Short story

Dear girls, here's a short story I've written recently. The end has a bit of a glued-on feeling. I have some ideas where the story could go, but I also don't have the time to write it. Thus, I tried to make it look like a finished one. Also, I have moved some of the parts back and forth along the storyline, I hope that doesn't show too badly

So, what's everybody up to? Bought any cute dresses recently? Worn them somewhere? Drop a line in the comments, tell us all about it.

With a feeling of destiny, I slowly walked towards the living room. To say I was embarrassed would be an understatement, but at the same time, wearing my girlfriend’s yellow dress, my feet squeezed into her only pair of high heeled shoes, somehow I couldn’t wait to show myself to my mother. For a second, it seemed that neither one would look up from the laptop screen as I made my entrance, despite loud clacking of my high heels. Eventually though, first Sarah, then my mother turned toward me. Before I could reach the table, she got up from her seat and met me halfway.

Perhaps her face showed mild amusement, but there was no sign neither of shock nor surprise, as if seeing her son in a dress was the most natural thing of all.

“This is what happens when you let women boss you around,” she said, very matter-of-factly, without a trace of scorn in her voice.

I found it fitting that she used the plural form, because even though it was Sarah who was doing the bossing around, I still felt my mother to be instrumental in the events leading up to this moment. On the other hand, I could have said the same about myself. Although politely friendly towards each other at first, they really hit it off when Sarah and I started planning our first joint real estate investment, and they both found each other a more relevant conversation partner than me. Accustomed to being the most important person both to my mother and my girlfriend, I would feel neglected when they became far more engaged in the conversation than me. In my boredom, I would try to attract Sarah’s attention with increasingly obnoxious behavior. For a while, she made an effort to accommodate my ego, but she quickly got fed up and turned to chastising me instead. The lack of any rebuttal on my part showed my mother who was the boss in our relationship. The lack of any protest, or at least discontent on my mother’s part, showed Sarah she had a willing audience. My meekness in these exchanges reinforced Sarah’s dominance over me, and as her dominance grew, so did my humiliations, until she openly threatened to make me wear one of her dresses. My mother stifled a chuckle, raising her eyebrows at me in amusement, while I pretended not to have heard anything, thinking it to be another one of the multiple, meaningless humiliations.

Our reactions were not lost on Sarah, though. As soon as my mother had left our house, she confronted me with the obvious.

“You’d really wear a dress with your mother in the house?” she asked me.

She sounded incredulous and unsure, though in the next fraction of a second, my hesitation in replying gave her all the answer she needed, and she became more and more demanding. Despite her persistence, I managed to avoid engaging in a conversation about whether or not I would wear a dress next time my mother came to visit, or which dress I would wear. However, that was a Pyrrhic victory, because the price I had to pay for not wanting to talk about wearing a dress was actually wearing one.

That evening in our bedroom, when she told me to take one of her dresses out of the closet and put it on, I found myself powerless not to do as I was told. Too ashamed to face her, I kept my eyes on the closet even as I fumbled with the zipper of the dress, but eventually, I had to leave this safe haven. Cringing with humiliation, I turned towards her, wearing a blue and white patterned dress.

I found her sitting on the bed, leaning on her elbows, biting on her lower lip, looking at me without saying a word. Honestly speaking, she scared me, but at the same time, I felt myself strangely excited.

“What?” I finally asked her.

“Nothing,” she said, hoarsely.

“Come here,” she commanded the next moment, and I did as I was told.

Unceremoniously, her hand reached up my skirt, making me gasp with fright, and took hold of my half swollen penis.

“What’s that?” she said, “You like this, huh? Looks like we learned something new about you.”

Without waiting for my answer, she pulled me towards her, kissed me, then pushed me on my back, hiked up the skirt of my dress, pulled down my shorts and rode me to a bone shattering orgasm.

