Erotic Evening

Being just over thirty Mary thought of herself that she still looked pretty good. A bit skinny, and because of that rather tiny boobs, but still a real waist and a firm butt. Long blond hair and a sweet face that looked its best with little make-up. Even at high school she never had real problems getting the boys interested, and in the end she had married John. The first couple of years it had been wonderful, just a little argument every now and then, but no real problems between them. But lately it had been different. It seemed like John was no longer pleased with her, did not really look at her anymore. And so she stood more and more in front of the mirror critically looking at herself, always coming to the same conclusion: she still was looking good for her age. And John also still looked good. Yes, a beginning belly, but being in his late thirties that was no shame. He still had a head full of long dark hair, reasonably well muscled, not like a bodybuilder but just enough. She still liked to look at him, and hoped that he thought the same about her.

Now she was sitting in the living room talking to her best girlfriend about last night. She and John had both agreed to have an erotic evening, four times a year, in which one of them had to do whatever the other wanted. They had made that agreement a few years back when they both had noticed that their sex life was not as good anymore as it had been before. Without any reason they just had less and less sex, sometimes weeks passed without any sex at all. They knew they were to young to let that happen, and this had seemed like a good idea to get things going again. Yesterday had been John's evening, but she was left with a very bad feeling about it.

"What has he done that you were so dissatisfied?" her girlfriend asked.

"Strapped me to the kitchen table, naked on my belly, and taken me anally. I totally didn't like it, and so little fantasy... If he goes on like this our sex life will be down the drain soon again. And just to prevent that was the reason to start with this whole thing. To get back the lust for sex, and I mean the both of us."

"So in three months it will be your turn again. That gives you at least enough time to think of something better. Do you want to lets say pay him back?"

"Yeah, something like that, but I wouldn't know how. Tying him to the kitchen table is not my thing, and I want to make sure that at least I will have some fun. I assume he had fun last night, even though I hadn't. SO if I can think of something that will not please him but does please me so much the better. But I got no idea where and how to start."

"Well, just last week I came across an advert on a sex-website. Yes, I get there more then once in a while, our sex life has also not been great, and I still have some fantasies. Anyway, this advert might help you on the right track to get things started your way, at least you can have a look at it. If you don't like it, nothing lost, right? I'll look it up and send you the link."

"Is your sex life down and you want to revive it? Do you need help? Don't want or can't afford professional help? Maybe I can help you. I am a dominant man with a broad fantasy for erotic dreams. I am a quite unusual type, but will tell you more about that when you react on this advert."

And under it was only an email address, nothing more. Well, an email cost nothing, and was anonymous enough, so the next day she sent an email. She explained her situation, her problem with John, without using his name, she asked about cost and also asked for an example of what this man could possibly do. A couple of days later she got a reaction.

"Hello,

So I am a dominant man, but I prefer to be dressed in womens lingerie, and sometimes also in a dress or skirt. I just tell you immediately so you know what to expect. You wrote that your sex life was low and you and your husband had agreed to four times a year have an erotic evening. And now you want an idea to get back at him while enjoying yourself. Suppose I come to visit the both of you, with some stuff, and you and I together will really surprise John."

And what followed was extensively described what the plan was, if she agreed to it. She would have to buy some things herself, and prepare John a bit. It would not be good if he immediately get upset seeing some other person in the house without being somewhat informed up front. She discussed the idea with John to have an extra person on their next erotic evening. She saw that his thoughts were about a second woman, and got excited by the idea alone. SO he had no objections at all, and that it would not be a woman she just didn't tell him, he would find out soon enough.

And the day came for their special night. The man had said in his email that he preferred to be called Simone, and wanted to be treated as if he were a woman. He would be at their door exactly at eight, so ten minutes before she sent John upstairs and ordered him to go to the toilet, because later on he might not have the possibility anymore, and to take a shower. She would put his outfit for the evening on their bed, and he was to put that on after his shower and then come downstairs.

