A Nightcap on the Road (Closed for Angeleyz)

Emily tried desperately to distract herself, counting the strokes. One, oh god, he needed to stop. Two, please, god... Three, it was too much...

Now Emily... You may cum now.

Softly spoken in that low, deep voice of his, those six words were all she needed to send her flying over the precipice, squealing in a silly chipmunk-like sound as her walls contracted violently and with an intensity that actually scared her. Her body quivered like a bowl of jello for what seemed like forever until it finally quieted down.

Sprawled across his lap with her face mashed into the couch, Emily slowly became aware of her surroundings. She didn't move, except for the occasional twitch, as she tried to collect herself, scrambling for something to say.

As soon as his words left his mouth, her body shuddered and she cried out with a squeaking sound he had never heard a human make before. His hand was clamped down tight by the contraction of her velvet walls around his fingers, so he held still, pressing upon her tender spot and holding on as her body bucked and quaked.

His hand was soaked to the wrist in her juices, her body glowing in a sheen of perspiration. She rode the wave of her orgasm to it's natural conclusion, her body eventually going limp in his arms.

Slowly removing his hand from between her legs, he gently stroked and soothed her back and thighs. Rubbing her gently and occasionally stroking her hair lightly to calm and comfort her after such an intense experience.

"Good girl... It's OK... Every thing is OK." Repeating soothing platitudes as she slowly began to regain her senses. "Your safe... Your OK... Everything is OK." Making sure she understood that what had just happened OK, that it was good, that she had nothing to be ashamed about.

Emily found herself breathing in and out in time with his strokes along her back and legs. Slow...2....3...4, back....2....3....4, soft...2....3....4, back...2....3...4. Eyes closed, his constant murmur of Good girl... It's OK... Everything is OK helping to calm the turmoil in her mind.

"Well that was.... unexpected....," she finally managed to murmur into the couch, feeling shy.

He felt her relaxing and slowly regaining her senses. Responding to his gentle caress he heard, "Well that was.... unexpected." softly escaping her lips.

His hands continued to soothe her, not because she necessarily needed soothing at this point, but because her skin felt exquisite beneath his touch. Pausing only for a moment to gather her hair back into a pseudo ponytail and out of her face.

"I'm going to have to assume you mean that in a good way." He replied, "What was so unexpected?"

Emily shivered as his hands continued to caress her back and legs. God that felt so good. So good that if she were a cat, she'd be purring. Eventually she felt him pull her hair up into a mock ponytail, exposing her face.

I'm going to have to assume you mean that in a good way. What was so unexpected?

Blushing a little, Emily paused before admitting sheepishly, "I don't normally...don't normally... You know....finish." Her shoulders rounded up a little at the confession as she turned her face back into the couch.

OK... So... stunned twice in two hours. First her thoughts spoken out loud by accident, and now this. Could it be? Could it possibly be that this gorgeous creature has never... ever... noooo. It couldn't be... could it?

He considered her words, continuing to rub and soothe her body. Finally, he had to ask. He just had to know...

"Really? Have you ever... finished? Or just not often?"

Really? Have you ever... finished? Or just not often?

Emily wasn't really surprised that he asked. Hell, she would have asked if someone had made the comment to her, but that still didn't stop her cheeks from heating even more. Wishing he'd let go of her hair so that she could hide behind it, she struggled to find the right words.

"Once or twice... Maybe? I usually... um.... stop it... turn it off I guess you could say before it happens."

Jim contemplated her words for a moment. This woman needed to embrace herself and surrender to the urges her body demanded of her. She needed to learn how to feel pleasure despite her minds need to rebel against it. She needed to be... he hesitated to even use the word in his own mind, but it was the only one that fit. She needed to be trained in how to embrace her physical needs.

He stroked her blushing cheek and spoke softly. "It's OK... I'm going to teach you how to enjoy your body. I'm going to show you what you can feel, and I'm going to make sure that you know it's OK to feel this way... crave it even. Remember, tonight there are no regrets."

He leaned over and kissed her neck, the residual perspiration giving a salty enhancement to her naturally sweet skin. Drawing her up in his arms, he lifted her so that she was sitting on his lap, her legs astride him as he kissed her again. This time he kissed her on the lips, fully, and with no mistaking his intent as his cock swelled and rubbed against her still wet folds.

Emily's lips quirked to one side as he stroked her cheek, feeling like a complete idiot. What kind of fool turned off her orgasms? However, she couldn't remember a time when she didn't disengage or cut herself off, but she had always hidden it from whatever partner she was with at the time, not wanting to have to deal with the whole 'play by play' breakdown to figure out what had gone wrong. She had gotten so tired of having to fake it, to avoid these conversations, that she had pretty much given up on sexual encounters with others.. and just dealt with her needs, as temporary as they were, on her own.

