Delivery for Jess

"Kiss me!" Jess said, and as Dan moved to stand up, continued "NOT up here, down there!" Opening her legs, Dan realised what she meant. "Start from my feet, one kiss per toe, then work up at the speed you think is appropriate. I will tell you where to stop and don't think of looking up, I want you focused on what you are doing!" Disappointed not to be able to gaze at her big, firm, tits again, Dan paused, then shook his head, not 100% sure he wasn't dreaming. She looks fantastic, she is young enough to be my daughter, she is almost naked, and wants me to pay homage to her body, he thought. "Yes, Miss, absolutely!"

Dan started on her left foot and kissed each toe, then moved across her instep to work slowly up her left leg. Her skin was firm; tight around the rather muscular calf, and then softer as he passed her knee to her thigh. As he closed on the top of her thigh, Jess placed her hand in the way and pointed to the other leg. Dan was happy to oblige. Starting at the foot again, he worked his way up to her right thigh, and this time the hand allowed him to reach as far as her soaking wet panties, which he kissed and licked several times whilst tasting her juices flowing through the lacy material.

Pulling her panties aside, Jess finally gave Dan access to her pussy. "Concentrate on what you are doing," Jess warned him "and make sure you do your best. I accept nothing less!"

To make things easier on him, Jess pushed up with her feet and slipped her panties off her ass, revealing her full glory to a totally gobsmacked, but deliriously happy Dan. Settling down legs splayed, Jess rested back and closed her eyes. "I really hope you know how to do a good job - get licking."

It had been years since Dan had been this close to a hot wet pussy, and never one on such a gorgeous woman. He was still having trouble believing he wasn't dreaming, but the scent emanating from Jess' secret place gave him renewed vigour. He had always enjoyed servicing his ex-wife this way, so starting on her labia, Dan licked and kissed as tenderly as he could, sucking the juices from her lips. First one side, then the other, Dan worked as hard as he knew how and was rewarded with several soft gasps and mewls from above his head.

Jess seemed to be enjoying it so far, he hoped! Her hand reached down and moved Dan's head, pulling it tighter in and forcing his tongue to enter her sopping wet hole. "Keep going." she demanded. Dan was more than happy to oblige, and put renewed effort into pushing his tongue as deep as he could into her, eliciting more happy sounding gasps from her.

After a few minutes, Jess removed her hand and allowed his head more freedom. Dan took the opportunity to switch over to her prominent clitoris. He knew to be very gentle here and was careful as he touched his tongue onto the nub. Jess let out a sharper gasp and uttered "More, and you can go stronger," giving Dan the permission he needed to exert a bit more pressure with his tongue. Working round and round with his tongue, Dan licked and sucked at her super sensitive clit causing more welcome sounds. Being brave, he inserted a single finger into her pussy, and, meeting no resistance, pushed it in fully feeling her juices coating it with the delightful secretions. Dan pulled the finger out and sucked it dry, then reinserted it, along with another finger, whilst still concentrating on Jess' pleasure from his ministrations on her hard clit.

Jess was getting much noisier now, and Dan, realising she was enjoying what he was doing, re-doubled his efforts. Suddenly, Jess sat up a bit, reached down with both hands and grabbed Dan's head, forcing it harder into her. At the same time, her thighs clamped down hard on the sides of his head, both actions holding it in place as Jess rode through an orgasm. "Don't you fucking dare stop." he heard, and moved his tongue as best he could to attempt to please her more. He was moving his fingers in and out of her now sopping wet cunt and trying to do anything which would bring about another orgasm. He needn't have tried too hard, as Jess was nearly there and, with the extra effort Dan was putting in, and the increased sensitivity of her little button, it took no time at all for Jess to scream out as her second orgasm tore through her. Dan's head was now being squeezed tightly from all directions so he just moved what he could, and tried not to drown from the juices squirting from Jess' pussy. "Oh my!, fuck!, Oh God!, don't stop, DON'T STOP!, ooooooh!" came from Jess' mouth as the aftershocks of her orgasm coursed through her.

Relaxing somewhat, Jess leaned back on the cushions and said "Not bad, for a first time. Maybe there will be........." She stopped speaking as she had heard noises at the front door. Jess started to smile. A very confused Dan started to move, but was stopped by a loud "DON'T MOVE" from Jess. "Stay just where you are, ass up." said Jess. "Hi Mom," she shouted, "we're in the living room.

