tagTransgender & CrossdressersMaking Work a Better Place Ch. 05a

Making Work a Better Place Ch. 05a


Why am I the best boss in the World? I get my people a two week vacation in the Caribbean at an exclusive resort with a built in expense account that normally only Chief Executives see. How did I do this wondrous thing? I haven't a clue. Peggy came into my office three weeks ago and told me I'd done it and that we would have to train up some temps to cover us while we were gone.

Did I have to get a temp? Peggy says I'm irreplaceable. Once I found out what irreplaceable meant I panicked. I thought I was going to have to stay here while they all went off to have fun. Peggy poured me a drink and calmed me down. Okay, Peggy poured me a drink and she called Paulette in to calm me down. I don't know what I pay them, but I'm sure it is not enough.

So here we are in the fun and sun. Everyone has an invitation for a second person. Paulette brings Donna, a lady (Peggy says I should stop calling girls girls) from R&D. She does sciency-stuff and Peggy says she's a doctor of something. She tells people how to make stuff. Paulette likes her so she's okay with me.

Walter and Keisha came together, but for the life of me I can't figure which one of them invited Mr. Winton with them. Apparently he likes to go around and get them stuff. I do know they brought a lot of luggage. Mr. Winton could barely carry it all. I offered to get him a bellboy to help, but Keisha declined on his behalf.

Louisa Rojas is with us. She invited her brother along. Gustav is a nice guy. He knows how to dance, party, and chase ladies. When he went skirt chasing I went with him. Louisa and Peggy did a serious cock-block on me and I still haven't figured out why. Peggy got upset so I took her back to the penthouse. She asked me to hold her all night long, which was nice since she looked great with the sunrise bathing her hair. I told her so and she kissed me. I wish her husband had been able to make it because I'm horny as hell and she is so close by.

The second afternoon I went off to get Peggy and I some drinks -- and flirt with the bartender, and when I came back she, Paulette and Donna were all talking together. They stopped talking when I came up and I hoped it wasn't because I hadn't bought enough drinks.

"Come with us," Paulette insisted as soon as I put the drinks down. I'm an idiot, not brain dead, so when Paulette starts dragging me off, I know what to expect. If I thought I could get away with throwing her over my shoulder and running off with her, I would. For some reason I thought that I would have to do the same thing with Donna and I wasn't sure how well that would work out.

"Let's go," Donna giggled. I stole a look over to Peggy because she always makes the confusion go away. She salutes me with a drink and I'm off at a sprint dragging the two smaller women with me.

"Horny," Donna gasps as we plunge into the elevator.

"I had to hold Peggy all night long," I groan. "Her nipples were so hard they left divots in my chest. If it wasn't for her husband I'd have been all over her."

"Peggy's not ..." Donna starts to say but Paulette puts a finger over Donna's lips. Peggy's not saying something but right now I'm busy putting my tongue is fighting for dominance in Paulette's mouth.

Donna comes over and starts rubbing my back. Paulette moans and presses herself into me. I move one hand to the small of Paulette's back, pulling her in even tighter. I take my other hand and slide it down Donna's side to her back. I wiggle it inside the bathing suit and around to her ass crack, moving it up and down.

We start exchanging kisses, Paulette to Donna, Donna to me, and me back to Paulette. When I'm not kissing I'm nibbling on one of their ears. At this time I think a description is in order. Paulette is five foot nothing, maybe one hundred pounds if that, and has long auburn hair that goes past her shoulder blades. Her breasts are small, but her nipples are very perky. Her ass is the best for her size I've ever seen. I'm one lucky guy for knowing her.

Donna is about two inches taller and maybe fifteen pounds heavier, but it is well distributed. Her chest is about a size larger (B-cup), tear-dropped shaped with large areolas and nipples. Her ass is nice and it's only fault is that it isn't as good as Paulette's -- so it's ALMOST perfect. Donna is African-American with deep chocolate skin and short kinky black hair. I so resent Peggy's policy of not letting me sleep with the corporate staff. I'll forgive her because sometimes she lets me off the leash like right now.

