Late Night Rendezvous

A month or two BC (before Covid) I started talking to a guy on Grindr. His name was Santiago; I learned that he had a young son and that he was straight but curious. He told me that he had fallen asleep on his brother's couch one day, when his brother's friend had started touching his dick. Santiago had woken up but pretended to still be asleep; surprisingly he had kind of liked it, making him curious about being with a guy.

I was still really into James at the time, but that wasn't going anywhere; Santiago was hot. I've always had a thing for Latino and Middle Eastern guys; Santiago was Latino and very attractive. His body was covered in tattoos that he'd done himself; his dick was big and juicy. I made it my mission in life to get to blow him.

One night, we were talking as I was closing at work. I had a pizza left over that was going to go in the trash, so I offered it to Santiago. He was in Midland for some reason, but he would be heading home around the time I'd be leaving and agreed to meet me somewhere in-between my house and his. It was finally going to happen.

I should have been more afraid to meet a stranger in a dark location late at night, but for some reason it worked as an aphrodisiac. When he pulled up next to me, I got into his car and set the pizza in his backseat. He made awkward small talk for a few minutes before he said that he was nervous and that I'd have to get him started. I reached down to the front of his joggers and started stroking him. Within a few seconds he was hard; a minute after that he was in my mouth. It didn't take long -- thankfully -- but it was a good experience. His cock was definitely thicker than it looked in the picture he'd sent me; if I had had to suck on it for more than a few minutes, my jaw definitely would have started to hurt. His cum had a nice taste to it, which was always a bonus for me. There wass nothing more disappointing to me than to go through all that trouble just to get a nasty load.

Over the next few years, we continued to meet up a few times a year; sometimes at his place, sometimes at my apartment. During one of our off periods, he'd started dating a girl he worked with and had gotten her pregnant. They didn't last long. As the years went by, I started getting annoyed that he would never touch me. He would come over, have me blow him -- sometimes twice -- and then he'd leave. Another part of my issue was that he would always want to do it at three or four in the morning, the time that I would normally be sleeping or settling down to try to sleep. I expressed my frustration with him, which just resulted in a fight. He said that I wasn't respecting him or his comfort level, that I knew he hadn't done anything with a guy before me. Then, we began a pattern of meeting up, hooking up, fighting, blocking each other, and then repeating.

During one our late-night rendezvous, I was giving him head, when he whispered that he kind of wanted to try sucking my dick. I was touched that he had taken what I'd said into consideration, especially since we'd been hooking up sporadically for a couple of years at that point. I had always made it well known that I enjoy giving head, but that didn't mean that I didn't ever want any reciprocation. It didn't help that Santiago was lasting longer and longer with each meeting. He also needed all of the lights to be off, which infuriated me. I'd always preferred to have some kind of lighting so that I could see what I was doing. I didn't think that he would actually go down on me, but just in case, I moved down so that legs were up by his head. He moaned in ecstasy as I worked my magic on his cock, licking and sucking. I'd never told him this, but the underside of the skin on the head of his cock wasn't smooth like every other dick I'd sucked was. He liked it when I flicked my tongue there, but I tried to avoid it because I didn't like the feeling of it. I knew it wasn't an STD or anything -- any time I'd been tested I was always negative for everything. I'd assumed it was just scar tissue from his circumcision, but by then I'd realized that he wasn't circumcised. How had I missed that? Right when his moans started to grow in intensity, he'd put me in his mouth, rendering me useless.

As I've said previously, it's hard to find someone that is good at giving head, at least for me. I usually spend the time trying to force myself to feel good so that I can blow my load and be on my way. With Santiago, though...wow! I wasn't sure what it was about his mouth, but it felt amazing. I felt like, for the first time, I was really getting to experience head.

He stopped before I could cum, but I was close enough to the finish line that a little hand work got me there. As I felt myself getting close, I'd straddled him and cum all over his chest. After he'd finished, we'd laid in my bed, cuddled up. He'd gotten more comfortable with kissing and cuddling but not touching me sexually. He asked me how his head was. I told him that it was honestly one of --if not -- the best mouths I'd had. That had made him happy, but he'd explained that the idea of me cumming in his mouth freaked him out. That disappointed me a little, but I understood. He was making an effort to be more for me, so I figured that I should return the favor.

