Crossdresser Pt. 05

Crossdresser Pt. 05

Part 5: Dan sees his ex again

Roughly another year passed, Dan of course kept up his daily routines, feeding his addiction. Time flies when having fun! 

Tracy kept growing on instagram, by now she had over 400k followers. She kept the posts coming. The original mystery black man was replaced multiple times with new black men. Dan could count at least 7 different black men over just the past year. Some of them were tagged so Dan could stalk them, some were mysterious like the original. When Dan could find their profiles, Dan would discover that they were always very successful men. One was a Music Producer, One was a NBA player, and another was a Banker from New York. Everytime without fail, they always had large athletic builds and were very tall. All of this content on Tracy's instagram had given Dan plenty to imagine and solo-cuck himself with. 

It now marked 4 years since Dan and Tracy divorced. Of course he had always sent her a birthday message and they always caught up a little bit once per year at that time. Tracy has done well for herself and by now, she had found a director level job for a large headhunting company. Whenever they did catch up, these were the things they talked about. So I guess you could say their relationship was professional. Tracy always seemed like she wanted the best for Dan. 

Dan's firm went under 6 months ago, eventually leading to a layoff. For whatever reason, he had been having trouble finding a new job. Luckily because he's quite good with his finances, he had been able to keep afloat so far with his emergency fund. Dan actually enjoyed the time off. Of course, he spent most of the time dressed up in lingerie and jerking off to all of his porn interests. But now after 1/2 of a year the emergency fund didn't have much room left so he became absolutely desperate to find employment. This lead Dan to do exactly what he was hoping to avoid, because he was embarrassed. Dan had no choice. Dan contacted his Ex-Wife Tracy looking for a job.

He messaged her and tried to be as professional as possible. He kept it simple, but mentioned he had been without employment for 6 months. He hoped that would motivate her to help. He knew her position at a headhunting company would be of serious value to him. 

A couple days passed, and Tracy finally answered, "Dan, I am sorry to hear you are going through such a tough time. Luckily, the timing is great. Usually I would help you apply to other companies, but I am actually recommending you for an open Accounting position at the company I work for. It's no guarantee of course, you will need to interview, but with my recommendation, you will be first in line. Call me today and let's work out a game plan."

Dan was flabbergasted. His heart raced as he read her message. Then his heart fell when she wanted him to call her. He hadn't heard her voice in 4 years. He waited a couple hours to play it cool and then he gave her a ring.

She answered with such confidence, "Hello Dan."

Dan was silent and speechless

She repeated herself, "hello?"

Hearing her voice was sending shockwaves through Dan's body.

Finally Dan said "Hello Tracy."

They had a little awkward small talk back and forth, all of the awkwardness coming from Dan's side of the conversation.

Eventually Tracy hit him with, "your interview is Monday, why don't you come up Friday to DC and stay in my guest room, we can catch up!" 

Dan couldn't believe it. She invited him to stay at her house. He accepted and asked her why she was so nice. She said she felt like she owed him one after abandoning him 4 years ago, even though she had to change her life, she still knew it was tough on Dan. She said she looked forward to seeing Dan and told him to show up at 7ish for dinner time. With that, they said goodbye and hung up. 

Dan was ecstatic, nervous as fuck, but very excited. He would get to see his lost queen, the now Nylon Queen of his dreams, Tracy. He hadn't really even had a real conversation with any women at all for 4 years and he was going to see the one and only Tracy in 3 days! 

With that, he ended up having the most normal fantasy he has had in a long time. He did dress up in some lingerie and stockings of course, but other than that he imagined having sex with Tracy again. He imagined she would be wearing sexy lingerie and stockings. He didn't imagine any black cock for the first time in a while. He imagined his own cock fucking her, he could last longer than he used to back when they were married because he had so much practice alone. Maybe, just maybe, he could give her a hint of pleasure that she had not had from the Dan of 4 years ago. He knew he couldn't compete with BBC, but maybe he could compete with his younger and more novice self. Maybe he could make sweet love to his long lost Tracy once again. He knew it was a long shot, but he had a little hope.

Friday came and Dan packed his bags. He brought some lingerie and stockings just in case he didn't get lucky and had to jerk it in the guest room. He honestly hadn't gone a day off of masturbation in 4 years, he wasn't going to start now, even if it was at Tracy's house. He got in the car and drove up to DC, making sure he would arrive at 7pm for dinner. He couldn't believe she was making dinner for him as well! It was as if she wanted to treat her lost King, Dan dreamingly imagined.

