Chapter 3 – First Time
Sunday, at exactly 2:00 pm, an extremely nervous and excited Dee pulled up to the gate and entered the code Julie had given her into the keypad. She noticed that a van had gone in right before her, and another car followed her in. As she got out of her car, a woman she thought she recognized from somewhere opened the back of a van.
“Oh my god!” Dee thought, there was a cage in the back of the van and the woman was unlocking it and waiting for a naked man to get out! Then she clipped a leash on his collar and started leading him towards the house.
No sooner had Dee watched that exhibition than she noticed another man was standing next to the car that had followed her in. He was calmly undressing, folding his clothes, and stacking them in the back seat. When he was done, this couple also headed towards the door. Nobody seemed to be paying much attention to Dee, so she followed them.
At the door there was a smartly dressed older woman in a black ankle length dress with a basket. Both ladies preceding Dee dropped something in the basket. Dee had a moment of panic trying to remember if she was supposed to bring something when the lady said “Ahh, you must be Dee, welcome, Julie and Mrs. Wainwright are waiting for you. Go straight through to the patio in the back.”
As Dee passed the lady she looked in the basket and saw… keys. Curious.
Walking through Mrs. Wainwright’s home, Dee wanted to look around and absorb the decorations, the art, the elegance of this huge home. She was, however, somewhat distracted by the two naked men being led along in front of her, especially the one who had come in the cage in the van. ‘Cage Man’ as she now thought of him was muscular with a very tight ass.
When she walked through the open double doors to the huge patio, she stopped dead in her tracks and slowly took in the whole scene. There were round tables spread around a grass lawn with a small cement patio at one end. On the patio was a long table with four chairs, probably the head table. Another table was set up near the house with covered serving dishes. Each of the round tables had six chairs, but the tables were large enough that there was room between each chair. It appeared that about half the chairs were occupied, some women were sitting, some were standing talking in groups. But beside and behind almost every woman knelt a naked man. Just like all the women were different ages, different ethnicities, different body types.
As she looked closer, she saw that most, but not all the men were wearing chastity cages, and they all seemed to be metal. Most were also wearing collars, some with leashes attached, others with leashes attached to their cages. And they were all being largely ignored by the women present. It was almost like they weren’t there, except they were there, naked, in chastity and leashed.
Dee was so absorbed by talking this all in that she almost missed Julie who was waving her arm trying to get her attention. Dee finally spotted her, waved back, and walked over. Julie was sitting with three other women and beside her chair knelt Will, head down.
“Ladies, meet my friend and future member Dee.” And Julie proceeded to introduce Dee to the other women at the table, completely ignoring the fact that naked men knelt beside each, unmoving and staring at the ground.
As Julie introduced each of the ladies, Dee already knew one of her tablemates as a fellow volunteer at the Food Pantry. She also recognized one of the kneeling men as the cable installer who came to their home last month to upgrade their Internet service. Even though Dee clearly remembered him, per her instructions from Julie, she showed no recognition and said nothing.
After several minutes of small talk, Julie asked Dee if she would like tea. Will jumped up, without being told, and carefully served Julie and Dee using a pitcher of hot tea already on the table.
“Since we don’t know Dee’s preferences yet, a broad selection Will.” Julie said without looking at or thanking her husband who scurried off to the food table, his leash trailing behind. Several of the other ladies at the table snapped their fingers and their men also served tea and ran off to the food table.
“We’ve been training them for years to serve us.” Julie commented when she could tell Dee was amazed by this whole process.
Will came back with an amazing assortment of fresh fruit, scones, pastries, and little cakes. It all looked delicious. Throughout the afternoon, the men kept their positions beside their wives or partners and made sure the teacups were full and favorite pastries never ran low. Only occasionally did Dee notice a woman giving her man a sip of tea or breaking off to hand feed a piece of fruit or pastry to a kneeling man. As the afternoon progressed, some of the men were given duties elsewhere at the tea, and when that happened, other men at the table automatically took over serving.
The conversation seemed to shift from mundane to men in just a few minutes. One moment they were talking about what the food pantry needed this week. The next moment the woman across the table was bragging that she had installed a winch in her basement so she could suspend her husband for his weekly maintenance beating.
“What’s a maintenance beating?” Dee asked.
Which prompted the women at the table to extol the virtues of regularly beating their men to tears, whether they had earned a beating or not.
“It keeps Axel in line,” one reported, “he knows it’s coming so he works really hard all week in the hope I’ll be merciful. Of course, I never am!” And all the ladies laughed at that. Dee noticed that not one of the men kneeling on the grass even looked up.
Shortly after the discussion on maintenance beatings, Dee realized that the woman across from her was slouching down in her chair. Then she heard it – Axel was kneeling under the table now with his head and shoulders under her skirt, and he was obviously lapping at her clit! And the whole table was ignoring the scene. Even when Alex brought her to an obviously satisfying orgasm, everybody at the table kept talking.
Julie leaned over to Dee and whispered, “Since Paul isn’t here, I’d be happy to loan you Will if you would like.”
