Meg Saunders

Pushing Damon towards Sissy, Meg whispered, "You'd better kiss her equally as well when you bring her back, Mister."

Damon couldn't believe his luck. Two of the hottest chicks to ever come into his restaurant were dancing with him and openly flirting. Especially the one named Meg. There was something special about the other, though. Anna made his dick throb every time she smiled at him. Oh, he'd fuck Meg at the drop of a hat, but Sissy had him intrigued.

When she returned to their table a couple of steps ahead of Damon, Meg quietly whispered in Sissy's ear, "When he brings you back to the table, let him kiss you and kiss him back."

Sissy-Anna gulped but nodded her assent. A few seconds later, Damon squeezed her bum as he danced closely with her to a slow dance the DJ played. To Sissy's surprise, her fettered cock tried to rise to the occasion. That she was turned on by a man casually groping her ass had her mind blown. But she nearly swooned when she felt Damon's rigid dick pressing against her abdomen.

'Gawd!' She thought. 'I can't be sexually excited about being able to turn a man on, can I?'

But the evidence was there by the throbbing head of her severely taped-down cock. Sissy kissed Damon back as passionately as Damon kissed her when the dance ended.

Close to midnight, Meg kissed Damon and said, "We can catch an Uber to my place, if you're up for it?"

"Gawd, yes," Damon exclaimed. "I've been fighting blue balls for the last hour!"

"No promises, Mr Demon," Meg emphasised. "You might be in for more than you planned!"

Initially, Meg had planned to pretend Sissy was on her period and that Damon would have to fuck her in the ass. But Meg liked Damon and hoped he'd become a permanent part of their lives, so she wanted Damon to know Sissy was a woman with an extras package before they fucked. So if he were game, he'd get to have them both tonight. If he freaked out, well, no loss, really. Grabbing Sissy and Damon's hands, Meg hurried them outside and into the Uber. This time, Meg insisted that Sissy sit next to Damon.

"He's hard for you, Sissy. Let him kiss you, and when he does, stroke the tips of your fingers over his cock," Meg whispered to Sissy before letting her slide into the car.

Knowing Meg would insist, Sissy encouraged Damon to kiss her by turning towards him and smiling. Hoping he wouldn't notice her breasts weren't natural, Sissy rubbed her 'nipples' across Damon's upper arm.

Then, letting Damon lean in and kiss her, Sissy asked, "Is waiting tables what you do, Damon? Or is it to make money for something else?"

"I'm studying C.A.D. (Computer Assisted Drawing), Anna," Damon answered. "Waiting tables allows me to pay for my college courses upfront, which will save me a heap of money in the long term."

"Well done you," Sissy said. "I'm an air conditioning mechanic by trade. Meg sells real estate."

"Wow!" Damon said. "There can't be too many female aircon mechanics?"

'If only he knew', Sissy thought. But she said, "There's not too many. But hopefully, with the positive practices the Colleges are instigating, there will be more in the future."

The Uber stopped in front of Meg's place. Regretfully, Sissy let Damon's hand go and slid out behind him as he exited the Camry.

'Oh, Lawd," Sissy thought. 'Did I just perve on his ass and think it's sexy? What has Meg done to me?'

Whatever it was, Sissy knew she wanted more. Being honest with herself, Sissy-Anna knew that she'd made love to Meg as three men dressed as women. But, if this progressed as Meg intended, it would be one male making love to two women. Could she handle that? Could she play the feminine role well enough that Damon wouldn't notice? Sissy doubted it because, after all, she had a cock, not a pussy, for Damon to fuck.

"Penny for your thoughts," Meg whispered into Sissy's ear.

"You want him to fuck me, don't you?"

"Oh, Gawd, yes!" Meg averred. "How Gawddamned sexy will that be?"

"Why?" Sissy asked.

"Because it's sexy, and I want to see it. Plus, baby girl, don't deny it, but you want to experience being fucked as a woman."

Meg opened her door, "The bathroom is down the hall on the left," she said to Damon. "Once you've finished, wait for us on the couch here. We'll join you in a minute or two."

Meg guided Sissy down to her bedroom, "I was going to make you pretend you were on your period and force Damon to fuck you in your ass. But, baby girl, I think he'll be up for it. So, when you begin to make love to him and me, spread your thighs, and let your cock out."

"He's going to freak out, Meg," Sissy insisted. "What if he tries to assault us both?"

"Then, like my asshole ex-boyfriend, he'll get my cast iron fry pan in the middle of his face as hard as I can swing it."

Sissy had to laugh, "That's a story you will have to tell me later, Miss Meg. But okay. If you think I can do this, and he can take it, let's go fuck Damon."

