Dan's a Crossdresser Pt. 01

Part 1: The Beginning

(Some themes you can expect from this story series include crossdressing, porn addiction, an emphasis on nylons and lingerie. Eventually the story leads to some SPH, interracial cuckolding and BBC action. There is no anal shit, I apologize to butthole lovers)

Dan is from Raleigh, NC. Dan is an average looking white guy, he stands 5'8", he runs daily and has small figure at 140lbs. He's kind of a shy, and a little bit of a nerd. He is a nice guy once you get to know him. He has a little bit of a sexually submissive side that has yet to truly take over (but it will). He is divorced and has only ever been with one person, his now ex-wife, Tracy.

Dan and Tracy met in highschool in their hometown outside of Raleigh, they both ran cross-country and got along quite well. In highschool, Tracy was one of those cute girls that didn't really know it. This kept her humble and likely how she ended up in a comfortable relationship with an average guy like Dan in the first place. They went to NC State together for university and after, got married and got jobs in Raleigh NC. From an outsiders perspective, besides the fact that Tracy was clearly out of Dan's league, Dan and Tracy seemed like a good couple. However, outsiders never really know the truth. After 2 years of marriage, Tracy wanted more. Tracy was very career oriented, she double majored in management and communications, but her outgoing personality was allowing her to climb very fast in human resources. Dan didn't seek career advancement and was perfectly fine keeping the same accounting job for the next 40 years. Along with Dan's non-dominant career attitude, Dan had a very non-dominant role in the bedroom. Dan pretty much let Tracy be the initiator for anything sexual. He didn't take charge. Even when Tracy initiated, Dan was always distracted by his video games. Not only that Dan wasn't really a performer in bed anyways. Although Dan probably thinks he's average, Dan has a little penis. Dan's penis is about 4 inches long while hard and has a circumference of 4 inches. When they rarely had sex he didn't know what to do with the little thing and he would always cum in less than a minute. Tracy was always left unsatisfied.

Tracy didn't think much of all of these things in high school and college as she really didn't know much better and she was also focused heavily in her studies. She figured marriage would somehow unlock whatever was missing from their sex life and their general lifestyle. She figured once they had jobs they would become more outgoing as a couple and get out there and try new things! Tracy wanted to go out in the evenings to nice dinners and bars, she had spent so many years sacrificing those things to focus on her studies so now she wanted to have fun! Dan however wasn't on the same page. Dan liked staying home. In university, he was an average student. While Tracy studied hard, Dan played video games on the computer he built. So now, while Tracy had ideas of hitting the town, Dan wanted to stay home and watch movies or play his games. Tracy was often left bored. Unfortunately, Tracy at the time had only semi-attempted to use her womanhood to inspire action out of Dan. If she gave it the thunder she now has today, it perhaps could of saved their marriage assuming Dan could put down the video games. Tracy eventually would learn fully of her womanly powers, but at the time, she just hadn't yet.

Eventually the combination of these differences led to a mutual agreement of a divorce. They were only 25 at the time of the divorce, and without that spark, they thought it would be a good idea to quit while they still had their youth. Tracy was the one who initiated the divorce. It was certainly hard for Dan because the divorce hurt Dan more than it hurt Tracy. Even so, Dan was aware enough to realize it was for the best to let Tracy free.

They went their separate ways. Tracy moved to DC in pursuit of a human resources management job at a fortune 500 company. Dan stayed in Raleigh at his accounting job. Tracy was quite active on Instagram so Dan was able to keep up with most of what was going on in her life with all of the posts she made. The only time they would talk is when Dan sent her a happy birthday message. They would catch up a little bit, and then it would be a whole year until they talked again. She never said happy birthday to Dan on his birthday which made Dan sad. He knew she was just busy with her new life.

Dan had to witness Tracy blossoming into a very sexy sophisticated beautiful woman without him all on Instagram. Tracy is a gorgeous blonde, has blue eyes, has a beautiful face, and a very fit body. Nobody now would ever guess she had been married before to a guy like Dan. She is quite tall for a woman at 5'7". She regularly works out, a habit she had learned back when she ran cross-country. In her adult life she does more weight training. While cross-country had kept her thin back in the day, weight training keeps the fat off the belly, and has allowed her to put on weight in all the right places. She has 32D breasts, long legs, and an ass that just won't quit. When she was with Dan, she really didn't dress to show off her assets. But when she moved to DC, she learned how to dress more sexually and she also completely changed her lifestyle. Dan would see an Instagram post every once in a while that would just blow his mind. She would go to bars and clubs in short skirts, pantyhose/stockings on her legs, 5-inch heels on her size 9 feet, blouses/dresses that showed off her cleavage. The 5-inch heels would make her tower over any average height man. She was truly a head turner.

Her Instagram showed all of this well. She was quickly gaining a significant following which led her to keep posting sexy pictures. Eventually she had sponsorships from lingerie brands. Lingerie photos of sexy lace and stockings would really get Dan going. He began to use her photos as jerk-off material! She had many friends that were just as sexy as her that would often be in her Instagram posts and they all made their own sexy posts as well. They all had the same style with the nylons and miniskirts. Dan found them all to be just so HOT and SEXY!

