Dan's a Crossdresser Pt. 02

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Dan's addiction deepens, Ex finds a black man.
1.2k words
4.28
18.5k
17

Part 2 of the 8 part series

Updated 06/10/2023
Created 01/05/2021
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Part 2: Dan Dives Deeper

Over the next few years Dan would take a deep dive into sexual exploration. Dan would end up exploring solo as his expectations in women were way too high. He wanted a Nylon Queen and that was just so out of reach for him. He tried going out a few times with guys from work to find chicks but it was difficult. He just couldn't talk to them even when he rarely got a shot. The guys he went out with weren't chick magnets either. Dan's addiction to hot instagram chicks and porn had made his sexual interests lie with the hottest of chicks, the kind of girls that would already decide "no" just by looking at Dan. He would go up to 9s and 10s, the ones wearing short skirts and nylons, and he would ask them if he could buy them a drink. They would either just walk away after one look at him, or they would get the free drink and then disappear. A few would even just be brutally honest to his face saying things like, "from you? No thanks." The constant rejection eventually took it's toll on Dan and he stopped trying. Perhaps if he lowered his expectations he would have better luck batting within his own league. But Dan was addicted to hot bitches. Staying at home, dressing up in lingerie and stockings, and jerking off to hot bitches was better than getting with some average looking chick. This realization is what began Dan's descent into his addiction.

Thus began Dan's weekday routine. Go to work, come home, dress up in panties, garters, and stockings, and heels, look at Tracy's new Instagram posts, start jerking, watch porn, edge for hours, then a huge cum blast. Dan could cum large quantities of semen. This perhaps was his only sexual gift, the ability to always cum a lot. It was likely because he was always thinking about something arousing. On the weekends he dug even deeper. Gooning to Tracy, Gooning to Porn. Edging all day. Prancing around all day in lingerie, feeling slutty, feeling feminine. He saved up his cum for night time, and came even more than he did on the weekdays. He had become quite the masturbater. Dan is an addict to the full definition.

With every crossdressing masturbation session, his psychology would change ever so slightly. As his brain released chemicals of excitation to all of the stimulus he used for sexual gratification, his addiction grew deeper. His ex-wife Tracy's photos, Tracy's friends, the bimbo pornstars, his own crossdressing were the things that were morphing Dan's mind. The slight changes in his psychology each time would add up upon eachother. Eventually Dan would seek out more and more stimulus. As any porn addict knows, everything and anything is available on the internet. Dan started to discover new things on his favorite porn website.

Dan began finding new categories to get that new sexual high. Before he had mostly just watched lingerie pornstar bitches having sex with pornstar men, from the big production companies. He would also watch amateur girls in lingerie having a cam session fucking dildos or their boyfriend's cock. He was always impressed with the size of cocks in porn but thought, only people with large cocks would even do porn so he didn't think much of those cocks relative to his own cock. Dan stuck to this kind of porn for a while. I guess you could say Dan was looking at traditional porn if there is a thing. He would only watch videos or look at pictures where lingerie and nylons were involved.

Dan's first find outside of the traditional was a thumbnail on the home page of his favorite porn site. It was a picture of a beautiful big cock framed by garters and stockings. This caught Dan's attention because he too loved to frame his own cock with garters and stockings. Out of curiosity he clicked the video and found a beautiful transsexual lady wearing incredible lacy lingerie. Thus the addition of Tranny Porn to Dan's favorites. Dan couldn't believe how a man could become a beautiful woman. It shocked him a little, thinking that a cock could be beautiful when presented in a feminine fashion. He certainly didn't consider himself to be gay. Dan thought, how can liking a cock not be gay? He justified it as considering it to be a girl's cock so therefor, not gay. A whole new world had opened up for Dan to explore. Tranny porn eventually led to finding crossdresser porn. Ones with excellent taste in lingerie were his favorite. Some even had sexy dresses, and did makeup quite well. The more convincingly feminine, the more Dan liked it.

Dan found that there are other crossdressers out there and they had their own profiles on the porn site. Dan decided to make one too. He created one and called himself CD-Danielle. He would add friends and go through their galleries, videos, and favorites. Dan would take pictures of himself from the waist down. Crossdressers and CD admirers would comment on his galleries and give him attention he had never had before. He had found a community where he belonged. He was loving life!

The routine continued on and on. He would order new styles of lingerie, even getting corsets, bustiers, new stockings, new panties, new heels, and new garters. He would dress up everyday. He would look at Tracy's instagram posts, watch various categories of porn, and jerk off. When he was done jerking he would go through all of Tracy's older posts and captions. Even if he had seen them many times before, she was so sexy it never got old. He missed Tracy so much, even though he never really knew the Tracy she was now. He would lament over the loss of such a sexy Nylon Queen. He had one, and he didn't even know it. He knew he fucked up for letting her go, but deep down he also knew she deserved better. At this point it had been 2 years since the divorce. It had flown by. Tracy was living the life she desired, and Dan was diving deep into his crossdressing paradise.

Then something happened. On a Saturday morning he woke up, and checked Tracy's instagram. For the first time she made a post with another man. This caught Dan's attention. Dan's heart was racing a mile a minute. She had posted a whole gallery of her Friday night out with her sexy girlfriends and some men. All the men were tall, dark, and handsome and seemingly wealthy. Visually they looked like professional athletes. They very well could be athletes, Dan thought, even though when it comes to sports, Dan is clueless.

One particular guy had his arm around Tracy in multiple photos. There was no tag on him, so Dan had no way of knowing who he was. He must have been roughly 6'5" and he had arms the size of Dan's head. He was in every way different than Dan. He dressed very polished in a nice suit and had a nice watch. He had a smile that could catch any woman's attention. One particular thing stood out the most to Dan. This mysterious Man is Black.

End Part 2.

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