tagFetishFisting My Young Man

Fisting My Young Man

bygreasycat©

I told the young man we were to meet in a motel room. We both love meeting that way. There is something particularly sexy and forbidden to me about motels. I've always admitted a peculiar fetish for them. The fact that it’s neutral territory. No real life interruptions or distractions. The knowledge that untold numbers of other people have had sex in this same room. Not to mention that I don’t get stuck washing the towels and sheets. 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.

I heard his knock on the door. Right on time. Good boy. Although it’s sometimes nice to have an excuse to punish him from the outset. Not to worry. I always discover or invent some transgression on his part that warrants attention. 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 pretend to be firm, but he knows how turned on I am. The fact that he is in his 20’s and I am 40 makes me appreciate him all the more. His young body makes me hot beyond belief, and his tight ass is my prize.

I tell him to get undressed and lie face down on the bed for me. I never fail to watch admiringly as his naked body is revealed. Then without another word, he crawls onto the bed and into position. He knows just how I like it. It’s the way he loves it too. He draws his knees up under himself slightly so that his ass is raised and spread open for me. I sit down beside him and caress my hand over the hot flesh of his taut butt. I feel him flinch and shudder slightly at the first feel of my warm hand on him. I ask him if he has been doing the tasks I set out for him. 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. He lets out a soft low moan as my fingers find his puckered asshole and begin tracing long lazy circles around it. 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.

I draw my hand back and give his ass a good hard slap. I tell him it looks awfully tight to me. SMACK I lay another slap into his cheek. 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 tell him I will be the judge of that.

Smearing some lube on his hole, I place the tip of my index finger on his tight rim. Instead of slowly working it in like I usually do, I suddenly jam it all the way in as far as it will go. He tenses and groans as I feel his ass tightly grip my finger, almost sucking it in with the tension. I tell him he knows better than to get all tense as I plunge my middle finger in beside the first one. I pull them out about halfway, and thrust them back in again quickly. I watch the muscles of his back relax, feel him settle down and his ass begins to open up for me. I add a third finger and begin a slow rhythmic motion in his hole. 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. His hips rise slightly to meet my thrusting fingers and his thick cock is rock hard.

I pull my fingers out and wipe them dry on a towel as I watch his ass pucker back closed. Without giving him a second to tense back up, I pick up a large, thick vibrator and slide it halfway in. It’s circumference shocks him, and I watch his hole stretch. I hold it there a moment, and begin firmly applying more pressure, pushing it deeper. 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 smack his ass cheek hard and demand he keep still. Tell him he is my male ass slut. Does he need the indignity of being tied up? I thought we had passed that point as he was learning to have his ass used. He pulls his arms back in front of himself, in the position he belongs in. He apologizes, begs his mistress’ forgiveness and swears he wants to be used. Tells me he loves the feeling of being totally filled. I reply by burying the vibe all the way to it’s end. Then I turn the switch and listen to the muffled hum as it buzzes deep inside of him.

While he moans quietly, eyes shut and ass humping the air slightly, I ask him how he would feel if someone could see him like that. Young, but still a grown man. Not a gay bone in his body. Proud owner of a nice hard cock. Being used like an anal whore by me. Following humiliating orders given by an older woman. How embarrassed would he be to have someone see him with a vibe buzzing deep in his intestines, my handprints glowing red on his skin from taking a spanking. He groans and tells his mistress that it would be awful. I lean down close to him. I lightly touch his strong back. I whisper softly in his ear to open his eyes and look up.

Standing there beside me, holding a video camera is his girlfriend’s mother. We all live in the same neighborhood. That’s how this whole thing between he and I came to be. Of course he can’t tell his friends about us. We can't exactly go out together. He can’t take me to bars full of college aged people. Our relationship is so different and special. We understand how it works. He has to have a girlfriend his own age. I accept that he fucks her like the twenty year old girl she is. The two of us share our own private secret. He and I know of course that she isn’t mature enough to give him what he really needs, so his ass belongs to me. His girlfriend’s mother knows about us though. She and I have known each other since he was a child. He didn’t have a clue however, until this very moment.

