What was your dating experience?

It would seem that we might have had a different dating resume than other guys.

You must be logged in to participate.
  • I never dated.
  • I rarely dated
  • I dated occasionally
  • This topic has 34 replies, 32 voices, and was last updated 1 week ago by Cece X.
Viewing 32 reply threads
  • Author
    Replies
    • #677599
      Cece X
      Lady
      Registered On: April 8, 2020
      Topics: 34
      Replies: 150
      Has thanked: 3322 times
      Been thanked: 1028 times

      Well, this is a question I never expected to find on CDH, Jennifer. Through my teen years, I wanted very much to experience dating, but I was not attractive and so I did not have the courage to pursue a relationship with the opposite sex. Spending four years in an all-boys high school did not help either. I wound up with men and teenage boys instead. My first girlfriend experience was when I was 19 and out of high school.

      I am adventurous and so I have never settled down to live a domestic life with a partner. Fifty years later, I am still alternating between dating men and women. Presently, I am dating a woman.

      2 users thanked author for this post.
    • #677338
      Jenny Thigh High
      Lady
      Registered On: August 10, 2019
      Topics: 7
      Replies: 307
      Has thanked: 1729 times
      Been thanked: 1625 times

      I didn’t date at all. Girls had no interest in me.

      While I was fighting to suppress my desires for men and other boys, I didn’t dare even consider “coming out” then. Even if I had talked myself into dating girls, they had no interest. I wasn’t strong and athletic and popular, which is all girls cared about.

      I definitely had the hots for a few male teachers and a couple other boys. However, didn’t dare act on it in HS. I had very intense fantasies though 🙂

      3 users thanked author for this post.
    • #677337
      Holly Marie
      Lady
      Registered On: August 8, 2022
      Topics: 3
      Replies: 62
      Has thanked: 64 times
      Been thanked: 232 times

      I never got a date at all when I was at school; this was owing to a combination of sheer terror of rejection (I did ask a few times but never had a positive – or even polite – reply) plus the fact that I was living five miles from nowhere – plus the indisputable fact that young girls DON’T like the quieter, more intellectually interested sort of boy!  Yes – you’re always told that it’s “personality, not looks” and that you should just be yourself, well – that is a load of CARP!  (I don’t like swearing on this site!)  As they get older, women may indeed become more interested in the inner person, but when you’re at school they are just going to ignore anyone who likes to read a book.  I have no idea what the situation may have been like for those ladies on the site who preferred boys in the first place; maybe they were a little less shallow?  All I can say is that I never met a teenage girl who thought personality and intellect were more important than looks and sporting ability.  Ho, hum:  I’m just glad that was so long ago…  Holly XXX

      3 users thanked author for this post.
    • #677333
      Dawn Judson
      Ambassador
      Registered On: November 26, 2017
      Topics: 15
      Replies: 195
      Has thanked: 471 times
      Been thanked: 923 times

      Wow! What a topic! This is going to be lengthy (I’m the hostess with the verbose-est).

      I remember being infatuated with a girl in 4th grade (about the time I started trying on my mom’s & sister’s clothes). I asked her to go to the carnival with me. She said that her mom wouldn’t let her because I wasn’t Jewish. Then, in 7th grade, there was a girl with blue eyes & long blonde hair (got me every time), but my feelings for her were unrequited. Throughout junior high, I used to daydream about being one of the pretty mini-skirted girls in my class. In 9th grade, a redhead was after me, but she wasn’t my type. Like many of you, I was shy. I was small & got picked on. I got involved with sports & tried to fit in, but never did. It wasn’t until my senior year that I finally had a steady girlfriend (stole her from my best friend), but that didn’t last long. I didn’t know how to act around her. We’d go park– and never do anything– not even make out. I think we stayed together, as long as we did, for status. She was a sophomore & I think she wanted to show off that she bagged a senior. For me, I wanted to show that I wasn’t the wimpy nerd, that people thought I was, & was capable of getting a girlfriend.

      The summer after graduation, I started going steady with a girl named Terry. I went into the Air Force, in the fall and, while in basic training, my best friend told me that she was seeing other guys. On my first leave, I met a girl who “popped my cherry”, but that was just sex after I found out that she was into a lot of spooky occult stuff. A year later, a friend arranged a blind date for me.  Another Terry, and I experienced a whole new feeling with her. Was this what love felt like? I was crazy about her. I thought she was the one, but it only lasted a few months. I wasn’t her type. Turns out she was a lesbian. I often wonder how she would have reacted if she had known about Dawn, and how she’d be if she met me (Dawn) now.

