Pegging story - Do ya think I'm sexy?

Do ya think I'm sexy?

By Twistedplayr

Royce slipped his e-reader into his bag as the train pulled into the station.  The weather was cool and he decided to walk the few blocks home instead of taking the bus.  Fall had set in quickly, but it was his favorite time of year.  While walking he enjoyed the stiff breeze and nip of chill in the air, humming to the music playing on his headphones.

 

The entryway of the building was empty and Royce retrieved his mail before stepping inside.  He was busy examining an envelope and didn’t notice the person sitting in one of the guest chairs.

 

“It took you long enough.  I was expecting you almost thirty minutes ago,” said the woman sitting in the chair.

 

Royce turned around as she stood.  With her head bowedhe couldn’t see her face, but could tell she was at least a foot shorter than him.  She wore a black skirt, stockings and matching black heels with a black trench coat that hid the rest of her body.  When she finished standing he could finally see her face, and though she wasn’t a model he did find her quite attractive.

 

“I’m sorry, have we met before?” Royce asked as the woman pulled a large piece of rolling luggage from the side of the chair.

 

“No, but we've had plenty of contact RJ.  I know you are not expecting me, but I finished some business a few days early. I thought I might surprise you for the weekend,” shesaid with a smile, the shape of her sexy red lips causingRoyce’s heart to skip a beat.

 

Royce felt stunned as he realized who the woman was.

 

“Tina?” He asked, knowing the answer.

 

“In the flesh honey.  I had thought about telling you I might be in town, but didn’t want to get your hopes up.  Fortunately I was able to finish early and my flight doesn’t leave until Sunday evening,” she said while walking toward him.

 

“You should have emailed me. I would have come home early,” Royce said.  He could only imagine what Tina was planning.  He had met her in a chat room a few months prior, and since then they had exchanged many kinky emails.  They chatted almost every night and he had shared more about his inner-desires with her than anyone else.

 

Tina leaned up and gave him a quick peck on the cheek before continuing to the elevator.  She pressed the button to call the car and stepped inside when the doors opened.

 

“Are you coming?” She asked.

 

Royce followed her into the elevator and pushed the button for his floor.  He tucked his mail underneath his arm, took a deep breath and turned toward his guest.

 

“I’m really glad you’re here, you just surprised me.  I would have left early to meet you had I known,” Royce explained, reiterating his earlier statement.

 

“I know, but then it wouldn’t have been a surprise.  Besides, I didn’t know I would have the extra time until earlier today. But If it’s inconvenient I can always leave,” Tina teased as she reached for the button to return to the first floor.

 

“No, no, you just surprised me. I’m glad to see you!” Royce sad, quickly blocking her way.

 

Royce took Tina’s bag as the elevator door opened on his floor, rolling the heavy bag down the hallway to his door. He fumbled with his keys before finally unlocking the door and ushering Tina inside his apartment.

 

“You have a nice place,” Tina said as she looked around the living room.

 

“Thanks!  I was planning on ordering in tonight.  Is there anything in particular you would like?” Royce called out from the guestroom where he was placing Tina’s luggage.

 

Royce placed the heavy bag next to the dresser and turned around just as Tina entered the room.

 

“I’m glad you asked.  I have something very specific in mind,” Tina said as she slipped off her black trench coat, pulling a small bottle from one of the pockets beforetossing it over her suitcase.

 

Without her coat, Royce could finally see all of Tina, and she looked exactly as she had described in her emails and chats. She was petite but curvy and her impish grin made promises that he hoped she was willing to keep.  A smile slowly crept across his face and it was obvious to Tina what he was thinking.

 

“You kept me waiting for quite a while, so I think we should do away with all the foreplay,” Tina said as she reached down and gathered the hem of her skirt.

 

Tina was always the aggressor during their online chats, but it still surprised Royce when she pulled up her skirt.  She rolled and tucked the front of the skirt into the waistband, and that’s when he saw it.  The dildo lie under her pantyhose, trapped against her right thigh.  Other than its size, the plump column of silicone looked realistic and stopped only a few inches above her knee.

