Meeting Greg

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Young man meets older online friend.
6.5k words
4.66
9k
19

Part 1 of the 2 part series

Updated 12/30/2023
Created 08/02/2023
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It was the late 90s, and I had just turned 18. The internet was a pretty wild, unsupervised place back then. Chat rooms were king, starting with AOL and then moving into IRC and other venue. On AOL, you could enter a chat room and get porn sent directly to your email, it was that simple. And finding people to chat with - especially sexually - was as easy as typing, 'a/s/l'

I was a shy kid, mainly brought on from emotional abuse from my parents that destroyed my self-confidence which led to being bullied through most of middle school. Most of that had ended by time I reached 18, but there were still remnants of it in my life. One of the more noticeable areas was my highly active online life.

Obviously if my parents knew I was using the internet to have cybersex with other men, they probably would have cut off my access. Shit if my parents knew I was interested in other men. From their language choices, I know my parents wouldn't have been approved. And culturally, we were just a few months removed from the tragedy of Matthew Shephard.

I didn't act on any of my sexual urges with another person exactly because of those fears. I could walk to a park that had a highly active, and very well known, cruising scene. But that felt weird and a little scary. I assumed I'd be uncomfortable, and I'd get forced into something I didn't want to do.

So, talking to men and pretending on the internet was the basis of my experience to date. I started engaging in phone sex with men when no one was around, them listening to me stroke myself while they told me all the nasty things, they'd do with me. Again, most of these ideas scared me a little bit, but it was all part of the pretend. And I was interested, just needed to build up my courage and confidence.

It was a Wednesday night, a bit past 9pm and I needed to log off and take a shower before Seinfeld reruns at 10 and 10:30 then lights out. I was casually browsing a few regular chat channels I frequented at the time, one being an 'oldermen4boys' channel. The hourly 'a/s/l/ auto-post refreshed and I added my details to the chorus of responses, "18/m/St. Louis, MO" when I almost instantly got an instant message:

"Hey neighbor! 46/m/in the central west end"

Interesting. Only one time before had I connected with someone from this channel in my area; we chatted a few nights, but he disappeared. There were a couple of the younger 'boys' I would chat with from time to time but had never met any in person. Before I could respond, he typed again:

"What are you up to, tonight?"

"Oh, not much, kind of quiet tonight. Probably signing off soon for the night"

"Aww, sad. I never see anyone from nearby on here, I was hoping to chat."

"Yeah, I don't either. I could chat for a little bit, but I've got to log off pretty soon"

"That's ok," he responded, "could I save your name and message you the next time I see you online?"

Interesting, usually when I try to politely blow someone off here, they get aggressive about not disconnecting. This seemed a little different.

"Sure, sounds great. I'm online a lot" I typed back, and quickly logged off. Even though I didn't need to, for some reason, I felt like keeping to my story.

I jotted his name down too, and didn't see him in the chatroom over the next couple days when I popped in. Finally, Sunday afternoon, I logged in and spotted his name in the room. I didn't message him directly but waited to see if he would first. I clicked over to my email client and before all the email could download - a 56kbps modem was what it was - I heard the ping of an instant message from the chat window. I opened it and saw a flashing notification from my new internet friend.

"Hi again!" it read

"Oh hey" I replied quickly

"Remember chatting with me earlier this week?"

"Yeah, of course."

"Good! I've been looking for you but haven't seen you online since then. I was hoping I would find you again"

"Yeah, just got busy with school stuff and the weekend. I'm in here pretty regularly, don't change up my screen name or anything"

"Great :) How was your weekend?"

And we went from there. I found out he was 46, grew up in town but left for college and law school. He's a lawyer - same as my dad which was a little scary to me at the time, I didn't want to 'know' this guy personally - and does a lot of volunteer work that he loves. He spoke in complete sentences and asked me questions about myself and my life that weren't sexual in nature. Guys in these chat rooms always turned conversation towards sex as fast as they could, but this guy was different. He never brought it up once, not what I was looking for or what my experience with guys was...it was just a conversation about our lives and our interests.

