The GILF Gets It in the End

This is an adult sex story.

All the characters are of the age of consent or far over it!

Any children named or mentioned are not involved in anything sexual.

This is story number fifty seven (57).

The previous story is titled "I Rub My New Banker the Right Way" which is story fifty six (56).

This is the continuing story of how I spent my summer vacation in Las Vegas, Nevada, USA.

Enjoy and thanks for the views and votes.

*****

My balls sent off that all too familiar tingle of an impending blast of my steaming baby batter into a wet, warm, waiting and welcoming female orifice.

I'd been waiting for this moment, this orgasm, as I plowed her oh so very tight sweet ass vigorously on my journey to nirvana.

I'd taken her virgin ass with relish.

From the first moment I laid eyes on her I wanted her.

I wanted to fuck, and to come inside of her, her pussy, her mouth and her very fine ass.

As for that ass, I had lusted after it like no other ass I'd ever seen before.

A large part of was visual; seeing her in her business attire at our first meeting, I knew, I just knew she had a great ass.

She knew that I knew too, because she caught me looking more than once. She smiled shyly in response.

Part of it was physical, once I got her naked and we'd fucked and oh how we fucked; it was a natural progression to take it to the next level of intimacy and trust to move to having anal sex.

For me at least; it took some coaxing on my part for her to experiment.

Part of it was psychological and my need to dominate; for her to understand that this kind of sex was something I expected from her as I received it from all my lady friends.

I love it when a woman is on her knees; thighs spread wide, head down in submission, ass up, me behind her, hard, and ready to poke that small hole, that rosebud, for the very first time.

On the bed, nude, her bung hole gave off the earthy fragrance of her shit but I didn't care.

I stroked myself, spreading the lube evenly.

Her ass was hot and wet with the lube I'd generously applied, initially using a couple of fingers in and around her rosebud.

I'd been gentle, but persistent with my rubbing and probing.

There was no stopping and no turning back.

Her ass was mine.

*****

All women have a butt.

There are butts, then there are asses, and then there are asses to die for.

Her ass was certainly in the last category.

It may have been in an even higher category all its own: asses to worship.

It was well shaped, muscled in just the right places, the proper size for her height and frame.

It was tan, except for where her tiny thong had covered her smooth, firm light bronze skin.

My hands cupped those cheeks quite well.

Natalie loved it when I held her ass; when I fondled it; when I smacked it as I took her from behind.

One of my favorite things is to cup a woman's ass and then probe for her rosebud with my fingers.

It gives the lady in question some idea as to what I ultimately want.

The first time I touched Natalie's rosebud she jumped a bit and laughed.

She may have been embarrassed or perhaps just nervous about my intentions. My intentions were always clear when it came to butt sex: I expected it. I wanted it.

And I would not be denied.

She knew it was going to happen; she knew how it felt -- nice -- very nice --- when I rubbed all around her bunghole and when I probed it, gently, with my finger, then, patiently, being very generous with the massage oil, lubing all around but not quite into her drainage hole, before I carefully, slowly, with no rush, slowly pushed my index finger into her tiny rosebud, stopping as she gasped at the initial feeling of a foreign intrusion back there for the very first time.

No pun intended, I did not push it.

One finger in, slowly and carefully.

She seemed okay with that.

I didn't do anything crazy or wild. I just probed, taking it slow.

I got in to my knuckle and moved it around a bit, working to open her up a bit without frightening or hurting her.

She allowed me, provided I continued to be a nice guy, and a gentleman about it (and I was both of these things), to continue to fondle, kiss, lick and oh so gently and slowly probe her asshole when we fooled around.

She teased me a bit, wanting to know what the big attraction was.

"Are you an ass man, Jack?" she laughed as I patted and rubbed her perfect hindquarters.

I simply replied "I want to love you all over."

That seemed to satisfy her.

I know she appreciated me taking my time to get to the destination.

The next day, two fingers went into her well lubricated hole.

But not before I rimmed her, something I knew she enjoyed but might not ever admit.

With the digits doing their cave exploration came some gasps: "OOOH ... AHHHH."

