Feminizing First Step Ch. 01

Author's Note: This is a work of fiction and a prequel series to my other published stories. All characters are age 19+.

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Today my mother and I went swimsuit shopping at a local department store. It was early in the afternoon, and we practically had the place to ourselves.

Upon entering the store, we walked past a large column covered in mirrors, and I caught a glimpse of myself. I definitely inherited my dad's diminutive body. It's almost like I never hit puberty. I am still at least one inch shorter than my mother, and probably with less body hair. I rarely need to shave. My mother talks about going to see a doctor about my "lack of development" -as she calls it. But I think she secretly likes me this way.

Since recently turning eighteen, I've been receiving more and more attention from her. She has always been a bit domineering. But things have gotten worse. Being her only child, and with my dad long gone, she has taken a special interest in me -given that I still live at home with her.

Looking away from the mirror, I glanced over at my mom as we walked through the store. She was wearing her favorite pair of black leggings and a tight, white halter-top. Her lean, athletic body was on show. Over her top, she had on a small, fashionable leather jacket adorned with all the typical zippers and buckles.

She brought me to the store today specifically to buy a new swimsuit. Her house has a large swimming pool, and she hosts her girlfriends there all the time. Last summer she paid me to be her "pool boy" during these parties and service her guests. She also required me to wear a uniform. A speedo-style swimsuit. Small briefs. I complained at first but she was insistent. I ended up wearing it all summer.

After walking around a bit, we finally managed to find the men's swimwear section. It was a small section. I had a feeling that this department store mainly catered to a female clientele.

Mom: Ah... here we are. Men's swimsuits. This purchase is long overdue, son. I did not like your pair from last year.

Me: What are you talking about? You chose that swimsuit for me. You made me wear it around the pool every day.

Mom: I know. I know. But looking back, I feel that it just didn't fit you. My mistake. Men's medium? What was I thinking? Way too big for you...

We both found ourselves staring at the racks of swimsuits. There weren't many speedo style pairs -mainly just board shorts and the like. I noticed my mom reach down to the lower rack and pull off a plastic hanger with a red pair of speedo style briefs.

Mom: Perfect! Here's one. And I love the color.

Me: Ah, are you sure mom? Aren't those a tad small for me?

Mom: No look. The hanger says... extra small. Should fit fine.

Satisfied, she handed me the hanger and went back to looking through the clothing rack.

Me: Okay...but what do you want me to do with these?

Mom: Try them on, of course! Silly. Now, there are changing rooms over there. Go put them on and see how they fit.

Me: That's ok. No need. Let's just...ah... buy them now. (I really want to get out of here.)

Mom: I'm not making the same mistake as last year. Now go. You're wasting time.

Without wanting to argue, I walked over to the small hallway with a row of changing rooms. About a minute later, I was staring at myself in a full length mirror wearing only the extra small swimsuit. I was about to take them off, when I heard a knock on the flimsy door.

Mom: Come out dear. Let's have a look.

Rather than fight this, I gave in right away. I knew she wouldn't take "no" for an answer. I opened the door and meekly walked out. We made our way back to the rack of swimsuits. My face must have been bright red.

Mom: The natural lighting out here is so much better. Okay, arms at your sides. Let me see how it fits.

She bent down in front of me and began inspecting the swimsuit. Her fingers pried at the waistband and probed the front pouch. After a while, she began tugging at the loose fabric around the pouch.

Mom: Oh no no no. You see this? You barely fill the pouch, dear. Just as I had feared. Too small yet again.

She stood up and crossed her arms.

Me: I think they fit fine. If anything, they are too small. I can feel them going up my butt.

Mom: Oh don't be silly! What we are going to...oh look there's Kendall! Hey Kendall!

A sales lady approached us amongst the racks of clothing. She was a beautiful, Hispanic-looking woman of about the same height as my mom. Her black hair was pulled back in a ponytail and she was wearing a tailored grey pantsuit with a black blouse -the store employee uniform apparently. Standing in her high heel pumps, Kendall loomed several inches over me.

Kendall: Oh hey! Thought I saw you guys in here! You should have told me you were coming!

Mom: It was kind of a spur of the moment thing. We're swimsuit shopping!

Kendall: I can see that! And how are we doing, young man? (She peers down at me with her arms crossed.)

