WHAT THE HELL CHERLY
- 3 years ago
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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."
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Love StoriesThe Creation of Cheryl By Jessica Martin Author's note: The concept of a man buying makeup and women's clothing and 'passing' with no preparation or experience is similar to blindly investing in the stock market and making a killing - it's not going to happen. I considered adding sex to the story, but decided at the end that it was unnecessary. The concept of "forced compliance" won't happen and the actual conversion is (at least for a very long while) a fantasy, too. This story is...
Tommy knew he was taking an awful chance, but if he was ever going to fuck Cheryl, he just had to let her watch him fuck either Miss Parsons or Miss Williams!!! If she could see how much pleasure he gave them with his big pecker, he was that then she would gladly let him put his penis into her cute little box!!! The trick was getting her to join him in Miss Parsons' room after school, if she suspected anything, she wouldn't show up! Then it hit him, why not have Miss Parsons make Cheryl stay...
EroticFirst impressions whether they be online or in person are not always accurate. I had posted online a thoroughly debauched tale of fisting and stretching – one of many. It is always good to get feedback and I often get asked if the stories are real or 100% fiction. The answer is a mix of the two. One of the stories elicited a response along those lines from a reasonably new user from the particular site I posted too. It is easy to become dubious of new posters that have profiles with very...
Catholic Schoolteacher I had been a schoolteacher for quite awhile and had even retired after thirty years of service but when Father Tom asked me to join the staff at the Catholic High School I did. He asked me to do so as a personal favor to him. He was not in the habit of asking me personal favors so I knew that he needed my help desperately. I soon realized why he was so desperate in the first place. The money was ridiculous, the classrooms were only half full, and they were...
Posted: April 21, 2002 - 12:00:00 am All good things must come to an end and the college student's summer sojourn with his aunt and her nubile daughters was no exception. His amoral activities during his four-month visit did, however, have a lasting effect that went beyond the debauchment of his adolescent cousins and the first manifestation effect of this involved eleven-year-old Sue. Dear Dairy - I sure miss Bill. And Jan, too. Cept she's sposed to be home weekends. I think Mom guessed...
Thu Sep 20 It was Barbara's turn to spend the night protecting Anita's (or maybe Reverend Gillis') virtue so John would be at home all night alone with his sister in law, Cheryl. His wife wondered briefly if it would be safe to leave him that close to the girl who obviously tempted him but then she decided that if he hadn't fucked the girl the night she sent him down to teach her a lesson about teasing, then it would be safe tonight. And if he had fucked her that night, then at least it...
Ariana lying lackadaisically noted with sheer boredom it was raining. No chance to walk in the park to work. She would have to take the shuttle. She was told to take time off. Paul hadn’t been gone for long. Their last conversation before he faded from her forever. She had no time to play the grieving, loving sister. ‘Ariana this is the truth don’t take time to figure it out from all angles.’ Peter whispered parched. ‘Peter, The Council of Salvage of Earth, are you certain?’ Ariana...
My relationship with Cheryl had just about run its course. Cheryl was a bleach blonde, medium height, pretty face, brown eyes, and a few extra pounds which she carried well, but her two most standout features were her large all-natural breasts and her magnificent bubble-butt. My problem was that Cheryl was such a control freak. Okay, that had its good points. We always got top-notch service in restaurants, although the way she chewed out sub-standard waiters made me cringe many times. But it...
Tommy knew he was taking an awful chance, but if he was ever going to fuck Cheryl, he just had to let her watch him fuck either Miss Parsons or Miss Williams!!! If she could see how much pleasure he gave them with his big pecker, he was sure that then she would gladly let him put his penis into her cute little box!!! The trick was getting her to join him in Miss Parsons' room after school, if she suspected anything, she wouldn't show up! Then it hit him, why not have Miss Parsons make...
Therapy, Part 1It was my medical doctor who suggested that I should speak to a counsellor, or ther****t about my sexual fantasies, and how they had started to overwhelm my life. At first, I was not particularly interested in talking to anyone about this, but obviously my doctor felt that a counsellor could help me, and that not seeing one could eventually harm me.I booked an appointment for two weeks ahead, thinking that this would give me some time to get my shit together, and I could call...
My name is Cheri, I live my life in lace and satin. I have always loved the way those materials feel against my soft skin. I have shoulder length red hair and bright green eyes. My friends used to call me Charles but about 18 years ago i had this epiphany that i felt out of place as a man and one night while I was out at a club with some friends, I realized that being a woman felt... I don't know, right, to me I guess. It's been a long road but I'm so much happier now. The first time anyone...
She MalesBecoming Zoe By Julie O Chapter 1 "I'm home," announced Zach Jones as he entered his apartment. "How'd it go?" asked his roommate Brandon Miller, as he turned around from watching the TV. Zack took off his hoodie and then flopped down on their beat-up leather couch. "No luck," Zach replied in a tone of defeat. "Another fucking wasted day." Brandon didn't reply and just let his roommate vent. "Man, I went to at least a dozen places today and no one is hiring. A few...
--Monday, 24th May, 1999-- I grimaced as I pulled my sword free of a monster’s body, the four-legged, spiny creature – like the progeny of a rat and porcupine – still twitching as it died on the cold stone floor of the Tristram cathedral. I was already tired, and I hadn’t even found level two yet. I stared around the dark room, the only light coming from a single torch on a nearby wall and several standing candle racks. The dark blood on my blade glinted wetly in the dim light. The torches...
