The Forty Year Old Virgin

by Mr Smooth

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© Copyright 2015 - Mr Smooth - Used by permission

Storycodes: F/m; femdom; punish; cane; controlled; escort; hum; bond; cuffs; bdsm; mast; sex; oral; climax; cons/reluct; X

Derek Evans was a forty year old virgin; yes the very same as the man in the film that was made: I will explain. He was a heterosexual red blooded male with the same desires as any other but he had never had a relationship with any female due to his domineering mother and his inability to stand up to her and make to his own mind up.

He had stayed at home to look after her all of his adult life after his father died when he was just eleven years old. An only child his completely selfish mother made sure that once Derek became an adult physically she manipulated him and kept him at arms length from any other females.

He worked in an all male factory environment which she had made sure of and kept him constantly under surveillance ensuring that any spare time he had she kept him at home looking after her. She would “fall ill” if he showed any interest in outside activities and so feeling sorry for her he would abandon any ideas of going out to meet people. His hobbies were stamp collecting and model railways so he had become a bit of an anorak.

Annual holidays were the same where he would take the train with his mother to the same Hotel every year to stay with her there being at her every beck and call.
Because of the sheltered life he led, apart from work he met few people and so he had little confidence with strangers and females simply terrified him.

His mother once caught him masturbating as a teenager and gave him such a castigating and a thrashing with her cane he would never forget; so much that it would remain ingrained in his memory forever. He then resorted to relieving himself only on rare occasions when he could contain himself no longer. She would continue to thrash him for any minor misdemeanours up until he was in his early thirties until she got too old to carry it out and he just took it from her.

Here now at forty years old his mother had died recently and with no friends to speak of there were only a few distant relatives at the funeral and so he was for the first time in his life completely alone with no one to tell him what to do. He always had a well paid job so had a good bank balance; also his mothers life insurance and the house was entirely his now and it was worth a considerable amount being in good order and detached in a decent neighbourhood but as yet he had not thought about what he should do now with his life as his mother had always made all the decisions for both of them.

He was here watching TV one evening a few weeks later after work when a very erotic section of a film was being played. He quickly switched it over as his mother would have done, with her tutting and making remarks about filthy sexual “goings on” He suddenly thought to himself, I was enjoying this film and I want to see it through and although feeling guilty he turned it back over and watched it avidly.

The blood was soon coursing through his veins and after he found himself masturbating furiously when the film had played out. Later sexually relieved he felt as if he had been dishonest somehow to his mother and so went of to bed sheepishly. The next day it began to dawn on him that he had been selfish too, only to himself though and that evening after work he began to take stock of his life. He mused to himself, why I shouldn’t have a life with a little excitement and worth having and maybe even share it with someone I choose to be with? And then his stomach churned over at the very thoughts of having a physical relationship with a member of the opposite sex.

One day at work one of his workmates ribbed him about his apparent non relationships and adding “If I were you with your money and opportunity I would have the time of my life even if I had to pay for it” and then added “you are only around this way once, think about it” Derek shrugged it off but his work friend had lit a spark.

Later at home Derek fired up his lap-top and punched in “female escorts” on a search engine. A list as long as your arm filled his screen and now enthusiastically he began to refine the search more to his local area and to the types of women that he preferred.

All this was a just a bit of fun and excitement for him just to start with and he finally settled his search on a mature and very attractive blonde haired lady called Caroline. She was around thirty five to forty and pictures on her site in her underwear showed she had fabulous long legs and she claimed to love wearing stocking and suspenders; his very favourite I might add. She was simply perfect and gorgeous to him and he saved her details with his heart beating fast just at the thought of even speaking to this lovely creature.

A week or two went by and he would regularly with hands shaking fill in her application form to arrange a meeting at his home but not actually go through with it.

One night as usual he was sitting there his finger poised over the send button, his heart beating fast having again filled in her form to the full, arranging a meeting for the coming Saturday evening when the phone suddenly rang. It startled him and he accidently hit the send button as he reached for the phone which rarely rang. He quietly cursed to himself as the call was a cold one trying to sell him something or other. “Damm” he said as he realised the message had been sent when he looked at his screen and his heart rate went up just at the thought of it.

