First Time for Daddy's Girl

I had been talking to him for a while now. This man. Daddy. Somehow the constant barrage of pornographic images and sissy hypnosis had taken a hold of me and brought me to the point where I had actually begun to develop a relationship with a man.

I had never thought of myself as gay, or had thoughts about men. I was the typical A-student, moderately athletic, all-American guy that his fair share of girlfriends due to my adherence to societal norms...but here I was, a 23 year old graduate student, sexting a 55 year old business man.

While I was never really attracted to men, something about dressing up as a girl for Daddy (and seeing his lust for me) drove me wild. I would often dress up and send him pictures of me in full makeup, wig, lingerie, etc. I had actually gotten quite good at the makeup thing mind you, watching YouTube videos. I was bit pudgy, but had a great ass and naturally feminine facial features. Give me an hour in front of a mirror, and I was a sexy, slutty looking girl.

Each time Daddy and I would talk, he would ask me to do things, training me. I did not know it at the time, but he was actually getting me prepared to meet him in person (something that never would have happened without the training).

The first, and most notable, task was to start wearing a pink chastity device. Daddy explained that this was necessary to establish the order of power between us. While he enjoyed giving me pleasure, I needed to know that he was the Alpha. The only one with a real cock. I bought his rationale, and before you knew it, I was wearing chastity constantly. He said it was mostly symbolic-but what I did not realize was that the longer I went without an orgasm, the more feminine I felt.

The knee-jerk, male desire to simply go and rub out a quick one was gone. Any pleasure or sexual gratification was going to have to cum from somewhere else, something or someone other than my tiny little clit. And guess who was there willing to help?

Clever, persuasive, persistent, I was admittedly destined for this result from the moment he answered my Craigslist ad. Each day, Daddy would make subtle suggestions about going over to his house, getting a hotel room, or meeting in the park. I would always entertain the idea, only to revert out of fear when it really came time.

After teasing this delightfully charming man for probably 3-4 months, a perfect set of circumstances arose. Christmas Break, roommates gone for several weeks, no school work, no accountability...Put simply, I had no excuse not to finally meet Daddy. Fueled by weeks of denied orgasms and the feminine forces from within, I decided that this was finally time.

I sent him a text telling him that I wanted him to come over in a few days. He laughed, not really believing that I was ready to meet him. I assured him that I was though. I even gave him the number to one of my roommates and told him that if I flaked, he could send my girly pics. Blackmailed myself perhaps, but needed to make sure we made this happen.

The night before we met, I shaved EVERYWHERE. Every little nook of my body, making me perfectly feminine. After I got done shaving, I covered myself in Victoria's Secret body lotion, body spray, and began painting my nails bright pink. That night I put on my silk, pink pajamas and fell asleep, waiting for the morning.

Daddy was going to come over on his lunch break. So I woke up at about 8:30 am to start getting ready. And did I ever get ready. I spent almost 2 hours on my makeup. It was so over the top. Not in a drag queen style way, but lots and lots of makeup. It was without a doubt the hottest I had ever looked.

I then slipped on my pink, satin thong, leopard bra, thigh high stockings, clip on earrings, necklace, stilettos, and 20-inch blonde wig. The final touch being the DD silicone breast forms that I just ordered off of Amazon. Looking in the mirror, I felt so proud. Jenna was finally here, and she had a Daddy to take care of.

The rest of the morning was spent toying and plugging my pussy. We had never discussed anything more than I blowjob, but I wanted to be ready for whatever Daddy wanted. He was a powerful man, and I was well aware I may not have a choice as to whether I was going to get fucked.

KNOCK. KNOCK. KNOCK.

My heart sank. Oh my God, no! I am not ready! Why am I doing this? Fuck! All the thoughts and reservations shot back in to my brain. How could I have gotten myself in to this predicament. I immediately regretted setting myself up for blackmail. Here I was, kudos to Jenna, she was coming out right at this very moment. Fuck my masculinity.

After maybe 45 seconds to a minute, I walked slowly to the door...and opened it. There he was, Daddy. He looked a little older than his pictures, but you could tell by the way he dressed and stood that he was a powerful man.

I sheepishly asked him to come in and set down on the couch. Instinctively, I straddle him. Rubbing my ass cheeks against his suit paints. I could feel him growing.

As he reached up and kissed my neck, a wave of comfort and femininity took over me. I was safe with Daddy, he wasn't going to hurt me. He just need a sweet little daughter to take care of his now growing member. With confidence, I became I total fucking slut for Daddy.

Taking his pants off, I engulfed his cock in my mouth. Squeezing and sucking on his giant ball sack. I looked up at his face and could see the pure joy. He was hard, horny, and feeling so good because of me...I had never felt so feminine.

As I sucked, he called me dirty names, encouraging me to get him off. "Suck Daddy's dick you little fucking whore," being my favorite. The whole time, I was leaking pre-cum through my little chastity cage like a water fountain. Looking at my panties you would have thought I was some young girl in desperate heat.

"Oh my God baby, baby girl, I am cumming. Take this fucking seed, you fucking whore, fucking swallow every damn drop!!" Gulping and gasping, Daddy had cum unexpectedly. To my surprise I swallowed. Like I had been doing it for years, and I loved it. I felt so slutty and proud of myself.

Daddy patted me on the head and told me how much he had enjoyed his lunch break, and how he wanted to meet tomorrow. I agreed, but was a little sad when he left. I really had wanted to feel him inside me, his manliness taking me. You could almost say I was desperate for the idea of being taken by him...

Daddy is so persuasive. To be continued.