Becoming Sammi: My Initiation

When I was young, I always knew that I was a bit effeminate. As a kid, I'd sometimes put on some of my mom's clothes. But, I never knew exactly where this would take me. Little did I know, this secret part of my life would eventually become one of the most important.

During my teenage years, I became aware of what crossdressing was and started to become more and more interested in it. A lot of this coincided when my parents broke up and my mom began dating Phil, who moved in not long later. While me and Phil got along, there was always a bit of a distance between us.

This would change not long after I turned 19. In the few months beforehand, I had delved head first into crossdressing, though I had always kept it secret, only wearing dresses and other clothes in my bedroom. I quickly became great at figuring out what online clothes would suit my body better and then making myself look a little slutty.

About three months after I turned 19, I was in my room trying out a new black dress. Phil worked as a truck driver, so he'd spend three weeks away from home and then one week off. The last I had checked, he was downstairs watching T.V. while my mom was out shopping.

He normally didn't get off the couch for hours at a time, so I felt pretty safe thinking that he would never pass my room. Despite being heavy-set, and us not being close, I was always a little attracted to Phil. Sometimes I thought about him whenever I dressed up and jerked off, and occasionally moaned his name.

Whenever I jerked, I sometimes thought about the one guy I had ever hooked up with, but we only ever did oral. I'd also think about what it would be like if I had Phil's man meat in my mouth. This was one of those times. I could hear the T.V. on downstairs, so I thought I could dress up and jack-off in peace.

Wearing my black dress and some sexy knee-high socks, I was lying on my back with my legs spread in the air and a small dildo in my ass, moving it in and out while I was jerking. Thinking about Phil while I ploughed my ass with a dildo was heaven. But, I must've been louder than I thought.

Between my bliss and the sound of the T.V., I never heard the door open. I had my eyes closed as I thought about Phil, so I never saw him walking towards me as I ended up blowing a load all over my dress and hand and I moaned 'Fuck yeah, Phil...'

'So you're a gay slut, then?'

My eyes shot open as I saw Phil standing at the end of the bed. Oh God, oh God, oh God, he was gunna kill me. I started to cover myself and sitting up on bed.

'You're a slut that wants my cock?'

'Well, I...I...'

'You were moaning my name and ass fucking yourself!'

Phil was getting angrier and angrier with each word.

'Yeah, but...'

As I tried to think of something to say, my eyes drifted down toward Phil's crotch. He had a massive bulk and I was lost for words. He came around the bed and started moving toward me.

'Looking at my dick bitch?'

'Yeah, I...I mean, I...'

'Take it out.'

I was caught completely off guard and managed only to say 'Wha-...'

'I said take my cock out you gay slut.'

Shaking, I quickly undid his zip and Phil's thick man meat burst out of his pants. It wasn't that long, but it was thicker than a beer can. It was eye level with me on the bed. Oh, my, God. My eyes went wide.

'That the dick you were thinking about?'

My cock was twitching again.

'I, uh...'

Before I could say anything else, he grabbed the back of my head and shoved it in my mouth.

'Suck it you sissy whore!'

He started thrusting hard as his dick went deeper and deeper into my mouth and down my throat. I was gagging so hard, but it felt so fucking good. My erection was pressing hard against my dress. I started stroking the base of his cock with my hand.

'Stroke the balls just like your slut of a mother you sissy!'

Oh God, what would mom think? Her boyfriend was throat fucking me in a dress. And I was loving it. I started stroking his balls just like he wanted.

'You like that you slut?'

'Mhhmm' was all I managed to saw around his thick cock as face fucked me hard and fast.

'Draw my balls just like your mother does.'

My cock twitched more at the thought of Phil face fucking my mom. With my free hand, I went to start stroking myself through my black dress. As soon as I touched it though, I should a hot load all over myself.

Holding my head in place, Phil fucked my face harder and faster. I could barely breath. After I few minutes, I could feel his balls tighten up and he started moaning. He was going to cum. I tried to pull his cock out of my mouth -- I had never taken a load down my throat before -- but he held my head in place as his jizz shot down my throat.

I started gagging and coughed as soon as he pulled out.

'You're not as good as your mother, but you'll make a good whore, you sissy fuck.'

He put his cock back in his pants and started zipping up as I tried to catch my breath.

'Don't worry. I won't tell your mother. I'd rather have two sluts living in this house than none. But you're gunna be my secret sissy and serve me whenever I want. Or you'll be out on your ass. Is that understood?'

'Yes, Phil.'

'And from here on out, I own you and you call me Daddy, alright slut?'

'Yes Daddy.'

'Good. Now clean yourself up and get changed. Your mother will be home soon and I want you to help her with the dinner. While we're at it, I want you to keep an eye out tonight. I plan on getting rough with your mother tonight and I'll leave the door a little open. You need to get an idea of how to perform.'

'Yes Daddy.'

He said 'good slut' and walked out. I still couldn't believe that I had just gagged on my mom's boyfriend's cock and now I was his property. What was I getting myself into?