But I was about to find out how it would feel.
Big Jim teased my asshole while Little Jim just sat still, in me, holding me up and pinching my nipples. That alone was enough to get my pussy vibrating and contracting. He eased off and just watched over my shoulder as Big Jim drove me into a deeper frenzy. His fingers nudged my sphincter open, winding in circles, slowly getting wider and deeper, teasing my asshole until the walls of my pussy ached.
"Please! Please" I cried. "I can't take this anymore!" A small pool of my juices dripped down one leg. I needed my release. Ass, vagina, mouth, clit, whatever. Just get me out of this orgasm prison and on the other side!
"OK, babe. You asked." Big Jim slowly pushed against my anus, gently pressing forward, then back as my muscles clamped down and forced him out. He moaned with pleasure, and I knew that sound -- Little Jim joined him and I hoped against hope that we could all come at once in one giant pool of lust.
Pain, but pleasure, too, all at once ripped through me as Big Jim broke through my ass and entered me. Little Jim began to thrust in small movements, and Big Jim braced himself against me, cock in my ass, stretching the thin wall of my vagina between the two men, both filling me in every crevice possible.
I felt complete.
And now, we rocked in unison, careful to move in ways that made us one, not three people but one large pleasure center of cunt, cocks, ass and anything that felt good. The climax rolled over me out of nowhere -- what I thought would take longer came like a tsunami, a huge tidal wave that threw me forward and back, with no control.
I was just a dripping cunt, no mind, no thought, no heart -- just the warmth and the thrust and Big Jim up my ass and Little Jim in my hot pussy and then I felt them both explode in me at once, filling me like a balloon, shooting so far in me I could almost taste it behind my eyes.
We panted our way down to earth, my muscles loose and sated, as I slumped forward onto Little Jim's lap. He caressed me and held me, smoothing my hair and murmuring sweet comments. I couldn't hear the words, but I felt the appreciating and the love.
Big Jim slowly pulled out of me and got dressed. Little Jim handed me my clothes and Big Jim helped me put on my shirt, my skirt, and smirked when he got to my ripped panties. I laughed and threw them in the trash. Once we were all dressed, Big Jim took a huge, deep breath, let it out, ad then turned to Little Jim.
"So, those regional reports?"
It was as if it had never happened.
On legs of jelly, I walked out of the room in a daze. As I crossed the threshold, Big Jim said,"Oh, and Alicia?"
"Yes?" I turned back.
"I think," he looked at Little Jim, who nodded, "it's time to make you Head Analyst. With a raise. And weekly, er...daily meetings with me and Little Jim."
I smiled and nodded. "I'd like that. I'm very good at analyzing head."
I left both men laughing as I walked back to my desk. Happy Father's Day, indeed.
Story 2: Big Jim's Coke Can Cock
“The alimony check is late!” My ex wife screamed into my phone, the sound so harsh I wanted to throw my mobile phone against the wall.
“Well, I can't do anything about that. I know they took the money out of my account, so it's just caught in limbo right now.” I could picture Celia right now, pouting and red-faced, angry because she couldn't get her nails done for her weekend with the girls. Oh, boo hoo.
My phone flashed; a call from my vice president of logistics at the trucking company I started a few years ago. Uh oh. This wouldn't be good.
“Celia, I have to go. Call on the other line.”
“You always say that, Jim! Don't you dare hang up on --”
Click. Man, that felt good.
“Hey, Little Jim, what's up?” My vice president of logistics was a young go-getter named James McDorfam. Like me, he'd been a college football player, Big 10, made for the NFL. And, like me, an injury blew him out. Hiring him was one of the best decisions I made when I created my trucking company. Hiring Alicia Jaymes, my new Rate Analyst, was a close second.
“Big Jim, man, someone routed a huge shipment to the wrong center. We have a double that went to Cleveland instead of Pittsburgh. The client is pissed.”
For a moment there, my cock had been nice and hard, thinking about Alicia. Now it deflated. “Ah, fuck. Another screw up with that department store? There goes a few hundred grand down the toilet if we don't fix this.”
“I know.” Little Jim sighed. “I'm headed in to the office, but it'll be a while. I was out four wheeling and I'm an hour from the office. See you there?”
