The Cedar Chests, Chapter 5

[Chapter 1][Chapter 2][Chapter 3][Chapter 4][Chapter 5]

During the drive home, Mary Jo said I should get electrolysis on my face to remove my stubble, so I didn’t have to shave morning and night, so she doesn’t have to completely reapply my makeup.

“But I enjoy shaving.” I told her.

“But isn’t bad for you skin to shave morning and night when we go out as girlfriends? I’ll book you for the lady who did my legs.”

We arrived home around 2:30 and I carried all our bags back up to our bedroom. I was still upstairs when I thought I heard the front door open. I assumed it was Mary Jo getting more items out of the car. Still in girl mode I came back downstairs and walked in just as Mary Jo said,

“Hi, Mom.” Mary Jo said to my mom. I froze.

“Is Tom here?” Mom asked and turned and looked directly at me and gave me scrutinizing look over from head to toe. I gave my polite girl smile at mom.

MJ replied, “I believe he said he was taking the AWD down to the check the progress on the docks. Oh, this a girlfriend of mine from college. Claire, this is Mrs. Taylor, Tom’s mother.”

I composed myself as best I could and said with a smile, ‘“My pleasure to meet you too, Mrs. Taylor.”

“Nice meeting you too, Claire. Have we met? I don’t recall us ever meeting before?” Then she turned back to Mary Jo.

“Anyway, when Tom comes back please have him call is father. He has some important meeting he wants him to do in Frankfort this week or something like that. Take care Mary Jo. My pleasure meeting you, Claire. Hope to see you again.” And she left as quickly as she arrived.

I collapsed on the couch in a sprawled unladylike position holding my heart and forehead. “I’ve never been so scared in my life!”

“Claire, can you believe your own mother didn’t even recognize you? I find that amazing! I never do when you are dressed either. It’s okay. Just call your dad in about 20 minutes. Okay.”

I just sat there on the couch in disbelief and shaking. “Mom and dad would disown me, and then dad would kill me and dump my body in Simon Alford’s pig pen for his pigs to devour if they saw me dressed like this.” Mary Jo came over and sat next to me on the couch and held my hand.

“You did just fine. I am so proud of you, Claire.” I was getting used be being called that name by now. “She didn’t see Tom at all. I still find that incredible. You passed very well.”

“I need some fresh air. I’m going to change and take a walk around our property.” I do that at least once a week to check on everything. It was a habit my dad taught me at an early age.

“No need to change. Just put on you work jacket, work shoes and ballcap.” I did and came back in about a forty-five minutes later and called my dad.

Over dinner, still dressed as Claire, I told Mary Jo, “There’s a new surprise in the barn. We have a new litter of kittens.” I always keep a couple cats in the barn as mousers.

“Kittens. Really. I’ll check them out after dinner. I love kittens. I’ll make sure mom has fresh food and water. And I’ll take out some clean rags for her too.” MJ said joyfully.” Then added, “What did you dad want?”

“I have to go up to the capital on Tuesday to sign a contract with a client for a new project now that the attorneys are finally finished with it. Should only be a day trip. You know you’re welcome to come.”

“Sorry, I am having lunch with Christy Sue. It has been ages since we have seen each other.” That night MJ was in bed reading mail and I was re-arranging my schedule for the week so I could leave town on Tuesday. Before going to sleep, Mary Jo said. “I really enjoyed this weekend with you, Claire.”

I replied, “I did find it exciting and especially that no one caught me, especially mom. It was fun and you made it very memorable. You are so damn sexy. I’ll never get enough of you!”

“Good. I hope we can do it again.” She gave me ‘that look.’ What was I to say,

“Okay, sure.” Did I just say that? She smiled and kissed me goodnight.

They next three to four weeks went by as usual. Mary Jo still dressed me. In fact, I now had to dress myself more and more. We went to lunch a couple times as girlfriends.

One evening Mary Jo was pulling out some of her long gowns from her closet. We attend many black-tie events in Louisville, Lexington and Frankfort, so I figured something was happening soon. So, I asked.

“What’s the event?”

“You know Martha Sullivan, don’t you?”

“Of course. She’s the governor’s wife. We’ve met them many times. They attended our wedding and are good friends of our parents. You know that.” I answered.

“Oh, she’s this year’s chairlady for a charity/auction gala/ball event next month’s Kentucky lady’s association. I told her I’d buy a table for 10. It’s tax deductible, too!”

