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I know that there are many nuances and varieties of human sexuality, and I mean no disrespect to the wide variety of appetites you may have. I just want to touch on two basic, broad options you have as a sissy. Let’s first agree on one thing: you enjoy being a female wearing feminine clothing . With that agreed upon, let’s continue!
I know there are many labels for everything sexual . I am going to keep this simple by calling all you gals sissies. In my opinion, there are two options for the sissy to partner with sexually- males and females. So you, identifying as female, either want to have a boyfriend or a girlfriend. Where it can get interesting of course, is if the female you desire is also a sissy, but that is just an added label I’m not getting into right now.
Have you considered that there just may be a woman out there who wants a sissy girl lover? That you may never use your penis again, but she may use her strap-on on you! Conversely, having a boyfriend means you get to be the lady of the house, and have a man who will potentially adore you. Even in a D/s relationship, there is compassion, affection, and respect.
Many people don’t consider that every sissy isn’t trying to be a little sissy housemaid down on her knees servicing her master. Your relationships are just as messy and complicated as people who don’t have any gender identity differences, who identify as the gender they were born with.
The takeaway message here is don’t let anyone put sissy in a box. You get to decide what your romantic and sexual relationships look like, even if you identify as submissive. You’ve heard the phrase “safe, sane, and consensual”, and that goes for every relationship you may find yourself in, no matter your sexuality. You give them control, they don’t take it!
Thank you for your educational material.
Thankyou for the educational materail .i look forward to being a better sissy in 2019 thankyou .thankyou subbie ted
subbie ted- I am glad you are finding the articles educational and informative! Here’s hoping your 2019 is already better as a sissy!
I’m not gay nor into guys but just like wearing bras/panties/dresses/lipsticks/perfumes/leggings/yoga pants/blouses/knee high and ankle boots/women’s turtleneck sweaters/wigs. It just feels so much better then my boy clothes as the fabrics are so soft against my girlish waxed smooth skin. My masseuse knows about this as she’s dressed/put lipstick/makeup on me along with wearing bras/panties/dresses/wigs taking pictures of me with her phone. With her doing this I’m no longer boyfriend material anymore as she can hit send anytime she wants. Though she’s married she told me not to worry about her husband and not care what others think. She said not to fight this and to accept that this is who I am and become.
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My First Time Cross Dressing WITH PICTURES

In 2015 I came out as transgender & started my transition from male to female. My purpose here is to share my triumphs & my struggles in hope to help others find a true sense of self. So be prepared for new content on: fashion, makeup, LGBT & life. Don’t be afraid to interact with me on social media and make sure you guys subscribe to my newsletter.
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It was freshman year of high school and I was friends with a few girls and for Halloween, we all wanted to get together and do this little trick-or-treat night together. I had never gone out trick-or-treating on my own. They were all like, “oh my God you should dress up like a girl, you should fully dress up like a girl” and “yes do it. Do it! DO IT!” and I’m like “fine, I’ll do it.”
In preparation for that night, I asked one of my friends to do my makeup. She brought her makeup to school and we literally sat on the bench during lunch and she did my makeup in the middle of the Courtyard at my high school. Then I just loaded up a bag full of the clothes I was going to wear that night and the wig and whatnot. I got like a $12 wig and this outfit though, you guys, kills me! I had some gloves from Hot Topic and my dress is actually a skirt from White House Black Market, I had borrowed it from my aunt. I was also wearing some women’s shoes too. I don’t think I have pictures of them, but they were also from my aunt. I borrowed the majority of my outfit from my aunt with a necklace and such. I totally slutted myself up, going all out. I looked… not good, but it was dark and people couldn’t see too much.
We went from house to house through two different neighborhoods. We all walked up to the house together and the three of them would say “Trick-or-Treat” and I’d be at the very end and in my deep “manly” voice say, “Trick-or-Treat” and “Thanks!” but it was funny, a lot of the reactions were like, “oh my God, best costume ever” and I got a lot of positive responses, not many negatives. I’m surprised to be honest because my friend lived at the moment in a more seclusive neighborhood and a lot of people here in Arizona are very religious and don’t like or support the LGBT community as a whole. I was already out as gay at that time.
