Taking My Princess' Cherry

Nick was nervous - he had fantasised about this day for a long time - he was sure it was many men's fantasies and this wasn't something he had ever imagined he would have the chance to do. He had met Nat, his gorgeous eighteen-year-old princess, a few weeks ago and they had chatted. At first it was just about his writings but she intrigued him and she seemed fascinated and interested in him. She was younger than him (eighteen compared to his thirty-two), and he had no intentions towards her other than just to chat - but the more they chatted the more they seemed to have in common and she seemed interested in submitting towards him.

As things went on Nat seemed to open up more and more, she found boys her own age too immature, she liked talking to more experienced men. Nick wasn't surprised when she said she was interested in playing with him but his heart skipped a beat when he told him she was a virgin and asked him to take her cherry.

He thought about it for a while. He was older than her, was it right? Would it be something she regretted later in her life that it wasn't with someone she loved? He could understand her reasons - she wanted someone she could trust, wanted someone experienced and she seemed to think that was him. He was sorely tempted - he had never taken someone's cherry before. She was gorgeous and he decided to talk to her some more first.

He put his worries to her and they discussed it and the longer they talked the more he was sure she had a sensible head on her shoulders and that she knew exactly what she wanted. Finally deciding he agreed he would be her first. They met briefly for a social chat and got on well in person - she was more gorgeous than he had though from her photos. Her flaming red hair always caught his attention.

They arranged to meet one afternoon to try and be naughty and see how it went - he wasn't willing to fuck her yet - he wanted to give her a chance to change her mind after playing so he was going to teach her how to give a blowjob. That session went amazingly well - she was a quick study and her technique kept improving the entire time until Nick exploded in her mouth. He kissed her hard afterwards then fingered her to a couple of orgasms before she asked to suck him again. That afternoon went amazingly well and he exploded in her mouth twice. She confessed afterwards that she had been nervous about swallowing his cum as her friend had said it didn't taste nice but she loved it. Grinning from ear to ear Nick had eagerly arranged to go to her flat the next time they were both off.

The days passed agonisingly slowly until the day dawned bright and clear - showering and shaving he made sure he was clean and fresh then drove round to her flat. She let him in to park and met him downstairs - she kissed him and he could feel her nerves and arousal. She was wearing a tight black dress that showed off her curves. Sliding his hand under he could tell she wasn't wearing any panties, just as he had instructed her. She let out the sweetest little whimper as his fingers teased her and his gentle suggestion that they head upstairs was met with eager acceptance.

They made their way inside and to the beginning of the first flight of steps when Nick's naughty side took hold again and without a word he pulled her dress up and over her ass. Her delicious shaven pussy and gorgeous ass were now on display to the whole world. They had three flights of steps to go up and she walked the whole way proudly showing off what her Sir was going to fuck later.

She fumbled with the keys to the flat and was obviously a little more nervous when she could hear voices from the flat next door but quickly she had the door open and Nick pushed her inside. The door was kicked closed behind them and his Princess locked it tight. As soon as she was done Nick had her up against the wall, fingers around her throat as he kissed her, his other hand between her legs teasing her soaking cunt as she sighed and moaned in his grasp.

Happy that he had excited her to the point where she was in need of her first orgasm he stepped back and she smiled that dark lustful smile that seemed so wrong on such an innocent face. That contrast has his cock as hard as iron in his pants and as she led him through to her room he found the butterflies in his stomach a hurricane. He stripped her slowly until she was naked then after stripping off his shirt he pushed her onto her back on the bed and spread her legs. She wiggled up the bed until she was against her pillows. Gently kissing the insides of her thighs he kissed his way higher, stopping every now and then to sink his teeth into her soft skin. Each time he did she whimpered - the pain was such a turn on for his slut.

