Teaching My Wife Ch. 06

I don't know how many guys you think you can handle but you did tell me before your first gang bang that you had the same equipment as the women in the gang bang videos I had you watch where it was not uncommon for there to be more than a dozen guys and just one woman. You took on six during your first gang bang, eleven during your anal gangbang and three plus a girl in your fraternity adventure so you have some reference.

Whatever number there are you will be alone with them and be at their mercy. By having you audition some of the men first you will get some solace because at least some of the men there will be men you at least were comfortable picking up and who did make you cum at least twice.

That familiarity is, however, a double edged sword. On the one hand you will know those guys to some extent. On the other hand because they have already had sex with you they will know that they can do what they want and some of them may be more aggressive and demanding of you than they were the first time.

The friends they bring are an open question. You will have no choice as to who these men are and they will not have passed the initial screening you used with the men you audition. Basically the guests will simply introduce themselves and then join in fucking and otherwise using you. Other than their name and who invited them you will not know anything about them.

There are two sets of toys in your luggage. You are to open the beige bag before the guys start to arrive for your gang bang and put on the contents and your CFM heels. You are not to wear anything else and are to open the door for your guests that way.

At 8PM on Friday night you are to open the second letter and read it aloud to the men who will be there for your gangbang. Leave the blue bag of toys out for the men.

Of course, you can just decide to call this off if it is too much of a challenge.

Smiles."

Ann dropped the letter on the bed when she finished reading it and felt the bottom of her stomach fall away. She said that her hands were visibly shaking as she got a drink from the mini-bar. When Ann finished her drink she carefully re-read the letter and said that she trembled even more the second time through it.

Ann dialed the phone and when I answered she said, "I just finished reading the letter a second time."

"And," I replied.

"I don't know if I can do it, the thought of being alone with that many guys scares me."

"You don't have to; you can always say that the challenge was too much."

"Bastard, I knew you would say that."

"Well, it's true; you can always just call it off and enjoy your conference in other ways."

"Why didn't you tell me you wanted me to have another gang bang instead of just saying this session would include something that was done in a previous one?" Ann asked.

"Now if I told you what was planned it would ruin the surprise, wouldn't it?" I replied knowing that this was not the activity to which I was making reference when I gave Ann my cryptic hint.

"Let me think things through and see what is worse, the gangbang and everything associated with it or having you smirking at me because I finally chickened out," Ann responded and we said our goodbyes.

I did not hear from Ann until early Tuesday evening when she sent me a picture of herself that she took with her phone. She looked gorgeous and was wearing the yellow top and CFM heels. The message with the picture said, "I made my decision."

Ann later told me that she could not believe how conspicuous her yellow top made her look. She said that she thought that almost all eyes were on her when she walked into the hotel lounge and took a seat on one of the bar stools. Ann said that she knew she would have to work fast to pick up her quota of three guys and she immediately started to cross and uncross her legs so that her lack of panties would be evident to the guys that were sitting around her.

It did not take long for a guy to notice and soon he was at the bar getting another drink and offering another to Ann as well. His name was Yoshi and he was a Japanese American from the West Coast. Ann said that he was very polite and based on that decided to invite him up to her room.

Despite her growing number of adventures, Ann had not had sex with an Asian man before. She said that she found his skin particularly smooth and his thinner pubic hair made his average sized organ look larger than it was. Ann said he fucked her to three nice orgasms before pulling out, taking off the condom and cumming on her face.

Ann invited Yoshi to her gang bang and told him to bring a guest. "My two colleagues are travelling with me so I will bring two guests," Yoshi said, "and we will do bukkake." Ann said she was a bit taken aback with her first guy asking to bring an additional guest but because Yoshi was so gentle when he fucked her she told him it would be OK.

Yoshi escorted Ann back to the bar and she gave him a deep kiss when they said their goodbyes. She took her place on a bar stool and sent me the following text message; "Yoshi, 3x, p, 2g, btw, wht is bukakee?"

