(A/N: this is a bit of a time skip into their relationship at the time of posting. May or may not add a few more chapters between The Second Date and this one)

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"Nathan," James called as soon as the door swung closed behind him. He had had a hard day at work but with the long weekend approaching, he was excited.

Nathan called from the kitchen. "I'm here, darling." He was making dinner right now, the soup simmering on the stovetop.

"I want to talk to you about something." He entered the kitchen and let his eyes wander appraisingly over his boyfriend's skirt, white knee-high socks and ruffled apron. He wasn't wearing a top or shoes.

"Sure," Nathan said, wiping his forehead with the back of his hand and putting the stirring spoon in the pot before turning around to look at him.

James came closer, running a hand over Nathan's arm. "A friend of mine is coming over this weekend. His name is Doctor Shriff and I want you to obey him like you would me. I value his opinion a lot and I don't want you disgracing me in front of him."

"Of course not, James," he kissed his boyfriend's cheek. "What's his favourite pie? I'll bake one for tea on Saturday!"

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Saturday morning came and with it, the reminder that Doctor Shriff was coming today and he would be staying for three days. Nathan had strict orders to be on his best behavior. For the first time, James had given him a dress code. Skirts, no pantyhose or trousers of any kind. Strings, tangas, or comando. Modest tops.

Being the good boy that he was, Nathan skidded to the door when the bell rang, announcing their guest. He was the picture of grace in his long, blue skirt, white blouse, white stockings, and black shoes.

"You must be Nathan," Doctor Shriff greeted, followed by an introduction of his person.

"It's a pleasure to make your aquaintance, Doctor Shriff," Nathan answered dutifully, "Please come in."

The Doctor smiled at him and entered. Nathan ushered him into the kitchen and deposited him at the table with the promise of coffee and some fresh fruit.

James joined them just as Nathan placed a pot of coffee and three mugs on the table. "I see you have already met," he greeted the room at large. "Doctor, I'm so glad you could come."

"The pleasure is all mine," Doctor Shriff answered. "So, when do we start?"

James smiled. "I was hoping we wouldn't lose any time, doctor."

"Fantastic!" The doctor exclaimed before turning to Nathan. "Alright, young man, please bend over the table and lift your skirt."

Nathan, frozen in the motion of putting two bowls of fruit on the table, stared at him. "What?" he asked incredulously

"Bend over and lift your skirt, boy. I want to take your temperature sooner rather than later."

A shrill laugh ripped out of Nathan. "Absofuckinglutely not."

James was out of his seat in an instant. He grabbed Nathan by the arm. "Language. This is the first and last warning you get. One more mistake and I'm washing your mouth out with soap and putting you over my knee."

Nathan made a face. "I'm not letting some stranger take my temperature in my ass like a child."

Using his grip on Nathan's arm, James maneuvered him towards the kitche door. "That's it. You're getting your mouth washed out, bottom warmed, and temperature taken anyway."

No amount of struggling helped, James was too strong. In front of the bathroom sink, Doctor Shriff hot on their heels, James paused and looked at Nathan seriously in the mirror. "Boundary?" He asked, their question if consent was being revoked.

After a brief pause, Nathan replied begrudgingly, "No..."

His answer hadn't quite finished to echo off the tiles, and he was already pushed forward and a piece of soap stuffed in his mouth. James sat down on a wooden stool they kept in the bathroom — Nathan suspected for just this reason — and pulled his boyfriend down over his lap.

"Ten spanks should be enough for his first offense," James explained while methodically gathering Nathan's long skirt and folding it over his back to expose his black tanga. "After the ten spanks, you may check his temperature and I'll take the soap out of his mouth."

Doctor Shriff asked in a pleasant tone "Do you have vaseline here? I use a special thermometer that is rather large."

"Of course," James replied just as easily, as if Nathan wasn't bent over his lap, "I have the same type of thermometer. The vaseline is in the cabinet over there."

With that conversation ended, he smacked his hand down on Nathan's right cheek without warning. "Don't squirm" came the firm reprimand before a second slap landed on the same side. A third followed briskly and then it was over to the other side. Seven and Eight were heavy, slow strokes against the underside of his buttocks and the last two quick stings on the backs of his thighs.

"Have you learned your lesson?" James asked to which Nathan could only nod. "Good. Doctor, do your worst."

