Richard and Elaine's NYC Day

Richard looked at the lubricant for a moment, unscrewed the cap and squeezed a liberal amount onto her pucker. She flinched saying, "Ohhhhh, that' cold!"

Richard mumbled, "Sorry," as he coated his rigid member with another dollop noting that, yes, it was cold. Elaine flattened herself more on the bed while presenting her rump higher in the air. Richard pushed his index finger into her anus, sliding lubricant into her. He could feel her anus tighten around his finger as he probed. He'd never done anything like this before, and was fascinated by watching her ass react to his probing. He could hear her sigh as he worked lube into her asshole.

Richard pointed his cock at her small, pink pucker, and touched it to her. She shivered when his wet cock touched her hole. He said, "Here I am," and began to push his rod into Elaine's rump.

Elaine, resting her head on her left cheek on the mattress reached behind herself and spread the globes of her ass to ease Richard's access. He pushed the spongy head against her pink pucker.., hard. He felt himself beginning to penetrate her tight asshole, and her felt her tight intake of breath. His cock was as hard as it had ever been as we watched the head disappear, suddenly, into Elaine's rectum, her sphincter tight around him. She groaned as he pushed another inch into her.

"Oh, wait, wait," she wailed. He looked at her face, which was crimson, her mouth turned down, teeth bared, and her brow furrowed and her eyes tight shut. Tears leaked from the side of her eye and pooled against her nose. "Oh, please! Please go slow..." she murmured.

"I'm going to pull out," Richard said.

"No, no. Don't!" Elaine sobbed as she breathed in raggedly.

"But, it's hurting you," he said.

"It's suppose to," Elaine said, "It hurts so good. So good..."

"Okay," Richard replied, "I'll go slow." Elaine nodded, smiling a little against the pain Richard's massive and rock-hard cock was causing.

As he began to push his cock deeper into Elaine, he could feel her pushing back. Her hands clinched the sheets tightly. Her grip was so tight that her knuckles we stretched white. Inch by inch he they pushed and Richards vein studded cock slipped ever deeper and deeper into Elaine's hot, damp ass. Richard couldn't believe how tight his penis was gripped by Elaine. Her cunt was tight, but this was unbelievable.

"Ohhhhh, Godddd," she yelled, startling Richard, "This is soooo great!"

"Yes," is all he could croak as cock disappeared completely inside Elaine. She wiggled her hips, seating him ever deeper. Richard felt his balls hanging against Elaine's vulva, rolling as she moved. His nest of pubic hair contrasted with the white skin of Elaine's beautifully rounded rump. Richard stroked Elaine's back, along her spine and then over her smooth ass. He slid his hands along her flanks, and leaning forward, reached under her and cupped her breasts. Her nipples were hot against the palms of his hands as he rubbed her breasts in small circles. Elaine purred and wiggled her hips again, stirring against his stomach and chest. Richard kissed her behind one ear, and she smiled. With one hand he pushed wiped the pooled tear from her nose, and she smiled even more.

"Ummmmm, you fill me soooo much." She whispered.

"Does it hurt? Does it still hurt?" he asked.

"Yes, but in such a special way that you can't imagine..."

"You like it?" he asked.

"Yes. I love the surrender of me to you. "I've never had a cock as big as yours in me before. It is so wonderfully filling..." She moved beneath him, trying to rise up under him.

Richard came up with her as she rested her elbows on the bed, her neck bent down, her auburn hair, the highlights reflecting wonderfully red in the ceiling light, forward over her. He could see her slender neck and the bumps of her spine. He gripped her hips and moved his cock slightly left and right. Elaine sighed, moving her calves up along Richard's sides, her silk clad legs feeling slippery against Richard's ass. She rested her legs, insteps over the back of Richard's ankles and wiggled her feet.

"Oh, Richard, Fuck me! Fuck my ass!" she said forcefully.

"Will it hurt?"

"Yes, of course it will hurt! That's the idea! Just fuck me. Fuck me hard! I want to feel your cock fucking me inside out!"

And, Richard began to move out, pulling his cock through the tight flesh vice that was her ass. He couldn't believe how erotic watching his cock slide from her rectum was. Inch by inch his pole was revealed, blue veins standing out under his skin, her tight ass gripping it, as he pulled outward. Elaine made a sound deep in her throat and she shook her head back and forth, tossing her hair; her gold earrings reflecting through it.

Elaine reached with her left hand under herself and touched her clit. It was like she had been hit with an electric cattleprod and her hips jerked. Richard's cock felt a pleasure burst up his cock and across his stomach, culminating at his nipples. Breathing slowly, she tapped her clit with just one finger, marveling at the sensations that leap through her body. Suddenly, Richard shoved his cock back into her with a powerful shove. Reaching farther back, she could feel Richard's cum-filled balls as they rolled in his fleshy, hairy sack. Her cunt dripped on her wrist as she cupped his scrotum. Richard also marveled at the sensations that ripped through his cock and balls as he shoved back into Elaine's ass and as her fingers caressed his balls. He sighed.