Somewhere along the line, Santiago began to drink more often. Usually when we met up, he had had a few beers, just to loosen himself up a little, but every time we got into a fight it was because he was drunk and ignorant. He'd get mad that I wouldn't come see him, that we never talked unless I was horny. I explained to him that since I was the one doing all the work -- giving him head for almost an hour at that point -- I felt it was only fair that he came to me. I reminded him that I have driving anxiety, that as I was getting older, my agoraphobia was getting worse, but he didn't care. In the back of my mind, I wondered if he hadn't started to develop feelings in some weird way.

The next time he'd messaged me to meet up, I'd been crushing on a friend and wasn't really interested in being with anyone else. I tried to break that to him as gently as I could; by that point I'd known all too well how tempestuous he could be. He acted as I had predicted he would: he freaked out. He called me a piece of shit and said that I should feel ashamed of myself, that I'd taken advantage of a straight guy and once I'd gotten what I'd wanted, I'd lost interest. I'd tried to explain to him that just because we had a history of hooking up, that didn't mean that I was obligated to be available to him for the rest of my life. I told him that I really liked the guy and wanted to pursue a relationship. Santiago blew up, asking me why I hadn't tried with him. I pointed out that he was straight and that I knew it could never be anything more than it was: casual sex. Santiago got meaner and meaner, saying that he wanted to knock me out, which made me nervous. Thankfully, he blocked me a few messages after that. What the fuck? How had I managed to make a straight guy so obsessed with me that he became irate at the idea of me wanting to be with someone else? In my experience with straight guys, they didn't want any sort of emotional attachment. This was all lending credence to my theory that Santiago had feelings for me but didn't want to admit it or act on them. I was worried that he would actually try to hurt me, so I purchased two cans of mace just in case.

A couple of weeks later, he messaged me again. When I was cold and short toward him, he asked if I was mad at him. I told him that yes, I was angry with him, that the things he'd said were hurtful and honestly quite terrifying. He said that he'd been drunk and hadn't meant any of it, in fact, he didn't even remember any of it. He was upset because his older brother had just died. I wanted to be there for him, but not if he was going to go insane if I was dating someone or threatening me with physical violence.

We ended up meeting at my place in the witching hour. We spent a long time just lying in the dark while he talked about his brother. Somehow, Santiago had found out that his brother had been gay but hadn't said anything to him about it. His grief was making him drink more, which was why he'd been so nasty to me that night. I wasn't going to just sweep it under the rug and excuse it, but I did feel better knowing that there was a part of him that was still rational. I understood that grief can be a terrible thing and that he was trying to lean on me because I was the only person who knew about his same-sex curiousity. In an odd way, I think that being with me made him feel closer to his brother.

With no job, no car, and nowhere to live, Santiago had moved back in with his mother. I didn't judge him for that; I'd lived with my grandmother for a decade, many years after I probably should have. His mother lived in Bay City, a few blocks from my aunt Julie; I told him that I would be more comfortable coming to see him because I knew how to get there. He proposed that we watch movies together in the living room. He said that his mom only left her room to use the bathroom and that she wouldn't hear us. I wasn't entirely whelmed with the idea of hooking up with him in his mother's living room, but I figured his bedroom would be okay.

Over the next few months, I would message him when I was making my weekly trip to Bay City; sometimes I would let him know hours in advance -- if it was a more spontaneous trip -- or a day in advance if it was my usual late-night Sunday run. No matter what I did, he wasn't able to meet. Either he had his son, or he fell asleep. I didn't care all that much, after all, I had absolutely no emotional attachment to him. I was putting in the effort that he had claimed I didn't put in, so morally, I was content. Sometimes the idea of something is more fulfilling than the actual action, at least in my experience.

Just as I was getting comfortable again, Santiago got drunk and messaged me. He said the usual things: that I made no effort to see him, that I was selfish, that I used him. By that point I was fed up with his bullshit. He blocked me as I was going to block him, but I blocked him still anyway, because deep down I knew that he'd sober up, unblock me, and try to see me again. It was a vicious cycle of abuse and insanity. I wanted no part of it.

Over the course of the next few months, Santiago would make new accounts and try to message me: Facebook, Snapchat, even texting a few times. I was done. I ignored each attempt to reach out, after all, I knew how it would end. I would not be his punching bag -- literally or figuratively -- any longer. The dick was not good enough to put up with all of the drama that came with it. Yes, the cuddles were nice, and his mouth was fantastic, but I'd rather have calm and serenity in my life than the occasional good head from a drama bomb.