Exactly at eight the doorbell rang, and she opened the door to a man that was in all aspects unnoticeable. Medium height, medium weight, middle aged or maybe a bit older, the only remarkable thing was a small mustache. She would have passed him on the street without noticing him at all. She invited him in, and asked if he needed any preparation. "Just changing clothes, nothing more. I have got everything we might need in my bag, and if you got what I asked you to get it will go smoothly. Maybe you can get us a cup of coffee while I change."

While she was making coffee she some little noises in the living room, and when she came in with the coffee Simone was not unnoticeable anymore. On the contrary, now she was a personality that would attract attention everywhere. From the floor up she saw shiny black leather boots with high heels, black stockings with black garters, a shiny black dress with a split along the side through which she could see black satin panties and the side of a black satin bra. The front of the dress was filled, it looked like at least a D-cup. Above the dress was still a masculine head, with that mustache, but it was crowned with a wig of long dark hair with curls in it.

"So, that;s something different! You look good, a lot better then what I expected. That's a very sexy outfit, I am almost ashamed for my own dreary clothes."

"No reason to be ashamed, certainly not if under your dress you are wearing what I asked. Show me please."

Mary took off her dress, and stood in just her lingerie. A white satin set of matching bra and panties with some lace, white garters, white stockings and on her feet white pumps with a moderate heel. She felt watched, and felt good about it. It had been a long time since anybody else then her own husband had seen her in just lingerie. As agreed she settled on the couch next to Simone, and together they drank their coffee. Just when she emptied her cup their was a shout from upstairs, if she was serious about the clothing she had laid out.

"Of course, otherwise it wouldn't be there, right? And hurry up, you're taking too long already."

It took about twenty minutes more before he finally came down the stairs, very slowly. Of course John was walking slowly, it was his first time walking on heels. Not very high, just under two inches, but high enough to make him unstable. He was still grumbling inside when he entered the living room Right at that moment he became very quiet, and his mouth fell open. He stopped right in the opening, looking a bit silly in his red summer dress and red pumps.

"Hi, I am Simone, but you will only call me Mistress tonight. Remember that, and make no mistakes. Understood?"

"Yeah, right, fine."

"No, not right and not fine. Even at the first sentence you make mistakes. You will call me Mistress, and you will always call me Mistress. Have you now understood?"

"Yes, Mistress." It did not sound convincing, but Simone left it at that.

"Because you need to be punished you will stay standing up while we are seated. And you also don't deserve coffee. Your wife here has asked me for help because you as a girl seem to be quite shy, and you need to get out of your shell a bit more, so she thinks. What is your opinion on this?"

"I'm not a girl, don't want to be one, so what do you mean?" and after a very short break he added: "Mistress."

"I can clearly see that you are a girl. Why else would you wear a dress and walk on high heels? And it looks like you're also wearing a bra, I can see the outline of it through your dress."

"Hm, alright, I guess for tonight I will be a girl. What else will happen tonight... Mistress?"

"Together with your wife here I will initiate you in what girls should know about boys whenever they are big enough to look at boys. And you definitely are big enough. But first take of your dress so we can see what you are wearing underneath."

John took the little dress over his head with some trouble, and then stood before them in just red panties and a red bra. He felt more then naked, specifically because the panties were of a sheer material so his penis was fully visible, completely flaccid now because he did not feel sexy at all. But, agreed was agreed and if this was what Mary wanted tonight it just had to be. His bra had open cups so his nipples were also free to be seen. All of a sudden he realized that his face was as red as his underwear.

"That looks good enough, and it is evident that you are no longer a little girl anymore. What do you think Mary, is she ready to learn more about boys?"

"I think so" Mary said with a wide grin. She was already enjoying herself.

"Great. By the way, what is the name of your girlfriend here?"

"Let's call her Hanna, that suits her."

"Good, Hanna, walk over to the table to that bag there and take out the black box on top."

John walked wobbly to the table, looked into the bag and saw a black box, about seven inch long and four by four inches wide. He took it and wobbled back to the couch and handed the box to Simone.

