Once Too Often!

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Soon all three lay there in a stack, breathing heavily and trying to recover. First the woman behind him pulled out of his ass, then Lou pulled out of the woman beneath him and rolled to the side on his back.

"Did you enjoy that? You can speak freely."

"That was fantastic. It wasn't what I thought of when you said I would have sex with two women at a time, but Wow!"

"Well that was only round one. There will be more as soon as you recover. Meanwhile, we are going to take turns riding your face until you're recovered."

They took turns and Lou did his best to bring them off. Finally they judged that he had recovered enough. This time they positioned him across the bed on his back so his ass was just at the edge of the bed. A woman climbed on the bed and sat on his face. As he began to eat her, his legs were lifted and his ass again invaded by a large strap-on dildo. The woman riding his face bent down and began to give him head. She was very good. But she did not bring him to orgasm, just pleasured him as he ate her and was fucked in the ass by the dildo. The woman with the dildo came, shoving it in his ass as far as she could as she clung to his upraised legs and spasmed through her orgasm.

The woman fucking his ass was replaced with another. After she came, the next woman lifted the woman who was giving him head from his cock and rolled a condom on him and then sat on his cock and rode him enthusiastically. She wold post for a minute or so then settle down with him buried all the way in and use her abdominal muscles and vaginal muscles to massage his cock. Finally the woman on his face came. Then the woman on his cock came and her spasms finally brought Lou to his orgasm.

The woman who had been riding Lou's cock got off and they removed the now full condom and cleaned Lou up. Lou was by now wiped out.

"You look totally wiped out. Could you use some food? It's dinner time."

"Yes, please, ma'am."

They got Lou to his feet and led him back down to the dining room and secured him as he had been at lunch.

"You may speak freely during dinner."

"Yes, ma'am. Thank you, ma'am."

"How are you doing, Lou?"

"I'm sore, tired, sexually worn out, embarrassed as hell."

"Good. You've got the rest of this evening and all day tomorrow to go."

"I don't think I can get it up again and my ass is sore from being fucked so many times."

"Don't worry, we have some more relaxing things to occupy the first part of the evening and give you some time to recover a bit."

"That's good."

"Now eat your dinner, you'll need to keep your strength up."

******

After dinner, Lou's wrists were again secured to his collar. He was blindfolded and released from the chair and led to the living room and they sat him on the couch.

"You've been good so we are going to reward you with a movie. I think you will enjoy it."

They removed the blindfold and Lou saw Carol start the video from the computer. There on the large screen was a naked Lou being cuffed and spread eagled on the bed and then having the hood placed on his head and laced up. Then the scene cut to him in the master bathroom trying to piss then trying to jack off and finally being jacked off then pissing. Another cut to a different angle then showed him being massaged with the hair removal cream. Another cut showed him in the shower washing away his body hair. Another cut and he was being dried and the camera panned around showing his now denuded body.

Carol stopped the video. "Some good shots there. Really shows you off well. Don't worry, we won't show this to anyone as long as you continue to obey and be a good slave on the weekends."

Carol then resumed the video. The video showed Lou with a large dildo attached to his gag and then him using the dildo to fuck a woman. Then it showed him fucking the second woman. Then it showed him on his back as two women mounted the dildo and his erection and rode him. Then the video showed him on his back being jacked off to an explosive orgasm. Next a montage of shots showing fingers in his ass leading up to someone finally fisting his ass.

"I hope you are enjoying the show."

Next the video showed him on the floor with his ass in the air as the enema tip was inserted then it cut to his belly being massaged and another cut to the enema tip being pulled out and finally to him on the john expelling the enema.

Another cut to showing him being led by his cock and positioned at the opening of a woman's vagina and then sinking in to the balls. It then pulled back and showed a woman with a large strap-on dildo behind Lou and then her inserting it in his ass and then fucking his ass and soon he was getting into it then the series of orgasms that ripped through the three.

The video ended and Carol said, "We have more video that we haven't had time to edit yet. But you get the idea."

"The video will remain safely stashed where no one can see it as long as you are a good slave on the weekends. We have copies elsewhere, so you don't have to bother looking around the house for them as the other copies are elsewhere."

"You are our slave on the weekends and if you don't behave, we don't have to tell you what we will do with the videos and how your friends and co-workers will respond to the videos."

