Mom's Ex-Boyfriend Vs. Virginity

While most of this story features man on man action, it does allude to the concept of bisexuality. If that's a problem, get over it!

If you want to read more about Jay and his sexual antics, you can check out "Pounding Patty's Cakes." If you want to read more about Austin, he's mentioned briefly in "Forgiving Mom." Go ahead and give me a follow, because this isn't the last you'll see of any of these characters--especially not if people like it!

Also, it should go without saying, but everyone involved is 18 years or over and there is no involvement of minors sexually in any way, shape, or form.

* * *

The last time I fucked a teenager, I was one. Not that it ever held much interest for me either then or now. I had other things to do then and I'd done my best not to be a creep now. But here I was, an eighteen-year old, freshly graduated from high school with his hairless asshole wrapped around my cock. I hadn't planned on this and I hadn't asked for it. Now that I was doing it, it seemed like the most natural thing in the world. From the way he was moaning, I think he would have agreed.

I'd fucked plenty of men before, but my ex-girlfriend's eighteen-year-old son was a new one.

But, I'm getting ahead of myself. I should start from the beginning.

* * *

My day to day life is pretty boring. The most exciting thing that usually happens in a given day is if Barbara from downstairs sends out a cat meme. Having a future sexual conquest call me up in the middle of the day is not usually in the cards. I have a pretty exciting life otherwise, but I make a point of keeping that sort of thing separate. HR typically frowns on that sort of thing. I don't blame them. That's probably why when I saw the unknown number on my phone, I picked it up. Sex was the furthest thing from my mind. When I figured out who was on the other end of the line, it moved even further way.

"Hello?" I asked.

"Hey. Jay? It's Austin," the voice said. I thought Who? Then, as if he could hear my thoughts, he repeated his name

Oh. That Austin. The son of one of my old girlfriends, Dena. But that was years ago. Why was he calling me?

"Hey, sorry, to call you out of the blue, but my mom gave me your number," he said.

"Oh, hey!" I said. I was still a little confused. "Long time, no chat."

"It is!" he replied.

Doing my math, Austin must have been nineteen by now? I hadn't spoken to him for five or six years. At least. I still talked to his mom every now and again, but beyond the usual "How's Austin doing?" I didn't know much about him. He wasn't my kid and unless she wanted to really talk about him, I didn't press. And it's not like I would have been much help anyways. I didn't have kids myself and, in my mind, whether it was true or not, I was still telling myself I was barely older than a teenager myself (not true and I had the knees to show for it).

I was a little confused, so I decided to press him on the only subject I knew we shared.

"How's your mom doing?" I asked.

"She's doing well!" he said.

He told me she was kind of excited to have the house back, which he didn't mind, as he was kind of happy to be out of there. I laughed and told him, yeah, I remember going to college.

"That's actually kind of what I wanted to talk to you about," he said. "I'm going away in August and my mom said you might be able to give me some pointers."

"Your mom said that?" I asked, incredulous.

"Yeah. I know you're younger than she is and she said so much has changed since back in her day and that you might know better about that sort of thing than me. Especially since I'm getting into the same program as you, or at least I'm thinking about it, so you could give me some pointers on that, too."

"You don't have an uncle or anything you can ask?"

"You're the closest thing I have to an uncle."

I thought about how much I liked to drink and how loud I got at family BBQs and that made a certain amount of sense. "I'll take that as a compliment."

I'd been called "daddy" before, but uncle? That was a new one. I don't even think my sister's actual kids called me that.

"Sure. I'd love to chat about it, on the phone or--"

"In person. If that's okay."

"Yeah. That's not problem at all," I said. "Yeah, sure. Are you free for the summer?"

"All summer. I'm actually free this week. What day works?"

I chuckled. I remember not having a job and just thinking everyone else had free days, too. "How about Saturday? You still living out of the east side?"

"I am."

"Great. I know a place over there."

"Cool. I'm looking forward to it."

"Alright. Say hi to your mom."

"I will."

We hung up.

What was odd about the conversation didn't strike me until much later. At the time I was thinking about how nice it was to have a normal conversation with somebody.

