No More Rules

For Craig, it had been the last straw. At 25, learning that his 18 year old sister was having sex on a regular basis was the final humiliation. Craig had always kept a strong moral viewpoint. He would not beg for sex, he would not degrade himself and he would most certainly not have sex with a prostitute. Craig was not unattractive; he simply suffered from a severe lack of confidence and ability to speak to women. Many assumed he was gay, but Craig knew this was not the case. He adored women, but it was this adoration that left him unable to communicate with them on a primal level. Add to this his rules and this had left him as a 25 year old virgin; but now this had to change. Egged on by his friends, Craig had learnt of a brothel run from one of the nearby suburbs. Far enough away to make sure no-one would recognize him but close enough to get to without drawing suspicion. He had no idea how much was charged at one of these places, so he saved up enough for all eventualities. He didn't want a show, he just wanted to know what it felt like to be with a woman, get his rocks off and get on with his life. He had become obsessed; he needed this out of his system.

The day arrived and Craig had a clear schedule. He nervously got in his car and drove down to the house that his friend had told him to go to. This friend had memorably told him he needed to "bring money and your dick, the chicks supply the condoms." Despite the rather vulgar use of language, Craig was happy to receive any advice.

Maria was having a bad day. She was tired of the middle-aged men that frequented her well maintained body. Often they would shout obscenities at her, calling her a "dirty slut" or a "horny bitch." She never understood why the men were so eager to degrade her. Whether it was because they were so unhappy with themselves, that the only way they could fuck a woman like her would be to pay for it. It was mid-afternoon; she'd already had two dirty old men sweat all over her, then churn their old watery splurge out on to her tits. Why couldn't they just cum in their condoms? Why did they always have to put it on her? The worst part about it was Maria had actually woken that morning feeling seriously horny, yet nothing these men had done had bought her remotely close to release. Trying to forget her start to the day, Maria stepped out of the shower and walked naked through the hall to her quarters. She slouched in the big armchair in the corner of the room. Couples would use the chair to sit in whilst watching their respective partner fuck another woman. Maria spread her legs and slowly rubbed her fingers over her warm, moist cunt. Her free hand ran over her thighs, then her neck and finally her breasts. Maria was fairly worked up now and she was starting to gasp a little. As her release finally came close the door swung open and her boss Mrs Albert burst in.

"Sorry love, we've got a new one and all the other girls are tied up," she said in her thick Yorkshire accent.

"Fuck, just give me two minutes!"

"Save it for the feller ay lass, come on don't leave him waiting."

With that Mrs Albert walked over to Maria and dragged her out of her chair.

"No please, just let me finish," cried Maria as Mrs Albert yanked her hand from between her legs and pushed her towards the next outfit that was laid out neatly on her bed. Maria let out a mock sigh as Mrs Albert watched her put on her lingerie with a wry smile.

"You really are my prize asset dear; your problem is none of these men realize they don't know how to handle a looker like you. What's the longest a guy's ever lasted inside that cunny of yours? It can't be more than a few minutes."

"Piss off" Maria replied as she gave Mrs Albert a jovial shove then swanned out the room.

Craig stood in the hallway, his heart beating in his ears. All he wanted to do was bolt back out the door and wank off into a Kleenex in the privacy of his own bedroom. Craig could hear the muffled cries of the customers currently being worked on by the other girls, despite the effort that had been put into sound-proofing the walls it was clear when a customer reached his climax. Craig was startled as he felt someone tap him on the shoulder. As he span round he cast his eyes over Maria, she stood before him with her hands on her hips.

"Oh shit," Billy whispered.

"What's wrong? Don't like what you see?"

"No no, it's just, I didn't expect you to be so; well, beautiful."

In that moment Craig cringed at how corny that line sounded, and couldn't believe he hadn't relieved himself before heading over. He knew it would be over in seconds.

"You don't need the lines with me, just make sure you can pay" Maria told him sarcastically. "Follow me."

Maria led Craig up the stairs. He watched her ass sway from side to side, he knew she was putting it on, but it was having the desired effect. Especially with the long legs that carried her up the stairs. She was a dream.

She strolled into the room she had previously occupied, staring longingly at the wet stain on the armchair, reminding her of just how close she had got. She told Craig to remove his clothes then ran through the various services she was willing to supply. Craig's hands shook with nerves, making the unbuttoning of his shirt a bigger ordeal than it should have been.

