A Wild Widow and Widower Ch. 06

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Len & T join with mom Jamie for Kaili's loss of virginity.
2.4k words
4.53
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Part 6 of the 7 part series

Updated 06/09/2023
Created 03/13/2019
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Participants (all based on people known to the author. Names have been changed and ages have been altered to fit the scenarios.)

Len – 64 – widowed 3 years ago (traffic accident)

Tammi – Len calls her "T" – 56 - Len's next door neighbor – widowed 18 months ago (pancreatic cancer)

Jami – 49 – Tammi's sister

Kaili – 18 – Jami's daughter

Previously: (full story in Ch 1-5)

Widower Len had, over drinks, invited Widow Tammi – his next door neighbor - to enter into a sexual relationship. After a wild fuckfest in the Honeymoon Suite of a nice hotel, Len asked T to think about what their future relationship would be. Four days later T suggested that they start living together. In a discussion over their sexual preferences T had told Len she had a lesbian and incestual involvement with her sister while Jami (just 18) was still in high school. T had invited Jami over – after telling her of the new relationship with Len. Jami had eagerly agreed and had insisted she bring Kaili who was looking to expand her sexual experience – she was still a virgin. While Kaili watched, Len, T and Jami had entered into an intense ménage-a-trois. As the last chapter ended Len had treated Kaili to her first intense BIG O!

Chapter 6:

When Len left to give Kaili her first quaking, screaming, ecstatic orgasm the sisters were left to entertain each other. They licked and kissed and sucked each others bodies from ears to toes, ending up in a 69 with each sticking their mouth in the other's pussy, using their lips to taste and suck their puff cunt lips. As their twats filled with pre-cum juices they both began to moan & mew with heightened sexual heat. Then their tongues began probing deep into their respective snatches, their tongues flicking the now fully engorged clits.

"Oh, my God, Jami . You are so tasty and sloppy! I want to put my whole head inside you."

"That would be pretty hard, sis. But I wouldn't object to you putting a bunch of fingers, maybe even your fist."

With that Tammi inserted 3, then four fingers, into Jami's hot, wet cunt.

"Ummmm. Nice. Yes rub those fingers on my clit. Try for my g-spot. Oh yes. That is so good – I am SO close to cumming."

T backed her fingers out, rubbed her entire hand and wrist in Jami's dripping pussy juice – then slid her entire fist through Jami's vaginal opening.

"Oh, my God – that is fantastic" Jami screamed. I am cuuuummmming!! Oh God, yes!!" Her climax was so intense she spurted juice all over T's wrist, up to her elbow. She grabbed T and held her tight as her orgasmic spasms consumed her, then gradually subsided.

"OK, sis. Now you need to do me" T begged. She grabbed her favorite vibrator, the one that had a curved end to get the vibes up to her g-spot while also hitting her clit just right. She handed it to Jamie who turned it on low and then carefully inserted it into T's cunt. There was plenty of sex juice to allow the vibe to slide in smoothly.

"UUmmmm" T purred. "Yes, that's right – right there. Oooooh fuck. Feels so good. Turn it up."

Jami moved the control up to medium, then higher. As T started to buck her hips up and down, Jami turned the setting to high, pressing her hand and the vibrator down to meet T's thrusts. She now had one hand free and used it to massage T's boobs, her thumb and forefinger pinching her rock hard nipples.

"Oh what a nasty sister you are" Jami said. "You are SO naughty. Naughty, but GREAT fun." She then grabbed hold of T's tit – and twisted it hard.

"Oww" T yelped in pain. "But don't stop! Keep going."

Jami kept twisted, then released the mammary. She kept up the routine. Twist & hurt. Ease up and kiss. Over and over, gradually increasing the hardness of the twist and pain level, causing T to scream in pain-pleasure and beg for more. Jami threw in a few "not so easy bites" on her sisters nipples, allowing her to twist one tit while biting the opposite boob.

"God, sis!! I'm getting close. VERY close now. Oooh, fuck. Yes, yes YES!!

I'm cummmminggggg."

With that T hit her peak, her body frozen in a final sex spasm, her cunt spurting a stream of cum juice. Jami removed the vibrator and the sisters clutched each other, twisting their bodies together and slobbering kisses all over their faces while gently rubbing each other's slits.