Nathan could feel the slim back of his panties being pulled to the side and the greasy tip of something very cold and very large touching his rim. On instinc he clenched down.

"If you clench," Doctor Shriff said calmly, "I will have to use more force to get the thermometer in. Or I will have to have James spread your cheeks. I suggest you relax, young man."

Nathan tried to relax, he really did, but the feeling against his hole combined with his position, the knowledge that the doctor had a full view of his anus, and the foul taste in his mouth, made it impossible.

"Fine," said Doctor Shriff. He used his free hand to push Nathan's left cheek out as far as it would go and then gave a mighty shove on the thermometer. It felt like at least three fingers had just been forced into him. He was sure he could feel his insides distending eight inches deep. He knew he was being dramatic but it felt huge. The cold intrusion made him jerk and cry out.

James reached down to his mouth. "You can give me back the soap now if you promise to watch your tongue." At Nathan's nod, James pulled the offending piece of soap out. "Three minutes, then the thermometer will be done."

Nathan wanted to argue but he also didn't want the soap again so he resigned to his fate.

"I'll take your temperature five times a day as long as I'm here. And I have talked to James. He will start checking it at least twice a day when I am gone." Doctor Shriff patted his buttock, twirling the thermometer and eliciting a small squeak from Nathan. "It'll be very good for your health."

Nathan just kept his mouth shut, fearing the soap again. His ass was on fire and he wished the doctor would just take the thermometer out.

"James," Doctor Shriff asked, "what do you think we should do first after the thermometer is done?"

Nathan felt like little child, completely ignored with a thermometer shoved deep in his ass while the adults decided his fate.

"The enema will be best to start with."

"No," Nathan whined, "I don't want an enema."

Doctor Shriff slapped his butt and finally pulled the thermometer out. "Too bad," he said, "you're gonna get it anyway."

A brief pause followed. Nathan felt James move but nothing was said. "What is it?" Nathan finally asked into the silence.

James patted his bottom. "Nothing, darling. Your temperature is a little high but we will check again after the enema. Maybe you're just constipated."

Nathan flushed a horrible shade of red. "I'm not," he mumbled. He was, of course, ignored again.

There was some movement and before long, Doctor Shriff stepped up to the basin to prepare the enema.

"I really don't want an enema," Nathan whined.

"Nathan," James said sternly, "you know I don't like when you whine."

"But it's an enema!" He complained further.

Something big pressed against his entrance before either he or James could say anything more. He tried to wiggle away but the thick nozzle forced its way inside. He clenched and jerked. It stretched him even more than the thermometer had.

"Here comes the water," Doctor Shriff warned.

Then, Nathan felt the weird sensation of warm water filling him from the inside. It moved way up inside him. It was a very weird sensation but the stimulation of his anus caused his dick to harden against James's leg.

"Oh, is that arousing to you?" James asked, stroking between his thighs. "Is your clit getting hard?"

Nathan stilled completely, his thoughts grinding to a halt. Aside from their first meeting, they had never again played at the feminisation aspect of his dress-style.

Undeterred by his inner termoil, James continued, "Maybe I should ask the doctor to do a proper internal exam with a speculum? I'm sure it would be very good for you to have your pussy checked before our wedding."

Doctor Shriff, fiddling with the nozzle, chuckled. "We can definitely talk about that."

Nathan just whined and tried to relax as the warm water, no doubt mixed with soap by the smell in the room, started to burn, making his stomach cramp. He couldn’t remember ever having an enema before. Suddenly, he felt a finger twirl around the thick nozzle. He instinctively clenched his hole under the stimulation, reminding him harshly of how stretched out he was.

"Just a few more drops," Doctor Shriff said, wiggling his finger against the nozzle and making Nathan cry out. "My, you are a dramatic one. Now, I'll pull the nozzle out and I want you to hold that water for half an hour."

Nathan sobbed. "No. I can't. Not half an hour."

James rubbed his back. "It's his first enema, doctor. I think less holding time will be enough. He'll have enough chance to hold it later in the weekend."

The nozzle was roughly pulled out of his ass. "Fine," Doctor Shriff said, "Five minutes then. But don't you whine about that."

Nathan couldn’t have whined about it if he wanted to, too concentrated on clenching his poor, stretched hole so none of the water would escape him before the five minutes were up.

"Once we're done," James said, "you can go lie down until the next temperature time comes, alright?"

Nathan just nodded with tears in his eyes