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First Time Pegging

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She’d always wanted to try. This past year had opened a world of adventure. Her sexual awakening had pushed her limits, opened doors to bliss she never knew possible, and started a hunger that seemed insatiable. Abby’s stories ran the gambit of variety from mild exposure to ropes and restraint. It was the latter that paved the way for today’s play. Logan, usually her master, was her subject today. In the few short months, the pair had played many times, Logan always the one calling the shots. Abby was always the one restrained. Today, however, the roles were to be reversed. It would be Abby leading the way with him, subject to her bidding. She was unsure if he knew what was planned.

As agreed upon, Logan arrived at Abby’s house right on time. She knew he wouldn’t be late, but she was anxiously waiting by the door, watching for his car to arrive. Even though she was in charge, she was nervous to see how it all would go. This would be new territory for both of them. Before the knock occurred, Abby opened the door.

“Hi! Welcome!” Abby said excitedly.

“Hi Abby! You look wonderful.” Logan responded. He took a step back to admire her. Abby stood there dressed, ready for the evening. A skintight, black leather bustier accentuated her fit and curvy form. The youthful 34Cs made even more perky by the gentle cup of her lingerie, almost spilled over the top of her attire. Her waist, hugged tight by the shining leather, was long and lean. Her firm, round buttocks caused the undergarments to flare out and hug the curve of her strong hips. Ribbon and hooks stretched taught from the bottom, connecting to thigh-high fishnet stockings. Nestled between her stockings and bustier was a tiny black thong, which barely covered her young mound and disappeared between her full, thick cheeks. The soft flesh tested the fabric, threatening to spill out of the sides. The ensemble was completed with a pair of 4-inch tall spiked black heels.

“You like what you see?” Abby giggled and gave him a spin.

“I love it!”

Logan gently closed the door behind him. Abby stepped forward, took his hand, and led him down the hallway. She led him past a few doors and paused briefly before the last door on the left. With a glance over her shoulder and a smile on her face, she opened the door and they slipped inside.

The door closed behind them and they were standing in a dimly light room. It was nothing compared to the “dungeon” Logan had set up at his house, but for tonight, it would be just fine. In the center of the room was a small bed spotlighted with a bright light. There was a dresser on one side. The top was empty. Only Abby knew what the drawers held.

“I hope you’re ready.” She said with a smirk.

“I’ve been waiting to see what you had prepared.” He responded.

Abby escorted him to the bed where she stepped into him, eyes closed and lips ready. He wrapped his arms around her and leaned in to meet her. Their lips met for a hot, passionate kiss. Deeply, their lips came together. Their tongues dancing, probing each other’s warm, open mouths. Abby’s hands found the hem of his tee and she lifted it up and over his head. Her hands traced their way down his muscled chest and rippling abs before pushing him back onto the bed.

“Oh, boy!” Logan chuckled after landing on the bouncy mattress.

Stepping to the bed, Abby climbed on top of him, a leg on each side. She sat back in his lap and then leaned forward to kiss him again. They stayed here for a few minutes kissing. Abby’s lips left Logan’s and began to explore his neck and ear with her mouth. Gentle kisses and subtle licks made his pants grow tight. Abby could feel his swelling from where she sat.

“Baby, that feels so good.” He said between soft moans.

Abby continued to kiss and lick his skin. Her attentions slowly moved south. First caressing his collarbone and chest, then kissing where her fingers were. Logan knew where her mouth was to move by where her hands progressed. She brushed, kissed, and licked her way down his hairless body, eventually reaching his jeans. With deft fingers, Abby quickly unbuckled his belt, unbuttoned his pants, and unzipped his fly. Tucking her fingers inside both his Levi’s and trunks, she tugged his clothes down. The sexual tension that was built up was finally released. His manhood jumped from its constraints. Straight as an arrow, Logan’s intimidating member reached for the ceiling. From his position on the bed, his piece looked as impressive as the numbers read. It stood 9 inches tall, capped by a swollen reddish-purple helmet, and was a whopping 6 inches around. Like his chest, his loins were smooth and hairless. His testicles were plump with anticipation and the cool room drew them close to his body, creating a plump little sack of smooth skin. Abby managed to pull his pants the rest of the way off and her attention turned back to his prone form.