 

The sound of ripping nylon cut the silence as Tina tore her pantyhose along the seam, freeing the massive dildo.  Shequickly tightened the straps of the leather harness that held the beast, causing its head to rise like a flesh-colored monster from the oceans depths. She hefted the dildo with one hand and wagged the bottle with the other.

 

"I brought the cock and the lube. I hope you didn't slack off in your training. You told me you finished using the dilators, and this baby is the size of the largest one," Tina told him.

 

Royce gulped and his eyes widened as he looked at the massive tool. At Tina's request, over the past few weeks he had been using a set of anal inserts called dilators. The set consisted of six short plugs that started off small, with each plug wider than the last. The plugs helped to relax the anal ring and train it to accept larger items. Royce had recently graduated to the largest plug, and could now insert it without any discomfort.

 

"Yeah, I've been using the largest one for the last four days or so," Royce said, his eyes bouncing between the dildo and her wicked smile.

 

"Oh that's fantastic. Then I won't need to go too easy on you. Now why don't you get your pants off and kneel on the bed?" Tina said.

 

Royce knew it wasn't a question and didn't think twice as he began unfastening his belt. Tina had been very clear and explicit about what she would do when they inevitably met. He hadn't known how much was mere talk and what she would truly go through with, but it appeared that she was a woman of her word. He finished unbuckling his belt and quickly unbuttoned his pants.

 

The belt buckle clattered as it fell to the floor with Royce's pants and boxer shorts. He bent to untangle his feet but Tina had other plans. She reached him before he could free a single foot and caught him by the shoulder.

 

"I've got a better idea. Leave them on and get onto the bed," Tina said as she spun him around toward the bed.

 

With his pants around his ankles, Royce shuffled like a prisoner as he moved toward the bed. He awkwardly climbed onto the mattress and stopped with his ass and feet hanging off the bed.

 

"No, no.  I can't fuck you like that. Flip onto your back," Tina ordered.  

 

No sooner had Royce landed on his back did he find Tina hoisting his legs into the air. She grabbed his pants and shorts like a handle and pushed his legs back against his chest.

 

"Take these and keep your legs out of the way while I get you ready to fuck," Tina said as she gave him the makeshift restraint.

 

Royce's legs and pants partially obscured his view of Tina, but he heard the snapping sound as she flipped the cap on the bottle of lube. He soon felt the cold lubricant pouring over his perineum and down to his waiting knot, where Tina massaged the lube into his anal ring.  After just a few circles she pushed three fingers into his anus, keeping her word about not needing to take things slowly.

 

"Oh yes, you are ready for this," Tina said with a chuckle as she spread her fingers.

 

Using her fingers like an open chute, Tina poured lube into her hand and let it flow down her fingers and into his ass. She continued filling his rectum with the cold liquid, and Royce could feel it traveling deep into his guts. He thought it would begin to pour from his ass, but found his canal more than able to take it all.

 

Tina poured half of the bottle of lube into his open hole before stopping. She flipped the cap closed and dropped the bottle next to him on the bed him before pulling her gooey fingers from his ass. Royce watched as she rubbed the slippery gel over the head of her huge prick and felt his ass clench at the thought of what was about to happen.

 

"Keep those legs up. It's time for me to get to work," Tina told him as she positioned herself between his legs.

 

Royce held his breath when he felt the tip of her dildo press against his slippery ring. Even though he had used the dilators and even a dildo on his ass, he had yet to find a woman to fuck his ass until now. This was new territory, and very different from playing by himself in his bedroom. He looked down past his balled up pants and legs to see the thick column of silicone and prayed that his training had been enough.

 

Tina applied steady pressure and the tapered tip of her cock began slowly forcing its way into his anal ring. Royce shuddered as the muscle stretched, growing wider and wider until the head slid into his anal cavity. He gasped from relief as his ring slid over the smooth surface of the dildo, his training making it a perfect fit.

 

"Oh this is going better than I hoped for," Tina said as she pushed another few inches into his ass.

 

Royce tried to concentrate on breathing as the dildo began spreading his rectal walls. The surprisingly warm column relentlessly slid deeper, displacing the lubricant as it went.The huge cock pushed most the slippery liquid deeper inside, but the rest oozed outward, greasing the shaftalong the way.  