As I got off the bed afterwards, I tried to show the best I could I was doing everything short of ripping it get the dress off of me. However, tried as I might to divest myself of the offending garment, I could not rid myself of the notion that my fate was sealed.

When my mother paid us her next visit, I was trying to be on my best behavior since the moment she entered the door, at all costs avoiding giving Sarah a reason to be displeased with me, but the tension was taking its toll on my nerves. For a split second, when Sarah opened her laptop at the table, my exasperation got the best of me. Even to me, my sigh was barely audible, but it was enough to make her turn sharply to me. I twitched on my chair with fear, bracing myself for the inevitable, yet still hoping to placate her somehow.

“I’m sorry,” she said, “Am I boring you with this, Corey?”

“No,” I drew back, nervously, “Shouldn’t we clean up the table first, though?”

 “Fine,” she hissed, “You know where the aprons are.”

Blushing furiously, I turned to leave the table, but then I caught my mother’s mischievous glance.

“Aprons?” she mused, “Looks like you’re getting off easy. I thought you’d be wearing a dress.”

I froze in my tracks, allowing a moment of silence after which none of us could pretend not to have heard my mother’s words. Slowly, I turned to Sarah to see her reaction. She raised her eyebrows at me, half amused, half challenging. Dropping my gaze, I admitted my defeat and wordlessly left for our bedroom.

Sarah only had a handful of dresses, and I knew in advance which one I wanted. Just like Sarah’s other dresses, from the waist down it flared out into a pleated, knee length skirt. What made it different from the rest was the sleeveless top with a neckline that came all the way up to the collar, which would best cover up the fact Sarah made me remove all of my hair below the neck, deaf to my complaints I wouldn’t be able to wear shorts with the summer just starting. Despite the yellow color and the rhinestone studded collar, from the waist up it had looked more like a sports top than an actual dress on Sarah. However, as I zipped it up at the back I realized that the bodice was tighter than I had hoped. I could feel the fabric squeeze my belly and, looking in the mirror, I realized that under the bright light, the sheen of the fabric made the yellow color brighter than I had remembered it to be, and that the lacy bra I was wearing underneath made the unmistakable illusion of a bust. Although the pleats of the skirt were softer than in the other dresses, they efficiently obscured any possible hint of my penis, safely tucked inside a pair of panties to match my bra. With my feel squeezed into Sarah’s black pumps with a three inch stiletto heel, I was suddenly aware that apart from my face, there was little else masculine about my look.

With my hand already on the doorknob, I toyed for a second with the idea of at least putting on a different, more revealing dress to shatter the unexpectedly successful feminine illusion. But then, taking a deep breath, as much as the tight dress would allow me, I took one last look in the mirror, forced my lips in a tight smile and made my way back to the living room.

“This is the dress you wore the last time we met in town, isn’t it?” my mother said to Sarah.

Despite making it all seem so casual, I could tell that they had been talking about me wearing Sarah’s clothes while I was changing, and by Sarah’s suddenly sheepish expression, I could tell that my mother learned the true reason for it.

Without waiting for Sarah’s answer, she turned to me.

“I have to say though,” she said to me, “It almost works better on you. You don’t have those broad, swimmer’s shoulders Sarah has, yours don’t stick out so much.”

“Way to insult the both of us, mom,” I said, in half whisper.

“I beg your pardon,” my mother replied mock-defensively, “I haven’t insulted anyone. I have complimented your girlfriend on her muscular physique, and I have complimented you for looking good in the clothes you’re wearing.”

She paused for a second.

“Except for these unsightly rolls,” she said in normal voice again, poking at my stomach, “You should lose some weight if you’re going to be dressing in your girlfriend’s clothes.”

Before I could ponder at the implication of her words, she turned to Sarah again, whom the remark about my weight had put in a noticeably better mood.

“He should get his own shoes, though,” my mother said, “Otherwise he’ll stretch yours out.”

“That’s okay,” Sarah said, “I don’t even wear them anymore.”

