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Same Mistakes, Part Un

The Sex Files

By Gabriel Bradshaw Published about 8 hours ago • 11 min read

I believe it is human nature to fall back on bad habits when you are in a slump. When faced with a void of nothingness it's natural to return to things that are old and familiar - for comfort, for entertainment, or even for lack of anything better to do. With Zane happily dating someone and my interactions with Whytt reduced to streaks on Snapchat, I was finding myself - for the first time in a long time - with no guys to talk to or hang out with.

One uneventful Saturday morning - around two AM - I was on the phone with my cousin - catching up - when I received a Facebook message from Santiago, my complicated fuck buddy. I hadn't forgotten our tumultuous past - how he freaked out when I turned him down and made me out to be some kind of monster - but I had an itch to scratch and despite all of the drama that sometimes came with Santiago, I did always enjoy our sexual encounters: he gave the best head I'd ever gotten and was an amazing kisser - it was rare for me to even want to kiss, let alone enjoy it.

I'd unblocked him - just to see if he would reach out. The last I'd heard, he was dating my cousin's maternal cousin, Taylor. She didn't know me or that I knew who she was, but a mutual friend had told me about her new relationship; I'd even seen them together - briefly - at Meijer the previous winter. I knew being involved with Santiago was like playing with fire - it was only a matter of time before I'd get burned - but I did miss how good it was when he wasn't drunk and malicious.

Hey

Hi

Omg hello
Lol

?

Idk sorry
Being funny
How are you
Surprised ur up

Talking to my cousin

Been a while
Oh nice
I live in Pinconning

Why?

I was about to head home
Cuz I work at dispensary lol
Had to

Ah

Yeah
Wanna play or naw

Play what?

Eavhbither

?

Each other
lol
With

I'm on the phone

Oh ok sorry
Night

Don't be sorry

Well you got nothing out of it night
Mother of us

Out of what?

Nither
Neither
Nothing
Night

K

Ok
So nothing
You got a friend?

What?

I might be gay

Oh?

Tired of girls

Why do you think that?

Just help

Just help?

Cuz I'm back here
That's why

Huh?

Nothing finding other guys
Sick of this bs

You're not finding other guys?

Should be this hard for a straight thanks
I don't look
Now I am

Okay?

Gave this a chance long enough
I'll download grinder again idgaf

Why are you telling me this?
You messaged me

For help again and you act like I ain't shit when there dudes who will keep helping me

Wtf are you even talking about?

I gave you a chance and you just got me to suck your dick and I got shit out of it
Nothing

Once again, he was making me out to be some kind of villain for not making myself wholly available to him when he was horny. I knew it was toxic and that the situation was never going to change, but I really wanted to feel his mouth wrapped around my cock.

Because I won't hang up on my cousin?
You've gotten plenty of out it.

I hated when he acted like I was the only one having fun. The truth was, if I wasn't giving him great head, he wouldn't keep coming back. I'd never wrap my head around his logic that just because he'd gotten comfortable - and turned on - enough to kiss me and suck my dick as well that I somehow owed him to be at his beck and call.

No I didn't ask you too

Then what are you mad about?

I rolled my eyes, wishing I had left him blocked. Here we go again, I thought, hanging my head. Why did I keep allowing myself to be involved with him - was I a masochist or something?

I asked for fun but it's my way of trying to covert it be bi
I will find out
Sorry
Cuz I'm tired of women

I didn't say no. But I'm helping my cousin atm.

Ok night
It's 3 am

We haven't talked in months. I can't just hang up on hee
Her

It's ok I'm sorry

His apology took me by surprise. Normally when he got angry enough to start saying that I took advantage of him, there was no reasoning with him, but here he was, apologizing and... seeing reason?

Unless you want to touch me while I talk to her lol

I wanna suck too

Hot

Well I need to get hard to

Mhm

But I will too

Hot

Let's play
I can come now
Be there by 3:45

You wanna do it while on the phone?

