Journey into Cuckoldry Ch. 15: Fifteen

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Three women, two new experiences, one amazing evening for CB.
10k words
4.43
45.2k
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14

Part 15 of the 18 part series

Updated 10/29/2022
Created 07/10/2012
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JennyGently
JennyGently
3,291 Followers

It was Thursday night, one week later. The Grandparents were babysitting our two kids while my sweet, unfaithful wife and I went for what we had described to them as 'a bit of light supper with some friends that might go on a bit late'.

The truth was that it was nothing of the kind. Food was definitely a secondary consideration; the entire evening had been arranged by the She-Devil Carmen in order to allow me and our new friend Hilary to have an intimate sexual encounter in their house.

For the first time in our Journey into Cuckoldry I, Mister Cuckold was actually the centre of attention.

Of course, no event organised by Carmen would be complete if it didn't end with my wife's vagina and womb being filled with another man's semen so naturally that was also on the menu for the evening.

Hilary, my partner for the after-dinner activities, had been my dinner companion at the recent New Year Ball. At least twenty-five years older than me, she still had a pleasant, svelte figure, albeit with suspiciously firm breasts for her age. According to Carmen had been a swinger for many years; she was bright, attractive, entertaining company and the two of us had got on very well indeed.

As well as being interesting, her conversation had also been littered with sexual innuendo which had helped distract me from the groping my wife was receiving alongside me under the table from Peter, the well-built, rugby-playing husband of our host Elaine.

Despite making considerable progress with Alice, Peter had eventually abandoned her and concentrated on our new friend Julie on his other side. This change of attack had proved admirably successful; he had gone on to fuck her brutally and bareback against the wall of an nearby unused room while her husband searched unsuccessfully for her in the bar and I watched, concealed by darkness.

After the ball, to my considerable surprise, Carmen had told me that Hilary had enjoyed my company so much and had heard on the swingers' grapevine (meaning Carmen herself) such good reports of my cunnilingual skills that she had asked whether the two of us could get together for me to give her a personal, private demonstration.

I had been stunned; the idea of Cucky-Boy becoming a Bull in any way was almost unthinkable but my adored wife had bolstered my confidence and agreed that if I wanted to have a sexual encounter with Hilary, it would only be fair.

My confidence as a cocksman had never been great and being cuckolded so frequently had weakened it further so Carmen had stepped in and arranged the evening's event. By being part of a larger group, I knew that, should Hilary need more than I could deliver, Carmen's stud of a husband Steve could step in and finish her off.

Having watched Steve in action with my sweet wife, I knew very well what he and his extraordinary cock were capable of delivering.

The guests at this 'light supper' were therefore Carmen and Steve, my new admirer Hilary, her soon-to-be-cuckolded husband Clive and of course my Hotwife and me.

The seating plan for supper had required a little thought. After we had drunk a glass or two of wine in their lounge and had the surreal, artificial conversation people have when they expect to be having sex with each other in a short time we were directed by the She-Devil to specific places at table.

Hilary was placed between me and her husband, Alice was on my other side and Steve next to her. This left Carmen between her husband and Clive, directly across the table from me.

Of course, seating a husband and wife together breached the normal conventions of an English dinner party but that evening it allowed Clive and me to watch and enjoy any activity that took place beneath the table between our wives and their soon-to-be-lovers.

For the first time since our Journey into Cuckoldry had begun, that night I, Mister Cuckold had fallen into this latter category. I was to be Hilary's illicit sex partner for the evening; it was her husband Clive's turn to wear the cuckold's horns!

Of course with the She-Devil in charge, it couldn't be that simple. At the same time as I was to play the unfamiliar role of Bull for Hilary and Clive, my own wife's body was to be plundered mercilessly by Steve in the room alongside.

I was to be both Bull and Cuckold at the same time. Two sets of horns at once. Carmen's perverse imagination knew no bounds.

Despite having recently complained about sex with Steve becoming routine, Alice was obviously excited about having another evening with her lover so soon after her last fucking and was bright and giggly from the start.

Though very enjoyable for me, our one attempt at sex during the week had been less than successful as far as my wife was concerned - she had once again failed to reach orgasm - but as usual she had tried to hide the fact to protect my feelings.

