• I met an awesome man the other day, and I’m still smiling about it.

    We originally connected on Doublelist and spent a few weeks flirting, talking, and exchanging some very naughty messages before finally meeting last Saturday. I’ll call him “Ken.” He’s in his 70s, White, with gray hair, glasses, and plenty of body hair—all things I find incredibly attractive. There was something about him that immediately made me feel comfortable.

    Yes, he’s married. I know that part may be controversial, and I’m not pretending otherwise. His personal situation is complicated, and I’m going to leave the private details of his marriage to him. I don’t pursue married men, but when an adult man makes his own decision to pursue me, I sometimes allow myself to see where things go.

    One of the things I liked most about Ken was that I didn’t feel pressured to become somebody else for him. I told him about a previous experience where a guy was disappointed because I didn’t show up in a wig, makeup, and a full feminine outfit. That really bothered me because, although I have a very feminine side, that doesn’t mean I always want—or am able—to transform myself into someone who looks completely female.

    Ken understood immediately.

    He told me he likes me exactly as I am: a feminine man with smooth skin, a softer personality, and my own way of expressing femininity. He has even started calling himself my “Daddy,” which, I admit, pushes several of my buttons.

    When we finally met, there was definitely sexual chemistry between us. We kissed, touched, explored each other, and tried a few things together. We jacked ach other off and sucked each other's dicks. He also tried to **** my asspussy, but I was too tight for full penetration. I told him as long as he got into my crack, it felt great.

    We them cuddled together on my bed naked. And that is actually the part that matters most to me.

    As sexual as I can be, what I really crave is sexual intimacy rather than sex for its own sake. I want somebody I can lie beside, cuddle with, spoon, kiss, touch, and feel completely comfortable around naked or in my girl clothes. The idea of spending an evening together on the couch watching television, wrapped around each other with nothing to hide, sounds almost heavenly to me.

    Ken seems to understand that side of me too.

    We’re still flirting and messaging each other, and he has already talked about seeing me again. I didn’t take any pictures or videos of our first meeting. For once, I was simply enjoying the moment instead of trying to document it.

    Whatever ultimately happens between us, I’m glad I met him. I felt desired without having to perform, dress a certain way, or pretend to be somebody I’m not.

    And that may have been the biggest turn-on of all.

    #sissy #sissyboy #crossdresser #shemale #tgirl #gay #lgbt #lgbtq #femboy #gurl #transgirl #transwoman #transgender #naked #nude #fullfrontal #oralsex #analsex #gaydate
    I met an awesome man the other day, and I’m still smiling about it. We originally connected on Doublelist and spent a few weeks flirting, talking, and exchanging some very naughty messages before finally meeting last Saturday. I’ll call him “Ken.” He’s in his 70s, White, with gray hair, glasses, and plenty of body hair—all things I find incredibly attractive. There was something about him that immediately made me feel comfortable. Yes, he’s married. I know that part may be controversial, and I’m not pretending otherwise. His personal situation is complicated, and I’m going to leave the private details of his marriage to him. I don’t pursue married men, but when an adult man makes his own decision to pursue me, I sometimes allow myself to see where things go. One of the things I liked most about Ken was that I didn’t feel pressured to become somebody else for him. I told him about a previous experience where a guy was disappointed because I didn’t show up in a wig, makeup, and a full feminine outfit. That really bothered me because, although I have a very feminine side, that doesn’t mean I always want—or am able—to transform myself into someone who looks completely female. Ken understood immediately. He told me he likes me exactly as I am: a feminine man with smooth skin, a softer personality, and my own way of expressing femininity. He has even started calling himself my “Daddy,” which, I admit, pushes several of my buttons. When we finally met, there was definitely sexual chemistry between us. We kissed, touched, explored each other, and tried a few things together. We jacked ach other off and sucked each other's dicks. He also tried to fuck my asspussy, but I was too tight for full penetration. I told him as long as he got into my crack, it felt great. We them cuddled together on my bed naked. And that is actually the part that matters most to me. As sexual as I can be, what I really crave is sexual intimacy rather than sex for its own sake. I want somebody I can lie beside, cuddle with, spoon, kiss, touch, and feel completely comfortable around naked or in my girl clothes. The idea of spending an evening together on the couch watching television, wrapped around each other with nothing to hide, sounds almost heavenly to me. Ken seems to understand that side of me too. We’re still flirting and messaging each other, and he has already talked about seeing me again. I didn’t take any pictures or videos of our first meeting. For once, I was simply enjoying the moment instead of trying to document it. Whatever ultimately happens between us, I’m glad I met him. I felt desired without having to perform, dress a certain way, or pretend to be somebody I’m not. And that may have been the biggest turn-on of all. #sissy #sissyboy #crossdresser #shemale #tgirl #gay #lgbt #lgbtq #femboy #gurl #transgirl #transwoman #transgender #naked #nude #fullfrontal #oralsex #analsex #gaydate
    Love
    Like
    6
    0 Commentarios 0 Acciones 14K Views
  • I haven't posted in a while. I just wanted to say hi!

