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Fun With Jack And Jill 2

"We swing with an older woman and her toy boy"

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January 30th, 2024

Jill's diary entry.

In just a few weeks our lives had completely changed. Jack and I had been married for a few years, and we considered ourselves loved up and content. Cue the interminable Covid lockdowns and we almost crashed and burned. We both played away to relieve the humdrum boredom but the one-night stands proved to be most unsatisfying for both of us.

Anyway, we got our heads together and talked frankly about our life and how things were getting dull in the bedroom, despite our still finding the other a true blessing. Our sex life was always brilliant but with too much familiarity things started to become a little bland. So, when we were lying in bed one night Jack asked me his mind-blowing question.

"Jill, have you ever thought about fucking another while I screw his partner?" 

"I told you, babes. I'm done with cheating."

"I know. But have you fantasised about the pair of us swinging? Wife swapping and all of that?"

I sat up and looked him in the eyes. He seemed truly honest and the thought sounded intriguing. The more we discussed it, the more we browsed the net. Studying this swinger website and that. One time when Jack was giving it to me big time, I had a flash thought in my head, and I imagined that I was watching him watching me get shagged by a well-hung stud. He, meanwhile was balls deep in his missus who was wailing and panting in abject bliss. I had a colossal orgasm that night and I came around to the notion of swinging. And pretty soon we were up and running. (See part 1)

x

February 3rd.

Jack's entry.

The next couple who answered our profile on the website UK Swingers appeared somewhat interesting. Victoria was forty-eight years old but was in pretty good shape thanks to her never giving birth and being a retired soccer player with Arsenal Women Football Club. Jack, being an ex-Tottenham player was slightly put off by the rivalry between the two North London teams, who fought like cat and dog every year. But when he saw her picture he soon warmed up to the idea of her sharing our bed. She had medium-length brown hair, a sexy plump belly, an enticing rounded bum, and a heavy bosom.

Her feller was her toy boy. A chap with youthful looks and a boy next door charm. At twenty-two he was even younger than us. Victoria claimed in their profile that Joe had a nine-inch cock, which was bigger than Jack's sizeable rod. I wasn't sure why they wanted to swing but guessed that the older woman was an insatiable MILF. The interested couple responded positively to our ad, and we arranged a visit for some hot sex on the first weekend of February. It had been over a fortnight since our most recent swinging adventure, and we were well up for another.

We drove out to Highgate and found Victoria's red brick Edwardian house. This part of North London has lost none of its attraction to this day, partly due to the wonderful green spaces from Alexandra Palace to Highgate Woods and Cemetery. It’s not all suburban charm though and, like much of North London, these areas are known for their artistic ways and left-leaning politics.

Jill looked great in her really short black micro dress which clung to her bum and the tops of her thighs superbly. She added a nice touch by wearing a black velvet choker around her neck. When we arrived we found just the young Simon by himself. He explained that Vicky would be with us momentarily.

We sat in the living room and chatted and then the MILF showed her face. Actually, a lot more than her face as when she appeared she stood in front of us and shrugged off the silky housecoat she was wearing to show us she was completely naked underneath! Up close, the five-ten female had a firm body, wide hips, and generously sized boobs that stuck out in front of her. Her nipples were already erect and I felt incredibly aroused myself.

"I so love to be naked. It makes me feel alive and sensuous. Don't you agree?"

She sat next to young Chris and continued. Her story was that her husband of fifty had passed from Covid-19 and that she had inherited his riches. He had been in politics and wasn't short of a penny or two, and the large house came with it. She had enough to live comfortably without working but found her everyday life to be humdrum and unexciting.

"I've not had too many lovers over the years but I'm old enough to know what I like. I've always had a little bit of a wicked side but do you know I never cheated on my husband? I had not had any sex for many months when I met up with Chris. He attended the same private school as my nephew. I plied him with all sorts of treats and such and took him as my lover. Within a year I had him fully trained, totally obedient, and made him worship my body. Chris is well-endowed and meets my needs splendidly. But he lacks finesse and a fair bit of experience, bless him, which is why I chose to register with UK Swingers. I need others to teach him some more skills shall we say."

I turned to Chris and he did look very green and impressionable. When Jill and I had chosen to swing I had not envisaged making out with a woman twenty years my senior, but Victoria did possess a fuckable body with those taut legs extending to a flattish stomach and heavily rounded breasts. And as for Jill, she had told me that although I had a perfectly lovely cock, it might be fun to have someone fuck her with an even bigger dick such as Chris. Victoria stretched her legs out nonchalantly and the open labia of her cunt seemed as pink as Jill's cheeks as they parted.

