Teaching My Wife Ch. 05

"Let me do that," Ann said as she reached out and discretely cupped Kevin's cock in her hand and felt it through his trousers.

Ann said, "From what I am feeling it looks like at least part of you is interested so let me show you the letter from my husband." She reached in her purse and gave Kevin the letter.

Kevin read the letter and said, "Are you kidding me, some of my fraternity brothers must have set this up to yank my chain."

"No," Ann replied, "I am completely serious. I need to know if you are willing to do what the letter says."

"Do you know what the letter says," Kevin asked.

"No, my husband and I decided after the first session that I would not know what would happen to me beforehand and dreaming about what will be done to me keeps me hot for a week before my trip," Ann said.

"OK, then let's get out of here," Kevin said.

"You understand the rules about letting me video tape the session and using a condom, right?" Ann asked.

"Sure, no problem," Kevin replied. He continued, "My whole frat has a rule about using condoms because a few years ago a guy who had graduated about ten years earlier died of AIDS and since then the national office has pushed safe sex on all of its chapters. They show us a movie every year featuring interviews with people dying of AIDS and it usually scares the shit out of everyone."

Just then the bartender came by and asked if Ann and Kevin wanted another round and Kevin asked for the check. The bartender put the check on the bar and Kevin started to reach for his wallet when Ann said, "No worries, I will just put it on my room; I remember being in college and not having a lot of money."

Kevin just smiled and said, "Thanks."

I got as terrific kick out of the whole episode because here was my wife picking up a guy who would soon be blistering her ass with his hands, belt and paddle and later fucking her and she was buying his drinks to boot.

Ann and Kevin got up and walked out of the bar together, the attractive mature MILF and the twenty something hunk.

They walked out of the bar and made their way to Ann's room. Ann said she remembers hearing the door click shut because she knew that sound meant that she could no longer say "No," except to violations of the video and condom policy or to anything that would permanently hurt or mark her.

Ann set up the video camera and said, "OK, what's it going to be?"

Kevin came over, took her in his arms and kissed her and said, "Let it be a surprise."

They kissed deeply for a while and Kevin got Ann's top off and he sucked first one and then the other of her nipples into his mouth. Ann started to moan and she was clearly turned on at the thought of this young hunk fucking her and more.

Her skirt came next and Ann stood naked before a guy less than half her age except for her black fishnet hose and CFM heels.

Kevin took Ann by the hand and led her over to the bed. He moved two pillows down to the center of the bed and positioned Ann over them on her stomach so that her lovely ass was elevated. He rubbed her ass a bit and then reached under her and played with her clit until he had her close to an orgasm. He stopped just short of making her cum and went over to where his trousers lay and took out his belt.

Ann said that she immediately knew that she was going to be the girl in the "Sucking" clip she had watched. Kevin finished undressing and got on the bed in front of Ann and said, "I am going to use my belt on your ass until you make me cum with your mouth and swallow it down."

He held his cock up for a second and Ann took it into her mouth and went to work.

Ann later told me that as soon as she realized that Kevin was using her as the suck whore in the "Sucking" video she tried to suck his cock as hard and as fast as she could to spare her ass as much punishment as possible. Despite her best efforts, it took a little over four minutes for Kevin to shoot his load and you could hear Ann yelp and grunt around Kevin's cock each time his belt struck her upturned ass. Ann easily took over 50 stripes on her ass before she made Kevin shoot down her throat.

Once Ann moved one of her hands down to rub or protect her ass and Kevin grabbed her wrist and said, "Keep your hands away or I will handcuff you." When she moved her hand away Kevin gave her an extra hard slap with his belt.

Ann let Kevin soften in her mouth and then sucked the last few drops of his cum as he withdrew.

They were lying in bed when Kevin's cell phone rang. He got out of bed and retrieved his cell phone from his pants.

On the video we could hear only one side of his conversation.

"Yo, Kevin here."

"What cha' doin"?"

"You aren't going to belief this but I am at the hotel with this incredible MILF."

"She already sucked me off and I have a letter from her husband saying he wanted me to paddle her ass for the rest of the night."

