High Heels and Stockings Tryout Ch. 02

Sam's finger went a bit deeper in my ass, and began to rub all around, while Janet's head bobbed back and forth. I thought of how many times she must have sucked off Sam's strap-on, fantasizing about just this moment, and how lucky I was to be her first cock. I reached down and held onto her shoulders while I waited for my orgasm to hit.

Between the fantastic, first time blow job, Sam fucking my ass, and me being all sluted up, it didn't take more than 30 seconds, and I felt that solid swelling when you know you're going to spurt. I tightened my asshole around Sam, and moaned out Janet's name.

Just like when I jack off all cross dressed, my first few spurts were all pre-cum, and Janet moaned with lust around my cock as I flooded her mouth, just like she wanted. Sam's finger was locked in my ass, and then the rest of my orgasm hit. I tried to keep looking down at Janet, so fucking sexy kneeling there on her stockings, skirt brushing around her thighs with every sucking movement of her body, looking up at me with thankful, loving eyes as I made her the woman she'd always wanted to be. The cum was dripping out of her mouth and down onto her blouse, as much as she tried to swallow it all down. But when my main climax hit me, I just had to close my eyes, and let out a huge moan as I emptied my balls through my swollen cock into that warm, wet heaven. I must have blasted 6 or 7 ropes of cum out, each one a special peak of even greater pleasure in a warm pool of escasty. I had to lean back into my heels to keep from falling over, as my cum took all my strength away, seemingly pouring all my energy into Janet's mouth. Finally, my cock stopped ejaculating cream, and I was able to open my eyes at sexy, sexy Janet, swallowing my load, and running her lips and tongue all around to get the rest.

Sam tenderly slid her finger out of my ass, making me jump with stimulations, and leaned over to her wife for a wet, spermy kiss. I drunk in the sight of them kissing the cum off each other's lips, knowing I would jack off to this memory for years to cum. I collapsed down to my knees, and joined them in a girly kiss.

"Did you like that sweetheart?" Sam asked Janet. "Did you like that hard, thick cock stretching your mouth, and soaking you with cum? You looked so good sucking on her, such a nasty, filthy little slut who can't get enough cock. Just like you've always wanted to be. Are you going to turn into a total slut now? I'll bet you won't be able to keep enough cocks in your mouth. And you," she turned to me with a smile. "Did you like fucking my slut's mouth? Was she good?"

"She was the best blow job I've ever had. Janet, you can suck my cock anytime you want to baby. As long as I can get a taste of you sometime too."

Sam recovered first from our shared cum high, and stood up to lead us to the king sized bed. She pulled the sheets down, and patted on the soft mattress.

"C'mon girls. Plenty of time to rest up later. For now, I wanna see you two fuck. Besides wanting to make a cock cum in her mouth, Janet's other nasty fantasy is to have her pretty little ass fucked by a real cock. I've tried to keep her satisfied with my strap-on, but despite all the good fuckings I've given her, she keeps wanting a warm, purple cock. Want to break her cherry?"

I looked at Janet, who was blushing again (so cute, she has cum on her blouse from sucking cock, and is still flushed at the thought of getting fucked), and smiled. "I would love to take you cherry Janet. May I?" I held her hand, and guided her down onto the bed, a soft pillow under her stomach.

She looked so wonderfully hot - heels, stockings, pushed up skirt showing her garter belt, blouse, and lipstick smeared lips, looking back at me with happy, horny eyes.

I got into between her legs and lifted her skirt up over her ass.

"First, your back door needs a bit of loving to get ready." I took the bottle of lube, and dripped big splat onto her, letting it run down her ass, making her squirm with the coolness of the liquid. Then I gently rubbed the top of her stockings, making her wait for her ass to be pleasured. Slowly I moved my hands up to her cheeks and spread them apart, exposing her most intimate area for Sam and I to see. Her asshole was beautiful - smooth, pink, and just so lickable. It glistened with the lube, and I couldn't wait any loner. I flicked my tongue out and made contact with her ass, causing Janet to moan, and Sam to curse.

"Yeah, that what I want to see. Two little sluts playing with each other's ass." It was thrilling to hear this sweet and tender woman turn into a nasty and demanding bitch during sex. Janet wasn't the only one turning into what she'd always wanted to be.

