To get where you’re going it’s critical to know where you are, and often helpful to know where you’ve been. I must confess that much of my childhood is shrouded in the fog of memory, but I will strive to share those moments which shine brightest in my mind’s eye.
Crossdressing at Age Five
Crossdressing Childhood Dreams
My earliest memory of being different was when I was about five years old. I can remember it as if it was yesterday. I was besotted with the idea that I would wear my mother’s nightie to bed, yet knew that this desire was wrong. At such a tender age I have no idea how I knew that it would be frowned on, though I’ve heard other ladies say that they were similarly aware at a young age.
As much as a five year old could, I hatched a plan. Early in the evening I would smuggle my mom’s nightie from her room and hide it in the hallway closet. When she came to check on me before going to bed I would pretend to be sleeping, and then wait the torturously long while until my parents went to bed. Once they were soundly asleep I would sneak out to get the nightie, put it on and enjoy a night of bliss.
I must say that I’m quite surprised my plan went off without a hitch, and the next morning I changed back and reversed the “nightie from mom’s room to hallway closet” routine. I remember feelings of anticipation, excitement and then a deep abiding calm as I drifted off to sleep in her nightie.
Crossdressing in Bathing Suits
Still in early childhood I recall one day when a neighborhood girl came to play and then sleep over. In the afternoon sunshine I convinced her to trade bathing suits before running to the pool and jumping in. We bounced around in the water, and I remember loving every moment of it. I was scared that my mom would think something was amiss, yet delighted when she noticed our swap with what I can only imagine was a joyful laugh at the innocence of youth.
Later in the evening we tried to swap pajamas, but the lack of any expandable material in hers meant they didn’t fit. I grudgingly spent the night in my own PJs. My first blocked crossdressing moment, and transgender disappointment…
Crossdressing Party – It’s Allowed!
One of my fondest crossdressing memory came not too many years after the bathing suit event. I’m not sure how old I was, at best I can remember I was about nine or ten. A neighborhood girl (she who was generous with her bathing suit) was throwing a “Crossdressing Party” for her birthday. Everyone had to come crossdressed as the opposite gender, and I went as a Hawaiian hula girl, complete with grassy skirt and appropriate chest coverings.
I had died and gone to heaven and then died again and gone to heaven’s heaven. I still remember my mom telling my to “sway my hips” as we walked around their pool for the final judging. I ended up winning the prize for “best crossdressed boy” (the girls had a similar prize). I don’t recall how I acted after that, though I suspect a combination of hesitant joy and uninterested aloofness. Crossdressing was a fun thing to laugh about, not something to truly enjoy…
All I Want For Christmas
The last memory from my childhood was about a Christmas wish almost fulfilled. Like many youngsters we wrote letters to Santa asking him in our most polite and grateful way what we would like for Christmas. As was routine, we would write the letter, mom would read it and then we’d put it in an envelope and mail it to the North Pole.
I couldn’t have been much older than eleven, when I remember desperately wanting a dress for Christmas. Somehow I knew that telling my mom I wanted a dress was not a wise course of action. I had planned to wait until after she read my Christmas list and then discretely add “A Dress” at the end of the list before mailing it to Santa. After all, what harm could come if Santa brought me a dress? It would be Santa’s fault, not mine.
Unfortunately I chickened out at the last minute. I’m not sure why – perhaps I was afraid that Santa would tell my parents, or that mom would take one last look at the list before I could safely wrap it in an envelope. Whatever the reason, I remember a sense of lost opportunity that Christmas morning despite my abundance of gifts that included a really neat Capsela building kit [Hey, I've always been a geek in my feminine heart…]
The rest of my early childhood fades back into time. I vaguely remember times I sat longingly watching my mom applying makeup. Perhaps it was just an imagined fantasy, but I seem to recall her doing my hair or letting me play with her makeup. Things would only get more interesting when I took my first tentative steps into adolescence…
What memories do you have of your early crossdressing childhood?
Part two:
This experience that night only last ed no more then perhaps three or four minutes…but in those minutes, I think my whole life changed…and to think it happened so quickly. From there as I wrote, my only thoughts were to somehow get to open my cousins lingerie drawer and look..it was like a driving force..even at six years old…those thoughts dominated me all day long, until I found the courage to wait for the chance to go into their room. How many times did i start and stop going into that room that held all that I ever wanted to see
Wow ,so many good stories. I remember having a poem read to me about how girls were made of sugar and spice and everything nice. I was about 3 years old and I just came right out and asked my mother when could I become a girl. She really didnt know how to answer that but I soon started wearing items here and there of my moms. By age 7-8 I had purchased a few items of female cloths and was regularly wearing panties and nylons under my male cloths. She found them but alowed me to have them anyway. I remember having her say I was her special child once and I knew exactly what she was saying. I never did like sports like my brother but would much rather have engaged in more female activities.
