The Room Ch. 03

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They explore pleasures on the dark side.
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Part 3 of the 3 part series

Updated 10/31/2022
Created 01/19/2004
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Chapter 3: Anal Adventures

Dear Reader

I invite you first to read The Room 1 and The Room 2 (search by jboase - they are in Erotic Couplings) before proceeding to The Room 3. This room actually exists. I would be honored if you were to email me should you enjoy the story.

Since teenage days my lover and I have each lived with the blessing and the curse that is obsessive sexual need. We have been lovers now for nearly five years, having discovered each other relatively late in life (I am now 60, she is 50). It has been fascinating as our relationship has unfolded to trace our respective histories of sexual need and gratification. And, of course, to enjoy the intense mutual arousal that our being together generates.

We have discovered a mutual curiosity for anal sex. Early in our relationship I became aware that she would respond quickly and strongly whenever my hand strayed to her anal opening. She would emit little cries when I touched her there. Her body would respond to my touch. I could sense her eagerness for me to explore further and I guess that my own excitement showed. I would be surprised if it didn't! Nevertheless I did not pursue anal endeavours beyond occasional touching and she did not request me to.

Things went to the next stage in the most amazing of circumstances. Early in our relationship I discovered - as one does! - that she had a lovely little bush of hair around her anus and a little trail of it down her arse crack. I found these hairs an immense turn-on and said so, naming them and addressing them 'my little friends'. I would stroke them gently during lovemaking, or lick them flat with my tongue. Occasionally, when in mischievous mood, I would threaten to extract a single hair with my teeth. I was happy for them to stay there. Then came the desire to see her anus bereft of hair, to enjoy the beauty of a smooth opening. I put to her the suggestion that I should remove my little friends.

'If that's what you want, let's do it', she said with generosity of spirit. I say that because I imagine having stubble there could be quite irritating.

We set the occasion. I went to her place one warm afternoon and we shared a bath and a glass of white wine. We both admitted to being buoyantly excited about what we were about to do. A first for both of us, the first of many firsts as our anal adventures progressed.

She got on all fours in the tub, exposing her arse in a most provocative way. I should say in passing that she has an arse - indeed, a body - that a woman half her age would be happy to have. I was treated to a visual feast of flesh and curves.

I proceeded to part her cheeks and to run a razor across her smooth skin, taking only a few hairs at a time before rinsing the razor. The work was made difficult - and amusing - by the fact that her flesh was slippery and my hand holding her cheeks apart kept sliding away from its appointed task. Nonetheless I completed the job, rinsed her and climbed back into the bath to admire my work. I sat behind her and used both hands to part her cheeks and examine my handiwork.

'That is simply stunning!' I said in awe. She has a kind of 'soft' anal muscle and it lay revealed, pink and hairless, for my eyes to feast upon.

'Do you like it?'

'Why ask a question when you know the answer?'

She laughed. She exploits my weakness for her shapely bum at every opportunity. And gets away with it, I might add.

'I'll have to rest my knees'.

She turned herself carefully around and sat facing me.

'Was that comfortable?' I asked.

'Yes, I would have said so otherwise'.

'I felt so damned apprehensive that I would nick you around the opening. Imagine that! It doesn't bear thinking about!'

'You did well. It feels fine'.

'I'd have to say that I think I prefer it shaven, even though I had such affection for my little friends'.

'You like it bare?'

'I love it bare!'

I'm sure we both sensed that we had begun the next stage of our evolving anal experimentation.

We didn't rush things. It took some weeks before our mutual inclination asserted itself again.

It was a very hot day and we had once more taken a bath to refresh ourselves. We dried each other off then took our glasses of wine into The Room where the mattress lay ready on the polished floor.

The inspiration hit me from out of nowhere.

'Lie on your belly'.

'This sounds interesting'.

'Trust me. I have something special in mind'.

She rested her head on a pillow and abandoned her body to my ministrations.

I straddled her, facing her feet, parted her cheeks and began gently sucking on her anus. She gasped and shivered in instant arousal. '0-100 instantly', as she says when overtaken by arousal at such times. I licked around it slowly, lifting my head from time to time to appreciate its beauty.

'Darling, you have the loveliest anus in the universe'.

I meant it.

It was obvious that she was immensely turned on by these sensations. Her pleasure-noises filled the air each time I touched her there. Her bum and legs would twitch instinctively, spontaneously. She wanted me to go further.

'Let me try something else, something quite different'.

She tensed and braced, wondering what was coming. We like giving each other little surprises.

I held her cheeks apart with one hand and straddled her opening with the thumb and two fingers of the other hand, pressing my fingers and nails into the skin and stretching at the same time. She cried out in surprise, enjoying the simulated violation of her body. She is not into heavy pain but loves occasional 'rough' treatment of her nipples or anus. She lay under me, pinned and unable to move, exposed, thrilled at being restrained and exploited yet rejoicing in the woman-power of her blatant display.

