Chantal Nights

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My first time with a transvestite.
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The craziest experiences of our lives always occur when we least expect them. People come into to our lives when we aren't looking for them. This happened to me on a business trip to Charlotte.

My boss had asked me to visit the store of a potential client for our consulting business. I hated these kinds of trips. No fun, just a quick flight in, a meeting, a half decent meal on the company teat and then back to the hotel for a night of cable TV and a six pack from a convenience store.

This time was no different. The owner, a beautiful middle-aged blonde in a flattering blue dress, seemed irritated that my boss had pawned the trip off on me. I explained that his wife's birthday had coincided with the trip which appeared to calm her down. As I ran through the consulting offer I couldn't stop staring at her shapely calves and black patent leather stiletto pumps. These business trips always made me horny. The hot women in the airport, the stewardesses, bar girls, etc. As we closed our meeting, I had the temerity to ask if she had dinner plans. She went from mild irritation to barely concealed disdain.

I packed up my attaché and bid Ms. Sexy Heels adieu. I told her I'd be in touch although there was no way I was calling that bitch. My boss could do that. I'd made this pointless trek on my day off and no matter how quickly I would've jumped on her sweet body, I was not going to add insult to injury by letting her have the pleasure of also turning down our business offer.

Back at the hotel, I headed straight for the bar. We weren't supposed to expense alcohol but fuck it. I deserved it.

"Myers and coke," I barked at the bartender. "No, make it 151 and coke."

"Yes, sir" he answered and efficiently produced my medication. "Should I start a tab?"

"Absofuckinglutely. Sorry, that was rude. Yes a tab...Mike?"

"Mike or hey you, whatever suits you."

"Can I also get a menu?"

"Absofuckinglutely, Mr?"

"Ed. But skip the mister 'cause that would just be weird."

I sat back in my bar chair and surveyed the dining room on the right. Empty. The wait staff was standing around looking bored. I sighed.

"Must've been a tough one," a feminine voice commented from behind me.

I turned to meet the voice and found a slender brunette smiling next to me at the bar.

"151 and a sigh. There are much tastier chasers for a drink like that," she winked.

I checked her out from head to toe. I know it was obvious and somewhat rude but I guess her surprise made me forget my manners. She was hot in all the ways I find sexy. Her hair was styled nicely, impeccable make up, red lips, luscious curves dressed up in a button down blouse and a black pencil skirt with a thigh revealing side slit, sleek black legs wrapped like a present in shiny black pantyhose, and perched on four inch black pumps. Men love a real, feminine woman.

She gave me a wry smile when I recovered my courtesy and met her gaze. All the horniness I had felt at the business meeting came rushing back and took up residence in my cock making it jump a bit.

"I've had worse but thanks for noticing," I offered courteously.

"I'm Chantal"

"Yes you are. What an exquisite name. French?"

"Maybe after I get to know you better, Ed." Chantal's eyes crinkled as she briefly touched my shoulder to slip up onto the bar chair next to me. I felt my heart race a little.

"What'll happen if you get to know me a lot better?"

"I just might give you a big surprise, Ed," she taunted as she hiked her skirt slightly and crossed her legs. The pointed toe of her shoe rubbed against my pant leg.

"Those are some seriously sexy heels you've got there, Chantal. Do they hurt your feet to walk in them?"

"Why, you want to try them out?" she shot back sarcastically.

I blushed. She got me. I felt a little like I was a pervert or something.

"I'm just teasing you. Yes, sometimes they're murder but it's worth it. I feel super hot when I wear them and men always notice me. These women and their comfortable shoes. Boring. They're missing the best part of being a woman. The privilege of being feminine."

"I couldn't agree more. I guess I'm old fashioned. I am absolutely enthralled my feminine women. I love everything about them. The hair, the perfume, the makeup, the sexy clothes and don't get me started about how much I hate barelegged women. A nylon calf, the sweet wisp of hosed legs as they strut by. God."

"Then you oughta love me. We have something in common already and we just met. Isn't that fun?"

I could only smile.

"I have about a hundred pairs of pantyhose and I'd wear every pair I own for you. Would that cheer you up?" She reached over and squeezed my thigh. My cock was now like an iron bar. She slid her hand higher. I watched as her bright red nails etched the outline of my bulging trousers and then lightly pressed my manhood.

