The Ballad of Jaimie and Vera Ch. 10

I learned that, no matter how slick you think your double entendres are, it is side-splittingly funny after the fact. It was embarrassing and hilarious to hear our drunken mating dance done sober with straight faces. My face was beet red the entire time.

One of the lesser known performers, a woman named Lola, got up next, and read a series of limericks and haikus. She really surprised me with some of them. One was an ode to Ron's penis, which she called dibs on. Most of them were shout outs to other participants she admired, but a few were either extremely deep or uproariously funny.

One guy got up and gave a testimonial about showing his video to his girlfriend, and how it had really opened the door for both parties. Although he doesn't do drag, they worked out a system like Kelly and Casey use to bring home other people.

During that guy's story, Vera got up and busied herself with something techie behind me. As he was finishing, she unrolled a screen up on stage, and showed a 3 minute video of outtakes from our Road Trip to the tune of Bowling For Soup's "My Wena". Most of the video was various peoples facial expressions matching what the song describes. She had cumshots that hit the camera. One time when I came in a girls mouth. When it hit the back of her throat, it surprised her and she staggered backwards, but I kept cumming and hit her in the eye at which point she fell backwards off the bed. A few shots of me whipping my cock around like a windmill. Footage of one time when Vera used a whoopie cushion during anal sex and I ran away screaming.

Etc.

It felt a little bit like a roast, but nothing was below the belt. I cried from laughter. Vera took the stage again after the video was over to a round of vigorous applause.

"Ok, ok! The last part of this is coming up. The raffle winners know what they have to do, and the rest of you are free to stay and eat, or roam at your leisure. And just remember, if you have any questions..."

"FUCK IT!!" came the roaring response from everyone. It took me a minute to remember that's how she tags all her emails.

"What raffle?"

"Oh, don't worry about that," Vera says, motioning me up. "I do need you to come with me though. It's for your birthday." The lesbian from #31 gives me a high five on the way out. What was her name?!

Kelly meets us in the hallway, and she's got on the biggest smirk as we take the elevator up to the top floor. 8 floors... I need to learn how to count! She's looking awfully damn good in a striped blue power suit. She takes the lead once we get out into the hallway, and ushers me into her room. Vera waits in the hallway, and I begin to feel like Kelly led me to another trap.

"There are three winners to the raffle. I'm the first, and I get the best job since I get to keep you in line!"

"Keep me in..." and then I see it. Spread out on the bed, complete with all of it's accessories, is... "Son of a Bitch!"

"That's right, girly. The French Maid costume." Oh, she is eating this up. "Put it on."

For a split second, I consider rebelling, but Kelly is... formidable. In my mind, I've built her up to be a master of Krav Maga, or something else equally lethal. For a split second, I feel uncomfortable with cheating on Vera and Roy, but they put me up to this! Those assholes! For a split second, I wonder who else won... but then that's the fun of it, isn't it? I have no idea... Kelly walks over to lean against the dresser. After a deep breath, I decide that I'm in and start moving.

"No," she barks, "do it slowly." Technically I don't have the costume on yet, but it doesn't feel very much in the spirit of things to ignore her at this point, so I comply. I turn away from her while I unzip my dress, and slide it down with deliberate slowness. I remove each of my shoes by hand, rather than kicking them off. I unclasp my bra, but turn around to face her before allowing it to fall to the floor. She looks me over from head to toe wolfishly. I unclasp the garter belt from the stockings, pull out my penis, and remove each one as delicately as I can.

I notice that the matching panties are missing, but that feels intentional. I start with the bodice, which Kelly is reluctantly kind enough to help me lace up. She's not gentle with the strings, but I look really fucking good in it when she's done. The stockings, heels, and gloves all go on with Kelly on the sidelines, soaking up every view with a grin that makes me just a teency bit nervous.

The last piece is the hat. I go over to the bathroom mirror and am fixing up my hair when Kelly walks up right behind me. Her head just appeared over my shoulder, but the real shock is when her hand clasps my buttock and her thumb starts pushing up. Her thumb is lubed! It slides up between my cheeks and presses against my anus. I pause, arms raised to pin the hat in place, while she breaks through.

