Happily Ever After Pt. 08: Epilogue

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A crossdresser at Disney World with his wife and friends.
16.6k words
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Part 8 of the 8 part series

Updated 06/12/2023
Created 03/15/2021
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Happily Ever After Part 8 The Epilogue

I apologize for taking almost ten months to come back this story. I ran into a real writer's block and just couldn't find the words. I thought about just moving on to another story, but I felt like this needed a definite ending. I finally was able to get something down that I was comfortable with, and I felt was fair to characters in the story. I am sure many of you will be disappointed with how it ends but I think it is realistic and ties both the original story Finally a Princess and Happily Ever After together. Thanks for reading.

The plane ride had been bumpy since we took off from the airport. As we started our decent into Orlando the turbulence was even worse and plane shuttered, dropped, and even felt like it moved sideways. It was a smaller plane, only two seats on each side of the row and I was in the window seat.

We hit another hard Bump and Jordie reached over, grabbed my hand and squeezed it tight. This last jolt had been so bad that the Minnie Ears I was wearing had almost fallen off my head. I looked out the window and could see the lighting in the distance from the storm that was causing all of this.

Another bump and Jordie squeezed my hand tight again. I looked over at her and smiled hoping to reassure her. She tried to smile back but I mostly saw fear in her eyes. I was struck at how different she appeared from when we left our house earlier. Then she was smiling, excited to be going back to Disney World.

It felt like we were past the worst of the turbulence, and I could now see the ground as we continued to descend. I wasn't as nervous as Jordie but I was going to be happy to be on the ground. I was looking forward to the upcoming weekend and warm weather. The forecast for the Orlando area was sunny and low eighties for the next couple days.

"We are almost on the ground. I told her.

"I am going to be really happy to land. I could really use a drink by the pool this afternoon." Jordie squeezed my hand quickly.

The next jolt we felt was the wheels hitting the runway and you could hear the sighs from the passengers all around us along with a little applause. The taxi to the gate seemed a little longer and I continued to watch the flashes of lighting from the passing thunderstorm.

When we stopped at the gate, I gathered my stuff from the pouch in front of me, pulled the Tinkerbell Lounge Fly back pack out from under the seat in front of me and put it all in there. I looked at me phone to see if I had any texts and saw one new one. I opened it to see that Disney was letting me know that our room was ready.

"Good news. Our room is ready to go so we can go straight there, change into our bathing suits, go to the pool and get your drink." I told Jordie.

"That is awesome." Jordie replied with a smile.

The plane door opened, and people were starting to exit the plane. Jordie stood up and turned her back to me, stretching her arms over her head. This pulled up the back of her pink Disney World spirit jersey she was wearing. I admired her butt in the tight black leggings she was wearing it. She really had a great ass.

I adjusted my Minnie Ears. They were purple sequined and went well with the lavender Disney World spirit jersey I was wearing with a pair of black leggings also. I was happy that it was still a bit rainy in Orlando right now. We dressed for the weather we experienced as we walked out of our house in Virginia not for the weather we were headed towards.

We made it to the concourse and Jordie said. "I really need to pee."

"So do I. There is a bathroom at the end of this gate area on the way to the baggage claim, we can stop there." I responded.

We found the women's room, there was only a short line. I thought that this may be the only thing I disliked about living as a woman, longer lines for public bathrooms. I realized that since I had gone full time, not just occasionally presenting as a woman in public, I didn't have the same level of nervousness I had in the past when using the women's rest room.

I finally made it to the stall, hung my backpack on the hook on the door before sliding my leggings down, then the thong panty before sitting on the toilet and peeing. When I done, I wiped myself and situated my pantyliner and it got my thong in place before pulling up the leggings. Looking down I saw the smooth flat front that I wanted.

I had grabbed the backpack and put it back on, washing my hands I admired my nails. Jordie and I had gotten them done yesterday. I had gone complete Minnie Mouse with red nails and white polka dots. The acrylic extensions were the longest I had ever had, I was still getting used to them.

