Stefan's Blackmail

When I was about 19 I started to crossdress. I didn't have gay feelings or strongly identify as feminine but I felt strangely attracted to my older sister's clothing. One day I tried on a skirt and I found this simple act feel so thrilling that at the next opportunity I tried on a two more things...a dress and and a pair of her jeans. I was always thin, especially when I was younger, and my sister was only three yeas older than me, so I had little problem fitting in most her stuff. Actually the stuff at the back of her wardrobe, the stuff a year or two old that she didn't really wear anymore was just perfect for me, and she never seemed to notice if they were disturbed. I started dressing up more often, experimenting with and combining outfits. It was fun. I eventually took the occasion of Halloween to buy a black girl's wig in a shop without any probing questions (internet shopping hadn't taken off yet…). I took a few pics with my digital camera, and hid them amongst the files on my computer.

But it wasn't something gay... though I did get a kind of sexual charge I never jerked off thinking of guys. Guys kind of disgusted me. In my mind they were just macho, sporty assholes, bully usually. Actually although I wasn't one of those typically sporty or macho or outgoing guys, I managed to date a few girls in that time. Though the crossdressing never came up in conversation!

My sister moved out, and then I grew up and moved out. I lost interest in crossdressing for a few years: it was college time and I was busy studying, partying and messing around with girls.

Then I started to crossdress again. I lived in a a mixed gender house share directly after college, and I noticed an interest growing in me in what the two girls who lived there wore, rather then the girls themselves. When I know everyone else would be out, I would try on the clothes of one of the girls. Not all her stuff fit like my sister's had, but it ignited the spark in me again. I bought a wig again, and even started to buy some clothes of my own (this time via the anonymity of internet shopping and my own credit card!) It felt special to have my own clothes to crossdress in.

After two years out of college, I had worked my way up to a nice job (I won’t say what). I continued to crossdress when I felt like it, though not all the time. I even load a few anonymous picture up on websites to get a reaction. I dated a few girls though never anything permentant. I don’t know why. It had the effect at least of never making my secret crossdressing become ‘an issue’. It was just one private little activity I did separate from the rest of my life. Fun escapism, with a small sexual thrill thrown in.

My laptop had broken, I didn’t really know what was wrong with it, so I brought it into the IT guy in my workplace, Stefan __________, who offered to have a look at it before I went out to buy a new one. About a week later he returned it to me, and he had seemed to have worked his magic and got it going again. He seemed a little strange with me, almost bemused. Thinking back, I know what had happened.

About a week later I got an email from his personal address. It was asap in the face when I opened to see a selection of my crossdressing pictures! He had obviously come across my protected folder. For whatever reason, curiosity or maybe just to see if he could, he broke the password. Now I was looking at pictures o myself in a woman wig and various girls clothing, my face plain to see, and the message: “We should talk about this, Don’t worry, I’ll be discreet” I was beside myself. Of course, besides the personal embarrassment, I had the kind of sensitive job, which I could lose if such a thing came to light. I tried to be optimistic despite my stress. Before I took any other action (like thrashing all my clothes or permeative quiting my job) I went t see Stefan. He told me that he found the pictures amusing. But he understood how stressed I must be. He suggested that he could imagine promising to forget such a thing. He had only sent me the pictures as a joke, to provoke me. He promised he’d delete what he had in front of me. He asked me if I was gay, if I’d ever fucked guys will dressed as a girl. I explained to him that crossdressing wasn’t connected to that for me. I like girls. I’d dated many of them. He smiled to himself strangely.
"All the same”, he said, “I’d like to fuck you while you are dressed as a girl, see what it’s like”
“No way I’m not interested!”
“If you don’t let me fuck you, I can’t control what might happen with these picture. Perhaps one day I’ll accidentally upload them to the workplace network”
I told him I would not give in to blackmail like that and left our meeting.
He sent me an SMS directly after: “You have 2 days to think it over”
By the next evening I was totally stressed out. I eventually convinced myself that it could be so bad to just do it once. It would be over with any then I could move on.

When I told me that I agreed to his demand I had to wait a day for any response. I received a hotel address and room number and a time. That Saturday at 8pm. Then I got an image from him. It was one of my images crossdressing. Under it was written “Exactly like this”

Saturday came and it was with growing nervousness that I went to the hotel with a small back of the requested clothes. I had downed a few Vodkas to try calm me. He opened the door with a kind of sleazy, triumphant smile.
“Come in”, he directed, “Get changed right away. I can’t wait to see if you look as good as you did in the photos.”
I was a little surprised by the compliment and unsure what to do with it or how I felt about it.
As I went into the bathroom he called after me “And I hope you brought make up and shoes too. I want the whole package!”

