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A few weeks earlier, just after the original sex education lesson:
"So what was your sex ed. like today?" Oliver asked Joanna as they sat in her room.
"Pretty dull. Lots of wear-a-condom lectures, don't-get-raped and so on, then we were just meant to sit and talk about sex with the other girls."
"So what did you talk about exactly?" Oliver asking, wondering what a group of girls would say about sex with no guys around.
"This and that. You just want some sordid details from the other girls don't you?" Joanna asked, her eyes narrowing.
"Yep," Oliver replied with a grin. Joanna laughed at his audacity.
"I'm not sure there's too much I can reveal. A fair bit of complaining about men, to be honest. Leah let slip that she really likes giving head. Her boyfriend is probably pretty pleased about that one! Paula said that she likes seeing guys wanking. Oh, and I get the impression that Ruby is pretty kinky. And slightly desperate to find a guy, to be honest. She also hinted that she had quite a porn collection, I reckon she spends a lot of solo time, if you know what I mean."
"What kind of kinky?" Oliver asked.
"All sorts. I get the impression that she's looking for a guy to really take charge, you know? Maybe tie her down and have his way, in whatever other strange fantasies she has. You always have to watch the quiet ones, they'll be the weirdest."
"Why do you sound so disapproving?" Oliver queried.
"Well, I mean each to their own and all that, but it's still odd. You wouldn't catch me doing anything like that, whips and chains and so on."
"I don't think it would actually involve whips and chains," Oliver pointed out.
"Yeah, but you know what I mean."
That night in bed, Oliver could not stop thinking about Ruby. The idea of a real girl who wanted to be tied up and surrender control entirely to her man was like a dream come true. It was definitely not something Joanna would ever conceive of doing. Oliver did not find Ruby particularly attractive - she was not ugly, she was vaguely pretty and large-chested (something Joanna lacked and that appealed to Oliver), but that was because she had a large figure. She was always so quiet when Oliver had seen her that he did not know much about her beyond whatever Joanna had mentioned.
Oliver was definitely curious to find out more about her and her apparent secret passions. He could not really just ask her outright. Joanna had mentioned that she had a porn collection, which was probably hidden in her room or on her computer. If Oliver could be alone in her room, he could surely find out what he wanted. He began forming a plan.
"Hi Ruby," Oliver said when he approached her at lunch a few days later. She was as he had remembered - a roundish, full face with a small nose. She had short brown hair that curled to a stop at the top of her neck and slim modern glasses.
"Hi Oliver," Ruby said as she looked up. Oliver was quite a handsome friendly guy, and would be considered quite a catch. Ruby had been interested in him until he had started going out with her friend Joanna. He had a slightly tall face, with a well-defined jaw line, and he had brown hair gelled into fashionable spikes. He had never seemed to notice Ruby much before, so it was a surprise that he had come over to where she was sat at lunch.
"I was having trouble with our Chemistry coursework and I was wondering whether you could help me."
"Yeah I can help you. Did you want to do it in the library?"
"I thought maybe I could come over to your house or something?" Oliver suggested. Ruby's eyes lit up almost imperceptibly.
"With Joanna?" she asked.
"No, just me." Ruby smiled; she had never had a boy back to her house by himself before. Even if he wasn't interested in her, she was still pleased at the prospect.
"Ok," she said, trying to play it cool, "I'll see you this evening then?"
After school Ruby hurried home to start preparing. She moved a lot of her stuffed toys into her sister's room - her sister was at university for the term - and put on some of her sister's perfume. She changed into some fairly new underwear - just in case, she decided - and wore clothes that looked good, but did not look like she had tried too hard.
Oliver arrived at seven and they began working through the homework. Ruby was concentrating hard on trying to make a good impression, and Oliver was concentrating on trying to surreptitiously look around the room for possible hiding places for pornography, but there were very few. The room had lilac painted-walls, with a single bed and a wardrobe to one side. On the other side was the long desk that they were working at, with a computer on one end and some cupboards and drawers underneath the desk as well as shelves above. Neither of them were very focused on the work.
