Fucking Femboys in Transit

This series is an anthology from the POV of lucky perverts on public transit. Each story in this series will be a different pervert and femboy.

I was sitting on the subway. My girlfriend, Abigail, had just dumped me after blue-balling me for weeks now. I thought last night would be the night she'd finally give it up but she decided to cuddle me to sleep again, then broke it off with me this morning during breakfast. No wonder she didn't want to fuck me. She's probably been taking it from some other dude.

The train began to get crowded and I noticed a leggy blonde in a cute skirt had stepped in front of me, being pushed up against my seat somewhat by the crowd. Listen, I'm a guy, and I was sooo horny after weeks of being shut down... so I let my eyes trace up her shapely legs, muscular but not in a gross masculine way. As my eyes reached the bottom of her skirt I began to will the sex gods to create a miracle that would allow me to see her pretty panties underneath. I'd love the jerk-off material later. But as I sat there, all but drooling like a total simp, my cock getting a little heavier, I hear a throat clear, pulling me out of my perverted trance.

I look up at the woman whose legs and skirt I had been eye fucking for the past few minutes, to discover that she's looking at me. Her mouth tilted in a light smirk. Her arm was reaching up and grabbing onto a safety strip so I couldn't help but allow my eyes to travel from her shapely lips down to her gorgeous figure, and now exposed midriff.

DAMN IT. I snap my eyes back up to her face. She smiles then as a man bumps into her from the other side she stumbles closer to my legs, practically straddling them, legs on either side of my knee. My cock jumps and I look at her again. She's biting her lip.

She reaches down her skirt and begins to do something out of my wet dreams. She begins to tug up on her skirt slightly, not a lot, but enough for me to catch a glimpse of the sexy pink panties before her skirt falls back down. YUP, I'm definitely firming up in my pants now. I use the heel of my hand to push down on my thickening cock as I stare intently at her skirt then back up at her. She smiles then pulls up on her skirt again, but this time she pulls up a little further... holy shit I'm about to have a heart attack when I realize there's something a little different about the topography of her panties... a definite peak instead of a valley. My eyes must convey that I'm completely caught off guard by this "woman's" tiny dick and balls inside her panties because she drops her skirt rather quickly.

Now I've always considered myself straight. Yeah, there are some dudes here and there that I thought if I were to experiment then it would have to be with THAT type of guy and I'm not homophobic but I've never actually considered doing anything with a guy, let alone got hard from one.

She backs up off my leg, looking nervous, like I might be angry at her. Right as she began to turn away from me, though, a make a move that I'll later find out would change my world entirely. I grab her leg to keep her from trying to move away from me.

She looks back at me, a confused glint in her eye. I heel my hard cock again so that she can see that her sexy little cock didn't turn me off. In fact, I have a primal urge to dominate her with my much larger cock now. She stumbles back. Now straddling my leg like she intends to sit on it. DAMN, this is hot. How can a guy have such a bubbly ass?!

Back when Abigail and I had first started dating she was a total slut for my dick and took it any way I'd give it to her, including the ass, so I'm definitely not averse to ass play, and this dude/woman (IDK her preferred pronouns but whatever she is she's hot) has a ripe peach.

She looks back at me. My hand is still on her thigh. She wiggles her ass a little, like she's leaving the ball in my court, so I immediately shift my hand around and up her skirt to grab a handful of firm ass. What I find there has me biting my lip to keep a groan in as my eyes shoot wide again. This girl's panties are assless... just 2 straps connecting the crotch to her waste band, kind of like a super feminine jock strap. I grope harder.

She arches her back a little, encouraging my totally pervy actions so I begin to massage her ass cheek, my thumb moving further towards her hole... because god help me, I want to see and feel every inch of this delicious ass. So I glance to the side, thank god I have a partician near me on one side and on the other is a group of friends chatting in a circle, the one sitting is faced toward them, not paying attention. I immediately lift up her skirt and spread her cheeks to take a quick peek at her hole... mmm pink and hairless... I dive in and lick the pucker quickly before allowing the fabric of her skirt to drop. She jerks in surprise but doesn't move away from me... so I begin to use the spit to push my thumb into her pucker... only to find that its already got lube inside of it easing my way.

I grab her by her hips and pull her back onto my lap. I whisper in her ear as I roll my hips and press my rock hard bulge into the crease of her ass. "Did you come on the train intending to get fucked or did you just come from getting fucked and that's another man's jizz in your ass?"

She uses her hand to push down on the small tent in the front of her skirt... mmm... my little lady boy is hard... "I wanted to get fucked. I like showing off my body in public." she said back. Only maybe I should say "he" since this bombshell of a woman had a more masculine voice than feminine? I guess it really doesn't matter at this point because I'm way too close to blowing a load either way.

"Can I put it in?" I ask as I roll my hips into her again.

"Fuck yes, I want your cum"

"Oooh, are you a little cumslut?"

"Yes, I like being used. Do it quick and I'll go home and jerk myself using the cum from my ass."

Damn... This dude's a fucking wet dream. I decide to hurry up before I lose such an obvious gift from the sex gods. I use her skirt to cover me as I pull down on the wasteband to my joggers, my cock now in direct contact with that sexy crack. I use my thumbs to part her ass cheeks as she lifts up slightly then I aim for that sexy, wet pucker and push up slightly, trying to take it easy, but she slides down quickly, leaving me seeing stars. God this dude must play with his ass a lot, it's trained to take a cock. I start pumping into this fine peach as subtly as a I can at first, until I can clock my surrounding and ensure I'm safe, then I begin thrusting into her faster and harder. At one point I feel her jerk and hear her moan, and with what little I know about the prostate I figured I may have hit it so I try hard to keep hitting that same spot.

I realize that fucking this guy's prostate and thinking about his hard little cock is making me more hungry for my release so I reach around (under the skirt) and start to jerk his sexy little cock.. just touching another guy's dick for the first time while his ass is clamped hard around my dick has me gushing my load deep in his ass, feverishly pumping weeks worth of blue ball, thick cum, deep in that tight, wet hole. As my wits begin to come back to me I realize I have something wet on the hand I was using to jerk him off with.... cum... he came in my hand...

I look up at him. He looks back with a dazed, wrecked look. "Fuck that was hot" he said.

I raise my hand up to his mouth "lick it off"

His eyes sparkle and he begins to lick his own release off my hand as my cock twitches inside him. "Mmm, I'm still going to keep your cum in my ass and use it as lube later" he says, clenching down on my dick before slowly popping off, keeping as much cum inside him as possible, and giving me time to pull my joggers back up over my cock which is at about half mast now.

"Damn, can I get you number?" I respond as he continues to sit on my lap and adjust himself under the skirt. "I can give you plenty where that came from whenever you want."

He stands up, reaches down, and grabs my phone out of my pocket. I unlock it for him, and he types on it for second then hands it back... Liam... His name is Liam. I save it quickly. "My name is Scott. I'll shoot you a text."

He smiles sweetly before hopping off at the next stop.... and that's how I drained my balls for the first time, but definitely not the last time, while on public transit. Liam and I got very well acquainted after that day.