One hand rested on each leg, just above his feet. She gently pushed his legs apart, creating space to climb back onto the bed. Her hands grazed his shins and knees while she positioned herself kneeling between his legs. Once seated, Abby tickled his thighs, brushed close to his loins, and massaged his rippling stomach. She tried hard to get close to his quivering pole without touching. His anticipation made it jump when she got close.

“Are you teasing me, Abby?” Logan said, smiling.

“Yea, to start. We are only getting started.”

Abby gently cupped his swollen sack; her fingers stroked his taut skin almost unperceivably. He twitched. A clear bead of liquid formed on the tip. Still caressing him, she placed a finger on this drop and gently swirled it around his pulsating head.

“Oh, fuck!” he muttered.

Delicately, Abby wrapped her fingers around his member and gently pumped her hand a few times. Logan thought she was going to progress using her mouth or her hands more, but instead she kissed the tip and stepped back off the bed.

“Off the bed, on your knees.” She demanded, feet apart and fists on her hips.

“Yes, ma’am!” Logan said jokingly. He sat up and knelt on the floor by her feet.

“Take my panties off.”

Logan reached up and unclipped the garter straps from the stockings. Once done, he gently tugged on the thin string holding her thong on her hips. The small underwear rolled up as he peeled it from her, the back string slipping from between her cheeks. The flimsy garment, pulled free from her firm body, fell down between her toned thighs. Abby stepped out of them and kicked them across the room. Logan looked back up to behold her smooth, plump mound perfectly at eye level. Her thighs framed the puffy lobes of hairless flesh, creating a soft V nestled where they met.

“This is how things are going to go.” Abby said with authority. “This is my house. You will obey my rules. You will address me with ‘ma’am’. If you aren’t willing to follow these simple guidelines, you should leave now.”

“Abby? This is unlike you. But I’m yours to command tonight.”

“Good. Now, lick my pussy. I’ve been a dirty girl and it needs a good tongue bath.” Abby spread her feet wide so Logan could have access to her lips.

“Yes, ma’am.”

He leaned forward and gently pressed his lips against hers. His tongue pushed forward as far as it could reach, then pressed against her cleft. Her puffy labia parted, letting his tongue slip between. A sudden river of wetness flowed into his mouth. The anticipation of what was in store had caused a welling up of arousal that was trapped behind her swollen pudenda. Abby moaned at his touch. Her legs bowed and she sank into his warm mouth. Logan reached around and grabbed her bottom, pulling her against his face. He lapped at her drooling snatch. Her sexual nectar coated his face as his tongue probed and rimmed her entrance. Occasionally, he’d stroke the length of her mound and slip his tongue under the hood, cloaking her pearl. Her body shook each time he did. Abby’s hand held Logan by the hair, pushing him firmly against her. Both moaning, they continued until Abby couldn’t hold the inevitable off. She then stepped away from him.

“Stay right here. Don’t move.” She commanded.

Abby walked to the dresser and opened a drawer. Logan couldn’t see what she pulled out from where he knelt by the bed. He watched as she stepped through a few loops of what appeared to by nylon webbing. Wiggling, Abby finally pulled the strap over her hips. One looped around her waist and there was a loop for each leg. She fiddled with the straps, pulling each loop tight around her body.

“Close your eyes.” She called over her shoulder.

“Yes ma’am”

The sound of footsteps told him that she was returning to where he sat. Her shadow fell across his face.

“Open.”

There before him hung a large, brown cock. Strapped tightly to Abby’s body was a harness holding the base of a phallic appendage. It was so realistic. The tip was round and ridged; the shaft crisscrossed with protruding veiny details.

“It’s not as big as yours, but it will do for today.” A smile spread across Abby’s face.

“I… um… uh…” Logan’s eyes grew wide. He stuttered some nonsense.

“Shall we continue, or will you back out?” she mocked.

Logan shook his head no.

“Good. Open up. Suck my cock!” she laughed.

Timidly, Logan leaned forward. The smooth, round tip pressed against his lips. An audible swallow came first followed by a licking of lips. He opened his mouth and wrapped his lips around the toy. Slowly, he began to tongue it and slid the toy around his mouth. It was a weird experience, but he gradually got over the mental hurdle. Abby grabbed his hair with both hands and helped him suck her member. Gentle thrusts of her hips pushed the toy to the back of his throat. His tongue cradled the shaft on its journey in and out. Being in control was exhilarating. Her pace quickened without her realizing. Soon she was fucking his mouth. Orgasmic sensations were growing in her from listening to his mouth slurping around the toy. Each thrust deeper until all 7 inches of the pole slithered down his throat. Before she got off, she thrust one last time and held her cock deep in his mouth. His body jumped as he choked on it firmly lodged in place. Abby let go of his head and pulled the toy from his mouth. Thick tendrils of saliva hung suspended between his mouth and the phallus before dropping to his lap.

