Oh, I was hooked. No denying. How it came to be I still don't know. It happened gradually. From watching beautiful women online, not necessarily nude, but dressed in sexy tight outfits. Leather, latex, pvc, nylon, satin, fishnets, high heels, corsets. It all worked for me. And not having a girlfriend or fuck buddy, it was obvious that I masturbated a lot.
The first time I saw it, I think, was a short video of a woman in a full size fishnet body, wearing incredibly high heels. Perfect breasts, perfect ass, my fantasies started really taking off. Until the last moment she opened her legs, and a hard dick flopped out.
At first I was appalled. Tried to edit the video to cut out the last few frames. But however these search engines or AI's work, I dunno, but I had lingered long enough on the video, and more pictures and videos showed up in my feed, of beautiful women with something "extra" between their legs.
When the first shock was over, I realized that girl-dick, as I started calling it in my head, was not like normal dicks, like my own. Typically hairless, clean, thin and sleek, they just had a female feel, a female appendage, if you like. I bet it would even smell female, and nothing like my own.
One particular video was a woman, masturbating herself. She was sweating, her breasts shiny with oil I think, as she was fondling herself, moaning sexily. Not until it had worked me up already did they show her girl-dick, which she was pumping, rather than the pussy I was expecting.
I had been playing with myself already, and was close to cumming, when I saw her male part, and the way she handled herself, together with her urgent cries, made me finish the video, and I came the same moment that she did.
So yes, that needed a bit of thinking of course. But every time I saw that video again, I grew harder than ever, and it was easier and easier to orgasm in sync with her. And it didn't take long before other pictures and videos, that included girl-dick, had the same effect on me. It must have been that slight taboo, knowing it wasn't one hundred percent right, that made it more exciting.
It took a while before I realized that, although I still collected pictures of "normal" girls, my masturbation sessions always started including she-males, transgenders, dick-girls, whatever you want to call them. And my fantasies about finding the perfect girl slowly started including this type of girl as well.
I've only had a few girlfriends, and our relationship never lasted very long. But I'd found them through the standard channels, like in a pub, or a bowling alley, and once at a company outing. But how do you find a transgender girl?
I had started reading more about the transgender lifestyle, realizing that she-male and dick-girl are more used at porn sites, and most trans women don't like to be called like that. I also found that their transitioning is an urge to match their physical gender to their perceived gender, and that most went through hell, as the majority of people are not very supportive, or flatly and sometimes violently against it.
Things started to change for me. Not only did I wonder what it would be to have a transgender girlfriend, but my sex life started anticipating it as well. No longer could I simply rub one out at the thought or image of a normal or cis girl. But with the image of a nice trans girl I started wondering how it would taste to suck her male part, or how I would take her from behind.
You ever hear the saying "once you go black, there's no going back"? I felt like that with trans girls, even though I had no experience at all yet. I considered going to a gay club, thinking the chance to find someone there may be bigger, but my own prejudice stopped that. Trans women are real women, so it wouldn't be gay to be with one.
I ended up checking dating sites and groups aimed at trans relations. But I was shocked how many women basically just wanted to make money, maybe to offset the costs of hormones, hair removal and surgeries. It just didn't feel right with me to pay like that for a relationship, or even a simple one night stand.
Until I found a woman, not too far away, who thought alike. Money matters would just complicate her tax returns, she joked. She wasn't really looking for a relationship either, but was open to it. Really, she just wanted a sex buddy, that included giving and getting in an equal way.
She set a few simple rules. Her place, her rules. Sex was either oral, anal or a hand job. I would pick first, and she'd give me exactly what I wanted. After that it was her turn. I could ask for a blow job or give one. If I'd give one, I could pull away when she'd cum, but if at her turn she would ask for a blow job, I would have to go all the way, which included swallowing. It seemed fair, but I really wasn't sure if I was ready for that. Not until she promised that at least the very first time she wouldn't expect me to go all the way, did I agree. At that point did she explain there was one more thing...
