Not IN Love Ch. 14

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Two women dress him up again and he does them anally.
6.6k words
4.68
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Part 14 of the 27 part series

Updated 06/15/2023
Created 02/18/2022
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This is a fictitious story. All characters are fictitious and any resemblance to real people is coincidence. Do not take any information in this story as health advice.

~~~

Saturday morning, Joe woke up with his arm on Jenny's chest. He opened his eyes to see Maggie looking at him from behind Jenny. She just stared for awhile and then whispered, "You're so beautiful, so much like Lucy."

Joe smiled and said using his female voice, "Thank you," He'd been using his female voice since getting dressed up as a woman, mainly because it seemed to make Maggie more relaxed. He then slid down between Jenny's legs and started to lick Jenny's vulva. Jenny woke up and almost came immediately.

Maggie watched as Jenny woke, came and then collapse onto the bed, apparently fully relaxed. She said, "That looks like fun."

Joe then slid out from between Jenny's legs and climbed in between Maggie's. He sucked on Maggie's vulva and flicked the tip of his tongue over Maggie's clitoris and urethral opening. She felt the need to pee and an orgasm coming. She wanted Joe to continue because of her impending orgasm but also to stop so that she could go to the toilet and relieve herself, but it was too late. She came and her liquids gushed out of her which Joe consumed. Maggie also collapsed onto the bed, breathing heavily and said, "Oh... that... that is so good... Thank you."

Joe answered, "You're most welcome."

Joe got up and went to the toilet and washed his hands. When he returned he said, "I better get ready to go."

"Go where?" asked Maggie.

"Shopping," answered Joe, "I need to buy some more clothes."

Jenny had gained consciousness and was listening to the conversation.

Maggie asked,"What time is it?"

Joe looked at his watch and said, "Half past twelve."

Maggie laughed and said, "Good luck finding some clothes. The clothes shops in this town all shut a noon."

Joe took in a big breath. Jenny realised that Joe was upset and said, "Don't worry Joe. We'll sort something out."

Joe blankly looked at Jenny and asked, "Like want?"

Maggie also realised that Joe was upset and decided to stay out of the conversation.

Jenny thought for a while. She had to formulate a good argument in order to calm down Joe. She said, "You've got one set of male clothes. Do you want to wear those on the drive home?"

"That would be nice," answered Joe.

"Yes," agreed Jenny, "Arriving home in women's clothes might be a bit risky, or risque," both Maggie and Joe laughed so Jenny was heartened that Joe may be less upset. She continued her reasoning, "So, it would be best to keep those clothes for the trip home.

"But what to wear for the next two days? We have a whole wardrobe to choose from."

"Of Lucy's clothes?" asked Joe.

"Well yes," answered Jenny, "We're going to the restaurant this evening and we've already established that you'll be wearing a beautiful dress from Lucy's collection. We know that you not only look beautiful dressed as a woman but your encounter with the policemen last night reinforces that you really do look like a woman. We have plenty of clothes here so you can just stay in character until we dress for dinner."

"What clothes are you suggesting?" asked Joe.

Maggie decided to breach into the discussion to help Jenny and said, "I think that a simple summer dress would be perfect for going to a cafe for lunch. It'll also match your runners. It would also be suitable to continue packing Lucy's stuff this afternoon."

Joe's stomach rumbled and the two women tried not to laugh. Jenny said, "It sounds like your stomach is in favour of going out to eat something. Besides, as Maggie said, we still have some packing to do this afternoon."

Joe tried to think of other options but couldn't unless there was a clothes shop open somewhere. He was very hungry and needed to eat. He didn't think straight when he was hungry and said, "Well let's get dressed so that I can eat something."

The two women jumped out of bed and Maggie asked, "Who wants first shower?"

Jenny answered, "You'd better go first, Joe and I need to be milked. "

"Oh," replied Maggie, a little disappointed that she wasn't going to drink their milk.

Jenny then said, "Or you can help milk us and then we'll decide," Maggie nodded enthusiastically.

Jenny pushed Joe onto the bed and said, "You go first because you're being such a good sport."

They emptied the milk out of each others breasts and Maggie suggested that Joe should have first shower because he was going to need the most time to get ready.

While Joe was in the shower, Jenny asks Maggie, "Why did Lucy have so many control briefs? She doesn't need them."

Maggie answered, "I think that she was going to encourage Joe to wear some more women's clothes."