"No, I don't need to have it, you can open it. But be careful not to drop anything."

John took the lid off the box and saw inside a big dildo on some black cloth. The thing looked lifelike, with balls and all. It was also bigger then his own dick had ever been, he noticed disappointedly.

"Tell me Hanna, do you know what this is?"

"Yes, a fake dick. Mistress." He remembered just in time to say Mistress.

"But decent girls call that differently. Help her a bit Mary, how do decent girls name that?"

"I normally say penis." said Mary.

"So you hear it Hanna, you will also call this a penis. Have you ever before had one in your hands?"

John was gonna say that he regularly had his own in his hand, but thought it not appropriate now, so he just shook his head.

"So you are a decent girl after all. Tell me Hanna, what do you think decent girls will do with a penis the first time they see one, just like you now?"

"No idea what I should have to do with it Mistress."

"Well, if you get a boy so far that you can see his penis he will want you to do something with it as well. You will understand that. So what would you do with it?"

John looked sharply at the dildo again, and wondered if he was willing to go ahead. He decided to go along with Mary's game, to the bitter end. He took the dildo out of the box and noticed that it also felt real. Soft but solid, only cold to the touch. He held it in his hand and bend a little forward to put the thing in his mouth.

"No, no, we are not there yet. That's a nice idea but decent girls like yourself do not start there. Try thinking of something else that doesn't go that far immediately."

John got red in the face again, and said they just had to tell him what to do. Simone looked at Mary and she replied immediately.

"You could try something with your hands, most boys seem to like that."

John took the dildo in his left hand, and made stroking movements with his right. It seemed to be what was expected, he heard positive noises from the couch.

"Right, that's where you start. And then you let the boy also go ahead if he wants to feel you up. Do you understand that?"

"Yes, Mistress."

"You don;t have much for titties, but it will have to do, and most boys don't care if you have a lot or a little as log as you have titties. And then, after you have done this for some time you go on with what you already wanted to do before. Let's see how you do."

And with again a red face John started licking the dildo, and he put a little bit in his mouth. In his mind he could already hear the comments that he had to go deeper, so not wanting to hear that he he did so himself. After some moments the biggest part of the dildo was in his mouth and he was really sucking on it.

"So Hanna, suppose you wanted to go further, what could you possibly do?" said Mistress Simone.

"Let it get inside I think you mean, Mistress."

"And inside where?"

With an even redder face, almost whispering, John said: "In my pussy... Mistress."

"You see Mary, she does understand real well. You could have had more confidence in her. But Hanna, what would you have to do first?"

"Get undressed? Mistress?"

"That too, of course, but should you not put something on first? At the boy whose penis you enjoy sucking so much?"

"Oh, I think you mean a condom Mistress."

"Well, get one."

"I don't have any, Mistress."

"Decent girls always make sure they are prepared. But for now I have one for you to use. In my bag, in a red pouch. Put that thing down for now, go get one, and then show us that you know how to use it. And Mary, while Hanna is busy, could you get us another cup of coffee? I feel I could us one."

John put the dildo back in its box, and wobbled to the table and got himself a condom. While he was walking back he passed his wife, who grinned at him, surely having a lot of fun. Then he was busy getting the condom out of its wrapper and putting it on the dildo as good as he could. Because he also had to hold on to the dildo it did not go easy and it needed his full attention. Therefor he missed that Mary had put her dress on again, and that under her dress, at groin level, she had a big bulge. Simone did see it, but she knew it was gonna happen, she had planned so with Mary.

"Yes Hanna, thats completely right. But just before that penis goes into your pussy there is one little thing you have to do, which is checking if you are wet enough. I'll just tell you, so you don;t have to think about it. But just imagine that you are not wet enough, then what?"

"I would have to use lubricant, but I don't have that either. I suppose you do Mistress?"

"Indeed, it is in a small brown bottle in my bag. But for now I think we are done with the theory, don't you think so Mary?"

"Yes Simone, I think so too. Is it time for the next round?"