It was Wednesday at this point and Derek tried hard to put the email out of his thoughts but his mind kept wandering to it. What will I say to her if she turns up? What will the neighbours think of me? These thoughts and more only made him feel almost sick with concern and yet stomach churning excitement at the same time. He couldn’t remember when he last had a personal conversation with a female, never mind someone who was as beautiful and sexually desirable and experienced as Caroline.

Meanwhile she had confirmed the appointment but he was too much of a gentleman and coward to cancel so Saturday evening arrived; he was shaking like a leaf in the wind and nearly dropped his mug of tea when his doorbell rang precisely at seven pm.
“Who is it” he shouted through the frosted glass in the top of the door. He could see it was a female. “It is Caroline” she replied quietly. “Oh my god” he muttered to himself as he opened it to reveal this stunning blonde in a long black expensive looking leather coat.

She smiled at him waiting for his invite and offered her hand. He blushed to his roots and shook her hand at this as she continued to stare at him as he looked away muttering and shaking his head “I cant go through with this, I will get your money”

He turned away to fetch her tribute and she now entered his hallway confidently but uninvited, she was carrying a small suitcase. He quickly returned with the cash surprised to see her in his house and stuffed the money into her hand “Well” she said “I don’t do business standing in the street for everyone to see, I must say this has never happened before, don’t you find me attractive or is it something else?”

He had great difficulty in looking her in the eyes and stammered “no you are so lovely its just that” He now broke down with all the pressures he had put upon himself and tears streamed down his face as he sobbed. Caroline was an intelligent lady and was soon able to sum the situation up guessing what the problem could be. She took hold of his shoulder and looking directly in his face said “I think I know what this is about, please now take a seat, I am a good listener and you tell Caroline what this is all about”

She closed the outside door and followed him into the lounge where he sat with his head in his hands and as she sat next to him it is so true that you can tell a complete stranger more than someone you know so he blurted his whole forty years of misery to that he had suffered, even to the canings his mother had dished out on him. She was a good listener as she had claimed and when he finished she said “Wow so you are a virgin and hoped to lose your cherry tonight. I have to say I thank you for choosing me, it will be an honour to show you the way”

“Oh god” Derek sighed his voice filled with emotion “I don’t think I can go through with it, I am terrified and I would be no good to you or myself so please go” “Nonsense” she said “I have been paid, my time is yours and I wish to stay here and help you, you need to get this sorted and over with, tonight is perfect, I insist” Derek shook his head “I don’t know” he said “I am ashamed of myself for this” Caroline took the initiative and said “Look, go and take a nice shower, freshen up to make you feel better then return in your dressing gown and meanwhile I will make us a nice cup of tea.

He nodded at her suggestion as he was always a follower and not a leader and made his way upstairs to take his shower. His mind was in turmoil as he showered; he wanted so much to get it over with and make love with her but knew it would be hopeless for both of them with the pressures he had put on himself.

He finally plucked up the courage to return sheepishly in his dressing gown as she had suggested finding her in a long silk dressing gown taken from her suitcase where she sat drinking a mug of tea. She smiled and beckoned him to sit next to her. During the next few minutes his hands shook as he sipped his tea and tried to make small talk and so now touching him on the right hand she said “put you cup down Derek and try to relax, just lean back, close your eyes and I will help you through this”

Derek did as he was told to and closed his eyes and relax. He then felt a warm soft hand enter his dressing gown at his chest area and touch his bare skin: it was the first time any female apart from his mother had ever touched him and it was and electric, taking his breath. Caroline moved in closer now to his ear talking softly. Derek was on fire with this and she now began to search his body lower down. He was now sucking in huge amounts of air quickly and now she placed her hand over his now leaking erection.

She slipped her hand inside his shorts and clasped her warm fingers around his hot dripping throbbing cock. He let out a cry of unbelievable and absolute pleasure at this and involuntary moved his hips to try to make himself cum. “Hold still and control yourself” she said firmly releasing her grip “you must try” Oh Jesus” he replied very near to cumming.

She took the initiative and now said “Come you will now take me to your bedroom where this can be done properly” she said very firmly. He stood up legs shaking, his face completely flushed he sheepishly took her to his room and she followed carrying her suitcase. “Lie down on your back” she now ordered him.

