Dancer Turns me out Pt. 02

The shrill phone alarm startled me awake. It took a minute to clear my head. I was still wearing my white, lacy panties, but they were far from pristine condition now. After my adventures with Gary at the club, I had returned to my hotel and jerked off twice into my panties before finally passing out. The crusty lacy was stuck to my hardening cock and was more than a little painful. I hopped into the shower with the panties on, letting the hot water release me from my dainty, sexy prison.

I left the shower and started the in-room coffee maker. Today was going to be a long day. Not only was I going to be sitting through an insurance conference all day, I needed to stop for new lingerie and be back to Devilish Angels by 9 pm to entertain Gary and any of his friends who were around.

The meetings all day were dry and boring, so my mind spent all day wandering back to the night before. I had a constant hard-on under the table and ran to the restroom several times to take care of myself. Between the stroking and sleeping in cummy panties, my cock was starting to get downright sore by the time the day's sessions ended.

I had room service bring me a quick dinner while I showered and shaved, preparing for the night. Gary had given me the name of a lingerie store that specialized in serving alternative clientele or, as Gary had said, "sissy bitches." I plugged the address into my GPS and headed off to find something pretty to wear for the evening.

My phone directed me to a small, dingy strip mall in a rundown industrial area that had seen better days. The bright neon signs in the front window left no doubt that I was in the right place. "Krystal's" was lit up in bright pink, dwarfing the small "Open" sign below it. From the outside, I couldn't see in thanks to the shimmery curtains that amplified the brightness of the signs.

The bell rang loudly as I entered the store, alerting everyone to my presence. The store was practically deserted. There was a middle-aged woman filing her nails behind the counter and a couple looking through the sex toys in the back corner, but otherwise I had the place to myself.

I quickly made my way to the lingerie area. I gently stroked in the soft, delicate fabrics and felt my cock stirring in my pants. There were so many choices and my head was swimming in confusion and desire. As I was searching the collection, a beautiful woman in a striking red dress came out of the backroom and headed my way. She was tall, 6' or more, and slender with large, prominent breasts. Her blonde hair cascaded down over her shoulders and bounced with each step. Her dress barely covered her tight ass, leaving most of her long, tanned legs exposed. My heart pounded as she approached.

"Hello," she said in a soft, raspy voice. "Can I help you find anything?"

"Um, yes," I said uncertainly, trying to remember my instructions from the night before. Then, with a bright red face, I looked at the floor and nearly whispered "Gary said for me to come in and pick out a few outfits suitable for a cocksucker."

Her eyes flashed and a big smile broke out on her face. "Gary did, you say?" she said, practically giggling at me. "Well, neither one of us wants to disappoint him. My name is Anastasia and I'd be happy to help. Did you have something in mind?"

"Um, not really. I guess I was hoping maybe you could help."

"Sure thing, sissy," she said, louder than I thought was necessary. "Has Gary seen you dressed before?"

"Yes, last night," I quietly replied, my face turning even brighter red and cock stiffening.

"And what color were you wearing then?" she asked, reveling in my discomfort.

"Um, white," I said, finally meeting her eyes when I spoke.

"Hmm...you need some color on you. Something bright, I think," she said, moving towards the racks. "How about something red? No, wait, pink. Definitely the perfect color cocksucker like you."

"Well, um, actually," I stammered, "I'll need two outfits. I'm supposed to be there tonight and tomorrow."

Her eyes got wide. "Really? Two more nights? Wow, you must be very good. I'm tempted to take you to the backroom and try you out myself, but I don't want to get on Gary's bad side," she said, laughing loudly at her own joke.

Anastasia started pulling lingerie off the racks, holding it up to me and quickly sorting through the options. Eventually, she picked out two outfits that met her high standards and practically dragged me to the checkout counter. The first was a pink fishnet body stocking with a halter neckline and a large cutout in the crotch. She accessorized with a matching satin g-string which was far too small to contain my cock. The second was a bright red stockings and suspender set, crotchless again, with a black lacy thong that would definitely give me a noticeable whale tail anytime I bent over. She even got my shoe size and picked out a pair of clear, platform stripper heels. The total was more than I expected, but I was in too deep to argue.

After my card was charged, I looked nervously to Anastasia. "Is there somewhere that I can, um, change?"