"Like at fancy dress parties?" asked Jenny a bit confused.

"Something like that," answered Maggie, "or just underneath his men's clothes."

"Oh," pondered Jenny, "I see. I guess we're continuing that trend this weekend."

"Yes," replied Maggie, "Fun isn't it?"

"Uh huh," giggled Jenny, "We'd better keep this just between us, okay?"

"Deal," agreed Maggie.

When Joe came out of the en suite, Jenny said, "You'd better put on what you had on last night. We can then go over to Maggie's room and choose something more casual to wear."

"Isn't that dress too formal for day wear?" asked Joe.

Maggie answered, "So many people come back to the dorms dressed in the previous night's clothes. We won't look out of place one, tiny, bit."

Maggie had a shower as Jenny helped Joe get dressed. Jenny said as she was applying some makeup to Joe's face, "You'll have to learn to do this yourself Joanne. I can't keep doing it for you," and then laughed. Joe wasn't sure if she was joking or not.

Jenny then had her shower as Maggie got dressed and after Jenny quickly got dressed, they drove over to Maggie's dorm.

They went through the different clothes to chose what each would wear.

"Take off your clothes Joe and put some lotion on your body to prevent ingrown hairs," She winked at Maggie so Maggie helped Jenny rub a very feminine smelling lotion all over Joe's body. Joe of course started to get an erection so Jenny said, "We can't have that," and tapped his penis. She said, "Quickly, put this on," and held out a pair of skin coloured control briefs for Joe to step into. Maggie pulled Joe's penis backwards between his legs and Jenny pulled up the briefs to trap Joe's penis against his premium.

Maggie selected a yellow summer dress for Joe to wear. Jenny slipped it over his head and down his body. She made a few adjustments and said, "Perfect. Now I'll just touch up your makeup and then Maggie and I can get ready,"

As Jenny applied some simple makeup, Maggie selected a pair of her sandals. She said, "You might be close to my shoe size Joanne. Try these on."

Joe was able to slip his feet onto the sandals. He looked at Maggie.

"I've got big feet," said Maggie, "The men at the mechanic shop said that I had big feet to balance my big tits. Otherwise, I'd keep falling onto my face."

"That's so cruel," said Jenny, "I think that you've got lovely feet."

Maggie said, "Thanks," but looked unconvinced.

Joe was dressed in Lucy's wig that he had worn the previous night, Maggie's sandals, skin coloured control briefs and a yellow summer dress that came halfway down his thighs. The dress felt so free on his body. It was just held up by the shoulder straps. It felt so much better than trousers that tightened around his waist. When Jenny and Maggie weren't looking he twisted from side to side and felt the dresses material slide over his skin. It especially felt nice as it rubbed his nipples.

Jenny also wore a summer dress but hers was cream coloured with red flowers. She had on a pair of Lucy's matching colour sandals.

Maggie wore a green blouse, black skirt and matching sandals.

They drove over to a cafe under Maggie's directions. It was fairly busy but they managed to get a table in the shade. They ordered food and drinks, and chatted.

Jenny said, "Lookout. That man who's be looking at us is coming over."

The man approached their table and said, "Hello again ladies."

Joe was facing away from the man. Jenny lowered her sunglasses and asked, "Do we know you?"

The man said, "I'm off duty now but I pulled you over last night and gave you a breathalyser test."

Joe looked up and recognised one of the police officers from the previous night. He looked back at Jenny with a worried look on his face.

Jenny said, "Really, and is that your wife?" She gave a little wave to the woman that the officer was with.

The officer was a little unsure of himself and answered, "Yes."

Jenny then said, "And how have you explained to your wife why you're talking to three strange women?"

"Um," said the officer.

Joe shifted sideways in his seat to look at the officer. He said, "Maybe you could tell your wife that you're just suggesting to some out of town visitors, some nice cafes to eat at? Just doing your civic duty."

"Um, yes. I could say that," answered the officer, who now seemed quite uncomfortable.

"And those cafes would be?" asked Maggie.

The officer suggested a few places to eat and then left them alone. The three of them waved and smiled to the officer's wife.

As they ate their meals, Joe asked, "Maggie, what do you think of the E-Trip?"

"I think it's wonderful," answered Maggie, "It's electric, it seems efficient, I love the little cameras on the outside for rear view mirrors and the inside screens that replace the mirrors, it's fun when it tilts around corners, it's nice and cosy," and she looked at Jenny when she said that, "it's seems easy to operate, what's there not to like?"