Alice looked stunning again, having chosen her favourite short red cocktail dress for the evening along with white stockings, white lingerie and very high red heels. A familiar and favourite combination, it suited her blonde colouring well and she had once confided it was Steve's favourite too.

She had once again blamed her hormones for a 'blotchy, teenage' complexion but as far as I could see, she was as clear-skinned and wildly sexily alluring as she had ever been.

I flatter myself that I understand women better than many men do, but sometimes I despair about them. My wife was without doubt the sexiest, most attractive woman I knew; adored by me, openly desired by most men she met; touched and even possessed by a few of them too. But no matter how much I said, no matter how strong the evidence to the contrary, she still managed to feel insecure in her own body.

Carmen however did not seem to be plagued by such doubts and was wearing the mid-thigh black number I had seen before, a dress that showed off her curves very well indeed; curvier still thanks to her pregnancy. With black tights, black patent shoes and lots of gold jewellery she looked very womanly and very sexy although I knew only one man had a chance with her that evening.

My intended partner for the evening looked simply stunning too despite her age. Hilary had eschewed the usual cocktail dress for a very short black skirt over which she wore a long, low cut top. This combination had the double benefit of showing off her long, if rather skinny legs and displaying her suspiciously firm breasts while leaving the shape of her tummy a mystery.

We three men looked smart but as so often happens, had unconsciously dressed very similarly. Blue striped shirts in various hues were much in evidence over jeans and chinos but of course, our appearances counted for very little.

Dinner started well and improved further as the wine flowed. Given all the emotions attached to the evening, the atmosphere had been surprisingly light and there had been a lot of giggling and fondling under the table throughout the meal.

Indeed, Steve had dexterously managed inch by surreptitious inch to raise the hem of my wife's tight red dress above her waist so that by the time the coffee arrived she was sitting at the table with her tiny white satin panties and stocking tops visible to all.

Both Steve and I had quite noticeable erections.

Hilary's skirt was so short that clever manipulation was not necessary to expose her body; the tight material had ridden up over her tiny black panties of its own accord long before my hand began to stray to her skinny thighs.

When it did so, her legs parted so willingly I found myself at one point with a coffee cup in one hand and my other cupping her silk-encased vulva. Her husband Clive was pretending not to notice but I could tell his eyes were fixed on her groin.

Although over sixty and technically old enough to be my mother, Hilary was like no mother I had ever met. Surprisingly tall and extraordinarily slim, she was bright and friendly and managed to work some kind of sexual reference into almost everything she said. Her skin was clear and bright if a little wrinkled, her greying hair coloured expensively.

The 'life less monogamous' had clearly served her well.

For a moment, I wondered what thirty more years of infidelity might do to my lovely wife. When we were both over sixty, would I still be bringing her to Carmen's house for a thorough fucking? And how many partners might she have had in all that time? My mind boggled!

"Penny for them?" Hilary asked softly, her hand on my thigh.

"Hmmm?"

"Your thoughts. You were miles away," she explained.

"Nothing. I was just wondering..."

"Wondering what?" Her eyes were bright and mischievous as she cupped my cock under the table.

I looked her in the eye and grinned meaningfully.

"It doesn't matter," I said. "We're not here to think!"

"That's certainly right," she grinned back. "I was wondering too!"

"And what was on your mind, Hilary?" I asked. "What were you wondering?"

The lascivious smile on her face was infectious as she said in a loud voice.

"I was wondering how long we have to wait before you and I can get started!"

As soon as Hilary's words had been spoken Steve looked at Carmen who smiled in an almost queenly way, nodding as if giving her consent to the activities that would soon follow as if she were a Roman Emperor starting the proceedings in the arena.

It was an indication of the way this extraordinary woman had us all in her enchantment that at the time, it seemed only natural.

Steve slowly rose from the table and casually moved behind my wife's back where he started to massage her shoulders under her long blonde hair. Taking her cue, Hilary started to massage my groin beneath the table.

A minute or two later and with surprising ease, the shoulder straps of my wife's dress slipped smoothly forward and down her upper arms, leaving her tiny, satin-covered breasts clearly visible. At first she gasped in surprise, then instinctively tried to cover her breasts with her hands, then abandoned the idea and raised her pretty face to Steve.

"I've been desperate to do that all evening," he whispered in a voice we could all hear.

"Then why didn't you?" Alice asked smiling up at him.