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“Turn around and bend over.”

“Yes, ma’am.”

As he turned to get into position, Abby returned to the dresser to fetch a bottle of lube. Logan couldn’t resist peeking over his shoulder to see what was coming to him. He had moved to face the bed, leaned forward and rested his elbows on the mattress. Once back, Abby used her foot to nudge his knees a little wider and pressed her hand to the small of his back, causing him to arch. In doing so, his hips rotated forward, spreading his cheeks and dropping his engorged member back and down. She then knelt between his feet. Her hands rubbed his muscled backside. Tenderly she pushed his cheeks apart, exposing his tight, puckered hole. She watched it clench tight with nerves. This too was smooth and hair free. Abby was relieved to see that.

“I’ll be gentle.” She cooed.

Abby squeezed some lube from the bottle. It landed cold on his buttocks, ran in a stream over his star and flowed down its taut bag where it dripped off. With one hand, Abby caught these drops and spread it over the dangling extremity. The thumb of the other spread the slippery liquid around the rim of his anus. Gently, she stroked his throbbing cock and massaged his back door, encouraging him to relax. She felt his muscles release beneath her fingers. Abby applied pressure to his small entrance and smoothly slid her finger inside.

Logan gasped.

He had never been penetrated like this.

It was strange but felt amazing.

Abby curled her finger and brushed against the bump inside his rectum where the sensitive prostate resided. It caused a tingle to swell in his glans. She had done her research. She knew what he was feeling. Hoping to keep him from completing before she wanted him to, she stopped stroking him and focused her attention on his penetration. Calmly, she moved her finger in and out as she caressed his back and cheeks. Occasionally, she would nip and kiss where her hand had rubbed. Logan moaned as he relaxed more and more. His grip on her finger grew looser by the minute. Abby’s finger slipped out; she squeezed more lube onto his backside, and applied pressure again, this time with a second finger. They slipped in easier than the first insertion, but quickly became squeezed by his virgin ring.

“Ugh…” Logan groaned.

The extra finger was stretching him wide. A few calming breaths and he relaxed again, letting her glide easily in. Abby resumed her gentle probing and soft touches for a little longer. Something landed on her leg. She looked down to see a droplet had fallen from Logan’s pendulous piece. Stringy drips trickled from his pulsating helmet. Her continuous prodding against his prostate produced an endless spring of precum. His rod twitched where it hung. Soon he grew used to the fullness. His ring relaxed. He was enjoying her treatment. She let her fingers recede from his backside. Leaning forward, she whispered in his ear.

“Are you ready?”

“I think so?” he said timidly. “Go slow?”

“I’ll be gentle.” Abby leaned back and spanked him hard.

Abby stood up and straddled his hips. She bent her knees and lowered her swinging dick to hover just inches from his now pink, soft hole. Grabbing the phallic instrument, she rubbed the tip in circles around his rim. A slight shift in weight and the cock’s head popped inside.

“Oh god!” he gasped.

“Shhhh…” Abby cooed.

She leaned into him. The widest point of the toy had already passed through his backdoor, now the rippled shaft slowly disappeared through the gate. Logan groaned as it moved deeper. It both hurt and filled him with a satisfaction. As it moved deeper, the crown pushed hard against his gland. Tingles shot through his pole and exploded in his throbbing mushroom cap. Once fully inserted, Abby paused, giving Logan a moment to adjust to the girth.

Placing her hands on the small of his back, she supported herself as she prepared for what was to come next. Abby pulled her hips back; the long, brown cock retreated from his tight anus. Stopping just before the head slipped out, the first real thrust began. From her position suspended above and behind him, she let her weight and gravity assist her penetration. Moving slowly but deliberately, Abby plunged the full 7 inches deep into his rectum. The molded silicone scrotum pressed firmly against his perineum. Immediately, she withdrew for the next thrust. Over and over, the thick toy sunk deeply.

“Ugh… ugh… ugh…” Logan grunted with each push. His breath ragged and forced.

“Do you like that?” Abby asked.

