The Longest Night

About a month after Max and I called it quits he visited me in a dream. We had not had any contact since that last day in the gas station, and I tried my best to focus on other things, but as more time went by, I found myself missing him. I didn't miss jumping through hoops to get a response from him, but I did miss how it felt when we cuddled, the way his face would light up when he spotted me, how he'd grin when I choked him during intimate moments. This was most likely the reason for his appearance in my dream rather than anything more cosmic or romantic, but in the dream he came into my work and surprised me with lunch. He told me he really wanted to see me when I got out; intuitively I knew that he wanted to win me back. When I awoke to reality, I was disappointed that it had just been a dream.

That day at work, I couldn't help but feel the loneliness of my position. I believed that the main reason that Max had not reached out at all was because he felt bad; he knew that I had liked him and letting me down -- however gently -- was not what I had wanted for us. I thought about texting him, but what would I say? The feelings weren't gone, and I didn't want to insist on hanging out just to torture myself. Then there were the boys to think about, as well. I didn't want to interrupt their status quo for my own selfish wants and needs.

In bed that night, I decided to send a message, but not to Max. I hadn't seen Santiago in about a month, and the best remedy for my wounded heart was another mind-blowing orgasm. I convinced myself that it wouldn't be like last time: he wouldn't take forever to cum and wouldn't ramble on and on about his feelings. I let him know that I was looking to hang out; he responded a few hours later.

*Bold is Santiago; Italics is me*

Hey

Still Hirny?

Always

Just got home I'll drive out there tho I gotta shower

I need to shower too

OK

Watching TV lol

lol ok

We should do something

One day

Split the money get a room

To shower together

Oh?

Yes

Try to just shower be naked and have sex

Could you even handle that?

The lights would have to be on

No they wouldn't I want dim lights but yes

Candle lit

Music

Romance?

Maybe a supplement to enhance sexual performance

Like?

Do you want romance?

I mean I like romance

I wouldn't mind having a situationship with you if that's what you mean

I had you cock in my mouth and liked it I just hope you take it seriously it's life changing having to do that

But let's think simple for now. For now I'm straight and like it

I get so hard

Lol. Same as if I let you fuck me.

What supplement?

Idk something to make us hard

And wym if you let me fuck you

You would?

We should get the think that we can both put our dicks in

Thing

Like Viagra?

You said sucking my dick was a big deal for you, life changing.

Me letting you fuck me would be a big deal. Life changing.

Yes if you realize that then it's easier.

And yes we'd toy

Lol

Sex toy

I had a butt plug but I gave it away

Still haven't showered

My tip can plug you

lol

But I'm showing now heading to you

Lol. I never used it.

See you so

Soon

He got to my apartment around 3:30 AM. Truth be told, I was already tired at that point, but I also didn't want to feel lonely and rejected. I was intimately familiar with his averseness to light, so I had turned every light in my apartment off, except for the TV. I had been watching Grey's Anatomy while I waited for him to get there. In the hustle of making my bed and tidying up, I'd misplaced the remote for the TV.

He was wearing his usual basketball shorts, hoodie, and hat. I could smell the familiar skunky aroma of marijuana on him, making me long for the days when I could smoke. For some reason, my heart was racing this time; it had never done that before. Santiago was the closest thing I'd ever had to a steady sexual partner, so why was I so nervous? I was in control; I had all the power and experience. Could it be that my heart was thundering in my chest because I knew that our newly formed truce was going to be as short-lived as my courtship with Max? Or could it possibly be that I knew that this meant absolutely nothing to me, but everything to him? I was using him for his mouth; the rest could disappear and I'd be fine.

We got into bed and lay there awkwardly, both of staring up at the dark ceiling. I alwys wanted cuddles and true intimacy to start, but I didn't ever bring it up; I knew that he wouldn't be down for that.

"I wish we had, like, a routine," he said, sighing. "We've done this enough times."

"That would make starting it easier," I agreed, burrowing under my blanket for warmth.

"Is there any way you could shut off that light?" he asked, meaning the TV. "I'm sorry."

"Normally, yeah, but I can't find the remote. And now all the other lights are off."

"I just prefer to not have any lights on."

"Well, close your eyes, and then there are no lights," I said, half-jokingly. I was not about to waste precious time looking for a TV remote. I didn't want this to be an all-night endeavor; time was of the essence.

"What do you mean?" he asked, making me roll my eyes in the dim light.

"Close your eyes, and then everything's dark," I explained with what I hope came across as patience. The truth was, I had little patience, especially when it came to Santiago. I just wanted to cum and then go back to my show until I was ready to fall asleep.

