Joanne's Outting Day 02

Author's note: I'd originally done Joanne's Outing as a one-off story featuring a wonderful sissy I met online. It was a kind of tribute to her after she was caught by her very vanilla wife and had to stop communicating with Me. My original hope was, one day she would see the story and remember the fun times We shared. The response to it was wonderful, so this follow up story isn't part of what sissy Joanne and I talked about, but it does follow the ending of the last one. I do hope you enjoy it, if stories about strong Women and submissive men are not your cup of tea, rather than leave a rude and condescending comment as an anonymous poster, just go somewhere else. It's a big internet, surely you can find something you enjoy.

After leaving Ms. Allison's company that night, Lee carefully drove home, parking in the garage and quickly shutting off the lights of his car. There was a small office and bathroom upstairs where his office was located, and just enough space to clean up and change before heading inside the house. The short blond wig was long gone, certainly it was too caked with cum to be salvageable. Scurrying up the stairs in the white lace sneakers, Lee caught another glimpse of himself in the mirror, the pink sweats and matching hoodie with "I <3 Cock" across the front would not meet the approval of his vanilla wife. However, it felt like a badge of honor at this point. He could feel the dried cum on his face, neck, chest and ass. Surely the pink thong he had on did little to slow the semen leaking from his freshly fucked pussy. Removing the hoodie and sweats, the pink bustier, thong and stockings were also covered in dried fluids as well. Everything needed a proper cleaning, but for now the lingerie would have to wait. Lee quickly showered, doing his best to dry his caged member before putting on the boring boy clothes he'd stashed for safe keeping before he left earlier.

His night was as vanilla as expected when Lee returned home, although, even dinner couldn't completely mask the taste of cum in his mouth. While the TV was on, his mind was far away from whatever was showing. Ms. Allison had cautioned him about the dreaded sissy drop, saying he would feel conflicted and guilty about enjoying his time in the glory hole. The fact was, he did feel some guilt over enjoying himself so much, he'd orgasmed twice while servicing two hard cocks at the same time. He'd thanked the manager for fucking his face, just thinking about Jeff's cock made his mouth water as he sat in his living room. Then there was the tender tingling of his well-used ass, it was sore, but if Ms. Allison called, he'd gladly offer it up again! Later that night, in bed, Lee slept soundly while his dreams were filled with being a horny and voluptuous cock crazed bimbo with real breasts and long blond hair. The only thing that kept her from a truly restful slumber was her caged manhood straining for release.

In the morning Lee mulled over his morning coffee, there were only two ways to have the cage removed, well two options provided by Ms. Allison. The small heart shaped chrome padlock could easily be cut, but he would never allow himself to do that. One option was to go back to the adult store, face Jeff, and ask for the key to the cage. The second option was to go to Ms. Allison's home, in lingerie, where an outfit awaited her arrival. As funny as it should have sounded, there was truly only one option. After breakfast Lee made an excuse and headed to the garage office. In his secret hiding spot were his pile of treasures!

"Good morning, Sir." Lee said as he removed an 8-inch realistic dildo from the hiding spot, giving it a loving kiss on the bulbous head. "I'll be with you in just a moment." He said before gently setting the suction cup base on the office desk.

Lee quickly shed his boring male clothing, gingerly stepping into a black satin and sheer lace thong. Looking in the mirror, the pink cage was easily visible through the sheer lace in the front of the thong, his eyes focusing momentarily on the small padlock imprisoning his appendage. Adding a matching waist cincher, Lee slowly rolled and slid the long black back seamed stockings up his legs, attaching them to the garter straps hanging from the waist cincher. It was amazing how just a few articles of clothing could change his mental being so rapidly. Next came a strapless bra with sheer lace cups, when he put the weighted breast forms into them, the hard nipples and dark areolas were perfectly visible. Lee didn't look sexy, he was still 6 feet tall and a body build of a weight lifter rather than an effeminate lady-boy, but he'd realized some time ago, the more he tried to build his manly frame the more he was trying to suppress his femme nature. Just a few articles of clothing and he was already Joanne, not just Joanne, but sissy cock sucker Joanne! Licking his lips, Joanne retrieved her black 4-inch heels from the hiding spot and slipped them on. Catching a glimpse of herself in the mirror, Joanne immediately noticed the small wet spot on the front of her thong.

"Sorry to keep you waiting Sir," Joanne's voice was softer and sweeter too, "I've missed you."

