Trans Femdom: Love at First Fuck

I had seen her on a BDSM dating app, a very nice looking woman aged 26. She was a mixed dutch-chinese with very long hair, dipped to blonde about halfway up. On all her pictures she had bold eyeliner wings and red lipstick. She wore tight black dresses or leather pants and skirts. She was quite short, only 5,1. That's why she was usually wearing high heeled ankleboots. Her style was classy, dominant but friendly.

I had seen on her profile that she was a pre op trans woman, I couldn't help but be intrigued by her.

I have been having a lot of fantasies about sucking a cock, and getting fucked by one.

I am a straight male but very submissive to women.

I didn't dare to send her anything, but it all changed when she messaged me instead. She asked me about my fantasies and previous experience I had.

After a while we decided to meet up, I was shy, but she knew what she wanted. She told me to wear a chastity cage. The thought of it made me scared to do so, but it also raced my body with excitement.

Fast forward to the day we meet, I am preparing myself for her, shave myself and put the chastity on.

We meet at her place, I ring her doorbell.

She opens the door, and in an excited manner she greets me and welcomes me inside her home.

She wore high plateau heeled boots, a panty and a tight yellow minidress, her hair falling just over half her behind. The contrast of her dipped black-blonde hair and the dress and black leather boots was very nice, and to me a little bit intimidating. Her hips and behind were accentuated by the dress, but I didn't dare to look at it.

We talked a little bit on her couch, and drank some tea. She asked for my key and I obediently gave it to her. As soon as she got it I saw her confidence rise a lot.

Then, she asked me: "So tell me about your fantasies, you are not bisexual you tell me?" She grinned.

I got shy, and didn't get out much more than a stutter.

"So you've never been fucked by someone?" She added.

"N-No," I stuttered.

"Then I think you need some getting used to." She said in a calm, dominant matter.

"Come sit on your knees here" She commanded as she opened her legs and pointed to the ground in beneath her.

I froze for a second, realizing what she wanted of me now. But I had given the key to my cage to her a few minutes ago, there was no way out now.

Embarrassed, I went up to her and kneeled in front of her as she had said.

She moved her hand toward the bottom of my chin, and pulled it up so I looked her into her eyes. "Don't be scared, I'll let you get used to it slowly." She leaned in and kissed my forehead.

She lifted up her dress, revealing her penis.

I gasped a little, I had never seen a penis in real life, let alone so close to it and on a woman like her.

It was a whole lot bigger than mine, was the first thing that went through my mind. Hers was as big flaccid as mine was completely hard probably.

"I want you to respect it." She said. "Do exactly as I say, I'll teach you how to please me."

"Y-yes Mistress." I said automatically, since I became very submissive.

She giggled, "Are you calling me your mistress already? Good boy you are, aren't you." She said.

"Lean in and kiss it for me, slave." She said playfully.

I leaned in and moved my lips toward her penis, i softly kissed the front of it a few times. It was warm, and smelled fresh of shower soap.

"Good boy, now you will have to do a lot more to get it up." She grinned as she pushed my head away softly.

"What do I need to do?" I asked eagerly.

"You are eager aren't you, I dont think you know what you have got yourself into." She smirked.

"Kiss my boots for a few minutes, show me you respect me like that." She commanded.

Without hesitation I moved down and eagerly started kissing her leather heeled boots. She let out a little chuckle.

I was getting submissive to her, and was ready to do anything she ordered.

She made me kiss her boots for more than 10 minutes, then she softly grabbed my head and pulled it up toward her waist level again.

"Thank you, I appreciate that." She said.

"Give me your hand." She ordered.

I gave her my hand, she moved it toward her penis and made me hold it.

"Okay, so if you want to please me, which you will, you have to show me good effort." She said, as I held her penis awkwardly.

"Push it back, expose my tip." She commanded.

I pulled back softly on her foreskin, and it exposed the tip of her penis. Her penis in my hand was already so wide that my hand couldn't fully close with all my fingers, and it was still not getting hard.

"Good boy, now, don't make me wait, lick your lips real good and take me in, open up as much as you can, I am not going to be amused with you if your teeth touch me." She said.

