I kept silent as Ilene turned back to face me, reached behind herself, and unsnapped her bra. Her heavy D-cups spilled forward as the bra fell to the floor, then the girl was bending and peeling her shorts out from between her meaty thighs just as her friend had seconds ago. Ilene stood back up to present rosy, erect nipples, a wide smile, and a completely shaved mound.
I took a deep breath, drank her in, silently thanked God for my good fortune, and pinched myself a little too. Delighted as I was that they were both naked, I still had no idea what I was going to do. God knew, I would never live down getting them undressed, then doing nothing!
“Well?” they sang, snapping me from my reverie. Be careful what you wish for, I thought as Ilene walked back to join Geena on the futon. They were positively daring me now to go on. Punishment. Punishment… The word kept rumbling through my brain. What could I do that would really make this night memorable? Sex was too easy, if they even would allow it…and my heart could stand it. This night needed something with wit, something with control, something hot, something that could only ever come from a man my age, with my experience. Something maybe even a little bit embarrassing. Something…
I sat up straighter as the idea hit me.
“What?” they asked.
“Well,” I asked coyly, “are you two even a little bit wet?”
“Mmm,” Ilene moaned in agreement while Geena looked down.
“Well, Daddy wants to see you get even wetter,” I suggested.
I rose from my chair as best I could considering the lump in my pants, and sat down between them, Ilene on my right, Geena wiggling to my left. I’m sure they were prepared for me to slobber all over them. Feeling the heat from the flushed nubile bodies of my naked bookends, I snuck a breath and continued. “You’re going to masturbate for me.”
Silence descended as I stared from one girl to the other and back again.
“She’s shy,” Ilene offered, and Geena leaned forward to look accusingly at her best friend.
“Ilene!” the thinner girl pleaded, then turned to look at me. “Jeff, I can’t. I mean I…”
“Yes you can, girl,” Ilene spat across me.
I couldn’t help but run my eyes up and down her voluptuous body. God, was she built, firm because of her youth, and open, white and so succulent. Man, how could I not be hot for these two?
“Well, I won’t!” Geena declared and marched across the room to her clothes.
“We have to!” Ilene demanded through a quick chuckle, walking over to her best friend. “We’ve been bad and we must be punished!”
I just sat and watched them—no longer in control, if I ever had been—Ilene standing over Geena, Geena bending to gather her clothes. If this went no further, I thought, I would still have a great memory.
“Tell me you’re not as wet as I am!” Ilene demanded.
Geena dropped the bundle of clothes.
“I just…” She addressed both of us. “I never did it like this, I mean…”
“You think I have?” Ilene asked. “There’s nothing to be afraid of.”
“Together, right?” Ilene added, turning to me.
“Well…”
“You’re really loving this, aren’t you?” Geena said, relenting.
“You know it, little girl,” I said and stood, ceding the futon to them.
Here was the tricky part, I knew. In order to come, each girl would have to be relaxed enough to let her inhibitions fly. It wasn’t enough for them to be wet; I knew they had to get into the moment, not feel threatened. Could that happen with them sitting right next to one another?
Silly as it sounds, I was nervous. Let’s face it, I knew eighteen-year-old girls could be easily bored, their minds could flutter from one thing to another. I remembered how hard it was way back in my first years of college trying to keep up with girls. I was hoping the masturbation was enough of a sexy stimulus to at least engage Ilene and Geena.
But how do I start this, I wondered?
“I got to…” Geena said hesitantly, and I nearly jumped as I thought we had lost her again. But she went on. “I got to be on my knees.”
Far be it for me to suggest positions.
Geena knelt then, circling her pelvis against the futon’s front, thrusting her ass toward me, spreading her knees. Ilene sat down right next to her, her thick thighs spread, her back slightly arched, her bare open pussy in full view.
I slowly moved my chair to the center of the room, but before I could sit, Geena said, her voice muffled into the futon, “I…Jeff, I need you to…”
Her voice was quivering.
“Anything, honey,” I said. I was teetering here, wanting to be close but not too close, my cock pounding in my jeans, my head swimming.
