Story of Sissy Blackmail Ch. 01

I have been debating writing this up for a while, but it truly is a really hot story, that I figured you would all enjoy... so enjoy! (And yes, the title does speak for itself; it's a true story...)

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I began cross dressing when I was 16 years old, and I am now 21. When I was 18 I moved away to college, and began living in a dorm on campus. I chose to live in a single room in a coed hall with a bunch of different sized rooms. My single room did not have its own bathroom, but it had a window, a nice closet, and a fair amount of space on the 4th floor.

Having my own room allowed for me to explore my sissy cross dressing side more than I ever had before, and I took my opportunity to do just that. Every night I slept in my girly panties, with either a bra or nighties that I ordered online. Having no bathroom however meant I had to use the community bathrooms to shower and everything else. This is where the story really begins.

Being an exhibitionist, who enjoys doing risky things with my sissy self, I always like to walk to the bathroom with my panties showing, or with a bra and panties on with a towel tied up like a girl would above the chest. These kinds of things drove me absolutely wild. Just the thrill of potentially being caught or discovered by someone and the humiliation that would accompany drives me crazy.

Now these fantasies of being caught have always been just that, fantasy. I have never actually had a sexual experience with any other guy, but my goodness have I fantasied about it. I frequently masturbate to the idea of being another man's slut, or another man's sissy. The idea of submitting to a man and sucking his cock have always enamored me, but I have never gathered the courage to go through with it, even as crazy turned on as I have been.

One night at about 2:30 a.m., and again this is all factual, I decide to take my nightly shower. I am on a weird sleeping schedule, with no classes until the afternoon, and I always love to shower super late because no one is in there and I can have the place to myself and have some fun. So, I get out of bed, wearing my favorite pink thong and pink sports bra that matches perfectly for not being a matching set, and wrap a towel around myself from the chest down, going just past my panties like a party dress would. I grab my shower gear, and a speaker and head to the bathroom.

Now the bathroom is just down the hall, about 25 rooms away, so not too bad. I make my way there, swipe my card, and enter. I check all the stalls underneath to confirm they are clear, and drop my towel. I go into one of the showering stalls and strip out of my lingerie, and turn on my speaker nice and loud. As a closet sissy, I keep my sissy areas down there all shaved and tidy, with a landing strip shaved into it because I think that's kind of sexy and would be humiliating if a girl ever saw that. Oh yeah I forgot to mention; I am at this point a virgin in every sense of the word. Never even been given a handjob or blowjob, the farthest I've gotten is making out, and even that didn't last long. This isn't to say I wasn't a bad looking kid at all. I'm actually rather good looking, I'm just not a manly man, I have a small frame, and lack the confidence.

So after shaving, and showering fully, I am incredibly turned on, but I have a rule where I don't like to cum because it makes me less horny, and less of a sissy sometimes, so I put my panties and bra back on, and decide to get daring with myself. Its past 3 in the morning now, so I know no one will be awake or here at this hour, so I decide I am going to brush my teeth and then maybe walk home just like this. I turn off my speaker, and open the stall door and begin the walk towards the sink, assuming no one was in there, but of course to my surprise there was another guy in there that I didn't hear enter because I was too busy singing to my music in the shower, but I didn't see him at first. I walked over to the sink, set down my towel right next to the sink thinking that if someone swiped their card I would have enough time to grab it and cover myself. So I grab my toothbrush, and just like that the stall door to the bathroom right next to the sinks open up and I turn and make eye contact with this guy who I've clearly seen before.

I quickly turn grab my towel and cover what I can, and as expected I turned a bright shade of red from the sheer embarrassment of this man clearly seeing me in my thong and bra. I go back to my toothbrush trying to pretend like nothing happened hoping he would just leave, but he comes up to the sink right next to me and begins washing his hands. My hands are beyond shaking at this point and I continue to turn a brighter shade of red by the second. When he was finished he walked over to dry his hands off with the paper towel, and I was counting my blessings that he was just going to leave and forget this whole thing. That, of course, was not the case.

This guy came over and says to me, "Hey don't you live in room 434?"