“Yes… I do…” he managed to say.

Clear liquid gushed from his hanging member like a river. The repeated pressure on his sensitive p-spot created an endless well of ejaculate. Strings stretched from his tip to the puddle forming on the floor. Drop after drop built with each thrust before cascading down to the floor. His throbbing cock swirled with tingles from her onslaught. The sensation was overwhelming, his mind blank as he experienced this new stimulation.

Abby also was incredibly aroused. Like Logan, a perpetual flood seeped from her swollen vulva. Her lips were puffy and pink from excitement. The droplets falling from her soaked snatched mixed with Logan’s puddle. She pulled back and stood up. The cock fell from Logan’s used ass. His hole remained open as if the toy still sat inside. Abby traced a finger around the gaping ring before stepping to his side.

“Climb onto the bed. Lie on your back and pull your legs to your chest.”

Logan obeyed.

She too climbed onto the bed. Resting on her knees with legs spread, she took a moment to admire what she was doing to Logan. She looked at him, his cock pointing to the ceiling, throbbing with his raised heartbeat. His sack still taut and smooth perched above his loose pocket. One hand stroked the toy between her legs, the other snaked underneath to rub her vibrating mound. It pulsed with arousal. She fingered herself while Logan eagerly awaited her next move.

“What do you want me to do?” she asked breathlessly.

“Fuck my ass.” He responded with certainty.

Abby shuffled forward and slipped her member back inside his waiting orifice. Once in place, Abby thrust with purpose and resolve. She was going to wear him out for her pleasure. Logan held his knees in his hands giving Abby an unobstructed alley to use him. Instantly, the spring of precum bubbled up and ran in rivulets down his bouncing dick. The clear ejaculate briefly pooled around the base of his member before flowing around his swollen scrotum, mixing with the lubricant for Abby’s ass fucking. Abby leaned her hands on his thighs, pushing his legs higher, his helmet now bobbing above his stomach. The pooling precum soon filled his navel before spilling over his stomach and flowing towards his chest.

“Oh Abby! I think I might cum!”

“Not yet! I didn’t say you could.” She scolded.

Shifting back, Abby pulled the toy from his ass for the last time that night. She stepped off the bed and loosened the straps of the harness and let the toy fall to the floor.

“Lie flat.”

Logan extended his legs so he was prone on the bed. Abby climbed back up and straddled his thighs. His girthy pole quivered with anticipation. Using her hands, she collected the pooled liquid. One hand gently stroked him, the other spread the slippery wetness around her puffy vulva. Her body shuddered under her touch. She shimmied forward until she was poised over him. Suddenly, she dropped down on his rigid member. It easily impaled her starved pussy. Her desire overtook her, and she bounced on him relentlessly. Even with minimal direct contact, the telltale signs of impending climax quickly built to a crescendo. With the power of an earthquake, she came. Her body shook uncontrollably. Her pussy gripped him tightly; the pulsating in her hot loins delivered the fatal blow to his attempts to hold back any longer. Tremors shook his manhood and ropes of hot, creamy cum coated her vaginal walls. Their bodies reverberated to the same frequency. Abby collapsed onto his chest. They sat like this until they were able to catch their breath. Eventually, she sat back up.

“One more thing.” She said with a wink.

Squeezing tightly, she pulled herself off his slowly withering member, careful not to drop a single drip of his seed and assumed a position on all fours.

“Lie down with your head between my knees.”

Logan did as instructed. Once in position, Abby sat back and rested her swollen pussy on his mouth.

“Lick me clean.”

Her muscles relaxed and the mixture of his cum and her tangy secretions oozed forth. Logan did not hesitate to lap at her warm folds, collecting all that flowed into his mouth. Swallow after swallow, he continued until nothing of their time together remained. Abby swung her leg up and over as she stepped from the bed. Walking over to where she had kicked her panties, she collected them and stepped through.

“Clean yourself up. I’ll be in touch.” She said as she pulled the thong back into place.

Without a glance back, she walked through the door, closing it behind her.

“Um… Ok…” Logan said to no one. He sat up, wiped his mouth with the back of his hand, and slowly gathered his clothes. After dressing, he made his way to the door. An unusual gait dogged his typical walk. Opening the door, Logan peered out. Abby was nowhere to be seen. Making his way to the front door, Logan left, hoping to hear from her again soon.

Published 
Written by Woodwright
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