Wearing a diaphanous gown of Meg's each, the girls walked down to the lounge to take Damon to bed. Underneath their robes, the girls still wore bras, panties, suspenders, stockings and heels. So, looking like whores in a brothel, Meg and Sissy entered the lounge and offered themselves to Damon to choose from. As they hoped, Damon let Meg and Sissy lead him to Meg's bedroom.

As they walked through the doorway, Meg hissed at Sissy quietly, "Before he has a chance to think, get on your knees and suck him off. Trust me, once he's cum in your mouth, he won't care you're a chick with a dick."

Following Meg's advice, Sissy-Anna had Damon's turgid cock in her mouth moments later. Given how much they had teased him, it was no surprise when Damon erupted into Sissy's mouth moments later. Damon, satiated temporarily, sagged onto the mattress. Meg cuddled into one side as Sissy hugged his other.

Taking Meg's advice, Sissy spread her thighs and lifted her knee up and over Damon's hips. Sissy was scared but very aroused, so as soon as she let her cock free, it began to grow and harden.

With his eyes widening, Damon felt Sissy's appendage swelling against his thigh, 'WTF!' He thought. 'Surely Anna isn't a...?'

Damon forcefully rolled Sissy-Anna over, and her thick cock bounced into view.

"Oh, Gawd, yes!" Damon exclaimed and immediately took Sissy into his mouth.

'Now there's a surprise,' Meg thought as Sissy's hands almost unwillingly went to Damon's head as he swallowed as much of Sissy's length as he could.

Looking into Sissy's eyes, as Sissy humped slowly up into Damon's mouth, Meg said, "Good, baby girl?"

"Oh, my Lawd, yes," Sissy groaned.

"Better than me?"

Sissy knew a loaded question when she heard one. But, although Meg was an exceptional cock sucker, the intensity of receiving her first blow job from a man had Sissy's senses overloaded. Nevertheless, she still shook her head and moaned, "No. Good though. Very, very good."

"Good answer, baby girl," Meg smiled. "But I can tell Damon's doing a fine job."

Damon let Sissy-Anna's dick fall from his mouth, "First time," he said before swallowing Sissy again.

"For Sissy or you?" Meg asked.

Damon let Sissy out again, "First time I've sucked a cock. I've always wanted to try a shemale, though, so this is freaking awesome!"

"Transgirl," Meg absently corrected as she observed again how well Damon gave fellatio. "You're good, Damon. Especially for a first-timer."

"I have one of these," Damon said, taking Sissy's cock out of his mouth and waving it at Meg. "I'm just doing to her what I like having done to me."

Kneeling close to where Damon's head bobbed on Sissy, Meg asked, "How much can you take? You've got a little over half in so far. Can you take the rest?"

"I keep gagging if I go any deeper," Damon answered as he let Sissy out.

"It takes practice, honey," Meg explained. "You can't speak sentences until you can say words, right?"

Damon's eyes watched her as he nodded.

Reaching for Sissy's cock, Meg said, "Here, let me show you."

Sissy groaned deep and gutturally as her dick slid from Damon's mouth. Then sighed almost as deeply when Meg swallowed her down. Meg held Sissy's thick 6-inch halfway down the shaft as she bobbed her head up and down. Meg swirled her tongue around the glans when her lips reached the crown of Sissy's cock.

Letting Sissy fall out of her mouth, Meg turned to Damon and explained, "I already know where my gag reflex is. So I wrap my hand around the cock just before that spot. Then I can bounce my head up and down as fast as I want. But, of course, to give the best blowjobs, you want to milk the cock with your hand as you suck."

Meg changed positions so she could use both hands. Placing her left hand at the base of Sissy's dick, Meg showed how she could now stroke her right hand up and down Sissy's shaft as she blew her, confident that her right hand would hit her left before Sissy's cock's head hit her gag reflex.

"You try," Meg said, offering Sissy's dick back to Damon.

Damon tentatively tried what Meg had demonstrated. A short time later, Damon bobbed up and down on Sissy's shaft, almost like an expert.

"I'm going to cum," Sissy gasped.

Meg and Sissy assumed Damon wouldn't want Sissy to orgasm in his mouth, but Damon surprised them both by swallowing as much of Sissy as he could before cupping Sissy's balls and squeezing them lightly.

"Yesssssssssssssss!!!!" Sissy hissed as he exploded into Damon's greedily sucking mouth.

Damon swallowed all of Sissy's gift willingly, but as he turned to wipe his face and lips clean, Meg kissed him passionately, swirling her tongue around Damon's lips to gather up the spillage. Smacking her lips to show she enjoyed the taste, Meg tongue kissed Damon again.

"Strip," Meg demanded of Damon.

He quickly complied, revealing a leanly muscled body with an erect, pretty good, standard-sized cock. Damon's penis was a little shorter than and not as wide as Sissy's.

