Change of Heart

[[names changed to protect the naughty]]

"Okay, Shasta--what's the deal with that chick?"

It was late January. Shasta and I were sharing a cigarette under the eaves of Rod's, one of the more notorious gay hangouts in the city. This one featured drag shows four nights a week, which tended to cause many of the bolder TG girls to visit at least for part of the night...especially on a Friday night like tonight. Of course, it was an open secret that many of the younger girls came to work the area as escorts too. As long as the streets stayed clear, the authorities tended to look the other unless there was a disturbance.

Shasta was one of my oldest associates in this scene. By chance we'd dated the same girl (who gave me my first TS experience) almost five years ago--and drifted in and out of each other's circles for months before finally befriending each other. He was a little older and knew more of the regulars than I did, so I tended to pump him for information. He followed my eyes and locked on a Black girl just about to enter the bar. She looked about three or four years older than me, with skin a shade or two deeper than mine, and about four inches shorter. Apparently she didn't wear wigs very often, as her natural hair was styled quite nicely. She didn't mind showing any skin either, even by the standards of this area. From what I could see, she was wearing a hip-length leather coat over a black fishnet bodysuit and a metallic silver tube top, with black and silver platform sandals. From the way her coat was belted tightly closed I was certain she'd left the underwear at home. Apparently she had a robust immunity to low temperatures. But her body was outstanding. She had the well-developed legs of a woman that...well, did quite a bit of walking. What also caught my eye was the fact that her hips were wider than her shoulders...not by much, but just enough to be noticeable even from thirty feet away. She had a nice set of breasts too...probably B-cups, but somehow they looked fuller on her athletic frame. Unfortunately her brow was frozen into a stormy, irritable frown.

"Ashley, that's Kaye," Shasta was saying. I turned back to him as he continued: "She's a pro...been around for about five years. Never been in trouble, but man she's got this thing for picking dudes that take advantage of her."

"Hm," I said blandly, filing this intel away and gazing back over the clubgoers passing on the street.

"Man, that's probably why she's pissed tonight. I'd heard her latest li'l issue was with them dudes spreading those counterfeit twenties...and some of 'em just disappeared from the scene last weekend."

I started to connect the dots. Chances were high that feds would be visiting Kaye's house with a warrant soon, looking for some shit she had no knowledge of. Yeah, I'd be fuckin pissed too.

I finished off the cigarette and went on talking about the new job I started. Kaye's business receded into the background.

Two months later, however, random chance intervened. On a whim I stopped at Rod's to wait out the evening rush hour--and found myself on a stool next to her. She was in a brighter mood this evening...and looking even prettier in regular street clothes. She saw me sit next to her and spoke:

"So finally I get to speak with the elusive Mister Ashley."

I wasn't surprised that she knew me on sight...I just hoped she didn't know me by rep.

"Hey, Kaye. So what do you mean?"

She looked at me innocently. "Well I was wondering when you'd work your way over to me. The girls say you do get around...."

She was half-right. After breaking up with Symone a little over a year ago I'd taken another break from dating. So during that time frame I'd been picking up any one of six or seven girls when I needed some private company. But I had picky tastes, and I'd contacted only one or two of those for a repeat rendezvous. So apparently the word was that I was "nice, kinda deep, a good tipper, a little freaky, but fickle."

I thought I was pretty restrained, and said so. After all, none of these girls would ever hear any of their private business being spread by me.

When I put it that way, she saw my point. "Well, Christiana--you know her as Maribel--" she explained. "--Christiana told me you were one of the fun ones."

As for ignoring her, I answered that every time I saw her she seemed disgruntled, so I didn't bother. She burst out laughing. "Boy, you are so silly. That's just so the cheap fuckers don't waste my time. If I really went around feeling like that all the time, I'd have a stroke."

"Mm--I'll accept that," I said. "And I'm thirsty. What can I buy you, Kaye?"

"Ohhh," she answered. "A gentleman. Nice." She gave me a long unreadable look. "Well whatever Mister Ashley is drinking is fine with me."

Forty minutes later, we were on our fifth round of vodka sours and actually beginning to become friendly, if not yet friends. We talked about our hometowns, future plans, the hustle game in general.... Then she started to pry into my romantic business. I said I had no prospects, and wasn't really looking. Simple as that...unless she was planning on volunteering herself. Kaye smiled and chuckled softly. "Well you're a little late. But don't give up. You never know what tomorrow might bring."

Then she leaned closer and said softly, "Ashley, you know what I do. You're cool enough and I know I wouldn't be bored with you in private, but if you want my special time when I have a boyfriend, then I need a favor too. But you've shown me a nice time already, so we don't need to worry about that today. But...when we hook up, you'll have to follow my lead."

"Fair enough," I answered. "You ready to get out of here?"

"Most definitely," she answered. "But just give me a few minutes." She went over to a younger Mexican boy in the back corner watching one of the TVs. I'd seen him around before, but never really paid attention since he looked like he was barely out of high school. I normally saw him at night on the weekends and only knew him by name. She spoke to him for a bit. He looked my way and smiled, then nodded his head and got up. Kaye waved me over and explained, "Leon'll be tagging along with us. We're going to chill at his place, okay? Don't worry, he and I are very cool."

