In the Club

No longer virginal, now degraded. That is my life as Dave's sissy whore Chandra. With my girlfriend Nikki and her boytoy Adam, we descended into our city's LGBT club scene with a fervor. Dave and Adam were only too happy to share their girls with their friends, and Nikki and I adored the attention, the sex, and the feeling of being desired by so many men.

Our favorite club was Whisper, an underground sex club for wealthy gay men, many of whom presented as straight, were married, but couldn't get enough ass and cock. When Dave called me and told me that tonight was going to be a big night at Whisper, I immediately ran over to Chandra's with my makeup bag and some new outfits.

We had our ritual down pat. First, a shower where we helped each other shave, kissed, and rubbed our little clitties together. Then, we dressed, applied makeup, put in our favorite gem-ended plugs, and thoroughly tarted up, waited on the men to pick us up.

Tonight, Nikki was wearing a set of tight leather shorts with the edges of her black thong pulled up, knee-high boots, and a crop top with black fringe. She had on a shoulder-length purple wig and smoky eyeshadow with black lipstick. I had chosen pumps with a short shredded black denim skirt, lacy pink boy short panties underneath, and a bralette with pink stitching. I had covered my nipples in little black Xs of electrical tape. I had on a platinum blonde wig and green eyeshadow, with some trampy hot pink lipstick. When Dave saw me, he remarked how nice it would be to have that smeared all over his cock. In response, I felt him, half-hard, through the front of his pants. He wormed a finger around to caress the crack of my ass, finding my plug already inserted. "What a good little slut you are," he whispered in my ear. I grinned and bit my lip.

Nikki took my hand, and we left the apartment, to Adam's waiting BMW below. The boys piled in the front, while we sat in the back, and drove out of town to the club.

With the cover paid and the memberships proven, we entered. We made a lazy circuit of the club, Nikki and I swaying our hips in time to the beat of the heavy electronic music. One of our favorites, a regular named James, saw us and whistled. I turned, and lifted my skirt a little. He let out a sigh.

"David," he said, motioning us to sit down. "I hope this means Chandra will participate in a show tonight."

"Of course, James. What is the point of owning a whore if you can't trick her out."

I knelt on the carpet beside Dave's chair, resting my head on his thighs. Nikki sat on his other side, her arms wrapped protectively around Adam's leg.

We watched as a young, twink-y boy was led to the center of the room. A very busty woman held a leash attached to a thin leather collar at his neck. "My name is Mistress Genevive," she said. "And here I have a new toy. He says his name is Alex, but that he has always wanted to dress up like a girl and get fucked in the ass."

There were howls of delight.

"He is not a good boyfriend," Gen pouted. "But maybe he can be a good girlfriend. What do you think?"

She switched across his ass with a riding crop, and he jumped. "Let's get those boy clothes off!" she shouted. He moved to disrobe, but Genevive switched him again.

"A proper lady does not undress herself," she chided. "She must have handmaidens to prepare her."

With that, a trans girl we all knew as Marley strode in, wearing white lingerie, a nice bustier that cupped her delicious-looking breasts and lacy white panties that I would have killed for. Her heels were scandalously high, and she strode over to Alex.

"Alex, Alex, Alex, what a terrible name," she simpered, lowering herself and unfastening the button of his pants. "You should be Alexis, I think." Alexis shivered in pleasure as Marley rolled down his pants, exposing the red and white thong.

"Oh my, panties!" Gen exclaimed. "Already halfway there."

Marley turned Alexis around, showing off the tight lines of his... no, her... body, the pert little ass, the tiny bulge of what I could only assume was not the world's biggest cock, and the tiny erect pink nipples in the middle of her chest.

"Just think, you were once like that," Dave murmured to me. "All innocent and virginal."

"Oh yes," I said, stroking his now obvious hard-on. "But you ruined me, darling. You made me into your slutty little princess."

"Yes, so why don't you share some lessons with young Alexis there?"

"Dave, do you plan to take her cherry?"

"I don't know; would you be jealous?"

I thought. In the months that I had been introduced to the fetish lifestyle, I had let go of many inhibitions. I did not think I was in love with Dave; I loved the sex, sure. And he was hot and kept me in clothes. But could I see him with another sissy, a younger and more virginal one? Yes, I decided. I would love seeing Alexis's virgin boipussy stretched over Dave's cock, to hold open her cheeks as she was first penetrated. To watch as my man pumped his seed into her waiting sissy womb, to welcome her to sissy womanhood.

