P.A. for a Day

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

At a nod from Mistress they both rose from the table. She rang a small bell. At that Nicole entered the room and stood waiting Mistress's bidding.

After a few minutes Mistress nodded and Nicole moved into place behind Charles. Inserting her hands into waistband of his panties she gently lowered them, guiding them over his throbbing hardness and down his stockinged legs until they fell to the floor of their own accord. How he loved the erotic pleasure of kiss of his silken panties brushing against his nylon encased legs. Charles stepped out of his panties. He now stood pantieless before Mistress and Nicole, his hot hard cock firmly erect framed on top by his garter belt and at each side by the garters. His cock moved up and down as he clenched and unclenched his pussy lips, working his sanitary pad further into his rosebud.

Mistress slowly encircled him inspecting his body. As she walked before him she gently stroked his cock and knob with her riding crop. Moving behind she used the crop to prod his sanitary pad and gently brush the tip across his buns. His panties still lay on the floor. If Mistress was dissatisfied with his performance she would signal for him to bend over and pick them up, and stay in that position until told to rise. As he bent Mistress would strike his buns with her riding crop, several times if she was really dissatisfied. Nicole had told him some horror stories of how Mistress would whip her sissyboys to such an extent that they experienced discomfort for weeks afterwards.

This time Mistress seemed to take longer than usual to decide. Or was she just teasing him, prolonging his agony. Finally she picked up his panties with the tip of her riding crop and draped them across his throbbing hardness. Mistress was pleased with him today. What further favour would she bestow on him in appreciation of his efforts?

Charles stood motionless as under Mistress's watchful eye Nicole gently caressed his shaft and knob with his panties, occasionally cupping his stones in the palm of her hand and gently squeezing them. How that girl knew how to please a sissyboy, especially when she caressed his most sensitive knob. Leaving his panties draped over his cock Nicole lifted her dress and gently rubbed her own pantied cock against Charles's knob. Oh what sensations of delightful erotic ecstasy flooded through Charles's body as their knobs kissed through the soft silk of Nicole's panties. Mistress herself showed her excitement of the spectacle as she fondled and rubbed her dildo to stimulate her pussy juices.

Nicole removed Mistress's loose robe, carefully folding the silken garment in her hands. Charles yearned for the touch of the warm silk against his most sensitive skin, especially his cock. He desired to partake of Mistress's erotic aura. However, Nicole placed the folded robe on one of the chairs.

Mistress now stood in her black bustier, stockings and evening gloves. Her bustier almost reached to her hips, her stance displaying the dildo to its best advantage. Although Charles was proud of his cock, Mistress had him at a disadvantage. Standing before him she allowed the knob of her dildo to kiss his knob, and then let her knob rub along the length of his shaft gently bobbing against his most sensitive skin. Finally she placed the knob of her dildo at the point where Charles's cock emerged from his crotch, the dildo was the longer by almost an inch.

Mistress gave him a coy smile of triumph. Although Charles wasn't a size queen he was proud of his cock and displayed it to other sissyboys at every opportunity. But this time he was beaten and by a dildo not a real cock, even though that dildo was a latex replica of a gay icon's cock.

Moving behind Charles, Nicole removed the rear tab of his sanitary pad from its clip and let the pad dangle between his legs. As she let it drop she examined it for sissyboy menstrual blood. Not finding any she looked up at Mistress and shook her head.

With a tube of lubricant Nicole moistened the knob and shaft of the dildo and then rubbed some lubricant along Charles's crack, giving special attention to his pink rosebud. As Mistress stood behind him, her gloved hands holding his waist in a firm grip, Charles spread his legs and bent slightly forward, his butt ready to receive the dildo. Mistress touched his crack with the tip of the latex knob and gently rubbed the knob back and forward. While Mistress was attending to Charles from behind, Nicole was on her knees tonguing his knob and fondling his shaft and stones with his panties.

Suddenly Mistress stopped and shifted her stance. Removing her hands from his waist she gently spread his buns apart. Charles bent over further allowing the dildo easier access. Still holding Charles's buns apart Mistress gently inserted the knob into his pink rosebud, stopping just after it had passed his sphincter gate. The worst part for Charles was now over. Although his butt had been regularly penetrated for years by dominas and sissyboys, his rosebud was still tight, but once he felt the knob inside him he could relax his butt muscles to receive the shaft.

Mistress resumed gripping his waist and adjusted her balance for the next stage. Her body tensed and Charles could feel the erotic pleasure of the latex shaft sliding up inside him, until he took its full length. It was heavenly. The erotic pleasure of the dildo up his butt was much superior that the pleasures he got from having sissyboys push their real cocks up inside him. As the dildo slowly slid in, Charles felt the warmth of Nicole's mouth as it took the full length of his cock.

Charles clenched and unclenched his butt muscles to welcome the latex shaft. It felt most comfortable, much better than many sissyboy cocks he had experienced. The feel of its springy softness was most erotic. The erotic sensation coursing through his body was only enhanced by the knowledge that of all the sissboys at her disposal Mistress had chosen him to deflower her new dildo. He felt it was a privilege, nay, an honour, to be so chosen. And the dildo wouldn't collapse inside him. Sometimes this happened with sissyboy cock when the queen on the other end lost the power of his erection, to the disappointment of both sissyboys.

Once again Mistress stopped to adjust her balance and get a firmer grip round his waist. Their bodies were touching. Mistress leaned over and showered Charles with her kisses. Starting with his shoulder her lips gradually moved to his neck and cheek, then round the back of his head and down to his other shoulder. As she kissed him Charles could smell the delightful odour of her perfume and feel the erotic touch of her long shiny black hair brushing across his skin. Ah, what erotic bliss.

