My Girlfriend's Idea Ch. 03

Story Info
A young man is delivered to a drag club by his girlfriend.
3.6k words
4.56
32.7k
41

Part 3 of the 3 part series

Updated 06/09/2023
Created 07/06/2019
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

I phoned her that night but reached only the answering machine. I was confused so I mumbled and tried to leave a casual "call me" message. On hanging up I felt embarrassed and flushed with shame. Later I tried to jerk off, thinking first of Cindy and then, inevitably, remembering sucking Clarisse off. It felt strange, I didn't cum. I took a shower and went to sleep.

The next day was a blur of lessons and an inevitable top 40 band fight over which of the covers should open the set. Not caring I stepped outside and watched suburban traffic. Cindy phoned that night.

"Hi! How are you?" She sounded cheery, hyper.

"I'm okay," I said. I was in love with her and the sound of her voice was an incredible relief.

"Oh that's good baby. You were such a bad boy in the studio!" She was laughing.

"Is that okay?" I mumbled and immediately regretted it.

"Maybe ..." She said, teasing. "Come over right now." She said and the line went dead.

Feeling like the relationship was now an entirely new world I drove to her apartment as fast as I could. I knew I was doing what I was instructed to do. I sat at a light and realized I had been erect since the phone call.

Cindy greeted me at the door in her white button down waitress shirt and black skirt as if she was at the restaurant.

"Hi sweety!" She looked at me half serious. "Did you brush your teeth?"

"Yes," I said.

"Oh that's a good boy." She leaned in and stuck her tongue in my mouth. I surrendered to the bliss of the French kiss. I felt her hands reach around and cup my butt. She broke the kiss and pulled me inside.

"But you were soooo bad in the studio!" She was laughing. I smiled at her, helpless.

"It was your idea." She led me to her bed and sat me down. She looked at me before kissing me tenderly.

"You're so sweet to do that for me." She leaned in and kissed me aggressively. I kissed her back. I felt her hand unbuckle my pants and her fingers reach in to my underwear. "mmmm boys underwear" she whispered before kissing me again. Her hand avoided my erection and she lay me back on a pillow, kissing me and bringing her hand to my rear end. She continued kissing me and her finger began to caress my anus. I involuntarily spread my legs. Continuing to stroke she pulled out of the kiss.

"My little virgin girlfriend. Are you my virgin girlfriend?" Her rubbing was sending pleasure into my stomach.

"If that's what you want," I choked. She stroked harder.

"Did you enjoy the other day?" She asked.

"Yes," I said, my lust rising.

"Oh baby," she whispered and began kissing me again. Her finger penetrated me slightly, tenderly. I moaned.

"Moan for me," she said. I let out a groan and felt myself begin to cum. She kissed me, stroking my anus lightly as I came. Spent, I relaxed onto her bed.

"That ... was incredible." She slid back and stood up. She raised her eyebrows. "My turn?" It was a question and an instruction. I looked at her. "Take off your pants," she instructed.

I slide my pants and underwear off as she retrieved a stack of bar napkins. Lying on her bed I watched her go into a her dresser and come up with a pair of panties.

"Wipe yourself off and put these on." I wiped up my cum off my stomach and slid on the silk girl panties. They were tight and cool and I felt my erection returning. She knelt up on the bed, hiking her skirt up. I realized for the first time she wasn't wearing underwear. She pushed me, gently but firmly, back onto the bed and straddled my face. I reached my lips out to caress her folds but she shifted, presenting me with her anus. I began to massage it and she pressed her cheeks into my face. She slid her rear back and forth as I attempted to work my tongue inside of her. Abruptly she adjusted and forcefully pressed her vagina into my mouth and nose. I did my best to help as she ground away at my face. She started shuddering and came, her sweat and vaginal juices covering my mouth and face.

She collapsed back on the bed beside me breathing hard.

"oh wow ..." She sighed. We lay there silent for a moment. I had nothing to say and wasn't even looking for words. Abruptly she slid off the bed and grabbed my hand.

"Come on it's time for a shower."

She led me back into the shower where we stripped and were soon standing in the stream of warm water. In the past we'd had shower sex but that didn't seem to be her plan. She soaped herself and rinsed very quickly before beginning to soap me, spreading soap under my arms before getting behind me as I faced the shower head. She began soaping my buttocks and I instinctually started bending over to give her access.

"You're going to have to keep this very clean," she said as her hand spread soap over my anus. She penetrated me for a moment and I became hard but it was apparent this was grooming, not sex. "We need a clean virgin bubble butt," she said matter-of-factly and then giggled, turning off the water. "Or so I've been told." She laughed and stepped out of the shower.

I put the girl panties back on as she dressed and she laughed with delight.

