Not IN Love Ch. 24

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Couple cross-dress and she cock stuffs his cock.
9.8k words
4.8
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1
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Part 24 of the 27 part series

Updated 06/15/2023
Created 02/18/2022
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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.

~~~

I was still dark. Joe woke early but didn't know why. He didn't feel tired so he decided to practise mindfulness. He laid on his back with his hands comfortably beside his body and started to scan his body.

Joe started at the very top of his head. He could feel the energy shooting out of the crown of his head. He then slowly scanned his scalp down to his ears and eyes, nose, cheeks, mouth and neck relaxing each part as he went. He then scanned down his arms. When he got to his hands, he could feel his energy emanating from the palms of his hands. He then came back to his shoulders and scanned down his body. He felt the energy seething out of his belly, just below his belly button. He kept on scanning down his legs to the tips of his toes. He paused and felt the energy radiating out of the soles of his feet. His body was completely relaxed.

Joe assessed his body. There were no sore spots, no pain or aches. He felt satisfied that he was healthy, according to what he could detect.

Joe then started to mentally step back and assess his thoughts. He let his mind wander and found himself thinking about sucking the come out of Jenny. He then had something to think about. He brought his mind back into assessment mode and wondered what was his first sexual memory.

The first thought that came into his mind was watching Jenny's breasts moving within her blouse when he as much younger. Her nipples brushed against her silk blouse. He smiled and felt his penis twitch but that was not what this exercise was about. He had to concentrate. He had to be mindful of his feelings and thoughts.

Joe observed himself watching the image in his mind. Why did Jenny's wobbling tits turn him on? He imagined what her breasts looked like without clothes. That was very interesting but is that what he thought when he was so young? Probably not, so what was it about Jenny's tits that spawned his desire?

Joe kept observing his emotions. He noticed his attention was on Jenny's nipples, how they brushed against the blouse's material. That was what turned him on, her nipples, but why? It slowly came to him. It was the thought of her nipples being stimulated by them brushing against the material. Her becoming aroused made him aroused. This was very interesting. Did he know, at that age, that women's nipples being lightly brushed would be sexually arousing for a woman? If he did, where did that knowledge come from? Was the knowledge that he gained at uni doing psychology influencing his thoughts. He paused for a moment to appreciate that this was a really interesting mindfulness session but then gently brought his attention back to doing the mindfulness exercise itself.

Joe cast his mind further back in time trying to find when he was aware that women, or girls, became stimulated. He found nothing in his memories. He did remember sometimes seeing his mother's breasts when she was getting dressed. His family wasn't concerned about nudity. They didn't walk around naked all the time, but if someone accidentally saw someone else naked, it wasn't a big thing. No one covered up his or her private parts, they just kept doing what they were doing.

He needed to look at this differently. There must be some other trigger to his own sexual awareness before he became aware of Jenny's sexual awareness. What was it?

Joe tried to think of things that happened to him when he was even younger. Something that could have triggered his awareness of sex. That must have been his awareness of the difference between males and females. What was his first discovery of that difference?

Joe felt that he was pushing too hard and that was impeding his self analysis. He let his mind wander again. He thought of girls and boys at school. They wore the same uniform except girls wore skirts and boys wore shorts. Was that a trigger? He couldn't find any incident that indicated skirts and shorts triggered any sexual feelings. What else was the difference between girls and boys?

Joe let his mind drift between daydreaming and mindfulness when thinking about things outside of school. Sports? Were they sexy? No, nothing there. Karate? No absolutely not except when Lucy sparred with him when she was wearing hot-pants, T-shirt and no bra. Joe realised that he was letting his mind daydream too much. He gently brought his mind back to attention and as he did so, it clicked, fantasy. Wasn't fantasy part of sex or was this his psychological training imposing on his mindfulness? What the heck. This was really interesting but getting nowhere so he started to think about fantasy things.

Joe thought of space adventures, space combat, Lord of the Rings, witches, elves, goblins, dwarves, fairies... wait... fairies? What did a fairy look like? For some reason he had in his mind a fairy in a tutu. Something like the ballerinas in Tchaikovsky's Swan Lake, but why? Joe concentrated on the image in his mind. The fairy was dressed as a ballerina but the colour was pink, then it came too him. He had a dream about this when he was very young.