I took a second to look at my makeup. I had gone light this morning, the eyeliner and mascara looked good along with the light-colored lipstick. Jordie stepped up to the sink next to me and was soon doing the same. I smiled at her in the mirror, and she returned it.

We walked to baggage check. The fact that I had checked a bag for a two-night stay was a definite testament to the fact that I was now a woman or at least living as one. I took some comfort in the fact that Jordie had checked a bag also.

As we came down the elevator, I saw a man holding up a sign with my last name on it. A part of me was disappointed that we weren't using The Magic Express to travel to our Disney Resort. My panties were still bunched that Disney had stopped that service.

"I can't believe I am back here without my kids again. I may be the worst mother in the world." Jordie said as we waited for the carousel to start so we could get our luggage.

"You are an awesome mom. I don't think the kids would enjoy being here for a bachelorette party. Plus, we aren't going to going to the Magic Kingdom or Animal Kingdom. Lastly, we are bringing them in the Spring." I told her taking her hands in mine.

"I know... still.... This is the second time I have been here in less than two months, plus the Disney Cruise last spring. I can't help but feel a little guilty."

I pulled her into a hug. "You have the most beautiful heart on this earth."

The alarm for the carousel sounded as it turned on scaring me and causing me to jump and maybe even squeal just a little.

"You really are a girl aren't you." Jordie laughed.

"Wow... you almost sound like Sara's saying you are such girl." I said as we broke apart.

"I am sorry... I wasn't making fun of you, I promise, and I didn't mean to sound like her that is for sure." Jordie eyes has widened.

"Gotcha!" I smiled wildly at her.

"Oh, you bitch! I actually felt bad for a minute making you think about her." Jordie laughed.

I spotted my luggage grabbed it. Jordie saw hers as I was pulling mine off the carousel and she quickly did the same thing. Our driver walked over and took the bags for us, we followed him to the Town Car. He opened the doors for us and loaded our luggage in the trunk.

"Ladies, we are going to the Yacht and Beach Club, correct?" He asked as he slide into the driver's seat.

I told him yes and leaned back into the seat. Jordie's comment had made me think about Sara and I was trying to determine what emotion that was causing. Our relationship had completely blown up on our last trip to Disney.

**********************************************************************************

While Sara had started that trip completely supporting my crossdressing and letting me live out fantasies and dreams that went back to my teen years. By the end of it we had both slept with other people. Actually, I had slept with one man and given a blowjob to another. Sara had also slept with a man who let her experience some fantasies she had for a long time.

Jordie and her mom had been on that trip with us. They were both supportive of my desire and need to have experiences as a female. Jordie and I had grown very close during it and now she was my biggest supporter of completely transitioning to a woman.

When we got back home things had gotten worse with Sara. She wanted me to go back into the closet most of the time. I wanted to burst out of it. Two things caused us to separate, almost immediately, after we returned.

Within three days of returning, I was making an appointment with a therapist who specialized in gender therapy. In Sara's opinion that meant that I was planning on transitioning as soon as possible. The reality was I just knew that I needed to talk with a professional to help me understand what I was experiencing.

The second was the Saturday after I got back, I went on a date with Matt. I had met him on that trip to Disney World. While we were there, I had a pseudo date in a club one night where we had a couple of drinks. We had been flirting for a couple days prior to that.

The morning after our date I had run into him and after finishing our coffee and a little breakfast I had gone back to his room. His sister had taken his kids to a character breakfast, and we took advantage of him having the room to himself and I gave him a blowjob.

He was the second man I had performed oral sex on, and I knew that I loved doing it. Sara had been encouraging my experimenting with men up to this point. I had found that her encouragement though was contingent on her being able to have some control on the when and who I was experimenting with.

***********************************************************************

As we drove under the large Welcome to Disney World Sign Jordie turned to me. "Are you okay? You are normally bubbling when you are here. This isn't about Sara, is it? I am sorry I brought her up."

"No, I am fine. I didn't sleep great last night so I think this is fatigue. I will be great once we get checked into our room, in our bathing suits, and we are enjoying a drink at the pool." I smiled at her.

