Feminizing First Step Ch. 02


(All characters are age 18+)


After purchasing my new bikinis, my mom made a special deal with me. As we sat in her car, she explained that if I agreed to be transformed into her “perfect pool boy” for the summer, she promised take me to see a doctor about my diminutive, effeminate body. And if necessary, begin testosterone hormone therapy to get a real man’s body. I agreed immediately to this arrangement. I felt that a few months as her little helper would be a small price to pay if it rid me of my embarrassing, undeveloped figure.

Her first requirement as part of this agreement was a new (or “proper” as she called it) haircut for me. We drove straight to her hair salon. Having gone to a barber my whole life, this was my first time at a fancy hair salon. After much deliberation with the stylists, my mom chose a pixie style haircut for me. My already lengthy hair was shortened and shaped into a messy bob. The salon ladies also dyed blond streaks in my normally light brown hair. My mom and the stylists seemed pleased with the results and giggled to each other upon my new hair’s reveal. In fact, they had so much fun, the salon didn’t even charge for the hair dye. It was “on the house” according to them. To be honest, I didn’t mind the haircut too much -it wasn’t too girly and it satisfied my mother. And it could have been much worse, I thought. Little did I know that this was just the beginning.

Now, over two months later, we were well into July, and a lot had changed. Today was the start of the weekend, and I had a big day ahead of me. Having just woken up, I was in the bathroom getting ready.

When I got out of the shower and went back to my bedroom, I saw that my mom had been there. She had placed my uniform for the day on my dresser. A new bikini bottom. This one was gold and adorned with little sparkling crystals. It was a bit small for me, but it was at least better than the tiny thong I had to wear yesterday.

I turned it over and stared at the back. It was a scrunch back style -made to hug the contours of my backside for a fuller, more rounded look. I felt my heart jump a little in excitement. Although, I had initially resisted to wearing these bikinis, a tiny part of me had grown used to them. I didn’t know why, but I had begun to look forward to wearing them. It also helped that my mom had bought so many that I practically had a new one to wear every day.

I took the bikini in my hands and pulled it up my hairless legs. I quickly tucked my little cock and balls back between my thighs as the bikini moved into place around my waist. I loved how it felt against me! So snug and tight. It rubbed deliciously against my cock as I walked around the room. Speaking of that…despite my best hopes, the hormone therapy was having no effect down there. It was still as little as ever, and if anything, smaller. I made a mental note to bring this up with my therapist.

As I mentioned earlier, as part of my agreement with my mother, she has allowed me to start seeing a developmental therapist for my “little” problem. Dr. Natalie Keawe came highly recommended from one of mom’s friends. And to my surprise, Dr. Keawe immediately put me on hormones, even just after one session. She promised me that this hormone therapy would help me develop into a figure more appropriate for my age. These pills come from an unlabeled, brown bottle that my mom helpfully picks up from the pharmacy. Every morning for the past two months I take one pill, and I swear I can immediately feel the boost of testosterone. I can feel it all over, but especially in my chest and between my legs. This treatment alone has made the whole summer worth it!

I see my therapist every Wednesday for about an hour. My mom drives me to these appointments gaziantep escort and usually waits in the waiting room. Last month, Dr. Keawe and I started hypnosis therapy -at her recommendation. I am not exactly sure what happens during these hypno-sessions, but I do feel great afterwards when she wakes me up and has my mother drive me home. My therapist says that these hypnosis sessions will provide an extra boost to the hormone therapy. I trust her judgement.

With the bikini in place, I rubbed tanning oil all over my body. When I got to my chest, I felt a weird tingling sensation as I rubbed the oil over my nipples. A strange, but electrifying, wave of sensation went through my body and down to my toes. Another thing to mention to my therapist, I thought. Once oiled-up, I looked at myself one final time in the mirror. I rearranged my hair a bit and hiked up the sidebands of the bikini to accentuate my hips. Satisfied, I left my room and made my outside, over to the pool area.

Already lounging by the pool, my mom and her guest were waiting for me. To my surprise, her guest was my therapist Dr. Keawe. Both were in swimsuits, and were laying on the sun loungers, talking to each other. My mom was wearing a black one-piece, but my therapist was wearing a tiny white bikini. Dr. Keawe must have been Hawaiian or something. Her white bikini really contrasted well with her beautiful bronze skin. And I had never noticed how large her chest was -I had only ever seen her in professional pantsuits and the like. Looking up at her face, I saw that her black hair was pulled back in a ponytail.