"Oh my, this is far too tight." Her thumb keeps popping in and out. "We're gonna have to do something about this, aren't we?"

"Yes, mistress," I say, trying to suppress a grin. I was never good at the straight face while wearing this. Not like Vera. She can play the naive waif like she was born for it when she wants to, but I have to really try. "Please stretch it out..."

"On the balcony. Now." I quickly finish pinning the hat in place while I strut out of the bathroom. "We're gonna have to work on your walk later. Your ass isn't shaking nearly enough."

"Yes, mistress." I open the door, and the view is quite lovely. Most of the buildings in the area are shorter than this one, so I can see pretty far.

"Against the railing."

"Yes mistress." I walk up close enough to bump my hips with it. Kelly's hands wrap around my waist to pull me back a foot and bend me. When I lean forward, my tits immediately fall out. The cupping is woefully inadequate. They're just hanging out over the railing for all the world to see. Then she pats my ankles a little until I've spread them out to her liking.

She doesn't do anything at first. She just walks behind me and stares. When she walks far enough behind me that I can't follow her over my shoulder, I take a moment to look back out over the city, and the degree to which I am exposed sets it. It makes my cheeks ignite with embarrassment, but I also can't stop the smile. Damn you, Vera.

After a minute, Kelly removes her jacket and lays it over the back of one of the chairs. Her short sleeved shirt reveals very toned arms, from her biceps all the way down. Then I notice the bottle of lube that has probably been on the table the whole time.

"Eyes forward."

I don't even get to watch?! Damnit! It's torturous to hear the clacking of her heels as she paces behind me. After a minute, she covers the distance from the table to my side. She places a hand on the middle of my back, and then...

Two of her fingers enter my ass. I try to twist my heels outward from the ball of my toes, but I get a sharp spank for my effort.

"You will do nothing that you aren't explicitly told to do until we leave this room."

"Yes, mistress! Of course, mistress!" Fuck, that stings!

Her fingers work slowly until the resistance is minimal, and then she begins to push and pull on the edges of my asshole. I have to brace myself on the railing to not be toppled over. It's not that I fear another slap, exactly, but I'm certainly not gonna go seeking them out! After a minute of pulling, she moves around behind me, and two more fingers from her other hand slide in. I bite my lip and throw my head back. The railing feels so cool against my underboob, but that's the least of my concerns when a fifth finger slides inside.

Now that she has fingers from both hands in there, she really starts to pull apart, which draws a sharp cry from me. The way it echoes between the neighboring buildings and down the street makes my stomach flutter. The fear/excitement that comes from being exposed causes me to whimper a little more. Kelly gives one more good pull in both directions, and this time I manage to muffle the response. My cock is poking the glass beneath the railing, thick as a tree trunk.

"Now we're getting somewhere," she says, and all of her fingers leave me at once. "Oh, look at that lovely gape. That's magnificent..." Her tongue slips inside my hole, and my eyes cross as she gets farther in there than I've ever had a tongue get. She only stays long enough to tease me, though, before she comes back around to stand beside me. Her hand returns to the middle of my back.

"This is going to hurt," she whispers into my ear. I want to look back, to see what's about to happen, but I think I already know...

Four fingers push into my ass. They get hung up at the beginning of her palm, where her hand gets much, much wider very quickly. I can't muffle the cry this time. I want to make sure no one is watching from across the street, but I can't open my eyes. I want to know that someone else is enjoying the view, but I can't pull my chin away from my chest.

She works just the fingers in and out, but each time in the pressure is just a little greater. I can't seem to relax the muscle any more so it's just a matter of stretching until it fits, and I have no illusions that Kelly will stop short of stretching my ass until it fits. Roy's cock has a thick section in the middle, and opening up enough to get past that is usually quite an effort. This is worse...

Ooooooooooh she keeps getting up to the knuckle and pulling back. It feels like I'm at the widest part, and I'm dying for her to go further. The next time in, when she pushes to the widest part of her hand, to where the thumb is pushed up against the edge, her fingers start wiggling. My neck tries to shrink down into my shoulders, and my knees wobble for a second.

"Steady, girl. Steady," she whispers. You know how sometimes, when people talk but you can't see their lips, you can still tell that they're smiling?