She rose to her high-heeled feet and stepped back from the table, holding her dress up with one hand; taking Steve's arm with the other then looked across at his wife, Carmen who raised a knowing eyebrow.

"When you've got to go, you've got to go!" the She-Devil said with a smile.

My unfaithful wife then looked at me as she held her lover's hand tightly.

"Enjoy yourself," I smiled.

The familiar tightness in my chest and stomach that is the cuckold's living agony returned, along with a tightly constrained erection as the mother of my children led her lover away from the table towards the door.

As the two of them were about to leave the room, Alice turned to me one last time.

"Have fun yourself, CB," she smiled.

I watched as my lovely, sexy wife left the dining room. There were footsteps on the stairs and the familiar low nausea in my stomach made its awful presence felt.

I was about to be cuckolded again; in a short time, another man's erect cock would enter my wife's skinny body and bring her the pleasures of the flesh that I could not provide alone. Another man's seed would enter the womb that should only have known mine.

In a short time, her body would be violated; defiled by a man who was not her husband.

And I would do nothing to stop it. Worse; I would love every moment of it.

A brief sensation of self-disgust washed over me. I gulped then, as the footsteps faded, became aware of an insistent pressure in my groin. I turned to look into the bright, pretty, expectant face of Hilary.

"Shall we go too?" a soft, pleasant voice asked.

It was time for me to perform! The realisation made me feel even more nervous; even more anxious but excited at the same time. Instinctively I looked across at Carmen for her reaction. She smiled indulgently.

"Clive and I will have another coffee down here," she said as if reading my mind. "It'll give you two a chance to get to know each other. He'll come up quietly once things have moved on a bit."

Smiling, Hilary's rose to her feet too. I took her offered hand and for the second time in a few minutes, an eager, expectant, unfaithful wife led a man who was not her husband upstairs.

As we crossed the landing I glanced through the half-open door of the master bedroom. My sweet wife and her lover were standing face to face, their mouths pressed together in a long, passionate kiss. Alice's arms were around Steve's muscular neck; her back towards to door; her long blonde hair cascading down over the tight redness of her short dress. She looked tall, slender, almost boyish and so, so desirable.

As they kissed, Steve's eyelids flicked open, his gaze met mine and for a second we stared into each other's eyes, mine nervous and uncertain, his sparkling and triumphant. Then, slowly and deliberately, his expert hands slipped my wife's red dress to the floor where it pooled around her high-heeled feet.

She stood, her back still towards me, in her tiny white lingerie; stockings, suspenders, microscopic panties and unnecessary bra, her mouth open wide to receive her lover's tongue. Steve's hands slipped around her waist then down to cup her bottom.

For a moment I watched as my wife ground her hips against Steve's groin, her tight, muscular buttocks flexing as she wantonly pressed her well-used vulva against his bulge then rubbed herself brazenly against his upper thigh.

Steve's hands had just slipped inside her panties when a soft voice alongside me brought me back.

"She's lovely, isn't she?" a soft voice at my aide asked.

I felt my hand being squeezed.

"Very," I sighed.

"And he's very good."

"So I've seen."

Steve's dextrous fingers had eased my wife's tiny panties down over her buttocks so the waistband lay in the crease at the top of her thighs. His hidden hand had moved to her groin; from the way her hips and bottom were writhing and squirming, he had to be fingering her and doing it well.

"Has he fucked her many times?"

"Quite a few. He was her first... our first, I should say."

Hilary chuckled knowingly as my wife pressed her vulva hard against Steve's fingers, her head falling backward, her blonde hair flowing over her smooth shoulders.

"Does it hurt to watch?" she asked.

"Always!"

"But you have to do it? Need to?"

I sighed.

"Oh God, yes!"

Alice's tiny bra was stripped away and a moment later Steve had picked her bodily from the floor and carried her over to the big bed. My lovely, pretty wife lay nearly naked on her back in full view of the doorway and as I watched, she raised her hips to ease the removals of her panties then spread her thighs wide for her lover, her shaven vulva on full display and a broad, lustful smile on her sweet face.

Steve moved out of sight. The door slowly closed. My wife was now his.

I sighed as the cuckold's familiar swell of nausea slowly passed through me.

"We'd better leave them to it!"

Hilary's words broke through my reverie, reminding me that this evening was different. This evening I too had a job to do.