As hot as the idea of him sucking me off while I was on the phone was, I could never disrespect my cousin like that. She was filling me in on all that was happening in her life; as close as she and I were, we often went long stretches without talking due to our similar responses to stress and anxiety: when it got too much, we both had a - bad - habit of disappearing until things got better. She'd listened to my kvetch about my incompetent coworker and the frustration that his inability to grow up, accept responsibility, and get his shit together was causing me; my love for her - if not propriety - would not allow me to check out while she vented to me.

Or sooner

Where are you? Lol

Yeah if you help get me hard
Close

I can get you hard
You know that

I know so I'm on the way
Right?

Right what?

One the way lol

Oh okay.
It's going to take you a half hour?

No I'll go fast

Haha
Eat my pussy

Nahh
Not there yet

I knew that he was nowhere near ready to eat my ass, but still, the idea turned me on immensely. There were a few times he'd suggested involving a girl in our bedroom deeds - I wasn't completely opposed to it, especially if I got to watch him eat her out, but it had never come to fruition.

Okay lol
We aren't going to be able to talk

Wym
I'm driving I

Because I'm on the phone. I'll have to multitask
Did you forget?

Yes I know
No I didn't

Lol okay

Ok what
lol at me when I sick
Look at me when u suck
I
When I stuck

Look at you while you suck?

Yes

Okay
Lights on

Get me comfortable lol

Idk how

You do

Suck you?
Can't suck until my cousin is done

I wan yeah I like being really horny then indoor

Huh?

When I'm really horny I wanna do a lot

Ahhh

I gotta get there
I'm here

I was a mess of nerves as I made my way to the door to let Santiago in. Although I enjoyed what we did in bed, something about him always made me nervous. I knew that he would never hurt me, but there was an air of unpredictability about him that raised my hackles as well as turned me on.

I opened the door for him and waved nonchalantly as my cousin kept talking. I led the way to my bedroom and then crawled into bed, settling in against the pillows.

"That's a little too much light," Santiago murmured, looking nervously at the lamp that was glowing on my nightstand. I reached over and twisted the knob, drenching us in darkness.

As my cousin and I started to make our goodbyes, I reached over and started rubbing Santiago's dick through his sweatpants. He sighed in pleasure and I could immediately feel him getting hard. There was something hot to me about being on the phone with an unsuspecting someone while I played with dick, but I wouldn't let it go too far - out of respect.

After another five or ten minutes, we ended the call. In the dim light of my bedroom, I could see Santiago's mouth open in ecstasy. By then, I'd slipped my hand under into his pants - under his boxers - and was fully playing with his erect penis, relishing the warm hardness in my hands.

Santiago yanked his pants down to allow me better access. "Take your shirt off too," I ordered, wanting to see his tattooed chest - as best as I could in the scant light. Surprisingly, he complied. He didn't like it when I sucked on his nipples, but I figured if I got him horny enough, I could at least play with them a little.

"Will you suck it a little? Just to get me started." Santiago's voice was husky, heavy with lust. I liked how horny he was for me; how easy it was to make him forget his straightness.

I climbed down the bed and took him in my mouth. His cock fit my mouth like it was made specifically for it. As I sucked and bobbed my head up and down - slowly - Santiago gasped. "Fuck. I've missed this," he whispered, "fuck! That mouth!"

After a couple of minutes he said, "I just got out of a relationship; I never got hard like this for her. I have a video of her sucking my dick - I'll show you I never got hard for her like I do for you."

I was grateful for the break - his cock was thick and hurt my jaw after a few minutes. I moved up to lay beside him as he found the video. "Do you have any videos of you fucking her?" I asked. I'd always been curious about how he fucked.

"No," he answered, eyes glued to his screen as he perused his video collection.

"Eating her out?"

"Yeah. It's not super great but --"

"I wanna see it," I interrupted him, feeling myself finally switch from focusing on my cousin to the matter at hand.