I thought about the break up with his mom, Dena. She was bubbly and blonde and nearly fifteen years older than me (give or take) and we hit it off as soon as we met. I was in my mid-twenties at the time and we both got together because it was harmless fun--and because it was a bit novel. As an older woman, she'd never been with a younger man and, while I'd been with older women before, I'd developed a taste for it. We got along well, though. So well, we went from friends-with-benefits to an actual boyfriend/girlfriend. And for a while, it was real good. Not being able to date around during the pandemic also helped.

We liked each other well enough that we didn't want to change each other. Hanging over all of this, though, was that we both knew it couldn't last. I was bisexual and polyamorous and she was straight and monogamous--and she had a kid. That was Austin. As rarely as I saw him or hung out with him one-on-one (I drove him to baseball practice a few times and I remember being honored that he didn't completely hate my taste in music), I liked him well enough and he was decent enough, as a teenager, to put up with the guy fresh out of college who was seeing his mom. Like I said, it was good, and it was that way until it wasn't.

Eventually it all came to a head. I knew she wanted a stable family life and I wanted to still be a slut. She didn't want to lock me down, I didn't want her to have to stop being jealous. It was what it was. We still talked and we still hooked up every now and again (getting even rarer these days). It was a solid adult relationship. The kind your parents don't tell you about that just exists. You fuck. You don't fuck. You don't hate each other. You don't ask for money. It just exists and you're glad for the company. Then things fade away. It's nobody's fault. It's just life.

I think it's important to point out that we didn't have big, dramatic break up, and I think because of that I stayed in her son's mind as one of her more decent boyfriends. I remember my own mom's taste in men and the few good ones stuck out. At least that's what he told me when we finally got coffee. By then I was so preoccupied that I didn't even notice Barbara's latest cat meme.

* * *

The summer was finally starting to warm the city up and I wore my best shorts and t-shirt (I'd have worn a button-up, but I really only did that for people I was trying to impress, you know, dates). I ordered a drink I knew would last and waited to see what on-time meant for a nineteen (eighteen?) year old meant.

He showed up five minutes after me. He had grown. Where he'd always been a gangly teen (he must have taken after his father), he'd filled out. Still young and still barely an adult, he looked good. Good enough that I could ignore he still had a little bit of ache and that he didn't know what he wanted to do with his facial hair yet (unless that was just the style now). The one thing he had from his mom was her eyes. They had always been kind eyes and I could tell just from looking at him that he had a good laugh, just like she did. He was a little shorter than me and had the same brown hair, albeit with a slightly better tan (playing baseball, as opposed to sitting in an office will do that). We could have passed for father and son--or for two brothers, as I told myself.

He spotted me right away and smiled. He made a bee-line right for me.

"Look at you," I said.

"Look at you," he said back. He had a good handshake. And then he went in for a hug. I hugged him back. He had filled out, alright. His muscles felt firm. He smelled nice. We broke away and he went to order and I watched him walk away. He was a man, alright.

When he came back, he had the gayest drink I'd ever seen. So gay I didn't even know it was on the menu. Then I realize, no, it wasn't gay, he had only stopped being a kid within the past year. He was still shedding old habits. Also, to his credit, the drink looked pretty good.

We chatted. We caught up. He played baseball and was getting a partial scholarship to play in Arizona. I told him to make sure he wore his sunscreen and told me that his mom told him the same thing. I told him she was not only right, but that she was always right. I talked him down from some of his worst worries about college--not that words could make up for being a real adult for the first time. I told him that, too. We rapped about the books he read and the books he wanted to write. I told him it was all work. He didn't believe me in the way that everyone with no real experience in life didn't believe an older person when they told them something. He'd learn, though. He seemed capable enough of it.

And then things shifted. I could tell he was nervous. I put it down to him being eighteen and me being a cooler, older brother-type (or something like it). I was lying to myself in a couple of ways.

"Hey, listen, I'll just ask, you're bi, right?"

I laughed. There it was. "Yeah. I am."

"Okay, I thought so. I mean, I knew, but I wasn't sure."

"I am. Are you?"

"Yeah. I mean, I think so."

"There's a couple of pretty good indicators on whether you are or not."

