I don't know how or why I got interested in trans women, I guess I must have liked once or twice a picture of a beautiful woman on social media, and the system must have concluded I had an interest, and thus showing me more.
The first time a picture showed up in my feed of a beautiful woman that had something extra under her skirt, I had clicked “like” already, before I zoomed in on what was undoubtedly a dick. It didn't matter that I unliked it again, as more and more showed up in my feed.
My state of mind changed I guess when a beautiful woman in sexy lingerie had a small dick “freed” from her panties, and it didn't look even remotely male. It was simply a very female looking extra piece.
It must be that moment when one had added a comment with her picture that said “liking a trans woman is not gay”, that I dropped my defenses a bit, and I clicked the little heart. And after that, anytime I saw a woman where her extra was displayed in an aesthetic way, I clicked the like button more and more.
Ok, I guess so far it all looks still very innocent, and maybe I look like a likeable guy even, but I got on a more darker site I guess, what some people would probably consider porn. And I got hooked.
On this site the women were still beautiful, but the dicks were openly displayed, often much bigger than my own, and often tagged as shemale, to which I subscribed.
Beautiful long hair, well done makeup, nice sized breasts, and a beautiful monster between their legs, became my ideal picture of a woman. And more and more I started wondering what I would do, if I met one in real life.
Would I dare play with her dick? Touch it? Lick it? Arouse it? And maybe suck it? Would I dare make it cum in my mouth? In my rear?
In my mind everything was game, and being online is not real life. So I started reposting and leaving comments how I'd love to suck it, or let her take me. And I started masturbating to these women, fantasizing myself in different positions, and coming harder and harder from these thoughts.
Again, I'm not proud of it, but my initial interest in the beauty of trans women turned into a desire for shemale porn. Some of the women that were supposedly in the pictures, started private messaging me. Some clearly after money, which I dismissed. Some asked if I was a sissy.
And that was the other piece that showed more and more. Not strong, athletic women that happened to have a large dick, but small, very feminine former males, who had locked up their dicks in tiny cages, and were looking for men, or shemales, to fill up their rear, or their boi-pussy as they called it.
They didn't have my true interest, but as sexily dressed as they were, and clearly submissive, had me wonder what it would be like to fuck a pretty one from behind. Whereas with the shemales I realized I would be the one being fucked. I would be the one more submissive.
Other than my late night porn fantasies I still had a regular life as well, and that included meeting up with friends at a bar or a restaurant. Friends that would never guess about my change in female preferences. Who would probably dump me, if only they knew.
So, with them, I kept up a front of being interested in “chicks”, or “normal” women. And one night, sitting at the bar, waiting for my friends to join, I met a beautiful woman. And although in the back of my mind I hoped she had something extra under her leather skirt, I managed a good conversation with her, about anything but dicks.
When I got a text that my friends were delayed, as they came from a different part of town, I was actually happy, and so was Jordyn, as I showed her the message. It was then that I noticed a tiny wet spot on her sweater, right over her nipple.
She was clearly embarrassed, as she started explaining that her twin sister just had a baby, and she was so in tune with her sister that her own breasts had started producing milk as well. An inconvenience, but not nearly as bad, as when she had all these urges for weird food, while her sister was still pregnant.
We were in a private area of the bar, and she actually moved her hand under her sweater, and when she pulled it back out, I saw some drops of milk on her finger. And she offered it for me to lick.
In mere seconds we went from casually talking to the very intimate offer of sharing bodily fluids. And I liked her forwardness and I decided to reciprocate. So, I took her hand and guided her finger into my mouth.
I had no clue what to expect, but definitely not that it was so sweet. And the way I sucked her finger clean was much more erotic than intended. She went back to her nipple for more and I sucked eagerly. That's when she gave me a choice.
She would have to go home to pump her breasts, or she would mess up her clothes real soon. And was I interested to go with her, and suck the milk straight from the source?
It was an easy decision, as it had been a while since I was with a woman, and sucking breasts was much closer to getting laid. But, I suggested we go to my place, which was only a three minute walk away. Quicker for her to keep her clothes dry, and less chance for me to run into a potential husband or boyfriend.
Let me state first that there was no sex. But the experience was incredibly erotic and satisfying. I had no idea that breastmilk could be so tasty. And the way she relaxed with me as I drained her had a promise for the future.
Afterwards we chatted some more and we exchanged numbers, and she literally asked me if I was willing to do this more often, as for her it was much more pleasant as well than using a breast pump. Any time, I told her.
She didn't go back with me to the bar, but she kissed me when she left. Later my friends asked where I had been, and I told them about meeting Jordyn, and I left it to their imagination how I had already gotten laid by then.
That night I had trouble falling asleep, as I could only think about the elixir I had drained from this woman's breasts. For one night shemales did not have my interest in my dreams.
When I woke up Saturday morning Jordyn had already texted me. She would really enjoy another draining by me, if I could make it by 11 am. And she gave me her address, which was only a fifteen minute walk away. A jolt of excitement hit me, and I texted her that I would be there.
I didn't eat much, just a bit nervous, but also because I didn't want to be “full”, as I realized the milk added quite some calories. I found her place in an awkward building, the front doors very close, like in a hotel. I wondered how big her apartment was.
When she let me in, with a big smile on her face, I realized her place was indeed not much bigger than a hotel room. A small kitchenette, a small bathroom, a large closet filled with clothes, and a large bed. No window, that I could tell.