      At my second tech school, in the Air Force, I was BMOC. Still shy, but I attracted the WAFs, I think, because I had been in longer than the other guys who were just getting out of Basic, so I had hair. I also had a car & managed to finagle an apartment off base. I used to go “fishing” at the local university, for college girls, but wasn’t very successful.

      Then, I started attending college, myself, & a whole new world opened up. During this period, my urge to dress & my desire to be a woman were still there, but on the “back burner”. I was dating a whole bunch of women (my mom used to say that I had a “harem”) & age didn’t matter. Some were as much as 16 years older than me & one was eight years younger. With her, I was 22, & got threats of a restraining order, from her dad. I asked why. “Because you’re too old. She’s underage,” he said. “Eighteen is not underage,” I replied, “She’s only four years younger than me.” “She’s 14!” he said. My response? “Sir, she told me she was 18 (& she looked every bit of it). You don’t need that restraining order. I’m done with that.” And if you’re wondering, yes, we did– often!

      Fast forward a few months later. I’m living with my parents & they go out of town for a week. What’s a guy to do but have a week-long epic party? My goal was to make the Guinness book for “most women bedded in a single week”. So Wednesday night, after a number of “conquests” already under my belt, a female friend asked if she could bring a friend on Friday. The more, the merrier, I said. They showed up and OMG! This girl walks in & is the most beautiful creature I’d ever seen. Yep! Long blonde hair & blue eyes. I spent the rest of the night, focused completely on her. She had to leave around midnight. After a long, passionate goodnight kiss, I told her that I’d call her, the next day. Right after that, I went on to my next conquest. 😉

      I called her & made a date to play tennis. The following weekend, I took her to a college football game, a pro baseball game & a concert & I knew she was the one. I had done a lot of bar-hopping, over the previous five years, but was ready to settle down. So I proposed & she said yes. Shortly after we got married, we were both getting ready for work, one morning, & I played a trick on her. She had her clothes laid out. While she was in the shower, I put on her bra under my clothes. It was driving her crazy. She couldn’t figure out where it went– until she hugged me. We both laughed. A couple of months later, we attended a Halloween party– as opposite sexes. She could see how much I enjoyed it & consented when I asked if I could start dressing, occasionally, around the house.

      I’m kind of getting off the subject, aren’t I? Anyway, we’ve been together a long time, now, & raised a family together. And Dawn’s still here. In fact, she’s more here than ever, but it’s still not enough.

      3 users thanked author for this post.
    • #677305
      Caty Ryan
      Baroness
      Registered On: August 27, 2017
      Topics: 121
      Replies: 1086
      Has thanked: 8 times
      Been thanked: 4332 times

      Bck in my teenage years I attended an all male trade school, (in OZ we called them “Techs”), so no girls in the school to “get to know”.

      Thus my teenage dating years were strictly “summer holiday romances” with introductions to girls via family or the local rock dance.

      Once 18, with a car and working, the opportunities expanded, but I never had a serious romance until my early 20’s.

      Met my ex at a Sunday night dance at the age of 23…

      Caty.

       

       

      1 user thanked author for this post.
    • #677297
      Erica Love
      Duchess
      Registered On: September 2, 2022
      Topics: 2
      Replies: 20
      Has thanked: 183 times
      Been thanked: 111 times

      Hi Jennifer,

      I dated a little in high school and in my early twenties. I got married at 25, had 2 sons and she left me after 5 years for another woman. Second marriage ended after I found out she was in an affair with a member of the church band. Had a third relationship for 20 years that produced my trans son but ended 4 years ago after her 6th affair. My woman picker is severely broken. Don’t think I’ll ever date another woman, don’t care to deal with those kinds of trust issues and happy being the best (single) parent to my 15 year old son.

      Erica ❤️

      4 users thanked author for this post.
      • #677368
        Gwyneth
        Lady
        Registered On: January 21, 2021
        Topics: 5
        Replies: 328
        Has thanked: 2027 times
        Been thanked: 1165 times

        I have an equally broken ladypicker. Only problem I’ve found since making “this” change in my life? MEN ARE PIGS!

