It had begun one night when Emma and Wayne were making love. As she straddled and then rode him in her usual energetic manner he had reached around and begun to play with her from behind, touching and probing until finally his finger had found its way into her anus. She was shocked at first, but then she was surprised to find it a strangely enjoyable sensation to have both a finger and a cock inside her at once, different but very pleasurable. It was something she had not tried before, but then, at the tender age of nineteen, there were plenty of things she had not tried before and she looked upon her older lover, Wayne was twenty-eight, as her bedroom teacher and mentor. He was the one to help her explore the world of erotic pleasures, or so she believed.
'Mmmm, that's nice.' She had told him, wriggling her bottom a little as she descended to force him deeper, wondering at the same time if she liked it because she shouldn't.
Wayne smiled without answering except to stab his finger as deep as he could reach, making her eyes to widen in shock by immediately triggering a colossal orgasm.
Later, as they lay enjoying a post coital cuddle, she voiced the thoughts that were unexpectedly marching through her mind. If a finger there felt that good, what would a cock be like?
'Wayne? You know where you put your finger?' She had asked. 'Have you ever had proper sex with anybody there?'
He turned his head and looked at her in surprise. Actually, he hadn't, but he wasn't about to admit that because he wanted Emma to believe he was fully experienced in all things bedroom related, and it was something he'd often wanted to do but had never had the nerve to suggest to any of his previous girlfriends. The fact that Emma had brought the subject up herself was cause for astonished elation.
'Just a couple of times.'
'What's it like?'
He hesitated while he formulated an honest sounding reply, thinking and hoping that just maybe she might like to try it. 'Well, from a man's point of view it's nice. It's tighter than a pussy fuck, and you need a lot of lube, but the odd times I've done it we've both enjoyed it.'
'Does it hurt?' She also turned her head to face him and was looking at him intently, her pink tipped breasts rising and falling rather more than their earlier session warranted.
'Not if it's done properly.'
She gazed at him silently for a minute or so, her eyes searching his face for answers to which only she knew the question, and then she rolled onto her side, her hand trailing down to find his spent and still sticky cock and to massage it hopefully.
'Would you like to do it to me?'
The residual sensation of his finger inside her rectum and pressing against the cock in her pussy was still exciting her, and the intriguing idea of taking such naughtiness to the next level was making her heart beat quicker.
'We'd need to use some sort of lubrication, but if you're sure you'd really like me to.'
She felt that she was ready to push at her sexual boundaries and try things she'd never done before. It was time to be a little more experimental.
'Yes, I'm sure. I really want to do it, if you're careful.'
'You get some lube then, and if you still want to next time, we'll give it a go.'
Both the idea and the responsibility of it were going to be down to her, he had been determined on that so that if it didn't work out, the fault would be all hers, but Emma neither knew nor cared about who would be responsible, she just wanted to try something new and just a little kinky and she was a bit miffed that she would have to wait, but her next trip to the mall was to buy a tube of lubricating gel.
'Shall we try it?' She asked him when they were alone together next.
'Try what?' He responded, pretending nonchalance as if he hadn't been thinking about 'it' ever since they had last been in bed.
'You know.' She felt herself blush. 'Shall we do what we said we would and do it in my bum?'
'Oh that? Yes, why not?'
'We don't have to.' She sounded puzzled and a little hurt.
'No, no! I want to.' He back-pedalled hastily.
'Be careful, won't you?'
'I promise. Are you organized?'
She nodded with her eyes bright with nervous excitement, knowing that he meant had she bought the lube.
'Come on then.' He took her hand and steered her towards his bedroom, unzipping the back of her dress as they went.
'You're enthusiastic all of a sudden.' She giggled, unclipping her bra as her dress slid to the ground.
'And I'm not on my own, am I?' He observed with a grin, watching her step out of her panties even as he unbuckled his belt.
Two minutes later she had handed him the newly purchased lube and was on all fours on the bed ready for him. 'Are you ready?' She asked, sticking her bottom out high.
'Don't you want a kiss and cuddle first?' He asked, surprised by her eagerness. Emma was not usually a girl to go straight for the main event.
'No, not this time.' She looked over her shoulder at him as he kicked off his boxers. 'I just want to do it and see how it feels.'
