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First Crossdressing Adventure

"Neighbor girl teaches me how to be a girl."

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When my family moved to Oregon, I had no friends living close by. I had just turned 18, and didn't know anyone except a cute neighbor girl. She was maybe 3 years older than me. She was very friendly and we got to know each other over the first summer. The first thing I learned about Kathy was that she was not into guys and preferred girls, something new to me. But it didn't affect our friendship.

Kathy and I spent a lot of time together. I enjoyed her company. We exchanged our secrets and I had confessed that I enjoyed wearing sexy girls' clothing, and she didn't make any judgements about me.

Kathy told me that any time I had the urge to dress up, she would love to help me. She said since I was small, with a slim build, I'd make a pretty girl. I can remember being very embarrassed by what she said, but at the same time, I was very turned on by the thought of it.

One Saturday, we were at her house when Kathy said this would be a good day to play dress-up if I wanted to. I nervously agreed, not knowing what she had planned. She said it would be fun.

She filled the bathtub with bubble bath and told me to take off my clothes and get in. I followed her orders and got into the tub. Kathy started washing me with a soft sponge, giggling every time she got close to my pubic area, which made me jump.

I didn't have a lot of body hair, but Kathy said I'd feel sexier if I was completely shaved, so I let her use a woman's razor on my legs, then my crotch, and then my underarms. She washed me one last time and helped me out of the tub. She carefully dried me off and as I stood there, nice and smooth, she asked if I liked the feeling. Well, I didn't have to really answer because my small cock was standing at full attention. She laughed and said it was cute.

Kathy sat me down in front of the mirror and started doing my makeup, foundation, some nice powder that she brushed in, then did some eyeshadow, false eyelashes, blush, and finally bright red lipstick. She got a medium-length brown wig and showed me how to put it on and how to brush it out and comb out the sexy bangs. As I looked at myself in the mirror, Kathy told me that I really made a pretty girl.

Kathy dressed me in all black lingerie, a sexy teddy with garters, thigh-high nylons, a pretty long-sleeved mini dress and then a pair of 4-inch high heels. She had me walk for her, planning on giving me some pointers, but I surprised her with my skill in heels, something I had been practicing for several years.

Then Kathy told me that if I was a girl, she would make love to me. I was embarrassed but thrilled that she was sexually attracted to my feminine persona. Kathy bent forward and gave me a kiss on the lips as her hands followed the contours of my body, stopping to massage my bottom.

We spent the rest of the day being girlfriends, nothing sexual, but it was fun to be accepted the way I wanted to be. We repeated our dress-up play every day for a couple of weeks before Kathy sat me down to tell me about a fantasy she had.

She told me that she dreamed of watching a sexy guy dressed up in free-flowing scarves, each one connected to the next so they could be pulled off one at a time until they were all gone. She said she wanted to see a crossdresser excite a regular guy while undressing and at the finish, giving the guy a sexy blowjob.

She was really turned on as she described the event, then asked me if I would be willing to help her with her fantasy. I wasn't sure what to say, but I thought I owed her for all of the help she had given me. So, I found myself saying that I'd be happy to help her. She hugged me and told me she knew a guy that would help. She said that he might want more than just oral sex, and I asked what kind of things she meant.

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She said she would teach me so I would make a perfect girl. Over the next week or so, Kathy taught me about vibrators and other sex toys. She would dress me up, then lay me across her bed and lube up my bottom and slowly insert vibrators into me. I found this to be very pleasing as Kathy slowly increased the size of each vibrator until I was easily taking an 8-inch dildo. I looked forward to every visit until she decided I was ready for the next step.

I showed up for my next visit and let Kathy do my makeup and then dress me the way she had dreamed about, which was a dress made up of silky scarves held together with gold rings. I looked at my image in the mirror, and I was very turned on. Kathy asked me if I was ready for my first time with a guy. I told her I thought I was ready.

She made a call and told me the guy was on his way over. Kathy got out some lubricant and had me bend over while she rubbed it into my bottom, which felt so sexy. Just then, the doorbell sounded and Kathy took me by the hand and led me out to the front door to meet my new lover.

As the door opened, a nice-looking older guy was standing there. Kathy knew him from college, and she welcomed him in. He was looking at me the whole time, smiling shyly as he took my hand and spun me around slowly. Kathy told him I was her sexy friend that had dreamed of being with a real man. I felt my cheeks starting to blush at that comment. This was her fantasy. But I was also turned on.

His name was Greg and he played football. Kathy said she would love to watch us dance together, but that Greg should get naked first. He complied as Kathy turned on some music. Greg's cock was hard as he turned to me and then took me gently in his arms.

As we danced, Kathy reached over to show Greg how to remove the outer layer of scarves. As we danced, Greg slowly pulled off the scarves until the last one hit the floor. There we were, both naked, still holding each other. Then Kathy asked me if there was something I wanted to do.

I slowly kissed my way from his neck down to his erect cock. I slowly took it into my mouth, just like Kathy had shown me with her dildos.

I gently sucked Greg as he moaned and told me how good it felt. I liked feeling his large mushroom head as it glided over my tongue and deep into my mouth. Greg gripped the sides of my face and slowly fucked my mouth. Kathy was begging him to cum in my mouth as he was slowly slid it in and out. Then I felt him tense up and he shot a huge load of cum into the back of my mouth and down my throat. He held me tight against his crotch to make sure I swallowed everything.

Kathy was busy rubbing her pussy as she watched, getting off from what she saw. Then she asked Greg if he wanted to make love to me and he nodded. Kathy helped me get on her bed on my hands and knees and then guided Greg's large cock gently into my bottom. Greg slowly made love to me and I really liked how it felt, the fullness and then the gentle strokes all the way in, with his balls bouncing off my ass.

When we finished, Kathy thanked both of us for the wonderful show. She asked if we wanted to help her with another fantasy sometime. I looked at Greg, and we both nodded, not even knowing what her fantasy might be. If it was half as nice as this one was, it had to be good.

I knew I had learned some things that would make my college years much more fun, thanks to a neighbor girl.

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Written by MikiDaniels
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