"Dave," I said. "If I don't see you come in her tight little ass tonight, I'll wonder if you still have the virility to claim me later on."

He grinned, a wicked smile. "You have truly embraced your degradation."

"It's sex," I shrugged. "We should share the pleasures of the flesh. Alexis is new, she will need a kind lover, just as I did. You are the best, and so you should initiate her into a life of serving cock."

"I believe I shall, but first, why don't you go help her get in the mood?" He reached down and lifted the bralette up. I stretched my arms overhead, letting him expose my titties to the club. James whistled again.

"When are you going to let me buy you implants, dear?" he said.

I smiled. "I don't need implants yet, James. I haven't decided if I'll transition."

James nodded. "You make a fine woman regardless. Now go show our new recruit the ropes."

"The only ropes I care for dangle between the legs of the men here," I said, but nevertheless began to crawl, on all fours, to the middle of the floor. Gen saw me moving, and stepped aside.

"Oh, what luck, Alexis," she crooned. "Here is young Chandra to teach you the ways of being a girl."

I crawled to Alexis's knees, and said, "may I kiss your clit, my sister?"

Alexis, now visibly erect, nodded. I pulled the lip of her panties down and began to lick and kiss the tip of her clit. She was very excited, and I ran my hands down her legs and ass crack. I felt her tense up.

I pulled off the clitty in front of me. "Relax," I commanded, and Alexis did, sinking down to her knees. Her hands felt experimentally for the tape at my nipples.

"May I?" she asked.

"Please rub my nipples," I said, bending to kiss hers. "You have such pretty ones."

"I don't feel pretty."

"Why not?" I said, switching to the left nipple.

"I'm still in just panties."

"We all start somewhere," I said, rising up to lock lips with Alexis. People cheered. I pushed her over onto her back. Gen slid a cushion by us, and I maneuvered her up onto it at a slight angle. Her legs parted.

I gave Alexis a light slap on the legs. "Not yet, precious," I said. "You will be fucked, but not by me. I'm just a girl like you." I giggled.

Alexis tried to giggle. "There you go," I said, encouraging her. "Get into it; let your mind drift to the feminine."

We stroked each other's bodies. "I love your skirt," she said

"I'll let you try it on," I said, "after your scene."

"Scene?" she asked.

"Yes, it's what we're doing. Putting on a show for the men. Once we've teased them enough, they'll come fuck us. My companion will take you. Don't worry, he's gentle and an excellent lover."

She gulped. "This is so hot. I mean, I've never had sex with a man before..."

"You came to the right place. We will teach you."

Genevive sat beside us now, her legs thrown open and one hand lazily diddling her clit through her now sodden panties. She produced a thin pink vibrator, covered in a condom, and handed it to me.

I took it and began to rub it alongside Alexis's clit. She shivered again.

"Turn over," I said, and she did, bending over the cushion, presenting that pink rosebud to me. The men cheered again.

"Fuck her!" someone called. I looked into their direction and wagged my finger. I ran the vibrator up and down Alexis's boyslit, pausing each time I teased her opening. Marley knelt on the other side of me.

"Your lingerie is gorgeous, doll," I said. "You have to tell me where you got it."

"Thank you," Marley said. "I really like your outfit tonight. But I think I'll get more sperm in me."

"Oh, you are on!" I said. Marley opened a tube of lube and began to squirt it on Alexis's crack. I used the vibe, still off, to spread it around. Alexis jumped.

Dave had crossed to us now. He took Alexis's chin in his hands. "Don't move," he commanded, and she froze, her eyes locked on the swinging dick now freed from his pants wagging in front of her nose.

"It's too big, sir," she said.

"Nonsense," I said, slipping the vibrator inside of her. Her ass puckered and tried to push back, but Marley was already soothing her.

"Relax, let it in. Push out, there you go. Good girl. What a fine slut you'll be."

Alexis moaned for the first time as I flicked the vibrator to life in her pussy.

"Say it," I said. "Say, oh that feels good in my pussy."

"It feels good in my pussy," she moaned.

"Say it again. I don't have an ass, I have a tight pink sissy pussy."

"I have a tight pink sissy pussy."

Gen shouted as she climaxed for the first time.

I was plunging the vibrator in and out faster and faster. My own little clit was not straining at my panties to get released. I felt Gen come up behind me, pressing her tits against my back. She began to rub my clit through my panties.

"Harder, faster," she breathed in my ear, her other hand starting to rub my nipples. I purred against her, feeling her wet crotch start to grind against me. I really began fucking Alexis with the vibrator now. She let out a series of girly squeals.

