Dan's a Crossdresser Pt. 07

(I apologize for taking so long to write this next part of the story, I can offer a short recap here for those who have read the previous chapters but forget exactly what happened. New readers be warned that it is certainly a spoiler and I would recommend starting at part 1.

Recap: Dan and Tracy were high school sweethearts, went to university together and then got married. Eventually they hit a rut and mutually decided, well mostly Tracy decided, that it was good to divorce while still young. Dan wasn't hitting it right, and he also wasn't giving her the lifestyle she was looking for. Dan wanted to chill and play video games, Tracy wanted to pursue her career and experience more of a high life.

They divorced and Tracy moved to DC with a great job. Tracy completely changed her lifestyle and became what Dan calls a nylon queen. She dressed sexy in nice dresses, high heels, and always nylons. She posted her lifestyle on Instagram which Dan actively followed. She went on dates, but it was always with black men.

Dan during this time became addicted to porn, and eventually cross dressing. He becomes addicted particularly to BBC porn and recognizes how small his own penis is which further drives him into more submission. Basically, he really messed up his whole mind with his addiction. The loss of Tracy and having to witness her blossom into a nylon queen that only dated black men was the real driver.

Eventually after 4 years, Dan loses his job and asks Tracy for help. She has him come to DC for an interview on a Monday, but has him come early on Friday to stay at her place and catch up. He thinks he might get lucky or perhaps rekindle a flame with her.

This doesn't happen of course because she has no interest in Dan. Also she has a man over, Jeffrey, her large black lover. They all end up drinking and hot tubbing where Dan embarrasses himself with a tiny erection. Eventually Tracy and Jeffrey exit to fuck while Dan cross dresses and jerks off while listening in another room and then falls asleep.)

--------------------------

Part 7: Saturday Snooping

Dan woke up to the sound of the garage door Saturday morning around 9am. He woke with his flaccid little cock in hand, his panties, garters, and stockings still on. He was a little sticky as he was covered in his dry semen from his wild orgasm last night. He couldn't help but get a little horny again just at the sight of the aftermath of his little crossdressing cuckold adventure last night.

"I must have fallen asleep right after I came," Dan thought.

He noticed that the door to the hallway was a bit cracked. "I got a little too tipsy last night and accidentally left the door open," he thought to himself.

He hoped nobody had peaked through the door in the morning, or they would have seen the same scene that Dan woke up to see himself. He thought it was unlikely anyone came upstairs, so he moved on.

Dan hid his cum covered lingerie in his bag, showered, and walked downstairs to the kitchen. He found a note on the kitchen counter. It read, "Jeffrey had to go to New York for a client, I went to the gym. There's coffee in the pot and bagels in the pantry, help yourself to anything! - Tracy <3" Dan thought the little heart was a nice touch.

"Help yourself to anything!?" Dan's mind ran to a naughty place. He figured the sound of the garage at 9 was when Tracy had left. If she went to the gym he figured he had till 11 till she got back. It was 9:30 right now. He wanted to explore Tracy's closet and see what kind of sexy things he could find. After all, Tracy is a nylon queen so she must have a great collection of goodies, Dan figured.

He creeped into the master bedroom. It was large and beautifully decorated and furnished. Through the bathroom was a walk in closet. Dan tip-toed inside to find the most heavenly room he had laid eyes on. The closet was basically a room. It was huge. One whole wall was shelving for Tracy's heel collection. Another wall had racking which hanging from it was a massive collection of her dresses, skirts, blouses, and other clothes. There was also a makeup vanity, and next to it, a large dresser with multiple drawers. That's where he would find the prize, Dan thought. He was right.

He opened the top drawer to reveal a collection of nylons that greatly outshined his own collection at home. The second drawer had even more nylons. She had over a hundred pairs, either neatly folded because she had worn them or still in their packaging. She had all of the brands you can imagine from all around the world. Cervin, Secrets in Lace, Oroblu, Fiore, Gerbe, Falke, Trasparenze, Girardi, Giulia, Wolford, just to name a few. There were many more than just that.

Dan moved on to the other drawers to find her lingerie. Sexy lacy panties, bras, corsets, bustiers, girdles, garter belts. You name it, she had it. Dan wished he had all day with this closet.