The hand on my back presses down gently, and Kelly makes one more push. Her thumb, tucked up into her palm, is much less of an obstruction than I'd assumed it would be, but it feels like it takes forever to get to her wrist. My hips feel so narrow with her in there...

...And then she's in. I exhale loudly. Deep breaths feel tighter, so it suits me to take short, shallow breaths accompanied by whimpers that vary in volume depending on how much is moving inside of me. She squats down next to me, and her hand moves from my back to grab my cock.

Oh thank god... but she isn't stroking...

The hand in my ass is the star of the show. She alternates between making a fist inside of me and pushing in/pulling back but not out, and spreading her fingers. Her fingertips feather my insides, and that's what draws the strongest response from me. Even my breathing gets a stutter when she works all of it at once. The fist is no cakewalk, but I sound like I'm having a seizure when she does spirit fingers..

I get a forceful reminder of just how strong Kelly is when her hand clamps down on my cock at least twice as hard as it had been. In rapid order, my voice starts rising higher and higher, and everything starts clenching. But just when it feels like I'm getting there, Kelly makes a tight, tight fist and pulls it back, back, Back, Back, Back, BACK, BACK, BACK AND OUT! GOOD FUCKING GOD NO!

My knees give out, and the wind is knocked out of me as I fold over the railing. There's a light breeze inside my asshole... Kelly is next to me after a minute, pulling one of my arms up over her shoulder and helping me upright. My cheeks are cherry red, and my pained expression amuses her to no end

"One down, two to go!"

"Two more? Fuuuuuck," I say.

"Don't worry. I think you're really gonna like the next one." She gets me a bottle of water, and I take a few minutes to catch my breath. Kelly looks extremely pleased with herself. Once I'm upright, Kelly crosses over to me to slap my arms just below the shoulder.

"You ready?"

"Yes Mistress." God damnit! 10 more seconds!! Oh god, I was so close!!

"Good. Now strut, and I want to see that ass shake." Working it causes my cock to bounce from outer thigh to outer thigh. Fuck, I really, really wanted to cum just now. "Much better." My tits are bouncing all over the place too!

We get out into the hallway, and Kelly directs me to the far side of the building. We pass a few rooms with open doors. Somehow Vera got the Lesbian from #31 to go down on Roy in one room. I can never remember her name. Daisy? I think it was a flower of some ki-

SMACK!

"Eyes forward!"

Fuck, that stings!! I correct my posture and continue down the hall. Finally, she taps my shoulder and points me into the next room. She closes the door behind her, but then stays there, arms folded and feet spread apart.

"Hey sis!" Carol Ann?! It takes a supreme amount of effort not to break character, but even more so when I round the corner and get a look at her. She just gave birth to their second child, a boy this time, about 6 months ago. I haven't seen her in a couple months, but she looks fantastic! She's got on a transparent black teddy, and her breasts are sooooo swollen. I can't take my eyes off of them. I come to a stop in the middle of the room, arms tucked behind me, but it's hard not to stare. She walks towards me grinning.

"Oh that's right! I forgot you were coming like this! To be honest, I was really just looking forward to fucking you. This," she pauses, dragging a finger over my costume at the stomach, "is just an added bonus." My cock hasn't dipped in the slightest yet. From the side, I really get a good view of how huge her tits are now. She's gotta be like a G cup!

She drags a chair over from the desk, plants it behind me, and then gives me a slight push. I land hard on my ass and wince. Kelly laughs from the door, but Carol Ann just looks sympathetic as she tucks my knees together.

"Poor baby... Did Ms. Kelly treat you roughly?"

"Ms. Kelly," she says from the door. "I like the sound of that."

I just shake my head, unsure of how I'm supposed to address her.

"Well good." I didn't notice that she's not wearing panties until she straddles my legs and sits down in my thighs. "No hands, understand?"

I nod, although I don't understand. Not until she reaches in and pulls one of those milk jugs out of her teddy and holds it up to my mouth. Her nipples are like a hand-span wide, and my eyes cross following the tip as it gets closer and closer... My lips purse around a knot almost as thick as my index finger. At the top of my field of vision, I can just barely see Carol Ann licking her lips as I start sucking.

