So we're going food shopping. I'm David and married to Jill for 40+ years. We live in the Caribbean on St Croix, a beautiful tropical island. We are just about to leave. We have the shopping list, the reusable bags and the cooler for the perishables.
She looks at me and says, " that shirt is to tight, either put on a bra or change your shirt.
I thought I looked good after choosing white 5 inch shorts and a heather gray v neck t -shirt with black slippers, Gold hoop earrings, nail and toe polish with subtle make up but my boobs and pierced nipples were noticeable hence her comment. So I put on my 34 B Hanes white T-shirt bra with the nipple petals which was clearly evident through the shirt.
Jill was ok with it as there was no comment just a brief look. So she drove to the grocery store and we shopped. To complete the list we had to go to 3 grocery stores but we did it. Man food is expensive on this small island.
My how and when cross dressing story began early in my life around age 5 or 6 years old. I was a twin at birth but my mother had a miscarriage early in her 9th month. Then in her hospital bed hours later she delivered me, thank the stars that they didn't perform a D and C .
My sister Jay is 4 years older than me and my brother 2 years older and had a more stocky build than me.
Mom was a talented seamstress and mended, tailored and made some of our clothing. Our out grown clothes were put in her sewing room until they fit one of us.
Mom worked full time as an RN usually from 3PM until 11PM. So we would see her briefly after school then again in the morning. She was a very busy person working, taking care of the house and us. Dad was a grocery wholesale salesman and worked 8 to 5 and wasn't always pleasant which I relate to him being an only child.
I hated scratchy clothes and preferred soft cotton or anything but wool so I began taking my sister's old clothes from the sewing room because of their comfort. First her underwear and cotton camisoles then after Mom finding in the laundry she asked me why. I told her I liked the colors and patterns and the softness. Soon tops, pants, shorts and anything that Mom deemed not to girly went into my dresser.
I never thought it was a big deal until my brother began teasing me and calling me a sissy but after a while and some words from Mom he stopped. Dad wasn't thrilled either and said some things.
Eventually my sister matured and her old clothes no longer fit but her panties and her old training bras still did. Mom asked about that too and I told that they just felt good.
Probably about 3rd or 4th grade I was wearing mostly boys clothes but would occasionally "borrow" a bra or panties from my Mom, not that they actually fit very well and they were very plain, mostly white.
Then I began taking swimming lessons from a college swim coach at his home pool. I rode my bicycle there about 3 or so miles. There was Beginning, then intermediate then more levels all the way to trained lifeguard. I did beginner and intermediate the first summer. Then the next summer I passed the lifeguard test.
All the students had to wear the uniform swim suit and swim caps. The boys wore speedos and the girls one piece speedo suits. I would have preferred the girls but I never brought it up.
I started surfing at the beaches in New Hampshire and Maine at about 13-14 years old and got pretty good at it. My speedos became to small and stretched out so my Mom surprised me with a Hawaiian style suit for my 15th birthday. It was a black bikini bottom with 2 Hawaiian print panels on the front and back like a skirt. It also had a tank top of the same fabric and because she used a girls sewing pattern it had a bra like thing sewn into to front. I liked and wore it a lot. Mom sewed another for me the next summer. Another Hawaiian print, this time a soft polyester with a shorter skirt and a dance belt thong as the bottom. The top had thinner straps, a lower back and v neck with a built in bra. I loved it and gave her a hug. I later sarr we the pattern and discovered it was a girls style
About the same time I began noticing that girls were beginning to have pierced ears. My sister had hers pierced when she came home for Spring break. I was infatuated! I wanted my ears pierced and wanted to wear little gold hoops.
I asked my Mom and she said it was just for girls but that led me on a quest to the library to find men that wore earrings. I brought several books home with photos of men from Romans to Shakespeare and into the present wearing earrings.
I kept bugging my mom relentlessly until she finally gave in. After her lecture about getting teased and being called a sissy she brought home a suture needle and thread she did mine and hers. After 2-3 weeks she put in small gold hoops and they stayed in all summer.
School started again and yes I was teased by the boys but I got used to it and it eventually stopped. Most of the girls thought it was cool but then a male teacher sent me to the office and I was sent home with a note saying that I was in violation of the dress code for my parents. Mom sent me back to school with her note saying that she had yreviewed the Dress Code and there was no mention of boys and earrings. We won but the code was later changed.
Soon I became interested in girls. Yes as girlfriends and also what they wore. I love looking at their bras under their blouses and their cute skirts and tops with envy.
I was still wearing panties everyday except gym days. My group friend Ruthie began smiling at me and asking about being in the band and surfing. She would tell me that I looked cute and we became boy and girlfriend and dated. Ruthie and I were about the same size and height and she had a nice figure with pretty blond hair. Mine was a darker bond and lighter in the summer. I kept it as long as I could.
I knew very little about sex but I knew I liked kissing and hugging which led to me getting to first base touching her breasts through her blouse and bra.
After about 6 months of petting she touched my penis through my pants then unzipped me and touched me again and discovered I was wearing panties. She thought it was cool and asked what size and colors I wore.
Our next date she gave me a set of pastel day of the week panties and a white satin training bra.
I got my drivers license and we'd go to the beach or skiing in the winter. Ruthie and her mother were very close and she told her everything so she knew of our relationship and love of lingerie.
With our Junior Prom coming her Mom bought us matching bra and panty sets with a garter belt and stockings for under her gown and my tux. That was our first time we made love. Ruthie and I stayed together through high school but it turned out to be our last summer.
Ruthie went to study in Boston to become a Registered Nurse and I went to a progressive college near Montpelier, Vermont and studied fine art photography and colonial architecture.
It was a very liberal school with no real grades so you were evaluated by your work. I learned to learn surrounded with creative people who were genuinely interested in creating something and connecting with people.
I met and hung with a woman from Hawaii who was a classical pianist. We developed a connection and just accepted one another as is, no commitment, no rules just something special that I think we knew was in the moment. We talked about and love and everything and anything and how we regarded life and love. She was a feminist and I embraced my fem side. I think that may have been when I admitted to myself that I was bigender, gender fluid and probably lesbian.
I did try gay sex but it never felt right but we did bring other women into our relationship a few times. In
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