Fourteen-year-old, willowy, golden-haired, blue-eyed Kenny sauntered up to the black Cadillac Escalade under the 7th Avenue, East Ybor City, Tampa, underpass below the connector road between I-4 and the Lee Roy Selman Expressway as the smoked window of the backseat rolled down.

“How old are you, kid?” a voice with a Cuban accent asked from inside the car. A muscular arm, covered with curly black hair, came to rest along the window sill. A “tough-guy” scowling, but handsome, young, swarthy face, with several days of growth on it, appeared.

“Eighteen,” Kenny said, crouching down to where his face was parallel with that of the young man in the backseat of the SUV. The man was maybe in his late twenties, handsome in a foxy thuggish sort of way. It was a face that made Kenny wonder why he’d have to be out here on 7th Avenue hooking up with young rent-boys. He must be someone important, Kenny thought, to be in an Escalade and sitting in the backseat with someone else driving.

The window whirred up half way. “Guess again, kid, if you want to make money. I’m looking for someone younger—much younger.”

“OK, I’m fourteen,” Kenny said.

“That’s more what you look like. That’s good, if that’s what you’ll go with. How are you at acting?”

“I give good head and great fuck,” Kenny answered.

“That’s not what I asked, kid. Can you role-play—act like it’s your first time and you don’t want to give it up?”

“Sure, if that’s what you want.”

That’s how Kenny got it in the backseat of the Escalade, as it glided around Tampa, working its way west, toward Old Tampa Bay. The boy didn’t see that the guy had a gun in an armpit holster until he’d gotten into the backseat. He went docile immediately, but the guy slapped him around and said, “No, I want you to fight against it. Don’t worry, I won’t blow you away. This here’s just a test of your acting skills.”

Kenny struggled, being forced to the floor of the car, between they guy’s spread thighs, and slapped around some more before the man held the boy’s head steady between his hands and made Kenny gag deep-throating him with his cock. The man remained fully dressed, with just a meaty cock in erection jutting out of his fly, when he lifted Kenny’s much smaller body up, slammed the kid’s head against the inside of the door, and laid him out along the backseat.

Kenny continued to struggle as the man came down on top of him, between the boy’s thighs, pulled Kenny’s shorts and briefs off his legs, and pinned Kenny under him. Kenny panted and cried out when the man’s fingers penetrated him and worked to get him open—and then again, trying to resist, as instructed to do, as the man put himself in position, mounted Kenny, worked his way inside the boy, and started to pump him. The man’s strong hands gripped Kenny’s throat and he controlled the boy’s gasping breathing while he vigorously fucked him. Kenny beat on the man’s biceps and chest with his fists in a weak attempt to fight him off—as instructed—but to no avail.

Eventually, spent, and more worried about breathing than getting fucked, Kenny collapsed under the young thug, going docile, hooking his knees on the man’s hips, and rocking with the fuck. The boy moved a hand between them, grasping and stroking his own cock, as they both raced now to an ejaculation.

Fifteen minutes and it was done—the popping of fourteen-year-old Kenny’s male cherry in the backseat of a cruising Escalade had been role played.

Afterward, the man said, “Very convincing. Was that really your first time?”

“It was if that’s what you wanted,” Kenny said.

The man laughed. “There’s a proper cleanup, a meal, and a couple hundred bucks in it if you can do that for an old man too.”

“Whatever you want,” Kenny said.

The Escalade had stopped—at first briefly for a set of metal gates to open—and then down a drive covered in heavy foliage into a parking area in front of a large, two-story white stucco mansion, with a Spanish-style red-tiled roof. Around to the side of house Kenny could see a lush garden area with the waters of Old Tampa Bay as a backdrop. They’d arrived in the exclusive Tampa, Florida, residential area of Bel Mar Shores.

“Into the house first,” the man who had fucked him gruffly said, taking Kenny’s arm and leading him up a flight of stairs toward double carved-wood doors.

Kenny was shown into the house and to the service wing, where, behind the kitchen and a servants’ lounge, he was taken to a small bedroom, with its own bath. His guide identified himself as Diego. He was a handsome, muscular man of dark complexion—a Cuban, Kenny surmised. Diego followed the boy into the bathroom and then into the shower, both stripped down. He fucked Kenny against the shower wall under cascading water in a standing bully fuck, with Kenny’s arms flung around his neck and his knees hooked on the man’s hips. Kenny didn’t mind the second fuck. He was being paid well and it wasn’t often that he was covered by a man this young or as hunky.

Afterward, as Kenny was dressing and Diego was strapping his gun holster back in his armpit, Kenny received his direction.