I could tell her breasts were full again, and my mouth started watering. We didn't waste much time, but she did ask if I was okay with her using a toy on herself, while I sucked her breasts. Of course I was!
She was wearing a leather skirt again, still narrow at the waist, but much longer and wider, covering most of her legs. She had some pillows stacked together on the bed, and as she rested against them she invited me on the bed next to her and to take my shirt off, so my top was as naked as hers.
Then she sort of straddled me across her lap, so that her arm was behind my head and back, while I put my head down just under her breast, my lips against her engorged nipple. As I started sucking, I could only think as if I was a very large baby, more or less cradled in her arms.
Once again I devoured the sweet milk, as she gave me soft words of encouragement. Then I could hear a tiny click from something she had in her hand, and I felt a vibration somewhere below her body. Was this a massage bed?
The vibration however stopped her soft words, as she started moaning. I tried to get up to see what was going on, but her arm kept me down, and she literally said, “keep on sucking baby”. I had to smile about that, but her moaning started to turn me on.
I could tell she had an orgasm, shortly after I switched over to her other breast. She kept my head tight against her chest and I could feel her heart bang against my ear. The vibration had stopped, as her breath slowly went back to normal. But, before I finished draining her, she clearly had another orgasm.
Afterwards her mood was upbeat, and I asked what toy she had down there. And as she pushed her hand under her skirt, it came back with a pink egg with a sort of tube hanging from it. “Wanna try?” she asked. I had no idea what it was but I wondered if she'd had that thing in her pussy. And I nodded before I realized the consequences.
She had me take off my pants and underwear, and she promised me a blow job like I'd never felt before. I was on my back now, as she cleaned the egg, then added some gel or something around it. She spread my legs and without warning pushed the egg into my rear door.
I think I yelped, more from the cool gel and unexpected feeling, than from any discomfort. It clearly wasn't very big, and slid easily inside me, only the round end of the tube sticking out from me. And I suddenly thought about my fantasies where a shemale filled me up from behind, and suddenly my dick came to attention.
“Mmmmmm….”, Jordyn said, “baby seems to like this.” And again, before I could protest, she lowered her mouth over my rigid flagpole. And any idea of protesting was gone. Her mouth was so soft, so warm, and she clearly knew how to pleasure a man. And I got more and more excited, knowing that my own orgasm would soon come. Then the vibration started…
I had already concluded that the egg had caused the vibration in her pussy, taking her over the edge twice, while I stimulated her breasts, all things together making her cum.
And now I was in a similar situation, her mouth sucking on my dick, and the vibration in my rear touching some sweet spot. I couldn't even warn her, as I came hard and shot my load. She kept sucking hard, draining my balls, as she swallowed all, like I drank her milk before.
As I had nothing left, I would normally come down from my high, but not with this vibration in my rear. It quickly became very uncomfortable, and I managed to cry “Please stop!”
The relief was instant when it stopped, and the smile on my face came back. She was right, never did I come so hard in my life. And as she laid down next to me I felt a surge of love for her. I think we both dipped into sleep for a second, until I heard a male voice. “What the fuck is going on here?”
As I opened my eyes I saw a man in a fur coat with oily hair and a very angry face, and I became very aware that I was completely naked. It was Jordyn who answered. “Sorry boss. This is Steve. He helped me drain my breasts, and I gave him a blow job as a reward.”
Boss? Her boss had access to her apartment? And she told him more or less that we had sex? What kind of job did she have? The next minute it became very clear.
“How much did he pay for sucking your breasts? And for the blow job? That should be at least two hundred. Maybe three.” And he grabbed my pants that were discarded on the floor, and took my wallet out. “Hey!” I protested, but the look on his face and a warning squeeze on my arm from Jordyn had me shut up.
“He doesn't even have fifty in his wallet. And that phone isn't worth much more.” And I saw him pocket both my wallet and my phone. Then he saw the little pink remote that Jordyn had used for the egg, and he grabbed it, and pushed the button. And a sudden vibration started inside me, as we never took the damn egg out. I tried not to moan, but a whimper escaped from my mouth.
The man had a smile on his face now. “I paid five hundred for that toy, so you owe me eight hundred minus the hundred that your phone and wallet are worth. How are you going to pay for the seven hundred?”
The vibration drove me nuts while I tried to clear my head. Jordyn was a sex worker? I finally managed to speak. “I thought I did her a favor, by draining her breasts. I didn't know it cost money, last night it was free…” I knew right away that was the wrong thing to say.
He looked at Jordyn now, furious. “He was here last night already? You never told me! That's another three. He owes me a grand now!”
I panicked now. I didn't even have a thousand in my bank account. “My credit card. In my wallet.” I sounded like a weakling, the continuous vibration inside me messing up my voice.
“You don't have a wallet anymore. And besides that, we're a cash-only business.” And I saw him opening my wallet, taking out my credit card, my debit card and my driver's license, and he pulled something from his pocket, pushed a button, and a blade jumped from it, the knife clearly very sharp as all three cards were destroyed in seconds. Then he took every piece of clothing that was mine and shredded it as well. My keys fell from my jacket, and he pocketed them as well.
With the knife still in his hands, his face came close to mine and he whispered this time, “How are you going to pay boy?”
I cried now. “I don't know…” And I feared for my life.