Feminization Locktober: Pt. 01

Authors note: Part 1 of a multi part series. This series is longer and a slower burn than my usual stories. I hope you like it as much as I liked writing it.

Xoxoxo

Desisissyvibes

September 29th!" Kelly said enthusiastically. I looked over at her from my chair, opposite her on our breakfast table. Her hair was disheveled, her make up was running and her eyes looked tired, which were all hallmarks of her having a good night with her bull.

Yep. Kelly and I were into the cuckold lifestyle. We were actually into a lot of kinks and fetishes that have so far only strengthened our relationship. "So..?" I wondered if I had forgotten a birthday or anniversary, before it hit me. Locktober.

Locktober had become an annual tradition for us, and 2022 would be the third year we would do this. It started in 2020, during the pandemic when we were locked up, pardon the pun, and decided to start exploring some of our fetishes. 2021 was the year we got into cuckolding and so Locktober that year had a cuckold bent. As for this year? Honestly it was on the verge of getting stale. It didn't help that I was regularly locked and unlocked for our cuckold play sessions with some of Kelly's bulls.

"Locktober" I said firmly. "Yup. Are you also thinking it's gotten kinda stale?" Kelly said.

"Yes!! We did it for three years and this time I've been locked for a good part of the year already!" I said. I wasn't currently locked and hadn't been for a few weeks.

"Yeah. I know what you mean. I was thinking, ``Would you be up to spicing it up this year?" Kelly said as she took a sip of her orange juice.

"I guess. But what could we possibly do to spice what we already have?" I said, not thinking about where the innocent question would take us.

"How about a locktober with feminization? Every day you'll get a feminization task to complete while locked up, and when you complete all tasks in 31 days you'll be unlocked." She said as a smile began to form on her pretty face.

"Feminization? I thought you didn't like it?" I asked. It was partly true. In the early days we experimented slightly with feminization but got distracted or rather more fascinated with chastity and cuckolding.

"Well we never explored it fully did we? We touched on it and then I got distracted with bigger cocks. I've actually been thinking about this for a little bit. The feminization aspect I mean. Because well, you've been pussy free for a while, and truth be told it's hard to see you as a man in any case. And I have started to feel like the cuckolding has taken priority over others and our spark could use some work" she explained.

She did make sense. The past few months, she had been seeing a few people but they hadn't been coming home that much. As for me, I'd just been content getting off on pics and vids that Kelly let me see.

"Okay. I mean sure. But how would it work? Like what tasks would I do?" I said as I started to wrap my head around this challenge.

"We could start slow, and ramp it up. You'll probably spend a lot of time shopping if not anything else. You'll definitely be unlocked by the end of the month. I'd need like a day to figure out the tasks, but I'd love to design this. I haven't been much of a mistress off late, so would love to have that power over you again." Kelly responded.

"Okay. But I guess I'm just worried about how far it'll go. I can't be completely feminized, I have a day job. And also shopping? Where would I get the money for that?" I said as I tried to get Kelly to see the reality of this fantasy.

"Riz. I'm a lawyer for the city's biggest firm. And you're a work from home consultant. I'll pay for this and you're barely out of the house anyway. That doesn't mean you won't be outside. That's kinda part of my plan" she said as she ended with a giggle.

"Alright. I'll do it. Will I be able to see all of the tasks tomorrow?" I asked.

"And where's the fun in that?" She said. "Every day you'll probably get a different task. Every day the humiliation is only going to increase. But that's okay because you do like the humiliation kink don't you"

It was true. I did. I had no idea why, but I loved the humiliation and embarrassment. It's part of the reason why, an Indian man lucky to married to the love of his life, turned to cuckolding. I loved the humiliation caused by my alleged inadequacies.

"Okay. Let's do this. Feminize me." I said as I accepted my fate, although happier than I should have been. Had our spicy sex life gotten stale too?

"Well not now Riz. You'll need to give me some time to come up with the tasks like I said. Plus it's only the 29th. You have two days." she said as she got up and gave me a peck on the lips.

"Wait. Does the last night rule still apply in this case?" I asked as she started to walk away from the breakfast table and upstairs to shower. The "last night" rule was something we came up with for me to have sex with her one last time before being locked up.

