Kinky Vacation Pt. 02

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"Hopefully soon." I say. "I start my new job tomorrow so I may be busy for awhile. As soon as I get my first paycheck I am going straight to Victoria Secret."

"I can't wait, there are lots of sexy things to show you."

My wife and I watch the video one more time.

"WOW." I say, "I can't believe it gets hotter each time I watch it"

"Yes it does, but we have work to do. Tomorrow is your first day of work, and there still is a lot you don't know. There is more to being a woman than dressing sexy and sucking cock. You need to act professional. Sometimes being feminine is more important than being slutty. We need to make sure nobody discovers you are a man. You can't just whip your cock out when you have to pee. You need to get use to wearing panties, bras, stockings, heels etc. all day, not for just a few hours. Plus I need to teach you some secretary skills. I recommended you for this job, so my ass is on the line if you fuck up."

Reality is setting in and I am starting to get nervous.

My wife tries to settle me down. "Here is the plan. Today you are going to dress yourself as if you are going to work. Pick out your own clothes, get dressed, do your own makeup. Then we will go out and spend the entire day as a woman. We will meet a couple of friends for lunch and see how you act as a woman, not a sissy slut. Then we will come home and review the day."

I pick out one of the conservative dresses. Put on panties and pantyhose. I am able to put a bra on by myself. I even manage to put on eye makeup by myself. Pink lipstick and the wig complete the look. As I glance to my wife she gives me a look of approvement.

We meet two of my wife's friends at a local restaurant where the two of us have gone a few times. Her friends are attractive, I would say mid 30's, Amanda and Sarah. I am introduced as her cousin who just moved here and will start working tomorrow as my wife's boss's new secretary. She tells tell that I am married and my husband is an accountant. We have a few minutes of pleasant conversation, then the waiter comes over to take our drink orders. Sarah and Amanda order wine, but my wife and I don't think that's a good idea so we just order diet sodas.

Then the waiter asks me,"How's you husband doing? I hear he got laid off. Any luck with his job search?"

"Not yet, thanks for asking. But I think his luck is about to change."

Lunch conversation is pleasant. The girls ask about our vacation and my wife just says we had a great time. The girls each have another glass of wine and are a little buzzed. Now the conversation gets to be a little R rated. A bunch of sexual innuendos, and a few..wow that guy is cute, I wouldn't mind getting into his pants. I guess part of my wife's plan was to show me how women act when they are with other women.

Amanda asks my wife, "Isn't your boss some kind of pervert? I heard he has a really big cock. Are you sure Brianna can handle it?"

My wife says, "I am sure Brianna will be fine. I will make sure she doesn't look too sexy."

Then Sarah talks about her very active sex life with her new boyfriend. "You should have seen what Tom and I did last night, we had our first threesome."

Amanda tells her, "Be quiet. Us married woman are lucky if we get laid once a month. Isn't that right Brianna."

"Once a month plus I get my pussy eaten on my birthday."

We all laugh. As we get ready to leave I see Amanda talking to my wife. They are both smiling and my wife says, "It's a long story, I will tell you later."

On the drive home I say, "Your friends are very nice, I thought lunch went well. What were you and Amanda talking about?"

"For the most part it went well, but Amanda recognized you as my husband. We need to talk about a few things when we get home."

I thought I was going to get a lecture, but my wife was very supportive. "You did great. Amanda is really smart and observant, she spots things that most people don't. I am sure you will be fine at work, try not to slouch, and don't offer to pick up the check when we go out to lunch. Everything else is good, you make a lovely woman."

"So do you, I am looking forward to going to work tomorrow."

"Me too, we will get up a little early so I can help you look extra beautiful your first day of work."

Monday morning I wake up early in anticipation of dressing up and going to work. I do most of the picking out of the clothes by myself, as well as the makeup. My wife does the finishing touches.

Then she says,"You look amazing, I can't even tell you are not a woman. All I can say is with legs like that and such a pretty face, all the men in the office are going to love you."

I smile and say, "I hope so."

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3 Comments
PRTNDRPRTNDR6 months ago

I loved this story. I think another chapter with Brianna meeting the boss would be great.

cdCindy1cdCindy17 months ago

Please continue. These 2 chapters are fantastic. I can't wait to read about Brianna sucking the boss' cock and getting fucked by all the hot men at the office.

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Kinky Vacation Previous Part

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