Chapter 2

"When are you going to find a woman and settle down?" my mother asked, and not for the first time.

"I don't know," I replied, shifting uncomfortably in my chair.

"You've been saying that since you were three," she complained. "Where did you leave your toys? I don't know. How come you didn't get an A in math?"

"That was seven years ago, Mom."

"I don't know," she answered. "Why did that lovely Marilee Johnson marry your best friend? What did you say, Robert?"

"I don't know," I sighed. Bringing up Marilee was kind of a low blow. She'd been my first and only girlfriend, until the night she announced that my friend Mike had knocked her up. I'd never even gotten a peek at third base.

"She was no good for you anyway," Mom said, contradicting herself the way she often did. "Will you stop fidgeting and listen to me? What's wrong with you today?"

"Sorry." I tried to ignore my throbbing rectum. Three days after being raped by a transvestite prostitute, my butt was still sore. My ego as well, since the guys at work had paid for it. Sometimes I really hated my job.

"Well, I have some news anyway ... Oh! Thank you," Mom smiled at the waitress delivering our lunch. "You're very pretty. Have you met my son? He's an accountant."

"Mom!" I frowned as my face reddened. The waitress was very pretty and my mother did that sort of thing all the time.

"That's nice," the girl replied, hardly giving me a glance. "I'll be back with your milk."

"Thanks," I muttered.

"No ring on her finger," Mom noted, "and you just sit there like a bump on a log."

"She's probably got a boyfriend."

"Hmph!" she rolled her eyes. "Marilee had a boyfriend too."

"Just..." I held up my hand. "Drop it, okay? I haven't seen her in forever."

"I saw her just the other day," Mom told me. "Pregnant again, can you believe it? That's number three for her, Robert."

"Great."

"That husband of hers must have some real juice," she said. "What was his name?"

"Please?" She'd known Mike for over a dozen years, ever since we'd first met way back in the sixth grade.

"All of my friends are grandmothers and here you are..."

"Can we just eat?"

"Are you gay?"

"What?" I blinked at her.

"You can tell me," she said, reaching for my hand and giving me a sympathetic squeeze. "I'll understand, Robert."

"Oh God," I breathed. "I'm not gay."

"Is that denial I hear?"

"What's your good news, Mom?"

"Hmmm ... Oh! Well, I'm not sure if it's good news or not now, but..."

"But what?" I asked, wondering why she'd stopped speaking suddenly.

Mom was staring past my shoulder and I turned my head to look. She could change the topic of conversation on a dime, more often than not without even realizing it, but making her stop talking entirely...

"I think she's looking at you, Robert!"

"What? Who?" I asked, a mere split second before I saw Shelly walking towards us.

"Now that's a real woman," Mom decided, smiling as she took in the woman's long, toned legs, her surprisingly round hips and narrow waist, and decidedly large breasts. It didn't hurt that Shelly had bright blue eyes and thick golden hair; Marilee had been a blonde too.

I didn't say anything, of course. My mouth opened and closed several times, but no words could escape my suddenly parched lips. When Shelly wiggled her fingers and smiled, I felt the deep, burning pinch of humiliation deep in my gut. This 'real woman' had raped my virgin ass with her very real penis! What was she doing here?

"Bobby! I'm sorry I'm late, darling." Shelly bent at the waist, kissing my cheek as I sat frozen in my chair. "Mmmm ... You smell so clean!"

"Robert?" Mom said, smiling patiently as Shelly decided to hug me. I could feel her firm, braless breasts trying to envelope my head. "Aren't you going to introduce me to your friend?"

What I wanted to do was jump up and run as far and fast as I could! My heart was pounding, the air trapped in my lungs as I'd forgotten how to breathe. My tender rectum spasmed with the painful memory of being violated in my own bed just a few days before. I had the vague hope that all of this was only a dream. Lord knows I'd dreamt of my mother often enough. Usually I was naked in those, however, and today I was fully dressed in a suit and tie.

No, I wasn't dreaming.

"You must be Bobby's mother," Shelly said, keeping her left arm around my chest as she extended the right. "He's told me so much about you."

"He hasn't mentioned you at all," Mom replied, shaking hands above my untouched salad. "Uhhh ... What is your name?"

"He hasn't?" Shelly took my chin in her fingers and turned my face upward. "Bobby! That's not very nice! I'm beginning to think you don't really love me at all."

"W-What?" I gasped, staring into her sky blue eyes and they were twinkling with humor.

