Teaching My Wife Ch. 06

Ann squealed with the pain of both the invader in her ass and the pain of having Jack's body pushing against her still flaming ass.

Jack pulled almost all the way out and then gave Ann another hard thrust. She was better prepared for this one and just grunted when Jack hit home.

He got a good rhythm going and sawed in and out of Ann's ass for several minutes. Jack reached around and found her clit with his fingers. Jack rubbed and pinched Ann's clit while he continued to piston his cock in and out of her ass.

All of the stimulation proved to be too much for Ann to resist and as she came she exclaimed, "Oh, shit, I'm cumming again." Jack gave her ass a few more strokes and then pulled out, stripped off the condom, got in front of Ann and shot his load in her face and hair. Ann winced as the hot cum hit her face.

Ann went to clean up and when she looked at her ass in the mirror saw that it was still red from the spanking Jack had given her and that several of his handprints were still visible. Ann felt mortified because she knew that everyone at the pool would see her ass and know that she, an adult woman, had just been spanked.

The marks from Jack's rough handling of her tits had also not faded entirely and Ann tried to adjust the top of her bikini to cover them but there was just too little fabric to work with. Ann glanced once more at her abused ass and tits, took a deep breath to gather herself and took Jack by the hand and led him out of her room.

They got to the pool and Jack escorted Ann over to the lounge she had used earlier. Ann reached up and gave Jack a deep kiss and Jack hugged her and kneaded her bare butt while she did. The kiss drew even more attention to Ann and she said that she was sure that everyone at the pool could see the handprints on her ass and her reddened tits and knew that she had just fucked the guy who had abused her body.

Ann remembered that she was to go into the pool each time she came to the pool and she quickly slipped off her heels and went over and got into the cool water. Ann thought that the cool water would soothe her marks and would also shield her a bit from the eyes that were focused on her.

Because of the limited time Ann had to complete her tasks she could only stay in the pool for a few minutes and eventually made her way back to her lounge. When she got there she found two of Jack's friends waiting for her.

The taller one spoke first and said, "I thought I would just come over and see if I could be next." The shorter one said, "I should be next because Jack and I saw you last night at the bar going in and out with different guys and he told me what he did with you in your room."

Ann said she was completely humiliated at this point because she thought that everyone within earshot would figure out that "next" meant "next to fuck her."

Ann tried to steer the conversation in another direction but the two guys were clearly impatient and looking for a quick fuck so they did not take the bait. As the arguing between the two guys grew in intensity and volume Ann could see that more and more people at the pool were tuning in and paying attention.

With her embarrassment mounting Ann just wanted to get away but she knew the only way she could do that was with a guy going back to her room. She also knew that picking one of these guys was not going to be a decision that the other accepted quietly so she took each of the two guys by the hand and said, "Let's go."

Assuming that these two guys made her cum at least twice, and they did, Ann had just increased the number of men at her gangbang by four instead of two.

Looking at the video later I could see that these two guys gave Ann a real workout using all three of her holes repeatedly. Although they were not gentle they did not treat Ann as roughly as Jack did.

Ann got back to the pool with a little less than an hour in which to find and fuck a third guy. As before she first went into the water to make her bikini transparent although she admitted that because she had been exposed for so long she did not even feel embarrassed anymore.

Returning to her lounge chair Ann again found another guy waiting for her. "I work with Jack," he said and before he could say anything more Ann took his hand and said, "Come with me."

Ann said that she knew that time was running out so she said that she fucked the guy hard and fast and made him cum twice, once in her mouth and once in her pussy. He returned the favor giving Ann the required two orgasms to earn himself and a guest an invitation to the gang bang.

"I literally had to drag the guy back to the pool," Ann told me and she made the four hour deadline with only minutes to spare.

With the time pressure Ann had not been able to send me any messages as to what had happened Wednesday or Thursday. She brought me up to date on Thursday when we spoke and I was surprised that the total had reached 17. Ann was now facing a gang bang in which she would be the only woman with as many as 17 guys, all of them virtual strangers. Ann was going to pull a train and it was going to be a long one.

"Are you sure you want to go through with this?" I asked Ann pointing out that because they guys were all staying at the hotel it was unlikely that any would drop out due to family commitments, etc.

"I thought I had to because I already started," Ann replied.

"Normally that would be the case but in the past you had only one session with the man or men and you could decide not to go ahead at anytime up to when the door of your room clicked shut and then you could only say "no" in very limited circumstances. Here even though you have already recruited the men for your gang bang it has not started," I explained.

"What's the matter, afraid that I will handle your challenges?" Ann taunted.

"No, I just wanted to be sure you understood your options."

"I admit that I am still apprehensive because there will be a lot of men and I will be alone and at their mercy but my pussy just oozes when I realize that once I start I will have to fuck and suck and otherwise perform until every guy is satisfied. Besides, I plan to fuck their brains out and be wanting more when there are no guys left who can still get it up."

"Be careful about having your words write checks your sexy little body will have to cash," I said.

"Want me to at least tell you what the second letter says," I asked.

