One Night Out

He gazed across the briefcase intently, drawing her eyes to his and holding her. "What is your safe word?"

"Pineapple." She smiled back, almost vibrating on the spot now. His grin returned and he stood.

"Over here. On your knees. Face down. Ass up." Her butterflies fluttered wildly as she did as she was told. They had never included this before! Maybe tonight he would finally... She crawled to the edge of the bed and turned her back to him, bent over supporting herself on her forearms and presented her most secret places to his wicked intentions. What was he going to do?

"Mmmm." She moaned as his tongue stroked her tightest little entrance. This part was always fun. Dirty, nasty and oh so hot. His lips and tongue soothed and coaxed her puckered star, his hands massaged her cheeks, the small of her back, and her thighs. If there had been any tension left in her body it quickly ebbed away. Slowly, he guided his tongue past her little ring of muscles. Gradually delving deeper and deeper into her naughty place. She surrendered to him. She knew she need never fear him. Only when they really wanted that did they carefully make it happen. This was safe and kinky and amazing.

It didn't take long before he could push his whole tongue inside her with ease. Two of his thick fingers sank into her slippery pussy and stirred new excitement in her. She couldn't help but grow more excited, but knew to keep her rosebud relaxed for him. After briefly soaking his fingers he removed his tongue and slowly eased them into her ass. She squirmed at the always familiar yet new feeling of him probing inside her like this.

He began to move faster and a slow moan escaped her. Knowing he may get her in trouble, but unable to resist, she reached back and spread her cheeks for him. Encouraging him to give her more.

"Getting greedy?" He asked amused. Unsure if she was being chastised or not, she held perfectly still and nodded meekly.

"Mhmm." She cooed. He chuckled and removed his fingers. Thinking she had been bad and was being punished, she whimpered at her sudden emptiness and let her hands down. Suddenly she felt the thrilling bite of rope at her wrist as it was bound to her ankle. His deft hands lifted and shifted, tucked and pulled, wound and bound in a new way they had never tried before. A slim gap separated her knees, and each forearm was bound to her calf on the same side, arms strait back. She had no choice but to rest her cheek on the covers and look back at him through the corner of her eye.

He grinned as she tested the bonds. She wasn't going anywhere. The most she could manage was to lift or raise her bottom a couple of inches. The excited fear bean to return. She was completely at his mercy again. That enormous man behind her could do anything he wanted to her and she couldn't stop him. She could feel her pussy spasming and her heartbeat quicken. Her safe word was as far from mind as she could banish it. He would take care of her.

The cold splat of lube on her asshole told her it was time for the toy. The plug was the largest they had, and she had managed to take the whole thing a few times now. Hopefully tonight she could finally feel him...

The slightly cool glass tip pressed against her ring and she happily took it in. After everything tonight, the first few inches were mastered in less than a minute. There was no tension left in her body, only excitement over the new experience, and she had complete trust in him. The toy was both long and thick. They had wanted to get something as near to the size of his monster as they could. Most people would have thought it was just a novelty toy, but it still wasn't as long or quite as thick as him.

A deep groan escaped her as he hit that sweet spot that demanded a little more attention. He eased back and added generous amounts of lube to the toy and strait inside her, before continuing. Slow and easy he worked the plug back, then pressed it forward and held it, letting her slowly grow accustomed and take a little more in. Back and forth, slowly deeper, stretching her, stretching her. Her obligated silence, and the tight bonds holding her in place made her heart race and her breath catch in her throat as the excitement warred with her need to stay relaxed. Inch after inch the toy slowly filled her. She was panting with the effort, but she wanted more.

Suddenly the toy propelled forward faster than expected. She tensed as her tight little canal circled the bulb of the plug and pulled it in deep clamping around the warm glass base. "Oh, gaawwd..." She breathed. It was in. the whole toy was in. It was a little uncomfortable, but it was also exciting, and she always felt accomplished. He let her relax again before gently pressing on it, pressing the unyielding glass just that little bit further. It hurt a little. Her pussy juices dripped down her leg.

He eased the toy back and forth. Ever so slightly. The pain receded and she began to coo lightly again. Slowly, carefully, he pulled the plug back. Reluctantly her body opened up to let the bulb pass. Once over the bulb the rest of the plug shot out and she was filled with a relief she wasn't expecting. Her hot, wet centre gushed its appreciation.

He eased it in again. Quickly to start, then slowing as they neared the swollen bulb. With a uncomfortable but satisfied grunt she pulled the last of the toy in again. Before she could settle completely he began to pull it out. Her body resisted letting it go, then rushed to be free of it again. The relief was still surprising. He did this a few more times, faster each time, until there was no pause between the penetration and the retreat. Her body hummed with conflicting messages that were quickly being overpowered by pure delight. Maybe tonight...

He pressed the plug in hard and not slowly, filling her and making her groan. Yes, she was definitely enjoying this. She felt him stand behind her. Her butterflies were back. But as usual he wasn't going to let her guess what he had planned. Suddenly his throbbing head was pressing into her still sloppy pussy from their previous fucking. The pain that lit behind her eyes was so unexpected that she froze. Her ass was already the fullest it had ever been, and now he had forced his enormous girth inside her tender twat. The sensation of full was so complete she was paralyzed, the pain that came with it was unbelievable. She was too full. Much too full. So full she thought she would burst. Her pain stricken mind began to search for the safe word.

But then he moved. The relief of some of the pressure was euphoria. And when he thrust forward again, every pleasure centre she had was stimulated completely. Every nerve he could have possibly tickled was assaulted by this overwhelming fullness.