It's OK... I'm going to teach you how to enjoy your body. I'm going to show you what you can feel, and I'm going to make sure that you know it's OK to feel this way... crave it even. Remember, tonight there are no regrets.

Emily wanted to snort at his words, thinking she had had too many years of conditioning behind her to think a single night would fix anything, but then again... he had managed to produce one miracle... Who was she to turn down such a tempting offer?

Just as quickly she wanted to giggle, as Jim pulled her up and shifted her so that they were chest to chest and she was straddling him. When his lips met hers, she brought her bound wrists around his neck and moved eagerly into the kiss. She could feel his hard cock pressed against her lips and tried to wiggle closer.

As her bound arms slid over his head in response to his kiss, Jim's cock throbbed. The head just beginning to tease the opening between her lips. Her hip wiggle nestled his head even deeper, her juices beginning to drip down his shaft.

Kissing her passionately, with his hands on her hips, he pushed her down firmly, but slowly. Forcing her pussy to slide down upon him. His head cleaving a path past her entrance and parting her slick muscled walls with his hard wet cock.

He let out a low moan as she slowly engulfed him. His hands pushing her down further until he was buried deep within her moist folds, her muscles spasming around him, massaging his head and shaft, in a most exquisite fashion.

Buried deep, he slowly broke his kiss with her and looked deep into her brown eyes, "I'm going to fuck you Emily. I'm going to fuck you hard and I'm going to fuck you slow. I may even fuck you against that window over there just to show the entire City that I'm not only fucking... I'm fucking you tonight." Raising her hips with his hands he held her at the very edge of penetration, his head just barely inside her. "But most importantly, I'm going to fuck you because you are Mine." Pushing down hard on her hip, impaling her on his shaft in one hard fast stroke. He held her there for a moment before rocking his hips and starting a slow, steady rhythm.

Emily moaned softly against Jim's lips as she felt his hard cock slip against and then just inside her soaked pussy. She was slightly distracted from the teasing entry when his warm hands caressed up her legs and skimmed her still sore ass. Those same, skilled hands then settled on her hips, guiding her onto his cock in a slow, methodical manner, until she was positive he couldn't be any deeper.

She whimpered in protest when he slowly broke off the kiss, but immediately quieted at his intense look. I'm going to fuck you Emily. I'm going to fuck you hard and I'm going to fuck you slow. I may even fuck you against that window over there just to show the entire City that I'm not only fucking... I'm fucking you tonight. 0h my god, that is so hot!

Whimpering again, when he raised her up so that she could just barely feel the tip of his cock brushing up against her, Emily's breath caught when he said But most importantly, I'm going to fuck you because you are Mine.. Her mouth fell open in a silent OH as he drove her hips down hard, penetrating her with ease. As he pistoned in and out of her sopping pussy, Emily tucked her face into the crook of his neck and alternated between kissing and suckling on the sensitive skin there.

Her expression as he impaled her on his cock made his mind swim. the sheer satisfaction her face held as he took her hard made his cock swell inside her.

He rocked his hips in a steady hard fucking motion as his hands worked to lift her and guide her up and down his shaft. Her body responding by lifting and falling back against him in rhythm with his thrusts.

Burying her head in his neck, he could feel her lips and tongue working the tender flesh, and driving him wild. He held her as her muscles contracted around his head and shaft, massaging him as he continued to occupy his new territory.

His head rocked back as he closed his moaning, “Ohhhhhhhhhh my Goddddd, you feel so good.”

Emily felt every blessed inch of him as he guided her hips forward and back, forward and back. Several times she wanted to drive down harder or wait just a little longer before pulling back, but he kept the pace maddeningly even, but oh my did it feel spectacular.

She continued to alternate kissing, licking and sucking, fighting the urge to scrape her teeth in the crook of his neck. The feel of his hard cock pumping in and out of her wet core was almost more than she could bear. They were rapidly approaching the point where she'd start shutting down in the past, and she had a slight worry in the far recesses of her mind that something would cause it to happen again. The sound of his moan, Ohhhhhhhhhh my Goddddd, you feel so good was a timely distraction, causing her insides to quiver deliciously.

Feeling so good, but wanting more, needing more from her, Jim grabbed her by the ass and stood up slowly. Her petite form clinging to him as he kept himself buried deep. Walking carefully the few steps to the window, he pressed her back against the cool glass and held her tight as he continued to stroke in and out.

Whispering into her ear, "Let them watch if they want... I'm fucking you tonight and I don't care who knows."

Emily giggled against his neck when Jim grabbed her by the ass and slowly stood up. Damn that feels good... She kept her arms entwined around his neck and locked her legs securely around his waist, but she really wasn't overly concerned about him dropping her with as easily as he moved her around.

