Bend Over For Me..Just Like That..

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He has his first experience performing anal sex.
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Justaja
Justaja
4 Followers

They had only been chatting for a few weeks online when he told he had never had the pleasure of being with a girl who would let him have anal sex with her. She was undoubtedly a fan of it and made that clear as day. His wife was too scared it would hurt, just like all his girlfriends before her. She told him she would gladly sign up to be his first and he quickly took her up on the offer.

They had met a few days earlier at a local hotel and had been having fun fucking every which way imaginable during his week away from home. She knew it had been on his mind since day 1 but she really wanted him to hold out for a bit which he had done quite nicely. She wanted to be perfect for him and that morning in the shower she had shaved her legs, trimmed her pussy, and picked out her favorite body wash - a simple vanilla. She hoped that every time he smelled vanilla in the future he'd think of her.

He would be at his work training from 9 to 5 and when he got back she'd already be nearly naked in his hotel room, waiting for him, wanting him inside her as soon as he set foot inside. She carefully chose an outfit - knee high black socks with lace at the top and a simple bow in the back, a black bra with a keyhole to match the neckline of a tight black dress that showed just the right amount of cleavage and just enough leg. She texted him a picture of her ass peeking out from under her dress just before 5 o'clock. She didn't want to torture him too much, he still did have to get back to the hotel in one piece.

He felt his phone vibrate and smiled to himself. Being with her had turned him into a master of keeping a straight face in any situation but god knows she had pushed his limits. It was one thing getting a cleavage shot when you were alone at night in your room and an entirely different one to get a spread wide pussy pic when you're at your friend's house playing poker. He still had 15 minutes of training to go and considered briefly waiting to look at his phone but his fingers seemed to work faster than his common sense and there was a wonderfully hot picture of that sweet ass he had spent more nights cumming to than is probably healthy. He was glad he was sitting as his legs had nearly failed him for less dirty pictures than this. It wasn't even so much the picture as the text that came along with it - "5:20pm" The diagrams and jargon and troubleshooting would all become a blur over the next quarter hour as his heart started to pound and his cock hardened and strained to get free of his jeans. He took a few deep breaths and turned off his phone, jamming it back into his pocket and trying to get back to concentrating for just a little bit longer. The twenty minute drive back to the hotel was going to be a challenge, but for now...

It had been months since she had had her ass fucked at home and she was as ready as she could be. She felt smooth and confident and sexy as hell. She loved being a bad girl with him, being a good girl with him, being with him. She glanced at the clock - 5:05pm - he would be back in 15 minutes and she had to consider just how she wanted to be for him when he walked in - looking out the window, sitting in the chair, straddling the desk chair backwards, sitting on the balcony - nonchalant? determined? Does everyone think this much about how to sit when their hot side piece is on their way back to the hotel for hot, filthy, raw, hardcore anal sex? Who knows. She chose the bed, laying on her stomach, reading a book like she wasn't expecting him any moment. She heard footsteps in the hall and looked down to at least make sure the book was the right way up. Oh, who was she fooling. It was all for show - he knew it, she knew it, and he'd be in her in no time.

He stood outside the door for a moment and adjusted himself, fuck that was a long car ride - all nineteen minutes of it, he thought to himself. He had spent the ride deciding how he wanted to have her tonight. He wanted his first time to be one to remember - he knew he wouldn't last long in her ass but that didn't have to wreck the experience. He imagined her on her back, legs up over his shoulders. He imagined her on all fours, ass right at hip level. He imagined sideways spooning with deep penetration. He...just needed to go inside and put his hand on her throat and look into her eyes and tell her that she was to get into position and be prepared to have her ass fucked until he had finished with her. *deep breath*

There she was, laying there without a care in the world. Her ass looked so perfect in that dress and those socks, oh those socks looked undeniably hot. He wanted to hurt her so good tonight. She got off so hard on that kind of pain and he couldn't wait to leave bite marks and handprints all over that round, pale, perfect ass.