'And who am I to argue with a lady?' He asked with mock chivalry, only to be taken aback when she burst out laughing, a nervous laugh that showed her anxious state of mind.
'And how can I be a lady when I'm kneeling like this waiting for you to do me up the arse?' She asked. 'If anybody else knew I'd die of shame.'
'Don't worry, nobody else ever will.' He assured her, climbing onto the bed to kneel behind her. 'Ready?'
'You will be careful and take it easy, wont you?' She asked, a little tremor in her voice. 'I really want to do it, but I'm as scared as hell.
'I promised you, didn't I?' He flipped the lube open. 'And anytime you want, just say and I'll stop.'
Reassured, she nodded. 'Let's do it then.'
There was a short pause and then she felt the cold slipperiness of lube around her anus. She shivered, partly from the sensation of sudden cold, but mainly with excited apprehension, especially when his finger tip pushed into her, rotating and sliding back and forth, making her ready for the intrusion, lubricating and opening her at the same time. This, she told herself, was what she wanted and she was going to enjoy it. She was going to experience her first taste of what in her eyes was extremely kinky sex.
But then his finger moved away and for what seemed like an age there was nothing. She waited impatiently with her eyes screwed shut and her hands clenched into anxious fists, but the expected penetration didn't happen. She looked around, peering nervously over her shoulder, wondering if he had changed his mind and decided it was just too dirty to do, but then smiling inside at her own silly anxieties when she saw his hand go from spreading lube on his shining cock to close the flip-top of the lube. He wiped his hands on tissue and then looked back at her.
'Okay?' He asked, seeing her staring at him.
She nodded and set herself once more, still looking at him over her shoulder, watching him with excited embarrassment as he pulled her cheeks gently apart and stared at her anus for a few moments before he shuffled closer and gripped her hip with one hand while the other guided his cock towards her. Her heart hammered and she could feel her breath coming in short little gasps, fear and arousal fighting for dominance. She turned her head to stare steadfastly to the front and waited.
The first touch of his cock against her body brought a gasp of trepidation and she had to resist an instinctive urge to pull away, making herself push back instead as he pushed against her. This really was it, she felt him leaning towards her, the pressure against her rosebud increasing until she needed to press back harder to prevent herself being moved forward. She was scared now that he wouldn't be able to penetrate her or that it would need so much force as to be painful. She willed herself to open and admit him and then, just as anxiety made her want to stop him, she felt her sphincter give way and open just enough for his cock to enter. The entry was unexpected and abrupt, and she heard him groan with sudden pleasure even as she gasped with relieved surprise. It had happened almost completely painlessly, with only a very brief and hardly noticeable moment of discomfort as her sphincter stretched to accommodate him. He paused with his cock head just inside her, allowing them both to become accustomed to the sensation.
'Okay?' He asked her again.
She nodded. 'Yes, I'm fine. Do it.'
He adjusted his position and took hold of her hips, pushing forward so that his cock slid deeper into her rectum until she felt his body press up against her bottom. She gasped at the sensation and again he paused, intent on making sure she was comfortable with what they were doing.
'Do it.' She told him urgently, the forbidden nature of what they were doing making her feel wonderfully naughty and just a little smug.
'Yes, do it to me.' Her voice was breathless with excitement. 'I want you to come inside my arse. I'll stop you if it hurts.'
Her words reassured him that at least it wasn't hurting so far and he began to thrust into her, slowly and cautiously at first but picking up tempo and power as he went until he was fucking her arse as hard as he would her pussy, grabbing at her hips and grunting with illicit enjoyment every time his cock slammed into her.
Emma could feel him sliding in and out of her, the sensation different to normal sex but without feeling so alien as to be unpleasant. In fact, she was happy to admit to herself, it was actually bloody good. She could feel his cock filling her, the close fit in her tighter passage magnifying the feeling wonderfully, as if she were being taken by a giant.
But for all that, the overall effect wasn't exactly what she expected. Sure it was exciting and it got her going, perhaps mainly because normally it as so taboo, but she felt as if she were missing out a little. She liked it, in fact she liked it a lot, but her pussy felt empty even as her rectum felt so beautifully full. Wayne's finger had entered her when her pussy was filled with his cock, and now she missed having something in there too. She had attracted to the idea of having something in each hole at the same time and this wasn't quite it.
