tagTranssexuals & CrossdressersHigh Heels and Stockings Tryout Ch. 02

High Heels and Stockings Tryout Ch. 02


Chapter 2: Bi-sexual Sluts in Stilettos

Author's Note: Thanks to all who read and enjoyed my first story. I hope you like this one too, and get so excited by it you have to jerk off and blow a big, wet load. Enjoy!


After my first semen-splattering cross-dressing experience, I was hooked on dressing up like a slut, and masturbating in stockings and high heels. Most of my wife's clothes were too small for me, so rather than fall into the trap of stretched out skirts and panties, I ordered my own. Actually, I would order two sets of slut clothes - one for me, and one for my hot wife. That way, I could have her wear a set, and while I fucked her, I'd think of how later I would dress us in the same outfit, and slide a lubed jelly cock in my tight ass.

It was so hot lying back on the sofa, in my favorite costume - a slutty schoolgirl with 3-1/2" heels, fishnet stockings, a garter belt, plaid skirt, and a tight white top. My rock hard and throbbing cock would stick straight up, and I'd rub it against the soft cotton skirt until it was leaking pre-cum, and then change over to using my woman's soft satin panties to stroke into. I'd watch porn until my cock was throbbing and ready to cum, then I'd stand in my high heels and stroke my cock until wet, hot jism would fly wildly of the the tip, all over some slut in a porn mag. I'd cum so hard in heels - it was so nasty and filthy to dress like a woman and spurt cum. Any spilled sperm on my finger would quickly and greedily get licked off.

It was lots of fun, but as the weeks went on, I began to think and fantasize about fucking another hot CD. The idea of getting all slutted up and having nasty fun with another whore with a cock was a favorite fantasy of mine, and when I'd bend my wife over and fuck her from behind, I'd imagine she was a sexy CD, who had a hot and smooth prick to pull on while I drove my cock into her asshole.

But where to find the right cock? I checked out an adult personal's web site, but nothing really caught my eye. I decided to throw a line in the water myself, and placed an ad.

"Sexy, slutty, shy CD wishes same or couple for casual meeting, then maybe hot times", I wrote. I got all slutted up, and took a few photos of myself, with my 7" cock sticking out from the under my school girl's skirt, all shiny with the cum that I'd spurted in my hand, then used to rub the into my cock skin, making it all slick and dripping.

I got lots of responses, but all most all were from horny non-CD guys. Then one day I opened up a message that looked interesting.

"Hi. My husband and I looked at your photos, and they really turned us on. He's looking to explore his bi side. He likes to CD, though he's shy about it too. I think he looks just wonderful in his panties and stockings. Hope to hear from you."

They'd attached a few photos of their own, and my heart began to beat faster as I looked over a shot of him from the waist down, in a French maid costume - high heels, seemed stockings, and a nice big bulge in a pair of black panties. The wife was nice looking too, with a fit body and good tits.

I responded to their message, and we chatted back and forth, getting to know each other better. They were new to the big city, having moved here for work, and didn't know too many people yet. They sounded like a very nice and friendly couple, and we set up a dinner date for later in the week.

I work in a lab, so was easy to tell my wife that I had to stay late to supervise a test. As a side note, I'd suspected for about a year my horny wife was having a fun-fuck affair with her best friend - they spent a lot of time together, and our downstairs bedroom seemed to have the faint smell of hot pussy after they'd spent a lazy afternoon around the house. If she could have some hot bi-sex and still love me, then I figured I could do the same.

Anyway, my wife didn't seem to bothered that I'd be gone till late, probably because she was thinking of the pussy licking she was going to be able to do later with her friend. I kissed her goodbye, and headed out for my date.

We'd agreed to just have dinner the first time, and see how things went from there. I got to the restaurant early and had a drink while I waited. About 10 minutes later, they walked in, and I recognized them from their pictures.

James and Samantha were their names. Sam was about 5'-5", with brown hair, a gorgeous smile and sparkly eyes. She was nicely dressed in a skirt and blouse. James was the prize though - a bit shorter than me, cute freckles on his face, round full lips, and a handsome body.

We talked, ate, and got to know each other. They were a really nice couple, friendly and down to earth. We didn't talk too much about sex that night, just admitting that we all were willing to try some new things At one point James went to the bathroom. Sam leaned in close, and said "James really likes you. He said he's, well, excited by you." She turned a bit red when she said that, which I thought was so cute, and endearing. I was hooked on them.

