tagTransgender & CrossdressersZara and Tom: First Holiday

Zara and Tom: First Holiday


Tom woke up to sunshine playing across his face. He looked around blearily for a few seconds, forgetting where he was, and then all the memories came flooding back. Coming back with Zara, tearing at each other's clothes, sliding inside her, urgent, desperate to feel her. Her face as she finally reached the sweet release of orgasm. Falling asleep in each other's arms. And the next few days and weeks: constantly texting each other when apart, rushing to meet up again. The nights they promised to go to bed early, but instead spent talking, hours passing in the blink of an eye. And the sex, the constant, never-ending sex. The best he'd ever had, that made every other partner he'd had look like a rank amateur. My god, the things Zara made him feel! They were feelings he thought were just hyperbole, clichés that people wrote about. He had never passed out before from pleasure or from cumming so hard. He had never seen stars or been unable to speak because of the things a woman made him feel. But with Zara, it was different. It was like their bodies were made for each other.

They had been together for just over 3 months now. Last week, she had taken the brave step of asking him to move in with her. He was surprised, but absolutely thrilled, and accepted right away. Life just kept getting better. They had even continued his 'treatments' (although Zara had become a more relaxed than in their first session), which had seen his cock reach and stay at just over 10 inches in length, becoming almost just as girthy. His balls were equally massive, and Zara constantly said he was easily her most successful client ever.

'Probably because you've fucked me way more than any of the others!' he'd quip at her.

'Well it's not my fault you're such a slut for my big cock!' She'd shout in mock anger. It was true, though, as much as Tom loved being dominant and doing the fucking, almost nothing beat the feeling of Zara sliding inside him, filling him up so perfectly. Her cock made him cum like a fire hydrant, and he adored the feeling of her cumming inside him, watching her strain, lose control and then empty her gargantuan balls, and then feeling her load pour out of his stretched ass. He knew she loved it as well.

It was Saturday, and Tom woke up to find, as always, his cock straining his pyjamas, completely erect. He played with himself for a little while, gently stroking the head of his cock. He and Zara fucked pretty much every day, and several times a day on weekends. She slept next to him, her hair surrounding her angelic face in a halo. He glanced under the sheets and saw her cock completely hard as well. He gently teased it out of her pyjama waistband and began jerking her off. Zara twitched, and then opened her eyes, smiling sleepily at him, making his heart break all over again.

'Well, good morning to you too, handsome.' She leaned forwards and kissed him sweetly. 'What did I do to deserve this?'

'Can a boyfriend not treat his girlfriend to a Saturday handjob?' Teased Tom. Zara laughed and shrugged, 'Well I don't see why not! Come take a shower with me?' Tom didn't need to be asked twice. He hopped out of bed and quickly took his pyjamas off. Zara undressed as well, and as always Tom's heart skipped a beat. She was a goddess. Zara's tits still hypnotised him, and she twirled on the spot for him, showing off and jiggling her thick ass at him, before turning around and chuckling as she took Tom's cock in her hands.

'Bit enthusiastic, are we?' She asked sweetly, before running her hands up and down his length. Tom moaned involuntarily, and Zara led him by his cock into the shower. They kissed deeply under the steaming water, Zara's huge erection slowly coming to equal and then even eclipse Tom's. He dropped to his knees and took her glans into his mouth, swirling his tongue around it like she had taught him to. Zara closed her eyes and moaned, but as Tom went to take more of her into his mouth, she stopped him, and make him stand up. Tom's cock was aching, and Zara gently took his testicles into her hands. They were full and swollen, and she grinned at him.

'Why don't we play a little game instead'

'So, it's called 'edging'?' Tom said dubiously, about ten minutes later. They were sitting naked on the bed, towelled dry after the shower, and to Tom's consternation, still with aching balls. Zara nodded.

'I do it sometimes to see how big I can make my loads. You, or someone else-' she gestured to herself, '-get yourself to the very edge of your orgasm, then stop. You do this over and over, until the slightest touch sets you off, and you'll cum, like A LOT. Trust me, even for us!' Tom grimaced.

'That sounds like torture, babe. Can't we just, y'know, fuck? I'm desperate!' He waggled his cock at her, and a drip of precum dribbled from his tip. Zara wiped it off with her finger and swallowed it, making Tom catch his breath. She leaned in close, her hand velvety soft on his glans, caressing it the way she knew he couldn't stand.

