Popping his Sissy Cherry

Please note, this story was written for my sweet sissysub, David. It is something we both found fun and sexy and thought you might enjoy it too, which is why we chose to share it. If you don't understand or enjoy the themes in Femdom or sissification then this is not the story for you. Please do not waste anyone's time by leaving hateful rants in the comments or via direct mail. All such ignorant ramblings will be deleted with extreme prejudice. All other feedback is welcomed.

If you would like to read about David's journey into sissydom, the stories in order in this series are Cucked by the Chairman and Burning for Her.

David was in torment.

His shaft was heavy and throbbing from five days of edging, balls burning with the twin sensations of ice and fire inspired by the generous layer of toothpaste he had applied that morning. This has been his daily routine since the night that his Goddess had commanded him to stroke his well-slathered cock for her while suckling her fingers that were drenched with her sweet, spicy cunt honey. Later, she had granted him permission to cum and then fed him every viscous drop of his rapidly cooling semen. It has been an intense experience and, by continuing the torture, he felt that he was honouring her with a daily act of worship which he hoped she might feel inclined to reward.

Since the night he was called into his Chairman's office, David instantly became erect whenever he was in Peter's presence which added a dangerous frisson to business meetings and presentations. He couldn't even hear his superior's name mentioned without remembering Peter's thick, heavy cock plunging into his Mistress' tight channel as he rutted her vigorously over his desk. He'd always known that he'd felt a deep submissive thrill at the hands of the dominant women in his life, but that night, kneeling under Peter's desk paying homage to his Mistress' clit, tongue sliding against Peter's rigid shaft while his balls butted him rhythmically on the chin, he understood that he had so much more to experience. Being naked but for the panties he'd been forced to wear at the time, opened up a whole new sissy headspace and he longed to fall further down this deliciously forbidden rabbit hole.

And so it was, with his burning flesh fit to burst out of the slutty lingerie he'd worn underneath his tight jeans, he found himself standing outside the elegant loft apartment that evening.

As he tentatively knocked on the door, he looked once again at the text message he'd been sent by his beloved Mistress Kate:

Sweet gurl. You have impressed us with your enthusiastic service and the way you have taken to being our sissy little slut. No innocent blushing virgin, it seems. What a cum-hungry cockwhore you have turned out to be. How delightful! Be at my apartment at 8pm sharp and wear something pretty for us. Tonight, you come to us an innocent little gurl, but we intend to teach you what it is to be a woman. Your cherry is ours, sweet one.

Each time he read it, the fear and excitement of anticipation only made his cock, his clit he corrected himself, throb even harder and he was already close to cumming. He took deep breaths to steady himself as he heard his Mistress' high heels tapping as they approached the door.

Standing on the step above him in her towering 6-inch stilettos and black bodycon dress, Miss Kate gazed down at her quivering sub, extending one long manicured finger to lift David's chin to meet her eyes.

'Any second thoughts, pet?' She asked gently. 'This is a big moment in any innocent gurl's life, so it's only natural to be a little nervous. But then, fear is so close to excitement, isn't it, sweetling?'

David was trembling with anticipation, but there was nothing, nothing, that was going to stop him from experiencing everything that his Mistress had in store for him. He had waited so long for this, all his life if he was honest with himself, and he was ready to offer himself completely.

Taking her offered hand and entering the well-appointed apartment which was straight out of the pages of a glossy aspirational magazine, David was led into a cosy sitting room with a roaring fire. In front of the fire on an elegant leather sofa, was his Chairman, Peter. Wearing suit trousers and an open-necked shirt, his waistcoat casually unbuttoned and a drink in his hand, Peter exuded an aura of masculine confidence with his legs spread, and his arm draped along the back of the sofa. David couldn't stop his eyes sneaking a look at his crotch, which he now knew hid an impressively thick shaft and a heavy pair of balls.

'Good evening, gurl. I just knew that you couldn't stay away. Like a moth to a flame, you can't help being drawn to the thrill of the forbidden, can you, you little slut?' he smirked. When David blushed, he raised a commanding eyebrow and firmed his voice. 'Strip.'

