Andy Miles (6:45)
People always ask me how I knew I was trans. And it started with somebody calling me daddy. I was lying in bed on a Sunday morning after an epic weekend of sex, and my lover whispered in my ear so quietly I could barely hear it. Can I please suck your cock, daddy? And my whole body went electric because nobody had ever quite done that before. But let me back up a little bit before that happened. It's 2014. I had just moved to San Francisco, just met Dixie, and I was so excited because this is a nerd wonderland and a sex wonderland and a sex nerd wonderland altogether. I moved here after being out and open as a queer, poly kinky, bisexual woman in an open marriage in Atlanta, Georgia. That was a little bit rough. So I got here, and I got the job first before my husband. So I moved out, and I was exploring everything on my own. There was sex education training, so I went and did my certification through Spicy. Met lots of friends there. I learned to explore all the things that I liked. I learned that my fist could fit inside another human, and it was amazing. I remember being with this gorgeous tattooed woman who was a crossfitter, and she tasted so good. And I was putting in one finger and another finger. No gloves, no lube. She was just that juicy. And when my hand slipped all the way in, I thought, oh, it feels so good to have her squeezing me. After that, I called my husband, who was still in Atlanta at the time, and said, hey, our wedding ring has been completely immersed in this amazing human. I'm so excited. He said, tell her welcome to the family. So I'm discovering the fisting. I'm discovering my sex ed training. I start going to sex parties and loving them. I start becoming a sex party facilitator and producer myself. And along the way, I also realize that I love fucking guys in the ass. So I buy my first strap on harnesses and my first dicks, and I'm playing with the boyfriend of one of my lovers. Because this is how you meet people, you know, like friends of friends, partners of partners. And after we're done playing, he looks up at me and he says, you are like a cross between a mad scientist and daddy. And I'm like, cool. I don't know what that means. I'm new here, but that sounds nice. So after some months, my husband Raj actually moves to San Francisco with me. We're not long distance anymore, which is great because when we got married, we promised to be nerds together forever and have adventures large and small together for the rest of our lives. It's actually engraved on our wedding rings. Nerds together. It's not the date or anything, it's just like, oh, we like to learn things together. We have book dates where we read books about all the things we're interested in in bed. And lots of those books are sex books. So he's here and I start introducing him to all the people. I introduce him to Dixie. We have hosted body storytelling rehearsal at our house for many years. And I start bringing him with me to parties. And we find ourselves at this party at a beautiful warehouse in Oakland. So this warehouse, it has big brick walls, tall ceilings, really beautiful, spacious floors. And I walk into this party, there are about 30 people arranged in a circle seated on cushions. And the organizer, who's this 6 foot tall blonde who's huge in terms of energy, is a former football jock, but also a teddy bear. He is pulling everybody together in this Northern California tradition of a welcome circle, which I love. It sounds so kind and wonderful. And it's a way to get people connected with each other so that they can fulfill all of the desires of their perverted little hearts. So one of my favorite parts of the welcome circle is the question, mildest and wildest. It goes like this. What is the mildest thing that could happen today at this event that would leave you with a huge grin on your face? Think about that for a minute and then ask yourself, what is the wildest? And go do that. So we're going around the circle. People are talking about their mildest and wildest. They're people of all genders and orientations. There are lots of lesbians with new dicks. And I'm not a lesbian, but I am a queer woman. And at this point, I'm showing up to the party in this form. Fitted red Ann Taylor dress that hits just above the knee and like calf high leather boots. And for context, I have huge breasts. I wear a 34F at the time, so I'm like fierce, hard, femme queer woman with short hair who also presents butch sometimes, but hella queer in whatever way you say. And I say, I too have a new dick today, and my wildest desire is for some guy to give me a blowjob and then let me fuck him. As I say this, I make eye contact with a beautiful stranger from across the room. He is maybe 6 foot, looks like an Elvis with really manicured sideburns and really bright blue eyes, full cheeks. He sees me make eye contact, his eyes get really big, and he grins like a kid on the first day of school and is like, huh, huh, huh. So I have my partner for this, and before we know it, you know, I go over, talk to him and he says, apparently his name is Jason, he lives in Sacramento, he's visiting, and he really likes giving blowjobs. He really likes getting his face fucked and slapped around, and he's very much looking forward to having my dick sink into his ass. So before we know it, he's on his knees in front of me and he is so lovingly appreciating my brand new dick, taking it slowly, making sure to caress all of it. For those of you who aren't familiar with the many options available for dicks, thick skin dildos are the best. They have a firm inner core that is silicone and a more squishy outer layer. And what that means is it feels pretty realistic to the touch. It maintains body heat, it always stays hard. It can't get anyone pregnant. There are all of these wonderful, wonderful things about it. So he's taking this slowly and appreciating the veins and the ridges and just treating it beautifully. And then he's taking it more as I thrust. And then he's really enjoying it when I start slapping his face around. And then I basically flip him over, find a mattress, and say, it's time for you to get fucked, honey. And he says, oh, can you use my dick? And I'm like, oh, well, I mean, I guess I can swish it out. It's detectable. It's really useful, it's handy. So I switch it out and he has a very, very small one. And I fuck him. He enjoys it. We have a lot of fun coming together. And then he says that he