Breaking in The New Boyfriend

She rode his cock, reverse-cowgirl style, hard enough to make the bedframe groan in protest. Tim's head rolled from side to side on the pillow, overcome with pleasure, his muffled moans echoing off the bedroom walls. Trembling, his hips rose to meet her as much as they could, his movements restricted by the leather cuffs at the head and foot of the bed. As he approached climax, his body started to lose the rhythm it had worked so hard to establish, and his moans became shorter, and higher pitched. Just as he was about to come, Rachel lifted herself off his cock in a swift movement. He tried to plead for her to continue, but the ball gag reduced his words to whimpers of protest.

His chest heaving when every breath, Tim felt on the brink of insanity. Rachel had been toying with him for hours. He never imagined their date earlier tonight would have led to him being tied to her bed, blindfolded, at her complete mercy.

Earlier that week, his friend Greg's wife had been pestering Tim to go out on a blind date with her friend, Rachel. Tim agreed, mostly to make life easier for his friend, who would undoubtedly be pushed to encourage Tim to go on this blind date. Greg's wife had given him the number, and on Wednesday Tim had called Rachel. The two of them agreed to meet on Friday at a local pub. Rachel had said she'd wear green, so he would be able to find her without having to ask every girl in the place.

Tim had walked in, looking around for a green shirt. When his blue eyes finally honed in on her, he couldn't believe what he saw. She had her long, red hair, down, and straightened it so it hung all the way down to the middle of her back. Her blue-green eyes, accentuated by her V-neck green shirt were scanning the menu, and she had already ordered a beer. Rachel had skin the color of snow; and her breasts were full and perfect, not too big and not too small. He paused for a minute, letting his eyes scan over what he could see of her until he was content.

Strolling over to wear she sat, he introduced himself before sitting down. They made the usual, polite, first-date small talk. In spite of the benign conversation, Tim felt unbelievably drawn to her, and from her body language suspected she felt the same way about him. As they made their way through dinner, and dessert, the conversation had begun to get flirty, with the both of them teasing the other and making each other laugh. The earlier awkwardness forgotten, Rachel and Tim finished their meal and eventually made their way to the parking lot.

"So, how about coffee at my place?" Rachel asked, shyly looking up at Tim, with strands of her thick red hair falling slightly over her face.

"Yea, I guess we could do that." Tim said, trying not to sound too eager.

The couple took Rachel's car back to her place, eventually turning up a long, winding gravel driveway surrounded by thick woods. When they finally pulled up to her home, Tim gave a low whistle of appreciation.

The house was a log cabin, two-story, with a wide wrap around porch. The windows were huge, each easily double the width of a traditional window. The front garden was neat and well-trimmed, and the house looked warm and inviting.

Taking him gently by the hand, Rachel led him inside, instructing him to make himself at home while she brewed the coffee. After looking around the living room for a bit, Tim eventually sat down on one of the large black leather sofas, legs stretched out in front of him.

Rachel appeared in the doorway that separated the kitchen from the living room, two large coffee mugs in hand. Tim rose to help her, taking one of the coffee mugs and adding cream and sugar to it when Rachel had brought out the little tray.

After enjoying a couple sips of coffee, Tim finally gathered up his courage to make the first move. He leaned towards her, his one hand sliding around her waist as the other slid up her back, pulling him towards her. She moved closer to him, her hand running through his hair as she passionately kissed him, her tongue intertwining with his. He ran his hand around her waist and up to her breast, needing her on top of her shirt before plunging his hand into her shirt to cup her tit and gently rub her nipple with his thumb.

Making small, mewing noises in her throat, Rachel leaned back to lay on the couch, bringing Tim with her hands intertwined in his hair, nibbling and teasing his lips with her mouth and tongue as she slowly grinded her hips up into his crotch. Tim rested his weight on his elbows as he matched the movement of her hips, his breath quickening against her neck as he licked and kissed the sensitive skin there.

Tim couldn't believe his luck. This blind date had definitely gone better than his expectations, and now he had this absolutely gorgeous girl, pawing at him, practically ripping his clothes off. Oh god, she felt so good underneath him... Oh god, her lips.... Oh god, he was coming!

Tim's fingers dug into Rachel's side, his head tucked into her shoulder as he bucked his still-clothed hips into her, grunting incoherently. After a few seconds, he moved to sit up, still breathing heavily and looked down at Rachel.