"Oh." He laughed. "You're funny. I never knew that about you before. There's a lot of things we don't know about each other, personally. Like I'm a very spiritual person."

His diatribe was interrupted by one of my cats, Prue, jumping up on the paisley upholstered chair that my grandma had given me. She knew that she was closer to dying than she was to being in the land of living, so every time I went over to her house she tried to send me home with something. I used the chair for gaming; it was comfortable and helped me see better, since I was gifted with terrible vision.

"Oh, a cat!" he exclaimed, as if he had no idea that I had several cats. Every time he came over, at least one of them came over and sniffed him.

"Prudence!" I said with mock severity. She wasn't hurting the chair; she just liked to sit up high and survey her territory.

Prudence -- Prue for short -- was a small gray and brown tiger cat, the twin sister of my Asher. Prue was an oddball; she really only wanted attention/affection on her terms. Any other time, she ran away if I came close to her. She'd never used to run away from me, but after the flea outbreak of the past summer and me having to force oral tablets in her mouth, she was more wary of me and sudden movements.

She jumped down onto the bed and slunk over toward Santiago, sniffing him curiously.

"Oh, my God!" he exclaimed like a child. "She came to me! Can I have her?"

"No," I replied instantly. Who the fuck asks someone if they can have their cat?

I took my cat rearing very seriously. If I 'adopted' a cat, it was for life. Plus, knowing how tempestuous Santiago could be, I couldn't bear the thought of him lashing out and hurting her in a drunken rage.

"If you ever get rid of her, can I have her?"

"You'd have to take her brother, too. I'm not separating them. They love each other."

It was not uncommon for me to come home from work to find Asher and Prue curled up together, looking like a two-headed cat. Aside from Asher being twice her size, they were pretty much identical twins. If anything ever were to happen where I had to rehome a cat or two, I would not allow them to be separated. The love that they had for each other made my heart swell every time I saw them snuggled up together or grooming one another. It was even more magical to me because I'd brought them home months apart. Asher had been an impulse rescue in the heat of June, and Prue a begrudging rescue on a mild September day. There was another sister at my grandma's house who was identical -- making them triplets -- but as much I wanted to reunite them, I knew that taking on too many cats was not a good idea. If I were to ever lose my job or get evicted from my apartment, I would be hard-pressed to find somewhere to live with half a dozen cats.

"I have my brother's cat!" Santiago continued excitedly. "They'd get along great, I think. My brother, the one that died, he wanted a cat, so I brought one home for him. It ended up dying, I'm not sure why, so I brought him home another one, but that one died too. The next time he got a cat I stole it from him."

I didn't want to point out that, at least in my experience, cats don't just die. Either his brother was not feeding or watering the cats, or he was neglecting them in some way. I didn't want to assume that he was violent toward them with no evidence, but that was an option as well.

"Good," I muttered, petting Prue for a second before she zoomed off into the darkness.

"It's crazy that she just came up to me like that. I'm very spiritual, like I said, and animals seem to love me."

I had to bite my tongue to keep myself from explaining that Prue was simply curious about this stranger in her territory. Santiago had a scent that was unfamiliar to her, possibly even smelling like his cat. Cats are curious creatures and extremely territorial; it had nothing to do with whatever spiritual bs he was trying to mask it as.

"The cat I have, she just sits outside my room and stares at the wall. It's almost like she's watching me through the wall. Whenever I come out, it's like she was just waiting for me."

Once again, I rolled my eyes at his complete obtuseness in regard to the world around him. It wasn't something mystical or otherworldly.

"I'm into witchcraft, too," he continued. "Cats are kind of like, that thing, you know...I don't know what it's called. A spirit animal?"

"Familiar," I responded, kicking myself for inviting this into my life. I could be cuddled up with my babies, enjoying the silence, watching Grey's Anatomy, but instead of I was listening to Santiago ramble on and on in hopes that he'd put my dick in his mouth and make me quiver.

"Familiar? What's that?"

"You know, a witch always has a Familiar. It doesn't have to be a cat; it can be a snake, or an owl, a rat...the Familiars act as assistants to witches."

Santiago was as much into witchcraft as I was into politics; the difference with me, though, is that I was honest about my lack of interest in politics and didn't go around talking as if I was learned on the subject. I wasn't sure if he was trying to impress me, or if he was just that desperate for any kind of meaning in his life.

"Oh, I didn't know what they're called. I just knew there was a word for it," he replied lamely, trying to mask his ignorance on the subject.

"You know, you could get naked," I pointed out, "that would help start things up."

"Naked?" he asked as if I was proposing he stick his head up his ass and try to make himself as small as humanly possible.