Unable to resist, Richard began to stoke in and out of Elaine's asshole. He would stop just as the flared head of his cock reach her sphincter before plunging back in again, and again, and again! Each time he drove his cock home in her ass, she grunted more deeply than when he fucked her vagina. She tossed her head back and forth as he plunged into her, driving his steel-hard cock into her over and over. His balls swung back and forth between them; her tits swung back and forth under her, the pulling adding to her exquisite agony, her the nipples grazing the sheets shooting electric thrills throughout her body. He could feel her fingers rubbing her clit and slit and touching his balls from time-to-time.

Richard began to really pound into Elaine, over and over, his cock sliding out, then it, out then in. At one point his cock pulled completely free of Elaine's hole, and he marveled that it gaped open to him. She shouted for him to put it back in dammit, so he moved his cock until it realigned and she shoved it in with a mighty push. Elaine's feet rose and fell against his ankles as he pounded her.

"Oh, GOOOOODDD!" she screamed over and over as she felt her orgasm building and building, her head tossing and tossing, her tits flailing about her chest and his cock sliding in and out, in and out of her inflamed ass!

Richard began to grunt each time he pushed into Elaine. Sweat began to drop from his chest like warm rain onto Elaine's lower back and rump. His eyes squeezed tightly shut as he felt his balls begin to pull up, his rod to swell and.., the head of his cock to feel as if it was on fire when.., suddenly, he shoved in as far as he could and the first blast of his sperm leapt from his cock into her ass. She could feel spreading warmth within her as his sperm flooded into her. Again and again his cock pulsed, spewing his cum into Elaine's ass, his cock become impossibly slippery from her fluids and his. His breath was ragged as he fell upon Elaine's back, exhausted and spent from the greatest fuck of his life. As he leaned his weight on her, Elaine could feel his cock continuing to flex, with more cum dribbling out to join the flood her in ass. She smiled as a warm, warm glow, less violent than vaginal orgasms, spread throughout her body. Richard's arms wrapped around her, squashing her breasts between his forearms and her ribcage, which added to her spreading feeling. She pushed her butt languidly back and forth along several inches of his shaft, continuing to fuel her warmth.

Elaine rested her cheek on the bed, and reached back to stroke Richard's head. "You are the best," she said.

"Oomph," he said. She could feel the vibrations from his throat against her neck.

After a time their heart rates dropped to something closer to normal, and their bodies cooled. Richard's penis began to deflate until, with a small pop, it slipped from her rectum and lay wetly against her cunt lips. He could feel her lips moving softly against his cock as if trying to swallow it. She clasped her ankles behind Richard's butt and closed her eyes.

Gradually, Richard rose above her. She released her legs from around him and rolled over, under him. They looked at one another, smiled and kissed. It was a small kiss. She hugged his neck saying, "That was absolutely in-cred-ible! That's the best ass fuck I've ever had."

Smiling, Richard asked, "You do that a lot?"

She looked at him seriously, her green eyes glowing and said, "No, rarely; not at all with my husband. He thinks it's dirty and won't do it. He won't even touch my ass much less kiss it and finger me there.., or, fuck me like you did." She rubbed his chest as he looked down at her.

"Um, well," she began, "I bet it's getting late."

"Yes, I suppose it is," he answered, leaning back on his haunches, looking at her naked body. Her black thigh-high nylons had slipped partway down toward her knees. He reached forward and stroked her tummy, slipping fingers through her pubic hair. She raised her legs and moved one foot to touch his cock, which gave a small twitch. She hooked her toes behind his balls.

"You have a great package there, boss."

"I pushed one finger along her moist pink slit," and you have one great pussy."

They smiled.

"Shower?" she asked.

"You bet, he said, moving to the edge of the bed. He swung her around by one ankle, then, gently; slip first one then the other stocking from her smooth, round legs. He reached forward and cupped her perfect breasts and tweaked her nipples. Her areoles were still dark with blood-filled passion from their lovemaking. He admired their weight, and loved the whiteness of them, the small necklace of freckles that dotted her chest. She reached between them and took his limp, but large penis in one hand and cupped his ball sack with the other.

"Let me clean you first," she said, moving her face to his cock. She lifted it by the tip and licked his shaft, first up one side and then down the other. She pushed his rising cock against his stomach, the tip coming close to his belly button and licked his scrotum, laving his balls. She sucked one into his mouth, then the second. Moving his balls to one side she licked between them and his thigh, first on the right, then the left. His eyes never left her while she licked him clean, from time to time glancing up at him her green eyes smoky. "You have the most wonderful cock. I love it," she said.

She sat back. He reached for her hands and pulling her up turned her toward the bathroom. She smiled at him over one shoulder, and reached back and grabbed his penis and pulled him behind her.