When Ruby excused herself to go to the toilet, Oliver quickly moved over to her computer - which thankfully was on. He initiated a search for picture and video files, then hid the window from view and left it searching as he took a quick look in the cupboards, wardrobe and under the bed. He did not find anything immediately, and sat back down at the desk as he heard Ruby return from the bathroom.
A short while later, Oliver asked for a cup of tea. He did not really like the drink, but it would take a few minutes to make. Ruby happily agreed to make him some tea. As soon as she left the room, he went to the PC to see the results of the search. Bingo, he thought (and almost said out loud). In one place on Ruby's computer was a neatly organised structure of video files, all with pornographic descriptions on them. Oliver turned off the speakers and began scanning through the videos, playing them and quickly jumping forward through them. He was shocked and delighted by what he found.
The videos all seemed to have the common theme of men dominating women. In most the woman (or women) was tied up (often in some heavy-duty bondage gear). The women were variously forced into sex, caned, spanked, tortured with various nipple clamps and clothespins. Oliver did not have time to look through them all, but he could easily see what Ruby was interested in. He opened up her web browser and looked at the history - sure enough, some of the sites in there were also pornographic, with similar content to her videos. He heard footsteps on the stairs and quickly closed all the things on the computer. He started thinking of a plan as Ruby entered the room with a hot cup of tea.
"Can I look something up for this on the Internet quickly?" Oliver asked a few minutes later.
"Sure," Ruby said, none the wiser.
"Thanks." Oliver went to the PC and opened up the web browser again. He made a play of accidentally opening up the history. Ruby saw some of the links in the history, recognised her own secret browsing habits, and panicked.
"Erm, close that down," she said urgently, trying to keep calm and hoping desperately that Oliver had not noticed some of the titles. Oliver made it look as though as he was trying to close it as he appeared to accidentally click one of the links. Suddenly the screen was filled with images of tied-up women, some being raped (or so the website claimed) and some with obvious cane marks on them.
"I don't know where that came from," Ruby said lamely, her face flushing deep-red with embarrassment. She wished for all the world that the ground could swallow her up. Oliver would know that she browsed the web for this serious sort of domination and bondage. Then surely Joanna would know, and eventually the whole school would know, and Ruby's parents might find out, and her life would be ruined.
"It was in your history," Oliver pointed out plainly, and Ruby felt for all the world that she was going to burst into tears. "It's ok," Oliver added, noticing her distress. He took her hand in his and squeezed it reassuringly.
"Really?" Ruby asked.
"Really," Oliver confirmed. "Come here, give me a hug, it's ok." Ruby embraced Oliver and wiped a wayward tear from her cheek. Oliver felt a pang of guilt, but otherwise his plan was progressing nicely. "Can you keep a secret?" he asked her when they released each other.
"Yeah, what's that?" Ruby said.
"You can't tell anyone, not even Joanna," Oliver warned. Ruby instantly became more curious. What secret could Oliver be willing to tell her but not even his own girlfriend?
"I promise," she said sternly.
"I actually quite like this sort of thing too," Oliver confided truthfully, gesturing at the screen.
"Being tied up?"
"No, the idea of doing the tying up - tying up women, and, well, taking control."
"Oh right. Oh," Ruby said. This was progressing from a nightmare into a bizarre situation. "And Joanna doesn't know?"
"No, she'd never do anything like that, she's far too uptight," Oliver said, trying to subtly compliment Ruby's tastes. "So this can be our little secret then? I'll never tell anyone you like it, and you never tell anyone that I like it."
"Yep, ok," Ruby said, relief washing over her.
"In fact," Oliver continued, "do you have any videos of this sort of thing? I have a lot of pictures but not much video. Maybe we could swap some stuff or something?"
Ruby was stunned for a second. This was becoming unreal. This attractive guy was into the same thing as her, and wanted to exchange porn behind his girlfriend's back. Ruby wasn't sure what to think. "Erm, sure," she said.
