Dressed For Her - Chapter 2 (Patreon)

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Sean's thoughts remained preoccupied with their phone conversation. To be honest, it dominated his mind over the next two days.  He found himself daydreaming, drifting back to his high school days.

The more he thought about it, the more he found himself remembering little things that she had done or said, had Addison always felt this way about him. He had always been a bit of a puppy, following her around and letting her make most of the decisions.

Where to eat after a game, what they were going to do when they were hanging out, little things like that. He had always been the "sweet" boy to all the girls.

It wasn't just with Addison; he had always been docile around females.  Saturday morning found Sean standing in front of his mailbox, looking at a medium-sized padded shipping envelope.  Tucking it under his arm and grabbing the rest of the mail, he rushed upstairs, closing and locking the door behind him.

Sitting in the den, the envelope on the coffee table, Sean stared at it.  The urge to open it and look was overwhelming.  It was nine in the morning and the return address was Boston MA.  Nervously Sean picked up his phone and selected her phone number.  "Hello Sean, do you have the package with my little gift?"

He could hear the excitement in her voice as she asked.

"Yes."  Sean's mouth was dry, and his hands were trembling as he pressed his earbuds in and paired them with his phone.  "You haven't been naughty and peeked have you?" Addison asked, her tone was coy and teasing.

"N, no."

"You were always such a sweet, good boy Sean.  I'm proud of you," she whispered into the phone.

"You can open it now.  I want you to describe what you see."  Without a word, Sean lifted the padded packaging envelope.  Gripping the tab he pulled, opening the end.  Reaching in, his fingers encountered something soft, silky, smooth.

Pulling the items out his heartbeat began to accelerate.  Laying everything on the coffee table, his eyes were locked, unable to look away.  "What's the matter Sean, cat got your tongue?" she asked with a sense of urgency.  Had she pushed him too far?  She wondered silently to herself. When she heard his voice, trembling with emotion, a smile crept across her face.

"It's...they...panties...panties, stockings, and a garter.

I don't understand," Sean mumbled while he ran his fingers across the fabric, feeling the softness.

"You're going to need to do better than that Sean. It took me a long time to pick these out for you.  I went to three stores, very nice stores.  I put a lot of thought into this gift.  Describe them to me.  I want to see them through your eyes Sean."

Her voice was dark and soft.  Closing his eyes for a few seconds, Sean tried to clear his mind.  He was trembling.

The sound of her voice, the thought of her, the panties on the table in front of him, but most of all it was his reaction.  Sean reached down with his hand, feeling himself.  He was so hard, more so than he had been in a long time.

Just the thought of what she was asking him to do was making him twitch.  "The panties."  Sean coughed a little, trying to catch his breath.

"The panties are dark green and very soft...they...they are satin maybe.

The front is covered with black lace...it looks like roses embroidered on them," he stammered with one hand touching the soft green and black fabric and the other hand reaching for the button of his jeans.

"Mm, but do you like them?" Addison's soft, feminine voice asked. Her voice coming through the earbuds made it sound like she was in his head.  Freeing himself from the denim and his boxers, Sean began to gently touch himself.  He had the feeling that he was completely out of control.

"Yes yes, they are."

Sean paused; he was afraid to say the next words.

"Go on, what are they?  What were you going to say, Sean?"

"Pretty, they are very pretty," he whispered as if he were trying to keep his words a secret, even from himself.

"Good, that is what I wanted to hear Sean.

I'm so happy that you think that they are pretty," she told him, then in a kind voice, she added, "You are pretty to Sean.  You have always been so soft and pretty.  I could never bring myself to tell you back then.  But I'm much, much stronger than I was in high school Sean.

I can say these things now, I know what I want, and I am not afraid of going after what I desire."  Sean sat, silent and transfixed.  What did he want?  He thought silently.

Had he ever been happy?

That was a silly question, of course, I have been happy.  I was the happiest man in the world when Rachel was born and everything she does brings joy to my life.  Sean was turning these thoughts over in his mind.  Everything was moving so quickly.

"Was there anything else in the package Sean?  Do you like the other pretty things that I bought you?" Addison asked, pulling him away from his self-reflection.  Next to the panties were a garter and a package of stockings, the garter was a perfect match to the panties.  The same dark green satin and black lace.

The stockings were black with lace tops, and the packaging itself was exquisite.  The label across the top read "Wolford."

