First Time With A DILF

Eric slicked up his cock with a liberal amount of lube before pressing one finger, then two, into me. I thought he was being a little hasty, adding two fingers so quickly, but he took his time to let me get used to it.


I never actually really liked beaches. Sand would find its way into places on my body that I didn’t know was possible to even get sand in, and it wasn’t like I rolled around on the beach or volunteered to have my cousins bury me in the ground and build a curvaceous bikini-worthy model on top, like those cheesy photos where the idiots are grinning just above obscenely large sand boobs. No, just thinking about doing that made me want to run and hide in the hotel room.

I know the first thing people tend to think of when they think “Latino” and “beach” are those genetic lottery winners that strut around Rio de Janeiro wearing the absolute least amount of coverage possible, but safe to say I had none of those genes switched on in my DNA. If there was any sort of genetic prize I won, it was my fast metabolism; I could eat, and eat, and eat, and not gain a pound. It didn’t mean I wanted to prance about and show off my body. I felt painfully awkward wearing my board shorts and T-shirt while watching frat bros with ballcaps turned backwards toss a frisbee and rough house with each other.

Okay, I enjoyed seeing all that hot, sweaty man-flesh collide and would absolutely fantasize that I could be in the middle of that frat sandwich. But it wasn’t enough to make me wish I could be just a little more covered, or that there should be less people around. I hated feeling like strangers were sizing me up, trying to figure out why the gawky Mexican was on a beach. Or worse: if they wondered if I was illegal. Which wasn’t the case. I always look out for that hesitation in people’s eyes before they open their mouths, making the split-second decision to speak normally or if they should e-nun-ci-ate in case I didn’t speak English.

My cousin Lucy smacked me on the knee with her paperback, drawing me out of my confused daze of simmering lust-demon and quiet wallflower. “Gabrielito, you need a drink or something because you need to chill the F out.”

“I’m fine,” I replied, tearing my eyes away from the frat boys and scanning the horizon for ships to avoid Lucy questioning me about where exactly my eyes were focused before she interrupted.

“This is your last summer before your senior year! How are you not living it up? Get on that app thing you use and find yourself some action!” She shimmied her ample chest, no doubt catching the attention of the aforementioned frat bros. It was easy for Lucy to say: she had guys throwing themselves at her left and right, and she was discerning enough to choose her company wisely. And those that made it past the first round could either handle her vivacity or they were quickly left behind. I envied her luck; that hadn’t been my experience so far through college, and even with the final two semesters ahead of me, it didn’t seem like my fortune was going to turn around anytime soon.

She noticed my eyes flitting towards the bros before they went back to the horizon, and she grinned. “Oh, is that it? Should I reel you in some grade-A college boy?” I saw her eye them one by one, making mental notes to herself, and I tried not to laugh when they obviously began putting on a show for her: flexing but not flexing, attempting to get what abs they had (some clearly spent more time in the gym than others) to pop, coming out on top of some playful scuffle over the frisbee.

“Lucy,” I began, grinning, “you don’t even know which of those boys isn’t straight.”

“Isn’t it a 10% chance one of them is gay? I guess if you add in the bi boys, that increases the odds. At least one of them has to be bi!” She looked proud at rationalizing the odds, though I didn’t actually know if her stats were even in the ballpark. It wasn’t like every gay guy scanned a group of men and did some quick statistical calculations to figure out which of them he could hook up with. Well, maybe some did, but that wasn’t me. I kept my head down and focused on making it through school unscathed. Sure, there were a few hookups, but they were infrequent—one or two a year at best. Somewhere, some poor gay angel wasn’t getting its wings because I wasn’t spraying my spunk underneath every college stud I came across.

“Lucy, I appreciate the support, but I think your energy is better spent back on that book.”

“Oh, I don’t know,” she replied. “There are a couple of guys over there I wouldn’t mind getting to know a little better.” Then she grinned wickedly. “Maybe at the same time.”

“Don’t let me stop you.”

“Didn’t plan on it.” Lucy put her sunglasses on and stepped from underneath our beach unbrella, tying her sarong around her waist and fluffing out her voluminous hair for maximum bounce before sauntering over to the frat bros. I watched as she made a big fuss about how good they all were at frisbee and felt the arms of the guys she planned to snare. Flirting came so easy for her; I was lucky if I ever managed to ask for a guy’s name.

