First time dressing Fem, with help from my Mom

My first sexual experiences, in my early teens, were sucking off older boys. I loved it and the more I had, the more I wanted.

I was never the typical boy, never played sports, actually spent more time with girls, but not in a sexual way. My features were more fem than masculine, slender, no body hair, even the hair on my legs was thin, and sparse. On more than one occasion my mom mentioned that I would have been a pretty girl.

When my mother caught me sucking off an older boy, she was very supportive. Shortly after that I found an erotic novel (she left it on her nightstand for me to find) about a young guy who dressed as a woman and would go to a couple's house to help the wife take care of her over-sexed hubby, especially sucking his cock and drinking the cum...the wife wouldn't, but the cross-dresser loved cum. I saw myself in him, or should I say the gurl! It never dawned on me that the book was left for me to find. So, naturally I went looking through my mom's clothes, and right on top, black lingerie: bra, panties, garter-belt, nylons, nightie. Again it never dawned on me that mom did this deliberately. I started dressing as often as possible. I felt so good expressing my feminine side. I would dress, but covered it in regular clothes when I sucked off the boys.

Two years later, after dad passed, mom brought those clothes into my room, and said these are yours...she had bought them for me. I was able to be open with her. She helped me and introduce me to a nice loving couple with a trans husband.

2022 Update
I want to add that Mom did this out of love. Some here on xhamster call he an abuser, which is not true. She was not abusive and initially let me explore myself, which at the time was in secret. I was 13 and immediately when I slipped into panties, then garter belt, hose and heels, I felt sexy. This went on for 2 years, again I thought secretly. During this same time I continued as a boy sucking off older boys, many times at home, with Mom knowing what I was doing in my bedroom and in the rec room with the boys. So at 15 when Mom came into my room with the lingerie, she was lovingly helping me be who I am. She helped me with picking out clothes, helped me with make-up, like the parents of transgenders do nowadays.
Published by MWMluvsGayMen
5 years ago
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55
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smoothmale
smoothmale 7 months ago
Mmm…, so wish I knew you at that age ♥️.  
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Baddaddy54
Baddaddy54 1 year ago
Extremely hot, I love it. 
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funpics70
funpics70 1 year ago
what a lovely mother
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Micki18 2 years ago
Great,wonderful mom,you are lucky man
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Naughtynev69
Naughtynev69 2 years ago
Yummy
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jojosmallone
jojosmallone 2 years ago
i started sucking cock and swallow cum when i first became a teenage (13). I am not sure if my mom knew but she started leave my sisters panties in my under draw and suddenly accidents would happen in the wash and some of my tighty whities were turned pink. It wasn't until i was 18 when she started sewing lace around my bell bottom pants leg that i felt she knew 
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iamagoodlicker
iamagoodlicker 2 years ago
OMG! I discovered this post after receiving a message from you that said, "I read your profile and I can relate." Well, I read this and thought the same exact thing. It also provoked a thought that I have entertained in my brain forever: why did my Mom have me model the dresses she made for friends' daughters when I have two sisters who could have done the same? 
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kara_sissy
kara_sissy 2 years ago
So lucky you had support
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erika4444 2 years ago
very nice makes me feel like the gurl i am
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al985
al985 3 years ago
Lucky......so lucky
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Plonk123
Plonk123 3 years ago
What a WONDERFUL Mom , you lucky boy . ☺️
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f0rm4lity
f0rm4lity 3 years ago
I wish I would have had parents like that.
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basm-2
basm-2 3 years ago
Yes, she is a wonderful mother who deserves respect because she feels you and understands your requirements
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562cple
562cple 3 years ago
I wish that happened to me
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jeanot84
Truly a wonderful Mom ....
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MWMluvsGayMen Publisher 3 years ago
to merlinhamster : Thank you.  She saw this in me, and helped me explore those feelings.
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merlinhamster
merlinhamster 3 years ago
great mom
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smoothmale
smoothmale 3 years ago
♥️♥️♥️
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Pat2610
Pat2610 3 years ago
Mmmm
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mwmfag
mwmfag 3 years ago
Incredibly hot.  And touching, since we know each other's background.  Thanks.
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harmrm
harmrm 4 years ago
to MWMluvsGayMen : Sounds like my girlfriend mom.  We are now actively playing 
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MWMluvsGayMen Publisher 4 years ago
She lovingly helped me explore and find myself.
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MWMluvsGayMen Publisher 4 years ago
to harmrm : Yes she was.  I adored her!  From the time my wife first met my mom, she loved her and they spent many wonderful times together.
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harmrm
harmrm 4 years ago
Wow.   What a supportive mom.    So sexy 
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MWMluvsGayMen Publisher 4 years ago
to 562cple : I love it.
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562cple
562cple 4 years ago
.... Raised..... Right
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MWMluvsGayMen Publisher 4 years ago
I loved her very much.
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MWMluvsGayMen Publisher 4 years ago
I love her and miss her; she made me feel special and sexy.
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MWMluvsGayMen Publisher 5 years ago
to jackit4me : She helped me a lot.  She was just ahead of her time; you see nowadays many moms are supportive of transgender children.
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jackit4me
jackit4me 5 years ago
What a great Mom you had.. she really let Candi flourish and blossom. So loving
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