It was a little white lie, but I knew Jordie would feel bad if I told her I had been thinking about Sara. She had been going out of her way to let me know she completely supported me and was on my side during all of this.

"Me either. Every time you got out of bed last night, I was awake. I love how you try to be quiet as you move throughout the house in the middle of night, trying not to wake me." She reached out and squeezed me thigh as she told me this.

**************************************************************************

Thinking back to what happened with Sara after our return from Disney, I remembered that when I returned from my date with Matt, she told me she wanted me out of the house. It might have been a mistake on my part to have set up the date so soon after we returned. I would admit that what I described as the teenage girl part of my crossdressing and interest in men had possibly got the best of me.

I had a serious crush on Matt and felt like something special had clicked between us at Disney. We had stayed in touch by text, including some very flirty texts and even a little sexting. I kept pushing to see him and he finally agreed to that date. He asked if I would want to come down to his house and go out to dinner.

I drove to his house which was about an hour away. I went over the top girly, lots of makeup, hair all done up, a short little black dress and bright pink pumps with about a four-inch heel. Honestly, I was hoping for a quick dinner and then to go back to his place and have him fuck my brains out. I was so sure that is what was going to happen that my purse had my cell phone ID, a credit card, mascara, lipstick and lube in it.

The first sign of a problem was when his sister answered the door after I knocked. I then heard his kids in background. He had told me when set up the date that his ex-wife had the kids this weekend. His sister's greeting was cold and they way she looked at my outfit made me feel cheap.

I stood there expecting to be asked in but suddenly Matt appeared, wearing jeans and polo shirt, making me feel way over dressed. I will admit that he looked good in his casual outfit.

"Hey Brandi, you look nice. Ready to go to dinner?" He said stepping out the door.

Before I could even respond he turned back to his sister. "Thanks for watching the kids. I should be back in a couple hours."

He led me to his truck, a Ford F150 of course, and he did at least open the door for me. It was a little bit of an adventure getting in the passenger seat in my dress and heels, but I did manage to do it without flashing my panties at him. Of course, concentrating on not flashing him made me think I had spent ten minutes deciding what panties and bra to wear because I thought he was going to see me in just those later this evening.

We made small talk on the way to dinner, mostly about his kids. We hadn't talked about where we were going to eat, and we pulled into an Outback after about a ten-minute drive. He had at least made the effort of making a reservation, so we were seated immediately.

Over dinner we continued to talk about his kids. I had really enjoyed meeting them and getting to know them at Disney. I told him about going to a therapist and that I we had set up a regular appointment schedule. When I mentioned Sara and our struggles, he got quiet.

I was surprised that I was happy when dinner was over. I felt like we had gotten to the point where the conversation was forced. We left the restaurant and and were headed back to his house. We turned into his drive way and slowly made our way down it before he parked. His house sat off the road and it was a little isolated.

"I would ask you in but, with my sister in there it might be a little awkward." He said as he turned off the ignition and killed the headlights.

"Yea... I think she only tolerates me at best. I didn't think your kids were going to be here this evening. I was thinking maybe we... would have had the house to ourselves. I might have been hoping for that actually." I smiled at him but felt nervous and awkward as I said it.

"Oh... yea their mom had a change in her plans at the last minute, sorry." He had turned towards me and didn't look like he was in hurry to get out of this truck.

Our eyes had adjusted to the dark and the porch lights and lights on the exterior of the stand-alone garage made it so we could see pretty well now. I was trying to read his facial expressions.

"Since they were here, I wish I could have at least said hi to them. I really like your kids."

"Of course. Maybe next time."

"Uh... yea sure. Or next time they will be at your exes, and we can have some time alone." I smiled at him.

"Well... we are alone right now, aren't we?" He said with a grin and raised eyebrow.

I immediately felt some butterflies in my stomach. We hadn't even kissed at this point, and it sounded like he was suggesting that we fool around in his truck. I just nodded yes, and he moved towards me leaning over the console and pulling my head towards me he kissed me passionately.

That kiss was followed by another, this one more passionate. I had one hand on his chest, and I felt him put one of his hands on top of it and slowly move my hand down his body until it was resting on his groin. It was obvious, even through his jeans, that he was hard. I squeezed and stroked it and heard him moan into my mouth.

