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Anal Analysis

Category: Anal Sex
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Charlotte’s expression was in step with her hesitation as she smiled weakly at the receptionist. Was this woman passing judgment? Charlotte worried. After all, this man specialised in sexual problems, so of course the receptionist would know that. How much detail was the woman privy to?

‘Mr Holmes is free; go right in.’

‘Thanks,’ replied Charlotte weakly. She was grateful for the small mercy of avoiding the ordeal of being under the apparently benign scrutiny of the crisp, efficient woman behind the desk. There was probably nothing going on behind the bland, professional façade, but Charlotte felt uncomfortable nonetheless, knowing that the woman knew she had a sexual ‘problem’.

‘Good afternoon, Charlotte.’

‘Mr Holmes,’ Charlotte replied as the tall man behind the desk rose, his hand projecting forward for a proper handshake.

This was Charlotte’s second visit to the therapist. On the first occasion, she’d been too nervous to take much notice of the surroundings; the whole visit had been vague and, the following day, the experience had taken on a distant, dreamlike quality. She was able to recall her initial reluctance to divulge any information to the impassive, professional man, and that he had eventually coaxed out the reason for her visit, but the detail of his appearance and his office layout was definitely blurred around the edges.

‘Please.’ Mr Holmes indicated the same comfortable armchair that Charlotte now remembered from her previous visit. ‘Now, shall we continue?’ Mr Holmes had returned to his own chair behind the large, oak desk, and was studying Charlotte over the top of steepled fingers, his expression questioning.

‘Oh, yes… Of course,’ Charlotte replied, flustered. She had been surveying Mr Holmes’ plush office, taking in the features that she had overlooked on her earlier visit.

It appeared that Mr Holmes was very successful at what he did. The room was large and airy, the furniture obviously expensive; most of the furnishings were functional, but Mr Holmes desk suggested a personal preference for the unique. The ornate carving along the edges, its very difference to the other, modern pieces in the room suggested that the desk was an indulgence; somewhat personal, and it was this intriguing aspect that Charlotte had been contemplating when the man had posed his question.

‘Where were we?’ The verbal question from Charlotte, when internally she was thinking: ‘He’s really quite dishy.’

‘We ended the first session with you giving me the outline of your …problem, as you put it.’

Charlotte self-consciously uncrossed and re-crossed her legs as a sudden flush warmed her face, and she was reminded why she was in this office to begin with. She recalled that Mr Holmes had eventually, after a degree of patient coaxing, managed to draw the reason for her visit from her.

Apparently unaware of Charlotte’s discomfort, Mr Holmes continued, ‘Yes, you revealed that you were unable to achieve orgasm from vaginal intercourse, and that this was causing a degree of disharmony between you and your current partner.’ Mr Holmes glanced up at Charlotte, smiled as though to put her at ease, and then looked at the notes on his desk once again. ‘You mentioned that you can only reach a physical climax from anal intercourse, in conjunction with manual manipulation of the clitoris.’ He looked up and appraised Charlotte with his direct gaze. ‘Is that correct?’

‘Erm… Yes, yes it is, Mr Holmes.’ The dry, clinical description did nothing to ease the woman’s embarrassment; her face glowed scarlet, and she found she was unable to hold Mr Holmes’ intent look.

‘I’m sorry if this is awkward for you, Charlotte,’ said Mr Holmes in his cool, practised voice. ‘I’m here to help you, and I promise you that nothing you say to me will cause me any embarrassment or lead me to judge you in any way. I’ve been listening to these kinds of problems for a long time, and I’d be very surprised if you were able to shock me.’ He smiled reassuringly. ‘Would you like a glass of water, or a cup of tea, perhaps?’

Mr Holmes summoned the receptionist, who duly placed a tall glass of water on the small table next to Charlotte’s chair.

‘Now, shall we continue?’ Mr Holmes asked when the door clicked shut. He didn’t wait for Charlotte’s response, but asked her to remind him of her current situation.

