Not IN Love Ch. 24

Joe sighed. He loved the feel of the stockings on his legs and how smooth his crotch looked. Jenny slipped the control briefs up his legs and secured his penis underneath his crotch. Joe sighed again as Jenny slipped the maid's skirt up his legs and secured it at his waist. She made him step back into the court shoes and stood back to appreciate what she'd created. Jenny said, "I like my cleaners to work topless," as she eased the negligee off Joe's shoulders.

Joe gazed at the image before him. The stockings, fabric of the skirt, the pumps all made him feel sexy. Jenny returned and gave Joe a cleaning cloth. Joe knelt down to clean his semen off the floor. He was about to wipe it off the mirror when Jenny stopped him.

Jenny felt strange. She felt that she wanted to take control. Jenny scooped some semen off the mirror with her finger, opened her dressing gown and wiped it along her labia. She said as she pointed to her slit, "You can clean that up first, maid."

Joe went to wipe Jenny's slit with a cloth. She pulled her pelvis away from the cloth and said, "Not with that. I'm so delicate down there. Surely you can think of something else to clean that area more gently?" as she smiled deviously.

Joe smiled up at Jenny. He kept eye contact as he knelt between her legs and gently licked her slit from bottom to top. Jenny closed her eyes and moaned. She looked down again to see a French maid servicing her. She felt powerful but also guilty. She hated misogyny but was extremely aroused by this beautiful, sensuous, sexy French maid, on her knees before her, doing whatever she commanded.

Jenny scooped another finger full of semen off the mirror and wiped it onto her labia. Again, the beautiful, dutiful, French maid licked the semen from her slit. It felt so good. It wasn't just the maid's tongue that felt so good. It was that the maid was doing whatever Jenny commanded.

Jenny was amazed at how this simple act was affecting her. Joe lost patience so he licked some semen off the mirror and sucked Jenny's labia. Jenny watched this, she pinched her nipples and she came.

Joe held Jenny's legs as she came down from her orgasm. He eased her over to the bed and Jenny sat down. She opened her eyes and wondered how she could have come so quickly? Was it just from the thought of having power over this maid?

She decided to have more fun and said, "You may clean the mirror now but don't scratch it. You know how to do that," She wondered if she was pushing too far but then Joe licked the rest of his come off the mirror. Jenny stared in almost disbelief. This was turning her on so much but why?

When Joe had licked most of his come off the mirror he asked, "May I use the cloth to finish?"

Jenny smiled and said, "Yes you may," and then added, "When you're finished you may wear that outfit for the rest of the day."

Joe smiled then said, "But my stockings will fall."

Jenny held out her hand and said, "Come with me. We may as well do this properly."

Jenny led Joe into the en suite and told Joe to take off his clothes. Joe was a bit disappointed until Jenny started using the Intense Pulsed Light epilator on him from his toes to his face. When Jenny had finished, Joe was completely hairless from his ears to his toes. He loved how the slightest breeze would tickle his bare, sensitive skin. He said, "It feels so sensuous, arousing, sexy. Do you feel that?"

Jenny smiled at Joe as she cleaned up the loose hair and said, "Yes honey, but you get used to it."

"Oh, that's disappointing," sighed Joe.

Jenny squirted some moisturising cream onto her hand and handed the bottle to Joe. She said, "You start at the front and I'll do your back."

Jenny watched Joe sensuously rubbing the lotion onto his skin so she decided to do the same on his back. Normally she would apply the liquid quickly and efficiently on her skin, but Joe was enjoying this so much that she took her time. She put a big handful of lotion onto her chest and used her breasts to spread the liquid over Joe's back. She worked her way down and smeared the moisturiser over Joe's buttocks using her breasts. She used her hand to spread the lotion on his perineum and as she drew her hand back, she let her fingers follow the crease between Joe's buttocks. Joe jerked as her fingers passed over his anus. Jenny registered that to use later but now she wanted Joe to be dressed.

Joe was fully covered in moisturiser and fully erect. Jenny reached between his leg and started to pull Joe's penis down and backwards. There was too much resistance so she said, "You'll have to learn how to control that Joe. It's not very ladylike."

"I'm trying," responded Joe and Jenny smiled at how compliant he was.

"Yes you are, trying," joked Jenny and they both laughed. She then said, "We'll let it go for now. Let's get you dressed."

Just then, Jenny's phone rang and she answered it. It was Tom, her son, and after she hung up she said, "Bother! Tom and Shelly are on their way over to pick up some papers. We'd better get dressed."

