A Cuban Takes It Deep

So, I just got back from vacation in Miami.  I have to admit I've always had a little attitude about Cuban guys and their over-exaggerated macho attitudes.  I think most of them of compensating for some other thoughts they are having.  So I decide to take one down.

My best friend, Craigslist, comes to my aid, as always.  The ad said:

"White top visitor wants to explore with married Cuban stud.  I host, my hotel, no one ever knows."  I add a chest pic and my stats and post.  Before long, my suspicions are proven as numerous Cuban married dudes starting vying for my dick.

Some of them clearly got some experience, regardless of being married, so I pass on them.  I choose a married "family man" who will be coming from work, and "isn't sure what he wants to do," but is needing some "male-male contact."  I tell him to come over and I'll take the lead (you bet I will).

He shows up and my dick almost pops out of my pants.  This guy is built and very handsome.  He is in a suit, so I say "Get that suit off- we would not want it to get ripped - might be hard to explain to your wife."

We get undressed, and I immediately put him on his knees.  That's not where we are going to finish, but hell, we can start there to get him comfortable, right.

I start fucking his mouth, and he is loving it.  He is stroking his dick, and a minute later, he pops.  What a pussy - no control at all.  He is embarrassed.  I say "no problem, a stud like you is good for two loads, I'm sure," and continue pumping his mouth.

I put him on all fours on the bed, and start licking his hole.  It is tight, and I suspect I'll cause a confrontation if I just stick my dick in (tempted as I am).  So I start licking his hole, and fortunately, he starts getting hard again.  Not that I'm interested in his release, it is just if he stays horny, I have a better chance of getting what I want (i.e., dick in raw ass).

I start finger-fucking him, that brings a little resistance ("I don't really do that") but it fades.  First one finger, then two.   Time for me to make my move.  I remove the fingers, then start licking again.  He is moaning, and expecting the fingers to go back in.  Surprise, in goes my cock.

I love it.  He squeals like a pig, and his body stiffens like a metal rod, which gives me all the leverage I need for balls-deep entry.  He starts protesting - "hey, I don't get fucked, just want to have some safe fun."  "Me too," I say.  "Now just hold still and be a good boy - it's my turn to pop."

I start fucking his ass and it is tight.  I'm not going to last long, and he can't take much more (I can tell it is hurting him pretty bad - he is not loosening up at all.).

He says, "listen man, please don't cum in me, I got a family to think of."  Right at that moment, I squirt inside him.  Timing is everything!  I hear him say "Oh God, No!" but it's too late.  I'm fully inside him and the geyser is erupting.

"I told you not to cum in me, asshole," he says.  I'm having a hard time keeping a straight face, but I don't want to fight, so I try.  "Dude, you got to say that before a man's in you balls-deep and past the point of no return."  "Fuck that, you ask before you get to that point," he spits back.

"Really, you always asked the girls you fucked for permission before you came?"  He says, "Hell no, but that's different, you little faggot, there are disease issues to consider here."  (Oh, I love it, only gay guys have STDs. - man I do love straight guys.)

"You got nothing to worry about.  Go home to your wife."  He brushes by him, using his shoulder to shove me aside (desperately trying to regain some of his manhood, now), and says "I better not."  He's gone, I'm satisfied.  Everything is good.

Public Sex - Warning and Advice

A buddy of mine was just arrested for propositioning a cop in a public bathroom.  It was in an out of the way bathroom in a downtown hotel known (in the right circles) for sexual opportunities.  I've never been a fan of such meetings for two reasons:  (1) given I like to butt-fuck, it's usually hard to get that done in a public bathroom where people can come and go with little notice and (2) I don't want to get arrested.  However, after some discussions with my buddy, and others familiar with this scene, I thought I give a warning and some advice.

Warning:

Having sex in public places is notoriously risky.  It is illegal, and far easier for cops to prosecute than you may think.  First, sexual contact is not necessary to be arrested.  If the cop can make a case that you were soliciting sex, he can arrest you even without sexual contact.  Remember Larry Craig getting arrested in an airport.  The arrest was based on toe-tapping and a hand being visible under a stall.  Craig (doubtless an asshole whom I am not defending) never touched the cop's crotch or anything like that.  Second, sex where it can be seen by members of the public can get you in trouble, even if you think you have privacy.  For example, getting blown in a car parked on the street (or in a secluded area of a park) can get you in trouble if the cop can see you getting it from a legal vantage point.

Advice:

I have compiled some advice from those in the know about avoiding arrest.  Nothing eliminates all risk (especially if the cop is a gay-hater willing to lie about the sequence of events, etc.).  So, use this advice at your own risk.

(1) At a minimum, allow the other guy to make the first sexual move.  Cops will not generally touch you sexually.  [First, the ones willing to do this shitty work are almost surely straight, and don't want to touch a guy's privates.  Second, if the cop is wrong about the other guy's intentions, it could be sexual assault, or even if the other guy is looking for sex, it may be entrapment.]  Bottom line, if you are standing in the bathroom, and a guy rubs your cock, he is probably not a cop.  (On the other hand, cops are very willing to smile, wink, rub themselves, etc., to try and get you to make a move and get arrested.  Don't fall for it!)  A smile, small talk, etc., is not going to be enough to support an arrest.  So, keep it to that, until he moves sexually on you.