"Yes, there is a garter belt.  It's...green, the same dark green with black lace...and four garter straps.  The hose are black," he told her.  Reluctantly he pulled his right hand away from what it was doing to help slide the hosiery out of their package.

"Ohhh, they have lace at the top.  Oh god, they feel so soft," he blurted out.  Addison giggled.

"Oh Sean, you do like them don't you?"  His mind was screaming at him to stop, just stop and tell her that all this was a mistake.

"Y, yes.  Everything is pretty.  Thank you," he whispered, his soul refusing to listen to his mind.  "I want you to wear them for me on Thursday Sean," Addison said, her voice changing, becoming more demanding.

"I want you to make yourself pretty for me, but only for me."  Alarmed, Sean's voice was panicked.

"I...I can't!  What if...someone, the airport?"  "Shhh, stop fighting yourself Sean," Addison told him, trying to calm him down.  "Wear them under your pants, it will be fine.  I will pick you up from the airport.  After you schedule your flight let me know and I will make sure that I am there to get you.  It will be fine," she reassured him.  "I want to know that you are still the sweet, obedient, boy that I loved in school.  Will you do this for me?  You said that they were pretty.  Don't you want to be pretty for me Sean?"  Staring at the lingerie against the dark cherry wood of the coffee table, he found it impossible to refuse her.

"Yes, yes, I'll try."

"Good boy," Addison purred.

"Now no being naughty...well until Thursday night.

There will be enough naughtiness then, trust me."

Sean was going to ask if he could just carry the lingerie and change when he got to the hotel, but Addison had already ended the call.  In frustration, he removed his hand, stood up, and adjusted his underwear then buttoned up his jeans.  He had promised not to be naughty until they met.  The next Wednesday night, I found Sean packing his clothes for the upcoming trip to Austin.

The reunion invitation was very specific about this being a casual event.  There weren't many attendees, so they were having it at a venue just outside of downtown and the theme was all Texas.  The food would be brisket, ribs, and chicken, all smoked on-site and there would also be a band there.

For the party, Sean packed jeans and a pullover sports shirt.  To his suitcase, he added a pair of khakis and a button-down shirt, along with a lightweight jacket.  A pair of shorts for working out in the mornings, some T-shirts, another pair of jeans, and a couple more sports shirts. Satisfied he was packed he zipped up the suitcase and set it by the bedroom door.  Next to it on the bed lay the dark green and black lingerie set.

With a sense of reverence, he neatly folded it and gently laid it on top of the suitcase.  The next morning he awoke before five, a good hour before his alarm was set to go off.  With a sigh, Sean got up and made the bed.

He didn't want to come back to a messy apartment.  His flight was at ten, so he needed to leave by seven thirty to be at the airport in time.  It was a direct flight so he should be on the ground in Austin just after lunch.  Addison had said she would be waiting for him as he exited security and they could get a bite for lunch together.

Going into the closet he picked out a pair of jeans and a black button-down shirt in a soft material.  As he reached for the pull handle of his underwear drawer Sean paused.  Addison was expecting something, but in truth, the thought of getting caught going through security at the airport terrified him.  With robotic motions, he pushed the drawer closed and walked back into his bedroom to stare at the lingerie set.

Blushing, he looked down to confirm what he already could feel.  He was rock-hard.  Was it the thought of meeting Addison or was it the panties, or was it both?  Was it how she almost demanded that he dress for her? Was it the promise of something more that she had alluded to?  Almost angry with himself for his weakness he grabbed the lingerie and carried it into the bathroom.

Laying it out on the counter, next to the sink, he turned the mixing valve of the shower to hot and undressed while the water was warming up.

Without understanding why he was doing it, Sean opened the cabinet and pulled out a razor, checking to make sure that the blade was new.  He could hear Addison's voice in his head, "Don't you want to be pretty for me?"

She had asked him.  The first stroke was the hardest.  Sitting on the tile shower seat, his leg covered in thick suds, Sean reached down and began to slowly pull the razor up his leg leaving a streak of soft, bare skin in its wake.

Methodically he continued until he was clean from his waist down.  He hadn't planned on shaving his legs, but he did.  As he stood in the shower looking down, it just looked silly, having pubic hair next to clean, smooth legs.

Without a lot of thought going into it, he had begun to shave himself clean down there.  When it was completed, Sean was a little amazed by how different it made him look. Somehow less manly.  The next, and the most daunting task was still before him.