I turn to him, still bright red I am sure, and muster a very shaky, "Uh... Yeah... I uh do."

"That's cool man, and hey don't worry your secret is safe with me. What's the deal with that anyway?"

I stutter yet again not really sure how to answer that question saying, "I just, I don't know, I like to just wear them I guess, its kind of been a thing for a while."

"So you've been cross dressing for a while huh... I don't mean to be too forward here, but I've seen you around here a lot this year, are you always wearing stuff under your clothes?"

At this point I'm getting annoyed by how comfortable this guy is asking me all these personal questions, but I didn't think I was in the position to leave, so I just nodded my head and continued to look up at him.

This guy clearly thought I must have been interested because I was not leaving and his next move was bold, true, and a huge turning point in my life. He reached up and grabbed the edge of my towel tugging down saying, "Let me see what you got I find this stuff fascinating."

With that tug came down my towel, revealing to him my matching pink thong and bra. He did this rather fast, and I didn't have time to react, so I reached down to grab the towel but his foot was on it and when I pulled up I came up empty handed.

"Just let me look for a second... What's your name?"

I have absolutely no idea why I did this, but I immediately responded with my full name, and for the purpose of this story, let's say my name was Russell Gordon. My mind was literally racing at this point, and at the time I didn't see an issue with giving him my full name, but regardless, I did what I did.

I stood tall and looked up as he looked me up and down, examining what I was wearing very closely. He walked around me very slowly once, and came to a stop right in front of me again, saying, "Well, you definitely have a cute taste in lingerie, even sexier than any girl I've ever been with." At this point my panties are starting to get tighter with the talk about lingerie and his past girls, and he definitely gave notice.

He laughed a little bit and said, "So you kind of like the compliment huh?"

Having calmed down since the first time I turned bright red, I kind of just nodded my head and said, "Hey, it's... like... kind of late so I ... um... I'm going to go to sleep now, goodnight man."

"Yeah sure man, I'll walk out with you." I turn around and grab my stuff off the counter, and he reaches down and grabs my towel. He begins to walk out well before me where I had to kind of jog to catch up and he was already out the door and I was fully undressed. What a dick this guy was. I peaked my head out because I don't need more people knowing my secret, and see him standing at the entrance of his room right across the hall holding my towel waving me to come get it. I shook my head no, he shook his head yes, and I rolled my eyes, looked both ways and ran across to get it. When I grabbed it he still held it firm, and said, "Come inside I have a couple more questions really quick."

At this point I'm standing in the hall, so ill do whatever it takes to get out of the open, so I rush in his dorm room and turn around waiting for him to close the door. He looks both ways, closes the door and turns to look at me. He tosses my towel on the couch and walks over to me, standing over me again.

"Go ahead, sit on the couch I really just want to ask you like two or three more questions and then I promise I'll be done with you."

Done with me? What does that even mean. So he goes over to his laptop messing around with something I cant see for a couple seconds, and about ten or twelve clicks later he's finished and turns to face me.

"So Russell Gordon, you've been cross dressing for some time now you said, how long?"

Annoyed, but he only said two or three more questions, so I figured I would just answer and get out of here. "Since I was 16, so about 3 years or so."

"Okay, that's a really long time so be dressing up as a girl, you said you do it almost all the time under your clothes, and basically whenever you can?"

I feel like I'm repeating myself, but I answer anyways, "Yes."

"So if you've been pretending to be a girl for so long, how many guys have you been with?"

At this moment, I froze. I literally didn't know what to say. My panties again got tighter; I hadn't cum in over two weeks so I was very horny all the time. Calmly I responded, "What? I'm not gay."

He just laughed, looked at me and while chuckling, "Of course you're not gay, you think you're a girl. And what do girls do? They hook up with guys. So how many guys have you been with?"

"None, I'm out of here."

"Woah, woah, woah I didn't mean to make you so mad. Just trying to figure you out. If you like to dress like a girl, acting like a girl is the logical next step right?"