Turning her back toward the office door, Joanne bent forward at the hips, crossing her wrists behind her back as she lowered her mouth onto the rigid phallus. Images of Jeff feeding his raging hardon into her mouth flashed through Joanne's mind as she slowly impaled her head onto the shaft. Joanne moaned softly as she rested her against the stubbly balls connected to the shaft. She loved how slutty she looked and felt deepthroating the dildo like a pro! Ten long and loving strokes with her mouth, she kissed and flicked her tongue over the tip.

"More later Sir," Joanne said as she lifted the dildo from the desk, "Ms. Allison wants me at her house today."

As silly as it may seem to be addressing a dildo, the fact was, it was an assignment from Ms. Allison and Joanne took it seriously. This version was the third, starting with a 5-inch that eventually got retired, so Joanne could work her way up to the current one. After successfully deep throating the first, Ms. Allison directed her to a larger one, after a week of successfully double teaming them with her mouth the 5-inch dildo took Joanne's pussy. From then on, Joanne learned the art of being put on a spit, all of which prepared her for the glory hole. It just all seemed so natural to her at this point.

Joanne pulled on a pair of jeans and a sweatshirt to wear for her drive, but on a whim, she put on the white lace women's sneakers she'd worn the night before. It was a little thing, but she felt so naughty and exciting descending the stairs to her car. In her hand she had the small backpack she'd used last night with her heels and a few other items she thought she might need today. Joanne breathed a sigh of relief as she pulled out of the driveway, it took considerable restraint to not speed, but she managed and arrived at Ms. Allison's just after 9. Hopefully, this would allow her enough time to put on the outfit that was awaiting her arrival. As she walked to the front door, Joanne noticed a hot pink post it congratulating her on making the right choice and telling her to step inside without knocking.

Entering the foyer, Joanne immediately felt the urge to remove her external boy clothing. As she stepped out of her jeans, she noticed another note directing her to place her clothing in the closet on the right where she would find her clothing for today. Joanne inhaled sharply as she looked at the short satin dress and full white petticoat hanging in the closet. Looking down, she noticed a pair of white ruffled bikinis and a silver plug with a pink heart jewel. Thankfully, she'd brought some lube just in case! Pulling her thong down, Joanne lubed the plug and inserted it easily, before stepping into the tiny white bottoms. The sheer front and sheer back covered with rows of ruffles did little to hide her cage or the plug's heart base. Joanne pulled the petticoat into place, then stepped into her heels, feeling they really needed to be on her feet in spite of how they'd make her toes ache later. The petticoat barely reached her stocking tops, sitting maybe half an inch below her panties, which she knew was exactly the point. Ms. Allison had discussed her sissy Amber dressing as a maid often and how the petticoat did absolutely nothing to cover her unless she were standing perfectly upright. It had always sounded incredibly sexy to Joanne, now it felt that way too! Joanne gingerly pulled the satin dress over her head, in spite of the short body of the dress it still had a small zipper in the back which sucked it tight against her torso. The top of her bra seemed to peek slightly above the white lace trim of her neckline.

Looking further into the closet, Joanne noticed other items. A small white satin apron, a blond up style wig with a small white cap pinned to the top, a black satin choker with a silver heart pendant, and white lace elastic cuffs. Joanne looked at the choker, the pendant having elegant script with the words "Sissy Joanne" spelled out made her smile. With everything set, Joanne looked over the closet one last time before setting her bag, sneakers, and boy clothing inside. Against the door was a full-length mirror, which allowed Joanne to look herself over one more time. While no one would mistake her for a sexy French maid, she felt beyond sexy! It was as close as a 6-foot-tall man could feel to being a super model! Taking as deep a breath as the snug fitting uniform would allow, Joanne stepped back and closed the closet door. On a whim, she tried to turn the knob. The door was locked! She had just locked away her male clothing, car keys and with them the ability to leave on her own. Undaunted, Joanne turned to walk to the living room where she knew Ms. Allison awaited her arrival. The closer she got to the doorway, the more light headed she felt, it was almost overpowering!

"Well, there's my baby girl!" Ms. Allison called out from the couch as Joanne entered.

Joanne blushed at the name "baby girl", it seemed silly that she would be referred to by either term, and even sillier having them put together by a woman she could easily overpower, but there was something about the term of endearment that made her giddy inside.