"We have almost matching panties!" My hard-on pressed against the fabric as she led me back to the bed. "I don't think we should have more sex tonight," she said and pulled me into a kiss. I French kissed her and we fell asleep.

In the morning I was dimly aware that I was awake before her so I slipped out of bed and into the bathroom to piss. I was turned on but not erect. Moving quietly back to the bed I knelt before her, running my tongue across the top of her panty line. We'd woken each other up with oral sex in the past and I knew she loved it. I slowly slipped her panties down and began to lick the top her her fur very gently. She sighed and her legs open.

"Oh my," she mumbled, half awake, and I began to lick up and down the folds of her vagina. She spread her legs further and I penetrated her with my tongue increasing her breathing. As she stiffened in preparation for her orgasm I brought my mouth back to her clitorus and massaged it forcefully with my tongue. With a series of shudders she came, her legs flinching as she made gasping sounds with her mouth. Then we were quiet, my now motionless lips resting against her pussy. I pulled away slowly.

"Well good morning!" She said.

She hopped up and into the shower, emerging fully clothed, her page boy haircut framing her perfect features. I had dressed when she was showering and she hustled me out the door and down into the standard apartment complex parking lot. Standing by her car she kissed me.

"Don't masturbate without asking me. Promise?"

"Yes," I said, and theatrically added. "I'll seek your permission." She got in her car and I watched her pull out before getting in mine.

-----------

That weekend we cabbed across the suburban streets into the rural edge of the city, to the rock and drag club that was the center of the scene in our exurbs. She had insisted on cabbing and she ignored the line, forcefully speaking to the enormous goth door girl who didn't even check her clip board, handing Cindy some drink tickets and waving us in.

The club was hot and crowded. I'd been here on drag night many times, to mix bands and Clarisse's track, but this was different. Cindy was wearing the white tube top, my absolute favorite of her outfits as it made her perfect breasts stand out while leaving her shoulders exposed. The previous best sex I'd had with her was reaching into the tube top while she went down on me. But now, this was different. She held my hand and directed me around the bar. When I'd arrived at her door she'd asked me forcefully if I'd showered, yes. And if I'd cleaned my rear carefully, yes. And if I was wearing her panties, yes. With a quick "good boy" she'd French kissed me and slapped my butt. Now, in the club, she led me through the drag night crowd to the bar and ordered hard liquor.

Claresse performed at the end of a revolving set of drag queens but the performance room was so crowded that I could only hear the dim thud of her track. I wasn't here on business so I didn't climb into the sound booth, standing instead with Cindy by the bar and finishing two drinks.

As the performances finished the DJ started up and Cindy turned to me. She looked like she was going to say something but instead pecked me on the lips and led me by the hand to the stairs that rose to the dressing rooms. The bored club kid on the door recognized us and let us pass and we moved up the stairs to a thin hallway that led to the dressing room above the stage.

Cindy stepped to the door and pushed it open.

"Hello", she chirped, sticking her head into the tiny dressing room before leading me in. There was Clarisse in full drag, plush painted lips, expansive wig, tight skirt, her coffee colored skin slick with sweat from her performance. I hadn't seen her since my first blow job in the studio and I felt myself blush a crimson red.

"And here you are! Did you get past the faggots at the door? I left your name and instructions."

"Yes it was no problem. They even gave me drink tickets!"

"Well I hope you put them to good use." There were two other drag queens in the room, a tall older woman and a slim, pale girl. The slim girl was stunning, pretty feminine cheek bones and perky breasts behind a tight shirt. A stylish short skirt and thigh high boots. "We have our own supplies here so we don't have to brave the idiot bartenders." Clarisse raised a whisky bottle and poured two drinks into plastic bar cups. One of the drinks was a triple shot and she handed it to me, the other was normal and Cindy took it, downing it at once. Clarisse addressed me, "How have you been? That was great the other day. Did you enjoy it?" Cindy squeezed my hand.

"uh," was all I said for a moment and then, "Yeah. I really did." She looked at me with affection.

"Drink your drink baby" I took a sip and felt Cindy slide behind me.

"Drink it all quickly," she whispered. I took the mouthful of whiskey into my throat and it burned, slamming into my head on top of my previous drink. A warm drunk glow took over.

"I'm going to check on the bar," said the older queen, stepping out of the door."

"Heather, be a dear and lock the door." the beautiful girl snapped the door lock closed. "I was really glad you called me," Clarisse addressed Cindy. Through my descent into fully drunk I realized that this party had been planned.

"You're so cool," Cindy giggled at Clarisse. I felt Cindy's hand on my neck and my legs buckled. In my dim mind I was expecting to kneel and started to face Clarisse but Cindy pulled my face to hers. Sitting back on the thin dressing room table she pulled me into a French kiss. Our tongues massaged each other and she took my hands and placed them on her breasts. I began feeling her and she guided my head down to her tank top. I kissed her nipple through the fabric.

