Indiscretions Chapter 9 Part 1

Because Lisa was currently out of her mind, I was **** to make a change to my plan. My first plan was to borrow Lisa’s clothes; I don’t know a thing about women’s clothes aside from a man’s perspective and preference, so I plan to let her dress me up to get a better feel of being a ‘woman’. And thus, in place of Lisa, it is now Jessica who dresses me up.

Jessica is rummaging through Lisa’s closet, and just throws away whatever she deems no good to the floor while putting a few articles of clothing aside.

“As expected, mommy’s wardrobe is so boring and lame; thankfully, there are a few acceptable ones here,” Jessica remarks.

I recognize a few of those clothes. Like the bold red dress that Lisa used to wear when I brought her to an office party. There were also a few sexy lingeries that she used to wear during our sexy time. Oh, I remember that one sexy sheer nightgown I brought for Lisa 6 years ago during our anniversary. She no longer wears it because it has become quite small for her.

6 years, huh. Oh, how time had passed. I recalled a lot of good memories I spent with my wife wearing those lingerie and dresses.

“Daddy, are you recalling something good?” Jessica teases me.

When I realize it, I have another hard boner under my panties. I quickly tried to cover it up with my hand. My face blushed red in embarrassment.

“It’s okay, Daddy. It’s not like I haven’t seen your cock. Don’t be embarrassed. I think it’s better for you to throw away your shame for now because you are going to try those cute clothes I picked for you,” Jessica said.

She was right, I should steel myself and throw away my shame. The next few days will be full of something that may be more embarrassing for me as I try to understand how my wife and daughter feel by putting myself in their shoes. Rather than feeling embarrassed, it might be better to embrace my freaky side. Despite that resolve, I still can’t bring myself to feel okay with showing my cock to my daughter; it was something that goes against my moral compass. The feeling of guilt gnaws inside me, but I can’t stop here.

“Can you wait outside when I get changed, Jessica?” I ask her.

“Do you think you can wear those by yourself? Some of them are more complex to put on than they look like, and need somebody to help you wear them if you have had any experience with them.”

I then look at the pile of clothes. As much as I think there will be no problem for me to put them on by myself, I decided to trust what Jessica said that it may be more complex than I think. I shake my head slowly to tell her that I am not sure.

“Hence, I need to stay. I will ensure that you wear those dresses properly.” Jessica says.

I let out a sigh. I failed to distance myself from Jessica, and she is here to stay through the dress-up session. Well, it can’t be helped.

I remove my gown and undress to my underwear. I look at Jessica and ask her, ashamedly, “Should I remove my underwear too?”

“For the dress, you don’t need to, but for the lingerie, you need to remove your underwear. It’s your choice whether you remove your underwear now or later.” Jessica answers.

I then pull down my panties and try to remove my bra, but I have a hard time unhooking it. I now understand why Jessica said some women's clothing is complicated to put on or take off.

Noticing my struggle with the bra, Jessica then walks behind me and unhooks the bra’s clip. She doesn’t move away after she helped me remove my bra, but instead proceeds to fondle my new big temporary tits from behind.

“Oh god, it feels so surreal. I’m fondling my daddy’s tits!”

I let out a moan because of the jolt of pleasure when Jessica fondles my tits and pinches my nipples. “Stop…Stop fondling my tits, Jess. It makes me feel funny!”

“You weren't feeling funny, Daddy. You were feeling turned on when I played with your tits. The psychiatrist seems to make your nipple extra sensitive. Do you like it, daddy?” Jessica teases me

To be honest, it feels as good as when I am stroking my cock. My already hard cock also throbs as Jessica plays with my tits. Fortunately, because I just cum several minutes ago in the bathroom, it took me longer to cum this time, and it gave me enough time to shrug off the pleasure jolt and gather enough resolve to stop Jessica from fondling my tits.

I grab her hand. “Enough playing, Jessica. Let me try on the clothes.”

Jessica finally takes a step back to give me room to change my clothes.

The first clothes I try are a bold latex leotard bodysuit I bought for Lisa years ago. It is Lisa’s only latex clothing in her collection. It was quite skin-tight. It is quite uncomfortable because it encases and presses on my cock without giving my cock any room to move. The leotard is also quite tight around my chest. Overall, I’m not a fan.