I looked down at myself. I'd been lifting, doing squats and presses, and when I weightlift I wear old, torn sweats. Hadn't showered in a day. “Yeah. I know the drill. I'll be in the office in an hour or so, too. Just meet me there. Any idea who's working the overnight?” The clock read 12:02a.m. Midnight? Seriously? Damn it.
A nice, evil chuckle poured through the phone. “Alicia.” His tongue played with her name.
“Hey now – she's mine,” I growled.
“Not if I get to her first, Old Man,” he shot back.
A surprising flicker of rage filled me. “I mean it, Little Jim.” He was like a 10-year-younger version of me, but blonder. I couldn't compete in the looks department these days. But I had ten years of experience on him, when it came to technique, he was the young Jedi and I was the master. Of raunchy sex.
“Well, you're an hour – and a shower – away, Young Whippersnapper. The spoils go to the man who gets there first.”
Click. My turn to get hung up on. Ah, fuck. I raced to the shower.
No way was he beating me!
¦ § ¦ § ¦
When I interviewed Alicia, I wondered why the hell someone that intelligent wanted to work at a trucking company. She was 21, fresh out of college, fucking gorgeous and smart as a whip. Flirting with her came easy, and I had to hold myself back. No sexual harassment lawsuit was going to derail my company; I'd worked too hard for this. Besides, if I wanted a woman, I didn't need to – or want to – harass or coerce her.
And Alicia made it abundantly clear that she didn't need to be convinced to consider sleeping with me.
She flirted, straight out, in the interview. Even managed to dicker me up five grand in her salary. Anyone who can negotiate like that would be great in bed, where upping the ante is always part of the fun.
A quick shower, some clean sweats, and I was off to the office. Walked in the door and saw her on the computer, coding away. She was damn fast, with fingers and eyes that coordinated beautifully. Within a month of working at Full Loan Trucking she'd become our fastest employee, earning bonuses and pissing off all the older Rate Analysts.
And here she was, working the overnight shift for all the guys who wanted to spend Father's Day with their kids.
A twinge of regret hit me. Celia. I found out too late that she didn't want kids. I hoped for some, but the right woman, obviously, hadn't come along. At 41, time was ticking.
A nice, smart 21 year old might be just perfect.
But first I needed to see if she was serious with the flirting. Sex at the office? Sure.
It's my company, after all.
“Hey, Alicia!” I shouted, waving a file folder her way.
She turned and gave me a big, slow smile. “Hi Jim! What are you doing here tonight?” Her blonde hair was natural and sun-kissed,, and I'd heard rumors that she modeled on the beach. Nude. Did she have suntan lines on that hot ass? Bikini string strips along her hips, curving into her warm, pink pussy? Damn, I was wearing sweatpants, and I felt my cock harden as I wondered, standing right across the office from her. I moved the file folder to cover my arousal and sighed.
Hard.
“Uh, it turns out there was a mistake in shipping. A double trailer went to the wrong city.”
She shook her head, pink lips moving into a worried line. A line I'd like to break with the head of my cock. “I'm so sorry! You must be so stressed.” She hissed the
last word, like a promise coming from those warm, wet lips, begging me.
Begging me? Get a grip, Jim. This wasn't some football groupie hanging out at the dorm, begging for a one-night stand or just a blowjob to tell her friends she'd done me. This was a hot, smart young woman with an ass like Jennifer Lopez's and lips like Angelina Jolie's.
And she was my employee. She wasn't interested.
Then she shocked me, walking over and massaging my neck.
¦ § ¦ § ¦
"You seem tense," she said, walking up to me and caressing my shoulders. "Let me give you a massage." My neck was tight, like granite under silk, and her hands were so smooth I almost cried with the sheer luxury of being touched by someone with such skills fingers. She made me relax, soothing my aching stress, releasing the stupid call with angry Celia from my body, putting all thoughts of pissed off clients aside, making me want to pull her into my lap and ride the big-ass monster hard-on that my sweatpants couldn't hide.
She gasped, and I opened my eyes and looked back at her. She was staring at my dick.
That was my invitation.
