Neighborhood Secrets Pt. 03

The Neighborhood- Part 3

I woke up just before seven in the morning. I was groggy, mostly because I had trouble falling asleep after my fight with Steph the night before. After what had been a pretty good day that included some physical intimacy between us, we had ended it with some ugly words. It felt like all the steps forward we had taken yesterday had disappeared.

I knew my insecurity and jealousy of her interactions with our neighbor Mark had been the primary cause of it. I also felt confident that I wasn't just imagining something there. If I was honest with myself, it made sense to me. Mark was definitely a masculine man's man, and you couldn't deny he was attractive.

The fact was I didn't give off a feminine vibe when I wasn't cross dressed, if you didn't know I was a crossdresser you would never guess I liked to dress up. The problem was Steph knew I was crossdresser, and, in my mind, that had to make her see me as less manly than our neighbor. That in turn made me insecure.

Yesterday she had made me bring some of my girl stuff home from my storage locker. She wanted me to dress in front of her after our daughter left for the day. I wasn't sure if she would still want that now after last night. If she didn't, I wasn't sure if I would be relieved that she wouldn't see me dressed, or disappointed that a possible opportunity to have her not only accept me, but also support my dressing would be lost.

I climbed out of bed and slipped out of the guest room and quietly went into the master bedroom. Steph was still asleep and I was able to brush my teeth and put on a pair of gym shorts and a tee shirt before heading to the kitchen. Callie must have gotten up while I was doing that, and I could hear the hall bathroom shower running as I went by.

I started the coffee and decided to make pancakes and bacon this morning. I wasn't sure what time Callie was leaving but figured it had to be fairly early. I cooked the bacon and had just mixed the pancake batter when she bounded down the stairs into the kitchen.

"Got time for a quick breakfast?" I asked.

"Uh... yea I guess they are picking me up at 08:15 so I should be good." She responded.

She sat her emerald green, Loungefly Tinkerbell back pack on the counter and took a seat at the kitchen table. She had her hair in a pony tail and was wearing a pale-yellow tee shirt with denim shorts, with running shoes on her feet, she was dressed for function instead of style.

"Will they let you in Busch Gardens with a Disney World back pack?" I smiled at her.

"I guess I will find out. At least I didn't add a Tinkerbell tee shirt." She laughed.

"But your Tinkerbell shirt is awesome." I said seriously.

Her shirt was a short sleeve white v neck with a full body color picture of Tinkerbell off set on it.

"You are welcome to borrow it anytime. I know you are fan of Tink." Callie said with a wink.

I gave her an uncomfortable smile. Again, I wasn't sure if it was my imagination, but it seemed like in the past few years my daughter had been making more and more comments like that. I didn't acknowledge it and tried to change the subject.

"What time do you think you will be home? Not prying just asking, I promise."

"Probably close to midnight. I doubt that we will leave before around nine o'clock."

I took the pancakes off the griddle and put them on a plate with some bacon and carried it over to her. I had just made my plate when Steph entered the kitchen. I sat my plate on the table in the spot that she normally sat at and poured her a cup of coffee before pouring more batter on the griddle.

Callie and her mom greeted each other with good mornings and started to eat while I made some more pancakes before joining them at the table. Steph and I hadn't spoken to each other yet and exchanged some awkward glances. We both asked Callie questions about her night, who was going today, and some questions about her upcoming week at school.

"Oh... wow. I need to run and pee really quick; they are going to be here any second. I didn't realize the time." Callie said jumping up.

"Good morning. How did you sleep?" Steph asked me after she left the room.

"Not great. You?" I said honestly.

"Not great." She said.

"They're here. I will see you all late tonight... or early in the morning tomorrow I guess if you are both a sleep when I get home." Callie announced stepping back into the kitchen to grab her back pack.

Both Steph and I said we love you in unison which did cause us to smile briefly at each other. We heard the front door open and close as she left.

"Can we talk about last night?" Steph asked.

"Yes." I said nervously.

"Actually, let's start with yesterday afternoon then talk about last night."

"Okay." I was still nervous.

