My [F] first tranny [TF]

There’s a tranny chaser up in here…

It’s me. I’m the tranny chaser. My entire sexually-active life I’ve had a very distinct interest in all things gender bending, androgynous, trans, drag, and cross dressing. I know very specifically what I’m into and it’s hard to make the stars line up in my favor. But, it finally happened. She contacted me as her male self on Plenty of Fish, which on my profile states I’m into TS/CD so she felt comfortable telling me right from the start she was a cross dresser with interest in going full-time. I’m feeling it. I’ve had men approach me before that cross dress in the bedroom, just lingerie and panties… that’s not my deal. I mean, I like those things too, but I want it to be more than just a sexy bedroom activity. Like fisting, or crying about my dead father.

When we hooked up the first time, she was a he. It was good, it was fun, I had many orgasms. Hanging out was cool, too. She’s cute as a dude haha. She tells me what caught her attention was reading through my blog and seeing I mentioned liking the band Jimmie’s Chicken Shack… it’s weird how music can bring people together, right? Rufio totally tuned in to my channel when I sent him a link to MY SONG. So we make the plan for her to come over and let me do her makeup, she’ll dress up for me. I want to see her as herself. Her true self. It was hard for me to even really picture her as a her, with her beard giving her a gruff appearance. But, I’m all in. I want this so bad I can taste it. Chicks with dicks is the best of both worlds. She visited my bitchin’ drag queen friend who works as a makeup artist, the one and only Anita. Twat. Then she sent me a pic with her face painted and I immediately melted. I must have her. I wanna sit on her dick while I braid her hair. Look, this is just as confusing for me as it must be for my parents. Thank god my dad died before I started bringing he-she’s home… I’m actually unsure if that’s better or worse than the darkies. Whatever, I was written out of the will years ago; the freedom is exhilarating. I’m on spring break.

The big day arrives, a Thursday, and she finally makes it over right as the previous week’s episode of RuPaul’s Drag Race All Stars is beginning. Perfect background stimuli while I put my tranny love in some paint, if I do say so myself. I fucked up her eyeliner and called a time-out for a redo. It’s distracting trying to put makeup on someone while you’re also uncomfortably aroused. Ask Buffalo Bill. It’s done, it looks good. I watched Alaska Thunderfuck5000 get crowned. I’m not surprised in the slightest. Lady Love excuses herself to go change, while I put away my supplies and dick off for what seemed like an eternity. Jesus what is she doing in there? When she comes out as herself I felt my jaw hit the floor like a cartoon. She’s beautiful. The kind of T-girl I’ve always wanted. Also I kind of fangirl’d over her boots for a hot minute, because the bitch has style. I can feel something happening in my face… what the shit is that… my eyes are welling up? Fantastic. I’m standing in front of one of my ultimate fantasies and I don’t know what to do with my hands. I can’t speak. I can’t breathe. I’m nervous!? HOLY SHIT I’M NERVOUS! That’s a rare feeling before sex. This is where I cross my fingers and toes and just pray to whoever’s listening that I don’t get scaredy farts.

I lead her to my bedroom and continue to just marvel at her. I’m in awe. I’m on my knees on the bed, she’s standing in front of me, I can’t keep my hands off of her. I feel the shapewear she’s got under the dress, like body armor. When I get cinched into my corset I feel invincible. Punch me in the kidneys, I can’t even feel it. She’s getting anxious to get down to business… I need to shake this nervousness off and fuck her like an animal. I don’t know how to make the first move and my stalling is becoming apparent. I finally get exactly what I want and I don’t know how to proceed… it’s kind of like that one Joker quote. Whatever, fake it until you feel it. Time to pounce. She’s laying back on my pillows, boots still on, everything still on. I straddle her and kiss her. My tits in her face. I put her hands on my ass as I grind down on her. I hop off, take off my panties, take off her panties, and climb on. I just pushed her skirt up and mounted her. I should stop here to tell you how the exact moment she was inside me, I turned into an animal. Hold her hands down and take every inch of her. She starts talking dirty to me and I’m losing my mind.

For once in my kinky freaky life… I wasn’t the one yelling TAKE THIS TRANNY DICK! Color me excited. She gets on top, still in full lady clothes and undergarments mind you, and starts plowing me like a maaaaaaaaan! She’s asking if I love her “girl cock” and what can I say other than YES, FUCK YES, FUCK ME HARDER! Right? She’s putting my legs in various positions, she’s bending me over, she’s fucking me on my side. Her wig is getting fucked up. She’s burning up in her dress, lacy undergarments, and other such things. Fuck it, we don’t care. KEEP FUCKING ME YOU BEAUTIFUL MESS! We get naked and continue to slam into each other for what could only be described as hours. I needed a thorough dickin’ until my legs shake and I can’t form sentences. You know, for a sissy she sure does fuck like a beast. I brought her to orgasm 3 times total, and I lost count of mine before she took charge. Though she’s not exceptionally endowed, she’s long enough to hit my spots just right and she knows how to work with what she’s got. That’s a talent. I’ve come to realize the perfect dick for me is about 6.5 inches long, and as fat as possible. With fucking and getting fucked by QuarterRican semi-regularly, we often use the smaller dildo attachment as opposed to the 8inch or above; you can get down meaner and rougher with a little less, because you’re not punching the cervix like whack-a-mole game. Maybe if my vagina wasn’t as shallow as the rest of me I’d be more open minded to the monster cocks flying my direction, but for now it’s working out preferring average-ish lap rockets. I can enjoy nights like this fully satisfied. And I was.

The last time she came I fell over and tapped out. I was done. That was that. She wanted to go “round two,” and I had to gracefully, exhausted, wave her away. I’M SORRY, LADY LOVE! I bring shame upon my famiree. She even had to work early in the morning, and it was 1 or 2 already. Hold up, wait a minute, I tapped out. I TAPPED OUT! I was so blissfully content. I’m dreary and sticky and the bed is wet from cumming everywhere. I’m sleepy. The insomniac is fucking sleepy. My ultimate fantasy complete, I’m going to sleep like a child extra on the Cosby show. She tells me she wants QuarterRican and I to tag team her with strap-ons next time… and she wants to tag team me with QuarterRican. Oh lawd. What did I do in a past life that was so good I earned this? Sign me the fuck up. Since this encounter I’ve ordered and received new steel boned corsets, I’ve supplied myself with new restraints and equipment, and I’ve started to frequent the one and only Alaskan BDSM sex club. QuarterRican wants to pack the strap-ons and fuck some butts on a Play Party night. I may or may not be excitedly encouraging the club owner to throw a Pegging Party. Let’s get weird Anchorage, Alaska! I am in you.

If you’d like to read more of my stories, my blog is called All The Dicks, and this story specifically has hyperlinks in it. Thank you for reading! This was a blasty-blast!

Source: reddit.com/r/gonewildstories/comments/59kdsk/my_f_first_tranny_tf