I flipped her, fast, into my lap, and the tip of my cock pushed against her ass. Ah, God, I could only hope. Fucking Alicia would be one thing; getting in that tight, sweet ass would be a form of heaven.
Hungry lips ate mine, and she kissed me like an animal claims another during mating season. I wanted her to mount me, to pound against my huge cock, to slap my balls against her taint and slip a finger in her ass, finger her clit and make her howl at the moon, exploding. As her lips and tongue penetrated into me, I fought back, trying to make her know that I was the man, that I had the power, and that she was mine for that moment.
Aggressive women turn me on, and she came right back with hands that wandered down the back of my pants, rushing to pull them over my hips, a teasing finger in the cleft of my ass. I was nearly pinning her to my possessive hand that now slid through her hair, teasing and owning.
One swift move and my muscled hands, so skilled with a football, ripped off her panties and flung them across his desk where they landed on a stack of accounting reports..
One finger plunged into her soaking pussy, then two, then three – if I could have fit my entire fist in there, I would have, except I wanted my cock to fill her. Not my hand. Throbbing and ready for her moist, dripping cunt, I shifted her in my lap, pulled up her skirt, and got her close. She wriggled, moaning.
“Please, Big Jim. Please. Fuck me,” she whispered, tonguing my ear.
"Not yet," I hissed against her neck, a warm teasing voice a promise to draw this out. I turned and hooked my finger up to stroke her G spot and she cried out, ready to climax.
But I had other plans.
One arm stretched out and swept everything off my desk, the mess making a series of dull thuds on the carpeted floor. Then I hauled her up as if she were a feather pillow, spread her legs wide, and dove my face into her, tongue fucking Alicia like I was a starving man at a buffet in the desert. My cock was stretched out so far I thought it was in the next county over, and if I didn't sink myself to the hilt in her soon I would die. Just die from tonguing her, tasting her, moaning into her clit and hearing her groan, her little hands sliding through my hair and pulling it, tugging when she was close, shoving my mouth against her and making me eat her out.
Of this world.
Her climax was so close, so close, and she dug her hips into my face, hands reaching behind my head to push my tongue into her. I sucked her clit and stuffed two, no three, fingers inside her aching hole again, filling it just enough to bring Alicia to the edge but not enough.
It was time to give her exactly what she wanted. She started to contract against my hand and my tongue and I stopped cold, pulling out and away and blowing lightly on her naked clit.
She nearly screamed with anguish. That's right, babe. Now who's the man in control?
"Please, Mr. Michaels. Please fuck me," she whimpered. She looked up and saw her reflection in the mirror behind my desk. Her pink, red pussy was dripping with juices, smearing my desk and begging for me to sink in, to fill her and release her, to release me from the raging orgasm that, finally, was ready to come out.
"Oh, Alicia, I'll get there," I said, ripping off my sweatpants. "But most women need a little preparation before they can get some of this."
She gasped, a hand going to her mouth. While my cock isn't long – maybe 8 inches – it's about the thickness of a butt plug. And not one of those tiny butt plugs. The size of a Coke can, my cock fills women, and more. But most of the ladies need a little attention and lubing up before they can find satisfaction with me.
And I would make sure Alicia was satisfied.
I reached into my desk drawer and pulled out a doubleheaded dildo. A warm shot of lighting seemed to lift her off the desk, hips first, and I swear I saw her cunt lips tremble and twitch. I planned to fuck her with the dildo and resume tonguing her, and get my lips on that pink starfish, too. As I slowly slid the 4” diameter dildo in her, she moaned and bucked against it, grinding for more, and I slowly licked her red clit with short, fluid strokes.
A knock on the door interrupted us, and as I shouted "Hold on!" -- in walked Little Jim.
Little Jim isn't really my son. James McDorfam -- yes, THAT James McDorfam -- joined the trucking company after his spectacular injury on national television, when he blew out his knee during the Big Ten conference finals. I took him under my wing and taught him the ropes; Little Jim, as everyone called him, was like a son to me.
But not quite.
And he wasn't little.