Marley was still whispering in her ear. "You're a woman now. You only get pleasure from penetration. Think about it. You want a dick in your pussy, right? All girls do. Well, there's one in front of you now. Just open your eyes!"

Alexis's eyes opened and beheld Dave's full erection in front of her face. Without thinking, by reflex, she opened her mouth and engulfed him. "There you go," Marley said. "What a pretty little cocksucker you are. Get that veiny monster all nice and slick and maybe he'll fuck you with it."

Untrained as she was, Alexis tried to focus on both the pleasure in her asshole and the invading cock in her mouth. After a minute, Dave withdrew his manly dick from her mouth and said, "Slut, has the virgin's pussy been properly prepared for me?"

"Yes, master," I cooed, removing the vibrator and switching it off. Marley took it from me and went to dispose of the condom. Dave walked around behind, and knelt beside me. I pulled Alexis's cheeks open.

"Hm, yes," Dave said. "That is a tight little pussy." He dipped a finger inside.

"Almost too tight," he said, putting another finger. Alexis grunted. Genevive took up the side opposite me and applied more lube to Alexis's soon to be deflowered hole.

Dave handed me a condom. I leaned forward, taking the foil packet, and sucked him for a few seconds, relishing the feel, the hardness, and the taste of my man's dick.

"Take her from the front," I said. "For a girl's first time, she should look into the eyes of the man she is pleasing."

Genevive groaned in pleasure as we helped Alexis turn around and positioned the cushion, elevating her ass and passage. I opened the condom and rolled it down Dave's dick. Gen and I each took one of Alexis's thin little legs and spread them apart, lifting her ass. Dave scooted forward, his dick making contact with Alexis's asshole. He paused.

"Alexis," he said, "please tell me, 'fuck my virgin ass, Dave. Fuck my virginity away.'"

Alexis, her face flushed, sweat beading her brow, whispered, "Fuck my ass, master. Fuck it good." I leaned over to kiss her nipples. Alexis screamed, "please get that dick in my pussy!"

Dave thrust into her gently, taking his time to ease his massive tool inside her tight pussy. Alexis grunted and groaned as she became accustomed to the feel and girth of a real dick. Once I saw his pubes come to rest against her cheeks, I said, "that's it. You're a real woman now. That's a man's dick inside you. Do you feel it?"

"Yes, yes I do," Alexis moaned. "Oh it's so big."

"You're taking it great," I said. "Put your legs on his shoulders."

Her legs came to rest on Dave's shoulders as he adjusted himself for the real thrusting, the true fucking.

"Fuck her, lover," I said fondling his heavy balls. "There's so much sperm in these. Some of it needs be in this whore in front of you."

Dave began to thrust, still slow and gentle, until he had worked Alexis's hole open enough to begin thrusting in earnest. Genevive leaned over and kissed Alexis, open mouthed, tongue lolling out. I reached out to fondle her breasts, relishing in the heavy weight of them in my hand. I looked over to see Nikki now engaged in jerking Adam off while watching, obviously entranced with the scene. I motioned for her to join us, but she shook her head. Too crowded already.

Dave leaned over and planted his own kiss on Alexis's lips. She moaned and slid her legs down his side, locking ankles behind his back. He began to thrust harder, and I saw white sperm shoot from the tip of Alexis's clitty as he pounded her prostate.

"Oh, fuck," she screamed. "Oh fuck fuck fuck fuck."

"Her first orgasm as a woman," Genevive said, smiling.

"too much, too much," Alexis screamed, and Dave withdrew from her. We laid Alexis back down, murmuring soft words. "You did so well," I said. "You can stop if you want."

"No," Alexis shook her head. "I need to make him come, right?" I nodded. "It is our duty to please our men," I said.

Dave crossed to the restroom and removed the condom. He wiped himself clean and came back. I helped Alexis into a kneeling position, and grabbed her face. "If you can't make him come with you pussy, then a good slut must learn to use her mouth."

Smiling a wicked grin, Alexis began to bob on Dave's dick again, this time with more gusto. I saw Dave reach down to stroke himself a bit, and I began to toy with his balls in the way he liked. In short order, he said, "I am going to come."

Alexis pulled off, leaning her head back and closing her eyes. I grabbed Dave's dick and directed the hot ropes of come all over her face. Genevive and I then went to licking it off, cleaning up Alexis's pretty and now come-covered face. Dave crossed back to his chair, where James handed him a towel and a bottle of water.