Lou was in shock.

"Do you understand your situation?"

"Yes, ma'am."

"Good boy."

"Now that we have this insurance, I don't think we need to keep you so restrained and we can be safe that you won't tell anyone about what we are doing to and with you on the weekends, so we can let you see my friends and helpers. We know that you won't let anyone else know about them and our weekends because we have these videos."

They released Lou's wrists and removed the collar so Lou could now turn his head.

"Close your eyes and roll your head around to loosen up your neck, it must be stiff after being in the collar for so long."

A few moments later, Carol said you can stop now and open your eyes.

Lou did as he was told and saw five of Carol's friends fully clothed in front of him.

"Hi, Lou. Enjoyed riding your cock," said Fran.

"I really enjoyed fisting your ass," said Jane

"I liked riding your face," said Ellen

"I liked fucking your ass with the strap-on," said Lori

"I liked it when you fucked me with that dildo in your mouth," said Karen.

"You really do look much better without all that hair," said Fran.

"I like it too. It is so much sexier when I fucked your ass to feel your smooth ass and thighs," said Lori.

Lou was blushing at their comments and being nude in front of the fully clothed women, some of whom were close friends.

"You blush so cutely," said Jane.

"And his cock is getting hard again," noted Karen.

"It looks as though we will get one last orgasm out of him before the night is over," said Carol.

They lay Lou on his back on the plastic sheet on the floor. Carol leaned down and French kissed Lou. Another woman started to give him head. He couldn't see who it was as Carol's head blocked his view. The women took turns giving him head and French kissing him. Finally the stimulation was too much and Lou came again for the final time that evening.

The women then thanked Lou for an entertaining day before they left.

Carol took Lou up to bed and tucked him in. Lou was exhausted and fell asleep in a moment.

******

Sunday morning Mike awoke rested but stiff and sore in a number of unfamiliar locations. He found that he was unbound, but still had the cuffs padlocked to his wrists and ankles.

"Shit! It wasn't a dream.", mumbled Mike.

He heard Carol, "Are you awake, Mike?" "Uh, yes."

"Well throw on some sweats and come on down to breakfast."

"Be right there."

Mike got up and hit the john and took a leak, washed his hands and face and rinsed his mouth out. Then he put on sweat pants and a sweat shirt and slippers and went down to the kitchen.

"I hope you got enough sleep. You were pretty tired last night. Breakfast will be ready in a moment."

"Uh, yeah I was tired. I feel a lot more rested, but I'm sore in a lot of places that I'm not used to being sore."

"Yes, I suppose you probably are. We did use you rather hard yesterday. We'll go easier on you today."

"Thanks, I guess."

"Mike, I want a straight answer. Are you unhappy with this arrangement of you getting to drink Friday night with your buddies and I get to use you as a slave and sex toy Saturday and Sunday?"

"Whoo. That's a hard one to answer. There have been some things that I definitely did not like. The embarrassment, and humiliation. The enemas were that and painful. The cramping hurt. Then denuding my body hair."

"But you do look so much sexier and you feel so much better without it."

"Yeah, it does seem to be more sensitive. So let's rate that as mildly disliked. Maybe I'll change my mind on it as time goes by."

"We will make sure to see what we can do to make the smooth look grow on you."

"Ouch, that pun hurt."

"Sorry. Anything else you didn't like?"

"I sure didn't like the butt play. When the whole hand went up my ass, it hurt."

"What part of it hurt. When the wide part of the hand pushed in. Afterward it was just sore."

"Was there enough lube?"

"Yes, that wasn't the problem. It was the size."

"Well be glad we used the woman with the smallest hands."

"Anything you didn't like?"

"Well my neck got real sore fucking the two women on the sofa with the dildo gag."

"Sorry, we didn't realize how much strain that would put on your neck. We won't do that again. Or at least we will do it differently so it doesn't hurt your neck. We need to keep our sex toy in good shape."

"Anything else you didn't like?"

"That's pretty much it."

"So what did you like?"

"Getting to fuck so many different women. Coming so many times. There were some great orgasms. Being played with and massaged."

"Anything else?"

"Yeah, I hate to admit it, but getting butt fucked was a new experience. I didn't like it at first, but then it started to feel good."

