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CHEEKY PICKUP
'Cheeky sod.' Caroline exclaimed to her friend when Dianne returned to their table, with fresh drinks. 'Who?' Dianne asked. Caroline nodded in the direction of a group of young men at the bar. The one with his back to us. Dark hair, blue t-shirt.' 'And how was he being cheeky?' Dianne asked. 'He asked if I "fancied a bit of fun with him" and gave me a cheeky wink. 'Okay, it was cheeky but it wasn't really bad, and,' Dianne lowered her voice, 'He's got a nice tight arse. What did he look like? I can only see his back now.' Caroline widened her eyes at her friend's cheek but in the end had to agree. 'Quite nice looking, though a lot younger than us.' Caroline told Dianne. "Quite nice looking." Dianne repeated her friend's words. 'So do you fancy him?' Caroline smirked.
Caroline and Dianne had taken a late season, cheap holiday deal to Benidorm. The hotel was busy but not full. They were a couple of weeks earlier than previous years. They had stayed in the hotel before and liked that it was not a high rise, had a big pool and only a 10 minute walk to the beach. What they had forgotten when they made the slightly earlier booking than usual was that, although schools had gone back to class after the summer holidays, universities had not. There were students in the hotel, cramming in cheap breaks before the university autumn term. They guessed that the "cheeky sod" was most likely a student.
A little later Caroline nudged her friend and nodded toward the bar. 'Oh he is quite nice looking.' Dianne said quietly to her friend, following her eyes to where the young man had turned so he no longer had his back to them. 'I see what you mean about him being young.' Dianne added, at the same time trying not to be obvious about looking at the young man. 'He must be less than half our ages, maybe still in his teens.'
After another round of drinks loosened her tongue, Dianne decided to be cheeky again to her friend. 'Caroline. When was the last time you got laid, and what would be wrong with having a "bit of fun" with that young guy?' 'Di, You're terrible.' Caroline exclaimed. 'Maybe' Dianne said 'but you didn't answer my question.' 'Okay well if I answer it, then you have to answer your own question too.' 'Fair enough Caro. You first.' 'Well I'm afraid the answer is, I don't really know. It's been a long time. I suppose over eighteen months, perhaps longer. Your turn, Di.' 'Probably about the same. I wouldn't mind a bit of naughty fun.'
'He keeps looking this way, Di.' 'Let him. It's kind of flattering being checked-out by a young man. Another drink.' 'Go on, then, Di. I don't want a hangover tomorrow but one more would be okay I guess, and we are on holiday.' 'Back in a few minutes, Caro. Theres a bit of a wait at the bar.'
At the bar Dianne glanced back and saw the young man had again approached their table and was chatting with her friend. She was interrupted by the barman to take her order. The young man had gone again by the time Dianne returned to the table with their drinks. 'Well? What did he say, Caro?' 'Same as before, though he wasn't quite so cheeky this time.' 'Okay, now as you said a little while ago "we are on holiday." that needn't just refer to our drinking. You could have the "bit of fun" he's suggesting. After all, no one back home has to know, I can keep my mouth shut and stay out of our room for a while.' Dianne grinned at her friend then said 'Back in a couple of minutes. I need the loo.'
When Dianne returned to the table a few minutes later, Caroline was already half way through her drink. 'Go a bit easy.' Dianne said to her friend. 'It's a bit of Dutch courage.' Caroline replied. Dianne studied her friend for a moment, then light dawned. 'Oh I see. You're going to have that "bit of fun", you saucy old tart.' Dianne chided her friend. 'I can stay down here for a while, if you're going to our room.'
'You're not staying here.' Caroline said. 'I'm only doing this if you do too. He came over again while you were in the loo. I told him that I'd only have a 'bit of fun' with him if we both could. You should have seen his face, what a picture.' 'What, you got me into this too?' 'Yeah, why not, after all it was your idea. I reckon you need to get laid too. To be fair to the lad, he said he didn't know if he could manage us both but he'd give it his best 'shot' and have a hella'va lot of fun trying.' 'Why you sneaky...!'
'Look, Di. He's coming over again. What shall we say.' 'Tell him to come to the room in about 20 minutes.' Caroline lowered her voice, leaned closer to her friend and said 'This is exciting. It's making me feel, you know.' She looked down indicating her lap to her friend. Dianne gave a mischievous smile and nodded agreement.
A few minutes later the two middle aged women strolled as nonchalantly as they could from the bar, giving the young man a barely perceptible smile as they went. In the lift up to their room Dianne asked 'Caro, do you think he'll actually wait 20 minutes.' 'Probably not.' Caroline replied. 'I think he'll want to get out of that bar before his 'excitement' becomes too obvious.' she giggled. 'Or maybe he'll get nervous and won't come at all.' 'I don't think we're that intimidating.' Dianne answered her friend.
'Caro. since we've come this far, how about a being a bit outrageousness when he comes?' 'Maybe.' Caroline replied warily. 'What do you have in mind?' Dianne outlined her cheeky idea as the lift came to a stop at their floor and they trotted back to their room. 'Di, really. What has got into you this evening.' 'Nothing yet' Dianne replied. I'm looking forward to what does.' she smirked. Since leaving the bar, the two women had given up all pretence of nonchalance and hurried back to their room.
