His groan has given way to panting and gasping now, and as a reflex without thinking, he reaches behind himself, flailing with one hand, trying to push my hands away. I hold it there a moment, and begin firmly applying more pressure, pushing it deeper. It’s circumference shocks him, and I watch his hole stretch.
Without giving him a second to tense back up, I pick up a large, thick vibrator and slide it halfway in. I pull my fingers out and wipe them dry on a towel as I watch his ass pucker back closed. His hips rise slightly to meet my thrusting fingers and his thick cock is rock hard. He is now moaning softly as he moves through the stages of first tolerating it, then getting used to it, getting off on it, and finally loving it. I add a third finger and begin a slow rhythmic motion in his hole. I watch the muscles of his back relax, feel him settle down and his ass begins to open up for me. I pull them out about halfway, and thrust them back in again quickly. I tell him he knows better than to get all tense as I plunge my middle finger in beside the first one. He tenses and groans as I feel his ass tightly grip my finger, almost sucking it in with the tension. Instead of slowly working it in like I usually do, I suddenly jam it all the way in as far as it will go. Smearing some lube on his hole, I place the tip of my index finger on his tight rim. As he stammers and swears he has slept with the plug in his ass as I have ordered, I watch the imprint of my handprint turn from pink to red. I draw my hand back and give his ass a good hard slap. He tells me he is my ass slut, that I am his mistress and he has been working his ass over and over for me. He lets out a soft low moan as my fingers find his puckered asshole and begin tracing long lazy circles around it.
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Working objects into his ass when he masturbates, concentrating on the full feelings in his anus as he jerks his cock thinking about us together. I ask him if he has been doing the tasks I set out for him. I feel him flinch and shudder slightly at the first feel of my warm hand on him. I sit down beside him and caress my hand over the hot flesh of his taut butt. He draws his knees up under himself slightly so that his ass is raised and spread open for me. Then without another word, he crawls onto the bed and into position.
I never fail to watch admiringly as his naked body is revealed. I tell him to get undressed and lie face down on the bed for me. His young body makes me hot beyond belief, and his tight ass is my prize. The fact that he is in his 20’s and I am 40 makes me appreciate him all the more. I pretend to be firm, but he knows how turned on I am.
As he enters the room and addresses me as mistress I try not to be too obvious in just how happy I am to see him. I always discover or invent some transgression on his part that warrants attention. Although it’s sometimes nice to have an excuse to punish him from the outset. As I always have a supply of lube and toys at the ready, making a mess with the towels and sheets is a happy result of our meetings. Not to mention that I don’t get stuck washing the towels and sheets. The knowledge that untold numbers of other people have had sex in this same room. No real life interruptions or distractions. I've always admitted a peculiar fetish for them. There is something particularly sexy and forbidden to me about motels. I told the young man we were to meet in a motel room.