My Best Friend and Her Husband Ch. 04

Author's Note: This was originally going to be one chapter. As a longtime reader I was curious what it was like to write a story. To put it simply...It's Hard! By the time you put an idea into words and then check for spelling, grammar, etc, it takes hours and sometimes days. I have no idea how others write these long stories. I am very impressed. Anyway there seemed to be interest in the 3 stories so far and I've been seeing feedback that people were upset that I ended it so quickly. So you've twisted my arm. If you've read the end of Chapter 3 you know how the story ends. Chapter 4 will start to fill in the gaps in between. Enjoy!

Chapter 4

"Babe, do you mind sleeping in your room tonight? Trent and I have a lot to talk about," Jess says to me.

I agree and walk to my room. I turn on the TV and get in bed.

MEANWHILE, BACK IN THE MASTER BEDROOM

Jessica went into the bathroom to change. Trent is still lying in bed, naked, with smeared makeup, his blonde wig all frazzled, and his cum all over him. He is staring up at the ceiling deep in thought.

Jessica comes out wearing a cute light blue babydoll nightie with some wet wipes in her hand and sits down on the bed.

"Here," she says and hands the wipes to Trent. "Clean yourself off and let's talk."

Trent wipes himself clean of the sticky stuff and gives Jess a confused look.

"Sooooooo," Jess says, "My hot husband loves cock and wants a nice pair of boobs."

"Come on Jess," Trent says, "I was just saying that in the moment because of all the pleasure."

"So you did enjoy it?" Jess asks. "Well of course you did. By my count you came twice just from being fucked in the ass. You didn't even try to grab your dick and play with it."

"I don't know what you want me to say," he replies. "I'm so confused."

"Do you prefer being a girl?" she asks.

"Do I have to pick one or the other forever, or just for this weekend?" he asks.

Jess leans in and hugs him tight. "Baby, it can be whatever you want it to be."

"Well I know I love you, but I am also loving this right now," he says.

"How do you want to handle the rest of this weekend?" she asks. "Tomorrow is his last full day with us and he leaves on Monday around Noon."

"I have to think. Are you okay with me doing this?" he asks.

"Yes."

"But why?" He asks. "Don't you want your hot husband back?"

"Sounds like you need to do this. You need to have these experiences. I don't want to be the reason you don't get the chance to find out what you need to be happy. Let's see how tomorrow goes and we'll take it from there," she says.

This time he leans forward, hugs her and gives her a peck on the lips.

She continues, "Why don't you get ready for bed. It's getting late anyway. Decide if you want to join us as Trent or the hot blonde we created. If you want to keep this up, think about what you'd like to do with him tomorrow. Then we'll see if he can stay a little longer so you can keep experimenting. Come in when you're ready."

Jess gives him another kiss on the lips and leaves the room.

Trent slips off the bed and goes into the bathroom. "Yikes!" He says to himself when he sees his reflection in the mirror. His wig and makeup are a total mess. He has made his decision and starts to comb his hair and applies some lipstick. Still naked he needs to find something to wear. Looking through Jess' side of the closet he sees a black and pink babydoll nightie with a matching thong that he bought for her. When he saw it at Victoria's Secret he knew she would look smokin' hot in it. Little did he know he would be wearing it one day. He pulls the nightie over his head. It is clingy enough to create a hint of cleavage over his flat chest. He steps into the thong and gets a little tingle in his dick as the back settles into his crack. He does a quick check in the mirror and walks towards the guestroom.

MEANWHILE IN THE GUESTROOM

I'm lying in bed and hear a knock at the door.

"Come in," I say and Jess walks in wearing her blue babydoll. I continue, "When did my best friend become such a hottie?"

"I've always been hot!" She says. "You just haven't been paying attention." Jess sits on the bed and continues, "So how are you doing with all of this?"

"It's been interesting. I never expected to wear your bridal lingerie, never expected to have sex with another dude, and I certainly didn't expect to have sex with you.

The last couple of days have been wild!" I reply.

"So do you want to keep playing with us?" she asks.

"Remember I am leaving on Monday, so if you we can certainly talk about tomorrow," I reply.

"Well," she says. "He's in our room thinking right now. I told him to come see us when he's ready. Let's see how he's dressed. That will give us an idea about tomorrow." Right on cue there's a knock at the door. "There's our little princess now," she continues, "or my hot husband. Let's see who it is. Come in!"