'Where would be the fun in that?' She whispered evilly. 'My record is 6 times to the edge in one hour. If you do that, I'll make you cum like a fucking fountain. You know I love huge cumloads! Please?'

'Well, I'll try anything once!' Tom smiled.

He lay on his back, his cock flopping onto his stomach. Zara squeezed a healthy amount of lube onto him and gently jacked him off. He immediately felt his cum rise in his balls.

'You wanna cum, baby?' Zara's eyes were all innocent, but Tom knew what a dirty, evil slut she really was. He loved it.

'Mmhmm' Tom thrust himself up into her grip, allowing Zara to caress his big ballsack as well.

'Good boy, so responsive, aren't you?' She breathed, quickening her pace. Tom felt the edge approaching. God he wanted to cum! Maybe she was just joking about stopping? But Zara felt it too and backed off, grinning at him and sticking her tongue out. Tom moaned in frustration, but Zara ignored him. He watched as she slathered her own pulsing cock in lube and jerked herself off.

'You like watching me do this?' She asked as she treated herself to both hands, going slowly along the entire length of her cock, and playing with her glans. She knew he did. She knew it drove him fucking mad.

'You want to taste it?' She shuffled forwards on her knees and offered her dripping glans to him. Tom leaned forwards and sucked on it like a lollipop. She always tasted so good! Zara closed her eyes in bliss.

'Good boy! I think that deserves a reward!' Whipping her cock away from him, she reached into their nightstand and got out a small buttplug, the kind designed to stimulate the prostate. It was one of Tom's favourite toys. A quick finger and a bit of lube, and Tom felt it nestling inside him. His hands reached up to stroke himself instinctively, but Zara batted them away.

'Remember the rules!' She said playfully. Tom could feel sweet forming on his face.

'Babe, I'm not sure if my balls can take this. They feel huge! I need a release!' Zara lifted up Tom's ballsack with mock care, caressing his now-enormous testicles, almost the size of lemons.

'Oh dear, baby, what can I do to help?' Without breaking eye contact, she leaned down and just, ever so lightly sucked on one of his balls. Tom was going mad. He couldn't take it! At the Alexe moment, Zara reached forwards and clicked a button on Tom's plug, starting its vibrations. They pulsed directly onto his prostate, making him gasp and twitch.

'Oh shit, Zara, it's too much, please, please...' But Zara was a master at her craft. For almost an hour she tortured him with bliss, turning the plug off and on, jerking him off, sometimes gently, sometimes like a whore, but always stopping just before he lost control. She praised him and kissed his neck, telling him how well he was doing. Tom had never known such agony. It was amazing.

Zara reached into the nightstand again and brought out a metal cock ring, which included a ring to tighten around the wearer's balls. She fitted it onto Tom, and his cock immediately engorged even further, its veins popping out along its huge length. Zara watched with satisfaction as his balls swelled as well, becoming bright red. They really were huge now, she thought. She would give him the release soon, but not just yet.

After another twenty minutes Tom was seeing stars whenever the buttplug was even turned on for a second, or if Zara breathed anywhere near his cock. She was jerking off freely next to him, building up her own orgasm, panting as she fought to control her urge to splurt her cum all over him.

'Baby, please...' Tom whispered, his body twitching and convulsing involuntarily. 'My balls, I need to drain them...please, just let me...'

Zara put a finger to her lips coquettishly, as though thinking his proposal over, her other hand never stopping sliding up and down her cock. The slick squelching sound of the lube and pre-cum between her fingers only added to Tom's torture. Her tits wobbled in time with her cock, and her tummy jiggled as well in that way that he loved. Suddenly, almost nonchalantly, her hands found Tom's plug and turned it on to maximum power. At the Alexe time, she used both her lube and cum-covered hands to jerk him off, as fast as she could. She knelt in front of Tom and jiggling her huge tits on his glans as she did so.

Tom's eyes rolled back into his head.

'You know what I want now, baby', Zara panted as she worked, one hand now caressing his huge, swollen, cum-filled ball-sack, feeling it vibrate from his plug. 'Impress me, make me proud!'

Tom cried out, and suddenly he was there, he had his release, he was in paradise. He thrashed out, completely out of control, as the strongest orgasm he had ever had ripped through him. Zara laughed and cried out with amazement as she was coated with rope after rope of thick, sticky cum, shooting out of Tom's straining cock with amazing force. His cum splattered against her tits and belly, spraying everywhere. Fuck, it was sexy!