"I desire a man to cater to my oral needs first and foremost. Ever since I ever had a man put his tongue in my pussy I've wanted more and more cunnilingus. And now that I have the time, money, and inclination, I don't wish to waste time. Now I find myself in a big house, comfortably well off, I crave a good tongue. Come on," she said to us with a rather authoritarian voice. "Let's go to our bedroom."

x


Predictably, the bedroom was large and filled with fancy furnishings and a thick shagpile. The bed was by far the biggest either of us had ever seen. A dozen pillows of different shapes and sizes were piled at the headboard. As Chris silently stripped off, both Jill and I took that as a cue to do the same. Being an ex-football player, I prided myself on my physique and knew that I looked pretty good in the buff. And Victoria looked quite happy with what she saw. She stroked my arm and felt my bicep, squeezing with her delicate fingers.

"I do so like the fit ones. I have no time for regular types. You are a lucky young lady, my dear."

The MILF stretched out her arms and pulled me to her warm frame. I cupped her breasts and their abundance filled my palms. Her head dropped back and her lips parted when I lowered my mouth to her left tit and bit lightly on the hard nipple.

Victoria was true to her word about the size of her toy boy's cock, which was fully erect and definitely a good nine inches in length. I was proud of my own manhood but even I was left in the shade of this organ. Jill took him in her arms and together she and he sought out each other's mouths with their tongues. As their nubile bodies entwined, my insatiable wife parted her legs a fraction, and he wasted no time in finding her hot slit. He thrust two fingers inside her and he moved in and out of her quim rapidly. I came up for air and saw the erotic image of Jill being frigged standing up, and teetering on the balls of her feet. I could feel a groundswell of excitement in me, and I was completely thrilled and turned on by the thought of us four getting down to it. Victoria looked over at Jill, who had a fistful of her young lover's thick cock, and she smiled in approval.

"I'm getting really turned on," she said as she started to stroke me up and down. "I do hope this will be a fulfilling evening."

Victoria fell onto the bed on her back and patted the space on her right for Jill to join her. They both aligned themselves on their backs so that they gave Chris and me a better view of their wet vulvas.

"Jack, I want you to lick my pussy and use me to teach my boy here a thing or two. He can use Jill as his guidance. Alright, Chris?"

"Yeah, super. Great. Can't wait to get stuck in. Hee, hee, hee!"

Jill and I looked at each other with a trace of a smile on our lips at the unexpected sound of the young chap's high-pitched voice and giggle. If it wasn't for his big dick, I wouldn't have expected he had much luck pulling the girls. I now found myself as a teacher of the art of cunnilingus. I went on my knees at the foot of the bed before the MILF and Chris knelt at the feet of Jill.

"I'm sure that Victoria wants to be pleasured orally and that she wants to savour the moment, so we won't dive in but we'll just take our time. I normally start with Jill's thighs. Watch carefully."

I gently brushed my fingers along Victoria's inner thighs from just above her knees to where her legs ended and her mound began. I made sure to keep gliding up and down with light strokes, making sure not to come too close to her muff.

"Soft and smooth strokes. Take your time. Scratch the soft flesh with your nails and bend over to blow air on her skin."

Victoria closed her eyes and moaned as I did this and Chris studied my technique and copied what I did with Jill. This normally drove my wife mad with the slow build-up and her sex was usually becoming nice and moist by this time. She would be getting fidgety for me to make any sort of contact with her pussy by now. Victoria's meaty thighs were trembling now as I placed my hands on her legs and forced them to open further.

"This is a delicious spot that most women find out to be most sensitive." Chris looked at me thumbing that small hollow that separated the pelvis from the thighs. He copied me pressing in lightly right there and both of our lovers squirmed and gasped at the exquisite caresses.

"My word! You're driving me insane!"

Victoria held my head in order to press my face to her snatch but I shook her off. Her labia were puffy and pink now and there was nothing more she probably desired than for me to lick her out.

"Now we can use our hands."

Her eyes were closed, seemingly concentrating entirely on what I was doing. She didn't say anything as I explored her dampness. For her age, her flesh there seemed extraordinarily delicate. I heard her catch her breath as my finger made a path along both sides of the smooth ridge of her wet and swollen outer lips. From my vantage point near her huge breasts rose and fell as she breathed and her thighs spread out to completely bare her sex to my hand.

I rubbed my hand over her entire mound and pushed down firmly. I made tantalising circles and then used my middle finger to probe her fuck hole. I moved it in and out, pushing in further until I was in up to the second knuckle. On my left, Jill was jerking on her back as Chris frigged her as well. We repeatedly stimulated them like this and then I pointed to my mouth for him and me to begin an oral addition.

