Not IN Love Ch. 26

Disclaimer:

This is a fictitious story. All characters are fictitious and any resemblance to real people is a coincidence. Do not take any information in this story as health advice.

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Jesse was in her male alter ego. He was painting Joe's toenails when he asked, "Do you want me to paint your fingernails?"

"I do but I don't," answered Joe, "I love having them painted but I'm anxious about what other people will think when they see them."

"Okay," said Jesse, "We can work on that later."

Joe loved the look of his newly painted, pink toenails. They weren't too bright to attract immediate attention but if one looked long enough, one would notice the nail polish.

"So what do you want to wear today?" asked Jesse as he used the Intense Pulsed Light (IPL) epilator to remove all of Joe's hair except his lovely long hair on his head. There wasn't that much hair to remove from his body because Joe regularly used the IPL and over time, less and less hair grew back. He loved the feel of being hairless. After each IPL session he would apply a light coating of moisturiser and then run his hands over his smooth skin. Inevitably, this would lead to an erection but not today.

"Summer dress, stockings, garter belt and high heels," answered Joe. It was what he liked to wear when relaxing at Jesse's home on the weekends.

"Do you think it's too hot to wear stockings?" asked Jesse.

"Probably," answered Joe, "but they feel so sensual."

Joe put on a short dress. It came to half way down his thighs. Usually he wore stockings because they felt so good on his legs but today was too hot. He also wore runners with half socks, no bra and light makeup.

Today was a big day for Joe. He was going out dressed as a woman. Jesse had helped him with the makeup although he'd become fairly good at applying it himself, but Jesse's touch gave him more confidence. Today, no one was likely to recognise him. He would be well away from his home town and it was a great opportunity for him to test if he liked being Joanne, or Jo for short.

Joe instantly became Jo, his female alter ego, when he, or now she, wore female clothes.

Jo certainly liked wearing the clothes. She loved how the summer dress flowed over her body. There was nothing tight around her waist. The material followed the line of her chest, down to her breasts, over her nipples and then just fell away. Jo felt the slight breeze on her legs and it felt wonderful. She also felt the breeze flow up under her dress. It caused the dress material to caress her hairless body. It felt so sensual, it was like a feather caressing her thighs, hips, waist and... penis. Her penis started to get hard. She'd have to do something about that.

Jo sighed and slid her control briefs up her legs to tuck her penis back under her groin. Jo wondered if she should have the operation so that she could walk around without underpants. That would have to be something to consider later. First things first, could he, Joe, comfortably walk around as her, Jo? If today's shopping trip worked then what next? She certainly liked screwing with her penis. It felt good to use it to penetrate others and to ejaculate. She wondered what would a constructed vagina feel like? She'll just have to imagine that whilst experiencing anal penetration.

Jesse asked, "Ready?"

"Yes," answered Jo.

"How do you feel?" asked Jesse.

"Nervous, but excited. I love the feel of the clothes. I feel quite sexy," answered Jo.

"You look sexy," replied Jesse with a smile. He kissed Jo on the lips and said, "We'll take my car."

They drive to the Canberra mall, parked and got out of the car. Jo took in a big breath and starting walking to the mall entrance. Jesse hooked his arm under Jo's and said, "Just a couple of lesbians going shopping."

Jo laughed and said, "If you keep saying things like that I'll have to screw you in the ladies toilets."

"Oh, promises, promises," replied Jesse with a laugh.

They looked for clothes for both of them but Jo loved only looking at women's clothes. They shopped at a lingerie store. Jo looked at sexy undies but realised she couldn't wear those because of her penis. It needed to be controlled. Jesse noticed Jo's disappointment and said, "Let's look at the control briefs. There may be some pretty one's there."

Jo browsed and Jesse showed her some nice briefs with lacy panels on either side. They chose Jo's size and took a few into the change room. Jesse helped her slip the briefs up her legs. Some appeared to fit, others didn't, but they did find a range of control briefs to suit.

Jesse brought in a range of suspender belts that matched the briefs and Joe chose a few that fit her. Jo changed into her original clothes while Jesse purchased the items and they then went shopping for more clothes.

They stopped at many different stores. Jo was amazed at how many more styles, colours and options there were to choose from women's clothes than there were for men's. She especially liked the summer dresses and bought a few in different stores. They also bought some blouses and pleated skirts.

In one store, Jo tried on a leather skirt and decided to buy it. She also bought a black dress. It was a fitted cut, which ended just above the knees. It was more of a business dress and Jo felt very sophisticated wearing it. In another store she bought a dress with a plunging neck line. The material was very light and if Jo bent forwards in a certain way, one could see her nipples. She liked showing off her breasts but not too obviously, this was the perfect dress in which to do that. It also had slits up the sides right up to the hips. She wondered if it was too much but Jesse suggested that it would match her G-string, period briefs so she bought it.

