04 - My Cross Dressing Dream

My Cross Dressing Dream

So, this dream was Euphoric partly because part of it was something that I have dreamed about and the other was just so happy but unrealistic.

So instead of us meeting after work to do my makeup, we decided to take the day off and you told me to come over to your place early in the morning. When I arrived, you had setup a makeup station. I sat down and you started to do my makeup. You were so kind, like you always are, in showing me different tips and techniques.

After you finished was done, you turned me around for me to look into the mirror and it overwhelmed me. I actually had a tear in my eye. You looked at me and said, "OMG sweetie, why are you crying?" I replied back, "I can't believe how beautiful you made me look."

"Did you bring your wig, like I asked?"

I nodded my head and pulled it out. I apologized for what it looked like and you said, "No worries. Let's see what we can do with it."

"While I work on this, how many outfits did you bring?"

"I brought a couple because I wanted some pictures in different ones."

"Ok, go change into one of your outfits and let me see what I can do about this wig."

I changed into one of the outfits which was my favourite blue top and a pair of my Torrid jeans.

When I walked out, your face lit up and this huge smile came over your face. "OMG. You look amazing. Come here and sit."

I sat down and you turned me around such that I couldn't see the mirror. Then, you placed the wig on my head. You made some small adjustments and then you had a big smile. I looked at you and said "What?" with a little giggle. You turned me around and said "You look. I think I did a pretty good job fixing that wig of yours."

As you turned me around, I looked in the mirror and that amazing tearjerker feeling came over me once again. Once again, my eyes started to swell up but this time I stood up turned around and gave you the biggest hug as I wept into your shoulder.

"Why are you crying?"

"Oh, these are tears of absolute joy. In a million years, I would never think I would feel like this. You really are overwhelming me here sweetie."

"Well why don't we keep that up and take advantage of you dressed up and looking good and let's go out!"

As I hear you say those words, I gasp out "Really???" Immediately, I have butterflies in my stomach. I have had the dream of a "Girl's Day Out" for probably the past year but I never thought it was possible and now it was really going to happen.

"Lets go through the outfits that you brought and see which one looks the best." So for the next 1/2 hour or so, I changed into the different outfits I brought and after all of that, we decided on the original outfit with the blue top, Torrid jeans and my suede booties with the 2" heels.

We even tried a couple of your own outfits because we thought that I might have fit into them but I am a little bigger than what we thought. As I was trying to put one of them on, we had a good laugh. It was close.

So, we pack up our things and head out. We get in the car and I turn to you, "Where do you want to go? Is there any specific store you want to go to?"

"Well, I have already told you that I love Torrid but there are no close stores from here. The closest would probably be the Eaton Centre but I don't think we want to drive all the way down there. Where do you like to shop?"

"Well for basic stuff and my basic needs, I usually will go over to the Dufferin Mall. It is easy to get to by transit. If someone is driving and I want to see some nicer clothes, then I'll probably head over to Sherway Gardens."

"Dufferin Mall sounds good to me. It has some nice stores like H&M, Marshalls and Winners. It also has some outlets, like the Gap, and Walmart."

"You know what. Let us go over to Sherway Gardens. Today is a special day so a nicer, special mall is better."

"Ok. Sherway it is." On the way, you told me about your past holiday in Mexico and how it was so wonderful to get away. We also talked about what stores we wanted to go to and eventually we ended up at the mall.

"Ok, lets go have some fun."

I could go into so much more detail as we went from store to store looking at clothing, jewellery, shoes and accessories. We even walked into stores like Kate Spade and dreamed about picking up a purse. We went to stores like Banana Republic and Club Monaco. We tried on some outfits, and you bought a couple of tops.

Then we stopped for lunch at Bazille, which is a restaurant inside of the Norstrom store. We sat down and ordered some drinks and then ate lunch.

This is the part of the dream that wasn't really realistic or maybe part of it was or wasn't, I don't know but it was really fun to dream about. LOL

When we were done, you said "Come with me". I asked, "where are we going?" You promptly said, "I need to freshen up a little and come with me to the ladies room."

A shocked look came over my face. "I can't do that. Or can I?"

"Michelle, you can do anything you want today. You are not your male counterpart. You are Michelle today, so Michelle uses the lady’s room." and you held open your hand to me.

I grabbed your hand and stood up and we walked to the washroom. I am saying to myself, "can I really do this?" and "OMG is this really happening" and then we walked in. First off, I was really surprised on how nice the ladies room is compared to most men's room. LOL. Off towards the side, there was a small couch for you to sit in and I was surprised on how bright it was also.

When we went in the washroom was empty and I was sort of glad of that. Both of us went to the washroom. We both came out and washed our hands. Then you turn to me and said, "lets fix you up a little." You applied a little bit more lipstick and fixed my hair.

As you were "fixing me up", another 2 ladies walk into the washroom. My heart starts to pound as I am thinking that I am about to get caught. Both of them look at you and then me and then one of them says, "OMG. That is such a cute top." Her companion turns and says, "It is. Isn't it. Where did you get that?"