“Touch her ass,” Ilene offered. “She likes that.”
I had no idea how Ilene was privy to this kernel of information, but I bent on one knee and began massaging her cheeks as she fed her hand up under herself.
I realized this was the first time I had really touched either of them.
I looked over at Ilene who was grinning, one hand clutching her big right tit, the other buried in her bare snatch, her fingers spreading herself.
There is a limit to how much good luck any one man should be allowed.
“Daddy’s girls were very bad tonight,” I said, caressing the hot cheeks below me. “Very, very bad,” I added, as Geena began to moan and circle her hips, and Ilene grabbed her tit harder. “And every time you are bad, this will be your punishment.”
With my cock all but aching to break out of my pants, I looked from where Geena’s long brown hair cascading between her shoulder blades to Ilene’s shaking tits, her crooked lips pursed. Ilene had her legs so wide that the smell of her pussy hit me square in the face…as I all but lunged to taste her.
“Come, my girls,” I teased as Geena’s moans increased in volume and she slapped her crotch against the futon and her buried hand.
“Jeff,” she called as Ilene opened her eyes wide, nearly sat straight up and looked over at me.
“Daddy, I…” she quivered, as she planted her even hand deeper.
“Who’s gonna come first?” I teased.
Ilene spread her hand and I saw her slip another finger into herself. Her breasts bounced as she released her hold on the one and placed that hand across her slight belly. Geena was mewing, little quick sobs escaping as she pushed hard against my hand and began to shudder.
“I wonder who?” I sang.
I let go and knelt to press my crotch against Geena’s ass. I tickled the outside of Ilene’s right thigh, too, and when I did, it was as if an electric spark ran through her. She threw her head back. “Ah, Daddy!”
I tried with all my might to concentrate on what was unfolding around me: pressing against Geena’s back, watching her hair swishing, hearing her muffled mewing, the sight of Ilene, my face mere inches from her thighs, those glorious tits bouncing as she stared back at me…
Ilene screamed, nearly sitting straight up as she pleaded with her big, blue eyes.
I smiled up at her, pushed my heavy crotch into Geena as hard as I could. “Go ahead, come for Daddy.”
“Ah… ah!” Ilene cried and began to quiver around her hand.
Whimpering , she kept her eyes on me as I watched her transform with her impending orgasm. She arched her back, her tits thrust out, finger-fucking herself until her whimpers became growls and her hips shook. But it really was her pretty nose and strong chin I watched as Ilene came.
“Fucking Jeff!” she screamed.
“Na…no. No No No!” Geena screamed in answer, pushing back against me one last time. Pushing her crotch against the front of the futon, she increased her hip thrusts until she was moving with piston-like spurts.
“Jeff…” Geena said, thrashing her hair across her back, pushing those hips, rubbing her ass against me.
What the hell, I thought and I tapped her ass with one quick swat.
The little girl screame
d as she fell flat over the futon.
I swatted her quickly three more times, and as Geena shook through her own deep orgasm.
* * * *
I walked back to my chair after leaning over to kiss Geena on the head, then standing and doing the same to Ilene. Geena stayed in place, too exhausted to move, while Ilene stared at me, her legs still spread, her fingers still inside herself.
“Very good, girls,” I offered, sitting slowly, my cock all but pushing through my jeans.
“Mmm, look at Daddy!” Ilene said, and Geena turned to stare over her shoulder at me.
“Well, if we can, so can you,” the darker girl dared me. I looked at them both…and began to unzip my pants.
“Oh, Daddy,” Ilene exclaimed, not moving her body or eyes from me.
I produced my hard cock and began to stroke myself.
“You should punish us more often,” Ilene said and massaged her tits.
“Yeah,” Geena said, and began to wiggle her ass.
“Um,” I sighed as felt my arousal spike at the sight of them, Geena wiggling her ass for me, Ilene grabbing her big tits. I gulped, pumping my cock through my fist. It wouldn’t take me long, given what I had just witnessed, but I did try to hold out. Ilene at one point even lifted her heavy right tit to her mouth.