"Mm--no problem," I agreed, and we walked out. Leon shared a duplex just a few blocks away, so we got there after just a few minutes' walk. His roommates were all gone until later that night. "So what's the deal?" I asked once we'd gotten comfortable. Leon was already quietly peeling off his clothes next to me on the sofa.

Kaye grinned as she started stripping off her own shoes and jeans. "Well...if you want to have me, then you're going to show me something I like seeing." Seeing where this was going, I slowly started undressing too.

"Which is...?" I prodded.

"I want to watch you boys play around," she answered. I shifted uncomfortably. She noticed and instantly her face darkened. "Don't play with me, Ashley. I did warn you I'd be running this. And trust me, I know just how much of a freak you've been with those other bitches, so you will do this for me." I knew she was right, and I caved in.

Leon stood in front of me holding up his dick, which was already stiffening. Kaye sat next to me, getting hard as well. It was my first good look at her body...and it was very hot. Slim legs, very thick thighs, and nicely filled-out hips with a very firm ass. She wrapped a hand around her uncut dick and it swiftly expanded to its full nine-inch length. I found myself heating up rapidly at the sight of her.

"Ready for him to suck you, baby?" Kaye asked, watching me closely but addressing Leon as he held the head of his dick at my lips.

"Oh yeah," he breathed.

She waved me on impatiently. I licked my lips and ran my tongue slowly around the head, licking it slowly and getting it wet. Both of them sucked in a breath and she urged me to keep going. I kept licking the underside of his shaft, enjoying their heated moans. Finally I opened wider and sucked Leon between my lips, stopping once he'd penetrated a few inches and still running the tip of my tongue around the head.

"Mmmm...that's nice. Is it good, baby?" asked Kaye.

Leon had his eyes closed and replied,"Yeah...he's got a hot little mouth. You should feel what his tongue is doing."

"Maybe I will later." Kaye was still rubbing herself gently, taking her time. A few minutes passed as I continued to tease Leon with my tongue, then started sucking him deeper, letting him work his hips back and forth and getting his full five inches sliding over my tongue. "Now let him fuck your face, baby. Let me watch you eat that dick for me." Leon gripped the back of my head firmly and started ramming his dick through my lips in a steady rhythm, stopping every so often to hold his dick in my throat until I needed to take in a quick breath, then pulling out and starting over.

"Damn, ya'll are making me horny," Kaye gasped. "I love watching a sloppy blowjob..." And it was. Leon's dick was trailing streamers of spit every time he pulled out, and it was leaking over my lips and covering his balls every time they slapped against my chin. "Oh yeah, baby...that's right...suck that fat dick, Ashley," Kaye went on.

Her heated encouragement was making us both horny. Leon's thrusts were starting to become less regular and more powerful, and his breathing got deeper. Without warning he pulled out with a grunt. "Was about to finish," he explained. He stood there for a bit while he got control of himself and then sat down between Kaye and I.

Kaye's eyes flashed as she reached over to stroke both of us gently. "So do you want some ass too, baby?" she asked with her eyes daring us to say no.

"Hell yeah," said Leon.

Kaye stared at me and said flatly, "Take care of him, Ashley. I want to see him fuck you right now." She reached in her purse and handed me a packet of lubricant.

"Yeah, c'mon, man," Leon insisted. I answered by greasing myself up and squatting above his lap with my elbows resting on the floor. "Mmmm...yeah, let me have that ass right fuckin now, man," grunted Leon as I did just that.

"Yeah, do it, baby," murmured Kaye, "Sit on his dick and ride it, baby." I wasn't sure how she could watch with her eyes closed, but her mouth was open in a perfect "O" of lust and her hand was now blurring furiously up and down her shaft. Her eyes cracked open just as I dropped my hips all the down and Leon entered me fully. I swiveled my hips until I felt comfortable, then slowly began bouncing on his rod.

"Oooooo shit yeah," they both groaned in unison.

Kaye rose and kneeled on the floor in front of me. "Here you go, baby," she purred. "I know you need it now, so I'll feed you some cum." She balanced herself with one hand on the back of my head and wedged her cock between my jaws until it reached the back of my throat. Just then Leon grunted out a quick warning and exploded deep in my ass. I stopped humping him and sat still, keeping him held inside while I started rubbing my dick and worked on Kaye--though that wasn't too difficult. She was bringing herself off with my mouth quite nicely, being incredibly aroused by watching two guys fucking right in front of her. Then she pulled out again. "Mmm--enough...that's good, baby." Her hand went back to her dick and started working it again, masturbating herself right in front of my eyes and rubbing her balls on my face every few seconds while Leon and I watched greedily. Moments later Kaye sighed deeply and showered my cheeks and mouth with several bursts of cum. That set me off in turn and I shot off all over my fingers in a brief but very draining orgasm.

After we could move again, Kaye asked Leon, "Better than the last time, hm?"

"Hell yeah," he answered. "That was some hot shit. Wouldn't mind doing it again." I got off his lap and he disappeared into the bathroom, returning with a handful of damp towels.