In their room, they quickly prepared themselves for their expected visitor. Sure enough after barely 15 minutes since leaving the bar, there was a knock on the door to their room. 'Shall we make him wait?' Dianne asked with an evil little grin. 'He is early.' Caroline just smirked. Dianne put her hand on the latch and began to count slowly and quietly. Not loud enough for it to be heard in the corridor but loud enough for Caroline to hear her. At 20 she said 'I think we've tortured him long enough.' and opened the door just as the young man looked like he was turning to leave.
The moment he stepped into the room the young man stopped at the unexpected sight of Caroline lying naked on the bed. His eyes widened and his jaw dropped in surprise. All the bravado he had shown in the bar when he had said he would "give it his best shot and have a hella'va lot of fun trying." had drained out of him.
As the door to the room clicked shut behind him, he looked back at Dianne, just in time to see the beach robe she had been wearing when she opened the door slide silently to the floor, revealing her nakedness too. For the first time in his life the speechless young man found himself in a room with two naked women. His arousal, which was already evident from the bump in his shorts, was getting uncomfortable as his excitement increased further at the sight of Caroline and Dianne completely naked.
Dianne stepped in front of the lad and gently put a finger under his chin, applying a little pressure until he closed his mouth. He seemed unsure where to cast his eyes until Dianne said 'It's okay to look wherever you want.' and smiled at him. He seemed to gather his wits and managed hesitantly to say 'I thought you were kidding when you said both of you.' 'Oh, we do everything together on holiday, young man.' Caroline told him. 'You look like you could do with a drink, why don't you get one from the mini-bar. I think you need to calm down a bit.' The young man seemed almost grateful to divert his attention for a few moments.
After allowing him to take a couple of quick gulps at the vodka he'd chosen from the mini-bar, Dianne stepped in front of him again. 'Now then let's make things a bit more comfortable than that tight bulge in your shorts.' She tugged at the loose ends of the waistband cord and eased his shorts down over his hips. He meekly complied. He kicked his flip-flops off and stepped out of the shorts as they dropped to his ankles.
Dianne took the glass from him, placed it on the dresser and then lifted the hem of his t-shirt. 'Arms up.' she said and lifted it over his head to drop it on top of the discarded shorts. She picked up his drink, put it back in his hand and said 'Finish it.'. He gulped the last mouthful of vodka and coughed as the liquid burned down his throat. A second later, Dianne slid his underpants down, briefly catching his erect cock under the elasticated waistband. The lad was now as naked as the women, with his erection hard and pointing toward Caroline on the bed.
'I don't think he'll last long, Caro. He's overexcited.' Dianne ran a fingertip along the length of the lad's cock. He gasped at her touch and she felt his cock twitch. A bead of pre-cum liquid expanded at the tip. 'What are we going to do to slow him down a bit, Di?' 'Hmm. I'm not sure we can do much about that level of excitement. Maybe he just needs to be relieved so when he recovers, he can try again with a bit less urgency. One of us could give him a quickie but I have an idea to try first. 'This way young man.' Dianne beckoned with her finger and sat down on the side of the bed waiting for him.
He approached cautiously and stood in front of her wondering what Dianne was going to do. She reached out and wrapped her fingers gently around his erect cock which, where he stood and she now sat, pointed directly at her. She started to stroke the lad's erection slowly, occasionally sliding her thumb over the tip. While Caroline watched her friend wank the young man, she played with her own pussy finger fucking herself and rubbing her clit.
The lad stood dumbfounded not knowing where to look: at Dianne's hand on his cock or Caroline's fingers plunging into her pussy. After only a few strokes of Dianne's hand and less than a minute he exploded. Dianne felt his cock jerk in her hand and heard a grunt escape his lips as his semen landed on her boobs, in a spray of sticky droplets. After a few seconds he released the breath he had been unconsciously holding while Dianne stroked his cock.
'Pass that box of tissues, Caro.' Dianne took the box from her friend and taking a handful of tissues from the box, gave them to the young man. Giggling Dianne said 'You made the mess, you clean it up.', indicating her breasts. Then she leaned back while the young man tentatively wiped his cum from her tits, enjoying the feel of his hands on her, stiffening her nipples. After cumming over Dianne, the young man's erection has softened slightly. By the time he finished cleaning his own cum off of Dianne's tits he was hard and erect again.
'Well then, aren't you going to do what you came for.' Caroline grinned and giggling went on 'I'm waiting to be' she paused, hardly able to believer her own voice 'fucked.' She spread her legs in anticipation while Dianne moved onto the other bed to watch.
The lad joined Caroline on her bed, kneeling between her legs. Just as he was about to lean down to enter her, Caroline said 'Aren't you forgetting something?' The lad looked confused for a moment then said 'Do you want me to wear a condom?'. 'No silly,' Caroline said 'I just want to know your name. I want to know who's fucking me.' 'Liam, it's Liam.' the young man blurted out before plunging his erect cock into Caroline's wet pussy, sliding in until his hips were pressed tight to her's. She caught her breath for a moment as he filled her then grabbed his arse, digging her nails in holding him in tight.