“He is an important man. Hector. His name’s Hector. You don’t need to know or ask about a last name. You are to play the role of a kidnapped boy, brought to him to provide him with sexual release. You are to give him a story of coming from wealth to justify kidnapping you for ransom. You are not to show you are too scared until it becomes obvious to you that he is going to use you roughly. As you did with me, you are going to be fucked for the first time, and you’re going to fight it initially. But he will be so masterful that you will, eventually, come to him, wanting it. Do you understand?”

“Yes, I think so,” Kenny said. “How difficult will it be—?”

“He is an old man, but he is strong and virile. He will do you totally. Maybe four, five times in a day. He hasn’t had any for a while. When you leave here, though, you will forget him entirely. Do you understand that?”

“Yes.”

Kenny found that the clothes he was given to wear were expensive, although it was athletic gear. In the scenario, he would have been kidnapped—taken off the street and into the Escalade—while he was out, running. The athletic shorts were silken, cut high up on the thigh. The silk top was a tank top. The jock was silky too. The running shoes were expensive. There were no socks. He looked at himself in the mirror and knew that he looked like sex on a stick, for anyone wanting a small-stature fourteen-year-old boy.

“That’s what the old man wants,” Diego said. “And remember, we have not had sex, you and me. At least yet. You have been kidnapped for ransom. You will be a virgin the first time he takes you. Fucking you isn’t part of the kidnapping. He’ll just see you and fuck you because he wants to and he can.”

“Yes, sir,” Kenny said. That would be the hardest part—denying to himself that the hunk who was Diego had not fucked him twice already.

Hector Garcia, although Kenny wasn’t given the man’s last name, was sitting on a covered patio at the back of the house when Diego brought the boy out. The garden, which surrounded the house and was covered with extensive lawns and sections of lush foliage that went to the edge of Old Tampa Bay in a large arc, was so large and developed that it was hard to believe that they were in the middle of a city. The man himself was old, gnarled, and with a skin of berry-brown leathery texture. He was somewhere beyond sixty. But he was trim and muscular, bald but with bushy eyebrows and a look of sharp wariness and a keen sense of assessment. He was poised like a cat, ever vigilant, a look that went with the gun holster strapped under his left armpit. He was wearing only khaki shorts that hung low on his hips and open-toed sandals. His toes, like the fingers on his hand, were long and plump. The scars on his torso and a couple of puckered areas where he’d taken bullets indicated he was a veteran of underground wars.

The only other item he was wearing as he sat at a patio table, a glass of wine and a place setting in front of him, was a tracking ankle bracelet. Even Kenny, at fourteen, understood that this was a man on house arrest—and very probably a man of great importance in the underworld to be living here, even if a prisoner of the state, rather than marking his time behind bars.

Three place settings were set at the table. Hector gave Kenny an assessing look, with command behind it, and gestured for him to sit at the table. Diego took the third seat. The Cuban who had been driving the Escalade around town while Diego fucked Kenny in the backseat served a luncheon. His age was somewhere between that of Hector and Diego. He was ugly as sin but muscular and quite capable looking, and he had an ugly scar slashing diagonally down on his face from ear to the corner of his mouth. He, like the other men, was armed with a gun holster and was dressed in black jeans and a black cotton tank top.

“Which one is this, Diego?” Hector asked. “Never mind. The lad can speak for himself. Speak up, boy, you’ll be fine. This is just business.”

Kenny wondered if this really was a role-playing game for the old man, but working on being cooperative as a veneer over fear and confusion, the boy wove a tale of his father owning several grocery stores in the area and his mother being a corporate lawyer for an oil corporation. He figured that would provide a reason why someone in the underworld would be interested in kidnapping him. It also was easy for Kenny to provide as a background because it basically was true, but in a reverse. It was his father who was the lawyer and his mother who was from a family that owned a grocery store chain. The fact, though, which Kenny included in his tale of woe, was that his parents were on an around-the-world cruise. They had no idea that Kenny had decided to have an adventure as a rent-boy.

He said his name was Alan. It was a name he liked to give to johns engaging his services. He’d always liked the name and was sorry that he had been named Kenton Kingsley instead, which he took as rather a pretentious name.

Hector acted more like a doting grandfather than a housebound Cuban mobster during luncheon, although he did lean into Kenny a lot and touch him here and there while talking to him. Kenny might have taken him as just an old-world touchy-feeling sort of guy if Diego hadn’t made clear that Kenny was here to relieve the old man’s boredom—to give him some fantasy and a good fuck or two.