"I like them," answered Joe with a smile, "I was wondering if you'd like to work for a while at the E-Trip company? It might be good experience for your career?"

"Do you think that you could get me a job there?" asked Maggie.

Joe answered, "Probably."

"What's the boss like?" asked Maggie.

Jenny interrupted before Joe could answer. She looked around to see if anyone was listening, leant forward and with a serious look on her face, whispered so only they could hear, "He tries to fuck me all the time. He even fondles my tits. I'm sure he'll want to fuck you," She then sat back into her chair.

The expression on Maggie's face was one of anger and disgust. She turned to Joe and asked, "And you work for him?"

Joe said with a serious expression, "I am him."

Maggie looked confused and then looked at Jenny. She saw a little smile on Jenny's face. Maggie realised it was a joke and started laughing. Jenny and Joe joined in. Maggie said, "All those perks and a job? Sounds interesting.

"So you want me to help assemble E-Trips?"

"No," answered Joe, "I want you to help me automate the assembly of E-Trips. Wouldn't that be more along the lines of a qualified Mechanical Engineer?"

"Yes it would," answered Maggie, "It would also be more interesting."

Joe said, "But there's a catch. The business is not taking in a lot of money. It's just getting started so I will only be able to pay you the minimum wage expected of a Mechanical Engineer. Also, I won't be able to employ you continuously. It would only be during the period of getting the assembly line going and, depending on finances, your employment may be terminated before the automation is completed.

"However, think of the experience you'll get and how that will look on your CV. It might be that stepping stone towards those more desirable employers that you mentioned."

Jenny chipped in and said, "You can also stay with us. That'll be free accommodation."

Maggie bit her bottom lip as she looked at Jenny and Joe. She had tears in her eyes. She said, "I only met you two yesterday and now you're offering me the opportunity of a lifetime. And yes, it would look fabulous on my CV. I'm going to say yes before you change your mind. Yes please."

Joe smiled and Jenny leant over and gave Maggie a hug. Jenny said, "It looks like we have your things to pack as well as Lucy's. We'd better get to it."

Joe payed the bill and drove them to Maggie's dorm. They packed up Lucy's clothes into three big suitcases, her books into four boxes and just a few things for packing into the pink port to go back with them in the E-Trip. They didn't want any inquisitive baggage handlers to go through the sex toys, computer and Lucy's book on deviance. They also chose some sets of clothes to wear that night at the restaurant and the next day.

Meanwhile, Maggie told the dormitory manager that she would be leaving on Monday. She had to have a final inspection and sign some release papers but the manager seemed happy with the situation.

They started to pack Maggie's things into some suitcases. Jenny laid back into and office chair and said, "Haven't we done enough for today? We've got to get ready for the restaurant and I don't want to be too exhausted to enjoy myself."

Maggie stopped working, looked around and said, "Yes, I think so. It won't take long to finish packing tomorrow and then we can organise transport on Monday morning. How are we going to get all this stuff to your home?"

"We can have it loaded onto a train and we can pick it up from the station at the other end," answered Joe, "Jenny, we can use your car to pick them up from the station and take them home. We'd better make sure that we have enough of Maggie's clothes for a couple of days, just in case they end up in Sydney or somewhere. I also suggest that we take your most precious items in the E-Trip but of course it has limited space."

"Okay," said Maggie, "I just need my vanity bag, a couple of changes of clothes and my computer. Everything else can be replaced if it gets lost."

"Good," said Joe, "Let's get these few things over to the hotel and we can relax a bit before we need to get ready for the restaurant."

"I'll second that," said Jenny and they headed off to the hotel.

Jenny ordered some gin and tonics for pre-dinner drinks and they also imbibed some of Maggie's cannabis to help them relax. After drinking their drinks they had showers and dressed for dinner.

Joe had on a long red dress with slits up either side almost to his hips. The tops of his stockings could be seen if the slits were in a particularly wide position but in general the gown was fairly respectable. The front was loose fitting and less revealing than the dress Joe wore the previous night but it still gaped open at the top if he leant forward. Jenny said, "That'll be most suitable if we get pulled over by the police again. Maggie laughed but Joe just smiled. Deep down he was hoping to have the opportunity to turn on some more police officers.