"Come here, let me do that for you," Maria walked across and unbuttoned the rest of his shirt. She could hear his staggered breaths, she could hear his nervousness. The men usually breathed heavily through arousal, but this was different. She had an idea what was wrong.

"Shit you're a virgin aren't you?"

Craig was dumbfounded, he could not figure out how she knew.

"Oh come on you're not gonna last two seconds!"

Craig didn't understand, he though she would probably want this over as soon as possible. Maria put her hands between her legs and gave herself a quick rub; she really was still very horny.

"Okay I'll do you a deal, usually this is extra but I really need to get fucked for longer than a minute. I'll give you head first, so that you're not full of spunk, then when you've recovered enough you can fuck me; does that sound good to you?"

"I can't afford all that" Craig uttered.

"Don't worry, I'll only charge you for the fuck."

Craig could not believe his luck; his erection was throbbing beneath his boxers. He had to give it a quick rub. Maria took this as his answer and removed the rest of his shirt before yanking down his boxers and freeing his cock from its prison. Maria was pleased to find he was clean, she could never understand how some men turned up without even showering first. She was also pleased to see it had not been an optical illusion, Craig had a pretty large cock, she estimated he had to be pushing around eight inches, but with a slight curve upwards.

She took it in her hand then gave it a slow rub. Craig gasped as a woman held him for the first time. He reached for his wallet and quickly handed over the cash, saved specifically for this occasion. Maria counted it in front of him, then locked it in a draw and returned to his dick.

"You promise you've never been touched? You've never put this in a girl's mouth, pussy or ass?"

Craig nodded "I promise."

With that Maria took him into her mouth bareback, forgoing the condom despite house policy. Craig cried out in delight as she lightly sucked on his virgin cock, swirling her tongue round the tip before working on his frenelum. She took hold of his balls then slowly worked them between her fingers.

Abruptly she popped him out of her mouth and asked "you enjoying this hun? You getting close?"

"I'm close, I'm real close, please please keep sucking" Craig cried.

With a smile she took him back into her mouth to finish him off. She sucked a little harder this time and ran her tongue forcefully over the underside of his cock. Craig shuddered and she felt him flex. She looked up at him and Craig let out a quiet moan, indicating his encroaching orgasm. Maria closed her eyes and smiled to herself as she made another virgin cum.

Craig cried out, his body tensed then his ejaculation pulsed through him. His semen splashed the back of Maria's throat. She swallowed the first few shots but had to take him out of her mouth, she wasn't expecting quite so much cum. She continued to jerk him off, allowing him to cum on her face, amused that only moments before she had been complaining about this particular practice and was now forcing the guy to unload onto her pretty features.

Craig looked down at the familiar sight of semen on skin, but this time it wasn't his hands that were dripping his seed, for the first time it was the pale, lightly freckled skin of a woman. He breathed heavily as Maria swallowed what was in her mouth and looked up at him.

"Did you enjoy that honey?" she asked.

Craig nodded again making Maria smile. She got up and moved to a chest of draws and removed some wipes to clean up her face.

"Okay then babe, as we're waiting for you to recover, d'ya want a closer look at me?"

Craig stuttered back "yes... um, yes please."

Maria took his hand and led him to the bed. She lay down and opened her legs for him to climb between. Craig sat back, hesitant to move any closer.

"Come on get in there, you're not getting anywhere from back there."

Craig slowly moved between her legs. Although the room was fairly dark he could still make out the folds of her vagina spread before him. Initially he was struck by the heat coming from her loins, he never expected her to be this aroused or for it to be quite so warm. She instructed him to have a feel around, Craig clumsily held the palm of his hand over her snatch and he instantly felt how wet she was. She urged him to go further by using her hands to open herself up to him. Craig poked his index finger inside her, normally this would be quite awkward but Maria's aroused state allowed him to slip inside and feel around. Craig was amazed, just the thought of having his penis inside this warm, moist space was enough to speed up his recovery.

"Now take it out" Maria ordered, "and give it a taste."

Craig was hesitant, but he wanted to learn, and she had just swallowed a huge amount of his ejaculate. So feeling he should reciprocate, he rather comically sniffed his finger then put it in his mouth.