"Don't you dare. When this started weeks ago I was dying to know what was going to happen to me. But now I know that it is going to be a gang bang and that I am going to be standing virtually naked in front of a group of guys reading a letter that tells them how they are to use and abuse me. I just cannot get that image out of my mind and know that my hands will be shaking and voice breaking as I learn my fate."

"There will be some surprises and some things you will not like doing in the letter," I told Ann.

"Aren't there always?" she replied.

"By the way, I ordered a party set up for your guests, mostly liquid refreshments. It will help lower their inhibitions and make things more interesting for you," I said to Ann.

"You're so sweet, you think of everything," she replied sarcastically.

We talked for a few minutes about other things and Ann said that she would call me when her adventure was over, likely sometime Saturday morning.

Ann said that she slept fitfully Thursday night and woke up several times to the image of her reading the letter to her gang bang crew. Her last seminar ended at 1:00PM on Friday and she went back to her suite to prepare for the night's adventure. She used her Jacuzzi tub for about an hour and then took a short nap.

She awoke to find that it was about 5:30PM, or less than two hours until her guys began to arrive. When she issued the invitations she told the guys to plan to arrive around 7:30PM but that the main event would not start until eight.

Even though she had done it the day before prior to donning her new bikini Ann shaved her pussy and legs leaving her silky smooth. She applied body lotion and did her hair and make-up to perfection. She knew that soon after her gang bang started that she would be a mess but wanted to at least start looking her best. When she was finished she put on the hotel robe and waited.

Around 7:00PM room service delivered the party set up I had ordered. Ann had the guy set it up in the sitting room part of her suite. She said that when she saw bottle after bottle of scotch, gin, vodka, whisky, etc. she knew that the men would not be thirsty and would likely be less reticent about using her.

When the room service guy left Ann decided to finish getting ready and opened the beige bag I had put in her luggage. According to the first letter, Ann was to wear only the contents of the beige bag and her CFM heels for her gang bang.

Ann gasped when she saw what was in the bag. There was a set of leather cuffs for her wrists and a set for her ankles. There was also a larger set to go around her thighs just above her knees. The final items were a wide leather belt that went around her waist and a matching collar for her neck. Each of the items had metal loops through which ropes could be run and clips that allowed the items to be joined together.

Ann said that she knew that if she greeted the guys wearing these bondage items that she would likely spend a good portion of the night restrained in some fashion. Even though she could still call things off she knew that she could not do so without causing at least a bit of a scene and when she glanced over at the desk and saw the second letter she knew that she had to feel what it would be like to be reading it aloud before a group of guys.

She put on the leather items buckling each tightly. Ann checked the beige bag again to be sure it was empty and found several lengths of rope that she took out and lay on the desk next to the letter, the video camera and the second blue bag of toys. She went to the closet and put on her CFM heels.

Ann sat down to wait. She did not have to wait long as at 7:30PM there was a knock on the door and she opened to admit the first two guys who would be fucking her that evening. One had fucked her earlier in the week and the other was his guest. They were astonished and delighted with how Ann was "dressed" and ran their hands over her naked body as she showed them to the bar.

Ann shuddered as she suddenly realized that a man she had not even met had already seen her naked and rubbed his hands over her breasts and ass. She also knew that he would not be the first total stranger to do that and more to her tonight.

This was when the reality of her situation finally hit Ann. Unlike her previous adventures, where she had time to flirt and chat with her soon to be lovers, this time she had to work fast to fit three guys in (pun intended) within the four hour periods for her hunting sessions. There had not been as much time for verbal foreplay as it were and with Jack's friends on Thursday at the pool there was no conversation, just let's get up to my room before I get even more embarrassed.

Ann realized that even though she had already fucked at least half of the men who would be here tonight that she really knew very little about any of them. She knew that she would know nothing about the guests they would bring. That meant that she really would be getting gang banged by a room full of strangers and would be utterly alone and at their mercy while it happened.

When we had first talked about having Ann do a gang bang she said that her biggest fear was being alone with a group of strangers who would try to one up each other in how hard they used and abused her. She said she had visions of being fucked by one guy while the others cheered and urged him on to, "Fuck her harder," and when that guy was done trying to fuck her even harder to prove they could do better.

As these thoughts ran through Ann's mind her fear increased exponentially and despite the air conditioning running full blast a sheen of nervous perspiration soon covered her naked body making it even shinier that it was from the body lotion she had used. At the same time Ann later told me her lust also seemed to go off the chart and she said she could not believe that her pussy became even wetter.

Ann's thoughts were interrupted by a knock on the door and Yoshi and his two colleagues were next to arrive. They had trouble bowing to Ann because they could not take their eyes off of her naked form. These men also passed their hands over Ann as they entered her room and did not introduce themselves until they were inside. Ann had again been manhandled by men whose names she did not even know.

Jack and his co-workers and their guests were next and Ann watched as a group of ten guys piled into her suite. They were boisterous and Ann felt many hands on, and fingers in, her body for what would be the first of many times this night.

A few minutes later one more guy arrived and explained that his guest had to go back home due to a business emergency.

That made it a total of 16 guys milling about and drinking in Ann's suite and as she had invited 17 the turnout was pretty impressive and meant that she would have a lot of fucking and sucking to do as the night wore on.