"I'm Shelly," she told my mother. "Bobby's girlfriend."

"Ahhh..." I opened my mouth to protest, having at last found a way past the shock and awe of the woman's unexpected arrival. But she wasn't about to let me get a word in, not if it meant contradicting her ridiculous lies!

"Oh my!" Mom gasped.

"Mmmmph!" I said, widening my eyes as Shelly covered my lips with hers. The woman's tongue, as light and delicate as I remembered, filled my mouth and teased my own. Her hands held my head like a vise, her sharp, pink fingernails pressing into my scalp with an oddly painful pleasure. I had no doubt she could draw blood if she wanted and more than anything else, Shelly frightened me!

Any other red-blooded American man would have pushed her away, possibly even punched her in the nose. I mean, Shelly wasn't a real woman, not with a large, stiff penis and sperm-filled balls swinging between her smooth thighs. Never mind that she looked like a gorgeous college coed on the outside, I knew all too well what lurked inside her heart. She'd raped me! And maybe that's the reason I didn't do anything but let her kiss me in front of my own mother, the pretty waitress holding my glass of milk, and countless others in the crowded mid-town restaurant.

"Be good, Bobby," Shelly whispered, breathing the words across my flushed face as she broke our kiss.

"Would you like a menu," the waitress asked, somewhat sarcastically, "or do you need a room?"

"I'm sorry," Shelly said, speaking more to my mom than anyone else. "We just get carried away sometimes. Don't we, Bobby?"

"Uh, yeah," I agreed softly, looking down as I'd become all too aware of the people around us. A few chuckles from the businessmen and whispered opinions from the secretaries didn't seem to bother Shelly at all ... or my mother for that matter.

"I can see that!" Mom giggled happily. "I had no idea Robert had such a lovely girlfriend."

"Thank you," Shelly replied, smiling as she combed her fingers through her hair. She turned it off when the waitress returned with a menu. They didn't seem to like each other.

I sat silently for the next thirty minutes, smiling as required by the ludicrous conversation, even laughing at times. Mom was determined to learn everything she could about my new girlfriend and Shelly was only too eager to oblige.

"Oh, we met by accident," Shelly explained. "I had a flat tire last Wednesday. Remember that terrible rain? Anyway, I don't know anything about cars and nobody would even stop to help me."

"It's terrible, isn't it?" Mom nodded sympathetically. "The men in this town..."

"Yeah," Shelly sighed. "It's so hard to find one like Bobby! He gave me his jacket and let me sit in his car while he changed the tire on mine. He was so sweet!"

She gave me a warm smile and for a second there I almost believed her, that's how good Shelly could lie. We held hands on the table and Mom looked ready to melt with happiness.

"My knight in shining armor," Shelly said, leaning close for another deep, soul searching kiss. This time my tongue moved with hers, even slipping into the girl's mouth, but I told myself it was okay because I didn't want Shelly to cause a scene. If my mom ever learned the truth...

"That's so sweet," she decided, dipping a spoon into her chowder while my girlfriend made out with me.

Of course, Mom had no idea that Shelly was anything but a real live woman. She bore none of the tell-tale signs one might expect from a transvestite. Her hands were small and delicate, like her feet, and while she must have had an Adam's apple, nobody could see it. Her voice was soft, high-pitched, and tinted with a light, Southern belle accent. She sounded like Scarlett O'Hare, not a man pretending to be a woman. Shelly didn't move with the exaggerated female mannerisms most drag queens tend to adopt either. Everything about her screamed female and her charade was as perfect as it seemed effortless.

It didn't hurt, or help, I mean, that Shelly looked like any other professional young woman. She wore a charcoal business suit, not overly conservative, but hardly what I'd have expected from a prostitute. The skirt fell to mid-thigh, the blazer tailored to show off her curves without suggesting a sexual harassment suit waiting in the wings. She wore a white blouse and a fashionable gold necklace to match her earrings. The first impression of her would be that she was just another secretary on her lunch hour, albeit a very attractive one.

A lot of men were keeping a close eye on her every move and Shelly seemed oblivious to the attention. All of her considerable charms were focused on me and as much as I hate to admit it, I rather enjoyed my envious, if completely fraudulent situation. I wondered how many of those men would have been so keen had they known Shelly's secret. Not many, I'd wager, and I suffered a genuine conflict as Shelly's unabashed affection began to have its intended effects.