Theo’s Photoshoot Ch 1

It was going to be a weird weekend. Theo already knew that agreeing to this job was probably going to be a bad idea. But pulling up to the beachfront cottage made it feel real--he was going to be living in this cottage with a stranger, modeling for erotic photos for a whole weekend.

Theo could argue that Tod wasn't a stranger. He had been messaging him since he first opened his account on the porn site. Needing extra cash, and hearing from some of his friends that old ladies online would pay to watch him jack off, he set up his account without thinking too much. He learned fast that old ladies really meant old men.

Theo knew how he looked. On the shorter side, lean with dark curls and long lashes, Girls had called him pretty all his life, so he was used to it. But seeing the messages flooding into his inbox from men telling him that was a bit jarring at first. However, while Theo had never thought of being with men and felt little interest in putting anything in his ass before this, he wasn't homophobic, and if these men were going to spend their money to chat with him, why not?

Theo wouldn't deny that money often bought his cooperation. At the start, he would chat with the men, tease a bit, and if they paid, he was happy to send dick pics--but he drew the line at his ass. He wasn't gay, and he wasn't about to go showing off his asshole to men on the internet.

Tod changed that. Theo couldn't say no to the $200 he sent over just for a shot of his bum in the mirror. Things escalated fast from there--first getting convinced to bend over a bit in the next picture, then sending a video of his finger rubbing against his tight hole, and finally the most recent video of his little ass eating the tiny plug Tod had sent him. Each time the bar was raised, Theo would try to say no, but Tod knew the moment he added another $100, Theo was easily convinced.

Now two years later, here he was, sitting in his car outside the nice beach cottage after having agreed to finally meet Tod. The offer was too good for him to refuse: $3,000 for one weekend of photo shoots. He would only have to pose for three hours each day, and all Tod wanted the rest of the time was to watch him enjoy the beach house dressed in scandalous clothes. Theo was even sent pictures of the jockstrap and Speedo Tod had planned, so not even that would be a surprise. Theo had been playing with his ass for the camera for the last year after Tod had finally worked him up to it; he even sent ass-play videos to other men now too--as long as they paid, he was happy to perform. Tod already knew the rules: Theo said touching was okay, but he wouldn't be touching Tod.

In Theo's mind, it wasn't gay as long as he didn't touch Tod back. He knew Tod wanted to grope him, finger his ass, and watch him cum. He was almost excited to have a weekend of handjobs freely given with nothing requested in return, cause he wasn't gay, and touching another guy back would be gay.

Taking a deep breath to calm his nerves, he stepped out of the car. Grabbing his small bag of stuff, he made his way to the front door.

He didn't have to wait long after knocking before the door swung open to reveal a huge, smiling man. Theo knew what Tod looked like--he had sent his picture a few times--but he couldn't help being surprised by how handsome he was in real life. He was much taller than expected, muscular in a working-man way with a thick beard on his kind face. And just as Theo expected, he was a warm man--instantly friendly, giving Theo a warm hug, taking his bag, and ushering him into the house while starting the tour right away to a constant stream of conversation about Theo's drive up to the cottage and how excited Tod was that he was there.

Barely saying two words, Theo was amazed as he was walked through the beautiful one-floor cottage, full of big windows that faced the scenic beach, decorated in light blues and whites throughout the house. Theo was surprised to learn that Tod was not renting this cottage--he owned the beautiful place, though he shouldn't have been surprised given the amount of money Tod would blow on him weekly.

Finally, they made their way to the end of the hall, which had two bedrooms on each side. Pointing to the left, Tod nodded to him.

"That'll be your room for the weekend. I've left the outfits we discussed on the bed, so feel free to change, then come join me in the kitchen." With a smile, Tod let his hand reach up and grope Theo's lean chest, making him jump.

Laughing, Tod looked at him as he kept rubbing his chest.

"Don't jump too high there, Theo. You already knew I was going to be touching you all weekend long, and you know how much I like your nipples--I make you send pictures of them to me often. Now go change; I'm dying to stare at your sexy body while I enjoy my lunch. Now, did you forget what you are supposed to call me?"

Feeling his face heat up, Theo was instantly embarrassed. This was the one part of the weekend that made him blush just thinking about it.

"No, Master. I'll meet you in the kitchen in a second." Theo's blush spread down his chest as he heard Tod laugh before spanking Theo's ass and heading down the hall.

Calling another man "Master" all weekend was going to be so embarrassing. But Tod had always seemed so nice online--like a gentleman, never super pushy or mean if Theo said no to things. But if Theo really thought about it, he didn't think he had ever not done what Tod wanted. Maybe not at first, but Tod would ask often, so nicely, and offer so much money that Theo had never said no.

At first, Theo had only agreed to come over for three hours to take pictures and leave. That had now turned into a weekend of basic nudity and touching. Regardless, Theo had never made this kind of money in just one week, so he was going to try his hardest to do well. Maybe it wouldn't be bad, and this could become a regular thing--two weekends a month and he'd be set. Life as a sugar baby might not be so bad.

At the same time in the kitchen, Tod was ecstatic. The first time he laid eyes on the young twink on the website, he was hooked. And learning the young man thought he was "straight" was hilarious, considering how easily he would fold for small amounts of money. Tod had greatly enjoyed corrupting the straight boy, still watching the video of the first time he fingered his own ass at least once a week.

But he had been craving more, and now he finally had it. Theo himself was in his house for him to touch all he wanted, and if everything went according to plan, Theo would officially be his.