As T's heart slowed and her panting eased she said "Maybe we should go check on your daughter. I heard some pretty intense sounds coming from her." She stood and pulled Jami to her feet and they moved toward the couch where Len and Kaili were holding each other as Kaili regained control of her faculties.

Jami knelt at the sofa by her daughter's head.

:

'Hi sweety. You doing ok? Sounded like you were having fun."

:"Oh, hi, mommy. Yes, it was great. I've never felt like that before, High School boys are such geeks. All they want to do is spurt. Not that I let them with me. Well, I guess I did dry-hump a couple and a few got themselves off when I used my hands on their tiny teenage fuck sticks".

T kissed Kaili on her lips and interjected "Hi, Sweetie. Sounds like you had a good time. Was Len all I promised? I can't wait until you and I get some time together."

"O, yes Aunt T. He was marvelous! I have never, ever felt like that before. He gave me thrills like I have never had before. Mommy?"

"What dearie?"

"I think I'd like to try – you know–-."

"You mean your first real fuck? Having Len stick his prick into you?"

"Yes. Will it hurt a lot?'

"It will hurt some – but I think you know Len will be as gentle as he can. And you know you have to do it sometime. Why not with someone you know will be loving and caring rather than with some brute who hurts you and doesn't care about you as he gets his jollies? The hurt will just be for a second or two. The pleasure will last for a lifetime."

"How do I know I won't get preg if I do it with Len?"

"Well, hon. Len had a vasectomy years ago. That is when he gets a tube tied - it's right behind his balls. It caries the sperm from him into his cum juice. He can still shoot his wad into you, but it will not carry any sperm that can get you PG. OK?"

"OK . That's fine. I never heard about that before. How do we start?'

"Hey, Len" T said. "Kaili wants to give up her maidenhood. You ready?"

"My, God. Yes!! I was just thinking I was going to have to masterbate – or have you suck me off.. I am so fucking ready to fuck!! Let's move back to our bed. That'll give us more space and comfort. And the ceiling mirrors will let us all watch everything that happens. I can't wait to see myself fuck a virgin teen cunt."

The foursome quickly moved to the bedroom

"Sweetie" Jami said. "Let's put Len on his back. Then Aunt T and I can help you as you slide down on his big pole. But first let's get you lubed up. Care to join us, sis?"

"You bet your booty I am!"

The sisters had Kaili lie down on the bed and got her knees up high and spread wide apart. They commenced to lick, kiss and massage Kaili starting with the insides of her thighs. Then Jami started to lick and suck her daughter's tight slit, finding her tiny clit, tongue lashing it from side to side. Meanwhile T was kissing and sucking Kaili's developing tits, throat and stomach.

T moved her head on down to Kaili's lower tummy until she and her sister were butting heads to get where they wanted to go. The sisters French kissed each other briefly, then turned Kaili on her side, allowing Jami to continue to lick and tongue deep into her daughter's slit which was already starting to get slick with mom's saliva, mixing with daughter's pussy excretions. Aunt T came from the back, getting her tongue into Kaili's vagina while Jami was farther to the front. T also teased and licked Kaili's shit hole and her "taint", the small underside which "taint" neither cunt nor ass.

Len was lying on the very edge of the bed watching the mother-daughter- aunt sex scene. "Come on, ladies! I am desperate. I'm about to shoot my jizz just from watching. I have to hold my own hands to keep from touching my dick!! If I did I'd shoot in a nanosecond."

"Ok, Kaili baby. You're ready for your big moment."

T and Jami moved Kaili to the side of the bed allowing Len to lie in the middle on his back. His BIG cock, now fully engorged and throbbing, pointed straight up to the ceiling. T put a coating of lube on his massive member, being very gentle and avoiding contact with his circumcised dick head.

"Come here, my little girl. You are going to enjoy this. It may hurt a little at first as Len's prick fills your sex box. You'll probably feel that your young twat is too small and that he'll never get that thing inside your fuck hole. But believe me – he will. And you will love the feeling after he does."

Kaili got on her knees, straddling Len. Her aunt and her mom got on either side of her and moved her into position with the opening at the bottom of her cunt lips over Len's rod. They then started to lower Kaili onto Len.

