Dear Diary: The Shoes May Fit, but the Strap-On Does Not

Hey everyone! This is another ‘Dear Diary’ blog post for you all! I have been very busy for the last few weeks, but that does not mean that I did not find time to crossdress. The large amount of time spent focused on work and life makes the moments when I am able to escape to be with Catie so much sweeter and more intense. I find myself daydreaming much more about crossdressing on my way home each day or lying in bed before I fall asleep.

In the limited free time, I was able to go shopping for my fem side and also explore more sexual kinks with my wife (and myself). Please read my last ‘Dear Diary’ update to give some context to the continuation of certain topics that I will discuss!

Being Thrifty

Every couple of months, I really enjoy shopping for my fem side. I do not always buy something, but I always enjoy browsing certain sections, like the makeup aisle or the clothing section, just to see if anything is worth buying. Recently, I had a free morning to spend time browsing a few different stores with the goal of finding more clothes that I could add to my wardrobe.

The first stop I made was at a Goodwill for some thrift shopping. This one was located in a busier part of the city I live in, so I was hoping that there would be more fashionable items to choose from there. Later in the day, I stopped at another Goodwill that was further out of the city as well, so more to come on that later.

I enjoy thrift shopping for a few reasons, the first one being that the items are not very expensive. This helps me to build my fem wardrobe more economically, and also, if something doesn’t end up fitting, I do not waste that much money on the item. I know you could say that at other stores, I could end up returning the item, but I don’t return items, usually, even in guy mode! So, returning items and getting a refund isn’t a personal preference of mine.

The second reason I enjoy thrift shopping is that when shopping for fem items, I don’t really want to be seen as a crossdresser in a public space. But when thrift shopping, I can rationalize in my head that the feminine clothes and shoes that I am browsing for could be for reselling. I don’t know if the people around me think that, but it helps me have the courage to browse relatively freely in this space.

The last reason I enjoy thrift shopping is finding hidden gems! It could be a pretty dress that costs so much more or cute shoes that are actually in your size! You just never know what you’re going to find there until you look, and it is so exciting.

The first Goodwill was disappointing, especially since it was in a better location, as I had mentioned before. I looked around in the dress section for 10 minutes with nothing really catching my eye. I was also trying not to buy similar things to what I already own, so it makes it slightly harder to find things. I really need more top/bottom outfits, so I looked for things in those sections as well with no luck, so I then moved on to the next Goodwill.

This Goodwill was a similar size, but I wasn’t sure if I would find anything that I was looking for there. This store was where I found my “Church Dresses,” as my wife calls them, so I figured that I would just find the same type of styles here. But thankfully, I was wrong! I found a cute pair of light pink cuffed pants that looked like comfy business lady pants that looked like they would fit. I also found a comfy knitted sweater that I liked that was in my size as well! Both of these items fit me well when I tried them on at home, so I am happy!

The hidden gem that I found, though, were these leopard-print high heels with a pretty gold-plated chain ankle strap. I could tell they were at least close to my size, but when I picked them up, it said they were size 42, and as an American, I had no clue what my size was in European Units. So I quickly Googled and found out they were definitely my size, and then I ran to check it out!

Shopping Spree Continues

I also made a stop at my local Target, where I like to shop for panties and other small clothing items. I like Target because a lot of their items are cute, and they also have self-checkout, so I don’t need to feel awkward or nervous about being face-to-face with another person when buying my feminine attire. I was able to find five different pairs of thongs for $20, and I was happy because my goal was to add some variety to my panty drawer.

I didn’t spend too much time shopping for other items there, and as I headed up to check out, I noticed that ALL OF THE SELF-CHECKOUTS WERE NOT OPEN! I had a decision to make: Do I chicken out and leave with nothing because I had to get through regular checkout? Or do I just get the courage to hand the cashier the thongs that I want to buy so that I can leave happy? I chose the latter after a 5-second contemplation in my head.

The cashier was around my age, and she didn’t make it weird at all. At this point in my life, I also didn’t act nervous or anything either so I am sure that helps in these situations. I grabbed my bag of thongs and headed to the last store for the morning, Kohl’s.