Gary's instructions were clear. I was to come prepared, and that meant wearing what I had purchased. My options were limited. I didn't have time to return to the hotel. Changing in a McDonald's bathroom or at a truckstop were not appealing options. Anastasia must have seen the desperation in my eyes, because she just smiled and beckoned me to follow her.

She disappeared through a doorway in the back and I quickly followed, the couple from the store giving me dirty looks as I passed them. I followed the clicking of her heels to a small office. The desk was covered in papers, invoices, and sex toy catelogues. As I entered, she closed the door behind me and strolled to take a seat behind the desk. She crossed her legs and looked up at me, indicating I should get started.

Because of the pink body stocking she had picked out for me, I was going to have to get completely naked to put it on. She clearly knew this and was looking forward to the show. I began by unbuttoning my blue dress shirt and carefully placing it on the chair across the desk from her. Next, I kicked off my shoes and pulled my socks off as well. Finally, I took a deep breath before unbuckling my belt and letting my pants and boxers slide down and off my body.

Anastasia looked at me, licking her lips like she was a hungry predator and I was to be her unwilling prey. I nervously gulped, then pulled out the body stocking, working it up my legs, over my hips, and eventually behind my neck. It was snug but not uncomfortable. I adjusted to fully free my cock through the hole in the crotch, then looked back at Anastasia.

Her eyes were glued on my cock, which had been hard and dripping for quite some time by now. Finally, she looked up at my face and said, "Wow, not bad for a cocksucker."

After a brief moment of uncertainty, I decided she was complimenting me. "Thank you," I said softly with a big smile on my face.

The satin g-string was next. I slid it up my legs, over the fishnet material, before reaching its final destination. I tried briefly and unsuccessfully to tuck in my hard cock, before leaving the tip emerging over the small, feminine panties. I quickly pulled my pants and shirt back on. I reached for my shoes, but Anastasia stopped me. "Uh-uh-uh, the heels, bitch."

I slid the heels on my feet, then slowly and unsurely stood. I had never worn any heels at all, and now I was in sky-high platforms. Anastasia laughed as I took my first few tentative steps. I wobbled with each step and almost fell over immediately. I was concentrating on my walk when I felt her behind me. She put a hand on each hip and forced them to sway back and forth. "Here," she whispered in my ear, "walk like this, it helps."

Whether it was because I was focusing on my hips or just adjusting, I did find it slightly easier to walk after her lesson. I was starting to feel the sexy beast come out in me and I was loving how it felt.

Anastasia helped me pack up my shoes and socks with my other purchases and guided me to the front of the store. She gave me a quick peck on the cheek and, winking, said "Maybe I'll see you later."

The dilapidated parking lot was much more difficult to cross than her carpeted office. I successfully, though slowly, got to my car without breaking an ankle or falling over. Once I reached the car, I slid my heels off, figuring it was better to drive in my stocking feet rather than trying to learn to drive in platforms on the fly.

I made my way to Devilish Angels with 10 minutes to spare. I sat in my car taking deep breaths, trying to calm myself before I just couldn't take it any longer. I slid my heels on and strode as confidently as I could to the door, swaying my hips like Anastasia taught me.

"Hi Jamal," I said as confidently as possible. "I'm here to see Gary."

He looked me over, smirking at what I'm sure was a startling combination of male clothes and platform heels. "I've gotta see if you're on the list," he said, staring right through me. "What's your name?"

"I'm JD," I replied quickly, then in a quieter tone I said, "But Gary calls me Jenny."

He laughed right in my face and turned to his clipboard, then laughed again, showing me the name "Jenny Cocksucker" in bold print and "9 pm" handwritten next to the name. Jamal looked me up and down again. "This has gotta be you," he chuckled, then opened a side door, motioning towards the elevator inside.

I pushed the button to call the elevator and heard it roar to life. There wasn't much light in this small entryway, making the red button look even brighter. The doors opened and I quickly got in, pressing "2" and taking a deep breath. There was no backing out now.

Gary buzzed me into his office. He was on the phone when I entered, but motioned for me to undress while he finished his call. I quickly removed my shirt and pants, folding and placing them in the corner of the room. I replaced my heels and stood in the middle of the room wearing just them and my feminine lingerie. My cock was peeking out of the top of my tiny pink panties.