I turned my gaze back to the horizon, watching the waves rush in then recede, the kids splashing around in the ocean under the hawklike eyes of their mothers. The water did look inviting, especially with the heat rising off the sand in a shimmery haze. With my luck, I would be carried away by a riptide and drowned while my cousin was busy getting spit-roasted, and I wouldn’t be missed until she got back to the beach and our umbrella and towels would still be on the ground. At least then I wouldn’t have to worry about my GPA.

I saw a head pop up out of the ocean, a man; a woman surfaced next to him. They were laughing, probably having a good time doing whatever they had just been doing underwater. Getting handsy, maybe? I crinkled my nose, imagining how brackish it would be to give head in the ocean. True, some cum could be salty—there had been one hookup that nearly made me gag after he came on my tongue—but that didn’t mean that salt water and cum were the same.

The woman emerged and I had to admit she was nice to look at. She could give Lucy a run for her money, and I glanced over to watch her frustration as her current targets’ attention briefly drifted to the fit woman walking out of the water like she was some Atlantean mermaid queen, if that were even possible. She stretched her arms out wide as she looked upwards, giving the entire beach an unobstructed view of her breasts barely covered by her bikini top.

My eyes darted to the man coming up alongside her. If the woman was the physical embodiment of a siren’s song, then the man was her male equivalent. Water dripped off his close-cropped dark hair over his bearded face, and I held my breath as each inch of skin rose above the water. A broad, tanned, muscular chest lightly dusted by hair gave way to a sculpted stomach, and—oh fuck—a pair of black swim briefs that looked like they were straining to contain him. He stepped from the ocean on powerful legs, and wrapped his large arms from behind the woman, nuzzling her neck as they shared a private joke and laughed. I felt a stirring between my legs as I imagined myself in the woman’s place, those strong arms around my chest instead of hers, his deep voice rumbling in my ear.

The woman gave the man a quick peck on the cheek and sauntered off towards the resort behind us. The man, left alone, seemed unsure what to do next until our eyes locked. I felt my stomach drop at being discovered and quickly grabbed Lucy’s discarded paperback, flipping the book open and pretending to be far more interested in Augustus laying bare Miranda’s supple milk-white skin before inserting his rigid member between her inviting womanly folds than I really was. I frowned. Was that really what Lucy was reading? I took a look at the cover; it proudly proclaimed the title was “Lady in Waiting,” by Claire du Champs, superimposed over a photograph of a shirtless Scotsman boldly embracing a woman in ecstasy wearing too little clothing for a wintry Scottish highland setting.

“Is that any good?” a voice asked above me. I looked up, past a prominent black bulge, past a broad chest, to see a sinfully playful grin on a handsome face that had no business being anywhere near me. I saw now that there were touches of gray at his temples and in his beard.

“I, uh, don’t know,” I stammered, dropping the book to the side. “It’s my cousin’s.”

He squatted to retrieve the paperback; a ring on his finger glinted in the sun. “‘Lady in Waiting.’ It doesn’t make any bones about what’s inside, does it?” he asked as he turned the book towards me to show me the cover.

“I guess not.”

He sat down on Lucy’s towel and I suddenly felt the heat coming off his body, and how little space there was between us. “You’d think that this lady in waiting would be wearing more layers for a Scottish winter.”

I shrugged, my mind racing to come up with something, anything, to say. I couldn’t understand why he was talking to me. Was it because I was staring at him? Was he going to gay-bash me? I didn’t think Lucy had brought her pepper spray to the beach with her, or maybe she did. It could’ve been in her bag, but it was behind the man.

“I’m Eric,” he introduced himself, holding out a hand.

“Gabe?” I replied, the uncertainty creeping into my voice. His hand, still slightly wet, felt warm, too warm, dangerously warm. Like a cold winter morning where the bed implored you to stay in all morning because the icy chill would hit you the moment you crawled out from underneath the covers. I shivered slightly, fighting to control the primal urge within me to crawl all over him.

“Not sure of your name?” He grinned, but I didn’t feel like it came from a place where he was mocking me. He seemed genuinely entertained by my reaction to him.

I shook my head. “No, it’s not that, it’s definitely Gabe.”

“What brings you here, Gabe?”

I studiously avoided looking at him, feeling his eyes on me as I stared towards the middle distance again. “I’m just on vacation. My cousins wanted to take me out to celebrate making it to senior year.”

