The Bailey's Play D&D

This is a silly idea I've been thinking about for quite awhile. I expect this will be a fairly casual thread. I'm not sure how erotic it will be though some fantasy shenanigans are sure to happen. What I'm saying is...keep expectations for this thread as low as possible, this is just for fun. I don't know how often I'll add to it or how long it will go but I hope we can have a few laughs along the way.

If you are new to Runt of the Litter this is NOT the thread to start with. I am going to assume a certain amount of familiarity with the characters and background. This is a thread for the long time readers.

Finally, I intend to give my Patrons some goodies along the way. The girls' character sheets have already been posted there (Patrons please don't give any spoilers) and I hope to do a few "in character" shorts there as well. I just wanted to be upfront about that as there may be some minor side-quest gaps in this story as things progress. I'll try to make sure nothing too important happens off site.

***

It's been just over a year since the big reveal and things have changed in your life and in the Bailey household.

You were still with Allison, though you really didn't know why at this point. She was HUMILIATING to be with. It started gradually but once things began to spiral there was no going back. She made fun of you, emasculated you, belittled you, and pointed out your sexual shortcomings every chance she got. She did so privately and publicly. Your reputation, especially among your friends, had taken a massive hit due to your acceptance to being Allison's beta male. It had started as kinky fun that, for reasons you'd never understand, was actually pretty damn hot for awhile. The exciting new kink has mostly since faded however and you were getting less and less out of the relationship with each passing week. You knew lasting damage had been done to your social life but you had allowed it to happen and you had to lie in the bed you made now. Your family all despised Allie but respected your choice to be with her. In your heart though you knew it wouldn't be long before you left her. But, for the time being, she was still officially your girlfriend.

Being a good and loyal boyfriend was important to you and it was this that kept you from fully partaking in the taboo family secret. You'd experimented a bit with them, mostly just masturbating as you watched them, but you had yet to taste that forbidden fruit. Not that you hadn't been tempted! Watching your dick slinging female family go at it was easily the hottest thing you'd ever seen in your life.

You were still in college, taking classes and doing your thing, but now Elsie had joined you. She graduated high school near the top of her class and was currently acing her courses in the first year of her computer science degree. Her years of staring at a screen however had caught up with her and she now wore a pair of round tortoiseshell Ray Ban style glasses that simultaneously made her look like a nerdy hipster and RIDICULOUSLY cute! She was still too shy when outside of the family and she still hadn't begun dating, but very slowly she was starting to open up. She had some real friends now that she could actually physically hang out with. She turned heads all over campus yet she always rebuffed any and all potential dates.

Fiona graduated from college with a business degree and has since moved out into an apartment of her own downtown, only a few blocks from your cousin. None of the family knows what she is doing for income but whatever it is she seems to be doing well for herself. She has deflected any questions asked of her and the family had since stopped asking. Her business was hers alone. The lack of constant proximity has done wonders for your mother and Fiona's always tense relationship and they were enjoying something of a truce at the moment. With the way Allison had been making you feel lately you haven't had much contact with your big sister. The last thing you wanted right now was another bully in your life.

Your mother, aunt, and cousin were all roughly in the same situation they were a year ago. You'd learned a few things in the meantime however. Your mother had pushed hard for you make yourself into a sissy. She bought you panties and dresses and all manner of women's things. You knew it stemmed from a deep twisted fetish of hers, the really weird part however was how TEMPTED you were by it all. But you held your ground. You might be a lousy lover and a pathetic man according to your girlfriend, but you had some pride left god damn it! Aunt Peg had tried time and again over these past few months to get you over to her house so that the two of you could have a one on one heart to heart talk. Sadly between your schedule and her insanely relentless work habits it just hadn't happened yet. And Chloe...well, she was a pest of the highest order. A constantly and incessantly begging pest. Despite her having a Sugar Daddy whom she was quite smitten with she pleaded with you to have sex with her every single time you saw her.

You'd learned your family had huge cocks, that they fucked each other, and that each of them were eccentric in their own way. But above all you'd also learned that they love you and you love them. Your confidence was in the shitter but you were damned happy that your family had your back when it really counted.