They also bought clothes for Jesse, some dresses, skirts, slacks and blouses. Jesse was also keen on some jeans. He quite liked wearing clothes that were more unisex. Jesse also bought a few more tennis outfits.

Jo took Jesse to a jeans shop and asked him to try on some men's jeans. They were a bit baggy at the front but they still bought them when Joe said, "You know Jesse, these would better fit you when you're a man."

They had lunch at the mall and Jesse noticed that Jo was much more relaxed than at the start of their shopping trip. He asked, "Jo, how do you feel dressed like that in public?"

"Oh," answered Jo, "I haven't really thought about it until you asked. It just feels natural to wear this. I've certainly felt comfortable being dressed like this with you."

They drive home and when they'd finally unpacked all their purchases, Jesse said, "Show time."

Jo jumped at the opportunity and slipped off her control briefs. She did like her penis being tucked underneath and pressed hard up against her perineum but she also liked being caressed as the air blew up her dress.

They tried on the different clothes and Jesse helped Jo coordinate different items to make up outfits for different occasions.

Jesse said, "Close your eyes. I've bought you a present," Jo obeyed. She liked Jesse taking control.

Jo felt silky smooth fabric encase her waist. The sensation of the material squeezing her waist felt so sensual. She trembled as her waist was constricted.

"How's that?" asked Jesse.

Jo opened her eyes. She knew that she was wearing a corset but when she saw the beautiful pink cincher, she felt like crying. She said, with tears in her eyes, "It's beautiful. When did you get this?"

"At the lingerie shop when you were getting changed," answered Jesse.

"It's beautiful and feels so sexy," sighed Jo.

"I also bought you this," said Jesse as he shook into shape a pink ballet costume.

Tears welled in Jo's eyes as she tenderly took the costume. She stepped into the leg-hole but Jesse said, "These first," and held up some pink tights.

"Yes!" cried Jo as she grabbed the tights.

Jo put on the pink tights and the ballet costume. Jesse slipped some pink leather, ballet flats into Jo's feet. He topped it off with a tiara as she said, "Happy birthday," and then passed Jo a magic wand with a star on its end.

Jo pressed her fingers to her lips and cried.

Jesse watched Jo tiptoe around, touching the wand to different items.

Jo loved the feel of the tulle tutu. It was soft like a cloud around her waist. It wasn't hard like the crinoline of the French maid's petticoat. She brushed her wrists against the tutu as she fluttered around the family room.

Jo froze when she heard Tom's voice say, "Joe? What the..." Jo turned to face Tom, Jesse's son.

Jesse asked, "Tom, what are you doing here?"

Tom answered, "I called and left a message, mum. I thought that you were out so I thought that it wouldn't hurt if I popped over to pick up some stuff."

Jesse looked at her phone and said, "Damn, I left it in Aeroplane mode while I was driving."

Shelly, Tom's wife, said, "Joe, is that your costume for your fancy dress party?"

"What?" said Tom temporarily looking at Shelly rather than gaping at Joe.

Jo mentally thanked Shelly for saving her and answered, "Yes."

Shelly pushed past Tom in the hallway and said, "It's wonderful! It looks so... fantastic!"

"Watch this," said Jo. She tapped the wand onto a dinning chair and the star sparkled.

Shelly put a hand to her face and said, "Oh that's perfect!

"Tom, haven't you got some things to collect?"

"Um... Yeah" said Tom as he went to his room.

"Thank you, Shelly," said Jo as her body relaxed.

"That's okay," said Shelly, "You look... beautiful."

"Do you think so?" asked Jo.

"Oh yeah," answered Shelly, "Any woman would be jealous of you looking like that.

"But..."

"But what?" asked Jesse as she stood next to Shelly, appraising Jo's costume.

"The ballet flats," said Shelly, "They're not quite right. I know that they go with the ballet costume but... are they what a fairy would wear?"

"What are you thinking?" asked Jo, as she evaluated her feet.

"You know in the Wizard of Oz, Dorothy's red shoes?" suggested Shelly tentatively.

"But they were witches shoes," answered Jo.

"I think I know what you mean," helped Jesse, "That style of shoe, but pink, not red?"

"Yes,"answered Shelly.

Jo kept looking at her feet. After a short while, she said, "Not sparkly. The wand is magic but the shoes are just practical shoes and part of the costume. Plain pink to match the tights, tutu and body suit," She looked up at the others for confirmation.

"Definitely," agreed Shelly.

"I think you two might be onto something here," nodded Jesse.

"I've seen just the shoes in Canberra," said Shelly.