Despite knowing that no other guests were expected Ann waited until 8PM because that was the time we had decided would be the equivalent of the door clicking shut in her previous sessions. At a little after 8PM, Ann herded everyone into the sitting room part of her suite and got them quieted down as best she could considering that more than one of them had had a couple of drinks already and some in Jack's group appeared to have had a few before they arrived.

She got her glasses and put them on. The glasses actually made her look even sexier. Picture a hot school librarian naked and dressed in bondage gear and heels.

Ann said that she was nervous and the feelings of fear and lust were overwhelming. She said that she could see her own juices leaking out of her exposed pussy and onto her thighs.

With trembling hands Ann opened the letter and announced to the assembled guys that it was from her husband.

She started to read the letter aloud in a quiet voice:

"The woman standing before you is my wife, Ann. Up until 10 months ago she was your typical unassuming wife in a monogamous relationship and with not much prior sexual experience. Like many of you I was long tired of the same old, same old and began to pressure Ann to open her sexual horizons. She eventually agreed and started out by having sex sessions with guys she picked up on her business trips. For each session I prepared a letter like this one that outlined what the man or men were to do to Ann.

At first Ann was a reluctant participant but somewhere after her first gang bang with six guys it was if a dam burst. Ann began to crave her adventures and to dare me to come up with more and more challenging scenarios for her. That is why all of you are here; tonight you are Ann's challenge.

The rules are simple. The entire session is to be videotaped and one of you should follow the action at all times with the camera. Safe sex is required and if you are in Ann's ass or pussy you must be wearing a condom. No scat or water sports and nothing that would permanently mark or injure Ann.

You cannot invite any additional men to join the party once it starts and the party is over when the last of you has decided he has had enough. All activities must take place in Ann's room.

Other than that Ann is yours to use however you see fit. If Ann refuses to do something you want to do you are free to force her to do it. She will sometimes complain, whimper and bargain to try to talk you out of things she may find objectionable but just ignore her. She understands that her right to say "no" except for violations of the rules ended at 8PM.

Like I had up until 10 months ago many of you probably have wives and girlfriends who deny you sexual activities you would like to do. Well, here is your chance. You can take out all of your frustrations of those denials on Ann.

You are free to use Ann's mouth, pussy and ass and can do so singly or in double and triple penetration.

For each of Ann's previous adventures I also listed in the letters a few specific things that should be done to her and here they are for this adventure:

1) Ann has not experienced having two dicks in her mouth at the same time or in having double vaginal intercourse. You should make sure that she does both before the night is over.

2) In the weeks before this adventure Ann pestered me to find out what I had planned for her. I gave her a hint saying that one of the activities would be something that had happened before. When she learned that I had planned her second gang bang she thought that was the repeat but it isn't.

During her first gang bang the guys made Ann suck them until they came in her mouth and then had her spit their cum into a water glass. When all of their cum was in the glass they forced Ann to drink it by putting binder clips on her nipples until the pain became unbearable and she did what they wanted."

Ann's hands started to shake even more as she read this part of the letter and her throat became dry making it even harder for her to get her words out. "Please," she said, "don't make me do that."

Ann looked out plaintively at the assembled men and saw that no one was going to speak up to tell her she would not have to do it. She kept looking out looking for some support when someone said, "Finish the letter so we can get started."

Tears welled up in Ann's eyes as she returned to the letter:

"Tonight whenever any of you cums in Ann's mouth you are to make her spit it out into a glass. Whenever any of you cums in a condom you are to drain the condom into the glass as well.

When you think there is enough cum in the glass give it to Ann and tell her to drink it. If she refuses there is a ball gag with a breathing tube through it and a funnel in the blue bag Ann has left out somewhere. Force the gag into her mouth, tighten the strap behind her head and attach the funnel. Hold or restrain Ann on her back and pour the cum into the funnel.

Otherwise do what you want and be sure that you use Ann to the max. She wanted a challenge so give it to her."

Ann dropped the letter on the desk and just stood there silently with a tear running down her left cheek for a few moments. She said her mind was racing thinking that she should have called things off and been less arrogant in demanding a challenging scenario but she knew that she now had to live with the consequences of her decision.

She did not stand there alone for long. In a few moments Jack and his group surrounded her. Jack ran his hands over her breasts and pussy. In one quick motion he slipped two fingers into Ann's cunt and when he felt how wet she was announced that fact loudly.

Jack fingered Ann a few times and she grabbed onto his arm and held on. In another few seconds her mouth opened and she moaned as she came for the first time that night.

Ann's moans brought cheers and applause from many of the guys and one of them said, "Sounds like this bitch is ready." Two of the guys with Jack led Ann over to a table and laid her across it on her stomach with her pussy on one side and her head on the other. Within seconds a guy was buried balls deep in her cunt and another was deep in her throat.

Ann had not fully come down from her first orgasm and the cocks hammering away at her pussy and mouth soon had her over the edge and as she came a second time she gurgled her cries of pleasure around the cock that was in her throat. This set off the guy whose cock she was sucking and he fired his load deep into her throat. There would be no cum to spit out.