"Ah, Jenny," Gary said as he hung up. "I have some big plans for you tonight. I hear you were a very good girl at Krystal's. That makes me happy."

He moved towards me, undoing his belt and eyeing me up and down. "Anastasia sure knows how to pick a killer outfit. Tell me, did you thank her properly?"

"Um, what do you mean?" I asked. "I told her thank you."

"I mean, did she get to sample your talented mouth?" he asked as he roughly shoved his thumb between my lips.

I shook my head no as I sucked on his thumb, moaning softly as I did.

"Pity," he said softly. "She did such a good job helping you. I'm sure it made her horny picking out sexy things for you to wear for me. And you just left her there unsatisfied."

"I'm sorry, sir" I mumbled around his thumb. I could tell he was disappointed in me, but I hadn't picked up any signs that she wanted anything from me other than my money.

"That's ok, Jenny. I'm sure it will work out," he replied cryptically while shoving his thumb deeper into my mouth. "Right now, I have something for you to take care of."

He gently pushed me to my knees and pulled out his hard cock. I could feel the fishnets trapped between me and the dirty carpet as I hit the floor. I immediately took his cock in my hand and guided it to my eager mouth.

As I sucked his salty cockhead into my mouth, he threw his head back and moaned loudly. His hands hung by his sides as I took more and more of his hard, manly cock into my mouth. I wished I had access to his balls, to feel and taste them, but knew it wasn't my place to ask for such a treat. I just focused my efforts on his cock and giving him all the pleasure I could.

I got into a good rhythm, bobbing on Gary's hard cock and sucking his length deep into my mouth. I could tell he enjoyed my efforts, but needed more. Finally, he grabbed my head with two hands, holding me in place. He roughly fucked my face, causing me to gag and drool. My eyes were watering like crazy when, with a loud groan, he pulled out of my mouth and started cumming all over my face.

Rope after rope of jizz coated my face. It dripped off my nose and got in my eyes, which stung like crazy. I greedily licked up any that got near my mouth. I was beginning to really like his flavor and I wanted as much as I could get. I started looking around through red, burning eyes for a rag or something to wipe the sticky cum off my face, but Gary stopped me.

"Leave it on," he ordered. "You look better that way."

Humiliated, I remained kneeling on the floor, blushing through my painted face. My cock was painfully hard and poking out of my tiny satin g-string. Any movement caused the string to rub against my ass, making me even hornier if that was possible.

Gary rubbed his cock in my hair, making it sticky with the last of his cum. He tucked his cock away and strolled back behind his desk, looking smug and satisfied. I stayed on my knees, not sure if he was done with me or if there was more in store for the night. My questions were quickly answered.

"So, Jenny," Gary said with a smirk. "I'm glad to see you're still an eager cocksucker. I have someone for you to entertain this evening. Do a good job and I won't have Harley come in and beat your ass. Speaking of ass, you'll be giving yours up tonight."

I looked up in a panic. A blowjob or two was one thing, but getting fucked? I was caught completely off guard. Not only had I never been fucked before, I'd never even had a toy up there. The fear made my cock shrink back into my panties.

"Wha-no, I can't do that," I begged with wide eyes. "I've never done that before It's going to hurt and I don't want to and you can't make m..."

Gary's temper flashed across his face as he interrupted. "They hell I can't! You will give up your ass and you will show them a good time, or God help me, I'll let Harley have at you and then sell the video of your cocksucking performances online. You hear me, bitch? I own your ass and I say who gets to fuck it!"

Defeated, I just bowed my head. He had me by the balls and I knew it. Part of me had always wanted to experience taking a cock, but fear had always stopped me. Gary gave me something to fear much more than some physical pain. He threatened global humiliation, which was too much for even me.

"When?" I asked him.

Gary pressed the buzzer to open his security door and smiled. I knew I had his answer.

I turned my head to look back at the door. I got the shock of my life when Anastasia and her bright red dress and sensual body strode confidently into the room. She passed me by and went straight to Gary, kissing him.

"Darling, you did such a good job," Gary said, motioning to me. "Pink is the perfect color on her."