"Yes, absolutely. After theory comes practice. Hanna, you'll be glad to hear that your friend Mary is willing and able to help you further. We don't have real penises here, and the one you have in your hand is not suitable for what we need to do. But as you see Mary has put on some more clothes again and under her clothes she has a nice surprise for you. Come sit before her, on the floor, on your knees."

John did as he was told and sat down on his knees in front of Mary. At that moment he noticed that Mary's dress was bolled up in front.

"Just pretend that Mary's dress is a boys' jeans and shirt and show us that you know how to undress a boy."

John took the bottom of Mary's dress and slowly lifted it up. She cooperated immediately so he could take it off over her head.

"Well Hanna, there we have a nice penis in underwear. It isn't boys underwear, but you can pretend it is for now."

And indeed Mary had a big strap-on dildo inside her panties. Almost as big as the one John had in his hands some moments ago.

"Take it out, and show us what you have learned tonight."

And again John did as he was told. He took Mary's panties down on the front, so that her dildo stuck forward, all in the open. He started to slowly pull on it and Mary made groaning noises just like a boy would when being pleasured.

"Look now Mary, it seems Hanna is enjoying herself. Her clitty is swelling up." And so it was. He was getting a hard-on. When he realized it he got red in the face, again, which was beginning to get very annoying. He heard giggles from Mary, but was not able to look up to her.

"Come on Hanna, speed it up, you're taking too much time, go on to the next step."

John bent forward, but before he could do anything he was called back.

"No, with a boy present you let him feel you up right about now. Let him feel your titties, take his hand and put it on your titties."

John grabbed Mary's hand and put it on his bra. She pinched his nipple hard, and it hurt him badly. That was something Mary had never done before. He had done it to her, quite often even, but being on the receiving end of it was not to his liking. He wondered what else he would have to go through. He found out soon enough.

"Right, now you can go further, give your boyfriend some pleasure. And your boyfriend will be played by Mary."

John bent forward again, smelling the known odor of Mary's pussy, but wisely decided it was not the moment to touch her there. He took Mary's dildo in his mouth and sucked on it. Mary played along by moaning some more, and by moving her hips to and from him. With every movement the dildo was pushed deeper into his mouth until he was gagging. So that's what it was like for a woman if you moved enthusiastically when getting a blowjob. Not very pleasant, he realized

"We'll just shorten this part, and go on to the next chapter. I'm sure you remember what to do, so show us."

John got up and took another condom out of the bag. He was getting acquainted to walking on his heels. He took the condom out of the wrapper, and put it on Mary's dildo. Then he looked at Mistress Simone, thinking he was finally done.

"What was it that you had to check at yourself at this time?"

"Whether I'm wet enough Mistress."

"Well then, do that."

For a moment John wondered what he had to do, and then slowly put his hand down the front of his panties.

"Yeah girly, normally that's where your pussy is, but not with you, right, because you're a special kind of girl. Feel your own pussy."

Hesitatingly John put his hand down the backside of his panties. He heard a deep sigh, and looked up.

"Girly, girly, that will not do with your panties still on. I know, we did not discuss this in our theory lesson, but you yourself knew to get undressed before going on. Did you forget that already?"

"No Mistress." and John turned around to take his panties off.

"Come now girl, we are all girls amongst each other and we don't have to be ashamed if we are a bit different from other girls. You don't have to turn your back to us, nobody will judge you. Let us see what you are doing."

Even more red then all the times before John turned back to the couch and took off his panties in one quick move. His rigid dick stood straight forward, but he did not touch it. He put his hand on his bottom, put his finger on his asshole and whispered: "It is very dry Mistress."

"You know what to do about it, and where to find it."

Again John walked to the table, dressed only in a red open cup bra, high heels and a solid erection. He was enormously embarrassed, mostly when walking back so the two on the couch had a perfect view on his swaying dick.

Back at the couch he hesitated some more, but took the cap off the brown bottle. He got some of the liquid on his hand, and rubbed it around his asshole.