First Time Fisting

First Time Fisting

I came to hookup, I ended up fist deep.

The first time I do anything is usually five minutes after it is offered up.

So one particularly lonely night, I was just about to take a seat onto my ‘All American 6.5 Inch Vibrating Dildo,’ when a really cute guy messaged me on Facebook.

Read related article: Sex Etiquette

The conversation went literally as follows:


Always thought u were super-cute but was in a relationship so I could never say anything.


Well thanks, thought you were super-cute yourself.


Oh, thank you, and your post about butts on facebook earlier is so true…

Even though I’m versatile.

*I posted earlier, ‘Even though I am a total bottom, I am such an ass guy’*


I was actually just getting lube when you chatted me

Lol I was going to have my ‘gentlemen’s time’


To put in your hand?? Like j/o with?

Come have that with me


I jack off with lube and other things




I think you’re absolutely adorable J


I think you are super-cute too J


I love using toys and stuff lol.

Thanks J


But being a random, this whole, ‘late night, still sad about-the-ex one night stand thing,’ gets tiring and can be misleading…

*He recently broke up with an ltr*


Oh well I am not meaning it like that…

So please don’t think that.



Where is this place?



Is that anywhere close?



Its only like twenty minutes away…


What do u like to do?


Well what do you hope to do this evening?


Well honestly i want to be a gentlemen if thats what you would like

Watch a movie

Cuddle lol

I have some pinot noir…

Now if you were in a more sexual mood….

I would lay you down on the floor, kiss your neck, and nibble your ear.

Then slowly kiss my way down to your stomach.

Then gently take your pants off and pleasure you.


I’m sure we can find some mid-ground.


Then flip you over and eat your ass out until you’re screaming because you love it so much


Expect me around 11:30-11:45, is that okay?


That’s fine with me

So like, do you top any? Or like to play with ass?


I like to play

Don’t top, but play


You like to play with ass?


Yeah, if that’s what you like.


So trying to open me up with your fingers?

I love, I mean LOVE to have my ass played with.


For sure J


Can’t wait to be opened…

So a mere twenty minutes drive later I arrived at this place. It wasn’t his, he was housesitting for friends, but it would do.

I always am very weird about knocking on doors of people I am hooking up with. I am not sure why, I think it is like a mix of fear that their parents will answer, or fear that I am at the wrong place. So I texted him, ‘I’m here.’

He arrived at the door a quick fifteen seconds later and let me into the rather messy, but large house. Iron Man was playing, and wine was out. Pinot Nior, just like he said.

We chatted for a bit, about this, that, and the other. About the people we knew, and the gossip we could trade. He was very cute, like very cute.

Shorter, like I like them, and had a nice ass. He was draping it in basketball shorts this evening, and if anything ever made an ass look good, it is basketball shorts.

Not to mention, if you cop-a-feel, you are a very thin silky material away from actually touching bare, hot ass.

So things got kinda sexual when he mentioned our chat.

‘So what are you into?’ He inquired.

‘I mean, I am open-minded and I like oral… of course. Bottoming is fun too. But I really have no specific fetishes at the moment. What are you into?’

‘I like really love to have my hole-‘ he stopped briefly and laughed.

‘Isn’t is funny how much easier it is to use phrases like ‘my-hole’ when chatting online as opposed to in person.’

Haha, yeah, I don’t think I have ever used the phrase ‘my hole’ in conversation before, so this is a tad bit unusual.’

‘So what do you like to do with your hole? Or like done with your hole?’ I laughed to relieve the discomfort of the exchange of conversation.

‘I love to have my hole-‘ he paused ‘opened up.’

‘You sure you are a top?’ I was a bit worried that I had traveled twenty minutes for nothing. Especially since I was about thirty seconds away from getting fucked by a vibrating dick before this guy chatted me.

‘Yes, I am a top. Well, I am very vers. But I love to have my ass played with. You like to do that?’

‘Yeah.’ I responded.

‘Have you ever fisted someone before?’

Whoa, that took a quick turn in the extreme sense, fast.

I had never fisted anyone before, and if I were to be totally honest, it was something I never planned to do, or be on the either end of that exchange.

However, I have prided myself upon being the kind of guy that never turns down a ‘first’ experience. I had no idea if fisting was something I loved, since I had never done it. This could be my only chance ever to fist anyone before I die.

It was that series of thoughts that inspired my responses throughout the rest of the conversation.


‘Like, have you ever wanted to fist someone?’ He asked, clearly unsure of how I was gauging the conversation, or what I was thinking.

‘I mean… I am not opposed to the idea.’

‘So would you fist me?’

‘I don’t see why not.’