He moved to the bottom drawer where he found her toys. She had multiple realistic dildos. They of course shared a common theme, they were all big and black. They came in different shapes and sizes, ranging from 7 inches and up. Dan grabbed an 8 inch one and held it up to his face. It had a strange smell, but it was kind of intoxicating. Dan's cock was hard. He unzipped his pants and let it out. He wanted to compare the dildo to his own penis as he had seen in so many pornos. With no surprise, it dwarfed his little cock. Dan liked it.

Dan looked at the time, it was 9:50. Dan had somehow decided till 11:00 was perfectly safe. He had 70 minutes to enjoy this room, and he did not want to let the opportunity go to waste. He didn't know if he would ever get a chance like this again. He had to wear Tracy's lingerie. He had to feel what it was like to be Tracy, and the best way he knew how was to wear her lingerie. They were about the same height and size as Dan was quite thin, so he was sure it would fit him. He stripped down naked and went through all the choices.

He selected an 8 strap black garter belt. Something he actually didn't own but always wanted. He selected the sheerest black panties he could find. And for stockings he selected some black deep welt lace top stockings. They looked like they were the ones that Tracy had worn to the ball back with the original mystery man. Dan strapped on the garter belt, slid on the stockings. He felt as if he was about to explode right then and there without even touching his cock. Just the excitement of dressing in Tracy's lingerie, in her closet, with the chance of getting caught was so exciting.

It was a lot of work connecting all 8 straps of the garter belt. It took some serious time away from masturbating. Dan thought he might have selected the wrong garter belt for the task at hand, but it was so sexy he forgot quickly. He slipped on the black sheer panties. They were so sheer, his cock was easily seen through the material, while pitching it's 4 inch tent.

Dan was loving this experience. He stroked his cock as he looked at himself in Tracy's full length mirror. He went over to her collection of heels and selected some high platform 6 inch stripper heels. Luckily Dan and Tracy had roughly the same size feet, it was a little bit of a squeeze for Dan but it worked out well enough. He went back to the mirror to admire the shape the heels gave him. They made his legs long, and his ass looked so good and feminine. The whole time he kept stroking his cock while admiring his feminine figure in Tracy's beautiful lingerie. He felt like such a naughty slut, for sneaking in here and doing this. His little cock was getting closer and closer to it's edge.

After looking at himself for quite a while in the mirror, he thought it would be hot to play with that 8 inch BBC dildo he was looking at earlier. It had a suction cup on the base of it. Dan fell to his knees and attached the BBC to the mirror, it stuck out right at Dan's mouth level. Dan wanted to worship it as he had listened to Tracy do with Jeffrey's BBC last night. Dan was pretending he was Tracy, after all he was dressed up in her lingerie and nylons. Dan looked at the black dildo and verbally said out loud, "I need your big black cock in my mouth."

Keeping one hand stroking his own penis, and the other on the shaft of the BBC in front of him, Dan slowly opened his mouth. He took the BBC dildo into his mouth. It was quite large, it's girth demanded an appreciation from Dan. Dan sucked it back and forth as he imagined Tracy would do the same. He felt a rush from the base of his little balls up through his spine as he sucked the big black cock. Dan's balls were tight and his cock was hard. It was a euphoria he had never felt before. Serving, honoring and worshiping big black cock was truly overwhelming even if it was just a dildo. It's sheer size had a power over Dan. It gave him a feeling of true submission that made him even hornier. He understood that this must be how Tracy feels when she too is locked into worshiping a giant black cock. Dan kept stroking his cock, and sucking the BBC. Falling deeper and deeper into a black cock and lingerie induced trance, Dan lost all track of time.

...

Dan was really getting into it, making sucking and slurping sounds. Dan's cock aching to reach an orgasm, it approached near the edge. There in Tracy's lingerie, sucking her big black cock dildo, Dan was about to cum.

...

"OH ... MY ... GOD... WHAT THE FUCK ARE YOU DOING!?" Tracy stood in the doorway, shocked at what she had found.

Dan had been caught, with the sound of Tracy's voice, Dan snapped back into reality. Dan turned to see Tracy in the doorway, he stared into her eyes like a deer caught in the headlights. Tracy took in the scene before her. Her ex-husband in her own lingerie had been caught red handed enjoying her black cock dildo. It was dripping in saliva. Dan's cock bobbed up and down begging for the job to be finished, but of course Dan couldn't now. Tracy's face showed Dan her astonishment, but also a slightly twisted smile.

