The Challenge

He looked sideways trying to gauge what she was intending.

She made him wait before speaking, "I have been asked to correct your thoughts. You seem to think only you is allowed pleasure. You demand service but fail to reciprocate. Today, I will begin your training. There are no safe words. I have been given written, explicit instructions that you are to become subservient to your mistress. She will return in three hours by which time you will be a delight for her to tease."

She moved in front of him. He could smell her arousal. His eyes saw the infamous Lochgelly tawse his parents had told him about from their schooldays. It had long been banished from schools. She was watching him closely. His breath was rapid. His eyes showed his fear.

She moved behind him. She did nothing, just watched his body as he waited for the first blow. As he slowly relaxed, thinking this was a prank, she brought the tawse down on his bum. He screamed. She held his mouth open and fitted a gag in it to stop further ones. She counted down from his age as she made sure each stroke covered his bum. It was red, very red. He was in tears.

Ron heard her rummaging in her bag. He wondered what next. He couldn't stop this. He felt some soothing balm being lightly massaged into his bum. It was arousing and painful in the same movement. Next, his eyes shot open as he felt something cold being inserted into his bum. He had never felt so stretched. Carole only used a finger or two and they had recently used a butt plug but this felt much wider and longer. His eyes watered as the fullest part finally entered him.

The woman came back to the front and removed the gag. She placed her leather boot under his head. "Kiss my boot, make it shine with your tongue. If you do it right, I'll maybe let you taste my pussy. Be warned if you do you'll never love another one as much."

Ron had no option so he tried his best to lick and shine the boot. The woman grabbed his nipples and twisted them until he cried out. She replaced her boot with the other one. She leaned closer and he could almost see her pussy juice drip onto the sheet.

She moved behind him and he felt his arms being released. He relaxed as he thought it was over but she pulled his arms behind him and locked them together. She locked his legs together and pulled him onto his knees. She lay before him. She had removed the pantie and he saw the tattoo. The python like snake was curled around her body several times until the head appeared. Its open mouth was her pussy. The skin so delicately tattooed either side was its head. Her pussy was going to devour him.

"Slave, kiss my boots to my pussy, both sides. Don't touch my pussy. If you do it well, I'll reward you. If not, I'll cage you."

Ron began kissing and licking his way up her left boot. At her thigh he continued until he felt the heat of her pussy on his head. He returned down and started on the right leg. He stopped for the same reason. She seemed pleased. She rolled him onto his back and straddled his head. She slowly eased down until her pussy split wide open. He could feel her dripping onto his face. She closed the gap but moved at the last moment so her bum hole caught his nose. She made him inhale her nectar. She began to move and told him to tongue her. He was not to stop until she said so. To reinforce this, she pressed hard against his cock which was not fully erect. He stifled a scream. He didn't want gagged again.

She moved around presenting her pussy to him, "Harder, deeper, faster, " was all she said. She came and almost buried his head in the mattress. She didn't have him stop, he attacked her pussy and bum again. He was vaguely aware of her nails caressing his balls and cock. She came again and held his cock firmly.

She moved down, he couldn't move being restrained. She took his cock and put in in her pussy. She never moved but her pussy massaged him, wringing his cock out. She spoke, "A woman is always in charge. No man can challenge a pussy like mine. You will desire all the woman you have to have such a pussy but only a few can use it like me." Ron tried to thrust into her but she was not having that. As soon as he appeared close to coming, her pussy held him so tightly he couldn't. Four times she held him off until she smiled and said, "Cum for me!"

Ron did. He had never felt so many spasms, he felt drained as he finished. She stood up and sat on his face. "Eat me clean, know your place!"

Ron had no option. He didn't know her tone had so scared him his cock shrivelled. He felt her place something on his cock as she came. His own cum was pouring out of her forced by her copious fluids. He was forced to swallow as he couldn't breathe otherwise.

She stood beside the bed, her tone a little gentler than at the beginning, "You did quite well but have still a lot of work to do. I'll let your wife know we're through for this evening. I look forward to our next training session."

She walked away leaving Ron lying on the bed. He was still restrained and whatever was in his bum was still there. He lay trying to work out what had just happened.