"You look pretty cheery already." She leaned towards me. I returned the favor by lightly running my fingers over her soft sheer nylon covered knee. Chantal made low humming sound of appreciation. She pressed her mouth to my ear and whispered.

"If you get that hard from just a little sexy talk, you're gonna explode when I do something really hot." With that she tugged emphatically on my cock like it was an exclamation point.

I gasped. I'm no prude but I checked to see if the bartender had seen this and for once was glad that he was not to be found.

"Describe really hot," I probed.

"Hmm. Pantyhose man. I bet you'd like to rub your dick all over my legs. Or press it hard into my hose covered butt crack. Maybe you'd like me to sit on your face? Or maybe me on yours"

"Uhh..." I was a flustered but totally intrigued.

"Anything else?"

"Maybe you'd like tie me up with my hose and do whatever took your fancy."

She licked the interior of my ear. Where was that bartender? I needed to settle up right now.

"That could be fun."

"Maybe you'd like to try a pair on and have me lick your big fat cock? Or how about you just fuck me 'til I cum all over your throbbing meat?"

Mike appeared from the kitchen. I waved.

"Check?"

Chantal's suite was way bigger than my room. I could hear her singing lightly as she did whatever women do in front of the mirror. The entire trip to her room had been surreal. She had kissed me in the elevator and then led me by the hand down the long hallway with a slow sexy strut.

Once in her room, she made me a drink and then excused herself to freshen up. When she returned I was in awe. She was wearing only a black silk slip, black opera gloves, sheer black pantyhose, and black patent leather stilettos.

"You like?"

I nodded. She strolled over to the loveseat and then stretched out sensuously. She motioned for me to join her. As I approached she raised her beautiful legs and allowed me to sit. Then she stretched them across my lap. I tried hard to get a glimpse under her slip but to no avail.

"Remember your question about my feet in those shoes? These are even harder on them. Mind giving them a little attention?" she asked coyly.

I was transfixed by her legs on my lap. From her thighs exposed just under the slip to the hot bit of toe cleavage peeking out of her pumps, I was in heaven. I removed her shoe and began what I intended to be my greatest foot massage ever. She moaned slightly as I worked the ball of her foot.

"Yes. You have good hands. That's a good sign."

"Of what?" I asked, my cock straining at my boxer briefs.

"An attentive lover, silly. Do my other one now."

I accommodated her wish and removed her other stiletto. I studied her nicely pedicured and painted toes. Deep red shone through the black nylon in a way that turned me on even more.

I continued the massage for a few more minutes, relishing every minute, every touch. Chantal's eyes were lightly closed. I was clearly relaxing her. I knew I was good at this. I had gotten in more women's panties via their feet than any other move in my repertoire.

"Oh, sweety! That is fabulous," she cooed as she sat up. "Anything I can rub for you?"

I looked at her slyly.

"Take it out."

"Why don't you take it out, baby?" I responded.

Chantal leaned over towards me and unzipped my trousers. I couldn't wait to get my cock out of its confinement. She gingerly pulled it out of my briefs and through opening in my pants.

"Nice cock, Ed" she smiled. "I'm gonna have fun with that."

With that she reclined again and started rubbing it with her pantyhose covered feet. What a sensation. She pressed my purple cock head between her insoles and rubbed it up and down until pre-come oozed from the tip. She took one toe, dabbed it, and then stretched a long strand up until it dripped away.

Chantal tantalized me with the deft use of her feet, the fabric stroking my cock head and the most sensitive under area. The blood surged making it as hard as steel. Sensing that I was about to explode, she stopped.

I watched with slight disappointment as Chantal rose to her feet but was encouraged by the sight of her putting her heels back on and standing directly in front of me with her gloved hands on her hips.

"Now for the real fun."

She strutted over to the dresser and turned on some slow romantic music. She turned to face me and started to dance a very sensually. The music was jazzy and full of sultry saxophone.

I noticed how fit she was. Fit without being sinewy. Her long legs were the nicest and shapeliest I'd ever seen in person. She was a skilled dancer. I loved that. She bent forwards and touched her right toe , running her hands up the length of her leg. She was not only fit but flexible. My cock was raging. As she reached the top of her thigh she turned sideways and lifted her slip up to her waist. She was wearing sheer to the waist pantyhose. No panel, totally sheer. Normally I was happy to catch a glimpse of a woman's hosiery, any part of it. Now I was getting it all.

