The first time that I saw him, he was sitting in a coffee shop, by the window. He was sitting straight up in his seat, with a steaming coffee in front of him. He was looking around, as if he was waiting for someone.
After I had placed my order and paid, I looked him over while I waited for my bagel. He was young, maybe 20 or 21, and probably a student. He had messy brown hair, probably from wearing a hat with wet hair. I wondered if he had just showered. He had thick, dark eyebrows set wide-apart, brown eyes, pale skin and red lips. He wore a long-sleeved, western plaid shirt with dome snaps and his chest hair showed at the neck. I imagined a hairy chest and a treasure trail running down into his jeans. I started getting hard.
If he had looked over my way, he would have seen me checking him out, but he never did. He was focussed on the door, watching for whomever he was meeting. His girlfriend? A date?
I left with my coffee and bagel and forgot about him, never expecting to see him again.
But I did see him again, a week later. It was pouring rain and we were both leaving the coffee shop at the same time. I could see his reluctance to step out into the rain.
"Walking to the subway? You can share my umbrella."
"Um, okay, thanks." His voice was unexpectedly deep.
I held the umbrella so it would keep both our heads dry and we walked the 50 yards to the subway together.
"Thanks."
"No worries. No reason for you to get soaked on your way to work."
"I'm in college, actually."
And that's how we got to talking as we went down the escalator together and waited together on the platform. He was in engineering, 21 years old, from a small town. He lived in a house with three other guys near my high-rise condo.
He got off the train first. I still had to go all the way downtown to my meeting.
"See you around." And he was gone.
Whereas the first time I had run into this boy, I had only felt a mild shot of lust, after chatting him up I was entirely interested. Of course, I didn't know his name, much less have a phone number or know if he was even gay.
I made that coffee shop my new hangout. It took until Saturday morning before I saw him again. I let him get his coffee and then waved him over to sit with me. He hesitated, but he came.
We chatted. He was on his way to the library to study. I introduced myself and offered my hand. He shook it and said his name was Mark. He was nervous and sipped his coffee quickly.
"Plans for tonight?" I asked.
"No, I'll probably stay in and watch the hockey game with my roommates. That's what we generally do Saturday nights."
"I kind of like to get out, myself."
"Well, I couldn't really afford it, to be honest."
"I remember what being a student was like." Awkward pause. "I'm surprised you're not out on a date with a girl tonight." A classic line for exploring the gay issue.
"Oh, I'm an engineer, we don't meet a lot of girls in class."
"I'm not the type to have a girlfriend, myself," I offered.
"I was, um, wondering that, actually."
"I hope I didn't come across as creepy."
"No, no. You seem really nice. I just wasn't sure. Well, I should go." He stood up. "It was nice talking to you again."
"Nice talking to you, Mark." At least he was polite about it.
I watched him leave, regretfully. I was starting to really like him, and I had suspicions about just how straight he really was. But I was probably too old for him in any case. I carried on with my day.
An hour later, he sent me a facebook friend request. I accepted it, and immediately started to check out his photos. There were a couple of shirtless pics at someone's backyard pool. He looked good and I started to bone up.
I sent him a message: "thanks for adding me"
"np. You seem like a nice guy"
Interesting... "you too"
I took a deep breath. Nothing ventured, nothing gained. "are you still set on watching hockey tonight or would you like to go for supper together later?"
"actually, I think I need to stay at school and do homework. I'm way behind in this class."
Ah. I started typing a well-if-you-change-your-mind message but then he sent another before I could send it.
"could we meet for coffee tomorrow maybe? Around 1?"
"I'd love to. Same place?"
"Yes. I'd better get back to work now. I'll talk to you later?"
"Sure. Just one thing before you go. You should know I'm gay and I think you're attractive. Is this a date?" I put all my cards on the table face up.
"Yes, I hope so."
"Good, me too :)"
"Cool. OK I need to finish this lab."
"Good luck, bye."
We met the next day. There was plenty of first date awkwardness. I tried breaking the ice with a safe subject, chatting about school. Once he seemed comfortable with me, I asked him if he's out.