It is another Thursday night at home and you are in your room doing some homework. You hear Elsie's girlish giggle come from her slightly ajar door across the hall. You smile and work a bit longer when you hear her laugh again. It was like this last Thursday night and the few before that. Always Thursday and always at the same time. Tonight curiosity finally got the better of you.

Standing up you walk across the hall and knock on her door. There is no answer. You knock again louder and call out. "El?" You peek your head into her room

She was at her computer with her big gaming headphones on. Her room was an unholy mess as always. You catch her mid-laugh and you are struck with just how effortlessly beautiful she was. Especially when she was smiling. Seeing you enter out of the corner of her eye she turns her head toward you. "Jesse, what's up bro?" She pauses the Twitch stream she was watching and turns her chair to face you.

You grin. "I heard you laughing. Whatcha watchin El?"

"Oh!" She waves you in excitedly. "I started watching this D&D stream. It's SO funny, sometimes sad though. It's just great! I love these guys."

"Like Dungeons and Dragons?" You ask, looking at the screen you see a bunch of plainly dressed 30-somethings sitting around a table. "Like the tabletop version? Not even a video game? They just sit there and talk?"

She nods. "Yep. Just need an imagination."

"You watch people play a board game?"

She nods. "Three or four hours a week."

"That sounds...really boring."

"It isn't! It's awesome!"

"You're such a nerd." You chuckle with good humor.

She giggles. "And proud of it!" She then quips with a guilty look. "The DM's kinda cute too."

God, both those statements made you made you feel good! Elsie's confidence really was starting to blossom. It was slow but it was noticeable. To be honest, you were jealous. Noticing a big book, crazy colored dice of all shapes, and some paper on her desk you point. "And what's all this?"

She grabs the papers in both hands and eagerly passes them over. "It's my character! Aerwyna."

You look over the character sheet, not really understanding what all the numbers and such meant but getting the gist of them. "Aerwyna? Character? Are you in a game?"

She blushes and sighs. "No. Felix is always working at the diner on the weekends and Casey's so busy with all her rehearsals and stuff." You feel your heart skip a beat at the mention of Elsie's gorgeous new college friend. You would dump Allison in a HEARTBEAT if you thought you stood a single chance with that red headed angel, but a classy girl like Casey wouldn't give a guy like you the time of day. She was nice enough to you the few times you met her but you knew that was only because you were Elsie's brother. El continues. "And Zoey...well, I don't think this is really her kind of game."

Looking over the different numbers and weird game terms on the character sheet you were **** to agree. The ditsy Zoey would be lost dealing with all of this math. "Good point."

El takes the character back. "I kinda just...watch and think about what my character would do is she were there with them. I sorta game vicariously through the show." She scrunches up her nose and pushes her glasses higher up with a finger. "It's pretty pathetic, I know. But I like it."

"Huh. Well...cool." You smile. "I'm glad you found something cool to watch."

"Want to join me?" She asks hopefully.

"Nah, this essay is kicking my ass." You point back over your shoulder. "I gotta get back to it."

"Aww, okay." She puts on her headphones and turns back to the screen. "Good luck with the essay. I love ya big brother."

You smile. "I love you too El."

You walk slowly back to your room and take your seat once more. Again you hear Elsie burst into a tittering laugh.

Huh. Elsie liked D&D. She watched it every week. She wanted to be in a game. But she couldn't get a group together.

It hits you immediately. You could be a DM for Elsie, it couldn't be that hard. It's not like your social calendar was anything but depressingly barren. It'd be something new to try. You knew there was a place near campus where you could get the books and the dice. She would be so excited and you'd make her so happy. She thought the DM on the show was cute...maybe if you DMed she would think you were...

You shake your head and **** the naughty thoughts away. "Focus Jesse." You mutter.

You sit up tall and nod your head. You would do it! For Elsie you would do it. You would buy the books, learn the system, and run a game for Elsie and her character. It actually sounded like it could be interesting. It would give you something beside textbooks to read anyway. The more you thought about it the more you felt good about it.

But...the more you think about the more you realize you didn't quite have all the pieces figured out. You COULD try to run Elsie through a game by herself but that didn't seem like how the game was supposed to be played. There needed to be other players there for Elsie to share the adventure with. On the video El was watching there must have been seven or eight people there. That seemed like too many for someone like you who was new to the game, but at least a few more people were necessary.

There was no way around it. You needed to gather a party.