As Mistress showered her kisses upon him, his mind went back to other erotic episodes in his life. His initial defloration when his boyfriend had introduced him to the delights of taking sissyboy cock up his butt, the pleasure of feeling the hot cum shooting into him as his boyfriend's body jerked in erotic ecstasy. His first experience of a gay gang bang when he joined a sissyboy group and all the members present had rammed their cocks up his butt and shot their load inside him. After that experience an older queen had introduced him to the erotic delights of sanitary pads to ease the discomfort he had felt for several days afterwards. His first experience of a dildo up his butt, which his then domina insisted was his real defloration, and afterwards as she lay fondling his cock she teased that he was now one of her dildo dollies.

All these experiences passed through his mind before he felt Mistress adjusting her balance again and he knew that the real pleasure was about to commence. Starting with long slow strokes Mistress rode his butt while Nicole sucked his shaft and knob. With each thrust Charles could feel the sac at the base of the dildo flapping against his own sac. Oh what erotic ecstasy he felt at being serviced from one end by a real lady while at the other end being serviced by a girl like himself. And even more erotic delights were in store.

Still sucking Charles's cock Nicole lifted her dress and fondled her cock and knob through her panties as a prelude to masturbating. Her masturbatory pleasures drove her to higher levels of trembling ecstasy and she sucked on Charles's cock even harder. Soon he could feel the sensation of his cum rising in his shaft. By now Mistress was speeding up her strokes as the dildos inside her got her more and more excited and the sac flapped faster and faster against his own sac.

Charles felt Mistress's body stiffen and then all three climaxed simultaneously in one orgy of erotic orgasmic bliss. As Mistress reached orgasm she arched her back and thrust forward, forcing her dildo even further into Charles. This touched off something inside Charles and his body jerked as he shot spurt after spurt into Nicole and he felt her greedily swallowing his cum. Nicole's own cum rose as she furiously rubbed her cock, writhing and shaking in her orgasmic convulsions, then the hot sticky cum flooded into her panties. The force of her orgasm made her so excited that for a moment, Charles was frightened that in her erotic ecstasy she would bite off his cock.

By now all three were exhausted and flopped down on chairs to recover. Nicole was the first to get up and leave the room, returning shortly after with a basin of hot water and towels. Kneeling in front of Mistress she gently washed her dildo, and after drying it sprayed it with perfume and dusted it with talcum powder. Then it was Charles's turn. He bent over to allow Nicole to sponge his crack and cock. After drying them Nicole sprayed his crack, stones and shaft with a vaginal deodorant, her fingers spreading the lips of his pink rosebud open so she could spray he cool air inside him. Charles loved the eroticism of the cool spray against his girlie bits as he liked to call them as it made him feel really feminine. Nicole then. Then came the cool feel of the talcum powder as she dusted his cock and ball sac. Finally she sprayed the vaginal deodorant on the sanitary pad before fastening the tab to the belt and gently placing it tightly against Charles's crack, her finger pressing it up into his rosebud.

The experience had left Charles with some discomfort down there and he was grateful for the soothing influence of the sanitary pad which felt like a cushion up his butt. Nicole then sprayed his cock and shaft with perfume before holding out his panties for him to step into.

Mistress and Nicole watched as Charles dressed in his street clothes. At Mistress's nod, Charles picked up his document case containing the letters he had typed. He would post them on the way home. Nicole accompanied him to the door gently kissing him on the lips as they had a final round of mutual fondling.

"Mistress was delighted with you today," she whispered in his ear. "And your cum has such a lovely flavour."

"Let's hope you get the chance of afters you naughty, sexy girl."

"We compared cocks last night and my cock is still the longest. If I'm good Mistress may let me play with it again, maybe when she is wearing it. It would be bliss for us two girls to fondle each other don't you think?"."

"Only if I am there to watch. You can tie me up so I can't play with my cock. That would be real punishment for this sissyboy. A hot throbbing sissyboy cock needs fondling, preferably through soft silky lingerie. The punishment of being denied that pleasure while watching you girls fondling each other would be most erotic to this sissyboy."

"I'll talk to Mistress and see if we can arrange something then", Nicole giggled as they kissed and fondled their farewells.

Charles walked round to Mistress's garage and got into his car. As the gates closed, he mused about how quickly the world can change. Whereas this morning life seemed pretty hopeless, now the world was opening up before him.

He already had the key to the executive washroom and the directors and senior staff obviously enjoyed fondling his cock. Some of the old queens were really sweet and after word of his passion for silky lingerie got around, they got even more passionate in their fondlings. According to office gossip getting the key to the executive washroom was the first step. The next was being invited to use the executive dining room, and the same office gossip was that he would soon receive that invitation. After that who knew, maybe an invitation to join the board.

And that sweet young sissyboy he had met in the bathhouse the other night. Didn't he make the first move, catching Charles's eye in the cruising area and following him into the sauna. And after the first fumblings to the erotic pleasure of the other sissyboys, accepting Charles's suggestion that they repair to one of the cubicles where behind a locked door they spent hours gazing into each others eyes, rubbing their smooth naked bodies together, fondling and kissing the night away with the occasional bout of mutual masturbatory pleasure.

Oh what a beautiful smooth body the young sissyboy had and so magnificently hung, his long straight cock ending in the most magnificently formed knob, and not a hair to be seen. A pure delight to touch and fondle. And didn't he give Charles his card with his private number as they were dressing. Handled right this could be the start of the love affair of the century.

Life for Charles was indeed looking brighter.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

Similar Stories

Being Taught To Wear a Garter Belt Teenager is taught what to wear by girlfriend.in Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
Patti Cake Ch. 01 "I won't tell anyone you're packin' pantyhose..."in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
My New Neighbours I get to know my new neighbours.in Transgender & Crossdressers
More Stories