It was strange, he contacted me first and his profile stated he was looking for a domme or trans to submit to. I guess the hidden desire to please a man won out. We communicated through mail and messenger for months. We even met for coffee and some groping, where I tested his desire for nipple play, some severe pinching and even squeezed his sac to express the control I wanted and what he could expect.
His affection grew with each interaction and finally the desire to consummate the bond was overwhelming for both of us.
We had made arrangements to meet when both of us could be gone for most of the day. I had rented a motel room and wanted something with a couch but that wasn’t available. There was a desk and chair that would do.
I was the first to arrive and when he came in I told him to go into the bathroom and dress. I had previously decided that I didn’t want him to wear lipstick because it would limit kissing, but I had changed my mind since I had planned to bring some solvent to clean off any remnants on my lips. When he walked out of the bathroom and presented himself in his feminine attire, I was amazed.
He was gorgeous, at least in my eyes. I grabbed the back of his head and pulled him against me, crushing his lips in a violent manner while pushing my tongue inside his mouth. He responded as I expected, after all, this was exactly what he had been searching for.
I took my other hand and grabbed his ass, pulling him completely against me and the result was that my now hard cock was pressed against his crotch. I ground into him conveying the fact that he was going to get fucked, and fucked hard. He knew this and responded with his kiss and his body, both punctuated by a passionate moan.
There was a lot of groping on both sides; I squeezed his bra, feeling for and finding the nipple. A shudder and moan indicated the nub was between my thumb and finger. With my tongue still buried in his mouth I began pinching, slowly increasing the pressure, waiting for an indication of a limit reached. The only response was his tongue frantically attacking my tongue and his mouth salivating in desire. The endorphins from the pain on his nipple only aroused him further.
The passions were escalating to the point where it was time to take it to the next level. I broke the embrace, stepped back a little and raised my arms over my head. It took him a moment to understand, and then he pulled my shirt over my head.
The desire was too much; he tenderly placed his mouth on my nipple and began sucking, like a baby on its mother’s breast. The feeling was as I remembered from past events, the tingle that ended in my cock which made it even harder. Finally having enjoyed his adoration, and wanting more, I pulled him off my nipple and pushed his head down. He dropped to his knees and frantically began unbuckling my trousers.
He was trembling as he pulled my pants down. When I had stepped out of them he reached up for my briefs. I said, “No hands.”
A moan escaped his mouth as his teeth began pulling on the elastic, first one side and then the other. When the top cleared my cock it sprang up against his cheek. He desperately wanted to touch it with his lips, but he knew better, so he settled for a brief press against his cheek. He finished pulling them down and watched as I stepped out of them. Then as I stood nude before him, he looked pleadingly up at me. I nodded and he bent forward to taste his first cock.
He was quivering and almost drooling when he opened his lips and placed them on the end of my cock. I was aroused and a small amount of pre-cum was present which he sucked out. The feeling of the vacuum on my urethra was very erotic.
Finally, what he had dreamed of, he open further and took all he could of my cock in his mouth. The vibrations of his moans added to the feeling. He was experimenting, pulling back while sucking and then plunging forward to take it all in. I reached down and grabbed his head, holding it still while my cock was as far as it would go in his mouth. Then I told him to yawn and as his throat opened up I pushed just the tip of my cock into his throat. He gagged and I quickly pulled out. “You will learn in time to take all of it.”
I helped him to stand and then pulled him over to the chair. I sat, reached under his skirt and pulled his panties down. I know he preferred to leave them on and just have them pulled to one side, but I wanted to see all of him. I told him to lift his skirt and hold it so I could examine him. He stood there like a shameless hussy which he was, presenting himself to me. I cupped his balls and with my other hand I stroked his cock. He was nervous and not hard, but with some attention he started to respond.
I had him hold his cock up out of the way so I could work on his balls. I took both hands and felt his sac above his balls. When I found his cords, I pinched them and pulled down; squeezing any remaining sperm back to his balls. I had a doctor do this to me when I was contemplating a vasectomy, it left my balls tingling all day. I wanted him to feel the same thing. I took both hands and with thumb and forefinger, I grasped his balls which now had some feelings he had never felt before. I know it never crossed his mind that I might want to suck his cock, but he was there for my pleasure. As he wondered what was coming, I bent forward and took his cock in my mouth.
As I covered his cock I felt it begin to harden. I worked on it and as he became aroused I squeezed his globes. I thought he would go soft but instead he moaned. He really did crave some pain, at least moderate to release the endorphins. I continued to suck him and I felt him stiffen.
He cried out, “Sir.” I continued to suck until he exploded in my mouth. I sucked him dry and then stood up and pulled him to me. As I kissed him he opened his mouth and I deposited his ejaculate inside it. His tongue worked to clean the sticky sperm off mine. I broke the kiss and looked at him, he knew enough not to swallow, we had discussed this before. I pinched his nose so he had to breathe through his mouth. With his mouth becoming full of saliva and his sperm, I allowed him to swallow.
Before we went any farther, I rolled a condom on his semi hard cock leaving a good inch of the end hanging to catch any further ejaculation which I had no doubt would happen.
I pulled him over to the chair and placed him behind it. I had him bend over it and spread his legs. I lifted his skirt and laid it on his back. I spent several minutes just looking, watching his reaction, his anus was slightly clenching from anticipation.
He said he would douche before we met so I decided to check. I pulled his cheeks apart and smelled, I couldn’t detect any smell at all. I took my tongue and touched his anus. He moaned and relaxed, I pushed in a little and couldn’t taste anything. I was glad he did what he said he would. I spent some time playing with his anus with my tongue, bringing him close to begging and possibly orgasm. I blew on his pucker and stood up.