Although cryptic I was able to figure out that the guy's name was Yoshi, he had fucked Ann's pussy and made her come three times so he was her first invitee. I was surprised that she had agreed to allow two guests but assumed she had her reasons.

I was intrigued that Ann did not know what a bukkake was but as her sexual metamorphosis had only been during the last ten months it made some sense. Even though Ann was getting more receptive to swallowing cum doing so, and having cum on her face, were not among the activities that she found particularly appealing.

Not wanting to ruin the surprise of her first bukkake, I sent Ann a longer e-mail talking about things that had happened at work and around our home and ignored her question. Apparently she was busy with other things because about seventy five minutes later I received a message saying: "Chet, 4x, m, p, a." Translated, Chet had fucked her mouth, pussy and ass and made her cum four times so he was also invited to the gang bang.

The third and last message of the night came in shortly before the four hour window was to close and read: "Loser, 0x, p, called himself pistolpackinpete, little pistol, fired too soon." Translated, the third guy was not much in the size or stamina department and had not gotten Ann off despite fucking her pussy.

That made the total for the first night, five, with two guys and three guests. The session Wednesday evening worked out about the same with two guys making the cut and two guests. When added to Tuesday's number that made it a total of nine if everyone showed up Friday night.

Late Wednesday night the phone rang and when I answered it Ann said, "You cannot be serious about me wearing that thing you called a bikini in public."

"Aw, come on, you are at an international resort. Lots of the European ladies will be topless at the pool," I replied.

"I would be better off naked because the fabric is so sheer you can see every bump on my nipples and if you are within ten feet of me you can see every bit of my pussy," Ann said.

"Sounds like good advertising for what you are at the pool to find," I replied.

"Look, if wearing the bikini is too much of a challenge just call the whole deal off. Of course, you will have to explain to the guys you already invited to your gang bang why you are calling it off," I continued.

"Why do you always make things so hard for me," Ann whimpered.

"You were the one who wanted a challenge, the one who taunted me until I agreed to come up with a scenario for you. Just admit you cannot go through with this adventure and I will only call you a 'quitter' and a 'chicken' for, oh, maybe, six or seven years," I countered. I knew that this would push Ann's buttons because she is very determined and even though quitting would be the easy way out Ann's pride would never let her do it.

"I hope the hotel throws me out," Ann spat out and hung up.

Despite having several drinks during her adventures on Wednesday night Ann set the alarm for early Thursday morning so she could prepare herself to wear the most revealing swimsuit she had ever worn. She shaved her pussy twice and made sure she got around her asshole because the only thing covering it would be the string that went up between her butt cheeks to the string that would go around her waist.

When she was done Ann put on more traditional business wear and went to her meetings and seminars. She said that her pussy was extremely wet and that she thought that anyone near her would be able to smell her arousal. Ann knew she would feel humiliated with everything she had to offer essentially on display once she put the bikini on but also said that it turned her on at the same time. Apparently she had gotten over her fear of the hotel throwing her out.

Ann finished her last seminar and went back to her room. She stripped off her business wear and stood naked holding the bikini in her hands. The bikini consisted of about three square inches that would cover her pussy and not much more that would cover her breasts and nipples. Because the fabric was sheer and almost transparent, whatever was covered would not be covered that well.

Ann put on the bikini and walked in front of the mirror. Her nipples protruded enticingly through the sheer fabric as did the outline of her pussy. Ann trembled as she realized how much of her would be on display at the pool.

Another dab of perfume and Ann finally had enough worked up enough courage. She took one more look at her visage in the mirror and flipping her hair back she strode towards the door. Ann opened the door to her room and stepped out into the hall.

She said that she felt extremely vulnerable as she walked down the hall to the elevator.

The elevator arrived and Ann was happy to see that there was no one on it and she pressed the button for the pool level. Ann exited the elevator and walked out onto the deck surrounding the pool. Ann felt as though everyone was staring at her as she walked over to an empty lounge chair. She stood patiently while a pool attendant put fresh towels on the lounge and took her drink order. She was going to lie down when she remembered that the letter said that she was to get the bikini wet each time she arrived at the pool.