The initial contact of the head of Len's prick with Kaili's slit made light contact with her swollen, but tiny, clit.

She shuddered in pleasure. "Oh, my God – that feels so fantastic." Her fuck handlers continued to let Kaili down as Len pushed up to enter her well-prepared cunt. His purple glans moved into her and his shaft started to fill her.

"No. NO" Kaili shrieked. "That hurts – Owwwwww".

"Be tough, hon. You are just about there".

Len gave one sudden thrust and had about three inches of his prick inside the newly made woman. Kaili gave one final squeal of pain, then allowed herself to sink farther onto the shaft that was filling and stretching her sex hole. A few drops of blood smeared onto Len's fuck rod.

Len began a rhythmic in and out with his cock, pushing a little deeper into Kaili with each inward thrust. Kaili moved her feet forward so that she was sitting on Len's cock. Her mother and aunt supported her to keep Len's prick from going too deep, too soon. Len thrilled to the vision in the ceiling mirror, watching his very large dick slowly move in and out of Kaili's magnificent, almost hairless, slightly bloody,cunt.

"Oh, wow, girlie. You are so nice and tight! This is only the second time I've broken a lady's hymen. Oh – I am SOOO close to coming".

T grabbed Len's balls with just enough pressure to make him think of something besides his desire to pop his wad. "Hang on, buster. Wait just a minute until you bust her."

With that T and Jami intensified their ministrations to Kaili. T licked her clit, matching the pace of Len's thrusts, then rubbing and licking Kaili's clit. Jami concentrated on her young, firm tits and her diamond hard nipples. She licked and sucked while massaging and tweeking the other boob. Some pinches and soft, then harder, bites of a nipple and a few twists of her boobs provided some "painful pleasure".

"Ooohhhh. Yesssss! Faster, harder, faster, faster!! Oh my God... Sooooo great. I've never ... Yes. Yes. Yes!!. Mommy, mommy, mommy!! I'm feeling ... mind blowing!.

Oh, fuck. Fuck me harder.

Kaili thrust her hips and dripping twat up to Len as hard as she could. Len matched her, fucking deeper and deeper into her now-receptive young cunt. He now had at least six or seven of his nine inch cock driving into Kaili's newly initiated vagina.

"Oh, yes, little girl. Take that! Oh, fuck!! You are so tight. Take that dick. Try to contract those cunt muscles. Yes, yes. God I am SO close."

Kaili screamed her pleasure. Finally she hit her peak, her body convulsing as she completely lost control of her mind and body. "Oh, yes!! I am .. going.. to cum!!' She gave a couple of intense thrusts on Len's cock as she hit her orgasmic peak. She had lost complete control. A short, quick spurt of pee shot into and out of her slit.

Len matched Kaili's intensity, thrust for thrust. "O, God. Oh, God. I'm almost there. Going to cum any second... Oh, yes. Fuck, fuck, fuck. Here... I... cummmmm!."

His white hot balls had been aching for over an hour and now erupted with a rope of white cum, spurting over and over. His ejaculate flew deep into Kaili, filling her slit and vaginal cavity. When his balls were finally empty, Len rolled over on top of Kaili, keeping his now limp pole inside her. Kaili looked at he ceiling mirror and saw her crotch, cunt and inner thighs now covered in Len's cum and her own pee. She reacted with a small gasp.

"Don't worry sweetie" her mom said. "We will get that all cleaned up. Aunt T and I want to start the clean up with our mouths so we can taste the combined sex juices you have. I am going to start on you while she starts on Len. Then we can switch."

"Did you like that, hon?" aunt T asked.

"Oh, my God – yes. When can we do it again?"

"I think you maybe ought to call it a day, sweetie. Your little cunnie is going to need to recover from that massive first fuck. There's going to be a little swelling and tenderness. The best thing will be for you to do a few douches with some cool water. I'll loan you my douche bag and show you how"

"Ok. Can we fuck tomorrow??"

Len, T and Jami all chuckled.

"I think maybe we've created a new sex hungry monster" her mom answered. "I'd suggest some tender loving by your mommy before you get more prick up your cunt."

(to be continued in Chapter 7, already in the planning with more exciting sexventures.)

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Rancher46Rancher46almost 3 years ago

Great hot sex story

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