"I know, I mean, I could be pan or flexible or whatever, I'm not sure, but I'm not straight."

"You don't have to know what to call yourself, as long as you know who you are. And even then, that's something you can figure out later."

"Right. I was right to talk to you."

"I mean, this is okay, right?" I asked. "I know you're asking, but I don't want to spill all this on you."

"No, this is actually one of the reasons I wanted to talk to you. I mean, I love mom and she knows--she's totally accepting, she doesn't care--but I can't exactly ask her for advice about this sort of stuff. She's pretty straight, you know?"

"She is a pretty square woman," I conceded. "Nobody's perfect." I smiled.

He smiled back. "And, you're poly, too?"

"I'm ethically non-monogamous, but you can call me polyamorous. I mean, again, the labels don't matter as much as what you do with them. I date around. I don't say I'm poly because that just makes me think of people that go to Renn Faires. My partner, my primary partner, she says we're swingers, which I don't see myself as, but it's a funnier term, at least."

"You're a swinger?"

I squirmed a little in my chair. I'm not ashamed of who I am and I'm not afraid of being honest with people. I think what got me was that it felt disloyal in a way that I could not quite put my finger on. Then again, if his mom didn't care, why should I? She knew better than me about what was good for Austin.

"Not a swinger, but it's better than ENM, which sounds like a British music magazine."

"I know ENM."

"Then you'd know why identifying as it is kind of weird. Ethical non-monogamy sounds like a clinical course. It takes all of the life out of it. Whatever. It's the least of my problems," I shrugged. "Why? Is that of interest to you?"

"Not exactly. I'm just curious. Well, I mean, it is of interest to me."

"Right. I'm sure. You probably don't run into a lot of guys like me hanging out with your mom."

"Not exactly. And, honestly, I don't think any of them are attractive enough to get away with it."

I let that slide. "Getting away with it is definitely how I feel sometimes. Which is why I'll tell you, whatever it is you end up doing, with relationships, I mean, it's going to be work. There's no free lunches and there's not free--do you mind if I curse?"

"No. Please."

"There's no free fucks. Just keep that in mind."

"I'm glad you mentioned that, actually," he said. He looked away for a moment before steeling himself. He had the baring of somebody who just stepped onto the plate. All that nervous energy went away and I was looking at somebody different. "I want you to help me out with my first time."

"Pardon?"

"I want you to take my virginity."

I almost did a spit take. I was flabbergasted. The idea of Austin as a sexual being had never even occurred to me. Even if it was technically okay, it was the furthest thing from my mind. You didn't have those kinds of thoughts about people if you've ever driven them to baseball practice--especially not if you've dated their mom. I think Austin must have known this, because he smiled and tried to wave it off.

"I thought about it, but only you want to. I totally understand if you don't, but just hear me out."

I looked at this kid--this man. And I tried to see him as the adult that he was without all of the baggage that came with this conversation. For a moment I could see it. This tall, handsome, chiseled baseball player. Young and fit and bursting at the seams with muscles and sweat and cum. And then I saw my ex-girlfriend's son. Then I remembered I was almost thirty and this was an insane situation.

"Even if I wasn't over a decade older than you, I used to date your mom."

"That's kind of why I'm asking you."

"Because you like older guys?" I laughed. This was too absurd.

"Well, yes, but no, I mean, you're a good guy and I trust you. It's better you than some drunk idiot at a party or some pervert who wants to take advantage of me or some girl who's all nervous or something. I don't want to be drunk and have it be miserable. Safe is the wrong word, I guess, but secure, maybe? Also, yeah, it doesn't help that you're kind of hot."

I'm kind of hot? He thinks I'm hot? And why only kinda? "I'm flattered."

"You shouldn't be, I'm telling the truth."

I narrowed my eyes. Who taught an eighteen-year-old to have game like this? Fortnite?

"Before you ask, I didn't even come up with this idea until after my eighteenth birthday."

"That was how long ago?"

"Nine months. I'm old for my class."

"And you're young for a boy toy."

"I'm actually the exact right age, arguably."

"That's debatable."

"I know. But what can I say, it's been a busy nine months."