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I planted a big wet kiss on Victoria's quim and made sure to dribble spit into her seam. She clenched her legs around my head in relief but I kept them open again. I made one circular motion all around her outer folds and again enveloped her entire cunt, sucking in at the same time. Her hips lifted to my face as she was eager for me to use more pressure on her mons. Her juices were now dribbling out and I parted her cunt lips with my fingertips and gave her slit a broad swipe with my flattened tongue.

"Goodness me!"

"Make certain to flatten your tongue, Chris. That way you cover more flesh."

"OKAY!" He giggled in that whine of his and he dove into Jill's loins with abandon.

I kept finger fucking the older woman as my tongue drove inside her hot cunt. Chris was doing fine, alternating between sucking and licking motions on my wife's pussy

"Oh!" she cried, "oh fuck!"

Good, I thought. The boy is learning fast.

"How is she?" I asked.

"Her pussy tastes sweet! I love eating sweet pussy."

"And now, the clitoris. Can you see Jill's little hood at the top of her lips?" Like Victoria, Jill's clit was already peeking out of its hood, hard and erect. "Use your pointed tongue to circle her clit, but gently."

My tongue explored Victoria's clit which she welcomed with a prolonged sigh. I flicked out over and over and her hips pushed her cunt into my face. Her legs clamped around my head once more as I went to town and sucked her tiny button into my mouth. My swirling tongue delicately flicked it with the tip and I alternated between sucking and flicking, stopping occasionally to lick her entire cunt which coated my tongue with her freely flowing juices.

Her thighs tensed as I kept going until I heard her start whimpering. I began to suck harder, latching my lips around her button as I flicked at it more quickly. Out of the corner of my eye, I saw Jill thrashing and writhing on her back as young Chris trapped her clit eagerly in his mouth. We both continued to mercilessly lick and suck both women until they both lost all control of their emotions and climaxed together.

"That was incredible," whimpered the MILF.

She and Jill lay on the bed with their legs sprawled apart and with saturated pussies. I gave Chris a high five as I congratulated him on a fine job.

x

Jill's entry.

Chris had been quite the pupil and he had teased me and driven me crazy. When his deft tongue met my clit, I jerked up with delight. He held onto my bottom and pulled my crotch to his smooth face. I spread my legs even more to give him ample room to eat me out. His tongue slid up, down, and around my snatch, between my labia, and finally onto my clit. My orgasm coursed through me and my cries of joy matched those of Victoria as dear Jack brought her off. I vaguely heard her rise up and speak.

"Now let us repay your kind attention. Shall we, my dear? I want to suck Jack's cock."

I nodded my head in acceptance and watched her take my husband's stiff dick and bend down to kiss the tapered head. She gripped his solid shaft and squeezed as she sucked him in. Her mouth opened wide and deep-throated him, moving her head up and down in sweeping motions. She glugged loudly and almost drenched his dick and balls with what seemed like gallons of saliva. Jack had his hands on his hips and he winked at me and pointed to Chris.

"Would you like me to suck you off?" I teased him.

"Yeah, great. Super. I'd love that."

He turned to me and his impressive-looking erection threatened to take my eye out as he came closer! Jack is big, but this young man was long, thick, and as hard as iron. I shifted on the edge of the bed and I licked up and down the fat shaft. He moaned accordingly as I pursed my lips and took the helmet into my mouth.

"That feels nice."

There was no way I could ever deep-throat such a cock so I suckled on the head and jerked his stalk in my fist. I kept his knob between my lips as if I were sucking on a lozenge. Jack was in heat as he started to thrust his cock into the mouth of the older woman. All the while her big breasts bounced and her upper body jiggled as she sat.

"I can't wait more. Give me that big cock now."

My pussy craved cock and I lay back and folded my knees for Chris. The virile fellow came between my thighs holding his dick in one sweaty fist and pressed the flared head to my cunt. He rubbed my labia with his bulbous knob and then pushed in. He stopped once the first couple of inches of his nine-incher entered me and I grabbed onto his boyish bum. He geared himself up and started stroking in and out. her. Slowly he raised his waist and plunged, and in my ardour, I bucked up.

As he increased the tempo of his pelvic thrusts, he gave me more of his length. With youth comes vigour and as I lifted my legs, the twenty-two-year-old Chris started fucking this woman of twenty-eight hard. While I squirmed on the bed under his ministrations, I glanced to the other side of the bed at Jack and saw much of the same thing happening there. He was burrowing inside Victoria with his entire length, surging in and out of the woman with a terrific pace. She had her legs wrapped around his lower back and she managed to pull herself upward to meet his mighty thrusts. Her hands stroked his hips and sides as he hammered her into the mattress.