I applied more pressure until I sensed that she had reached her pain threshhold. I held her there, listening to her erratic breathing and her little cries, gauging her state of mind. Then, to give her relief, I released my fingers and captured her anus with my lips, taking her from a sensation of mild pain to the balm of a warm mouth; then completed the little ritual by tonguing her opening.

I lifted from her and allowed her to lie there, coming to terms myself with the potency of pleasuring we had achieved.

When she was ready I repeated the stages: fingers and nails pressing, with increasing force, around her muscle; holding the final pressure until she reached her limit; putting my lips around the 'hurt spot' as a balm; licking her slowly to completion.

Most of our little rituals happen in three phases. After that we find that the sexual intensity becomes overwhelming, sometimes even scary as we probe the subconscious.

I did it a third time, this time with an embellishment.

'Stroke yourself with your finger'.

She slipped her arm under herself. I could feel her manipulations as her flesh shifted. By leaning forward I could see just her fingertip at work.

She chose to come soon after I clamped my 'healing' mouth on her opening which gave me the joy of having her anus pulse on my lips, a very private and special experience.

'I need to be held'.

I lay next to her and drew her to me. She was vulnerable and needed a sanctuary. I wrapped her in my arms, saying nothing, giving her a safe place while she gradually returned from the frontier of sexual adventure. Indeed, we had both been to the frontier and it had been an amazing journey.

There was no hurry to go further. A few weeks later we shared a mutual desire to something more and we found ourselves in The Room, on the mattress, exploring my arse this time.

I have to say that to this point that I had never had anything bigger than a woman's finger in my arse. In truth I had not found it all that pleasurable but I was prepared to go there again with this sexiest of women. She was very keen to explore me there.

I lay on my belly, using a pillow to elevate me slightly. She lubricated me with KY, her fingers unintrusive which I appreciated. She probed for my prostate and managed to stroke it with her fingertip, a feeling I found incredibly erotic.

'I must come some time when her finger is doing that' I thought to myself but it was not to be on that occasion.

'See what you think of this'.

'What are you going to do?'

'See if you can guess'.

I felt pressure on my anus, then a slight burning sensation as she inserted what I found later was a vibrator. I adjusted my body angle then allowed her to insert it further, all the time solicitous of my comfort.

I knew when I had had enough.

'Stop there'.

She held it in that position for a short while, then switched it on to a low speed.

'Wow, that's a different feeling!'

'Do you like it?'

'Yes, but I wouldn't want it any further up.There is fine'.

'Would you be able to bring yourself off while it's in?'

'I doubt it. Interesting thought, though'.

She eased it out and used a warm cloth to cleanse me of the KY. My arse was sensitive for some time afterward.

'How did you feel about that?' I asked her.

'I loved it', she replied.

There were two further stages of exploration before we achieved anal intercourse.

On the next occasion I turned her on her front and used my fingers on her anus. Beginning with one fingertip, then one finger inserted and held... then slowly moved around... then held again... all the time assessing her comfort and her level of arousal and need. The visuals of watching one's finger in a gorgeous anal opening are something else again! We progressed to two fingers, aided by KY made warm before application... the same gentle routine. I went one finger more... a three-finger probe... gently stretching her opening then relaxing it... pushing the fingers in until she reached her limit... expanding them within her... holding them expanded while she experienced that unique pleasure... then withdrawing until just my fingertips were inside her.

I repeated this intense little ritual, twice, as is our custom.

We found on that occasion that her 'soft' muscle was proving receptive, that it seemed able to expand and accept without giving her undue discomfort. That was a most encouraging sign, defying things we had read.

On the next occasion I used a condom, lubed liberally with KY. This proved to be frustrating and unfulfilling. I should explain that I am no friend of condoms. On the few occasions I have used them in my life I have not been able to go on with it, sometimes wilting quickly without coming, reacting adversely to the artificiality of the device. So it was on this occasion, much as I wanted it to be otherwise. She lay on her front and I got to make the insertion, amazed at how easy it proved to be. That 'soft' muscle of hers prepared her for my entry and the KY on the condom made her very receptive inside. My cock, however, wilted from the condom and, I suspect, from apprehension that I might hurt her. My cock is long and thick which means that it provides a fairly solid object for her bum to accommodate. I was concerned that I would tear something inside but she was confident there would be no problem. As it turned out, she was right but our anal experiment proved short-lived and unsatisfactory that day. Fortunately we know each other well enough to have been able to laugh at my misadventure. I mean, what else could we do?

We determined the occasion of our ultimate adventure quite by chance, over the phone. In the course of a conversation to arrange a liaison I asked her, out of the blue: 'Do you feel adventurous this time?'

'Adventurous' had become our code for anal exploration.

'Yes', she replied.

We first had a bath, sipping chilled sauvignon blanc from her cellar. This was a special wine for a special, nay a very special occasion. Two anal virgins, in the real sense, about to do something about it at the respective ages of 60 and 50, for god's sake. In high spirits we enjoyed the bath and the wine.