really wants to keep in touch because this was fun. Raj is there at this party, and I was like, hey, it looks like you had a good time. You're going to follow up with that guy? I'm like, yeah, definitely. So I follow up and we start seeing each Other on the weekends in Sacramento, whenever I have a chance to go along the way, I know that I really like getting blowjobs, and I know that I really like fucking guys in the ass. And at least one person has called me daddy, but I don't really know what that means. And I start through all of this to also meet lots of gender bending people and lots of trans people. And I start dating some. And they all ask me, have you ever played with gender? Have you ever thought about this? And I say, well, no, not really. And then one of my lovers has top surgery. And I find myself instantly jealous because, well, I'm not sure why is it that I want a flat chest? Is that I want the feeling of a T shirt against my skin? I'm not really sure, but I'm jealous and I want that. So I start to ask myself, huh? Like, does that. Does that mean that I'm a man? Or does it just mean I want a flat chest? And then I'm like, well, I really like how he looks in a T shirt. And I also like it when butch dykes look like that in a T shirt. And I also like it when all kinds of androgynous people look like that in a T shirt. So I start buying all these men's clothes. I buy T shirts like this one, but they don't look right on me because at this point, I still have a 34F chest. And I'm very frustrated, but I don't know still what it means about gender. And I'm just having all the sex that I can have in the meantime. So one of these times, I'm on the train on the way to Sacramento to visit Jason, and it is a Friday after work. I have spent all day at work with my bag full of, like, bondage tape and dildos, hoping that it doesn't spill out of my office bag. And I've been anticipating how pent up he's going to be because I have instructed him not to come since Tuesday so that he will be ready for me when I get there. And we get there, we can't keep our hands off each other. We must have eaten food and slept at some point. But all I remember for this weekend is fucking and fucking and fucking and coming and coming and coming up until that Sunday morning. That Sunday morning. By this point, I've already identified that I want a flat chest. I've already identified that I want T shirts to look dude like on me. But I don't really know anything else. And we talked about it but at this point, my pronouns are still they and she and I don't know much else. It's this Sunday morning, and Jason whispers to me, can I please suck your cock, Daddy? And I say, yes. And I think that he is going to want me to go put on my harness and. And my dick, but he doesn't. He just pulls off the sheets and starts going down on me. He starts licking me and sucking me with no extra equipment. He says, I love feeling your cock at heart in my mouth, Daddy. I want you to come down my throat, and I want to swallow, Daddy. And at that point, I felt. I feel like maybe I do actually have a dick attached to me that I was born with. It's a total and complete mind fuck. And I come really hard. And then I tell him that it is very, very much now time for him to get fucked again. And I pick him up and move him into his sex sling, which is one of my favorite features of his house. It's this beautiful leather sling with metal chains attaching it to the ceiling. And I cuff his right ankle and his left ankle and his right wrist and his left wrist. And then I tie up his cock and balls for good measure because I know that he's going to want to touch himself, and I know that he is going to wish that he had more movement there, but he will come much harder if he has to wait. So I have him tied up and I go back and put on my favorite Vickskin dick with my favorite brown leather and brass harness. And I start slowly teasing him and. And fucking him. But this time I imagine that I actually have nerve endings in that dick and that I can feel his ass squeeze me as I'm sinking into him, and that I can feel myself get harder as I thrust, and that when I come, I'm actually coming into him. I do that. I pound him the way that he likes, as much as he can take it. And then I give his face a few slaps and a forehead kiss and say, you did a great job. And I untie him and then ask him to fuck me. And as I do that, I move to take off my harness. He puts a hand on my arm and says, you don't have to do that. And I said, well, what do you mean? He says, I can fuck you while you're still wearing that. And I was a little bit confused, but went with it. He puts on a condom, slides his dick into me, and then with his right hand starts jacking off the dick that I'm already wearing. And tells me that he loves sinking his dick into my front hole. New word. Like it? It's great. And jacking me off at the same time and telling me he wants me to come in his hand. And then he takes his left hand and puts it on my sternum and says, you have a beautiful chest, Daddy. Nobody has ever referred to this as my chest. Not while I still have big boobs like that. I feel so seen and loved and cared for in a way that I didn't even know how to ask for. I had not conceptualized myself as a man, but he saw me in that way, used male pronouns and terms for the first time, calling my chest, my chest, my clit, my dick, my vagina, my front hole. And as we wrapped up there, I just. I held him and I cried and just said, thank you. I didn't have any more words at that point. And then it's Sunday morning, and I live in San Francisco and we're in Sacramento, and so I have to get back home. So I'm going back to the Amtrak, and I go to order a coffee at Starbucks and the barista calls me ma'. Am. I'm instantly snapped out of it. And my first reaction is like, wait, what? This is crazy. I'm obviously a dude. Can't you tell? You must be delusional. And then I look down and I see my chest. At this point, when I look down, I cannot see my feet because my tits are literally out to here. And I just feel crushed and alone because if this person can't see it, then nobody can. At this point in the world, it is only Jason who could see the man in me. And me. So I'm getting on the train, going back home, and I'm crying because I am married to a straight man. I am married to a straight man who, on our second date, when I came out to him as bi, said, oh, thank God. I said, what are you doing? Excuse me?