Joe's dream, when he was much younger, was about a fairy. She was dressed in a pink ballerina outfit with a tiara and magic wand. There was a star on the end of her wand. She smiled at Joe. Everything else was dark except the fairy and Joe. Joe was naked but not embarrassed. He loved the look of the fairy. She was so perfect in every way. He wanted to look just like her. They didn't talk to each other yet the fairy smiled, held out her hand and touched a white pill in her hand with her wand. There were sparkles and then the pill turned pink. She offered the pill to Joe and he ate it.

Joe felt the sparkles spread throughout his body. It felt wonderful. His whole body tingled from the top of his head to the tips of his toes. He looked down and saw sparkles around his toes and he started to grow pink, leather, ballet flats on his feet. The sparkles continued up his legs and pink tights encased his legs. His penis shrunk into a little groove like his mum's but there was no hair. His groove was covered with pink satin that grew up his body. A tutu formed on his hips as the satin grew further up his waist. His breasts grew and large nipples formed and then the satin covered them up. The satin formed into the beautiful body suit just liked the one the fairy was wearing. His hair grew longer, down to shoulder length and a tiara held it in place. Joe looked around to thank the fairy but she was gone. She had given him his wish of looking just like her without ever exchanging words.

Joe laid there assessing his feelings about the rediscovery of his dream. This explained it all. This is why he liked wearing stockings. They felt so nice on his legs. This is why he liked wearing women's clothes. He wanted to be just like the beautiful fairy. He not only wanted to wear clothes like she did but he wanted to be a beautiful female nymph. This explained everything except, why did he have this dream in the first place? Why was his first sexual thought about becoming a fairy, or looking like the fairy nymph? Was it just the perceived beauty? Was it a sexual thought or just a dream?

Joe reassessed his feelings in the dream. He couldn't be sure but he didn't remember having sexual feelings when he originally had the dream. Was it just wanting to feel beautiful? It wasn't the magic because he had no magical powers in his dream. He just felt wonderful being just like the fairy. Joe concentrated on that feeling. Was it sexual? It certainly turned him on now but did it turn him on when he originally had the dream? He didn't know. All he could remember was that he felt wonderful in the dream when he became just like the fairy.

Joe sighed. He probably wouldn't know why he had the dream but he now knew why he liked feeling sexy in women's clothes and why he loved having breasts. It probably all started from that one dream. He was happy with his mindfulness session. This was the best one he'd ever had. He sighed again.

Joe became aware of his penis being held. He brought himself back to the present. He opened his eyes and saw Jenny looking at him with her hand gently stroking his full erection. She was propped up on her left elbow. It was unusual for him not to be aware of her movements near him. It must have been because he was concentrating on his mindfulness. She raised one eyebrow and seductively asked, "Thinking about me?"

Joe laughed and said, "Swan Lake."

Jenny frowned and asked, "Tchaikovsky's?"

"Yes," answered Joe. He wondered how he was going to handle this without lying so he asked, "Did you do ballet?"

"No," answered Jenny wondering where this was going.

"Have you ever thought of wearing a tutu and the other stuff that the ballerinas wear in Swan Lake?" asked Joe.

"No, is this a fantasy of yours?" asked Jenny.

Joe shrugged and answered, "It could be nice.

"The pink, leather, ballet flats. One hundred percent leather mind you. Not that reconstituted rubbish. Pink tights and tutu, body suit and a silver tiara."

"Are we talking about Swan Lake or the other lesser-know ballet of Tchaikovsky's, Flamingo Lake?" asked Jenny as she smiled.

Joe laughed and said, "Well, I may have been taking some poetic licence there."

"Yes, I think so," said Jenny, "I remember the swans being dressed in white and the tiara? I thought that the swans wore white headbands?"

"Well pink's a bit more feminine and sexy, don't you think?" asked Joe.

"A bit more, fairy, if you ask me," answered Jenny.

"Well it is a fantasy," replied Joe.

"Maybe you're thinking of the Dance of The Sugar Plum Fairy," suggested Jenny. She then squeezed Joe's testicles and said seductively, "from Tchaikovsky's Nutcracker Suite?" Joe moaned as Jenny kept squeezing and manipulating his testicles.

"Hmm," contemplated Jenny, "I would have thought that a nurse's uniform would be more your fantasy thing?"

"Go on," prompted Joe.

"Well," continued Jenny seductively, "dressed as a nurse, I could give you your treatment. Maybe you need a sounding or maybe I could help you provide a seminal sample as Dr Helen did?"

Joe's penis twitched and Jenny smiled. Joe chuckled and said, "Your fantasy outfits are so much better than mine."

Jenny laid down on her back and said, "Well, we'll see about that, but aren't you forgetting something?" she then pointed towards her groin.