Meanwhile, I too thrashed about on the bed as young Chris plunged into my pussy with his long organ. He was green but eager and his magnificent prick crammed into my muff delightfully. Again, I looked over at my hubby and saw Victoria was on top of him in the cowgirl position, moving slowly up and down on his upright pole. Her mammoth tits swayed as she happily speared herself on his yummy dick. At the same time, he thrust upward, driving his shaft deeply into her yielding cunt. She moaned at the immense pleasure he was dishing out and her body glistened from their shared perspiration.

"Let's do it like that," I told Chris, who quickly got on his back too.

I got onto his lap in a reverse cowgirl and used his knob to ease my slippery lips wide apart. Facing down his legs, I skewered myself on most of his awesome stiff. When I'd got five inches inside my gaping pussy. I felt his hands on my bum, pulling my buttocks out and tickling my puckered anus. The cheek sod! I sighed happily at the incredible sensation of his big cock repeatedly sliding up and down and I leaned back while continuing to grind into him. In this position, I was able to rub my clit and the resulting waves of pleasure were sublime. Jack was rapidly bringing Victoria close to an orgasm, as his cock drove in and out of her at a rate of knots. Her moaning and whimpering grew louder and her voluptuous body jiggled and swayed in his lap.

"Oh, oh, God!" the woman cried loudly as she flung her naked body down again and again, impaling herself on the hard cock of hubby.

Sweat ran down her heaving breasts and she flung her head back, sending her long hair in every direction as she approached the edge of orgasm. Jack grabbed her waist tightly and thrust his cock deep inside of her.

"Fuck!" she yelled in an even louder voice. "Fucking yes! Fuck me, give me that big beautiful cock! Shove it in me!"

She came with a shriek and her arms and legs clamped onto Jack as she clung tightly to him. He reached out, grabbed her wide hips, and pulled her toward himself while continuing to ram his cock in and out of her sodden pussy. She slowly fell forward on top of him, sprawling across his chest, still pitching from side to side.

Once they disengaged, Jack rolled over to me and Chris and he placed his hand on the back of my head and held up his slick cock. I directed my mouth to his bell end and gobbled it up. I tilted to my left and I started sucking him into my mouth, forcing down half of his length with each stroke. I was still thrashing down on Chris, squirting all his groin as I was double-teamed. Jack must have been slightly put out as he then wrapped an arm around me and tossed me onto my back. He held me down with a wry smile as he pushed in and penetrated me fully in one long steady stroke.

"Fuck me, baby! Fuck me!"

x

Jack's entry.

Having seemingly satisfied the MILF, I turned my attention to Jill.

"Just fuck, babes." I began pounding away, sliding almost all the way in and then out, keeping up a steady rhythm that saw her hold on to me tight. "Yes, you fill me so perfectly!"

I was fully buried inside my wife and with my thighs holding hers wide, I had her pinned beneath me. I slammed into her

intending to get myself off. I grunted and ejaculated inside of Jill. I pumped my load and a few seconds later I slipped back out of her with a plop, and my cum flowed out of her and ran down the cleft between her buttocks. Jill rolled away curled up in a ball panting softly.

Chris was still in heat and he was on top of his older lover whose naked frame flailed wildly beneath him. As he rammed into her pussy, her legs kicked up and out. Her hands clung tightly to his bottom as he pitched and tossed on top of the grateful woman. His hips bucked involuntarily with the urge to go deeper. His long dick was fully inside of her as they both looked to be dangerously close to coming.

He surprised me when he pulled back out, but I assumed that he had been instructed by his mistress to do so. I looked her in the eyes and she gave me a big smile as Chris fed her his turgid dick. She licked his hose with her skillful tongue and I saw him swelling and throbbing as she sucked faster on the bulbous head. Using both hands she stroked the slippery shaft until he finally erupted. Quickly, Victoria opened her mouth and she managed to swallow most of his spurts. He put his hands on the sides of her head, guiding her as she pushed her mouth down on his deflating cock. He pulled her head up from his dripping cock and they both relaxed.

x

Jill's entry.

After a few minutes, we had all recovered some strength and Victoria moved over to sit Jack and myself.

"Tonight was just wonderful, you two," she enthused. "I do hope you can come back another time."

"I think so," I replied as I fondled Jack's cock.

There was nothing for us to do other than to get dressed and take off. It had been the most fun of any swinging we had ever done so far, and we were extremely happy about how the evening had gone. With the right partners, we agreed that after a wonderful start, the best was still to come.

END

Published 
Written by moasan
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