‘Well,’ Charlotte began, ‘my boyfriend finds the fact that he can’t… erm… satisfy – and that’s his phrase by the way…’ Charlotte paused to emphasise the point. – ‘Because he can’t satisfy me, he feels that it’s an affront to his virility. His ego is bruised, I suppose.’ Charlotte shrugged her shoulders.

‘By “satisfy”, you mean through vaginal intercourse, is that correct?’


‘But you can achieve orgasm from anal intercourse?’ Mr Holmes questioned.

‘Yes, combined with masturbation.’ Charlotte felt less uncomfortable now. The proper language used to describe what, to her, was an embarrassing and very personal issue, helped to put Charlotte more at ease.

‘Tell me,’ Mr Holmes continued to question. ‘Tell me a little of your history. Describe your early sexual encounters.’

Charlotte hesitated; she paused for a moment while she gathered her thoughts and looked back over time, calling to mind her memories. She took a deep breath and began. ‘When I was young I had the notion of being a virgin bride. I wanted to save myself for my husband, to remain intact for him, and to be de-flowered, as they say, on my wedding night.’

‘Please, go on,’ Mr Holmes said quietly when Charlotte paused.

‘Well, at university, I was suddenly very… popular with the boys. I was a late developer and, as such, hadn’t had much attention paid to me during my early teens. It wasn’t until I left school and went to Uni that boys, and even men much older than me, began to take an interest.’

‘But you had the ideal of remaining virgo intacta uppermost in your mind, even with this sudden interest in you physically?’

‘Yes, yes, that’s it exactly,’ Charlotte nodded.

‘And what happened?’

‘I went out with a few of the boys; you know? They asked me out for a drink, that kind of thing.’

‘I understand,’ nodded Mr Holmes. ‘Please, continue.’

‘Some of them were easy to put off at the end of the night,’ Charlotte said with a shrug of her shoulders. ‘But others were more persistent.’

‘And how did you cope with these men?’ Mr Holmes questioned further.

‘I’d… I’d use my hand on them… You know?’ Charlotte made the appropriate jerking gesture with her half-clenched fist, ‘I gave them a wank, that sort of thing.’

‘I see,’ said Mr Holmes, his expression impassive. ‘Is that all?’

‘Well, no,’ admitted Charlotte. ‘I sucked a couple of them, too.’

‘And why was that, Charlotte? Did they ask you?’

‘Yes, they asked,’ Charlotte confessed, adding: ‘But I was turned on as well. I wanted to suck them.’

‘Did you also want to have sexual intercourse with them, Charlotte? Did you want to go further than taking these men orally?’

‘Oh God, yes,’ Charlotte whispered. ‘But… but I wanted to remain intact; I wanted to be a virgin for my husband.’

‘I imagine the frustration must have been immense, Charlotte,’ Mr Holmes said kindly. ‘How did you reconcile this frustration?’

Charlotte paused again. She was surprised that she found it so easy to tell this virtual stranger the most intimate details of her personal life. How easy it was now that they were over the first, daunting hurdle of that first session. The darkly handsome, mature man, so professional behind his desk, was so easy to talk to. Charlotte felt suddenly comfortable, like she could tell him anything.

‘I would masturbate when I got back to my room,’ Charlotte revealed, a blush rising along her throat and washing up through her cheeks.

‘I see,’ said Mr Holmes in his usual calm manner. ‘And how did you progress from your manual and oral ministrations to anal intercourse?’

‘It was my father’s best friend,’ Charlotte revealed. ‘He… he seduced me during my first vacation.’

‘Seduced you? How?’

Charlotte laughed, her expression one of wry humour. ‘When I say “seduced”, there was nothing too subtle about it. He was staying with us while he closed down the office he’d been working at before he moved north to his new job… before he moved up to his wife and children.’

‘So you knew just about everything about this man? That he was married etc?’

‘Oh yes,’ replied Charlotte. ‘I told you, he was dad’s friend. They’d been friends since before | was born. I knew his wife… and his kids.’