After adjusting the shower, they stepped in. He soaped her body, paying slippery attention to her breasts and under her arms. She signed as he touched her there, saying, "I think you've discovered a new erogenous zone there."

Richard soaped her stomach and ass with his large hands, slipping them between her legs both in the front and the back, being tender. He slipped his fingers into her slit after soaping her silky pubic hair. He touched her anus and felt something different, more slippery that soap. Turning Elaine, he leaned her against the wall, and squatted behind her. He spread her wet globes and looked. He could see a thin stream of his cum leaking from her behind. He touched it with this tongue and heard Elaine exhale, then sigh while pulling in a breath. He probed her anus with his tongue, tasting her and him. His penis stirred.

Richard leaned back and rubbed both her legs with soap, ending by cleaning both her small feet. He pulled them up and kissed each one on her instep. She smiled down on him in wonder, Nobody had every kissed her feet before. She felt her cunt warm.

When he rose, she wrapped her arms around him and gave him a lover's kiss, deep and passionate. Then she washed him, stroking his semi-hard cock with her hands, noting with wonder that her hands looks so small around his massive organ. Like he did, she turned him around and squatted behind him. She spread his ass cheeks and rimmed him with her tongue. She licked his ass, and then the ridge between his anus to his balls. Soaping up one finger, she pushed it into him and began to finger fuck him. His cock rose, and she reached between his legs and began to masturbate him as she fingered his ass. Richard moaned above her, pushing his backside backward. He reached down and, wrapping his fingers around her wrist began stroking himself faster and faster.

"I'm gonna cum," he grunted, turning about. She quickly took his semi-erect cock between her lips and sucked and sucked while he continued to stroke himself. She held onto him with one hand and reached under his balls and reinserted her finger into his ass and moved it around in circles.

"Arggggg," he said as he came in her mouth. It wasn't a flood, but some, and the tip of his cock was so sensitive that it hurt. He tried to pull away from Elaine's sucking mouth, but she moved forward not surrendering his organ. "God, Elaine," he shouted, pulling his cock from her lips. The water splattered over them as she looked up at him and he down at her. She opened her mouth, and showed him the pool of white sperm on her pink tongue. Then, she swallowed his seed, and smiled up at him.

Rising, she wrapped her arms around his waist and laid her head against his chest. "This was so special, Richard." The water began to cool.

They toweled each other off. Elaine went into the bedroom, scooped up her clothes, and picked up her large bag. Then she shooed Richard from the bathroom and closed the door. He could hear her moving about in the bathroom. He pulled on his shorts. His cock was sore as he adjusted it within his boxers. He put on his shirt and buttoned it, pulled on his pants and buckled his belt. Reaching for his watch he noted that both wine glasses were still half full. Bending over, he combed his hair. Then he picked up one of the glasses and sat down on bed to wait.

Richard reflected on this assignation. He didn't think he had cum this often in one session since he was a teenager. He thought that it probably hadn't even happened then because sex wasn't so available back then. He sipped the wine, feeling sexually as satiated as he ever had.

Elaine came back into the bedroom. She was transformed. She was wearing a pair of light gray-brown espadrilles, well-fitted blue jeans, a grey sweatshirt that couldn't quite disguise the swell of her lovely breasts, and no earrings. She had her hair pulled back in a ponytail held in place with a ribbon that matched her shoe color. Her ears were tiny and shell-like, and looked beautiful to Richard.

Her only adornments were her thin gold necklace that glittered around her throat, her gold watch and wedding ring and the blood-red nail polish she used. Her makeup was minimalist. Richard's mouth dropped open in surprise and appreciation at how different she looked.

"You look wonderful," he said, "So young..."

"Thank you," She replied. "I am young, though." She smiled at him. She looked so much smaller without her heels. Almost the same size as his daughter, he thought. She stepped closer to Richard and put her hands on his cheek and rose on her heels. She gave him a sweet, lingering kiss with just a taste of tongue. "You are wonderful lover," she said. "Maybe the best man in bed I have ever had," she continued.

"You are definitely the best woman I have every slept with," Richard said with feeling. He took her head between his hands and looked deeply into her eyes. She was so lovely his heart ached. "I think we need to go now," he said softly.

"Yes, we should," she said, gathering up her bag and purse.

He checked around the room, took his jacket from the hanger in the closet, patted his wallet, opened the door saying, "Can we meet again?" he asked. He felt foolish, like a schoolboy.

"I'm not so certain that would be a good idea," Elaine answered as she walked through the door. "We might get to like it too much. You have a wife and family, and I have a husband we need to think about."

With a sense of sadness he closed the door with a small click of the lock. The wine bottle, over half full, was left on the table. The bedclothes were so mangled they were beyond "mussed."

At the door to the hotel, she kissed him lightly on the cheek. She turned to the right heading down toward Penn Station and the train to New Jersey. He turned to the left toward Union Station and Connecticut.