Still lying on the couch, Rachel looked up at Tim with a look that was one part disbelief, one part disdain. "Are you fucking kidding me?" She asked, her voice dangerously low. "Did you really just...... are you fucking kidding me right now?!" Her voice rose with her temper, her blue-green eyes now green in her anger.

"I'm...I'm so sorry.... That hasn't happened to me in, god, I don't know. Forever?" Tim stammered weakly, ashamed that the evening's mood had been spoiled by him. "Rachel, I.... I can make it up to you. I've always had great stamina, please, please let me prove it to you, make it up to you." he rambled, smoothing his hair back from his head one-handedly.

"Un-fucking-real!" Rachel, her eyes narrowed in disgust, yelled before fixing her clothes and marching out of the room to the bathroom.

Sighing loudly to himself, Tim chastised himself for being such an idiot. He couldn't believe he had blown his load so quickly. What was he, a 14 year old again?! "Shit!" Tim muttered under his breath, sitting up and cradling his head in his hands. He was so lost in his thoughts he didn't notice Rachel walking back into the room, arms crossed across her chest.

"You know what, Tim? I'm gonna give you one more chance. But this time, I think it'd be better if we did things my way. We tried your way, and that really only worked out for you, don't you agree?" Rachel asked, her voice innocent.

Tim couldn't believe his luck, there had to be some guardian angel pulling favors for him big time! First, he actually gets a blind date from heaven, then blows it, and now he's actually getting a second chance?

"Yeah... I mean, we could absolutely try it your way, whatever you say. Just give me a chance to prove to you I can last longer than a two pump chump." Tim quickly stammered, still unbelieving that this knockout hadn't kicked his ass to the grass by now.

"Hmmm, well, we'll see. How about this? You come upstairs with me, and so long as you do everything I say, I'll give you that second chance." Rachel said, with a small smirk on her face.

Hesitantly, Tim agreed. "Ok, so long as it's nothing dangerous or crazy." He realized what a precarious position this put him in, and it really sunk in that he really didn't know Rachel all that well. However, he was too eager to prove himself to her that he didn't over think it, and stood up to follow her to her bedroom.

Eyeing her ass as she moved slowly, deliberately up the stairs, he couldn't help but feel elated that she was still interested in him. He followed her down a long, carpeted hallway, taking a brief moment to survey his surroundings. The hallway had four doors across from each other, and one larger door, undoubtedly the master bedroom at the end. The carpet was lightly colored, light enough to make the dark wooden doors stand out but not light enough to showcase every spec of dirt.

As they got to the end of the hallway, Rachel stopped to turn around and look at Tim. Staring straight into his eyes, she asked him, "Are you sure you're willing to do anything to prove to me you're not some little boy?"

Tim's imagination was too vivid and aroused for him to really consider what he was getting himself into. "Yes, definitely yes." His eyes moved up and down to enjoy every visual detail he could soak up.

The jeans she had paired with the green V-neck were a dark wash, tapered to her legs and so tight they looked almost painted on. Her legs were strong, but not overly muscular, and she had paired the jeans with short black boots that had a high enough heel to make her almost even with his height. The V-neck highlighted her full chest, and the slimness of her waist and came down at the perfect length to meet her hips. Her hips were wide enough to give her the ever-popular hourglass figure. Moving his eyes upwards to her face, he drank in her milky, smooth skin; her small almond shaped eyes, and full lips.

She smiled, pulling him by the hand closer to her and placing one hand on the back of his neck. Almost chastely, she kissed him, running her lips across his before gently probing his mouth with her tongue. Restraining his urges, Tim wrapped his arms around her waist and kissed her lightly back, trying to get a feel for the tempo she wanted to set.

Pulling away from him, she reached behind her to open the bedroom door, revealing a large bed, nestled between two night tables. Leading him to the bed, she instructed him to strip and lie down in the middle of the bed. Without hesitation he stripped down fully and lay down, one arm angled above him head, the other resting on his lightly toned stomach. Rachel pulled her shirt off over her head, letting it fall to the floor as she stared down at his already hardening cock before unhooking the clasp in the front of her bra and letting the straps slide down her arms. Her fingers quickly undo the button of her jeans, and she reaches down to unzip the side of her boots before taking them off and stepping out of the jeans.

