He paced back and forth in the front hall, waiting for Leyland to answer, running his hand
through his hair. When he picked up, Ricky said, “The escort you called earlier is at my front
door right now. Get over here. He wantsyou
“No,” Leyland said. “I’m playing cards right now. He wants you, not me.”
“Get over here right now,” Ricky said. He spoke with a low tone, but his voice was filled
with panic. Nothing in school had ever prepared him for an event like this.
“You’re just going to have to handle this yourself,” Leyland said, with his wise professor
voice, as if he knew what was best for Ricky. “Just relax and enjoy it. You can thank me and tell
me the details in the morning.” Then he hung up the phone before Ricky could tell him there was
a six-foot-tall she-male standing on his front porch.
The doorbell rang again, and the elaborate chimes made him swallow back hard. He put
the phone down on the island, paced back and forth a few more times, and walked back to the front door. Before he opened it this time, he fastened the chain latch and turned the knob slowly
(you never know; this guy Dawn was bigger than Ricky). When he opened it and peered over the
gold chain, Dawn’s back was facing him. He cleared his throat and said, “I’m sorry about all this.
There’s been a huge misunderstanding.”
Dawn turned and said, “Ricky, be a nice boy and open the fucking door so I can make a
phone call. I took a taxi here from the city and I have to call another one to get back.” He spoke
with resigned cynicism in his voice, as if he’d been through this sort of thing many times before
and Ricky was just another dumb kid from New Jersey playing around with him. “Do the cool
thing, sweetie. I swear I’m not gonna hurt a hair on your pretty little head.”
Ricky hesitated for a moment, then unlatched the chain. When he opened the door all the
way, Dawn sent him a frustrated look and sashayed into the house with an exasperated sigh.
As Ricky led Dawn back to the kitchen so he could use the phone, his high heels clicked
and his earrings tinkled. And Ricky couldn’t help noticing the way his ass wiggled and moved in
the short tight dress. If he hadn’t been so tall and his features hadn’t been so large, he could have
passed for a real woman, especially from the rear.
In stronger light, Ricky could see how heavily his makeup had been applied and how
brassy his wig was. The lip gloss alone looked wet to the touch, his eyelashes had to be an inch
long, and there were glittery little sparkles all over his cheeks and forehead. He looked more like
a caricature of a woman than a real woman. But it was none of Ricky’s business, so he smiled
and said, “I’m sorry about this.” He put his hands in his pockets and stared down at his sneakers.
“I didn’t mean to put you out in any way.”
Dawn walked to where Ricky was standing and ran her long fingernails across the left
side of his face. “Don’t worry, sweetie. It’s all good.” Ricky looked up and smiled. “It’s nothing personal. You’re very attractive, and all. It’s
just that I’m into guys, not girls.” This was the first time he’d said this aloud to another living
person. It felt so natural and easy. Besides, he wanted to be honest; he didn’t know how to
approach this without being too blunt. Though he knew Dawn really was a guy, he wanted to
make it clear he wasn’t discriminating against him because he was a she-male. “I think what
you’re doing is fine. I support you all the way as a person and a citizen. It’s just that I’m not into
it, is all. I were into it, you’d be perfect.” He folded his arms across his chest and nodded, trying
hard not to offend Dawn.
Dawn smiled and waved his fingernails. “Blah, blah, blah,” he said. “I really don’t give a
damn what you’re into, so save the political correctness for someone who cares. I just want to be
compensated for my time, sweetie. I came all the way out here, and I never come this far out in
“No problem,” Ricky said. He held his hands up and smiled. “It’s only fair.” He seemed
like a nice enough guy, in spite of the high heels and lipstick.
Dawn reached down and squeezed Ricky’s shoulder a couple of times. He bit his ruby lip
and shook his head back and forth. “It’s such a shame, too. You are a fine-looking young piece
of male flesh. I’ll bet I could make you very happy if you let me. I can teach you things you
never knew existed.” Then Dawn reached between Ricky’s legs and squeezed his balls. “And
you’ve got a nice handful, too, sweetie.”
Ricky stepped back and took a quick breath. No one had ever grabbed his genitals this
way either. Oddly enough, he felt a hint of arousal. But he didn’t want to admit this aloud and
encourage Dawn. He’d never been with a man and he didn’t want his first time to be with a she
male. He wanted his first time to be somewhat special. He wasn’t looking for love, but he did want the guy to roughly resemble the Keanu Reeves man of his dreams. Besides, Ricky kept
wondering how he’d look wearing Dawn’s sexy black high heels. If he hadn’t been so terrified,
he would have asked if he could try them on. “I’m sorry,” Ricky said. “I’m just not into it.”
Dawn shrugged and turned. “I’ll live.” He lifted the phone from the island and said, “I’ll
need travel expenses and money for my regular session. She’s not greedy. She just wants to be
paid for her time, sugar.”
“One hundred fifty.”
“I thought you advertised sixty bucks.”
“The rest is for her travel expenses. She didn’t swim over here from Manhattan in high
heels, doll.” Dawn tended to slip into the third person when he spoke.
Ricky smiled and reached into his pocket. He handed Dawn one hundred and fifty dollars
of the money his mother had given him and said, “Sounds fair.” He smiled again; he was just
glad he was getting rid of him.