"I really enjoyed yesterday afternoon... and not just because of the incredible orgasm you gave me." She smiled. "I enjoyed it because we talked, we were honest with each other, it was fun, I felt really close to you for the first time in... well a long time."

"I liked enjoyed yesterday afternoon also. Even if I was scared to death talking about it. And I really liked kissing you and going down on you." My accent on the word it made Steph grin, and she smiled broadly when I said kissing you and going down on you.

"I want us to keep being honest. Can we do that?" She took my hand in hers.

"Yes. I hope so at least."

"Okay... well... here goes. You are right... I was flirting with Mark. I do have a little... I don't know... I guess crush on him. That is it though... there is nothing happening between us beyond that." She squeezed my hand and looked right at me.

I took a second to absorb what she said. It wasn't like she was telling me something I didn't know. I wanted to be honest in how I responded.

"Thanks for being honest. I shouldn't have attacked you last night about Mark. I wish I wasn't so insecure but..." I stopped not sure I could finish.

Steph waited a minute then said. "But what? Tell me. Yesterday was so great because we were being honest with each other. Just tell me."

"But... I know he is the things that I am not... especially when... when we actually acknowledge that I am crossdresser. When all of that is kept hidden I can at least pretend that I am a manly man." I blurted out.

Steph smiled. "Here is a secret for you. Even if you weren't a crossdresser, you aren't a manly man. You might have a manly man job, although there are some badass women that work with you so... Never mind going off track... what I am trying to say, badly it appears, is... you are kind, you have empathy, you see things... differently."

I started to protest.

"Let me finish... do you know what the women who know you tell me?"

I shook my head no.

"They tell me how lucky I am to be married to someone like you. They start with how much you help with the housework and chores, how great a dad you are to Callie, but they end with your kindness and empathy. They are right, I am very lucky." Steph reached for my hand and squeezed it.

"Yea... except that comes with someone who wants to wear dresses and heels... and things." I said looking down at the table.

"Yes... but maybe that is why you are special. Look, I haven't helped this at all. I always reacted wrong when I discovered things. Although you don't help either by not being honest." She looked directly at me as she spoke.

"Can you tell me why you seemed to have done a complete 180 on this? It is very confusing to me. I keep waiting for the other shoe to drop or something." I told her.

"Do you hope that shoe is a platform pump?" Steph giggled. "Sorry... trying to lighten the mood. It isn't any one thing exactly... it is a combination of things, starting with I am worried about our future, what happens when Callie goes off to school and it is just us here. Maybe I am more mature now so I am more understanding, I don't know. I am tired of fighting over stupid things."

"I have those same worries about our future, and I hate fighting with you also." I said looking down.

"So, let's stop fighting and start talking and be honest with each other. I will tell you... what you said about why you worry about Mark. That makes sense to me. I hadn't thought about it from your perspective. I can promise you... I would never leave you for him. I don't want that much masculinity in my life every day." She smiled at me.

"Thanks... I..." I stopped not sure exactly what I was going to say.

"Now... that much masculinity in my life for an evening, or a day.... Maybe even a long weekend... I might enjoy that." She said laughing.

I smiled and then laughed lightly. I realized I liked this banter between us. I liked that we could joke about it.

"I am pretty sure he would enjoy a long weekend with you also." I told her.

"I also want to apologize for what I said about Rob last night. I purposefully wanted to say something mean and hurtful and that is what I blurted out, sorry."

"Uh... well... in the spirit of honesty..."

She cut me off her eyes wide. "Really, Rob?"

"Not like all the time but... yea... you might have been right with what you said about me... you know, doing that, at least a couple times." I couldn't look at her as I told her that.

"What I said is that you were thinking about Rob while fucking yourself with your toy. I am trying to decide if that is kind of hot. It is going to kill me to not tell Kim." She laughed.

"Please... never! Promise me... you have to promise me!" I begged.

"I promise. I promise I won't say a word to anyone about any of this as long as you are honest with me, deal?"

"Yes... I promise I won't lie. I can't promise I will just offer stuff up... I will try, but I still get nervous and scared although I am doing better, I think." I responded.

