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How It Started

"I looked and saw her panties in the hamper."

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At twenty five and being a blonde haired blue eyed light skinned guy, I had little hair except on my head. So, it didn't take long to achieve the smooth feminine look that I wanted. Of course, I left some "down below" because I looked young and if I shaved it all off I feared looking underage. My blonde hair was long, during the week I wore it in a guy style. On the weekends it was different, it was curly and girly.

So, I was preparing for my weekly encounter. I had my hair looking pretty and my makeup and lipstick were all in place. My nails were done on both my feet and hands and it was time to "get dressed". What would Darren like? What would please my man. I knew that he loved red panties on me, that always got him so hard.

As I picked through my lingerie draw I thought of the first time with Darren. We were both seventeen. I was at home alone, or so I thought. I had been cross dressing for a year, this started when I was sixteen and I had gone in to take a shower. I undressed and when I went to put my underwear in the hamper I saw my older sisters panties in there. They were light yellow and had some small lace around the waist and legs. I touched them and they were so soft and silky. I picked them up and rubbed them on my dick, just to see what it would feel like.

Then, I got this crazy urge to try them on, no one would ever know. I stepped into them and pulled them up. When they engulfed my cock and snuggled against my balls I didn't get real hard. No, just a semi erection. But I felt different, I can't explain it. I looked in the mirror and I felt like myself for the first time, so soft and tender... so girly.

Well, this went on in secret for a while. I had bought some girly clothes and had them hid and when the family was away, I would play! One day I had the house to myself, all alone, just me. I had plans, you see I didn't dress like a girl just to get hard and jack off, ok, sometimes I did. However, the greater pleasure was wearing the pretty colors, feelings the satin and acting (was it really acting?) like a teenaged girl. I loved to sit and just look pretty. I would have a mirror handy so I could admire myself.

So, I had put on my makeup and some red fishnet silk stockings along with the matching panties and had a sexy camisole on as well. I was standing in front of a full-length mirror practicing my girly mannerisms when suddenly a voice broke me out of my trance.

"Bobby, what in the fuck?!" Darren asked in a state of shock

Shit! I had forgotten about Darren, he is the captain of our school football team. He is about six foot three and has to weigh at least two hundred and thirty pounds. Darren was a big seventeen-year-old, in all departments. I had seen him in the showers at school and he had a huge cock. Not to stereotype, but Darren was black. I was supposed to tutor this jock so he could stay on the football team.

I turned and he stood gazing at me, his mouth hung open and shaking his head. "I forgot to lock the door." were the first words out of my mouth. "Please, Darren, I will do anything, anything, but don't tell anyone." I pleaded.

"We all have our secrets, our troubles, ya know?" Darren said as he looked me over. "You know what my secret is? Well, my girlfriend won't put out, I never get any." He said as he rubbed his crotch.

"I'm not gay," I told him, I could tell what he was thinking. To be honest, I didn't know what I was. I had no real interest in girls, except for what they wore. I was so jealous that they could wear such pretty, soft silky clothing and I was stuck in those damned white briefs and blue jeans, unless I was alone. I did like looking at the guys in the shower, but never thought about doing anything with them, unless I was masturbating. But that doesn't count, does it?

"You don't look too straight," Darren told me as he chuckled. "You look like you might like cock. You know, a nice big, thick, long, hard, black cock," he said as he pulled his zipper down. Then he unbuttoned his jeans and let them drop. I loved his bulging junk in his white briefs, they contrasted with his skin and it made them look even whiter. "Look, I ain't gay or nothing, but, this don't count because today you're a girl," he told me as he licked his lips. "Just help me out and it will be our secret."

I felt like I had little choice and I also found that my smaller than average dick was stiff in my panties.

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I decided to do whatever it took to keep Darren happy and quiet. Also, his cock looked so good as he pulled his waistband down and hooked it under his balls.

"Okay, I have never done anything like this, but, well, you have a wonderful cock. I want to keep my secret, so just tell me what to do." I said in a meek fashion knowing that if I did this that I could never claim to be straight... not that I was very sure that I ever was.

Darren smiled, he had beautiful white teeth. Why had I never noticed this before? "Get over here and get on you knees, I need to have my dick sucked and while we do this your name is Julie, I can't have someone with a boy's name touching my dick."

So, there I was. On my knees looking at eight inches of hard dick. Darren had taken his shirt off as well and he was solid muscle. His penis throbbed as his heart beat. I kissed his huge dick head and left red lipstick on it. Then I ran my tongue around his cock head, I searched every area, every place tasting Darren. I went back to kissing it up and down his long shaft. I wrapped my fingers around it and found that they barely made it all of the way around.

I looked up for approval, "Go ahead, Julie, it feels so nice, make it feel good, suck it, suck it for me," Darren said, almost begging.

I put my pretty red lips in the "O" position and gently slid them over Darren's glans, then I swirled my tongue around that wonderful dick head. I played with his piss slit as he groaned and ran his fingers through my blonde hair. I ran my lips down his smooth, hard shaft as far as I could. Darren was groaning and thrusting his hips into my face. I was bobbing up and down making love to his ebony man tool.

"Oh shit! Yessss, suck it for me, be my girl. Take care of your man, take care of me, baby!" Darren begged. "No one has ever done this for me before. You do it so good, suck your man. Yes, just suck that big black cock, you sexy girl."

Then with a loud cry, Darren shot like a canon into my mouth. I had never tasted my own cum and now I had Darren's in my mouth. I followed my instincts and swallowed. Then I licked his big dick until he took it away from me.

Darren looked down at me and grinned. "This can't get out, you know what will happen if it does," he said in a threatening tone. I looked up at him from my place on my knees and nodded in agreement. "You know, you look good as a girl. I could never do anything with a guy, I'm not 'like that'." He looked at my girly looking body again and smiled. "I wouldn't mind doing this regularly, maybe a couple of times a week." He continued, "Maybe we could do other stuff, like you know, let me fuck you?" "But, you gotta be a girl, wear girly clothes, never try to get me to do gay stuff."

I didn't have to think long about what to do, "Yes Darren, I will be a girl for you and you can fuck me, but just go slow, I've never had a cock in my ass before."

And so it began, once or twice a week Darren and I (or should I say 'Julie'?) would get together. The first time his massive cock went into what he referred to as my 'little cunt', I thought that I would be split in two. But I began to enjoy it after a few minutes, the pain of entry was well worth the joy of the fuck. I loved looking pretty for my man. It felt so good to have him make love to me.

Then, we graduated, he married his girlfriend and I went away to college. I missed Darren, but he was straight and I was only there because he needed sex, a place to plant his seed. I finished school and got a good job back in my hometown. I had my own place and spent most of my time there dressed in sexy girly clothes. I felt so good when I look like a woman. But I missed getting fucked, I missed Darren's big cock in my 'little cunt'.

Then one evening the phone rang, I recognized the voice. "Look, I know it's been a while, but I need some help, ya know what I mean?" Darren went on to tell me how he had two kids and his wife just didn't care about sex. "I would love to come and see you, could you, you know, dress up?"

That was six moths ago, Darren comes over twice a week just like back in high school. So, here I am, all dressed up and waiting for my man.

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Written by Imabadboi66
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