Still, we'd agreed to just a dinner, and as we paid up, we made plans for Friday night to meet at a fancy hotel, and see how things went. Sam hugged me as we left, and as I shook hands with James, he looked at me, took a deep breath, and hugged me too.

It felt exciting. Exciting to have his body pressed against mine, and exciting that I'd turned him on enough for his to overcome his shyness about being excited by another guy.

What is it about brand name Gay that's so off-putting to most guys? Is it just prejudice, like it used to be about difference races? Is it that our sexuality is so much a part of who we are that we recoil if we start to feel that identity turned? Or is it that when most guys think gay they have a picture of either some lispy wedding planner, or a Freddy Mercury type in leather chaps and a jock, marching in a Pride Parade? Waiting for the Hammer to Fall indeed.

I know with James I felt an attraction to him as a person, and towards a sexy person the same way I would with an attractive woman, It some something new and exciting to me, and I relished the thought of a hot threesome with him and his sweet wife.

Friday night I told my wife that I'd be gone all night supervising the test, and that she should make some fun plans herself. Unsurprisingly, she said she would do something with her friend. Someday I'd find out what that was, but for now I was happy to have her occupied, and probably headed for a good licking and fucking from her pal.

I met my new friends that night at a hotel, and with racing pulses we headed upstairs. I'd splurged a bit and gotten us suite with two bathrooms, one for each of James and I to change into our girly clothes. We'd briefly talked over dinner about our love of sexy women's clothes, but I felt too much discussion of it would take away some of the magic of our first time. So we put some soft music on the radio, and same lit some candles she brought along. I told them I wanted to see them dance, so they held each other and swayed to the music. Besides the sexual attraction I felt towards the both of them, I also felt honored that they were sharing their intimacy with me.

After a song, James said Sam and I should dance, while he made us drinks. Sam sauntered towards me, looking more confident and relaxed than I'd seen her before. She was getting into the moment, and realized what a wonderful night it was going to be.

"You and James moved so nicely together," I said. "You two are are great couple." We embraced, and slow danced.

"We are. He's the love of my life. That's why I want him to explore his fantasies, and share them with me. And you." She looked at me and slowly came in for a kiss.

Her lips were soft and warm and she smelled of sweet flowers. I eased back from her kiss, and looked at James. He was flushed with excitement from watching us, and with attraction for me. I waved him over, an the three of us embraced and softly touched each other. Sam gently moved back and guided James and me together. He looked at me with nervous, vulnerable eyes, as Sam whispered to him to relax and go with his desire. His kiss and lips were even softer and sweeter than his wife's. I kissed him back with the same slowness and tenderness. We broke off our first bi kiss.

"Thank you for including me in your fantasy," I said.

"Thank you for being my fantasy." I picked up my special bag and headed to one of the bathrooms.

I took a quick shower, and then rubbed lotion on my smooth skin, having shaved myself silky that morning. Now it was time for me to dress up like the slut I was, and give and get a good fucking.

I fastened the bra around my chest, and stuffed each cup with soft panties. My white and red trim button up blouse went on next, and I adjusted it to give myself some nice bulges in the chest. A satin garter belt went around my waist, and I leaned against the counter as I slowly rolled on my fishnet stockings, and let out a small moan of pleasure, the way I always did when I put stockings on. I fastened the straps of the garter bet, and slid my panties on afterwards, like a good little slut. The red plaid of my school skirt contrasted so well against the white top and black stockings. Now it was time for my favorite pieced of my slut gear, my strappy high heels.

They're so sexy. Black, 3-1/2" heels. A strap over my toes, and an ankle strap to hold them in place. I feel so sexy and excited whenever I slide my feet into them and fasten the strap.

My cock, which had been stiff and aching the whole time I was dressing up, now got iron stiff as I stood up, and turned around to face the mirror. I looked like a total slut, and I loved it. I was drinking in the view when Sam knocked on the door.

"Can I come in?"

"Yeah, sure," I said, my heart racing in my ears. No one had ever seen me all dressed up, and I was as nervous as a little girl.

"Wow. You look so hot! Can I go back to school too?" She walked in with a small bag, and told me to sit down.

"You never said anything about makeup, but would you like to try? I do James', and he loves the way it makes him look."

I said yes, and Sam spent the next 10 minutes fixing me up - blush, eye liner, and bright red lipstick.