‘Please, tell me what happened.’ Mr Holmes eased back in his chair, and Charlotte followed the lead of his relaxed body language and began to talk.

‘He and I were alone in the house. It was a Friday night, mum and dad had gone away, up to Gran’s it was, and Leon and I were on our own. He seemed surprised that I wasn’t out that evening. He made some remark about how a pretty girl like me should be out enjoying herself.’

‘How did you respond to that remark, Charlotte?’ Mr Holmes interrupted.

‘I was a little embarrassed. He’d called me pretty, a mature and sophisticated man like him. I suppose I was flattered too.’


‘Yes. Like I said, he was sophisticated. Far more mature than the boys at Uni. Not just in years but in outlook too. I’d always thought he was a good looking devil, but I never expected a compliment from him.’

‘It was a rather innocuous statement though, wasn’t it Charlotte?’ Mr Holmes interjected.

‘I was nineteen; he was coming up for forty. I’d only just found out I was attractive to men. I’d had all the frustration – the sexual frustration – from trying to maintain my virginity, and now a handsome man had paid me a compliment. However obscure it may seem to you, to me, at that time, it was important.’

‘Of course, forgive me, Charlotte, it wasn’t my intent to make you feel ill at ease. Please go on.’

Well, I must’ve given him some encouragement when I replied. I can’t honestly remember what I said, but he seemed to take an interest in me then. We opened a bottle of wine, at his suggestion, and settled down in the front room to talk.’

‘And the talk led to sex I would assume?’ asked Mr Holmes quietly.

‘It did,’ affirmed Charlotte. ‘We drank one bottle, and then he opened another, only this time he sat next to me on the sofa. He sat close to me and I remember him putting his hand on my leg. I was wearing a skirt, and he put his hand right onto my bare skin.’

‘And how did you feel at that point?’

Charlotte looked at her questioner curiously. Mr Holmes showed no sign that he was feeling anything as she told her story. He remained as professionally calm and inscrutable as when the session had just started. He gave no hint that he was finding the unfolding tale of sexual debauchery arousing. Outwardly, it appeared that Charlotte was just another case to him; a puzzle to be analysed and examined.

‘My body began to respond to him,’ Charlotte murmured. ‘I became aroused. My juices leaked from me, my breasts hardened, and my nipples and clitoris ached. I wanted him to touch me.’

‘What next, Charlotte?’

‘He knew what he was doing,’ Charlotte smiled lightly. ‘He knew I was aching for him.’

‘What did he do?’

‘He teased me. He just stroked my thigh, making little circles, around and around with the tips of his fingers, just on the inside of my thigh.’

‘Can you show me where, exactly?’ Mt Holmes asked.

Charlotte looked up sharply at the request. ‘Show you?’ she asked.

‘Yes,’ Mr Holmes replied directly. ‘Show me where on your thigh he was stroking you.’

Charlotte was a little uncertain about this request, but nevertheless she stood and lifted her skirt up over her thighs. ‘Here,’ she indicated a point high on her leg, right up high, close to the gusset of her knickers where the skin was soft and creamy.

‘Thank you, Charlotte,’ Mr Holmes said abruptly. ‘You can sit now, and continue if you please.’

Caught a little off guard, Charlotte allowed her skirt to cover her modesty once more. She sat, slightly bemused by what had just happened. ‘Shall I go on?’ she asked.

‘Please,’ said the man. ‘He was stroking your thigh… How did that make you feel?’

‘Feel? How do you think I felt? I was fucking horny.’ Charlotte was so amazed at the question that she was oblivious to the expletive that she had just used. ‘I wanted him to take me right there, right in the living room… God I was so turned on.’

‘But you didn’t let him, did you, Charlotte? You might have wanted him to take your virginity, but something stopped you… Am I right?’

‘Yes.’ Charlotte’s answer was a near whisper.