"Really?" asked Jo hopefully.

"Ah ha," answered Shelly, "We could pop over there on Monday?" she added hopefully.

"I've got tennis on Monday," said Jesse.

"Oh," said Shelly disappointed.

"Mum, do you know where my black shoes are?" called Tom from his bedroom.

"You two go," said Jesse as she headed towards Tom's bedroom, "It'll be fun."

Jo saw Shelly's eyes almost begging, so she said, "Okay, why not."

Shelly clapped her hands in excitement and said, "We can buy you some beige pumps or some white sandals to go with that blouse and slacks that you wore the last time we were here."

Jo was sympathetic with Shelly's enthusiasm and said, "Both of course."

"Yes!" said Shelly excitedly, "Shall I pick you up just after lunch?"

"No," answered Jo, "Let's have lunch out."

When Shelly's excitement settled, she said, "You know, when you wore that French maid costume at the Central Primary reunion, Lucy asked me if I'd like to dress Tom up as a French maid."

"What did you say?" asked Joe.

"I didn't answer her. I was afraid of Lucy. I knew she could verbally tear steps off me," answered Shelly.

"She didn't..." Joe started to ask.

Shelly interrupted and said, "No she didn't, although I saw what she did to Dick. Half the time, I don't think that Dick realised what Lucy was doing, but most of the time, Dick deserved it."

"Dick was such a Dick," said Joe imitating Lucy.

They both laughed. Shelly then said, "I should have said to Lucy, 'Yes, I like men cross-dressing', but I didn't."

"I'm not wearing the French maid costume to the party," said Jo, "Why don't you borrow it for Tom?"

"Will it fit him?" asked Shelly.

"If not, it can be altered," answered Jo, "Um... You'll have to buy another pair of fishnet stockings. My pair... um... are damaged."

Shelly laughed and said, "I wonder how?" as she winked at Jo.

"What will you wear on Monday?" asked Shelly.

"Oh, I haven't yet thought of that," answered Jo.

"Why don't you wear Lucy's blouse and slacks that you wore when we were previously here?" suggested Shelly.

"Okay," answered Jo.

Shelly jumped with joy and said, "Thank you Joe. This means so much to me," She then hugged Jo who hugged her back without thinking. Shelley gasped, "Oh God!" She steadied herself on the table and then sat down. She said, "Lucy said that you give great hugs but I wasn't prepared for that," as she continued to gasp.

"Sorry... Sorry..." said Jo.

"No no," said Shelly, "It's alright," She stood up and whispered to herself, as she walked towards Tom's bedroom, "I'm going to fuck his brains out."

Jesse almost bumped into Shelly in the hall. She asked, "Are you okay, Shelly? You look a bit pale."

"Yes, I'm fine," answered Shelly. She then called out, "Tom, hurry up. We're leaving."

Jesse quietly asked Jo, "What did you say to Shelly?"

"Nothing bad," answered Jo, "I just gave her a special hug."

"How intense?" asked Jesse concerned.

"Full on," answered Jo.

"Shit!" said Jesse as she looked down the hallway, "Tom's in for it then."

"I didn't mean to..." said Jo concerned.

"I know honey," reassured Jesse as she brushed his cheek with the back of her fingers.

Tom and Shelly said their goodbyes as Shelly rushed Tom out to their car.

"Let's get you changed," said Jesse as he led Jo towards the bedroom, "We don't want you dirtying your costume."

Jesse stripped Jo down to her cincher. He caressed the smooth silky material. He said, "I'll be back. Put on some stockings while I'm gone," and disappeared into the en suite. Jo slipped some sheer stockings into her legs. The cincher had suspender slings, which Jo used to hold up her stockings.

Jesse later appeared with a bulge in his pants, "Let's have some fun."

Jo sighed as she felt the sensual touch of Jesse's hands over her stockings. Jesse had strong hands which felt wonderful running up and down Jo's legs. Jo ran her fingers through Jesse's short hair as Jesse kissed Jo's breasts. Jesse avoided Jo's nipples, which made Jo more desperate. She whispered, "Please don't tease me Jesse. I'm so horny."

Jo felt the bulge in Jesse's trousers as he abruptly grabbed Jo's waist and pulled her close against his body. Jesse looked deep into Jo's eyes and said, "I'll do whatever I fucking well want."

Jo breathed heavily as Jesse ran his hands across the back of the cincher and aggressively sucked a mouthful of Jo's breast into his mouth. It hurt, but it also felt so good. Jo felt a little bit of milk seep out of his nipple as Jesse continued his relentless onslaught.

