Lonely Mature Ch. 02

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My mature ‘friend with benefits’ continues to surprise me.
3.2k words
4.63
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Part 3 of the 4 part series

Updated 06/11/2023
Created 09/25/2021
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All characters are over the age of 18 by some considerable margin.

Lonely Mature Ch.2

You may remember that things progressed much faster than I expected after I replied to Jill's advert. They happened so fast I probably didn't even mention her name!

We met up in a pub, had a drink and a chat and, to be honest, I thought it would end there for a first encounter. It didn't, and the full story of how I was lead to a hotel bedroom and robustly shagged is the subject of the first part of this story.

We met several times after that, with variations on the same theme. She was so confident sexually, and so comfortable in her own skin that I was completely absorbed. She even delighted in telling me the antics that she and her husband enjoyed, after she gave him a detailed account of our afternoon together.

This appeared to fire him up and lead him on to some pretty athletic sexual activity with the lovely Jill. Jill, for her part, was enjoying our encounters and the extra enthusiasm it sparked off in her husband was a bonus, so everyone was happy.

We met up in our usual wine bar, for a little pre coital chat. Oh I love that expression. Pre coital! We both knew that the pre coital chat was going to lead to some pretty erotic coital coupling, not to mention post coital euphoria. We both knew the outline plot if not the definitive script.

By this stage we almost always finished up with missionary position sex. Once the foreplay had produced the desired results, Jill liked me on top so that she had access to my balls. She said she loved the feeling as they lifted of their own accord, signalling the start of my orgasm. It was her cue to look straight into my eyes, say something incredibly dirty, and watch the expression on my face as I ejaculated.

One Tuesday afternoon, as we lay side by side in our post coital euphoria, and still joined by my slowly deflating penis.

"So, when I met you," she opened with, "would it be true to say that you were something of a shrinking violet?"

"I think that's fair."

"So how do you feel now?"

"Less shrinking for sure, oops there is a pun in there somewhere!"

"So more confident sexually?"

"Without a doubt."

"Do you remember our first meeting?"

"How could I forget?"

"Remember how I lead you and relaxed you?"

"Yes but where's this going?"

"OK, confession time. I have a very dear friend who is, let us say, very inexperienced in matters sexual."

"Go on."

"OK, please just listen first and talk later. She and her husband divorced some time back and she and I do girl talk. She has never had what you might call an adventurous sex life. She and her husband only ever had a Friday night, lights out, missionary shag."

"Mmmm."

"No listen! We do a lot of girl chat. She knows about my open marriage and envies me my varied sex life. So one evening, when she was bemoaning her lot, I suggested she put out an ad just like I had. Well you'd have thought I'd just suggested bonking the pope!"

I giggled and the inevitable happened. My shrinking penis fell from its divine haven, producing that tickling sensation occasioned by bodily fluids escaping from where they had so recently and forcefully been put. Jill continued.

"Our chat continued and the bottom line was that she would really like to meet you."

"Me! I can't see myself as a latter day Don Juan or Casanova. Makes me feel like some sort of extra on Karma Sutra comes to Britain."

"OK, but this is important. I am asking you to introduce her to some of the joys of human sexuality. Joys, I know from experience, that you are good at."

"Bloody hell! As McEnroe was famous for saying. "You cannot be serious!"

"Oh yes I am, totally serious."

"A million questions. What if she doesn't fancy me? Does she know she's being set up? What if I don't fancy her, as yet I have no details? What, just what? What? What?."

"OK, one step at a time. She has intimated to me that she is open to the idea of being seduced by an older man who knows his way around the female body."

"Intimated? Open to the idea! Seduced! How on earth am I going to seduce someone. My seduction technique, at the best of times, was pretty pathetic, and that's now at least forty years out of date."

"Just let me take care of that." She slipped me a photo, "This is the lady in question."

My eyes nearly popped out of my head. She passed me what must have been a holiday snap judging by the number of others in the picture. A tall, mature, olive skinned lady, at least ten years my junior, wearing a black one piece swim suit, starred out of the picture.

Tall? For sure. Striking? Certainly. Small breasted? Yes. Pert of bottom? Agreed. A lovely looking lady, no question. Her features were soft with a slender neck and nearly every finger bore some sort of adornment, mostly silver rings,

"So," said I, stating the blindingly obvious, "she can have almost any man under seventy, other than a eunuch. This is a joke right?"

"No joke!" Said Jill. "This is deadly serious. Are you up for this or not.?"

"What do you expect me to do?"

"Bonus question! If you're on board, I want you to take her to our hotel, undress her, just as I undressed you. Lay her gently on the bed, as I did with you, and give her your five star blow job. I'm not even asking you to shag her. If you do to her, what you did to me, she will ask for that herself!

"All I ask is you introduce her to the delights of oral sex."

"It doesn't sound like too much of an imposition!"

"Are you up for it?"

"No brainer, yes, but how do you feel about me having a sexual encounter with someone else?"

"No problem. I do it all the time with you and hubby. It might even give us something exciting to share in those 'I'm just about to cum' moments." Jill never ceased to amaze me.

We met up in our usual wine bar the following week and chatted.

