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.

My cock was hard!

"Robert, you simply have to bring Shelly over for a proper dinner."

"But..."

"No buts, young man." My mother smiled at Shelly. "He comes over every Sunday for a home cooked meal."

"Ohhh ... That's so sweet," Shelly cooed.

"So this Sunday I'll expect to see the both of you," Mom insisted. "I can't tell you how happy I am that he's finally found a good woman."

"We'll be there," Shelly promised, massaging my cock beneath the table. She'd been teasing me for the last half hour, torturing me while telling my mother all about her imaginary life.

I'd listened with growing disbelief as Shelly reinvented herself, adding details on the fly, and Mom had eaten it up. So far as she was concerned, her only son was dating a college graduate. My new girlfriend rented a loft in the Village, kept a cat named Mr. Tibbs, and worked as a stenographer for a prominent law firm. Shelly made up family members as she needed them, regaled my mom with unhappy stories about ex-boyfriends, and expressed her desire to get married and start a family. A big one, she claimed, which was music to my mother's ears.

And all the while, Shelly was jerking me off through my trousers. Talk about a mind fuck!

"Are you insane!" I said, because it wasn't really a question at all.

"Shhh ... In here," Shelly whispered, glancing over her shoulder as she pulled me into the men's restroom.

My mom had already left the restaurant. I'd paid for our lunch and I should have been on my way back to work, but I wasn't. I had to find out what was going on.

"Are you stalking me?" I asked, paying little attention as Shelly pulled me past the empty urinals and into a stall.

"Of course not," she replied. "Sit down. I really need to drain my balls, Bobby."

"What? Hey! Oh!" One quick shove had me sitting on the toilet with Shelly standing in front of me.

"That was so much fun," she sighed, pulling up her skirt and tugging her panties to the side. "I kind of figured you for a momma's boy ... Open up."

"Noooomph!"

Shelly pushed her swollen cock past my lips, guiding her erection with one hand while cradling my head with the other. The smooth head of her circumcised penis slid over my tongue and my lips formed a moist, round hole as they were stretched taut around the shaft. I'd never sucked a cock in my life, and more to the point, I'd never wanted to! I gagged and choked, and tried to push her away, but Shelly grabbed my head with both hands and held my face firmly impaled on her fat prick.

Jesus! She had a big one and I hadn't gotten a real look at it the night she'd fucked me. Now I had no choice but to admire not only the size, but the strength of her arousal. It was like sucking on a piece of iron! There was no give to her flesh at all and Shelly's erection stood straight and stiff as an arrow. I had half of it in my mouth, perhaps not even that much, and couldn't possibly take any more.

"I know what you're thinking," she whispered. "You're not queer, right? Well neither am I, Bobby. Just think of it like a big clit, that's all. A big, sexy clitoris for you to love."

"Nnnnmph..." I tried shaking my head, but I think that only made it better for her. The only thing she didn't seem to like were my teeth as they occasionally got in the way of her pleasure.

"Watch the teeth, Bobby," she warned. "Or I'll have to bend you over and find some other way to ... Shhhh ... Someone's coming!"

I froze with the acute fear of being discovered. We were in the men's room of a popular restaurant and I was sucking a girl's dick! Oh man! If we got busted my life would be over. Shelly probably wouldn't care, she was just a whore anyway, but I had a job, a career. I was a CPA with an influential and very conservative clientele. Sucking off a transvestite hooker on my lunch break would be like jumping out the window of my 38th floor office - messy, painful, and utterly final.

The man's footsteps echoed off the tiles. He was humming softly and the sound of his zipper coming down made me jump. I could hear his piss hitting the porcelain and Shelly decided to fuck my mouth. I had to fight my gag reflex as she began moving her hips, smiling down at me as I begged her silently to stop. I had my hands on her stocking clad thighs, squeezing her toned flesh as I tried to make her see reason. I couldn't do this!

The guy seemed to piss for an eternity and before he finished someone else had come into the restroom. Two men, apparently friends, were discussing some business deal with friendly chuckles and inside jokes. I felt trapped and helpless, sitting on the toilet and praying no one would notice Shelly's feet beneath the stall door. To make matters worse, I was already late for work, and even if I left that very second I'd have to come up with a reasonable explanation.