He must have fallen asleep as he jerked awake as Carole came into the bedroom. "Ron what have you been up to? First Cindi and now this!" Her voice matched her look of anger.

She saw a piece of paper on the bedside cabinet. She collapsed onto the chair beside it. She was waving this paper. Her voice was quivering, "Ron, when we spoke with Sharon about your fantasies, this was one you said you wanted to experience. I said I couldn't beat you up, denigrate you like that so you ordered Mistress Domino on an evening I was going to be late. From what she's left here, you failed. She felt you didn't eat her properly so she caged you. She's left me the key with instructions."

Carole looked aghast at Ron, "Tell me you didn't fuck her!" Ron looked away, "She fucked me, I had no choice. I was restrained like this. She fucked me and made me lick her clean. Carole, I thought it was you, roleplay, love month. It was only when she belted my arse so hard, I knew it wasn't you as you couldn't do that. By then I was restrained and I couldn't speak. I was gagged. She said you'd told her no safe words.

"Carole, I love only you. Twice now, I've thought it was you playing but it seems I'm wrong. You won't trust me and I'll lose your love. Please give me a chance to make it up to you."

Carole looked thoughtful, "Did she complete your fantasy? Do you want to order her again?"

Ron spoke softly, "She didn't. She must have run out of time. I never ordered her. I thought it was you going above and beyond to give me my fantasy. I'm sorry I've hurt you."

Carole was sharp, "What did she fail to do?"

Ron looked down, "Carole, she didn't end it. She never dragged me to the shower and pissed on my worthless arse."

Carole groaned, "So you'll need to order her again to fulfil your fantasy."

Ron looked so sad, "Carole, I never ordered her. I don't know how. I don't even know if I want to repeat it."

Carole spoke slowly, "It can't have been that bad if you don't know. It means it's still a possibility in the future."

Ron spoke firmly, "Carole, I'll never order her. I love you too much to let a fantasy break us apart. Even if it was everything I ever dreamt it would be I wouldn't risk losing you." His eyes and face showed his remorse.

Carole stood up and hauled Ron off the bed. She dragged him into the shower and raised her skirt. He saw the python as she unleashed her built up piss onto him. Once she had finished, she stripped and released him so they could shower together.

Once dry they cuddled in bed. Carole spoke, "Ron, I stopped when I did as I was so confused. I was enjoying this side of me, I never knew I had. Many of the roleplays have seen me doing things I haven't done but this was way beyond anything, way out of my comfort zone. I shouldn't have been enjoying hurting, abusing you.

"I had to have a long think about myself. Initially, I came to the conclusion I was so wet because I was giving you your fantasy. I thought my enjoyment was only based on your enjoyment but in truth, I was shocked to find that I did enjoy it as well. I saw how you veered between loving and hating it, just like you feared. It appears I have a dominatrix inside me I never knew about. If you want to do it in the future, I think we can. Not often though."

Ron cuddled in and kissed her, "Carole, I love you. You hurt yourself giving me my fantasy. Let's just take our time."

Carole held his eyes with her as she said, "I love you so much but I need to cum badly, eat me. If you do it well, I'll release your cage tomorrow."

Ron began kissing her and going lower. Five orgasms later, his tongue was beaten and his cock was sore from bashing that cock cage. Why had he said that bit in front of Sharon?

Day 22; - Wednesday - Revelation 3 -Babs (mild crossdressing)

As Bob drove home, his mind was running through how the evening would go. So far, he hadn't lasted long as Babs told him about the Love Month. He doubted tonight would be much different. He hoped he would still be hard when they came to his greatest experience before last Thursday. If Joanna had been Babs. Maybe nightmare if it turned out she wasn't. He knew he would erupt if he lasted until she told him about that walk home.

Once home Babs was very happy. She was dressed to entice and flirt, not have him cumming over the table. It didn't help that when she put down his dessert he saw the nipples rings. His cock was rising and Babs saw him. She licked her red lips. His heart took a few extra beats.

She made them coffee and they sat and discussed their day as their stomachs dealt with the dinner. Once she was happy, she told him, "It's story night. I have laid out what you are to wear. I'll prepare myself. Shout when you are ready."