She slipped off her dressing gown now standing before him to reveal her black lacy underwear and stockings. He couldn’t believe where this had gotten to. He felt faint with the adrenaline rush as she now lay beside him on her side and draping a warm soft leg over his thigh she opened his gown and traced her right hand down his chest to his belly. His breathing was erratic and now she lifted the waistband of his shorts and pulled them down exposing his purple throbbing and dripping cock.

She comforted him by saying. “Well that’s nothing to be ashamed of Derek now let me start teaching you” Tracing her fingers now up and down his swollen member he almost passed out with pleasure and a couple of moments later he screamed as his boiling sperm shot into the air landing on his chest.

She continued to stroke him dry as he now cried with joy at the unbelievable pleasure she had just given him. “Thank you, thank you, thank you” was all that he could muster in his croaking voice as she wiped away his seed. “I haven’t finished yet” was her reply “in fact I haven’t even got properly started on you. You have so much to learn tonight and I wish to make sure that you will be taught properly; I intend to enjoy this too, and can I suggest that if you double my fee I will stay until morning and see this through that is but I must now secure you gently so that I can take complete control, do you agree, I promise you will be safe in my hands?” He nodded and reluctantly agreed.

.She opened her case and produced two sets of handcuffs and slipped them onto his wrists as she understood by now that he would do as he was told by a forceful woman. “Shhh” she said as he questioned her motives and now fastened a handcuff onto each corner post either side of his head he lay helpless. She now removed his boxers completely and slipped leather ankle cuffs on him; in turn fastening these to the bottom corner posts so that he was lying in an X position; he felt helpless to resist and really didn’t wish to so as she took complete charge of him.

Returning she straddled his lower thighs in her erotic underwear and now began to toy with his cock again which was still fairly hard. Cupping his balls and sliding oiled fingers up and down his shaft she knew all the tricks to give men pleasure and he was very soon close to a second orgasm. She sensed this and stopped leaving him on the edge. “Sweet Jesus” he cried “please let me cum” “You will cum when I am ready to let you” she said very firmly “now control yourself”

After a few minutes of him begging and her simply massaging his legs and belly and him not being able to do anything about it she again started to stroke his purple throbbing cock. Stopping again she edged him and he kept his eyes closed though as he was still incredibly embarrassed. “Open your eyes and look at me” she demanded and stopped again. She leaned into him and said “now this time you will watch me as I pump your cock and extract your spunk.

Glassy eyed with lust now she soon brought him to another incredible climax and again he screamed with pleasure as his hot semen squirted and bubbled from his knob and gently but firmly she squeezed every last drop of it from his cock. After wiping his seed away from his belly she lay at his side and draped a warm stocking clad leg over his thigh, cuddled up close to him and nestled her head in his neck for a minute or two as he slowly came back to reality.

“Oh my god” he kept repeating to himself in a low voice. She now leaned up on her elbow looking into his face which was still turned away. “Look me in the eyes now” she said firmly “and tell me whether or not that was the best experience of your forty years to date” He turned his head to her as she searched his eyes. “Yes” he replied “it was fantastic Caroline, just the best” and now he blurted “I love you” She smiled knowing that she had him on her hook which she had baited.

She was clever, also a little devious and had soon realised that this situation could turn very much in her favour. Here was a single man with a nice house; obviously he had money too and he could be manipulated by a strong female. This may be a pot of gold and help secure her near future she thought but she knew she would have to take it easy to start with and slowly reel him in.

Derek sighed deeply now; it was with happiness the like of which he had never known in his forty years and here was this beautiful creature lying by his side who had the means to supply it. “Are you going to release me now, I feel very vulnerable like this?” he asked. She thought for a moment and shook her head “im not ready to do that yet, you have much more pleasure to come tonight and later I will show you and teach you about my body too and where everything can be found: I intend to have some pleasure from you too”

At this Derek’s mind went into overdrive at the thoughts of him actually being allowed to touch her most intimate places and failing to perform properly later with her; he sighed loudly turned away and muttered “oh god” again. He was still semi-hard and Caroline traced her fingers back down to his cock gently caressing him, bringing him back to a throbbing erection again.

Gently stroking now he lasted a little longer this time and a couple of minutes later he was in the throws of ecstasy as she brought him off for the third time in less than an hour. “There’s nothing wrong with you Derek that I can’t put right” she said to him to give him confidence and now released his bonds.