Me: Nice to see you Dr. Keawe.

Natalie: Oh please call me Natalie. At least for today. There’s no need for formalities when we’re out of the office.

Me: Okay, Natalie. Can I get you anything?

Natalie: No thank you. I’m fine. Just had a nice long chat with your mother. Brought her up to speed on your recent progress.

By now, both women had propped themselves up on their lounge chairs and were staring at me standing before them in my glistening bikini. I could tell that they had some news to share with me.

Mom: I know how much you want to have a real man’s body. And I know how much this treatment means to you. So, I have decided to help you out and make you a new offer.

Me: Okay… what are you suggesting? (I try not to sound too excited.)

Mom: Your therapist and I have agreed to increase your hormone dosage. Double it, in fact…but only if you promise to do some more things for me.

This was too good to be true! I could hardly contain my excitement.

Me: Okay!

Mom: I love your enthusiasm honey, but don’t you want to hear the conditions first?

Me: Oh yeah right. What are they?

Mom: Just a few little things. First off, none of this changes (she gestured at my outfit). I love your new look, and I want you to stay as my cute little pool boy for the rest of the summer. You look great in a bikini. But I feel you could look prettier…at least while on the job. To that end, I want you to start wearing makeup and some proper footwear.

I was taken back a bit by this news. What an odd suggestion. Why did she want me to wear makeup?

Me: Ahhhh…that’s kind of weird mom. Why makeup? Girls wear makeup.

Mom: Don’t worry about it, dear. It’s just a little dress-up. And it will make me happy -that’s all, I promise!

Me: Just at home? Or do I have to go out wearing makeup?

Mom: Oh just at home, silly. And one final thing, I want to take you to the tattoo parlor downtown and get some piercings. Not sure where on you, yet. But I definitely want to get that done too. At the earliest.

Me: What!? Piercings? Tattoos? konya escort That’s too much mom. No deal. No way.

Natalie: If I may interject, she just said piercings…so just calm down for a sec. And besides piercings are only temporary, they can heal over and go away with time. Nothing to worry about.

Mom: Exactly! They’re just temporary, but your treatment, your man hormones…that is forever. Again, this is all your choice. We can stick with your current hormone dose and keep everything the same.

When they worded it like that, it didn’t sound so bad. Doubling my testosterone levels would help me achieve my goal faster. And I guess a little cosmetics never hurt anyone. In fact, when I heard her mention the word, “makeup” for the first time, I felt a yearning desire deep within me. Couldn’t put my finger on it, but there was something strange going on.

Me: No, you’re right. I’m not thinking long term. I guess I’m ok with it. Let’s do it. It’s just makeup after all.

Mom: Really? That’s wonderful!

Natalie: I’m happy for the both of you. You made the right choice. You’ve come so far in the past two months. I can tell your body is already starting to change. Before you know it, you’ll be a man’s man. So big and strong.

Me: I hope so. I can already start to feel it in my chest and… elsewhere. But, I need to talk to you later about something. It’s just…some things are still not changing.

Natalie: Let me guess… your boy parts?

Me: Yeah… (I stared at the ground as I made this embarrassing confession.)

Natalie: Well don’t give up hope yet. There is still time. Mind if I do a brief examination right now?

She turned to my mother before glancing back at me, as if seeking her approval first.

Mom: I don’t mind. Why don’t you peel off your bikini and show us dear. Come on now. Don’t be shy. (She winked at Natalie.)

Me: Do I have to mom? It’s so embarrassing…

Mom: She’s a medical professional. Please, now you’re embarrassing me…

Wanting to get this over with, I put my thumbs under the bikini’s side bands and pulled it down. I let it fall down to my ankles, before stepping out of it. And now free of its confinement, my cock sprung out and dangled in front of the two women, their mouths now agape.

Natalie: Hands behind your back now…and come closer. I promise I won’t bite.