"Good morning Ms. Allison." Joanne replied, slowly stepping in front of the seated red head.

In stark contrast to Joanne's formal yet revealing outfit, Ms. Allison sat on the couch in yoga pants and an oversized sweatshirt. It instantly displayed the contrast between their roles that day, Ms. Allison was dressed for comfort while Joanne was dressed to display her submission. Ms. Allison motioned for Joanne to turn slowly around, which she dutifully did, hoping Ms. Allison was pleased by her appearance.

"You look quite sexy baby girl," Ms. Allison smiled, then picked up a small bell from the end table, "but you need some makeup to complete the look."

With a couple flicks of her wrist, the bell rang, which was then quickly followed by the familiar sound of high heels on the wood floor. Joanne struggled not to turn and look as the other person approached. Who else was going to see her dressed up like this? It was exciting yet scary beyond belief! She felt the person stand close to her, then speak.

"Yes, Ms. Allison, how may I be of assistance?" The femme voice next to Joanne asked.

"This is sissy Joanne, you know about her," Ms. Allison said matter of factly, "please take her to the powder room and help her with her makeup."

"Of course, Ms. Allison!"

"But do introduce yourself first," Ms. Allison instructed, "turn to face each other sissies."

Joanne turned to her right, eyes someone downcast as she focused on balance and turning on the thick rug. As she looked, her eyes followed the black nylon clad legs perched on a pair of black patent heels that disappeared under a full white petticoat. Continuing upward, she came face to face with another sissy clad as a French maid, but instead of a towering blond wig she had on an upswept auburn wig. Joanne towered over the other sissy, who had a slender build, tiny waist and softer features than her own. Had Ms. Allison not addressed her as a sissy, Joanne would wonder if she were face to face with a natural woman.

Joanne tentatively extended her hand, "Hi, I'm sissy Joanne."

"That's not how we say hello my sweet sissy sister," the auburn-haired sissy responded, taking both of Joanne's hands lightly in her own, "lean forward slightly." Joanne did as instructed, feeling cool air on her rear end as she leaned. "That's better," she said as she leaned forward, lightly kissing the air while touching her soft cheek to Joanne's on either side, "I'm sissy Amber."

Joanne's heart lept and eyes went wide as she heard the name. It was the stories she'd discovered about amber that had first drawn her to Ms. Allison, now she was standing toe to toe, holding her hands! She'd clamored and tried her hardest since first talking to Ms. Allison to be Amber, now she was here, in the flesh! And, she was stunning! Unlike the false breasts she'd pushed into her bra in the garage, Amber's breasts seemed to be a part of her chest, matching her skin perfectly and moving with her as she breathed. Amber squeezed Joanne's hands, snapping her out of her daze, then letting them go so she could face Ms. Allison again.

"I will see to it right away Ms. Allison." Amber replied, then daintily grasped the edges of her hem, dipping into a deep curtsey.

"I know you will sweetie!" Ms. Allison winked at Joanne, who'd finally managed to face her too.

"Thank you, Ms. Allison!" Joanne attempted to curtsey as she'd just seen amber, but felt like a bull in a ballerina outfit.

"Come along sissy." Amber sweetly said, taking Joanne's hand in her own and leading her out of the room.

Following Amber was a struggle, while Amber seemed to glide in what had to be 5-inch heels, Joanne felt as if she were lumbering along behind her. She moved with an elegance Joanne couldn't comprehend, as if she were made to walk in those towering heels. Joanne wasn't even sure where she was being led, but it didn't matter, she longed to follow and learn how to be as femme as Amber was and move as she did. Before she knew it, Amber had led her into a small bathroom, standing Joanne with her back to the mirror.

"You look so sexy Joanne!" Amber gushed, taking both Joanne's hands lightly in her own again. "I heard you were amazing last night as well." Joanne blushed deeply at Amber's praise. "Jeff can be quite a mouthful," Amber giggled, "but I understand you handled him like a pro!"

"Thankfully," Joanne responded, desperately trying to sound more effeminate than earlier to try to sound more like Amber, "I was really ready for him by that point!"

"I know," Amber winked, "I saw your pictures!" Joanne blushed even deeper at that. "Don't be embarrassed sweetie!" Amber gripped her hands as she spoke. "Be proud of the fact you know who you are and aren't afraid to embrace what makes you happy!"

"Thanks." Joanne replied, feeling more encouraged by Amber's words.

