Nailing [M]y First Crossdresser- The First Date [M][M]

[Pending how this is received, I will happily provide a follow-up of the second time I got to meet Toni. I thought perhaps that a burgeoning sissy may see this and feel a bit inspired to hear about an anon meet from the other side of the equation. I’ve added a bit of narrative for effect, but 95% of it is true to the best of my (rather high) recollections. For your consideration, I present an overly-detailed account of my first time nailing a crossdresser]
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I can still taste her tight little ass whenever I think about it. Or, more accurately, his tight ass, but when you’re fucking a cute bubble-butt thats so tight and tasty, does it really matter? To this day, the smell of coconut oil takes me back and I can still feel the faint patter of what has to be tone of the top five most intense orgasms of my entire life. Fuck, I came so hard that it makes me hard just to remember how hard I came.

Most happily married men, let alone happily married bisexual men,  would never get a shadow of an opportunity to do what I was able to. Deciding to open up our marriage to have the experiences we’d always wanted,  I found myself on FetLife looking to answer some questions about myself that I’d been curious about for a long, long time. Casting a wide net (i.e. chatting up as many local gurls as I could), I found a tattooed beauty who we’ll call Toni that was filthy in all the right ways with a profile full of pictures for me to drool over. She was a bit older than me, but sissydom isn’t limited to just the waifish girls that you see plastered over most good porn sites.  What started off as an innocent icebreaker of asking what she was into (a simple message really) escalated when she responded back with “I like sitting on your face while you eat and tongue fuck me, all while I stroke your cock and watch it shoot all over”

She had my absolute attention, every bit of it aching and throbbing. My chest fluttered at the possibility while I pawed through her pictures. She was hung. She was so fucking hung. 8″, and decently thick too but not overly so. A small vein ran up the length of it, like a highway for my now-watering mouth, and with a nicely sized head to top it all off. Shaved smooth and bare far beyond what I could have ever hoped to achieve, her ass was a thing of beauty. It was a cute bubble-butt, pale and full, complete with an invitingly pink little hole. But what really got me was just how inviting her ass was and just how much I wanted to worship it when I imagined it on my face.

I replied near instantly, wasting no time in trying to find out more. We went back and forth, my cock achingly hard each time I heard a notification. It was distracting, to say the least. Working from home has its benefits, and being able to freely whip out my cock and edge to pictures, texts, and videos is amazing. I took full advantage of that freedom with Toni. Finally we settled on a day and time, a nice Thursday start to a trip downstate. I put together a small gym bag with the essentials, packed a vape near full to bursting with some excellent bud, and counted down the days.

I was nervous-it wasn’t my first time with a man,  but it had been a long while since my last encounter. I also, admittedly had never rimmed someone before. I try to give new things a go,  and I figured that maybe I’d like it. [Spoiler alert: I did]

Finally, it was the morning of. Toni had worked a night shift, and used that morning to prepare- a bubble bath, a joint, and a fresh shave. As for myself, I drove the entire way with bated breath, excited and nervous, imagining her from every pic I had seared into my memory. The then-illegal weed I had on me didn’t help calm the drive either, in retrospect. As I neared, Toni gave me her apartment information and before I knew it, I was there. She was fashionably late, and I amused myself with some saved Aubrey Kate videos in the apartment complex’s parking lot (sidenote: that woman makes whoever is eating her ass *make* them love it!). I went up each stair with excitement and I think she must have heard me, because a cracked door and dark hair greeted me as I made the third landing.

I stepped inside, and took off my shoes. It was dimly lit, and Toni kept her face tilted to the side so that I couldn’t get a good view of her. She sat down, and offered me a hit of her joint. I took her up as her hand gently toyed and rubbed at the front of my pants, still keeping her face just out of sight. I smoked a bit more of my own stuff, mistakenly looking for a stronger buzz. As she stood and started to grind her ass against me, I knew it was showtime.

The mystery of her face was overshadowed by the feeling of my hand sensuously touching her ass and the growing bulge in the front of her dark blue denim skirt. Her black thong panties were silky under my fingers as I gently stroked across her warm and firm bulge. And they were a perfect match for the black thigh high black socks that I nearly felt my mouth water for.

We moved to the small living room area, in front of  a big TV with some killer porn, the moaning just a bit faint in the background. She was trying to stay discrete and keep her neighbors from talking. Wordlessly, Toni lay down on her stomach, spreading her legs out behind her and wrapping her tattoo’d arms up and under her head . She wiggled her ass enticingly.