David's mouth was dry, and he wished he too had a stiff drink to knock back in order to bolster his courage, but he knew that this was his first test, and he wasn't about to fail it. Quickly, he slipped off his shoes and peeled off his socks revealing toenails he'd shaped and painted a glossy fire engine red, before stripping off his soft, baby blue cashmere jumper and tight jeans to reveal what he had chosen for the night. To say that he'd agonised over his look for the evening was entirely accurate. In fact, the trip to the waxer -- a petite, but surprisingly strong Korean lady who'd taken what could only be described as an unnaturally sadistic thrill in ripping out every single body hair she could get her hands on, even going so far as to make him bend and spread his cheeks as she tweezed any remaining hairs that had escaped the hot wax -- was an experience that would long stay with him. He wanted to look pretty for his Master and Mistress, as he'd come to think of them, but not too innocent. In many ways, he wanted to seduce them with his choice of lingerie, to impress upon them that he may be inexperienced, but he was ready for this, eager to give himself to them fully. And so it was that he'd chosen the sluttiest of the outfits he'd furtively bought for himself.

The little black teddy he'd worn made him feel seriously sexy and feminine. It had flirty lace around the high legs to accentuate his slim hips and matching lacy cups that chafed delightfully against his sensitive nipples. Nipples that had been made even more tender by the cruel little clothes pegs he'd punished them with earlier that evening. The stretchy, wet-look fabric that stroked his freshly waxed body felt like a caress every time he moved, especially where it cupped his throbbing clitty. But it was the thick, double-ended gold zip that he hoped would most entice his alphas, starting as it did between his diamond-hard nipples, working its way past the heat of his clit, between his thighs to end just above the curve of his butt. He was shaking just imagining it being unzipped, leaving his quivering cheeks so vulnerable, to expose him for whatever his superiors wished to do to him.

'Very nice, pet,' Kate murmured appreciatively, 'but I think we just need something more.' She sat on the couch next to Peter and beckoned David closer, dropping a throw pillow to the ground and indicating he should kneel before her. Reaching for the patent red cosmetics purse on the side table she removed a gold compact, which she used to brush powder over his upturned face, the soft brush contouring his cheekbones as he preened like a kitten with each tantalising stroke. Next, she uncapped a thick, black mascara, and applied it to his naturally full lashes, accentuating David's wide eyes, desperate as he was to please his superiors. A touch of eye shadow and blush was applied before his slightly parted lips were painted with a slick layer of trashy bright red lipstick giving him a brazen fuck-me pout. And then the masterstroke -- Kate reached behind her to pull out a long, wavy blonde wig, which she tugged over David's short hair. On seeing his reflection in her compact mirror, David was overcome with emotion. He did look feminine, pretty even! The flowing golden curls softened his jaw, and his eyes, with their long, feathery lashes, were wide and innocent. But it was his lips, blowjob lips, he thought to himself, that drew his gaze. Surely Peter would be unable to resist their appeal.

Peter chuckled with pleasure, 'There's our dirty little fuckdoll. Next time, I expect you to come fully made up for us. And no more jeans; I expect my slutty little gurl to dress to impress. There's nothing like flipping up your skirts to give you a thorough rogering, now is there?' he smirked, licking his lips appreciatively. 'Well, slut? Tell us what you need from us tonight.'

David was sinking further and further into his sissy headspace. 'Please, Miss Kate, Master Peter. Will you teach me how to please you? How to be your good gurl? Make me yours?'

'Gladly, pet,' Kate sighed sensuously as she inched up her tight dress, slipping her red lacy panties down her stocking-clad thighs and languorously toying with her pussy. Reaching out one manicured hand and ruthlessly seizing David's head by his soft, blonde locks, she thrust it between her parted thighs and forced him to breathe in her sweet, spicy perfume. Needing no further encouragement, David snaked his eager tongue from between his own glossy red lips and lapped diligently between Kate's until she pushed him away, instead forcing his head between Peter's spread thighs where he'd begun slowly stroking his girthy alpha shaft which he had released from his perfectly pressed suit trousers, a steady stream of precum leaking provocatively.

'Ah, ah, greedy gurl. Not so fast. You want a taste of my cock, then you have to beg for it,' chuckled Peter.