If things seem too good to be true, they typically are, so I braced myself for disappointment. She was probably just a freak, I imagined. But what she wanted didn't seem too unreasonable.
In essence she had the same desires as me. She preferred sex with a female, but she needed dick as well. Her solution was that I wear something female. She'd give me a choice between two items and I would pick one. As a matter of fact, for my first visit, she'd let me choose between wearing a skirt, or a pair of heels. That didn't seem too extreme, I figured, although I had not really a desire to dress female myself.
And that's where the catch was. Say I'd pick the skirt, which was more likely in my mind than the heels, I'd wear it during "her session", her pick for sex. But if there ever was a follow-up session, it would start with dressing me in the same skirt, and then when it was her turn, I'd have to pick again from two items. Long story short, the more sessions we'd have, the more female attire I'd end up in. And she was pretty clear that it was not necessarily clothing, it could very well be a wig, or makeup.
It took a bit of time before I realized that she indeed had the same needs as me. And also, that I was still in control. If I didn't like what I was to wear, then I simply would not have another session with her. One thing kept nagging though. So I told her I was okay with it, as long as it wasn't like bondage and stuff. I was just too scared of losing control. She actually laughed, because it took one of her own worries away, as neither was she.
So the date was set for Friday night, allowing both of us to "recover" the next day, not having to work. It gave me time to prepare. What exactly was it that I wanted? It took a while, before I could finally confess it. More than anything else did I want to taste her dick. Was it indeed a female appendage? And would I be able to control it? And if I did, would I dare to go all the way? I knew I didn't have the answers. It would be a game time decision. But was that not what I had fantasized about?
When Friday night came, and I had driven for just about an hour, I rang her doorbell. Was it possible she didn't even look like her profile picture?
But I was not to worry, when she opened the door. If nothing else, her profile was outdated. She looked even more beautiful. And when she smiled, I knew she had worried about my own profile as well.
So after official introductions, "hi Kayla, hi Ronald", and some smalltalk she asked the question of the night. What was it that I wanted? And I told her I wanted to taste her.
Not much later I was on my knees in her bedroom. Her fashionable skirt was pulled up and her panties down. In real life her dick was even prettier than I had seen in some of her pictures. It was perfectly smooth, not a hair in sight, standing slightly up with the start of her arousal, being exposed like this. I smelled, and I had expected a female scent, but nothing like the perfume she must have used in the area.
I don't mind a woman smelling nice, as long as it's not over the top or too much. But this scent was pure seduction, an invitation, a message of sex and desire. It hooked me, I wanted to take it in, take more in. My nose touched the tip of her manhood, and suddenly I knew the seductive smell was at the base. I simply opened my mouth, so I could move my nose closer to her skin, and just like that I took her whole length and I was in heaven.
In my mind I had practiced a few times already. I would kiss her tip, lick around it a bit until she'd start reacting, and then slowly and teasingly I would take more and more of her. I was in complete control and I'd slowly take her over the top. The only thing I had never gotten past though was what I'd do if she'd cum.
Basically nothing like that had happened. The delicious smell had entranced me, my need to find the source had taken her member in without a thought. And her movements, pushing in deeper, then pulling back, caused her to grow rapidly in my mouth. She was in control, as I held her rear in my hands, trying to pull her into my face, as not to lose contact. When I sucked a vacuum it resulted in her member growing thicker, and sliding slowly towards my throat, but as a result my nose stayed where I wanted it, and I just breathed her in.
I added my tongue around her, holding on to her monster, giving her no chance to pull back again. Her hands were now on the back of my head, holding me close, keeping me exactly where I wanted to be. And then she cried out, her voice that of a siren, a song that merged with her scent, spiking my desire to hear more. And her moan remained, blessing my hearing, as her tip twitched in my throat.
I had no desire to pull back, did not even consider it. My mouth suddenly filled with nectar, as my taste buds slowly won the fight with my smell and hearing senses. I swallowed her fluids, trying to avoid it from squirting out of my mouth. And when her member got softer, I tried to squeeze out the last drops, before it pulled out of my mouth with a pop.