Bob set off. As he went through their bedroom to the ensuite, he saw her red suspender belt, red stockings and red thong which she had been wearing that Saturday night. She'd read his mind. He was breathing quickly. There was a note on the clothing. He was to shave himself completely and wear it. He quickly showered. The razor blade and gel were in the cubicle. They had played like this in the past but only his pubic hair. He wasn't particularly hairy so it wasn't a difficult job but just stroking his cock and balls had him almost cum.

Once he was dressed he called Babs. Babs was dressed in a red leather corset which held her breasts high. There was a matching thong with red stockings and red shoes.

Babs spoke severely, "Good. I see you have made a good job of your instructions. Your cock does like those panties doesn't he. Lie on the bed. I have prepared it."

Bob moved to the bed and saw the restraints. The pillows raised his head so he could see all of him. Babs restrained his arms and legs. As she did, she gave him instructions to kiss and bite her nipples. Bob did as well as he could.

Babs sat across his legs, the leather thong hinting at the pussy behind. She was running her hands lightly up his thighs, above the stocking tops to the thong, tweaking and lightly caressing his cock. She did it in time as she spoke. As her cadence changed so did the level of caress. His cock was already saying, I'm about to blow. She smiled, as she said softly, "I know you know the rules but so there is no debate, you can only cum once. I will have as many orgasms as I require. Last week it was six. Who knows what tonight will bring. Have you been exercising your tongue?

"Last week we reached you coming home to be met by the doctor. You came as I described sitting on you. I'll begin just after that. It was never a part of the roleplay the girls and I had planned. It just came to me.

"I knew you had that fantasy of licking me clean and I forced you to tell me. I also wanted to taste you and me. It turned me on so much to hear your trust in telling me something so personal. We were both a little reticent as we started but when we got into it, I couldn't believe the feelings you were generating in my pussy. I had you deeper in my mouth than I ever had, I was so turned on. We both had explosive orgasms.

"The look on your face afterwards was fantastic. It showed your love for me, your great delight in doing that. I had been worried about you being annoyed at me for forcing the issue but I saw in your eyes your delight. I had to do it again. As I sat on your face, I never imagined I could have a bigger orgasm but I did as you got all of us out of me. I'm sure the doctor had emptied your balls. We hugged and slept such a contented sleep together. When I woke up, I had to blow you. It was me saying thank you for such an epic experience.

"That night, I was the stripper gram. I was always shy about doing any erotic dance for you as I'm not a good dancer. Debbie was our choreographer. She helped us all move, time our displays. When we practised it for the first time, I was Debbie's guinea pig. She danced around me, caressed me. My nipples were trying to get out to see for themselves. As she stripped off, I was so turned on.

"I saw your face as I danced for you. The joy in your eyes, the standing ovation by your cock. I could tell you wanted to be released from the restraints so I was glad you were. Each time I removed a piece of clothing or ran my fingers over my body, your cock twitched, saying I'm here, play with me. As I dropped my panties and bent over, I could see your precum running from him. As I held my pussy lips apart and fingered myself, I could see you struggling not to cum.

"When Debbie had reached the end and simulated fucking me, I came like she did. We were both shocked. I never thought that was possible but my mind had been playing me doing it to you as she danced. As I dived onto your cock, I came. I knew you wouldn't be long but you held long enough for me to cum again. I could feel each burst of sperm as you fired, you were so aroused. It was everything I wanted to do for you.

"As we worked through what we could do, we did discuss some of the easier fantasies our husbands had. We never discussed any sensitive ones. We didn't discuss our own sensitive ones. One fantasy each of you had was for us to be braless. You almost came the week before when I handed you my knickers close to the end. This time you knew I was braless from the very beginning. I was watching you. When we discussed something like this with Sharon, you were so conflicted. Sharon helped you see you weren't a pervert. I saw the pride you had in me and I relaxed as I knew it would never go further. At the table, I saw how you loved all the intriguing views especially mine you were getting. I saw that fear, that conflict but also the desire in your eyes for the others to see more of me. You did and you didn't. A conundrum. Like can I cum now or can I wait?

"When my dress started to unzip, I was stunned. All the other men wanted the zip to go all the way down. You did too but were scared. We were both happy the zip stuck on my nipples. It gave me time to think. When I'd stopped by you as I headed to the toilet I saw how hard your cock was. I knew you wanted the zip to fail but you couldn't say so. Your eyes showed your conflict. Many of the others had similar conflicts in their eyes. The others may not have been so perilously close to exposing themselves but the men were fantasising about it.