She stepped closer to the bed, hands on her hips, letting her eyes graze her body. A small scowl appeared on her face, and for a moment Tim felt panicked. "Something wrong? Don't like what you see?" he said quietly, hoping that whatever was wrong could be resolved quickly.

"No, no. I very much like what I see, but you see, I'm wondering if maybe there's a way we can better ensure that you behave yourself and last for me." She pondered aloud.

Smiling evilly, she walked over to the top right side of the bed. "Give me your arm," she said, reaching for it. Unsure, Tim put his wrist in her palm, and she reached under the fitted sheet to pull out a leather cuff. Deftly wrapping the fleece lined cuff around his wrist, she buckled the restraint and move down towards the bottom of the bed, reaching underneath the fitted sheet again to buckle his ankle in another cuff. She moved around the other side of the bed, repeating her movements until he was restrained to her liking. Moving back around to the foot of the bed, she put her hand over her mouth and inspected her handiwork. Tim laid there, motionless, his pulse racing in his throat, his mouth dry and unsure of what to expect next.

Finally making eye contact with him, she arched one eyebrow and proceeded to crawl up the bed to him. His eyes were focused on her tits, hanging and jostling with her movements. As she reached his stomach, she lowered her chest as she continued crawling up to him, tracing her hardened nipples up his abdomen. He inhaled softly, wishing for more contact with her body but savoring the teasing immensely. When she reached his face she kissed him, nibbling on his lower lip before her tongue found his. Rachel lowered her body onto Tim's, grinding into him, and letting him feel every inch of her soft skin brushing against his. Tim ground his hips up into her as much as he could. God, her body felt fucking incredible. Before he could stop himself, he began shaking and quivering. Sensing he was close, Rachel lifted herself up off of him and sat on his legs, her hands on his hips.

"God, Tim, you're like a little teenager," Rachel laughed. "Geez, I really am gonna have to teach you patience, aren't I?".

"Rachel...I....I just can't believe how amazing you are. I mean, my god, your body is just fucking incredible." Tim said in his defense.

"Hmmm, maybe that's the problem. Maybe looking at me is just too much for poor you to handle." Rachel said, looking down on him naughtily. She lifted herself off his legs and crawled over his prone body to the night stand. She opened the drawer and took out a blindfold. She slid it over his head, adjusting it so it fit properly and Tim couldn't see a thing.

"Is that better, Tim?" Rachel asked teasingly. "I figure now that you can't see me, you should have an easier time lasting."

Tim was nervous. He'd never been tied up before, let alone blindfolded. This was completely new to him. However, his hesitation was overruled by his desire for her. He felt the bed move as Rachel moved down between his legs, using her knees to force him to spread his legs out wider to accommodate her. Leaning down, she grabbed his cock firmly with her hand, and proceeded to lick and suck just the tip of it lightly until she had coaxed the first drops of pre-cum out of it. She then licked slowly up and down his entire length, until he was making small noises in his throat.

"Are you sure you want this, Tim?" Rachel asked, stroking his cock with just enough pressure to make him thrust his hips as far as he could eagerly. "If you don't, just say the word and I'll untie you, and you can just walk out of here, no questions asked."

Tim swallowed a couple times, his dry throat making speech difficult. "Yes." He whispers, barely able to believe his own answer.

Rachel giggles. "Are you sure you really do want this?" she asks again, the tone of her voice suggesting she already knew the answer.

"Yes, please." Tim whimpers. He couldn't think straight, not with her hand slowly stroking his well-lubed cock. All he knew is he didn't want her to stop.

Satisfied with his answer, especially with the "please" that followed it, Rachel smiled to herself. Tim seemed like a lover who would be eager to pleasure his partner, and she knew that trait was rare to find nowadays in a man. With a little training, Tim could be the perfect playmate for her. He already had naturally submissive tendencies, otherwise she would have never been able to convince him to go this far. Now, it was just a matter of conjuring them out of him.