He visited the bathroom to clean himself up as she had suggested him to and when he returned she had only a low side light turned on and had climbed into bed waiting for him. Naked he felt embarrassed still and covered his genitals to walk from the bathroom. She tapped the bed and invited him to get in with her which he quickly did.

She was naked too now and she took his breath when she cuddled him as he could feel the solid warm flesh of her ample breasts pressing against his body. This was all very erotic and he soon had his erection back to full flow. She reached under her pillow and retrieved a condom in its metal foil cover. This she opened and reached down to roll it on his stiff cock expertly with her one hand. Now she opened a second one and added this over the first. “This will help your control” she said seductively and now straddled his waist.

Reaching behind her she lifted herself up and slowly buried her glorious wet pussy down his cock to the hilt. She started to move on him looking down to his now glassy eyes she said “I am now making a real man of you so lie there and enjoy this fuck” She placed his hands on her breasts and showed him how to caress her nipples gently. “Oh god Caroline, oh god this is wonderful was all he could say as she rode him gently for a short time.

He was not to be long even wearing the two condoms and as he began to spurt and squeal with lust she nestled her delicious warm body down into him increasing his enjoyment of this very first time for him as they lay together now entwined for several minutes.

She finally rolled off him and said quietly in his ear “I have just taken your virginity away, there’s no going back now” She then chuckled at her remark and he turned towards her looking directly into her eyes said “I don’t mind a bit Caroline it was about time wasn’t it” They both laughed now and Derek very much more relaxed with her and so pleased with himself, they fell asleep in each others arms.

Caroline used the bathroom during the night which woke him up and she again straddled him as before using two condoms to slow him down somewhat. At seven o clock Derek used the bathroom and when he returned she guided his hand to her moist pussy. This was the first time he had touched her there and she now showed him what to do and where her clitoris was.

After some clumsy fumbling to start with she patiently corrected him and eventually he bought her to a climax. Now she made him slip on two condoms with his shaking hands and this time she guided him on top of her between her warm smooth thighs and just two minutes later he again cried out with pleasure.

He rolled off her and apologised profusely but she touched his lips gently and whispered “you have only just started and it takes time to learn to make love properly, do not worry about it, that’s what I am here for, to teach you.

They got up later and had a light breakfast. Derek’s confidence had grown and he was able at least to make some sort of conversation with Caroline and look her in the eye occasionally. Then she said around ten o clock “I have to go now will you settle up with me please” she reminded him.

It took a moment for it to register that he had to pay extra for her overnight stay; then he realised. “Oh yes, I forgot” he replied and went to get the remainder of her fee. On return he said “would you consider staying here today, I will pay you whatever you think is appropriate” She was reeling him in “I never do paid work on Sundays” she replied firmly “it is my rule” she added as she took her money.

He looked disappointed, there was a pregnant pause and he shifted on his feet awkwardly. She took the initiative “however I am free for dinner this evening if you would like to take me out and enjoy my company. I do love good Italian food and there is an excellent one in town that I know if you agree and book it now before I leave”

He wasn’t used to eating out and this would be his very first date too, but he jumped at the chance to be in her with her and so agreed. He phoned immediately and secured a table for two. She agreed to pick him up as he had no car at seven thirty and on leaving she kissed him on the cheek tenderly and said her goodbyes; his head was now swimming with his thoughts.

She picked him up as arranged; she looked stunning in her low cut skin tight dress that showed off her very curvy and fit body. He was wearing his new suit which he had only recently bought for the funeral; she then drove him to the restaurant. All of this was very strange to Derek and so Caroline took the initiative to order the food and wine which was quite expensive to say the least.

Derek didn’t care though, his head was swimming with delight at the whole experience and as he looked around he could see the attention that Caroline was getting from most of the men in here and this boosted his confidence no end. The meal over Derek paid the hefty bill, she drove him home and stopping outside his door he looked at her in the semi-light and touching her arm he said “thank you Caroline for the most wonderful time of my life this weekend, I will never forget it”

He made a move to leave and said his goodnights as he ventured to kiss her gently on the cheek. As he moved away she caught his arm gently and smiled as she thought quickly; she said “well Derek if you wish to see me again to continue your training you have my number”

His heart rate already high went up even more “oh yes of course” he replied “im sorry I should have said something” and then ventured “I don’t suppose you wish to come in for coffee do you where we can discuss your next appointment” “I ought to go” she replied and then paused for a moment playing him on her line; she then continued “just may be half an hour or so will be OK”

Inside Derek prepared the coffee in the kitchen while Caroline sat in the lounge and she made sure that she would be sitting opposite and so she adjusted her dress to show something of her long legs and stocking tops for his return. He carried in two coffees and sat opposite.