 

The dilators had prepared his anal ring for the girth of the beast, but not the rest of his rectal tube. The soft walls easily expanded to fit the intruder, but Royce's belly soon felt full, his rectal cavity bloated by the modern day serpent. He couldn't see how much of her cock was in his ass, but sighed loudly when she stopped pushing.

 

"Shit, you've taken as much as possible without more serious training.  How does it feel? Is it all you hoped for?" Tina asked as she held still, letting him grow accustomed to having his ass stuffed.

 

"Oh...it feels fantastic," Royce managed to grunt as tremors rippled through his body.

 

With his deflowering complete and no longer a need to guide her weapon, Tina let go of the dildo and placed her hands on Royce's legs. She used her hips to withdraw a few inches of cock from his ass, and watched as he squirmed and gasped.  She rocked her hips forward and burrowed back into his ass, laughing as his head fell back against the mattress.

 

Tina began fucking him slowly but deeply and Royce found that he couldn't breathe. He felt as if his brain was too busy concentrating on the hundreds of myriad sensations coming from deep inside his ass to bother with trivial things like breathing. Even his eyes refused to respond as he stared unblinking at the ceiling. His head began to swim until finally his autonomic system kicked back in and he gasped for air.

 

"Oh baby this is the fuck of your life," Tina said as she, pulling further and further out of his ass with each stroke.

 

Royce growled and gritted his teeth as Tina fucked his ass, relentlessly pounding him with her cock. He felt his rectum expand with each thrust and swore he could see his abdomen swell. The thick cock slid over his prostate, massaging and pressuring the excited gland. Royce managed to raise his head and look at his cock, surprised that it was still soft. Instead of a rock-hard erection, his cock lie against his stomach, a steady stream of sticky fluid oozes from the tip.

 

Tina increased her pace, moving faster and faster until she was pounding into his ass.  She pushed his legs back as far as possible and adjusted her stance, increasing the force of her thrusts. She fucked him with amazing skill,ravishing him without slipping too deep while forcing moans of ecstasy from his lips.

 

Royce wailed and tossed his head as the beastly cock punched into his ass. He lost all conscious thought, only able to feel the heat and pressure of the tool pounding into his rectum like a jackhammer. Without realizing it hebegan babbling, an incoherent stream of words flowing from his mouth. The talking didn't end until he climaxed, long surges of sticky spunk flowing out of his cock to pool in his belly button.

 

"Yeah, that's it.  Come for me baby," Tina said as she slowed down, almost pulling out with each stroke.

 

Tina finally slowed to a stop and Royce collapsed on the bed. He didn't move until she withdrew her cock from his no-longer-virgin ass. He yelped like a puppy as the head of her monstrous cock cleared his ring, followed by a hot, wet torrent of slippery lube.  Royce was too exhausted to keep his legs up so he simply lowered and let them hang off the bed.

 

"That was a wonderful start to the weekend. But now I'm hungry. When you're ready why don't you order some Chinese," Tina said as she unfastened her harness.

 

"Okay," Royce managed to reply.

 

Tina left the room for the bathroom across the hall, and Royce could hear her washing her dildo and harness. Hemanaged to raise his legs again before reaching down and touching his ass.  He easily slipped two fingers inside, and was curiously exploring his slowly closing ring when Tina called out.

 

"I didn't check out of my hotel room, so we'll have to go there sometime tomorrow to pick up my luggage. I didn't know if you would be here, so I only brought my toy bag," she said, referring to the rolling bag that he assumed was her only luggage.

 

Tina returned and silently stood in the doorway, smiling as she watched him finger his freshly fucked ass.

 

"Oh I'm glad you're still up for more. I plan to useeverything in my bag before I leave, so it's good to know I have an enthusiastic partner," she said, startling Royce.

 

Tina turned and left, and Royce could hear her whistling as she walked down the hall. She was whistling ‘Do yathink I’m sexy?’ by Rod Stewart and Royce couldn’t help but laugh. He looked over at the rolling case and his assquivered. I knew she was sexy, and it looked like it was going to be one hell of a weekend.