One of my biggest turn-ons is body worship. Running my hands along skin and reveling in the sensation is such a pleasure when you’re high and enjoying some good, high sex. She placed a bottle of coconut oil next to her and murmured “Use as much as you want Daddy”. While my head flashed to her entire body slicked with oil, I drizzled just a bit over her back and beautifully inked arms and legs. I let my hands go to work, sliding along and pressing in. I brazenly worked my way to her ass and spent a good, long oil-y while massaging every part of that beautiful sissy princess’s ass that I could lay my hands on, eventually parting her full ass cheeks with my thumbs and began to gently tongue her tight little hole, getting more and more into it.

Eventually, I was slobbering away in her ass like I had been starving. And Toni loved it- little sighs and groans, begging Daddy to get in deeper. And I obliged.  She popped up on her knees so that I could eat her ass even deeper, and I started to gently toy with her dangling cock, stroking it up and down slowly. It had been far too long since I had laid my hands on a cock, let alone one as big as hers. She had lied in her pictures- her ladystick (as she called it) was massive. 8″-9″ easily, with a beautifully thick head. Coconut oil was slicked all over my face from my mid-morning snack, and I poured a bit more on my hands and started working her cock, enjoying the way the skin slid along rock hard firmness below, to say nothing of the feel of the oil.

I eventually pulled away from tossing the hell out of her salad, and lay on the floor so that I could taste more of her. Now, I could say that I sucked her cock excellently, like the world’s most talented pornstar. But I didn’t. I had never done it before, and fumbled like the worlds most inexperienced virgin. I could barely get her into my mouth, and when I did, my teeth spoiled any streak. Still, I persisted, and I’d like to think I approved judging from the gush of precum that erupted in my mouth. It was delicious, but she pulled away so that I could eat that delectable pussy again while she jerked her cock a bit.

Here’s a lesson kids- kief kicks hard and (for me, at least) dries your mouth out something awful. I had to take a break and grab a sip of water and swish some Biotene I had brought with just for this very case. In a small fit of anxiety (I think brought on by a mix of being hungry, caffeinated, horny as fuck, and high as giraffe pussy), I tried to make an early exit. Having a moment to breathe in the middle of it all allowed for me to clearly remember that I was here to fuck this sissy princess.  I say this because, to anyone reading this, its OK to have anxiety about anonymous sex. Take a moment and breathe She asked huskily if I had brought any condoms and I gave a very pleased “Oh fuck yes I did”.

I laid back down on the blankets she had strewn on the floor.
She flared her skirts up so that her ass was easily accessible (I had long since discarded her cute black thong with a pearl-type of string as the thong portion) and took a hold of my cock to roll the condom down. I’m average sized, nothing terribly impressive but it gets the job done. I figured that for most gurls it was the perfect type of dick for anal, or so I hoped. The fact that she was hung like a horse, compared to me, was a big turn on for me. Once the condom was on, she put her knees down on either side and all but told me that she wanted to ride reverse cowgurl. Toni was in total control, and I lay back and enjoyed her work. She was tight but she took it fairly fast and before I knew it, she was bottomed out and groaning heavily. It was firm, like a tight fist with a very strong grip around where I was currently impaling her and as she began to ride, I lay back in bliss. When I’m high, I love to take in the sensation- which, unfortunately means that I couldn’t call her all the filthy names that I had floating through my head.  There was even one point where the squelch of lubricant began  to synchronize to her small moans and groans.

But all good things can’t last forever, and Toni was hungry for cum. She dismounted off of me and pulled off the condom, all the while putting her ass back within range of my mouth. The angle was weird, so I couldn’t quite eat that pussy quive as voraciously as I wanted to, but soon enough her skillful mouth had me distracted. I was close while she riding, but I now found myself riding one of the most longest, most ball-draining orgasms ever. I swear to you I saw stars from that sissy princess’ mouth, and while my view was taken up by this crossdressing beauty’s ass, I had to have been shooting ropes in her mouth. She did pull off and I felt more splatters on my legs. She cooed “Oh yes Daddy, cum for me” and massaged my legs, licking it all up. After catching my breath, I couldn’t leave her hanging. Both of us wanted to cum, and I most definitely wanted to see her finish. Her hand started to pump and she stroked that magnificent ladystick until eventually dropping a substantial load on my chest, warm and thick.

We cleaned up, neither having much to say to each other now that we had both gotten our appetites slaked (or, at least, I had- I like to think that she had another cock inside of her afterwards because who doesn’t love a cock-hungry slut). She opened the door and I stepped out with a playful smack on my ass. I did have the privilege of meeting (and eating!) her one more time after, which was an even better fuck. I won’t bore you with the mundane details afterwards, but being balls deep in a crossdresser’s ass set off a special admiration for the hard work that sissy princess’ do for lucky men everywhere. Of course, don’t write off the older gurls either- there’s experience there that ages extraordinarily well. 

Source: reddit.com/r/gonewildstories/comments/ndz6v6/nailing_my_first_crossdresser_the_first_date_mm