Finally at the apex of her legs he licked her virgin pussy, tasting its sweetness as he slowly ate that beautiful slit. She ran her fingers through his hair as he expertly teased and aroused her beyond the meagre experiences she had enjoyed so far. This was to be her cherry day and he was going to enjoy every sweet second of it. More than that - he was going to give her a day she would never forget.

His tongue slid between the folds of her pussy to find her clit, teasing that young nub until she cried out, asking her Sir if she could come. With his permission she came hard - the first time a man had ever eaten her sweet pussy to orgasm.

Standing up slowly Nick slid out of the rest of his clothes. He was naked and very, very hard. He looked down at her sweet innocent body and asked her one last time if she still wanted this, if she was still happy to go ahead. She eagerly nodded and he pushed her legs wide apart. He pressed the head of his shaft to her virgin hole and slowly began to push.

It was the tightest pussy he had ever tried to enter. His thick cock split her lips apart and he looked down for a brief moment to enjoy the view - he had barely got the head in and she was shaking and trembling with the pain of him penetrating her. "Are you okay? Do you want me to stop?" He asked looking down in concern.

"No, keep going!" she gasped...

So he did... slowly and purposefully thrusting forwards, breaking her, splitting her and filling her. Soon his cock was fully inside her sweet, tight hole and she had her arms round him. "You're mine Princess." He whispered in her ear. Giving her a few moments to get used to his thick shaft deep inside her. He slowly pulled almost all the way back out, looking down to see the slickness on his cock and the evidence of her broken virginity.

He began to fuck her, using every skill and technique he had picked up over the years - lifting her hips slightly to change the angle of his thrust. Finding that sweet spot inside that gave her the most pleasure as he filled her deeply. Her first fuck and he was going to make it her best. His shaft was an average length but thicker than most. He used that to his advantage filling her over and over, aiming for the best parts inside her. The initial pain of the first penetration quickly past and he saw her eyes fill with lust as his cock fucked her.

Taking at slow as he could he let her experience the pleasures of a shaft stretching and filling her to completion. His cock drilled slowly in and out of her. Long purposeful strokes that drove her higher and higher in pleasure until she begged to cum again. If Nick was honest he was surprised - he knew she was a horny little thing but had thought it would take longer and more practice to find how to make her cum on his shaft. He willingly gave her permission and watched in delight as the first orgasm this beautiful creature had from sex was whilst impaled on his throbbing shaft.

She was so tight but wet at the same time, deliciously warm and as he quickly fucked her to a second orgasm he was struggling to hold back now. He lifted those ankles to his shoulders and drove his cock in and out of her harder and faster. She peaked again, crying out her third orgasm to the empty flat (and listening neighbours no doubt) as her newly opened pussy felt the full force of Nick's hard thrusts. As he came for that third time Nick bit down on her breasts, viciously hard making her cry out in pleasure and pain, buried his cock deep inside her and exploded - filling her sweet innocent pussy with stream after stream of his thick creamy cum.

Her first oral, her first orgasms from someone else, her first fuck and a pussy filled to the brim with her Sir's cum. And that was just the start.

Slowly sliding out of her Nick took her in his arms and kissed his Princess gently. Checking she was okay and that it had been what she had been hoping. She nodded affirmations of everything and the look of bliss on her face was enough to reassure him that he had done the right thing. He kissed her softly and let her catch her breath then slipped away to clean up the little bit of mess that remained.

Returning quickly he slid onto the bed next to her and started playing with her gorgeous full breasts - teasing the nipples, making her whimper again. He guided her hand to his cock and watched those little fingers wrap around his semi-hard length. She stroked and teased it and in no time at all was back to full hardness. She leaned down and wrapped those luscious lips around it. Taking a handful of her red hair he pulled her head up so she looked into his eyes as she sucked his meat. He loved that look of pure pleasure and lust in her eyes as she made her Sir happy.