"Yeah."

To demonstrate my point, I slipped my robe off, revealing my naked body. Sure, he couldn't see much of it in the scant lighting, but my point was made.

"I just..." he sighed wearily, "I don't like to just go right into it. I like to go slow, build up to it."

I wanted to point out that we had had almost the exact same conversation the last time he'd been over, but I didn't want to seem like I was being a dick. If anything, I was trying to avoid having to suck his dick forever to get him horny enough to even touch me.

"Here, come here." He pulled me into a cuddle, my head on his chest. He was warm against my cold, bare flesh. It felt nice. "Oh, you're naked."

"Yeah. I took my robe off."

"I know, I just didn't know you didn't have anything on underneath. I guess I could..."

He pulled his hoodie and t-shirt off, pushing them down onto the floor. Next came his shorts and boxers. As soon as he was naked, he was pulling me to him again and his hands started to roam my body. Instinctually, I started to touch him too, rubbing my hands up and down his chest, grinning when he winced in pleasure. I could feel his body relax, the nervousness fleeing.

Santiago pulled me into a kiss, his lips hungry. "Give me your tongue," he moaned against my lips. I complied, and I felt our teeth gnashing together as his tongue invaded my mouth and started caressing mine. "Fuck, I don't ever want to be turned on by another male," he said, getting more aroused with each touch and kiss.

Suddenly he was on top of me, my legs up on his shoulders. We'd been in this position before, once, but he had been unable to get the Cadillac into the garage so to speak. I was not about trying again that night, but I was okay with what he did do. He dry humped me, his cock sliding along my hole, his weight on top of me. With each thrust, I groaned involuntarily; not due to any pain or discomfort, just the act itself. I could see why gay sex is so noisy.

Before long he rolled onto his back and pulled me on top of him. I started grinding my hips on his pelvis, simulating that I was riding him. He moaned, his head thrown back in ecstasy. His hands made their way up to my chest, caressing the little bit of breasts that I had. He was pretending that I was a woman, and that was okay by me, I just wished in that moment that I had big enough breasts that he could sit up and suck on my nipples. Maybe if he got turned on enough, this would be a quick tryst; we could get each other off and then I could go back to Grey's Anatomy.

After a while, I got off of him and lay back down. My hand found his hard cock, rubbing it, caressing the tip. "That feels so good!" he encouraged, moaning. "I want to get horny enough to suck you."

"It feels like you're already there," I replied, knowing full well that he would not get 'there' without my sucking on him.

"Can you use your mouth? That really gets me there," he said, proving once again that I knew him far too well.

I knew that my jaw would only hold out for a limited time -- his cock was very thick -- but I also knew that if I ever wanted us both to cum, I'd have to shut up and do it. I moved down by his legs and took him in my mouth.

"Oh fuuuuuuuucccccccckkkkkkkkkk!" he groaned, his body going slack. I appreciated the compliment, I just would have preferred it come from someone I actually liked, at least in a romantic way. If Max and I had been intimate in that way and he'd groaned like that as soon as I'd slipped him into my mouth, I'd have been over the moon; with Santiago it didn't hit the same way.

I sucked on him for a while, using my hand to help relieve some of the tension and strain on my jaw; if I just focused on the head and let my hand do the rest, I'd be able to hold out for a lot longer. I hated having to stop so that my jaw could rest a little; it made me look like a wimp and it delayed the grand finale that I always looked forward to. Most guys didn't last very long in my mouth, certainly not long enough that I needed to take a break, but it seemed as though the more Santiago and I did this, the longer he lasted, much to my dismay.

"I want to 69," he whispered, his fingers brushing my hip.

"Okay." I took advantage of the break and popped him out of my mouth, moving my pelvis closer to his face.

"I'm not totally there yet, but I'm close."

"To cumming?"

"No, to being ready to suck you, too. I just need you to get me there. I want to take a video of us 69ing."

I was always down to make naughty videos, especially if I got to show off my skills, but I didn't want to do it with just anyone. It helped tremendously that Santiago and I had been hooking up for almost six years; I knew that I didn't have to worry about the video getting leaked or passed around. It would sit on his phone, coming out when he was horny. Of course, the original would be on my phone, which somehow made it less scary to me.

"Let me get my phone," I said, scrambling in the dark to find it. I had had it on my person when he had let me know that he was pulling up, but I couldn't remember if I'd left it in the pocket of my bathrobe, or if I'd put it in the drawer of my nightstand.

"No, on my phone."

