Same Mistakes, Part Deux

The truth was, talking about Santiago's ex - Sabrina - had killed the mood. I wasn't mad; I figured he needed to talk about it and maybe didn't have anyone else he could talk to. Even though we'd been hooking up a few times a year since 2020, we'd never delved too deeply into our personal lives. Santiago never mentioned friends, just his exes, his mother, his kids, and his deceased brother. I got the impression that he didn't have very many people in his life, though I didn't struggle to see why, considering how acerbic he got when he was drunk.

He was lying beside me on the bed, practically trembling. I knew that he was nervous, afraid that I would tell Sabrina about our hookups, but I would never do that - not because I felt a responsibility to Santiago - but because outing someone - maliciously - was not something that good people did. I could tell that he still wanted me, but that he was going to need some help to get back to where we had been before I'd mentioned his ex by name.

Without a word, I shifted so that I was down by his legs and took his flaccid penis in my mouth again. It didn't take long before the tension left his body and I felt him swell in my mouth. The little gasps and whispers of pleasure spurred me on, making me suck harder, deeper - anything to get him where he needed to be. As much as I enjoyed giving him head, I was really in it for the head that he would give me. I couldn't explain why, but of all the DL straight/bi guys I'd hooked up with, Santiago gave the best head - and so effortlessly. Even when we weren't speaking, I still thought back on what his mouth could do to me.

I knew that my mouth was doing the trick when he whispered, "move closer to me."

I did as I was told and was overcome with pleasure when he took my semi-erect penis into his mouth. Ecstasy burned through my veins with each movement of his mouth. I had never particularly enjoyed 69ing with anyone - except for Santiago; it didn't ever feel as good for me as I wanted it to, probably because the other guy was too lost in his own pleasure to fully perform to ensure mine - no hard feelings. But with Santiago...

I tried to lock in for a minute or two, matching my rhythm with his, but his mouth was making me feel so good that I couldn't focus on attending to his cock, not properly. I didn't want to be sucking him then, I just wanted to lay there and let him ease away all my stress and tension, to enjoy every moment until I reached my climax.

As amazing as his mouth felt, I forced myself to pull away from him. "What are you doing?" he asked as I came to lay beside him again, head-to-head.

"I couldn't focus," I admitted, sighing. "It's time for me to just lay back and get taken care of."

"It's hotter when we're sucking each other at the same time," he contradicted, not quite hiding the disappointment in his voice.

One the main issues I had with my affair with Santiago was that everything was to his liking. I couldn't have lights on because he didn't like it. I had to suck his dick to get him horny enough to even touch me. We never met at a reasonable time; it was always at the witching hour when he'd have enough to drink to allow himself to give in to his homosexual urges. The only thing that went my way was that we did it at my place, where I was comfortable - and even that was a point of contention between us, because he liked to vilify me for never wanting to come to his place.

Rolling my eyes, I straddled him, staring down at the tattoos on his chest in the scant light. I wasn't sure why, but in the last couple of years, I'd started to be attracted to tattoos - especially sleeves. Santiago had told me once that most - if not all - of his tattoos had been done by himself, which both fascinated and unnerved me; I had never the dexterity nor the constitution to give myself tattoos - and from what little I had seen of them in light, they looked good.

I started grinding my hips, hearing him sigh with pleasure. My cock was underneath me, but with each thrust of my hips, it was stimulated as it rubbed against his belly. His cock was being stimulated by my ass with each flex of my hips.

As it began to feel great for me, I started to move faster, getting into it more. "Oh, fuck, papi!" I moaned, my hands going to the headboard to steady myself.

"Put my cock up against your hole," Santiago groaned, the deepness of his voice somehow turning me on even more. As I did it, he moaned, clearly very turned on. I wouldn't let him penetrate me, but I was okay with simulating it.

I quickened my pace again, mindful of the sounds of my bedframe squeaking as I 'rode' him. I lost myself in the pleasure, moaning, the heat from his body fueling my desire even more.

"Fuck, papi!" I gasped, as my rapture grew exponentially.

If Santiago wasn't so deeply in the closet that all he could offer me was late-night trysts that I couldn't talk about, I could see myself letting him fuck me. In the moment, I imagined how hot it would be if I actually was riding him then; how amazing it would feel to have him inside of me, stretching me and hitting my prostate with each thrust.

"Oh, fuck, don't stop!" he cried, which spurred me to pick up the pace even more. I wanted us both to cum like that, from me 'riding' him; the closest either of us could get to the real thing. "Give papi that load."

"Fuck!"

I nearly cried out in exaltation - and surprise - when he reached up and started kneading my chest like they were a woman's breasts. With each squeeze, my chest hair was pulled - which hurt - but it also felt good, adding to the heady mix of sensations that were encircling me. Right when it was about to be too much, he sat up and started sucking first on my left nipple and then right.

I threw my head back as I felt my climax quickly approaching. "I'm gonna cum!" I gasped right before my I shot my load all over his stomach, my thrusts smearing it in the hair on my legs and ass. I quivered as I continued to buck, each movement of my hips overstimulating me - in a good way.