I licked my lips wet and moved toward her penis, my hand held it up and I opened up my mouth and wrapped my lips around her.

"Good boy, don't move it in and out yet, you will need to get used to my taste first, just stay still, use your tongue and suck on it a little bit."

Her head was now in my mouth, the salty taste of it made me struggle in my cage a lot. Her cock was so big already without being erect, I began to get scared. I knew I could never get her fully in my mouth. I licked the bottom of it and softly sucked on it a little.

"There you go, you are starting to become a real slut for me." She said proud.

Her hand took the back of my head, and started slowly forcing her penis deeper in my mouth.

I panicked, her penis was making me gag really quick, I already gagged on it a quarter of the way in.

She giggled. "Just wait until I am erect. Remember I can force it all the way in, don't do anything brave." She threatened.

Her penis started getting hard, I had tears in my eyes and pain in my jaws from having it in my mouth.

She laid her head back and let out a sigh of relief.

I sucked on her penis as good as I could, trying to struggle it deeper in my throat each stroke.

"Very good boy, you will sit on me like a good slut won't you?" She smirked.

She pushed me back, and her cock fell out of my mouth, onto her lap. It was now almost fully erect, and halfway past her upper legs.

"I-i don't know if it'll fit in me." I said while looking shy at the ground.

"Oh it will hurt in the beginning, we will take it slow and get you used to it." She said affirmative.

I got really nervous, my stomach began to ache. I have had some experience with toys up my behind but I always needed a lot of time to get used to larger toys.

"P-please be gentle with me." I stuttered.

"Awh, don't worry, I am not cruel! Of course we will take it slow. You can do it. Believe in yourself a little bit." She grinned.

"It's about time for you to undress yourself, show me you are giving yourself to me." She said.

I got really shy, but my submissiveness took over and I quickly stripped all my clothes off. I hesitated a bit before pulling down my underwear.

"What's the matter?" She asked playfully.

"I am shy to show myself. I am a lot smaller than you are." I stuttered while looking down at the ground.

She put her hand under my chin and raised my head, making me look her in her eyes.

"Hey, don't be ashamed. You are good the way you are. But right now you are locked up anyways, so does it really matter?" She grinned, playful as she had been.

Her nice words combined with her dominant matter made my heart race.

"Now strip, I wont ask again." She grinned lovingly.

I pulled my underwear down and exposed my caged penis to her. I stood there awkwardly before her.

She took my caged penis into her hand, cupping my exposed balls. Her warm hand felt amazing.

"You are very cute. You look so good!" She said lovingly.

"T-thank you so much Mistress." I stuttered.

"I think it's best if you start on top of me, that way you can control how deep I go in you whilst getting warmed up." She said caringly.

It came to me that it was now really time to have sex with her. My stomach turned.

"Y-yes Mistress." I let out.

"H-how do I do this? Please instruct me. I am a little lost." I said ashamed.

"Don't worry, I'll teach you. I have some lube and a condom here, I think it's best for you to use them." She grinned.

She gave me the condom and the bottle of lube.

"You know how to put on a condom, I assume?" She let out playfully.

"Y-yes Mistress." I said.

Clumsily I took out the condom of it's wrapper and rolled it onto her erect penis.

I put some lube in my hand, and started stroking her penis to lube her up.

"Come up on my lap." She said.

I didn't hesitate and got up on her lap. She moved down a little bit on the couch so her hips aligned better with my behind.

"Now, take it and press it against your hole until you feel comfortable enough to slide me inside of you." She ordered.

I did as she said, I had done this before with toys. I took her penis in one hand and slowly lowered my body onto it. At first it didn't fit at all, but my asshole slowly relaxed and stretched, allowing me to get her tip into me little by little.

She chuckled. "Harder than you expected?" She asked.

"Y-yes Mistress, you are very big." I moaned.

After a while of slowly trying to get her in me my hole stretched enough for her tip to make it into me. I lowered my body a little and suddenly she slid in me a whole lot deeper.

I let out a big moan, it was a little painful but the sensation was incredible. I very minimally started moving up and down, getting used to her penis stretching me out.

She laid her head back and let out a sigh.

"That's it, good boy." She let out.

She moved her hands to my hips. Slowly pulling me down on her.