'It'll be perfect for taking Sissy's virginity tonight,' Meg thought. Then she giggled to herself, 'And it'll be perfect for my ass when they double-penetrate me later.'

Cupping her hand behind Damon's head, Meg kissed him as she pulled him with her as she lay down. Meg was so hot from watching Damon blow Sissy that she didn't need warming up, so she encouraged Damon between her firm thighs and guided him into her sopping snatch.

Reaching out her hand, Meg pulled Sissy in close for a kiss before whispering in her ear, "Kneel on either side of Damon's legs, baby girl. Then tongue his rosebud for him."

Gulping, Sissy moved to do as Meg instructed. Damon's cock was fully seated inside Meg, but at this stage, he was only pulsing his cock inside Meg as he kissed her lips and nibbled on her ears. To Damon's surprise, he felt Sissy's hands massaging his buttocks. Then, Damon groaned as Sissy's warm, wet tongue swiped from over his rosebud up to the cleft of his ass before probing and tonguing that same sensitive spot.

Damon groaned as his dick jumped inside Meg. Forcing himself to relax, Damon continued arousing Meg with his mouth and fingers as Sissy spread his ass cheeks and ran her tongue in tightening circles around his pucker hole. Damon moaned again as he felt Sissy's tongue probing into his sphincter. Damon had never had this done to him before, and he was already struggling to contain his orgasm. The fact that Meg was squeezing him rhythmically with the walls of her pussy wasn't helping, either.

Damon almost called a halt to proceedings when he felt Sissy's finger pushing into his ass. But as he opened his mouth to protest, Meg kissed him hard and thrust her hips forcefully up at him.

"Relax and enjoy this, Mr Demon. Live a little sinfully, as your name suggests," Meg hummed into Damon's mouth.

Meg was shocked at how far Sissy was going, but she was determined to let Sissy play with Damon as far as she would go. Meg would make Damon let Sissy do whatever Sissy wished by continuously distracting him with her body. Meg's assets were hard to resist. Meg knew that. Damon would allow Sissy to do more to him than he could imagine as long as he continued to sample Meg's charms.

Meg lifted her knees higher and gripped Damon more firmly with her thighs as she began thrusting forcefully up at his invading cock, "Now, Mr Demon, you need to fuck me. You need to fuck me right now!"

So Damon did. As he thrust forwards into Meg, Sissy's tongue followed his rosebud, but when Damon pulled back, Sissy's tongue flattened against his starfish. This, along with Meg's pussy tightly gripping his todger, brought Damon swiftly to the edge of orgasm.

"I'm nearly there, Mr Demon," Meg panted. "Fuck me hard, really hard, and cum inside me."

Three more pounding strokes were all Damon could endure. Being with his first 'lady boy', sucking his first cock and having it cum in his mouth and now, having his chocolate starfish rimmed as he stroked into one of the prettiest women he'd ever met was too much. With an expansive groan, Damon jetted his semen into Meg's tightly gripping pussy.

Feeling her new man cumming inside her was enough to send Meg crashing into her orgasm. Her moans echoed Damon's as the pair thrust together.

Coming down, Meg noticed Sissy was kneeling beside her. Sissy's throbbing erection speared out from the top of Sissy's panties, "Bring that here, baby girl," Meg moaned. "I want to taste you again."

Sissy loved how Meg always referred to her 'boy parts' in feminine pronouns. Instead of saying, "I want to suck you,' as she would to a man. Meg said, "Taste you," as if Sissy's dick was a vagina to taste. Dressed as sexily as she was, being addressed in feminine terms added to Sissy's arousal and made her feel very sexy. Shuffling across the bed quickly, Sissy offered her thick erection to Meg's lips. As she took Sissy into her mouth, Meg pushed on Damon's chest and encouraged him to go down on her.

'Would he?' She wondered. 'He'd happily swallowed Sissy's orgasm, but would he lick her pussy knowing it was full of his cum?'

Without hesitating, Damon slid down Meg's body and soon had her clitoris hood pulled back so he could tongue it properly. He was a little high, though. Damon was good, but unlike Sissy, he hadn't found 'little clittie' yet. Meg moaned around Sissy's cock and pushed Damon's head down. Misunderstanding her needs, Damon lowered her mouth onto Meg's labia and opening.

Although it was mentally exciting to have Damon eating his cum out of her pussy, it wasn't bringing Meg any closer to the orgasm she craved, so Meg demanded her two lovers change positions. Damon, of course, was keen to have his cock sucked, but Meg was again surprised about how readily Sissy attacked her cum dripping pussy.

Unerringly, Sissy found little clittie, and Meg was soon simmering on her way to another orgasm, "Yes, baby girl," Meg moaned around Damon's dick. "Just like that!"

