“God, Jimmy,” she moaned. “Thank you!”
“Are you ready?”
“Yes! Come inside me now. Please,” she gasped. “I want to feel you inside me.”
Jimmy took her at her word and lifted himself above her. Her fingers shaking, she unrolled another condom down his length. Either she wasn’t faking her arousal, or she was the best actress he’d ever seen. She slid him inside her and sighed as his fullness found its home. This time he rested on his elbows and allowed their bodies to meld. He took her head between his hands and massaged her temples with his thumbs. She wrapped her legs around him and twined her fingers in his hair.
“You’re the best, Jimmy,” she breathed and bit his ear.
He began to pump quietly inside her. This time he was determined to go slow, to milk the fuck for every ounce of pleasure for them both. Then Monica sunk her teeth into his upper arm. A hickey. She was giving him a hickey. Thoughts of slow pleasure evaporated into animal lust and the pace of his cock quickened. Jimmy slipped his hands from her head and down to her buttocks. There was something he wanted to know before he got too lost to think.
He slid one fingertip around and around her soft asshole. Monica sighed and arched up into his body. His hand followed her movement and his finger grew bolder. He pressed the tip inside her anus. She didn’t protest. He thrust further and felt the squeeze of her vaginal muscles. Was it protest or… No, it was coming orgasm, he decided as her buttocks clenched around his finger even as her vagina hugged his cock in a pulsing embrace. Jimmy held tight to his control until he felt her ass relax around his finger. She’d been here before. She liked it.
Jimmy left his finger inside her as he pumped harder. Her squeezing augmented every sensation and soon he was lost to blind and primitive rutting. Dimly he heard her encouragement as he pounded inside her harder and harder, closer and closer. The explosion when it came was stronger than the time before. Jimmy collapsed onto her chest, then raised himself and kissed her bruisingly on the lips. His mouth attacked and devoured her as his cock had eaten her softness below. She belonged to him, his primitive brain crowed.
But she didn’t. Sense returned. He paid her and so did a lot of other men. But, God, she was good. He rolled off her and lay on his back, still panting. His cock wilted slowly in the cool air. Monica rolled onto her side and draped herself over his chest.
“You really are the best, Jimmy,” she crooned.
“You’re not bad yourself,” Jimmy chuckled.
“Not bad?” she teased. “I’m the best too. What we have here is the best and the best.”
“Sounds like a new sitcom.”
“More like a porno movie,” Monica laughed.
They lay quietly for several moments. Then Monica’s hand found Jimmy’s cock.
“It’s so cute when it’s limp,” she commented, stretching and twisting it above his belly.
“It won’t stay that way for long if you keep doing what you’re doing,” Jimmy warned.
“Good.”
Monica knelt over Jimmy’s legs and lowered her head to his crotch. She maneuvered the still limp penis into her mouth, where it instantly sprang to attention. She sucked gently then raked the growing shaft with her teeth. Then she raised her head.
“How old are you, Jimmy?” she asked.
“Forty-two.”
“Amazing,” she murmured and lowered her mouth to its task.
As Jimmy felt himself approaching the point of no return, he lifted Monica’s head.
“Will you let me come into your anus?” he asked.
“Yes,” Monica whispered.
“Do you like it?”
“I…” Monica began enthusiastically. Then her expression softened. “I’m okay with it.”
“I won’t try to have an orgasm. It would take too long on the fourth go. I just want to feel myself inside you.”
“Come on in,” Monica offered with a smile. “How do you want me?”
Jimmy positioned her frog-like before him as he stood beside the bed. This time he put two condoms over his organ then slicked her asshole with jelly.
“Here I come,” he warned.
He held her buttocks steady and pressed his penis into the little rear mouth. It tensed and he waited for her to relax. When the opening felt soft, he pushed hard once and heard a gasp as the muscles tightened again. The pressure was almost too much for pleasure, but not quite.
“Try to relax,” he murmured. “I’ll go slow.”
“It’s okay,” Monica gasped. He could hear how hard she worked to steady and slow her breathing. “I’m ready.”
Though the muscles were still tight, Jimmy thrust again hard. Sometimes quickly was the best. Monica trembled and he held her steady in his hands. One more good push. Ah. He could hear her panting now and feel the throbbing of her overstretched muscles. But God, it felt good. He tried a gentle in and out, barely an inch. Monica gasped. She was too tight.
Jimmy leaned over her back and wrapped his left arm around her waist to hold her firm. He knew his penis shifted inside her with the movement and he apologized mentally. Just hold on for one minute, he promised. I’ll make it better. His more agile right hand found her cunt and cupped the softness for a moment. Then he slid a finger into the crease and found her clitoris.
“No,” she protested weakly. “You don’t need to…”
“Hush,” Jimmy whispered. ‘This will feel good.”
He massaged her gently, knowing the ache in her rear made arousal slow. But it would come. Patiently he worked each sensitive spot, touching and teasing and then pressing insistently. All the time his cock throbbed in the snug embrace of her penetrated rear. Eventually her breathing became more regular and then shortened to aroused rather than pain-managing pants. He slipped his finger inside her dripping cavity and knew she was almost there. He twisted his finger inside her and savored the almost-orgasm.
Then his hand went back to work and he stroked and twisted and pulled. Now that he knew she was ready, he pushed her insistently. Stroking and stroking and pinching until… Her vibration spread from womb to anus and then engulfed her whole body. Jimmy braced his legs to hold her safe as he surrendered to the beautiful tremors. Her muscles kneaded him like the most skillful masseuse, the contractions more rapid than could be achieved by volition. Ah, to be in a woman’s ass when she came.
Slowly the tremors subsided. He wanted to feel it again. His cock ached for the massage to continue. His hand adjusted on her crotch and his finger snaked out toward the clitoris, the key to her and his ecstasy. Monica whimpered and Jimmy’s desire began to fade. She was a limp weight in his arms, he realized. He couldn’t do this to her again, not even for what he planned to pay her. He eased himself slowly from her backside and lay her gently on the bed.
“Are you all right?” he asked as his hand smoothed her hair.
His only answer was her trembling. He lay down beside her and cradled her body spoonlike with his. He murmured nonsense to her as his hand rubbed her back. Slowly her trembling ceased.
“Did I hurt you too much?” Jimmy asked. “Did I go too far?”
She turned in his arms and hugged him fiercely.
“I’ve never done that,” she admitted. “It was…”
Jimmy waited.
“Unbelievable.” Monica smiled. “Overwhelming. I’m just now recovering.”
“I’m sorry if…”
Monica put her finger to Jimmy’s lips and hushed him.
“No apologies. It was good. It was so powerful, I fell apart a little.”
“You are quite a woman, Monica.” Jimmy kissed her forehead. “I’m going to leave now. You sleep here till the morning. The room’s paid for. Order up whatever you want for breakfast.”
“Thank you.”
Jimmy took a short hot shower followed by a cold rinse which effectively doused his lingering erection. By the time he dressed and returned to the room, Monica was fast asleep. He kissed her once more on the forehead and tucked a five thousand dollar tip into her fist, then turned and walked out the door.