Me: I'm ok, Kendall. Thank you.

Kendall: Good to see you again. You haven't grown a bit since last summer. I really miss all those pool parties!

Mom: Me too! But summer is here again, so we're just getting ready...

The two women conversed a bit while I stood there in my little swimsuit. I was used to my mom and her friends ignoring me. I could see that other shoppers were beginning to notice me, even through the maze of clothing racks. It didn't help that we were right by the women's section.

Kendall: So, is there anything I can help you with?

Mom: Yes. We have a problem here. (She points to my small swimsuit.)

Kendall: I can see that. That is far too large. Would you like me to find something smaller? We carry even smaller sizes in the backroom.

Mom: Would you? That would be a big help. Thank Kendall for her help, dear. Be polite.

Me: Thank you Kendall.

Kendall: Happy to help. I'll be right back. Don't wonder off you two!

Kendall turned on her heels and headed off to the back of the store.

Mom: You do know we're hosting a summer kickoff party this weekend? I want you to look perfect.

Me: You hadn't told me that. And who's...who's going to be there?

Mom: A dozen or so of mommy's girlfriends. Including Kendall. You will of course be there to serve drinks and help the guests with all their needs. You did such a wonderful job last summer.

I just stared at the floor as she continued to talk at length about the party. Another humiliating summer then, I thought. Most of the time her friends didn't even bring swimsuits or undress at all -they just lounged about the pool with me at their beck and call. I almost shuddered at some the memories from last year. One time, her friend Allison slipped ice cubes into my swimsuit as a practical joke. They all had a good laugh at that one. Another time, they made me dance and shake my ass on the table as they did karaoke.

A few minutes pass before Kendall made her back to us. She had in her hands two hangers with black swimsuits.

Kendall: These are all I could find. Why don't we start with the XXS speedo?

Mom: Great idea! Now honey, go try these on and come right back to us. Leave the old pair in the changing room on its hanger.

My mom nodded to Kendall and she handed me the XXS one. I again walked over to the changing room and put it on. It was much tighter than the first pair. The black, Lycra fabric was very snug against my skin. I hoped this would satisfy them. Leaving the changing room, I made my way across the sales floor as stealthily as possible -trying my best to avoid any attention. Kendall and my mom greeted me with warm smiles upon my return. I could tell they were pleased with this new pair.

Kendall: Why so nervous, boy? No one is going to mind you in your little swimsuit. Besides it's the middle of the day on a Wednesday. The only people shopping now are middle-aged housewives. You have nothing to fear from them.

Mom: She's right. Ok stand still, honey. Kendall and I are just going to have a closer look.

Keeping my arms at my sides, I watched as both Kendall and my mom crouched down in front of me and began inspecting my new swimsuit. They both began tugging at the pouch fabric. They glanced at each other knowingly and chuckled.

Kendall: Spread your little legs more...ok...that's better. (She shared another look with my mom.)

Mom: I agree. There is still too much loose fabric...too much room. It doesn't look right.

My mom tugged at the bit of loose fabric on the front pouch and then loudly sighed. They both stood back up and looked at me. All this time, I'd been focused on keeping myself from getting hard. I somehow managed to do this. But I couldn't keep my mouth shut about this anymore.

Me: You think they are loose? You have to be kidding me. They are fine. There is no extra room.

Kendall: Sorry honey, but this is what I do for a living -and these are clearly too large for you. I have to side with your mother.

Me: They are not too large! They-

Kendall: Oh please. You hardly fill them up. Your mother and I want you looking amazing this weekend and this one does not suit your little...anatomy. Not one bit.

Mom: My son is just too little... down there. But what are our options, Kendall?

Kendall: We still have one more pair. (She points to the hanger laying on the bench to her right.)

Mom: Oh that's right!

They both stared back at me. Without being told, I again grabbed the final swimsuit and marched back to the changing room. This time I had to pass by a group of teenage girls lingering by the perfume counter. They sniggered as I walked by, my speedo slightly squeaking with every step. Back in the changing room, I hurriedly removed the extra-extra-small swimsuit and put on this new black one. At this point I was worn out, and I didn't pay it much attention as I slipped into it. As I snapped it into place around my groin, I did notice its snugness and silk-like fabric liner. This better satisfy them, I prayed. I hung the old suit up on its hanger and walked back to the women. My mom and Kendall were now sitting on the bench by swimsuit racks. With my hands behind my back, I walked and stood in front of them, awaiting their judgement.

