Crossdresser’s Unexpected First Time

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Just want to say firstly, that this story is 100% true. Secondly, it was much better in person. I’m just getting around to writing it after several years.


I’m a 20 year old guy, very good looking, easy to get girls. Brown hair, green eyes and a sexual appetite that’s hardly ever satisfied. I had always had a craving or tendencies towards being a little bi, and had only every played with myself; anything i could use for a dildo from time to time, jerking off to sissy and CD porn. That kinda thing. Almost always though, after I came, I lost interest and went back to being 100% straight. Sound like you? Well let me tell you, just do it. ONCE. And you’ll see that you want to do it again. At least, if you had a similar experience for your first time.

I was living in Charleston, SC at the time (alone) and would drive up to Virginia to see a few girls I knew semi-regularly (like once every month or so). So before i leave for another trip up north, I’m extremely horny, looking at sissy hypno and found myself getting more and more emboldened by it. Now, I had been crossdressing for a few years, so I had a few outfits, heels, a wig, etc. but had never ventured outside wearing any of it. Totally closeted. I went to the shower to get ready and found my razor (I like to keep things totally shaven down below and since I use my ass from time to time, that’s shaved also), but this time I said fuck it. Its winter, I can get away with it, so I totally shaved my legs, face and downstairs. Hey, if any one says anything, I’ll just say I lost a bet. Who cares?

Well as I’m doing this, I again, said fuck it and instead of boxers, I opted for a cute little pink thong and some knee high white stockings (which were on under my jeans and under my socks). I packed a bag full of my girlie clothes (and my regular clothes) and set out.

I’m now just coming up on South of the Border (NC-SC Line) and I notice a car coming up behind me, which was unusual because I was moving along about 80. Not being a complete asshole, I pulled into the middle lane and as the car came up alongside me the driver casino oyna and I locked eyes and he just gave me the head nod and kept moving. Well. I wasn’t about to be shown up, so I floored it and caught up to him. For the next 50 miles or so (no cops thankfully), we were hauling ass, following one another and in general being a couple of idiot kids. I saw him pull over into the far right lane so I was about to make my move to pass him and noticed he was slowing down a lot; too much to just give a casual wave, he was going to take the next exit. Not really thinking anything of it, I just pulled alongside him, going to give him the thumbs up and smile when he looked at me, smiled and did the unmistakeable signal for sucking a cock.

At this point I’m torn. I recognize that I don’t know this guy, I’ll never see him again and I’m already dolled up a lil bit and had been fucking my ass just earlier that day with my 6in dildo…why the hell not now? I’m still horned up, and thinking, its just a BJ and at least you’ll see whether or not you like it, and so I flashed him the thumbs up and nodded and he motioned for me to take the exit with him.

About 10 mins go by of us driving down some small city streets, I see him point his arm out the window signaling to park along the street. I do it and I get out of my car as he pulls into the parking lot of an apartment complex across the street. I follow and he gets out of his car and looks me over with the elevator eyes; hes a good looking guy. I’ve never considered myself able to say “he’s cute”, but I am comfortable enough saying when a guy looks good. He’s about my age, in shape and slightly taller than me. He just says, “lets go hotshot”. And that was about the extent of our introduction. No names, no back and forth banter, no “do you have a significant other” etc etc. It was just, lets get down to business.

We get upstairs and fortunately he lives alone also, and he just says, “what do you wanna do? What are your limits?”

I responded with, “very few, but if you trigger one, I’ll let you know.”

He starts pulling slot oyna off his shirt and tells me to come over to him. As I walk over, he’s still undressing me with his eyes and so I just sit on the couch expecting a BJ. He pulls my pants down revealing my pink thong and his eyes just go wide with surprise, “is this your normal underwear?”

“No”, I replied, “today just felt right…that’s not the last you’ll see also” as I started pulling down my pants revealing the thigh highs.

He smiled and said “my my…today was a lucky day indeed.”

He starts to go to work on my semi-hard cock and to my surprise…nothing. I wasn’t getting hard at all.

Then I remembered a bunch of the sissy hypno videos I had watched earlier and started to wonder if they really had gotten to me after all, and then the second thoughts of “do I really wanna do this” rolled in. I said fuck it, why the hell not and kept going. This time though, I stood up and said, “I want you in my mouth first.”

After revealing his easily 7in cock, which was sculpted beautifully by the way, I took that right into my mouth without a second thought. After I started getting into a rhythm, he started moaning and I started to get rock hard. As it turns out, the more pleasure I gave him, the more turned on I got.

After a little while, I asked him if he had condoms and lube, to which he replied, “no condoms, but definitely have lube.” At this point, I became hesitant. I could just continue sucking this dude off and call it a day after he reciprocates, but again…fuck it “I want it in my ass” I told him.

He didn’t hesitate. I pulled the socks off, the jeans from around my ankles and was just sitting there in my pink little thong and white thigh-high stockings. He flips me around and lubes himself and my ass up and just presses his cock against my quasi-virgin hole.

“Tell me how much you want it sweetheart…”

“I want it bad, I NEED it, fuck my ass”

He pushes into me and its just pain at first. Its just the head that’s in right now and I’m now really re-considering this whole ordeal. canlı casino siteleri I just relax and he starts sliding in more and more and after a few moments, the pain was replaced by pleasure. After a little while of his cock sliding in and out slowly, I start pushing back on it and he picks up the pace. Next thing I realize, I’m moaning like a real girl, getting railed by this good looking dude. It all clicks for me, the stockings, the slutty moans I’m making and this guy just pushing in and out of my ass; my cock had gone back to being semi-hard, but I realize as he’s hitting my prostate that my cock is starting to involuntarily spasm and leak.

As the moaning increases and his panting starts to increase I just unload, cum gushing from me, harder than I’ve came before and all I can do is scoop it up. I have him pull out and I slather his beautiful cock with my own cum as he pulls me in and kisses me full on the mouth. We sat there a second making out and I was just in heaven. He pushes me down on my back and my ankles on his shoulders with my cum acting as our lube and I can feel his body start to stiffen up a bit.

It was at this point that I knew I was about to be bred like a real girl. All I could do was say “fuckin cum inside me baby”.

He starts moaning and saying, “oh yeah sweetheart here it comes…!” As he emptied his balls into me, I could feel every splash and spurt against my insides and all I could do is smile. Finally, I had done it. I was no longer a virgin and I could honestly say I loved every bit of it.

As we both lay there collecting ourselves, I just pulled my thong back on and started to gathering my things. He asked if I wanted to shower or freshen up at all and I declined. I knew I wanted to carry his hot cum inside me until I got all the way to my destination.

After I left, I sat in the car for a minute and just tried to compose myself. Taking a few deep breaths and just thinking about what had transpired, all I could do is laugh and put the car in gear. Once I arrived and met up with the girls, my ass still squishy from his cum, they all noted how I had a different glow about me…

If they only knew…

Since then, I’ve had a few other encounters with men, but nothing that comes close to what my first time was like. Maybe I just need to dress up more often…

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