A Sissy's Awakening Ch. 01

I really had it all, I was 25, handsome, had a luxury apartment and because of a sizeable inheritance that kicked in when I turned 21 I only needed to work freelance. I had a beautiful girlfriend, we had amazing sex - everything was perfect.

My girlfriend, Jenny, came over one evening to tell me that work was sending her out of the country for a few months. They had often sent her abroad for a few weeks here and there but this was a big deal, we had a lot of sex that night to "tide me over" as Jenny said. Ah, if only that had been so...

Two days later I was at home on my own and I decided that I'd watch some porn, seeing as I was on my own for a while. I scrolled through all the usual categories: Lesbian, Gangbang, BBC and none of them piqued my interest. Then I saw a category called sissy hypno that I hadn't seen before. I clicked in and laughed to myself thinking "oh yeah, because these videos really work"

I must have been tired because the next thing I knew it was four hours later and the sissy hypno videos were still playing. I turned off the laptop and went to the kitchen for a bite to eat.

Despite my unplanned nap I was still pretty tired so went off to bed a couple of hours later. All night long I dreamt of cock, of sucking cock, of being a sissy. I woke up the following morning with a raging hard on. I tried to pass the dreams off as nothing and headed for a shower.

Later that day I cracked open a beer and put the game on, I can't remember what game now but I found myself looking at certain players and wondering what their cock was like. I shook my head and thought "what the hell is going on with me?"

After the game I had an overwhelming urge to watch more sissy hypno videos. I fired the laptop up and took my cock out. Within minutes I was stroking my cock watching these videos, I came just as the words "FAGGOT" "COCK SUCKER" and "CUM SLUT" flashed up on the screen.

I looked down at my hand and it was covered in cum. I almost chickened out but at the last second licked a little bit of it off my hand. I had never tasted cum before, it was a little salty but it wasn't bad. Before I knew it I had licked my hand clean and was scooping up the rest of the cum from my stomach.

For the next few days all I could think about was cock - morning, noon and night. I watched more and more sissy hypno videos and followed the instructions - eat your own cum, call yourself a faggot or a cocksucker. After my latest binge I went to the ATM and took out $1,000.

I drove 50 miles out of town so nobody would recognise me. I bought a few sets of matching lace underwear, skirts, a number of slutty outfits, wigs, makeup, butt plugs and a neon pink cock cage. I paid in cash and kept my head down, just in case.

That night I watched a number of makeup tutorials to learn how to do it just right. I shaved off my beard and as I wasn't particularly hairy I was able to do the rest of my body quickly. With that done I sat down and applied makeup, put on false eyelashes and my blonde wig. I couldn't believe the transformation in front of me. I didn't recognise me at all.

Emboldened by how well that went I put on a black lace bra with silicone inserts, a white see thru blouse, matching lace underwear, a plaited skirt and knee high white socks. I had some trouble with the butt plug as Jenny and I hadn't done much butt play, however after a few attempts I managed to fit the smaller one in. Finally, I snapped on my pink cock cage to complete the outfit.

I couldn't believe how hot I looked, I was getting horny looking at myself. For two days I walked around the house dressed like that. Jenny emailed me to say she was going to be unreachable for a while which suited me just fine.

At night, I would slip into silky negligee as opposed to my usual boxers. I loved the feeling of it rubbing against my now smooth skin.

Eventually I knew I needed to take the next step, so I scoured a few meet up sites before striking up a conversation with a guy named Steve. He was keen to meet up so I picked a motel way out of town. When I got there Steve was already in the room, I was nervous and wondered if I'd be able to go through with it.

But once he unbuckled his pants and took out his cock I was on my knees, drooling with my mouth open. I immediately started licking up and down the shaft of Steve's cock with my tongue moaning as I did. Eventually I took most of his cock into my mouth and sucked it only taking it out to suck on his balls. Eventually Steve was clearly pretty close so he flipped me over, pulled up my skirt and ripped off my panties.

He saw the butt plug and chuckled and said "my cock is a lot bigger than that little thing". When he pulled the butt plug out I moaned and said "please fuck my boipussy with that big (8 inch by the way) manly cock of yours." This got him really worked up and he started pounding my ass calling me "FAGGOT", "COCKSUCKER" and various other demeaning words which only turned me on more.

Before I knew it I was bucking in time with the thrusts of his huge penis making the orgasm even more intense with my poor cock straining against the cage. Steve started to speed up and I knew he was close so I said "cum in my boipussy with your big manly cock Steve. Breed me like the cum hungry bitch I am." I had no idea where this was coming from but in seconds Steve dumped three loads in my ass.

Steve left and I cleaned myself off and drove back to my apartment. I lay there in bed that night in my negligee playing it over and over in my mind, I slipped off my cock cage and jerked off thinking about that night.

I had never had sex like that before and had never been that horny before, I had a feeling that this was just the start of something...