His eyes were drawn immediately to her sexually provocative position which she used to draw him in. He very soon had an erection which he found difficult to hide as they sat there making small talk and arranging for her next visit the following week, then Caroline said “thank you Derek for a lovely evening but I must be going now” and she stood up. Derek didn’t know where to put himself as he was also obliged to stand and attempted to cover himself when he did.

Caroline smiled and touched his cheek gently. It was like an electric shock to him and he groaned with embarrassment and lust. “Well” she said “I think I had better do something about that swelling you have or you wont sleep tonight will you” Derek was mortified that she had mentioned it but his lust was greater and he was so glad that she was about to give him relief.

Then she seized on a chance and said “do you still have the cane your mother used on you?” He looked flabbergasted shook his and replied “yes it is in kitchen broom cupboard” “Hmmm” she replied and then she led him upstairs.

She now made him remove his coat and shirt etc. and lie on his bed where she now removed his trousers. He turned away totally embarrassed as usual as she said “we don’t want a mess on your best clothes do we” She fetched a towel from the bathroom layed it on his belly then knelt between his legs hiking up her skirt revealing her stockings and black silky knickers.

His cock was now pulsing wildly with blood and she now insisted that he looked at her. Now she said “I am to set you a task, I am about to touch your cock now and if you lose control before I give you permission then you will have to take six strokes of the cane. I do hope you understand that it will be very painful for you but you have no choice in the matter and will have to see it through”.

He began to shake both with fear and excitement at her threats but he agreed. “Good” she said now prepare yourself. His eyes glassy with lust she gently with one finger traced a line underneath along the length of his shaft from his balls to his knob It took his breath and he shouted through his teeth “Oh my god, oh my god” at this unbelievable pleasure she was now giving him.

She castigated him now as she gently took his cock in her smooth hands and began to stroke him gently and very soon his balls were hard as rocks. “Do not even think about cumming or you will taste my cane” she said in a very serious voice as he struggled to contain himself. Of course this made matters worse and very soon his whole body stiffened as he lost control. He squealed with pleasure and she pumped his cock until again his hot load shot in the air.

She continued to castigate him as she pumped his sperm from him calling him a dirty fucker and worse. He screamed her name as she emptied his balls and he now lay there breathing hard, satiated and she gently wiped away the cream that was still oozing from his knob. Her hand still dripping with his hot cum she leaned over him, looked deeply into his eyes and said firmly “you’ve been a naughty boy Derek and disobeyed mommy; so you will now have to take your punishment, turn over while I get the cane” She soon returned with it and tested it through the air with a scary sound a couple of times as he lay on his face groaning with fear and excitement at the same time.

She layed the six strokes on and made him squeal and beg for mercy. She brought tears to his eyes and after a couple of minutes went by; he calmed down somewhat. Now she said gently but again very firmly “because you made me so very horny you can do something for me now” she now touched his mouth “with this”

At that she slipped off her tiny black knickers and pressed them onto his nose. “Smell my juices” she said and he took a long deep breath of her perfumed underwear. She now straddled his face and he saw for the first time a real pussy close up. She lowered herself down and now told him what to do. Eagerly he stabbed his tongue into her musky crevice and she now coached him how to do it correctly.

Caroline loved fellatio and kept him there for an age to take her own pleasures. Finally she had enough of his mouth and by now Derek listening to her squeals of delight was feeling randy again and had regained his erection fully, so she slipped a condom onto his cock and mounted him. This time he managed to control himself for several minutes and so she too had some pleasure from his body much to his delight..

Afterwards as they lay there for a little while, Derek contemplated that he was in a place he wished to be; he had never known such happiness.

So far in her life Caroline had only bad or poor long term relationships with men and Derek it seemed could be the answer for her. He was relatively wealthy, not bad looking and clean as she knew he had been with no one else and he needed someone like her to guide him. She had a lot to teach Derek and she would see to that.

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