Reacquainting Oneself Ch. 04

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Diane spends an afternoon with the ladies, learning her role.
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Part 4 of the 7 part series

Updated 06/11/2023
Created 11/26/2021
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I awoke the next morning, a little disoriented by my surroundings, and a little sore.

Robert remained fast asleep, so I rose quietly to avoid waking him. I slipped into the washroom, and took a shower. The warm water helped to relax me.

I took care to use the flower-scented body wash and shampoo, not thinking why that was available.

I quietly filtered through my options in the suitcase Robert thought was mine. It did now seem rather dubious that it was an accident, but rather a deliberate attempt to feminize me. Regardless, it did seem to be what everyone wanted, and after last night it was worth giving it a try.

Initially, I figured I would find the most androgynous of clothing. I pulled out some shorts and a V-neck shirt. Yet, then I had the urge to be daring. If they want to feminize me, then I would shock them by wearing the most feminine clothing available. I selected a white summer dress with a floral print. Figuring, they wouldn't be seen, I selected some cotton panties and the matching bra.

Yes, this suitcase was definitely a setup as it was an A-cup bra that could fit me. Carol was most definitely more than an A-cup breast size.

Not surprisingly by this point, I also found a hairbrush, dryer, lipstick, and a few other basic cosmetics. I grabbed the clothes, cosmetics and accessories, and went back into the bathroom. Noting on the way in that Robert remained fast asleep.

I wasn't quite certain I knew what I was doing with the makeup, but I tried my best to remember past lessons such as Carol's quick tutorial last night. It turned out good enough. I didn't want to over do it, not for a sunny weekend by the lake.

I was afraid the hairdryer would wake Robert, but it appeared that he could sleep through most anything. With this new hairstyle Carol had given me, I wanted it to look good. Fortunately, it was straight, so it wasn't too difficult to maintain.

And then came the clothes. The panties were straight forward, and oddly comforting. I struggled with the bra, before remembering that you could clip the straps together, and then twist it around to fit. Strange how the bra gave the impression of breasts, even if there really weren't. It truly set the tone for femininity. More than I could have imagined.

Finally came the dress. I slipped it over my head, and allowed it to flow down over my body. Some minor straightening, and that was it. I stared into the mirror, and was shocked at the overall impression. Perhaps I was a little tom-boyish with the tiny breasts, but the overall look screamed feminine. These clothes fit me in a way that my regular clothes never did. And most importantly, I looked cute.

I did a little twirl, and swayed my hips to let the dress helm flare out. A light breeze flowing over my panties. I had to muffle a giggle. This was fun.

Satisfied that I looked like an attractive young woman, I snuck out of the room and down the stairs. At first, I was thankful that the house was quiet. Yet, rationally that didn't make sense. They were all going to see me dressed en femme eventually.

The only other person awake this early was Mitra. I found her in the rec room, curled up on the sofa, reading her tablet. She smiled when she saw me. "Good morning Diane."

"Good morning." She made no notice of my dress. Was this what they all expected of me?

"I made some coffee, so help yourself. I usually wait for the others to have brunch, but you're welcome to have whatever you like." She casually stated.

"Sounds good. Can I get you anything?"

She pointed to her coffee cup. "No, I'm good. Thanks."

I nodded, and went to pour myself a cup of java. I didn't want to spoil the brunch, but I was surprisingly hungry considering the large BBQ last night. I settled on a toasted bagel. And with bagel and coffee in hand, I returned to the rec room.

Mitra smiled, welcoming me to join her. "I like your dress."

"Oh, thanks. I wasn't sure if this was really me. It's not mine. There was a mistake with our bags." I knew this was a lie I had been told, but how else do I explain this?

"Well, it was a good mistake." Her tone suggested that she knew the truth. "The dress is much nicer than the ill-fitting shirt and pants you were wearing last night."

Of course, she had gone to her room with Kyle before the hot tub and the subsequent play in this room. She had only seen me in my regular, male clothing. Yet, she didn't think those clothes fit me. What did that say about me? I could only blush.

"I was so glad that I didn't find you huddled out here over night."

I knew what she was referring to, Robert's last guest hiding away the night. "Oh, you know about that as well?"

"Of course. I was here that weekend. In fact, I'm always the early riser. So, unlike the others, I saw the poor thing before she took off. She was shivering in fear, as if Robert would ever hurt her. Such a shame. Poor sissy."

Poor sissy? "You mean poor Robert?"