"I noticed you seemed to get into it after a couple of minutes."

"Yeah it was mind blowing to be fucking a nice hot tight pussy while my ass was being fucked. Every move was stimulating both my ass and cock. I always wondered about those women who claimed to like being the filling of a sandwich screw. Now I know how it feels. It's great!"

"Well we will have to see what we can do about doing that more with you."

"I'm all for that."

"I do have one request. I spent all day pleasuring you and your friends. I was naked all day and all of you got to see me. But I only got to see all of you dressed at the very end. That's frustrating. I'd like to see what I'm doing and what's being done to me."

"Lucky you. Now that we have sufficient blackmail material to be assured of your compliance and silence, you will not be blindfolded all day today."

"Now, here is your breakfast. Three eggs over easy just the way you like them. Toast and strawberry jam. A couple of slices of Canadian bacon. And a big glass of milk. Now dig in and make sure you finish it all. You'll need the energy for later."

"Yes ma'am."

"When you're done. We'll go upstairs and give you an enema before the girls come over. It'll be less embarrassing for you. I'll also try to do it so as to keep any cramps to a minimum."

"Thanks, I guess."

After Mike had finished eating and Carol had cleared the table and put the dishes in the dishwasher, she took Mike upstairs.

"Ok, strip and I'll get the enema ready."

"I'll be there in a moment."

Carol gave Mike three rounds of enemas this time, but she didn't make him retain the enemas for too long and when Mike began to cramp, she would let him release the enema into the toilet. By the time the third enema was released, Mike was cleaned out.

"I'm going to take off your cuffs so you can shower. Then after you're dried off, I'll replace them."

"Yes ma'am."

After his shower, Mike came into the bedroom and Carol replaced the cuffs on his ankles and wrists, locking them in place. The girls should be here shortly. Let's go downstairs to the living room to wait."

They went down to the living room and Mike sat on the sofa while Carol sat in the lounger.

"I'm going to put the hood and a blindfold on you for when you greet the women. The blindfold will come off soon after they get here. I talked with them and they would feel a little more comfortable with you hooded for now. They want to keep this separate from their relationship with their friend Mike, for now. Are you good with that?"

"Yeah, I can deal with it for now."

"I'll order a new hood that will leave your lower face open so you can eat us out rather than being limited to that dildo attached to your gag. Would you like that?"

"Well, if I have to wear a hood, that would definitely be a lot better."

"You know I love you. But you really did tick me off. So I am glad we could find a solution that would make both of us happy."

"I love you too. And I don't think I'll be getting so drunk again on Friday nights anymore. I'll need to be sober and at full strength for you and your friends on Saturday mornings."

The doorbell rang. "I think the girls are here. Let me get you laced into your hood and blindfolded."

Mike stood up and Carol quickly hooded and blindfolded him.

Carol answered the door.

"What took so long to answer the door?"

"I needed to hood and blindfold Mike."

The girls entered the living room. Mike was standing naked except for his hood, blindfold, and cuffs.

Carol and the women carried on a quiet discussion for several minutes. Mike couldn't hear what they were talking about. Several minutes later the discussion ended.

Carol said, "Mike we've agreed that you can see what you are doing today. But you need to be collared and restrained."

Someone behind Mike reached around and fastened a collar around his neck and he heard the click as it was locked in place. He recognized it as the smaller collar, so he would be able to turn his head. Then his wrists were secured to the collar.

The blindfold was removed and Mike could see the women now. They were all clothed. Fran grabbed some lube and put some in her right hand and then came over and stood behind Mike and reached around and grabbed Mike's penis and began to manipulate it, causing it to stiffen. She then began to slowly masturbate Mike. She whispered in his ear, "Enjoy this, Mike."

The stereo was turned on and the women began to dance and one by one do a strip tease. They did everything they could think of to tantalize Mike. Meanwhile Fran kept slowly masturbating him. Mike was hard and horny, but the women were playing with him and wouldn't let him come.

A now naked Jane came around behind Mike and Fran let go of his erection and moved in front of Mike. Jane put lube in both her small hands and rubbed up against Mike's back as she reached around with both hands and grabbed Mike's erection and began the slow masturbation again. Fran now did a strip tease. If possible, she did an even raunchier dance than the others had done.