Santiago turned his phone so that it was facing me. On the screen, I saw his hard cock- it looked just as hard to me - as his ex-girlfriend sucked it. He moaned and told her how hot she was - even though she had small breasts and didn't look very enthusiastic.

"See? I wasn't as hard then as I am now."

I wanted to point out that he was - in fact -the same amount of hard, at least in my expert opinion, but he was trying to butter me up and I was desperately in need of some compliments and validation. "Now let me see the one of you eating her out." As he started the video, I said, "Taylor doesn't look very enthusiastic."

Santiago immediately tensed, sat up, and stopped the video. "Wait, you know Taylor?" he asked, panic in his voice.

"I know of her," I corrected him, pulling my robe more tightly against my body. "She's my cousin's cousin, but I don't really know her."

Santiago was silent for several seconds. "I'm kind of uncomfortable now," he confessed, his voice no longer laden with lust. "You figured it out pretty quickly. I take it you already knew I was dating her."

"What?" I asked, feigning ignorance. I could sense our fun train going off the rails and I wanted to avoid that as much as possible.

"You knew her name already."

"You showed me the video," I pointed out. "Her face was clearly in it."

"Yeah, but you recognized her pretty quickly. Almost like you already knew."

Maybe Santiago was smarter than I'd given him credit for. Of course I'd known about his relationship with Taylor. Taylor and I had mutual friends - friends who knew about Santiago - and had more than willing to keep me up to date on the gossip. I couldn't tell him that, though, not without admitting that I had told people about us.

"I saw her face - clear as day," I continued, rolling my eyes. "I know who she is. It isn't anything major. I mostly know her because she accused a friend of mine of raping her, and I would bet my life that he didn't."

"He probably did," Santiago said. "She's a manipulative cunt just like her mother. We'd been going out for a while - and everything was fine - until recently. She didn't have a car and had tickets for a concert; I drove her and thought we had a good time, but as soon as we got home, she was different. She got her car back from the shop and then started acting cold toward me. There's this girl at work that was flirting with this guy, as soon as Taylor found out, she started flirting with the guy and now they're going out. It's like she couldn't stand not to be the center of attention. She never showed any interest in that guy before."

I listened to Santiago complain about his ex for about twenty-five minutes before he grew silent. I didn't know what to say, so I just lay there, staring at the walls. "I'm sorry," he said in a quiet voice. "Do you want me to leave?"

"You don't have to..."

The truth was it was past three in the morning, and I was ready to get settled in for bed; I wished - not for the first time - that Santiago and I could have a sexual encounter without any unnecessary drama. I didn't want this to turn into an endeavor that would carry on until seven - at the earliest.

"I feel like you're not really into it anymore. You're not being touchy like you were before."

"I'm not going to touch your dick while you talk about issues with your ex-girlfriend," I pointed out, keeping my tone patient when in reality I was already growing annoyed with him.

"I just wish I didn't know you knew her."

"I don't," I repeated, fighting the frustration burning inside of me. Why couldn't he just let it go?

"It's just going to take me a few minutes to get back into it."

I knew that if we were going to salvage this hookup, I was going to have to take charge and make him forget all about his ex-girlfriend. While I didn't mind being in control sometimes, I also wanted Santiago to be dominant and show me how much he'd missed me, how turned on being with made him. Once he got horny again, the chances of that happening would increase, but there was never any guarantee that he would be able to lose his inhibitions.

If I wanted to wrap it up, I would have to fake being into it and get him horny enough - again - so that he'd touch me and get me horny again. It was a vicious cycle. I really wanted to just kick him out and read until I fell asleep, but I forced myself to lock in and prepared to blow his mind.

erotic

About the Creator

Gabriel Bradshaw

I've been dating for twenty years, and I have some insane stories to share. Join me on my quest of love: romantic love and the love of labels. The dating world is savage, but I won't give up until I get what I want.

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    Written by Gabriel Bradshaw