"Cool. Shall we get back to the work?" Oliver suggested. Both of them did so, but with their minds totally occupied by what had just happened. Nothing more was said about it during the remainder of the evening. When it came time for Oliver to leave, he leaned over and gave her a peck on the cheek.
"Thank you for your help," Oliver said as Ruby smiled. "I like your perfume," he added as he got up to leave.
Later that night, Ruby lay in bed thinking of that kiss, trying to work out if Oliver was possibly interested in her or not.
The next evening Ruby found a message in her inbox from Oliver. As he had promised, it had photos attached of various bound-and-fucked women. The text of the email was short:
Hi Ruby,
I'm sending the photos like I said I would. If you have any vids that would be cool. If you let me know what you like exactly then I can try and find some suitable pictures for you, and I'm quite interested anyway. I don't get to talk to anyone else about this sort of thing so having you around is good.
Oliver.
PS I've been thinking about you a lot today!
Ruby read and re-read the message a few times, dissecting its minimal content. So her and Oliver were friends, they now had a common (naughty) connection and he seemed to be sending positive vibes. He was still going out with Joanna, but Ruby could still have something going with him, even if it was just emails. She sat and carefully composed a reply:
Hi Oliver,
I've put a video on the email for you. If you let me know what you like, then I can find the right one for you too.
As to what I like: I particularly like the woman being tied up. Sex while they're tied up is good but seems to be rare in pictures. Spanking is good, caning and whipping less so. Nipple and pussy clamps are not bad. I do sort of like the idea of women being ordered around but you can't really see that on a picture! That's more a thing for stories - do you like reading erotic stories?
Ruby.
PS I thought about you as well.
Ruby re-read the email and decided to send it before she began trying to make changes. No point thinking too much about it, she told herself. Ruby tried to get on with some schoolwork but she could not stop wondering whether she had a reply. She ended up checking her email every two minutes to see if anything had come back from Oliver. In the end she did not receive another email until the next day:
Hi Ruby,
I've added more pics for you. I also like the idea of tying a woman up and having sex with her. I like the idea of making her do whatever I want. I haven't read many stories. Since you like the idea of being ordered around, here is my order for you: write me a short erotic story of something that you'd enjoy. I expect it in two days at most.
Oliver.
Ruby read the email and then slid her fingers into her knickers. She could feel her own wetness already coating the inside of her vagina and she began fingering her clit as she read the email again, imagining Oliver sat there behind her, ordering her to write the story, and kissing her on the cheek when she did well. Afterwards he would tie her up and then it would be his finger on her clit, teasing her. Ruby masturbated until she came, and then began thinking about her story.
Over the next two days Ruby carefully wrote her story. Each night she had a sexual dream involving Oliver. She wrote a story about a woman being tied up by her boyfriend and spanked and then fucked from behind while he fingered her clit. She sent it off to Oliver and awaited his reply, which came the same evening:
Ruby,
Wow! Really great story, left me very horny I have to say! I'm guessing you would have liked to be the woman in the story and I certainly would have liked to be the guy! We should get together again some time - are your parents out any time soon?
Oliver.
Ruby's heart was pounding as she read it. What was he implying with that last sentence? Surely he couldn't be thinking what Ruby was thinking?
Oliver,
I'm glad you liked the story. My parents are out at the theatre in the evening, in three day's time on Monday. After that, they are unlikely to be out again until the carnival, but I'm guessing you'll be going to that. What do you mean get together - to talk about things?
Ruby.
PS I had a sexual dream last night, and you were in it. Thought you'd like to know.
Ruby stared at the last line, debating whether to delete it or not - whether it made the email seem too forward. She impulsively clicked send and then regretted it. What if he wasn't interested; he was going out with Joanna after all? The email back was thirty agonising minutes later.