I guess I hadn't thought of it quite that way before. "Well, I see what your saying but-" He cut me off, "But nothing. Listen just hear me out. Tell me you haven't been at least curious and thought about it before. Tell me that much and I'll be done with you."

I sat looking at the floor, still seated on the couch, for what seemed like an eternity never really giving an answer or looking up, and he took this as an admission of my desires.

"Exactly. It only makes sense. Here try something for me, then you'll know if this is for you or not. I'm going to pull out my cock, and I want you to just look at it for a minute or two. If you want to touch it like I'm sure you will, fine. If you want to do anything else, which I know you will, that's fine too. But you owe it to yourself to at least take this step."

I hadn't moved an inch and I hadn't looked up the whole time. I just let what was happening around me happen. This all happened so fast and I didn't know what to do or what to say. I could hear him undoing his belt on his jeans, and I heard the zipper being pulled down. Next came the rustling of his jeans being pulled down, and I could see them bunched up at his feet in front of me.

I looked up for the first time at his boxer briefs in front of me, with a bulging tent being formed in them. I looked up at that and stared for a few seconds, then looked up at him.

Now this guy was as college as it gets. He was probably a former high school athlete, as obvious by his genuinely fit body and bigger arm muscles. He had a nice short on the sides long on top haircut, with some 5 o'clock shadow. A really good looking dude.

I looked up at him and he said, "Pull down the boxers and just take a look."

I took a deep breath, reached up grabbing the sides of his boxers, and pulled straight down his boxers slowly. It slowly revealed the base of his cock, showing more and more until it finally sprang free and bounced around in front of me. I dropped the boxers and they fell to the floor joining the jeans in front of me. He stepped out of both, leaving himself naked from the waist down.

At this moment, I got undeniably turned on. My panties became extra tight, and my hands were shaking.

"So what are your first impressions?"

This guy has such a confidence and cockiness to his voice that I just find hypnotizing. "It's... well... it's definitely bigger."

"Bigger? Bigger than what?"

Realizing I had slipped up, I corrected myself, "Big. I meant Big."

He chuckled again, "Well by the looks of things you like them 'bigger'" He emphasized the word in the sentence and nodded towards my panties with the growing bulge in them.

"I guess." That was all I could muster out.

"Well sissy, go for it. Touch it." That word sissy sent shivers through my body.

I lifted my right hand without thought, and grabbed it by the top. I then removed it quickly and looked up at him expecting him to say something. He just nodded. So I reached up again and grabbed it by the base, stroking it once towards me and letting go again. He was still growing, but this guy was every bit of 7 inches, and closer to 8 when he was fully hard.

"Grab the balls you'll like those."

I reach up with the left had while holding the tip of his cock with my right and felt his balls. He had shaved balls, and just pubic hair above the base of the shaft.

"That's a good girl, you're a natural already."

My heart was beating so fast I didn't even hear him I just was looking at this cock twice as big as mine in front of my with amazement.

"Kiss it."

Okay, that was too much. Touching a man's cock was enough for me. I had settled the curiosity I should call it a night.

"I don't know man, I think this is a little much."

"Come on, I know you want to it's not a big deal. No one will every know."

Considering his words, I figured why the hell not, and I removed both my hands, put them on my knees, and leaned forward planting a long kiss right on the head of his cock. He seemed to like this, and told me to do it again, to which I obliged. What's a second kiss I suppose?

After the second kiss he asked, "So what do you think now?"

"Much different than I expected. It's... Different."

"You sounded like you wanted to say something else for a minute. Like you were going to say it's hot? It's sexy? It's what I've been waiting for?"

I began to feel my face turn red, and at this moment, I'm sure he knew he had me.

"Go ahead, suck on it. Suck my cock."

At this point, you really didn't have to ask me twice. I was already dying to feel this cock in my mouth and on my tongue. It was the sexiest thing I could ever imagine, and I needed more.

I took another deep breath, leaned in and took it in my mouth. At first only a little, then it became more wet and I decided to take more and more until it finally hit the back of my throat and I gagged off of it. I caught my breath, and looked up at him kind of rattled.

"It's okay, you'll get good with practice," he said, as if I would be practicing?