"Hmm. Yeah sure. Why not? It's been a while, and you may not have sex like this in a long, long, time. But, tonight if you fail to make me cum, you'll have to go down on me. Even if it means eating your own cream" she said as she started to take last night's clothes off as she walked up the stairs.

"Deal babe!" I said as I started to clear the breakfast table.

The rest of the day and the next day was pretty uneventful. Kelly left for her job while I started working on mine. I rustled up some dinner and waited for Kelly to come back home. We opened up a bottle of wine, finished dinner and headed upstairs.

Kelly wasted no time in getting naked. If I was a girl I'd be envious of her body, with her curly brunette hair that went down to the shoulders, pert breasts with pink nipples and round ass. She was around my height, five foot 9 inches, tall for a woman but not amazon-esque exactly. Meanwhile I was Indian with light brown skin, not exactly well endowed with a 4 inch penis, and a slim figure that I'd tried multiple times to bulk up in the gym to no avail.

Kelly pushed me to the bed and started sucking my cock before I had to stop her. I held her and flipped her over to take her missionary style, and entered her wet warm pussy and started to thrust. As predicted, it didn't take long for me to cum and despite my best efforts to hold it in I couldnt and came in what I estimated to be 4 minutes (that was established to be my average in any case). I got off Kelly exhausted and she giggled. "Yup. I know" I said as I started to make my way down to her pussy.

"Well no. It's not what I expected. It's just I thought of you as a girl, which you will be for this one month, and I really think you'll have a lot more fun when you aren't pressured to perform" she said as I started to kiss her inner thighs before going down on her, despite my own salty remains.

After she was also satisfied I took her in my arms, kissed her and told her I loved her and we fell asleep.

When I woke up in the morning she wasn't in bed. I put on my robe and head downstairs and didn't find her there either. I checked my phone and found a text from her.

"Check your email at 9am. See you later in the evening" read the text. I glanced at the clock. It was 830. I thought I might as well get on with my day before I get her email.

I showered and started to eat my breakfast when my phone rang twice. Two emails? Yup. Both from Kelly. One said task#1 in the subject line and the other said "Read me first". I opened the "read me" first.

"Hi sissy!

Welcome to feminization locktober. Or femme locktober? Or sissy locktober? We can workshop the name.

For the next 31 days you're at my mercy!Well kinda. You are to address me as Mistress or goddess or Miss Kelly. (We can workshop this too).

Every day you will receive an email just like the one I sent today. That will contain instructions for the task, how you can complete it, and what you need to do to complete it. You should have the whole day to complete each task unless mentioned. Some tasks require video or photo proof. Some tasks need me to be present. Everything should be in the email. If it isn't? Don't bother asking. I have better things to do than answer your silly questions.

You will be locked in chastity throughout the month. The cage will get smaller and smaller through the month. Every 7th day of the month will bring a cage change. I will be there to change your cage.

You will maintain your body properly. Work out at home as much as you need. Go to the gym if you need.

In addition to the tasks you'll also have sissy rules to follow. Certain tasks may need to be constantly repeated ever so often. I'll mention this in the task itself and this would be a rule.

Here's your first rule:

Sissy rule #1: Always wear your chastity cage.

Not like you can unlock it. The key is safe with me, round my neck until I lose it.

Here's another rule for you that we used last year that I'd like to bring back:

Sissy rule #2: A sissy cuckold sleeps in the guest room.

Not much to explain there but since I'm the one that's actually getting dicked down for now, I should get the bigger bed.

Open the next email for your very first task!

Love Kelly.

I opened the second email.

Welcome to your first task on the first day of Sissy Locktober!

Before we start there are some pre requisites I want you to complete:

1. You need to pick a new femme name for yourself. Riz Khan doesn't work for a woman now does it? You will also use she/her pronouns.

2. You need to collect all your male underwear and throw it out. Seriously. Put it in a trash bag and put it in the attic. You won't be needing this till next month.

3. Yes, even the pair you're wearing now. No male underwear at all.

Women are expected to shave their body clean and be hairless and sexy.

So your first challenge is to shave your body smooth. Including your face, neck, arms, legs and bikini area. There should be no hair at all whatsoever other than the hair on your head.