Ruby,
On Monday I will come round to your house at eight. I will tie you up. After that you get no say in matters, except to use your safe-word (pineapple), which would finish off the evening. Tomorrow, as confirmation that you accept this, I expect you to send me a list of things that are completely forbidden for me to do to you. Bear in mind that I could do anything I want to you, and if it's not on the list then I might well do it. I expect you showered and smartly presented.
Oliver.
Ruby stared at the message. In a way, it was her ultimate fantasy, and yet it was also sort of scary. She did not have to do it - she could simply let things drop. But this was what she had secretly hoped for - that Oliver would dominate her. Ruby decided that she may as well write the list - she could always not send it once she'd written it.
Ruby started listing some things. She did not want to lose her virginity yet so full-on sex was out. In fact, she did not want Oliver to see her horrible body at all. She would not know what to do with Oliver's bits if she was presented with them, so that was out too. She did not want to leave her room at all, that was worth mentioning. Then she began to worry - what if he brought a friend with him? She doubted it, but she listed that too. She did not want to try any painful things just yet either. She kept listing things she was paranoid about. When she had finished, she looked at her list:
No sex
No inserting anything into my actual vagina
No coming on my vagina
No undressing me
No blow-jobs
No hand-jobs
No leaving my room
No other people involved
No spanking
No caning
No whipping
No painful toys (e.g. clamps)
No painful or uncomfortable bondage
No blindfolding me
You must go before my parents get home
Do not take any photos or similar
No taunting or insults as part of the domination
The list was very thorough, she realised. In fact, there was little left that Oliver was allowed to do - tie her up and kiss her? If Ruby sent him this list he would probably not turn up, thinking she was amazingly frigid. She began adjusting it, trying to cut out as much as possible:
No sex or inserting anything into my actual vagina
No coming in my mouth or on my vagina
No leaving my room
No other people involved
No whipping
No painful toys (e.g. clamps)
No painful or uncomfortable bondage
No blindfolding me
You must go before my parents get home
Do not take any photos or similar
No taunting or insults as part of the domination
That list looked much more acceptable. Some reasonable restrictions, including no sex. Ruby could probably live with the things she had removed, and she always had her safe-word if it turned out she did not like them. The question now was whether to send it or not. Ruby began composing the email for if she did send it - in the end it was simply the list plus a quick note to say that she was excited but nervous. Ruby hovered over the send button, debating whether or not to send it. Then her finger slipped, clicked the mouse button, and the email was gone.
She was aghast - should she immediately send an email and say that she was still deciding. No - that would make her look like she was not interested. She probably would have sent it anyway, right?
Oliver looked at the list in the email. It seemed quite reasonable - sex would feel too much like cheating on Joanna anyway. As it was, Oliver did not plan to do too much with Ruby that he considered was out of order. It was only going to be playing around with a friend a bit, nothing serious. Foreplay was not really cheating anyway, he decided.
By the time Oliver arrived at Ruby's house, she had already spent two hours preparing. Her bedroom was again prepared for Oliver, she was wearing her very best underwear, smart clothes that would also be easy to remove. She had showered, washed and conditioned her hair, shaved her legs and put on some perfume.
Ruby led Oliver up to her bedroom with a mumbled "come on up,"; neither of them really sure what to say. They both sat down on her bed. An awkward silence followed. Ruby could feel her stomach churning with nervousness and anticipation. Oliver reached into his back pocket and pulled out a pair of metal handcuffs. Ruby smiled and put her hands behind her back as Oliver carefully put the cuffs on her. He took hold of her torso and forcefully guided her to lie down on her back. Ruby shifted so that the handcuffs were not digging into her back.
Ruby's heart was thumping as Oliver began awkwardly sliding her skirt up her prone legs.
"Are you cold?" he asked her, noticing that her legs were shaking.
"No," Ruby admitted, "just nervous."