After a minute or so Caroline released her grip on Liam's arse, letting him begin to fuck her. Dianne, sitting on the next bed, was fingering her pussy watching her friend being fucked. Unconsciously, while Dianne watched and finger fucked herself, she matched each plunge of her fingers into her pussy with the rise and fall of Liam's bum while he fucked Caroline.
The young man was inexperienced and even after Dianne had wanked him, he was still getting carried away fucking Caroline. He was thrusting his cock into her faster and faster. Fortunately for Caroline, because she had been fingering her pussy while she watched Dianne stoke Liam's cock. She had her orgasm moments before Liam's final thrust when he expelled his cum in her pussy. As her orgasm coursed through her she grabbed Liam's ass hard, her finger nails digging in while she let out a long soft moan. As her orgasm ebbed away, Caroline released the breath she had unconsciously drawn and held at the end of her moan. A panting Liam collapsed on top of Caroline. Dianne too caught her breath as she brought herself to orgasm finger fucking herself, while watching her friend being fucked.
After resting for a few minutes Caroline spoke up "Off you get, Liam. It's Di's turn for your 'services'." she grinned. Liam raised himself off of Caroline slowly, almost reluctantly, withdrawing his still semi-erect cock. Dianne stared for a moment then said 'Not bad, Liam, but I want you fully erect again.' 'I want what you had, Caro.'
Caroline sat up on the side of her bed, then like Dianne had earlier made Liam stand in front of her. For the second time Liam felt a woman's fingers wrap around his cock, this time Caroline's. Unlike Dianne had earlier, Caroline did not stroke his cock by hand. She supported his semi rigid member with her hand then lent forward, kissed the tip of his cock then flicked her tongue over the tip too. The instant Carolines tongue touched Liam's cock she felt it twitch in her hand. 'I think he'll be ready again pretty quick, Di.' Caroline giggled to her friend, then slipped her lips over the boys cock taking the tip into her mouth. In moments Liam was hard again, his cock pointing upwards again with no sign of droop.
Dianne lay back on her bed, spreading her legs and raising her knees. She was as ready as Caroline had been, since she had been finger fucking herself while she watched Liam fucking her friend. Liam looked a bit like he was in a trance. It seemed he could hardly believe what was happening when Caroline gave him a gentle but firm push toward her friend. 'Go on Liam. Dianne is waiting.' He stopped for a moment at the side of Dianne's bed, looking down at the second naked woman waiting for his cock to slide into her pussy.
Liam knelt on the second bed between Dianne's open thighs. For the third time that evening he felt a hand grasp his cock. Dianne was impatient and had reached up but instead of stroking Liam's cock she gently but firmly drew him down onto her, guiding his cock directly into her waiting, wet pussy. The instant she felt his cock slip between her pussy lips, Dianne switched her grip to Liam's arse, pulled him down until his cock slid all the way into her pussy then wrapped her legs around him too. She savoured the feel of a man's cock filling her for the first time in well over a year of only self pleasure. Caroline, watching as Liam's cock slid easily into her friend Dianne's waiting pussy, was already pleasuring herself again, rubbing her clit.
After savouring for a few moments the feeling of warm male flesh deep in her pussy, Dianne released her tight grip on Liam's bum, allowing him to start to slide his cock in and out of her. It was not long before both women were moaning softly, Dianne being fucked by Liam also panting slightly for breath, Caroline alternately playing with her clit and dipping two fingers into her already fucked pussy watching Liam now fucking her friend.
Liam, even after two ejaculations was nearing his peak for a third time. Panting and moaning between breaths he shuddered and expelled himself into Dianne's pussy this time. Dianne feeling his cock jerk and throb spilling his semen into her felt her pussy contract, clenching around Liam's cock as her orgasm blossomed causing her to tremble and expel a long breath that she had unconsciously held in, in the moments before her orgasm.
Caroline watching her friend, realising Dianne had cum, frantically finger fucked herself with two fingers of one hand while her other rubbed her clit until she orgasmed moments after Dianne. As Dianne's peak of passion began to subside, she moaned 'Damn, Caro, I never realised how much I needed that until now.' 'Me neither.' Caroline panted.
Later, after the young man had left the women alone together, they were still talking about their naughty, sex filled evening an hour later, while they were getting ready for bed. Just before switching out the light Dianne said to her friend 'You know, Caro, this is a holiday I won't forget soon.' 'It's not over yet, Di.' Caroline replied and leered at her friend before dousing the light.
Liam went back to the bar after leaving the women, wondering if any of his mates were still there. 'Well well, look who's back.' Liam heard one of them remark as he rejoined them at the bar. 'Where have you been?' Russ asked. 'If I told you, you wouldn't believe it. Probably just make fun of me so I'm saying nothing.' Liam smiled to himself thinking back to barely fifteen minutes earlier.
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