I dressed up as he had requested: a bustier top, black panties, stockings with suspenders and black high-heel shoes. I completed it with my wig and putting on make up to feminise me. I started to feel a little bit better. I was separated from my normal self, I was in character. I could do this.

When I went out to him he was sitting in an armchair beside the bed and he took a long time to admire me. Though I was still really resentful of the situation he had put me in, and though I feel exposed, I got a strange buzz out of being crossdressed in front of another person after years of just doing it alone in my bedroom.

I was still processing all this when he told me to come over and get down on my knees before him. I complied and just knelt there, not fully looking at him, kind of looking to the side.
“Don’t be so shy. Unzip me. The sooner you suck me the fast this will go”
As I unzipped him I could feel he was already hard under his jeans. It was strange to feel the hardness of another man. As I fully opened his jeans his cock sprung out, coming to full erection. It was not a monster but it was thick and strong-looking and was certainly bigger than mine. I hesitated for a few seconds until he goaded me on: “Take it in your mouth, now.” I closed my lips on it and started to move them up and down a little on the head of the penis. After a minute I could feel a hand on the back of my head. I was gradually, gently being encouraged to move further down on his cock.
“That’s it, properly suck it”, I heard him softly say, “suck it like the good slut you pretend to be. Don’t let me down now”.
I made a bit more of a show of sucking him, hoping this might satisfy him enough. I felt I could manage it somehow enough to satisfy him. I’d gotten a few blowjobs from girls, and I'd seen porn stars do it online.

After a while I realised that if you took the infuriating situation of out it, that it wasn’t such a big deal to have a cock in your mouth. It was actually a strangely nice feeling to suck on this hard fleshy thing. Satisfying on some deep level I wasn’t able to work out then.
He started to moan, his hand guiding my head into a slightly faster rhythm, “That’s more like it, you’re a good little ******y slut.”
“I’m not a ******”, I tried to say, but it only came out as a mumble because of the enlarged cock in my mouth.
I pulled my mouth off him and looked up at him in attempted challenge, “Crossdressing isn’t about that for me. I’m into girls!”
“Well, crossdressing is about being a cocktease, you can’t deny that!” he growled angrily and pushed me back down on his cock.
“Your a ****** and a cocktease!” he told me as he pushed the hard head of his penis past my lips,”now make good on it or else.”
“I’m not a ******!”I protested, but again it only came out as an impotant mumble because of my cock-filled mouth, “I’m not enjoying this.”
“Well I am!” he exclaimed and I felt a second hand grab my head as he took total control, holding my head as he started to make rapid and powerful thrusts into my mouth. For the first time (but not the last), I started to feel totally violated as he selfishly fucked my mouth. I could feel that my mouth was just a hole, a thing to use for him to get off. The veiny hard walls of his cock rubbed against the ring that my lips were forced to make around it, the head of his penis speared deep in my mouth, jabbing against my throat. I felt I might gag at any minute.
At the same time I hoped he might cum soon with such thrusting, then I might get out of it easy. I lost myself in the moment and submit to the experience of having my mouth fucked by this asshole Stefan.

After what felt like the longest time, by which time I felt my mouth had been transformed from a mouth and into some kind of soft wet pussy-hole for this guy, he eventually did get tired of the thrusting and pulled my head from his cock. I saw the shaft was covered in the red of my lipstick. I wondered how my face must of looked, all the carefully applied feminine make-up probably didn’t look so careful anymore, though perhaps still feminine in the whorish kind of way this guy probably liked.
“Very good my slut”, he said, “you don’t just like to look the part, but you can play the part too. But you didn’t think that that was all I was going to want, did you? I said want the full package.”

I knew it was inevitable what would follow, so I didn’t even bother protesting or tying to get out of it. I had little energy or resolve left after that long, hard face-fucking anyway. He’d managed to chip away at enough of my dignity,and by that stage, I just wanted the ordeal over with. I went over and bent over the bed, pulling my black panties down some of the way, and professing him my ass. I made him promise to use lubrication. I had brought a small tub of vaseline, I didn’t have or need anything more specific in my life up to then. But he manoeuvred me around on the bed, he specifically wanted me longways in the middle of the bed - I didn’t know why at the time (though I found out later….) - and commanded me to get up on all fours. As I felt him rub the cold Vaseline in around my asshole I prepared myself. I knew this was going to be a different game than taking a cock in my mouth, both in how hard it would be, and what it would mean to me later, as a straight guy.