"Of course. I'm sorry," I mumbled, looking at my pretty companion.

"It's okay; I understand," she said and I instantly knew it was true; Hilary really did understand what it meant to share the most precious thing in your life.

"You will... be gentle with me, won't you?" she added.

To my surprise, now that the bedroom was in sight and our encounter imminent, the confident innuendo had gone from Hilary's voice. I looked again into her pretty face and to my surprise saw hesitation, perhaps even fear.

"Are you okay?" I asked.

"I'm not... as pretty as your wife," she said. "And not as young."

"You're very attractive," I insisted truthfully. "Very sexy indeed."

"And I'm not as experienced as you might have been told either," she added anxiously.

"I thought Carmen said..." I began.

"Carmen doesn't know everything," Hilary said quietly. "But she does speak highly of you."

"I hope I live up to expectations," I said genuinely nervously.

I squeezed her hand gently then led the lovely lady into the guest room and part closed the door, leaving a small opening between it and the frame.

"Goodness!" Hilary whispered behind me.

I turned towards her and looked around.

Carmen had clearly wanted to set a romantic scene; the room glowed orange-red with the light of a half-dozen candles that sat on the dresser and bedside tables. The room was warm, the bedclothes already pulled back and welcoming.

A large cheval mirror stood at the foot of the bed, clearly not angled to allow the occupant to address their clothing; it would however provide anyone lying on the mattress with an excellent view of anything taking place between their legs.

"It's ridiculous but I feel very nervous," Hilary said.

She looked it too as we stood together at the edge of the mattress, her face angled up towards mine.

"I do too," I confessed. "I'm not used to... to this kind of thing."

"Well let's try and help each other, shall we?"

Hilary closed her eyes and raised her lips. Instinctively, I lowered my mouth to hers. Our lips touched and for the first time in many years I found myself in a sexual embrace with a woman who was not my wife.

It felt electric; strange and unfamiliar but exciting. Hilary was a first class kisser too, her lips active on mine, her tongue instantly in my mouth. I sucked on it, thrusting back with my own tongue in response and a moment later our arms were around each other's bodies, mouths wide open, fully engrossed as if we were teens.

Hilary's arms rose around my neck and my hands fell to her buttocks, kneading the tight muscles firmly, pressing her vulva against my upper thigh as I had just watched my wife do with her own lover only minutes before.

I have to admit, it felt good; good to have an attractive woman in my arms; good to feel attractive again myself.

We kissed with increasing passion, my hands mimicking Steve's as they fell to Hilary's waist and fumbled with the zipper on her skirt. I was relieved to find that my teenage skills hadn't abandoned me; the short fabric band that passed for Hilary's skirt was soon bunched around her ankles leaving my hands free to caress her taut buttocks beneath their black satin covering.

Encouraged by my exploring fingers, Hilary pressed her groin hard against my upper thigh, rubbing herself slowly up and down. I moved my leg forward a little and felt the pace of rubbing increase as her tongue plunged deep into my mouth.

My hands released her buttocks and began to raise her long top up and over her tummy then her breasts. Hilary released my neck and held her arms upright like a child as I peeled the top from her slim body to reveal her full, over-firm breasts supported by a low-cut black lace bra.

Without hesitating, she reached behind her back and released the clasp of her bra then slipped the garment down her slender arms and cast it aside. Her breasts stood firm, hard and rounded on her skinny chest.

"Do you like them?" she asked, looking into my eyes with a cheeky grin. "They were very expensive."

I grinned and reached out to touch them; they felt strange; not obviously unnatural but suspiciously large and firm for a woman her age. I cupped them in my palms then toyed with her firming nipples.

"Mmmm. That's nice," Hilary purred.

We kissed slowly and deeply, our tongues entwined, my hands enjoying the feel of her breasts. I twisted and flicked her nipples between my fingertips, the dark circles firm; her teats hard and protruding.

It felt good! Cucky-Boy was enjoying another woman's body at the same time as his wife was surrendering hers to one of her lovers. I felt attractive, wanted sexually. I began to understand how my wife must feel whenever she gave herself to another man. Hilary's fingers were active on my shirt buttons, then on my belt buckle and zipper. Before I knew it, my trousers were around my ankles.

JennyGently
JennyGently
3,291 Followers