"You want to cha cha with me, lover boy?"

"No, I'm fine right here."

Chantal danced towards me and then turned her back. She shook her ass to the slow beat. My cock throbbed hard. It was the second time I nearly came. I thought of everything I could to not blow my load. As if she sensed that I was struggling to not cum, she inched her slip up over her butt cheeks offering a full view her black pantyhose covered ass with one black g string running up the crack of her buttocks. I could see her wonderful plump ass with nothing in the way, possibly one of my biggest turn-ons. I wanted to run over and grab that ass or bite it or lick it or fuck it, but that seemed like a long shot. I'd settle for her turning around so I could see her hot little pussy. I wanted to see how nice the it looked before I fucked her silly.

She dropped her slip back down over her ass, turned and strode towards me. Without a word she pulled me to my feet. I couldn't help myself. I grabbed her waist and pulled her against me, my cock pushing between her legs. She squirmed a bit but then relented. I held her with one arm and with the other pulled her mouth to mine. I kissed her hard. She opened her lips and accepted my probing tongue. She squeezed her thighs tightly around my cock nearly making me cum again but I managed to hold onto my juice. In a mad whirl of passion she kept kissing me while she undid my belt and fly, sending my pants to the floor. I kicked off my shoes as she pulled down my briefs and unbuttoned my shirt. I wiggled out of it and now was completely naked in front of this gorgeous woman.

"Now it's your turn," I chided.

"Not quite yet," she answered as she pushed me down on the couch. She got down on her knees and opened my legs. She examined my manhood carefully.

"9 inches of beautiful cock would be my guess, Ed. You should be proud. I don't get to see many that big and perfect. Love the fat head on it, too. I should take a picture. My girlfriends will never believe me when I tell them about you."

With that she ran her tongue from the back of my balls to the tip of my head three times and then ran it around the head so many times I lost count. She licked me from the tip to the base and went to work on my balls, kissing and fondling them. Then she drove me mad by tracing the ridge from my balls to my asshole, lightly tapping and darting around my hole and then in and out of it. No woman had ever done that. Wow, I was reeling. It was all so unbelievable. I was sure something would go wrong. But it didn't. It just kept getting better. If she was a pro, so what? She was worth the money. I hoped she wasn't. I liked thinking she was actually attracted to me.

Her hand gripped hard at the base of my cock. What a grip that was! Chantal put her lips over the tip of my cock and slowly worked me into her warm moist mouth, moving an inch at a time and then moving back to the tip. Back and forth, in and out until she reached her gloved hand near the base. She moved her hand to fondle my sack and then went to the bottom of my cock. I could feel the fabulous sensation of her lips around the root of my penis.

I was lost in lust, enjoying every millisecond of her splendid cocksucking. Some women wouldn't suck your cock. Some did but acted like they didn't like the taste but wanted to make you happy. Then there were the Chantals of the world: hungry, loving, world class cocksuckers. She knew everything a man could like. It was like she had ESP. I was almost catatonic. I didn't want to blow yet but wasn't going to last much longer with this kind of luscious mouth sex. But who cares. I'd hump her later. Fuck it, I was going to let it loose.

In the middle of my pre-explosion spasms she slipped her mouth off and grabbed the tip hard, preventing me from cumming.

"Oh..." I yelped in frustration.

"Oh, baby. If you pop, you'll miss the chance to fuck me," she taunted.

"God, no woman has ever done that kind of suck job on me. It's like you were in my head the whole time. You must love cock."

"Hmm. Yes I do," she agreed standing in front of me. "I know a man's cock inside and out."

"Sucked a lot of them?" I giggled.

"Yeah, baby. Including my own. Want to see me do it? I'm really limber, Ed"

"Say what?" I stuttered.

" Remember I said if you were good I'd give you a big surprise? Here it is." With that she raised her black satin slip and I found a huge cock staring back at me.

"What the fuck? You're a dude?"

"No honey, I'm not a dude. I'm the hottest girl you ever met but with a little bit of extra skin."

And she wasn't kidding. Her cock was almost as big as mine and the head was a little larger. As I took it all in, she reached in under her pantyhose and untied the sides of her g string. She tossed her thong to the floor and straddled my leg, pressing my head towards her crotch and what happened next will remain a mystery for life.