"Now, let's get you looking even sexier than you are already!"

Amber was a flurry of activity applying makeup as Joanne did her best to follow her instructions. Joanne was impressed by the concentration she had while applying the mascara, doing so while leaning forward so their petticoats wouldn't smash together. Finally, Amber announced that Joanne was done and helped the taller sissy turn to face the mirror.

"I think you look amazing!" Amber exclaimed as Joanne stared at her reflection. Still, Joanne could see the man underneath, but he was getting harder to find with each passing minute. The dark red lipstick, smokey eyes and blush making her cheekbones look higher gave her face an elegance and sultriness she never thought possible. "What do you think?"

"I look amazing!" Joanne blurted. "Thank you so much!" Joanne turned to face Amber, desperately wanting to hug her. "I've wanted to meet you for so long," Joanne gushed, "I'm so excited to finally be this close to you!"

"Excited huh?" Amber had a gleam in her eye as she replied. "Let me check!" Amber's hand deftly found its way under the petticoat, the palm of her hand landing on the tip of Joanne's caged appendage while her long red nails lightly rubbed against the thin material of her bikinis. "You do feel quite excited!" Amber giggled, taking her palm away before slowly licking the precum from her palm. "Mmmm, you're a tasty girl!" Amber smiled, watching Joanne for a reaction. "I've been excited to meet you too," Amber paused for a moment, "you can check if you want."

Joanne hesitated for a moment. The glory hole had been one thing, but this was somehow different. However, she was so attracted to Amber, so enamored by her, she couldn't resist. Leaning forward, Joanne's hand found Amber's stocking tops then the small bit of skin between them and her panties. Joanne cupped, rubbed and gently squeezed Amber's caged crotch, feeling the same wetness against her palm.

"I don't want you to stop," Amber cooed, "but, if you keep this up, we will both get in trouble!"

"Oh, sorry." Joanne replied, quickly pulling her moist hand away. "You taste yummy too!" Joanne giggled like a giddy schoolgirl as she pulled her hand from her mouth.

"Come alone sissy sister," Amber said as she took Joanne by the hand again, "I'm positive there will be an amazing award at the end of the day if we do our absolute best!"

"More reward than this?" Joanne's reply went unanswered as they reentered the living room.

"Look how sexy you two look," Ms. Allison called out as they entered the room, "how do you feel now sissy Joanne?"

"Very sexy Ms. Allison." Joanne replied unable to hide her smile.

"That's great to hear," Ms. Allison sat back, relaxing into the corner of the couch, "every girl should feel sexy, even sissy girls!" Joanne blushed and smiled at her words. "Now, how are your hands?"

Joanne looked confused momentarily, she hadn't been sure where to put her hands with the big petticoat on, so she followed suit with what Amber was doing and rested them near her apron. She was sure that wasn't what Ms. Allison was talking about though. "My hands Ms.?"

"Yes, baby girl," Ms. Allison held out her bare right foot, "kneel in front of me and show me how well you can massage my foot." Joanne was happy to comply, her feet where aching from the heels! "I'm sure you appreciate how sore your feet can get wearing heels," Ms. Allison teased as Joanne carefully lowered herself to her knees, "if you do a good job, you can assist Amber in a bit."

"Thank you, Ms. Allison." Joanne replied, gently taking the Dominant's foot in her hands. Joanne slowly kneaded and rubbed the sole of Ms. Allison's foot, starting from below the arch and moving up to her toes. She wasn't a professional, but she knew how to give a decent massage.

"I'm gathering you've done this before?" Ms. Allison asked, a hint of relaxation in her voice.

"Once or twice Ms. Allison."

"Well then, it's settled," Ms. Allison placed her other foot on Joanne's thigh, sliding it deftly underneath her petticoat, "Amber go set up the table!"

"Of course, Ms.!" Amber replied from behind Joanne.

Joanne could hear Amber exit the room, her heels lightly clicking on the hardwood floor, as she felt Ms. Allison's foot glide to her inner thigh. Trying to focus on the foot in her hands, Joanne stifled a moan as Ms. Allison's foot pressed and rubbed against her panties. It was tough to focus as her foot pressed against Joanne's swollen balls, which were already constrained by the small bikinis she had on.

"Seems you're a bit wet," Ms. Allison said as she dragged the top of her foot over Joanne's crotch, "did you find out if Amber was wet as well?"