"What do you mean WE?" came the retort, then "OH, WOW, NICE!" as the person behind the voice entered the room. Dan's face was as red as his ass now, and not because of the effort he had been putting into Jess' orgasms. "Did you do that, Jess?"

Jess smiled. "Yep, and he enjoyed it, in the end."

"Looks bloody painful to me," came the reply, "but well done, that's as good a whopping as many I have given over the years. Your Dad's ass glowed like that many times and it never did him any harm."

"Thanks Mom," Jess answered, causing Dan to wonder what he had got himself into. "This is Dan. He brought my bookcase and then spent all his time ogling my tits, pussy and ass, so he ended up here. He hasn't cum yet, and I am not sure he should be allowed to. What do you think?"

"Well, gee, you caught me on the hop here," replied Mom "Was he really staring bad? Has he made up for it yet? And do we need to leave things as they are, or can we hurt him some more?" Dan didn't like the way this conversation was going and looked up to Jess with pleading eyes.

"Oh he has nobody at home to worry about him, well, except the dog." Jess laughed, remembering Dan's response to her earlier question.

"Well, turn around boy." said the voice which Dan knew now to be Jess' Mom, "Lets see you!"

Dan looked at Jess, who nodded Yes, so he turned whilst remaining on his knees. If Dan thought Jess was gorgeous, it was clear where she got it from. Standing in front of him was a slightly taller version of Jess, but, unbelievably she looked more like Jess' sister in terms of age - she looked early thirties at most, he thought. Long dark hair, not quite black, in a ponytail, a pair of very big tits and a willowy height; she must have been nearly 6ft tall - this was "Mom"!

"Why did he let you whop him like that without stopping you?" asked "Mom."

"Oh, I had him cuffed so he couldn't really defend himself." replied Jess.

"Good, put the cuffs back on, hands round his back." said "Mom," "I have an idea. We shall allow him to decide for himself how much more he suffers, or enjoys, for the rest of his time here."

"I got the rest of the...." said a voice, coming into the room and stopping, startled by the vision in front of her. Her sister naked on the sofa, her Mom standing to the right and a naked man kneeling on the floor between them, not just that, but a naked man with a bright red whopped ass. "Did I interrupt something?"

"Hi Molly" said Jess, "this is Dan and he is just deciding how much more pain he is going to get before he goes home!"

"I have rather too many questions for now," replied Molly, "....so, when is tea, Mom?"

"I will help Jess here first, then I can put on tea. Do you want to watch, or help? You might learn something about controlling your man!"

Molly looked at her Mom, then at Jess and then at Dan. "I can help you, but I don't want to hurt him."

"Mom" turned to Dan who was still kneeling on the floor with his hands cuffed behind him and said "My name is Carol, without an e, remember that, just in case! I like my men just like you are now, so please do as I ask, and there will be no issues. Now, with Jess' agreement me and you are going to play a game. It's one I have played before, with variations, but it will reveal just how submissive and how much of a pain slut you are. Jess, will you let me lead on this?"

"Of course, Mom" replied Jess "and will you help, Molly?"

"Suppose so," replied Molly, "but as I said I don't want to hurt him. What do you want me to do?"

Carol mused for a moment, then broke out into a wide grin. "I know" she said. Oh this will be fun. Moll, get that coir mat from the front door. Jess clear a space on the floor." Pointing at Dan, Carol said "You just stay there, and when Jess has cleared the floor, lie down there in line with the sofa, on your back."

The girls set about their tasks, but Dan was totally distracted as Carol reached up and pulled her polo shirt over her head revealing a very full half cup red bra holding her magnificent tits. She then popped her jeans button and pulled the zip down, revealing what looked like matching lacy panties, but left the jeans on. The girls returned. "Put the mat down there, in line with the sofa."

"Dan, it's nearly tea time and I am hungry, so this better not take long. Get your ass on that mat - yes, I know it's rough - that's the point! Jess says you haven't cum, even though I bet you thought you would have by now, and I guess you want to?"

Dan looked up at her from his position prone on the floor, hands cuffed behind his back, and nodded Yes. "OK, this is what will happen........"

"I see you are pretty hard there already, so, Jess, please get him as hard and erect as you can. I am going to lie on top of you, Dan, pressing your sore ass onto that rough mat. I will "grapevine" your legs and "rub you up the right way" to force you to cum. Oh, and I think a nice breast smother will add to the pain. Have you ever heard of vegetables done 3 ways, well I call this "Pain, 3 ways."