She lowered her head and proceed to continue licking around the sensitive head of his cock as her hand kept slowly going up and and down his thick length. As she climbed up towards the nightstand, she grazed her nipples up his stomach and chest, eliciting a small sigh from Tim. When she reached his face, she kissed him, expertly teasing him with her tongue, while grinding her body against him. His rock hard cock was pressed up against her smooth, hairless pussy, and he could feel how wet she was becoming. Before the sensation became overwhelming for him, Rachel quietly laughed and sat on his chest, reaching over to the nightstand to take out a few things she needed. She wanted to make tonight something Tim would never be able to forget. She grabbed a vibrating cock ring, a clear cock sleeve with stimulating bumps all down the length of it, and some lube.

She lubed up his cock generously, twisting her hand around him until he was moaning and panting before sliding on first the cock ring, then the sleeve. Rachel turned on the vibe on the cock ring, knowing the pulsing vibrations would add to his pleasure as much as it would hers. Tim was quiet; unable to see what was happening to him he was reduced to guessing and listening. Rachel moved to position her hips over his now aching cock. She grabbed him with one hand, and slid down slowly, enjoying the added stimulation of the sleeve. Bending forward, she placed both hands on Tim's well-defined chest as her wet pussy swallowed him, inch by inch. Tim let out a low moan, his hands instinctively reaching out to grab her hips but restricted by the restraints. Unable to do more, Tim started moving his hips, sliding himself in and out of Rachel's tight hole as much as he could. She slid upwards, allowing him to have this moment of savoring being inside of her, before sliding back down and pinning his hips to the bed.

"Now Tim, ", chided Rachel, "we can't have you getting too excited again. You wouldn't want to disappoint me again, would you?" Her voice was light and innocent, yet he could sense that she wouldn't stand for being let down a second time. "Now you keep still, and if you're very good, maybe, just maybe I'll let you cum again." Her words made Tim a little anxious. If I'm good, maybe she'll let me cum again?? He couldn't quite believe what he heard, but was too turned on by everything he'd felt so far to think too deeply about it.

He held his hips as still as he could as she slid down his cock, enveloping it inside of her warm, now soaking wet pussy. God, she was so fucking tight. She slid up and down his cock a couple times before grinding her clit into his pelvis. She leaned forward enough to allow her nipples to sweep his chest with her every motion, moaning as she adjusted to his considerable girth. Tim could feel the bumps of the cock sleeve massaging his cock as she moved, the vibrations of the cock ring adding to the pleasure.

"Oh, fuck baby you feel so good!" Rachel cried out, her nails now digging into Tim's arms as she got closer and closer to orgasm.

Finally, with a loud moan, and a series of wordless noises, Rachel came, sitting upright as she firmly ground her clit on Tim, her fingers rolling and playing with both nipples, heightening the orgasm.

Her moans of pleasure, combined with feeling her pussy tighten around him and the sensation of the cock ring was almost too much for Tim. He began to grunt and moan loudly, his hips straining to get the friction he needed for release. He felt the build- up coming, and was just at the point of going up and over that sweet edge when Rachel hopped off of him. He came so close that all he could do was wordlessly voice his frustration, as the familiar ache of blue balls came over him.

Breathless, he pleaded with Rachel. "Baby, please, I'm so goddamn close, oh my god, please Rachel. I'll fucking do anything, just please make me cum." Upon hearing his pleas, Rachel couldn't help but giggle to herself. If only Tim knew what levels of desperation he had yet to reach.

"Oh, but honey," Rachel said in an oh-so-innocent voice, "I'm not even close to being done yet."

Fuck, Tim thought. He was so close his whole body was shaking, but he was determined to fully satisfy her, especially after his earlier performance.

Rachel climbed up the length of his body until she reached his face. Taking care not to disturb the blindfold, she positioned her pussy right above Tim's lips. Tim could almost taste her sweetness, and reached up with his face, eager to taste her.

"Ah, ah, ah," Rachel chided playfully. "Not so fast!" She spread her legs out as far as she could, careful of hurting his arms. Reaching between her milky legs, she began to rub her clit right above Tim's face. Able to hear what she was doing, but unable to see made Tim's blood pump faster and his already aching cock swell more. He could hear her fingers going over the slickness of her clit, her whimpers and moans driving him crazy with lust for her. After what seemed like an eternity, she finally lowered her hips enough to let him lick and tease her clit as she held onto the wall and a handful of his dark, curly hair. Lightly flicking his tongue against her clit, he then slowly, deliberately licked as much of her pussy as he could reach, every so often coming back to her clit.