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missjane2000 46F
13 posts
1/12/2022 6:09 am

Desperation is NOT Good for Boys

Stephen a fantastic sub. Over our time together, I had found lots of interesting ways to push his boundaries and though he offered some resistance, he never disappointed. This particular evening no different.

Stephen and I had gone out for some drinks and found ourselves in a local gay bar, not a place Stephen would've anticipated as he insisted he not interested in men. Enter Jackson. While enjoying our drinks, an adorable man approached Stephen and myself. Jackson sweet and chatty and could not help himself, shamelessly flirting with Stephen all night.

at Stephen I commented, Wow he is really into you.

Stephen, boyishly: Yeah thats not my thing. But if you told me that that's what you wanted from me I would do him in a heartbeat.

Me: Oh? Is that so

Stephen: Yeah only because I feel I need to prove myself to you.

Pondering this for just a moment, it didn't take much, I then looked him in the eyes "Perhaps you should prove yourself."

dumbfounded, Stephen replied, Seriously?

I nodded and to his credit, he jumped right into action. He let down his guard and began to return Jacksons flirtations. Jackson, thrilled to have broken Stephen down, invited us back to his place for a few drinks with he and his friends. Graciously accepting the two of us joined the group headed toward Jacksons home.

The night seemed to go on forever and Stephen growing impatient. He had worked himself up for hours and now it a waiting game. Waiting on Jacksons company to leave, waiting for his opportunity to make me proud. Finally, it just the three of us. Stephen and I sitting on the couch and Jackson on the loveseat. I proceeded to rub Stephen's cock through his jeans as Jackson watched with enjoyment. As he got hard his size becomes painfully obvious, bulging in his pants.

Jackson looks at me and says "I'm sorry I can't take anymore of this can I please go down on Stephen."

Me: "Of course you can."

He looks at Stephen and begins to ask the same. Cutting him off I respond "You dont need to ask him sweetie"

I look at Stephen. Unzip your pants and put your cock in Jacksons mouth
Stephen obediently unzips his pants and pulls out his coc Jackson is practically drooling when he sees Stephen big hard cock, which I have to say .. its impressive. Jackson gets down on his knees in front of the couch and proceeds to go down on Stephen.

Such an eager boy.

After a few minutes he asks if we could please move into the bedroom. When we walk in the room I direct Stephen, Take off your clothes and sit in the middle of the bed. He does as a good boy should.

Jackson has some experimenting of his own hed like to do. He looks at me Ive never made out with a woman before, do you mind?

I pull him over and we make out as I slip out of my clothes and his lips move from my lips down to my breasts. He gently sucks and licks my nipples, rolling his<b> tongue </font></b>around each one. He then asks if I would let him go down on me and try to make me cum. I get up on the bed and lay down next to Stephen ,Be a good boy and show Jackson what he needs to

Stephen proceeds to coach Jackson in just how I like to be pleased orally. Lucky for me Jackson is a fantastic learner and within minutes he makes me cum, my orgasm accompanied by me squirting and exploding all over him and his bed. He squeals and giggles and yells, Oh my God I had no idea women did that. That's Amazing!

Jackson continues to please me and I caress his head telling him what a good boy he is. Each time he makes me cum I tell him what a good boy he is and I can see Stephen is growing noticeably concerned.

Stephens goal is always to be the best boy in the room. Stephen watches and strokes his cock I can tell by the look in his eye that he will take out his concern and frustration on Jackson.

Me: Jackson sweetheart I think that my Stephen needs a attention.
Jackson: Yes maam

Me: Who knew you were going to be such a good boy.
I placed my hand on his cheek Then I moved my hand to the back of his head, firmly but gently, guiding it to Stephens cock Jackson is on the bed chest down wrapping his lips around Stephens cock But it seems no matter how much effort he puts into it Stephen cant seem to get hard enough.

I get up on my knees and whisper in Stephens ear, I am so proud of you such a good boy, look how eager he is, he wants your cock so bad, he is desperate to get you hard.

I can be quite the cheerleader when I need to be.

Stephen's cock gets harder and harder with ever word. He tells Jackson to turn around. Jackson turns around his chest to the bed his ass in the air and Stephen almost panicking puts a condom on slides his cock in without any assistance. Jackson moans.

Me: What a good boy do you like the way that cock feels in the tight ass of yours? You be a good boy and take it as much as he wants to give you. Do you understand?

Jackson nods. Steven is pounding his ass, eyes clenched, occasionally opening them and down but he cant stay focused because Jackson keeps popping up on all fours reminding Stephen who he is fucking. He pushes Jacksons back down forcing his chest onto the bed so he can focus on just his ass. Jackson pops up again and again and the scenario replays itself over and over.

I alternate between the two whispering in their ears. Reminding each of them what theyre doing and why theyre doing it and who theyre doing it for. I straddle Jacksons back forcing his chest to stay on the bed leaning forward whispering in my subs ear.

Me: Such a good boy I'm so going to reward you. God I love watching you fuck him. I love hearing that moan. Are you gonna cum, are you going to explode in his tight ass? In the sweetest tone Stephen replies,Mmhmmƒ

Me: Well lets get on with it, Im waiting.

Stephen: Yes maam. Stephen begins pounding harder and harder. repeating for my sake as well as his own, over and over again Im your good boy. Finally letting out a growl. Jackson who has never played the role of a submissive nor explored the dynamic exhales and collapses on the bed.

Jackson: That fucking amazing! do you have other subs? Could I be one?

I tell Stephen to get his contact information and he does.

When Stephen and I get back to the car we relive some of what just happened, and he lets me know how frustrated he is with Jackson asking to be a sub.

Fast forward three months....

I told Stephen that I wanted Jackson's information because they exchanged it at the end of our adventure. He refused to give it to me. His concern that he may not be my favorite bouncing around in his head made him a possessive. This, being completely unacceptable behavior, led to me ending my relationship with him.

At first, I just got lots of messages about how he wanted to prove himself again and all I needed to do tell him what else I wanted and he would do it. No matter what.

Then I started getting messages from him scenarios that he thought would turn me on and perhaps persuade me into meeting him. And then one day I got a short video.

He had gone back to the bar where we met Jackson several times in an attempt to reconnect with him. And finally he found him and talked him into going back to his house so he could fuck him again, videoing it for me. In the video Stephen tells Jackson he's a good boy and tells him to say hello to me

Stephen: Do you like that Jane do you like watching me fuck his ass? I'm going to fuck him so good for you. Jane likes that Jackson she loves watching me fuck you.

-Miss Jane

# mommydom # love good subs # head # master # bd/sm lifestyle # good boy# forced bi # domme # dom mommy # master # slut # fuck # pussy # love good boys # head # squirt

Latinobuddy01 45M  
3 posts
1/23/2022 1:51 pm

What a great recollection miss Jane of a great encounter. wonder if you would try to find Jackson now hehe

missjane2000 46F
3 posts
1/24/2022 10:58 am

I'd love to find Jackson! He was such a good boy!

opencbusmale1 48M  
2 posts
2/11/2022 11:21 am

mmmm so many things that I want to explore and limits I crave to shatter in this story, Miss Jane!!

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