A Trip to Washington DC

By Becca

          16-year-old Benjamin had been planning this day for the last 2 months. It was to be perfect. His parents were taking him with them on his fathers conference trip to Washington DC. It was a simple plan, he just needed to pack some of his favorite “girls” clothes in his suitcase along with his regular clothes. So pack he did and since he was to have his own adjoining room he threw in a nighty to sleep in too.

 At dinner the first night everything was falling into place, in the morning his parents were to leave early for the conference opening breakfast. He would meet up with them again that evening for dinner. A whole day to himself to explore Washington DC.

   That night Benjamin slipped into his panties then put on his sweat pants and kicked back to watch TV, when he was sure his parents had gone to bed he put on his training bra and nighty then modeled it in the large mirror before climbing into bed.

  He could hardly sleep, his mind was racing with thoughts of his adventure tomorrow. Suddenly there was a knock on the adjoining door, he froze, not sure what was happening. Then his mom’s voice, “ honey I need to use your bathroom so we won’t be late” then she opened the door. When he realized what he was wearing he darted under the covers, his heart was beating so fast and when she went into the bathroom he quickly slipped out of the bra and nighty and anxiously waited for her to be done. When she left his room he put on his sweat pants and clicked on the TV until they left for the conference.

  Once they said their goodbyes, Benjamin jumped into the shower to get his plan underway. With his fair skin and light hair there wasn’t much to shave but he ran the razor over his face, arms and legs just the same. Once out of the shower he checked the clock, 7:15, the breakfast was underway so he could now get dressed for the day.

  Out of the suitcase he took a fresh pair of light yellow panties, his favorite tan pleated skirt, white blouse, knee socks, a comfortable pair of walking shoes and an auburn wig. After dropping the towel he had wrapped around his chest he slid his panties up his smooth legs and tucked everything away nicely in the panties. A quick peek in the mirror then he sits down and pulls up the knee socks. Next the pleated skirt. Benjamin loves this skirt, it’s just the perfect length, long enough to be modest but not so long as to be frumpy. He bought it after seeing a girl in school wearing it and over heard her say it was from ‘Target”. Two days later he was wearing his own and just loves it. He put on his shoes that he bought just for this trip, he had been wearing them at home every chance he could so they would be broken in for today. Then grabbed up his blouse and wig and headed into his moms room for her make-up.

  As he walked past the large mirror he couldn’t believe it even without the wig and make-up he look like a girl. Just his luck, mom had left all her make-up out so he would not need to worry about putting it back. He placed his blouse and wig down so not to get anything on it and began to sort the make-up to find “his” colors. Just a touch of peach foundation, a hint of pink eye shadow, charcoal eyeliner and “sungold pink” liquid lip shine. Benjamin was so pleased, all that practice at home paid off. Next came the wig, it was a short auburn wig with a white headband, he paid plenty for it but couldn’t resist it when he first saw it. It was his prized possession. He kept his natural blonde hair very short, so the wig always fit perfect with no tell tale signs. The headband was not only cute but help to keep the wig in place. Once settled on his head, a few adjustments including pulling a few pieces of hair forward of the headband and he was set. Now for his bra and blouse…

  He picked up his blouse and looked around for the bra, then it happened, his mothers voice… “I think your bra is in your bed from this morning”… Benjamin didn’t know what to do, he just stood there frozen, with his blouse covering his bare chest for what seemed like an eternity.

Then his mom spoke again, “sorry dear, I didn’t mean to interrupt you. I just came back for a sweater, the conference center A.C. is blasting.

  Then Benjamin spoke, “You’re not mad? Or surprised?”

“Mad? No, not mad, but a little surprised. I’m surprised how cute you look. Are you going out like that?”

  “Ahh, yes I was, but I’ll get changed now”

“For what? I just wanted to know if you are going out, because I have a purse that you could use. Be sure to take your cell phone and don’t lose my purse.”

Benjamin couldn’t believe what he was hearing, he didn’t know what to say or do and just continued to stand there…

“Here let me find that bra for you” said his mother as she stepped away to the other room.

Benjamin’s legs were finally able to move and he followed his mom into his room. There he was standing in front of his mother wearing panties, a skirt and holding a blouse with his make-up done perfectly for a teen girl, only problem was Benjamin is a boy.

“Here it is” his mother said holding up Benjamin’s training bra.  Benjamin held out his hand to take it and said to his mom, “I thought you would be upset with me? You’re acting like I dress like this all the time, like I’m your daughter.”

“To tell you the truth, I was upset about 3 years ago when I found your girls clothes in the back of your closet, but then your father and I had a talk and we decided it could have been worse, you know, drugs and stuff. So we decided not to say anything because you were not hurting anyone and getting in any trouble. Plus I sort of liked the thought of pretending I have a daughter. Of course I never imagined you would look so good.”

“You mean dad knows? And he is OK with it are you sure?” For the first time this morning Benjamin felt at ease. He started to untangle the bra in his hands and a slight smile came across his face.

His mom glanced at the clock and said “ Oh my, your dad is waiting, I only came to grab a sweater. I’ll leave the purse out for you and have a fun day, but be careful things are a little different for girls you know”

Benjamin said “Thanks mom” as she went into her room. Then he stood in front of the mirror and put on his bra and was buttoning his blouse when him mom called out from the other room.

“Honey, I can’t be calling you Benjamin the way you are dressed, can I? Do you have a name picked out?”

Staring at the reflection of a cute teen girl he replied, Sara, I always liked the name Sara.”

“That is a nice name, I’m putting  $50 in your purse in case you go shopping and see something you like, you can treat yourself. Now I really have to go, come give your mom a kiss, then touch up your lips.

Sara happily walked into the other room, her skirt swaying with every step and gave her mom a kiss on the cheek. As her mom walked out the door she turned and said, “ I hope Sara can meet us for dinner tonight…”

Sara then went to touch up her lips, put the lip shine in her purse with her room key, cell phone, Benjamin’s wallet and the $50. A deep breath then it was out the door…