"That is fair... are you ready to... I guess... play dress up? Is it okay to call it that? I don't want to say something that offends you, but I also want this to be fun. Again being honest, I am a little surprised but I am really looking forward to this." Steph said sincerely.

"That doesn't offend me so we can call it that. I might be too nervous for it to be fun but I will try and have fun with it. This is the first time I will have ever let anyone intentionally see me wearing women's clothes." I told her.

"I know. I am excited to see what you picked out for your debut."

"Uh... I picked out two outfits. Is that okay? I couldn't decide between them, and they are both kind of my favorite." I didn't look at her as I spoke.

"Of course, that is okay, and it sounds like a woman thing. Can I ask a question... actually two... when you dress up do you... umm... well do you think of yourself as female while you are dressed, like do you want me to treat you like a girlfriend. I mean as a friend that is a girl." It was Steph who was now nervous.

"I hadn't thought that deeply about it, especially specifically with you. Uh... I think so, I guess. Maybe we need to see how it feels. Figure out if you are even comfortable with seeing me dressed and me being dressed in front of you."

"Yea... that is fair and makes sense. Uh... the other question... do you have a girl's name that you think of for yourself when you are dressed?" This time she smiled.

"Uh... sort of. I like Brianne." I blushed and felt my checks redden.

"Oh... interesting. Is that because it is close to Brian? Or is it because of Brianne from work?"

The truth was it was both. One of the firefighters I had gone through rookie school with and shared a station and shift assignment, during parts of my career, over the years was named Brianne. She was a tall, very athletic, and fit woman who fit in great in the male dominated culture of the firehouse. She was also attractive and a very girly girl when she was off duty. I was jealous of the clothing I would see her in, or her outfits she would post on social media.

"Yes." Was all I said.

Steph laughed heartily. "Well, I think Brianne needs to go take a shower. Why don't you start with using my shampoo and conditioner. It is completely up to you but at least think about shaving your legs and under your arms. Then shave your face as closely as you can."

I stood up feeling the butterflies build in my stomach. Steph stood up also and stepped in front of me and leaned in and kissed me passionately. We broke apart from the kiss and she stepped aside and I moved out of the kitchen she swatted me on the ass.

"You know... for a boy you have always had a great ass. Hopefully you picked out something to show it off."

I didn't acknowledge her and headed up the stairs and quickly got into the shower. I followed her instructions for the shampoo and conditioner. I enjoyed the scent of them and had used them before when I dressed up. I stared at her razor and shaving cream on the shelf before tentavily reaching for the shaving cream and lathering my leg up. I then quickly took a razor to my leg that was resting on the bench of the shower so I wouldn't change my mind.

I followed that with doing under my arms. I currently didn't own any sleeveless dresses because of the hair under my arms. I was excited that I could possibly get one now.

When I stepped out of the shower and felt my smooth legs rub against each other a small thrill ran through me. I dried off and went to work on my face getting it as smooth as possible. I heard a rap on the door.

"Hey... two things- crack the door open to let the steam out so it is all gone when we start your makeup. Also... if you shaved anything besides your face make sure you put some lotion on it. It will help prevent itching." I heard Steph say.

I followed her directions and when I was done, I started to step out of the bathroom. Right before I did, I brought the towel up under my arms and tucked it tightly around me. I then nervously stepped into the bedroom.

Steph was sitting on the bed texting and didn't see me at first. She eventually noticed movement in the room and when she looked up a big smile spread across her face. I think because of how I was wearing the towel. I noticed she looked down at my legs and saw the hair was gone and her smile grew a little more.

"So, I think the best way to do this is... I will do your makeup then go downstairs and you can get dressed. Since it is still early I will make us a couple Bloody Mary's and when you are ready... you come down and make your debut. What do you think?" She asked.

"The Bloody Mary part sounds good. All the rest of it scares me to death but I am not backing out now." I told her with a small smile.

She smiled back and hopped up off the bed and went into the closet. She came out with a mid-thigh length floral print silk robe and handed it to me before heading to the bathroom. I removed my towel and put the robe on and followed her in.