She looked back at him and smiled the most innocent smile she could "Do you want to go get something to eat?" she asked while keeping a straight face-ish, somehow, kind of. He walked over, grabbed her hair, turned her face away from him and smacked her ass as hard as he felt comfortable...the night was still young. That was so not what she expected and she was surprised...surprised that she didn't cum right that second. She whimpered in pain, that kind of pain that can only be tied so closely with pleasure when the person you're with is driving you mad with lust. He tugged her hair hard enough to give her the hint that she needed to get up on all fours and inch towards the edge of the bed. He pushed her face down into the bed and stood behind her admiring the view. He could be so into this power position when the mood struck him, it was so good for working through latent frustrations and unmet needs, plus he knew her inner filthy whore loved it. He moved her dress up just enough to give him a clear view of her ass, now complete with one well-defined handprint which complimented the whole scene perfectly. "Don't move." He was still fully dressed, taking his phone from his pocket and taking a picture which, although he would never forget it in his mind, would still be a gorgeous shot for those late nights alone.

Her face was as burning hot as the handprint on her ass and she felt as though she might explode if he didn't fuck her and quick. He was the only person to ever make her blush, she had had to check this some nights in the mirror - yep, pink cheeks indeed...sonofabitch. The power play always came back into it and he had her so badly. She told him this many a time and he had always replied that she had him just as bad. "Please fuck my aSHHHHHHH. I will when I choose to and not a moment sooner."

He was so fucking good at this it should be illegal. Part of it was that face, he was so damned boyishly fucking hot that it made him look innocent. It had taken her many months of conversation to finally admit he was not as angelic as he seemed. It was when she realized that although she had picked him up in an adult chat room she HAD picked him up in an adult chat room i.e. he was on the prowl too. She had tried to tell him that she was a worse influence on him then vice versa but she had finally compromised that they were equally bad influences, but still didn't really truly believe it...until now. She adored that very bad side of him and made it no secret that she loved being controlled by him in the bedroom. And at this point her body was certainly not keeping any secrets of its own from him...

She could feel her legs begin to shake and betray her ability to stay still like he told her to. She wanted him inside her and it felt like an eternity until she sensed him begin to move again behind her. She heard his jeans unzip, heard him take a deep breath, felt the heat from his hand through her dress as he placed one on her up her upper back. His other hand was tightly around his dick as he rubbed it up and down her pussy which was well past the point of being soaked. He entered her for just a few quick, slow strokes before pulling out and sliding the head of his cock up and down her ass before starting to push in slowly. Despite loving to be rough with her this whole prospect made him a little nervous and he didn't want to hurt her in that not fun way. She had told him she loved anal sex and she had reassured him that he wouldn't hurt her but still he was cautious and slow on his entry.

He realized he would have to push a bit harder as she was as tight as she had described. He leaned some of his weight into her and felt the head of his cock pop inside her, she gasped and he tensed up "Are you okay?" he whispered quieter than he had expected. She nodded and he pushed a little deeper tentatively. This was the quietest their room had been since they'd arrived. The air was heavy with his concern for her and her concern for him...okay so her concern was for him to start fucking her solid but still...

She whispered, "It's okay, you won't break me..." as she pushed back into him ever so slightly. She started rocking back and forth until he moved in time with her at which point she went back to having her face buried in the mattress. He seemed to ease into it and picked up momentum, his hands beginning to grip tightly at her hips and ass. He suddenly stopped and after what felt like an eternity took a deep breath and began to pound into her so hard it nearly laid her flat against the bed. She moaned and cursed loudly, urging him to finish inside her. He knew he had seconds left and took this chance to leave a matching handprint right below the first before reaching up to grab a fistful of her hair and yank hard. Her head snapped up as she arched her back and he filled her ass with a day's worth of cum. He continued to pump into her as his orgasm subsided, her hair slowly becoming free of his grip until she collapsed. His hips followed her ass down and he pulled her off the bed onto the floor with him. He slipped out of her as and she nuzzled her head up under his chin as he wrapped his arms around her.

She loved the afterglow that came with great sex. They had always joked that neither one of them was much for long cuddling sessions. Her usual modus operandi was to have a shower, a bite to eat, maybe a drink, and let her brain dissolve in front of the TV. He usually played some video games and just generally relaxed but at that moment neither wanted to be anywhere but right there - intertwined on a hotel floor, breathing heavily, sweating, and happy as can be.

Justaja
Justaja
4 Followers
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AnonymousAnonymousover 7 years ago
Great title

More please...

AnonymousAnonymousover 11 years ago
Excellent

I loved the build up in this story; I felt I was part of it- fantastic

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