Chapter 3

"What are you doing here?" I'd expected a guy selling vacuum cleaners, or some Jehovah's Witnesses or something.

"Surprise!" Shelly smiled at me. She stood on my doorstep like a little girl, hands behind her butt, twisting on her hips.

I have to admit I was at a complete loss. I probably should have slammed the door in her face. I could have called the cops maybe. At the very least I should have told her in no uncertain terms to get the hell out of my life, but I didn't do any of that. I just stood there blinking at woman ... er, man, I mean.

Except she was posed in a red mini-skirt, the stretchy kind, and her legs didn't belong to any guy I'd ever heard of. Neither did Shelly's breasts, which were kind of right there, jutting proud and firm between her slender shoulders and flat tummy. She wore a short halter top, a black one, and it said, "Naughty boy ... Go to my room!" across the front. Her golden hair fell in waves around her beautiful face. Her blue eyes twinkled and her pink tongue teased her ruby lips. Jesus! Even her teeth were perfect.

"Aren't you gonna let me in?" she asked, mocking a pout that made my heart stutter, but I wasn't about to fooled again.

"Uh ... no," I replied with a hard swallow.

"Bobby!" Shelly put her hands on her hips, the stern little girl now. "Do you want me to tell your mommy on you?"

"What?"

"You're so cute!" She giggled and kissed my cheek, slipping past with a quick rub of her tits against my chest.

"Wait! What are you doing here?" I repeated, spinning on my heels as she dropped her purse on my sofa.

"It's Friday night, silly!" Shelly replied. "You're taking me out, remember?"

"I am?" I shook my head. "No, that's not ... I never ... We didn't even ... Don't you have to work or something?"

"I've been working all day," she sighed. "Would you be a dear and give me a foot massage?"

"This is crazy," I decided, shutting the door before one of my nosy neighbors happened to walk by. Not that I had nosy neighbors, I didn't, but why take chances? I liked my apartment a lot.

"No, it's not," Shelly said. She sat on the sofa, looking over her shoulder because it faced the wall and my big flat-screen television, and ... What was she doing here?

"Look, I don't understand any of this," I told her, honestly. "I'm not gay, alright? I'm not looking for some weird transvestite girlfriend thing."

"Excuse me?" She narrowed her eyes and I felt my stomach knotting up. I wasn't very good at confrontation.

"Um..."

"Did you just call me a weird transvestite?"

"Kinda?" I said, making it sound like a question. You know, like maybe we hadn't heard me right. It didn't seem to work as she stood up again, smoothing her skirt and walking towards me.

"For your information, Robert," she poked me in the chest with her finger, "I'm not a transvestite and I'm definitely not weird."

"Sorry," I mumbled, looking down as she poked me again.

"I'm a non-op transsexual," Shelly explained, except I didn't know what that meant. "You can call me a tranny. You can call me a shemale. You can even call me a chick with a dick, I don't care."

"Alright," I agreed quickly.

"But don't ever call me a transvestite."

"I won't," I promised. "I was just confused for a second there."

"Tell me you're sorry."

"I am sorry."

"Prove it."

"Huh?"

"Massage my feet for me and I'll forgive you," Shelly said, smiling again as she led me around the sofa.

I don't know why I gave in so easily. I didn't want to, believe me, but Shelly just didn't give me a chance to be forceful. Just as I thought I was getting up a head of steam, she deflated me completely. I've never been good at dealing with girls anyway and even though I knew she had a penis, the rest of her looked so ... girlish! It wasn't fair at all. Boys aren't supposed to look like that, or sound like that, or have size seven feet!

"You like my feet, don't you, Bobby?"

Shelly had pulled me down to my knees, tugging on my necktie until she had me right where she wanted me. Her legs were bare, but she had such smooth skin, tanned and toned, she didn't need stockings. Shelly wore patent leather shoes, expensive ones, probably, with open toes and spiked heels. Her toenails were red like her lips and fingers, and she had small, female feet. I'd spent three years selling shoes at Pay-Less as a teenage boy, so I had a lot of experience with women's feet and Shelly's were incredible.

"Yeah," she sighed, tilting her head with satisfaction as I removed her left shoe. "You're a foot guy, I can tell. Some men like legs, some of them like tits or ass, but you like feet."

"Ahhh..." I cleared my throat. "I guess so."

"You're shaking like a leaf!" Shelly giggled. "It's okay. Relax, Bobby. Nobody's going to steal Christmas from you, I promise."

"I'm sorry," I said, for no good reason at all. I could feel myself blushing as well, and my hands were trembling as I cradled her naked foot.

"We've got all night," she whispered. "Go ahead, baby. Kiss my foot. Mmmm ... Right on my toes. Do they smell good?"

"Yeah," I breathed, closing my eyes and inhaling her decidedly pleasant scent.