“You still might, someday,” my mother replied, “In any case, he should have shoes that fit properly.”

Then, she took me by the hand and led me around the bookshelves that separated the dining area from the rest of the living room.

“We’ll be right back,” she said to Sarah, then led me to the couch.

“Sit right here, honey, I’ll just grab my purse,” she said.

Gingerly, I sat down, happy that I had some privacy as I girlishly smoothed the skirts of my dress under my thighs as I did so. In another second, my mother came back to the couch and sat down facing me. Before I knew it, she pulled out her compact from her purse and started dabbing my face with a broad brush. I tried to pull away, but she stopped me with a stern look and a firm grip on my hand, and I resigned to my fate as she proceeded to apply more makeup.

“I have a bunch of my old clothes packed up,” she called out to Sarah, as she was applying mascara to my eyelashes, “I was going to give them away, but I think they would suit him just fine.”

She painted my lips bright crimson with her lipstick. Obediently, I pressed them together like she showed me to, then she put everything back in her purse. Lastly, she took out a few hairpins and put them in my hair.

“All done,” she announced, got up and helped me get up, too.

“Much better, don’t you agree?” she said to Sarah as we made it back to the table.

Sarah simply smiled in response. I fidgeted nervously, standing before them, as my mother took her seat at the table again.

“Well?” my mother said, “I thought you said you wanted to clear up the table?”

Hastily, I nodded, happy for an excuse to get away from view.

“Though now you really need to wear an apron,” she added.

I gave myself as much work in the kitchen as I could find, though eventually even that was over and I had no excuse not to rejoin the table. Handing up my apron by the doorway, I walked back to the table just as Sarah was getting up.

“Bathroom,” she replied to my questioning glance.

I waited until I could hear the bathroom door close, then leaned closer to my mother.

“Could you please not push this any further than it needs to go?” I said, in a hushed, urging voice.

“Whatever do you mean?” my mother mused.

“The makeup. Your old clothes,” I said, “I don’t know what Sarah told you, but I don’t actually enjoy all this.”

“You don’t hate it, either,” my mother replied, matter-of-factly, “Do you?”

“Well, … I mean…” I stuttered, but she didn’t really listen to me.

“At any rate, you don’t hate it enough to stand up to your girlfriend,” she said.

“Well, you don’t need to help her,” I said, with a hurt voice.

She paused for a second.

“I’m trying to help you,” she said.

“How?” I moaned reproachfully, “By making me wear makeup?”

 “I get the feeling that this isn’t the last time Sarah will want you in dresses,” she said, “The next time you do it, do you want to look like a woman, or like a man in a dress?”

I dropped my gaze in silent acceptance of her logic.

“Listen,” she said, “No one knows better than yourself how you feel about dressing like this. If you really don’t like it, then talk it through with Sarah. Until you do though, you better learn to speak with a softer voice. It might save you some embarrassing situations in the future.”

I sat silently, pretending to look at the laptop screen, while waiting for Sarah to come back. When I heard her exit the bathroom, I immediately turned my head towards the staircase.

She took her seat, and, ignoring my obvious act of getting up, pulled her laptop towards her.

“Where were we?” she asked.

“Actually, Sarah,” I said.

“Yeah?” she said, a little impatiently.

“I would like to change now,” I said.

“Into a different dress?” she said.

“No,” I said, awkwardly, “Into my own clothes. Wash my face.”

“Absolutely not,” she said.

I felt my mother’s curious, challenging gaze on me.

“This is how you show your gratitude to your mother, after all the trouble she went with your makeup?” Sarah continued, “Don’t you find it a little insulting to wash it off right away?”

Panicking, I looked at my mother for support, but her expression didn’t change. If I argued that I had been wearing my makeup for almost half an hour now, Sarah might not agree. I wasn’t wearing a watch, anyhow.

“But I’m cold,” I said, finally.

My mother’s expression morphed to a friendly smile.

