Blackmailed Crossdresser , part II

A few weeks after that first incident with Stefan where he had blackmailed me into having sex with him, I got a text message off him. I was a bit surprised, as we had managed to ignore each other in work. I was growing optimistic that this incident was behind me. Even though it was left me feeling violated and with lots of confused feelings about myself.

I was shocked to open the message on my phone and seen two pictures of him fucking me in the hotel! I was on all fours on he bed, in bustier, stockings and heels, with a wig on but visible to see.And he was behind me, obviously fucking me. This wasn’t ambiguous. What had he done? There must have been a secret camera on that dresser opposite the bed. He then messaged me again: “there is a video that goes with these images. we have a problem it seems. but I am sure we can work kit out”

This would be the beginning of his exploitation of me.

I agreed to meet him again. I was already prepared in my head to let him fuck me once more. I had managed to get through the last time, in reflection, the cock-sucking wasn’t so bad. It was the anal that hurt. If that was the price of buying him off, then I could do it one more time. But I would pick the place, I told myself.

But in the end he didn’t want to meet in any hotel, either of my choosing or his. We met in a café. He told me he would keep the video a secret, protect the truth of my transvestism, and all he wanted in return was to be involved in my crossdressing. To see more pictures as I made them, to be allowed to by gifts of clothes for me and make requests. And to occasionally be allowed to show his appreciation physically.
Though I was sceptical about letting him further into my life and I already knew what he meant by his last request, I agreed to go along with it.
I felt I didn’t have any other options, and also thought if I played along for a while he’d either get bored, or I would get a chance to steal back the material he had on me. And I admit there was a part of me that was a little excited to have an audience for my crossdressing after years of experimenting in secret on my own.

About a week later a box came from an online shop. It was a a pair of very small denim short shorts, a little bit slutty and tacky looking with some thin gold chains hanging at the front, and a long red and blonde wig. A message followed from him requesting pictures, and demanding I make it “sexy”. it was strange to have some else picking out clothes for me to wear, but I found it kind of exciting. I also found the shorts and wig pretty sexy. I couldn’t wait to try them on. That evening I painted my nails and dressed up in nylons and the short shorts. I put on the wig and took a few pictures on my phone. I sent them over to Stefan.

Half an hour later he rang me up.
“Come over to my place and bring exactly those clothes. I want to see how they look in person.”
I deliberated for a while whether to follow up on his request. I knew what might be in store, but I was not only scared of him following through on his blackmail, but also a little bit flattered by his interest in how I looked when I crossdressed.
An SMS arrived with an address…

Within an hour I was over at his place and dressed as I had before, but now standing before him as he relax on an armchair. His hand on the obvious bulge in his jeans he asked me to pose a bit. Turn to the side, turn around and look back at me, bend over a bit, that kind of thing. At one point, when I was half bend over to my ass protruded, I heard the zip on his jeans open. When I looked back I saw he had taken his cock out from his jeans and he was slowly stroking it. I noticed how hard it already was, how big and stiff. I admit I felt a little bit excited but was also threatened by it.

I posed a little bit longer for him. Then he told me to get down on all fours and come over to him that way. As I got down and then cam over to him as he commanded, his cock was at eye level. It seemed to loom above me as I approached him. I ordered me to suck it. I wasn’t so apprehensive this time, and I took it in my mouth without too much hesitation. I didn’t pause at the top of his penis either, this time I started straight off by taking him completely in my mouth and then began running my lips slowly up and down his shaft. I looked up at him while doing it and could see he was a little impressed. By the time of our second meeting I was already sucking his cock without protest. Not bad for a straight guy. He put his head back and closed his eyes while my lips pleasured him. Maybe if I did it right this time, I could avoid an anal fucking?

After a while he put both hands on my head and started guiding me movement while thrusting gently into my mouth, and though I started to get scared he might roughly face-fuck me like the last time it never got as aggressive as that. He kept his head back and his eyes closed. As his hips thrust towards me, his cock pushing itself slowly in and out of my mouth I could here him whisper: “Good slut. Good fucking slut. I’m going to train you. Oh yes, good sissy slut.”

The suddenly he stood up. He kept a hand on my head, forcing me to remain on my knees, pushing me back down lower so that I was sitting while kneeling. He had properly grabbed me by the wig and stood in front of me, his hard cock pointing towards me, a few centimetres from my face. I opened my mouth in anticipation and he just smiled.
“Good fucking sissy”, he said, “I’ll train you well.”
With that he shoved his cock into my open mouth and starting fucking it, not aggressive but harder and faster than before.
He was moaning and shout in pleasure as he continued to fuck my mouth. For some reason I didn’t mind it too much. I was a little excited to be able to make someone so horny and give them so much pleasure. I wondered if he was going to cum soon and what cum might taste like and if I even wanted that.

But right at the moment when his face-fucking of me most intensified and I was sure I would be getting his cum squirting down my throat pretty soon he instead pulled out his cock, grabbing it hard with one hand and with the other grabbing my head and pulling it back at an angle. With a few more vigorous strokes on his penis i felt the shock of a sharp jet of warm cum shooting across my face. He pulled me a little closer to him and aiming his penis and made sure the sperm that followed sprayed and flooded over my face. As he guided his cock across my face, warm thick drops fell over my cheeks, across my nose and down around my mouth. I was kind of stunned into silence. Mixed with disgust, there was little bit of excitement in my belly. I didn’t have too long to reflect on my mixed feelings though, for as soon as had he shaken the last drops of sperm from his cock onto my face he shoved his cock back into my panting open mouth. This time he just moved the head of his penis slowly in and out between my lips a few times. I’m not sure if he was just trying to get an additional few seconds of orgasmic enjoyment out of me. Maybe he was making sure every last drop of cum would be out of his penis or wanted to be sure that I had to taste his sperm (which I did) because covering my face wasn’t enough domination for him.

I don’t know because he just stepped back, looked at me once, smirked and zipped up, leaving the room. I knelt there for a minute unsure of what to do. His cum dripped slowly down my face. I felt utterly humiliated there, in my girl’s wig and short shorts, with a man’s sperm covering my face. Stefan had used and degraded me yet again, and I knew that in combination with allowing him to ejaculate in my ass, my masculine dignity had taken a beating. I felt then that a big chunk of my manhood had been taken from me, possibly permanently. As the sperm started to drip from my face and land in droplets on my legs and on the short shorts he had bought me and told me to wear for him, I got up and washed, changed and left with a further word to him.