We chatted for almost 2 hours, and it was getting close to dinner, so I told him I had to go. He asked me if I'd like to chat again, and I told him I'd love to! He then asked me my real name which I told him - Michael - and he told me his name was Greg. And he wished me a good night as I logged off.

We chatted online almost daily after that. I wouldn't see him online before 8 or 9pm, so I started adjusting my online schedule to accommodate his. Eventually I mentioned some of my concerns with 'dating' and being 'out' in the political climate, and he was very forthcoming with details on how he meets men, what dating as a gay man looks like, etc. And I admitted to him that I'd never been with a man before - I'd never even kissed another one - and I wanted to, I did, but I was scared and nervous at the same time. And he was very understanding, and again, shared his experiences with me as a way of empathizing with my emotions.

It was a couple weeks of daily chatting before he broached the subject of us meeting in public. I was overly excited about the prospect, and got instantly hard when I read the message on my screen from him,

"Would you be interested in meeting in person this weekend? Maybe grab a cup of coffee and just chat in person?"

I couldn't type my reply back fast enough, but i didn't want to appear too desperate either. So, I stood up from my chair and paced the room a couple times just to bide some time, before typing back a simple answer,

"Yes."

We arranged to meet at a coffee shop closer to his house, but with which I was familiar and could easily bail if I needed. We had exchanged a couple of pictures over email, but there I was still concerned I wouldn't recognize him, so I arrived about 10 minutes early. But as I approached, I saw him sitting outside already waiting for me.

We made eye contact and I smiled and waved a bit, he stood up to meet me and I realized i had never asked him his height, obviously, because he was easily 6'3" or 6'4", he towered over my 6'0" frame. He had broad shoulders and big arms, his hand dwarfed mine when he extended it to shake hands. He had told me he played some college football before injuring his knee, but he must still work out regularly to look like this. He had jet black wavy hair and was wearing a pair of aviators with a button down and slacks. I thought to myself how much I hoped to look like him when I was his age

"Hey, Michael, glad you made it" he said, smiling broadly as we shook hands. "I was really excited to meet you, so I got here early, hope that's ok?"

"Yeah," I trailed off, not sure why I'd be upset about him arriving early. "I got here early too so it works out, I guess" shrugging my shoulders a bit. It was quiet on the street, no one passing by and no one sitting at any of the outdoor tables.

"Well, I'm glad to finally meet you in person"

"Me too" I smiled back at him, then looked down a little nervously.

"Do you want to go in and order something?" he asked, and I followed him in to do just that. While this place was closer to his house than mine, I was actually kind of a regular here and knew the woman working behind the counter. We were in the 'alternative' area of town, and i spent a lot of days and nights just loitering around this area walking back and forth between the record shop and the various head shops. He was obviously surprised to find out I knew the barista because it was the first thing he mentioned when we were back outside with our drinks.

"So how do you know the owner?"

"Oh, that's not the owner. Patrick owns the place, he's usually here during weekdays. That's Sarah, he usually works nights and I guess weekend days? I don't usually come down here this early on a weekend." It was 11am.

"Ohhhh, so you're a man about the place, huh? Is that why you suggested meeting here?"

"Yeah. I mean i suggested meeting here because I knew it wouldn't be far from you, and if you didn't show - or it got weird - I know my way around here pretty well. I didn't want to meet in a Denny's or something"

"No, that's fair' he said, taking a sip from his cappuccino. "Did you think I wouldn't show?"

I shrugged. "I don't know, I haven't really done this before. I was really nervous walking over here, I even turned around at one point and started walking back to my car"

"I know" he said, reaching over and touching my hand with his. "I was sitting here and watched the whole thing from down the street. I knew it had to be you" he said laughing a little bit.

I felt a little embarrassed and called out here, which he could immediately sense.

"Oh, I thought it was so cute, Michael. I understand why you'd be nervous and scared to meet me, given your history with men. Or lack of history, right?"

I just shrugged; I didn't know how to respond to that. He was right, of course. But I still felt embarrassed by my inexperience and nervousness. Again, he sensed this immediately and reached across the table to touch my hand again.