Trent walks in wearing his babydoll.

"Aaaannnd we have our answer!" I say.

"Ok Baby," Jess says. "I see you've made your decision. What are your thoughts on tomorrow?"

"I was thinking," he says, "Why don't we all go out to Sunday brunch?"

"I have a better idea," she replies, "Why don't the two of you go on a Brunch Date alone and then later I'll take my BFF out to dinner. That way you can experience what it's like to be on a date with a man and then you can be alone to think while we go out." She looks at me and continues, "It that ok with you?"

"Sure, sounds fun!" I say. "Now that we settled tomorrow, I'm kinda tired. Why don't we all get some sleep so we're well rested for our big day."

Jessica and Trent agree and walk back to their bedroom.

MASTER BEDROOM- MORNING

Trent wakes up alone in bed. He's still wearing his wig and his nightie. He starts to feel very nervous as he has a date this morning. Not just any date, a date with his wife's best friend, a man he's is finding more and more attracive when he spends time with him dressed as a woman. He gets up and heads to the bathroom to pee. On the vanity there's a note from Jess.

"Good Morning, Baby. I hope you're excited for your big date. I thought you should try getting ready yourself. Help yourself to anything in my closet, makeup table and jewelry box. I'll be in the kitchen. Just holler if you need any help. XOXO!"

He walks into the closet and starts looking through his options. Wow does she have a lot of clothes. He sorts through what's hanging and finds the perfect little yellow sundress for brunch. All he has to do is try it on and made sure it fits. A rush of excitement comes over him as he looks in the mirror. It's perfect. It covers high enough so he can wear the breast forms, and the hem stops short of mid thigh showing plenty of leg. He takes it off and it's time to check out underwear. Jess has so many things to choose from. After rifling through her drawers he ends up choosing a black lace thong with a matching bra.

He takes a shower running a razor all over his body and face to make sure everything is baby smooth. He loves the feeling of running a razor over his legs. After toweling off he does his best to tuck and slips on the black thong panties. The bra is a little tougher, finally clasping it in place and inserting the breast forms in the cups. Then he slides his sundress over his head. He does his best to apply light makeup with pink lipstick to match his already painted pink fingers and toenails. Of course his ears aren't pierced, so he has to see what Jess has in her jewelry box. At the bottom he finds a pair of dangly gold clip-ons, and just his luck there was a necklace that matches. He puts on a pair of black sandals so he can show off his toenails. The last thing is his wig. He looks in the mirror to check out the hot blonde.

IN THE KITCHEN

Jessica and I are sitting at the kitchen table when we hear click-click, click-click.

Trent walks in.

Jess says, "You took your sweet time! I guess you didn't need my help."

"It was definitely worth the wait," I say. "You look beautiful!"

"Thank you," he says in his normal voice.

"He's right! You look fantastic sweetie! Are you excited?" she asks.

"A little," he says shyly.

"Think you can do a female voice?" Jess asks.

"Sorry... how's this?" he says in higher pitched soft voice.

"Wow, not bad. We should be ok in the restaurant," I say.

"Oh, good," he replies, trying to get used to using the female voice.

"What about a name?" Jess asks, "We can't keep calling you Baby, especially in public."

"How about Bella?" He says. "It means beautiful in Italian."

"Sounds good, Bella," I say, "Ready to go?"

Bella nods and walks toward the door. "Bye Jess," we say in unison.

"Have fun you two," she says, "Don't do anything I wouldn't do!"

DATE WITH BELLA

I place my hand on Bella's back as we walk to my rental car. I open the door for her and she gives me a surprised look. Since this is her first time out dressed as a woman, she's not used to this treatment. I can tell she's nervous.

"Hungry?" I ask.

"Yeah, starving!" she says. "Jess and I love this place. We go here all the time."

She is sounding more confident as we drove and sorta reverted into Trent mode. That all changed when I pulled up to the valet. The attendant who opened her door took a long stare at her legs as she got out of the car. Her mind began to spin. She was out of the house dressed as a woman, on a date, at one of her favorite restaurants. She hesitated as they opened the door to the restaurant for us. I put my arm around her shoulder and escorted her to the maitre'd. "Two please," I say.

"Good morning sir, have you dined with us before?" He asks.

"No," I reply. "We're from out of town, but we hear this is the place to go."

"I'm sure you'll enjoy it," he says. He looks at Bella and says "Ma'am, if you'll follow me."