David had never forgotten the taste of Peter's sperm, which he had received second hand via a kiss from his Mistress, and today he wanted more. He wanted to know the feeling of having his slutty lips stretched by a thick, powerful shaft, the hot, heavy weight on his tongue. With the thick, musky head so close to his face, David was so aroused his mouth was watering and he couldn't hold back the desperate moan. He did want it. Want to taste it, choke himself on it and, most of all, to please his Master.

'Please may I have a taste, Sir? I just want to make you feel good, to please you. I want to suck your big, thick cock, Sir. Please, may I?'

And as he looked up at Peter, never breaking eye contact, his desperation and arousal painted on his face, it was clear that the time for teasing had passed. The hands in his long hair forcing him down on the throbbing head was accompanied by a groaned 'Fuuuck!' of approval.

It was hard to tell who was the most aroused -- Kate, avidly strumming her clit as she watched every hard thrust that made David's eyes water, or Peter, as he forced his thick meat to the back of his kneeling sissy's mouth, her long hair wrapped around his fist as he mercilessly claimed her tight throat, as was his right. Or maybe it was David, whose eyes were watering not just from the hot, thick shaft he was trying so hard to accommodate, but with the gratitude that such a powerful man was taking time to train his little gurl how to please him so well.

With his lips swollen from his service to his Master, David's carefully-applied lipstick was smeared around his slutty mouth as he sped up, Peter taking control of his head with both strong hands that muffled his ears so that his whole world became cock - the salty male taste, the texture of velvet over steel as it stroked his tongue and stretched his shiny, red lips, the obscene sounds as his throat struggled to take Peter's length, the scent of his Master's groin as his nose was ground into the wiry silver hair with every hard thrust.

Seeing David so thoroughly dominated, Kate strummed herself faster as she issued the order, 'Play with your clitty for us, sweetie. Frig yourself with your fingers, but remember, good gurls don't cum without permission. And you do so want to be a good gurl for us, don't you?'

Then, forcing her hand away from her aroused petals, she stood, watching for a moment as her sweet gurl bobbed up and down, choking herself on her Master's cock, before reaching for the long, thin, lacquered box sitting on the end table. Lifting the lid, she smiled as she stroked her fingers down the thick rubber of the double-ended dildo. Cherry red. How very appropriate.

David was unaware of what was happening behind him, so intent was he on following his Mistress' command as he stroked his aching clit which had grown so hard, so very tingly, knowing what a dirty little gurl he was as he laboured over his Master's cock, his mascara staining his tear-streaked cheeks.

With a voice gravelly with arousal, Peter asked, 'Are you ready, gurl? Ready to take a full alpha load in your pretty little mouth?'

And, yes, thought David, nearly cumming with excitement, yes, he was ready. His stuffed mouth was watering, hungry for the bellyful of warm seed he craved.

And then Peter fisted David's hair and pulled back so that his bulbous head lay on his tongue. Grunting his release, he gifted him the full taste and texture of the heavy gush of sperm that he unloaded into David's eager little mouth until his cheeks bulged.

'Hold it like a good gurl,' Kate cautioned, knowing that without her steadying command David might forget himself and greedily swallow down his salty treat. 'Show us.'

David was in heaven. All his taste buds were firing. He revelled in the rich taste and scent of the semen pooled between his slutty lips, and opened his mouth to show off the thick load of frothing alpha spend, cheekily waggling his tongue through it to bathe his taste buds in the gift.

'What a good little cocksucking slut,' Peter murmured as he wiped his cock clean against David's cheek, marking him as his property. 'Now, swallow it all down and don't you dare spill a drop.' Both alphas watched as he gulped the rich mouthful several times and licked his red lips to ensure that none was wasted.

Still on his knees with his arse up, head now resting in his Master's lap, he closed his eyes, a feeling of pride and utter contentment relaxing his limbs, turning him languid, despite the fact that his clit was aching with unspent arousal. When he felt strong, masculine hands stroking his hair, he almost purred like a kitten.

But his short rest was over, he discovered, as he heard Peter's warm baritone at the same time he felt his Mistress' soft hand on his upturned buttock.

'That's right, sweetheart, stretch her out for us. Stretch out her sweet, untouched little gurlcunt. There's more to being our little slut than just being good with her mouth. She needs to be our submissive little cockwhore in all ways, don't you, pet?' he asked, his hand still stroking possessively.