Joe rolled over and slid down Jenny's body until he could perform his ritual morning cunnilingus. It was Saturday morning and they had all day to do whatever they liked.

Joe loved the flavour of Jenny's sweet, golden nectar and cherished sucking out her come every morning. He slid his way up to Jenny's breasts ready to drink her milk but Jenny guided him up so that his erect penis was at her vaginal opening. Joe slid in easily and after some time, Jenny's cervix dilated enough for his penis to slip into her womb. They slowly screwed, savouring the feeling of this intimate intercourse. Jenny came a couple of times and eventually Joe came. Neither had a mind-boggling orgasm. Their orgasms were warm, tingling feelings with a final release of mental tension.

Joe kept his penis hard against Jenny's cervix until it had closed thus keeping his seminal fluid locked inside her womb. Jenny loved the thought of her womb filling up with Joe's come.

Joe and Jenny drank each other's milk and relieved the pressure on their breasts. They lay together in each other's arms relaxing and sometimes gently suckling until they became hungry and thirsty.

Joe got up to make brunch. He put on the diaphanous dressing gown that Jenny gave him to wear on the very first morning after they'd slept together.

Jenny said, "I should take a turn getting breakfast for us."

"Why?" asked Joe.

"Because you do it every morning and that's probably not fair," answered Jenny.

Joe said, "I get up a bit earlier than you. You enjoy lying in bed, I don't. You don't have any reason to get up. I have to get up and go to work so I'm used to it. You don't, so there isn't any logical reason for you to force yourself to get up to make breakfast when I don't mind unless I make tasteless breakfasts?"

Jenny laughed and said, "No, I can live with your cooking.

"We should probably get you a proper dressing gown."

"This one is perfectly serviceable. Don't you like it on me?" asked Joe.

Jenny got up, reached into the negligee and caressed Joe's penis. She said, "I love seeing you wear it. I love seeing your breasts, body and especially this," as she helped Joe's penis become semi-hard.

Joe laughed and moved away to make brunch.

They sat down and ate brunch. Jenny noticed Joe still had a semi and asked, "Didn't you have enough sex this morning?"

Joe looked at Jenny questioningly.

Jenny nodded towards Joe's semi.

Joe smiled and covered up his semi as best he could wearing a see-through garment.

Jenny watched Joe as they drank their cups of tea. She asked, "You seem deep in thought. Is everything okay?"

Joe looked at Jenny, smiled and answered, "All good."

This was unusual behaviour for Joe thought Jenny and that worried her, so she pressed him a bit harder, "Are you sure? You look a bit worried."

Joe opened his mouth, took in a breath and then sighed.

Jenny was now worried. She asked, "Have you had enough of us being together?"

Joe suddenly looked at Jenny seeming more worried. He answered, "No, not at all. I'm very happy with our arrangement. Are you sick of me."

"No," said Jenny relieved. She leaned over and caressed Joe's cheek, "You're perfect for me. You're handsome, intelligent, funny, kind, a great lover and a great cook."

Joe chuckled at her last trait. He asked, "Handsome? Dressed like this?" as he gestured towards the negligee.

"Well, beautiful in that," answered Jenny.

"Do you think so?" asked Joe seriously.

Jenny was a bit confused. She said, "Yes, beautiful. I love how your breasts wobble freely and how your nipples push out the material," She was starting to get aroused looking at, and talking about Joe's breasts.

Joe sighed, "Just my breasts."

Jenny hadn't seen Joe like this before. She gently stroked his hand and said, "I love all of your body."

Joe sat there for a while enjoying Jenny's attention. He liked how she caressed his hand. He sighed.

Jenny asked, "Come on, tell me what's wrong?"

Joe looked at Jenny and wondered if he should tell her. Eventually he said, "I like this gown. I want to keep wearing it."

Jenny smiled and said, "Of course, you may keep it. It's now yours to wear whenever you like."

Joe smiled and Jenny was a bit relieved to see Joe getting back to his usual self. She asked, "Would you like another one? Something in a different colour?"

Joe's eyes lit up for a moment and then he looked a bit concerned, "A pink one? Although they're very expensive aren't they?"

Jenny laughed and said, "I think that between us millionaires we can afford it."

Joe nodded. After a while he asked, "Do you remember when you and Tracy dressed me up to see if I would be suitable to join the Woman's Tennis Club?"