        Gwyn

        2 users thanked author for this post.
    • #671807
      Rayna Carlian
      Duchess
      Registered On: March 4, 2020
      Topics: 3
      Replies: 463
      Has thanked: 597 times
      Been thanked: 1635 times

      I haven’t replied to the poll yet because, I dated a LOT in high school. I spent 3 years out of the 4 in an all male military school, and the girls at surrounding schools were into it.

      So, as “dating occasionally” was the most active dating option in the poll, I didn’t even choose and answer.

      So, there’s me, high school hooligan and out there chasing skirts. Now, I wear the skirts…haha.

      Have fun out there,

      xoxo

      Rayna

      4 users thanked author for this post.
    • #671580
      Emily Alt
      Duchess - Annual
      Registered On: August 24, 2019
      Topics: 17
      Replies: 917
      Has thanked: 806 times
      Been thanked: 4379 times

      I hated my high school and didn’t date.  I made up for it in college.  It was an “interesting” time in my life.  My mother would pester me when I was going to find a “good” girl and get married.  I would tell her I was skipping over my first 2 divorces.  It’s a good thing too.  Girlfriends 1-5 were definitely divorce material.  I’ve only had 1, so I guess I’m doing good. Right?

    • #671563
      Paula Here
      Lady
      Registered On: April 13, 2020
      Topics: 22
      Replies: 194
      Has thanked: 889 times
      Been thanked: 1231 times

      I only dated a few girls before my wife.  We have been together for 34 years. We started before my 18th birthday. She knows about my crossdressing, and seems to accept me.

      3 users thanked author for this post.
    • #671335
      Kelli Marlowe
      Lady
      Registered On: August 4, 2020
      Topics: 13
      Replies: 166
      Has thanked: 2052 times
      Been thanked: 945 times

      Dating was tough in high school…till I got wheels.Hard to date without a license in a rural area, no public transit.
      Spent most of my first 20 adult years married(twice) Dated a lot after the second divorce,but still single and have given up.
      Sometimes it’s just easier to become the girl you want, rather than try to find her,lol

    • #671230
      Donna Ceedee
      Lady
      Registered On: January 17, 2022
      Topics: 1
      Replies: 38
      Has thanked: 31 times
      Been thanked: 213 times

      I also did not date in high school. I was painfully shy. I did have my eye on several girls. Mostly for the way they dressed. Short pretty dressed and pantyhose. Loved those pantyhosed legs. I would sneak my sister’s or mother’s pantyhose to wear at that time not really knowing why I had such a desire. I wasn’t really familiar with crossdressing term.

      I did end up marrying the first girl I dated. It wasn’t really my intention but I thought she really loved me. I did expose her to some of my crossdressing tendencies. She didn’t like that at all. Things slowly started to fall apart for many reasons.

      I divorced and remarried. My current wife found out about my crossdressing. Tolerates it which is better then nothing. Can’t complain, life is pretty good now.

      7 users thanked author for this post.
    • #671222
      Kris Burton
      Lady
      Registered On: August 6, 2022
      Topics: 0
      Replies: 62
      Has thanked: 147 times
      Been thanked: 270 times

      Thank you for starting this thread, this is a big subject for me that I have not been able to address effectively until recently. I always perceived myself as unattractive, nerdy and hopelessly naive – so therefore I was. My junior year of HS I became interested in the sister of a friend of mine when she transferred to my HS from Catholic school. She was new and friendless, but she knew me a little, so we latched on. We were 16, and would be together through HS and college, even though we attended different schools, and married shortly thereafter. Prior to our marriage, we were not intimate, still I was 100% faithful. WE lasted 2 1/2 years, she had an affair with her boss 16 years her senior, and filed for divorce. So I was suddenly 25, single, and having never really dated.

      I caught the break of a lifetime when I met my now wife a few years later. Curiously, despite our now 41 years of successful marriage and two children, not to mention the fact that I am now 70 years old, I am still haunted by my lost years of social/sexual activity. Somehow though, crossdressing gives me release from these negative feelings, and I know the two things are for me connected. Just the very fact that I dress makes me feel less socially inept and naive, and I have this big secret no one knows about except for my wife. It’s a very good place to be – and Jennifer you are right, you are never to old to be who you really are.