It made my cock hard, that faintly sour musk of female sweat, but don't think Shelly was dirty or anything. Her feet were pristine, scrubbed pink during a recent bath, I imagined. Her pedicure must have been new as well, the crimson lacquer applied perfectly to her wonderfully shaped nails. She had been walking around, however, and feet tend to grow sweaty with even the smallest exertion. Not much, but just enough to make them interesting and feminine and a wonder for the senses.

"Someone likes it," Shelly teased, pressing her right foot against the tent in my trousers. She still wore her shoe and I didn't mind the pressure, even if it did humiliate me getting caught like that.

"Mmmph..." I groaned, massaging the deliciously soft sole of her foot with my thumbs while I closed my lips around her big toe.

"That's a good boy," she whispered. "Like a pretty little cock, isn't it? Use your tongue, baby. That's it ... Ohhhh ... You've done this before, too!"

I wasn't about to tell her that I'd done it for Marilee, my first and only girlfriend. Looking back, it may have been the only reason the slut had gone out with me at all. Besides getting free shoes, I mean. I'd probably spent more time kissing Marilee's feet than I had kissing her mouth, and I'd only gotten to kiss her tits once. She wanted to save herself for marriage, or so she'd claimed. Yeah right! Saving herself for my best friend's dick, more like. The only girl I'd ever loved had betrayed me, but for the moment I took solace in the realization that Marilee couldn't hold a candle to Shelly in the foot department.

Or any other department, now that I was thinking about it.

Look, I know how ludicrous it sounds, believe me. I mean, Shelly had a penis. She'd raped me with it. Butt fucked me in my own bed and then a couple days later mouth fucked me in a public restroom. Okay. I get it. Thank you. My asshole still burns, but as I knelt on the floor, sucking her toes and feeling my cock throb beneath the heel of her shoe, I experienced something unexpected and unwanted. A confusion of joy and excitement, perhaps even more than that, growing deep in my gut and spreading through my flesh like a cancer. She wasn't just pretty. She wasn't merely cute. The girl was a transsexual escort for a reason, you know? She walked, talked, tasted, smelled, and even laughed like a normal, gorgeous, sexy, well-adjusted young woman.

"What's wrong?" Shelly wondered, narrowing her eyes as I'd frozen with surprise. Or shock, maybe. Surprised shock.

"I love you ... your, uh ... toes," I stammered. "They're, um ... nice."

"You love me?" A smile crept over her face. "Or just my feet?"

"Well..." I licked my lips and she curled her toes, briefly teasing my tongue. She used them to pull my bottom lip down and I shivered.

"No, don't tell me," Shelly decided, pushing her toes gently, but insistently into my mouth. "Let me figure it out all by myself, baby."

She soon had all five of her toes between my lips, forcing my mouth wide and giggling happily. I used my tongue to worship them, that's the only word for it. I teased, tickled, and wriggled the tip over, around, and between her toes like they were candy. I didn't have to hold her either, Shelly was more than content to tilt and turn her foot, pushing and pulling with it as if fucking my face. That allowed me to reach down and free my swollen erection. After I'd removed her other shoe, of course.

"Do you want to cum on my foot?" Shelly wondered, massaging my penis with the unbearably soft underside of her foot. "Go ahead and use my foot if you want. Jerk off for me, baby. Show me how much you love me."

I made muffled noises of agreement, using my hands to hold her foot and trap my cock against the sole. Her smooth heel would rub against my balls as I worked her foot up and down along the shaft. Shelly played with the head of my penis and she'd turn her foot slightly to the left and right, gathering precum on her toes before pulling then downward. She was quite dexterous, too. She didn't have very large toes, as I mentioned, and very small feet for man, but she could spread her toes nearly enough to fit my erection between them. She certainly liked to try and pinch me, but I didn't mind.

To be honest, I almost wished my very average sized manhood was a bit smaller, because I would have loved to slide it between her toes and make love to her that way. The erotic sensation of Shelly's foot jerking me off felt heavenly for me. Like nothing else I'd ever experienced in my life, but I have to admit that I'd dreamt of such things before. Not with Shelly, though. I mean with Angelina Jolie, mostly, and I guess I just have a thing for strong, intimidating women or something.

"What?" I gasped, feeling dizzy as my orgasm perched ready to explode any second.

"I said, don't cum yet," Shelly repeated, having pulled both of her feet away from me. "Kiss the other one for a little bit. It's feeling neglected."

But the other one glistened with my own precum, I wanted to protest. My cock was leaking like a faucet, drooling clear fluid over her skin, and even if the stuff tasted like pistachio ice cream, I didn't want it in my mouth. Shelly didn't give me a choice, however, and as it turns out, that precum stuff doesn't taste like anything at all. Thank goodness!