"No, I don't have much experience."
"You're confident enough to meet men at a coffee shop."
"I wanted to try something besides grindr. And you looked interested."
"Grindr isn't for everyone."
"All the guys I talk to on there only want to hook up."
"You're looking for a relationship?"
"Maybe. I want to try dating before doing anything more."
"That's reasonable."
"Most guys on grindr don't think so. I get blocked when I say I don't want to have sex right away."
"Grindr is a hookup app, for getting off. You might have more luck on Plenty of Fish. Not that I want you to keep looking for new guys to date," I winked.
I learned that he had exactly one lifetime sexual partner, where he had received (but not given) a blowjob in the dorms in his freshman year, two years ago. I also learned that he had never done anything with a girl beyond the briefest peck on the lips and he had no intention of ever going beyond that point.
"I'm gay. I've always known I was gay. I've always been reluctant to act on it up until now, but I could never be with a girl."
"Does the idea of fucking a girl freak you out?" I asked.
"A little," he admitted.
"Me too."
After we had lingered in in that coffee shop a little too long, he suggested a walk and we wandered around aimlessly for an hour. I told him about my job and how I had got hired and whether I would stay with my current company or switch to earn more.
He conveniently ended the date at the subway entrance. "Okay, so this is me. I should get going. I have some studying to do."
"I had fun today," I responded.
"Me too," he looked down at his shoes and then shyly looked up again. "I'd like to see you again, if you're willing."
"Of course I am."
There was an awkward pause. I broke it by leaning in and giving him a long, firm hug that hopefully said, 'I'm into you but I also respect your wishes to take it slow.' "Take care. Text me tomorrow and we'll make plans."
"Okay! Right, goodnight!" He turned and disappeared into the subway.
I walked home to jerk off.
Around 4 pm the next day, I got a text from him thanking me and saying he would like to do it again sometime.
"Supper out?" I replied.
"Sounds good," was his answer.
We settled on a restaurant and time on Thursday. I picked something was probably nicer than what he was used to as a student but not so nice that he would think that I was trying to obligate him to something. We talked easily all through the meal about everything under the sun - school, job hunting, politics, the latest terrorist attack, movies - everything.
When we had finally finished dessert and coffee and I had paid the bill, we got up and stood outside on the sidewalk.
"I really like you," he said.
"Would you like to come home with me?"
"I think I'm ready for more."
When I got him home, we sat on the couch in the living room beside each other. He was very nervous, so I didn't press him. We made aimless, empty, awkward small talk until he finally leaned towards me. I kissed him properly, open mouth, tongue.
We made out for quite a long time, exploring. I slid my hand up under his shirt. He did the same to me.
"Let's go to the bedroom."
I led him in, and we made out lying down for a bit more. Then I stood up and undressed down to my boxer briefs, which were tight and outlined my erection. He stared, wide-eyed.
I straddled him and unbuttoned his shirt, then unbuckled his belt, then opened his jeans. His boner was straining at the fabric of his plaid flannel boxers. I felt his hardness through his underwear, and he gasped. I took his hand and put it on my package for him to feel a hard dick for the first time. We kissed again as we groped each other.
I peeled off my underwear so I was stark naked now and tugged his jeans and boxers down to reveal his dick.
As I suspected, he had a hairy, natural bush that spread up his stomach to his navel and then narrowed to a line and spread out again across his pectorals. He was cut, like me, and his dick was average, but hard as a rock and ready to go. I sucked him until he came in my mouth.
I rolled on my back and he pounced on my cock like a dog going for a bone. It was definitely his first time, but knowing that really turned me on and more than made up for any lack of technique. When I came, he attempted to swallow it but it mostly went down his chin as he gagged. We cuddled afterwards.
As we lay there, I started wondering how far this would go. Are we going to be boyfriends? Am I robbing the cradle?
Mark started stroking my cock back to hardness. I could feel his boner was back, pressed against my hip.
"I need to know what it feels like to be fucked," he whispered.
Time for Round 2, I said to myself.