"What do you think?"

"Not too bad, I could get used to it" he replied, with an assurance Maria had not yet heard from him. She looked down at his crotch and noticed his now almost fully erect penis pointing towards her. She wasn't ready yet, so she knew she had to get a move on.

Maria leaned forward, grabbed his head and forced it into her lap, no more teasing. She told him to start by licking her slit and she would open herself up and point to the areas she wanted him to focus on. As he moved around she asked him to change the intensity of his flicking tongue, as some areas needed it more than others. For now Maria rubbed her clit, she wanted to teach this guy, but she wasn't letting him loose with her prized possession just yet.

Maria let out a grunt. "Oh fuck, get up now."

Craig was a little worried, what had he done? He though he was doing okay, he didn't think he was hurting her.

"What's wrong, did I do something I wasn't supposed to?" he fretted.

"No no, I need you inside me now, no more foreplay" she replied.

Maria reached into her bedside draw and pulled out a condom, tore off the wrapper then grabbed Craig by the hips and slipped the latex sheath over his erection.

"Ready to become a man?" she said with a wicked smile.

Switching places she climbed on top of his virgin body and placed him at her entrance. With a smile she slowly worked her way down his cock, making him shudder with pleasure. For everything he expected, he still couldn't comprehend the feeling of her pussy wrapped round him, it was incredible. Maria worked her hips first, moving him around inside her, then she worked him up down, letting him admire her tits as they bounced around in front of him.

"Okay sweetie, I want you to take me from behind, you've seen porn right? You know what a mean?"

Craig nodded as she slipped off him and got on her hands and knees.

"Just take hold of my ass, line up your willy and push forwards."

Craig did as he was told and was once again engulfed in her womanhood. A few minutes passed with him thrusting into her pussy, much to Craig's delight. His stomach was smacking into her ass making it jiggle a little and his balls bounced around, occasionally slapping the top of her mound. He ran his hands over her back, stroked her face and grabbed her thighs in quick succession, enjoying being able to feel a woman sexually, loving the feel of skin on skin.

Eventually it became all too much, Craig started to involuntarily grunt. Maria was not letting another punter finish before she at least got one good orgasm. Her hands went back to her clit and to her surprise this instantly did the trick. Her pussy flexed round his dick, Craig could not believe it could feel any better, but this really did push him over the edge.

"Keep going, please keep going, I'm almost there! I'll take a hundred pounds off the bill if you cum with me."

It was no use, Craig had no control now. The base of his cock vibrated and the tension built and built then suddenly Maria bucked in front of him. He held her up and pushed as far as he could inside her and with an almighty moan, ejaculated inside a woman for the first time.

Maria was elated, she finally had her release. She could feel the warmth of his semen inside her and this pushed her into another orgasm, right off the back of her first. Despite his sensitive state, Craig stayed inside her, gently rocking backwards and forwards to feel her pussy grab hold of his cock, squeezing it, trying to force out more cum. Eventually he stopped tensing up and the flow of semen stopped. Maria climbed down from her second orgasm and Craig slipped himself out. He stared down in wonder at the load he had deposited inside the condom. This wasn't just any load, that semen had been drawn out of his body whilst fucking a woman's pussy. He could not get that thought out of his head, and smiled to himself.

"Someone's pleased" Maria joked. "You probably should be though; you know you made me cum right?"

"You're joking? That wasn't fake?"

"Sweetie, when a pussy ripples like that round you, it means she came. Look at the mattress." He hadn't noticed before, but there was a distinct dark patch where Maria's juices had leaked out onto the bed. "Honey I came; twice."

Maria threw on a robe and left him with some tissues and wipes to clean himself up. He couldn't stop smiling as he threw the used condom in the bin, cleaned himself up, put his clothes back on and headed outside. Just before he left Maria called to him.

"Will we see you again?"

"Definitely" Craig replied.

Craig jumped into his car and let out a long breath then drove off. "Why did it have to be so far away" he thought, "I can't wait until I'm home." He pulled up next to a wooded area, got out of his car, found a hidden enclosure and masturbated whilst thinking of the amazing experience he had just had. As his seed splattered over the plant life he thought to himself, "it may have taken 25 years, but wow was it worth it!"

He wearily walked back to his car and drove away, trying to work out when he could afford to go again.