Once this is done you must moisturize your body with scented body lotion.

You have until 5pm to do so. At 5pm I expect you to wait for me at the door naked. You may be unlocked now however if I find out you have masturbated before that, the consequences will be dire.

Everything you need should be in the bathroom cabinet. Although in due time you are expected to buy your own shit.

At 5pm, I will come by for your inspection and lock you in your first cage for the month. I will also give you a gift or two that will serve you well.

See you then.

Xoxoxo.

I closed the emails and glanced at the time. 9:10AM. I should have plenty of time right? How long would this take? An hour? Maybe two? I didn't want to start off with finding out what her" consequences" meant. I had to admit, I liked this dominant nature of hers, and it was definitely something that drew me to her when we were dating back in college.

When I first admitted my kinks and my fetish for femdom and humiliation, she didn't take it very well but she warmed up to it soon enough. Unfortunately, we got into a comfortable rut even with the fetish play, and this locktober may be the kick we need to spice our lives back up.

I started to plan out the day. Even if I took 2hours to shave, that would be plenty. The other thing I needed to do was dispose my male underwear and choose a female name. My name was Riz Khan. Rosie? No. That didn't sit right. Rosanne? No.

Razia. I liked that. It sounded sexy, powerful and feminine. I immediately texted Kelly my new name and regretted it when I got the response:

"Great. But don't text me unless I text you back or ask to text you"

A small fear started to emerge. How far would this go? What if instead of bringing us closer as I had imagined, it instead drove a permanent wedge?

I glanced at the clock again. 10am. I had work to do before the tasks of the day. I immediately sat down and tried to focus.

As the clock struck 2PM, I realized I was way too excited to work. I decided to instead go forth and do my tasks for the day.

I started with the easiest task, throwing away the boxers. I just stuffed all my underwear into a trash bag.

I then started another shower to start shaving my body. I started with my chest and went down to the pubes. The "bikini area" proved to be tricky, particularly around my butthole but I had time and tried it multiple times. I checked myself with a finger and found it to be smooth. The legs, arms, and under arms weren't as challenging.

I checked the time. 4:45PM. Just in time! I didn't have to wait long because Kelly entered the door at 4:52PM, 8 minutes ahead of schedule.

"So. What do we have here?" She said as she entered. "I'm ready for sissy locktober Mistress." I replied as Kelly brought her bags down. In addition to her regular office bag, she had another bag from Victoria's Secret.

"Are you now? I'll be the judge of that. Come here and stand next to me, so I can inspect your body."

I nodded and came close to her while she appeared to inspect my body. She turned around and started to inspect my butt and gave it a light spank.

"Say Razia" she started as I registered the first usage of my femme name. "Are you sure you moisturized?" she said.

Fuck! I totally forgot to moisturize after shaving! I couldn't lie.

"Um. No mistress. I forgot" I said sheepishly.

"Well in that case, you're about to find out what happens when you disobey me. " she said as she sat down. "Come here and bend yourself over my knee". I did as I was told not knowing what to expect.

Suddenly I felt her hand spank my ass cheek hard. I winced. She paid no heed and continued to spank me for a total of five times. I started to whimper in pain. "Will you disobey me again?" She asked.

"No mistress." I said as I got up and wiped the tears of pain.

"Good. You passed today's inspection. Barely and with a punishment but make sure you obey all of my instructions to a T. Now, I think without further ado, it's time to get this officially started" she said as she pulled out a pink cage from her bag.

"A new cage? What was wrong with the one we already had?" I asked as she gave me a glare. "Did you just address me without using a honorific? " she asked as she glared at me.

"Sorry mistress" I replied.

"Better. Now didn't I say we would keep changing the size of your cage? This cage is slightly smaller than what you're used to. By the time locktober is done, your clitty would shrink down to nothing! Plus, this is pink, your new favorite color!" she said as she giggled.

She got on her knees to fix the cage on, and in a second I heard a snap and a click of a lock. It pinched a little but not as much as I imagined. The cage definitely was more snug than I was used to.

