Today is the day

I've never taken a boy's ass with a strap-on.

Seriously.

I've come close. Real close. I had the head of my big purple cock inside babyboy's very tight ass. One thrust of my hips and I wouldn't be writing about this cherry of mine. But I was using the harness and dildo a former girlfriend and I had purchased together. We had selected a length and size we'd both enjoy vaginally. I never thought for a moment I'd use its ample length and girth on an ass let alone a male ass.

The truth is I don't feel compelled to play with every ass I come in contact with. And although I maintain a theory that every male is an ass slut or an ass slut ready to happen, I haven't played with many trained for regular ass play.

They all have tight little pseudo virgin asses. None could have taken the girth of my purple cock.

I have enjoyed watching a few of them suck it, pushing my big purple cock deep into their throats.

And then I broke the harness on the girl. *sigh* Good times.

The purple dildo remained in my toy bag and occasionally made appearances in play such as when I tied my sub to a table and forced him to suck it, then masturbated with it before I forced him to suck it some more.

*sigh* Good times.

Could I have bought another harness and a more reasonable sized cock and fucked a boy's ass before now? Sure. But the truth is I have enjoyed the anticipation of taking a boy's ass for the first time.

Perhaps I've nearly romanticized it. I've waited so long and I want it to be with the right guy at the right time.

I can't even type that without giggling at the ridiculousness of that idea but it's probably true. I've been "saving myself."

And today is the day.

Smart boys with waxed assholes

Two nights ago I had a conversation with babyboy that reminded me why I enjoy intelligent boys above all else. They are feisty. They are a challenge. And they are never boring.

Below is our IM chat history about the Brazilian I have planned for him.

Me: I wonder if you'll scream when the guy waxes you. Your asshole that is.
babyboy: the guy?
Me: The waxer. He's male.
babyboy: on come on, cant you have a woman do it?
Me: I suppose I could but he comes recommended.
babyboy: lol...how so?
Me: He does 10 - 15 male Brazilians a week The guy at the salon I called says he sends all his male Brazilians there. To this one guy.
babyboy: you want me on all 4s, while a guy puts wax on my ass and balls?
Me: Or whatever position he wants you in.
babyboy: youre so bad.
Me: You have no idea.
babyboy: that would be very fucking humiliating...
Me: Oh really? Would it? I had no idea.
babyboy: uh huh...lol
Me: I can't wait!
Me: His name is Richard
Me: He was very nice over the phone.
babyboy: fucking a ...you're mean ... cruel ... wonderful.

I tell him the name of the salon and where it's located.


babyboy: i know the place... i was staring at the sign, while i was running on the treadmill...
Me: Well there's a guy in there who is going to rip all the hair off your asshole and balls.
Me: I want you to think of 6 questions you can ask him about the procedure or aftercare that you can ask before the procedure.
babyboy: like what?
Me: LOL. It's YOUR assignment baby. You figure it out. I'll want to see them before we go. So you might want to write them down as you think of them.
babyboy: yes Miss, i imagine, youll be watching it.
Me: Of course I will. And listening to you ask 6 questions about it :D
babyboy: lol...
Me: At least I'm not telling you what to ask. However, if I don't find your own questions to be intelligent, I may replace them with my own.
babyboy: im going to be an attorney, i can come up with very benign questions... whats the temp of the wax, will it hurt, how long will it take to grow back, how long does the precedure take, whats your experience level, and whats your name.
Me: LOL. Maybe 10 questions would be better.
babyboy: how long have you lived in vegas, where did you go to beauty school at, do you get paid by the hr or commision, are tips allowed?
Me: LMAO. Damn. YOU are not playing fair.
babyboy: im good at this...
Me: But ok. I'll give you credit. Damn. A challenge. I love it.
babyboy: i can keep going.. come on....im good stuff like that...i have lots of game.
Me: Clearly. What are 3 questions you could ask him that would humiliate you? Without doing so to him.
babyboy: wouldnt you be more suited to think of them? because i can pose questions, which could be humiliating but, really arent.
Me: It's hot when remind me you're intelligent, I must say. I want you so badly at my feet right now
babyboy: lol....thank you.
babyboy: im good at this stuff though.....my bread and butter.
Me: 3 questions that would honestly humiliate you and not him.
babyboy: should i cut and paste, what i just wrote...the point is a bit moot. dont you think?
Me: I'm asking you to be honest with me
babyboy: what would you like to hear......do you want me on all 4s sir, will you be bleaching my ass, too......if i get hard, will you be mad....
Me: Would that do it for you?
babyboy: my cock did just get alittle semi...

His last proposed question, "If I get hard, will you be mad?" was my favorite because it sounds SO submissive. 

babyboy: what would you do, if that actually happened? if I got hard?
Me: LMAO. What do you think?
babyboy: im sure you would fucking love it.
Me: I would

The player gives up dating for sport

Babyboy is a player. He's in his mid 20's and has enjoyed dating lots of girls who he openly admits he easily wraps around his little finger.

It seems to me he enjoys this little sport, dating vanilla girls. He's a good looking guy who prides himself on staying in shape. He says this is because he's a bartender and it helps his tips. I know those tips are mostly from women and, although I haven't seen him at work, would be willing to bet he flirts his way to better tips. And I'm certain he flirts in a way that makes each female feel special.

Yep, he's THAT kind of player. The non-cheesy kind that plays you before you realize you've been played.

I really enjoy knowing that he's out there playing the confident, assertive guy and wooing women when I know deep down all he really wants to do is be my little whore. I REALLY enjoy knowing that.

Then today babyboy tells me he's done dating girls. That he's all mine.

Part of me is thrilled he wants to give up dating for sport for me. But part of me liked knowing he was out there wrapping girls around his little finger. It amused me.

My boy, babyboy

D/s relationship status: former submissive

Relationship status: friends

Babyboy is one of the first potential submissives I developed a relationship with when I began to consider taking on submissives in the summer of 2008. He's originally from the mid-west and in his late-twenties. He's a bartender and law student.

Read blogs about babyboy.