Tracy's instagram really showed off every element of her life. She would post mirror shots of her work outfits as well. The outfits Tracy wore to her office were, much more conservative relative to her weekend outfits but certainly not conservative. She wore pencil skirts that would end above the knee, tight fitting blouses that only showed a hint of cleavage, and she always wore pantyhose or some kind of nylon. Dan hoped that everytime she was wearing stockings, but of course he couldn't always be sure as the thighs were covered. Sometimes she did have a backseam on her nylons, which excited Dan. To work, she always wore heels. Actually, besides her photos at the gym working out where she wore tennis shoes, it seemed like she always wore heels.

Dan was absolutely addicted to Tracy's Instagram. Dan would come home from work everyday, and look to see if Tracy had made a new post. She pretty much posted something at least once a day. The sexier the better was Dan's opinion. Dan would look at Tracy and her friends profiles to get himself revved up while he stroked his cock. This would eventually lead to Porn. Compared to normal boys, Dan was a late bloomer to pick up watching porn. He thought it was for people who weren't in a relationship. It took his divorce and Tracy's sexy instagram to lead him down this path of horniness. Because Dan was a gaming nerd, he had the perfect setup for the task. Dan had quite the computer setup with 3 large monitors and great audio. It didn't take long for Dan to develop an addiction to Porn along with his addiction to Tracys Instagram profile. Dan would seek porn with hot chicks wearing pantyhose, and particularly, stockings. He loved Lingerie, Panties, Nylon legs, Nylon feet, Heels, and pretty much anything extra feminine became his sexual vice. This needed to be a component of any pornographic material he consumed. He became well educated on all female attire but particularly Nylons. He loved garter belts, thigh highs, pantyhose, fully fashioned stockings, RHT stockings, lace tops, etc.

Dan became so obsessed with feminine attire, he eventually decided, he had to touch some. Going out to find a woman was not in Dan's wheelhouse. Plus Dan figured the probability of him finding what he called a "Nylon Queen" was near impossible. Dan decided that he could just order some online. He used multiple websites to order about $500 worth of lingerie, nylons, and a pair of stilettos similar to what he saw in Tracy's instagram. He was jerking off the whole time he was filling his online shopping cart. He couldn't help but look at the lingerie models, modelling the lingerie he was purchasing. So many stockings, so many garters, so many panties! He was so excited to touch them and wear them. He ordered them all in his own size, as he thought, since he has no woman to model them for him, he has no choice but to model them himself. It would be 4 long days till everything would show up from the various websites Dan had ordered from.

As the days passed, he jacked off everyday to Tracy's instagram posts, and he also prepared his body to model the lingerie. Naturally he's not very hairy, but he made sure he was perfectly hairless, just like the women he admired. Conveniently, everything showed up on a Friday while he was at work, which was perfect because it gave him the weekend for this new experience. He came home and brought all the boxes inside. He couldn't contain his excitement. His cock was stiff just opening the boxes. He spread out the assortment of lingerie and stockings on his bed. He felt he had died and gone to heaven.

He quickly showered the day away, and came back to his assortment to decide what to wear. Grabbing a pair of black lace thong panties he slid his legs in and pulled the panties up. His cock made a lovely little tent in the panties, and he could feel himself getting harder. Next was a black lace 4 strap garter belt. He loved the way the straps framed his stiff penis. Then for the real treat, he chose a black pair of fully fashioned nylon stockings. He had ordered gloves as he knew these were fragile. He took them out of their packaging and took in the amazing nylon material. He lightly touched one to his cheek and then took in the smell of fresh nylon. It was better than he had imagined. He rolled one stocking leg up and slid it up his hairless leg.

As he did he felt a sexual rush unlike anything he had ever before. His cock was the hardest it had ever been. He looked at it and thought, "damn look at that huge hard cock loving these stockings!" Dan thought his cock looked bigger. He put on the other stocking and made sure all the garters were attached. He tiptoed over to where his stilettos were and slid them on. He began walking around the apartment carrying a little feminine sway around with him. He couldn't believe the feeling going through his body. He was loving this. He found a full length mirror and his jaw dropped. From the garter belt down, he looked like a sexy woman. Besides the little penis in the panties of course. Somehow the lace made his cock look feminine, Dan thought that was strange, but he liked it.

He loaded up some porn and began jerking his little cock. He edged himself over and over for multiple hours. So long that he forgot about even making dinner. He was completely lost in a crossdressing and porn trance. Watching girls in stockings fuck dildos or suck/fuck cocks. Dan imagined himself and Tracy wearing matching lingerie and stockings while Tracy sucked his dick. Eventually he was at a bursting point. He couldn't withstand another edging moment. He just kept stroking his cock past the point of no return. He experienced the first crossdressing orgasm of his life as his penis head pulsated and exploded. Dan must have spasmed 10 times and nearly came a quart. The cum shot up a foot into the air and landed back on him. It was all over his garter belt, panties, and on his stockings. He laid there taking in the sight of the dirty thing he had just done. He felt no shame, it was beautiful. This orgasm would mark the true beginning of Dan's new life without Tracy.

End Part 1.