I hesitated. While it wasn't a huge deal to me, I also wanted to be able to watch it as my leisure or send it to prospective partners to show them what I was capable of. Of course, if Santiago's face was in it I'd crop it out -- out of respect for his privacy -- but a faceless body getting head was fair game in my book.

"I'd want a copy," I replied, idly stroking his cock to keep him hard.

"Let me go home and watch it first. I want to make sure it's hot. If it is, I'll send you a copy. No one's ever seen me suck a dick before; I want to be the first."

I couldn't argue with that logic, so instead I just went back to sucking him.

Before too long -- thankfully -- I felt his hand on my cock, stroking it. This is it, I thought excitedly, he'll stroke it for a minute or two and then he'll suck it! This was what I had been craving all night.

I gasped when he slipped me in his mouth. I was no stranger to 69ing, but it was only difficult with Santiago, difficult in that his mouth was so good that I had a hard time focusing on taking care of him as well. I thought it would be hot for us to cum together, but I knew that that was highly improbable. He'd make me cum and then I'd have to continue working on him, desperate for him to finish.

After a few mintues, he stopped. "Can we turn that light off?" he asked. I knew that he was referring to the TV. I still hadn't been able to find the remote, not that I'd been looking. "It's kind of bright."

"Just close your eyes," I whispered, trying to keep my irritation masked. What did it matter if there was some light in the background? Didn't he just close his eyes and suck, like I did?

"Let's use the blanket," he suggested, pulling my sherpa blanket over both of us. I was immediately plunged into total darkness, but I figured his phone had flash, so the video wouldn't just be sucking sounds and moaning. "It's really hot when you grab my ass, too. Last time you did that, it really turned me on."

Even with my eyes closed, I could see the flash from the camera. Santiago must have liked what he was seeing, because he started to thrust into my mouth as he sucked harder and deeper on me. I wanted to just lay back and enjoy getting head for once, but I knew that that was almost definitely not going to happen. I would have to just do my best to focus on my own task at hand. I reached around and squeezed his ass cheeks, eliciting more moans from him.

I found myself moaning in tandem with his thrusts. How was it that the only person to ever give me amazing head was a total closet case who drove me crazy? I'd gotten head from plenty of out and proud gay guys, but that had left me wondering what the big fuss was all about. I couldn't help but wonder if it was some psychological defect, where I was only really attracted to 'straight' guys. Sure, Terence had given me really good head, but it hadn't been like it was with Santiago.

He threw the blanket off after a while and started watching the video. I kept sucking for a bit, going faster as he gasped more, until he stopped me. "Go slow," he commanded. "It feels better."

"Don't you want to cum?" I asked, gritting my teeth in frustration. Why was he always trying to drag it out?

"Do you want me to?" he shot back.

"Yes!"

"I don't want to cum until I've made you cum, though."

"If you just keep going, you'll make me cum. It doesn't take much with you."

I was not above playing to his ego and vanity if it got us both there faster. I'd glanced at my phone and groaned when I'd seen that it was well after five AM.

"Just get me there again," he begged, his voice husky.

"Is it because you're uncircumcised?" I asked, stroking his cock. "Is that why you don't want it fast?"

"Kind of. I mean, how does it feel for you, going fast?"

"It feels good. That's what gets me to cum."

"Oh, well it's kind of different for me. When you go fast it feels good, but...."

"Overstimulating?" I supplied helpfully.

"Yeah."

I started sucking him again -- slowly -- hoping that he'd be ready to work on me again before we basically had to start over. The idea of starting over wasn't completely horrendous to me, but I had been close enough before he'd stopped that I was annoyed. I wanted my orgasm!

I stroked and sucked him for a while until my jaw was cramping and I had to take a break. I moved back up to the pillow, intending to jerk him off for a little bit until my jaw had had a sufficient break, but once again, Santiago surprised me. He moved down by my feet and started kissing my dick. "This is what I want you to do," he said.

He kissed my pelvis, the head and shaft of my penis, before working down to the balls. For some reason, this really got me going; I found myself panting even though proper stimulation hadn't even happened yet. My legs went back up on his shoulders; his arms hooked behind my thighs. I wished that he was open to rimming in that moment; it would have been incredibly hot for his tongue to flick and tease my hole. Maybe one day we'd get there.

"Don't cum in my mouth," he said, taking a quick break. "It was okay last time, but I didn't have a choice. I don't think I want it again, at least for now. It's still weird for me."

"I get it," I assured him. It had taken a few years of me sucking dick to be comfortable with a guy cumming in my mouth. After that first time, though, I was hooked.

I started moving my hand on my cock, knowing just how to get myself there. Santiago's mouth could do a much better job, but I didn't want to have to rush to get out of his mouth before I came. I also didn't want to give into pleasure and stay inside him, letting his warm mouth envelop me and my load.