His face turned a deep red, his mouth opens in shock and astonishment. I notice his erection has wilted like an ice cream cone on an August day. He looks at me in disbelief, then back to her. I can see his confusion mingling with his embarrassment. He doesn't know quite how to react. I enjoy his discomfort. She keeps the camera running and laughs. Tells him she is shocked that the nice young man she trusted her daughter to be with has turned out to be such a sex freak. I explain to him she had been hiding in the bathroom the whole time, taping us through the half closed door. Then I suddenly pull the vibe out of his ass and tell her to look at that wide open gaping hole. Get a good picture of it I tell her, holding his cheeks wide apart. She tapes for a few moments, moving around to get several different angles. Then she tells me she thinks I could probably get him open wider. Much wider she says with a wink.

He still can’t believe it. His blush has spread down to his shoulders. He buries his head in a pillow and begs me to stop. The other woman and I laugh and I tell him to get used to it, we are all going to watch the tape together very soon. But I needed some more action in my little movie first. She drew a chair up close beside the bed, sat down and continued to tape as I prepared my next move for her daughter’s boyfriend.

Spreading his legs wide, and inspecting his ass, I saw that the interruption had made him shut back up tight as a clam. I whispered to him that I thought a good hard fucking would do what I needed. He began to plead and beg as I fastened the straps of the dildo harness around my waist and legs. I gave the dildo a good twist to make sure it was secure, as I applied a dab of lube on the tip, crawled between his legs, and positioned the head against his asshole. I leaned forward, feeling the resistance, leaning a bit more weight into him, and the resistance gave way. He shuddered and let out a long throaty groan as I sunk the strap on into him up to the hilt. I held it there a minute, massaging his ass with both hands, urging him to relax and open wide, calling him my sweet baby, telling him how I owned and loved his ass.

His tense body gradually eased it’s clinching and I withdrew halfway, and gently pushed back against him. I pulled out a bit more each time until each stroke was thrusting the entire length of the dildo into his willing dirt hole. His body couldn’t fight the waves of pleasure it felt. The girlfriend’s mother, the video camera, his exposure and embarrassment were all overshadowed by the feeling of having his ass fucked by his mistress. His groans of discomfort had turned to moans of pleasure as he bucked his ass up to meet my hips.

Pulling out, I told him to turn over. Lying on his back, I took his legs and put them on my shoulders, rolling him back until his ass was easily within my reach. I told him I needed to look at his face and hard cock as I used his willing slut boy ass. I re-inserted the dildo and began to rock against him. Only now I was doing it harder. I pushed against his legs for leverage as worked my hips faster. I was going hard and deep, faster with every thrust. I began to feel the little beads of sweat break out on my face as I started slamming him as hard as I could. I looked down past my jiggling breasts and watched his hard cock twitch and jerk with every movement of my reaming. I studied how his face contorted in an expression of pain mixed with pleasure. His hole was wide open and I pounded him until I was nearly exhausted. He began to beg me to let him jerk himself, beg me to jerk him, anything just please allow him to cum.

I glanced at the woman with the camera and nodded my head. She had gotten out of the chair when I had turned him over and was circling the bed, taping from every angle. She put the camera on the dresser, aimed at the two of us and left it running as she knelt on the bed. I leaned back a bit, letting his legs down just enough for her to reach his throbbing hot cock with her mouth. As she took the head in her mouth and began to suck, I slammed the huge dildo into his butt harder than ever. Bucking with wild spasms he tangled both hands into her hair and pushed her head all the way down on his aching cock as he moaned and thrashed wildly on the bed. I could hear him crying out for her to suck his dick, while he begged me to fuck him. She sucked him deep into her throat as I continued to split him. Then his body tensed like a coiled spring. My friend pulled her mouth away just as the first spurts of his hot load began shooting. She caught a stream of it against her face, then pointed the spurting cock at me as I felt the warm jiz plop on my tits. The last stream hit my belly as I withdrew the strap on and admired his gaping ass.

