My Second First Time

Story by ParamountYak on SoFurry

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A sweet natured piece of erotica about a transgender cat's first time with another woman as a woman. From a writing prompt I was assigned "First Time as a Girl".

I struggled with whether or not to write this because, as a cis man, I know that with the best intentions I may end up fetishizing trans people. I want to write about an arousing sexual experience that others can enjoy without putting an emphasis on trans bodies and accidentally become dismissive of trans lives. However, as a writer I do feel a certain commitment to diversity, and if called upon (this was a writing prompt from a transgender woman) I want to write about transgender people for trans people.

I eagerly await more requests like this, and will do my best to be both sincere and accurate. But I will not write transgender stories for myself or other cis people.


The chubby, tan furred bovine ran her hoof fingers down my back, stopping just be my rump, and right back up to the shoulders. She spent time over where the bra strap had dug into my skin. The hooves provided the needed pressure, and just as it was starting to be a bit too much, she used the furry palm of her hand. The other hand slipped right into my pant waist.

She leaned in for a kiss. She stopped inches away after realizing that I was not leaning in. Only a few hours ago I had managed to overcome my anxiety and speak with her after several weeks of little more than smiles and an occasional 'hi, hello'. That and whatever else a waitress and customer normally share with one another.

"Nervous?"

I nodded. It's been a long year and half of HRT and I was finally starting to see myself the person I knew I was. I loved the woman I was. I kept my red hair short. My body was small and toned, having kept up a workout routine most of my life. My chest had filled out nicely, still quite small but flattering to my figure.

"It's my first time all over again," I told the older, plumper woman. I don't know if it was the hormones playing with my sex drive or if I was simply not ready to be with somebody in my new body quite yet, but it had been quite some time since I had been with another person. Tonight I was confident, perhaps eager, but the reality of what seemed to be losing my virginity again for was starting to get to me.

"Let's make it memorable," she said, running her hand from the back of my pant waist to the front. She unbuttoned the jeans so fast that I thought she snapped the button off. She ran it back up my thigh, gently grabbed the back of my head with the other, and gave me a kiss. It was a gentle, closed kiss, giving me the opportunity to kiss back with just a hint of tongue. Her much larger tongue twirled about mine.

My heart pounded in my chest. She pulled back and nudged me back in the direction of her bed. I laid down for her and unzipped my pants. Before I could get them off she was on top of me. She dampened my white fur with her tongue, running it up the underside of my breast and then curling around my nipple. She lightly scraped at my other nipple with a hoof-finger.

I giggled a bit, listening to her moo as she swapped over to the other breast. She reached into my pants, rubbing over my part with the furry part of her hand while the finger rubbed the entrance to the inguinal canal, testing it. I let out a bit of a gasp. It was an intriguing sensation. I've attempted to stimulate myself there before but would either move too fast or lose track of the geography. Soon she was stroking inside of it with ease and I was biting my lips with rapture. Then she added teeth to the nipples and I cried out in ecstasy.

"Feel good?" she asked with a long drag of her tongue over the nipple.

"Yes," I said, sounding more mouse than cat. My body was shaking with ecstasy. She knew how to work my body better than I did, a fact that I was quite jealous of.

"Because I can do better," she said, pulling her hand back the sliding it under my rump. She leaned up and nudged me onto my belly. She pulled my pants down the rest of the way, and my panties down to my knees. She put two of her large fingers between my buttocks, spreading them. She put that tongue of hers to use, keeping it in a curl and spinning it around my anus.

It was alright, but I needed more. I wrapped my tail around her head and pushed forward. She got the hint and penetrated me with her tongue. It rubbed against that little button that was hidden inside of me. The tongue was wider by the sphincter. A few flexes of her tongue and I could feel the entrance stretching. It was enough to make me cry out.

That must have unnerved her because she tried to pull out. I tightened the grip with my tail. "Please don't stop," I said, following it up with a humble "mrow."

That's when she started to twist inside of me. I pushed my rump back to get more of the wider part. She spun her tongue backward, scraping against the top as she pulled out. Long licks between the cheeks soaked into my fur. She poked her tongue back in and bobbed back and forth. This continued for a bit, her tongue leaving me for just a moment's time, giving her a chance to catch her breath and for me to let out a few meows to beg for more.

She signified that she was done by giving my wet-with-spit rump a firm slap. I didn't move. I was still aching for more of that large cow tongue. The sounds I made were embarrassing, to say the least. I was dripping and anxious for more. She pet my back playfully. She made me feel so comfortable I purred for the first time in ages. I couldn't see for myself but I can only assume this made her smile from cheek to cheek.

I became nervous when she left my side, so I turned over on the bed. She was by the closet, inserting the smaller end of a double sided toy into her, with a longer equine shaped part facing forward. I scooted back in the bed. It made me nervous. The flared head looked like it could be a rough fit.

"If you think this is too much," she said, reading my body language, "We don't have to."

"No, I want it," I said nervously, "Just take it slow."

She crawled up on the queen sized bed with me. She held her plump body up on her knees as she made her way between my legs. She lifted me up gently. Though my body was still wet with the spit of her tongue she did smear two fingers of lubricant on the entrance. After placing the lubricant back on the night stand, she poked the hoof in just to see how accepting my body was. It took the fingers in with only a bit of fight.

"Oh," I said as she stretched her fingers back and forth inside of me.

She was looking down at me with the eyes that somebody has when they are absolutely smitten. Equal parts love, lust, and confusion. 'How did I end up in this position' they asked me. She pulled out her fingers and ran the tip of the equine head against the well-lubricated pathway. She nudged forth gently twice before the tip popped in.

I heard the high pitched noise leaving my lips but I was never consciously aware that I was making it. It turned into a series of moans. I tried to maintain eye contact on the lovely lady but couldn't maintain focus. The toy must have been doing at least half as good of a job on her end as it was on mine because panting and mooing started to make up much of her vernacular.

I squeaked like a rodent. My body was heating up and moisture poured from my paws. I licked my lips in hopes that my partner wouldn't notice me drooling. She leaned in and ran her tongue around my nipple. My body trembled, finally coming into that orgasm that she had brought me so close to before.

It was a few dozen more thrusts before the loud mooing sounds subsided, and she collapsed on the bed next to me. We placed our arms around each other. Occasionally, we got frisky enough to grope or caress, but the intimacy of just being with one another was more than enough to punctuate the night.

Perhaps tomorrow, I'd go back to work, she'd come in, and things would be normal. Perhaps we'd go out again, and end up in bed together again. Maybe we'd skip the going out part altogether. I had a few conversations with her in my head, asking about what happens next. The apprehension kept me up for a few hours even after I had already kissed her goodnight.

But none of that was important. I had that night, and that was all I really needed.