"Oh, it hurts. Oh it hurts. Oh my gawd it hurts. Oh my gawd it hurts. Oh, gawd. Oh gawd." She panted her mantra against the covers as the tears threatened the corners of her eyes. He heard no safe word, so he continued to go faster and deeper. She knew this, and her excitement grew. Eventually he began to truly fuck her. Gripping both hips hard and thrusting deep and fast. Filling her pussy, ramming her cervix as the huge butt plug stretched her ass.

"OohhOhhOhhOoohhOhhOohhOohhOh! Fuck! Ya! Fuck! Ya! Fuck! Fuck! Fuck! FuuUuuUuuUUuuuUuu..." He reached around and tweaked her nipples gently. It was just enough. She screamed out loud as her fourth orgasm of the night turned her to jello beneath him. The night had been so overwhelming, and this was the most overwhelming experience of her life! Pain and pleasure mingled and blurred, her vision went black and her whole world was pulled out from under her. The intensity of yet another orgasm had her completely spent.

When she came to she couldn't move. Still bound, the first thing she noticed was the alarming emptiness inside her. He was gone. The toy was gone. It was such a terrible change that she could have wept. A heavy hand rubbed her back and massaged her ass.

"You ready?" He whispered as he leaned in next to her ear. She shook her head. He leaned in closer, "What do you need?" She almost drunkenly wiggled her face closer to his and kissed him lightly. Then she nodded. A cheshire grin split his handsome face. He kissed her brow, then returned to his place behind her.

She heard the click of the lube cap before he held it to her puckered and tired ass and squeezed a large amount into her. Then she heard him slather himself and drop the tube beside them. She was so tired, but the spark of excitement smoldered again.

As soon as his head touched her, she knew he had wanted her this exhausted and weak. He was still so much more than the plug, and he didn't start small. Her fear weakly made her heart flutter, but she couldn't handle much more than that. Her addled brain found some excitement in that.

His swollen head pressed, pressed, pressed. Slowly, ever so slowly she opened, and his head eased its way in. Yes, he was absolutely larger. The pain was mild, but immediate. Her fear picked up a little. So did her excitement. She realized she might be too weak to use the safe word even if she wanted to. Her anticipation grew.

Slowly he sank deeper. A pained moan was the only resistance she could offer. She was so weak and limp. She was at his mercy. Slowly he retreated. A reluctant whimper let him know he wasn't unwelcome. His own excitement was gnashing at the reigns! Finally! Finally! He eased himself a little deeper. "Ooww." She cried lightly. He retreated. In a little deeper he sank. "Oowww." Came her groan. With each thrust he sank just a little deeper, with each thrust her reactions became a little more clear.

"Ooww! Fuck!" She suddenly exclaimed. He stopped. The toy had never reached here. This was virgin territory. Her clit tingled lightly. He was finally... "Don't stop..." She whispered. He pulled back, and slid in deep. Deeper than she had ever known. "Ooww, fuck!" She cried. Confident she would stop him if she needed it, he sped up just a little. Smooth strokes back, and long strokes forward to the new territory. Unable to hold himself in check any longer, he gave her the last inch all at once in one deep hard thrust!

"Ooowww!" She cried. Tears had fallen from the corners of her eyes. He stayed there. Buried to the root. She felt his hot balls pressed against her pussy and she laughed. The pain was terrible. His balls against her pussy were scalding. "You made it." She whispered. "Hmmmm." She blinked at her tears as she held him deep inside her. Finally he was in, and not just in, but all of him was in. She fixated on his enormous girth and length painfully stretching her and her pussy moistened his balls. She took a couple steadying breaths. She clenched her hands a few times.

"Please." She whispered.

"What would you like?" He asked gently.

"Don't stop till you cum."

His erection flexed inside her and she winced. He gazed at her tenderly. "What's your safe word?" He asked in a low voice. She took a couple steadying breaths and then answered, smiling through her tears.

"Pineapple."

His cock throbbed again, producing the same wince. Slowly he drew himself back till only his head had her stretched open. She sighed. In one long, even stroke he buried himself completely again. She winced, sucked in a breath through her teeth and then let out a tense groan. He retreated again, and pushed forward again, slowly gaining speed. Her discomfort grew with the speed, and then began to fade as his balls slapped against her pussy faster and faster.

"Oh, fuck! Oh, Fuck! Please! Fuck! Don't stop! OooOoooOoohhHhhh! Her pain disappeared as her lust began to take over. Her pussy was wet and hot, her clit throbbing gently and his grunts and groans behind her had her aching to feel his release. "Come on, baby! Come on, baby! Oohh, Fuck! Come on, baby! Fill my ass. Fill me. Fill my ass!" With a series of savage thrusts his body tensed as he pulled her hips firmly back and drove himself completely inside her. The two of them cried out as his hot seed spilled inside her. Shooting out pulse after laden pulse, filling her with a deep warmth that she knew she would look forward to again.

After his enormous growth finally quit spurting inside her he collapsed over her back, the two of them stuck together by a thin layer of sweat. With his face buried in her hair he panted for breath. She adored his weight bearing down on her. Slowly his shaft began to wilt inside her. While the relief was incredible, she missed the absolute fullness too.

"Thank you." She whispered.

"Thank you." He whispered back.

Slowly he stood up, and eased himself from her raw and angry little ring. No cum leaked yet. He quickly untied her, dropping the rope on the floor. She sagged in his arms as he scooped her up and carried her to a dry part of the bed, where he turned down the covers, laid her out, covered her with the sheet and then climbed in behind her to spoon her in his enormous frame.