By the time Fran was done with her dance, Mike was hard, horny, and breathing hard. Jane said, "Do you prefer my hands on your cock, or up your ass?"

Jane then let go of Mike's erection with her right hand and stepped slightly to the left and brought her well lubricated right hand to Mike's ass. She pushed her hand forward and her fingers met his asshole.

"Relax and open wide for me."

Mike tried to comply as Jane's fingers began to penetrate his ass. Jane went slowly and took her time. Ellen took over for Jane on Mike's erection as she cooed, "Doesn't this feel good? I bet it feels almost as good as Jane's hand up your ass. I bet she is really stretching your ass as she works her whole hand up inside you."

Mike could feel Jane's hand stretching his ass as more and more of her hand was forced into his ass. He was feeling very stretched and it was beginning to be painful when all of a sudden her hand was in and his ass clung to her wrist.

Jane put her left hand on Mike's shoulder and with the hand on his shoulder and the hand up his ass, she guided him behind the sofa and bent him over it. He was bent over so that his chest rested on the back of the sofa.

Ellen then came over and began to stroke Mike's cock. Jane then said, "I'm going to see how far up your ass I can get my fist. I understand some gays have gotten all the way in up to their elbow. I'm small, so it should be easier and I won't be able to go as far as a big dude could. So relax and enjoy the ride."

Jan then began to twist her wrist and push. Karen and Lori took turns lubricating Jane's arm as slowly more and more of her arm disappeared up Mike's ass.

"God this is so hot!"

"Yeah, this is even better than watching gay porn!"

"Do you watch that stuff?"

"Yeah, it's hot. Guys always say how hot it is to watch two women making love. Well, I find it really hot to watch two studs going at each other."

"That's perverted."

"No it's not. At least not any more than two women going at it."

"I agree, it is hotter than hell to watch two guys in a sixty nine or fucking each other up the ass."

"You both are perverted."

"To each their own."

"God, I've got half my arm up Mike's ass!"

"You go girl!"

"You rock Jane!"

"How does it feel, Mike?"

"Full, very full and my ass feels like it is being stretched so wide that it'll never close again."

"Do you want Jane to stop?"

"No. It feels fantastic, especially with Ellen jacking me off at the same time."

"You heard the man. Keep going Jane."

"It's getting harder, but it feels great up his ass. I can really understand why gays are so into fisting."

Several minutes and Jane said, "I think that's it. I can't go any further."

"Let me get a couple of good shots of this," said Karen.

Mike heard the sound of the clicks of the camera and saw the flashes as the pictures were taken.

"Don't worry, no one will be able to tell that it's your ass, Mike."

Jane began to twist her hand up Mike's ass as Ellen sped up her masturbation of Mike's erection. Soon Mike came into Ellen's other hand and his ass clamped down on Jane's forearm with each spasm of his orgasm. Soon Mike's orgasm ended and Jane and Fran pushed Mike forward and he collapsed over the back of the sofa.

Jane slowly began to withdraw her arm from Mike's ass. Her hand easily passed out of his now very stretched asshole. After she withdrew her arm from his ass, Mike's asshole remained gaping open. Karen took a number of shots of his gaping ass. Two of the women inserted their fingers into Mike's asshole and gently stretched his ass open from both sides in imitation of the Goatsee picture on the internet. Karen took more pictures. "This is so hot. I'm ready to come. One touch and I'm going to go off like a rocket."

Karen came around the front of the sofa. Mike felt someone release his right hand. Karen then grabbed his wrist and guided his hand to her slit. "I'm so hot. Make me come, Mike."

Mike was still wiped out from the fisting and his orgasm, but he was rapidly reviving with the new stimulus. He began using his had to do everything he could to get Karen off. It didn't take long. She was right. She was very near a big orgasm and Mike's hand provided all the extra stimulus she needed to come, hard. She screamed and shook and her thighs clamped together trapping Mike's hand until she was done.

"God! That was Hot," said Fran. "My turn."

Now Fran replaced Karen and Mike soon had her coming on his hand.

The women took turns using Mike's hand to get off. After the women had all used Mike's hand to get off, they gathered behind Mike.

"His asshole will take some time to tighten up."

"Well it is a good thing Carol gave him an enema this morning."