Advice For A Son (5) Update

For those of you who have invested in my son through your unselfish contributions of love and advice, I thought I would give you an update on how he is doing.


I think I last left you with he and I having a discussion about keeping his interests between him and I for now and that I would take him shopping soon to pick a few things out for himself. A few days later, I did take him shopping and he was able to find several things that he really loved. To be honest, they were a little more feminine than I was comfortable with at first because I was concerned that some of the feminine elements would be either visible through his clothing or that his own carelessness might expose them to his school friends. But even with my own discomfort, I totally supported his choices.

While in the lingerie section, I also asked him if there were any other things he couldn’t live without and he embarrassingly admitted that he would like a soft nightgown like the ones I wear. I could see him eyeing the other lovely things, especially the bras but he never indicated that he was interested in one so I didn’t have to have the first bra discussion with him yet. I know that some of you reading this adore bras as I have read your stories and profiles but I guess I am a little uncomfortable about the whole bra thing especially when he has no breasts. I assume that if he thinks he needs one later, I will just treat him as I would a daughter and start him off with a training bra. I hope that is much later but we will take it as it comes I guess.

After selecting his intimates and a couple of cute nightgowns, I moved on to the clothing section to not only look for me a few things but to teach him about the differences in girl’s clothes versus boy’s things. He was of course fascinated and all ears when I was teaching him but he either was not interested in any outerwear right now or was too shy to go that far with me at this time. He was however, extremely interested in makeup. He watches me put on my makeup every morning so I should have known he would be fixated on it but until I walked him past the makeup area, I hadn’t realized that he was so interested.

I took his hand and walked over to the MAC counter and talked to him about what each of the products were for and which ones I thought that would look best on his skin. I also talked to him about skin care and eye makeup. I didn’t offer to buy him any makeup but I did tell him that I would teach him more at home if he was interested to learn all about it.

Essentially, it was a learning experience and field trip for him. I wanted him to learn more than anything else. Once guys truly see the extent to what girls go through in order to present the packages that they present, I could imagine that most guys would just forget the whole thing. In fact, there are quite a few women who could care less about all of it too. Those girls are pretty easy to pick out in a crowd.

Once we got home, we both changed into our nightgowns and watched television until bedtime. He couldn’t keep his hands off of his nightgown. I could tell that he loved the feel of it on his skin and who wouldn’t really. On Saturday morning, my husband took us to a B&B in the mountains near Helen, GA and we all had a very good time exploring the area and sampling the fattening Bavarian foods of the area. So far, he’s been very careful around his father, I know that a discussion with him is inevitable and that I should have it before I get caught but I admit that I’m more than just a little concerned with his reaction.

Cute30sMom Cute30sMom
31-35, F
15 Responses Jan 22, 2013

you are one grate mum all the best

Thank you so much!

Your a good mother with rare understanding . ;-)

I did stress to my little (brother)Sophia how important it was not to be un -lady like when wearing fem under things . I like that both genders wear skinny jeans . Just be careful when bending & sitting .Pretty bras & tops can hidden with a hoodie or jacket .

I'm afraid that if you talk to your husband, he's going to think it is your fault that he turned out to be a sissy. This can be very traumatic. But you know your husband better than anyone so use your own discretion.

I remember being confused and going down that path in my own. Not understanding why I was drawn to mom's undies, pantyhose, skirts, dresses etc. But I remember feeling this intense sense of rightness and wrongness at the same time. I felt whole and right, but I knew society would think I was wrong. Thus the guilt and trying to bury this side of me.

You are helping your son follow his path and yes it's scary for you both and unknown and and and... But you are stepping beyond your comfort zone to help him so he's not alone in this. That shows great courage, love, and conviction.

All the confusion muddied the water for me and I didn't know who or what I was until my 30's. It's looking like your son will be able to freely and openly find himself much, much earlier in life thanks to your nurturing.

Today I'm a well adjusted CD who is happily married and still enjoys hosiery, skirts, and some lingerie. I love who I am and wish everyone can find comfort in their own skin.

You are a great mother!

My dear Cortina, you are a lovely Italiana girl who is desperate to get the knowledge of we transgendered souls. You want to know if your son is experimenting and learning about the opposite sex, does he admire his sexy mama, is he a cross dresser, or is he transgendered as I am?

First, Una buona mamma vale cento maestre. “A good mother is worth a hundred teachers.” You are worthy of this phrase and I commend you for loving your son so unselfishly and unconditionally and with so much passion. He will always love you and he will never forget what you have done for him.

You have some work to do I think. From my experience, I think all boys are fascinated with anything that touches the intimate parts of women. Straight boys play with panties all the time and never become cross dressers or homosexual. His eagerness to wear them with you however is a strong sign that he is not the casual ***********.