"You remember I mentioned my friend last week?"

"Not a conversation I'm likely to forget in a hurry."

"So, normally we go to the hotel now and have a brilliant afternoon, but today is different." She took her phone from her handbag and pressed a saved number, "today you are going to meet Alexis and show her something new." She put the phone to her ear.

"Yes dear, here, now. Come and join us." And ended the call. I was stunned.

"What? Today? Right now? But what about you, what about us?"

"Believe me, this will bring me almost as much pleasure." As she placed her hand conspiratorially over mine and passing me an electronic room key. "Almost! You get to meet Alexis and if you click you go off to 'Our hotel', room 403 is ready."

I had been caught totally unawares: again. I thought we were talking hypothetically, about the future, not today. Alexis must have been involved in the plot too as she appeared within five minutes. The introductions were made and she was every bit as striking in real life.

I don't know if you can imagine just how awkward this meeting was. I have conditionally agreed to, lets face it, go down on this lady that I've never met, subject to her final say so.

We chatted about this and that when, eventually, Jill announced she had to leave.

"Are you coming Alexis?" This was presumably her get out of jail card and I was pleasantly surprised when she refused.

"No thank you, I think I'll stay a while." Now it was all up to me. I don't remember exactly how we overcame our mutual embarrassment, but we got to the hotel, through the lobby, and finally entered the lift.

The journey to the fourth floor seemed interminable, only slightly shorter than the walk down the corridor to 403. I held the plastic key to the sensor, praying that it would work first try. There was a satisfying click and the door opened.

Jill had certainly done her homework, she must have had a pretty good idea that I would be on board, but what about Alexis? The lighting was subdued, the large kingsize bed was spread with pillows and cushions.

There was even a bottle of sparkling wine chilling on the table. I took the hint, popped the cork and poured two small flutes.

"Cheers," I said taking a sip. She responded with a nervous smile and took a healthy mouthful. Not wanting to break the spell, I stood in front of her and started to undo the buttons of her white blouse, very carefully, one at a time. She took anther healthy mouth full as it fell open revealing a pretty black bra. I ventured a kiss, more of a peck really, and was delighted by her enthusiastic response.

"I am so nervous." She breathed into my ear as we broke from the kiss. "I've never done this before: ever." I felt it would not be helpful to tell her that I was petrified! Luckily my mouth just said.

"Relax and enjoy it. We can stop at any time."

In no time at all our tongues were intertwined as I freed her from her skirt. The button gave way at my first, less than expert, attempt. The zip slid down easily, and I let it all fall to the floor. Black bra, black panties and a loosened white blouse.

If she was stunning in a one piece swimsuit, she was drop dead gorgeous in bra and panties. Tall, statuesque, a truly lovely looking lady, made even more lovely because she was breathing heavily in anticipation.

I shed my clothes down to my boxers and gently laid her down on the bed. Our mouthes met again, in a passionate kiss, as I managed to release the catch on her bra. Her pert little breasts popped into view, not large, but a delicious shape, topped with darker areolae. I kissed them both, leaving a little moisture on each nipple, which I blew on softly and they responded visibly.

A little moan escaped her lips as I made my way slowly down to her navel. When I reached the waist band of her panties I gently inserted my fingers and started to inch them down slowly to reveal the delights underneath. By now she was actively joining in and lifted her bottom gently to assist me.

I think I was expecting a generous quantity of hair, after all she was not particularly sexually active so why shave? To my surprise, and delight, there was not a hair in sight. Totally waxed smooth. You just don't get that bare with a razor.

I don't claim to be an expert on female sexual anatomy, but I have always been led to believe that the clitoris can be illusive. This one was certainly more obvious than the few I have been privileged to examine in any detail.

I resisted the temptation to head straight for such an obvious target and kissed her inner thigh from the knee up to her mons, nibbling gently with my lips as I went. First one leg then the other with no actual sexual contact. After some time I started to massage her outer lips gently and as they started to open with her growing excitement, I felt her hands on my head, urging me on.

Gentle laps on her clitoris alternating with fondling her outer lips was clearly producing the hoped for result. Her hands pressed my head into her sex with ever increasing vigour.

I took this as a cue to take the whole area into my mouth and suck vigorously, while tickling the end of her clit with my tongue. Little short gasps were followed by her forcing her sex into my mouth.

So as not to rush, I reverted to the thigh kissing, until it became obvious that my tongue was required elsewhere. Returning it to her clit, I sucked and lapped for a while and eventually her hands clasped my head, forced it down, her thighs clasped around my head as she pushed me ever deeper. Then there was a shudder and she relaxed.

I have to admit to feeling a little proud of myself. I had achieved the result we all hoped for and I moved up the bed for another languorous kiss. As our tongues battled, her hand slipped down inside the waist band of my boxers.

If there is one thing that is guaranteed to produce an erection it is a woman orgasming. Alexis' hand found that proof and started to stroke it gently.

"That feels so good." She said, "I really want to feel it inside me: deep inside!" I slipped off the boxers and we lay side by side naked. She fondled my cock, leaned into my ear and breathed.