I was standing strong in my resolve until my crush turned me down. I shouldn't have been as distraught about it as I was, but I spend so much time controlling my emotions and acting rationally and responsibly that every so often I do have a little meltdown of my own. I don't hurt people, I don't threaten physical violence on anyone, I just give up and make bad decisions that feel good in the moment. I was in one of those states when I unblocked Santiago, just to see if he'd unblocked me. He had.

I was in bed one night, finishing a chapter in my book as my melatonin kicked in when I got a Facebook message. I figured it was my friend who sent me reels she thought I'd find funny but was surprised to see that it was Santiago.

"Hey. Are you up?" he asked. It was 2:52 AM.

"Barely," I replied, my eyelids heavy. Melatonin helps me fall asleep faster, but it does nothing to rid me of the exhaustion I feel when I wake up.

"Ohhh sorry."

"You're fine."

"I have a car now."

"That's good."

"Yeah. Sorry I bugged you."

"What'd you get? You didn't. My melatonin is kicking in though."

"Your good I'm just going to block.

Just needed someone to

I hope your doing good

Goodbye."

I could tell by his poor grammar and lack of punctuation that he was drunk. I was depressed and exhausted, so I turned the light off, rolled over and went to sleep. When I woke up the next day, I was instantly annoyed when I saw that he had kept going after I'd gone to bed.

"Cool nice talk

You made me wish I never opened up to you

Peace of shit

Thanks alit."

How was I the asshole here? I'd responded to his messages; I'd told him that I was about to pass out, yet, somehow, I was the bad guy? Wasn't he in the wrong for expecting me to exist solely for his own purposes? I decided that I really was done that time and blocked him.

Even though I was determined to not speak to Santiago again, I couldn't help but think of him from time to time. I hoped that he got the help he needed. I didn't want him to drink himself to death and break his mother's poor heart; she'd already lost one son. Every time I was in Bay City, I kept an eye out for him. I'd run into him at Meijer a few times over the years; I wasn't sure what I would say or do if it happened again. Thankfully, it didn't.

After Max and I ended things, I was feeling vulnerable. I wasn't mad at him, but I was hurt by the situation. I had done everything right, and once again, I'd gotten burned. Did it pay to be irrational and immature? It seemed to me that the worse the person, the more people liked them. After a few glasses of wine, I found myself scrolling through my Facebook message history.

I figured I'd unblock Santiago long enough to see that he still had me blocked, and then I'd re-block him and be on my way. I should have known that he wouldn't still have me blocked.

"If you promise to be a good boy, I might let you cum over tonight."

I was going for funny and flirty; he'd know exactly what I meant. This wasn't about love or feelings; it was about an orgasm. He didn't message back and Grindr was bust; I went to bed that night sad and horny.

The next day, he did message back. He said that he'd been thinking about me. Perfect. We made plans to "hang" soon.

He came over shortly after four in the morning. I was already slightly annoyed because I wanted to be watching Grey's Anatomy or sleeping, but he had said that he wanted my dick in his mouth. As much as I didn't like Santiago at times, I did like his mouth. In one of our previous conversations, he'd said that he wasn't comfortable with me cumming in his mouth yet, but that he had thought that it was really hot the time I'd straddled him and busted all over his chest. He had even suggested that I cum on his face.

As we got into bed, he started talking about how he was still reeling from his brother's death, and how he'd hooked up with a girl over the summer, but she had a boyfriend already and wasn't going to leave him to have an actual relationship with Santiago, so he'd quit talking to her. I mentioned that I'd fingered a pussy recently. He asked me if I'd liked it, if it was a step closer to me putting my penis inside one. No.

He told me that he wanted to start slowly, that his favorite porns were the ones where there was kissing and touching before anything sexual happened. I rubbed him through his shorts a little before letting him take over while I ran my fingers up and down his chest under his hoodie. His breaths started to come faster and longer. As I rubbed his nipples, I could see through the dim light that he was biting his lip. He asked me to come closer, so I started grinding my pelvis into his hip as I rubbed his chest and arms.

Before too long, the clothes came off and he asked me to suck him a little -- just to get him horny enough to take care of me. For some reason he wanted me between his legs instead of leaning down; it didn't really matter to me. As I sucked him, I ran my hands up and down his legs, realizing that he did not have a lot of body hair. His legs were smooth, like a woman's, as were his arms. He had a few tufts of hair around his nipples and navel, but aside from armpit hair, he was bald. Even his facial hair was sparse. If he hadn't had a full head of hair I'd have wondered if he was going through chemo or something.

His cock fit perfectly in my mouth, like slipping on an old, well-used glove. His sighs and moans of pleasure turned me on, making me happy inside. He had told me once before that I gave him the best head he'd ever gotten; that he'd never gotten as horny with women as he did with me. I licked and sucked teasingly, delighting as he quivered.