“Oh, uh, thank you, but, uh, I wouldn’t without telling Paul first, uh, you know.” Dee stammered, caught completely off guard by the suggestion.
“I understand but know that the offer stands. Will is a slut and a pretty good cunt licker, I trained him myself.”
Dee couldn’t get the image of Will kneeling between her legs out of her mind for the rest of the Tea and she wondered if there would be a wet spot on the back of her skirt.
About that time there was the sound of a water glass being tapped by a spoon and the patio went quiet.
“Welcome Ladies to a beautiful afternoon in Chain!” Mrs. Wainwright said in a loud clear voice.
“First of all, I’d like to recognize Dee, stand up dear!” She continued. “Dee is considering membership in our Ladies Tea Society, so everyone be sure to make her welcome. She has her husband Paul in chastity but that’s about as far as they have gone so she will need lots of advice, ideas, and guidance. Her sponsor is Julie, so she is already in good hands!”
There was a general round of applause while Dee stood.
Then Mrs. Wainwright called on the program chair, Carly Blane.
“Today ladies, three of our members have prepared a short presentation on pegging.
Our presenters are Carrie, Diane and Mary and I’ll turn the program over to Mary who organized this program, Mary.”
Three of the members walked forward, followed by their husbands, or partners, Dee wasn’t sure which. Two of the men were on leashes, only one of them was wearing a chastity cage. Carrie’s husband looked almost happy, Diane’s husband didn’t show much emotion, but Mary’s husband looked scared. Mary’s husband was also the only one of the three whose hands were cuffed behind his back.
The women had all three men bend over the head table with their asses facing the assembled audience. Carrie’s husband wasn’t wearing a leash, but he was wearing a chastity cage, so Carrie first asked Mrs. Wainwright for the key she had deposited in the basket when entering. Once Mrs. Wainwright found the right key, Carrie released his penis instructing him sternly to stay bent over the table and keep hold of the far side of the head table with both hands. His penis could be clearly seen by most of the audience, starting to grow between his spread legs.
Diane took her husband’s leash and handed it to one of the ladies sitting at the head table, asking her if she would be so kind as to tie it to a table leg on that side, effectively keeping her husband bent over the table. She then took out her cell phone and showed the crowd that she was turning off her husband's Ultimate Chastity device. [author’s note – more info on this device coming in the next chapter!]
Finally, Mary bent her husband across the table and handed his leash to a member sitting at the head table asking her to also tie the leash to a table leg on that side. But Mary took the added step to tie each of her husband’s ankles to stakes that had been driven in the ground in front of the head table, effectively spreading his legs and trapping him across the table. The members at the head table could clearly hear Mary’s husband whimper as she took out her cell and showed the audience that his Ultimate Chastity device was set to maximum pain on even a minor erection.
“Ladies,” Mary started the presentation, “today we are going to demonstrate three possible ways to use pegging on your men.”
“What’s pegging?” Dee whispered to Julie.
“Mary, you might explain pegging quickly, not all of us,” Julie said loudly, “may know the term.”
“Oh, I’m sorry,” Mary continued, “I forget that we have prospective and newer members present, thanks for reminding me Julie! Pegging is basically fucking your man’s ass with an artificial, usually silicone, penis. After all, men are always wanting to fuck us in the ass, where we get little or no pleasure from the act, so why shouldn’t it work both ways. Besides, the male anatomy can get more pleasure from the act than the female anatomy as we’ll see shortly. As I said, we’re going to demonstrate three possible ways, and possible outcomes from pegging. Carrie will start us off.”
Carrie began talking as she removed her skirt. “You may have noticed that my husband walked up with a smile on his face. That’s because if he behaves, he’s going to have his first orgasm in over a month in the next few minutes.” As Carrie was saying this she was, with Mary’s help, strapping on a harness with a life-sized silicone dildo. If you want to give someone pleasure with any type of ass play, there are a few things to remember. One, have your submissive thoroughly clean themselves out. This boi gave himself three enemas before we left the house today. Second, use lots of lube, preferably lube formulated for the ass.” As she said this Carrie was liberally squeezing lube on her fake dick and rubbing it around. “Third, you need to get the ass to relax and open it up a little.” With that Carrie started sticking her finger in her husband’s ass, pushing it in and out, then added a second, then third finger.
Carrie’s husband was now sporting a raging hard on and he was starting to wiggle his ass as she continued to stretch his sphincter with her fingers. She then removed her fingers and placed the tip of her dildo at the opening.
“I’ve spent years training my husband to enjoy this.” Carrie explained, and then thrust into him with one swift motion. “Also ladies, if you position your dildo correctly, you get a rather pleasant ‘bump’ on your clit with each thrust.”
Carrie then started to fuck her husband’s ass with a nice steady, slow rhythm.
“The pleasure for the man comes from stimulation of the prostate, which is, in this position, below the anus. So I’m intentionally angling the dildo down to rub along the prostate.”