The master bath had a long double sink vanity with a space to sit and do makeup. Steph grinned when she saw me in the robe and indicated I should take a seat. I saw her raise an eyebrow as I used my hand to sweep the back of the robe under me.

"Our coloring is pretty similar, your skin tone is maybe a touch lighter than mine. Depending on how this goes you might want to get your own foundation for the future that matches a little better. Now watch what I do so you can eventually do it yourself."

I paid very close attention as she blended the foundation in using brushes. I was surprised to see that any hint of facial hair completely disappeared. I was lucky because I had light facial hair to start, and it was blonde. When she finished it had made my cheekbones seem to stand out a little and pretty much removed any hint of male facial features.

"Do you like what you see?" She asked.

I nodded yes as I felt myself growing a little more comfortable with this process. Steph did step back for a minute and give me a good look over. She then asked if it would be okay to thin up my eyebrows just a touch. I told her okay but worried a little about how that would look in boy mode.

Some precise plucking later and I could see a real difference, but I didn't think most people would notice it. Next she started on my eyes, beginning with eyeliner.

"Umm... so... I am asking out of honest curiosity... and well girls talk about stuff also... when you bring your...stuff home because you are going to be alone do you bring your toys every time? I guess what I really want to know is does dressing up mean you are also going... to... get off?" I could tell she was nervous asking the question.

"No... in fact, most times I don't. My desire for that... well... it... I guess you could say it kind of... builds up, maybe. Like I will do it and not need to do it again for weeks or months even."

Her face showed she listened to what I said and seemed to understand it.

"And... uh... I feel like I am prying but... well I guess I am, but I am little fascinated by all of this. When you do that... do just think about getting... getting fucked and that is what the toy simulates? Or do you... do ever think about or fantasize about giving a blowjob?" Her voice almost cracked a little as she asked that.

I had told her I wouldn't lie so I built up the courage to answer. She looked at me in the mirror as she waited for my response.

"I definitely think about and fantasize about giving blowjobs." I blurted out.

"I guess that isn't surprising. That is a pretty girly thing to do." She winked in the mirror. "If you got the chance to, do you think you would really do it? Or is it more of just a fantasy thing?"

"I wouldn't because I would never cheat on you." I told her immediately.

"If I said it was okay... like it was hall pass type thing or get out of jail free, whatever, would you want to do it."

"Yes." I said without any hesitation.

"Interesting... and do you think you would want to... swallow?" Her grin in the mirror was back.

"Yes... at least once to see if I liked it." I told her.

"Well... you know my feelings on that part of it. Not a fan. I don't mind giving head, just have never liked swallowing cum. Have you ever... tasted your own?"

I did know that. It had been established pretty much from the start of our relationship twenty years ago. I don't know about previous boyfriends, but she had only swallowed my load twice and it had been at least fifteen years since the last time it had happened. She would still occasionally suck on my dick, a little, but I was much more into giving oral than she was.

"Yes."

"More than once? And did you like it?" She asked.

"Yes, more than once... and I didn't... not like it..." I told her.

"Interesting..."

Steph asked a couple of questions about the outfits I had picked out to put on. Mostly about the color but also a little of the details telling me it would help with the eye shadow she would use. In the end she decided just to go with a neutral color and not put it on very heavy.

"Can I ask about... well... does it feel good when you use your toy in your... your butt? The one time we tried that... when you fucked me in my ass. It wasn't very enjoyable, or at least it wasn't for me."

I had been shocked when Steph had let me do that. We were celebrating our fifth anniversary. Her parents were watching Callie and we had gone to a resort for a long weekend. She said she wanted to do something special for me and try something a little different to spice things up.

I could tell afterwards that she wasn't a fan and I never asked her to do it again. I did love knowing that I had done it though. Almost every time I looked at her ass in a tight pair of pants, I thought to myself, I fucked that butt. It killed me not to be able to tell anyone that I had done it.

"Yes... it feels really good if I am honest. I have heard that for guys, because of the prostrate it is different. I have also found out that lots of lube is important. Umm... I can actually orgasm from it."