"Hey, I'm sorry if I'm making you uncomfortable. That's not my intention at all. I'm trying to say that I can relate to your feelings, and there's nothing wrong with expressing these emotions, especially with me. I'll be a safe person for you to talk with and feel comfortable with, I can do that for you at least."

I felt something change a little inside me because of those words. There was a sincerity in his voice and coupled with his actions during our chats and today, I believed him. I relaxed a lot after that, I could feel a weight come off my shoulders and our conversation just flowed easily from there. Whereas our online chats were more centered around me, I spent almost the next hour grilling him with questions on his life and interests; why he chose law, what kind of law he practices, why he moved back to St. Louis, his family house down at the lake that "you must come see some time' and the house in Michigan he's thinking about buying.

When I asked him for the time, it was nearly 2pm. My stomach was growling and asked him if he wanted to grab a bite to eat. There was more than a dozen restaurants on this street to grab a bite to eat, but when he offered to invite me back to his place, "and I'll make us something casual," I couldn't respond fast enough that, "I'd love to do that," and we arranged to meet with our cars so I could follow him back to his place.

I didn't know where this was going, but I had butterflies in my stomach as I followed him the short distance from the coffee shop to his home. And it wasn't just a house, but one of those three-story old Victorians that are prevalent in the area, the kind of house that makes you think, "who can afford to live in there?" when you drive by.

He pulled in front, and I parked behind him, then followed him up the short flight of stairs and inside. And if I thought the exterior was nice, the interior was like a show room of antique furniture and art pieces. I just stopped in my tracks when I entered the foyer.

"Nice, isn't it?" he said without really stopping, continuing through the large square space, and heading back towards the kitchen area. I followed behind him into the bright white kitchen with an attached sun porch that looked out onto the backyard. "It was my grandparents' house, I spent all of my holidays here as a kid. When my grandpa died and we had to put my grandma in assisted living, we wanted to keep the house in the family, and I was the only one really prepared to take on the maintenance costs...so it's mine now!"

"No way" I said in disbelief.

"Yep, true story. Let me tell you though, the maintenance on this is NOT cheap. These old homes are a pain to heat in the winter and keep cool in the summer. Plus, I only use like three or four rooms total so I have all this wasted space."

"Still, not a bad deal. This place is amazing" I said, looking out onto the yard and the rows of rose bushes.

"No, certainly not a bad deal. And we still hold family gatherings here so it's not a total waste. I should put in a pool out back, there's more than enough space, and I wouldn't even touch the roses. Trust me, I can't touch the roses without starting the War of the Roses" he laughed amusingly to himself, as he came along side of me and draped his right arm around my shoulder. He pointed out past the rows of rose bushes to the open lawn and described where the pool could go, the pool house out beyond over in the corner of the lawn. He tried to show me the hot tub and bar area he put in a couple summers ago, but our view was restricted.

"I'll take you out there later, but now, let's get lunch started" he declared, turning on his heels and heading around the large kitchen island towards the refrigerator. "What are you hungry for?" he asked over his shoulder.

"Ohh, I don't know, what do you got?"

"Well, I could whip us up a couple sandwiches pretty quickly if you're super hungry. I've got some tomatoes in here, I could make a little pasta with tomatoes and basil if you'd like, doesn't look like I've got any chicken..."

"Whatever you want to make is fine," I said a little dismissively. I hate this ring-around of, "do you want this, do you want that?" I really wanted him to just decide something and make it; obviously, I was a little hangry.

"I've got some left-over focaccia bread over there. If you help, we can knock out this pasta dish really quick and sit outside on the patio and enjoy it"

"Sure" I said, and he smiled broadly back at me before reaching back into the fridge and pulling out a container of grape tomatoes. "There's a large pot of basil right outside the back door, can you go out there and pluck me off like 12 big leaves?" he asked as he began to roll-up the sleeves of his button down. He was getting serious. And it was hot.

"Sure thing" I said, bounding across the kitchen to the patio doors. I stepped outside and looked around for the pot, taking in the bar and patio area he was eager to show me earlier. I found the pot of basil - it was not right next to the door like he said - and plucked off '12 big leaves' and brought them back inside.

"I'm sorry," I started, "But the basil is NOT right next to the back door" I said a little bratty.

