I was on a mission. I needed to take my femininity to the ultimate level. But I could wait and plan. I wanted my first time to be magnificent and as pain free as possible. I would have to be completely seductive if I were to get my man. I had to make him question my sexuality in some way and then I would spill the beans and hope for the best. I knew he liked me and was convinced he would like Rita even better. I had to prepare my pussy for the big event. I went online and ordered a dildo. A very realistic dildo. When it arrived I was, luckily, the only one home. It was bigger then I thought it would be so I waited and used some other options to gradually work my way up to using it. It was early summer and I just turned 17. Denise was engaged to be married and she asked me if I wanted her bedroom after she moved out. I was thrilled because her room was a bit more feminine than mine. A lot more actually. So I jumped at it. It also faced towards Danny's house. Nights would find me refining my makeup skills, practicing walking in real stilletoes and stretching my little love tunnel. At first I didn't enjoy it at all but I was persistent and eventually I was beginning to get some very, very nice sensations from my snatch. I used the "big boy" , as I dubbed him to practice my cock sucking skills. The poor dear was so coated with lipstick some nights it was hard to get him clean.
One Saturday afternoon I saw Danny doing some yardwork. He had his shirt off and I was overwhelmed with lust. I was hard as a rock in my panties. I deftly lowered my cutoffs and rubbed myself to a delicious cum. After licking it off my fingers I started devising a plan. I pulled my hair out of it's ponytail and brushed it out. I put on a tank top that left a tiny bit of my tummy exposed. I highlighted my cheeks with the barest bit of blusher and hiked up my shorty shorts. I sauntered out to my backyard keeping a slight sway in my steps. I went up to the fence and gave out a low wolf whistle saying..."Looking good!" Danny turned to me and I gave him a little wink! He came over to me and asked what had gotten into me. I answered nothing really I was just in a playful mood. He asked what I was doing that night and I said just hanging around the house. He asked if I'd like to see a movie instead so I said yes. He said it in all innocence but I was of the opinion that he had just asked me out on a date! What to wear? What to wear?
I really had to consider what to wear. I wanted to wear a dress but that would have been a dead give away, don't you think. I opted for a tighter than usual pair of jeans and a simple red tanktop. Not overly feminine but not overly macho either. What I did do though was wear a lacy black garterbelt with stockings underneath. Panties were a given because that's all I had in the undies department having parted ways with boys undies (yuk!) a long time ago. I kept my hair loose around my shoulders and added just a smidgen of mascara.Not to be noticeable but to keep me in a girly frame of mind. (As if it was ever anything but!) When he saw me he didn't say anything about my appearance and off we went. Damned if can remember the movie. I just remember wishing he'd put his arm around me. But alas! As we were walking home we talked about life in general. He asked what my plans were after highschool. I told him i was thinking of becoming a fashion model....jokingly, of course! (sure) He said I could probably make a go of it...jokingly. (I think) Anyway, I let that go and asked him what his plans were. He said his dad would get him fixed up with the local utility company as an apprentice lineman. I just pictured him in his work clothes with a hard hat and all. My clitty jumped in my panties at the thought. I always carried a lipstick on me wherever I went. More of a security blanket then anything else. I wanted so bad at that point to whip it out, put it on and yank his pants down to his ankles and swallow his cock. But alas! We sat on my porch and chatted for a bit longer. I made a point of touching him on the arm every once in a while as we chatted. I read somewhere that that was a girly thing to do. He didn't seem to mind. He then looked at me and said "Don't take this the wrong way but I feel like I've been out with a girl tonight." I could feel the blood rush to my face. I said I was sorry and he said not to be and hoped he didn't piss me off. Piss me off? I could have kissed him! I told him that I knew I wasn't the most macho guy in the world and I had come to except it. He then reminded me of that Halloween a few years back when I dressed up like Alice. "Oh, yeah", I replied, "That was fun. Maybe I should do that again this Halloween." He gave me a long look and said I'd probably look great. My heart was pounding under my little titties. "I'll look into it" was all I could get out. After that he went home and I went in to the house with such a case of the horns! I stripped down, put on a nighty and for the first time took in all of the "big boy" in my pussy thinking about the boy next door.
Two days later...walking home from school. "I'm going to do it." "Do what", he asked me. "Dress as a girl for Halloween. Denise can fix me up." I told him after all it was his idea. I mean it was, wasn't it? I told him I would have to practice a bit so I wouldn't look foolish. And I left it at that. I didn't need to practice but I did anyway. The next day when I came home I femmed up to the max. Full makeup, nails and two recent purchases...that put a huge dent in my saving. A really cute long haired wig in a deep brunette shade and my new breast forms! These were wonderful and felt so real when tucked into my bra cups. They could be affixed to my own little titties but I wanted to wait for "the right moment" to do that. I slipped into one of Denise's old LBD's put on my heels and startred cooking dinner. When mom came down stairs after waking up she was a bit miffed. I told her I was just getting used to things for next Halloween. "It's a bit early for that." was all she said. Anyway, her mood changed when she tasted her dinner. I made veal Marsala that night. It's her favorite. After she went into work, I freshend up my makeup and spritzed myself with her Chanel #5. I checked my stockings, put on a pair of shoes with a five inch heel and picked up the phone. Guess who I called? I told him I wanted to show him something and get his opinion. He said he'd be right over.
I looked at myself in my mother's vanity and was very impressed with what I saw. I thought I was lovely, sexy and at least fuckable. I heard the doorbell ring and descended the stairs to what I hoped would be a life changing experience. More soon.