“Sure, I can go. I like the governor’s events. Black tie I assume.”

“You don’t understand. It’s a lady’s event. There may be a few men there. But you will be the only man at our table.” Then with a long pause and big smile as she turns toward me, “Unless, Claire wishes to join us girls. I do have two seats left to fill.” With emphasis on ‘I do.’

‘Uh, uh…” I stammered. Mary Jo starts that sexy mesmerizing walk swinging her hips toward me with that pouty look in her cobalt eyes and runs her hands and fingernails down my chest and gently holds and massages my balls.” I knew then I was doomed.

With her hands massaging my balls it is difficult to think straight. I finally fumbled out, “Won’t your friends recognize me. Women are so good at scrutinizing everyone, you know.” I was doing my best to get out of it, but she kept pressing and rubbing her perky 34B tits against my chest and rubbing my cock. My cock started to grow. I started daydreaming about her hand job under my skirt in the movie theatre, fucking her in the dressing room and all the blowjobs too! I was rock hard and losing this battle very quickly.

As I felt and heard my zipper being lowered. “So that is a yes?” As she looked up into my eyes.

“Okay, okay. Claire will go with you.” My cock was raging hard and ready to burst out through the flimsy panties I now had to wear every day.

“Good. Let’s find you a gown.” She started to walk away, then turning and looking back with a smile at my protruding predicament. “Why you poor boy, I promise to take good care of that for you.” I gritted my teeth because my balls were turning blue and ached for release. She came back to me and took hold of my penis. “Come with me, Claire” as she used my penis as a leash to guide me to the next room.

We went into what we now call, Savannah’s bedroom, from the name on the back of the photograph. “Undress, dear.” Mary Jo started pulling gowns out of the two cedar chests and laid them on the canopy bed. I was standing there with a full raging erection stretching the satin panties with my pre-cum already on them.

“Oh dear, you can’t be trying on dresses in that state. That’s so unladylike, Claire.” As she looked thought dresses with one hand, she started jerking me off with her right hand. She handed me a tissue to me to catch my cum.  My knees buckled when I came, and I fell to the floor. She looked down at me. “I assume you enjoyed that.” Without missing a beat. “This dress will look much better now we’ve solved your unladylike issue. Change into these panties so you don’t stain these beautiful vintage gowns. Oh, you need a bra too. Here put this one on for now.”

“And put these in your bra.” The bras now were modern bras she had purchased for me. In the past she filled my bra with her old pantyhose. These were silicone breast forms. “The ladies ‘will’ notice unrealistic breasts.” I started poking the soft breast forms with my fingertip.

“Stop playing with your breasts. You only get to play with mine.”

One by one Mary Jo helped me into a six or so gowns. “Which ones you like, Claire?”

“I really don’t know.”

“You would make all of them look fantastic. But we must do something about your waistline as well. Maybe some hip padding will do the job?” She finally narrowed the selection down to four gowns.

“Put on your high heels.”  I tried each one of four gowns on three more times. “This one.” After a short pause. “I think four or five-inch heels would work best and help your hips swings nicely. We need to buy you some.”

“Those will make me 5’ 9” or 10”! Can I even walk in heels that high?”

“I do it all the time. Don’t worry, Claire, we’ll practice; it’s only an inch or two higher than what you wear now. And we need to get this hemmed for your correct heel height.” She lifted the hem to check that there was enough material to lower the hemline several inches.

The gown she selected was black long sleeved and very fitted. There was some lace trimming around the neck and cuffs. ‘You’ll need a gaff too to keep from showing that unladylike bulge of yours. We can’t have you getting too excited in public, can we? This dress will do for Saturday night. Now we need to find you one for Sunday.”

“Sunday?” I asked surprised. “I thought it was only Saturday night?”

“Yes, Sunday too. Saturday night is the charity/auction ball and Sunday will be a luncheon fashion show luncheon where we can buy any outfits we like. All proceeds go to charity. I told Martha to sign me up for a table for both days. You’ll need a cute cocktail dress.” Mary Jo started hang up the gowns on the vintage cedar hangers. “I really don’t see any dresses here that could really work as a nice LBD or cocktail dress for you. We need to shop for one for you this weekend.” When we (MJ) were finished I looked at the clock. It was one forty-five in the morning. “Wasn’t this fun, Claire.”

I smiled with a nod and all I said was. “I have to get up in less than three hours.”

To be continued…

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Tags: crossdressing, featured, fiction, Transgender

Category: Fiction