Ann slipped off her CFM heels and then made her way over to the shallow end of the pool. Ann walked down the steps and descended into the cool water until it was almost up to her shoulders. Her nipples, which had already been sharp points due to her embarrassment and arousal, hardened further due to the cool water. It seemed like only seconds before a man appeared next to her and started to strike up a conversation. The conversation, for what it was worth, was about her swimsuit and how hot she looked in it.

"Would you like a drink," the man, whose name was Jack, asked.

"I ordered one before I got into the pool. It should be by my chair now," Ann said.

"Great, I will get my drink and join you," Jack replied.

He took her by the hand and helped her up the steps and out of the pool. As they started to walk across the deck Ann looked down and saw how transparent her bikini had become due to it being wet. She gulped as her already high level of embarrassment grew. Ann was sure that everyone could see her nipples and pussy.

Ann sat down on her lounge and closed her thighs in an attempt to shield her pussy from wandering eyes. Jack sat down on the lounge next to her and they continued to chat. After a few minutes Jack said, "Now I know who you are. You were in the bar last night wearing a yellow top and yellow heels, weren't you?"

Ann pleaded guilty and Jack continued, "I was there with a few of my co-workers and was going to come over and try to meet you but it seemed that you were always either coming or going with a different guy on your arm." Ann smiled weakly as she realized that people had noticed her slutty behavior.

Knowing that she had to get started to make her quota, Ann decided to be more forward and said, "Would you like to be the one who goes with me now?"

Jack readily agreed and Ann explained the rules about videotaping, condoms and the other limits she had.

Jack stood up and helped Ann to her feet and into her heels. He put his arm around her waist and let his hand rest on her hip as he escorted her from the pool and into the hotel. As they were walking into the hotel, Ann saw Jack look over at a group of guys and noticed that they were smiling and giving him the thumbs up sign and realized that again people had taken notice of her slutty behavior.

While they were waiting for the elevator that Jack pulled Ann towards him, hugged her and kneaded her naked butt cheeks. When they got on the elevator she said that he took one of her nipples between his thumb and forefinger and squeezed it hard enough for her to cry out. Despite her cry, Jack held on to her nipple firmly until the elevator got to Ann's floor. Ann said that she then knew that Jack would be a rough fuck.

Jack followed Ann into her room and the door clicked shut. Ann said that every time she heard that sound she would shudder because she knew that her options to say "no" had just become very limited.

Ann got the video going and Jack pulled down his swim trunks and pushed Ann to her knees saying, "Start sucking, bitch." Ann took the first couple of inches of Jack's cock into her mouth and reached up with her hands to hold the rest. "No hands," Jack said as he pushed Ann's hands away. "Just use your fucking mouth."

Ann redoubled her efforts to satisfy Jack with her mouth but before long he had grabbed her hair and was roughly face fucking her. She sputtered as she tried to keep up with his efforts to force his cock into her throat. Suddenly Jack released his grip on her hair and grasped a nipple in each hand and squeezed and twisted roughly. Ann shrieked around the cock in her mouth and Jack slipped into her throat.

Jack released one of her nipples and put that hand at the back of Ann's head keeping his dick lodged deeply in her throat. "Now, milk me with your throat," Jack directed Ann and she did what she could to bring him off.

Ann pushed her hands against Jack's thighs trying to dislodge the dick that was now fully in her throat. "Put your hands down," Jack commanded, "that dick stays where it is until you make it cum and you will be sorry if it doesn't."

At this point Ann became truly frightened of what Jack might do to her and she decided that she had better get him off as quickly as possible. She started to suck harder and use her tongue on the base of his cock and it seemed to be working as Jack started to moan. Jack continued to hold on to the back of her head keeping his dick wedged as far into her throat as it would go.

Jack moans grew louder and Ann knew that he was getting close to cumming. She continued to suck as hard as she could and to use her tongue on the base of his cock. Jack took his right hand off of the back of Ann's head and used it to grab her left nipple. He squeezed it roughly and twisted it as far as it would go. Ann shrieked in pain around his cock and suddenly Jack started to spurt down her throat.