I felt two hands on my hips from behind, gently bending me over before caressing my butt through my pants. I continued kissing Cindy and I looked up at her. She was grinning through flushed cheeks, looking at the room behind me with expectant eyes. She reached up and pressed her thumb in my mouth which I began sucking. With her other hand she gently pressed my head until my hands were on the dressing room table. I felt the hands from behind reach around and unbuckle my pants, sliding them down.

"Nice panties!" I heard Clarisse from across the room. I clenched my eyes shut and continued to suck Cindy's thumb. I felt the panties slide down to my knees, exposing my rear to the slightly cool dressing room air.

I heard a sound and felt something wet hit my anus. I realized that the beautiful girl had spit and I felt her finger rub around the edge of my asshole, penetrating for a moment and then withdrawing.

"Relax baby," whispered Cindy. "You're going to love it."

Nerves took over through the booze and I frantically tried to deep throat her thumb. I felt something big press up against my anus and I knew it was Heather's cock. Two hands took my hips and steadied me as the penis began to push in, stretching my muscles. I felt my ass stretch, maybe rip, and pain shot into my rear and I cried out, a grunt, a moan and a scream at the same time.

"That's the sound of a cherry popping," Clarisse commented from somewhere far away and Cindy laughed. My ass stretched as more and more of the cock slid slowly into me. Abruptly Cindy's thumb withdrew and she seemed to step away. The pain in my rear grew and I groaned out loud pulling back. Suddenly missing the fullness of the penis I thrust back into the pain, a thin white hot flame of pleasure growing at the tip of the girl's cock.

Through waves of pain I felt flesh against my face and I opened my eyes, looking up to see Clarisse looking down at me from beyond the head of her penis. I took her in my mouth, remembering deep throating her in the studio, and began attempting to massage her cock with my tongue. Her hand pressed on my head and she started guiding the blow job, gently rocking her hips as I sucked.

The cock in my ass began to move in and out and I thrust back in time. My pleasure was growing, displacing the sharp pain and I wished I could lubricate her with my mouth. I felt something growing in my testicles which I realized was aimed at my own erect penis, flailing in the cool dressing room air.

"Reach around Heather," Clarisse instructed and I felt the hands come off my hips and around to my groin. One clutched my penis in a light fist and the other began massaging my balls. Electricity shot through my cock and I felt my ejaculation rise like being swept over a water fall. From behind me I heard a slight moan and then a grunt. Clarisse pressed on my head and I opened my throat, taking her as deep as I could.

Behind me, far above, Heather started moaning little girl moans. Her penis thrust and trembled and I felt her sperm begin to lubricate my anus. She moaned louder, sliding now easily back and forth and coming in my ass. Clarisse pressed my head, forcefully pushing her cock into my throat and I gagged, the gag turning into a shuddering orgasm. A hand squeezed my penis while the other hand pushed my balls away from my body and I came like a rocket, semen shooting across the dressing room and between Clarisses legs to stick to the wall under the table. I rocked back and forth on the cock in my anus and I felt Clarisse tense up, pulling her penis head back until it was in my mouth, not my throat. With a spasm her warm sticky cum filled my mouth and she rested her hand on my head. The cum flooded my mouth. Clarisse grunted and thrust again. I realized I was covered in sweat as my orgasm continued, my now empty penis twitched over and over in the girls hand.

Then the dressing room was silent, only the thump of the disco from the main room crowding the roaring in my ears. I realized I was soaked.

"Oh wow baby, that was so sexy," Hearing Cindy's voice I felt myself blush as Clarisse removed her cock from my mouth and I swallowed her cum. I felt Heather withdraw and I leaned on the dressing room table, now empty and spent. I glanced up at Cindy and her face was flushed, her hand resting inside her pants. As she withdrew it slowly I realized she'd masturbated herself to orgasm while watching. She stepped over to me, placing her finger in my mouth. The taste of her pussy mixed with Clarisse's cum. I sucked her finger, silent, shaking.

"We have a little bit of a mess down here," it was the Heather's voice and I turned to look at her. She was incredibly beautiful, the femininity only offset by her now partially erect penis resting in the air.

"Clean her off sexy," Clarisse instructed and I knelt before her on the floor. Her cock was mostly limp with little streaks of brown and cum. I took her in my mouth tasting what I knew was fecal matter from my rear and her cum. Her cock was much smaller than Clarisse's and I dimly realized that her size was part of Cindy and Clarisse's plan. As I licked she pressed her fist around her cock, becoming hard again and pumping away at my mouth.

"That was amazing girlfriend, thank you," Clarisse and Cindy were casually watching me pleasure Heather. I took Heather all the way into my throat enjoying the warmth of her penis head as it stroked from the roof of my mouth and beyond.