I let that slide, too. "What is it about me? Because, I'll tell you, your first time isn't as special as TV or movies make it out to be. It's just a thing that happens. You aren't better or worse for it, one way or the other. It's like saying you don't want to drive until you get a Ferrari. That's not how life works."

He seemed to consider this and then he bowled past it. I remember being fresh out of high school and being hornier than God himself, too.

"Listen, I don't want to be a virgin in college. I want to do it right and be free so I can worry about everything else. And I want it to be with somebody I trustAnd I wasn't lying to you when I said that I wanted to talk to you. My mom was right, there's things about college that I should know about that she can't teach me."

Not according to some people I know, I thought. "It's a little different than learning how to live with roommates" I said.

"It's true. But you're pretty different."

"You've been thinking about this."

"I have been and the conclusion I keep coming to is the same one. I want you to help me out."

"By taking your virginity."

"Yes. Is that a problem?"

"I think you kind of know it's a problem."

"With me?"

"With--no, with the fact that you're practically a kid."

"I'm not a kid. In fact, I'm almost nineteen. My mom was nineteen when she was with my dad."

"Not a great argument for me and you."

"Well, you're not going to get me pregnant."

"I would hope not."

"Sorry to spring this on you. You don't have to say yes. I understand. I know it's still weird. You can think about it. I think you should. I really want you too."

"That's a very mature way of thinking about these things," I said.

"Thanks. I hope you don't think I'm just saying all this because I think you want to hear it."

"No, I'm just surprised. Your mom did a hell of a job with you."

"She did, didn't she?"

"Let's move on, okay?"

He didn't mention it for the rest of the conversation. We talked about a few other things, but the conversation--the date?--ended not too long after that. Hard to go anywhere else from there. I think he knew it. We made some promises to talk more and for him to ask me some questions about college if he had any and we kind of left it at that.

Except we didn't.

"You have Snapchat?"

You're damn right I have Snapchat, you little shit. "Yeah."

"Here," he presented his code. "If you change your mind. I can take the hint."

I scanned it, telling myself it was just to get rid of him and save him the embarrassment of rejection. We hugged goodbye and he lingered a moment as we did. And I didn't fight him. It wasn't because I wanted to say no. It was because I was thinking about it. Because he made some good points. And because even if he didn't make any good points, a door had been opened in my mind.

He left. I texted Shay if she wanted me to bring home a coffee and she did, so I ordered her something to go and I thought about the conversation. I thought I did well. I felt good about it. Flattered, but more importantly, I felt like I hadn't completely fucked this kid up--this man up, I realized. And I said no. That was huge. I had resisted the urge to jump into the first hole that presented itself, which, if you knew me, you'd know that was rarely the case.

I was going to tell him no, I thought. Give him a few days and say that I thought about it and I was flattered, maybe a little curious, but no. It wasn't right. My erection said otherwise. It was hard the whole ride home with my girlfriend's coffee.

I wasn't going to fuck this eighteen-year old's ass, I told myself. No matter how much un it would be.

It wasn't the first lie I told myself and it wasn't the last one, either.

* * *

I told my primary partner, Shay, about what had happened (this was after she got her coffee). We didn't keep secrets. It was one of the key things that kept us together--and kept us spicy. She liked to hear about my adventures and I liked to hear about her adventures--even if some of the people she hung out with kind of drove me nuts (but what do you expect from bohemian-types? Consistency?). She was watching an old movie on the TV when I got out of the shower when she started to ask me what I thought about the whole situation.

"You're not interested?" she asked.

"It's not that I'm not interested, it's that it's not appropriate."

"Not appropriate? You sound like a vice principle."

"You know what I mean? The whole dynamic is messed up. I used to date his mom, and I'm, well, I'm not going to say how much older, but old enough to be his step-dad, which I might have been. There's a word for that sort of a guy and it starts with a G and I don't even want to have the appearance of being one."

"Since when do you care about what people think?"

"I'm talking about what I think. I think it's weird that my would-be ex-step son wants me to take his virginity."

"Alright," Shay said, finally pausing her movie. "If the situation was different, if you didn't know Dena and you didn't know Austin and he was just some plucky college freshman, what would you think?"

"If it was all different, it wouldn't be the situation."