I generally like Kohls for men’s and women’s clothing, so I did browse all of the sections while I was there. I mostly shop the clearance racks there because I feel like there are great deals to be had. I found a few cute feminine things, and I decided, why not go and try them on in the dressing room? I like Kohl’s dressing rooms because there is no one working there to see how many or what kind of items you are trying on. I tried on a cute, sparkly blue skirt with a basic white top first. I didn’t hate how it looked on me, but I wasn’t blown away, either. I also tried on these super comfy baby blue lounge pants. They felt great, but I also wasn’t in need of this type of item at the moment. I ended up leaving without anything cute, but it was the first time that I had tried anything feminine on in a store dressing room.

Is It In?

Switching gears from shopping fun to bedroom fun, I also recently received the strap-on toy that my wife and I decided to purchase. The strap-on has one large vibrating shaft for me, and there is also a smaller vibrating dildo attached for her to insert as well. It is pink and very cute. My wife and I had a little date night, and afterward, she tried it on, and she very much liked the feel of having the strap-on between her legs. The only issue for her was that the small dildo was not really at the best angle for her to insert. So for this experience, it remained not inserted.

I was on all fours again, just like in the last Dear Diary post, ready to take the toy. As she went to put the lubed toy in, it kept slipping and not actually going inside me at all. We ended up trying for 3-5 minutes to find a good angle to get it to fit, but we could not find it. I think it had something to do with the angle and how the strap-on was shaped. But we pivoted and brought out the same toy as last time for her to play with on me, and it was again an enjoyable experience.

But I was curious about how the strap-on would feel inside of me. I definitely wanted to feel the vibrations of it as it slid in and out of me. So, the next free afternoon I had, I tried it by myself. I also decided to put something a little more sexy on to really enjoy the experience alone. For some reason, I really enjoy being dressed up when having sexy fun with myself.

I prepped the toy and myself with lube. It is at least a 7” shaft and has some nice girth to it, so I was curious if it just would not fit this time either. But as I pressed the shaft against my hole, it slowly entered, and I couldn’t help but moan a little. Forgive me if this sounds like a sex scene; I don’t want it to be, but I honestly couldn’t help the moan! But the really sexy thing was that after the toy was fully inserted, I turned on the vibration, and almost instantly, I leaked cum. I typically only have that happen when I am really backed up, but never as much as this time. It made a mess on the panties that I was wearing, and I was ultimately pleased with how the toy felt and fit inside me.

Why Is the Lube Out?

So, after my science experiment on the fitting of the strap-on, I didn’t finish and waited for my wife to get home later on, to have sex with her because I was totally in the mood at this point. I cleaned up and waited patiently for her to arrive. It was a couple of hours later, but she finally got home.

While she was gone, I was supposed to do the dishes and clean up the house a little bit. I did not do any of these things because I mostly just played around with the strap-on instead. So she asked me what I was doing instead of cleaning. I lied to her, for some reason, probably because I felt a little bit of shame from playing without her. I told her that I just got lazy and didn’t get it all done like I was supposed to.

She took that as an answer, but only 5 minutes later, when she walked into the bedroom and asked, “Why is the lube out?” Being as though I had already lied to her once, I was definitely not going to do it again. I immediately told her everything. I admitted to her that I really was just checking to see if it actually fit. If it didn’t fit, I would’ve probably gotten rid of the toy. She assumed that I had finished, but I told her no and that I was waiting for her to come home to have some sexy time with.

She was okay with that answer but still was mad at me for not cleaning the house up. It was a very interesting situation to get caught in, but I could only imagine how the situation would’ve gone back only a couple of years ago. It probably would’ve been awkward and turned into an argument, but at this point, I have been vulnerable enough with her to be able to not outright lie about things that I enjoy in the crossdressing space. I just need to be better about not telling the entire truth the first time.

What Is Next for Catie?

Truthfully, at this point, I am not sure what is next for my crossdressing adventures! I am working on practicing my makeup more and potentially going out shopping with my wife for clothes, accessories, and makeup. I also have been making really great friends with whom I hope to make plans as the months go on!

Thanks to everyone for reading. Stay tuned for next month’s Dear Diary post, where I hope to have some new things to discuss with you!