Well, everyone knew I had lunch on Thursdays with my mother, so that wouldn't be so bad. I could get away with being ten or fifteen minutes late, but that meant I had to make my escape soon and the only way to do that was ... I had to get Shelly off! She wasn't going to let me go until she had her orgasm, I'd figured that much out, and she probably didn't care if it took all afternoon to do it! The woman looked quite content to fuck my mouth slowly, smiling with her head cocked to the side so she could listen to the oblivious patrons draining their bladders just a few feet away.

I'd have to sneak out behind the two guys who had just walked in. Assuming nobody else came in during the meantime. I had as much time as it would take them to piss and wash their hands. Two minutes? Three? Maybe five if I was lucky and they were obsessive about cleanliness. That meant I really had to suck Shelly's cock like a pro and I'd only had one blowjob in my whole life! I'd never given one before and the idea was repulsive, as you can imagine, but what choice did I have. The only good news was that I already had her dick in my mouth, so at least I knew it wouldn't kill me.

"Hmmmm..." Shelly moaned. "What's gotten into you, Bobby?"

She'd whispered, of course, but the sound of her voice was almost enough to give me a heart attack. Thankfully, the two men outside our stall didn't seem to hear anything as they congratulated themselves repeatedly for whatever it was they'd done. They'd probably been celebrating with martinis, a lot of them by the sounds of it.

I pushed them out of my mind and concentrated on using my tongue to tickle and tease Shelly's penis. I suckled quietly, carefully as I wanted to remain as silent as possible. Even so a wet raspberry would escape my taut lips every now and again. I would gag too, it couldn't be helped as Shelly would push just a bit too much with her hips. The two men, who must have assumed I had serious intestine issues, politely ignored the obscene sounds. Well, mostly, I should say. It did prompt one of them to tell his friend about a vacation to Mexico or some such place.

"Yeah, that's it, Bobby," Shelly breathed. "Suck my clit ... Ohhh ... Play with my balls, that's it. You've done this before, huh?"

I didn't bother trying to answer. I had my eyes closed, concentrating on sliding my lips up and down the shaft in time with her hips. Spit and precum filled my mouth and what I couldn't swallow spilled from the corners of my taut lips. I held Shelly's clean shaven scrotum and large, cum-filled balls in my right hand. I rolled them gently, amazed by their size as much as the silky texture of her sack. My other hand massaged her wonderfully firm, round ass. The musk of her arousal became pronounced and she filled my senses. The taste of her sweaty skin, the sound of her sexy, breathless voice, and the feel of her distinctly feminine form, all seemed completely at odds with the cock I now willingly worshipped.

"Open your eyes," she commanded. "I'm going to cum."

As soon as I did that, I realized the two men had left and I hadn't even noticed. How long had I been sucking her? My jaw had begun to ache. My lips were bruised and swollen, my tongue tired from its incessant wriggling. I'd lost track of time and I had both hands on her ass, actually pulling Shelly into me as I bobbed my head up and down on her steely erection. My own penis was hard as well, I'm ashamed to say, and I took solace in the belief that Shelly couldn't possibly know about that!

"Ahhhh ... Swallow it, Bobby! You bitch!" she gasped. "I'm cumming!"

I had no choice as her cock began to throb excitedly between my lips. A flood of hot semen filled my mouth quickly and with the first swallow, I knew I'd made a mistake. It was salty and slimy and ... Ugh! I was swallowing her sperm! I gagged, coughing around her prick and spitting cum down the thick shaft. I couldn't swallow anymore of the stuff and I was sincerely afraid I was going to puke, but I didn't. Neither did I get loose from the woman. Shelly held me on her spurting cock for several long seconds and didn't seem to mind one bit the mess I was making.

"Too much?" she teased, actually letting me go with a giggle.

I took a deep, ragged breath, but my gratitude was short lived. She'd taken her cock in hand and her orgasm wasn't yet finished. She stroked the last few spurts onto my red face, painting me with jism as I just sat there like an idiot. I was dumbfounded and trembling, even as she slapped my wet cheeks with her cum soaked erection. Shelly wiped her penis clean on whichever part of my face seemed unspoiled and then tucked it away inside her white lace panties.

She fixed her stockings and smoothed her skirt, kissed her fingertips and touched them to my spermy lips.

"Thanks for the blow, Bobby," Shelly said. "I'll see you on Sunday."