"So I have those regional reports from the -- ah -- the -- oh, my GOD!" he shouted, suddenly realizing what he'd walked in on. He was good at playing dumb. He also winked at me, and I knew he was thinking that he'd been so close to beating me.
If you can't beat them, though – join them.
I turned bright red and moved slightly, one head of the dildo grazing Alicia's clit. She groaned and couldn't help it, her hand reaching down to stroke off. She started smashing up against the dildo head, seeking it out. I pulled back and watched as she fucked herself with one hand and played her clit like an instrument in an orchestra, her fingers strumming where my tongue had just been. I slipped one hand under her ass and added some light strokes to the edge of her anus, making her buck like a bronco. She was in full climax, her face twisted in orgasmic joy, a nearly painful look on her, as dripping juices poured out of her pussy.
A cockeyed grin slipped over Little Jim's face as he stood there, transfixed. His boner screamed out for attention, too. We'd double-teamed a few employees before, all women like Alicia who were looking for some adventure. Two of the women were upper management at the company, and while we didn't do menage with them anymore, they were mighty fine women with a bright future at the company.
Like Alicia.
"So, Little Jim, exactly how much of this business do you want to learn from me?" I asked. Alicia couldn't stop coming, wave after wave hitting her. She practically didn't need us, her pink fingers traveling over her vulva and breasts, pinching and wringing every last drop of orgasm out of her. When I slid my finger to capture some cunt juice and then carefully poked through her ass muscle, she screamed in joy.
Little Jim covered her mouth with one well-manicured hand. Quarterback hands.
Hands that know how to handle a ball.
He didn't need to RSVP my invitation; Little Jim grabbed the dildo from me and pulled it out of her, then leaned over Alicia. "You look like you're not quite done yet, honey. Let's see how much more you have in you."
"Yes, yes, please," she begged. Her eyes were wide and big, unfocused and frenzied. “I've wanted you both for so long,” she crooned.
Little Jim eased the 14" dildo in her, one head going in at least 8 inches.
"Whatever that feels like, baby, it's not enough. I've got more coming," I gasped, one fist wrapped around my now aching cock, slowly sliding it along the shaft, taking my time
. One part of me wanted to jizz right then and there, my hand and the scene before me too sweet to ignore. But I wanted to slide into that wet, dripping tunnel more than anything in the world. Using my hand wouldn't cut it, and it wasn't necessary.
Not with that fine, begging woman right there.
"Come here and let me lube you up," she demanded. I walked over, dick at full mast, and she slipped her hands over my tight ass as she took me in her mouth, instantly full and content. Meanwhile, Little Jim undressed quickly and leaned down, one hand fucking Alicia with the dildo, his mouth descending on her clit in a ripping kiss of tongue and heat.
Alicia's mouth was full of my cock, as thick as a Coke can, her pussy being fucked by a solid 8 inches of dildo, and Little Jim tongue fucking her clit. Just when I thought I couldn't handle any more, Little Jim stopped.
What the fuck was he doing?
Then he unzipped, and although I'd seen his dick plenty of times, I still couldn't tear my eyes away.
It was bigger than mine.
Alicia gasped. Little Jim grinned at her reaction and nudged me.
"Turn over," Little Jim urged her, licking a line up her neck to her ear. She shivered and her long, curly blond hair sliding over the wet trail he left, making her shudder again with anticipation. Little Jim turned her over on her belly and he leaned her over the desk, then pulled her back a bit, climbing on the desk.
So he wanted the pussy. That left me the brown starfish. Just when I thought my cock couldn't get any bigger and that the night couldn't get any better. I used one hand to fondle my balls and the other to tweak Alicia's nipple from behind. She groaned, and then Little Jim positioned her on top of him, sliding deep in her slick hole. He leaned her forward on top of him, and reclined back.
"Astroglide. The Breakfast of Champions," I laughed, pulling a bottle out of my desk drawer. I took the Astroglide and squirted it all over the cleft of her ass. Spreading her ass cheeks gave me a full-on, awesome view of Little Jim's cock in her, his balls cradled between her warm folds and the top of his thighs. My hands gently parted her buttocks and her pink, hairless asshole stared at me, beckoning me to fill it.
Double Entry: The Collection (3 Menage Stories) Page 2