We did that for a long time it seemed to me, but not long enough. Shelly kept alternating, playing musical feet with my cock and mouth every time I'd get too close to cumming. Talk about frustration! I was almost desperate for release when she put her legs around me, and willing to do just about anything if it meant I could cum.

Shelly pulled me closer as she raised the hem of her skirt up her smooth thighs. I hadn't noticed, but she was sporting her own tent, and a much larger one than mine. I knew what was coming too, no pun intended, and I took a deep breath as she exposed her long, thick cock and hairless pink scrotum. She wasn't even wearing panties?

"Do me first," she said. "Come on. I want to cum in your mouth, baby."

Unlike the first time I'd given her head, Shelly didn't make me do anything. I felt kind of guilty about that too, but after playing with her feet, loving them with my hands and mouth while she teased my cock ... I couldn't refuse her. She'd found a way to short circuit my common sense, my manhood it seemed, and her soft voice appealed to something deeper and more essential to my nature. I don't pretend to understand it, I only know that I couldn't help myself as I took Shelly's firm erection in my hands and kissed the tip.

"Hmmmm..." she sighed happily, rewarding me with a languid, sexy smile. "I knew you could do it, Bobby. We're perfect for each other. Suck me nicely now."

I didn't know about being perfect for each other, but my lips parted easily as I took the pinkish head of her cock into my mouth. The shaft felt hot and heavy, filling my fists as I began stroking her silky skin and the rock hard muscle beneath. I stared at her tummy, which was flat and taut, revealing her female abs like a sexy washboard. I wondered if Shelly worked out and decided that she must. The woman had no waist at all, nothing about her shape suggested that she'd been born male. Not her long legs or narrow, rounded hips, and certainly not her ripe breasts as she pulled her top up and over her head.

"A little more," she whispered, cupping her tits and rubbing her thumbs around her dark nipples. "Take as much as you can, baby. Up and down, that's it. Nice and slow, yeah, just like that. You're such a good cocksucker, Bobby."

"Ummph..." I agreed, pumping her cock in time with my bobbing head. The idea that I was a cocksucker bothered me, as it would anyone else, I'm sure, but not enough to make me stop. Shelly's nipples were growing long and stiff above me. Her tongue played between her smile and the girl's brilliant blue eyes glittered like diamonds. She was a vision of pure beauty and even her large erection seemed somehow sexy and feminine, but don't ask me why.

I cradled her balls with my left hand, earning me a deep throated moan of pleasure as I rolled her testes and gently tugged at her scrotum. The skin felt buttery soft and smelled of peaches. Shelly must have used some sort of body lotion, but I couldn't taste it on her cock. Spit and precum filled my mouth and I swallowed eagerly, hunching my hips to fuck the sofa with my own dripping penis. I ached with urgency and I wanted to cum. I needed to cum as a nearly painful lust for release pushed every other thought from my mind.

And still, I didn't stop nursing on Shelly's fat prick. I bobbed my head faster, ignoring the odd sensation of her cockhead hitting the back of my mouth every few seconds. The wet, sloppy, slurping noises I made were punctuated with the occasional gag and muffled cough, but I didn't stop or even slow down. I wriggled my tongue as juice spilled from my bruised lips, spilling down the shaft and around my fingers. That only made it better as I massaged her steely flesh, coaxing Shelly to ejaculate into my mouth with a sharp gasp and jerk of her hips.

I was cumming too. As soon as I felt the first jet of semen across my tongue, my sympathetic balls surrendered completely. We were cumming together and I swallowed as quickly as I could, drinking Shelly's hot load while she panted words of encouragement. My own semen sprayed uselessly onto the sofa and the carpet beneath me. The stuff landed on my thighs, even on my stomach as the violent pleasure pulled my helpless cock in random directions. It felt wonderful and I suckled Shelly's even after she stopped spurting, not minding the creamy texture or salty, almost sour flavor at all. I sort of found myself enjoying it for some reason, and I know I liked the feeling of her warm sperm filling my belly.

For a while there, I didn't even feel guilty about it. I just burped softly and blushed, licking my lips as Shelly giggled.

"Penny for your thoughts," Shelly whispered, kissing my face as we sat together on the sofa, We were both naked and after cumming, she'd wanted to cuddle and make out.

"I'm not thinking about anything," I replied, but that wasn't true.

I had my left arm around her shoulders, cradling the girl to me like ... Well, like she was a real girl, except my right hand was holding her hard cock. Shelly held my somewhat smaller, but no less aroused penis in her left hand. We'd been making out like a couple of teenagers and jerking each other off all the while. Occasionally, she would push my head down and sigh contentedly as I licked and nibbled at her breasts, but mostly we shared deep, soul searching French kisses and a part of me felt as happy as I'd ever been in my life.