"Very hot," James said, "but unfulfilling for young miss Chandra here."

Dave smiled. "I'm spent, but perhaps you, James, might assist me in this?"

"I would be delighted," James said. I stood, allowing James to lead me by the hand to a private room in the back. Once inside, I sat down on the bed, crossing my legs and batting my eyes at him.

"Can I fuck you bareback?" he asked. "I can show you my test."

"Dave has cleared you," I said. "I prefer to take my pies creamy."

"And I prefer to come inside," James said, pushing me back on the bed. I maneuvered my ass up so that he could pull off my panties, which he did, but left them dangling on an ankle. He grabbed my cheeks and spread them apart, gasping as he saw the plug.

"How pretty," he remarked. "May I remove it?" I nodded, and he took the plug from my fuckhole, setting it beside the bed. He knelt again, and plunged his tongue forward into my gaping sissy pussy. "Oh yes," I crooned, enjoying being eaten out.

"You taste like honey," he said, licking all around the entrance. A finger found its way inside me. "And feel like velvet."

Another finger joined the first, and I whimpered. He liked that. I felt my panties drop from my ankle as he repositioned my legs.

He unbuttoned his shirt, revealing a powerful and muscular chest. I unbuttoned his trousers, finding him commando underneath. "Oh my," I gasped. James's cock was huge, at least ten inches. "I had heard you were big," I said, " but this is... this is a weapon."

"And it's all yours, my dear," he said, letting me draw it out of his pants. He kicked them away, and I relished the feel of him growing hard in my hands.

"James, that is not going to fit in me," I said.

"Oh, it will," he chuckled. "I'm going to have you suck me until I'm as hard as I can be, then I'm going to bend you over this bed and fuck your ass until I shoot my sperm inside you. Then I'm going to plug you back up, filled with come, and you're going to go back out there and tell Dave how much of my sperm is in you."

I love that kind of dirty talk. "I'm not sure you have enough sperm to fill me," I said. "I am a wanton whore and I've taken more dicks and sperm than you know."

"You haven't had mine, dear," James said, standing and offering me his now erect penis. I smiled and kissed the mushroom tip, opening my painted lips and sinking down on that massive tool. He gasped appreciatively as I tongued the underside. His hand tangled in my wig as we settled into a rhythm. I glanced up at him through my lashes, and he smiled down at me.

"Such a pretty little cocksucker," he said. "Did you enjoy watching that new bitch her get ass spread open by Dave?"

I moaned an affirmative around his weapon.

"God I bet she was tight," he said. "But obviously without your skills at sucking cock. I saw you help finish Dave off."

I ran a pink-nailed hand up to his balls and began to play with them as I sucked.

"See, now that's a slut move," he said. "You are a true sissy whore, pimped out to your man's friend for fucking and breeding."

"I am yours, sir," I said, rising and turning, presenting my open hole to him. "I am a vessel for your sperm and nothing more."

"Just an empty-headed sissy with a gaping asshole to be filled by a real man's dick," he said, pushing toward my opening. The head slipped in, and I grunted as I tried to adjust to the sheer size of the dick now fucking my pussy open.

"Slow," I said. He didn't listen. Oh, by the goddess he didn't listen. He shoved forward, I yelped, and he slapped my ass.

"A real whore doesn't complain when she's fucked," he growled. I wanted to submit to him so bad. I willed my ass to open for him, and it did. My pussy enveloped him. I felt his weight press against my back, the intoxicating feeling of that massive hard dick driving into me.

"Harder, harder," I gasped as he began to thrust, expertly running across every sensitive spot in my pussy.

"Oh fuck," he groaned as I tried to squeeze him.

"Oh fuck me," I said as I felt my own orgasm building. How could I not with a huge fucking dick like that pressed against my sensitive sissy spot? I grunted and shot sperm all over the sheets. James pulled me up, hands on my hips, fucking me as my little clitty exploded again. I let out the girliest scream as I felt so feminine and precious impaled on that giant dick, nipples erect under their tape barrier, skirt flapping wildly as my asspussy was ravaged by this huge cocked hunk now balls deep in my tight pink little pussy.

His orgasm was a fiery explosion deep in my guts. I felt him throb and shoot, seeding me, breeding me, making me shiver and shake as he came in me again and again.

I fell forward, spent, abused, my gaping hole thoroughly creampied by this massive tool now deflating behind me. I felt James replace the plug as I lay there panting.

"Jesus fuck that was good," he said. I could only moan, no words could be formed. "Most girls never let me get that deep."