I want to go back a little bit to talk about getting all dressed up. I’d say it took probably 4 hours with putting on the nails, making sure the makeup looked good, doing the hair, putting on the clothes, making sure I felt confident enough, and of course getting down the walk because I had not really worn high heels before that. I wore high heels for the night which was a mistake. I tripped a few times and decided to take them off while we were still out, which was disgusting walking around the neighborhood barefoot. But we circled around the block to go grab my shoes because I was not feeling it, but we still wanted to be out.
I looked like a hot mess back then. I had oil problems and acne. My friend who did my makeup literally just did like my eyes. I was at my friend’s house and I got all dressed up and I took some pictures in her bedroom cuz she was in the bathroom getting ready and so used her room. You know, I honestly didn’t know what to think about what I saw. I was scared and actually cried. I thought I looked pretty, nothing like supermodel status, but it was scary. I had never even thought about being feminine in any which way at that point. The thought of something different was kind of intriguing. I don’t know if you know this, but I grew up Mormon. My family was really pushing the Mormon beliefs. My grandparents on both sides are Mormon. My dad has now left the church and is now an accomplished tattoo artist, feel free to check him out on social media @JohnHansenTattoo . My mom is still Mormon, so that made me nervous especially later in life when I came out as transgender. When I went home I was still kind of dressed up. I think I changed back into my boy clothing before I went home, but I still had the face on and they asked “how did it go?” and all I said was “it was great, it was great” and I went to my room and didn’t talk to anyone the rest of the night.
The importance of my first time cross-dressing
The reason why I bring up this story is to show people that I had never even thought about anything like being transgender and that was how it all started. I’m not kidding, within two weeks I was wearing eyeshadow and painting my nails every single day for school every single day. I have some pictures from the following Christmas. I dressed up full glam, well, full glam for back then. For the Christmas party with my family, all the pictures I had full out eye shadow, I loved the eyeshadow. Dressing-up was honestly one of the most important parts of my transition and really helped shape me into the person I am today. If it wasn’t for my friends pushing me to do it, I feel like I would have never felt like I had finally found myself. That’s really the most important part, for you to love who you are. I’m glad for myself that I had realized this, because who knows if it could have been another 10 years before I finally realized this is why I’m not happy with myself. Thanks to those friends freshman year, I realized I did not like looking like a boy, it just didn’t suit me, personality-wise, and everything else. I just thought I looked awful all the time. The second I put on that “dress,” all I knew was that I liked how I looked.
Thank you for taking the time to learn about my experience with crossdressing for the first time! I definitely think that it’s important for us to communicate with each other, so go ahead and continue to follow my journey on social media and share with me your own stories of discovering a new part of yourself and finding ways to love who you are!
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Master has confirmed the rules he has laid down for me, and i am going to share them here:
1. Panties to be worn at all times. Hold up stockings, suspenders belt and stockings, ankle socks and longer socks are permitted. Tights are not permitted in masters presence, but may be worn for ballet lessons. Stockings, socks etc will be worn under gender clothes at least three times a week. Panties 100 percent of the time. 2. Sissy shall wear female attire at all times whenever master visits. 3. A Journal of sissy thoughts and desires to be kept and summarised for masters perusal. 4. Body should be kept hairless as far as is possible. 5. Personal hygiene is top priority. Master will fully inspect sissy at each meeting to ensure compliance. Bathing an essential part of part of preparation for masters visits. 6. Sissy will always sit when using toilet. 7. Sissies clitty will not be played with unless master gives permission beforehand. Nb master understands these needs and reasonable requests will not be denied, but sissy will have to ask permission first. 8. Sissy shall expect to be spanked and paddled on a regular basis. The cane may be used if rules are broken. This is to ensure sissy understands and benefits from the true meaning of submission to her master. Self spanking will be undertaken when master is not around. Such experiences to be included in her journal. 9. Sissy will obey her kindly master at all times and strive to please him and take care of all his needs. In return Master will always treat sissy with respect and kindness. 10. Sissy will also strive to improve her oral skills.
One thing i should point out is that Master has amended rule 3 from the original list, and he no longer requires daily journal entries. However, i intend to keep this diary going on a daily basis whenever possible, with the knowledge that there is no longer quite the same pressure.
In the coming days i will explain further what these rules mean to me and how they have changed my behaviour.
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