"Geez, Guinevere, I hadn't thought of that."

"So it's you and George and his girlfriend, Angie."

"OK, I will see you in a while."

Kevin turned to Ann and said, "Get dressed; we are going over to my frat house."

Ann protested both about going somewhere besides her room and getting other people involved but Kevin picked up the letter and said, "I don't see anything in the letter that says you don't go where I want you to go and do whatever I want you to with whomever I want you to you."

She took the letter from his hand and scanned it quickly. When she was done she slumped her shoulders as she said, "You're right," I have to go where you want me to go and do whatever you want me to do." She also rubbed her still stinging ass with one hand and shuddered because she now knew from reading the letter that her ass was in for more punishment.

Ann put her filmy top back on and her nipples protruded enticingly. She had not cum during her spanking and was still turned on from the other attention Kevin had paid to her body. She stepped into her skirt and gently tugged it up over her hips and pulled the zipper up. The tightness of her skirt further pressed against her otherwise naked and now reddened ass again focusing her feelings on the part of her that would continue to be abused.

Ann put the video camera into her purse and said, "What about the toy kit?"

"We have everything we should need at the house."

Kevin opened the door and they walked into the hall and out of the hotel.

Kevin led Ann over to his car and opened the passenger door for her. He got in the other side and they were off.

They had driven only a mile when Ann said, "Shit, I forgot the condoms. You have some at the house, right?" she asked.

"Actually we don't as we had a couple of wild parties recently. I was supposed to pick some up on my way back tonight. Don't worry there is a drugstore a few blocks from here."

Kevin turned right and then left and pulled into the parking lot of a drugstore. It was one of the national chains and the lot was brightly lit. He parked the car and Ann assumed that he would leave her waiting in the car. Kevin got out of the car and walked around to Ann's side and opened the door.

Ann stammered for a second and said, "Can't you just go and get them? I'm not sure I'm dressed for this."

"Sure you are," Kevin said as he took Ann's hand and pulled her out of the car. "Besides, I want everyone to see the attractive woman I am spending the night with."

Ann said that she could feel her face flushing as her embarrassment mounted as they walked across the parking lot. She said that the bright lights of the parking lot felt as though they were going right through her filmy top and she knew that in the brightly lit store her top would do little to hide her nipples or the outline of her tits.

It got even more humiliating once they were in the store.

"On the tile floor my heels made a sharp click with every step and without a bra my tits jiggled. The lights left no doubt that I was bra less and my nipples were even harder than they were back at the hotel," Ann later told me.

Kevin led Ann over to the condom display, paused for a few moments and then selected two 36 condom packages. He reached into his pocket, counted out some bills and gave the bills and the condoms to Ann saying, "Here, buy these."

Ann felt like running away as her humiliation mounted. She was going to have to walk to the cashier, wait in line holding two big boxes of condoms and nothing else and then complete her purchase. Her almost see through top, very short skirt, fishnet hose and CFM heels made her look sexy as hell and left little doubt that she was going to get fucked. Having this young hunk standing next to her while she bought six dozen of condoms only made it only worse.

Despite her humiliation Ann said that her pussy was soaked and she could feel her juices leaking down the insides of her thighs. She said that even her breathing had grown more rapid.

Shopping done, Kevin got Ann back in the car and they were off again.

In a small voice Ann asked, "How many people will be at your fraternity?"

Kevin knew Ann was worried about becoming the center of an all hands on deck gang bang so he said, "Well, it's Friday night and there is usually a party so I would say 40 or 50."

"Oh my God," Ann replied.

Kevin talked about how wild their parties were for a few minutes and then said, "I'm just kidding you. The college is closed for the break between quarters and most of the guys have gone home. It is only me and two other guys and the girlfriend of one of the guys."

Ann breathed a sigh of relief and said, "I thought there were two girls because you mentioned Angie and Guinevere on the phone."

Kevin smiled and said, "Well we call her Guinevere and assume she is a girl." He paused for a few seconds before continuing, "Don't worry, you will meet Guinevere soon enough."