    http://chrissyinsd.hotviber.com/

    #sissy #sissyboy #sissies #sissyboys #sissygirl #sissygirls #femboy #femboys #femman #gurl #crossdresser #crossdressers #crossdressing #tgirl #shemale #shemalechrissy #sissychrissyinsandiego #chrissyinsd #trans #transgirl #transwoman #transfemale #transgender #lgbt #queer #pantyboy #meninpanties #dress #menindresses #bra #meninbras #pinkbra #thong #gstring #gaydate #gayboyfriend #loveislove #gaylove #translove
    I haven't posted in a while. I just wanted to say hi! http://chrissyinsd.hotviber.com/ #sissy #sissyboy #sissies #sissyboys #sissygirl #sissygirls #femboy #femboys #femman #gurl #crossdresser #crossdressers #crossdressing #tgirl #shemale #shemalechrissy #sissychrissyinsandiego #chrissyinsd #trans #transgirl #transwoman #transfemale #transgender #lgbt #queer #pantyboy #meninpanties #dress #menindresses #bra #meninbras #pinkbra #thong #gstring #gaydate #gayboyfriend #loveislove #gaylove #translove
    Love
    6
    1 Commentarios 0 Acciones 53K Views
  • A photo my new boyfriend took of me on our date:

    #sissy #sissies #sissyboy #sissyboys #sissygirl #sissygirl #gurl #gurls #crossdresser #crossdressing #crossdressers #CD #TS #tgirl #gay #lgbq #shemale #trans #transgirl #transwoman #transfemale #femboy #femboys #femman #gaydate #loveislove
    A photo my new boyfriend took of me on our date: #sissy #sissies #sissyboy #sissyboys #sissygirl #sissygirl #gurl #gurls #crossdresser #crossdressing #crossdressers #CD #TS #tgirl #gay #lgbq #shemale #trans #transgirl #transwoman #transfemale #femboy #femboys #femman #gaydate #loveislove
    Love
    Yay
    Wow
    8
    0 Commentarios 0 Acciones 33K Views
  • Just got done shaving for my date tonight! We're going to shower together! Kisses!

