Tacking into the Wind

[[names changed to protect the naughty]]

"Ashley, I need to talk to you, baby." She came into the living area and joined me on the sofa. I put my laptop away and looked up at her.

"Yeah, Kaye, what's up?"

"Wanna make some money, baby?" she asked, smiling devilishly and looking absolutely beautiful as she stretched a leg across my lap, wearing only a tube top, g-string, stockings and heels.

"Well of course," I answered, brushing out her long dark hair with my fingers. Kaye has been a close friend for years, having moved in with me a little over a year ago after I quit my last job to focus on my webcomic and photography side-business. Funds were a little tight then, and I needed someone to share my expenses. At nearly the same time, she had finally broken up with her previous boyfriend. It helped that I'd had a crush on her that survived several relationships, and she had no small attraction to me as well, as even when "attached" she'd found herself sneaking over to "wear out her favorite piece of ass." So when she became available, inevitably we got involved. Also, she was a highly skilled transsexual escort with a fairly reliable pool of regulars. So far, things were going well. I covered the rent, and she covered all the other expenses. Even so, what she said next kinda caught me off guard.

"I want you to come in with me," she said simply.

I must have looked confused, because she went on: "Come on baby, I've seen how hot you can look. And sometimes I need a partner. And I trust you more than the other girls I know. Besides, you know you're the only girl that I even get hard for."

She was right. Almost ten years ago another crossdresser I'd hooked up with had insisted that I dress up for her before we'd do anything intimate. I was still very inexperienced then, so I went along with her on a whim. Since then I'd done it few times for anyone that had a kink for that. Slowly I realized that I did seem to make a rather sexy girl. When I met Kaye, I hadn't really planned on sharing that with her, since I'd already heard she wasn't at all into feminized boys or other t-girls. But she surprised me by apparently making an exception in my case. Still, I was a little nervous. "Come on, baby," she pleaded. "I know we'd make a very good team. And besides, I know you've been known to trade a little ass for favors in the past."

She had me there, though I was still uncertain about taking what seemed like a giant leap forward. "I'll start you off slow," Kaye promised.

"I bet," I said, raising an eyebrow and smiling wryly. "So what, you're trying to pimp me now?"

"Yes," she grinned. I couldn't tell if she was joking or not.

What the hell, I decided, let's see how it goes. "Okay, we can try it on a trial basis. Trial basis."

Kaye nodded, looking quite pleased with herself. "Thank you, baby. We're going to start right now. Rick wants a double tonight, and I've seen the way he looks at you when he comes here. Let me tell him he'll get to see you tonight after all. Give me a few minutes and then I'll help you out in the bathroom." She bounded off the sofa and disappeared into the bedroom, leaving me both disturbed and exhilarated at how quickly I'd agreed to this. But then I shook it off and went on into the bathroom, stopping by the closet to pick out a few pieces of clothing.

Just as I'd finished bathing and dressing myself, Kaye joined me in the bathroom. I had no idea how to do makeup yet, so she was going to handle it. She nodded approvingly at my outfit, which was a simple setup of ultra-sheer red stockings, red lace boyshorts, and a white camisole. "He's going to really like that," she said as she slipped a long black wig on my head and began braiding the hair into a single long plait stretching to the center of my back. "Rick's really into thin frames and long legs. If he wasn't used to me after dating for so many years already, he'd have found someone else. I'm a little too curvy for his tastes now." Kaye was right. She'd started out with a body like mine, only seven inches shorter--but over the years, hormones and then surgery had reshaped her body into an outrageously blatant package of sexiness, with softly angular facial features, 34DD tits, a 26-inch waist and 38-inch hips. And the nine-inch rod of thick black hardness tucked between her thighs didn't hurt.