Mom: Wow! I have to say this is a definite improvement. We may have finally found one that fits. But it doesn't look any smaller though. There is just something about it...it just fits better!

Kendall: You're absolutely right. Perfect fit. And you can hardly see his little member there. Just a little bulge in the front.

Mom: Ha! If you can call that a bulge. Do a little spin for us, dear. Let us see the back of it.

I twirled around slowly so they could see the back, before facing them again. They both nodded in approval. Finally!

Kendall: We can go smaller if you want. There is always the children's department.

Me: No!

Mom: You sure honey?

Me: No more! This one is good enough. It feels great. End of story. Can we just buy it and leave now?

Mom: Pity. I had wanted to check if the children's sizes fitted you better. But if you insist, we can go with what you are wearing now. And you're right...it does fit you well.

Me: Great! Then it's settled. You like this one. I like this one. Let's go with it.

Kendall: There is just one slight problem.

My mom and Kendall looked at each other and began to smile together. I sensed they had some news to share with me.

Kendall: Like I was saying...there is just one thing you're missing dear.

Me: What? (I can't help but sound a bit scared)

Kendall: You aren't wearing a speedo.

Me: What!?

Kendall: You're wearing a bikini. A woman's bikini bottom.

Me: No!

My mom and her burst out laughing upon revealing this deception. I glanced down at my swimsuit and examined it closer. There were no Speedo logos anywhere. The brand was one I was not familiar with. I didn't look inside to check, but I suspected the inner liner was similar to the ones found in women's panties. I wanted to get out of it. Immediately!

Mom: We just knew you'd never properly fit into any men's swimsuit...not with your little...bits.

Me: But I can't wear a bikini! It's for women!

Mom: You just said how much you liked it. You just said it "feels great."

Me: But...

Mom: But what's changed? Nothing. Absolutely nothing.

Me: But I can't wear it! I'm a boy... I just can't!

Mom: I am sick of hearing you complain. First you said you loved it. Now you hate it. You will wear it. And that's final!

My mom's raised voice caused some other sales ladies to look our way. I hoped they didn't come over.

Mom: Why the sad face? Don't you see what this means? We can wear the same bikinis now! But don't worry, I won't make you wear the tops. At least not yet.

Me: Not yet? (Yet? What is she talking about?)

Mom: Never mind that. Kendall, now that we have finally found his size, can you show us some more patterns and styles?

Kendall: With pleasure. Right this way you two.

We had to walk halfway across the store to get to the women's swimsuit section, attracting even more attention from the other staff. I immediately spotted the rack where my bikini bottom came from.

There we were, standing among scantily clad mannequins, perusing ladies swimsuits. Kendall and my mom were having a great time. I dutifully followed them around as they picked out different bikini bottoms for me. After about twenty minutes or so, my mother had what she needed -a summer's worth of swimsuits for me. Polka dot bikinis, frilly bikinis, and string bikinis were just some of those I spied... before they were placed in her shopping bag. I even saw one bikini with the word "Juicy" written across its backside before it was tossed into the bag. But at last, we made it to the final swimsuit section.

Kendall: And here we have our Brazilian bikinis.

Mom: They are adorable! So sexy!

Kendall: They are practically thongs. Or at least something halfway between a normal bikini bottom and a thong. They are very popular with the younger generation.

Mom: I can see why. My boy must have one.

Kendall: I think so too. Here, this one seems more your style. A woman's size small.

With that, Kendall grabbed a hanger off the rack. Hanging from the plastic clips was a bright pink bikini bottom. It was embarrassingly small. She held it out for me and I slowly took it from her. It could not get any worse than this, I thought. I also noticed more sales women were making their way over to our section. Kendall was waving them over. I glanced over at my mother.

Mom: We'll wait dear. Go ahead. There are changing rooms over here in this clothing section too.

Wanting to get away from these women, I made a beeline to the nearest changing room. With the door shut, I took a deep breath and had a closer look at my new outfit. Taking it off the hanger, I could hardly tell which side was the front and which side was the back. They looked the same. I decided right then to get this over with as quickly as possible. Off came my old black bikini, and taking another deep breath, I stepped into the new pink one. I pulled it slowly up my hairless legs until it was around my waist. I felt the back sliding its way up my bottom like a thong. I was worried about the front coverage, but after looking myself over in the mirror, I found that everything was luckily tucked away and hidden. After a final once over, I opened the door and walked back over to them.

