A Wild Widow and Widower Ch. 05

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Len gives legal teen Kaili her first intense big O.
2k words
4.28
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Part 5 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 nextdoor neighbor -- widowed 18 months ago (pancreatic cancer)

Jami -- 49 -- Tammi's sister

Kaili -- 18 -- Jami's daughter

Previously:

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 it over. Four days later T suggested that they start living together. In a discussion over their sexual preferences T had told 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 describing her 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 Kaili had just decided to stop watching.

Chapter 5:

Len stood up and slowly walked toward Kaili, his body led by his large prick that was fully engorged and throbbing.

"I think -- uuh -- well I might want to ---- well maybe - get involved a little bit."

" Hey, Kalie. No reason to be hesitant. It will come naturally, believe me. Sex drive is ingrained in all of us. I am guessing that, when you saw three naked bodies meshing together, you got pretty hot -- maybe some tingling in your nipples and a lot of wetness in your hot box?"

"How did you know? I never realized mouths could be used like that. I got really hot when I saw my mother and aunt lapping up each others dripping wet vaginas. I ended up rubbing myself a lot. But that isn't enough. I need to get rubbed by them -- or by you."

"First, you don't need to use formal terms like vagina or penis. Just call them cunt, clit, slit, vaggie, fuck hole, pussy and cock, dick, prick, fuck tool, rammer. Anything like that. If you are sure you are ready we can get you rolling. Are you sure?"

"I'm sure."

"OK. The first thing we need to do is get those clothes off. Would it be all right if I undress you. I guarantee you will enjoy it."

"I guess so."

Len led Kaili back to the sofa where she had been sitting and sat her down. He kissed her gently on the lips, then her neck, then licked and sucked her armpits, getting a slightly salty taste.

Kaili reacted with a small shiver.

Len moved his mouth on down to her cleavage, sucking the inside of what appeared to be ample teen titties. Then he was sucking her now diamond-hard nipples through her sports bra. She shivered again.

"Liking this?" Len asked, taking just a momentary break from his ministrations."

"Oooh, yes. That feels so rad. Please don't stop!"

Len continued downward, his lips and tongue gently working on her flat tummy -her navel- more tummy just at the top of her yoga pants,

"Is it ok if I keep going down?"

"Ooohh -- yes -- please. My slit is getting really wet and needs some rubbing."

"Just so you know Kaili. Most guys are selfish jerks and just want to hop on a girl as quick as they can so they can get their rocks off in a hurry. They care nothing for taking care of a lady's needs. I am different. I've found that going slowly -- very slowly _- builds a lady closer and closer to orgasm and ends up with her having intense cums, maybe several of them. You saw me when I walked over. My cock was hard and hot. Eventually I will ejaculate -- cum- shoot my wad. And there are many ways that can happen. But for now I just want you to have one fantastic experience and the best orgasm ever."

With that Len moved his attention to the inside of Kaili's thighs, then to her cunt lips. The aroma was pungent, the wetness revealing the hotness of her snatch.

"I'm guessing no panties, maybe a thong at most -- right?"

"No- I came commando. I like feeling the tightness of these pants -- they actually can make my box feel pretty good."

Len slowly worked down Kaili's legs. When he got to her feet he slipped off her shoes, then started licking and sucking her feet, taking each toe into his mouth for a gentle suck. As he moved from toe to toe he licked the gap between them.

"Oh my God!! That feels soooo good. I never thought about my feet being involved in sex -- this is wonderful."

"I always like getting into a woman's hidden places -- armpits- belly button -- feet -- shit hole -- all of them. In just a few minutes I'm going to get to lick your most treasured hidden place. And I'll get deep inside your cunny."

With that Len reached up to Kalies chest, massaging her boobies and tweeking her nipples. Then he slowly lifted her bra, moving it over her head.

As he had suspected Kaili's nice, bulbous teenage boobs were already larger than her mother's. The areolae were pale and her nipples were still small, but stood erect with sexual heat.

"Oh my God!" Len reacted. "Your chest is just perfect!! Can I get a little taste of these gorgeous breasts?"

"Sure, I like it when they get rubbed and sucked."

Len moved his lips to Kaili's nipples, gentle sucking each nipple in turn while his hands massaged her tits.

"Nice size" he thought to himself. "These may grow some -- but they'll never be saggy."

"Ummmm" he purred. "You taste so wonderful. These titties are the perfect size and are so young, nice and firm!!"

Len's pleasuring had his prick swollen with excitement and anticipation. He already felt precum oozing from his dick head. As he continued to suck and rub Kaili's mounds she purred and cooed with pleasure.

Then he felt her move her arm, reaching her hand down toward her crotch. Len reached down and stopped her.