A grunt; a groan; she did not protest, so I continued.

As I pushed in the second finger she moved her ass away so I stopped and slowed things down.

It took a few minutes but eventually both fingers made their way into the tight bunghole of backdoor love. I got them knuckles deep and then pushed in a bit deeper.

"It's not unpleasant" she told me; "It's just different."

A new feeling. A stretched out feeling.

Having broken new ground with her, and having received no resistance, I decided to change my strategy up a bit.

The following day, I reintroduced her to the two well lubed fingers which she took with only an "Ahhh" which was better than the "Go slow damn it!" from the day before.

My new plan was to get her used to something bigger and longer in her ass, so she'd be better prepared, mentally, and physically, for my hard cock pushing past her tight ring.

Since we met I had been fucking her ass in my mind, going balls deep while she came over and over again ... on my cock as I pummeled her ass to its fullest.

I pulled her up on her knees and with two fingers from my right hand finger fucking her still very tight rosebud, I reached around with my left hand and found her love button just waiting to be played with.

As I suspected because I could smell it, her pussy was already quite moist and her pussy was desirous of some male attention.

She immediately responded positively to this program to pleasure her by responding in a way that bode well for my plan.

Remember the song "Dueling Banjos?"

I was going to do her with dueling fingers.

Bucking on both of my hands, I had soon had her ready to come and I started to slow down the pace of my thrusting fingers in and out of her ass and ramped up my pussy play.

She was so worked up and invested her own pleasure she didn't realize that the second she started shuddering as her orgasm approached, I pulled my fingers out of her ass and slowly began to insert into her dilated rosebud a well lubricated plastic butt plug about half the size of my cock.

So caught up in coming, she could only try to clench her butt cheeks together to stop the alien invasion but I would not yield until the healthy size unit made its way fully inside of her pulsating ass.

Natalie came for a second time with a groan, a scream and a gush.

I pushed her butt to the sheets while she shivered and moaned at the intense orgasmic pleasure I delivered to that divine body.

*****

As for the dildo, she didn't like it, her eyes watered (no tears) but she knew better than to ask me to take it out.

She said she felt full and I responded with "Like you need to take a shit?" and she laughed and replied "Yes."

I helped her get up off the bed and walk around the suite to get used to her new anal partner.

There were some small grimaces but generally she took it quite well.

Keep in mind that she'd just come and me, well, I was hard as a steel beam.

What she did do is ask me how long she had to keep it inside of her.

I replied by getting off the bed, cock bobbing, and going to the closest to get a brand new bathing suit for her to wear at the adult pool downstairs.

As I handed it to her, I said "The bottoms on this suit will cover your cheeks and no one will know that you have a butt plug hiding in that world class ass of yours."

She nodded and smiled, impressed with the gift I had given her. The suit was extremely flattering and she knew it.

She looked at my very hard bobbing cock, my male digit that had given her so much pleasure in our relationship and then she lifted her eyes and smiled at me.

"My, my, that sure looks interesting Jack. And big. Did I do that to you?"

I nodded, wondering if she was going to fix the problem she created.

As in, give me some relief.

One of her patented blow jobs would be nice. Or maybe a quickie.

I'm not a fan of hand jobs; if I wanted one of those I could do it myself.

Smiling, she said "When this thing comes out of my ass, I'll address that" pointing to my hard on.

Natalie continued with "And not one second before."

I know I frowned or looked disappointed and she laughed and said "If you can't wait that long you could go beat off in the shower. I'll watch."

*****

Down at the pool, more interesting things happened that afternoon.

She was pretty enough, with a rocking body, so she turned heads wherever she walked.

We got to the cabana and she surprised me by dropping her bag on a chair and taking off her top immediately.

What surprised me was that she wasn't shy about it; she went to the opening of the tent and took off her top in plain view of anyone that was looking.

Given her good looks, she had a lot of eyes on her.

This pretty conservative woman, a professional by every measure, had never been topless in public before and her nipples took notice of their freedom.

God had blessed her in this department.

Her pink nipples rose to the occasion, with my full support and with the unspoken thanks of those who were also by the pool that afternoon.