I took him back in my mouth and was a little more cautious of the amount I was taking in my mouth, but my goodness, I was loving every second of this. Like I had been born for this moment right here. Like everything I've ever done has led to this moment of sitting in a college kids dorm, wearing pink lingerie, sucking another man's cock, and loving it to death.

He took his cock by the base and pulled it out of my mouth, which watered clearly wanting it back.

"Suck my balls baby get them nice and good."

He stepped forward and placed his huge balls right on my chin and expected me to go to work, which of course I did. I spent what felt like forever licking and sucking these balls, they were amazing. After about five minutes of this he stepped back stroking his cock and looking at me.

"So what do you think?"

"I love it."

"You love what?"

Realizing what I just said I loved, I hesitated but continued, "I love your cock."

"I don't think you just love my cock, I think you love all cocks is that right?"

"Yes, I guess I love all cocks."

He clearly enjoyed this, so he stepped forward and pointed his cock in my face and let me suck it again. I eagerly took him back in my mouth and began sucking this wonderful cock again, this time with more enthusiasm. Again after a minute he stepped back stroking his cock and said, "I think you need a new name I can call you, do you have a sissy name?"

I hadn't even thought of it. "No I don't."

"Well, lets change that, and from now on you will call me sir, is that clear?"

"Yes... Sir."

"So as for that sissy name, lets go ahead and pick the name of a girl that you maybe have a crush on, but you are way to pathetic to ever get. Have one in mind?"

Immediately I knew who it was. "Jenna..." I said ever so quietly.

He laughed pretty good now, "Jenna it is. But of course I'll call you what I want."

He was getting more and more comfortable, realizing he had me pretty good now.

"Alright faggot back to work."

I got weak in the knees, I didn't want to admit, but these names were driving me crazy. I took his cock back in my mouth and began to suck his cock, but I could tell I was getting better at this. I was using my tongue and everything now. I could feel him tensing up, but just when I thought I was going to have to deal with the finale, he pulled out and stood over me.

"Not so fast. Didn't think I'd let you off that easy did you? You're going to have to beg for it like the pathetic sissy you are."

I have no idea what came over me, but I gave it my absolute best and said, "Sir, I have enjoyed sucking your cock more than anything in the whole world. Please let me finish the job."

"Really? You've enjoyed this more than anything? More than when a girl has sucked your cock or when you've fucked some other girl?"

Of course, not having had any experiences with a female I didn't have a whole lot to say here, so I just kind of said nonsense.

"I... Uh... Yeah... Uh... Yeah."

"Wait, don't tell me you've never hooked up with a girl before. Well, I guess that would make sense, you've been doing this since you were 16 and you probably haven't hooked up with one since the day you started. Oh my goodness. This is remarkable."

Looking up I saw him thinking so I softly said, "Sir?"

"It's just, you are on your knees right now, happily sucking the cock of another man, and meanwhile, you have no idea what it's like to have your own dick sucked. How humiliating and degrading this must be. You are literally giving a blowjob before you have ever received one. This is incredible. As a man, this has to be the most emasculating thing that could ever happen. You are serving the needs of another man sexually, you can't get any yourself, and you said it best, you love it. This is wild Jenna."

He stepped back up before I could say anything and put his cock in front of my face as my queue to suck it but when I opened my mouth he grabbed my hair and held me there. He then took his cock and began to slap my face with it all over. He began with my lips and cheeks, but didn't stop there he made sure to slap his cock all over my 'pretty little face' as he called it. He then pushed me down and just rubbed his cock and balls all over my face, so, 'some of his manhood might rub off on me.'

When he was good and done he put his cock in front of me but instructed that I stay put. I did as I was told, and stood there just starring at it. He turned to his laptop and turned on the screen to reveal something I couldn't even imagine. He had been recording us this entire time. I had said so much, I had done so much, I had admitted so many things to him that I thought would stay in this room. He put his cock back in front of my mouth and simply said, "Now, put on a show for the camera, beg for it now that you know the camera is watching."

"No way, how could you do this I trusted you? This is ridiculous!"