“Yes, Daddy,” Geena whispered.
“Come for us, Daddy,” Ilene agreed.
How could I deny these sweet girls of mine anything? I thought as I came in a fount.
Backwards
by Kris Cherita
Lisa was careful to arrive as soon after seven as possible, not from any fear of punishment—Greta was free to punish her according to her whim, no matter how perfectly she behaved—but out of respect for her beautiful mistress. She knew better than to be early, in case she met any of Greta’s other clients leaving, but didn’t want to waste even a minute by being late.
Greta answered the door on the second knock. She was wearing a black silk dress slit up the side almost to her hip, with a neckline that showcased her magnificent brown breasts, almost—but not quite—revealing her nipples. It was part of their pact that Lisa had to earn the right to see her mistress’s breasts in all their glory, and only as a reward for perfect obedience would she be permitted to suck on them.
“Good evening, Mistress,” said Lisa, quietly as the door opened. “May I enter?”
“If you promise to obey me, you may,” said Greta calmly. In fact, neither had ever breached their elaborate pact—Greta knew exactly what orders Lisa would obey, what punishment she would accept—and it had been several months since either of them had used a safe word.
“I promise.”
“Come in, then, and close the door. Now get those ridiculous clothes off. What do you think this is, a gymnasium?”
Lisa quickly stripped out of the bicycle pants and sweatshirt. It was another part of their ritual that she had to come in wearing something that accentuated her ass and left it accessible to Greta. Lisa was a small-breasted blonde, a little on the skinny side, but she’d been blessed with a gorgeous, appleshaped ass, to which her husband, Terry, paid scant attention. He’d never kissed it, spanked it, or even praised it, much less fucked it, as Lisa often wished he would. At most, he’d hold on to it sometimes when she was on top, his fingers never seeming to come within an inch of her asshole. She was technically still a back-door virgin, though Greta had over the past year butt-fucked her with fingers, vibrators, and an assortment of toys.
When she was naked, Lisa slowly bent over to pick up her clothes, offering her ass to Greta. Sometimes this would earn her a spanking for turning her back on her mistress, while at other times…
“Cute,” Greta drawled. “Cute butt.”
“Thank you, Mistress.” said Lisa, then added, sincerely, “Not as beautiful as yours.”
That, as expected, earned her a relatively gentle swat on the cheek. “Did I say you could speak?”
“No, Mistress.”
Another swat. “Go and put those away, have a quick shower—three minutes, no more—then go and bend over the bed and wait for me.”
* * * *
The toys were waiting on the bed—fur-lined cuffs, spreader bar, slim vibrator, inflatable butt plug, bottle of passion fruit-flavored lube, and ball gag. There was also a glass of scotch and Diet Coke. Lisa knew she could remove any item she didn’t want used, but none of these were a problem. In fact, she was mildly disappointed not to see one of Greta’s strap-ons. Whips, crops, canes, paddles, and hairbrushes didn’t appeal to her, and she didn’t want to have to explain the marks to Terry, so although she loved being spanked, it had to be skin on skin, and Greta had agreed. Lisa took a mouthful of the drink, locked the spreader into place, put the gag into her mouth, then bent over the bed and cuffed her hands to the far side. She left herself enough slack that she could remove the gag in an instant, or fumble for the spare key taped under the bed in case of an emergency.
She was ready—slightly more than ready—when she heard Greta walk in behind her.
“Good,” purred her mistress. “Now, I only have a few minutes before my guests arrive, so I’ll have to make this quick.”
Guests? Lisa started, but she didn’t remove the gag.
“Some friends of mine,” Greta amplified. “Another mistress and her slave. I was thinking of leaving the door open so they can see your pretty pink ass, but none of them will see your face.” Lisa heard her pause to see whether there would be any objection, but Lisa only continued to listen. “Of course, some of them may want to play with your ass a little, the way I do. Nothing too rough, of course; no cocks, no whips, no toys that aren’t on the bed. It should be fun, don’t you think?”