"I loved it!" said Cindy.

"Well you're going to have to bring me more virgin boys."

"Oh I will. And my boyfriend is going to help," realizing what they were saying my cock became hard suddenly. I felt Heather's penis twitch and she came in my mouth. I stayed still, rubbing her little cock with my tongue as a small amount of cum coated my mouth. She withdrew abrubtly when she was done and quickly tucked herself away. I stumbled to my feet, her cum in my mouth.

"Swallow it like a good boy," instructed Clarisse and Cindy giggled. I swallowed it and Clarisse almost tenderly handed me another plastic cup of whiskey. "Swirl it around in your mouth first." Which I did.

"Oh honey. You're leaking!" Cindy was laughing. I felt cum dripping out of my rear.

"Did you bring him some feminine hygiene products."

"I did!" Cindy was overjoyed with herself. I felt warm cloth press up against my anus as she applied a pad before pulling my panties and pants up.

"That was amazing," said Clarisse. Heather looked at me with a stunning beautiful smile and leaned over, sticking her tongue in my mouth for a moment.

"Thank you my little virgin." I kissed her back. We made out, her tongue strangely aggressive, masculine in contrast to her beautiful female face. She reached under my shirt and started fondling my chest, my tits. She pulled away from the kiss and nibbled on my ear. "You taste like cock" She kissed my neck and pecked me on the lips and sat back. I was hyperventilating with lust.

"You're still hard. Why don't you jerk off for us before I have to ... return to my fans," Clarisse drawled like a silent movie star. My cock was hard again so I stood in the dressing room and stroked it. My girlfriend and the two drag queens watched and I spread my legs, the burning sensation of their eyes bringing me to orgasm.

"That's a good boy," giggled Cindy. "And now we'll get a cab because we're not driving tonight." Clarrise handed me some tissues for my hand. Heather's eyes burned into me, half triumphant, half hungry. Cindy pulled me from the room.

"Goodbye all. Till next time."

"Goodbye sweetheart," I heard Clarisse say as Cindy dragged me down the hall. At the top of the stairs she stopped and looked at me. There was affection in her gaze but also an edge of steely power.

"That pretty queen wants you for herself," I didn't know what to say. "I'll permit it ... sometimes ... but you're my little slut, understand?"

"Yes," I said.

"Say yes Cindy."

"Yes Cindy."

"Good boy." She led me down the stairs. Moving through the packed club I felt it was obvious that I was the straight boy turned dressing room groupie and my cheeks were on fire with blushing. Into the cold night air Cindy began looking for a cab and turned to me laughing. I didn't know what to say so I looked at her helplessly.

"You're lucky I'm in love with you," she said and a warm reassurance washed over me. I felt the cum soaked sanitary pad in my panties and a contented erotic heat settled over my body. She saw a cab and waved for it. As it pulled over she took me by the hand and looked at me. "Next time I want to watch you suck off a straight guy."

"Yes Cindy," I sighed my consent, erect as we got in the cab.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
AnonymousAnonymousover 3 years ago
More please!!!

This is a great story. So hot! I love the way you're having Cindy lovingly and gradually turn this boy. First Cindy got him used to taking girl cock and now she has him agreeing to suck off a 'straight guy' for her. Super job! Please write more!

AnonymousAnonymousabout 4 years ago
Brafisto!

Del moy selabri constabli brafisto!

El uchi conaftico moy abri constablo.

Cona abri del constable much festa amecro.

Brafisto.

AnonymousAnonymousabout 4 years ago
Well done and entertaining.

This series of stories is well done and entertaining. I enjoy your writing a lot. I have a suggestion though. Heather seems to have appeared without much set up or background of who she is. I don't think Cindy would have just allowed a random trans woman be the first to fuck her boyfriend. Perhaps we find out Heather used to be Heath, Cindy's former boyfriend or perhaps brother. I think Cindy would have had some previous attachment to the women she let take her boyfriend 'a ass for the first time. Just a suggestion. I do hope you'll continue this series soon.

AnonymousAnonymousabout 4 years ago
More chapters please

I have enjoyed this story very much and can't wait to read more! I love the fact that Cindy is a loving dominatrix who has deduced her boyfriend is submissive and into trans women. She has directed him to do what she wanted him to do knowing he wouldn't offer much resistance. Will Cindy begin to transform him to a her? Please continue writing more of this story as Cindy continues expanding her submissive little slut's limits and molds him into her perfect little bitch she desires.

liqueurliqueurabout 4 years ago
great writing. great story

please, more! soon?

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
Tamed by Meg Megan introduces me to the pleasures of being penetrated.in Anal
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
Her Presents She had a number of surprises for him.in Fetish
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
More Stories