They shared a little chuckle as I meekly approached them, with my hands behind my back. As I got closer, Natalie straightened her posture on her chair and quickly readjusted her bikini top. Now standing right next to Natalie at waist level, I watched as she deftly took my cock and balls into her hands and began her examination. She poked and prodded for a while. It felt like an eternity. My mom watched with a curious fascination.

Natalie: Oh yes. Definite improvement here. I am very happy with these results.

Me: Are you sure? Are you sure the hormones are working?

Natalie: Absolutely!

Me: It’s … it’s just that nothing seems different to me. Nothing’s changed.

Mom: Listen to your therapist, honey. She knows what she’s talking about.

Natalie: Yes. Exactly. The initial results are clear to me. Here take a look, your cock is almost as big as my thumb. See?

I looked down as she placed her thumb right next to my penis for a side by side comparison. I didn’t want to tell her that it had always been that size. Maybe even a bit larger.

Natalie: Satisfied?

Me: I guess. But a higher hormone dosage? Double? Are you sure I’m ready?

Natalie: Yes. More than ready. And you can start today.

Mom: That’s perfect! I guess I’ll start giving you two pills every morning! kayseri escort Thank you, doctor! And I am so proud of you son!

Natalie: Your mother’s right. Quite an accomplishment. And you can put your uniform back on now. We’re done for now.

She raised her arm and pointed to my bikini laying on the concrete patio. Without needing to be told twice, I scurried over and quickly put the bikini back on. I instantly felt better, almost as if a part of my subconscious needed me to wear it. What strange feeling, I thought to myself, before I walked back over to the women.

Natalie: There is one final thing. Your mother and I were talking about this earlier.

Me: And what’s that?

Natalie: Well to be frank…we feel that your masturbation habits are adversely affecting your treatment.

Me: What!?

Mom: You play with yourself too much. You spend all this time in your room and we all know what you get up to in there…

Me: Nothing I swear! I play video games on my computer…I…I…

My face had turned bright red at this point. How did they know?

Natalie: Studies have shown that too frequent masturbation can negatively impact your therapy. Throws off your hormone levels. And none of us wants that. So, I am going to have to recommend a change. An orgasm schedule… if you will. You can still jerk off and do all the things boys do…just a little less frequently.

Me: Ummm… how less frequently?

Mom: Your therapist and I believe once a week is a good starting point.

Natalie: Yes. Once per week. And the good news is that your weekly release, so to speak, will take place at my office. During your therapy session.

I didn’t want them to keep talking about my jerk-off habits, so I didn’t protest the once per week thing… but at her office? That was too much.

Me: Why at your office? That seems unnecessary.

Natalie: We are going to be following the honor system and as a trained medical professional, I can tell whether you are holding up your end of the agreement. For that reason, you will only be allowed an orgasm under my direct supervision. And don’t worry, I can promise you that you’ll be looking forward to these sessions every week.

Mom: You see, dear, we are trusting you to have some self-control. And you are to report any involuntary releases you may have as well to me and your therapist.

Me: What happens if I slip up?

Natalie: Failure to exhibit self-control will have consequences. And trust me, we have ways of assuring your compliance. (She gave my mom a knowing glance.)

I did not like this new development one bit. I jerked-off at least once a day. And I had started to leave the bikini on when I did. The tightness around my cock and balls really heightened the experience. But when I thought about it more, how would they know if I broke the rules a little bit? They would never know. I guess I could agree to this after all.

Me: Okay. I’ll give it a try.

Mom: It’s for the best dear. You will be perfectly chaste for mommy.

Natalie: That’s a good word. Chaste. And you should start today. Keep your hands off yourself until our next session.

Me: But I-

Mom: Yes! That sounds like a great idea. Now, with all that out of the way, both Natalie and I need some suntan lotion. Especially on our backs. Why don’t you be a peach and help us out.

I gave them a resigned nod, and watched them lay back down on the loungers, this time face-down. I spent the next several minutes rubbing lotion all over their scantily clad bodies. I really wasn’t listening as they teased me about the growing bulge in my bikini. My mind was racing about what the future held for me. Makeup? Piercings? Where was this all headed?

To Be Continued.


Please leave a comment or use “send feedback” feature. Suggestions or ideas for where to take the story are appreciated. Even anonymous. I planned on this being a prequel series to my “Mommy’s Chastity Boy” series. I would like to keep it lighter than that earlier, more darker series.