“Oh? Congratulations!” I felt a burst of joy from his adulation despite him being a complete stranger. “Where do you go?”

“Central State.”

Eric let out a brief gasp. “Hey, I graduated from there! I mean, it was about 20-someodd years ago. Cool, man, to meet a fellow Eagle.” I turned to see him make the claw-like gesture that we were encouraged to hold up in the air during football games. He was the only person in the world capable of making it look suave instead of kitschy. I didn’t think he was putting on an act; he was genuinely excited to know that we went to the same college.

I allowed myself a small grin. “Small world.”

“Hey, let me buy you a drink.” Eric gestured towards the resort. “The poolside bar back there is pretty good.”

I froze. “I don’t know. My cousin is over there.” I nodded my head towards Lucy and the frat bros. She still had them wrapped around her finger, all except one, a bro whose dirty blond hair peeked out from underneath his backwards cap. He seemed more frustrated at the lack of frisbee than interested in getting between Lucy’s womanly folds.

Eric quirked an eyebrow. “She looks busy, if you ask me. I don’t think she’ll miss you.”

“I don’t know…”

He nudged me, the heat from the brief contact spreading over my skin. “What else are you going to do, read about Scotsmen ravaging Scotswomen?”

I blushed. It was clear from his wedding band and the woman—his wife, clearly—that he was married, and there was no way he was flirting with me. It had to be all in my head. Eric was just being friendly, offering to buy a drink for a student from the college he used to go to. And true: I didn’t really have anything to do at the beach while Lucy was working on turning her threesome into a veritable orgy.

I thought back to how the counselors advised us to network and build those bridges with alumni to leverage a good post-undergrad job. Not that talking to Eric was a guarantee of a job, but maybe it would be helpful to work on my networking skills, which were sorely lacking; being quiet and reserved weren’t conducive to the socialization that networking demanded.

And hey: a free drink was a free drink.

“Well, okay. I guess.”

“That’s the spirit!” he grinned broadly. “C’mon.” Eric pulled me to my feet and led the way towards the resort. I could feel eyes on us as we walked by, and the contrast between us—me, a scrawny-looking Latino wearing board shorts that were maybe a little too long, and him, a buff older white guy striding confidently in what amounted to black underwear—couldn’t be more apparent. All eyes had to be on him, and surely they wondered why some kid was following him. That, or they were hoping he would divest himself of the only article of clothing he seemed to be interested in wearing.

As we approached one of the poolside gates, it opened, and out strode a 20-something guy wearing gym shorts and a tank top. He held the door open and said a friendly hello to Eric while giving him a hungry once-over that was far too obvious. I might as well not have even existed; I expected him to let the gate swing shut before I could get in. Eric, though, turned to me and pointed out the poolside bar, which sat beneath a palapa and had a few standing tiki tables that were getting some use from the myriad of people looking to beat the heat by way of an alcoholic beverage or two.

“Eric!” the bartender exclaimed as we approached the bar. “Monica was just here. You guys have a good swim?”

“Hey, Michael. The water felt great! Is our tab still open?”

The bartender, whose name appeared to be Michael, nodded. “Monica actually just ordered a couple of drinks. What’ll it be for you and…” He glanced at me, attempting to place a name with my face.

“This is Gabe.” Eric clapped a hand on my shoulder. “I think we’ll have a couple of frozen margaritas. That sound good, Gabe?”

“Yeah.” The flurry of activity around and Eric’s instant familiarity towards me felt like too much. I was going with the flow, but there was no way my head was above the water.

“Can I see your ID, Gabe?” Michael asked. “I’m pretty sure Eric wouldn’t try to serve alcohol to a minor, but you just look awfully young.”

I dug around in my pocket for my wallet and pulled out my driver’s license, offering it to Michael. He peered at it for a split second and handed it back. “Barely 21! Oh, to be young again. I’ll get those drinks for you two.”

Eric leaned against the bar and noticed my discomfort. He furrowed his brow in concern. “You doing okay?”

I nodded. “Yeah, it’s just a lot of people around is all.” And how much of an effect he was having on me, but I definitely didn’t want to tell him that.

“We can head somewhere quieter if you want.” Eric surveyed the lounges around the pool and motioned towards a couple of chairs towards the corner. “Not many people over there.”

“That’s fine.” As soon as Michael placed our cups on the bar, I mumbled a thanks and made a beeline towards the unoccupied chairs, leaving Eric behind me. About half my drink was gone—mostly out of sheer nervousness—by the time Eric managed to catch up with me.