To my horror, several other sales ladies were there too, talking with Kendall and my mom. Some were talking amongst each other by the clothing racks. As I approached, my heart began to race. I felt everyone's eyes on me.

Kendall: Now isn't that a sight!

This elicited laughter from the assembled crowd. I snaked my way past the clothing racks until I got where Kendall and my mom were standing. I stood in front of them with my back to the opposite wall. I wasn't ready for what was about to happen.

Mom: How do you like your new bikini, dear?

Me: It's ok, I guess.

Mom: Just ok? I love it on you! And it's your favorite color!

As if this humiliation wasn't enough, the bikini fabric started to rub against me just right. I began to get an erection. Without missing a thing, Kendall raised her arm and pointed at my crotch.

Kendall: Oh my god! What's that! I think I see a little bulge. Are you getting excited?

Me: No ma'am.

Mom: Oh I think he is. Yes, very excited. Ladies, look away!

More laughter from the crowd. I felt my little cock straining in futility against the tight Lycra material.

Mom: It's alright son. Don't feel embarrassed. We're almost done. Now keep standing there, but turn around and face the wall. And arch your back! Thrust your little butt out. Give us a good look at the backside. We all want to see this bikini up close.

I submissively complied...at least now I could hide my face from them. Turning away from Kendall, my mom and the gathered sales ladies, I faced the wall. With my hands on my hips and legs spread wide, I stuck my bikini butt out for all to see. I could hear a few women taking photos with their phones.

Mom: Isn't it adorable? Such a cute little tush.

Kendall: Soooo cute!

Staring intently at the wall, I could just sense them approaching. In preparation, I arched my back further. My ass jutted out even more.

Mom: Now don't move, son. We're just going to feel the bikini material.

Right away I could feel their hands on my ass, tugging and probing at the tiny bikini. Immediately, something began to stir in me. I could feel myself swelling again, becoming rock hard in an instant. With their hands caressing me, my excitement began to build and build. I wasn't sure if they could see how aroused I was. I prayed they wouldn't make me turn around...

Kendall: This bikini fits him perfectly! I love the Brazilian cut! He will make an adorable little pool boy.

Mom: I know! And I can't believe I had him wearing a man's swimsuit. This fits him so much better! My little bikini boy!

They continued to toy with me. I could feel their fingers sliding under the fabric, tugging at its edges. I started to feel my heart begin to race and my breathing quicken...but then, a probing finger brushed past and then pressed firmly against my little asshole. This pushed me over the edge. It was too much to handle...

I came right then and there. Straining to suppress my involuntary orgasm, I managed to let out a little, singular grunt as I ejaculated into my bikini. I attempted in vain to stop myself humping the air in front of all these women. But hump the air I did. Several times.

As I came loads and loads, one woman let out a gasp. Another snorted in laughter. I didn't hear anything from my mom or Kendall. I was too embarrassed to turn around. Although they did abruptly stop touching me.

Mom: Did he just do what I think he did?

Kendall: Oh my god, he did. Didn't he? Just from that?

Mom: Oh my god. Turn around boy. Let us see.

Dreading this, I slowly turned around, avoiding eye contact with any of the women. My hands covered the front of the bikini.

Mom: What are you hiding?! Move your hands...

Me: I don't want to. Please...can I go change...

Mom: You aren't fooling anyone. Put your hands on your hips and spread your legs. Now!

I moved my hands to my hips and spread my legs. There I was, standing in a ridiculous superman-like pose, my little wet spot in full view. When they saw the dark spot on the bikini, Kendall and my mom had a little chuckle and mockingly clapped their hands.

Kendall: Looks like he had a little accident. Soiled his pretty new bikini.

Mom: I am so embarrassed. Sorry girls.

Me: I'm sorry mom...I couldn't help it. Please can I-

Mom: I know dear. But you are right to apologize. Now you are going to have to wear this bikini home.

Me: Yes mommy.

The fun now over, the other sales ladies slowly left us and wandered back to their normal stations. My mother rose from her seat and began collecting her bags.