Now topless, she turned and asked me what I wanted from the bar. I gave her my order and she strode over the bar with all eyes in the place on her and ordered us a couple of ice cold bottles of Corona, with slices lime of course.

Carrying the liquid gold back to the cabana, her ass swinging with some exaggeration, she bent over, her tits falling off of her chest, hanging almost in my face, and asked me "Did you like my little show?"

I laughed and said that I did.

"Well Big Boy, I'm not done yet."

With that she reached into her bag and took out the sun block lotion, which she squirted into her hands and started rubbing all over her front!

She took extra care and took her time making sure those tits and nipples were well coated.

Natalie lifted and separated those tits of hers and her fingers not shy about applying the lotion.

At one point she teased me by pulling on her nipples telling me "I can't let these be sunburned because then you can't suck them!" to which my cock responded by throbbing in my shorts.

Laughing at my discomfort, she turned and waved at someone. In a minute one of the cute little girls from the bar came over and proceeded to take care of the rest of Natalie's bare body.

The bartender was not only generous with the lotion, Natalie let her hands wander all over and I had to struggle to get comfortable with the huge erection this girl on girl fun created.

"Come back in about 15 minutes hon" Natalie said to her as she slipped her a $50.

Now gleaming with the cream rubbed in all over her, Natalie smirked at me.

"You thought you could stick that thing up my ass without paying for it, didn't you?"

I didn't know what to say so I just smiled at her in response.

Natalie came over to me, and straddled me, her generous lathered tits rubbing against my hairy chest.

She kissed me and I kissed her back.

My hands were on her back and I know she could feel the huge rocket ship I had in my shorts.

Her hands were in my hair, which is something I love when women do it to me.

Breaking off our kiss, sitting nose to nose, she looked me right in the eyes, smiled and said "I intend to give you the worse case of Blue Balls you've ever had. You want my ass? You'll pay the price Mister Pleasure Stick."

*****

I stayed in a state of semi arousal all the time we down at the pool.

Natalie did things deliberately to turn me on.

She was quite the tease.

I knew that having butt sex with her was well worth the wait, and the discomfort.

*****

She knew from the start, and I had made it clear, that all my lady friends were three input women.

Meaning, I take them in their mouth, then their pussy, and then their ass.

It's the ultimate conquest, taking a willing female up her virgin poop shoot for the first time, and depositing your load there.

Those were the rules of the game, and if you wanted to play with me, well, you knew what was expected.

*****

I'd already planned to pass on whatever relief she was thinking of giving me.

I had a rendezvous with destiny: her virgin ass.

After a couple of beers and more teasing including a very heavy make out session, back in the suite, in the bathtub, I pulled the butt plug out, slowly and then had her use the bathroom.

To clean her out, once she got back into the tub, I gave her two warm wat5er enemas and then massaged her nude body to calm her down on the bed.

We made out on the bed, my hands all over her, and she stroking me, softly, and gently, then I got her up on her knees, head down.

*****

I was going to bury my cock in that ass of hers, to the hilt, balls deep.

The first time my cockhead touched her rosebud, she flinched.

"Relax baby" I cooed her, gently pushing her ass down to better line up for my successful penetration.

Her hole winked at me in fear of my entrance.

Yes, I could have rammed my dick into her, but that would gone over like a turd in the pool (movie reference: Caddyshack).

"Haven't you heard? Ass is the new pussy" I grinned as the head of my dick fought its way into her winking, stinking rosebud and past that first tight ring of defense.

"Yeah, right ... OH GOD IT FUCKING HURTS" she responded, as tears fell down her cheeks but not before first grimacing at the sharp stabbing pain and then verbalizing her whole negative attitude with a "Slow The Fuck Down Jack!" protest.

Safely past the tight ring, I felt her ass muscles pulsate around my cockhead.

I waited patiently for her to relax for the next phase of the invasion.

"Breathe" I told her as I rubbed her back.

"OH FUCK JACK" she cried out as a sharp pain shot up from her ass to her tummy.

"Breathe" I coached her again.