"Take me. I want you. Fuck me now!"

She layback, open legged, on the bed, in the most inviting pose a woman can adopt and repeated the instruction.

"Please, fuck me now!" I rolled over between her parted thighs and allowed my cock to find its own way into her moistness. Pausing at the very entrance with the tip just parting those flowering lips, I was stunned by the contrast.

A fully erect, pink, cock entering an olive skinned vagina! This moment needed savouring. She was hot, she was wet, and she was encouraging me. My cock slid in easily as we started in missionary. It was erotic beyond words to watch the pinkness of my penis vanish into her darker skin and reemerge glistening with the evidence of her excitement.

As things got hotter, I pressed one of her legs to the bed and rolled her on top of me.

This gave me access to her buttocks and I was able to massage her back, while she controlled the rhythm. I allowed my finger to run over her most secret place and use some of her excitement to lubricate the area as I gently inserted a finger into her rose.

That, together with running the finger nails of my free hand gently over her buttocks, lit another spark, which she turned into a fire by grinding her clit against the base of my cock.

I pressed a little harder on her rose and she relaxed enough to allow one finger to slip inside its warmth.

Eventually she pushed down so hard that my cock reached the very bottom of her sex and pressed hard against her cervix. This always has the same effect on me, and this was no exception. My cock jerked as the ripples of pleasure ran along it with each contraction. She squealed as I withdrew my finger from her bum and emptied myself into her. I felt her muscles clamp around me.

She flopped on top of me panting and murmuring. She smiled and pressed her mouth eagerly to mine in a passionate kiss.

"I had no idea it could be like this!" Was the greatest compliment I'd ever personally heard.

*****

A week or so later Jill and I met up again for one of our regular encounters.

"Did you have fun with Alexis?"

"I certainly did. And you had set the room up beautifully, thank you."

"It wasn't going to be wasted. If your hook up with Alexis hadn't worked, we would have used it. Now come to my boudoir and tell me all about it." We took the lift to the fourth, she lead me along the corridor and pressed the electronic key to 403. The door opened to exactly the same setting, lighting, pillows and sparkling wine.

"I don't know what you did to my friend but she was like the cat that got the cream. I want you to tell me all about it, every detail and show me, right here, how you pleasured Alexis. Every tiny detail, on the same bed!"

I popped the cork, poured the wine and we took a sip or two. I managed to relive the undressing, the caressing and the oral sex while performing the same manoeuvres.

"You know how I like a sexy story while shagging, something to tell hubby tonight while I'm doing him."

I couldn't resist telling her about the incredibly sexy sight of my pink penis sliding in and out of her olive skinned vagina while I knelt between Jill's parted thighs and pushed myself slowly into her.

"It has to be one of the most erotic sights I've ever seen, the contrast, the implication of planting seed. I can't describe it, it's just so cummy."

"So is my little pink pussy not enough anymore?"

"Your little pink pussy will always be special." As I reached full penetration.

"More detail, more detail." I gave a nearly blow by blow account as we coupled and when I got to the bit about rolling her on top she said.

"Like this?" And suddenly I was underneath being ridden at a slow rising trot.

"So she's cum once by now?" And as I described the scene, she increased the pace of her trot. More description followed and the trot got more and more vigorous, particularly when I described inserting my finger into Alexis bottom.

"Pinch my nipples now. Hard!" As I did so, I felt her muscles grasp my cock as the spasms of her orgasm washed over her.

" Delicious! Fucking delicious. Just wait till I get hubby in to bed tonight, he won't know if it's Monday or Thursday week, particularly when I push my finger into his bottom. We both like a good story but this one is so special."

She climbed off, and my, still fully erect, cock fell free. She placed her head in my lap and started an expert blow job, licking the sensitive join at the frenulum, until every nerve was screaming. Her mouth then seemed to engulf my entire penis and draw it down deep into her throat. It didn't take much of this treatment to overcome my self control and I gave way to the urgent need to ejaculate.

"I'm right on the edge!" Jill likes to be told as I approach the final moments.

"I'm just about to come!" The suction deepened and she massaged my balls.

"I'm coming right now!"

I felt the ripples of orgasm sweep along my cock as I came, and came.

As most of my readers know, feedback is my main motivator. I love to hear readers comments, good or bad, on my little stories. I totally understand the desire for anonymity, but it denies me the opportunity to thank you. If you comment using my bio page and your Literotica name, I will only be able to contact you via Literotica. If you would like to comment directly that is even better.

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14 Comments
BaldingBaldingover 1 year ago

Great story with believable characters and accurate, realistic sex play. Only slightly marred by:

"lead" for "led"

"peak" for "peek"

and a few others which could be rectified by a proofreader.

oldtwitoldtwitover 1 year ago

You have a good plot with good characters and your descriptions are spot on

KallMeTTKallMeTTover 2 years ago

Good story. Well told.

AtrampboyAtrampboyover 2 years ago

Beautifully written and oh so hot, thank you for sharing

jon123litjon123litover 2 years ago

Your stories are all A1 that I have read this being no exception. I never rate over the middle even for the best I give your stories a 4 to 5. Keep up the good writing please

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