He had asked for some spanking and since he was obeying agreed-on terms to the letter I decided to reward him, he would be the judge if it was a reward. I reached under him to hold his cock and then brought my hand down hard on his ass. He yelped, he had asked for some light spanking, but that wasn’t in my plan. I continued to thrash him until his cheeks were a rosy red. I doubt if that was what he had in mind, but it was what I had envisioned.
Now it was time for what we both dreamed of. I took the lube and coated my middle finger, and then just rubbed it around the outside of his sphincter. He was beside himself. He was trying to open his anus and coax penetration, I didn’t respond, happy for the moment to feel the hard muscle and enjoy his frustration of being denied. I slowly increased the pressure on the muscle, watching it dilate in uncontrolled passion.
When he started to shake, I plunged my finger all the way inside him. He clamped hard on my finger and grunted, not in pain but passion. I ceased all movement and let him enjoy and adjust to being impaled for the first time. I pulled my finger out and squeezed a dollop on his star shaped opening. I began small penetrations, working the excess lube into his passage.
When all the lube was inside him, I began exploring. The first thing I did was pull my finger out slightly and rub across his swollen prostate. He gasped from the jolt of electricity that coursed through his body just as I knew he would.
I continued working his passage and was careful to avoid that tender gland. I concentrated on the sphincter, by bending my finger I could feel the inside of the ridge of muscle. I felt the full circle of the now quivering muscle, pinching and squeezing it which resulted in dilation. He was enjoying this as much as I was. I pushed back into him the full depth of my finger. Now I rotated and felt the walls of his colon. He and I were both thinking what those walls would feel like when impaled on my cock. There was so much to explore, and so many new adventures.
I pulled my finger out and pushed it back in with another alongside. The pair easily buried in his slightly dilated opening. The fingering had aroused him even more, he was almost begging now. He knew what milking was and I decided to give him a firsthand experience.
I grabbed his balls with my other hand and squeezed just enough to give a feeling, and then began a severe stroking of his prostate with my two fingers. I felt him responding and could see his cock get hard again. I kept it up and when it looked like he was about to orgasm, I increased the pressure on his globes until he grunted and his cock started to soften.
I never stopped the massaging of the now swollen gland, pressing harder yet until I saw some fluid escaping into the condom. I continued milking him while squeezing hard on his balls until no more fluid was stripped from him. This might have been cruel, but I thought the numbness of his cock and balls would distract him of the pain from being penetrated for the first time.
I coated fingers on both hands and pushed two fingers in his anus with my right hand and then with a little difficulty two more from my left hand. The intrusion of four fingers took some time, I took my time to keep any pain to a minimum, I wanted the pain to happen when he surrendered his virginity.
With four fingers in his opening, I began pulling sideways to stretch the muscle. I had my fingers buried to the second knuckle which allowed me to bend them into hooks for anchoring while pulling them apart. I kept this up until I could actually look inside his colon and see the walls. I pulled my fingers out and quickly replaced them with four fingers from my right hand; he was now dilated and ready to be impaled.
With my left hand I coated my cock heavily with lube, spread his cheeks and removing my fingers, placed the tip on his greasy anus. I reached under, grabbed a nipple, and leaning forward whispered in his ear, “Are you ready to lose your cherry, I am going to take it.”
He moaned a faint, “Yes”.
With just a little pressure I felt him relax and the head slipped in. I let him get used to that. I knew he thought that his cherry had been taken and that he had performed perfectly. Little did he know that it was the easy part, I had prepared him as much as possible for that but the real deflowering was yet to come.
I then pushed a little more and felt the resistance of the inner sphincter. “This might hurt a little when I take your Maidenhead.” I pushed a little harder keeping pressure on the reluctant muscle but not forcing it. I could feel him moving trying to find a way to allow me in but there was no entrance.
I thought maybe with position the sphincter would dilate and allow penetration, but that didn’t happen. There was only one way now to achieve entrance. I grabbed his hips, told him to push out, waited until I thought I felt a slight dilation and then rammed my cock through the barrier.
He screamed in surprise and pain, I stayed still while he adjusted to the new sensation of penetration. I felt him push back a little as an indication he wanted more so I slowly pushed in until my cock was over his prostate. I could feel him clamp down and moan from the sensation only a man could feel. When he had calmed down, I buried my cock fully inside him. I bent down and nibbled on his ear. “Good girl.”
I pulled out until I felt the head at the inner sphincter and then pushed back in. I could tell he felt it when it went over his prostate. I began a steady rhythm of fucking, enjoying the contractions of his man cunt and the moans of pleasure from his throat. I left his nipple and found his cock; it was starting to get hard in spite of the milking. He might not have any juice left to ejaculate, but he would enjoy a dry orgasm.
The pill was keeping me hard and prolonging my orgasm. I picked up the pace and began a royal fucking, withdrawing and slamming hard into his ass. He was moaning unintelligible grunts of encouragement. This continued until I finally had to let go and cum. I gave one last deep push and let my seed enter his dilated contracting cavity.
I felt his cock jump also and knew he had reached his peak also, whether it was wet or dry didn’t matter, he enjoyed it. I left my cock in him, enjoying the feeling of the walls grasping my now tender cock. I let it soften on its own and finally slip out of him.
I lay down beside him and pulled him onto me, cradling him as he came down from the high of his first fuck. As he lay on me I reached over and got the home made plug I had made, the exact size of my cock. I found his anus and pushed it into him until the flange nestled against his anus. “Keep this in until you go to bed and use it after that any time you want, it is yours.”
I pulled the condom off his cock and placing the end in his mouth, squeezed out the juice I had milked out of him. When it was empty, I kissed him and pushed my tongue in to taste his cum. I pulled away and told him to swallow.
“Next time it will be my cum in your mouth."
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