"This Saturday night became something else. I've never experienced anything like it. The girls have never discussed anything like this. It was just meant to be a tease, okay a lot of teasing and when home a lot of sexual release. That part we managed. What happened was never discussed with any of them. It grew in me that evening as I saw how you were so excited but scared. I have thought about what happened a lot. I must admit it turns me on so much, I've masturbated thinking of it since. I cum even harder if I think of you there watching me. You've never asked me to masturbate for you but I'd love you to be dominant, demand it, tell me what to do. Sometimes I think of Margaret, John, Tracey and Mike watching me. I flood at the thought."

Bob was shocked as Babs exclaimed, "Fuck it, I was going to try and just say everything but I need to cum." Babs never swears.

Babs removed the thong and sank her soaking wet pussy onto his face. She leaned forward so she could play with his cock. She loved the smooth feeling and the way the thong showed of his cock. She blew on him. She didn't want him to cum just yet. Bob was expertly licking her dry and she came as he rimed her. She moved slightly so he could tongue her pussy lips and clit. The second orgasm came very quickly. She raised herself to check that Bob hadn't drowned. She rubbed her whole pubic area over him until she came again. She had to rest for a few minutes.

She returned to straddling his legs. Her pussy was wide open. His cock wanted to be engulfed within her but Babs held herself away from him.

"Bob, this is so turning me on. I love you in suspenders and stockings. I can see how you like me in them. The tactile sensation as I caress you changes. But back to the story.

"When we left, I gave you the option as we turned into the park. I was almost going to fuck you but I so love you, I wanted to give you something you'll always remember. I was shaking as you totally unzipped me. On one hand I didn't want you too but on the other, I wanted to give you your greatest fantasy. As we set off, I could feel you want to run but I made it slow as I didn't know if I could ever do it again and I wanted you to enjoy your torment.

"Meeting Margaret and John had me really soaking my thong. It was already very wet. John could see my pussy but Margaret probably couldn't at the beginning. She did when she moved. As I saw her become excited by me, I almost flooded myself. I was so aroused by the thought I'd turned her on. I saw his cock standing to attention because of me. I was just as surprised how much I enjoyed that. He wanted me! Even your cock grew bigger as your fantasy was realised. Margaret's nipples showed how much she was turned on. She was licking her lips as she viewed your cock.

"I was so turned on, I don't recall much of the walk after that apart from your hand on my breast, something I've never allowed before when we're outside. Meeting Tracey and Mike just added to everything. If you had leaned me over and fucked me in front of them, I wouldn't have been able to stop you.

"Once in the house you were fucking me like I demanded. When you screamed they were watching I came and came!

"Oh! You've just cum. We'll have to continue the story next week."

Babs climbed over Bob until her pussy was on his face. She scooped some cum in her finger and fed it to him. "Just you, not us. I love your taste. I hope you do so we can exchange more body fluids. Drive me to more orgasms. Can you beat last week?"

As Bob tongued her, Babs caressed his legs and balls. She didn't go near his cock. Soon she reached orgasm number seven. Bob's stomach showed how much fluid he'd ingested from her pussy which was flowing like a river. Babs untied him and they cuddled.

Babs held his face as she gently kissed him. "Bob, this is the second time, I've dressed you in stockings. Each time I have been so turned on. Will you consider letting me do this again when the love month is over? We can discuss how much, how far you will go if you're happy to do so."

Bob's reply pleased her, "I'll do it for you. I see the pleasure it gives you. We can discuss it more. I do like the feelings so I'm happy."

Babs great big passionate kiss revived his cock but she was adamant, once only tonight. He'd need his strength for the rest of the month.

Day 23; - Thursday - prostitute - Jessie

As Ted headed off to the pub, Jessie was breathing quickly. Last night, she had managed to tell him about the challenge up to the point where they were discussing fantasies to play on their husbands. As she described how that led to her talk with him and what that afternoon meant to her, how she had felt arousing him and having him fuck her like that, Ted came and came. He seemed to love cumming in her satin panties.