As Jack started to soften he told Ann, "Be sure to suck every drop of cum out of my cock." Ann did what he wanted and he finally withdrew from her mouth and wiped his dick dry on her cheeks.

"That was good, baby," Jack said, "Now it's my turn to return the favor."

Jack helped Ann to her feet and led her over to the bed. "Get rid of the bikini," Jack told Ann and she pulled the top over her shoulders and slid the bottom down her legs. Jack positioned Ann on the bed so that her pussy was right at the edge of the mattress and knelt down in front of her.

He spread Ann's nether lips open and put his tongue on her clit. Ann said she was hoping that Jack would not make her cum because she was afraid of him and did not want to have to invite him to her gangbang. Her body, however, betrayed her as Jack no sooner had his lips around her clit sucking the little bud into his mouth when she started to gyrate her hips on the bed.

Jack continued his assault on Ann's clit and she held out for only a few more minutes before she came hard on his tongue. One more orgasm and Jack would likely be at her gang bang.

Jack spun Ann around on the bed so that her head now hung over the edge. He put his dick into her mouth and said, "Get me hard so I can fuck you."

Ann started to minister to his cock and Jack soon began to get hard again.

Jack kneaded Ann's tits roughly while she sucked his cock. His handling of her tits was rough enough to redden Ann's tits and leave hand prints so that anyone who saw her tits in their current condition would know that her tits had recently been roughly handled.

Jack let Ann suck on his cock for a few minutes before saying, "Do you want me to fuck your pussy or your ass?"

"It's your choice," Ann told him before she put her mouth back on his cock.

"My wife doesn't let me fuck her ass so it is your ass," Jack told Ann.

Ann took her mouth off of his cock long enough to say, "There is some lube over on the dresser."

Jack pulled away and got the lube from the dresser. "Lie across my lap and I will get you ready," Jack told Ann. She draped herself over his lap and waited for him to lube her ass.

Instead of feeling the cold lube being applied to her asshole Ann felt a sharp sting as Jack brought his hand down on her left butt cheek. "Ow," Ann said both from the pain and the surprise.

"Gotta warm up that ass a little bit first," Jack said and he proceeded to give Ann another three hard spanks on each of her butt cheeks. Because Ann knew these spanks were coming she was able to bit her lip and keep silent for the most part with only a "mnffff," escaping every now and then.

Ann started to kick her legs and brought her right hand around in an attempt to protect her butt. Jack grabbed her by the wrist and told her to keep her hands where they were. He reminded her that she said he could do anything he wanted to her with a few exceptions and a hard spanking did not fit into any of the exceptions.

Hearing this Ann forced herself to calm down and knew that she was in for one of those moments in her adventures where something would happen to her that she did not like but because she had agreed to the session subject only to the specified limits she had no choice.

"OK, I am going to give you twenty more on each cheek and you better stay still and not try to protect your butt or I will start over," Jack told Ann.

"Do you understand," Jack asked.

"Yes," Ann meekly replied.

Jack then gave Ann the promised spanks and you could hear a sharp crack each time his hand hit her butt. After the first couple of spanks Ann began to grind pussy against Jack and you could tell she was beginning to get aroused.

About half way through Ann started to sob and begged Jack to stop but made no attempt to interfere with the blistering of her butt and kept grinding her pussy against his leg. Jack ignored her pleas and gave her the last ten which seemed even harder than the first ten. Ann convulsed and came on Jack's leg right before he delivered the last two spanks.

Ann's ass was now a bright red and you could make out the outline of several hand prints on each cheek.

"Wow," Jack said, "you just came while I was spanking you." Ann just sighed and acknowledged that she had and knew that she now had to invite Jack to her gangbang.

Picking up the tube of lube Jack squeezed a generous dollop on Ann's ass and worked it inside using one, two and finally three fingers. Jack positioned Ann on the bed in the doggie position, slipped on a condom, lined up his cock with Ann's asshole and pushed his full seven inches to the hilt in one thrust.