He could hear his own heart pounding as he pulled up to the address. The house was stunning and in a nice neighborhood. The garage was open and there were two cars inside. "She even has two cars, wow" Dan thought. He had to take a moment to breathe before getting out of the car to walk to the door. Luckily he was smart enough to bring a bottle of wine and a thank you card. He was dressed in his best clothes and had a nice vest over his button up shirt. 

Dan walked up to the large front doors and rang the doorbell. A few silent seconds passed, but then his ears perked as he heard her heels clacking on the hardwood floors as she walked to open the door, getting closer and closer. Was she all dressed up for him? Dan was very pleased thinking she was. He saw a hint of her figure through the purposefully foggy glass around the door. And then she opened the door and Dan had to try his hardest to not let his jaw drop to the floor. 

She was the most beautiful woman he had ever seen in his entire life. He knew she would be from her Instagram, but in person, it was next level. She had on a black and white plaid pencil skirt extending to an inch or two above the knees, and a black lacy blouse that showed ample amounts of cleavage and was tight at her waist-line. Her beautiful blonde hair was long down to her mid back, and she had on large hoop earrings. Her makeup was light and perfect as she didn't need much because she was naturally perfect. And on her legs were black nylons and on her feet were black stilettos. 

The stilettos were about 5 inches long which made her tower over Dan. This was something Dan had not witnessed in real life. She made him feel so short. Her heels made her legs appear to be a mile long. He saw that on her right ankle was a thin silver anklet. It had a little black charm on it but he couldn't quite get a glimpse of exactly what it was. It was on her ankle but under the nylon layer. He had not seen this anklet before in her Instagram posts. "It must be new", Dan thought.

Dan realized too many seconds had passed while he was taking her all in, he said, "I'm sorry you just look so beautiful!" 

He thought to himself, "wow Dan that was actually smooth". 

She responded with a thank you and asked him to come in and thanked him for the wine and card. 

They shared some small talk about the drive at the door and then she said "let me show you your room so you can put your stuff down". 

Dan followed her up the stairs. As he followed her he got an incredible look at her backside. On the black nylons he saw seams, he followed the seams to the top, but the skirt was too long and only allowed him to get so far. Her ass was perfectly formed in her skirt and her waist-line was nice and tight. He followed the seams down to the back of the ankle and he saw what he would recognize anywhere, she was wearing fully fashioned stockings. He could tell by the squared off cuban style reinforced heel. "Oh my goodness, she really is a Nylon Queen", Dan thought. On the right ankle he still couldn't get a good visual of her black anklet charm as she moved too quickly up the stairs.

She let him put his stuff down in the guest room and then gave him a little tour of the upstairs. There were 3 bedrooms upstairs, the guest room had its own bathroom and the other two rooms were connected by a bathroom. She mentioned that she bought this house for the bedrooms as the two connected by a bathroom would be great for a future family. Dan mentioned how awesome of an idea that was. Even though it struck a little jealousy in him knowing of what that would mean if he couldn't get her back.

She said "dinner will be ready in 30, go ahead and settle in and I'll see you down in the kitchen soon." He watched as she walked away so beautifully, staring at her legs and those beautiful seams as she walked. 

Dan cleaned his face and rubbed a little cologne on his balls just in case he got lucky. He was getting hard just thinking about possibly unwrapping her skirt and revealing her garters and stocking tops. He gave his cock minor strokes as he imagined it. But he knew not to go too far as he needed to save himself for later just in case he got the chance to pleasure Tracy. He figured he had a 50/50 chance of getting some. "After all, why did she really let me stay here?" Dan questioned.

After 15 minutes he decided he could go downstairs to the kitchen a little early and talk to Tracy. He gave himself some time to let the little boy in the pants settle back down. 

He walked downstairs, turned, and walked to where he heard noise coming from the kitchen. "Did she have a TV on?" Dan asked himself as he thought he heard a Man's voice. He walked into the kitchen and reality hit him like a bag of bricks. There sitting at the head of the kitchen table was a man. Not just any man, the Banker from NYC, from her Instagram post from about 2 months ago. 

The man stood up and walked toward Dan with an open hand for a hand shake. As he approached Dan, he towered over Dan even more than Tracy did. He had to be 6'6". He was built like a machine. His voice was so deep and powerful the neighbors could probably hear it. He shook Dan's hand while he thanked him for the wine and introduced himself as Jeffrey. Even his hands were huge and belittled Dan's hands during the handshake. He asked Dan if he wanted a beer and Dan gladly accepted. He would need a little alcohol to get through this evening. 