Dan had completely lost track of time, he looked at the clock above the doorway where Tracy stood, it was 11:10. He couldn't believe it, he couldn't believe that much time had gotten away from him. He looked at Tracy as she stood there in her workout clothes, with her arms crossed.

"Well!?" She demanded an explanation even though she knew there was nothing to explain. She wanted to tease him, give him an opportunity just to see what he would come up with.

Dan was speechless. He couldn't even make a sound. He just stayed there on his knees looking at Tracy with eyes wide open. His little cock poking out the side of the panties looking at Tracy as well.

"You fucking sissy slut, you are going to ruin my lingerie!" Tracy yelled.

"I'm sorry," Dan finally managed to say, "I'm so sorry, I didn't mean to do this, I got carried away, I don't know what happened!"

"You know exactly what happened you fucking little dick sissy, stand up, follow me," Tracy commanded.

Her words stabbed Dan's heart. She grabbed him by his little dick and led him to the bed. She pushed him onto it. She commanded him to lay in the middle on his back and spread his legs and arms. Her bed had bondage straps at each corner, which Dan found arousing that she even had that. She strapped each of Dan's limbs to the bed, he wasn't going anywhere.

She began to explain the situation of his predicament to him, "I had a suspicion last night that you were a little bit of a wanna-be-cuckold. Last night, I saw that you recognized the little queen of spades charm on my anklet. When we made eye contact after you saw it, I saw the lust in your eyes. When I saw your little erection in your briefs, it confirmed my hypothesis. Jeffrey and I saw you looking at Jeffrey's big black dick. You just stared for a few seconds too long. Either you are dumb, or it's just too attractive for you to look away. Of course, I figured your attraction was really the thought of your ex-wife, the one whom you were never able to truly satisfy with your little dick...or should we call it a clit? I mean compared to BBC, it really is a clit isn't it?"

No answer from Dan.

She continued, "the thought of your ex-wife fucking a big beautiful black man's cock, a real man's dick, turns you on. That's the only way you would recognize a queen of spades charm, because that's what is all over the internet. It's all the rage with white boys these days. I knew you were drunk and horny, I knew you would go upstairs and jerk yourself. I knew you would listen to us, I am sure you could hear us through the vents, I am sure you were cucking yourself with the audible sound of pure pleasure of a big black cock fucking a little white black cock whore like me. You fucking loved it. Please, at any point, jump in and tell me I'm fucking wrong!"

Dan had nothing to say, she was right on the mark.

"That's what I thought," Tracy continued, "This morning, I remembered how you used to fall asleep after a drunk orgasm back in the day. My curiosity led me to quietly walk upstairs and peek in to see if that happened again last night. Lo and behold, I was right. But to my surprise, it was so much more than that. I expected to find you naked on the bed or on the floor next to the vent. What I found was a sissy bitch dressed up in lingerie and stockings, covered in dried cum. It was then I knew that not only were you a wanna-be-cuck but also a wanna-be-sissy. I had struck gold! So what did I do?...I came in and took a picture and then snuck out leaving the door cracked to keep you on your toes. Then I came up with a devious plan. We are going to have fun today!"

Dan was very curious, but Tracy told him she would finish the story soon. She wanted to take a shower and get into an outfit that would set the mood. With that, she walked into the bathroom, shutting the door, leaving Dan on the bed, still in lingerie, strapped to the bed, and his little cock still standing straight up towards the ceiling.

An hour later, Tracy returned. She had done her full makeup, she was wearing a black corset that made her breasts look gigantic. Connected to the corset were wide garter straps. Connected to the garter straps were black lace top Cervin RHT stockings. She had on 6 Inch heels that had straps that went around the ankles. Hanging off the straps were black spades. She had on thong panties that had printing in white letters on the front side stating "BBC Only" and then an arrow pointing towards her pussy. It was especially slutty. In her hand she had a little box.

Dan's cock which had gone flaccid during the wait, sprang instantly back to life at the sight of Tracy.

Tracy resumed explaining her plan, "I wanted to use the photo that I had taken of you to my advantage. After going to the gym, I bought a little gift for you and I was going to use the picture to blackmail you into wearing it."

Dan knew exactly what it was.