Things continued as they were at the Harrison household, though now Helen started bossing her mom around more when I was present. Sometimes, Cheryl did what she asked, at other times I intervened. It began slowly, but soon Helen demanded to know why I was interfering with her mother. "I like your mother. If I can help her, I will," I told her. "By getting her to disagree with me?" she asked. "By helping her avoid doing what she does not want to do," I replied. "You can't help Ken,...
The next time I was over at Helen's house, things were definitely different with Cheryl. The first thing that I noticed was that she had gotten a new hairstyle. Her blonde hair used to fall just below her shoulder blades. Now it was sculpted close to her head. "Nice haircut," I told her. "Thank you," she replied. "I'd hoped it would be to your satisfaction." "My satisfaction?" I asked. "Yes, that it met your requirements," she responded. "What requirements?" I asked. "You...
Keith’s first and last season as assistant softball coach/assistant football coach at Westside high school was unofficially coming to a close today, which was the last day of school for all students. He knew the day he was hired that he probably wouldn’t be stuck coaching high school sports for long, and sure enough he’d gotten the call he’d been waiting for from Georgia Southern, and starting next week he’d be back in college, coaching football full time. They weren’t a top program, but they...
Part 1: Through the Window It's late at night, I'm totally exhausted from my long day and it's time for me to relax. I take a nice, long, warm, soothing shower. The warm water easing my tired aching body. I retreat to my bedroom and toweling myself dry, I look out the window, noticing a full, silver moon. Its soft glow shining down making the night almost like day. I decide to open my window to share my evening with the warm summer wind. As I stand there, naked, letting the warm breeze...
To the readers: There is no sex in this story. It’s a story about a man and a woman and how they met and lived. It’s a story written for Valentine’s Day. The story is told by their eldest daughter. A special ‘Thank You’ to Estragon for editing this story and making it a much better read. Chapter 1 This story is about my Mom and Dad. They both had passed away a few months apart. Mom went first at age eighty-one and Dad at age eighty-four. They had been married sixty-two years. This story...
Becoming Brittany I Lori and I are deeply in love. We are kindred souls having grown up together and now happily married. Our mothers had been best friends since grade school and both married their high school sweethearts. I am older than Lori by a full 27 minutes, both of us being born on June 1st in the same hospital. We grew up living directly across the street from each other, and other than the fact that our families were close friends, we received no pressures to become...
Pulling up to the motel my cock was already rock hard just thinking about Cheryl. It had been a few months since my last trip to Baltimore and I so wanted her. We had met on craigslist about a year ago and rendezvous a few times. Now it is kind of a regular thing whenever I am traveling through. Cheryl always grabs a room at this seedy super 8 and then text me the room number. Cheryl looked so sexy today she had dark brown shoulder length hair that curled at the end, nicely lined eyebrows, long...
I had been what I thought was staring discretely at this girl for a couple of days, ever since the beginning of criminology class. For the longest time most of the class thought she was deaf, the only communication she ever exhibited was sign language. She stayed to herself, "talking" only to a couple of guys who knew sign. I couldn't help but notice her the first time I saw her, she was exquisite. Not really gorgeous, but certainly pretty. Her name was Cheryl and she had long, frizzy dark...
Becoming by Jack Andrews --- Special thanks to Ed Miller for creating Jackie in his classic "Addicted." This story always screamed MORE to me. It took me thirty years and my entire family fortune...and here it is. --- I took a long, slow deep breath and pushed the button. The five or six seconds that I waited for a response felt like two or three million years. "Yes?" "Hi, is Jackie there?" I said through the speaker. "Um, who is this?" "My name is Chase." "Ok,...
Becoming My Girlfriend by Jaana "A college boy unwittingly swaps his cock for a pussy, his girlfriend tricking him into believing it's a temporary thing, but it becomes harder and harder to believe as piece by piece, she steals the rest of his body. But is this seeming nightmare really a blessing in disguise?" *** WARNING: The following story contains graphic depictions of sex, female transformation and female arousal. You have been warned! *** "UUNNNNNGGG...." Bernard...
My husband bought us tickets for a show in Edinburgh so w decided to make the most of it and go for the week end. We booked into the Carlton hotel on Edinburgh's north bridge for two nights.On arrival we were shown to a room on the first floor over looking the bridge and directly opposite some offices across the road.Once settled into our room we opened the bottle we had brought and poured a drink and lay on the bed for a cuddle before venturing out for the night.As we lay there I noticed...
Chapter 10 How the sun shined through the window and onto the bright yellow plastic children play table made it pop out even more in Sally's room. The only things in the room brighter than the table were the two little girls playing afternoon tea. How could they not be the brightest things in the room, those two had so much fun together. Having afternoon tea was the best part of the play date with her cousin. This was for the little girl next to her was not a real girl, but...
Barbara went to sleep immediately after her husband confirmed that he had taught her sister the lesson she much needed. And Barbara awoke before five in the morning with a vague sense of unease. A vague sense that quickly became unambiguous. He had been close to her sister in a compromising situation and he hadn't immediately thereafter fucked her, his wife. The twenty nine year old woman lay there agonizing over what had happened or, more precisely, what had not happened. Had John gone too...
The Researcher By MadQuill Please remember this is a copyrighted work and all legal disclaimers apply. This is a work of Fiction and will have additional chapters. Thank you for your comments. One She and I had known each other for nearly a year when she asked me if I would move in. My world wasn't much to leave behind but I'd paused since I had felt I should be contributing. "The apartment is spacious Jon but my father's company owns it and therefore I don't pay the...