In her mind, Charlotte was back on that sofa. Her body was tingling; her breasts ached and her nipples were stiff points against the soft caress of her brassiere. She could feel the clenching of her insides as the oily wetness slithered from her opening and stained the gusset of her underwear. She shifted uncomfortably in the seat, fully aware of Mr Holmes intent gaze. ‘Fuck, is he made of ice?’ Charlotte thought. ‘I’m feeling so fucking dirty, and he just looks on as though he’s studying an interesting specimen. Has he any blood in his veins?’

‘Carry on, Charlotte,’ urged Mr Holmes gently.

‘I wanted him so badly,’ Charlotte’s voice had become thick and hoarse as her lust ignited at the memory. ‘I wanted him to take me, and he was going to; he was so thick and hard, poised at the entrance to my body… I was wet, so very wet, my juice was literally dripping from me, but I don’t know… I knew it was wrong… In the back of my mind I knew I shouldn’t let him.’

‘So he took you anally instead? Is that what happened, Charlotte?’

‘Oh God, yes!’ Charlotte cried. ‘That’s what he did. I closed my legs and pushed him away from me. I started to cry, and he was so very understanding… When he first suggested it to me, I was appalled… I thought it would hurt so much… But he convinced me.’

‘Convinced you, Charlotte?’

‘He was so gentle towards me. I thought he’d be angry… Angry that I’d led him along. Some boys at Uni had been angry when I wouldn’t let them… let them…’ Charlotte fell silent, unable to continue.

‘You can use the word if you wish, Charlotte,’ Mr Holmes said calmly. ‘You can use colloquialisms… I won’t be offended if you say, “fuck”.’

‘…when I wouldn’t let them fuck me,’ Charlotte finally uttered the word.

‘So Leon wasn’t angry…’ Mr Holmes gently probed.

‘No, he was so very kind. He held me. We were both naked by then, and he cuddled me and whispered to me. He kissed me gently and eventually I calmed down and my tears dried up. Then things got heated again and he was suddenly thick and hard in my hand… God, he was so stiff. It must have been the excitement of being with a nineteen year old girl… He was so wound up.’

‘And you were aroused by his erection?’ asked Mr Holmes.

‘I should say,’ Charlotte answered; her eyes ablaze at the recollection of her lover’s virility. ‘I was wanking him, and he was fingering my clit… I was on fire for him again. To be honest, I think if he’d tried to use that gorgeous cock against my cunt again, I would have just submitted… To hell with virgo intacta!’

‘How do you feel right now?’ Mr Holmes asked. ‘Are you sexually aroused now?’

Charlotte looked into the man’s eyes. Was he coming on to her? She couldn’t be sure. He was so damn calm – so damn cool – but he was a good-looking bastard, and it was true she realised with a jolt, she was feeling so aroused.

‘Yes, Mr Holmes,’ Charlotte murmured, ‘I’m sexually aroused.’

‘Do you want to masturbate?’ The question shocked Charlotte, but she recovered quickly and, suspecting that the good-looking man wanted her to masturbate, answered:

‘I do, Mr Holmes. I want to masturbate so desperately,’ she replied quietly, her cheeks burning. ‘If he needs the green light, then he’ll get it,’ Charlotte thought.

‘If the need is so great, Charlotte,’ Mr Holmes said in a low voice. ‘Then please do so… I won’t be offended, nor will I be shocked. Please continue though,’ he added.

‘We carried on using our fingers on each other,’ Charlotte continued hurriedly. She was becoming short of breath, and the pulse between her legs was growing urgent and insistent. ‘He asked me outright if he could put it in my arse. He just came out with it. I was apprehensive, but I wanted to come so much… I just decided to let him try.’

‘Describe it to me, Charlotte; tell me how it felt, tell me how you felt.’

‘I knelt on the sofa and just pushed my behind up… I suppose I offered myself to him; my arse high in the air for him to use as he wished.’


‘He got behind me, with one knee on the sofa and one foot flat on the carpet kind of thing. He smeared my own goo onto his fingers and I felt him part my buttocks. Then he daubed my hole with what was coating his fingers and tickled the opening a little.’