I took a step in, and my hand, like it always does, found his already semi-erect penis… And gripped it firmly.

‘So would you fuck me after?’ I whispered into his ear.

‘I don’t see why not.’ He regurgitated my words in such a way that made it more than clear that in a matter of minutes I would be disrobed with a dick inside me, or rather my fist inside him.

So my premonition held true. We made our way up to a guest bedroom upstairs, all the while making out and dry humping each other.

He threw me on the bed, and just as he said he would, he began to ‘bite just a little on my neck.’ After that, true to form, and his word, he ‘slowly kissed his way down my stomach.’

I don’t know at what point my clothes came off, but at this point I noticed nothing was still draped on my body. I was nude, hard, and fucking horny.

He sucked me dick for a bit before coming up for air. To my lips.

We kissed passionately and rolled around until I managed to get him face down and on top of him.

Oh the things I would have done if I were a top…

I started behind his left ear and made my way down to his ass. Kissing every inch or so, as his bum rose in anticipation.

After a bit of rimming, I decided he was ready.

My brave index finger made the plunge. Feeling around as if searching for something, my finger’s curiosity was validated with very loud, and very passionate moans.

 I decided it was time for my middle finger to enter the premises. It was more than welcome, and his hole was more than size accommodating. So I ventured to stick in another, then another.

I had my four fingers submerged into his guy, and he was moaning as though it was the most incredible thing to happen in his young life thus far.

With my hand folded into what I like to refer to as a ‘taco-formation’ I decided to go all in. And all in I went.

The fact that I was inside a human body, feeling around as though it were some sort of hands-on-museum-exhibit, totally outweighed my thoughts of anything else. It was when he looked back and asked me to go further that my head was brought back from the clouds.

I didn’t know much about fisting; I just knew I wanted to avoid hurting him, or killing him.

‘How far?’ I asked, curious and without a clue as to what the answer may be.

‘Just hold still, I will just ride it. Keep your arm firm.’

I obliged, and held my arm as firm as I knew how. I was not going to be a bad fister.

He rode my arm like it was a mechanical bull, and he was determined to win the grand prize. It was not long until my forearm had completely disappeared, submerged inside him. He was at the cusp of my elbow when I had my answer.

That was how far. Now I know.

He rode for a while longer then asked me to ‘lube up both hands and punch in.’

I used my context clues and did exactly as I was told. I pulled out both hands and lubed them up and then began doing an exercise similar to that of a move I saw on a ‘Cardio-DVD-Infomercial.’

You pull back both arms, keeping them elevated at chest height, and with one punch the target… into the target, then back, and the other hand takes a shot.

I burned somewhere around 1000 calories in the ten minutes that he had me do that, and he shot one of the biggest loads I had ever seen in my life. Or even in porn.

He then proceeded to go for another round, and fucked the fuck out of me. Like we are talking… POUNDED ME. Not only was he a top, but also he had some impressive sexual endurance, for a versatile fist-ee.

To my surprise, it was amazingly clean, other than the sheets being a whole new shade of wet, and white, the whole act was ‘porn-perfect.’ And I left knowing that I don’t make a bad fister.

 Yet another skill to add to the resume…

Now, it would be irresponsible for me to not address the issue of fisting from more of a knowledgeable and medical perspective.

Read related article: The Top 5 Things First-Timers Should Know About Anal Sex

Going ‘too far’ or ‘too hard’ while fisting can be very, very dangerous, and even in some cases fatal. So if you do choose to explore this fetish, you must do so with extreme caution and slowly. There is not rush, or contest to see how much you can fit.

The human body is fragile, and the tissue in your anal canal is very thin, and easily ripped. Odds are you have done it before, ripped it that is. It is not as painful as it sounds, and nothing to ashamed of, disgusted about, or even upset about. It is almost an inevitable part of anal penetration, but with this, you do not want to go about penetration too hard, with such a large object.

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“image is a copyrighted photo of model(s)”

To Swallow or Not to Swallow

To Swallow or Not to Swallow

To Swallow or Not to Swallow

Cum: salty, sticky, and sometimes smelly.

Should we really be swallowing this, especially if we do not know the person well, or in some cases at all? This question, as every gay sex question goes, is extraordinarily subjective and will vary from person to person. I can’t say much for my own opinion since I am very split myself. I can however tell you about my stories of spitting and swallowing.

I was blowing my boyfriend of a few months and I could tell it was going really well. His ass was clenched, his stomach was doing that ‘suck in, push out’ thing at an Olympic pace. I was queen of oral sex, and he was getting close to cumming.