    http://chrissyinsd.hotviber.com/

    #sissy #sissyboy #sissies #sissyboys #sissygirl #sissygirls #femboy #femboys #femman #gurl #crossdresser #crossdressers #crossdressing #tgirl #shemale #shemalechrissy #sissychrissyinsandiego #chrissyinsd #trans #transgirl #transwoman #transfemale #transgender #lgbt #queer #pantyboy #meninpanties #dress #menindresses #bra #meninbras #pinkbra #thong #gstring #gaydate #gayboyfriend #loveislove #gaylove #translove
    Just got done shaving for my date tonight! We're going to shower together! Kisses! http://chrissyinsd.hotviber.com/ #sissy #sissyboy #sissies #sissyboys #sissygirl #sissygirls #femboy #femboys #femman #gurl #crossdresser #crossdressers #crossdressing #tgirl #shemale #shemalechrissy #sissychrissyinsandiego #chrissyinsd #trans #transgirl #transwoman #transfemale #transgender #lgbt #queer #pantyboy #meninpanties #dress #menindresses #bra #meninbras #pinkbra #thong #gstring #gaydate #gayboyfriend #loveislove #gaylove #translove
    Love
    7
    0 Commentarios 0 Acciones 58K Views
  • I met a really wonderful man last night We met at one of my favorite places in San Diego’s Hillcrest neighborhood—Baja Betty’s. It’s a spot I go to often and one of the few places where I feel completely safe being my true self as a trans woman, where I can relax, let my hair down, and just be me.

    We started talking and somehow time just disappeared. The conversation flowed so easily, and we kept discovering how much we had in common. He’s older than me—I’m 47 and he’s 76—and honestly, it feels kind of perfect. I don’t have “daddy issues,” but I am very drawn to older men. I love the calm confidence, the grounded, paternal energy, and the way they make me feel cared for and protected.

    What makes it even more special is how beautifully complementary we are. In public, he’s very masculine—confident, composed, and steady. In private, he’s a crossdresser, which he shared with openness and trust. That balance, that shared understanding of gender expression and vulnerability, made me feel seen in a way that’s rare.

    I’m trying not to get ahead of myself—we did just meet—but there was definitely a spark A sense of comfort, attraction, and mutual understanding that felt natural and exciting. We just fit. I’m really hoping this sweet beginning turns into something meaningful.

    http://chrissyinsd.hotviber.com/

    #sissy #sissyboy #sissies #sissyboys #sissygirl #sissygirls #femboy #femboys #femman #gurl #crossdresser #crossdressers #crossdressing #tgirl #shemale #shemalechrissy #sissychrissyinsandiego #chrissyinsd #trans #transgirl #transwoman #transfemale #transgender #lgbt #queer #gay #dancing #twerking #pantyboy #meninpanties #dress #menindresses #gaydate #gayboyfriend #loveislove
    I met a really wonderful man last night 💖 We met at one of my favorite places in San Diego’s Hillcrest neighborhood—Baja Betty’s. It’s a spot I go to often and one of the few places where I feel completely safe being my true self as a trans woman, where I can relax, let my hair down, and just be me. We started talking and somehow time just disappeared. The conversation flowed so easily, and we kept discovering how much we had in common. He’s older than me—I’m 47 and he’s 76—and honestly, it feels kind of perfect. I don’t have “daddy issues,” but I am very drawn to older men. I love the calm confidence, the grounded, paternal energy, and the way they make me feel cared for and protected. What makes it even more special is how beautifully complementary we are. In public, he’s very masculine—confident, composed, and steady. In private, he’s a crossdresser, which he shared with openness and trust. That balance, that shared understanding of gender expression and vulnerability, made me feel seen in a way that’s rare. I’m trying not to get ahead of myself—we did just meet—but there was definitely a spark ✨ A sense of comfort, attraction, and mutual understanding that felt natural and exciting. We just fit. I’m really hoping this sweet beginning turns into something meaningful. 💋 http://chrissyinsd.hotviber.com/ #sissy #sissyboy #sissies #sissyboys #sissygirl #sissygirls #femboy #femboys #femman #gurl #crossdresser #crossdressers #crossdressing #tgirl #shemale #shemalechrissy #sissychrissyinsandiego #chrissyinsd #trans #transgirl #transwoman #transfemale #transgender #lgbt #queer #gay #dancing #twerking #pantyboy #meninpanties #dress #menindresses #gaydate #gayboyfriend #loveislove
    Love
    2
    0 Commentarios 0 Acciones 57K Views