'Can you finger my pussy too?' She asked.
Wayne tried to reach down under his cock to her, but he had to lean sideways and even then he couldn't quite reach. All that happened was that his rhythm was interrupted and he nearly slipped out.
'Sorry, sweetheart.' He apologised breathlessly, taking hold of her hips again and thrusting steadily once more. 'I can't do both.'
She could see that it wasn't possible, but she still felt disappointed, robbed of the complete sensation, even though it wasn't really spoiling her enjoyment of being so naughty. It was, she thought to herself, a shame he didn't have two cocks, one for each entrance. Nevertheless, she loved the feeling of having him inside her arse and she could feel an orgasm building steadily.
She came roughly five seconds after he did, her climax finally triggered by his cock twitching and jerking inside her rectum as he pumped his spunk into her. The exciting knowledge of what he was doing made her come explosively, a short but extremely powerful detonation that had her yelling out with surprise at its intensity before slumping forward, dislodging his slippery cock from her well filled arse.
'A pity you couldn't have me in both holes at once.' She gasped, finally voicing her frustration as they lay side by side to get their breath back.
'I'd have to split into two to do that, unless I get someone to help me.' He joked, not realising what seeds he was sowing.
During the next few days she and Wayne tried anal sex twice more, but even though she got an illicit kick from it each time and a powerful orgasm, still she wasn't happy and finally she decided that, just as he had jokingly suggested, two cocks was what was needed. The next week was spent persuading Wayne to go along with her fantasy, and eventually she got her way by promising him that he could count it as her birthday present in two weeks time and that when his birthday came around she would find another girl to make a threesome up for him.
For Wayne's part, he found that he wasn't as against the idea as he expected he should be and the thought of seeing another man with his cock up Emma was actually quite a turn on, especially as a couple of months later his own birthday would see her repaying his big-heartedness. He didn't feel at all jealous at the idea; after all, they wouldn't be making love in the romantic relationship sense, just being kinky. He set about finding someone.
'I've found a fella to help us out.' He told Emma excitedly one day.
He heard her ecstatic breath. 'Who?'
'Carl.' He told her, naming one of their mutual friends. 'And Debbie is prepared to be the other women when it's my turn.' He wasn't going to let her forget her side of the bargain.
Emma frowned briefly. Her hastily made promise had come home to roost. Still, she told herself, at least I haven't got to ask embarrassing favour from among my friends and it won't be some strange girl that I don't know.
'There is a condition though.' Wayne sounded worried, as if he didn't expect her to agree to whatever it was. She looked at him questioningly.
'We have to do the same for their birthdays.'
Emma's mouth opened but it was several seconds before any words came out. This was something she hadn't bargained for.
'So you want me to go there on Carl's birthday, and you when it's Debbie's?'
'Yes.' He shrugged his shoulders as if to say it was nothing to do with him.
Emma suspected otherwise. She thought about it for only a very short second. 'Yes, all right.'
Why not? If she was going to be experimental, then why not take it a step or so further?
'Are you certain?' His eyebrows shot up in surprise.
She nodded and smiled brightly. 'Of course. Then you'll get the chance to stick it up Debbie's bum, won't you?'
'I don't know if that's what they want.' He replied seriously, missing the tease in her voice. 'Would it bother you?'
'No. fair's fair. Just ask Carl around on my birthday and then you can do what you like when it's Debbie's.'
They made love, this time by unspoken agreement via the normal entrance. It would be that way until the night of her birthday some two weeks later. She expected to be nervous at least, if not scared stiff, but when the day came she found herself just excited and aroused. To have two men intent on satisfying her sexual curiosity was a massive turn on.
Even though they all knew each other, when Carl arrived there was an awkward silence at first while they sat looking at each other and wondering what to say. It was Wayne who eventually broke the deadlock.
'Look.' He announced. 'I just want to say that whatever we do tonight is all right with me. This is Emma's day and I want her to enjoy it.'
Carl nodded and gave them each a rather embarrassed little smile, but Emma reached across and took Wayne's hand, squeezing it gratefully.