Jeffrey was one of those people that could carry on a conversation with anyone. He was super charismatic which really helped out Dan. Dan was surprisingly able to hold a decent conversation with Jeffrey, and it was mostly due to Jeffrey's charisma. They talked about what Tracy was like back in the day. Tracy would chime in cracking jokes about Dan loving his video games or how Dan talked in his sleep. 

Overall the conversation between the three flowed well, and so did the alcohol. Dan finished his beer quickly and Jeffrey noticed and commented on how a long drive can make a man thirsty. "let's bring out the good stuff" Jeffrey followed up, bringing out a brand new blue label Johnnie Walker and a bottle of Grey Goose. He took 3 shot glasses and poured the vodka in all 3. With that, Jeffrey raised his glass and said "to old friends" and they all drank. And then the oven alarm went off, lasagna was ready. 

Jeffrey shared the blue label during dinner served neat in a sipping glass. Dan matched his drinking speed with Jeffrey, and when they finished, Jeffrey filled the glasses again. Dan commented to Tracy on how great the dinner was, Jeffrey mentioned that Tracy always had something good to eat and then him and Tracy shared a little stare smiling at the innuendo. Dan pretended to not notice even though it most certainly gave him a little tingle downstairs. Dan shifted his mind to move on from it. By now Dan was certainly feeling a little tipsy as he had two glasses of scotch, the shot of vodka, and a beer.

Jeffrey mentioned that the three of them should get in the hot tub out back and continue drinking and chatting, "after all it's Friday night" he finished his suggestion with. 

Dan showed a little hesitation mentioning that he didn't bring a swim suit. 

Jeffrey replied, "non-sense, I hottub in my boxer briefs, you can too." 

Luckily Dan was wearing briefs instead of some panties like he likes to do sometimes. He originally wore the briefs for when he would get with Tracy, but now he knew that wouldn't be happening. 

Tracy said, "well you boys can wear your briefs, I'm going to go put on my suit." She left to go to her room.

Jeffrey poured some vodka cranberry drinks for the three of them. He told Dan to come with him to the hottub, "we can get in while Trace gets ready". Dan noticed that he called Tracy by a nickname. 

They walked to the hottub and Jeffrey set the drinks down and started stripping leaving his clothes on the lounge chairs near by. He looked up at Dan who was like a deer in headlights witnessing this massive man strip down to his underwear. Jeffrey said, "well come on man, the water is hot!" And then Jeffrey jumped in. Dan stripped to his briefs and joined him. 

They were drinking and chatting for about 5 minutes and then Tracy appeared. She walked to the hottub in a tiny pink bikini. The top barely contained her breasts and as she hopped over the edge of the hottub, Dan got a glimpse of her ass in the pink thong bottom. This view inspired an instant erection hidden under the bubbles of the hottub. 

The three chatted, and Jeffrey kept the drinks coming. Tracy had brought the vodka bottle and cranberry juice to the hottub on her way out. Eventually they were all pretty drunk, Dan definitely the most as he's a light weight and Tracy didn't have scotch like the boys did at dinner. 

The more drunk they got, the more hands on Tracy became with Jeffrey. Eventually she was whispering in his ear saying God knows what. Dan tried to pretend like he wasn't watching them, but he was. Tracy was all over Jeffrey and Dan couldn't help his curiosity. Dan had never seen so much lust in Tracy's eyes before. The contrast was so apparent with Tracy's white skin over Jeffrey's dark complexion. 

She leaned back on Jeffrey's chest and put her feet out on the side of the hottub out of the water. There, Dan got a perfect view of her anklet charm on her right ankle. It was a black spade with a capital Q on it written in white. Dan's cock and balls instantly tingled and this finding only helped to maintain the erection he already had. He knew exactly what the anklet charm meant. 

Dan looked at the anklet for too long and then he made eye contact with Tracy. She knew Dan had seen the anklet just then and Dan knew she caught him looking at it. Tracy could tell by Dan's facial expression that Dan knew what it meant. While they shared eye contact for a few seconds, Dan's mind thought, "I don't deserve her". Tracy gave Dan a devious little smile. 

In that moment they both thought the same thing:

Tracy is a Queen of Spades.

Tracy is for black cock only. 

End Part 5 

(the next part gets fun!)