“Yes I spank your mother about once a month as she told you. There are also two of her friends who enjoy very similar sessions. I cannot believe she sent you to me to discuss a spanking for you. You are what 20 years old and I thought you are planning your wedding. What would you want with a 60 year old when you could have any young man of your choice to spank you?’

“I love my fiancé very much but I know he will never spank me. I want to experience the thrill that mum says is unrivalled by anything she has ever experienced. If I don’t experience it now I never will. Mum says you can play her like a musical instrument. Nobody of my age has got your expertize. Please Mr Walker agree to spank me just like you do Mum.”

“There is nothing I could imagine that I would enjoy more than taking complete control of your stunning body. We need to talk about what you want and what you don’t want. If you are sure you can come here tomorrow after lunch.”

“I do not want to discuss what we do as I want to be completely under your control. Mum mentioned using a safe word, how does that work?”

“We agree a word which you say if you want me to stop what I am doing. The word pensioner seems very apt and easy to remember.”

“Would you mind if I dress up as a schoolgirl? It would help my feelings of submission and helplessness that I would want to enjoy.”

“If I did not know you better I would have wondered that this was just one big wind up. I hope you really are serious about coming tomorrow. I will see you at one o’clock if you do not come to your senses or chicken out first.”

“I am so excited right now I know I will be desperately waiting for one o’clock to arrive. I better go now before I embarrass myself. See you at one.”

Jessie was right; she slept badly and spent the whole morning excited and apprehensive about the spanking to come. She was delighted that she was able to fit into her old school uniform. The knickers were a little tight as her, always substantial; bottom had muscled up with all her training. She delayed putting her knickers on until she was due to leave as she was getting very wet in anticipation. She knocked on the door a minute before one.

“Jessie you know you are here to be spanked. You will obey me all the time. Do you figure out and agree?”

“I figure out and agree Mr Walker. I know I deserve the spanking I am about to receive.”

Jessie could not believe how natural it was to be led into his study. Mr Walker was treating her as a schoolgirl and it felt surprisingly comforting as well as frightening.

“Take your coat, cardigan and shoes off please and put them on the chair there. Go and stand in the corner with your hands on your head.”

Jessie had expected to be taken straight over his knee and spanked. She realized that her mouth was dry and her heart was beating hard and fast. After what seemed like hours his voice was authoritative as she was told to drape herself over his knee. As he tucked her skirt into its’ own waistband Jessie was sure that there was much more contact with her knicker-covered bottom than totally necessary.

“We will begin with a dozen firm spanks to begin to warm your exquisite bottom. You will keep your bottom relaxed and count out load after each spank.”

Jessie concentrated on keeping her bottom relaxed and let the sting of each contact spread out. The spanks were not that hard but covered the whole area covered by the full but slightly tight knickers There was just a nice warm glow all over the area after the first dozen. Jessie’s heart rate jumped as she felt the knickers pulled firmly down below her knees.

“After each dozen I will sooth your bottom and let the spanking take full effect. Are you okay with that?”

“Mum told me everything and I want the full experience. Oh that is so sensual, I think I could nearly doze off.”

He was caressing her bottom very lightly with just the tips of his fingers. From the sighs that Jessie was making he realized that she was as easily aroused as her Mum.

“For the next dozen I want you to keep you cheeks very tense at the point of contact. You will discover the feeling is very different. You may concentrate fully on your bottom, no need to count these. Relax and enjoy.”

Even the sound of each spank was completely different to the first dozen. He applied the first six to one side and second six to the other. Each cracking noise was accompanied by a much harder and crisper pain, which did not spread out as quickly. She kept her bottom tense as he started the massage.

“You can relax your bottom now. After the next dozen I will apply some cream but for now I will massage you much more firmly. You will not want me to be so firm later.”