Bella smiles as if she passed the first test. We walk to our table and the maitre'd pulls back her chair. She sits down with a swoosh of her sundress.

"So far so good?" I ask. She gives me a big smile. I continue, "Just a couple days ago you were just my best friend's husband. Now it's like I'm seeing you for the first time, everything about you is so feminine."

Hearing this, Bella starts to feel a stirring in her panties. "What can I say...Jessica is a great teacher. Even though it's happened so quickly."

We resume some small talk, and in spite of the strange circumstances, we soon lapse into familiar conversation, except as man and woman, chatting about this and that as if we are any other couple. The waiter comes to take our drink order and I say "The lady and I will have the Bottomless Mimosas." Bella gave me another big smile as I had referred to as a lady.

Our drinks came and we started to order food. I liked this kind of Brunch. Instead of constantly going up to fill your plate, all you had to do was tell the waiter what you wanted and they'd bring it. Bella and I ordered several times and I made sure our drinks were always full.

"What were you thinking for the rest of the day?" I ask.

"You're a Yankees fan, right? My Angels are playing your Yankees. I thought maybe we could watch together." She reaches over and takes my hand.

"Sure, that sounds like fun," I reply.

She starts rubbing her thumb over the back of my hand and says, "Thanks again for helping me figure this out."

"My pleasure," I say.

She lets go of my hand and starts massaging my thigh. Before I know it her hand is under table and rubbing my cock. "Ready to get out of here?" she asks.

"Oh yeah," I say. "Check Please!"

I pay the bill and we walk to the valet.

On the drive back to the house Bella starts to run her hand up my thigh again. Then she moves it over my shorts and rubs my dick, which is starting to grow. We stop at a red light and she grabs the back of my head and pulls it towards her. Suddenly her mouth is on mine. Our tongues find each other and we kiss passionately. I break the kiss when the light turns green but her hand is still rubbing my crotch.

"Thank you so much for a lovely Brunch!" she says.

She stops rubbing and unzips my fly. She grabs my now rock hard cock and starts to stroke. I lift the center armrest to make it easier for her. I put my hand on the back of her head to make sure she knows what I want. She leans over and kisses the tip of my dick. I ran my hand through her hair as my dick springs all the way out of my boxers. She gives it a slow lick and then a longer one. I start to moan and breathe a little faster. She has one hand firmly wrapped around my dick while she continues to kiss the head. She stops for a second to look at her hand wrapped around my dick and notices her pink nails. A quick glance up saw that I was noticing this also. Any regrets she has are gone and she moves her mouth down to feel the ridge of my head on her tongue. She gets as much in her mouth as she can and hears me say "Oh Bella!" She begins to bob up and down while circling her tongue over the head and sucking. I have my right hand in her hair stroking her head, while the left one is on the wheel. She continues bobbing and sucking like a pro. I am loving this and can't believe how good she is. I am trying to concentrate on the road and I have slowed down considerably.

"Oh Bella," I gasp, "This feels amazing. I am going to cum soon."

She sucks as hard as she can and I feel my dick began to pulse as I scream,

"Bella!!!"

My first shot of cum sprays against the roof of her mouth and I keep spurting more out. This is going to be a huge load. She is swallowing as fast as she can while trying to taste it. Once she is sure she couldn't suck out another drop, she pulls off. She uses her finger to scoop the cum on the side of her lips into her mouth. Then she leans back down and licks up the little bit that was left on my dick.

She looks me right in the eyes and says, "Well, that was yummy."

"That was awesome!" I say.

We're just about to pull up to the house as I zip up. I park the car and open the door for her again. Holding hands we walk to the door. As we walk in Jessica is sitting at the kitchen table waiting for us.

"Hey Jess," I say. "I've gotta run to the bathroom. Then I want to change my clothes and there was some talk about watching some baseball."

"No problem," she replies. "I want to have some girl talk with Bella."

I walk to my room and Bella sits down at the table.

"Well don't you look like you've been doing something naughty." Jess says.

Bella smirks.

"Details, Girlfriend! Did he treat you right?" Jess asks.

"We had a wonderful time. He treated me like a lady. Everyone in the restaurant thought I was one. We ate and talked and ate and talked. It was like old times with you and me." Bella says.

"That's really great," Jess says. "Now get to the naughty part..."