In another minute they were at the house and Kevin led Ann inside. Introductions were made with Kevin introducing Stan and George, his two fraternity brothers, and Angie, George's girlfriend, to Ann. Stan went and got five bottles of beer and handed them out and Kevin set up the video camera.

Kevin looked over at Ann and said, "Why don't you tell everyone how you happen to be here."

Ann started at the beginning of how her training sessions had been arranged and what she had done and had done to her during each. She even told them about what Kevin had done to her earlier in the evening. Finally, she said that Kevin had the letter that detailed what was to happen to her tonight and the rules about condoms and permanent marks.

"The letter basically says that we are to punish Ann's ass until she sucks and fucks us to our satisfaction," Kevin said.

You could see Ann visibly tremble at his words.

"Well let's get this show on the road," Stan said. He walked over to where Ann was standing and said to her, "Show us what we are going to be working with tonight."

Ann's hands slowly moved up and she started to open her filmy top. When it parted in the front everyone could see her hard nipples and her breasts moving up and down on her chest with every breath. Ann pulled the top completely off and stood topless in front of four college students less than half her age. She said that she felt a mixture of embarrassment, lust and satisfaction knowing based on the bulges she saw forming in the guys' pants that she still had what it took.

Ann next opened the button on the side of her skirt and pulled the zipper down. She wriggled as she pulled the skirt down over her hips and stepped out of it when it hit the floor. As she bent down to pick it up you could see that her ass was still red from the strapping Kevin had given her earlier.

"Time to meet Guinevere," Kevin said and Stan and George went over to the corner and pulled an old wooden spanking horse into the center of the room. You could tell it has been around for a while as the wood was worn in spots as were the various leather straps.

"Guinevere has been in the fraternity for over fifty years," Kevin said, "She gets used when we initiate our pledges."

He led Ann over to Guinevere and said, "Let me show you how it works."

Kevin showed Ann the various straps and how the person who was going to be paddled was positioned. He also showed her how they had modified it to fit a vibrator in a strategic place for when it was used on a girl. He explained that one of the sororities had started to borrow it for their initiations and had come up with the idea.

Ann stood silently and listened to him and offered no resistance when he positioned her behind the horse and pushed her down over it. Hands quickly put the leather straps around Ann's ankles and above her knees. Two other straps went over her back and shoulders and two more secured her hands.

Ann said that she had reached the moment that she both dreaded and looked forward to in her sessions. That is, the moment when she knew that she had no choice but to have her limits pushed further than they had been before. Ann silently bit her lower lip as she awaited her punishment to begin.

Kevin reached under her butt and turned the vibrator on. Ann jumped a bit as she felt the vibrations hit her already engorged clit and then settled down, pushing herself against the vibrator as hard as she was able.

Ann watched as Kevin walked over to a rack on the wall and took down the wooden paddle that was hanging there. As Kevin walked over to where Ann was restrained in a trembling voice she said, "Please remember what the letter said about not doing anything that would permanently hurt or mark me."

"Don't worry about that, we have done this before and know how hard we can hit. Your ass will stay red for a while and it will be uncomfortable for you to sit for a few days but other than that you will be fine," Kevin replied.

"When we do this to the pledges we usually give each a set number of strokes with the paddle. However, the letter says the punishment is to motivate you to suck and fuck better so here is how it will go. One of us will get behind you and give you three swipes with the paddle. Someone else will get in front of you and after the third swipe you will start to service them with your mouth. The person getting serviced will, if they are satisfied with your efforts, hold up their hand which will tell the person paddling you to stop. Otherwise your ass will continue to be paddled. When you have made all four of us cum with your mouth we will move on to the fucking part."

You could see Ann's eyes open wide in surprise. Four to service meant that she was going to have to make Angie cum with her mouth as well. Ann later told me that she had assumed all along that Angie was going to just watch. As Ann had never licked or sucked another woman's pussy before this night was going to have another first.

Stan got undressed and walked around the front of the horse and George picked up the paddle. "Here we go," he said as he landed the first blow across both of Ann's butt cheeks. Ann said that the first blow stunned her more than anything and that the pain did not immediately start to register. On the second and third blows Ann let out an "Owwww," as each blow landed.