“Hey, man,” he said as he sat on the lounge chair next to mine. “Really, are you okay?”

“I’m just not great around crowds.”

“Wanna know a secret? I don’t like ’em either. I like being one-on-one with someone instead of dealing with a group of people.” Eric moved to sit next to me and nudged my shoulder. “Just focus on me, okay?”

I looked up and he offered a friendly smile as he sipped from his straw. If only it were so easy; I could get the focusing-on-him part down pat—not hard when he looked like the definition of DILF—but it was the way my body reacted to him that I wanted to make sure wasn’t obvious. As far as he knew, I was just some nervous straight college guy who was painfully shy. I didn’t really think he would be grossed out if he saw my rising boner if his intent was just to be friendly and chill out while his wife was doing who-knows-what. Maybe he would even take it as a compliment. Gay guys had to hit on him all the time, especially the ones who had daddy issues. Not that there was anything wrong with that. Some guys maybe just needed that strong, guiding hand… as they were on all fours, a gentle probing from behind—

I shook my head and refocused on Eric’s beard, looking anywhere but his eyes. “I’m sorry.”

“What do you have to be sorry for?”

“I’m not really good company.”

Eric shrugged. “There’s few people in the world that are truly terrible company. You’re just hard on yourself. So you get nervous around crowds and you wanted to get away from them.”

I sipped my margarita slowly, feeling slightly light-headed, though if it was from the adrenaline or the alcohol, I wasn’t sure yet. “You didn’t come here to babysit me.”

“Nah, I’m not babysitting you.” He nudged me playfully. “I’m just getting to know you. And right now, I know that you don’t like crowds.”

I wanted to scoot away from him so he would stop being so familiar, not because I didn’t like it, but because I liked it dangerously too much. I wanted to lean into him, rest my head against his chest, and feel the brush of hair against my cheek. He would be comforting, like a big teddy bear I could wrap my arms around.

Except teddy bears weren’t supposed to give me a raging erection.

“So, Gabe,” Eric began, “what’s Central State like now? Sorority chicks still hot?” He chuckled, not lasciviously, but almost nostalgically. I didn’t feel like being reminded that he was straight.

“I don’t really know. I guess?” I gulped down the rest of my drink; it was better to get it out of the way, like ripping off a bandage. “I’m gay, so I guess I’d be paying attention to the frat guys instead.”

“Oh, those bros were pretty hot back in the day, too.” He cupped his chin in thought. “They usually didn’t mind who was between their knees as long as it was good head.”

I stared at Eric. “Come again?”

“What, you think I’m straight?”

I pointed at his hand. “Monica’s your wife, right?”

“My wife and I are both very happy, and very bi.”

“Oh.” I turned this new information over in my head. I hadn’t actually considered the possibility that Eric might be bi. Perhaps Lucy had been on to something when she tried to add bi guys into the mix as she studied that group of frat bros on the beach. Truth be told, I had never really thought about if a guy who caught my eye was anything but gay or straight. It seemed easier to consider him either/or instead of somewhere in the middle.

Eric shrugged as if his bisexuality was as apparent as the color of the sky. “We all like what we like. Some like only dick, or only pussy, and I happen to like both. No reason to tie myself down when there’s a whole world out there, right?”

“I guess if that’s how you see the world. I can’t really picture myself with a girl,” I said as I scrunched my face, imagining being in bed with a girl. It felt weird.

“And that’s fine. Like I said: you like what you like.”

“So,” I began, “you’ve had relationships with both guys and girls?”

Eric sensed that the frank and honest discussion about sexuality relaxed me—which it did because I no longer had to worry about him being straight and looking at me funny for staring at him—and he laughed. “Of course. Before I married my wife, I was in a years-long relationship with a man. I could’ve married him.” His face softened slightly. “We didn’t work out. But being with him helped me figure out what I needed in a partner, and then Monica came along.”

“What happened?” I wasn’t normally so inquisitive, so it was clear that the tequila in the margarita was getting to me.

Eric looked away from me. “I wanted to open up our relationship, and he didn’t. He wasn’t comfortable with the idea, and after we called it quits, I really tried to figure myself out. Was I in the wrong? Wasn’t it possible to be with someone and still have that trust to let them find what I couldn’t give them? Then I met Monica, and she was exactly on the same page. So here we are.”

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