Jamie locked his bike up at the top of the road and walked down. The area was beautiful, full of large and old houses. He had not known that his date was so wealthy, and it certainly didn't hurt to know that now. It should be number 5, he reminded himself, though in the dark it was difficult to spot. He walked down, seeing the house numbers ascend, until he saw it.
He checked the app again and made sure it was the right number, and had to hide his phone from a passer-by until they were safely out of eyeshot. He looked again, opening his chat, and saw the dick pic that had tempted him here. He felt so horny. It was the right house. He walked through the gate, closing it behind him, before taking a deep breath in front of the door.
It was his first time using an app like this. He had flirted with the idea many times, but he never felt like the time was right. He thought he must surely meet someone like him at some point. But he had been so solitary for so long that it was never going to happen, and had eventually resigned himself to this.
The guy had seemed relatively safe and seemed hung, so naturally he gave in to his impulses and told him he'd be there in an hour. He was a couple of minutes late, but hoped that it was worth it. He put in effort for tonight, wanting to feel as hot as possible, shaving his body hair, putting on his makeup, and picking out his cutest outfit in a hurry.
He never wore it in public, but loved dressing up in it, only feeling pretty while wearing it. It was nothing crazy, just a black crop top, chequered red and black miniskirt and black thigh-high silk stockings. But it made Jamie feel cute, and he hoped it would turn on his date. He'd worn a thick long coat above it, though, afraid of seeing someone he knew or of being perceived in general. He wanted his private life to be private, and didn't want anyone else to know.
That was what had stopped him from going on apps earlier. The fear of discovery, the shame of someone else knowing, it had all been too much for him. If he could choose, he would get rid of all his gay feelings in an instant, but they never did, and so here he was. He had tried to get out his sexual urges with porn for years, but every day just increased his curiosity for what the real thing felt like.
He knew he was incredibly repressed and horny, but had no idea how to control it. He had tried giving up porn entirely, but could only go a week or so at most before the temptation was too much. He had tried watching straight porn, but the women never did anything for him, and he always found himself staring at the huge dicks.
This is all a more complicated way to say that Jamie found it impossible to watch anything other than twinks getting railed by masc guys.
Over the years, his tastes had escalated. He felt that his shame and sexuality were so interlinked that there was no separating them, and they fuelled each other. When today's date, still only known to him as T, had asked him whether he'd do whatever he asked, Jamie had eagerly complied. He would become this man's slut, for the night, and that idea made Jamie hornier than anything as he waited in the cold and composed himself.
He closed his eyes and remembered the man's cock, before texting him to let him know he was here. His host had asked him not to ring the bell, not wanting his neighbours to hear a late-night call, and Jamie could relate only too closely to his desire for privacy. The thought of hiding who you were even at the age of forty-three reinforced his cynicism, knowing that there was no escape to the secrecy and shame, no matter how independent you were.
He saw a light turn on at the top of the stairs, and heard footsteps, until he saw a figure descending through the frosted glass window. He felt excitement in his chest, which he hadn't felt for a long time, mixed with anxiety. He feared that his makeup would look stupid, that he would disappoint his host, that his lateness had annoyed the man. As the door opened, his heart raced, and he forced a smile, as he let out a nervous greeting. The man opened the door and rushed him in quickly, the entrance of his house still being dark.
He turned and took off his coat, looking at his match from head to toe for the first time. He was as beautiful as he could have ever hoped. He was a good six inches taller than Jamie, who stood at a mere 5"6, and had a wonderful salt and pepper colouring to his hair and beard. He wasn't slim, but not too fat either, and had a nice stocky masculine build that pleased him greatly.
He took off his coat and put it up on the coatstand, having to reach up to the higher pegs that would accommodate his long coat, and turned around, holding his hands on his bare stomach as he nervously looked up at the man. He stared at him with his mouth slightly open, and then reached out a strong hand to Jamie's shoulder, which made his skin tingle with excitement.
"You're...beautiful," he said, leaning forward and kissing Jamie's head. Jamie felt a rush of joy, feeling so validated for the first time in his life. He'd posted pictures of himself online before, with his head cropped out, and loved receiving compliments there, but that paled in comparison to how good he felt being appreciated in real life. He could have squealed with delight, but kept his cool, beaming as he hugged his host.
"I'm Thomas," his host announced, as he rubbed Jamie's back, pulling him tight to his manly chest. Jamie breathed in, taking in Thomas's masculine scent as he felt himself harden at the compliments and the feel of a man's embrace for the first time. He felt suddenly safe, warm and free, after the nervous wait in the cold.
"I've never really done this before," Jamie said, feeling comfortable telling this stranger such intimate details of his life, "I'm a virgin," he continued, stepping back and looking up. Thomas nodded, and smiled.
"You're so cute," he said, taking Jamie by the hand and guiding him up the stairs. He led him to a room with a couch and TV, which had its own private bar at the side. Jamie felt amazed that he owned all this, and wondered whether he shared the place with anyone. He wandered over to the doors at the side of the room, and saw a jacuzzi outside on a balcony. He wondered whether they'd make out naked in the jacuzzi later, before the main event.
"This place is amazing," he said, unable to contain his excitement.
"Thanks. I don't get much use out of all this stuff lately, now that it's just me. You're welcome to anything you like from the bar," he offered, and Jamie smiled, gratefully shuffling up to the bar and having a look at the wide range he had stored up. A lot of the bottles were half empty, with almost none full, making Jamie suspect that Thomas either had people over a lot, or spent evenings drinking alone. Having done the latter occasionally himself, Jamie projected that assumption onto his host, wondering how lonely this big house must get. It was immaculately clean, however, which made Jamie think he must have friends for whom he kept everything so tidy.
They both sat on beanbags which occupied the spacious room. This was as awkward as Jamie had expected it to be, but he didn't really care, as long as he crossed the bridge he'd procrastinated crossing for so long.
"I assume you ate before coming here? I can order something if you haven't," Thomas offered.
"Oh yeah, I had a light dinner, don't worry," Jamie lied. He'd starved himself for the whole day so that his first time wouldn't be embarrassing. He hadn't prepared enough to have ordered an enema kit, so he had played it safe. He didn't want the anxiety of having a humiliating first time, and he knew from conversations he'd had online that it would be worth it.
"That's good. My fridge is stocked if you want anything else,"
"You're very kind,"
"Not really. Just want you to feel comfortable,"
"You make me feel so comfortable,"
"Oh, that's nice of you to say,"
There was a deafening silence after that exchange, not due to anything bad having been said, but just what Jamie assumed was the natural awkwardness of trying to make small talk with a man you'd be taking in the ass in an hour's time. Eventually, Thomas got sufficiently bored to ask Jamie if he'd like a drink.
Jamie asked for a cider, which made Thomas laugh.
"That request alone makes me want to see your ID," Thomas stated, which made Jamie laugh anxiously.
"Why, it's so much nicer than beer or spirits," Jamie said, which made Thomas lean forward.
"I'm not asking you because you asked for cider, but I would like to make sure you're old enough. To be drinking, of course."
"Why, do I look like a kid? I said I was 20 on my profile, didn't I?"
"People lie. And sometimes hard to tell the age of a guy who already looks like a twink, especially after they put makeup on."