"Let's style that hair up" she said, and fixed my hair with some mouse to give me a woman's short cut look. I have to say, now I did look like a hot little bitch.

"Oh, you're so sexy. I can't wait till James sees you. He's so horny, his cock is almost ready to cum by itself." It was the first time I'd heard her swear, and somehow it was really exciting. It meant that she was ready for sex too.

"Now just stay here while I toddle off and get slutted up myself, you nasty bitch."

It seemed only yesterday that I first slid on my wife's stockings. Now I was dressed like a woman, waiting to have cross-dressing sex with a hot couple. I was so excited I had to while away the waiting by rubbing my cock against my silky panties.

Finally, I heard the other bathroom door open, and Sam called out "We're ready." I smiled at the the pretty girl in the mirror, and walked out in my heels.

The sight I saw next was one I won't ever forget. Sam was dressed in heels, stockings, garters and a sexy bra that pushed her plump boobs together. And James. Oh James.

Imagine the sexiest French Maid you've ever seen. Now image her with a thick bulge filling up the front of her skirt, as she stood here in her black pumps, seemed stockings, short skirt, low cut top, and ruby red lips. She was the hottest thing I'd ever seen.

"I'd like you to meet Janet, my maid" Sam said. "What's your name?"

I'd never thought about giving my schoolgirl a separate name, but now it seemed so right.

"Jenny. I'm Jenny."

"Well Jenny and Janet. Say hi to each other." We moved towards each other, and I hope I looked at her as dreamily as she did to me. Her eyes just sparkled with desire and joy, and her face glowered with a shy smile.

She put her arm around me, and drew me in close. I could smell the same sweet flowers on her as Sam used, and I drank in the scent. Our legs touched, seemed stockings touching fishnets, and then our skirts, then our cocks. We both gasp as we felt the stiffness in the front of each other's skirts. We slowly swayed with each other, like we did before, except both of us were now dressed up in our finest sex clothes. It seem so right, so correct, so nice, to be dressed up holding onto another hot CD.

I couldn't wait any longer, and grabbed her body, pulling her in for a kiss, as our hands found each other's ass.

"Oh my God. You two are so fucking hot," Sam whispered. She began to rub her pussy though her panties, and within seconds they were soaked with juice. I trailed wet kisses all down Janet's neck, and stroked her her soft legs. It was all too much for me. The touch, the feel, the scent. My legs gave way and I dropped to my knees on the soft carpet.

I licked her inner thighs, and she moaned out my girly name. I lifted her skirt up, and saw her cock, trapped inside her panties. She was too big and thick for the confining satin, and I gently lowered her panties down to her ankles.

Free from the satin, her cock grew, and began to gently throb in from of my face. She was 6 inches long, smooth, with a beautiful plum head, all shiny with pre-cum. Janet's cock was simply the most beautiful I'd ever seen, and it was there in front of me, available for sucking.

My face felt hot with blood, and my hands were shaking as I flicked my tongue out and ran it along the underside of her cock. She moaned with joy, and I traced her shaft to where it met the head. A big drop of pre-cum dripped out onto my tongue, and now it was my turn to moan.

I opened my lips and took her inside my mouth. As my lips closed around her warm and silky skin, I knew I was going to be a cock sucker for the rest of my life. It just felt so right being on my knees, slutty heels fastened around my ankles, short skirt rubbing against my thighs, with this wonderful cock filling my mouth with a fullness that I'd only fantasied about until then. From that day on, Janet could fuck my mouth whenever she wanted, and I was always going to have some sexy CD available for stuffing my mouth.

I was surprised how easily cock sucking came to me. I guess by having one, I knew how to take care of hers, so I bobbed my head back and forth, letting my lips and tongue gently caress the shaft, pulling off to lick and suck just the oh so sensitive head. Janet moaned and told me how good it felt, which only added to how happy I felt being her cock sucker.

I felt Sam join me on the carpet, and she asked if she could have a lick too. I pulled off Janet's cock, and guided it to her mouth as I licked and took Janet's balls into my mouth. I came up for air, and Sam and I tongue kissed Janet's cock, sharing the sweet pre-cum flavor.

Guys, I know you don't want to be gay. But there's just nothing as hot and sexy as being cross-dressed, on your knees, sharing a CD's cock with her sexy wife.