      Kris

    • #671207
      Jocelyn Beyoody
      Duchess
      Registered On: May 4, 2022
      Topics: 0
      Replies: 86
      Has thanked: 183 times
      Been thanked: 281 times

      I’ve been reflecting on this very issue of late. I did ok. Had my fair share. My mom always said, “they love you the first week. The second the hate you.”
      Sadly not an exaggeration. I’m on my second marriage. I wasn’t mean or abusive. Always starved for attention. Which leads always to cheating.
      I’m more ashamed of my track record than my CD.
      I was confused and afraid. I just couldn’t connect with anyone, boy or girl. My life became very small and lonely.
      The type of girl, same size and features that resembled me. So I could fit into their clothes.
      I’m just now coming to grips on who I am. I hope that my days of aimlessly wondering are over.

    • #671195
      Araminta Purdy
      Duchess
      Registered On: January 23, 2020
      Topics: 10
      Replies: 496
      Has thanked: 1056 times
      Been thanked: 1873 times

      Oh, phew! I thought I would be the only one to say she never dated during High School except for a bit before graduation that I forgot about until just now. That’s one of the reasons why I created ‘her’.

      Araminta.

    • #671184
      Jill Quinn
      Lady
      Registered On: July 24, 2021
      Topics: 1
      Replies: 169
      Has thanked: 1588 times
      Been thanked: 769 times

      I seem to be in the minority here, as I never dated any girls nor went on a date. Girls were always saying I was sweet or a doll, but they never seemed to like me enough to want to be around me longer than they had to. And God knows I loved them. I was very small, a loner, and most people said I was ugly. Honestly, no arguing that. I never found a woman to marry until my wife came along when I was in my 30’s. We were married five years ago when I was 44. She knows about Jill and accepts her and even encourages Jill to be a part of my life as a man. I’m very lucky to have her.

      Jill

    • #671162
      Susan Talbot
      Lady
      Registered On: June 28, 2022
      Topics: 1
      Replies: 247
      Has thanked: 2317 times
      Been thanked: 918 times

      I didn’t date a lot on high school I was kind of shy the but then I bloomed and dated a lot in college and after college. Got married at 32 that was a big mistake but it seems like we learn a lot from bad relationships in the sense that once you have a bad one you know what you don’t ever want again. Now engaged and never been happier she is the only one I have ever told about my dressing and she totally supports me in every way.

      Susan

    • #671029
      Gwyneth
      Lady
      Registered On: January 21, 2021
      Topics: 5
      Replies: 328
      Has thanked: 2027 times
      Been thanked: 1165 times

      I’ve read all these wonderful stories. Glimpses into the lives of my great friends! I was just beginning to realize that girls really didn’t have cooties (i.e., puberty hit me like a ton of bricks). I started a new smaller HS where I could now make the football, basketball, and baseball teams. First serious girlfriend (cheerleader) came my way in my junior HS year. And after several months, THAT happened for the first time. OMG! I had to marry this girl. She just didn’t have this same desire. After hearing of her other boyfriends, we broke up. I had a couple other nice, but not serious girlfriends. Met my 1st wife at the end of my senior year. Dated for 3 years before marrying. I knew I was in trouble on our honeymoon. We stayed married for 10 years before I met another woman that was in just as horrible a marriage as I was. Affair, promise to leave our spouses and live happily ever after. I left my wife; she didn’t leave her husband. At the end of this, I met wife2. Blind date. Fast forward and we’ve been married for 30+ years. Tumultuous at best. Maybe I’m not husband material.

      My conceived (rightfully or not) mistreatment is what I blame for my desire to crossdress. That’s another story. Just to say I was always a manly boy as well as a manly man in my early years. Maybe it’s hormonal, but I’ve gone through a lot of changes in the last 15 or so years.

      Gwyn

    • #670960
      MelanieElizabeth
      Lady
      Registered On: January 9, 2021
      Topics: 19
      Replies: 255
      Has thanked: 751 times
      Been thanked: 1572 times

      Hi Jennifer. This a great poll, never seen any like it in my time here! We have a lot in common  Jennifer and it’s not just our preferred clothing, I also married the first girl I dated. I have often wondered about my choice in a partner, not because she isn’t a great person but because I never really experimented with others. I knew I was attracted to wearing femme clothing long before I was attracted to women themselves so it was odd as an adolescent, entering into the dating world. Maybe it was low self esteem or some other factor but my wife and I always got along and things just worked out between us.  I never felt a need to look elsewhere for a mate even as the years past and I realized that cross dressing wasn’t just a some kind of kink or a passing phase of my life. I have been exclusive with my wife since high school and have known her since we were about 10 years old, we have a good life and are in the midst of raising a couple of great children so I wouldn’t change a thing! Other than maybe telling her I was a cd when we met in third grade! Lol. Maybe if I had she would have grown to be a little more accepting and possibly extending me her blessing to go out as Melanie once in a while. One can dream.

