Lolita Wolf's Predictions & Predilections

As a BDSM Sex Educator and Author, I don't just talk about it. I do it! And then I write about it.

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Straight Boy Gets Fucked in the Ass

October 31st, 2007 · 9 Comments


I used to play a lot with Adam. He was a TES member and a very adventurous player. That was years ago until he moved out West. Now, he’s been back on the East coast for a while and I run into him occasionally. Recently, I got an email from him. He explained that he has a new Mistress and she has ordered him to get fucked by a guy. He would like to comply but is not sure where to find such a guy. Would I know anybody?

Hello! Would I know anybody??? My rolodex doth overflow with all sorts of men who would love to take the cherry of a straight boy.

“Sure, honey, I can fix you up.”
“Oh, great! Will you be there, too?”
“Yes, I want to watch.”
“You could help.”
“No, I just want to watch. And maybe take pictures.”
“You’ll take pictures? My Mistress would love that. You could help, too.”
“No, I just want to watch and take pictures.”

Adam’s a good boy. He deserves an expert. I contacted Jefferson, of course.


Jefferson straddles Adam as he sits on the couch.
“So, you have never been fucked by a guy?”
“Right! That’s why I’m here.”
“Ever have anything up your butt?”
Oh, sure!”
“Ever suck a cock?”
“I’ve sucked a cock or two.”
“A cockatoo? We’re not talking birds here! Have you sucked cock?”
“No, I mean yes. Once or twice when a Mistress forced me to do it.”

I am suppressing a guffaw. I think Jefferson is funny. Adam is very nervous. And it does not help that Jefferson is asking questions and chewing on his neck.

All this time, I am watching and taking photos with Adam’s camera. His Mistress is keen on the idea of getting photos of the event. But I am not doing it for her as much as for myself. I love taking photos of people having sex. You’ll never see the photos here. They’re private. Usually I am not using my own camera and often I don’t even get copies.

“Hey, guys,” I interrupt. “This camera says ‘memory full’ and I only took like six pictures.”
“Let me see that.”
I hand the camera to Adam.
He looked at it. “My regular camera wasn’t working so I got this instead. I don’t know why it isn’t working.”

Jefferson piped up, “We can use my camera,” and handed it to me.
Adam agreed, “That would be great.”
I was concerned, “Adam, you do realize that now Jefferson will have possession of the photos.”
“Yes, I understand. I trust him. I trust you. That is why I contacted you in the first place.”

“OK, boys, carry on.” I began shooting again.


The boys are naked on the bed. I am prancing around with the camera getting shots from all angles.

“I want you to suck my cock,” Jefferson tells Adam.
Adam voraciously gulps Jefferson’s cock.
“Whoa, slow down! You’re going to be doing that for 20 minutes.” Jefferson eyes the clock.

I’m shooting with the camera and the pictures look good. I mean, it looks like that boy can really suck cock. However, in reality, he is gagging and not very good at sucking cock at all. Apparently, that is not a problem for Jefferson. He is rock hard. Afterwards he explains to me that the cocksucker’s enthusiasm is about 80% of it for him.

There is much cocksucking in a variety of positions. At some point, Jefferson has put on a glove and is using some lube to warm up Adam’s butthole. I circle around getting lots of pictures. After 20 minutes of cocksucking, Jefferson announces, “I am going to fuck you now.” Yes, it is like an announcement. Like an announcement of intention. Like, this is it. Last chance to turn tail and flee.

But Adam is willing, very willing. And he takes Jefferson’s directions to position himself. Jefferson struggles with the condom packet. His fingers are just very slippery from the lube. I tear it open and hand it to him and he slides it over his beautiful hard cock. Jefferson’s slips it in to Adam’s butthole and it glides in. Soon Jefferson is fucking him hard and fast. Adam is working his butt forward and back for Jefferson.

I am propped up at the head of the bed with the camera. The boys are fucking at the foot of the bed. I have a great view. I say, “Adam, you really like this.”
“It sure looks that way, doesn’t it?”
I am disappointed with that answer. “I want to hear you say that you like it.”
He doesn’t answer me at all. I don’t push it. We negotiated fucking, not domination.

I continue taking pictures.

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9 responses so far ↓

  • 1 Jefferson // Oct 31, 2007 at 2:25 pm

    He also gifted me a very large bottle of bourbon, which is really all the foreplay I need.

  • 2 Jocasta // Oct 31, 2007 at 4:19 pm

    I wanna see the pictures!

  • 3 Lolita // Oct 31, 2007 at 4:35 pm

    No, Jocasta!

  • 4 Cub // Oct 31, 2007 at 7:45 pm

    Thankyou for sharing, that was really hot!

    Only wish there was men like Jefferson known to me in Sydney!

  • 5 adam // Nov 3, 2007 at 12:43 pm

    yes, it was really hot…enjoyed it more than i expected…

  • 6 petboy // Nov 9, 2007 at 8:13 pm

    Wow…. it’s fantasy of mine too… though i’d want the domination too!

    Please tie me up, and then fuck me, Jefferson!

    … running away, somewhat scared…

  • 7 sunny // Aug 1, 2010 at 10:14 pm

    That shit was so hot my prick still hard wish it was more

  • 8 Megs // Feb 13, 2011 at 7:43 am

    wish there was someone here in Durban to do that to me.I would love to experience being fucked in the arse and totally dominated

  • 9 Mistress Anne // Apr 30, 2011 at 12:26 pm

    So hot. Just what I like to see.. and do.. 😉

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