Janet's moans were coming non-stop, and I felt so happy to be giving her the greatest thrill of her young life.

It took all my will power and control not to just keep bobbing my slutty lips over her beautiful cock until it spattered that wet sperm all over lips and face. I'd jacked off so many times, thinking of having a warm she-cock in my mouth. But I wanted to give Janet a taste of what she wanted too. They were such a sweet couple, and I felt so honored to be included in their intimacy. As the addition, I felt it was my job to pleasure them, as a return for the favor they'd shown me. So with a hungry mouth I released her cock, helped by the fact that I knew I'd have it again.

My own cock was in danger of bursting my panties, and so I got up, and slowly slid them off. My cock tented out the front of my skirt, and I felt so sexy standing here in my stockings and heels, towering over the sexy couple on their knees in front of me.

I began to stroke myself, smiling at them, turning them on even more with the movement of my hand over my long and stiff cock. I squeezed out a big drop of pre-cum, and smeared it over the head so I was all nice and shiny. Janet looked so nervous, excited, and flushed that I thought she was going to faint. Sam must have noticed too, as she held Janet with one arm, softly telling her to breath and relax. Sam guided one of Janet's hands to my ass, and the other to my cock for support.

"Relax sweetheart. It's right there for you. The cock you've always wanted. Hot, hard, and sticky. Enjoy."

I reach down and cup the back of Janet's head with my hand, and slowly pushed her towards my cock.

"Don't worry Baby. I know you're going to do a good job." I said, and pushed my cock closer and closer to making contact with her lips. Finally, the magic moment happens, and Janet's soft lips touch my hard cock. Both of us moan out like little naughty girls, sharing a forbidden and taboo pleasure. I've made Janet into a stocking wearing cock sucker, and am the first cock to ever slip past her virgin lips. I felt so proud and contented to be the one to help her lose her virginity.

Just like me, once she got the rush of feelings of finally having a cock in her mouth under control, she sucked a mean cock. Janet swirled her tongue all around my head, and greedily slurped up the pre-cum that was now dripping like wild from my slit. Then she opened her mouth wide, and took me down as far as she could. She got about 3/4 of the way down my 7" cock before she had to come up for air.

"Good girl. Such a good cock sucker you are. Don't worry, you'll get lots of practice. You can suck me anytime you want to. I'm yours for the asking." I said, and Janet beamed such a beautiful smile.

Her shyness gone, she stared to become the cock sucking whore she wanted to be. My cock was licked, sucked, and kissed with lust, greed, and passion. She popped my cock head out of her mouth, and held it out for Sam to close her lips around. Now I was having my cock sucked by both them, husband and wife, though the husband was a bit feminine looking right now in her stockings, heels, and maid uniform. They passed my head back and forth, then both of them slashed their tongues over my head and shaft, making me let out a girly moan, and another big drip of sticky juice.

Sam decided to turn up the action, and grabbed a bottle of lube from her bag, lubing up her fingers as she looking at me with sexy, slutty eyes.

"How would you like that little schoolgirl ass fucked with my fingers?"

"Oh yes baby, please. My little virgin ass need a good fucking. Please be my first," I moaned out. She reached between my spread legs, and found my tight little hole. Like all men, I dearly love having my ass penetrated by anything long, smooth, and hard. She lubed me up good, smearing lots of cool gel around me, and then slowly and sweetly slide inside my backdoor with her index finger. If I was a slut before, now I was a total tramp, cross-dressed, standing there in high heels, a CD maid sucking me off, while her wife screwed my ass with wet, slick fingers. I'm not sure what I'd done in my life to deserve such a treat, but whatever it was, I'm glad I did it.

"So my little slut likes her ass fucked. You're so tight sweetie. You're grabbing onto me with every stroke," Sam said. "Is it turning you on, being fucked on both sides? Does it make you pump out that cum? Janet, is she soaking your mouth with juice?"

Janet pulled off my cock with a slurp, licking her lips. "She's dripping all over my mouth. I can't believe she hasn't cum yet. And that's what I want Jenny. I want that wet sperm flooding out of my mouth. Please give it to your little maid whore. Fuck my lips, and cum in my hot, wet mouth." She licked my swollen purple head dry (for just a few seconds, until the next drop of pre-cum spilled out), and then covered my throbbing erection with her young mouth again.

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byneon_noodle© 20 comments/ 174980 views/ 44 favorites

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