His fingers caressed the soft material, the dark green satin sliding across his hand, the lacy brocade of black roses on the front.  With a sigh, he bent over and placed his foot through the leg opening, then the next.

Sean was shocked at how soft they felt against his legs as he pulled them upwards.  As he gave the final tug and lifted the panties across his butt and then tucked his still rock-hard penis down into the front, Sean's body gave off a shiver.  Was it excitement or fear he wondered?  Putting on the garter belt was no less eventful.

This one did not have an elastic waist, but clipped in the back and wrapped around his trim waist snuggly.  As he took a step forward to retrieve the stockings from the counter, he felt the soft caress of the stocking hold-up straps tapping against his thighs.

"Oh god!" he whispered to himself, taken by surprise as they brushed against his skin.  Quickly sitting and catching his breath, he carefully rolled up the first stocking.  Pointing his toes so they were straight, Sean slipped his foot in and aligned the thin seam with the line of his toes.  Using his hands to pull, while stretching his leg down and outwards, the soft nylon slid unfettered up his freshly shaven leg.

The sensation of the material, so snug, like a gossamer second skin, was unlike anything that Sean had experienced.  His breath was coming in short, staccato gasps.

"Oh," he moaned as the sensation began to overwhelm him.  He was doing this for Addison, for his Addie, so he could be pretty, just for her.

The second stocking was just as stirring, sending his emotions and senses into overdrive but the most intense reaction came when he took his first step.  The gentle tug of the garter, lifting the top of the hose ever so slightly while the strap pulled tight against his thigh was maddening.

A wave of femininity crashed over him.  "Now I understand why women feel so sexy when they wear stockings," he whispered, amazed at his discovery.

He was almost saddened by the thought of having to put jeans on over them. Would he still be able to feel the tender tug and touch of the lingerie under the heavy denim?

Sean was a nervous wreck as he walked into the airport.  With every step, he felt the tug and pull of the garters and the slide of his jeans against the nylon encasing his legs.  His eyes scanned the early morning crowd.

"Can they tell?  How could they know?"

He thought to himself while walking past the lines at the electronic ticketing kiosk.  For such a short and informal trip, he had no luggage to check, just one small carry-on suitcase.

This time he didn't even have his briefcase with the ever-present laptop.  He was retired, unburdened from the shackles of office email and virtual meetings.  The only technology he carried was his smartphone.

The line was not particularly long.

As he stood waiting for his turn to go through security he watched as people began to remove their shoes.  "Shit!" Sean thought to himself.

Wearing the jeans and loafers there wasn't much of his hosiery exposed, but when he took his shoes off that might be a different situation altogether.  Panicking, while trying to not look like he was panicking, he took step after step towards the security station and the conveyor with its stack of grey plastic tubs.

Trying to be nonchalant, he removed his shoes and placed them in the tray, with his carry-on case behind that.  Sean pushed them both across the metal rollers until they were captured by the conveyor.  A quick glance down revealed that he was clearly wearing hose, not socks.  The sheer material and the thin reinforcing line at his toes screamed out, "Hey!

I'm a guy wearing lingerie!" in his mind.  Shuffling forward he stepped into the scanning machine and assumed the pose shown in the diagram.  As the machine whirred around him another thought came to mind.

"Can they see...what I am wearing?"

After the scan was over a much calmer Sean was signaled that he could exit and pick up his bag.  Sliding his loafers back on with a sigh of relief he glanced at his watch for the time and then to the terminal board to double-check his boarding gate.  It was eight fifteen, boarding would begin at nine-thirty, and there was time for coffee and a light breakfast.

The flight was uneventful and as much as he would have liked to take a nap, his mind was far too active to allow that.

So many questions kept rushing at him.  Would Addie still be attracted to him after seeing him in the flesh or would she regret contacting him?

What did she have in mind for them?  The one thing that continued to bother him the most was, "What would Rachel think of this if his secret somehow got out?"  Could he trust Addie? It had been such a long time.

What in the hell was he doing taking a risk like this?

The questions and doubts continued to weigh on him as the plane drew closer to its destination.  Sean tried to clear his mind of the apprehension that was assaulting him, it was too late to turn back now anyway.

Other than staying in the secured section of the terminal and hiding until he could book a return flight, he had no choice.  As the flight attendant announced their arrival, he pushed any thoughts of hesitation out of his mind and decided to concentrate on having a good time.  With a strained smile, he settled into his seat and awaited permission to disembark.  "Sean!