"Hmm," she frowned, looking at my lower jaw in the mirror. "Your shadow is a little dark, but I'll show you how to deal with it later. Tonight we gotta move quick though." She skillfully applied foundation and concealer until my face was evenly toned. A few minutes later she stepped back and checked my face out closely, then nodded to herself. "You can handle the rest. I'm going to go keep Rick occupied." Kaye sashayed back into the bedroom, while I decided on applying some lip-liner with dark crimson lipstick, then eyeliner. No eyeshadow this time, and I decided against spending the time to do my nails too. I lotioned myself down and spritzed my body with a few dabs of perfume, After slipping on a pair of white heels, I joined them in the bedroom.

Rick craned his head to look at me directly as I sat down next to him. He was already naked as the day he was born, displaying an impressively toned Latin body. "Wow," was all could say as his eyes travelled all over my body. "I kinda wasn't expecting you to look this good," he confessed.

I decided to blow that off, deciding to take the compliment in the spirit it was meant. Kaye broke in with a quick introduction. "Ashley, you already know of Rick. So Rick, this is Ashley, as I promised. Now be nice to her."

"Of course," he answered, already slipping a hand up my stockings and inside my panties. He fished out my meat and squeezed it gently until it swelled into a raging erection. "Definitely seven inches," he murmured. "Nice, I love it Ashley."

I didn't trust my shaky voice to not spoil the illusion, so instead of speaking I leaned in to kiss Rick hotly. A quick glimpse at Kaye revealed her sitting back against the headboard with her knees up and thighs spread wide apart, watching with a smugly satisfied smile as she idly played with her stiff nipples. Her g-string had been jerked to one side, exposing her balls, while her cock laid back over the flat of her stomach, twitching every so often.

Rick guided me onto his lap, still fondling my dick and playing with my pre-cum as it leaked from my head. I wrapped my legs around his midsection, squeezing him tightly with my thighs and running my hands over his chest, which was as smooth as my own. His nipples stiffened and I started lightly squeezing and brushing my fingertips over them too. He reacted by sliding his other hand down the back of my panties and probing my ass with a single thick finger. "Kaye tells me you're a bottom slut," he murmured in my ear softly. "Is that right?"

"Mm-hmm," was all I could get out, as he'd inserted a second finger just inside my hole. "Get on the bed," he directed. "Spread your ass open and keep it high." I rushed to comply, doubling over across the bed with my knees drawn up to my chest and my face pressed into the sheets near Kaye's feet. "Good," he said. "Keep it open, like that."

Rick spit three times directly in my crack and used his fingers to wet down every inch. Then the bed shifted as he climbed behind me and began trying to get his thick bare cock in my tight ass, "Wait!" I gasped, almost pulling away. "You can't fuck me bare!" Only Kaye got that privilege.

"Yes he can, baby," Kaye corrected, now stroking her own cock. "I've got his STD screening. Rick's okay. Now be a good slut and give him your pussy. Right now it belongs to him just like it belongs to me." Well, that was all right then. Just as I allowed myself to relax, Rick buried his own seven-inch duck in my pussy with a single rough thrust. I was still just a little too dry, so my hole was burning like fire with every jab. I was getting distracted by the pain and my hands slowly relaxed, letting my cheeks close up again. "Keep them open, Ashley!" Rick shouted. "I like to see my pussy spread wide open when I fuck it." I gritted my teeth and pulled my cheeks apart again as ordered. Rick responded by shifting position to a sort of standing squat and pounding nearly straight down into my ass, which was not loosening at all. My hips rebounded with each powerful thrust, and my dick swayed crazily between my legs, flinging thin streams of pre-cum on my stomach, thighs, chest and sometimes my face. Finally after a few minutes of Rick's brutal fucking, sweat and other fluids began to lubricate us enough for the pain to slowly fade. Not much later Rick's steady pounding became truly enjoyable as his meat jerked back and forth over my prostrate. I got the familiar urge to pee that normally signaled masterful stimulation of my pussy as it finally loosened up. I turned my head to look at Kaye, who was still calmly watching with that same self-satisfied smile and playing with her dick as I failed to hold back a thin feminine gasp every time Rick bottomed out inside me. Then she slowly extended one of her trim legs in my direction, pressing her toes insistently against my lips. Without thinking I opened up and she immediately jammed her toes against my tongue, moving them slowly back and forth between my lips.

