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

 

Roberts Vacation

by Robert / Bobbie

 

I remember it all so well; it was the summer I turned 13. My parents and I went to the Jersey Shore (Wildwood) for the week. We make this trip every year with my aunts, uncles and cousins all staying at the same hotel. We arrived Saturday and went to the beach after lunch. By mid afternoon everyone was checked in and to my surprise my older cousin Rich was not there. Rich and I are the only boy cousins on my mothers' side of the family. Auntie said now that he is 16 and working he could not take off from his new job. I was bummed out but figured he was getting to old to want to hang out with me anyway, so I would have to make the best of it.

After dinner everyone hung out around the hotel pool. I got to meet my cousins' friend, who came with them for the week. Her name was Lisa. The night was uneventful and everyone eventually called it a night and went off to sleep.

The next morning the adults said they were going to take the shuttle bus up to Atlantic City for the day. All the cousins were planning on going to the water park. Note I said planning, because by the time the shuttle bus left the skies were getting cloudy. By 10am there was no sun at all. We decided to hit the boards (the boardwalk) and checkout the games and rides. After lunch it started to rain so we made our way back to the hotel.

There were five of us, myself, cousins Stephie (14) and Cassidy (12), Carol (13) and her friend Lisa (14). We hung out in Carols room because she had the kitchenette. We played cards for a while then found a "Trivial Pursuit" game in the hotel office. The girls were kicking my butt badly and wanted to make the game more interesting. I suggested strip "Trivial Pursuit" and got laughed at. Stephie said "truth or dare", if you got a question wrong you had to answer a question truthfully or take a dare. I agreed so long as no one (me) has to run around naked, seeing as I was losing so badly.

The game started out good and the truth answers mostly involved kissing and that kind of thing. What else do 12-14 year old girls ask about? Then came the big truth question, they asked me if I ever play with it? I didn't know what to say and stared blankly at them, as I'm sure I turned bright red. After some giggling from them, I said I'd take the dare. The four girls started to whisper and then really giggle! They wanted me to dress up like a girl and finish playing the game like that! It took some pleading by Lisa (yeah right) and I agreed to do it. What they didn't know was it was a dream come true for me.

I liked girls, and loved their clothes. I always have, I had even worn some of Carols clothes when we visit their house. They had the clothes hamper in the bathroom and I would love to check out what there was to wear as soon as I got there. One time I put on her panties and decided to leave them on for the rest of the night, and make a potty stop just before we left to take them off. What a big surprise I got when I woke up in the car already half way home and still had on the panties! I was always scared she would find out or worse my mother finding out. I don't think anyone ever knew?

I pretended to be shy about it and the girls told me to go in the bathroom and take off all my clothes. Put them in the beach bag hanging on the door. While I undressed I heard lots of laughing and draws opening and closing. My heart was pounding!! What would I be wearing? Will they be making me look silly or just regular girls clothes? Maybe Carols pink shortalls? My mind was racing my head spinning!! Was this really happening? Then a knock at the door, are you undressed? I said yes as calmly as I could! I was told to pass out the beach bag. I was nervous so I wrapped a towel around my waist and slowly opened the door to find a waiting hand, which quickly grabbed the bag and handed me a shopping bag. Moments after closing the door and locking it a voice asked if I like my new clothes? I didn't even have a chance to open the bag I replied.

The first thing I saw when I opened the bag was the light pink "baby" tee shirt Lisa wore to dinner last night. (I always notice what the girls are wearing). I carefully laid it on top of the toilet tank. Then I took out a denim skirt with small pinstripes. But what I found next almost made me fall on the floor. It was a bra!!

Not just any bra, but a training bra. I knew that because I always checked out the catalogs and advertisement fliers that come in the Sunday paper. I would always look at the girls in school to see who was wearing one and if I could tell what kind. I had only dreamed of wearing one and now the girls are expecting me too. I couldn't disappoint them could I? It was a "Teen Charm" size 34AA. It had a little padding in the cups and a single pink rose in the middle. My knees were shaking by now and I almost forgot there was more still in the bag. I pulled out a pair of white cotton panties, light pink socks and a pair of white "Keds".