"Well, yes, poor Robert too. A handsome guy like that shouldn't suffer from blue balls all weekend." I was surprised by how crude she was being, but said nothing.

"...But I was referring to the poor little sissy. Too scared to accept who she really was. Afraid to admit that she was a sissy, and that she should submit to a real man. So sad."

I pondered her words for a moment.

"Oh well, all's well that ends well. Here you are. And judging from what I heard last night, everything is going great between you and Robert."

I nearly spit out my coffee, and my face turned beet red. "You heard us!"

"Oh yeah." She had a wide grin, before putting me at ease. "Don't worry, it's not like the rest of us are nuns."

I chuckled. "Yeah, I heard you too."

She laughed. "Yeah, I'm kinda notorious for being loud."

Just then, Kyle entered the room, coffee in hand. It was amazing how a muscular guy could look so handsome wearing old jeans and a T-shirt. "What's so funny?"

"Oh, we were just debating which of us was louder when being fucked." She was so nonchalant about sex.

I buried my face in my hands, dying of embarrassment.

Yet, Kyle was not prepared to let this juicy conversation die. "Hmm, hard to say. Fortunately, we have the weekend. So, it seems that we will have to have further tests." He leaned over and kissed Mitra.

The sparkle in her eyes was all the answer that he needed. I thought about what this meant. Was Robert going to fuck me again? I hadn't considered this, but now that I did, it seemed likely.

Mitra looked at me, and spoke to Kyle. "Don't you think Diane and Robert look good together?"

She called me Diane, not Dan. That now seemed to be a given. Although, as I was sitting there in a dress, how could I argue?

"Yeah, they do." Kyle seemed indifferent. He had no interest in a discussion about relationships, and certainly not someone else's. Looking at me, appraising me. "Robert's a lucky guy. Diane is very pretty."

Mitra playfully swatted him. "Hey buddy."

Classic catch-22. He wanted to compliment me, and assure the new girl she was pretty. Yet he was sitting beside his girlfriend. "I just mean, if I didn't know already. No offense Diane." He looked between Mitra and I. "... that I would consider her very hot."

Mitra gave him a dirty look. Keep digging that hole buddy.

I giggled. How could I possibly compare with a beauty like Mitra? How could I possibly make her jealous? And yet, how did I end up with a gorgeous man like Robert?

To my relief, they switched topic. "Any plans for today?" Mitra asked.

Kyle shrugged. "Not sure. Robert and Stu were talking about taking out the canoes. That could be fun. I've also been wanting to check out the caves nearby."

Clearly, neither of those options appealed to Mitra. Nor did she expect them to. "I'm thinking of just doing some swimming, catch some sun, and Carol promised me a pedicure."

Her activities had an equal appeal, or rather lack thereof, for Kyle. He nodded, and looked at me. "What about you?"

On the surface, it was a friendly inquiry. Yet, the real question was do I spend the day with the guys doing masculine activities, or do I relax by the lake with the gals, and get my nails done?

I was tired of pretending, and proving time and again how weak I was compared to other men. "I think I'll stick with the swimming and sunbathing."

Kyle nodded and smiled. Jesus, did everyone prefer me as a girl?

Lisa and Steve entered the room holding hands. "Good morning."

Like the rest of us, they had the same morning after glow from a night of passionate sex. And like the others, they seemed to prefer me in the dress. Lisa complimented me on it, and I simply thanked her.

Shortly afterwards, Robert and Stu sauntered downstairs, and joined us in the living room. I had a lump I my throat when I saw Robert. He wore khaki pants, and a T-shirt. Yet, even in this most casual of clothing, he was stunning. His chest pressed against the shirt, outlining his muscles, and his biceps were like tree branches of solid muscle. This was my guy.

And the smile I received when he saw me sitting here, wearing a dress. It made my heart melt. He sat next to me, and kissed me. "Good morning sweetie."

I blushed. "Good morning."

He wrapped his arm around me, pulling me in close. This was a safety and comfort that I had never experienced. I was someone's significant other. I was his girl. And he wasn't just some guy, but a tall, gorgeous man who exuded success and power. He could choose anyone, and he chose me.

Before we could get too shmaltzy, it was decided by the group that we start brunch. Our group moved to the kitchen. I did ask, "What about Carol?"

Lisa responded. "That girl could sleep the day away if we let her. We're not waiting for her."