Lisa knew that all she had to do was shake her head. Instead, she nodded, telling herself she could always change her mind later.
“Good,” Greta said and sat down beside her on the bed. She picked up the vibrator, lubed it up, then put another dab of lube onto her index finger. This dab she spread around Lisa’s twitching asshole, then slowly worked her slippery finger inside up to the first joint, then the second. Lisa whimpered around the ball gag as she began coming, and Greta removed her finger and reached for the vibrator. She rubbed Lisa’s clit with her other hand while inserting the vibrator inch by inch into her lovely ass. Lisa lost count of how often she came before the vibrator stopped buzzing in her butt, and only slowly became aware of the rather tentative knocking sound coming from outside the room.
“Sorry,” said Greta. “That should be the first of them. I’m going to shut the door. If it’s who I think it is, I’m going to let him rim me for a few minutes. Don’t worry, he’ll be cuffed to the chair, so he won’t be able to touch you, and gagged so he won’t speak. Of course, how much he hears is largely up to you.” She caressed Lisa’s ass, and gave it another swat. Lisa nodded. “I’ll be right back.”
* * * *
Lisa lay there in an erotic fog for what might have been a few seconds or the better part of an hour before Greta returned. She vaguely heard the chair creak as somebody sat, and heard the click of handcuffs being locked. Greta sat beside her again and proceeded to spank her on one cheek only until Lisa suspected half her ass was rose-red, the other half milk-white. She was on the verge of coming again when Greta stopped, and left the room to answer the door again. She heard muffled breathing from the man in the chair, and then the door opened again.
“Oh, wow,” said a young woman’s voice. “Who’s your decorator?” She laughed, then snapped, “What are you staring at, slave? Haven’t you ever seen a woman’s ass before?”
“Yes, Mistress,” said another young woman, meekly.
“Well? Have you forgotten what to do?”
“No, Mistress,” said the slave girl, a little hesitantly. She knelt behind Lisa, parted her cheeks, and said timidly, “You have a beautiful ass. Please, may I lick it?”
Lisa was startled—she’d worshipped Greta’s gorgeous ass with her lips and tongue for many hours s
ince coming to her as a client, but had never been rimmed herself. “She’s Greta’s slave,” said the first woman, before Lisa could respond. “You ask her permission.”
“Please, Mistress Greta?”
Greta stepped forward, and gently ran her finger down the crack of Lisa’s ass, watching her tight little ring open slightly in anticipation. “Is she a good ass-licker, Naomi?”
“She’s enthusiastic, and I’ve done my best to train her,” said Mistress Naomi, “but she still needs practice.”
Greta nodded. “Show us.”
The slave lowered her face, kissed Lisa’s white cheek, then her still-tingling pink cheek, then ran her tongue back and forth between the two kisses, flicking it lightly over Lisa’s hot little hole. Lisa gasped slightly, but the gag muffled the sound. The licks became shorter, homing in on her puckered portal, until her tongue was circling the star-like creases and spiraling in towards the core. It felt strange and wonderful, and she was soon only vaguely aware of the voices in the background. Her asshole tightened as she began to come, and she began squirming on the bed, trying to rub her clit on the satin sheets, and the slave girl parted her cheeks and began licking a little faster with a little more pressure until Lisa felt the orgasm hit her like a huge wave. She lay there, basking in the afterglow from her orgasm, only vaguely aware of faint applause from behind her.
* * * *
“I could do with a drink,” said Greta as Naomi tugged gently on her slave’s leash. The young woman reluctantly stood, giving Lisa’s ass one last quick kiss that left a scarlet ring of lipstick on her cheek. “I should’ve asked you to bring your maid.”
“He couldn’t have made it,” Naomi replied. “It’s his anniversary. He’s taking his wife out to dinner.”
“Pity. He looks cute in his uniform. Does she know about you?”
“Darling, she sent him to me, and she tells him how much to tip me. She’s an angel. What about your other slave, here? Can’t you unchain him for a moment?”
Wicked Pleasures: Stories of Kinky Love Page 14