Tracy opened the box revealing a CB6000-S chastity device. She continued, "but then I came home and found you dressed like a bitch sucking a black cock dildo in my lingerie. Now you are strapped to my bed, and you have no choice but to wear the device." She took a couple more photos of Dan's predicament. "I could use these photos to ruin your life, but, I won't if you agree to be my sissy slave, what say you?"

Dan paused, he tried thinking of a way out, but really he was loving this, surely it wouldn't last forever he thought.

"Yes," Dan said.

"Yes Mistress, you mean?" Tracy insisted.

"Yes Mistress," Dan said it right.

Tracy left the room and came back with a bag of frozen peas. Dan could hear her heels clacking around the house and it was such a hot sound. The frozen peas sent a painful shock wave of coldness through Dan's body as Tracy put it on his penis and balls. His cock went limp, his balls pulled in close. Tracy attached the chastity device using the smallest ring of course. Then she slid in the lock, and

...Click...

"My little clit is locked away," Tracy said. The cage looked perfect under the sheer black panties.

Tracy calling it her little clit made Dan squirm. Dan was so fucking horny, he hadn't gone a day without cumming in forever, he sometimes even came twice or three times in a day. Now he was locked in chastity. He had seen many photos and videos of sissies locked up, but he loved to cum, it wasn't in his interest to go without cumming, so he had never played with a chastity device. He hoped Tracy would have her fun today and then eventually she would let him out tonight.

"Okay, now let's make you a real sissy! Not this half ass from the waist down bullshit," Tracy untied the bondage straps, she told him to go upstairs and shave his face and then come back and meet her in the closet where the makeup vanity was. Dan's body was already shaved as he always kept it that way to make his lingerie look feminine.

Dan did as he was told and then came back and sat down facing away from the mirror towards Tracy, she was so beautiful up close. He saw that around her neck hung a necklace with the key to his chastity device nestled in her cleavage. She worked some concealer, eye shadow, blush, lipstick, applied some shading here and there and everything necessary to give him a feminine look. She strapped a corset around his stomach real right. She gave him some jewelry to wear around his neck and some fake hoop earrings. She even had a couple wigs, she took a brunette one and put it on his head adjusting it's position to make it look proper. Her artwork was finished.

Dan turned around and was shocked to see what he saw in the mirror. He looked so hot. He looked like a passable sexy woman. He couldn't believe it. "Wow you look sexy Danielle," Tracy said. Dan was surprised she knew his sissy name, but then again it's pretty obvious. Dan told her that he loved it. She said, "great, I will pick out a dress for you, we are going to lunch!"

Dan's heart fell, "what! like this!?"

"Yes like this, I will wear a dress too, I love showing off, you will too," Tracy said.

Tracy chose a tight fitting dark blue dress for Dan that had a high neckline, "thank god," but a short hemline, "oh no," Dan thought. The bottom of the stocking welts would show when he walked in the dress. When he sat down almost the whole lace stocking top would be revealed. Tracy added one final touch, an anklet with some charms on it that read "BBC Slut". Dan freaked out, what if someone saw it? Tracy insisted, no one will and that was the end of discussion.

Tracy's dress was black, showed off cleavage and was tight fitting past the knees where it had some ruffles. They got in her car and went to a fancy italian bistro. As they walked in everyone's head turned to see the two hot women that walked in. Dan could feel everyone staring, Tracy was used to it and thought nothing of it. "Does everyone really think I'm a woman?" Dan wondered, but then Dan had to order a drink. Tracy wanted to see what he would do. Dan had practiced a female voice when he had sissy sessions multiple times in the past. He spoke, and to his surprise, the waiter was unphased. Tracy let Dan know that she was impressed.

They finished lunch and on the way out they ran into one of Tracy's girlfriends as she was walking by. Tracy introduced Danielle to Amber and vice versa. Dan recognized Amber from Tracy's instagram. Amber was a sexy brunette, with proportions similar to Tracy. Dan remembered multiple photos with Amber getting cozy with black men. He looked her up and down, she had on a simple white V neck tucked into a wavy blue skirt. She was wearing nude nylons underneath and blue pumps to match the skirt. Then Dan saw it, an anklet under the nylons matching the one Tracy wore. Amber too was a nylon queen and also a queen of spades. The two girls kept chatting until eventually Tracy told her to keep her Sunday afternoon open. Then everyone said goodbye.