The group nodded in agreement, even Stu. So much for chivalry, and coming to her defense. Mind you, you could tell from his nervous smile, that perhaps she hadn't gotten much sleep.

We were out on the patio, part way through our brunch, when Carol did appear. She still looked half asleep, and gave a groggy good morning to everyone. Her eyes did perk up a bit when she saw me in the dress and makeup.

No one was rushing anywhere. We sat back, chatting, and finishing our brunch. As we lounged around, it dawned on me how comfortable I was. I was typically a nervous wreck in social settings. Talking to women, particularly beautiful women like these three, had been near impossible. Yet now, everyone seemed to like me.

I found myself staring at Robert periodically. He was so handsome. How did I never notice that? I mean, objectively I always knew that. Yet, now I had to resist the urge to drag him into the bedroom and ravage him.

As the guys set off in the canoes, I had second thoughts about not joining them. Wouldn't it be great spending the day with Robert?

Carol noticed my pining look. "I recognize that lost puppy look. Don't worry. Let the guys enjoy their rugged outdoor sports. They'll be back. And after a day of relaxation, pampering, and caring for ourselves, we'll drive them crazy with our feminine wiles."

I laughed. Once again, her exuberance, and good-natured slutty attitude, helped to boost my spirit.

"Come on. Your bikini briefs are still in my room. I'm assuming the top is still in the case."

I nodded, and followed her up to her room. Lisa and Mitra were just behind us. We all agreed to meet at the pool.

I retrieved the bottoms from Carol, and was about to dash off before she stopped me. "Aren't you going to tell me about last night?"

I shook my head. Still too embarrassed or confused to put it into words.

Carol dramatically pouted. "Oh come on. Being coy. I know you loved it!"

How does she know? I guess my ecstatic screams did kind of give it away. I blushed. "I don't kiss and tell."

She chuckled. "Gentlemen don't kiss and tell. Girls gossip about everything."

It was my turn to laugh. I guess I was now one of the girls. I winked, and exited the room.

"We're not done with this conversation!" Carol called out after me.

Safely in my room, I undressed, and donned the bikini briefs. My little penis once again easily tucked out of sight. Then I retrieved the top from the case. The string top which I wouldn't even dare touch last night. It fit me well, and looked super cute. The final touch was a pair of sandals with a short heel.

I pondered how everyone was reacting to me. Carol was a boisterous and fun-loving tart. Yet, she did have a point. Women talked about things that men would not. What did I know about any of this? I looked great as a woman. Really, I did. Far more than I had ever imagined. Yet, how do women act? What mannerisms should I adapt?

The one question I was not asking myself, why am I doing all this?

I was the last to arrive at the pool. Lisa and Mitra were in the water. Carol was by the mini-bar, setting out some glasses, and opening a bottle of red wine.

They were all gorgeous in their sexy bikinis. It gave me a moment's pause. Would I be caught staring? How could I possibly compare to these goddesses?

"Finally." Carol proclaimed. "What took you so long? I thought you only had 1 choice of what to wear?"

There was no other choice, but for me to wear a 2-piece bikini? I sidestepped the question. "Isn't it too early for wine?"

"It's never too early for wine." She responded in her usual jovial manner. "And I'm not driving anywhere."

"And Stu wouldn't let you drive his car," Lisa chimed in.

"Tell me about it. Men with their cars. What's up with that?"

Carol's question was rhetorical. There were no men here to respond.

She walked up to me, and reached up to my ear. "You probably shouldn't wear those in the pool." She removed the earrings.

I was stunned. How could I have completely forgotten them?

Carol set them to the side and returned to pouring herself a glass of wine, She offered me one, but I declined, choosing to dive into the pool. It was a decent enough size that I could do a few laps. Forgetting myself in the water, as I often did.

Lisa and Mitra relaxed at the shallow end of the pool, standing in the water, chatting, and enjoying the sun. Carol sat along the edge with them, glass in hand.

Nervously at first, I joined them. It felt strange to be standing within the pool next to 3 scantily clad women. Perhaps I should have taken Carol up on her offer of wine. However, there was no reason to worry. They were all so welcoming.

Lisa touched my shoulder, surprising me with its intimacy. "This is a cute bikini. I like the little hearts." Mitra and Carol nodded in agreement.

I blushed. I was not accustomed to compliments, and certainly not from a beautiful woman. I mumbled, "Thank you."

It made me conscious of my breasts, or lack thereof. Most of my life I had been obsessed with what I lacked downstairs. It felt strange to now worry about what I lacked upstairs.