Donna reached between Paulette and me massaging us to hardness. In my case that was no effort at all. Did I mention that I had a nipple pressed into me all night long? Even if the nipple was Peggy's and her husband could kill me and make it look like an accident. I really like Peggy, but I like breathing through my lungs too. One day I'll have to decide which one I want more.

The door opens and we stumble out into the hallway. We make our way to Paulette's and Donna's room, fall through the door after Donna finally finds the key, and start rolling around. I look up at the bed and am totally confused.

"We need a bigger bed," I tell them. Paulette and Donna look at their queen-sized and then at the three of us.

"My room has a huge bed," I inform them.

"How big?" Donna asks skeptically. I am undeterred.

"If I put my toes on one side I can barely touch the other with my fingertips."

Donna thinks for like a millisecond and goes, "Deal." We are up and staggering out to the elevator in record time. One of Donna's hands is busy because I've untied one side and she's trying to hold them up. We get into the elevator and Paulette notices something about access to the penthouse.

"It has a security code," she says. Donna and Paulette are both looking up at me. I'm forgetting something, but I can't remember what it is. Paulette smiles intelligently.

"What's your birthdate?" I tell her and she puts it in. When Donna looks at Paulette, she answers, "It would have to be something that he could remember." Donna nods.

I reach into Paulette's bikini bottom and start stroking her. Donna joins me and when Paulette's not being French kissed she's moaning like a woman possessed. I take my other hand and slip it into Donna who is really wet by this time. Her clit is not very pronounced so I have to feel around for it with my thumb. When she has that deep intake of breath, I know I've got her.

We move into the penthouse with a mingling of regret and anticipation. I grab their hands and rapidly lead them to the bedroom. We collapse onto the bed a tangle of limps and bodies. Somehow I end up in the middle. Paulette and I are kissing again. I love the press of her delicate little lips on my tongue. Donna has my trunks down and is starting to make love to my cock.

I pull Paulette up so that I can get first one nipple and then the other into my mouth. Donna and I have our hands collide on Paulette's cock. Donna decides to intertwine our fingers together as we start slowly jerking Paulette off. By this time she's arching her back and using one hand to push her breast into my mouth while the rests on the back of my head; Paulette is really getting into it. Donna has worked about half of my cock in and that seems about all she can manage.

Donna moves up and starts licking Paulette's shaft. I move a hand down her body until I grab a hold of her leg. I have to break off my contact with Paulette's breast to do so and she groans in disappointment.

"I'll be right back," I promise her. I now pull Donna's torso around so that I can fit a finger easily inside her. I've got my thumb on her clit and a finer pushing deeply in.

Donna and Paulette now maneuver around so that I can get my lips back on Paulette's nipples. I tickle in one nipple and then bite it.

"Donna," Paulette gasps. Her hand goes to Donna's head and pushes it further down as Paulette shudders and thrashes about. Donna makes hungry slurping noises.

I know it is time to give Paulette a break.

Donna props herself up on her elbows and wipes a trace of semen off the corner of her lip.

"Mmmm ... that was much more than normal," she teases Paulette. "Has something gotten you all riled up?" Paulette pants and points in my direction. "What do you want to do now?" she says to either one of us.

"I want you ..." Paulette sighs deeply as she reaches out and caresses my hair, "inside me again. Donna, let me taste you."

"I can do that," Donna grins. She scoots around in front of Paulette while Paulette slowly pushes her way up onto her elbows and knees. I head to the lamp table and get the lube. It is right where Peggy said it would be. Man, she has to be psychic.

By the time I get back to the pair, Donna has her legs up on either side of Paulette's head. She's put herself up on her elbows so that she can see me on the other end of Paulette. Donna watches me as I put the lotion on my cock the pour more onto my hand. I oil myself up well the move to Paulette's ass. I tease her with one finger and I hear Paulette moan. Donna gasps.