He whispered that wanted to 69, so I adjusted myself accordingly. At first, he wasn't touching me, but then he started to jerk me off, his moans growing stronger and more frequent. As I sucked him, I waited with anticipation for the big pay off.

When he finally slid me into his mouth it felt so good that I almost had to stop sucking him. I'm not sure if it was because he was "straight" or if he was just blessed in that department, but he was able to make me quiver in a way that few guys have been able to. As he got more into it, he pulled my body closer, his hands grabbing my ass and squeezing my cheeks. It was hot. I started to thrust my hips, matching the rhythm of his bobbing head.

Suddenly he climbed on top of me, ass in my face, and started sucking me faster. It was an awkward angle for me to suck his dick, because it was so big, but I did my best. What he was doing to me felt amazing; it took all I had in me to move on his cock at all. I'm normally quiet during sex, but as he worked on me, the pleasure grew and I felt myself getting close to orgasm. I couldn't warn him, because his cock was in my mouth, but almost as if against my will, I started moaning low in my throat. As I came, I felt all of the tension leave my body as pleasure shot through every synapse I possessed. Holy fuck! I'd needed that. It was the best orgasm I'd ever had.

After I finished, he got off of me and lay on his back. " I can't believe that I just deepthroated you."

"It was good."

"Are you close at all?" he asked, as I adjusted myself to continue working on him.

"I came already."

"You did?"

"Yeah, like a minute ago," I panted, feeling delirious.

"You came!?" he demanded, not quite sounding angry; more surprised.

"Yeah. You didn't feel it?"

"I didn't taste anything."

"The head was good," I explained, shrugging. "I thought you heard me moaning and felt me convulsing."

"I did a little, but I didn't taste anything."

"My cum is usually pretty sweet."

"I thought we'd be at it for a long time. It would've been hot to go for hours."

I wanted to tell him that he'd done such a good job that I couldn't help but cum, it was the truth. It had also been over a month since I'd gotten head or touched in any way.

I started sucking him again as he continued touching my dick. "Are you close?" I asked, hoping that we could get this over and done with so I could go to bed.

"Not really. So, that taste is my mouth is semen?"

"Yes."

"I expected it to be salty."

As I continued working on him, I grew frustrated as he started talking. "It would be really hot if you face-fucked me," he said.

"I already came," I reminded him, popping his dick out of my mouth. Thankfully he couldn't see me roll my eyes in the darkness.

"Can't you cum again?"

"Eventually, but I need a recharge period. I'm old, remember?"

"You're not old."

I put him back in my mouth, feeling overstimulated as he played with my dick for a bit before popping it back into his mouth. I wanted to scream in ecstasy: my cock was overly sensitive from just coming, but him sucking it felt so good that I had to keep myself from shaking.

After a minute or two, he stopped and said, "I was hoping you'd get hard again."

"It's overly sensitive right now," I pointed out. How was it that he knew nothing about dicks? He had one!

"Oh yeah. I probably shouldn't have done that, then."

"You're fine. It felt good, just not in a way that would make me get hard again."

"I get it. After I cum I'm usually done."

After I sucked on him for another fifteen minutes or so, he asked if I still had the videos we'd made together a few years previously. The original video had been over twenty minutes long, just me sucking his dick. I'd had to splice it into smaller videos, but I kept it so that I could send them to prospective partners. In fact, those videos are what had convinced my friend James that I was serious about sucking dick.

For awhile, I sucked him while he watched the videos. He moaned and gasped in time with himself in the recordings. I hoped that this meant that he was about to cum, but alas, I had no such luck. As six o'clock came around, I knew I wasn't getting to bed.

Eventually, he took over and started jerking himself off. "I'm really sorry that it's taking forever," he said as I moved up onto my pillow.

"It's fine. I'm just tired," I replied, my voice gravelly with exhaustion.

"I get it, I am too. I thought about you. I thought about calling the pizza place and ordering a pizza, just so you'd talk to me."

In the darkness, I rolled my eyes again. I didn't understand why he was trying to make conversation at a time like that. Talking was not going to make him cum any faster.

As he jerked his cock, I sat up and pulled on my sweatsuit. It was cold in my apartment despite his body heat. I'd never been able to sleep naked except in the summertime when my room is always unbearably hot.

"You're getting dressed already?" he asked, sounding disappointed.