"Oh," Oliver said. He was excited and slightly apprehensive but he now realised that it must be worse for Ruby. "There's no need to be nervous," he told her, and he moved up the bed to touch her face reassuringly. His hand wandered sideways and began stroking her hair as he smiled at her. Impulsively he leaned down and kissed her forehead. Ruby inclined her neck slightly and Oliver recognised her want and kissed her on the lips. It was not Ruby's first kiss - although still a virgin she had at least kissed many boys before. Oliver was fairly average in that department as far as she was concerned.
"Do you still want to do this?" Oliver checked.
"Do I have a choice?" Ruby asked with a devilish smile.
"Nope," Oliver replied with a wink. Ruby bent her legs, raising her knees into the air. Oliver slid her skirt easily downwards, letting it spill over her chest and to the side, leaving her legs like two over-long stamen amid the petals of her skirt. Her thighs were round rather than slender, with smooth milky-white skin that contrasted with her black panties. Oliver placed his hands around the inside of Ruby's ankles so that his thumb was stretched away from the rest of his fingers and then ran his hands up her calves to her knees and back down her thighs to her crotch, leaving his thumbs resting on her buttocks and his fingers on the top of her thighs. He slowly slid his hands outwards and upwards until his fingers were on the waistband of her knickers at her hips. He hooked his fingers inside the waistband and paused momentarily.
Ruby's pulse was racing. A man was about to pull down her underwear and become the first person to ever see her sex, while she was tied up and unable to stop him. She was more aroused than she had ever been before in her life.
Oliver tugged at her underwear and yanked it from underneath her bum, then pulled it all the way down her legs, the panties pulling her legs together as they slide down. Oliver eased her legs apart again and grinned as he gazed at the triangle of wild, curling dark brown hair. He shuffled closer and noticed the drops of moisture clinging to the hairs in the centre.
"I see someone's wet," he noted as he ran his finger lightly down the middle of her pubic bush. Ruby reddened at the betrayal by her body, and the thought that this man was able to know more about how wet Ruby was than she did - she had no idea she was so wet until she felt his finger brushing her damp labia. Oliver eased his thumbs between her labia and pulled them wide apart.
Ruby felt vulnerable, her private parts fully exposed for him to inspect. Oliver spent a few seconds admiring her dusky red clitoris and inner labia. "Is it... normal?" Ruby asked, worried at how long Oliver was waiting while looking at her genitalia.
"Yes, of course. Am I the first guy to ever touch you down here?" Oliver asked.
"Ummm-hmmm," Ruby answered affirmatively, and Oliver's dick swelled. There was something indefinably, primitively attractive about the thought of sexual intimacy with a virgin. He had a sudden urge to lick her juices and decided to give her head instead of using his fingers as he had planned. It was something Oliver sometimes felt in the mood for but largely tried to avoid with Joanna if she was not too insistent about it.
He dipped his head fully between her thighs, extended his tongue and ran it up the inside of both of her labia in turn. Then he began gently lapping at her clitoris, like a kitten at a tray of milk.
The feeling of Oliver's tongue on Ruby's clitoris was electric. She instantly understood what Lisa had meant many days earlier when she had talked about how great it was. Ruby instinctively moaned out loud and then felt embarrassed - she had never done so when masturbating on her own. This was the stuff of her dreams, Ruby thought to herself; tied up by a handsome man while he licked away between her legs.
Had his mouth not been wide open to allow his tongue free movement, Oliver would have smiled when he heard Ruby's moan. He began licking faster to try to induce more of the same. It worked and Ruby was soon moaning uninterrupted and unabashed - it was so pleasurable that she was distracted from all thoughts of propriety and decorum that had made her initially try to contain her expressions of enjoyment. Ruby's groaning quickly became more insistent and Oliver realised that she was already close to her climax, after only a few minutes. In contrast, Joanna usually took half an hour or longer.
Ruby came with a shuddering moan that suggested her vocal chords were shaking as much as her legs were as her body hummed to the tune of her orgasm. Oliver pulled his head away and crawled up the bed to kiss Ruby, enjoying the thought of her juices that surrounded his mouth transferring to surround her own lips, his drying tongue that tasted of her seeking out her own soft tongue in the entwining of their mouths. Ruby was too caught up in her post-orgasmic bliss to even notice such things.
