Feminized by Girlfriend

Carla and I were watching Netflix at home just relaxing after a long day of work. I remember laying down next to her and looking at the pink toenail polish on her feet.

I taunted her as said "I could do a much better job painting your toes than you could."

Carla smirked and said, "It's much harder to paint your own nails than you think."

I just laughed and mentioned that it could not be that hard. We continued to watch our movie and nothing more was said on the topic. Before we knew it, we had both fallen asleep on the sofa and then moved into bed.

The following morning, we were both getting ready for work. There was a storm brewing, and it was icy cold outside. As she was getting ready, I noticed her pulling pantyhose up her legs and tucking her blouse into it.


"How the hell do those things even keep you warm in this weather? I go out in track pants and I'm still cold."

Carla looked at me and said "These are quite thick, they come in different ratings. You can get really sheer ones or thicker ones for colder days like today."

They definitely did make her legs look amazing; I've always loved her legs. I also noticed how her lacy underwear was riding up her bum which is when I made a side comment.

"How is it comfortable to have your underwear riding up your bum all the time? It seems quite uncomfortable."

Carla looked at me with a raised eyebrow and said,

"I'm just used to it, and I kind of like it. They're soft and silky so you can barely notice them."

Nothing more was said as we both started to get ready for our work day. Days had passed and I didn't mention anything of it. Not before long it was Friday night and we had just finished dinner with the plan to watch Netflix and fall asleep like most Friday nights. Whilst watching Netflix, Carla asked

"Have you ever had your makeup done by an ex-girlfriend?"

I mentioned to her that I had it done once as a joke, and it was quite boring for me because I didn't look that great in the mirror. I remember looking at myself thinking I looked disgusting, but I hadn't shaved, I didn't have long hair, and I overall feel like the colours didn't suit my complexion.

"I noticed you've been asking a lot of questions about things like my pantyhose, my underwear, and even my toenails. Since we have nothing better to do, how about you prove to me that you're so good at painting toenails like you mentioned the other night?"

I chuckled. I knew I had very good dexterity in my hands. I have always tinkered with small electronics for much of my younger years so I didn't think it would seem like much of a challenge.

"If I paint your toenails better than you, you will always want me to do them for you and that's not something I am prepared for!"

Carla then thought about it for a second.

"Well, instead of painting my toenails, how about you paint your own?"

I was intrigued. The thought had never crossed my mind to ever paint my nails. That being said, I have been envious of all the outfits, colours, and styles that women get to wear. Generally, as a male, I've never been able to deviate that far from what I deemed as acceptable male clothing.

"If I can paint my own nails without making a mess, you have to give me a massage."

Carla looked at me with an intrigued looked on her face which then spread into a cheeky smile.

"But, if you make a mess, you have to keep them painted all week in a hot pink colour."

Having dwelled on it for a short while, I decided my fine motor skills were good enough to not make a mess when painting my own toenails. I'd easily have this bet in the bag. Besides, what's the worst that could come out of this? No one would see my pink toes if I lost the bet, and better yet, I would get a massage if I managed to do a good job.

"Deal."

With a little squeal of excitement, she rushed off to the bathroom and came back with a baby blue nail polish bottle.

"Go for your life, I can't wait to see you with toes pink for a whole week!"

As I instinctively shook the bottle like I did with small electronics cleaner, Carla got her phone out and started to record me.

"Can you please not record this, it's a little embarrassing!"

"Baby, no one will see this. Trust me, and this is just for us. I would never do that to you."

That was enough to keep my concerns at bay. The smell of nail polish became apparent as I unscrewed the bottle. I bent over with my feet on the floor whilst still sitting on the couch and decided that I should put a paper towel underneath my feet, so I don't accidentally get any on the timber flooring in the event of a spillage. I decided the best strategy would be to start from the smallest toe and work my way to the biggest so I wouldn't have the nail polish ruined if I accidentally touched it whilst moving across to the other toe. Layer by layer it started to come together. The further I got into it, the more feminine my feet started to look.

It definitely was a different sight, one that I didn't quite mind. After finishing one foot, I moved to the other foot. She watched in amazement at how carefully I was able to control the brush with each stroke.

"Have you ever painted your toenails before? With your level of skill, you look quite natural at it."

"Honey, you're forgetting that I used to work with small electronics where I had to deal with screws smaller than most people can see."

After about 5 minutes, I had painted all 10 toes without making a mess or spilling any nail polish. I was quite proud of myself and smirked.

"I can't wait to collect on my massage tonight." She seemed somewhat disappointed about not having won the bet, but none the less she was quite amazed at how well I painted my toes. I sat there and let them dry while the movie finished and then we started to get ready for bed. I got the coconut oil out of the bathroom cabinet and proceeded to lay down in bed in my underwear.

Carla climbed on top of me resting on my thighs and began to give me a nice slow massage on my back. She pulled my underwear off and began to massage my buttocks and thighs as well. She was always good at giving massages to the point where I never needed to go get one. It was blissful, her hands were melting into my back relieving any built up tension.

"Honey, you have a really nice bum."

"Thanks honey, I don't go to the gym every day for no reason. I want to look my best for you."

Out of nowhere, she then asked "Do you remember how you asked if my underwear was uncomfortable riding up my bum? Well, why don't you give it a try? I have a nice set of baby blue underwear that would match your toes quite nicely, then you can decide if it's uncomfortable or not yourself."

I was surprised. Never in my life have I considered wearing women's underwear. It's not that I didn't want to, it's just that I never really had any reason to. I'm not sure where this was going to lead us, but I didn't really have any reservations with what she had proposed.

"It seems a little weird, but why not. I'm sure if you can do it every day for work, I can do it tonight for a little bit."