Carrie just kept stroking, in, out, in, out. After just a few minutes it was obvious that he was thrusting back. Carrie slowly increased the pace, pointing out what she was doing to the audience. After about five minutes of this, he made a noise from deep in his throat and his penis started ejaculating cum on the ground between his feet. Carrie matched her thrusts to his ejaculations until he was finished then withdrew. The ladies were applauding!
“The trick, ladies, is to never allow your man any sexual stimulation except by being fucked in the ass. And NEVER allow him to cum except by this method. It may take months for the prostate to build up enough fluid before he will have his first orgasm this way. But eventually, something like a ‘wet dream’ occurs. You know that men who aren’t allowed to cum will leak fluid at night right. Well, we can cause that ‘leakage’ by stimulating their prostate with a sound fucking. IF you keep fucking them as they start to cum, they will have something that approximates a real orgasm. Keep training them this way, denial, followed by pegging till they cum. Do it every month for a few years and you can make them cum reliably this way. You never have to give them a hand job again!”
After the applause died down, Mary introduced Diane. During Carrie’s demonstration, Diane and Mary had both removed their skirts and strapped on their harnesses.
“I’m going to show you a crueler version of what Carrie has demonstrated. My husband has cleaned himself out, and I’m going to use some lube, but I’m not going to open him up first and I’m going to ruin his orgasm.”
With that short intro, Diane reminded her husband to behave, keep his legs spread and, without hesitation or ceremony, thrust her dildo balls deep into her husband’s ass. His cry could be heard in the back of the lawn. Even though it obviously hurt, Dee noticed that he was also sporting a huge erection hanging down between his legs.
Diane didn’t start slow; she pounded her husband’s ass. After a few minutes, Dee appreciated what great physical condition Diane must be in to keep up such a pounding. After several minutes of this Diane reached around her husband’s waist and grabbed his penis.
“Ladies, I need to hold this thing so I can feel when he starts to drip pre-cum since I can’t see it.”
After another few minutes, Diane announced loudly “All done!” and withdrew the dildo so quickly that it made a sucking sound and a pop when it came out. Dee noticed that fluid was slowly but steadily leaking out of Diane’s husband’s penis.
“And that, ladies, is how you drain a prostate without allowing a satisfying orgasm.”
And with that she pulled out her cell phone and re-engaged his chastity device but left him bent over the table still dripping.
“And I’m bringing up the rear!” Mary announced to great laughter at her pun.
“I’m going to show you how to do a punishment pegging. I don’t think that needs any more explanation.”
At this point, most in the audience realized just how HUGE a dildo Mary had strapped to her crotch.
“Oh my god!” Dee exclaimed and Julie just smiled at her.
“Now I should tell you,“ Mary continued, “that we did have to work up to this size. I normally don’t use this large a dildo and he’s only taken this size once before so this should be interesting!”
Turning to her husband Mary asked, “So do you want to tell the audience what you did to deserve this fucking?”
“I didn’t do anything wrong!” her husband sobbed!
“Now we discussed this, do you really want to make me angry right now? Why do you deserve this fucking?” Mary asked again.
“Because I’m a man and men deserve to know what it feels like to be fucked,” he said quietly.
“I don’t think the ladies in the back of the lawn heard you!” Mary said angrily.
“Because I’m a man and men deserve to know what it feels like to be fucked,” he said loudly between choking back sobs.
Mary didn’t use any lube, she just spit on the end of the dildo. She then turned to the audience, grinned, and shoved the first inch or so of the dildo into his ass. He cried out. She grabbed his handcuffs with one hand and guided the dildo with the other hand as she explained.
“This dildo is four inches in girth and seven inches long. Sometimes, when I’m in a mean mood, I coat it in hot sauce or rub fresh ginger on it. But I’m being nice today.”
And as Mary said ‘nice’ she shoved another few inches of the massive prick in and the audience laughed.
Her husband was openly crying as she started going in and out. And with each thrust she went in a little deeper until, after about ten thrusts she was all the way in.
“When you think he’s had enough ladies, raise your hand. I’ll stop when it’s unanimous.” Mary said and started vigorously pounding him. Slowly, hands started going up. So slowly that Mary started encouraging her audience to have mercy, not by asking for it but by making comments like, “He’s not going to be able to walk for a few days.” And “We’re going to get some blood here soon!”
Of course, those comments also had a psychological effect on her husband too.
Dee raised her hand after about 20 thrusts, but Julie waited until almost all the other ladies had raised their hands. Finally, the last hand was raised, and Mary stopped.
“Thank the members for making me give you a nice long pounding!” Mary instructed and her husband responded, “Thank you for my ass fucking!” To Dee’s surprise, he sounded genuine and sincere.
All three of the men were left bent over the table while the ladies finished socializing. Mary put her harness and dildo on her husband’s back so the ladies who wished to could inspect his ass and the tool of its destruction and the other two did the same. Under the guise of wanting to pick out something from the food table, Dee went by the head table to get a close look at the three harnesses and the three asses on display.
When Dee got back to the table, she had to ask Julie, “So, tell me about this ‘ultimate chastity thing?”
“Oh, I’m not the one to tell you since the inventor is at the next table, let’s go meet her.” Julie said as she rose from her seat.