Tom McCallister

Three Weeks Ago

"Screw her, man," said Tom to his best friend John. His one date with Gwen Roberts didn't turn out very well, and she just 'wanted to be friends'.

"That's what I was trying to do," replied John, sarcastically. "At this point, I'm going to die a virgin."

"Maybe ask Nichole or Janice on a date?" replied Tom in confusion.

"Fuck that," said John. "I'm fed up with these nerdy girls. First Erin, now Gwen. Might as well go all out and ask Ji-Yoo if I'm just going to get rejected out of hand." John slammed his locker shut, as Tom grabbed a magazine out of his and quickly hid it into his bag. "What's that?"

"Nothing. Listen, I need to skip out early. See you at seven?" Tom asked.

"Maybe. Unless you're going to ditch me too..." said John, still worked up and angry, as he tends to get.

"You have to buy me dinner first," joked his friend, which gave John a little bit of a chuckle.

Tom got into his luxury car and pulled out the magazine. Pregnant Cuties was the name, and the issue dated to the late '90s, before Tom was even born. Or John, in this case, as Tom recognized the woman on the cover. A young Mrs. Doe, pregnant, and topless on the adult magazine. Pictures inside showed her in her full glory, something Tom took full advantage of in his private times. He was a child of the Internet, with full access to all the depraved, sickest pornography one could imagine. This last vestige of a bygone, innocent era of printed preggo porn, wouldn't amount to a shrug to anyone else, except for that one factor of familiarity.

Ever since middle school, Tom enjoyed going over to John's house to play and hang out. He grew an infatuation on his best friend's mother, Karen Doe, that was bordering on obsession these days. He barely mentioned her to John anymore, for fear that his friend would notice and kick him out. But that obsession somehow led to him discovering this magazine, and the pregnant model "Merry Kerry", which was unmistakably a younger Karen Doe, Karen Smith at the time, pregnant with her first daughter. The circumstances around her nude shoot baffled Tom, since she was the daughter of a well-off politician and didn't seem to have ever suffered want for money.

But Tom wanted more. "Merry Kerry" never appeared in another magazine, as far as he could find, nor any video or other record of her career existed by the year 2019. It was probably a one-time fluke, that she grew skeeved out by the industry, and didn't bother to take further pictures during her second pregnancy (with John) or at any other time. Her pictures were reprinted a few times, including a few additional ones circa 2006 in the final issue of Pregnant Cuties, but they were all obviously from the same '90s photo session.

After several weeks of back-and-forth letters, emails, and veiled threats, Tom is now getting what he wants. Some alone time with Mrs. Doe. He pulled up to the motel near the freeway, and breathed hard as he saw her car.

Karen sat tensely in her motel room, eyeing the door, as she awaited her blackmailer. At first, she thought it was her former husband, who had left nearly sixteen years previously. She knew he was shunned by his family and living mostly as a drifter these days. Perhaps he needed cash? But, no, her PI had quickly fingered the culprit. One of Johnny's friends who had not covered his tracks. She laughed when she recognized the name, but convinced her PI not to "rough him up" or whatever he was prepared to do.

She sat in the dark room with the blinds closed, a briefcase nearby on a table, as she received a phone call from a burner phone.

"Mrs. Doe..." came the voice, disguised via some cheap app.

"Yes, sir," she said, masking her humor with some fake fear.

"Do you have the cash?"

"I do, sir."

"Are you alone, as we discussed."

"I wouldn't want anyone to find this out," she stifled a laugh, remembering how her whole family found out twenty years ago, and it was a minor scandal that cost her father his chance at reelection. Certainly, Tom could've figured that out.

Tom sat in his car, across the street in a large lot, and gulped as he heard her stifle a laugh. This was a joke to her. Maybe she had someone in their ready to beat him up. He pulled up the binoculars and focused on the window to the room he had purchased under a fake name, but it was drawn closed. Was this all a game? Did she not mind? A part of him feared that she had a man in there ready to beat him up, but certainly nice old Mrs. Doe would never go that far.

"Good," he lied, unease in his throat that he hoped the VoiceMasker app covered. "There-" he stopped, "there are handcuffs in the first drawer." He didn't know why he thought this would work.

"What do you want me to do with these?"

He stopped and thought through with his plan. Just pictures. That's all. No ****, no ****, nothing horrible. "The agreement was..." he said, ready to agree with what had been discussed over several weeks, over the phone, "that we spend the afternoon together, and you give me a monetary donation in order for me to forget about these photographs." He had coaxed his words to prevent any threat of criminality, but was sure she understood his meaning. "I think the best afternoon together would be in this bedroom, with the lights off, and perhaps a relaxing full body massage."

He gulped. "So, uh... remove your clothing, turn out the lights, and handcuff yourself to the bed. I'll be in shortly."

Tom put his hood up and got out of the car, carefully avoiding being seen should anyone peek out that window. He found his way out of sight and crossed the street, walking close to the motel as he came closer and closer to the motel room door. He was one room over now, and stopped. Taking out the keys, he opened the door to the adjacent room that he had also purchased for the afternoon. He quietly closed the door and walked up to the unlocked door connecting the two rooms. He placed his hand over the doorway, and breathed heavy as he prepared to enter.

Then a black hood was placed over his head.