This is my recollection of my first time in girl's clothes. This happen over 20 years ago. The names have been changed to protect the not so innocent. The locations and incidents are true, so if you were a teen in the early 80's and vacationed in Wildwood NJ you may have seen me. Robert/ Bobbie

This is part 2 of a serial story, Please read " Bobbies Vacation" first.

 

Bobbie on the Boardwalk

by Robert / Bobbie

 

I was now on my way. My fears subsided and I was making my way past the pool and onto the street. No turning back now I thought! The street was a buzz of activity with people everywhere. As I walked along I don't think anyone even gave me second look. As I approached the first intersection there was a crowd of people waiting to cross. I confidently stood among them waiting for the light to change.

The crowd of people including myself now made our way up the ramp to the Boardwalk. By the time we were actually on the boards the crowd became a group of about five. There I was on the Boardwalk in Wildwood N.J., walking along with strangers while wearing girl's clothes. What had I gotten myself into? Annie's Pretzels is only about 8 blocks down, I'll make it I thought.

Not wanting anyone to look to closely at me I stopped at the rail and looked at the beach for a few minutes. When I was confident those people had moved on I continued on my way. The late afternoon sun after the rain was bright but not too hot as I continued down the boards. The feel of the hem of my denim skirt on my thighs, the slight tugging of my bra straps, my mind was a million miles away. Suddenly! "Watch The Tramcar Please! Wa, Wa, Watch the Tramcar Please" the very familiar somewhat annoying recorded voice, used instead of a horn on the tramcars on the boardwalk. I quickly stepped off the tramcar path and was snapped back to reality.

Now I found myself in front of the old Wildwood Convention Center. (Since has been torn down and replaced) I glanced in the window of the fudge shoppe and couldn't believe what I saw? It was me! Sort of anyway. Staring at my reflection I could see the slight bumps on my bra covered chest! My hair, the bangs, even the barrettes were visible in the window. The lady in the store must have thought I was looking at her as she waved me in. "M.. E.." I mouthed. She smiled and shook her head yes. As I walked in she said they had free samples and would I like some? Well, she only just said two of my favorite words in the same sentence, "free" and "food". I thanked her and took my samples as I continued on my mission.

I had now completed three blocks of my eight-block trip. As far as I knew, no one even gave me a second look. With my fudge in hand I pressed on. The next five blocks would be the real challenge. The boardwalk was now lined with tee shirt shops and games of chance. The kind that after spending $10- $20 you win a stuffed animal worth about $1. There were people everywhere. I couldn't not walk near anyone. But walking the last 30 minutes and talking with the fudge lady, my confidence was at an all time high. I just no longer cared. I walked along looking at people and what was happening around me. I spotted a group of girls heading towards me and I was checking them out, noticing how they were dressed. I noticed a few had bras on others had their bathing suits under their clothes. As we passed each other I for some reason just looked and smiled at them. One girl smiled back and gave a little wave. My heart was suddenly pounding and I felt like I did when I first stepped out of the bathroom a few hours ago. I headed for the first available bench and sat down.

My mind was once again racing. I was sitting there just looking at my legs and feet. Once again my thoughts focused on the hem of my skirt as I tugged at it gently. I remembered what the girls had told me back in the room about sitting with a skirt on. Actually I was already sitting properly, with my knees together and my ankles crossed. As I glanced down to my ankles I saw how cute my feet were in those white Keds sneakers. The pink anklet socks made the look complete. It was as if I was looking at someone else's feet. After checking myself out I decided I had better get moving. One more look at my little bra covered chest, I took a deep breath and regained my confidence to continued on.

The further I went the more crowded it was. At this time I thought of turning back. So far I'd been lucky and I thought my luck might just run out. But as I looked around I realized there was so much activity and noise and so many people that I would be OK. One more block and once again I walked along as if I was a real girl, without a care in the world.

The smells in the air were incredible, fried dough, cotton candy, hot dogs…if you have ever been to the Jersey Shore, especially Wildwood, you know what I'm talking about. There is just something special when you mix the fragrance of carnival food with the ocean breeze. My goodness I can almost smell it while I write this…mmm.

Without realizing it I now found myself in front of Snow Whites restaurant. That means two things, first, the best roast beef sandwiches, and second, just about one more block to Annie's Pretzels. My final destination. After debating on whether to spend my only money on a roost beef sandwich or bring pretzels back to the girls. I marched on to Annies.

There I was, at Annies Pretzels. More than eight blocks from my hotel, which in itself is not so incredible. But the fact that I was a thirteen year old boy in a denim skirt and pink baby tee shirt, with girls panties and a bra underneath. As well as barrettes in my hair and white Keds on my feet. Now that made it a big deal to me. For the third time today I was overcome by the thought of what I was wearing. This time I was able to regain my thoughts and calm myself without sitting down. I guess I was just more confident.

As I stood in line, I realized the girls never told me what kind of pretzels to get them. Maybe they didn't think I would make it? It is almost my turn I had better make a decision soon. "Next please" a voice said. As my mind once again raced, I was barely able to speak. He said, "speak up cutie!" That was all it took I almost fell over. I was just called cutie by a boy only a few years older than me. It wasn't the fact that a boy called me cute, more that I once again fooled someone face to face. When I finally looked back up I said "five pretzels please, 2 cinnamon, and 2 salt". "That's only four", he said back. Not expecting a reply back I just stood there staring into space. "Working on being blonde?" he chuckled. "Excuse me?" I replied. "What kind of pretzel is the fifth one?" He asked. "My favorite, cinnamon please".

After paying I turned and looked down the Boardwalk towards my hotel. The first thing I noticed was how crowed it had gotten in the few minutes it took to get the pretzels. I had no choice but head back.

The journey was uneventful and I really enjoyed the walk. As I approached my hotel it was strangely quite. I looked up to my room to find no one there. Figuring the girls are in the room I made my way up the stairs. However, waiting for me at my door was the beach bag with a note attached.

Bob,

Thanks for being a great sport! The guys down stairs asked us to go to "Mini Golf". You can find us at Ocean Towers on the boards. We hope to see "Bobbie" later.

Lisa, Carol, Cassidy, and Steffi.

 

What was going on? Did they want me to join them dressed the way I was? Were they going to embarrass me in front of those guys? I know I didn't want to get changed! But I didn't want to see the girls either and let them know I was enjoying myself.

I found my room key in the bag and let myself into my room. I fell onto the bed and lay there thinking about the last few hours. How it all started and how it made me feel. I couldn't help but trace the outline of my bra with my fingertips.

When I finally reached for the television remote, I saw I had a phone message. It was from my parents. They wont be back till after midnight. I should buy dinner on the boards with my cousins. Looking at the clock it wasn't even 6 o'clock yet, I had close to six hours left dressed as girl. I planned on taking advantage of it and not letting my cousins know.

I stood up and walked around the room a little watching myself in the mirror as I walked. If I didn't know it was me, I would never guess I was a boy. From the barrettes in my short hair, to the way the denim skirt hugged my backside and legs, everything seemed just right. It was then I decided to put my plan into action.

I packed the beach bag with a change of my (boys) clothes and almost forgot shoes, I would have looked funny with white girls keds and my beach trunks and "AC/DC" tee shirt. I left a note for the girls saying I would eat on my own and see them later. However, I had no intention of actually seeing them. It is a big Boardwalk, so I thought!

With money in my pocket and my beach bag in hand I left for my adventure. I started walking the opposite way from the boardwalk, as to not run into my cousins…

 

Watch for the continuation: Part 3 "Bobbies Beach Bag"

  

  

  

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