Carla jumped off me with a level of excitement that I have never seen before. She ran to her bedside drawer and swung the draw open. She pulled out a set of blue lacy underwear and ordered me to stand up. She handed them to me.

"Be careful with them, they're delicate unlike your briefs. They may be a little tight so just take your time pulling them up."


I slowly put my legs through the panties and pulled them up to cover my semi-erect penis and bum.

"Damn girl, they match your toes really well, and I can tell you're enjoying this, is there something you want to tell me?"

I knew this was going to be a problem with my growing erection becoming ever harder to hide. Was I enjoying this? Am I a crossdresser? Why do they feel so nice?

"No! This is just different, and they feel a little nicer than my underwear. They don't feel that uncomfortable at all."

Carla just smiled at me and said let's get back into bed. She was rubbing my penis through the panties which felt absolutely amazing. Carla could tell I was getting excited, and to her credit it was quite the experience.

"I didn't know my panties would turn you on this much."

"It's not the panties turning me on!"

I lied.

"It's your hand honey, you really know what you're doing and how to handle me down there."

I was trying to hide the fact that I enjoyed wearing them, but I wasn't doing a good job at it, my erect penis was defying my minds orders. I tried to make sure I didn't come across too keen to give away that I was really enjoying this.

"Well, regardless, you look super sexy with your matching toes and panties."

We cuddled for the rest of the night as fell asleep in each other's arms.

The alarm woke us both up at 7am for the work day. As I got out of bed, the feeling was the panties was quite electrifying. It was quite odd to look down at my toes and see the baby blue polish. I wasn't quite used to it yet, but I did really like it. Did I want to get used to them being painted? My mind racing with all these thoughts about something that is so minor.

As I started to pull the panties off to get my normal underwear on, I heard Carla pipe up

"Leave them on, I want see something else on you."

I slowly pulled them back up whilst waiting for her to come back from the wardrobe. She came back with what looked like a black sock rolled up in her hand.

"I remember how you asked if my pantyhose kept me warm during the colder days. Seeing you get a little excited down there last night gave me an idea. I think you like the panties and your blue toenails, so I definitely think you're going to enjoy this honey."

I looked quizzically at what she held in her hand. I couldn't exactly make out what it was.

"These are the sheer pantyhose which are thinner and more transparent. Given how you've been so curious I thought you should just try them on for yourself."

"Don't you think that's a bit much honey? I mean the panties and toenails was just something for fun between the two of us last night."

"It's just an idea so you can experience it. You don't have to honey, but I just thought given your curiosity you may want to have tried it. Plus, you're also in my underwear with your toenails painted, sheer pantyhose won't hurt at all, it's just a bit of nylon material. It's also cold outside today so you could do with a little extra layer."

I thought to myself what would it matter if it was cold? It's not like I'm going to wear them outside of the house. However, I couldn't argue with her logic, so I stuck my hand out and she gave them to me. I sat on the end of the bed and unrolled the pantyhose. They felt quite nice in my hands but seemed quite delicate.

"Be careful, they're quite thin so don't pull them up too hard." she said.

I slowly rolled up one half of the pantyhose to one knee, then pulled the other half up to the other knee. I then stood up and took the waistband and pulled it up to my waist.

"Honey, you're a natural. I'd have mistaken you for a girl given how easy you make it look at putting on your own pantyhose."

I paid particular attention to how she said that they were my pantyhose.

"Babe, they're your pantyhose, not mine."

"They're yours now, and you will keep them on. I'll be back in a second."

Carla disappeared into the wardrobe and came back with my suit.

"Today you're going to wear my pantyhose to work underneath your suit."

So that's why she said it's cold outside and they'll keep me warm.

"People will see my pantyhose between my shoes and pants when I sit down".

I was surprised that I didn't say no. My mind went straight to the thought of how I could get away with wearing pantyhose out in public. I also noticed how I said they were my pantyhose. I was starting to get a little uneasy at this point in time.

"Don't be silly, put black socks over the top of your pantyhose and no one will notice a thing. Come on honey, do it for me, please?" she said while she rubbed my penis through my pantyhose and panties.

"There is nothing wrong with this, I just want you to see what it's like given how curious you are. You don't have to do this if you don't want to, but it can be our little secret. If you do this for me, we can have some fun tonight."

This was kind of thrilling and fun so I decided that I would go through with it. What's the big deal anyway? It's just some material that is covering my legs that will be hidden.

"Give me my pants and socks, I'll do it, but just for today."

"We'll see about that. I might not even have to tell you to put them on, part of me feels like this is something you'll want to be doing frequently."

"Oh yeah, we'll see about that."

As I pulled up my work pants, I noticed the sensations of the fabric against my pantyhose. It was something completely different to anything I had ever experienced. It was smooth and silky.

"Also, honey, if you're going to wear pantyhose, you should probably look at shaving your legs. It doesn't look good with all that hair poking through."

She wasn't wrong, it didn't really look good at all. But then the thought of shaving my legs seemed like a step too far that I probably wouldn't consider.

"When you get home tonight, I'll show you how to shave them so you can wear pantyhose how they should be worn, on a bare leg."

I just smirked and continued to get dressed for work. It's not something I think I'll want to do, unless Carla wants to reward me with more massages, then I might consider it. I finished getting ready for work. In my black suit it was impossible to see, but underneath I was wearing blue panties, black sheer pantyhose, and my toes were painted baby blue. It was an odd sensation, but one that I must admit, felt quite nice.

As I stepped outside, I kissed Carla goodbye and felt the sensation of the panties and pantyhose whilst taking my first steps out in the cold. They definitely did a better job at keeping me warm under my clothes which was an added bonus. Maybe this is something I could get used to.

Thank you for reading. This is my first time writing a story and I would appreciate any feedback at all. Let me know if you would like a part 2!