Read related article: Biggest Fear

This was probably my fifth blowjob, so in gay terms, I didn’t know shit. I was practically a virgin. I just knew when it came out to be ready, and for the most part that it would taste like a cocktail of salt and bleach. Or what I would imagine bleach would taste like.

‘I’m so close baby.’ Followed by a string of moans and an ‘exorcism-style’ back arch.

I could practically count it down.

Breathing stops: Five

Ass Clenches: Four

Hands grab the bed: Three

Back Arches: Two

Muscles Flex and Pelvis Thrust: One

It shot like my childhood ‘super-soaker’ water gun. Except the by product was opaque, 100 times thicker, and warm. I don’t know why I didn’t swallow, but I simply didn’t. I held it in my mouth like a child with a mouthful of vegetables. I did that smile that you can only do with a full mouth.

‘That was so good.”

MMMMhhhmmmmm.” The only noise I could communicate.

I then made the worst judgment call of my sexual life. I decided I would start with his feet and slowly kiss him all the way up to his mouth. Each kiss, letting out a bit of my ‘boyfriend byproduct’ that had stuffed me like a thanksgiving turkey.

I figured, if I let a very tiny bit out with each kiss, it will not even be noticeable, and I will be off the hook.

I was so fucking wrong. I made about 20 puddles of cum all over his body, and he was anything but pleased.

“Why the fuck are you covering me with cum?”

He was ex-military so when he was mad, it was horrifying. Like I’m talking: bladder-clenching, throat-tightening, hands-in-defense-mode horrifying.

If I were a car, the fuel odometer would read about a quarter full. So I did a nervous gulp and emptied the tank that was my mouth. Shit, improvise!

“I thought it would be hot to get you all messy, so I didn’t have to take a shower alone.”

Fortunately, my cute explanation got me out of a lot of trouble, and possibly a session of ‘angry-sex’ of which I usually enjoyed. You have not been fucked until you have had angry sex with G.I. Joe. It was typically incapacitating.

The next story is even more mortifying, and I would like to let you know that I like you guys so much that I am communicating this dark moment to you. Plus, I don’t want you to ever have to deal with the same problem. Ever…

So same story different guy, I was giving professional head and doing it like it was what I was born to do. My parents would have been so proud, I know.

This was post-starbucks, so I had all my caffeine stored up, and was using it at an exponential pace. My head was a fucking jewishdreidel. Spinning around, tilting I was blowing like for the fucking Olympic Trials.

He was moaning, and like popcorn, the period of silence in between the moans were how you measured the ‘finishing time.’ However, unlike popcorn, it was the increased frequency as opposed to the decreased popping of corn.

Moan, three seconds, moan. Moan, two seconds, moan. Moan, one second moan.

If this were a Disney ride, I would head some animated voice count me right down to the finish.

Moan, pause, pause, moan: Five

Moan, pause, moan, pause: Four

Moan, pause moan, moan: Three

Moan, moan, moan, moan: Two

Muscles Flex and Pelvis Thrust: One

Like the Forth of July the fireworks went off. It was the grand-fucking-finale. And from the flow of fireworks shooting into me, this was one grand, grand-finale. My mouth was so full.

I was about to swallow when the idiot decided to tell me a particularly hilarious joke.  I would communicate it, but it was an inside joke we had cooked up for dinner before this point.

Like a cannon of laughter, I shot his load all over his face: into his eyes, mouth, and about a mile up his nose.

Being a sexpert, even I did not know the right answer for what to do after this. So I did what I was trained to do in any embarrassing moment: fucking get the hell out of there. After a quick sorry, I grabbed my shit and ran into the hallway of his apartment complex hopping like a pogo stick into my skinny jeans.

I was running like this was Texas Fucking Chainsaw Massacre and I was Renée Zellweger. I know it was a bit dramatic, but even my saucy humor and tranquility couldn’t have got me through that. I just prayed that he would not drown from the explosion of cum I had so-accidently shot at him.

Read related article: Sex Etiquette

The moral of the story being, if you are going to swallow, do it fast. Or don’t sleep with someone who is particularly funny, with a knack to break-the-ice-after-oral.

When it comes down to it, be careful. I personally swallow. Unless the guy is ugly or I sense bad hygiene, both of which usually inhibit me from going to bed with them anyway. But, we all have those nights of desperation… so don’t judge me.

Of course you should worry about STD status, but the likelihood of contracting anything-serious via-oral-sex is slim to none. Cum is also a great source of protein, but then again, so are mosquitos. Use judgment, and keep it sexy. Nothing turns me off more than someone running out of bed after I finish to go vomit up cum in the toilet. But if you know a sexy way to ‘spit’ go for it. (That rhymed, I am a poet)

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