After Dawn called the taxi, they waited outside on the front steps for what seemed like
hours. Conversation was awkward at best. Dawn kept opening his legs and flirting with Ricky,
and Ricky kept looking up to the sky and rocking on the balls of his feet. At one point Dawn
lifted his dress and showed Ricky his penis. It wasn’t bad, about nine inches and fairly thick. But
Ricky shook his head no and smiled, and Dawn shrugged and put his dick back into his lace
panties. When the taxi finally pulled into the driveway, Ricky looked up at the sky and sighed,
then walked Dawn to the car and opened the back door. Before Dawn got into the car, he pulled a small slip of paper from his purse and handed it
to Ricky. “You seem like a nice boy,” he said. “If you’re ever interested, call this number and
ask for Chad.”
Dawn laughed. “Chad is all man. He’s what every gay boy like you in Jersey wants. Trust
me, he won’t let you down. He’s one of a kind, and only twenty-two years old.” Then he climbed
into the backseat and told the driver to take him back to New York through the Lincoln Tunnel,
not the Holland.
An hour later, Ricky was flat on his back in his bed. He should have been exhausted after
such a long day, but he couldn’t control all the disconnected thoughts running through his head.
Though he was relieved the situation with Dawn had been easy to fix—(it could have been much
worse—he was still horny and still frustrated. So he slid his palm beneath the covers, into his
white briefs, and down to his dick. He spread his legs and squeezed his balls, hoping a good jack
session would relieve all the pent-up emotions he was experiencing that night. But when he
closed his eyes and started to fantasize about his dream guy, the only images that passed through
his head were reruns of past nightmares.
He drifted into a daydream and tried to imagine the hot, dark-haired dream guy who
resembled Keanu Reeves standing over his bed. The room was dark but there was enough
moonlight passing through the windows to see the guy was wearing nothing but a white bath
towel around his waist. The dream guy looked down and Ricky and smiled. He had heavy five
o’clock shadow and his thick black hair was messy on top. Then he reached forward and yanked
all the covers off Ricky’s bed. When the dream guy saw Ricky was only wearing white briefs, he
reached down with both hands, yanked the briefs down Ricky’s legs, and tossed them back over his shoulder. Then he removed his white towel and stood back. He had the biggest, thickest cock
Ricky had ever seen. It was even bigger than Glen’s dick.
That’s when Ricky smiled and nodded at the handsome stranger in his room. He spread
his legs as wide as they would go and lifted them in the air for the man of his dreams. It only
took seconds for the dream guy to climb on top of Ricky and push Ricky’s knees against his
shoulders. He grabbed his dick and rubbed the head against Ricky’s opening. With one quick
push, he went all the way into Ricky’s virgin hole without so much as a flinch. It didn’t hurt in
the least. It felt as if Ricky’s body had been designed to accommodate him to perfection. And
when he started to buck his solid slim hips into Ricky ass, Ricky arched his back and moaned so
high, he sounded like Tiffany had sounded with Glen earlier that night.
But a minute after that, while the dream guy bucked and slammed into him, Ricky heard
sirens and a commotion outside the house. He noticed red and amber lights shining through his
bedroom windows and people were shouting up at the house from the front lawn. Ricky laced his
fingers around the dream guy’s neck and the dream guy put his arms beneath Ricky’s knees so
he could hoist him up. Then he carried Ricky to the window, pushing his penis inside Ricky’s
body the entire time, so Ricky could peek through the blinds and see what was happening outside.
The house was surrounded with police cars and men in uniform. An officer in plain
clothes who resembled Ricky’s math teacher held up a megaphone and said, “Ricky, this is the
police. The house is surrounded. Put down your slutty legs, get that big thick cock out of your
ass, and come outside with your hands above your head, you little whore.”
Ricky’s mother and father came running across the front lawn. His mother’s expression
was pinched and she had one hand pressed to her throat. She grabbed the megaphone and said,
“Please, honey. Do what the police say. Tell that man to stop doing that nasty thing to you with his huge penis and come downstairs. It’s not too late, dear. Don’t ruin your life by doing naughty
things with men who look like that nasty brute, Keanu Reeves.”
Then Ricky’s divorced neighbor from next door pulled the megaphone out of Ricky’s
mother’s hands and said, “Listen to me, you little pervert. I saw you jerking off outside last night
by the pool. I saw it plain as day. You licked your fingers and your own come. You’ll never go
to college now, pal. You’re nothing but a little gay creep and it’s time to come clean. I have
photos to prove it.”
The dream guy bucked his hips into Ricky’s ass and said, “You eat your own come?”
Ricky nodded and tossed his head back. Though he was terrified, he loved being
suspended in mid-air in the arms of his dream guy, while his dream guy was still buried in his
“That’s so hot,” the dream guy said.
Ricky tilted his head toward the window. “Not according tothem
“Fuck them,” the dream guy said. “I only care about you, baby.”
But before Ricky could reply, he snapped out of the dream and opened his eyes. He left
the dream guy standing there alone and jumped out of bed. He switched on the light on the
nightstand and rubbed his eyes. This was getting bizarre. He was so frustrated he couldn’t even
fantasize about his dream guy anymore without giving himself a guilt trip. He needed the real
thing. He needed a man, he need to find out what it was like to be with a man, and he needed it
So he went to his desk and opened his laptop to find the website Leyland had been
viewing when he’d called Dawn the she-male. They couldn’t all be she-males on the site. Maybe
there was a normal male escort who appealed to him, one who resembled his ultimate dream guy and could help him lose his virginity with tenderness and affection. It was worth a try. And
though he’d never admit any of this to Leyland, it did seem like the best way to get laid with the
least amount of complications.
But all the escorts listed on the website made him feel creepy. When he read their
advertisements, the hairs on the back of his neck stood up straight. One guy was into licking feet
and sucking toes, another was into something called water sports (whatever that was), and there