Helping a Crossdressing Sugar Daddy

In a possible occurrence, you may meet a Sugar Daddy who is interested in crossdressing as a woman. This is a very exciting opportunity for a sugar baby. This allows for more interaction and a different form of dress- up than would occur in a more standard arrangement.

Your dressed up daddy can come with you to the fitting room, and participate in activities as a female companion or as a Sugar Mommy.  It provides more opportunities to bond with your Sugar Daddy. As an experienced baby with a Daddy who loves to dress up like me, I will be giving you a few tips on helping a crossdressing Sugar Daddy.


This is a key character trait and is one of the most important parts of trying something new. Your SD may have little to no experience, and lack of patience when it comes to trial and error.

As a lady, we all know how frustrating it is when a cute dress we like doesn’t fall right on us, or the store does not have our size. It’s important for you and your Daddy’s experience that you be very patient and stay positive. This will help reassure your daddy that a solution will come, and the fun can continue.

Makeup tips

Makeup is a key tool to transform a face. For your Daddy, it is important to moisturize with male skin products. Plan on investing in drag make-up skin color. There are many shades and skin tones that will work well. Some experimentation may be needed.

If your SD is comfortable, take a trip to Sephora and experiment with different makeup brands and colors prior making a purchase.   Most have experienced makeup artists, who are knowledgeable about all skin types. If he prefers to do this in private, then do it in the bathroom of one of your private homes.

Eyes and lips are the keys to help distinguish your Daddy from your Mommy. Help flatter their eyes with neutral and smokey eyeshadows with long false lashes. If their eyes are more round, use mascara and give a sexy cat eye. It will help make their eyes the focus. Use neutral eyeshadow colors for brown and blue eyes, purple shades for hazel/green eyes, and nude for blue eyes, but black mascara (thicker for bigger eyes, and thinner for smaller eyes) is always a strong detail for the eyes.

Lips are always sexy and kissable if done correctly. If your SD has fuller lips, use a nice, dark red to make them sultry, or clear gloss to look like Angelina Jolie. If their lips are medium-sized, a mixture of gloss and color helps make the lips appear larger and more full. For SD’s with smaller lips, like mine, dark colors like purple and black, with a mix of red gloss, help make their lips more interesting and sexy.

Accentuate the cheeks with pink blush. Created a rounded cheek look to help your Daddy appear innocent and sweet, or blush on the cheekbones to accentuate strong facial features.

Clothing Tips

Men’s body are naturally different from a woman’s, as men don’t naturally have the curves of a woman, and tend to be larger, with bulkier shoulders, and less of hips and a bottom for some. And of course, they lack womanly breasts. They can invest in artificial  breasts and an appropriately sized bra. This will help them look believable.

If he doesn’t have them yet, or is not sure/interested in that investment, they can get tops with built in bras that can be stuffed with anything from toilet paper to small foam balls. This takes much more practice to make them look believable, but it is achievable.

For hips, there are form implants that can be used to help give the appearance of hips. However, if Daddy is already curvy or has a good bottom, making the waist appear smaller with Spanx, corsets, or dresses that accent some of the curves they have will work.

Scoop necks should be avoided if they want to look feminine. Tights and sexy leggings are great to show off legs, especially with a cute dress or skirt. Heels are the best thing to tie the look together.  A great, sexy, black pump is always hot. However, the most important rule when it comes to shoes is that your daddy needs to be able to walk in them.

With these tips, you will have a fun and different adventure with your SD. This can help create a stronger bond, increase trust, as well as have more room to play around. Confidence and having fun will create a positive experience for both the SB and the Daddy.