"I'm cold," I told him, not even trying to hide the irritation I was feeling. "And I don't really like being naked." Seeing as Santiago wanted all of the lights off because he wasn't pleased with his body, I figured he of all people would understand that I had the same issue. Ironically, up until the age of twelve or thirteen, I'd always been naked. My entire family had seen my naked prepubescent body far too many times. When I started going through puberty at the tail end of eighth grade -- when I was turning fourteen -- I'd suddenly developed a total aversion to be naked. Ever.

I was so comfortable, that I shifted onto my side, my back to him. The rocking motion beside me was soothing; if he didn't hurry up, I'd fall asleep. Romana, my favorite of all my cats, jumped up and settled into the crook of my arm like she does every night at bedtime. I wish, baby, I said silently.

"Pull your ass out," Santiago said, panting. "I want to rub my dick on it."

At that point, I was so desperate for him to cum so that I could sleep that I would have done just about anything. I pulled my sweats down for him. First, he rubbed my cheeks with his hand, but then he started to rub his dick along the crack, smacking it on the cheeks. "You still haven't taken a dick?" he asked.

"No," I replied, hoping that he wasn't going to try to change that. We'd already tried once and he hadn't been able to get it in. I didn't mind, his thick cock was not a good starter cock, and if I was going to let someone inside of me, I wanted it to be meaningful, with someone I loved. Or at least was dating.

"I wish I could just stick in in you, have my way with you, bust a fat fucking nut in you."

"It wouldn't fit," I mumbled, wishing I had not allowed him to come over.

"Why not?"

"Your dick is very thick. I'm virgin tight. It would take a lot of lube and a lot of prep to even make it possible."

"Maybe we could get you some toys to practice with." A second later, he got on top of me and started dry humping me. "Fuck! I want to know what it feels like."

He moved back down and resumed jerking himself off. I casually checked my phone and snarled when I saw that it was now closer to seven than six.

Finally, Santiago came. It was so explosive that I felt it hit my legs, the same strength of impact as a paint gun. Wow, he really had been turned on.

I gave him a towel to clean off with and then stripped out of my sweat suit and into a robe as he pulled his clothes back on. I didn't want any more chit chat; I wanted him to go so I could sleep. "My son and I came through here not too long ago. I thought about stopping into the pizza place."

"I might not have been there," I pointed out, swallowing my irritation. "And if I had been there, it probably would have been a long wait. We've been busy lately."

"It was a month or so ago."

"Yeah, we were really busy up until the last few weeks. It could've been up to an hour wait."

"I really liked having your wiener in my mouth."

Despite my exhaustion, I laughed. "Yeah?"

"Yeah. What? Why are you laughing?"

"You called it a wiener."

I felt a pang in my chest as I remembered Max. We had often joked about how he had grown accustomed to watching his mouth around the boys; I'd teased him and told him that I'd wanted to suck his wiener while he licked my butthole.

"What would you call it?"

"Dick. Cock."

As I slid into my shoes to walk him out, he said, "You have Hey Dudes? I have Work Dudes."

"Work Dudes? I didn't know that was a thing."

"Yeah, they're non-slip."

Thankfully as soon as I opened the door, he was out and gone with a quick, "have a good night."

I climbed back into bed, pulling the blanket up to my chin. My eyes shot open when I felt a wet, stick substance. Come the fuck on! He got cum on my only clean blanket, too! Now I had no clean pajamas and no clean blankets, great.

Despite my lack of sleep, I felt great when I woke up; that orgasm had done wonders for my mental health. I couldn't but wonder if the reason that I was so crabby all the time was because my sex life was basically nonexistent. I'm good at taking care of myself, but it's not the same, and when I did hookup, it was usually awkward and disappointing. Maybe Santiago and I could find a way to get along better; I would not be mad if he wanted to come over -- at a more appropriate time -- and make me cum that hard again. If I was having orgasms of that magnitude regularly, I could be a completely different person, more relaxed.

It will take me awhile to get over the disappointment of losing Max, but I know that it will subside. Plenty of my connections have gone poorly, and although it feels in the moment like things will never get better, they eventually do. I had really liked Max, but I wasn't going to wait for him to decide that he's ready for more than friendship. I deserve better than to wait for someone else. I could never date Santiago, but maybe a friends with benefits type of relationship could give us both what we need, at least until he started acting crazy again.

I'm still looking for that special guy who will enhance my life. Maybe I've already met him, maybe he's just around the corner. All I know is that I deserve the same happiness that everyone else does, and that with patience and hard work, I would get it.