Considering this was only her third blowjob she was incredibly good and had him throbbing and hard in no time at all. This time he put her on all fours to fuck her and started thrusting in from behind. Whether it was the bed or something else it wasn't working for both of them (it does now) so he got her to straddle him and as she lowered herself onto his thick cock she groaned in appreciation as it filled her. This worked well and within a few minutes she was riding him to another orgasm and another as she ground herself down onto his hard cock. Several orgasms and position later he came deep inside her again and they curled up once more - giving her newly broken in pussy a chance to recover.

She was truly his now and he had something for her. Leaving her horny, aroused self in the middle of the bed he walked over to his bag and drew out a collar. It was pink and had glittering studs and he fastened it around her neck as she smiled in obvious delight. He then pulled out the lead and fastened it on. It had a lovely leather handle that as he put her on her knees he knew what he was doing to do with it.

His little fucktoy loved pain; it turned her on nearly as much as his tongue, fingers, cock and naughty mind. He had promised her a proper spanking and she was going to get one. He spanked her ass hard. His bare open palm slapping down onto each cheek over and over again as she whimpered under him. He could tell she was getting more and more turned on. He used the end of the leash to whip her ass making her cry out in an incomprehensible mixture of pleasure and pain. Her ass had turned crimson now. He grabbed the cuffs from his bag and fastened the soft leather and chains around her wrists. Flipping her onto her back he pressed the ball gag to her lips. She eagerly took it into her mouth. With her bound and gagged he gave her permission to cum whenever she needed to and then rammed his length inside her.

So far his taking of her had been fairly gentle and restrained but with their stop signal agreed he was going to use his little toy how he needed and wanted to this time. Teeth bared he savagely bit her glorious breasts as he rammed his fat cock in and out of her newly taken hole. He pounded her down into the bed, slapping her tits, kissing and biting her all over as he thrust hard, deep and brutally fast in and out of her pussy. She was turning red; he could tell that she was almost constantly orgasming every few minutes from his relentless assault on her body. The final straw was when he wrapped both hands around her throat and squeezed. With five hard, sharp, full thrusts into her vulnerable, innocent body and the look of lost need on her face he exploded inside her again.

Collapsing down next to her after emptying his full balls inside her he quickly removed the gag allowing her to breath her amazed thanks to him and he cuddled her in tight. Again checking that she was okay after the roughness of that fuck. She simply thanked him and told him that she loved it.

After a few minutes of slowly coming back down from their highs she started teasing his cock again - quickly getting him to full hardness again. This time he remembered something that she had told him about her fantasies and he took the lead in his hand and led her through the house. First to her parents' bedroom where he pushed her on her back and spread her legs wide. It seemed even naughtier taking this freshly fucked virgin on her parent's bed but she was such a hot little slut that even though he was Sir and Dominant at that point he would have done anything for his Princess. He pounded her hard again and she came - one of the hottest orgasms she had all day as she spoke the dirty words that he loved to hear.

Not cumming himself he stood and pulling on the lead took her, shaking legs and all, through into the lounge and kitchen area. He squashed her onto her back on the sofa, tucked into a helpless ball and fucked her again until he emptied himself a third time inside her.

They were both wearing out now. This was the most he had fucked in years - let alone the fact that this was the first time her pussy had ever had a cock inside it. They collapsed onto her bed and he took the restraints off her but left the collar on. She looked so appealing in just the collar on her bed. His pretty princess, taken, used and abused and loving every minute.

He raised himself over her and spent a good few minutes tenderly kissing and caressing her. Feeling himself grow hard once more. He entered her slowly. She was tender and beginning to get sore inside from the hard pounding so he went slowly and gently and pushed her to a couple more orgasms before pulling out and spraying his cum all over her pussy.

Spent and worn out he lay next to her, taking his princess in her arms and thanking her for the honour she had done choosing him. He would remember this day forever. She kissed him softly and said that it had been everything she could have hoped for and more. They lay that way for a while and Nick wished it could have been an eternity but he slowly rose, dressed and kissing her one last time left quietly out the door, leaving his Princess to recover from her first full play session with Sir.