"Oh, we had such a good time I wanted to thank him. We got in the car and I couldn't help myself. I was gonna give him a handjob while we were driving. I started rubbing but then he pulled up the armrest and put his hand on the back of my head. I knew what he wanted so at that moment I decided I had to know what it felt like to give a blowjob to completion and swallow the entire load.

"You gave him road head? You Slut!" Jess says as she laughs "I've never even done that!"

"Yeah, I know," Bella says. "Anyway now that I've done all this I think I'm gonna change back to Trent for a while."

"What? Why?" Jess asks. "I thought you were loving this? You have been getting to live out a fantasy."

"When I'm dressed this way I feel so desired and attractive as a woman. All I want to do is kiss him and fool around with him. That is why I think going back to male mode is what is best for our marriage," Bella says.

"Are you saying you don't think you would have those feelings if you weren't dressed as a girl?" Jess asks.

"Yes, I think it's the clothes that are making me feel that way. Don't you want your hot husband back?" Trent asks in his normal voice.

"I just want you to be happy," Jess says. "I love you no matter what."

"I love you too," Trent says. "That's why this is so hard. I'm gonna change and watch some baseball like we planned."

"No problem," Jess says. "But remember we're going out tonight without you."

LIVING ROOM

I've changed into my casual clothes and am sitting on the couch. Trent walks in wearing a T-shirt and Shorts.

"Hey dude," he says. "What's up?"

I'm surprised to see him dressed as Trent but didn't say anything about it. "Hey bud, nice to see you," I say. "The game's just about to start. Jess told me to tell you she went to the grocery store."

He takes a seat on the couch and we watch the game. We talk like normal dudes about the game and about sports in general. He's back and forth in the kitchen, bringing out chips and pretzels while we have a couple of beers. In the 8th inning I excuse myself to get dressed for dinner. I quickly put on a nice button down shirt with a pair of pants. I come back into Living Room to watch the rest of the game.

"That was fast," Trent says referring to my quick outfit change. "I remember those days."

We both laugh and clink our beers in a toast. Jess had come back sometime in the middle of the game but had spent that time in her room. The game was entering the bottom of the 9th as we hear the familiar click-click, click-click, of her heels as she walks down the hallway. We both don't look at her at first as we're trying to watch the end of the game.

She clears her throat and says "Ahem, hi guys."

We both turn our heads and say "Whoa!" simultaneously.

She is wearing the classic Little Black Dress. Low cut so her ample breasts are sticking out and short enough so we can see her spectacular long legs. Her makeup is perfect and she is a total smokeshow.

"Ready?" she asks me.

"Just one more out," I reply.

She takes a seat on the couch as the three of us watch the game together.

"Strike Three! Yes" I scream.

"Bullshit! That was outside!" Trent yells.

"Hahaha, you lose!" I say. "Damn, I should've bet you something."

"I think we're already even," he says while winking.

Jess stands up and says "Now can we go?" I stand up and she's towering over me. "I hope you don't mind," she continues. "I wanted to wear my 5" Fuck Me Stilettos, so I'm gonna be a bit taller than you tonight."

"Whatever you want, sweetheart," I say.

"Have fun you guys," Trent says. "Don't do anything I wouldn't do."

Jess laughs as it was the same line she gave him earlier. "Ha, don't wait up!"

DATE WITH JESSICA

I escort Jess to my car the same way I did Bella. I open the door for her and she gives me a wink. The restaurant she picked is only a few miles away so it's a short drive. We check in and sit at our table. I start to look at the wine list and Jessica excuses herself to go to the restroom. I order her favorite Pinot Noir. She'll probably be surprised that I remembered the one she likes. Turns out she was about to surprise me. I see her walking back from the bathroom with her right hand balled up in a fist and what I can only describe as a naughty smirk on her face. She sits down and doesn't say anything.

"What's up, Babe?" I ask, curious to see what she's up to.

She doesn't answer and instead she drops a ball of pink lace on the table. Out of the corner of my eye I see the waiter coming with the bottle of wine. I quickly grab it as he reaches the table.

"Who would like to taste the wine?" The waiter asks.

"He will," Jess says, seeing that I'm flustered.

The waiter pours some wine into my glass and I go to reach for it with the pink item in my hand and quickly switch hands. Jess is laughing at me and the waiter is giving me a look. I tell him the wine is great and he says he'll give us a few minutes with the menu.

"Who are you?!" I say to Jess.