I broke away from his kiss but didn't move my hand from his lap. I looked down and then back up at him and his eyes made it clear what he wanted. The console in the middle of his truck was going to make this difficult and I took a quick look at the back seat. There wasn't much more room in the back of it with two booster seats strapped in for his kids.

I drew up my knees under me and was kneeling in the passenger seat. I brought my other hand down and using both hands I unbuckled his belt and then undid the button of his jeans. Next, my hands went to his zipper and pulled it down. I snaked my hand into the opening and could feel the heat of his penis through his boxer briefs as I ran my and over it.

"I think you would enjoy this more if we can slide your pants and boxers down." I told him looking into his eyes and smiling.

He immediately lifted his hips up and grabbed his pants and boxers and slide them down his thighs stopping when they got to his knees. I smiled at him and then kissed him while my hand wrapped around his now exposed dick. Breaking the kiss, I quickly looked into his eyes and then dropped my head down to his lap.

I gave the tip a quick swirl of my tongue and then took his cock into my mouth. He audibly gasped when I did that and felt a hand on the back of head. He wasn't pushing on it but was more petting and caressing me.

I began to bob up and down while my nostrils took in the manly, masculine, musty aroma from his crotch. I wanted to suck his balls into my mouth, but this angle wasn't going to allow that. While sucking on his dick I let my hand move to his nuts and gently caressed them. This brought out another moan.

His dick was already becoming more rigid, and his balls were starting to draw up. His moans were louder also, and I knew this was going to be over quickly. I was happy about that since being on my knees on the passenger seat, and leaning over the console to get his dick in my mouth, wasn't the most comfortable position. I imagined how this would look if someone where to see us.

"Oh, fuck that feels amazing. How did you get to be so good at this? You suck dick like a pro." I heard Matt say.

"Fuck, fuck, fuck... don't stop that."

I had brought my hand up from his balls and was using it to slowly jerk him in time with my mouth moving up down his cock which hardened even more.

"Oh God. I am cumming." He yelled out.

Cum had already shot out and hit the back of my throat by the time he said that. I was doing my best to swallow it all as he just kept shooting wads of it onto my tongue, but it was escaping out of the sides of my mouth.

When he finally stopped, I lifted my mouth off him and sat up for a second. I felt cum on both sides of my chin and tried to scoop it with my finger but knew that some of it had dripped down and landed on the front of my dress.

"That felt incredible. God you can suck a dick." Matt said to me.

I was still cleaning my chin but told him thanks and then put my head back into this lap and used my tongue to clean up the last bit of sperm that had leaked out. I gave the tip of his dick a quick kiss and sat back up. I went to kiss him again and he pulled back.

"Uh... sorry but uh... you are kind of messy right now."

I was surprised at that and a little hurt. When we were at Disney, he had let me kiss him after I sucked him off and swallowed his load. It was now really awkward in the cab of his truck. I wasn't sure what to say.

"I am sure my sister heard us pull in and she told me she would be anxious to leave once we got home. I probably need to get into the house." He said nervously.

"Oh... sure. Okay... I guess... I guess I will be going then. Uh... thanks for dinner and for the umm... desert." I tried to smile at him as I said the last part.

"I should thank you." He said forcing a laugh while opening the driver's side door.

I opened my side and stepped out. I thought he would walk around and at least give me a hug before I left but he just stood there looking at me over the hood of his truck.

"Okay... well will you text me or call me tomorrow?" I said hoping it didn't sound like I was pleading with him to do it.

"Uh... sure. Have a safe drive home." He turned and headed towards his house.

As I sat in my car and buckled my seat belt, I could feel tears forming in my eyes, by the time I had turned on the ignition and turned my car around in his driveway I was fully crying. I knew I was far from the first girl to give a blowjob in the front seat of a car, but I felt like I had just been used.

The drive home seemed to take forever and when I entered the house Sara was waiting for me. I am not sure what I expected from her when I got there but it definitely wasn't the reaction that I got.