Now I had to get dressed! There was a lot of giggling going on just outside the door. The girls asked if I liked my new clothes? My reply was something like, "it could be worse". By this time my little "fella" was standing at attention and I didn't know what to put on first? The training bra or the panties? With the girls telling me to get a move on, I slipped the panties up my legs. When I got up to my hips I quickly tucked myself down and back between my legs and pulled the panties the rest of the way up. That gave me the flat look of a girl in front. I had practiced this move many times before. The panties fit me so well; I couldn't believe it was me in them. They were plain white cotton with scalloped edges at the legs and waist. When ever I had worn panties before I always looked for pink or flowery designs that screamed girlie! But these plain white panties I was wearing made me feel more like a girl than ever! The girls hollered to get a move on or they were coming in to help me! That snapped me back into reality!

Next came the training bra. I had seen many pictures and studied girls wearing one but I never actually put one on, or touched one for that matter. I knew how it should look on, but getting it that way took some trial and error. Multiple attempts at reaching behind to hook it failed miserably. I even tried hooking it and putting it on like a shirt. Guess what, no good! The bottom band kept getting twisted. Then as if a light went on in my head I tried hooking it at my waist and pulling it up. Ta! Da! I was hooked!! I couldn't help but stare into the mirror; I had tiny boobs just like the girls in school! I had to keep looking because I couldn't believe it, no matter what angle I looked they were there. Tiny as they were, but definitely boobs. I figured if this bra could do that on me then most of the girls in my class were probably as flat as I was. Any way I loved everything about it, right down to the pink rose. I almost didn't want to put the shirt over it.

The girls were getting impatient so I slipped the pink "baby "tee shirt over my training bra, and when I smoothed it out I still had little boobs. The shirt had a little bow in the middle of the neck opening and the sleeves and bottom edge had a wavy stitch around them. It was unmistakably girlie. Next came the skirt. It was blue denim with pinstripes. I stepped into it and pulled it up over my panties. A chill came over me as I looked down to zip the fly and snap it closed. I imagined looking down at my smooth flat front wearing panties all the time. The skirt came about half way to my knees and two small pockets in the front. The girls were now banging on the door trying to get in. I said I was just putting on the sneakers and proceeded to pull on the little pink ankle length socks they gave me. To my surprise I was able to squeeze my feet into the white "Keds". As I stood up and saw myself in the mirror my knees almost gave way! My heart was pounding and I momentarily gasped for air! I wanted to cry! (Tears of joy of course) I could not believe I was about to walk out in front of girls, dressed in their clothes.

I took a deep breath and unlocked the door! I slowly opened it and tried to pretend I was embarrassed and not enjoying this at all! After a quick giggle the girls started checking me out for real. They were as surprised as me at how well everything fit and how good I looked. I remember Stephie saying "I didn't think he would wear my bra; I'll never wear that one again!" Carol asked if I had on the panties as well? And does she need to check? I quickly lifted the bottom of my shirt and pulled the panties waistband above the skirt. My head was still spinning when the girls said "OK lets get back to our game". I had almost forgot how this all started and I reluctantly turned and headed towards the bathroom. Lisa said, "where are you going?" the dare was to dress like a girl and play the rest of the game like that. I reluctantly (yeah right) agreed, and sat down on the bed to play the game. The feelings going through my body were unbelievable, the snugness of the skirt on my thighs as I sat, the pulling of the bra on my shoulders. The bra made me want to keep my back straight and my shoulders back, not because it was to tight but because, I don't know why, just because I wanted to I guess? I kept fidgeting on the bed and Cassidy wanted to know what was wrong? Lisa chimed in he is getting use to his new clothes. Stephie suggested I get up and walk around. As I did they all started giggling again. Lisa said I needed some lessons in sitting in a skirt! I said I hadn't had any practice before. "Lets try it again" said Lisa. This time I kept my legs closer together and slid my backside onto the bed leaving my legs off the side. Not bad they all agreed. After a few rounds more of "Trivial Pursuit" I instinctively slid one leg onto the bed and folded it under myself and continued to play. Carol noticed and said that was very girl-like of me; I just gave her a look as if I was mad for her saying that about me. (I really wanted to thank her). Stephie said she would be right back and went out side, when she returned she opened the door and said SMILE as a flash went off. It was her dads Polaroid camera. Now you will have something to remember this by and she handed me the picture. When it finally developed I couldn't believe it. It was a picture of four girls sitting on a bed playing "Trivial Pursuit". Looking at the picture made me all dizzy and light headed, if I wasn't sitting there in a bra and panties with a skirt and top on I wouldn't believe it was a boy in the picture. Stephie said I could keep the photo and as I looked up the flash went of again! She said this one is for them!