This was not the sensual teasing like before but massaged deeply into the toned muscles. Jessie was aware that as his hands stretched her cheeks near her pussy he would have a perfect view of her all of her charms. She knew she was very aroused and embarrassed that he would be able to see it.

“Don’t worry Jessie. I know you are aroused but there is no need to be embarrassed by it. Your Mum arouses easily it is so lovely to see. You have so much in common with your Mum but some distinct differences.”

“Explain more about the differences.”

“Well your Mum has a lovely bottom but I am sure it has never had the wonderful muscle tone yours has. It is obvious you spend time in the gym. Please take my next opinion as the compliment intended. There is the most arousing aroma to your excitement. It is a sweetness that I have never experienced and it was evident immediately you went over my knee.”

“So am not only embarrassingly aroused but that arousal smells strongly.”

“Now I have upset you, sorry. The sweetness is something you will grow to love. I bet your fiancé loves it but being young is unable to say anything without risking upsetting you, like I have. Take it from an old man like me, if you are getting half the pleasure I am getting from your current arousal I am delight. Embarrassed or not revel in it.”

“Now it is me that is sorry. Part of my embarrassment is that I have got so aroused by someone who is so, is so mature. I am a little frightened by my reaction.”

“The word is old by the way, cheese is mature, compared to you I am just old. Let’s get back to what you came here for. The next dozen will be applied very quickly. One of my ladies loves to hold her breath during this stage, but that is up to you.”

They were both quick but also the hardest so far. Jessie took the advice and held her breath. After the last of the dozen the release of her breath was half grunt half shriek.

“Boy that was intense. I am glad I held my breath otherwise I would have been yelling the house down. My skin is tingling, no exploding with sensation. Some is pain but some I can’t describe.”

“We will slow things down a little. I promised to apply some cream to your troubled bottom. It will; cool, soothe, calm and reduce bruising. There will be no more spanking for a few minutes. I want you to relax every muscle in your body.”

The cream had been in the fridge and was therefore very cold. The initial contact made Jessie jump but the gentle application soon had her barely aware of the fingertip caresses the spanked area. There was no particular point that it registered that the caresses were now lower towards the tops of her legs and the junction between them. No more cream was being added to the caresses but they remained gentle almost teasing. He realized long before she did that she was gradually spreading her legs further apart and pushing herself up towards the stimulation.

“You may wish to stop the spanking there. It is your first time with me and I would hate to spoil your obvious enjoyment by going too far.”

“Would you please just carry on with what you are doing for a few minutes? I can’t imagine stopping the spanking now. I am feeling sort of fuzzy, distant as if in a cocoon. Please let me experience it a little longer.”

He did as she requested but allowed his fingers and hand to include the area from the core of her bottom to just short of her clit. As he expected she shifted her position and strained her body to ensure that her clit was included. They both were fully aware that he had long ago stopped treating her sore bottom and was now focused on simulating her already very aroused pussy. Increasingly he allowed the contact to concentrate on her clit until he sensed more urgency in her movement.

“There, there I know you are enjoying that but if you are wanting me to spank you more let’s just slow you down again.”

She did not understand why he was reaching for the cream again until she felt his moistened middle finger circling her anus. The circling became more and more focused until with a small push the finger entered by an inch or so. Jessie was confused as to why this felt so erotic. She had always seen it as a dirty area that no one had ever touched. It surely should have been painful, but it was anything but. For the second time his next comment suggested that he could read her mind.

“Oh that is so lovely you have never experienced anal stimulation. It does not need to be painful or distasteful. I have known women orgasm from anal stimulation alone. Most discover combining it with more traditional stimulation can greatly improve their excitement and their orgasms. I think you may not be quite ready for me to show you those delights yet. I would recommend that you work out how to educate your obviously vanilla boyfriend so that you can both experiment with anal stimulation. For now I am gonna gently fuck the first couple of inches of your bottom, my finger will not hurt you. Your body will tell both of us whether you want me to stop or carry on a little deeper.”

