What A Girlfriend Wants - Part 3

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Mary Jo selected a plain tan full skirt for me that fell just below my knees and a light pink long-sleeved pullover top with a scooped neckline to wear to breakfast. We saw the two men in the buffet line who bought us drinks the night before. When I smiled at them, they quickly turned their heads away.

That day Mary Jo wanted to go see a movie and do more shopping. Mary Jo was always in charge of the social activities planning for our household. My basic three responsibilities are transportation, admission, and popcorn, so to speak and I simply tag along to give her an arm to hold onto. We shopped awhile but didn’t see anything we (MJ) liked so we headed out to lunch at the Brown Hotel followed by a movie she selected. During the movie, MJ gave me a hand job under my skirt. She noticed me grabbing the handles of the chair and knew I was about to erupt so she put a tissue on the end of my cock when just before I exploded. I had to put my wet dripping sticky cock back in my panties myself. The gusset was soaked. MJ scooped up two fingers full of cum on her finger and put it in my mouth and then kissed me. I almost came again. She grinned and smiled. “That was nice, wasn’t it?”

Still panting from my hand job, “Incredible, MJ. You are so damn beautiful and hot.”

“Oh, I’m not done with you yet. I just getting started.” I thought to myself, ‘I’m a dead man.’

“Oh, I’ll clean your cock with my tongue later.” I was getting aroused again. “Now keep that cock of yours hidden, Claire. You know it is not proper for a Southern lady to show a bulge under her clothes.” MJ whispered with a smirking grin.

“You keep turning me on.”

“Don’t you think it is also the excitement of the clothes and being out in public as a girl too, Claire?”

“Both!” I can’t believe I just said that.

I couldn’t wait to get back to the room. I took Mary Jo’s clothes off her and laid spread eagle on the bed. I stayed dressed. I began to pleasure her with my tongue. She orgasmed multiple times. I couldn’t get out of my skirt and my damp panties fast enough to enter her. She was so wet. I collapsed.

“Oh my God, MJ. I’ll never get enough of you.”

“Good.” We took a short nap.

We woke about 3:30 or so. “Where would you like to go for dinner, Mary Jo?”

“I was thinking Italian since we really don’t have any good places near us. Okay with you?” She said. I agreed and she called the concierge to make us reservations at a nearby place. She turned to me, “I sure love you dressing and going out with me. I find it very stimulating, fun, and sexy.”

“I enjoy it too.” I can’t believe I just said that either. She came over and gave me a big hug and kiss.

“We need to get ready for tonight. I think dresses are appropriate again, don’t you?”

I nodded in agreement since I really didn’t have a say in the matter. Mary Jo picked a light purple sheath dress for me that zipped up the back. It rode just above my knees. Same heels and the night before and most of the same accessories as the night before.

We arrived at the restaurant and headed to the bar waiting for our table. For dinner, we both ordered manicotti and a salad. MJ kept rubbing my nylons with her foot turning me on.

Before we headed to the bar in the hotel for a nightcap, Mary Jo said she needed to use the lady’s room. “Come with me, Claire.”

Inside she put her arms around my neck and told me how much she loved me and how much she enjoyed me dressing as up as Claire. She led me to a handicapped stall and closed the door behind us. MJ sat on the seat and lifted the hem of my dress and told me to hold it up with my fingertips. She pulled down my pantyhose and panties and began to blow me. I was about to unload in her mouth when I heard the door open and the two female voices. I couldn’t hold it any longer and blew my load in her mouth as the door closed biting my lip not to make my normal male primeval groans as I unleashed my load. MJ stood up and kissed me pushing my warm cum into my mouth. She opened the stall door leaving me a bit exposed.  “There that safety pin should help you with that broken bra strap for now.” I quickly pulled up my panties and nylons and straighten my dress. I met her at the washbasin.

“Wow, Mary Jo. That was incredible.” I whispered. The two ladies came out of their stalls as we were leaving. I wobbled on my high heels to the bar with weak and shaking knees from her blowjob.

“The blowjob in the ladies’ restroom or the cum kiss?” she asked.

“Both!”

We order two wines in the bar and talked about the day. Two young men in tailored suits came over and sat next to us and ordered us another round. I was more frightened than scared. This dress was shorter than the one the evening before and rode up a good three inches above my knee with my legs crossed. The man to my right looked like he was securitizing every inch of my body. I tried to maintain my smile and thanked them for the drinks, and we all chatted for a while. Thankfully, MJ bailed us out. “Sorry gentlemen, we have an early flight tomorrow. It was nice meeting you two and thank you so much for the drinks.” The men stood up and pulled our chairs out when we left.

In the elevator, MJ said, “You did fine. That guy was sure checking you over. If I thought you were bi, I wouldn’t blame you for staying with him. I thought he was really cute.” I knew or hoped she was teasing.

“I’m not gay, I’m not bi either.” I injected.

“Tom, I am so sorry. I am so caught up with dressing you. I love it and how incredible you look. You look and act like a girl. Your dressing really turns me on. The only bi relationship I ever want is with my new girlfriend Claire and my husband. And, by the way, I don’t only want sex with you dressed as Claire either. Okay?”

We undressed and took off our makeup and held each other until we fell asleep. The next day, in jeans we head back home to Covington.

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 your 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 check the progress on the docks. Oh, this is 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 his 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 your work jacket, work shoes, and ballcap.” I did and came back in about 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 of 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 your 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.

The 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 of 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 turned toward me, “Unless, Claire wishes to join us girls. I do have two seats left to fill.” With the 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 turned and looked 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 through 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 six or so gowns. “Which ones do 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 the 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 swing 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 to 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.”