We had been playing about 20 minutes with me dressed when I missed a question and decided to take a dare, figuring how much worse (better) could it get? The girls dared me to let them put makeup on me to go with my clothes. I protested for effect but was hoping they would follow through. They didn't disappoint me and Cassidy went back to her room for her make up stuff. With me now sitting on the end of the bed they spread the cosmetics out on the dresser. Lisa said, "remember she is only 13 and just started wearing a bra; lets not go overboard with the make-up". That was the first time I heard them refer to me as a girl. I don't know if she did it on purpose or not, but a warm feeling came over me when I heard it.

As they brushed, dabbed, rubbed, and smoothed things on my face, the events of the last 2 hours started running though my mind. I had always had an attraction to girls' clothes, and even pilfered a pair or two of panties, but what had happened to me today was incredible. I wondered if I was gay? For wanting to be dressed as a girl? How could I go from wanting to wear panties to sitting here dressed totally as a girl right down to the "Keds" on my feet? How could I not ever wear girls' clothes again? My mind was racing again and the room was a blur! Stephie ask if I was all right? I snapped out of it and said, "Yeah I was just afraid of getting caught". They told me I had nothing to worry about and asked me to look in the mirror. I just sat there and stared into the mirror! The girls were as surprised as I was, even with my short hair there was now way I could be mistaken for a boy! They asked if I would let them do something with my hair? I said so long as you don't cut it and I can fix it back then have fun!!

Lisa started digging through her suitcase and brought out some hair clips and berets. Cassidy got a water spray bottle and started wetting my head down. I will not forget the tingling sensation I got when the first comb pulled through my hair. I was in heaven! I would let them comb my hair all day if they wanted. They brushed and combed and pulled, then brushed and combed again. I couldn't see what was happening, but I didn't care at this point. They could have cut my hair, and if I noticed I wouldn't have cared. When they finished Lisa kissed me on the cheek and Stephanie snapped a photo of the kiss. The results were unbelievable! I now had cute bangs and berets on both sides, where they found enough hair to put in berets I'll never know? But it looked great! I was now so comfortable in the girls clothes I hardly noticed them in the mirror. When I reached to touch the beret in my hair my arm brushed against my small boobies and reminded me what I was wearing.

I suggested we get back to our game before it gets to late. Carol said it had stopped raining a while ago and we should end the game now. I still didn't want them to know how much I was enjoying wearing the clothes and makeup so I asked for my clothes to get changed. The girls started giggling again and I knew something was up. They said they left the beach bag with my clothes down by the pool. If I wanted it I would have to go get it! From the room I could see it on a chair downstairs. I took one more look in the mirror and confidently headed out the door. The coolness of the after rain air on my legs was so different then when I wore shorts. Maybe, just the reminder that I was wearing a skirt made me feel that way? Then I realized just how half dressed girls must feel in a skirt. The breeze blowing against my little cotton panties! Just a small piece of cotton between me and the world. I started wondering if the girls knew how I had tucked myself and gave myself a nice flat front under my skirt? What would they say if they did see me? Enough wondering I had better enjoy my little trip and get back to the room. I walked down the outside balcony/hallway to the stairs. As I turned to go down I froze in my tracks! Someone was coming up the stairs! I just stood at the top frightened not knowing what to do. Who was it? Do I know them? Will they recognize me? It was the father of some boys I met that were staying a few rooms away. He just looked up and gave a friendly/hello smile then went on his way. When my heart rate went back to normal I went down and out to the pool. I picked up the bag and headed back upstairs.

When I got back to the room I found the door locked with the girls sitting outside. "Very funny" I said, and proceeded to go to my room. That door was also locked and when I reached in the bag to get my key from my pants pocket I got a big surprise!! All I found was a couple of towels from the room. The girls broke out in laughter, probably from the look of terror on my face. I said, "that's not fair, I've done everything you asked, a deal is a deal!" They said "just one favor? PLEEESE!" Not wanting to really get changed anyway I said "what?" Lisa asked me if I would go to "Annie's Pretzels" and get everyone a pretzel? She said it was her treat and handed me $10. "But that is 8 blocks up the boardwalk?" I said. Carol said " Then you better get going! I made a few more pleas not to go but in the end I started on my way to "Annies Pretzels"

 

Watch for the continuation: "Bobbie on the Boardwalk"

  

  

  

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