"Oh, I'm sorry. But you found it, yes?" he said, not looking up from the garlic he was chopping then placing into a pan with olive oil. I set the basil down on the counter in front of him and pulled up a chair to watch him. He was confident with the knife, dicing an onion with ease and adding it to the pan with the garlic. He worked through the tomatoes quickly as well but set them off to the side for later.

"Can you go into the pantry and grab me some pasta? There are a couple different types in there, choose what you think is best."

"Uhhh, where's the pantry?" I asked, looking around, but not too hard. He pointed with his knife to a large door off to his left, and I hustled over. When I opened the door, I realized his kitchen pantry was maybe larger than my bedroom at home. How could i even find pasta in here? Oh, there it is, on a shelf in neatly labeled containers. I grabbed the angel hair and brought it over to him. Then pulled up my chair and watched him continue his prep work, noticing in my absence he added a pot of water to the stovetop. The garlic and onions had started sautéing, filling the space with a flavorful aroma that just made me hungrier.

We chatted about this and that, him giving me pointers on some food prep techniques and showing me how he likes to roast tomatoes in a pan just so, then remove them from the heat so they don't burst in the pan. He asked if I minded adding some mushrooms to the dish - I didn't - and he had those diced and into the pan before I could get two drinks for us out of the refrigerator. Within minutes he was plating the dish and carrying out two plates to the patio, me opening the door for him with two cans of soda in my hand.

The patio was very spacious, broken into two tiers. We stayed on the top section, under the awning of the house with a large ceiling fan providing a cooling breeze. Off to the left was the new bar area, and further to the left was the hot tub Greg mentioned earlier. I was ravenous and ate very quickly, barely stopping to chat or even take a sip from my drink. The dish was so simple, yet so delicious that I wanted to lick my plate when i was done. Greg probably had a third or more of his dish when I finished mine, and he pushed his plate over offering more. I politely rejected, just mentioning that "I must have been hungrier than I thought" which made us both laugh.

After we were done, I offered to take in our plates while Greg walked over to the bar area to fix himself 'something a little stiffer' as he put it. He had taken his shoes off but was still wearing the same button down with the rolled-up sleeves and khakis he was earlier; he looked really hot, and I understood later why George W. Bush was such a big fan of the look. I got back to the table first, and he joined me just a few moments later, a dark brown drink in one hand, and a clear, bubbly drink with a little lime in the other, which he offered to me. I took a sip, wishing/hoping it was vodka or something, but it was plain club soda. He returned to his chair and took a hearty drink from his, polishing off about half of it.

"You're going to need another one if you keep that up" I said, smiling and putting down my drink.

"I'm a big guy, I take big drinks" he responded in laughter.

"Yeah, what are you like 6'4" or something? And your arms are huge, is that all from playing football?"

"I'm 6'3" but thanks for the flattery. And no, I haven't stayed in shape all these years from playing football 20 years ago. I go to the gym every night on the way home from the office; I'm trying to get the partners to go in for a gym at the office, but no dice yet."

"Are you a partner?" I inquired.

"Not quite, but I'll get the offer in the next year or so. The last couple of years have been incredibly good for me and the firm. I didn't go directly to law school after college, I went out to Colorado to be a ski bum for a few years. Then I took some time off when my grandpa was sick to help out around here, so I'm a little behind where I should be, professionally."

"Well, that's alright, you seem to be doing ok for yourself" I said, pointing around to things.

"True. And I'm not married to my job like a lot of other lawyers are." Shit, he must know my dad. "I work enough to live my life; I had this case kind of fall into my lap a couple years ago that I won a huge settlement on which attracted some other plaintiffs and we put together a class action which is just about to settle. Once that hits, they'll make me partner for sure, it'll probably be the biggest settlement the firm has ever won."

"Woah, that's awesome" and it truly was, that had to be an amazing feeling for him, professionally.

"So yeah, I'll settle this case, make partner this summer, buy a house up in Michigan as a treat to myself" he trailed off, then picked up his drink and finished it in one big gulp. Without saying anything he got up and fixed himself another one, returning quickly with just the one drink this time. He gave a little raised-glass cheers and we both took a sip of our drinks.

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