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Take The Midnight Tran

This post is also available in: German

Sometimes when you date a girl she drops hints that send up red flags.

“I usually need to get to know a guy before I have sex.”

“I don’t drink.”

“Ew, you’ve done it in there?!”

“I missed my period. Oh, and I’m pro-life and my dad’s a paternity lawyer.”

So it was with some trepidation that I dated this one girl who joked a few times about being a tranny. On our first date I mentioned I liked her artsy shoes and punk makeup and she said “Yeah, I bet you think I dress like a tranny.” OK, that got me concerned. I looked more closely at her shoes and face and wondered if it could be true. She didn’t have a low voice but I’ve read about cosmetic vocal cord surgery for old people who want to sound younger.

The second date we were making out and groping and I reached down and ran my hand under her skirt and near her pussy, hoping to put my worries to rest. She gently pushed my hand away, smiled, and said “Are you checking if I’m a tranny? Naughty.” Now I was really freaking out on the inside. When people blurt out weirdness more than once it is a sign of them hiding something. Could she really have been a man in her past? Was I going to have a crying game moment? She didn’t look like a tranny, but with the state of medical science these days you can’t take anything for granted.

Between the second and third dates I dwelled heavily on the possibility that she might be a guy with one operation to go, or a former guy with a butchered fake vagina constructed out of sheep intestine. A few sleepless nights passed. I googled “transsexual dead giveaway” for information about warning signs. I contemplated not calling her back. Nope, I had to see this through.

On the third date, sex was the farthest thing from my mind. I was concentrating hard on inspecting her head to toe for traces of maleness. Again, she let slip with an awkward “joke” involving the word tranny. Mentally, I was a mess. I thought about how she walked with this loping bouncy gait. And how she had these exaggeratedly feminine gestures in the way she sat down and crossed her legs very slowly, and how she carried her purse dangling off her forearm with her elbow bent at 90 degrees and her hand turned upward, palm out. Oh my fucking god, that’s what trannies do! Then I remembered… she was always paying me blatant compliments about my physique. Girls never do that on the first couple of dates, even when they are completely into you. 100% tranny. 100%.

The squirrel in my head was running frantically on his wheel.

Still, she looked pretty good, so I started french kissing her. Gradually, I moved my mouth down and kissed her neck. I began probing her throat with my tongue. This aroused her suspicion. 

“What are you doing?”

Think. “Mm, I love kissing your neck. So smooth.” Like a giraffe reaching out for the highest succulent acacia leaves, my tongue pressed around the area where her Adam’s apple would be if she were a man. I detected nothing. Phew! Or did she have it surgically removed? I pulled back for a visual examination. No scar. Phew again!

Occasionally, I would stop and stare deeply into her eyes, but what I was really doing was getting in close to see if she had the shadow of a mustache or a missed spot of stubble. I wondered if apn entire beard could be lasered off. No, her face was hairless and of an even coloration. Another test passed. I glanced at her forearms. Also hairless. So far so good. I gripped her hand; she gripped back. Not too strong, it was an appropriately weak girly grip. Feeling better. I moved my hand under her shirt and burrowed under her bra. This was the first major test. I squeezed and kneaded like I was giving her a breast exam. Then I pushed aside her bra and pinched a nipple. It got hard and pointy. There’s no way a fake tit or hormone replacement could do that. I was confident enough to move to the final stage.

In the bedroom, I lit a small candle. I would need some light to work by. Best to get this over with quick. I maneuvered my hand up her skirt and placed it on her crotch. Her panties felt thick, padded. A rush of fear. Was s/he tucking? For the first time in my life I prayed that a girl I was about to fuck was on the rag.

This was it. Crunch time. No turning tail now, I had to know. But the risk was huge.

Other than blowing out my ass with explosive diarrhea in public while wearing white linen pants, I can’t think of a more psychologically scarring scenario than reaching into a girl’s panties and grabbing a schlong. I had already made up my mind to soldier on because I calculated that the regret of giving up sex with a girl was worse than the regret of having near sex with a man.

Off came her shirt. A muscular back. Stay focused.

I pushed her backwards onto the bed and pressed into her pelvis. Nothing rose on her to meet my erection. Do or die. I closed my eyes, grit my teeth, and ripped off her skirt and panties and in one mighty uninterrupted motion plunged my hand into her furrow.

Labia. Wet. Hole. Wet. Clit. Wet.

A wave of relief swept over me. I pried my eyes open and smiled warmly at the authentic vagina before me. A short sniff of my fingers confirmed the presence of natural juices. No lube.

Afterwards, she snuggled in my arms and belched. I dumped her a week later.

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