For some reason, a reason I'll never be able to provide, I put my mouth right on her nylon covered cock head. I wasn't forced, tied up, offered money, or anything. I put my lips and tongue right on her beautiful, hard cock and then I was past the point of no return. I licked every inch of her cock, loving the feel and the sight of it through her hose. After I few minutes, she stretched her hose down under her scrotum and stroked herself. Man, she had a nice cock. Even straight guys can admire a nice looking cock. Without urging I took her in my mouth and sucked her as if it was my own. She began to verbally urge me on but I couldn't manage the length without gagging. I don't know what got into me but today, for first time it was another man's cock.

"Maybe if we get together again, I'll show you how to do that without gagging," she whispered. "But for now, I want you to fuck me."

"Listen, I'm not gay, okay?"

"Yeah honey, neither am I," she laughed.

"No I mean it. I've never done this before. I had no idea. I just thought you were the hottest woman I've ever met." I smiled. She smiled back.

Chantal somehow managed to put that fat cock of hers back inside her hose. The site of her erection stretching at her pantyhose almost made me cum...again.

"That is so sweet. I am the hottest woman you've ever met and in a bit, I'll be the best piece of ass you've ever had in your life, too."

Chantal stood and then pulled me up with her. She grabbed my hands and placed each palm on an ass cheek and then pulled me against her mouth again. We kissed passionately. She whispered in my ear.

"Fuck me. I need fucked and I'm tired of my rubber cock. It's been way too long."

She kissed me hard. I loved the feel of her ass in hose. I always loved that but most women don't appreciate how much men love hose. If they did, they'd all wear them. In fact, women don't appreciate the allure that their lingerie and undergarments have for men. Now that I'd met Chantal, it occurred to me that maybe cross dressers understood this or maybe they dressed up to match the women that turned them on. Or maybe I was overthinking, looking for a rationale to justify the fact that I was deeply attracted to another man. I had kissed another man. Another man had sucked my cock better than any woman. I had sucked another man's cock and loved it. I was getting ready to fuck another man's ass. I didn't see Chantal as another man, though. She was in her own category.

Chantal led me to her bed. She stretched out on her back assuming a very alluring pose.

"Don't keep me waiting, lover."

"Why? What if I do?" I toyed, rubbing my swollen meat to tease her." Maybe I'll just jerk off while I stare at your hot bod. Come all over your hose covered dick." I ran my hands all over her legs and then squeezed her dick hard."

"Don't! I'm just about to explode, sweetie. I want to do it with your cock buried in my ass. You won't believe how good it'll feel when I come all over your hard cock. Fuck me."

I didn't need much more prodding. I climbed on top of her. We began to kiss and rub our cocks against each other. It was a wild sensation of pure lust as we dry-humped. Chantal then raised her knees to her chest. I licked the backs of her knees and calves and then kissed her budding little tits. She moaned appreciatively. I spotted a rubber on the night stand and seized it, ripping open the packet. I couldn't fathom what was happening to me but I liked it. I stretched the latex over my cock. Chantal grabbed the lube from the stand and handed it to me. I hurriedly applied it.

"Be generous. I'm a little scared of your size, honey."

"You should be."

"Pull down my hose, hurry. Fuck me, now."

That really got me going. I grabbed her arms and pressed them to the bed behind her head.

"I'm in charge now. I'm gonna do whatever I want. Maybe I don't want to fuck you now. Maybe I'm gonna just rip those hose right off you and suck you off instead."

"No, be nice now. Give it to me," she pleaded.

With that I grabbed the stretchy fabric that so drove me insane and tore an entry way towards her pink little hole. My cock had never felt this hard, this sensitive and honestly I think it was actually bigger and longer than ever.

I pressed it against her opening and then in slightly. There was some resistance and then the head popped in. Chantal moaned gutturally. It felt so good that I pulled back out and stuck it in again. I eased in slowly. I was aware of not wanting to hurt her, not wanting to have this end too soon or pop too fast. The tightness was exquisite.

"Slow. Let me get used to you."

"Does it hurt?"

"Not in the least but don't go in farther yet or it might."

For some reason it's hard to not cum when you're trying not to. I wanted to fuck her hard and yet I didn't want to pop too soon.

"Kiss me for a minute."

We kissed. It was so passionate. I felt like I really liked Chantal. That scared me.

My fear was short lived and gave way to pure raw lust.

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