I turn around and look at Jessica to give her a look.

“How do I look in this attire?”

“Kinky. You look like a fetish model in that getup, Daddy. I didn't expect that Mom had this kind of latex attire in her closet. You are such a lucky guy, Daddy. You can see Mom wearing that attire in private.”

I don't know why I blushed. Do I secretly like it when she compliments me that I look like a fetish model? Or because she said I lucky that I can see Lisa in this kind of attire from time to time.

“Don't just stand there, Daddy, there are still several clothes for you to try.” Jessica reminds me.

I removed the latex leotard bodysuit and moved to the next article of clothing. This time it was a frilly babydoll. Another lingerie that Lisa used to wear. Unlike the latex bodysuit, Lisa still brings this one out from time to time.

The babydoll feels far better than the latex leotard for his cock. I can feel the spring breeze hit my cock. Should have worn panties with this type of dress. I take notes in my mind.

I look at Jessica once more, waiting for her commentary before I change to the next one.

“You look cute in that, Daddy. Is this what Mommy often wears when you two have a sexy time?”

“Sometimes,” I answer her question.

Lisa prefers to just be in pajamas most of the time, but if she were in the mood, I might have gotten quite lucky to see her wear one of the spicy lingerie sets.

I move to the next one. It’s no longer lingerie, but an outer dress. It is a hip-hugging bodycon dress that I often suggest Lisa wear when I bring her to a company party. It was a tight dress, thankfully not as tight as the latex leotard.

“Twirl and strike a pose, Daddy. Let me see how fabulous you are,” Jessica instructs.

I follow her demand and spin around to show her the dress. Both my hands on my waist as I try to strike a pose like a model. “How do I look, Jessica?” I don’t know why I anticipate her answer.

“Fabulous, but it will be better if you wear high heels right now with that dress.”

I feel proud when Jessica says that I am fabulous. Proud that it proves my taste is good and my decision of making Lisa wear this dress for many company parties wasn’t wrong, and proud that I can wear the dress as good as Lisa.

But the latter part of her sentences made me feel that I am still lacking. I can still look better if I wear high heels.

“Can you bring your mother's high heels here, Jessica? I want to try wearing it.” I ask Jessica to fetch Lisa’s heel for me.

“Sure, but we don’t know if it can fit your size or not. Just wait here. I’ll be right back.”

Jessica left the room.

While waiting for the girl to come back, I look at the tossed clothes on the floor, those clothes that Jessica doesn’t pick and considers lame. I pick a few of them and slip into them.

Contrary to the first three clothes Jessica picked for me, this long-sleeved blouse and long skirt weren’t sexy at all. It is something that Lisa typically wears at home before all this madness started. Something that I should prefer as a man with high moral integrity who doesn't want his women in his life dressed like a slut, but right now, when I look at the mirror and see my reflection, compared to the previous three clothes I wear, I can only feel it’s lame. Boring and dull. A woman shouldn’t be **** to dress in this kind of clothing. I suddenly felt a little bad because I often told my wife and daughter to dress ‘properly’ in this kind of clothing. Thankfully, now I understand how they feel and have a new perspective. The only proper clothes for women are those that are sexy and liberating. No, that sounds wrong.

But my body had moved to undress from these lame, too much skin-covering granny clothing and picked another sexy dress that Jessica chose for me. A sexy cocktail dress. This dress brings back memories. Lisa used to wear this one when we were still newly married and still in the honeymoon phase. I don’t expect that she will still keep this dress instead of throwing it away or giving it to a thrift store. The dress has a waist cincher, and the skirt flares wide. The dress gave something a classic ballerina would wear. Elegant yet sexy.

Jessica returned to the room after several minutes.

“Wow,” Jessica says in amazement as she enters the room. “I don’t expect that you manage to put that on by yourself, Daddy.”

She was amazed that I managed to put on the waist cincher by myself. Well, I will not say it is easy; it took me a journey down memory lane on how Lisa did it before. I recalled that I had done this once. Back then, before Jessica was even born, there was one occasion where I helped Lisa put on this dress. Luckily, I could recall and emulate the moment. Need a few tries to get it right though.