"Thank you, Gary. Jenny gave me a lot of freedom. It was fun to shop for her. I see you already baptised her this evening," she said with a hearty laugh.

"I did," Gary replied with a nod. "Someone had to break her in tonight. I hear she didn't take care of you, though. Is that true?"

Anastasia nodded. "Yes, but I didn't push it. I knew I'd have my chance."

"Would you like your chance now?" he asked her.

"Do you mind?" she asked, looking over at me.

"Go right ahead. I'm going to need a few minutes to recover anyway," Gary said with a laugh.

Anastasia strode right up to me, looking down into my eyes. I didn't know what to think. I was going to get to lick the pussy of this goddess? It was like a dream come true.

"You're such a mess," she said with a disdainful voice. She pulled her bright red dress up over her head and off her body. "I don't want you getting any cum on this."

I examined her body. Her golden hair hung down to the top of her large, bra-less breasts, almost directing my eyes to her nipples, which were hard and protruding from her mounds. My eyes drifted lower, across her smooth stomach to the small, delicate red thong that covered her...bulge? I had expected a mound, but she clearly was not your typical woman. I felt like my eyes were going to pop out of my head.

"Surprised?" she asked with a giggle. "Gary sent you to me for a reason. And now, you're going to thank me properly for the excellent service I provided you tonight."

I just nodded. I could see her bulge growing inside her panties. She was obviously getting excited, and I must confess, so was I.

Anastasia grabbed a handful of hair and dragged me over to the couch on the wall opposite Gary's desk. She slid the silky thong down her legs and bent over in front of me, with the clear implication that her asshole was to be serviced. She spread her cheeks and I dove in.

I licked over and around her rosebud, then down over her balls as well. My tongue worked in and out of her hole, fucking her ass as best I could with my mouth. Her moans and rocking hips told me I was doing well. Suddenly, she spun around and slammed her cock deep into my mouth and throat. I didn't get a good look at it, but just how it felt inside me, I knew she had to be bigger than Gary.

She held my head and forced her dick deeper and deeper until my nose was pressed against her sweet, smooth abs. My air supply was cut off and I was starting to panic when she let go. I gasped loudly, trying to suck in as much oxygen as I could. Anastasia grabbed me by the hair again, pulling me roughly up onto the couch, positioning me with my ass high in the air and face down in the cushions.

"Don't move or I'll really make this hurt," she said firmly.

I felt something cold drip on my asshole, causing me to pucker. Anastasia smacked my ass hard, then slid a finger inside me. She turned to Gary and said, "Oh yes, definitely a virgin."

She took her time opening me up. Once I loosened up around one finger, she added another, and then another. I could tell she had done this before and knew just what to do. Finally, she pulled out of my hole. I suddenly felt empty and pushed back against air, wanting to feel full again.

Anastasia bent over to whisper in my ear. "I'm going to fuck you now. It's going to hurt at first but I promise you by the end, you'll be begging for more. Do what I say, ok?"

I just nodded yes. I didn't trust my brain to produce the proper words. I felt Anastasia move behind me. One of her delicate hands grabbed my hip, pulling me back slightly. I felt her hard, hot cockhead press against my asshole. There was no turning back now.

"Relax," she said as her dick began to penetrate me.

I tried my best to relax, but between the nerves and my tight virgin hole, it was hard for her to push into me. Then, she pushed harder and I felt my ass swallow her cock. Generously, she stayed still, allowing my burning asshole time to get used to her size. Slowly, she started rocking gently, opening my ass up more and pushing deeper inside me.

It started to feel really good and I moaned involuntarily. Gary and Anastasia both laughed at me.

"You must be good," Gary said to her. "One minute inside her ass and you've got her moaning already. When I take a virgin ass, they usually scream and try to run away."

"That's because you don't know how to break in a bitch," she said, smacking my ass hard.

Anastasia pumped my ass slowly but firmly. I could feel my cheeks bounce off her firm body as she thrust into me. Long strokes filling my ass, making me moan and causing my cock to leak all over the couch.

She started fucking me harder and faster, grabbing my hips to add even more force to her thrusts. I could hear her breathing getting ragged as she pounded me faster and faster. Finally, she pushed deep inside of me with a groan and I could feel her warm cum filling my ass. I had never felt anything like it before, but knew I wanted to feel it again soon.