    • #670948
      Michelle McQueen
      Lady
      Registered On: June 14, 2021
      Topics: 28
      Replies: 1506
      Has thanked: 9742 times
      Been thanked: 7371 times

      I dated a girl or two in high school but it wasn’t very long each time. I was very shy around girls. I heard a girl on our bus liked me and wanted to date so we dated the entire time in high school. She was very pretty and it was a hot affair. Everyone thought we would naturally get married after school but I caught her cheating on me when I was drafted in the service when I came home from boot camp. That was the end of that relationship. I knew my current wife as a friend about 7yrs before we started dating after she got a divorce from her first husband. He turned out to be a drug dealer and got busted and since I was in law enforcement at the time he always told everyone I did that to him… I did not. I never told any of my girlfriends about my dressing. In hindsight, getting married was probably the worse decision I ever made.

    • #670947
      Lisa Leigh
      Lady
      Registered On: April 20, 2022
      Topics: 4
      Replies: 204
      Has thanked: 624 times
      Been thanked: 849 times

      Yes, I could say I dated in High School. Like almost everyone here I got along better with the girls. Boy talk never was my seen, nor is man talk now. I hung with the girls, growing up was a trip! In my neighborhood myself and another buy, we’re the only two guys. While we had 9 girls. So we mostly hung with them growing up. Once in HS it seemed we all went different directions. Again I levitated toward groups of girls. One that I knew were a group from church. One of the girls I met was Lisa, who did go to our church. A couple of the girls in the group I knew were like sisters, and I would hate to ruin a relationship! Lisa and really clicked and started dating. Lisa and I were on and off again over the next 3 years. The next girls name was …. Lisa! It just happen to be. We got along great! My former Lisa was driving me nuts! We had decided to sign up for some the same classes in the fall, well, we had one! Together. So I still saw her every school day. But the current Lisa and I were still going strong. Then she dumped me! I really don’t remember why. Meanwhile the first Lisa hears the news and the next morning at my locker? Yes, Lisa, she wanted to get back together again. So we’re off after a few months. And summer is here and … she finds a new summer boy friend. So that summer I teched in a small community theatre. There I met a prop girl, her name is Lisa… what the heck! Just so you know, I kinda liked all of them before I even knew their names. So I wasn’t attracted because of the name. We went together for a few month and around Christmas break she or we broke up. And then Lisa and I were together again, that’s the first Lisa. And we were together until college as she went to one and I another. So that’s my HS dating history and that also why my name is …

      Lisa Leigh

    • #670925
      Deborah Sullivan
      Lady
      Registered On: February 27, 2020
      Topics: 2
      Replies: 974
      Has thanked: 4671 times
      Been thanked: 4158 times

      wow so glad to hear you girls share these experiences. I was very popular with girls but never considered to be dating material but rather being best friends. Look back I realize I was probably too effeminate acting and realized I was bi. Anyway never married but no regrets since I have been able to enjoy life as I was meant too. For this reason I never had to hide my dressing and go through all the anxieties most of you have had coming out to a wife and kids.

    • #670922
      ChloeC
      Duchess
      Registered On: November 5, 2019
      Topics: 12
      Replies: 602
      Has thanked: 2215 times
      Been thanked: 2812 times

      Well, I was terribly shy in high school, going on actual dates with 2 girls, although I knew a lot of young women, easily having conversations, some involved, and later, thinking about it, I strongly suspect some of them would have said ‘yes’ to a date if I had asked.

      However, there were other issues going on besides my inner desires which I was working hard to suppress, which went along with my absolute fear of rejection as I always felt those desires were easily seen – they weren’t, but I still felt that way. I had a stepfather who swore that no (step)son of his would ever drive one of his cars, so getting a car to take a girl somewhere was almost out of the question. I eventually did as he slowly relaxed his dictates, but I had to go to extreme lengths to even ask. Wasn’t fun, ever.

      When (junior) college came along (and still living at home, and working part time), I had more access to a car and I started getting my nerve up and started asking more girls almost all of whom said yes of which some dates were really interesting – the mother of one called the police as we were extremely late getting back.