David experienced a whole-body shudder in fearful excitement as Kate gently, but insistently tugged the zipper over the curve of his butt, only the rasp of the teeth and the crackling of the fire breaking the charged silence. Kate continued the path of the zip until his clit was freed, then stopped when she reached his navel. David didn't move his head from his Master's lap but he could feel the heat of the fire caressing his naked cheeks as she gently parted the sides to reveal his forbidden gurly hole to her gaze.

Kate's finger probed at the tight, shy little rosebud and, even with her fingers slippery with her own arousal, she could tell that she was going to need more to gain entrance to such a tight, untried hole. Moving her hand to his head, she pushed her honey-slicked fingers into his mouth to add his own moisture. However, instead, he eagerly set to work cleaning them for her; a job he took very seriously as he ensured every molecule of flavour was diligently licked clean. As she slowly slid her fingers out, he moved his head forwards sucking desperately, his eyes on her, pleading to be allowed even a few more seconds contact. Kate smiled knowingly and ran her finger around his lips, chuckling indulgently as David looked up at her through eyes hooded with lust, licking his lips like a cat that got the cream.

'You, pet, are incorrigible! I wanted you to get my fingers wetter, not suck them dry!' she chastised, playfully.

'Oh, but she's so good at sucking us dry, isn't that right gurl?' asked Peter smiled, his eyebrow raised. And David felt a glow of feminine pride infuse his body, making his swollen clit throb harder than ever.

'There's only one thing for it. You're going to have to show us how you touch yourself. Don't think we don't know that you finger your tight little hole when you think of us.' Kate gently took David's hand, pressing his fingers between his glossy lips. 'Suck, pet.'

David blushed as he bathed his own fingers in saliva, then shyly but in no way reluctantly, eased them down his body to his exposed cleft. His quivering opening welcomed his slick fingers -- first one, then a second -- as it had so many times before in the last few weeks. The fact that he was being watched by both his alphas made it that much filthier, and his clit jerked, begging for the attention he would normally be paying it. However, he hadn't been given permission and he did so want to please, so he neglected its insistent call and just focussed on pumping his fingers into his hot little channel. Rocking his hips, he spread his thighs wider and moaned at the delicious stretch, flaunting himself for their entertainment.

'Oh, look how easily they slip in. She's loving it!' Kate exclaimed. 'She was born to take a thick cock, don't you agree, Peter?'

'Add a third now, gurl,' Peter commanded,

'make yourself feel the stretch. You're going to need to really gape that sweet little cunt if it's going to accept what we have to give you.'

David tried, but the scant saliva was now gone, and his hole was so tight that he whined in discomfort and frustration.

'Slicken your fingers again, sweetheart. Suck them well to ease your way. We don't want you to hurt yourself, pet,' Miss Kate cautioned.

David knew she was right but slipping his fingers back into his mouth as he was watched, tasting the earthy scent of his gurlcunt, was possibly the most depraved thing he'd ever done and that thought thrilled him even more, sinking him further and further into his sissy headspace.

But now David had a new focus as Kate had joined Peter on the sofa, bringing a lacquered box with her. Peter pulled her into his lap and kissed her deeply, passionately, as he stripped her of her dress, leaving her in just her heels, stockings and a tight black corset that nipped in her tiny waist and pushed up her generous breasts to the older man's lips and tongue. David continued to finger himself eagerly as he watched the show in front of his face, wishing that he were man enough to take his Mistress so confidently. As she bounced her hips, grinding against Peter's cock, the plump, pale globes of her arse were mere inches from David, and he longed to rock forward and bury his face between them to worship her with his tongue. But no, it was not his place. He was a sissy little gurl preparing herself to be plundered of her innocence and he wouldn't have it any other way.

As Kate pulled away from Peter, her face flushed and her breasts heaving for breath, she reclined on the sofa and spread her thighs wide, exhibiting her glossy, swollen petals to the two sets of hungry eyes. Opening the box, she pulled out the long, thick jelly dildo and handed it to Peter.

'Help me with this, won't you, love? Let's show our gurl how to open herself to receive a nice, thick shaft.'

Sliding two fingers between her aroused lips, Kate spread them wide, exposing her innermost petals and her slick, welcoming hole.