Jessie knew exactly what he meant but was desperate to not appear over-enthusiastic. She therefore passively let his finger move in and out, the first three times. Her confusion melted away quickly when she found herself pushing up to welcome the invading digit. This penetration was comparable to the first time she had enjoyed intercourse. Had that lasted for more than 30 seconds she was sure she would have orgasmed. This now was however less demanding but no less devastating. She was scared that his friend might not be the only one who could orgasm by anal only. As if reading her mind again he pushed once more, this time as far as his finger could before reluctantly withdrawing it.

“I have been here about an hour and I have learned more than I have since I lost my virginity when I was 18. I could explode under your expertise in various methods you have already shown me, and probably many others that I have no understanding of. Given all that, I want more spanking as I may never have the chance to be spanked when so aroused.”

“I am only happy to give you one more dozen spanks. Your mum is one of only two women I have met who can cum from spanking alone. To achieve climax she has to be spanked harder and longer that I would be happy subjecting you to on your first time. Please trust me on this.”

“I would love to be brave enough to see whether I could orgasm all over you while you spank and spank me. Reluctantly, I will trust your greater knowledge. Please spank me as hard as you dare. I might even prove you wrong in just twelve hard spanks. If not we will just have to take stock.”

“The next dozen will be harsh. You may wish to stop me using the safe word. Do not feel you have failed if you need to. You have done brilliantly for a first time. I have never enjoyed a first session with anyone as much as this, thank you.”

Jessie felt pride at hearing his comments. She was not going to use a safe word; it was a matter of competitive pride. Each spank was hard and accompanied by the briefest visit of his finger to her clit. She knew she was not going to be able to stop the embarrassment but excitement of exploding on his single finger. He however had other ideas and amended his stimulation to ensure she was kept boiling but just frustratingly short of climax.

After this last dozen were completed he gently caressed her bottom but kept clear of her anus, pussy and clit. She relaxed quietly crying for the first time while with him. She had no idea why she was crying but could not help herself.

“Do not worry my little one. Your emotions and body are just totally confused. When you are ready let me know whether you want me to; carry on massaging you as I am, help you figure out just how anally arousable you are or tease your clit until you explode.”

“All of those options are wonderful but there is one which tops them all. Please I need fucking and bringing to orgasm like I have never needed before. Mum said that she has never experienced sexual pleasure that gets close to what she enjoys when you fuck her”

“She did distribute everything with you didn’t she? I can’t explain but I can’t fuck you, you are too young.”

“You have done things to me which are more intimate than I have ever imagined. You have played me like an instrument. You have dominated me completely. You have been a gentleman through out. Surely we have both earned a good fucking. I know I am young but that should not matter. You are still fully clothed, please strip for me so that we can at least give each other the climax that we both deserve.”

“Are you sure that you want to see my old body. It may ruin the whole experience for you. I think this is a mistake.”

Her eyes were alight as she nodded head. He started to undress slowly. She was delighted to see what good shape he was in. He turned his back as he slid the last two garments, his trousers and pants, down his legs and over his feet. Turning his head first to look into her eyes as he turned fully round.

“Holy shit, what the fuck, that thing is massive. It can’t be real. Is there any blood in the rest of your body. Oh I am sorry you must hate reactions like that. It is utterly gorgeous while frightening the shit out of me at the same time. Can I please hold it, it looks like it could do with some TLC.”

“Your Mum didn’t tell you everything then. Trust me that is one of the most lovely reactions I have had. Now you know why you are too young. I have never made love to anyone who has not gone through childbirth first. Most mothers do as all the rest, call me a freak and run away quickly. Now you see why I can’t fuck you.”

“Would you please let me try. I can promise nothing but I would regret not trying for the rest of my life. Please would you let me try Mr Walker I will do anything you suggest to make it happen?”