Everyone looks at me and thinks that I knew I would be a woman from age 5 but I did not. I did, however, wear panties from age 5 and strongly associated my gender as feminine but I was far too confused about sex and gender to understand where I was and how I would live my life. At about the age of your son, I did recognize that I was attracted to boys. With a strong association with being feminine, very feminine characteristics, and being homosexual, I sought out a TS prostitute a few years later and knew then that I would take this journey. She dressed me up that very night and afterwards, I kept girls clothing in the luggage compartment of my vehicle and after school I drove to Taksim square to sell my body.

You do not want this life for your son. Trust me. I had to hide all of these things from my abusive papa who only tried his best to make a man of me which was impossible. I say this because if your son is Transessuale, the attempts made to masculinize him will be pointless and horrifying for him. My papa placed me in Karate classes. All that happened was that I was repeatedly beaten. I gained nothing but disdain for my papa.

I think a lot has been said, some of which I believe is very well thought out. Some of it is complete fantasy and not worthy of your mostly kind responses. Chi si prede cura dei bambini deve accettare il bene ed il male. “Those whose job it is to take care of children have to accept the good with the bad.” I think you will agree that your job is most difficult but you are taking the exact right approach by being accepting to whatever life brings you with this child and embrace it like it is a gift from God which I personally believe it is.

You have opened a door for him, trust me, he will make his feelings known in a short time. Once you open a door such as you have opened for him, one that he could not have opened by himself, emotions and feelings once repressed will be released like a damn breaking and he will not be able to control his emotions or thoughts. That is, if he is transsessuale. If, however, he is not…he may say nothing at all and just enjoy his little soirée into the life and tastes and intimates of women. Either way my love, you have already solved your riddle.



Amazing response! You're a real gem and gorgeous to boot. I'm blown away at how beautiful you've become. And I'm already seeing in him exactly what you were describing. We've made much progress last week and over the weekend I just havn't had time to write about it yet but I will very soon. Grazie! Your awesome and I appreciate your friendship and advice.

Again I have to say , your support is beyond praise . Don't forget about yourself CuteMom , you're a hottie yourself...

I'm glad to hear things are going well with your son. There is nothing better than someone who loves him the way you do to be supporting him in the manner in which you are!
You are going to have to approach your husband with this soon though!
I think he will be even more upset with you knowing that you are not trying to help your son dress more like a man and allowing him to explore his feminine side. I know this because when I came out to my wife she was very apprehensive at first, almost as if I was cheating on her and was angry that I didn't tell her sooner. So before your husband see's all of the clothes you bought him, or even worse catches him in them you should start to begin to break it to him gently for both you, and your son's well being!
My hat is off to you as far as your support. It is very difficult finding people that understand just how we feel when we dress up. It is very hard to explain the enjoyment we get out of it whether it be sexual, or the feeling of the materials, or just wanting to be a woman!
Your son is young and he is enjoying dressing the same as I did as a child.
My Mom would let me wear her old dresses around the house and not say a word about it.
I enjoyed the feelings of the materials as it brushed up against my skin. I remember the satin nightgown that she gave me to wear to sleep. It felt incredible on my body, I remember running my hands all over my body and enjoying the feelings that it gave me.
That is what started me wearing her stockings, bra's, slip's, dresses, and corsets!
And it only progresses as then I wanted to see what I would look like as a girl and played around with make up and her wigs.
It wasn't until my neighbor next door caught me in her house in her clothes that I was able to take it to an even higher level of dressing and sex at that point! (Read my story "Caught by my neighbor 1 & 2 and you'll see why I am the way I am today) I love who I am and so does my wife. I am a heterosexual male who just loves the feminine side of myself and I like to let her out once in a while and enjoy the other side of myself!
I just hope your son has the same luck that I've had in my life in finding the support to be who he wants to be! And it seems so far he does!
Please feel free to email me if there is anything I can do to help you in the support of your son!

xoxoxo allwrappedupinit

Love your perspective! With each persons response, I learn more and more about what makes him tic. Thank you so much!

Feel free to PM me anytime you like and if I can help I will!

First, let me say to my fellow Italiana, Piacere di conoscerti mi chiamo Efe. You are a striking woman and write so beautifully. I read all about your journey with your child and I am surprised with how well you have dealt with his expressions of gender. I know many things about boys such as your little one for I myself began my life as a little boy. I think I will be a very good resource for you if you reach out to me through a private message, I will share email addresses with you and I have a book which is published only in Italiano which I will be happy to send to you if you can read the language. I look forward to our first conversation and I hope one day to meet your family.

Thank you! I will contact you.

That's great u support ur son I'm a gay man and my family supports me

Good approach

It is inevitable that conversation with his dad, but u got ur boy for a reason, u will fight for his soul
Good mamma

This is heartwarming to hear the updates and about the progression. Your doing great

Perhaps it's time for a cute sexy swimsuit??

Thank you so much for keeping us up to date with the latest on your son's exploration. To experience this through your eyes (and thoughts) is refreshing, and an insight into the unconditional love you have for him. No doubt, he sees you as his favorite role model. I can only imagine what you look like from head to toe, but I'm sure he wants to emulate you.