When All Else Fails Ch. 01

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An eccentric genius decides to Crossdress as a bet.
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*****

"I'm so bored." Shane Danielson stared off as one of his few friends, Joshua Cross, dealt out another hand of poker. The weekly tradition began the year before when they met at a party and continued despite the unique relationship the two shared.

"Maybe if you focus on the card game instead of the ceiling tiles you could solve some of your problems." Joshua was a giant is anyone ever seen one. He stood easily a foot over his opponent for the night and made sure the smaller boy knew it every moment they share together. After being recruited by the basketball coach upon entering high school, the tall boy enjoyed the perks that came from his near seven-foot toned frame.

Shane scrunched his face and tilted his craned head forward to focus on the dull hazel orbs of his closest confidant, Joshua, "Listen, you know I don't have the attention span for meaningless activities when I'm between the psychology departments research projects."

Both boys attended the same university as freshmen. While Joshua was recruited under a full ride athletic scholarship, Shane came to the college in an unofficial capacity two years prior as a gifted student. While he may have been smaller than most of the other boy's in his class and targeted for his physical genetic disadvantage, Shane used his mind like a scalpel which opened doors he could never have imagined. One of these doors was near-unlimited resources to explore any faucet of psychological research he desired.

"Well maybe you should get yourself a project before I decide to entertain you by seeing how long it would take you to ingest a deck of playing cards." Note: Closest confidant, not exactly friends. Joshua basically is the only person who tolerates Shane's eccentric daily behavior in his personal life. Shane's own family ostracized him save for his older sister Denise who attended the university as well.

"Joshua, it's not my fault that I get distracted easily. No need to take it out on me. Jerk face."

"Ugh, don't get sensitive with me Shane. All I want to do is finish winning all of your money so I can then go back to my dorm and fuck my girlfriend stupid. Ah, why don't you call...what's-her-name?" What's-her-name was Joshua's pet name for the variety of women who paraded in and out the revolving door known as Shane's front door.

Shane rolled his eyes at the thought of dealing with the feminine species. Last thing he wanted was some sensitive girl to leave the apartment crying...again.

"Diana. And I'll pass. The last time she came by I lost interest and for some "strange reason" she left. I don't know man; maybe I just need to find something new to grind my gears."

Joshua's eye brow rose as he ran his hand through his copper locks, "Wait go back, lost interest? You saying you couldn't get it up?"

His dark orbs locked onto Shane's ice blue ones before bursting with laughter. "Heh, so you're telling me you, Shane. The conquering her of freaky pussy everywhere, finally fucked his little dick into submission? This is great, maybe I should make this front page of the college news feed. The little bitches everywhere will cry for your loss...ha!" Josh threw the cards on the table before his laughter made him double over into fits.

Shane rolled his eyes before discarding the cards into the now forgotten mess of poker chips and beer cans and brushing his tattered blonde hair out of his face. "Do you want a beer? Maybe something sobering instead...like arsenic laced lemonade or a rat poison cupcake?"

The laughter gave Shane his answer as he walked into the kitchen and pulled a couple bottles from the fridge and walked back to his hyperventilating giant.

Shane popped the top of the cap off of the beer before shoving everything off of the table top and filling the sudden void with his 130lb. slight frame.

"Dude, we weren't done playing the game! Oh come on Shane. How are we going to decide the winner of this card game now? I was about to take a huge chunk of the chips that hand. I would have had you ready to beg off the game." Joshua still fought to suppress the laughter quaking through his body while he grinned toward the flustered Shane sitting on the now clusterfucked table.

"You can take the money, I don't need it." Shane took another swig of his beer before bringing his knees to his chest staring into the half empty bottle.

"Oh don't get all emotional Shane. You know I'm just fucking with you. Ok, let's break it down then and solve the problem logically. You love logic right? So you, slayer of vagina, have lost interest in women sexually. Have you tried different types of sex? Like...you know...the kinky stuff?"

A slight smirk danced over the blonde boys features before he tilted his head back and slammed the rest of the liquid before leaning all the way back into a supine position on the table, "Of course, I done collars, and wax, and anal, and whips, and chains, and handcuffs, and roleplaying. In the last few months it's become a serious problem. I know it's just a mental thing but I'm sure I'm just bored of the same type of skanks walking in and out every night." Shane let out a deep breath before continuing, "Maybe I need to do something drastic, knock me out of this silly funk. Maybe I just need a super rad research topic to occupy my mind and shake things up."