"Not yet sweetie. No self-stimulation. Part of a great sex experience is not being able to control what is happening. I'll get down to your box as soon as we get these tight yoga pants off you. I can't wait to see and taste your legs and young cunt. Why don't you stand up it'll be easier."

Kaili stood and Len turned her around.

"I want to see your cute butt first and save the magic box for last."

He gently rubbed between her legs, feeling dampness -- her seeping cunt juices. Len took hold of the waistband of her pants and slowly move them down over her hips. The pants were so tight it was not easy. Len slowed even more as he moved her covering down over her butt cheeks. As they became more and more exposed Len first stopped to massage her ass halves.

"Wow -- so fantastically firm, smooth and round" he thought. "This young girl is an experience I've not had since high school -- and I didn't really appreciate it then. I was in too much of a rush to get my cock spurting."

He continued moving her pants down her legs -- slowly -- slowly -- taking time to feel the silkiness of her skin, especially on the inside of her legs. Len finally got the yoga pants down to Kaili's ankles and she stepped out of them. Len looked at her perfectly figured backside -- then very slowly turned her around.

Seeing her magnificent upper body Len slowly lowered his eyes. Her cunt was perfect!! There were strands of amber, silky hair at the top of her teen clit, shaved down to her bikini line. Her labia were soft, slightly puff lips; her slit was tightly closed, showing no evidence of penile or digital intrusion.

"Kaili, your body is perfect! Both front and back. I've never seen such perfection. I am pretty sure you are a virgin, right?"

"I guess. I've let a couple boys rub me there, but never let anyone stick stuff in me."

"May I use my mouth on you?"

"Sure -- I am anxious to feel that. I am soooo hot and tingly right now. I want you to help me finish hitting my high point."

Len had Kaili sit back down on the couch, then helped her move her feet up on the edge, spreading her knees apart widely.

He marveled at the beauty of her sex. Using his fingers Len gently opened her puffy cunt lips, revealing a beauteous, pink inside of her cunt. The slit was moist with Kaili's sex juices.

Len moved his lips to her lower tummy, kissing and sucking her navel. Then he moved down, stopping to bury his face in her soft, thin, auburn cunt hair. The scent was incredible -- pungent, sweet, stimulating. His cock throbbed harder. Len licked and sucked her labia and his tongue flicked into her tight pussy slit. Gently he used one hand to spread her slit. Looking inside he saw unmolested pink skin and her pearly clit, nicely erect. He inserted his middle finger into her, feeling the tightness of her vaginal entry. There was enough moisture from her sex juices so that the probing was not painful.

When Len started his pussy ministrations Kaili's purring and mewing intensified to moans and groans of pleasure.

"Mmmmmm -- oh that is good. Oh- yes-yes --yes. Keep doing that. Faster -- harder." As Len stuck his finger inside Kaili gave a little yelp, but then relaxed.

"Oh -- my - --- God!!! Please don't stop."

Len had turned his finger so its tip could explore the inner wall of Kaili's vagina, searching for her G-spot. He couldn't feel anything.

"Is she so young it hasn't developed" he thought. Len wasn't even sure all females had one.

"Fuckkkk!!! This is so good. I've never ever felt like this!"

"Do you want me to stop or give you your first real orgasm?"

"No!!! Don't stop. It just keeps getting better and better."

Len used his fingers -- 2 were inside now -- to rub her clit faster and harder, seeking the elusive magic spot. Then he sucked on her clit while his tongue flicked it as fast as Len could get his taste muscle to move. He sensed Kaili's cunt lips begin to convulse; her twat was dripping with juice. Len loved the smell and taste of her excretions.

Kaili's hands were gripping the sofa cushions. He back was arching, thrusting her wet snatch upward toward Len's probing lips and tongue.

Kaili was almost screaming. "Oh -- yes -- yes -- yes. Lick me. Suck me. Rub me. Right there -- don't move -- stay there. More -- more -- more. Oh, yes -- fuck me with your fingers and tongue. Fuck me hard!!"

The young teen gave out a series of soft screams as her hips bucked faster and faster. She had reached the climax of her first great orgasm.

Panting and gasping, Kaili began her cool down, her heart rhythm starting to slow. She pulled Len up, kissed him and hugged him tightly.

"Thank you, thank you, thank you. I'll remember that the rest of my life. I don't think I'll ever feel that way again."

Len chuckled. "Young lady, you've just experienced you first great sex. There is a whole new world of sex before you. I guarantee you will feel like that many times -- even better -- as you ripen and relax. There's a LOT more for you to experience and learn."

(to be continued as the four melt into a naked mass. Will Kaili get her first penile fuck?)

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