"Yes of course, but we didn't get around to deciding if you could join the club," answered Jenny. "I remember that you answered the door dressed in that negligee, stockings, stilettos and control briefs to the surprise of the delivery woman. What was her name? She was certainly impressed by what she saw. That was a real turn-on."

Joe brightened up again, "Randy was her name."

"That's right, Randy," answered Jenny, "I wondered if that was her name or her condition?"

"Do you think so? Were you?" asked Joe.

"What?" asked Jenny smiling.

"Randy?" asked Joe.

"Oh yes," answered Jenny, "That was a real turn-on."

Joe stared at Jenny wondering if he should ask. He decided he would. He took in a breath and asked, "Because I was beautiful?"

"Well lots of things," answered Jenny, not understanding. "The surprise on her face. The way she responded, not shocked but aroused, we were very stoned and it all came together."

Joe sighed again and Jenny thought about what Joe had asked, she finally understood and said, "But most of all, you were so beautiful and I'm sure that's why Randy got randy."

Joe looked at Jenny to see if she was mocking him. She didn't appear to be. She was smiling kindly not mockingly. Joe smiled.

Jenny could see that Joe was more relaxed and probed a bit more, "Do you like being beautiful?"

Joe nodded and asked, "Is that weird?"

"No of course not," Jenny combed a tiny bit of Joe's errant hair behind his ear. She wondered if she should press further or would it embarrass Joe. She asked, "Why don't you wear that all day? We don't have anything planned to do today. We can just lay around relaxing."

Joe smiled broadly so Jenny stood up and said, "Just a minute. I'll be back."

Jenny returned with the black pumps that Joe wore to the fancy dress party, dressed as a French maid. They were the same ones he was wearing when he answered the door to Randy. She took off the slippers Joe was wearing and slipped on the court shoes. She said, "That looks better," and smiled at Joe.

Joe stood up and walked around in the shoes. Jenny noticed that Joe was getting a semi-erection again. She smiled and said, "You look beautiful."

Joe, again smiled broadly and asked, "Do you think so?"

"Definitely," answered Jenny. She walked over to Joe, stroked his penis and started kissing him deeply. She then nibbled his earlobes and nuzzled his neck.

Joe closed his eyes and sighed. Jenny led Joe into the bedroom and in front of the full-length mirror. She stood behind Joe but still stroked his penis, which was fully erect. She turned Joe to face the mirror and whispered into his ear as she nibbled his earlobe, "You are so beautiful... You know you're beautiful and sexy... I know that you know that because of how hard your penis is."

Joe sighed. He looked at his reflection up and down in the mirror. He groaned. Jenny caressed his breasts with her left hand as she pumped his shaft with her right. She kissed and bit his neck. Joe groaned and closed his eyes. Jenny said, "Don't close your eyes. Look at yourself. Look how beautiful you are."

Joe opened his eyes and moaned. Joe felt that he was beautiful. Jenny was pinching his nipple and squeezing his breast. The shoes made his calves and legs look curvaceous. The silky feel of the negligee felt sensuous against his body. Jenny rapidly pumped his shaft and when she pinched and pulled his nipple as hard as she could, Joe came. His body buckled forward. Jenny pumped his penis as fast as she could. Strings of semen pumped out of Joe's penis onto the mirror. Five or six times Joe's come sprayed the mirror and then some spurted onto the carpet.

Jenny eased the grip she had on Joe's breast and nipple. His body spasmed. Jenny slowed her massaging of Joe's softening penis. Joe almost collapsed but Jenny steadied him. She led him to the bed and guided him to lie down. Jenny laid down beside him and caressed his body. The negligee's material did feel nice so she slowly stroked his whole body until Joe feel asleep. Jenny fell asleep not long after Joe.

Jenny later woke and stroked Joe's body. Joe woke up and started to get out of bed. He looked at his semen on the mirror and said, "I'll clean that up."

Jenny smiled deviously and said, "You'll have to wear the right clothes to do that."

Joe was confused so Jenny said, "Wait here."

Moments later Jenny returned with a clothes bag. She opened it and pulled out the French maid outfit that Joe had worn to the fancy dress party. She told Joe to stand up as she started to take off his pumps. Joe watched himself in the mirror as Jenny slid fishnet stockings up his legs. Jenny noticed that Joe's penis started to get hard again so she reached between his legs from behind, grabbed his glans and pulled back. Joe buckled forwards but then became used to the feeling and stood up straight. Jenny massaged his penis against his perineum and the crack of his buttocks. She whispered into his ear, "Don't you look good with that smooth pubic mound?"