The ladies were focusing on me. Not in the taunting manner that I was accustomed to. Nor in a sensual way that I had only fantasized about. Just sisterly interest, like I imagined girls acting in a sorority. What did I know?

What I did know was the effect their attention was having on me. My little penis pressed against the thin fabric of my bikini briefs.

For the moment, the water was up to my chest disguising my little tent. Yet, this did present a problem as Lisa and Mitra decided to exit the pool.

I attempted to be coy, saying I would swim a few more laps first. However, Carol saw through this ploy. She must have seen me blushing.

"Oh no you don't. You're just trying to hide your excitement." Then speaking to the others, "You have to see Diane's little weenie. It's so cute."

I wish I could say this humiliation helped to reduce my erection, but it had the opposite effect. Resigned to my fate, and head bowed in shame, I exited the pool.

"Oh wow, it's barely noticeable!" Mitra exclaimed.

"What about when it gets hard?" Lisa asked.

I hated to admit it, but I suppose the masochist in me wouldn't permit me to lie. "I am hard."

Carol attempted to cheer me up. Although, her motivations were always suspect. "Doesn't it feel better wearing a bikini or panties? It fits much better."

It was still hard for me to admit this. Yet, it did reconfirm the way women had always treated me, as too small to be a man. The difference now, they liked me in my new guise.

I was not offered much of a reprieve as Carol asked me to apply some sun lotion to her back. She lay down on the lounge chair, giving access to her firm ass, and her smooth skin.

My hesitancy was ignored, as Lisa began rubbing the lotion onto Mitra.

Seriously? I could rub oil into this beautiful woman's back, and essentially massage her ass cheeks? That was ok? Stu wasn't going to beat the crap out of me for touching his lady? Apparently, it was ok, so long as she wasn't be touched by another man, and no one saw me that way.

Even more unnerving was when Carol reciprocated by applying lotion to me.

Yet, they all seemed fine with this. I was fantasizing about erotic massages, and oil wrestling. They were just sunbathing, and looking out for one another.

Our inhibitions declined as we got into the wine and marijuana. That was when the need for gossip, and pestering me for details really started. Carol had threatened this wasn't over.

"So, tell me Diane, was Robert always such a hunk? Even back in high school?"

Did all the ladies have a thing for Robert? Not that I could blame them. Yet, it did raise a good question of my perspective over time. "I guess you could say that."

"You guess? No rendez-vous under the bleachers, or in the back seat of cars for you two?" It wasn't clear if Mitra was serious, or making fun of me.

"Oh, no! I never thought of him that way."

Carol persisted. "There must have been something between you two. Why else would he seek you out after all these years?"

Once more, I had to ponder Robert's references to an attraction back in high school. I voiced my thoughts to help me understand it all. I explained how I was routinely taunted as a sissy, and called Diane. And for the first time, I was the one telling the story of the locker room incident with the cheerleaders. The story told by dozens throughout the school, now in my own words. I described my humiliation. And yes, Robert was there. Robert always seemed to be there, calling off my tormentors.

The ladies listened to me drone on for a while. It was incredibly therapeutic to just let go of all this after so many years.

"High school can be a hornet's nest of peer pressure, bullying, and a variety of taunts." Lisa's observation was accurate, but I had trouble believing someone as beautiful as her experienced any taunts or bullying. Fending off sexual advances from every dork in school, that seemed more likely.

"Surely, you must have experimented in college, or somewhere along the line? You're so pretty, surely some guys took notice."

Guys? Mitra's compliment did say a lot. "No, no GUYS. I never wore a dress again, at least not in public. And why aren't you asking about girls?"

Now, it was my turn to provide hidden meaning in what was not said.

Carol picked up on that, rather than answering me. "You said never publicly. That suggests part of you accepted your true nature. How often do you dress as a woman at home?"

Even now, I felt awkward talking about this. Yet, thus far, it felt good to unburden my secrets. "Not often. I still have the clothes from that high school locker room, and a few others. And when I feel particularly lonely, or down on myself, I like to wear them."

"Dressing up feels nice. It makes us feel desirable. Every woman gets that." Mitra observed.

"Every woman." I confirmed, attempting to note what I thought was an obvious distinction.

"Yeah!" Carol jumped in. It was her business to help women be beautiful after all. "And that's why I bet no woman ever responded to you in a romantic way. You're so clearly one of us. Any sexual advance you made would have just been confusing."

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