Our ritual started in the bath, though we had not planned it that way. She slid forward and took my erection in her hand, stroking it with her usual appreciative touch. She then sent me the most blatant signal, a spontaneous gesture that I found utterly overwhelming: she stroked my cockhead across the skin around her anus. Fleshy cockhead rubbed on little wrinkles and crinkles sent me into cloud-cuckoo land. I'd never felt anything like that, ever! And all the time she watched my face intently.

She then changed the angle of her body and moved my cockhead to her anal opening. Somehow, cleverly, skilfully, she manoeuvred the head of it inside her and flexed her muscle to squeeze my cockhead.

Two unique sensations already!

She exited the bath first and I watched her dry herself, deliberately standing with her back to me, her bum not far above my face. I was able to reach up and part her cheeks. No way to treat a lady, perhaps, but then what we were contemplating was hardly ladylike!

We walked to The Room, naked and holding hands, beginning to come to terms with fulfillment of a powerful 'dark side' element in our psyches. It was awe-inspiring to think about.

It happened easily and naturally. We kissed and cuddled initially, as we love to do. I pressed my cock on her clitoris and she worked me with her hand. I used a familiar trigger to bring her to orgasm.

'Come for me! I want to watch you and listen to you!'

She adores responding to this demand. It sends her over the edge instantly. She can't help herself.

Her eyes glazed over, then shut as she came with mind-boggling intensity, shuddering with the emotional impact. She pressed my cockhead against her clit, jolted by after-shocks, uttering noises of disbelief in the force of her come. We both knew that this initial orgasm would help to relax her, to prepare her. Her anus would be the more receptive after the release of her initial tension. As things turned out, it proved a good decision, well-attuned to her responses.

We had laid out the KY and a condom but as circumstances turned out, we used neither. I always produce a goodly quantity of so-called pre-come and we found it sufficient for our purposes.

First time she lay on her back. I held my cock to her opening and squeezed it from its base to get out every available drop of liquid which I proceeded to spread around her opening. I then put my cockhead to her opening and eased it in. It was the simplest and easiest thing I have ever done. She looked at me and gasped in amazement. We had done it, without discomfort, pain or burning! Moreover, we went on to achieve full penetration with two or three easy strokes!

'That feels wonderful!'

'For me, too!'

I hesitated to move about much but she asked me to start thrusting so she could assess the effect. I picked up the pace, all the time watching her face to gauge her comfort level. I guess I held back a bit, still worried that I could hurt her but she gave rein to her pent-up curiosity for this and simply let go.

'Fuck me!'

I began a steady, full thrusting, each time drawing cries from her soul. What began as a physical experience transformed quickly into a spiritual experience. Neither of us could believe the beauty of the moment. It far transcended the coupling of two bodies.

We tried other ways: her on top, which she was unsure about but which turned out to be stunningly different again; her on her side, my legs under hers; her on her side, spooned back onto me; and her on her belly.

On her belly proved to be the most provocative position. I took my time, spreading her cheeks and taking in the loveliness of her opening. It was slightly distended from our earlier explorations.

'Darling, your anus is still opened... just a tiny bit... It really is brazen in what it is telling me... I think I should oblige...'

I put my cockhead to her opening and slipped it in. Again, so easily, incredibly easily! A wonderfully firm fit for me, no discomfort for her.

As before, her anus proved an effective means of bringing liquid out of my cock for lubricating. As I stroked, the muscle would clamp on my vas, drawing fluid out, making it available for her internal lubrication. There can be advantages to having an 'over-active gland', as she describes mine. The viscosity of my liquid was perfect for the purpose.

I left it to her to dictate the pace. I will never forget the sight of her shapely arse rising to take in my thrustings and the sight of my cock penetrating her opening. She lost the plot, completely and wonderfully, and came with a powerful intensity. Her arse convulsed on my cock, her body abandoned in fulfillment of the 'dark side'.

I could not hold back.

From the depths of my being I came, the tight grip of her muscular ring emphasising the strength of my pulsings. I knew the joy of spurting my seed into her mysterious and wondrous place other place. She told me later of her excitement at feeling my cock pulse into her arse and of the warmth of my spurtings. She said she had come close to tears when claiming my come in fulfillment of her long-cherished fantasy.

We clung together afterward, unable to move or speak. God knows how long we stayed that way. We had been overwhelmed by something beautiful and we were desperately trying to come to terms with it.

Yeats, considering the Easter Rebellion in Ireland, wrote the line 'A terrible beauty is born'.

We had known, that afternoon, 'a terrible beauty'. We had each broken through a personal barrier. We had each discovered a new dimension of sexual pleasure. We had each indulged our 'dark side'. We had come to know each other just that little bit more.

We had each been liberated, just that little bit more.

It was a wonderful feeling.

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READ MORE OF THIS SERIES

The Room Ch. 02 Previous Part
The Room Series Info

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