“Who do you think your daddy is?” I say smugly.

The shame of dressing in women's clothes has been greatly reduced. It is still there, but I no longer feel awkward in these dresses in front of my girls. Maybe I will have a different response if the one in front of me isn’t Jessica, but let’s say my coworkers. But right now, the only one in front of me is Jessica. And I am trying to put myself in a woman's shoes, her perspective. And with every compliment from her, I think that I am doing a great job in this endeavor. The shame had diminished from every compliment Jessica gave me. Only a proud man was left.

“So, where are the high heels? And what is in your hand?” I ask her.

Jessica then put down another set of clothing in front of me. It is a uniform, a schoolgirl uniform, her school uniform, but not the standard kind. It has been modified to be sexier by cutting the length of the midriff of the top, which turns the shirt into a crop top. There is also a fishnet stocking coming with it. It is similar to what Slut#2 in Mistress Noir wears.

My expression turned serious, “Where do you get these kinds of clothing, young lady? Do you keep this kind of clothing in your closet without me knowing? Have you worn it outside?”

“Uhm…yes, a few times. Less than five, I swear.” Jessica answers. Her face showed a slight hint of guilt.

The previous me would already get flipped and angry at my daughter for daring to wear something this revealing outside. I will berate her with a long lesson about decency and then ground her for days for ever daring to wear something like that. But the current me only lets out a sigh; it seems like my anger is suppressed before it can erupt. My expression softens, and I try to give her a smile. “It’s okay. I will not be angry at you for wearing that. I just want you to be careful if you are out wearing something that is quite sexy. There are a lot of bad men out there who don’t know what a boundary and consent are.”

“Thanks, Daddy.”

After that short interruption, I finally put my focus on the high heels that Jessica brought along with her uniform. My feet are unexpectedly able to ‘fit’ Lisa’s heel. Well, maybe calling it fit is a stretch; I still need to **** my feet in. One or two sizes more, and it will truly fit me.

“Alright, I get my feet in, now, how do I like, Jess? Am I looking perfect now?”

“Better than before. Try to walk in those shoes, daddy.”

I try to walk with the heels. And the result is not great. My steps are wobbly. I almost strain my ankle if I am not careful. How can a woman seem so effortless when walking in these heels?

I give up and remove the heel from my feet. “How can a woman walk on these without a problem?” I ask my daughter.

“Training, and mostly getting used to it. It takes time to get used to walking in heels. Some do not even get used to it even after a long time. Honestly, letting you directly try mommy's 4-inch heels isn’t the smartest decision; the higher the heel, the harder it is to walk in it. We should start with the 2-inch one, that one won’t be much different from men’s shoes.”

“No need, don’t underestimate your father. I will master walking on these 4-inch heels as soon as I get my hands on shoes that fit me perfectly. Anyway, help me undress, I will try your costume; you brought it here for me to try, right?”

“Yes, Daddy.”

With Jessica's help, it is much easier to remove the clothing that I have trouble putting on. I then pick the uniform Jessica brings.

I don the uniform and then look at the mirror. Somehow, I feel sluttier wearing this uniform than when I wear the gown Ray gives me for emergencies. My mind flashes with all the scenes where Mistress Noir's sluts were donning this uniform.

“Daddy, you have a hard boner again. Have you thought of something naughty again?”

“Sorry. I can't help but imagine some risque scenario after seeing how slutty I look.” I answer. It is the truth, I just don't tell her that the risque scenario in my imagination involves a slut that looks like her and Sheila.

“This one really brings your slutty side out. You look like a freaky slut.”

It is certainly an insult, but I don't know why I didn't feel any anger when Jessica called me with a slur like ‘Freaky slut’.

“So, Daddy, have you decided which one you will spend the night in?”

The babydoll is perfect to sleep in; others are not so much. But my choice fell to this uniform. Maybe because I watched a lot of these porn videos, it makes me more curious about the uniform than the other dress presented to me.

“This one. I will keep the uniform, you don't have any problem with it, do you?”

“No, that's okay. You can borrow the uniform.”

Done with our dress-up session, Jessica left the room in the room.

Continued in part 2

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