I waited until the feelings subsided - and the world stopped spinning - before I hopped off of him, my hips already starting to ache. If I'd known what the night had in store for me, I'd have stretched and done some warmups, but like everything with Santiago, it was spontaneous, spur of the moment.

"I was so close at one point," Santiago said, voice tinged with disappointment, "I really wanted us to cum together."

Even though my body was practically useless - drained of everything - I moved down to suck him off again; I just hoped that he'd been close enough that I wouldn't have to spend ten or fifteen minutes sucking him until he came and hit the road; I wanted to get some sleep.

There was a split second of hesitation as I grabbed his cock and prepared to latch onto it - his dick has been against my hole for a few minutes. Did I really want to put it in my mouth after that? I knew my hole was clean - I'd taken a shower a few hours previously - but a part of me couldn't help but fear that somehow, it would all end with me sick to my stomach and praying for death - the routine occurrence every time I had one of my bad stomach attacks.

I quietened my fears and anxieties and slipped him into my mouth. I was grateful when the only taste that filled my mouth was the taste of him flesh - the exact same taste that had been there before I'd tried to ride him like Seabiscuit.

I knew that there was only a short window before I'd be useless. On top of already being exhausted, the orgasm had completely sent my body into relaxation mode. I tried sucking him at a faster pace, hoping it would get him to finish sooner, but he winced and whispered, "Go slow. Slow."

I wasn't uncircumcised, but I knew that - for me - slow was not going to get the race to finish line to come any faster. Did he get overstimulated when I went too fast? Or was it just another or his controlling tendencies rearing its ugly head?

I slowed down, hoping I could hold out. It had to be past four in the morning by that point; I needed to head to bed so I wouldn't be a complete zombie when I got up for work in ten hours. I made up my mind that when he did cum, I wouldn't be able to swallow - a shame - because I was in the fasting portion of my intermittent fasting schedule; I wasn't sure how many calories were in cum, especially Santiago's huge loads, but I knew that even one calorie was too many.

"I'm getting close," Santiago whispered, granting me a fresh rush of energy. All I had to do was get him off and then I could take a quick shower, brush my teeth again, and go to sleep. I started sucking harder and faster, giving him everything I had. "Oh fuck, I'm gonna cum!"

I felt - more than tasted - his thick load shoot into my mouth. I wondered why his loads were always so big - was it because he was so turned on? - as I sat up and - regretfully - spit his load into my bedroom trash. "Sorry if it was a lot," he said, a cute shyness in his voice.

"It's fine, I just can't have any calories after midnight; I'm doing a fasting thing, trying to lose weight," I explained as I pulled my robe back on, tying it tightly as I went to go get a towel to clean off with. I could still feel the wetness down below from where my cum had been; I wanted to jump in the shower, but knew that I couldn't until he left.

When I came back to the bedroom, Santiago was still lying there. "I need a little clean up, too," he said, laughing. I walked back to grab the towel and then handed it to him. While he cleaned himself off, I pulled my sleep pants back on and tried not to think too much about the things I'd said and done in the midst of our wild bout of passion - had I been too submissive? Too feminine?

After Santiago finished cleaning himself off, he got up and started putting his clothes back on. "Where are my shorts?" he muttered, before finding them in the tangled mess of my comforter on the floor at the foot of the bed.

Post orgasm, we usually didn't talk much. Sometimes he'd try to make awkward conversation - presumably to assuage his discomfort - but I never really wanted to talk. As hot and intense as things got in the moment between us, post-orgasm, I did not want anything to do with Santiago; he wasn't the kind of guy to kiss and then cuddle with. Maybe I was protecting my heart - or maybe I was more of a guy than I - or others - gave myself credit for. All I wanted was for him to leave so that I could clean up and get to bed.

I was over the moon when - once he was dressed - he slid his shoes back on. "Can I use your bathroom real quick before I head out?" he asked, "I have to piss." In all the years we'd been hooking up, he'd never used the bathroom.

"Uh, sure," I said, pointing abstractly toward the bathroom - as if he didn't know where it was.

I wished he'd come earlier in the week - I cleaned my bathroom on Tuesdays after work - by Saturday, the cats had tracked litter all over the floor - no matter how often I swept - and I had shed enough body hair to be plainly visible. He had never judged me - that I knew of - for the chaotic disorganization that often ruled my apartment; I figured he wouldn't be too worried about some cat litter and pubic hair.

We were silent as I walked him to the door. As he stepped out into the cold, early-autumn night air, he said, "see ya," disappearing around the corner to his car.

"See ya," I replied, quickly pulling the door closed behind him.

What the hell was I thinking letting Santiago back into my life? I knew that it always ended badly; I had enough stress and drama in my life without adding his mentally unstable bullshit to my roster and yet...the orgasms he gave me were the best of my life. Was I addicted to the drama? Was the imminent threat of danger the catalyst that made my encounters with Santiago so much more satisfying than those I had with regular guys? At almost thirty-six, was it logical - and acceptable - for me to keep playing with fire for the sake of a great orgasm when I could simply work harder on finding a more appropriate - and not DL - guy that I could grow to have great chemistry - and eventually orgasms - with?

I got washed up again and crawled into bed, wishing - not for the first time - that my love - and sex - life could at least be simple and fulfilling.