Now that everything was ready, Carol lay down on top of Dan, pulling the head of his hard penis up to rest on the lacy part at the top of her panties, Wrapping her legs around his in a classic grapevine, Carol swiftly moved her legs apart until Dan resisted. "OK, here we go. Dan, you just have to last as long as you can without cumming, and if you make a really good effort, we might let you come back again." She smiled.

Increasing the pressure into her strong thighs, Carol slowly moved Dans legs apart more. "This is starting to hurt." he thought. From her advantageous position on top of him she could feel he was trying to resist. Using her hips, Carol started to slide up and down, rubbing his penis head on the lace of her panties, she knew Dan was beginning to feel a bit of pain, and pleasure, as his penis was getting lots of stimilation. Suddenly the coir mat came into play and his, already raw, ass was getting seriously painful from the rough surface. Dan let out a yelp as the pains in his arms, ass and legs started to overwhelm him.

"Too noisy!" said Carol, pulling his head up straight into her deep cleavage. Dan was in heaven,..... for a few minutes until the pain and his shortage of breath became seriously uncomfortable.

Dan was losing it with the shortage of air and Carol causing him pain right through his body. Any of the stimulations and pains would be ok singly, but as a whole, it was too much for him. The big question was, would he cum first from the stimulation or pass out from the pain. He couldn't see anything, but the feeling of soft breast flesh smothering his face, was something he definitely liked.

Carol started to move quicker, looking at her daughters to check they could see what she was doing, and started to grind harder on the suffering man under her. She knew her legs were really strong and her breasts around his face big enough to seriously reduce the amount of air he was getting, so she didn't expect him to last too long. Really, the pain from his ass would determine the result of this situation. If he was a normal or dominant man, the pain in his legs, ass and arms would cause him to pass out pretty soon as giving up was not an option. If however, the stimulation from his penis, the feeling of her big soft tits on his face, and the fact it was a woman doing this to Dan, was the overriding sensation in his brain, then he would cum very soon and reveal himself to be a submissive.

Suddenly, Dan started to jerk, wriggle and try to roll Carol off him, but she was ready for him and steadied herself, powered into her thighs, spreading them further apart, clamped her tits harder round his head and moved up and down his body faster. That was all it needed and Dan screamed out, so loud that his cry was easily audible in the room, and then fell still. Carol smiled, then laughed, as she released his head, and started to rise. All across her bare stomach was the evidence of a massive ejaculation as the stimulation had exceeded the pain, but it looked like it had been a close thing!

"Quick, Moll, get a glass of water. I think he is going to need it. Get some paracetamol too, he might have a sore head when he comes round too. Oh, and a damp cloth to clean all this cum off me!"

Molly fetched the water and Carol dumped half of it on his very red face, causing him to cough and splutter as he came round again. "Drink!" said Carol, "then we can talk." Carol wiped her stomach with the cloth, removing the evidence of Dan's submission.

Dan was dizzy and confused, but took the remaining water and drank it all in one go. "More, please." he croaked. Molly took the glass and went for more.

"Just stay there and don't try to do anything too quickly." said Carol, sharing a conspiratorial smile with Jess who had just watched a man get devastated by her Mom. "Do you need a paracetamol too?"

Dan considered his head, and realised it was throbbing, but not too badly. "I think I will, thank you." he said.

"Five minutes to get yourself sorted, then we can talk." said Carol, pulling her polo shirt back over her head, and refastening her jeans. "Jess, you best get dressed - I'll start tea in a short while. He needs to be dressed and gone by then, unless I have done him some permanent physical harm!"

.................

Ten minutes later, Jess now had her pyjamas on, Dan was dressed, and wonderful smells were coming from the kitchen. Dan and Jess sat in silence, neither too sure how to start a conversation. Carol came into the room and sat in the chair across from Jess on the sofa and Dan still on the floor.

"So, how are you feeling, Dan?" started Carol "I guess you are in a little pain, and somewhat confused?"

Dan considered the question and decided he was as Ok as could be expected. "No, not confused." he said "You have clarified in my mind if I am a submissive or not, and think I must be, because, although Jess really hurt my ass earlier and you basically destroyed my body and mind just now, I don't feel unhappy or angry. I didn't enjoy all the pain, but I, sort of, "wandered off" in my brain, and I think that stopped the pain from being too excessive. Overall, I wouldn't have swapped this afternoon for what I had planned." Dan smiled to himself, "but I must be off now; got to get back to the depot then home."

Carol looked over at Jess and Molly and said "Have you two got anything else you need to buy for your rooms? I think Dan might want to come back with more deliveries for us very soon."

They all, including Dan, laughed.