"We'll see," she replied, watching me with a thoughtful expression. Soon Kaye and I got dressed again and walked back to the bar. We had a few more drinks and talked a while longer, then I called it a night.

The next hookup four days later was just between us. Apparently I'd passed some kind of test, and from there we got together at least once a week. Eventually we started to become friends rather than just associates. I came to see her as a remarkable girl--very clever and self-aware, very creative and strong-willed. So I gradually found myself going farther out of my way to look out for her. I shot some pics for her and set up a website as well--which eventually put in the view of travelers and visitors with deeper pockets. By then she was no longer trying to charge me, instead asking me to share dinner or pick up a few minor things for her. Her visits started increasing to twice and sometimes three times a week, as she would just say that she "had to play with her favorite ass and couldn't wait." Then we'd fuck each other's brains out, cool down by watching TV, get some food--or maybe just lie there talking--and then she'd sneak back home. To anyone else observing, it would have been clear what was starting to happen, but no one else was even aware of just how much time we were spending together.

Fall passed, and then winter, then spring again. And then again. Not much changed except I'd begun and ended another relationship, which was a little less disastrous than the previous one. So had Kaye—but her latest one continued even though it was had been getting quite rocky. Then almost exactly two years after we first met, Kaye vanished for a few weeks...and suddenly resurfaced just before summer with an amazingly-enhanced body. That was when she went from simply pretty in an aloof kind of way to strikingly beautiful. Oh yes, she was pretty happy with her doctor, and I was impressed.

The next weekend she gave me a call and told me she was on the way. I quickly picked up and got my place relatively clean just before she knocked. When I opened the door I went speechless. I hadn't yet seen her up close since she'd come back home. She was lovely beyond measure...almost literally my ideal image of a woman. I waved her in and she sat down. Finally I found my voice...enough to say "Damn girl, you look incredible. Seriously, you're so lovely I can hardly look at you. So what happened?"

She stood up and did a slow semi-pirouette. "34DDs up here. 38 inches down there. Left my waist alone. Had my face softened a little. That's it." She sat back down and looked at me very seriously.

"But if not for you it probably wouldn't happened til next year or even later. Remember the man from Minnesota?" Sure, I remembered. A random internet hookup last winter had led to a couple that wanted a 4-way. I suggested Kaye and myself. I was willing to do it just for the experience, but explained she would need some consideration. They agreed, but made it clear they were recording the whole thing for their own site. The guy in Minnesota saw that video, tracked me down, and so I referred him to Kaye's site. The next time he flew in he wanted to see both of us. So I did that as a special favor for her and eventually forgot about it.

"Anyway," Kaye went on, "he flew me up there to spend a weekend with him. The ad revenue from the site and his payment put me just enough over the top to pay my doctor up front. So...thank you so much, Ashley. You don't know how long I've looked forward to this." Then she shocked me by kissing me with real heat and passion. And then I probably surprised both of us by responding in kind. Then we slowly disengaged, remembering that I was unattached in any way...but she wasn't. I just looked at her. It was obvious: some time in the last few months I'd let my feelings get out of control, even though I'd barely let myself become aware of it. It wasn't love yet--but it could be with a little more deliberate effort. Worse, she knew it now--and she also became aware that her feelings had deepened too.

"Damn," she said.

"Well this is a nice little soap opera," I said dryly. "Kaye--what's the deal with you and Jackie? You know I normally don't dig into your business, but a couple of years you almost got wrapped up in that drama with Ryan. And now we both know Jackie is well...breaking the code. You can do better, babe." The code was pretty simple. If you're sharing a space with someone, don't use the household funds on stuff you wouldn't both agree on--like other chicks. Worse yet, don't admit it out loud.

"You're right, Ashley--I'll handle it," she declared. "But not just yet. I have to get a few more ducks in a row first."

I nodded in understanding. But.... "Kaye," I started. "We can still dial it back, at least for now. It's hard, but we're old enough to know it can be done. We don't have to make it harder just yet. I can rationalize a lot of things, but not deliberately breaking people up...not yet anyway."

She looked down at the floor. "I don't really want to, Ashley. I knew for months how you felt, but I always found a way to blow it off. I just thought maybe the sex was confusing things. Or maybe it was just an intense friendship that got a little overcomplicated. But I can't tell myself that now." She kissed me again, touching my lips for just a few seconds. "I know you'd be good for me...you've never judged me or tried to play me. And I'm not perfect, but I can be the kind of woman you need. If you can give me a little longer, it'll work out."

"Now," she said, brightening up. "I came here to let you check this body out very closely." She pressed her breasts against my chest and whispered, "What do you think so far? Need to look closer?"

I slid a hand to her perfectly formed bottom and pinched it gently. "Hm, I reckon you might be right, Lady Miss Kaye. Let me get you unwrapped." On impulse I kissed her deeply, not trying to keep anything in check this time. She felt it...and accepted it happily. "I'll wait for you, lovely," I promised. "As long as I can."

"I can live with that," Kaye answered. "Race you to the bed."

She won.

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