I lost her, but I stroked her skin, put a few quick kisses on her disappearing member, as her moan turned into a soft cry. I looked up at her face and saw indeed tears in her eyes, but the look on her face was one of bliss. She laughed, then finally said, "that was amazing!"
Amazing was the right word. I had just sucked my first cock and swallowed till the last drop, without a second thought, already wondering when I could do it again. I knew I had not been in control for even one second, and I didn't care. No, I did care, it was a bliss I'd never felt before, I'd do it again, anytime she wanted.
I didn't realize until now that the whole experience had left me rock hard. Kayla noticed though and she said, "you like my perfume then? It's officially called 'Oblivion' but commonly known as 'Hooked'. You need help with that?" And she pointed at the strain on the pants I was still wearing. I just nodded, and she had the button open and my pants down, before I realized what was happening.
She explained. "You got me so hot! I figure I'd return the favor on my turn. Just want you to wear a girly thing before we start, so what's it going to be? Skirt or heels?"
I picked the skirt, as I had decided earlier that week already. Just didn't expect it to be leather. It sat high on my waste, then flaring out across my butt. A skater skirt, she explained.
I never really had any desires to wear women's clothing, but this skirt was actually nice. Or was it the leather? No mind, I was pushed back on the bed, her hands now on my leather covered butt, and her face under the skirt, teasing my now rock hard dick with her tongue. I'd really like to brag I'm a stud, but when she took me in her mouth, one hand caressing my skin through the leather, the other tickling my scrotum, as she literally vacuumed my hard-on, I don't think I lasted more than a minute.
She drained me completely, as I kept shooting cum down her throat. For the second time in less than an hour I was in heaven, but again without having control at all. And again I wondered, when can we do this again?
We spent a bit of time cuddling, both exhausted, both satisfied, both not wanting it to be over. Afterwards, she offered me a drink, and we had it in her kitchen. I saw the leftovers of what seemed a so-so dinner, and I had to stop myself from starting to clean her dishes, being the clean freak I am.
But a thought hit me, and I suggested next time I bring dinner. From where I worked I was already halfway to her place, so it would be less driving and I would be there sooner, giving us a chance to spend more time together. What I didn't say was that whatever I'd bring, it would definitely beat her leftovers.
The other thing that was not said, but was clear to both of us, was that we'd see each other again, and in the smile on her face I could see she wanted it too. When we said our goodbyes a bit later, she kissed me softly on the cheek, and although we felt both awkward, it also felt good. I wondered if this could become a friendship, rather than just being fuck buddies.
Throughout the week we chatted online and I felt more and more comfortable with her. She told me she'd let me pick between heels again, or a bra-top that would match the skirt. Just for the fun of it I let her pick between Asian or Italian food.
Friday came fast, and right after work I picked up my favorite Chinese food and took it over. She looked even better than last week and she had me put my skirt on right away. She asked if I was okay with picking my next piece already, so a minute later I wore a bra, in the same leather as the skirt, for the first time in my life. It was more a top really, but thanks to the built-in padding as female as the skirt.
She enjoyed the food I had brought, and I enjoyed her company. At first we talked a bit about ourselves, we were rooting for the same sports teams, and definitely had more things in common. I took control of cleaning the dishes and took care of a part of her kitchen as well. She watched me, saying she could get used to that, and then went on to say how nice I'd look with a wig and some make-up. I don't know about that, but it did open up the conversation on her transition, and I learned a lot about the lesser fun things like hair removal, dieting and working out. Or the effects of the hormones, the pleasure of slowly seeing her own breasts develop, and the reactions at work, and from friends and family. Being transgendered is definitely not an easy path.
After a while, back in her bedroom, I submitted again to her wonderful perfume, enjoying every second of being face fucked. And after she had recovered, I was on all fours, losing my anal virginity. It was the weirdest sensation, painful at first, but slowly becoming more and more pleasurable, but what was really surprising was that my own dick started to react. I erupted, when she came inside me, messing up her sheets. But she was as thrilled as I was confused.