They arrived at the restaurant just as they started to buzz from the cannabis so they were all in very good moods. They also had the munchies so they ordered mains and desserts. Jenny and Maggie had most of the two bottles of wine that they ordered. Joe only had a couple of glasses because he volunteered to be the designated driver.

Jenny and Maggie were obviously tipsy by the time they finish dinner. They climbed into the E-Trip with Jenny at the back. Jenny put her arms around Maggie and started playing with her breasts. Joe drove off but they were again stopped by a police patrol car. This time a female officer approached the E-Trip and Joe opened his window.

"I've heard about this vehicle full of lesbians," said the officer.

Joe was a bit shocked that she would be so blatantly calling the occupants, lesbians. He asked, "Is there anything wrong officer?"

"No, no," said the officer with a smile, "I just wanted to see for myself, but I had still better give you a breathalyser test. Could you please blow this?" asked the officer as she presented the end of the breathalyser to Joe.

Joe leant forward through the window to take the test but it was difficult. The officer said, "It might be easier if you open the door and lean forward," as she flashed her eyebrows.

Joe realised that the officers of the previous night must have mentioned that he exposed himself and that this officer may be a lesbian and also wanted a look. He wanted to test his theory, he asked, "Do you think the other officer wants to join us?"

"No," answered the officer, "she's not that way inclined and she's doing some paper work."

"Okay," answered Joe. He opened the door and spread his legs to get out of the E-Trip. His right leg was exposed through the slit in his dress, past the top of his stocking. A very small part of his underpants was also exposed. He waited a while before moving his other leg to let the officer have a good look at his leg. He quickly glanced at the officer and she was definitely looking at his right leg. She had a very big smile on her face. Joe moved his other leg out of the vehicle and let the dress' material fall between his legs, exposing both if his legs through the slits.

Joe leant forward and felt the neck of his dress fall open. He looked up to see the officer looking down his dress with a giant smile on her face. Joe felt pre-come leak out of his penile meatus and start soaking his panties. His nipples hardened and the officer sighed. Again Joe felt that feeling of pride knowing that the officer was being turned on just by looking at his sexy body. He said seductively, "I'm ready to blow officer."

The officer laughed, moved forward between Joe's legs and presented the breathalyser to Joe's lips. She bit her lip and pressed her crotch against Joe's knee. Joe looked down at her groin for a moment but then pressed his lips against the breathalyser and blew. The officer rubbed her groin against Joe's knee. Joe was getting randy but kept blowing. The officer kept staring at Joe's breasts and rubbing herself on his knee.

Joe ran out of breath and leant back a little bit too give the officer a better look down the front of his dress. The officer said, "Thank you," and after a cursorily look at the breathalyser test results, said "That's perfect."

The officer sighed and stepped back from Joe's knee. Joe looked at her crotch and could see that she had a very obvious camel toe and the material of her trousers was very wet. Joe looked the officer in her eyes and smiled. She smiled back and asked, "Are you in town for long?"

"We leave on Monday morning," answered Joe.

The officer looked disappointed and said, "Well you continue to have a pleasant stay here."

"It's been wonderful so far," answered Joe. Joe leant back and put his left leg into the vehicle. He paused and looked at the officer who smiled at him. Joe then put his other leg into the E-Trip and closed the door.

The officer pulled the trouser's material out of her camel toe, turned and returned to the patrol car.

Joe indicated, gave the officer a little wave and drove off.

Meanwhile, Jenny had been pinching Maggie's nipples as they watched Joe's performance. As they drove off Maggie said, "I'm so horny."

"So am I," said Jenny.

"You're horny?" asked Joe, "I'm the one that has policewoman's juice on my knee!" They all laughed.

Back at the hotel, Joe let Maggie and Jenny out at the reception and parked the EV. As he was walking back to reception, he passed two men. One man said, "Hey girl, do you want us to show you a good time?"

Joe turned to face them and asked, "How old do you think I am?"

"Um, about twenty?" answered the man.

"And you still call me a girl?" asked Joe.

"Well... what do I call you then?" asked the man.

"Lady, would be a good start," answered Joe, "Or woman of you're rude."

"Oh... um," hesitated the man.

"It doesn't matter," continued Joe, "I have two, very beautiful ladies, waiting for me in my room," he then looked down at the man's crotch, wiggled his little finger and said, "I'm sure they'll be able to show me a much, better, time," He then smiled, turned his back to the men and walked away as sexily as he could.

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