‘How did you react? Did you enjoy this?’

‘This part was divine,’ Charlotte groaned and rolled her eyes at the exquisite memory. She was growing more desperate to feel herself now that she had started to describe the opening scenes of her first anal encounter. Despite the presence of Mr Holmes, and without any embarrassment, Charlotte hiked her skirt up to her thighs and spread her legs wide. She hauled the thin material that covered her sex roughly aside, and then sighed deeply when her fingertips touched the slippery heat of her opening.

Mr Holmes remained impassive as his subject slid her fingers through the slick labia and swirled round and round her tight, throbbing clitoris. He waited patiently for her to continue until he felt the time had come for some gentle prompting.

‘What else, Charlotte,’ he murmured. ‘What happened next?’

‘He licked me there,’ she groaned. ‘He used his tongue on me, right there, on my “dirty hole”, as he called it.’

‘Did that excite you, Charlotte?’

‘It was fucking divine,’ Charlotte groaned and slid a finger into her clenching opening. ‘He wriggled his tongue around and then probed at the hole… Fuck, it felt so good, his tongue wriggling inside me, in such a deeply private place. Then he pushed the tip of his finger into me. That was fine too; it didn’t hurt a bit… It felt weird, but I was so sexed up, I didn’t care.’

‘What else was going on at the time, Charlotte?’

‘He’d moved and was knelt to the side of me. I was almost upright, and we were kissing… I was kissing him like I’ve never kissed another man. It was so hot, so urgent, I wanted to take him into my mouth, I wanted to have his tongue in my mouth and I wanted his big cock to invade me… Front or back, by then I didn’t care.’

‘And he did… He took you from behind?’

‘Did he ever! Jesus, I thought he was going to split my arsehole…’ Charlotte revealed coarsely. ‘He seemed to be having trouble shoving it in me. I suppose I was wriggling a bit, but he managed in the end.’ Charlotte had unbuttoned her blouse and her breasts hung over the cups of her brassiere. Her nipples were thick and long, and she used her fingers to pluck and tweak the rubbery teats as she fingered her readily lubricating sex. ‘I remember him spreading my arse cheeks and murmuring how lovely I was, how beautiful was. I felt the big dome of him bump me and then I felt the stretch as he pushed. His hands were on my hips and he was moaning about how tiny my waist was, how fucking gorgeous I was. He was holding me tight and I could hear him grunting like an animal as he pushed harder against my sphincter. Then, as he pushed in, I felt a burn, and I sort of panicked. He was too big, I thought, he was going to split me, and it felt as though I needed to push him out of me, like he was invading me and I had to squeeze my muscles to repel him.

‘Did Leon say anything?’

Charlotte’s eyes were closed as she frigged herself furiously. She could feel the onset of her climax, and she knew she would come hard and violently as she told the torrid tale of her anal de-flowering.

‘He was muttering about how tight I was… How sweet I felt around his cock,’ Charlotte groaned. ‘I begged him to stop, to pull that awful bludgeon out of my body, but he was insistent. He fed more and more of it into me until, finally, I just submitted. I relaxed and he slid the final dirty inch or two into me. He was fully home in my arsehole.’

‘Did it feel good at that point?’ The relentless questioning continued.

‘I felt stuffed,’ Charlotte replied and arched her back as a wave of pleasure, a precursor to her climax, rippled through her like an electric current. ‘It didn’t hurt any more, and I didn’t have the urge to push him out… It just felt so… so complete. And then he began to move.’ Charlotte’s voice was a mere mutter, her eyes were closed, and she was oblivious to her questioner now. She was caught in the maelstrom, reliving that moment, the moment her lover began to move his penis in and out of her body. She remained a virgin in one definition, but she was about to be royally fucked all the same. ‘I felt his fingers digging into my hips,’ Charlotte sighed. ‘He was crouched low over my back and I felt his breath on my neck moments before his kissed me there. He was moaning and sighing, and talking to me in a whisper of half sentences.’