"Welcome to girlhood! You're going to love not having a dick!" She said as she giggled. "Now, I did say I got you a present! This is from the girls at Victorias secret!" she said as she pulled out a pair of pink frilly lace panties. "From now on, you will always wear panties. No exceptions. In fact, until you get better clothes, you are expected to wear just panties at home. Nothing else. Even when I'm not there. If you disobey me, I will know. Am I clear?" She said as she handed me the panties.

I deftly wore them and made sure things fit correctly. They felt good on my soft, smooth shaven skin.

"You're done for today. You're free to do whatever you want, other than masturbating of course. Don't soil these panties just yet. As for me? I got a date with this" she said as she showed me a picture of a throbbing veiny penis. "Don't wait up for me!" she said as she went upstairs to get ready.

I made my way to the guest room and took a long hard glance at myself. I was shaved smooth and wearing pink panties. This was going to be a wild month.

I woke up the next day in the guest room to a new email from Kelly.

"Good morning Razia!

Are you ready for sissy task#2? As I mentioned sissies should always be wearing panties. In fact let's make that sissy rule #3, shall we?

Sissy rule#3: A sissy should ALWAYS wear panties a underwear. No exceptions!

Now, that said, it's easy to guess what today's task is right? Yup! You're going panty shopping! And you're going to go to the Victoria's Secret in the mall near our house. You can not go anywhere else to purchase your panties. You can go anytime you like but it has to be today. In terms of what you should buy, I have a list of essential things I think you should get. Anything additional you want on top of that is up to you. Here's the essential list of 7 panties:

1. A thong, any color and material

2. A V string, any color and material

3. A pink panty, any type.

4. A PINK panty, any type.

5. A granny panty, any color.

6. A panty with writing on it

7. A favorite panty of someone who works there.

Sounds simple right? Are you worried about #7? Don't be! You're going in as a man to Victoria's Secret, you're going to be hounded by the girls there asking to help. YOU MUST USE THEIR HELP. YOU CAN NOT REFUSE. They're there to help after all. Also, if they ask if the panties are for your gf or wife, you must not lie! You have to tell them it's for you. What exactly you tell them is up to you. If you lie, I'll find out, and the consequences will not be good for you!

Lastly, the sales girls may ask you if you want a matching bra. You must refuse as you're not ready for that yet.

For proof of completion of this task? Send me pics of all your panties, plus the receipt so I know you bought them and didn't steal them from someone or have someone else buy this for you.

Talk to you soon.

Xoxoxo,

Kelly"

I read the email again to make sure I got everything. It didn't sound too hard, but the last part definitely made me nervous. What would I even tell the salesperson? "Hi. I'm a sissy cuckold and need to buy panties for myself so my little clitty can feel good while my wife gets her back blown out by a real man?".

I could hear Kelly giggle viciously if I did end up saying that. I glanced at the clock. I realized I didn't have much time to get this done in between my other chores for the day so I left for the mall.

As I approached the VS store, with its bright pink facades and hyper feminine appeal, I felt a large sense of apprehension. I took a deep breath and went in. As I expected, I was the only male in the entire store. A few ladies looked at me, most just went on with their shopping. I walked towards a display that said "5 panties for $30" and started to rifle through them with my trembling fingers until I heard someone approach me.

"Are you finding everything you need sir? Anything I can help with?" the salesperson said. She was dressed like the other girls in a black PINK t-shirt and a skirt with a measuring tape on her shoulders and an earpiece. She had pink hair, tied back into a ponytail, and her nails were painted bright pink. She had a name tag that said "Erin".

I took a quick breath. "Yes actually. I was looking for some panties. Wanted to start off with some thongs and V strings. " I said, trying really hard to not let the fear show in my face.

"Oh okay! Come with me! We just got the newest dream angels collection, and some of the panties are to die for! Your girlfriend will love them! And you'll love seeing her in them!" she said nonchalantly.

I couldn't let her go without correcting her. Although how would Kelly find out? I could lie or just let this go uncorrected. I must have looked stressed out trying to figure this out because Erin then said "Oh you don't have a girlfriend, I mean wife then! Sorry, you just looked like the type who had a gf" she said as she continued to walk towards the dream angel shelf.

"Um actually. The panties are for me." I said and tried to leave it at that. Erin stopped and looked at me.