My cock is throbbing, jammed up under my left tit, as I coax out the first few drops of milk. It's so delicious... Hers is thicker than mine or Vera's were, and sweet. Like cream. I purr between swallows, and her lips break slowly into a smile. I can just make out the shadow of her teeth between her slightly parted lips. The lids of my eyes become heavy, and I close them.

The loss of one sense immediately strengthens the senses of taste and touch. Her hardened nipple fills my mouth as I draw more of it in. The milk is coming out on the back of my tongue, squirting harder. I can feel her squeezing her tit with her hands to increase the flow, and I quietly thank her with my tongue. My cock is aching...

And the taste!! Dear lord!! I grab hold of the chair back to stop them from rising, because all I want to do is sink my fingers into her pillowy bossom and drown. Or suffocate. It's intoxicating!! In the back of my mind, I wonder if she's been loading up on aphrodisiac foods, but the rest of my mind is too busy hoping that is the case for it to become a concern.

On and on. It comes in dribbles and streams. I barely notice when she leans back and swings her other massive mammary around to slap my cheek.

"Oh dear," she exclaims, but I instantly forgive her when the nipple is presented at sucking range. More. More.

"That's gooood. Oh, that's fucking good." Her voice is a whisper I can't be sure I was meant to hear, but the reinforcement that I'm doing a good job puts the flush back in my cheeks.

"Jeeeeeeesus fucking christ," Kelly laughs. "That is disappearing into her mouth..."

"I know!!" Carol Ann's slightly distracted, slightly high tone feels so far away. I just want more, and my cock is ready to explode...

"Aaaaaaaaaand stop!" WHAT?!?!

"Nooo," I whimper. My lips follow her tit as she pulls it out and backs away, but Kelly steps up in my peripheral vision, and I immediately regret both actions.

"Don't worry, slut. We're heading to the end now." I hesitantly get up and head towards the door.

SMACK!!

I yelp, and get my posture as perfect as I can.

"That was for speaking out of turn, slut."

SMACK!!

"That was for continuing after I said stop."

SMACK!!

"...that was because I like watching your ass jiggle!"

As if it wasn't sore enough back there! Kelly directs me back down the hall, and I swear we end up right back at the same room we started in. Kelly steps aside so that I enter first, and once again takes up position in the short hallway to block any sort of escape. I don't recognize the naked woman looking out the window. Her blond hair, lighter than Kelly's but still dark, looks so familiar though.

"Hello, Bradley," she says. No, it couldn't be... "although I hear it's Stone now?" She starts to turn around, and

"Kara?!"

I immediately glance at Kelly out of the corner of my eye, but she makes no move to punish me. She seems content to just watch me squirm, but when I then take a half step back, she shakes her head at me. I try to resume my upright posture, but it's extremely difficult...

"Lie down on your back," she says, and I swear it's like I can hear my own authoritative voice echoing behind her. I slowly get down, although it takes longer than it should because I refuse to take my eyes off of her.

"That's good enough," she says just before I get all the way flat. I'm still up on my elbows as she steps over me. Her sneer is in full effect. My cock is practically vibrating as she gently kneels down over me and eases it into her pussy. She only ever pushes deeper, never pulling back, although she takes forever to lower herself down until...

I hit her cervix again, but she's not changing direction... She closes her eyes, bites down on her lip, and wiggles around a little. She gives a little gasp at the same time I feel the tip of my cock find a soft spot, and then she starts pushing again!! Holy Fucking Shit, my head is pushing through!!

Kara's hands are planted on my stomach, and her fingernails scratch red lines as my enormous head pushes, pushes, pushes, aaaaaaaaaaaaaand

"Holy fucking shit!" She's panting, but a self-satisfied smile creeps over her lips as she finally looks down and makes eye contact with me. "Now you can cum," she says, and my shocked expression changes very little when I do just that.

"Happy birthday," Kelly whispers. I hadn't even heard her come up next to me. She gives my cheek a light slap, and then she's exiting the room. It is a huuuuge load... Kara's hair is covering half her face, but it's big enough that I don't need to see it all to know it's there.

"You can talk now," she says.