(2)  Suggest going to a walk. If you're in a park restroom, suggest a walk in the woods.  Chances are a cop is not going to leave his equipment, backup, etc., to take a walk with you  Not a guarantee but a good indication.

(3)  Don't be stupid.  If you're 50, fat, and balding, and there is a hot 30-something, clean-cut and built, seemingly inviting you to touch him, get a clue.  It's a cop.

Rationales for Taking the Risk:

So, as I mentioned, this is not my thing.  When I ask my buds, why do this, they respond with two lines of explanation.  First, it opens up a whole new type of guy to play with.  While hotel guys are usually white-collar professionals, the park guys are a mix of blue-collar, ethnic, and professional guys.  Almost always macho, mixes of ages and interests.  Second, guys also love the absence of drama or red tape.  It's quick and easy.  A smile, a rub of a crotch, and you are off to the races.  No exchanging pictures, long chats, wondering if the guy will show up, etc.  Still not worth it as far as I'm concerned, but to each his own.

A Liar Gets What's Coming to Him

The ad was simple enough:

"Married, late 30s, visiting businessman, bottom, looking for similar but top."

Only problem was he was in a hotel on Capital Hill, pretty far for me, but I decide it's worth the subway ride to get a little ass.

At the Holiday Inn (yeah, that should have been a warning for me), "John" (yeah, people still give that fake name) opens the door.  What a fucking liar, he must be in his mid-50s!  This time I decide I'm going to call him out.  Here is the dialog:

"I'm John, glad you could come over."
"Where is the guy who posted the ad?"
"That's me, I'm ready."
"The ad said you were in your thirties."
"Come on dude, everybody shaves off a few years in those ads.  I promise, I'm a real good bottom."
"Listen dude, I don't like being lied to, but since I'm here, I'm inclined to go ahead and fuck you, but only if you keep that pruned-up mug of yours face-down in the pillow, so I don't have to look at it."

He looks hurt, and I feel so proud at calling this motherfucker out.  I say "you want it or not?"  He says, "let's get undressed."  He gets on his stomach in the bed, and I start lubing his hole.  He points to the nightstand, and say's "there's a condom there, I only take it safe."  I say, "absolutely, me too."  I put the condom on, shove his face down in the pillow (reminding him of our deal that he stay face down if he wants to get fucked), slip off the condom and penetrate his ass.  I fuck him a good ten minutes before I flood his ass with cum.

I pull out, and tell him to stay face down, as I don't want to see his face again.  I put my pants on, shoes on, and walk out, leaving my very special calling card of an empty condom on the floor.

I can't resist, on the way home, I stop by the bookstore and check me email.  And, yes, John has written me, and his is one unhappy old fart.  "What the fuck, the condom I give you is on the floor and dry. I told you I play safe ONLY and you said you did too.  What the fuck just happened??????"

I respond as follows:

"Yes, John, I told you that I only play safe.  But, in fact, I only fuck guys raw, planting cum deep inside, where, as we speak, my little sperms are searching in vain for egg in your ass to fertilize.  As far as me telling you that I only play safe, that was a lie, sort of like you being in your late 30's.  But as you said, everybody tells whopper when hooking up.  Don't write me again."

But he does:  "Listen, you fucking little faggot.  I don't get fucked  raw ever.  I'm a lawyer and what you did was rape.  NO CONSENT to the sex act performed - it's just like you drugged me and fucked me.  You going to jail unless you come over here NOW, show me a driver's license so I got your real name and address, go get tested for all FUCKING KNOWN STDs, and show me the results.  Else, I call the cops."

Oh well, we'll go another round:

"Dude, you're not going to call the cops,  As I lawyer, I'm sure you know that the police report would be public, and under my right to confront my accuser, I get to know your full name, address, etc.  And about 15 minutes after I find out, your wife is going to know what you do when you are here in DC (and probably everywhere else  you take you over-fucked ass).  And shortly after that, I'll make sure everyone in your office gets a copy so they know the efficient use you're making of the company travel budget, doing business during the day and getting fucked by random guys in the evening.  I don't have any diseases and I hope you've learned a lesson about lying about your age, appearance, etc."

He did not write back and no cops have busted down my door (yet)....  Who would have thought, me and a "teachable moment."

Musings On Strategy

A commenter asked if I have particular strategies for getting raw ass.  Well, you see some of my strategies in my postings, and over the years, I found some strategies that have some likelihood of success and others very little chance of success.

First, try to delay the discussion of the nature of the fuck (i.e., raw) as long as possible.  Try to avoid discussing the details of the fuck when you are setting up the encounter.  This is for two reasons.  First, some guys are so paranoid about raw fucks that, if you hint that you are interested in a raw fuck, they will refuse to meet you even if you agree to use a rubber.  Second, if the issue is discussed, the guy will usually say that he wants to do it "safe."  Once he takes that position, getting him to let you fuck him raw later is very hard (read: almost impossible).  So, avoid the topic when you set up the time and place.