"She likes that, and so do I," Donna tells me. "It makes her drive her tongue in deeper."

What can I say? I'm a team player. I'm soon knuckle deep in Paulette and she's going to town on Donna. I work my second finger in and Paulette bucks slightly.

"Oh yes," Donna encourages me, "keep going."

When Paulette loosens up a bit more I try for a third finger. Paulette momentarily pulls away from Donna and give the second sexiest moan I've ever heard. I few slowly gentle intrusions and I think Paulette is ready.

"Paulette, I'm going to start fucking you now," I tell her. I pull out my fingers and line up my penis against her anus. I don't even get to push in; Paulette pushes back violently against my thrusting my head quickly inside her.

"Fuck," I exclaim. Even with me opening her up with three fingers Paulette is damn tight. I know what she wants so I grab hold of her hips and begin pushing in. The first time I halt to let her adjust, she trusts against me again. She's the boss so I don't' stop pushing until I'm balls deep in her.

I sense her breathing irregularly so I give her a moment. I lean over Paulette until I have to put one hand down on Donna's knee.

"Are you ready now?" I whisper into Paulette ear. She licks and sucks on Donna's clit for several seconds then nods once decisively. I lean back and start to steadily pull out.

When my head is half way out of her anus, I plunge back in. Paulette grunts and Donna collapses back onto the bed.

"I can feel you pounding her all the way down here," she moans. "Don't stop." Since I had no intention of stopping this is an order I can get behind. I keep rocking hard into Paulette and I hear her gasp and grunt as I slam all the way down. I catch a hint of Paulette slipping her hand into Donna who grabs the sheets in two fists.

Paulette pushes her way up, breaking contact with Donna. Donna seems too gone to care. I take the opportunity to start biting Paulette's neck. I feel her tighten up her ass on me as I come close to drawing blood. I can see down at Donna and notice the Paulette has to fingers in her pussy and one in her ass. I keep pounding with my hips and move my hand around to Paulette's stomach.

I stroke her belly for a moment then make my way down. When I feel Paulette's cock, I start stroking it. Paulette gives me this delicious little whimper.

"Am I doing this right?" I whisper into Paulette ear.

"Yes," she whispers back, "please yes please." She's not making too much sense but I get the feeling I'm doing it right.

I stroke Paulette all the way up the shaft until I wrap her head in between my fingers. As I pick up my tempo, Paulette is hammering her ass up against me, driving me even deeper in. I press her forward and I swear she starts crying. I stroke down, dragging my thumb behind me the way I like it and by the stream of 'please' coming from her, I am guessing she likes it too.

"I'm close," Paulette pleads, "I want to be in you Donna." Paulette puts one hand around to my ass and pulls me forward. I let go of Paulette's cock. At the same time Donna shakes the erotic cobwebs from her mind and pushes her body forward under Paulette. The whole sensation of falling forward while deep inside someone is something I have never experienced before but, man-o-man, I want to do it again.

"Oh yeah!" Donna cries out as Paulette slides into her and then my weight falls onto both of them. I quickly push myself up on my arms. Paulette is pounding feverishly into Donna and I'm trying to match her rhythm. Donna is trying to wrap her legs around both of us. It is the weirdest sensation to feel someone else entering a third person while you are entering them. I highly recommend it.

"I can't ... I can't ..." Paulette screams as I feel her whole body shudder. Her ass squeezes me like a vise. It hurts so much it feels good, if that makes sense.

"Give it to me Baby," Donna pants. "I ... yeah Baby ... fuck!" Not knowing what else to do I keep pounding into Paulette but Paulette is so tight around me that I'm slamming straight into Donna.

Paulette reaches up with one hand beside my ear and grabs my hair. She yanks down until it hurts. She's trying to say something to me but doesn't have any air in her lungs. The whole pleasure-pain thing is getting too much. I push in even deeper into Paulette/Donna and give out a primal grunt as I shoot streams of semen into Paulette's willing ass. Like a man possessed I keep pounding and pounding until my muscles start cramping.