“If it’s just that, I can help you out,” she said.

She opened her handbag, rummaged a little, then handed me a fresh, still unwrapped pair of pantyhose.

I looked at her incredulously.

“Not the best fitting shade, but they’ll do,” she said.

“See?” Sarah said, “Now you won’t be cold anymore. Go put them on at the couch.”

I came back to the table, my legs now shimmering in a smoky grey tone.

“Feeling better?” Sarah asked.

“My arms are still cold,” I said, desperately.

Without a word, my mother reached for her black blazer that she had hung on the backrest of her chair and handed it to me.

“Here,” she said, “I want to see how my clothes fit you, anyway.”

The smooth lining felt cool on my skin as I slid my arms through the snug sleeves.

“Fits perfectly,” my mother said, buttoning up the blazer, “I don’t think you’ll have a problem with the rest of my clothes.”

“Fine,” Sarah said, feigning disinterest, “If we’re done wasting time, could we now get back to work?”

I sat down at the table and looked at the laptop screen. Aimlessly, I looked at the clock at the bottom of the screen, when it hit me.

“It’s been half an hour,” I said defiantly.

“I beg your pardon?” Sarah said.

“It’s been actually thirty five minutes that I have been wearing makeup,” I said, suddenly confident that I would be able to argue my case for washing it off.

“Time to freshen up your lipstick, then,” Sarah said.

Defeated, I looked at my mother, who was already reaching for her handbag again. I took her compact and lipstick from her, then did as Sarah had suggested.

Silently, I tried to follow the discussion at the table, but was too absent minded for that. However, it wasn’t until almost an quarter hour later that Sarah realized I wasn’t paying attention. Exasperated, she got up and came back moments later.

“Here, use this if you’re getting bored,” she said, handing me a bottle of purple nail varnish. I put it down on the table and, this time for real, tried to catch up with the conversation. After a couple of minutes, I had to admit I wasn’t going to, and started painting my nails.

Sarah and my mother kept it up for another quarter an hour, until she finally got up to leave. Sarah said goodbye right in the living room, making it clear I was supposed to walked my mother to the front door. I was of course hoping to be able not to leave the house, but my mother insisted I walk her to her car.

“I’ll need my blazer back to get home,” my mother said, “But you can keep the pantyhose.”

When I got back to the house, Sarah was sitting on the living room sofa.

“Why you little sissy,” she said to me, “You little pansy boy.”

I looked at her, dumbfounded.

“Look at you, letting your mummy put makeup on you,” she said, “Wearing her pantyhose.”

“But I…” I tried to interject, but she would let me.

“Freshening up your lipstick like a little sissy that you are,” she said.

“Come on, that’s not fair,” I said, as I started tears of shame welling up behind my eyes, “You wanted me to do that.”

Then my tears started to flow. Sarah watched me in silence for a while.

“If you’re going to cry like a girl, let me give you something to cry about,” she said. Before I could react, she pulled me down over her knees, hiked up the skirt of my dress and started spanking me. I squealed with shock and wiggled as I tried to get up, but her grip was too strong. Eventually, I had to concede I was not getting off until she would let me, and started weeping in earnest.

I didn’t even notice she had stopped, when she lifted me off her lap, then pulled me down again, only facing her this time, and started kissing me possessively. Hurt, insulted and angry at her, I pushed against her, but to no avail. Just like during the spanking, I realized that I wasn’t getting off her lap until she decided so. I stopped pushing back and welcomed her thrusting tongue in my mouth, feeling her lips, stiffly pressed against mine, smear out my lipstick. Feverishly, she reached under my skirt, pulled down my pantyhose and panties, then pushed me back on the couch and straddled me.

When she collapsed on me afterwards, breathing heavily in my ear, my mind started to wander back to the closet. It looked like it was going to get filled up with more clothes, but that was probably going to take a couple of days. I had to figure out what I would wear until then.