Joe said, "Oh, how disappointing. Don't get me wrong, I like Tom and Shelly, but I was hoping to play dress-ups. Now I suppose I'd better put on my own clothes."

Jenny felt compassion towards Joe. She smiled, ran her finger down Joe's chin and said, "Maybe we can still play dress-ups. Why don't we dress you in something that's unisex or ambiguous. It won't attract attention but maybe it will still feel nice?"

"Like what?" asked Joe.

"Let's see. I've still got Lucy's clothes," said Jenny and walked to Lucy's old room. This was the room that Joe was apparently occupying while he stayed with Jenny. Their arrangement was supposedly, and outwardly, a mutual benefit where they shared the cooking and kept each other company, but in reality, Joe always slept with Jenny in her bedroom and they had sex morning and night.

Jenny opened some suitcases that held Lucy's old clothes. She rummaged through a couple of ports and decided on a cream-coloured blouse with some slacks. She held them up to Joe and said, "Try these on."

Joe's penis had become flaccid again so Jenny pulled his penis back between his legs and pulled up a pair of control briefs to contain his penis against his perineum. She smiled and said, "At least you can feel feminine with that tucked away," Joe then put on the blouse and pulled on the slacks. Jenny assessed the look, adjusted the blouse at his waist and said, "I think that looks good. What do you think?"

Joe looked at himself in the full length mirror. One had to look closely to see than the clothes were for a female. He said, "Why not."

Jenny asked, "Do they fell nice?" as she offered Joe some slip-ons to wear.

"Not as nice as the dressing gown but it's the thought that counts," answered Joe.

Jenny laughed and said, "Yes indeed and my thoughts are naughty."

There was a knock at the door as Jenny was getting dressed in a simple summer dress. Joe answered the door and greeted Tom and Shelly, Tom's wife. They exchanged small talk and Tom then went to his room. Jenny followed Tom, so Shelly and Joe sat on the leather lounge in the sun-room.

Joe asked, "Would you like a cup of tea?"

"No thank you," answered Shelly, "I don't think that we'll be long. Tom has some forms to urgently fill out."

After a while they fell into a comfortable silence. Shelly then said, "I was with Lucy when she bought that blouse."

Joe felt himself become tense. He'd been discovered wearing woman's clothes. He hid his discomfort well and looked at Shelly.

Shelly bit her bottom lip and said, "I didn't mean to embarrass you. I... I was just reminiscing about shopping with Lucy. It looks good on you. It goes well with her slacks."

Joe didn't now what to do. He felt trapped. Shelly didn't seem to be critical but she had noticed that Joe was wearing Lucy's clothes. What could he do other than accept that she knew? Shelly, was certainly taking his wearing of Lucy's clothes well. It was up to HIM to overcome HIS fears. He internally resigned to accept what would happen when it happened. Shelly was a nice lady but if she wasn't going to accept this then that was HER problem.

Joe looked at Shelly. Joe realised Shelly wasn't being critical. She seemed to be more uncomfortable than he was. He smiled and said, "Thank you. They're very comfortable to wear."

Shelly smiled when she realised that Joe wasn't upset and said, "They fit you well although... I think that you need some sandals to match the outfit instead of the slip-ons."

Joe laughed, looked at his feet and said, "Yes they're not the most attractive slippers are they?"

Shelly laughed and said, "I reckon white sandals, or if you're going out, some white pumps. It depends on where your going. Casual or a bit more formal. Anyway, you can work on that later. If you need someone to go shopping with, I'm available. I really enjoyed shopping with Lucy before..."

"Before she died?" asked Joe.

Shelly bit her lip again and said, "Yes. We were getting along so well and she had to do that. It's not fair. I don't have many friends and when I thought Lucy and I were becoming good friends she... She did that...

"I'm sorry. That sounds so selfish. I know that she didn't mean to be... hit by a truck but... I feel so lonely now that she's gone," she looked at Joe and bit her lip again.

Joe smiled. This poor lady was so self conscious and yet she was letting out her feelings. He said, "We all miss a good friend and thank you for offering to go shopping with me," He wasn't sure if Shelly wanted to go shopping with Joe for female clothes or male clothes. If it was the former, it was a big acceptance of Joe.

Joe then asked, "How are you coping with..."

"The loss of our baby?" prompted Shelly.

"Yes," continued Joe, "It wasn't only Lucy we lost at that time. You had a traumatic experience with your..."

"Stillborn," prompted Shelly again, "Yes... two tragedies so close together.