She was a little surprised when she felt something cool press against her back. It took her a moment to realize it was a window. She would have protested if he hadn't whispered in her ear, Let them watch if they want... I'm fucking you tonight and I don't care who knows. Moaning softly, she pressed her lips against his, thinking that perhaps she didn't care either.

Jim moaned loudly as her lips pressed against his, her tongue dancing with his as if in a fiery tango of their own design. His continued thrusts penetrating her deeply, feeling every inch of his shaft being massaged by her flexing walls. Her legs gripping him, her ass flexing in his hands as she thrust back against him.

So good, everything feeling soooo good as he thrust in and out. His hands gripping her ass hard, the still hot flesh yielding under his grasp. The coolness of the glass making an erotic contrast to their heat.

His cock swelled, the head expanding as his shaft rippled within her warm caress. His hips moving faster as he continued to fuck her hard for their ‘audience.’

“Don’t hold back Emily… let it go… let it all wash over you. Feel what your body demands of you.”

Emily couldn't remember a time she had ever felt so out of control and she didn't really care. All that mattered was how incredible he felt inside her and how she didn't want it to stop. Her kisses grew more and more frenzied, mimicking the movements of her hips.

Don’t hold back, Emily… let it go… let it all wash over you. Feel what your body demands of you.

She shivered as his words skittered across her senses. How was it that she could feel them wrap themselves around her body, slowly sliding down her spine and down into the very core that he was so energetically fucking?

God, everything about this was so hot. From the way he gripped her still sore ass to the way he pistoned in and out of her, to the way his moans echoed in her ears to the coolness of the windows pressed against her back. And then there was that thought that somewhere outside someone might be watching their frenzied movements...

As her kisses became more frenzied, his arms became more tired. Holding her against the glass his hands firmly palming her ass was incredibly hot, but he had another idea.

Easing her down slowly and kissing her with blind lust, Jim slowly withdrew from her. The expression of confusion, craving and surprise on her face almost caused him to laugh out loud. Removing her bound hands from around his neck, Jim turned her around. He pressed between her shoulder blades, forcing her to bend at the waist, her arms against the glass, her ass in the air waiting to be filled. He could see see her face reflected in the window, her eyes drawn inexorably toward the lights of the city below.

With his hands upon her hips he slammed into her from behind.

"Oh Yesssssssss"

Picking up the rhythm where he left off, he couldn't help but give her another hard smack across her red cheeks. Just one, to remind her what it was her body truly craved. Moaning as the change in angle provided him with a whole new set of sensations up and down his cock. He continued to fuck her as he watched her reflection in the cold hard glass. Her eyes still locked on the lights below.

So caught up in Jim's kisses, Emily didn't notice him lowering her until he pulled out. She immediately wanted to howl in protest... No! Not yet... It felt sooo good... Don't stop now!!! When he pulled her arms from around his neck and turned her around without speaking, she was devastated. What did I do wrong? What did I do?

Emily released a soft sigh when he pressed a warm hand between her shoulders. Oh thank god... He's not going to stop... She dutifully bent over, unsure if he was going to spank her some more or what, but happy to take whatever he was willing to dish out. She didn't want this delicious experience to end! The lights below caught her attention, and she peered down wondering if anyone was watching... staring up at her, as she was bent over, full breasts hanging down almost painfully.

Preoccupied by that thought, Emily was caught off guard when Jim thrust deeply into her wetness, and she almost banged her head into the window as a result. He immediately began a sweet assault on her senses, withdrawing and invading, teasing and plundering, faster and faster until all she could do was try to clench her muscles around him, to hold him tight if only for a second or two.

The smack on her ass startled a cry out of her, but one of pure pleasure despite its stinging blow. Her mouth then opened and closed soundlessly as she struggled to contain the fine tremors that were building in her legs and core. His moans of pleasure traveled up and down her spine, making them harder and harder to control, so she tried to use the lights below to help distract her.

Jim felt her body quiver as he thrust in and out of her. Her heavy breasts swinging freely back and forth with each thrust. His hands sliding forward from her hips and grasping them firmly on the back swing to hold them tight. Squeezing the tender flesh tightly as he continued to fuck her with deep penetrating strokes.

He could feel he was close to cumming as he recited... Ty Cobb... all time batting average...367... Barry Bonds... All time Home Run leader... 762... Pete Rose... Most games played... 3562... Ricky Henderson... Most stolen bases... 1406...

It wasn't working... Emily was just too much for simple tricks like reciting Baseball statistics. He pinched her nipples hard as he thrust deeply into her.

"Fucccccckkkkkkkk"

Exploding inside her as her body lurched with his thrusts and spasms. Feeling his cum splash against her walls. Groaning deeply at the intense sensation flowing through his body. Feeling his cock pulse and throb deep within her, each flexing throb bringing more pleasure than the last.