Even after you arrive, try to delay the disclosure that you are going to do a natural fuck for as long as possible.  Put you  tongue in his mouth, get him undressed, put your cock in his mouth, loosen his hole up with your fingers. The idea is to get his juices flowing, so he wants to be fucked bad.  Your hope is his horniness coupled with your wedding band will overcome any hesitation he has about being fucked naturally.  The best case is that he realizes that you are going in raw when he sees you lubing your cock right before you penetrate him.

Finally, if you are going to fuck a married guy, you should have a wedding band handy.  Married guys often won't get fucked raw by a gay dude because they think that we all have AIDs.  Wear a wedding band, and you have a chance.

Certain things don't work.  Agreeing to fuck with a condom and then not taking one is a recipe for being shown the door.  Arguing with the guy over a raw fuck never works.  If he insists, just fuck him with the condom - it's still a fuck..

Operation Deep Injection – Mission Accomplished

Jim knocks on the door right at 3:20, just like he promised.  Just what I expect from a military boy.  He’s about 25, I’d say.  Close cropped hair and thin body.  He’ll do fine for my purposes

He seems nervous, so I put my left hand on his shoulder and tell him that this is going to be safe and fun.  He doesn’t need to be nervous.  Tell him that no one other than him and me will ever know this happened.  He notices my wedding band and palpably relaxes.  “I’m married too,” he says.  I tell him that traveling on business is my only opportunity to play, and I don’t like to waste it.  He says that he understands completely.

Just to bust his balls a little and set the right tone, I pull him in tight and kiss him in the mouth.  He says he doesn’t really get into kissing guys.  I tell him to get undressed and we’ll get started with what he does get into.

The tee-shirt and jeans come off, and he’s wearing camo colored briefs.  Too fucking hot for words!  I assist him out of his briefs. 

I bend him over the bed and grab the lube.  I start loosening up his hole with my fingers.  He sees me lubing my cock and asks “aren’t you going to use a condom?”  I tell him that my wife is on the pill, so we don’t keep them at home.  That’s why I do other married guys, so I don't have to worry about catching something. He looks concerned but does not tell me to stop.  I view that as a gold-plated doorway for entry, which I drive a Sherman tank through.

I push into his ass and start to power fuck him.  He is moaning and begging for more.  I cum deep in his ass.

He asks if he can shower before he goes home.  I say “sure” and take him to the bathroom and turn on the water.  He gets in and I join him.  I can tell that is not really what he wants, but hell, it’s my hotel room, so I don’t much care.  I tell to wash my dick, and he reluctantly complies, while reminding me that he doesn’t have much time.  I tell him that we won’t be in here long.  My dick is starting to tingle a little from his attention.  I turn him around and soap up his ass.  His hole is still stretched from the fucking, and is nice and soft.  Well, hell, I’m hard again.  I soap up my cock and promptly insert it in him.  He is not expecting that; his body tenses and he cries out.  That reaction makes me even hornier, after about a minute of in-and-out action, I climax.  Another load in his military butt.  I get out of the shower and leave him to clean himself up,  I’ve clearly made him late as he rushes out of the bathroom, dresses, and leaves in a hurry.  After he leaves,  I slip off the wedding band.

MISSION ACCOMPLISHED

Operation Deep Injection – The Prep Work

In order to increase the likelihood of my success in putting my cum deep in the gut of my soon-to arrive military target, I decided to use my secret weapon.  A couple of years ago, while vacationing in Florida, I found myself in a pawn shop looking at jewelry.  I noticed a wedding band.  Average size, gold, with little diamonds across the top.  Not gaudy at all, really quite classy.  It was $50, probably left there by some guy whose marriage had crashed and burned.  I bought it and have put it to good use.

After I began to target married men for my fun and games, I learned quickly that married guys prefer to fuck around with other married guys.  They clearly think that is preferable from both a discretion and safety perspective.  And I aim to please.  If they want a married guy, they get a married guy (well, sort of, at least I’m wearing a wedding band.)

About 15 minutes before Jiim is due, I put the ring on and look down at it.  It looks good on me, real good.

I'm Fucked Up But Not Fucking Crazy

No, I didn't try to fuck the trooper raw.  Cops can do bad things to you, like flashing a badge at the front desk and getting your name, etc.  Thought it was too much of a risk if he figured it out.  So I made up for it by fucking him as hard as I could.  Like so many tough guys I'd seen before, he wasn't going to complain that it was too hard on him, etc.  Too much pride for that.  He just laid there and took it, his face scrunched up like he was getting a tooth pulled without anesthesia.  When I came deep in him and pulled out, I hoped the rubber had shredded, but it was in tact with my semen trapped inside.  He got up slowly and unsteady, then got dressed.  He said that was the hardest he'd ever been fucked.  I told him to come back tomorrow, and we'd see if we could reach another milestone.  He looked doubtful and he did not come back.

Not exactly the conclusion I'd hoped for, but still a good fuck.  But it made me even more determined to drop the load uninhibited in my upcoming military fuck.