Jo gasped as Jesse pulled backwards with his mouth and then released Jo's nipple. Jo trembled as Jesse pushed down on her shoulders and said, "Suck me. I know you want to do it, don't you?" Jo nodded and went down on her knees.

Jo ran her fingers over the bulge. She recognised the shape of the strapless strap-on under Jesse's trousers. She knew if she pulled the dildo forwards, the end that was lodged in Jesse's vagina, would press against his G-spot. She looked up into Jesse's eyes, which were full of lust. Jo pulled the bulge away from Jesse and Jesse groaned.

Jo smiled to herself as she kept pulling and twisting the bulge and Jesse went weak at the knees. She kept stimulating Jesse's G-spot as she unbuckled Jesse's belt, his trousers' button and slowly slid down the fly. Jo let Jesse's trousers fall and guided Jesse out of the trousers. Jo kept manipulating Jesse's cock and Jesse closed his eyes and sighed.

Jo dropped Jesse's boxer shorts and stared at the fully erect, lifelike penis. She licked her lips and ran the tip of her tongue along its underside. Jo knew from experience that this is a very sensitive area and hoped that Jesse also realised the gesture.

Jo slid the flat of her tongue down the shaft as Jesse watched. Jo knew that Jesse couldn't feel much of what she was doing but hoped that he could appreciate the suggestion. Jesse smiled, so Jo upped her antics.

Jo slowly slid the flat of her tongue up Jesse's shaft. When she reached the top of Jesse's 'penis', she engulfed Jesse's glans and pulled it away from Jesse. Jo was rewarded with a groan from Jesse as the other end of the dildo pushed against Jesse's G-spot.

Jo used the roof of her mouth to bend down Jesse's 'penis', which caused another groan and tremble from Jesse. Jo held Jesse's 'penis' down as she slid it down her throat, always keeping eye contact with Jesse. Jesse trembled again as her G-spot was stimulated.

Jo kept performing fellatio on Jesse's artificial penis. She closed her eyes and gave it all she had. She did her best to treat Jesse's 'penis' like a real one. Jesse said, "That's it honey. Suck my cock. Be the slut that you want to be. Make me come with your mouth. Let me squirt deep down your desperate, dirty, dick-sucking throat."

Jo, encouraged by Jesse's dirty talk and alliteration, sucked Jesse's 'cock' as fast and as deep into her throat as she could, always making sure that the other end of the dildo was pressing and stimulating Jesse's G-spot.

Jesse closed his eyes and panted, "That's it honey... Oh yeah... Keep going..."

Jo's mouth was getting sore but she wanted to make Jesse come. She kept pumping Jesse's 'cock' in and out of her thirsty mouth. She wrapped her fingers around the shaft and pumped her hand up and down. She made sure that the dildo pressed against Jesse's G-spot. She must have been doing the right thing because Jesse closed his eyes and said, "That's it honey... Keep going... Make me come... Oh shit... Oh shit!... OH SHIT!... OHHHH!"

Jesse collapsed forwards onto Jo. Jo only just managed to get Jesse's 'penis' out of her mouth before she was impaled by Jesse's shaft. She held Jesse up as Jesse recovered from his orgasm.

Jesse recovered, pushed himself away from Jo and said, "Get on the bed and spread your legs. I'm going to fuck you until you can't stand up."

Jo wondered how Jesse was going to know when Jo couldn't stand as she backed up onto the bed. She spread her legs wide, as told, and watched the approaching Jesse and his 'penis'. Jesse smirked as he knelt on the bed and slowly moved in between Jo's legs. He kept stroking and swinging his 'penis' until he arrived at his destination.

Jo watched Jesse point his 'cock' at her crotch. She gasped in anticipation as Jesse lifted her legs and placed them on his shoulders. Jo tilted her hips forwards as Jesse lined up his 'glans' with Jo's anus.

Jo sighed as Jesse wiped lubricant over her buttocks and anus. She trembled as three of Jesse's fingers spread lubricant over Jo's rectum. Jo had been stretching her anus and rectum in preparation for such an event, but gasped, then shuddered as Jesse drove his 'penis' deep into her arse.

Jo shuddered multiple times as Jesse shoved his 'cock' in and out of her bum. She watched in fascination as she saw a lump in her belly move backwards and forwards as Jesse thrust in and out of her bowels.

Jesse's 'glans' was rubbing Jo's prostate and pre-come oozed out of the tip of Jo's penis. Jesse scooped up some of Jo's pre-come, wiped it roughly over Jo's face and said, "Drink it... Get used to drinking come because there'll be a lot of it."

Jo watched Jesse's eyes in defiance as she greedily licked Jesse's fingers each time Jesse wiped Jo's pre-come across her face. Jesse tilted his head back and laughed as he pumped his shaft in and out of Jo's arse.