in."
There she is. This is the second time my heart has jumped tonight.
As I move toward her, she comes inside and closes the door behind her. When I reach her, we just stand there staring into each other's eyes. Her eyes sparkle with excitement. Is she wound up from the show or is there maybe more?
"J-"
I interrupt her by cupping her face with my hands. We press our foreheads together, staring into each other's eyes, noses touching. I move my mouth towards her to gently taste her lips for the first time. It is a sweet, soft kiss. Breathless, I wait for a reaction.
Her hands move up to wrap around my neck with one hand stroking my "Cher" hair. She moves to taste my lips this time. Another gentle close-mouthed kiss.
"More," she whispers. "I want more."
I will never forget these words and passionately press my mouth against hers. Our lips move together, perfectly synced. I hear her breathing faster, sucking in air through her nose. My tongue pries open her mouth and we discover tongue play together.
"I want you," she whispers.
"Do you want me to change back to Jason, first?" I was unsure of her comfort level with my Cher persona.
"No, this is a part of you and I want to know all of you."
"Well, at least help me out of my dress. I need to untuck a few things," I say laughing.
I turn around and she giggles while unzipping me. She watches with interest as I release my privates. My cock is rock hard and was uncomfortable being restrained anyway. I reach for the top of my stockings and she grabs my hand.
"Leave them on."
I smile at her as she looks back at what's between my legs and reaches for me.
"Jason, you are huge! I mean you are tall and have big feet, so I guess I should have known. But, I don't see how you hide that thing!"
I laugh again answering, "Well, it is a little bigger now than usual - thanks to you."
Her hands continue to stroke me and I am in heaven watching her. Shaking my head, I still can't believe what is happening. I release her hand from my cock and lead her to the couch, laying her down on her back. I slide on top of her and kiss her beautiful lips. She is a wonderful kisser - the best I have experienced, I think.
A mirror is behind her and I can't help but stare at my reflection. A beautiful woman looks back from the mirror, flushed, ready to fuck. Rising up on my knees, my hands slide her skirt down and over her feet. I gaze down at her teeny tiny black bikini - the last barrier. Hooking my fingers and thumb in her waistband, I take my time sliding down her panties for the intimate reveal. She is shaven bare - my favorite.
Sliding back up her body, she spreads her legs, welcoming me between them. I probe her lips until I found her opening, and push my cock inside. Using just the tip, I push and withdraw, push and withdraw, watching her face flush with arousal. Her legs lift and wrap around my waist and I fill her completely, giving her the length of my cock. Holding my position, I look into her eyes, brushing her hair back from her face.
"Jason, you are beautiful. You are."
"I love this feeling, Jess."
"Jason ... make love to me."
And with those words my hips start to move, slowly thrusting inside her wet pussy. She is tight for me and I feel her stretching with each push. Her walls tightly hug my cock, each time I pull back. Our eyes hold one another while I fuck her. Words aren't needed right now. Her legs tighten around my hips as she begins meeting my thrusts with her own. Like our kissing, we move perfectly together.
She feels so good inside, I am quickly feeling out of control, wanting to fuck harder. I don't want to rush our lovemaking but may not last much longer. I think she senses the growing urgency.
"Cum when you need to, baby. We can do it again, right?" she whispers, smiling.
"Roll over," I instruct. Now we can both watch in the mirror.
I withdraw and lift up to give her room to roll onto her tummy. I lift her ass, scooching her knees forward and plow back into her. My self-control abandons me. One hand tightly grips her hip while the other slips around to attack her swollen clit.
"Oh, God, Jason! Harder" she begs. She looks up holding my eyes in the mirror. I love the reflection of us in the mirror. Seeing myself in drag fucking her is so hot!
I fuck her with raw abandon now, pummelling her pussy as hard as I can. In and out. In and out. My pelvis smacks against her gorgeous ass, balls thumping her. Mirror fucking is so erotic - watching her face contort. Oh my God, what sensual shapes her mouth forms as she moans and pants. Every muscle in my body is taut. I tear my stare from her gorgeous face to watch my cock piston in and out of her pussy.
"Jess!"
"Jason!"
The side of her face is now mashed into the cushions and I see her eyes close and her mouth open. The room is filled with our animal sounds.
Her body suddenly stops moving and she smashes her face into the couch, her screams muffled. I feel her pussy shuddering around my cock and I explode. Watching my own face in the mirror, I thrust three more times, spurting my seed inside her. "Fuuuccccckkkkk!"
I reluctantly pull out and we reposition ourselves to face each other on the couch.
"That was ... amazing," she purrs, rubbing a thumb over my lipstick-smeared lips.
"A long time coming, for me. I dreamt of this many times, Jess," I confess stroking her hair.
She twists my long back hair in her fingers. "Well, I never dreamt I would fuck Cher, but I am glad I did."
We both laugh, cuddling, kissing. It feels good. I didn't think I would find a woman who would so readily accept this side of me. Could this turn into something real? I smile at this unforeseen turn of events and think of Cher's words, "If grass can grow through cement, love can find you at every time in your life."
Mikayla
- 08.05.2021
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- Crossdressing