"Tom and I have been to counselling and we've come to terms with our loss," explained Shelly, "It was much easier to not lose a live baby. To me, there was nothing to love, just a small, dead body. I think it would have been much worse if the baby was born alive and then suddenly died."

Shelly seemed to cheer up and said, "Anyway, it's all good now. Thank you for asking."

Joe smiled and said, "I'm sorry if I opened old wounds."

"No, no, that's fine," reassured Shelly, "It's okay to talk about it. You know, it's funny that everyone avoids talking about that but we're over it now."

"I guess people don't want to keep reminding you," suggested Joe.

"Yes," considered Shelly, "It's not something people are comfortable talking about. Yet death is inevitable. We should talk about it more."

Just then Tom came out of his bedroom with some papers in his hand followed by Jenny. He held them up, smiled and said, "Found them," he then asked, "Have you two been okay?"

Shelly smiled at Joe and then answered Tom, "It's good to have the opportunity to just chat," She looked at her watch and said, "We'd better get going."

Tom kissed Jenny and said goodbye and Shelly took the opportunity to privately say to Joe, "I hope that you enjoy the rest of your day... and change your shoes. Maybe you'd like a different style of haircut," as she winked and looked up and down at Joe's outfit.

"Thank you," said Joe. They all exchanged good byes and Tom and Shelly left.

Joe was feeling good. Shelly seemed to accept him being dressed in feminine clothes and they felt good on him. Jenny cuddled him and asked, "How'd it go?"

"Well, I think,"answered Joe, "Shelly recognised Lucy's clothes but seemed to accept them being on me."

"Really?" asked Jenny as she raised an eyebrow, "That's interesting."

Joe then said, "She offered to go shopping with me."

"Well, that's a start, did you accept?" asked Jenny.

"No," answered Joe, "We were interrupted and... I'm not that comfortable going out in public, even dressed like this."

"Don't worry," reassured Jenny, "Just get comfortable wearing women's clothes at home and then you might change your mind. Take off those and let's get you changed into something more comfortable," Joe took off his blouse, slacks and briefs.

"I think we'll start with something simple. What about a summer dress for today?" Joe nodded. Jenny turned Joe around so that he was facing the mirror. She stood behind him and watched Joe smile as he cast his eyes over his hairless body. Jenny held up a short, summer dress in front of Joe to examine it in the mirror, "What do you think?"

Joe sighed and nodded so Jenny lifted up the dress, put it over Joe's head and let it drape down over his body. Joe shivered and said, "It feels so soft... So free... There's no tightness around my waist... It just flows from my shoulders and then... caresses my skin when I move," Joe swung his shoulders to demonstrate what the dress did. His breasts also swung with the movement and his nipples were brushed by the soft, sensuous material of the dress. He sighed and trembled.

"You like that," stated Jenny more that ask.

Joe nodded. He looked at Jenny in the mirror and saw her looking at his body in the reflection. She was smiling. He wondered if she liked what she saw or was laughing at him. Joe asked, "What do you think?"

"I... I wish that I could have that feeling again," she answered as she watched his reflection, "That... sensual feel of feminine clothes, but... I've worn them for so long they just feel normal and I... I guess, that I've been desensitised to that feeling."

"You poor thing," said Joe, "Wear some men's clothes and then you'll know what rough feels like."

Jenny looked at Joe's reflection in contemplation. She then said, "Alright, I will. May I borrow yours?"

Joe wasn't serious about Jenny wearing men's clothes but when he saw the look on her face as he turned around to face Jenny he said, "Yes, yes of course. Why not? Wait here."

Joe returned with some of his clothes. He started to fit his sock onto Jenny's foot but she pushed him away and said in her deepest voice, "What's wrong with you woman? Don't you think that I can dress myself?"

Joe looked up surprised but then smiled and stepped away when he saw Jenny smiling. She was enjoying this new role-play.

Jenny dressed herself in Joe's clothes: a simple, long sleeve shirt; baggy trousers; brown belt; socks and her own tennis shoes -- Joe's would have been too big for her feet. She assessed herself in the full, length mirror. She put her hair into a ponytail with one of her hair elastics, stood back and said in her most masculine voice, "I'll have to get a haircut," She then looked at Joe, caressed his hair and said, "Have you thought about growing your hair longer?"

Joe looked at his reflection and said, "Why not. There are plenty of men with long hair."

Jenny said, "Let's finish your look."

Jenny sat Joe down at her dressing table and explained to Joe how she was applying a very light layer of makeup. She then showed him how to apply lipstick, that was very close to the colour of his lips, and then stood back to considered the results. She pulled out the wig that Joe had worn when he was dressed as a French maid for the fancy dress party and adjusted it on Joe's head. She contemplated the results, smiled and said, "We'll get you another wig and you can switch between the two until your hair is long enough to wear without a wig."