I'm panting so hard I'm afraid I'll pass out. Donna says something but I miss it.

"Huh?" I wheeze.

"Heavy," she gasps back and I feel Paulette pushing up against me. It takes me a second to figure out that Donna has three hundred pounds of lover(s) on top of her. I roll to the side taking Paulette with me. Donna squeezes her leg out from underneath us so it doesn't get crushed. I finally feel myself retreating from Paulette's body.

"No," Paulette whispers to me. She pulls me close and I push myself back into her. She gyrates her hips for several seconds. "It always gets better," she tells me as her hand now massages my damaged scalp. Donna responds with a breathless chuckle.

"Next time I get to be on top," Donna manages to say, "but there has definitely got to be a next time."

"Deal Donna. Paulette?" I ask.

"Yes," she purrs as she wiggles deep into my arms.

"What were you trying to say to me a few seconds ago?" That earns me a giggle from Paulette.

"I said 'don't you dare stop'," she sighs.

"Oh," I grin. I guess I've lucked out.

(A few minutes later)

We are sitting at the top of the bed resting. Paulette brought us hot towels so we can clean up and we've all tossed the in the general direction of the bathroom. Paulette is between us. Donna is idly drawing a line from Paulette's mind thigh to her crotch an around to her hip. I have an arm around Paulette's shoulder with my hand reaching down and am fondling her breast. She's gently licking my nipple when she tilts her head up to me.

"What do you want to do now?" Paulette asks me.

"What is there to do here anyway ... or is it what can't we do here?" Donna says.

"We could go sailing," I suggest.

"You know how to sail a boat?" Donna asks. I sense Paulette tense slightly.

"Oh God no," I laugh. "I'm lucky I can drive a car and I would get lost driving to work if it wasn't for OnStar."

"Joshua, what would you do if you weren't rich?" Donna asks.

"Donna, don't," Paulette pleads to Donna.

"It's okay Paulette, I don't mind. Donna, I've never been poor so I can't tell you what I'd do. I guess I'd be flipping burgers somewhere." I look into Paulette's eyes. "I know I'm not all that bright, and the only times Peggy has called me brilliant I had no idea what I'd done to deserve it. I guess I'm smart enough to know I can trust Peggy and you though."

"Joshua ... you are not what I expected. I thought you would be more full of yourself," Donna confesses. I laugh.

"Donna, I know I haven't earned a damn thing in my life. Peggy had to explain to me that not all university professors drove new BMW's. Only mine did."

"Then she had to explain what that meant," I sigh. "It never dawned on me that I didn't really earn my degree from college. I assumed everyone went for seven years of intense partying and fun," I explained.

"What are you going to do when your Dad leaves you the company?" Donna inquires.

"Do what I always do: listen to Peggy. All I have to do is act like I know what I'm doing and not make any decisions without her," I respond.

"What happens if Peggy isn't around?" Donna persists.

"She said I should listen to Paulette," I answer immediately.

"Seriously," the two girls said simultaneously. "She told you to come to me?" Paulette adds.

"Sure. She says you are smart and you like me and you know how to make the best use of me to keep the company going," I tell them. Now they exchange looks.

"I didn't know Peggy liked me that much," Paulette exhales in surprise.

"Of course she does. She trusts you with me, doesn't she?" I respond. Paulette looks at me with something like real affection.

"I guess she does," Paulette said in a quiet, confident voice. She leans over and kisses Donna and then pulls down my head and kisses me too. I guess it isn't every day that a Paulette learns she's in line to become president of a large corporation. It is also not every day that Donna realizes that the girl she's been seducing may one day be her boss. It is far less likely that I will ever figure any of this out before Peggy tells me.

On days like today I know I have the best job in the World and the best friends in the World, and I didn't even have to work to get it. When I tell Peggy this she smiles at me and tells me I'm smarter than I look.

(More vacation fun to come)

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