"Thank you," Ruby said when Oliver pulled away slightly, her moist lips forming a smile, a definite gleam in her eye.
"It's not over yet," Oliver pointed out as he knelt on the bed. "You're still mine," he said as he briefly caressed her chin. Ruby felt a spike of fear and worry, tempered by arousal at the thought of being powerless to resist whatever he had in mind. "Sit up," he told her as he pushed her skirt back down over her legs. Ruby did so, and grimaced at the unpleasant damp patch on her skirt that she could feel beneath her ass. "Move up so your back's against this," he told her as he began to put pillows against the headboard of her bed. Ruby shuffled awkwardly up the bed until she was sat leaning against the headboard that was almost flush against the wall.
Ruby could only watch as Oliver unzipped his trousers and pulled down his boxer shorts, revealing his hard cock. In proportion to his body it seemed a normal size, based on what Ruby had seen in porn, but in the flesh it looked positively huge. Ruby wondered how her vagina would ever be able to accommodate something of that size. Oliver moved to stand in front of her, his legs apart, planted either side of her thighs on the bed. His cock was now only inches from Ruby's face and her mouth instinctively clamped shut as she began to suspect his intentions.
"Open wide," Oliver said. Ruby did nothing. "Open wide," he repeated. Ruby looked up at him, her mouth staying closed while her eyes pleaded with him.
"Ok, we can take it slow," Oliver said, annoyed but trying not to show it. He had been looking forward to the next part of his plan for a while now. "Just suck on the head."
"I don't want to do it," Ruby complained, looking at the intimidating prick in front of her face. She had thought that a blow-job would be fine for her to be made to do, but now that it actually came to it, she realised that she strongly did not want to be forced to do it. She prepared to use her safe-word.
"Ok," Oliver said, and stood there for a few seconds, his dick wavering in the cool air as he considered what to do. He knelt down and reached around Ruby to uncuff her hands.
"Are we stopping?" Ruby asked, feeling a mixture of relief, disappointment and shame.
"No, not yet," Oliver said as he pulled her hands in front of her and cuffed them together again. "You're going to jerk me off instead," he informed her as he sat down and lay back on the bed, pulling his jumper upwards to reveal his bare chest. Ruby rolled onto her knees and crawled next to him before taking his cock in both hands. She knew the basic motion from watching porn, and she began to pump his dick up and down with both hands, her handcuffs rattling as they were shaken up and down.
Oliver moaned softly. The motion was slightly awkward but a hand-job was a hand-job, and it was fun to watch her struggle with his prick while both of her hands were cuffed together. Ruby kept pumping away. His cock did not seem nearly as intimidating now. Eager to prove that she was not too scared of it, she bowed her head and kissed the head of his dick. It was an easy thing to do and emboldened, she began kissing all over his cock. Oliver smiled; it was not particularly pleasurable, but it was good to see her getting to used to having her mouth near his dick. She even began licking up the side of his prick.
"Good girl. Now hands," Oliver said simply, becoming impatient to be finished off. Ruby returned to masturbating him powerfully with both hands until he began moaning loudly and jets of come shot from his penis onto his chest. Ruby had seen it on screen before but she was fascinated by the streams of semen arching through the air. After Oliver had finished coming, Ruby held out her hands to be uncuffed and once free she fetched a wad of tissues for Oliver. He cleaned himself up and redressed. There was an awkward silence.
"I guess I'll be going now," Oliver ventured.
"Ok, yeah, that's fine," Ruby said, glad that he would leave. It was close to becoming too overwhelming for one evening, she needed some time on her own to relax . Oliver made his own way out and Ruby sat there for a while, stunned by all that had happened. Then she realised that she was horny again and she began masturbating as she replayed the events of the evening in her mind.
To be continued.
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