'Thank you, darling.' She smiled broadly with happy relief, then paused for a moment and looked from one man to the other. 'Shall we go into the bedroom?'
The move from one room to the other was enough to give them the momentum they needed and once the bedroom door was closed they impatiently undressed, excitedly watching each other remove each item of clothing until they all stood naked and trying to appear nonchalant.
The two men were almost the exact opposite of each other, and that somehow made it all the better. Carl was tall and relatively slim, while Wayne was short and stocky, and more muscular. He was also far more hirsute, his body covered in dark wiry hair in contrast to the scarce fine blond hair that was almost unnoticeable on Carl's tanned body.
Emma gazed at them both, cheerfully contemplating the two erect cocks that now stood before her and wondering which she would prefer where. Wayne's was shorter than Carl's but made up for that by being thicker and uncut, whereas Carl's longer, slimmer one was fully circumcised. It was girth that finally made her mind up for her, she would have Wayne in her pussy and Carl, with his slender clean cut cock, in her arse.
She shivered with excitement at the thought, knowing it was down to her now to get proceedings underway. She moved forward between the two men and reached for their cocks, taking one in each hand and gently stroking them, feeling and enjoying the difference between the two rock hard shafts. This was the first time she had ever touched two men at once, and certainly the first time she had touched someone with her boyfriend present, but it didn't seem wrong, just exhilarating. She ran her fingers up and down the two shafts, smiling to herself at being so wicked before standing on tiptoe and planting a quick kiss on Wayne's forehead by way of thanks.
'Come on, let's get started.'
She released them both, climbed onto the bed and spread her arms out across the pillows, nodding to either side for them to join her.
'Come on, play with me and make me ready.'
The two men hesitated briefly; looking at each other to make certain each was comfortable with the other's presence, before Wayne climbed on the bed to her right and Carl doing the same to her left. Once again they hesitated, looking at each other over Emma until, eager to continue, she placed a hand on the back of each head and put and end to the dithering by simply pushing them down to her breasts, sighing with pleasure as they each closed their lips over a nipple.
Emma was sure that with his face only inches above her heart Carl would be able to hear her it thumping with excitement at the prospect of what lay ahead. But she didn't care, she wanted him to know how she was looking forward to having him inside her at the same time as Wayne. She squeezed the back of his head and pressed him more firmly against her breast, smiling a tiny happy smile when he answered by gently biting her nipple.
Wayne was sucking hard on her nipple, pulling it into his mouth and swirling his tongue around it, his free hand sliding down her body to seek the join of her legs. She opened them ready for him, hooking her thighs over those of her lovers to spread herself wide and exposed in invitation. She felt Carl's fingers cautiously finding their way towards her pussy and groaned with sheer delight at what was happening. It was going to be two men touching her at the same time, two men playing with her pussy, whatever could be better than that?
Wayne's hand was wandering along the length of her thigh, teasing her, pretending to touch her but turning away at the last moment, making her lift her pelvis in encouragement, waiting to be touched and wondering if it would be Wayne or Carl, who's fingers trailed softly over her stomach, who would find the first. She was rapidly getting to the point where it didn't matter who, so long as someone did. She groaned again, gripping their hair with her fingers in her excitement and pushing them harder into her breasts.
In the event both men found their target at the same time, Wayne searching and finding her entrance and then sliding two fingers into her at exactly the same moment that Carl's tiptoed over her pubic bone and trapped her clit between two of his own. She gasped and thrust up automatically with her pelvis, overwhelmed by the naughtiness of what she was doing, impaling herself on Wayne's fingers and trying hard not to dislodge Carl's.
'Oh yes.' The words were gasped from deep in her throat as she felt the first signs of an orgasm. 'I like that.'
In truth she did more than like it. She'd never felt anything even resembling the feelings generated by two men playing with her at the same time, each touching her in their own way. Wayne was, as always, trying to penetrate her pussy as deeply as his rather short stumpy fingers would go, ramming and screwing them into her, while Carl had nipped her swollen clit between the fork of two fingers and was very gently and quickly stroking its tip with his thumb. She could feel an unexpected orgasm rapidly boiling up inside her, a wonderful combination of sensations heat and pressure within her pelvis that were becoming stronger and stronger as it came closer to fulfilment.