Another part of me felt guilty, even ashamed of what we were doing. After I'd cum, I'd regained my senses, so to speak. I wasn't gay. I didn't want to be gay, but I felt kind of gay, you know? I mean, I could still taste her semen on my tongue and feel it in my stomach. Her cock filled my hand and it seemed to pulse with a heartbeat all its own as I worked my fist up and down the shaft. That had to be gay, right? Except kissing her felt so wonderfully natural I never wanted to stop. Her lips were soft and luscious, her tongue so amazingly light as it fluttered against my own. And her breasts and hair and eyes and every other part of her I could find seemed so perfectly female to my senses.

It wasn't fair at all.

"Come on," she teased, laughing lightly. "Tell me what you're thinking, Bobby. I want to know."

"Why are you doing this to me?" I asked, searching her eyes with mine. "What do you want from me?"

"I want you," she said. "I'm doing it because I love you, haven't you figured that out yet?"

"But..." I swallowed hard. "You're a..."

"Transsexual?" she offered with a smile.

"Prostitute," I said, regretting it immediately, but it was on my mind. I mean, bad enough I was making out with a shemale or whatever, but Shelly was a whore. She'd met my mother!

"Oh." She nodded. "I understand. You don't want to share me, do you?"

"Uh..." That wasn't exactly what I'd meant.

"I don't blame you," she said. "I'm the jealous type, too."

"You are?" I winced as she rubbed her thumb around the head of my penis, but only because it felt so good. I kinda loved the way she jerked me off.

"I'm not really a prostitute," Shelly said. "I used to do a little escort work in college. You know, just on the weekends to help pay my tuition, but not anymore."

"You don't? I mean, you're not?" I blinked at her. "But my birthday..."

"One of your friends remembered me from college," she explained. "We sort of bumped into each other at Clyde's and I asked him about you."

"The bar?" I almost smiled, but I still felt a bit confused.

Clyde's was a downtown tavern, a place where a lot of business people went for drinks after work. Sometimes during work, actually, but that's not important. I didn't go there often, but I'd certainly visited the place more than once. The guys I worked with liked to tease me about being too shy and introverted, and so they'd drag me along sometimes. The bar usually had a lot of women, too. Secretaries and low level executives, young and single, looking to tease more than hook up, but a guy could get lucky. Or so I'd heard, not actually having tried to pick up anyone myself. Had I seen Shelly there without even knowing it? And then I had another thought...

"You were telling the truth?" I stared at her.

"Hmmm?"

"That stuff you told my mom," I said. "At the restaurant. You're really a, uh..."

"Stenographer," Shelly agreed with a giggle. "I work at Rowe, Johns, and Morgan. The law firm?"

"But you told me you were an escort!"

"I saw you at the bar and I wanted to meet you," she said. "Haven't you been paying attention?"

"Yeah, but..."

"And when Kevin told me about their plans to get you a girl for your birthday, well..." She shrugged. "It seemed like a good way to break the ice."

"Kevin?" I felt more than confused. "He knows you're a, uh ... transsexual?"

"Of course, silly!"

"And he had sex with you?"

"We went on a couple dates back in college," Shelly admitted. "But that was just business. I told you, Bobby, I'm a good girl now. I don't do that stuff anymore."

"He's not gay though!" I protested, and with good reason, I thought.

Kevin was like the manliest man in the whole office. He'd been a big football player in college, almost good enough to turn pro. He loved women. Shoot. He even had a seriously hot girlfriend, some oriental girl that he practically worshipped. I couldn't even imagine a guy like that paying for sex with a girl like Shelly!

"He's got a girlfriend," I said, thinking out loud.

"You mean that yummy little lady boy he lives with?" Shelly asked. "He met her online, I think. Flew all the way to Bangkok and brought her back home."

"Lady boy?"

"You didn't know?" She rolled her eyes. "She's got a bigger cock than mine."

"She does?" I felt dizzy. I'd met Kevin's girlfriend and she'd looked incredibly sexy. I got hard just thinking about her, or I would have if my cock hadn't been hard already.

"You'd be surprised how many men like that sort of thing," Shelly told me, being quite serious about it. "Straight men, too. I'm not talking about fags, they're just annoying."

"You don't like gay men?"

"Nope!" She giggled at the look on my face. "I'm serious, Bobby. That's why I like you so much, you need some convincing."

"I do?" I laughed, nervously.

"A lot of guys love my dick," she explained. "I want a man who loves me. Someone who doesn't see me as anything but a beautiful woman."

"But..."

"With a little something extra," Shelly whispered, kissing me again, and I quickly figured out that she'd grown tired of talking.

She wanted to make love and for some reason, it didn't seem to hurt nearly as much as it had the first time. I actually enjoyed it, or maybe I just liked the way she kissed me while she filled my ass with cum. It was kind of hard to tell because I was cumming, too. Like it or not, I had a new girlfriend. Sorta.