      Now, what happened during that time was that at least two of the young women I dated wanted a whole heck of a lot more from me than I was anywhere near ready to provide.  One got pregnant and married the boy she dumped me for – in that order. And the other, I began to understand exactly what she was aiming for (something very similar) and, hating myself, I had to end our relationship (ok, dump her).  The reality was that as a ‘boy’ I was still emotionally about 15 or so, but knew what the birds and bees were about, and knew I wasn’t near ready for the intimacy being offered.

      Hugs, Chloë

       

       

       

    • #670919
      Rozalyn Richards
      Lady
      Registered On: July 27, 2022
      Topics: 0
      Replies: 180
      Has thanked: 185 times
      Been thanked: 645 times

      I didn’t date anyone while i was at school, when i left school in 1968 i was 15 and started work not long after, I dated a few girls till i met my wife when i was 18 , I was a bit nieve because i was still a virgin when i met my wife, I didn’t know i was bi till i was in my 20’s but that’s another story, before that i had no interest in boy’s, I’ve only ever met one other crossdresser and i was able to go round to his/her house and dress up together,

      Hugs Rozalyn X

    • #670915
      karley delaware
      Baroness - Annual
      Registered On: October 23, 2017
      Topics: 10
      Replies: 442
      Has thanked: 2399 times
      Been thanked: 1387 times

      It was always……” you’re a nice guy ,but………………”  I did not know it but karley was always with me ……………showed herself whenever I dressed ………………..provide that release teenagers need …………….I did not see it that way for the longest and   was ashamed  of my activities………………she’s a good woman……………….these days she and I have very deep conversations …………have helped me overcome  multiple traumas and understand them better ……………..karley is the girl I was supposed to be………………………….karley

    • #670894
      Lauren Mugnaia
      Duchess
      Registered On: November 1, 2021
      Topics: 15
      Replies: 349
      Has thanked: 3573 times
      Been thanked: 1866 times

      Interesting question and topic. Like many have already pointed out, my relationship with girls has always been from a far different point of view than ordinary cis males. I knew early on that I was ‘different’ and liked girls, girl’s things, girl talk, I liked being with them, and being girly. I was already spending time with them so why did I need to ask them out on a date?
      I eventually met a young lady while on a skiing trip and we just ‘clicked’, no dating, just being close friends and spending time together, she knew about my feminine side. We eventually married and raised two kids, were happy together until she lost her battle with cancer 8 years ago.
      Since than I have transitioned, I’m now legally a woman and live as one full time. Almost all my friends are women, so there’s really no point in dating anyone.

      Hugs,

      Ms. Lauren M

    • #670890
      Саманта
      Managing Ambassador
      Registered On: January 21, 2018
      Topics: 681
      Replies: 1651
      Has thanked: 9623 times
      Been thanked: 5910 times

      I’m also sure that many of my girlfriends wondered where some of their cute bras and panties disappeared to, as back then I would often “borrow” a nice item of lingerie or two to add to my own collection. Yes, that was not the honest or right thing to do, but proximity to all of those wonderfully feminine items did tend to make my fingers wander at times back then.

      Heh, I had that experience a few times also, not gonna lie… and then there was the lost & found bin at the laundromat… 😅

      I did date occasionally and although I liked girls I was a bit shy with them. I had always admired girls but usually the relationships ended with, ‘You are a nice person but…..’  Mixing with girls was quite easy as I seemed to have a bond with them and could talk among them but found it difficult to ask them out.

      I also had this experience quite a bit. Altho meeting girls wasn’t usually too big a challenge, they often decided i was best as a friend. And that was fine too, but occasionally frustrating. Eventually i learned how to get them attracted, but once i got decent at that i realized it was more of a game, & that naturally i was more like one of them than anything else, so it started to make sense…

    • #670887
      Angela Booth
      Lady
      Registered On: August 1, 2020
      Topics: 9
      Replies: 1150
      Has thanked: 4356 times
      Been thanked: 5144 times

      I did date occasionally and although I liked girls I was a bit shy with them. I had always admired girls but usually the relationships ended with, ‘You are a nice person but…..’  Mixing with girls was quite easy as I seemed to have a bond with them and could talk among them but found it difficult to ask them out. Of course I had my underlying secret which stymied me in a longer term relationship. When I hit that age area where my friends were getting married I still had the issue of my dressing and couldn’t admit this so I was the single one. Eventually I did have two relationships where things were going towards marriage and I came out to them. The first was a very abrupt end  and the second was an acceptance with long chats about how it would work, but ended all the same. So I decided that I would not get involved and am still single having progressed to living full time now.