I positioned himself behind, putting one hand on my hip with this other presumably holding his cock pointed at my asshole, and then telling me (half laughing, the jerk) to “relax”. I felt the pressure of the head of his penis pushing against my asshole. He gently wiggled the head against the ring of my asshole, slowly (and masterfully, I had to admit) increasing the pressure. I gasped as I felt my asshole open up and the head push through.
“Good slut” he said maintaining his position so just the head of his penis was inside me, “just relax.”
It was already feeling uncomfortable, but only hurt a little bit, not as much as I imagined. Now with both hands on my hips he started to move his cock a little bit back and forth, the Vaseline helping him glide in and out as he progressed bit by bit so that his cock worked its way gradually inside me. I don’t know how deep he was in me at that point, perhaps half way (?) but the pressure in my ass was building and it was starting to hurt. I was wincing in pain, my head lowered. He worked his way al little deeper and grunted in satisfaction. I could start to feel his body touch up against my ass, so maybe he had reached in as far into my asshole as he could go. My asshole felt strange and stretched and full and under stress. It was something I had never experienced before.

Then he started to properly fuck my ass, slowly glad almost fully out and fully back in. The Vaseline surely helped, but it was already painful.
“If you tell me still that you don’t finally feel like a ******, then I won’t believe you", he laughed between satisfied moans.
I had no real answer for this. He had gotten me in this position and here I was in a hotel room dressed up in fairly slutty women clothing and a wig, with a guy fucking my ass, the taste of his cock still in my mouth. I knew I wasn’t a ******. I had been forced into this. Never in my years of crossdressing had I imagined such a scenario. But I had to admit it didn’t look good. I felt used and emasculated, even perhaps feeling a little like a whore. He was certainly treating me like one. And maybe it was what i deserved for crossdressing all those years, the kind of slutty girly clothes I was drawn to and the poses before the mirror informed by pictures of sexy women I saw in magazines and in soft-core porn.

Stefan started to fuck me quicker and harder and it hurt more and more in my ass. He was really going in and out in full thrusts by now. It hurt so much but he had me firmly in his grip, gasping my hips on each side as his hard cock pushed into my ass. He was getting increasingly worked up.
"Oh yes my slut, your my fucking slut now!” he moaned between pants,”fucking cock-teasing ******!”
I was speechless. The pain and overpowering feeling of violation had put me in a delirious, switched-off head space. I felt I had lots all control of my person and my body. He was fucking me like a sex-doll. In those minutes, I wasn’t myself, so I could only have been the whore he pictured me to be. I was just a feminine body in a bustier, stockings and high-heels.
“Yes, yes, good ******. Good ******!” he shouted as the thrusts intensified. I could hardly take anymore.

Then i felt warm wetness as let out a loud moan what must have been cum shot into my ass, filling my asshole with his semen. Psychologically, it was a very very strange moment for me. Another man’s cum was in my ass. This jerk, Stefan, who had exploited me and abused me, his semen was now inside me, like normally a man’s would be inside a woman. I felt so violated and dirty. I felt degraded. I felt absolutely emasculated. I couldn’t argue in that moment that he had made his bitch. He had a moment of property over me. He had used my mouth and then my ass for his own selfish pleasure, putting his cock inside me twice and finally deposited a bit of himself (his sperm) inside my body. I still wasn’t sure if the experience meant I was a ******, since I had been forced to do this, but there was not question over who was the man and who was the bitch. Nothing in my years on trying on women’s clothes had prepared me for that feeling.

He withdrew carefully out of me, giving me a little patronising pat on the ass.
“Good job slut. Don’t worry, I’ll keep my promise. I’ll never tell anyone that you like to dress up like a woman or what happened here today.”

I heard him go towards the bathroom. I didn’t move for a minute or two. I needed to recover for a moment, physically and mentally. As I heard the bathroom door re-open I got up and made my way on unsure legs towards the bathroom to change, returning his mocking face with a hateful look. I threw off the wig and started to take of the high-heel shoes, stockings, and bustier. I didn’t want to look at my face. My asshole still hurt and was feeling stretched. Touching it gingerly I could feel some of that bastard’s sperm leaking out of me onto my fingertips. I got in the shower, washed my makeup off and tried to point the shower-head towards my ass, hoping to was his semen out of my body. I couldn’t take the thought of a part of him still being in me. His thinking he still possessed me somehow.

I got dressed and came out of the bathroom with a mission to exit the hotel room as quickly as possible.
“OK, you got what you wanted” I told him angrily, “its over, and I donT’ want to see you in the workplace. We ignore each other when we can.”
He was sitting on the bed, still naked. His cock was now flaccid, thankfully. I never wanted to see his big, hardened cock ever again. He seemed preoccupied with looking over the contents on top of the dresser across from the bed. He smiled to himself.
I walked out of the room without any further desire to talk to him. My asshole still hurt, a shame burning through my straight clothes in memory of how he’d made me his bitch. As I walked out the door he called after me.
“Don’t worry, I won’t ever tell anyone about the pictures. I promise.”

I hoped then that that shameful night would be the end of it. Of course it wasn’t.
But that’s another story.