I felt myself growing close; I climbed up on top of him again and busted my load all over his face. As the aftershocks electrocuted my body, I continued jerking myself a little, feeling my cum in the bristles of his beard.

"That was really hot," he said, as I climbed down from him and the bed and raced to the laundry room to get a towel. "Are you still going to help me?"

"Of course," I replied, stumbling in the darkness with the towel. "Just try not to make it a thing. It's six in the morning."

As I went back to sucking him, I saw the flash once again and realized that he was getting ready to take another video. I opened my eyes and peered up at him over the frame of my glasses.

"Is it okay if I film it?" he asked, biting his lip.

"Yeah. Just send it to me."

I gave it my all for quite a while, long after he'd stopped filming, before my jaw hurt too much for me to keep going.

"Here, I can take over," he said as I moved to the pillow. "Sorry it's taking so long."

"It's fine." It really wasn't but I didn't want to make him feel worse than he already did, and I certainly didn't want to start a fight.

I lay there, eyes closed, running my fingers down his stomach and around his thighs as he jerked himself. At one point, he stopped and I looked over at him, confused.

"Did you stop?" I asked, quirking an eyebrow.

"No." As soon as he said it, I felt the motion resume.

"I didn't feel anything," I explained, closing my eyes again.

"I've learned to do it without moving anything but my hand," he replied. I wasn't sure if he was referring to himself jerking off with his sleeping son in his bed, or one of his girlfriends; I figured it was best to just let that one lay.

After a while, the motion stopped again, and I started to hear soft snores gargling out of his throat.

"You're sleeping," I said, loud enough to wake him back up.

"Just a little."

"I can't have you sleep over," I continued, feeling my annoyance with the situation grow more intensely.

"I'm not trying to sleep over," he assured me.

"It's almost seven AM now," I pointed out, not quite politely.

I was exhausted after a long, stressful workweek. All I wanted was to go to bed at that point; I'd finish Grey's Anatomy when I eventually woke up.

"Yeah, if I don't cum in the next five or ten minutes, I'll just wait until I get home. Maybe I can watch those videos."

"Try porn," I snapped, grumpily.

He turned porn on, but I did not open my eyes to watch with him. It was taking everything I had just to stay awake; I knew that if I fell asleep, he would, too, and then I'd wake up with him in my bed, desperate to do it again.

The five or ten minutes went by and still no big finish. "I don't know why it's taking me so long," he groaned in frustration.

"It's after seven now," I told him, barely able to even open my eyes.

He started masturbating furiously and in the blink of an eye, he finally came.

I pulled my robe back on as he got dressed. "I'm sorry I took so long," he said again, sliding his pants back on.

"It's fine," I lied, holding my arms around myself. Even though the heat was on, leaving the bed had made me cold almost immediately. One good thing about Santiago staying the night would be his body heat, if only I could have that without the rest of him.

We made sure that he had everything before I rushed him out the door into the cold, early morning air. As soon as the door was shut behind him, I ran back to my bed, threw the sherpa blanket over me, and fell into a deep, blissful sleep.

Was the sex only good with Santiago because I barely tolerated him? Was that the secret to avoiding catching feelings and having mind-blowing orgasms? I knew that I should be nicer to Santiago, more patient, but sometimes he just made it so hard. Up until recently, we'd kept the conversation to a minimum and he'd cum a lot faster; that worked a lot better for me. I didn't want to be unkind, but when it comes to ruining my precious sleep, no one is safe. Maybe someday we could manage to get together earlier, at a more decent time, see if that would help with my annoyance. Or maybe the problem really was that I didn't like Santiago anymore -- at all -- he'd said too many cruel things and pissed me off far too many times. Should I just cut him loose and risk the consequences? Or was it okay to keep him on the back burner for when I wanted a great orgasm?

I did know with full certainty that I was not in the market for a situationship. I want labels and commitment; I want at the least the possibility of a future with the man I'd potentially be blowing and having sex with. Why was it so hard to find a guy that I had romantic and sexual chemistry with? Why did it always have to be one or the other? It shouldn't be like having your cake and eating it too, in my opinion. I was no stranger to the cold realization that life was rarely fair, but I couldn't help but feel as though I was being personally victimized by the universe.

I'm sure Santiago and I will meet again, but in the meantime, I have not gotten downtrodden enough to throw in the towel in my great search for true love. I'm still young, I can still bounce back. I won't give up until I've gotten what I want, or I realize that I'm better off alone and decide to focus all of my free time and energy to the pursuit of being as fabulous as I can possibly be.