Joshua leaned back thoughtfully staring at his drinking buddy, watching his legs kick over the edge of the table while he finished the thought. The taller boy kept staring at the diminutive boys swinging legs then something clicked in his brain.

"Shane. Did you shave your legs?"

Another deep exhale was followed by a bored tone, "No, I really don't grow body hair and when I do its just wispy and blonde. It's there you just need the right light to see it."

Joshua stared for another moment until the light bulb in his brain clicked on, "Shane. What about gender bending?"

Shane's head snapped up with his face screwed up, "What?"

"Gender-bending, you know being the opposite sex or playing dress up. I don't know what it's called."

"Cross-dressing?" Shane now sat back up and leaned in still processing Joshua's sudden burst of enthusiasm.

"Yeah sure, whatever. Think about it. This kills like all your birds with minimal effort. You dress as a girl, you get a unique research thesis or whatever-"

"A case study on cross-dressing?"

"Case study, I don't know what you idiot in the science labs call it. Just think though, it's new, unique, and it would for sure give you something to shake the dust and would most definitely brighten your sex life."

"How would putting women's clothes on me help my sex life?"

"Quit being dense genius boy. It would allow you a whole new perspective on the other side and maybe allow you to find other kinky avenues to get off on." Joshua stared at his friend with enthusiasm. The dark eyes of Joshua's met with the pale blue orbs of Shane's as the light went on inside his head as well.

"Wait. Josh, you're absolutely right. A social experiment is perfect. I haven't done anything in that field yet so it would broaden my perspective there. I could have Dr. Molly examine my behavior over a set period of time and we see what changes." Shane leapt off the table and began pacing around the living room, "But there are some issues. How far would I go? I can't just throw on a skirt and call it a day can I? No, I have to go all the way. This will have to be a longitudinal case study though, very expensive. I can swing it with a strong enough argument. But, what would everyone think? I have a social life to think about. I could find myself on the outside looking in. Wait...I'm already there anyway. The only reason people interact with me now is manipulation or necessity. Next we -"

"Shane, you're rambling."

"But what about - oh, um sorry lost in the thought."

"I noticed, so why not start right now?"

"Now?"

"Now."

"But there is so much I have to do. A Thesis paper, research, approval. You can't just rush into these things."

"Shane...how about this then. This is a huge decision you're talking about. Give it a trial run. Halloween is next weekend. If you are seeing benefits after just a single week then you make up your mind then."

"I don't know..."

"Fine. I'll make a bet with you then. Just to get you to shut up and make a yes or no choice. If you make it the entire week as a woman 24/7...I'll give you anything you want for an entire day. But if you don't make it and you bitch out, you have to do all of my term essays for the rest of the semester."

Shane stared at Joshua for a long moment, "Fine. Under one condition."

"Name it?"

"You have to get someone to help get clothes and make up and everything. If I'm going to do this, I'll have to be perfect at it."

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7 Comments
BrendaNWBrendaNWabout 4 years ago
Loving it !

Thank you for a wonderful start chronicling Joshua investigating crossdressing at college. Please continue, you have me hooked for sure. TG Tiffany

mel_pomenemel_pomeneover 9 years ago
Good luck finding an editor

You've done pretty well without one, to be quite honest, but it's always good to have a fresh pair of eyes. I hope you manage to hook a good one!

As to your story, I thought it was very good, especially as a first submission. Keep writing, welcome to Literotica, thanks for your story and please have four stars!

AnonymousAnonymousover 9 years ago
This is not a bad start--press on.

This would be good if he went through with it and found himself more attuned to being a working-class, down to earth woman, unlike his male persona and grew to like it more as time passed, so he wound up being a waitress, a secretary or some other lower-level position and was way happier that way,.

silentviper69silentviper69over 9 years ago
giving it a chance

You won't know, what will happen, if you don't try. Would like to see chapter 2.

AnonymousAnonymousover 9 years ago
Grabbed My Attention ...

Great start, please continue ... the story line holds promise, now all you have to do it continue and keep it interesting, laced with touches of sex, sex, sex ... and maybe a little danger or humiliation ... and if he does this experiment correctly, his is absolutely going to become addicted to "All Things Feminine"

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