Emily could no longer hold back the low moans spilling out of her mouth. Moans that started with each thrust forward, trailing off as he all but withdrew, and kicked off again as he slammed back deep inside. Each thrust causing her breasts to jerk to and fro in time with his movements.

His hands on her hips biting into her skin controlled the steady pace, although Emily detected a small quickening. The faster he got, the deeper he pushed in until she was almost afraid he was going to punch through her stomach. The trembling in her legs became too much to control and she turned her head to the side, pressing her cheek to the cool glass and closing her eyes.

Emily kept reaching for the release she wanted desperately, but terrified her nonetheless. She really should stop herself... more than once in one day... one week... hell, one month would leave her constantly wanting more and she'd never be able to recreate what he was so deliciously doing to her with just her fingers and a toy.

Jim's hard pinch to her nipples as he thrust forward almost brought her to her knees in pleasure. Eyes snapping open as he cried out, Fucccccckkkkkkkk,", she rocked back and forth as she felt his hot seed begin to jet into her very core. Oh yesssssssss..... She pushed back onto him, trying to extend their time, even as her mind begin shutting down her body, pleased that he had found his release but telling herself to relax. Feeling like she had two totally different factions warring within her, she bit down on her lip to keep the frustration from spilling out.

Knees shaking, hips quaking, cock throbbing as her walls griped and massaged him. Feeling the last of his cum ease out as she pushed back against him. His head swam as the intense pleasure of his orgasm washed over him. Both of their bodies covered in a sheen of perspiration.

Jim leaned over to hold her close as his cock rested within her. Slowly softening to a semi hard state, he felt light headed as they pressed together. Lifting her up so they were standing front to back, he took a few moments to hold her, caress her and watch the City watch them.

Eventually, he eased her around so he could look into her eyes, "My god Emily, that was... intense."

Though they had just met, Jim felt an intense feeling of possessiveness over Emily. He had not had an evening of pleasure like that in a very, very long time. The way her body responded to his touch and the way she visibly fought her own pleasure were both areas he wanted to explore much further with her. What other buried desires lurked under that proper, professional exterior.

Feeling Jim wrap his arms around her as he leaned over her back, Emily was surprised she didn't want to babble some inane excuses and try to leave. Hooking up with complete strangers wasn't her thing, but here she was pressed against an open window, hair disheveled and feeling his slow withdraw and all she wanted to do was to stay exactly as she was for however long he wanted her to do so.

Following his unspoken direction to straighten up, Emily felt a little stab of loss when his cock finally slipped free from her body, but that was quickly eased when he continued holding her close to him. The light caresses he bestowed to her arms raised goosebumps on her rapidly cooling skin, and she pressed back against seeking to share his body heat.

The embarrassment that had been lacking earlier hit her full force when Jim turned her around, looked her in the eyes and said, My god, Emily, that was... intense. She dropped her eyes to his chin, suddenly overwhelmed with mortification. He must think I'm a complete slut.... Her mouth opened and then closed, unsure what to say.

She looked away as he finished his words, embarrassment sweeping over her face, her mouth opening to reply, but closing silently. This would be the regret creeping in. Her conscious mind rebelling at the things she allowed herself to do. Her fears and phobias surfacing after an evening of banishment.

Easing her away from him briefly, he untied her wrists. Tossing the tie aside it was obvious that it would never serve as neck ware again, but that was by far the least of his worries. He kissed her now free hands and put an arm around her, guiding her to the bedroom gently, "Come with me, let me hold you. We both need a rest."

Opening the bedroom door, the bed already turned down by the night staff, he guider her inside "And you need to know... nights like tonight are not something I do all the time. In fact, hardly ever. It's been a very long time since I've felt what I've felt this evening. You did nothing wrong, remember that."

Emily watched in silence as he untied her wrists and tossed the tie to the side. Her lips quirked when he kissed her hands, charmed by the almost old-fashioned gesture. Come with me, let me hold you. We both need a rest. She offered no protest when he placed his arm around her and guided her to his bedroom, the idea of cuddling with him appealing.

The bedroom was dimly lit, something she was grateful for when Jim tried to assure her she had done nothing wrong. She had followed a stranger up to his room and had fallen into his arms minutes after entering it, and she had done nothing wrong?! She had encouraged, begged even, him to bite her nipples, and she had done nothing wrong?! Had sucked his cock, had been licked and fingered herself to orgasm, and she had done nothing wrong?!

Her poor ass was still sore. She probably wouldn't be able to sit through her meeting the next day, and even if she could, each shift of her weight on a chair would remind her how she had been sprawled over his lap while he paddled her. And she had done nothing wrong?! He had fucked her up against the open window for anyone to see, and she had done nothing wrong?! Even now, she could feel their mixed juices slowly traveling down her leg, and she had done nothing wrong?!

She looked up at him, eyebrows knit as she considered the fact that perhaps she really hadn't done anything wrong...