Wow! That's an early start, so wonderful your mom was so supportive
My earliest story is this: The girl next door would come over and play house with my brother, who is one year older. They were the Mom and Dad and I was the baby girl. This was definitely pre-school, so I;m guessing that I was about 4. I found a little nightgown that one of sisters must of had and ran around the back yard. Maybe, someone said something, because after that I always dressed in secret and was never caught. Except maybe once, The family were all in an enclosed porch watching TV. It was a hot summer night. I went upstairs to my sisters room where one of had a cute bikini that I was dying to try on. I might have been 12-13. I put it on, slipped a bathrobe over it, exited the front door, walked around to the back, disrobed and dived into the pool. Anyone could have heard me and maybe decided to join me and I would have been trapped with no place to hide. But no one did. After my swim I reversed the process and returned to the family room. The phone rang. They asked for me. girl, maybe the one who lived behind us, said, "I saw you" and hung up. Another word was never spoken.
Kay
Sex Reverse Role Play
I have always enjoyed cross dressing. Although, I felt like more than just a cross dresser because:
1.I’m not happy hiding in the closet.
2.I feet more sensitive and emotional than the average male. (I cry at Hallmark cards)
3.I dressed from age four, but masturbation was not part of it until my first wet dream at age 20.
4.I have a traditional female perspective with regard to my virtue. I saved myself until marriage and have always been faithful to both wives. (my only sexual partners)
Despite this, I never considered myself transsexual as:
1.I have never had a homosexual experience.
2.I’m not effeminate.
3.I would not pass well as female.
4.The societal sigma has caused me to reject the notion.
However, for the twenty five years of my marriage to my second wife, my wife and I sleep in soft feminine nightgowns. She is not a lesbian and not masculine in any way and yet the sexual role play that is part of every sexual activity usually goes as follows. ( I apologize if this is too graphic. I should also point out that physically the sex is completely normal.)
Our favorite position is one where I am on top with my legs spread straddling her. That frees her hands to play with my little breasts and pull on my nipples. But, first we engage in some foreplay. She will say something like, “Does my girl feel like giving me a blow job tonight?” (Meaning oral sex ). I always respond. “Yes.” “Then get down there girl and do your thing. Does sucking cock make my girl wet?” She inquirers. And I respond “Yes.” “Mmmm, that’s a good girl. You do that so well. You are just a natural born cock sucker. Put that butt of yours in the air for all to see that pretty and inviting pussy of yours. Guess what? A guy just came in. My God! He saw that pussy and is taking off his clothes. Keep sucking sweet heart. Would you like to fuck my girl?” She asks the intruder. “He said ‘yes’, sweetheart. You don’t mind do you my lovely little girl? He is very hard. “No.” I reply. “Then tell him, sweetie.” “Please, fuck me, sir.” I respond. “That’s a good girl. You keep sucking while he fucks you. Is he hard? Does he full that wet moist pussy of yours? “Yes.” I answer. “Well, then, tell him how much you are enjoying this.” “Oh, that feels sooo good, sir. He touches me in just the right spot.” I explain. “ I’m in heaven with one cock in my mouth and another in my cunt. I’m just a littlee sex toy. ” I moan with girlish delight. “Tell me when he cums and tell me what you feel, sweetie.” My wife requests. And soon I tell her. “Oh my God! He exploded with such force.” “That’s a good girl, but I’m not ready for you, yet. I just asked him if there was someone else outside and he told me there was, so I told him to tell him to come in. My girl would like to see how many men she can please in one night.” And the process continues until my wife is satisfied and then she’ll say. “OK, now it’s my turn. Spread your legs. Oh, my girl is so wet. I slide in so easily to that lovely pussy.”
The sex is fantastic. We are both well satisfied when it’s over. I enjoy this so much that I have started engaging in phone sex with men. I disguise my voice so that they think I’m female. As a female it seems perfectly natural to have sex with men. It makes me feel so loved and so fulfilled as a female that I enjoy nothing more.
Am I a transsexual and have denied it all these years?
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