Damon's insistent grunts and pants made it clear he was about to cum in Meg's mouth. She didn't want that this time, though. Meg wasn't sure about Damon's staying power, so she wanted him to cum in her ass before he flagged. So, letting Damon's dick fall from her mouth, Meg instructed Sissy to lie on her back and hold her thick, erect cock so it pointed at the ceiling.

Lowering herself onto Sissy, Meg glared at Damon, "Well?" She asked archly. "Are you going to leave a girl wanting?"

Again misunderstanding, Damon offered his dick to Meg's lips.

"Wrong hole, Mr Demon," Meg informed him.

"What?" Damon sputtered. "You're what? Offering up your ass?"

"As long as you prepare it properly," Meg answered.

"I've only had anal sex the one time, Meg," Damon confessed. "She was up for it and didn't need me to do much. She took me in her mouth to make me wet and then rolled over and told me to go for it. I started gently because I was worried about hurting her, but she demanded I fucked her hard. So I did, and she came several times before telling me to fill her up."

Sliding off Sissy, Meg got onto her hands and knees, "Sissy, show Mr Demon how to prepare an ass for a fucking." Turning her head to Damon briefly, Meg said, "Mr Demon, you've fantasised about fucking shemales, but haven't studied how to get them ready?"

"Well, the girls in the movies seem to be able to take a cock up their clackers without any preparation, Meg," Damon replied.

Meg rolled her eyes, "Yup, Damon. And every girl on the planet loves ass to mouth."

"Do they?" Damon inquired.

"Fuck no!" Meg spat. "You take your cock out of my ass and try and put it in my mouth, and I'll rip your Gawddamned balls off!"

"Oh," Damon murmured. "I thought it was too good to be true, but I hoped. You know?"

Getting the lube from the top of Meg's dresser, Sissy spread Meg's ass cheeks and gently ran her tongue from the entrance to Meg's vulva, along Meg's perineum and onto her soft, chocolate rosebud. Following this path several times, Sissy ensured Meg's crack was well lubricated and ready for penetration. Then, Sissy slid her index finger into Meg's ring. Next, adding lube, Sissy rotated her finger gently around, stretching Meg's sphincter wider.

"Oh, Gawd, that feels good," Meg moaned.

Adding more lube, Sissy inserted a second finger. If it were Sissy screwing Meg in the ass, she would add another finger before swapping to her cock. But Damon's girth was nowhere near as wide as Sissy's, so two fingers would stretch Meg enough. Next, Meg took Damon's rampantly erect todger into her mouth and swirled spit all over it with her tongue. Then, to make doubly sure, Sissy poured a generous amount of lube onto and into Meg's rosebud. Finally, Sissy took Damon's cock in her hand and guided him into Meg's ass.

"Ohhhh!!!!" Meg sighed as she felt Damon slide home. "Sissy, get over here, girl. I need you in my pussy."

Meg and Damon moved, so they stood on their knees on the bed. Then Sissy slid underneath Meg. Taking Sissy's thick cock in her hand, Meg lowered herself onto it. Another luxurious sigh eased from Meg as the two cocks slowly filled her to capacity.

Damon held Meg's hips tightly as he knelt behind her and gently stroked into her ass. Sissy, underneath her, thrust into Meg's quim in time with Damon. Sissy delighted in feeling Damon's big hairy balls bang lightly against her smaller bald pair. To Meg's delight, neither lover inside her seemed to be in any hurry. This meant Meg could savour many minor orgasms as she built towards her epic cum event.

Underneath her, Sissy bent her head forward to lick and nibble on Meg's crinkly hard nipples. Meg sighed again, her voice deeper and more profound than before. Sissy knew Meg was swiftly climbing to her orgasmic peak again and would soon need her and Damon to thrust faster and more firmly as Meg neared her climax.

Hoping Damon would take the hint and increase his speed with her, Sissy started thrusting into Meg with greater urgency. Fortunately, Damon moved along with Sissy, and Meg's soft sighs of bliss changed to moans of desire, then finally to grunts of pure pleasure as her climax neared.

Finally, it was on her. Throwing back her head, "Meg shouted, "YEEEEEEEEEEESSSSSSSSSSSS!!!!!!!!!!" Then thrashed about as her orgasmic contractions shuddered through her.

Damon hadn't cum, yet. But, after Meg's orgasm ended, he backed out of her and quickly walked down to the bathroom to wash his cock and balls. It wasn't that he was disgusted by having anal sex with Meg. Instead, Damon was bothered about Meg's ass-to-mouth comment and wanted to ensure his pubic area was sparkling clean if the girls wanted further play.

Luckily for Meg, Sissy knew Meg liked to lie on her lover with their cock 'marinating' in her pussy as she waited joyfully for the after-orgasm shakes to wash over her. Sometimes, if her lover was patient and Meg's body co-operated, Meg could orgasm again.