On cue, Stan took his hard dick in his hand and pushed it into Ann's mouth. It was no sooner in than a fourth blow landed and Ann's "Owwww" was muffled by the large cock pushing its way into her mouth. A fifth blow landed and Ann again voiced her muffled displeasure and she realized that the only way to stop the punishment of her ass was to suck like she had never sucked before.

Ann started to suck as hard as she could and you could see her cheeks indented from the effort. She also started to move her head up and down on the dick in her mouth as fast as she could. Because of the way that she was restrained Ann could not move her head enough to run the full length of Stan's cock in and out of her mouth but she did what she could. Another blow landed on her ass and Ann tried to suck even harder.

Stan raised his hand to stop the spanking and let Ann minister to his cock. Ann was doing her best to maintain her frenzied pace but it was tiring and whenever she slowed down for a respite Stan would drop his hand resulting in another blow to Ann's now reddening butt.

Stan started to help Ann by pushing his cock in and out of her mouth. On one out stroke he pulled all the way out and Ann said, "Push it all the way into my throat." Stan obliged and in one hard thrust had his balls resting against Ann's chin.

Ann later told me that she knew she could not keep up the pace for long enough to protect her butt so she decided to get the guy she was sucking to deep throat her because he would do the work and she would get a break.

Her strategy worked on two levels as Stan took over the work of moving his cock into and out of her mouth and got so aroused by being deep throated that he blew his load shortly thereafter.

Stan pulled out of Ann's mouth and she gasped for air and hoped that she would get a few moments to rest.

Her rest was short lived as Angie stripped off her jeans and top and had one of the guys bring an ottoman and put it in front of the horse. Angie climbed on the ottoman and presented her pussy to Ann, virtually shoving it under Ann's face. Ann could see the cunt in front of her glistening with the juices Angie was secreting and said that she could also smell Angie's arousal.

Stan, meanwhile, had picked up the paddle and administered the first three blows. Ann grunted loudly with each.

Angie said, "I will help you out because your hands are tied," and she opened herself up with her fingers.

Angie was about 5'6" and very slender with almost a boyish figure except for her medium sized breasts that protruded enticingly from her chest. Angie had green eyes and although her hair was blond it looked from the darker roots that it was chemically engineered. Angie was shaved and had a small tattoo of a rose just above her pussy. Ann was still taking all of this in when Stan let her have two more blows with the paddle. Ann squealed with each of the blows and quickly got her focus back to the matters at hand.

Ann had never eaten a pussy so she was not sure of exactly what to do but decided that she would do the things that the men who had eaten her pussy had done to her and hope they also worked on Angie. Ann started to lick Angie's pussy up and down and when she found her clit pushed her tongue against it. Angie started to respond but she had not yet raised her hand so the blows continued to rain down on Ann's ass.

Ann yelped or squealed with each blow and you could hear her clearly because unlike when she had a cock in her mouth there was nothing to muffle the sound as she licked Angie's cunt. Ann then pressed her lips to Angie's cunt and started to suck the folds of her labia into her mouth. Angie must have liked that because she soon raised her hand giving Ann a respite from the blows that Stan was delivering to her ass.

Angie started to rotate her hips and in the process rubbed her cunt over much of Ann's face. When Ann pulled away for a second you could see Angie's pussy juice on Ann's cheeks, lips and chin.

"Suck my clit," Angie directed and Ann found the little nub and sucked it into her mouth. Ann would suck Angie's clit into her mouth and then keeping the pressure on she would move her head back letting it slip out of her mouth.

"Stick your tongue inside of me," was Angie's next directive. "Deeper," Angie said and you could see Ann's lips plastered up against Angie's cunt as Ann tried to force as much of her tongue into Angie's slick tunnel as she could. "You can get deeper than that," Angie said and dropped her hand.

Stan immediately gave Ann two blows with the paddle and although Ann jumped on each she kept her lips firmly planted against Angie's cunt and continued to try to force her tongue further in.