I have been practicing my female voice for awhile now and I was trying to use it during the day in the different stores, so I reply back, in a soft and faint voice, "Torrid sweetie. This is my favourite top." You blurt out, "Doesn't she look amazing in this outfit?" Both ladies look at me and nod their heads and say, "You do look good."

The ladies introduce themselves as Kathy and Kim. They are best friends having a shopping day, just like us. It seemed like we were in there for close to a half hour and all four of us talked about all the different stores that each of us has been to. Kim says, "You have to check out Aldo Shoes. They are having a great sale today. If you need shoes or boots, you have to check it out." I turn to you and say, "I think this is where we are going after we leave here."

We say our goodbyes and say that we will see each other again walking around.

We head back to the table and the bill comes and I insist in paying for the lunch as for everything that you have done for me, this was the least thing that I can do. After a little argumentative talk, you reluctantly agree and I take care of the bill.

We walk out of the restaurant and head out of Nordstrom and take a look at the map where the Aldo shoe store and it happens to be on the other side of the mall. We say to each other, "OK we can make it there eventually." and both giggle.

We stop by the Sephora store and we talk to one of the sales girls, Kelly, about getting some makeup for me. I look at you and lean in to whisper in your ear, "I can't afford any makeup today." You whisper back, "Don't worry about it sweetie." and give me a little peck on the cheek. We walk around the store looking at different makeup brands and we end up look at the Sephora's own brand called Sephora Collection. Kelly tells us that it is a great collection of makeup at a reasonable price. Great for a beginner, like me. So, we go through everything that I would need to start and then you turn to Kelly and say, "We'll take it."

I look at you and say in a stern but still soft voice, "If this is for you, go for it. You are not getting me this."

"Michelle, just be quiet Ok. Let me do this for you. I want to."

You look at me with these eyes and how can I say No. And then the swelling of my eyes starts to come back. I ask you, "Why are you so nice to me?" You look into my eyes, go into your purse and pass me a tissue. Not wanting my makeup to run, I dab my eyes.

Both you and Kelly look at me a little weirdly. "What is it?" You smile and say, "Michelle sweetie, you might want to look in a mirror." Kelly passes me a small makeup mirror and I look at it. I am shocked to see my mascara and makeup is running down my face. I didn't realize that I was crying that much.

Kelly turns to me and says, "Don't worry girl. We'll clean you up. Might as well use all of this makeup that was given to you." "OMG, don't make me cry again." Everyone has a giggle. So, for the next 30-40 minutes, I have one of the pro makeup artists at Sephora putting on my makeup. After it is done, I turn the artist, Jackie, and ask her how much I owe her. She turns to me and says, "Sweetie, it was my pleasure working on you. For being so bold and proud of being out, this one is clearly on the house." This whole time, I didn't see what Jackie was doing to my face but I was looking at you and the smile on your face told me the whole picture.

Jackie turned me around but covered my eyes. Before removing her hand from my eyes, she asked a couple of other salesgirls, including Kelly to come over. Now I have a whole crowd of salesgirls looking at me.

She removes her hand and I am in complete shock again, just like I was earlier this morning but the makeup looked perfect on me. Nothing too bold and out there but still with a little flare. And the incredible thing is that I didn't see myself, I really saw Michelle. I quickly said, "Ok, I have to stay calm because if not I am going to ruin this amazing makeup. All of the girls pulled out their phone, including yourself, to take a picture of me. I didn't know if they could see that I was blushing but I definitely was.

The emotions and feelings that I was going through that day was at times overwhelming and the day wasn't even over.

We walked out of the Sephora store and walked down the hall and strolled into the Aldo shoe store and started looking at shoes, boots and, my favourite, booties. The store was having a BOGO 1/2 off just this day sale.

You picked up a pair of shoes and told me, you have to try these on. They were a pair of black wedges with a nice 2" wedge. I asked the salesgirl if they had a size 10 and she said she will go check. You also picked out a pair of shoes that you wanted to try on.

The salesgirl brings out both pairs of shoes and gives them to each of us. I try them on and they look great and they are very comfortable too. You look at me and smile. You try on your shoes and love them too. I give you a smile and tell you that they look great.

Then you turn to the salesgirl and say, “I’ll take both please.” I look at you and you just look back at me with that look from before and I know that I am not going to win this battle. I just say, “If you have to but please don’t.”

“You know I am going to do this.” All I say back to you is, “Thank you.”

We leave the store and continue to walk the rest of the mall until we get to the entrance that we came in. We look at each other and just smile. You say, ‘Is there anywhere that you would like to go back to?”

I shake my head and say, “No. I think we have done it all. Anyways, I don’t want to find something that I am going to like and you are going to buy it for me.” I pause a little bit and then continue, “What you did today is well over amazing. It is incredible. I think you can look at my face today. I haven’t stopped smiling since I got to your place earlier today. I know that I can’t express how I really feel in words on how I felt today and right now… And then, to top it off, you buy me these things.” I open my arms and we embrace with one of my most memorable hugs that I have ever given and received.

And then I woke up.

The Euphoria that I felt at that moment when I remembered this dream was literally overwhelming for me. I don’t cry much but thinking about this, I couple of times writing this, I could feel my eyes filling up.

#crossdressing #dream #makeup #sephora #aldoshoes