Over here!" came an excited call.

Looking to his right Sean saw a beautiful woman waving at him.  She was dressed in a teal maxi skirt and a sleeveless cream top.  Her smile was bright, and her eyes shone with glee.

"Addie!" he answered back a bit louder than he had intended.

God she was so pretty, she was always so pretty and so vibrant and free.  Rushing towards each other they embraced in a hug, swaying back and forth.

"I can't believe you're here, after all these years.  Sean, it's so good to see you, thank you for coming," Addison told him while squeezing a little tighter.  "I should have never let you get away from me."

Sean was about to say something, to try and make some cute joke, until he felt the wetness of tears against his neck.  Fighting back his emotions he pulled her tight and whispered into her ear.

"Why does it take us so long to see the beautiful things that are right in front of us?  I'm sorry for not being more honest with you, and myself Addie."

As he said those words, he knew that he meant every one of them.  He had been so afraid of stepping outside of the norm, of taking any risk.  Breaking their long embrace, Addison pulled away just enough to make eye contact.

"You sir are one hot item.

I can't believe that you're still single.  I was so afraid that you would get scooped up by someone else. If I had truly remembered that you were this pretty I would have flown straight out to New Orleans and laid my claim the day after your divorce was final."

Blushing, Sean couldn't find a response to her comment.  He kind of wished she would use the word handsome, but she was right, he was pretty.

Rugged good looks were not something that he had been graced with.  His mother had always doted on him, and she was always so proud to point out how kind-hearted he was.  Her friends always referred to him as precious, and sweet.

He felt a tug on his hand as Addison began to lead him through the crowded airport toward the parking garage.

Pulling his suitcase along he followed behind her, taking in the view from the rear he smiled.

As Addison walked, he stared at her behind as it wiggled and watched as her small black leather purse swung, tapping against her hip and butt in time with the sway of her hips.  There was small talk in the elevator, mostly centered around what to do for lunch.

"Do you like seafood?" Addison asked him.  "I know a place that has incredible oysters."

Sean smiled and decided to play along and have some fun since she was being so flirty.  "Well, if you think that we'll need the stamina, oysters sound great," he replied with a mischievous chuckle.  His comment was countered with a giggle from her.

When the elevator door opened, she grabbed his hand and pulled him along once again, her heels clicking against the concrete floor of the parking deck.

They came to a stop in front of a beautiful silver Mercedes AMG GT roadster.  With a wicked smile, Addison used her key fob to open the trunk for his luggage.

"Oh my!" Sean exclaimed as she opened the passenger side door for him. He found himself almost falling into the soft, black leather seats.  Still smiling, Addison slid the small purse off her shoulder and set it in his lap.

"Will you be a dear and hold onto this for me?"

Sean nodded and his eyes followed her form as she walked around the long silver nose of the sports car.

The powerful car glided along the road, and Sean leaned back in his seat, enjoying the early afternoon sunshine afforded by the convertible's lowered top.  He found himself shifting his gaze from the road disappearing rapidly under the nose of the lean sports car to the beautiful woman sitting at the controls.  Smiling like a child enjoying the simple pleasures of a fine day outside, Sean could not remember feeling so giddy in quite a long time.

"Smiling suits you," Addison said, "it looks right on you.  I think that you have been too serious for too long.  I'm going to change that.

I want to make you smile more," she told him, her eyes darting quickly from the road to him.  "I warn you when I set my mind to something I don't give up easily."

Lunch was fun and consisted of an incredible salad, a round of oysters on the half shell, and grilled red snapper fresh from the Gulf.

There was also a lot of laughter and catching up on all that had occurred in their lives over the past thirty years.  Sean opened a recent picture of Rachel on his phone and handed it over to Addison.

"Sean!  She is beautiful, she takes after her father," Addison gushed.

"And so successful and smart.  You are right to be proud of her.  She sounds like a wonderful woman."

His daughter was the one point in his life that Sean was willing to openly brag about without shame.  Addie was right, Rachel was incredible and was the best thing that had ever happened in his life.

For a while, Sean had even forgotten about what he was wearing under his jeans.  He had been carried away by the conversation and found it so easy to talk with Addie.  He had never been able to freely chat like this with his ex-wife, even after over 26 years of marriage.  Other than giving birth to his daughter, and her being a great mother, he felt as if their marriage had been a failure.