My first time having sex as a trans woman

So I’m 19 my name is steph, I just came out as both bisexual and transgender and as such I’ve never had sex as a woman nor have I had sex with a boy…

Until last night that is…

I have two tinder accounts, one where I present as a man and one in which I present as a woman, while I understand the duplicitous nature of this you have to admit most people on tinder just want to get there cock sucked and I’m just the guy/girl to do it ;)

Last week I received my first match with a guy, he was a handsome blue eyed guy the kind you figure writes music or reviews old films for a living so we went out and we had a great time talking about video games and politics and comics i like him though I suppose you aren’t here for that:

(The good part)

So we went back to his place and started kissing, my first time with a boy, I nearly ruined my new panties ? however it’s at this point I have to do the right thing and so I tell him “I’m a trans girl, my tits are fake I have a penis” 0he smirks and says “yeah I figured by the tent you’re pitching” (I thought my skirt would cover it up)

“It’s cool if you don’t want to do this”

“I don’t mind, I think trans girls are kinda sexy”

“Would you like to suck my cock?” He asks boldly with i wry smile pressing his thumbs to my lips no doubt admiring there glossy red sheen

“Yes” i whimper as I get on my knees

He stands up before me and unzips his pants and out falls a massive erect cock maybe 8 inches, about twice the size of mine I begim with apprehension and nervousness, I lick it like a popsicle, run my lips across it and kiss it, it tastes like body wash and coconut oil (remember boys and girls hygieneis important) most importantly it’s fucking delicious

I gradually move further, sucking his balls gently, he’s too big to fit it all in and he knows it however I’d regret it if I didn’t try to suck it for real so I wrap my cherry red lips around it, I rub it on the inside of my cheek and against my tongue (fuck it tasted good) and pretty soon he’s ready to finish, he does so on my face and in my hair and on my big fake $150 dollar crossdressing tits

After catching his breath he says that was the hardest he ever came but he pauses…

“But we aren’t done yet starshine…how would you like to get fucked like a girl for the first time?”

I almost beg him “yes, please” nearly crying

After lubricating his gargantuan serpent (taking a lot of lube as you’d expect) he bends me over and yanks my pink panties down “please be gentle” I whisper like a prayer to the apathetic God that is this man’s cock

“No promises” he says as he spanks my ass so hard i audibly yelp “you may be insecure about your body but you have the ass of a woman” he says probing it with what I’d later realize was his finger. It hurts but I shoot up almost instantly he pushes his cock in slowly, everything is on fire and the world goes white as he pumps the agony is indescribable he’s just too big but it feels good for him and that’s all that matters, soon I feel good too he squeezes and tugs on my tits while he pumps, occasionally he grabs on to my erection as though he were climbing everest and looking for a handhold, he says he might cum and i preempt him, painting a streak across his whole bed as he makes a similar canvas of my insides, he pulls out and at that moment regardless of whether either of us want it or not, I’m his

I apologize for the cum stains all over his bed he apologizes for the ones in my hair and on my clothes that I had nearly forgotten about because of how natural they had felt, like it was an intrinsic part of me to be covered in cum, we kiss as I call a cab, and he asks if he’ll ever see me again, I laughed “in your wet dreams pretty boy, no more hookups during pandemics”

“Hey i really do like you…please text me…if you like”

I’m teary eyed this boy likes me for real and not only that but despite spending two hours cumming in my face and railing my ass like a sexdoll he respects me so much he seems shy, i made a guy with like a foot of cock insecure

“OK I will”

Epilogue: my asshole bled and was sore for like 3 days and I had wet dreams of getting throat fucked by anaconda but it was worth it, we’ve been texting each other and are planning to start dating when covid numbers start to go down in the area, it’s going to be worth the wait i plan to wake him up sucking his cock everyday for the rest of my life

Source: reddit.com/r/eroticliterature/comments/mvhai8/my_first_time_having_sex_as_a_trans_woman