‘What were his words?’

‘He was saying how bad I was. What a dirty girl I was. How tight my dirty hole felt, and how he was going to fill me with his seed.’ Charlotte’s fingers were busy and quick inside her scarlet opening. Her sex dribbled and squelched, loud and obscene in the ordinary office. She punctuated her story with grunts and groans, and Mr Holmes knew she was on the brink of release.

‘More, tell me more,’ he urged.

‘He moved faster and faster, in and out… I thought my arse would catch fire… It was so hot it burned again, but it felt so fucking good to have him there. I possessed him. I was the cause of his urgency. I was going to make him come. Me, little Charlotte, was going to make a mature man come with my arse. I felt I had the power’

‘Did he do it, Charlotte?’ Mr Holmes demanded. ‘Did he do it for you?’

‘Oh God, yes!’ Charlotte cried. ‘He gave a huge grunt, his fingers dug into me really deeply and he pushed that big fucking cock right into my backside. I thought he was going to push it out through my throat the way he stuffed me… And then I felt it… I felt this fluttering inside me… So deep inside… And I realised he’d come, he was shooting his seed into my arse.’

‘Did you react?’

Charlotte’s reply was lost as her orgasm rippled through her body. Her mouth clenched tightly shut, she mauled at her jutting breasts as they hung heavily over her bra. Mr Holmes watched the viscous dribble leak from her body and trickle down through the fissure between Charlotte’s buttocks, and spread in a pool onto the leather chair.

She grunted and groaned as her climax eventually tapered, and then she looked up at Mr Holmes with a slightly bewildered look on her face.

‘Oh my…!’ she cried, appalled at what she’d done. ‘I can’t believe it… I didn’t…’

‘Charlotte,’ Mr Holmes said kindly, ignoring the fact that the woman’s breasts were jutting through her gaping blouse, and that her leaking sex was pouting and dribbling its juices onto his furniture. ‘There’s nothing to worry about. We’ve made very good progress over the last hour. I promise you that your next visit will show great leaps forward. I’m sure we are very close to finding an answer for you. Don’t let the scene here embarrass you. You’ve been superb.’

‘But…’ Charlotte was lost for words. ‘I can’t believe I lost control like that… Why oh why..?

‘There’s no reason to be so critical of yourself, Charlotte. What you did was perfectly natural. Your body craved release… That’s all.’

‘I’m so sorry, Mr Holmes,’ Charlotte was mortified despite the man’s assurances, and she struggled to cover herself.

‘Another hour next week, Charlotte?’ Mr Holmes insisted, sweeping the woman’s apologies to one side.

‘Yes,’ she agreed meekly. ‘I suppose I’ve gone so far… Another session won’t hurt.’

‘Excellent,’ Mr Holmes beamed. ‘Now, if you’ll excuse me.’ He indicated the door. ‘And please ask Mrs Withers to come in,’ he asked when Charlotte, her modesty returned, left his office.

‘Yes, Mr Holmes?’ the attractive receptionist asked when she appeared at his doorway.

‘Did you see and hear that?’ the man asked.

‘Yes indeed, Mr Holmes, she replied with the same hoarse timbre of lust that Charlotte had displayed earlier. ‘I had the monitor on at my desk.’

‘And how did it make you feel, Mrs Withers?’ he questioned.

Without comment, Mrs Withers hiked her skirt up over her hips. She was bare beneath, having removed her underwear while she masturbated in the outer vestibule during Charlotte’s session. She leaned forward over Mr Holmes’s ornate oak desk and parted her buttocks with her fingertips. She offered the stain of her puckered opening to the man with an invitation:

‘Come and stick your fat cock into my dirty hole… Fill me with that big fucker… Split my arse… You know you want to.’

Smiling, Mr Holmes moved towards his receptionist, his hand unzipping his flies. ‘That saucy bitch turned me on, too,’ he muttered.

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