It hurt, but not too much for me to want to stop. I felt dedicated to take her. She made me so submissive.

I leaned forward a lot, and started moving my body up and down her shaft more and more, getting more comfortable on her penis.

"You are doing great!" She confirmed.

We both started moaning intensely with every stroke.

She moved one hand and grabbed my throat, pushing my body back, making it so that I was sitting up straight, and so I kinda fell onto her penis, making it enter me a whole lot deeper.

I gasped so hard at the feeling of her big penis so deep inside me, I could feel every detail of her penis moving in me.

"T-thank you Mistress, please use me." I moaned, the submissiveness now taking over any form of shame.

"Good boy, work for me." She gasped, as she started slowly thrusting her hips synchronized with my body movement.

We had sex like this for a while, my cock was struggling in it's cage, letting out a whole lot of precum with every stroke.

Suddenly she slowed me down.

"Would you be ready for me to get behind you? I really wanna orgasm in you." She asked.

"Y-yes please Mistress, please use me for your pleasure." I moaned like a good little slut.

"Good. Get up then." She commanded.

I slowly took her penis out of me, and got up off of her.

Before I could even ask where she wanted me, she already got up and firmly guided me towards her kitchen table. And laid me down on it with my stomach, spreading my legs so my behind was in the air at the perfect height for her penis.

"Oh my god, yes please." I gasped.

"Now you will be a good boy for me. Would you mind me taking off the condom? I like filling up good little boys like you." She grinned.

My submissiveness had completely taken over any rational thinking at this point. I could only ache for her to use me as her little toy.

"P-please fill me up, Mistress. I wanna be nothing but your slut. Please." I moaned.

"Good boy." She said.

She took off the condom, lubed up her bare cock and slid it in me, almost immediately pushing it deep inside me.

I moaned and struggled, but her firm hands held me down on the table.

"Take me then. Slut." She said.

She started thrusting into me very hard. Precum leaking from me every stroke, which fell down, partly on top of her boots. She didn't notice.

She moaned loud, and fucked me incredibly hard. I couldn't do anything but take it, and experience this intense moment.

She started thrusting faster and faster, leaning over me while holding my hands on the table. She kissed me in my neck.

"I am going to cum." She said.

"Please Mistress, please cum in me." I moaned.

She continued fucking me until she started moaning even louder, clearly indicating she was having an orgasm.

"Ohh yes, that's it." She let out as she pushed her penis fully in me.

Her balls touched my balls and I could feel both them and her penis pulsing as she cummed. The sensation of having my asshole filled was new for me. It felt incredible.

She collapsed over me, laying on top of me while her dick was still pulsing from her orgasm inside of me. She let out a big sigh.

"T-thanks Mistress." I begged her.

"Shh, she said. You did very well. You can be proud of yourself." She confirmed me.

Slowly she got up, and pulled her half erect penis outside of me. Part of her load immediately started dripping out of my hole.

"Don't worry, lay still, I will clean you up." She said.

My knees were completely shaking at this point and felt very weak.

She lovingly cleaned my legs and hole with some toiletpaper.

"You are such a good slut. But look what you have done." She said.

I got up, and she pointed at her boots, on which some of my precum had dripped.

"I'd really enjoy it if you cleaned that before we go to bed." She said lovingly.

"C-can I stay here for the night?" I asked surprised.

"If you want, yeah, we can cuddle and watch a movie if you'd like." She said.

I knew this might be the start of something incredible. And eagerly I confirmed I wanted to really bad.

"Good, but you will have to clean this little mess up first." She grinned while pointing at her boots.

She walked back to the couch and sat down. She pointed at the ground in front of her and snapped with her fingers.

Completely in awe of the whole experience I didn't even hesitate and kneeled in front of her. I eagerly licked off every drop of my own precum off of her boots.

She chuckled. "A boy like you is rare. I appreciate you a lot. Thank you." She said to me.

I blushed. And continued cleaning her up.

Later that night we went to bed. She big spooned me, firmly pressing her penis against my behind. But holding me very tight and lovingly. She kissed my neck.

"Thank you for today. I appreciate you a lot." She said.

I was processing what had happened today. I think I fell in love.

Who knows what else will come out of this.