"Lick my sluts asshole. Get her ready for that big cock. I've just fucked her with a small strap-on, so she'd stay nice and tight. But look at her now. Rotating her ass back on your tongue and mouth like a cheap slutty bitch. You like having this schoolgirl lick you ass. Makes you feel like a real woman, with a real pussy. You just wait, little slut. She's going to fuck that hole of yours good and hard." Such filth coming from such a sweet mouth. I loved it.

Once Janet's asshole was all wet, hot, and lubed, it was time for her to be turned into a whore for good. My cock had swollen back up again, and started to throb with my heartbeat. For good measure, Sam put her lips over it and gave it a nice wet suck.

"For luck. Now fuck my slut's ass."

I lubed my cock up till it shined in the light, and scooted forward on the bed. Janet got up on her hands and knees, and lifted her ass towards me, like a well trained little whore. Sam must have taught her well how to take a cock. But she'd never had a real cock, all warm and hard meat, under a soft and smooth skin. My cock was the first part of my body to touch hers, and my cock kissed her asshole, saying hi for the first time. My cock and her ass. Meeting each other for the first, but not the last time. Janet moaned cheaply as she felt the warm pressure of hard cock on her asshole. Our bodies were joined in a tender exchange of intimacy, every jerk of my cock stimulating her ass. Gently I leaned forward, pressing my head against her hole, as I grabbed her firmly by the waist, getting a hold of her bunched up skirt and hips. She was tight. Tighter than any woman I'd ever had. But we were both so wet and lubed, my cock was so hard, and her ass so hungry that after a few seconds of blunt resistance, her asshole opened up and welcomed my inside like a long lost friend.

The feeling of my cock sliding into her virgin ass was indescribable. The fact that we were both so slutted up made it so nasty, kinky, and hot.

Janet's slutty moans filled up the whole room, until her wife shut her up by kissing her hard on the lips. Then she just whimpered like the bitch she was, getting her first good fucking. We bucked back and forth, our stockings and heels rubbing against each other, and we fucked like little schoolgirls. I held onto her garter belt, keeping a good grip on her, and Samantha started calling Janet a slut and our bitch.

"You little slut. You've finally gotten what you've wanted all along. A big hard cock in your tight little asshole. Do you like it slut? Does it make you feel like a real woman to bring pleasure to that prick? Then fuck him! Fuck him good. Work that asshole around his cock. Make that cum boil up from his balls. Make that stud cum!"

Finally, it's all too much stimulation for me. The nasty cross dressing. The feel of the stockings and heels. The way Janet's ass gripped and rubbed my cock. I gave out, and let myself cum.

I tightened up my asshole as my cock went rigid in Janet's ass. She felt the stiffness of my cock, knowing it was going to splash her asshole with sticky hot sperm, and she groaned without control. My cock went iron stiff, and I felt the cum shooting up through my rod, into her now well fucked asshole. The sensation of all that hot fluid filling her ass, knowing that she's made a hot cross-dressing stud cum was too much for her, and without even touching her cock, she blew semen all over the sheets. I kept spearing her asshole until my legs gave out, and we collapsed on the bed, her anal virginity taken.

We laid there for about a minute, getting our breath back. Slowly and tenderly I pulled my still hard cock out of her now slutty ass, and she whimpered with delight. She was truly now a slut, having made a cock cum in her mouth, and her ass. Next time I'd ask to have the favor returned, and get my cherry broken, but for now it was her night.

The three of us stretched out and relaxed in the king sized bed.

"Janet sweetie. Did you like making that cock cum? I'm not going to be able to keep cocks out of your mouth and ass, am I?" Samantha said, running her fingers along Janet's stockings.

"As long as Jenny here wants me, I'm hers alone." she replied, making me blush with joy.

I kissed them both on the forehead and we snuggled for the night, Sam's two studs still slutted up, me in the middle of this wonderful couple.

I thought about what would happen next - me getting fucked. Maybe a DP of Sam with our two hot cocks. Maybe ever bringing my wife into the action. But for now, nestled and surrounded by these two hot people, there was no place else I'd rather be.