      I wouldn’t be honest if I said it is perfect as I would love to have an accepting partner but my view is that it takes a very special woman to accept you as you are and I wouldn’t want to cause angst or dishonesty to a partner.

    • #670883
      Holly Morris
      Lady
      Registered On: April 15, 2022
      Topics: 63
      Replies: 149
      Has thanked: 1863 times
      Been thanked: 1631 times

      There wasn’t an option for “I dated all the time” so I couldn’t actually submit a vote. However, even though I dated a lot of girls, I also wanted to “be” one of the girls I dated. Perhaps because I might have been more sensitive than many of the more macho teenage boys, I was attractive to girls? I’m not sure, but I had a lot of girlfriends throughout high school. I’m also sure that many of my girlfriends wondered where some of their cute bras and panties disappeared to, as back then I would often “borrow” a nice item of lingerie or two to add to my own collection. Yes, that was not the honest or right thing to do, but proximity to all of those wonderfully feminine items did tend to make my fingers wander at times back then. I was a teenage boy who wanted to be a girl and didn’t understand why I felt that way, so sometimes I behaved in less than the best way that I should. That’s why when I moved into my own apartment when I was 18, I was finally able to buy my own lingerie, clothes, heels, makeup, etc. and start exploring what it really meant to be a crossdresser.

      Hugs,

      Holly

    • #670869
      Саманта
      Managing Ambassador
      Registered On: January 21, 2018
      Topics: 681
      Replies: 1651
      Has thanked: 9623 times
      Been thanked: 5910 times

      I dated a fair amount i suppose.  I only had one serious girlfriend the whole time i was in high school, & that relationship lasted about 7 months.  So i was mostly single and i dated a fair amount.  I wasn’t great at it but i was in a band so it was pretty easy to meet girls & eventually i got better at it.  Nowadays i’m single & i like it that way, i can’t imagine trying to date now, the world is a different place 😂

    • #670861
      Lara Tucker
      Lady
      Registered On: September 29, 2021
      Topics: 2
      Replies: 1066
      Has thanked: 23573 times
      Been thanked: 3772 times

      Hi Jennifer,

      I ended up staying with the second or third girl I dated in high school. Or she stayed with me?
      We got married as soon as she finished college, and we are still happily married.
      I just discovered my inner woman about 3 years ago, and am still closeted. Hopefully that is going to change soon, with happy results. 🤞🏻

      💕Lara

    • #670852
      Julianna S
      Lady
      Registered On: July 29, 2022
      Topics: 3
      Replies: 52
      Has thanked: 23 times
      Been thanked: 227 times

      I was terrible at dating. Very shy, could relate to girls as friends, but very difficult to work up the nerve to ask one out. I am still like that now, in my 50’s. I honestly don’t have any regrets about it. It’s just the way i am.

      5 users thanked author for this post.
    • #670845
      Jennifer Swanson
      Duchess
      Registered On: April 20, 2019
      Topics: 67
      Replies: 249
      Has thanked: 5403 times
      Been thanked: 2030 times

      I realize there are limited choices in this poll.  When I was writing this poll I must have hit the wrong button and it posted unexpectedly. However I’m still curious because I think most of us had a different social life.  My boy self went to my 50th high school reunion 3 years ago and nothing had changed.   I knew everyone but had nothing in common..  I never had one date in high school.  The one girl I had a crush on but never dated had passed away.  I married the first girl I dated at the end of college.  We stayed together for 35 years with 2 kids and 3 grand kids.  However I do love having found the girl in me.  My second wife accepts me as Jennifer because she can see how much happier I am. You’re never to old to be who you truly are.

    • #670839
      Anonymous
      Topics: 0
      Replies: 0
      Has thanked: 0 times
      Been thanked: 0 times

      At school I was a typical nerd and so, being part of that demographic, my chances of school dating were pretty much zero anyway. Even if I had thought about it, being self-conscious about wearing women’s underwear would have done nothing for my confidence and would probably have held me back anyway.

      I only had two semi-serious relationships post-school, and both of them ended when they found out about how I dress. The first time I was caught, the second time I owned up at what I thought was an appropriate stage in the relationship. The end result, however, was the same in both cases.

      5 users thanked author for this post.
Viewing 32 reply threads
  • You must be logged in to reply to this topic.
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

or    

Forgot your details?

Create Account

If you don't see the captcha above please disable ad and tracking blockers and reload the page.