He was still panting, gasping for breath when I told him to turn back over on his stomach. I had never used him this much, and wanted to push him to his limits. He told me he was spent, that his ass was throbbing, and could his mistress give him a break for a few minutes. Without saying a word, I walked over to where he had left his jeans in a heap on the floor. I pulled the belt free from the belt loops and walked around to the head of the bed. I leaned over, the strap on just inches from his face and asked him if he wanted to lick it clean. Oh no he protested. He told me I knew he didn’t do that, reminded me of his limits. I asked him if I was his mistress. Asked him if he was truly my ass slut. Asked him who owned his ass. He told me I was, and with trembling lips opened his mouth. I moved away. I told him that was all I needed to hear. Just knowing that he would have done it was enough for me. I respected his limits, but wanted to remind him of his place at the same time.

I kept the belt handy as I unbuckled the dildo and put it aside. I walked behind him, and brought the leather belt soundly down across his ass. He jumped and yelped. Asked me why I had done that. I told him it was because I had felt like it, did he have a problem? He meekly replied that his mistress could do whatever she pleased. I put the belt down and pulled his legs wide apart. Sitting down between them, I got comfortable on the bed. I took the lube and began to soak my entire hand with it, working it between the fingers and all the way to my wrist. I told the other woman she may want to get some close up video of this.

As she settled in with the camera, I parted his ass cheeks with my dry hand. Then I squirmed three lubed fingers deep inside. The dildo had worked him open nicely and he was ready for whatever I had in store for him. I tucked my little finger under the three already inside, and slowly worked all four back and forth in his ass. There was none of the roughness or violence of my dildo fucking. I worked patiently but firmly until I felt his ass giving way and accepting my fingers. I tucked my thumb up and began to slowly twist my hand into his ass. I would get all the way to the knuckles, and retreat. Pushing back slowly again, more firmly each time. Finally on one push I got past the stretched hole with my knuckles. The rest of my hand slid in easily to the wrist.

He was breathing deeply, trying to stay relaxed, wanting to accept it, and when my entire hand disappeared in his ass he gave a deep groan that told me he was in another zone entirely. I felt his ass close around my hand. Knowing he was feeling filled like never before. I waited for his panting to slow and began to slowly flex my hand inside him. He moaned like a cheap porno actress, only I knew he was feeling something so deep and intimate he was totally unaware of any sounds coming out of his mouth. I pulled my hand out about halfway, and then pressed it back inside. The muscles of his ass had a grip on my hand like it was being milked. I pulled back and pushed back again a bit faster, a bit deeper.

I looked at his face. There were tears in the corners of his eyes, his mouth was open, he was panting and moaning, but he never asked me to stop. I thrust my hand in and out again faster and he let out a strangled scream. I did it harder and deeper. He cried out and begged me to stop. I punched his tortured rectum again with my fist. Then one more time, burying my fist deep past my wrist. He screamed, his eyes were filled with tears and he finally called out our safe word. I stopped immediately, and slowly withdrew.

His ass gaped open wide as a canyon. I asked him if he could feel the cold draft in his hole. My friend took video of it all as his muscles finally regained their memory and began to close his shit hole back to it’s normal clench. I rubbed his cheeks and back while he regained his composure and told him what a total ass whore male tramp he was. Told him how much I enjoyed it. That I knew he loved it too.

I stretched out on the bed beside him. He was still too spent to move. He knew what I would do though. I would caress his body, paying attention to his ass in particular, all night. I would have him make me cum over and over. By morning his anus would be better and ready for more. We would watch the videotape together and he would tell me what he liked best. He would make his request of what he would like to do next.

My friend got ready to leave and came over and kissed him on the forehead. He blushed deeply at her touch. The reality of their relationship both embarrassing and exciting him. He grinned shyly and thanked her. She told me she would see me at the neighborhood watch meeting. She smiled at him and told him she would see him Saturday night when he came by to pick up her daughter.

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bygreasycat© 0 comments/ 146846 views/ 20 favorites

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