'Oh good boy, Tom, that's it, empty your balls for me baby, keep going, keep going!'

Zara jerked herself off as well, climaxing quickly and covering Tom in with her load. This only spurred her boyfriend on, and she lost count of how many thick spurts he'd given her after twenty. Zara smiled in helpless amazement. She knew that her cock could perform miracles, but what it had done to Tom...she really was lost for words

Finally, after almost a minute of non-stop cumming, Tom subsided. His balls, previously straining at against the ring, were now much smaller, their torturous load finally spent. His cock shrunk from its gargantuan size, and Zara, her balls also empty, dizzily released him from the cock and ball ring and lay down next to him. They were both covered in each other's cum. Tom was breathing heavily, his eyes still closed. There was a squelch as his tortured cock flopped to one side, sliding through the thick cum, both hers and his, covering his chest

'Enjoy yourself?' Zara asked sweetly. She picked up his half-limp cock and sucked it clean, squeezing it gently to coax his last drops out, swallowing them all. Tom looked down at her, punch-drunk, grinning like an idiot. His vibrator was still going, and his cock twitched in time to it.

'Let's do that again sometime.' He said, 'only it can be your turn!'

'TOM! ARE YOU FUCKING READY OR NOT?' Zara's angry shriek reverberated up the stairway. Tom couldn't help but smile as he finished packing up for their holiday. She would be so calm and chilled out leading up to a vacation, but the minute the clock started, Zara could be one hell of a whip-cracker.

'Just a few minutes, darling!' He replied acidly, looking around to make sure they hadn't forgotten anything. Zara had packed all their favourite toys and lube, and Alex and Chloe were bringing most of the booze along, they had said. Initially, Tom had been a bit reticent about going on holiday with Zara's two closest friends. Both tall, slim, elegant women, Alex and Chloe had been nothing but nice to him, but they were Zara's friends first, and a part of him worried about to what extent they knew about Zara and her lifestyle, not to mention where HE fit in.

He threw his bag in the back of the car and jumped in the passenger seat. Zara glowered murderously at him, thumping a hand on the dashboard and making him jump.

'If you were fucking ready when I ASKED you to fucking ready, we wouldn't be RUNNING BEHIND! Why can't you just do what I say?!'

Tom kept a straight face for about five seconds and burst out laughing. Zara tried to stay angry but couldn't help grinning at her boyfriend, who had tears rolling down his face.

'Come on,' Tom chuckled, still snorting, 'let's go, we don't want to be late for Alex and Chloe.' He ducked as Zara aimed a slap at him.

Two hours later, Tom threw himself down on the huge bed in their room and breathed out a contented sigh. He and Zara had booked this trip a while ago, at a plush hotel out in the country. Originally a Gothic-style mansion, they had seen its turrets from miles away, and the landscape around it was breathtaking, deep, blue lakes and snow-capped mountains, together with the green forests that surrounded it all. They had convoyed with Alex and Chloe's car, and the two women were staying in the room across the hall. Zara was busy fussing around the room, unpacking and wondering aloud where she should put things.

'Fancy a swim and a sauna?' She asked him over her shoulder, holding up their swimming costumes. Tom nodded, swinging his feet off the bed.

'Any excuse to get you to take your clothes off.' He pulled Zara towards him, kissing her, his hands slipping down her jeans and squeezing her ass. She laughed and patted his crotch, cocking an eyebrow at him when she felt the hardness there.

'You'd better put this away before you take someone's eye out, hot shot,' she said, grinning, 'besides, Alex and Chloe are coming as well.' As if on cue, there was a knock at their door, and the two women came in, carrying their swimsuits and towels.

As much as Tom was crazy about Zara, and was definitely more into girls with some meat on their bones, there was no denying how attractive Alex and Chloe were. Alex was slim and willowy, with small, well-proportioned breasts and hips. Her long blonde hair ran halfway down her back, and she could easily have been a model. Chloe, contrast, had short, choppy brunette locks, and slightly wider hips than her friend. Both were capable of stopping traffic with their looks. Tom had had to try hard to stop himself grinning like a complete fool as they were all checking in, catching the clerk's eyes as he stammered and blushed in front of the three stunning women.

