Desperate 10

*This is a true story only the names have been changed to protect the identity of those involved.

Stephen was 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 was no different...

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

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

Stephen, boyishly responds: "Yeah that's 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 a moment I look him in the eyes "Perhaps you should prove yourself."

Looking rather dumbfounded, Stephen replied, "Seriously?"

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

The night seemed to go on forever and Stephen was growing impatient. He had worked himself up for hours and now it was a waiting game. Waiting on Jackson's company to leave, waiting for his opportunity to make me proud. Finally, it was 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 him."

To which I respond: "Of course you can".

He looks at Stephen and begins to ask him the the same question. Cutting him off I interject: "You don't need to ask him sweetie."

I look at Stephen. "Unzip your pants and put your cock in Jackson's Mouth"

Stephen obediently unzips his pants and pulls out his cock. Jackson is practically drooling when he sees Stephen big hard cock. 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 enter the room I direct Stephen "Take off your clothes and sit in the middle of the bed." He does as a any good boy should.

Jackson has some experimenting of his own he'd like to do. He looks at me "I've never made out with a woman before... do you mind?"

I pull him into me 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 tongue 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 "Stephen, Be a good boy and show Jackson what he needs to do."

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 reiterate what a good boy he is and I can see Stephen is growing noticeably concerned.

Stephen's 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.

I pull Jackson head up: "Jackson sweetheart I think that my Stephen needs a little attention."

He responds: "Yes ma'am."

I encourage his continued good behavior " 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 Stephen's cock. Jackson is on the bed chest down wrapping his lips around Stephen's cock. But it seems no matter how much effort he puts into it Stephen can't seem to get hard enough.

I get up on my knees and whisper in Stephen's 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 barks at 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 little ass of yours? You be a good boy and take as much as he wants to give you. Do you understand?"

Jackson nods. Steven is pounding his ass, eyes clenched, occasionally opening them and looking down but he can't stay focused because Jackson keeps popping up on all fours reminding Stephen who he is fucking. He pushes Jackson's 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 continues to replays itself over and over.

I alternate between the two whispering in their ears. Reminding each of them what they're doing... why they're doing it and who they're doing it for. I straddle Jackson's back forcing his chest to stay on the bed leaning forward whispering in my subs ear. "Such a good boy I'm going to reward you....God I love watching you fuck him. I love hearing that moan. Are you gonna cum for me, are you going to explode in his tight little ass?" In the sweetest tone Stephen replies "Mmhmm"

My tone changes from sweet to impatient "Well let's get on with it I'm waiting."

Stephen replies: "Yes ma'am." He begins pounding harder and harder. repeating for my sake as well as his own, over and over again "I'm a good boy." finally letting out a growl. And Jackson who has never played the role of a submissive nor explored the dynamic exhales and collapses on the bed.

He is weak but excited: "That was 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. No doubt his concern that he may not be my favorite bouncing around in his head had made him a little possessive. This, being completely unacceptable behavior, ultimately 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 was tell him what I wanted and he would do it... No matter what.

Then I started getting messages from him played out 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 "Say hello to Jane." Then he addresses me "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