This series of stories are all standalone so can be read in any sequence. They are about my favourite fantasy --- my first time wearing, or first time being caught wearing panties. Obviously then they all involve lingerie wearing men and the consequences may include cuckolding, creampie eating or cock sucking men amongst other things. If any of these are likely to offend you I suggest you stop now ... Otherwise please read on and enjoy. I do appreciate your comments and constructive feedback.
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At 21 Karen had never had an orgasm with a man, but had given herself plenty whilst masturbating. Admittedly she had only had three boyfriends she had slept with, but one thing for sure, she wasn't going to discuss her inability to orgasm with a man with her mother! Both her parents were very prudish and still thought she was a virgin, and would certainly not be happy if they knew she masturbated at least twice a day.
She had just accepted a big promotion that meant she needed to move out of home and to the city a couple of hours drive away. She had found an apartment to rent and was looking forwards to moving in there and being free to masturbate when and where she wanted! She was looking forwards to changing the cosmetics bottle she used to fuck herself with to a nice cock shaped vibrator. She wasn't in a hurry to find a new boyfriend. When she did find a new boyfriend she would make sure she really liked him before she let him get into her panties. She had promised herself at least three months of dating before she let him fuck her.
Then a few days before she was due to move she received a call from the real estate agent to say the building had been badly damaged in a fire. They returned her security deposit and first months rent but promised to help her find something else as quickly as possible, but the residents who were already living there and we're now homeless would be given first preference.
Karen was upset, but not too much. Her uncle Neil lived quite close to where she had arranged to move to. That had been deliberate as she got on very well with him and expected to visit him a couple of times a week, or have him visit her for dinner. She rang him and explained the situation and he immediately told her she could stay with him for as long as it took her to find somewhere nice to live.
Neil was in his late 40's and a widower. His wife had passed away a couple of years ago from complications from flu. He loved his niece Karen. Maybe partly because she reminded him so much of Joanne when they first met. Short, fat, and very sexy! Joanne had been that way until the day she died. Having Karen stay with him would be wonderful for a short period of time, and he was glad she was going to stay close after that so that they would still see a lot of each other after she moved out.
He could live with the inconvenience of having her stay on his usual habits. Around the house he had been wearing just panties and either a nightie or a slip for many years, since about a year after Joanne and he had been married. Whilst Karen stayed with him he would need to cover his panties with normal male clothing. But when he got back to his bedroom he was sure his masturbation sessions, with nightie or slip now in place, would be fantastic having spent a few hours, or all day, with his short plump niece who looked so much like Joanne.
She arrived at 6:00pm on the Saturday and Neil had a delicious dinner nearly ready. They had a wonderful evening talking before both retiring to bed.
Karen was glad her bedroom was right at the opposite end of the house to her Uncles. Despite the fact he was more that double her age and was her Uncle he made her horny. She loved a nice arse, and her Uncle had one of the best! She badly needed to masturbate and didn't want to be quiet about it! Her orgasms as she fantasised about her uncle coming into her room and fucking her were the best of her life!
Neil was also masturbating in his pink panties and favourite pink silky nightie. But he didn't cum. He wasn't due for an orgasm for at least two more days! For years his wife had limited him to one orgasm every three or four days. They had still played around every day and of course Joanne had always had at least three orgasms a day, it was just Neil that was restricted! He stopped himself just before the point of no return. It took ages for his erection to subside and for him to fall asleep.
The next morning Neil showered and dressed. Today he was wearing another favourite. White cotton panties with pink polka dots. He knew Karen loved pancakes so began preparing them so that he would have breakfast ready when she woke.
Karen woke randy. She gave herself a quick orgasm before getting out of bed. She slipped on a pair of panties and was about to put a dress on when she stopped. She remembered that Joanne often spent all day wearing just one of those cotton nighties with the cute pictures on them. She had a few of those too, although she always slept nude. She slipped one on and headed out nervously hoping that her Uncle wouldn't mind.
Neil was glad that he was standing in front of the kitchen bench when she emerged. It hid the erection that instantly occurred at the erotic sight of that short plump body dressed just like Joanne always did ... and if they were alone he would have usually been wearing a matching nightie. Unless of course he was due for an orgasm in which case he'd be in a silky nightie or a slip.The only difference was that Joanne wouldn't have been wearing panties unless they were visiting his sister the prude ... Karen's mother.
They spent all day together again. Neil already had enough food in the house for lunch and dinner so they didn't have to leave at all. Karen spent all day in that nightie, admiring Neil's arse. She was pleased from the outline that he clearly wasn't wearing boxer shorts. She liked a man in underwear that was tight enough fitting to show his package once he removed his pants, but not tight enough to damage it! She was certain her Uncles underwear would be perfect based on the outline in his shorts. She also thought he had quite a nice sized cock and was sure that after she had accidentally given him a peek at her panties he'd gotten an erection. Of course this just made her hornier. That nights masturbation session was even better than the previous evenings.
She was determined to give him plenty more 'accidental' peeks at her panties from now on. She would need to buy a few more nighties since she would be changing into one the minute she got home from work.
Neil again cock teased himself. But he could hardly touch himself this night as spending all day with his sexy fat niece in that nightie had him very horny! He was really looking forwards to tomorrow night when he would be allowed to cum! He was sure that he would cum so hard that he would get some in his own mouth.
But it wasn't to be. An hour after falling asleep he awoke to his first wet dream in many years. He had a clear memory of the final scene in his dream. He was standing in front of his niece dressed in his pink nightie and the pink polka dot panties. She was on her knees and had released his cock from the confines of his panties. She stroked his cock, just once. He came all over her face and matching nightie. He lay there imagining the follow up scenes as Karen demanded he make up for cumming too fast ... becoming his second mistress as he obeyed her every command, just as he had always obeyed Joanne's.
Karen began work on Monday and during lunch bought herself another four nighties. Every night that week she changed out of her uniform and into one of them as soon as she got back to her Uncles house. They shared the cooking duties and really enjoyed each other's company. Karen made no effort yet to find somewhere else to stay, thinking that staying with her Uncle might work out perfectly. After all, staying with him wasn't getting in the way of her masturbation, in fact it seemed to be enhancing it!