As they walked through the hotel, Tom couldn't help but notice that it was nearly deserted. The school holidays were months away and it was the middle of a week in February, hardly a popular holiday period. All of his party had booked this off work months in advance, but he hadn't expected it to work out quite this well. The girls went into their dressing room and he went into his, smiling a greeting and the one other man in there. Tom felt a thrill as he stripped off, casually turning round buck naked and showing off his huge cock. He saw the man freeze as he watched it flop obscenely from side to side. He didn't think he would ever get tired of showing this thing off.

Zara chatted and laughed with her girlfriends as they got undressed in the ladies' changing. There was no one else in there at all. Although there were cubicles for privacy, her, Alex and Chloe had been friends forever, and they had all seen each other naked countless times before. She had even fooled around with both of them in the past. She hadn't told Tom this, though, telling herself that it didn't matter, but something did gnaw at her, especially as her heart quickened washing her two friends strip off. Pretty soon they were all completely naked, laughing and completely at ease.

'Zara, you just have the BEST body!' Alex said, laughing as she jiggled Zara's tits up and down. 'I mean, look at these! They're HUGE! God I wish mine were that big!' She stuck her face in Zara's cleavage and motorboated for all she was worth.

'Bigger isn't always better,' said Zara, laughing with her hands on her hips, her chest thrust forward for Alex to play with. 'Although I get on ok, I suppose...'she stuck out her tongue at her Chloe, who laughed.

'Well, I certainly wish more guys looked like you in the OTHER department.' Chloe said, sitting on one of the benches and gazing at her friend's enormous cock, her blonde hair messy about her face. Alex voiced her agreement, and Zara felt herself blush.

They were so hot, she thought involuntarily, and she loved that they kept their pussies natural, no shaving at all. She felt her cock start to stiffen in the cool air, and turned to look for her swim suit, hiding her blushing, guilty face.

'What does Tom think about 'bigger isn't better?'' asked Chloe, shimmying into her bikini bottoms, her tits still bare. 'I can't imagine he would be with you if he thought that!' She nodded lightheartedly at Zara's bobbing cock.

Zara shrugged as she pulled on her one-piece, pulling the shoulder straps up and adjusting her breasts.

'I've never really asked, but the amount of sex we have, I think he likes what he sees.' She could help but smile.

'Do you fuck him as well?' Alex asked, adjusting her bikini top, a playful, inquisitive smile on her lips.

'Like a champ,' replied Zara, 'we both do everything. He is Bi remember, so I don't think it's a huge leap for him. Besides, he isn't exactly 'small' himself anymore!'

They were all ready. Zara twirled in the mirror, making sure her assets were properly secured. She had to admit, her ass and tits did rock this bathing suit...

Tom was glad he was waist deep in water when the girls came out of the changing room. His cock was immediately rock hard. He had seen Zara naked, but something about her in a bathing suit drove him mad. The other two girls looked dynamite as well, and they all climbed down the steps of the deserted pool and swam smoothly towards him. He glanced surreptitiously down to make sure his cock hadn't escaped. This was going to be a tricky exercise...

The pool was completely empty aside from the 4 friends. With floor-to-ceiling windows showcasing the stunning countryside outside, together with the waterjets, whirlpools, and miniature waterfalls dotted around it, it was a genuine paradise. Tom and the girls splashed around laughing and joking for around half an hour, before Zara suggested they take a quick trip to the sauna. Tom's pulse quickened. The water had hidden his package thus far, but out there, there would be no escape. He hoped Alex and Chloe wouldn't think he was a pervert, but even just watching them climb dripping out of the water, squeezing it from their bikini tops, he felt his cock stiffen again.

'All ok?' Zara asked, half out of the water, looking back at him. Tom swallowed, and nodded down to his crotch.

'I'm a bit...exposed in just my shorts, babe, I don't want to freak anyone out...'

Zara smiled and climbed out of the water. Turning round, Tom started as he saw her raging hard-on, clearly visible through her leotard.

'Do you think that I should be embarrassed?' said Zara, hands on her hips, completely unashamed. 'It just my body, Tom, nothing to be self-conscious about.' She motioned him out of the water, and, holding hands, they went into the sauna.

'Besides,' said Zara, 'it's nothing they haven't seen before, and we're all adults here.'

Soon the four friends were sitting in the deserted sauna, basking like lizards in the heat. Tom sat next to his girlfriend, facing Chloe and Alex on the wooden slats opposite. The air was humid and steamy, but Tom had a front-row seat to the two gorgeous women opposite him His cock strained at his shorts.

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