Joe nodded and said, "Thank you," He had a slight tear in his eye which Jenny noticed but didn't comment on. They wore their attire for the rest of the day.

Joe loved the sensual feel, not only of the light, silky, summer dress but also how the hairs of his wig stroked the skin of his neck and shoulders each time he moved. He became quite proficient at walking around in the pumps and loved how his legs looked longer and more curvaceous each time he caught his reflection in a mirror or a pane glass He kept walking and sometimes running around to evoke the effects.

Jenny sat around with her legs parted and sometimes leaned on the breakfast table, reading her phone or just watching Joe. She was surprised at how comfortable she felt in men's clothes. She considered what it would be like to be a man. She certainly didn't have the equipment to be a man but her mind liked the idea. She thought about how would a woman, dressed as a man, fit into society? She looked at Joe and thought it would be just like how a man, dressed as a woman, would fit into society. She made a decision and said, "I want to change my name."

Joe stopped thinking about how good he felt dressed as a woman and sat down next to Jenny. He asked, "To what?"

"Well," explained Jenny, "It's not really changing my name. I... I just want to be called Jesse."

Joe smiled and asked, "Your middle name? Like Jesse James instead of Jumping Jenny?"

"Yes," answered Jenny, "You remembered."

Joe laughed and said, "Of course, Jesse. I think that's a good idea if you want to be called that. Why not?"

"It's a bit more masculine," said Jenny tentatively.

"Well it suits the outfit," reassured Joe with a smile.

Jenny cheered up and then said proudly, "Yes. Why not? In fact, I can switch from Jesse to Jenny and back again whenever I feel like it."

"Or just stick to Jesse," suggested Joe, "You like it and it suits both genders."

"You're right," said Jenny confidently and then a bit more uncertainly, "I guess it'll take time for people to get used to it and I can use the different names for different situations. It's settled then. Jesse and sometimes Jenny.

"What about you?" asked Jesse, "Do you want a more feminine name for when you're dressed like a woman?"

"Um... I guess Joe is a sort of a unisex name," considered Joe, "It could stand for Joseph or Joanne couldn't it?"

"If course," answered Jesse with a smile, "Joe, or Jo, without the 'e' it is, and sometimes I might call you Joanne."

Joe swirled around in his dress and considered, 'Joanne'.

Jenny, or Jesse, could feel her clitoris twitch when she glimpsed Joe's breasts and nipples under the dress. She enjoyed watching Joe strutting around, swishing his dress and hair. She was a bit confused about her feelings. Was she seeing Joe, or Joanne, as a woman for her alter ego as a man to have sex with, or was she feeling those lesbian urges that were triggered when they had sex with Maggie or Tracy? Did it matter?"

Jesse stood up and grabbed Joe's waist from behind. She leaned in and kissed his neck. Joe trembled. She then nibbled his earlobe, breathed into his ear and she said, "I'm going to fuck you Joanne."

Joe started to breathe heavily and his penis hardened making an unladylike tent in his dress. He said in a feminine voice, "Oh. Well what is a girl to do?"

Jesse smiled and was willing to continue this role-play She pinched Joe's nipples and said, "Take my huge cock up your tiny little pussy."

Joe spun around in Jesse's arms to face her and said, "Well what are you waiting for?" and kissed Jesse on the tip of her nose.

Jesse groaned and lustfully looked up and down Joe's body. She held Joe's hand and led him to the kitchen bench. She jumped backwards onto the bench, undid her belt, let her trousers fall to the floor and pushed down her boxer shorts. Joe looked at Jesse's clitoris with lust. Jesse's clitoris was huge because of a previous hormonal imbalance. It was just like a small penis.

Joe said, "What a beautiful cock you have," he then lifted his semi hard penis and ran it along Jesse's clitoris from her clitoral hood to its tip. Joe pushed his glans towards Jesse's vulva but instead of penetrating her, he ran his glans along the underside of Jesse's clitoris, then back towards its tip.

Joe kept slowly wiping the tip of his penis along the top and then the bottom of Jesse's clitoris starting from her clitoral hood, along to it's tip, back underneath it's shaft to her vulva, then back along the underside, up to its tip and then along the top to her clitoral hood. Joe kept doing this backwards and forwards. It was a massive turn on and soon his pre-come was leaking out of his penis, coating the whole of Jesse's clitoris with a slippery solution.