"Suck them for me baby," Kaye hissed. Her voice was choked with lust, enough for her to do something she'd never done with me. "Come on, lick my feet for me, baby. Do a good job and I'll feed you this hot cock too." She held it up so I could see it clearly, now completely slicked down with her pre-cum. "Or would you rather taste my ass instead? Rick fucked it just like he's fucking you now, and it could use your hot mouth on it."

We'd done enough 3-ways for her to know exactly what was going on in my head. I had long ago switched my mind off and turned myself completely over to their desires. I felt her toes fucking my mouth gently and my tongue swabbing them over and over. "That's right, baby," she whispered. "That's why I wanted you with me. I know you can't help letting yourself get bitched out. I just don't think you should do it for free, baby."

With Rick's continuing fucking and Kaye's encouragement, my body and mind were shifting into a delirium of pleasure. I barely felt the bed shift again as Kaye removed her foot and moved in front of me, facing away from me and bending toward the wall, with her g-string again pulled to the side and spreading her own ass with her hands. Rick saw it too, and began fucking me faster, no longer pulling almost completely out but instead short-stroking with only half the length of his dick. "There's your present, Ashley," he gasped out. "We both made it for you."

She'd always teased me about making me clean her out after a fucking, but I'd figured it was just talk since she hardly ever allowed anyone to penetrate her and always used protection if she did. Obviously she was intent on getting it tonight. Irresistibly drawn to Kaye's spectacular ass, I began licking her crack from top to bottom, while she groaned deep in her throat and pressed her ass ever harder against my face. Soon her motions caused her hole to suddenly spasm and a stream of white cum steadily seeped out of her winking ass. I placed my tongue just above her smooth brown balls and let the cum pool on its surface, then slowly lapped it up. Before any more could leak out, I sealed my lips around her hole again and began sucking it gently. She opened up again and the remaining cum trapped inside her drained into my mouth. "Yes, oh yes, that's so hot, baby," whispered Kaye. "Rick, do you know I've never had anyone eat my ass after a fuck before? But Ashley loves my ass so much she'll do it. I can always expect her to do what I need to feel good."

Rick couldn't answer, being no longer to hold back. His climax came with no warning--suddenly I heard him grunting and felt his cock throbbing. He kept on pounding me even while his cum coated the inside of my ass, not stopping until his spurts finally ceased. "There you go, Ashley," he said. Amazingly he was barely out of breath. "Now I've left a present for you too." I couldn't do anything but remain frozen in place. My ass was throbbing and burning again, and I was too overexcited to have gotten my own orgasm. While I tried to calm down, Rick wiped himself off on one of my stockings. "Keep this bitch around, Kaye," he said. "The next time I'm back in town I'll be seeing both of you again."

Finally I relaxed enough to roll over and sit on the edge of the bed. Kaye joined me, sitting sideways across my lap with an arm around my waist. Both of us were still uncomfortably erect and still extremely turned on. Rick watched us kissing passionately and fondling each other as he got dressed.

"Stay here, baby," Kaye muttered, breaking our embrace as Rick finished lacing his shoes and gathering his gear. "I'll get him outta here and then we can finish up." They left the room, conversing softly. Seconds later I heard the door slam and Kaye came back with a tightly folded wad of bills in her hand. She sat down straddling my lap again and kissed me deeply. "Mmmm I knew you wouldn't disappoint me, baby. You did sooo good." She broke off and quickly counted through the cash, which looked to be around $300--a little less than I'd expected for this job, but then I remembered that Kaye and Rick went way back, so she'd probably given him a break. "You'll get most of it...this time." She folded up ten twenties and tucked them into the band of one of my stockings, while dropping her portion into her purse on the floor.

"This time?" I echoed sarcastically. "What makes you think there'll be a next time?"

Kaye stood up and kicked off her g-string, now stretched irreparably out of shape by tonight's activities. Her lovely brown cock pointed nearly straight up, still fully hard and still glistening with her juices.

"Pretty sure I'll get my way," she promised as she held my face steady and guided herself toward my lips.

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