He was seated on an armless chair fully lubricated as he gestured her to face him and sit astride him. They cuddled each other close feeling the contact where his prick was rubbing along her clit, stomach and up nearly to her breasts. Reality set in for Jessie as this brought it home as to where it could reach to inside her.

“My Mum is able to take the whole of this gorgeous monster and still breath?”

“It took her five attempts and some stretching exercises at home before she was happy taking it all. She loves to use every last centimeter of in now.”

It seemed like a challenge to Jessie who slid up his body until the purple head of his prick was lodged firmly between them and hard against her wet pussy. She started small movements trying to find the exact position and angle to start the penetration. They hugged each other close, their heads on each other’s shoulders. She knew it was now or never. A frightening wave of excitement and terror coursed through her body as she attempted to impale herself. She became worried when the feeling of her pussy being painfully stretched got worse and she knew that not even his head was fully inside her. She gave one last push and felt a relief as it pushed through.

“Fuck that is big, but I said I could take it.”

She lent back to see his reaction and to show him how proud she was feeling. Her face was alive with happiness as he smiled at her in an almost fatherly way. He desperately tried to drink in every one of her complicated emotions.

“That is amazing Jessie. You are fitting me like a glove, if one that is two sizes too small. You should probably stop now we don’t want to damage you only six months before your wedding.”

He did have real concern but knew that Jessie would see this as a further challenge. She had risen to every one so far as her mother had predicted. He knew if she thought that she was doing something no one had done before she would stretch herself, quite literally, to rise to the challenge. A little white lie or two would not hurt.

“No one has ever taken me fully on their first attempt. If you do want to carry on a little you will have to relax, you are understandably very tense.”

She would show him she would take every inch her body could possibly manager. Driven on by this she pushed a couple of inches further before rising up and repeating. It was at this stage that her body started to remind her that she was extremely aroused. She was desperate to be taking all of him before she had her orgasm. She tried to lengthen the downward thrusts but the pain was returning. She had almost no warning as the orgasm hit her harder than she had ever been hit.

“Oh sorry, sorry, sorry I can not stop it, it is far too powerful.”

She was now frantic as wave after wave crashed and shuddered through her pain-racked body. He was actual frightened when her body went limp. With all tension gone she collapsed down impaling herself fully on his prick. His concern grew as she appeared to have passed out. He shifted himself to get a better view of her face. She shook herself as if waking up.

“If that is heaven I would be happy to die now. That was like nothing I even knew could exist. It was obviously the wonderful fucking, but it was that with the pain of both my bottom and my pussy. Thank you.”

She had not at this stage realized that the combination of passing out and the relaxation caused by the orgasm had resulted in him being buried in her fully. He made the smallest of thrusts to bring her fully back to reality. When he only got a happy gasp from Jessie he increased the movement.

“I did it, I took the whole of that monster. You must be ready to explode. It is your turn. I am gonna nearly take you out before I bury you deep. I am gonna tease every inch of your gorgeous cock until you lose all control and cum.”

“You just cum again for me and I will cum with you.”

“I have never cum twice but I am happy to fuck you until you are ready to come.”

“You will cum again when I am ready and we can cum together. I would like this to last forever but I think it would be better for you not to over stretch yourself for too long. Jessie you are to cum now, cum on my massive prick and cum like you have never cum before.”

“You fucking bastard you had to prove your total control over me. If I could control my hips I just might be able to stop my ——–oh this one is gonna hurt it is so —–what are you doing to me —-“

“Just fucking you as you asked me to.”

With this he held onto her and fucked deep and hard ignoring her screams.

It was ten minutes later before she was able to speak.

“When will you spank me again, I can’t wait?”

“I think it better if you put all your energies into preparing for your wedding. You are getting married in six months and I think you need to teach your fiancé what you need from him.”

“Mum says you see each of your ladies once a month. You could spank me six times before the wedding and teach me so much more. I have years to teach my fiancé what I need. I am not sure that six months is enough for you to teach me what all my needs truly are.”