She seemed to relax a bit and I thought I could continue by efforts.

I told her to reach back and pull her cheeks apart for me.

When she hesitated, I slapped her cheeks twice so she knew I meant business.

I wanted her as an accessory to this crime I was committing.

Okay, it wasn't a crime anymore but you know how when something feels so fucking good it should be one?

If they gave out medals at the Olympics for ass, she'd win a Gold.

Muscled in the right places, toned by exercise and baked perfectly in just the right places by the desert sun, she was a hot piece.

And it was mine.

There's something about taking a woman's ass when the woman has a dominant, no bullshit personality.

To see her submit, on her knees, thighs spread wide, pushed apart by my legs; head down on the bed, holding her ass cheeks apart to acknowledge my total dominance.

To her credit, she only tried to move away from my invasion of her back door once.

She wouldn't have gotten far.

I had her in a position where she had nowhere to go. All she could do was take what I was delivering.

Now pushing past the tight ring she initially tried to squirm away from me and my thick tube probing her, but I held her hips firmly and she dropped her head to the mattress in submission as I slowly pushed deeper into her tight virgin back channel.

She groaned, she winced; she cried a few tears and she begged me repeatedly to pull out but I would not be denied.

I did slow down my thrusting so she knew I heard her and wasn't being a total asshole about this.

After a few more minutes, I finally buried my cock as far as I could get it to go.

Lodged deep, I grinned at the sight of this prim and proper lady being fucked in the ass for the very first time.

Taking her in long strokes which she only sort of enjoyed, as it was truly virgin territory, I successfully managed to distribute the various lubricants up and down the length of her tight shit chute.

I took her deep, slowly, stroke after stroke, savoring the newness of this ass, pulling her hips into me as I thrust, pushing my cock as far as I could go and then, with just a final effort, I went a bit deeper.

Which earned me a little gasp from her; music to my ears!

I loved hearing her soft "Oh Ah" as I drove my cockhead as deep as I could go; grinding it against her bowel walls where no man had ever gone before.

All the while she clamped down on me, and pushed back to expel me, as if taking a bowel movement, but all she really did was make it better for me.

God it was good.

Soon, just a few minutes into the dirty deed, she shifted into overdrive and her body had responded by contributing bodily fluids of her own, making the act of ass fucking more pleasurable for both of us.

I asked her "Do you like it in the ass?"

Her reply between the weak sounds of her mewing was "Yes it's incredible."

I continued my robotic thrusting, going deeper and deeper.

She broke the silence with "I like you in my ass Jack."

With that I rubbed her back in thanks, knowing that she'd be up for another round of being ass fucked soon.

In response her body began to respond at a higher level.

My fucking, my thrusts were gaining traction.

Her natural lube kicked in. More lube was never a bad thing, especially when ass fucking.

Was she tight? Oh My God. Tight doesn't begin to describe it.

Her ass was so tight it took me a long time to get into balls deep, despite her half-willingness to accept my large hard cock into her virgin hole.

And, once having conquered her ass, I was delivering a pounding, pulling back to the point where only my tip was inside of her rosebud, then pushing into her as deep as I could go, with that little extra thrust at the end, time after time.

She finally got into it, and responded by matching my thrusts with her parry.

How much did she like my dick in her ass?

I stopped fucking her; I stopped thrusting into her and she started fucking me!

She had gone from protest to acceptance to pleasure.

They all do; once I'm inside their ass they learn quickly to enjoy the new sensation, a new way to enjoy sex and to orgasm.

Her ass was twerking and riding my pole like I'd never experienced before.

It wasn't just her movements; she started talking dirty talk like I'd never heard her before.

I knew then that this was only the first of many times she'd take taking my cock up her ass.

She started moaning, and then panting; then groaning as her orgasm built up.

Her right hand found its way to her wet soppy pussy, and she began to masturbate for her own pleasure.

My hot cum moved through the pipes in my balls and my sack tightened and my cock actually grew thicker and longer, ready to plant my seed.

My hands gripped her hips as the moment neared, and I simultaneously pushed my cock deeper into her while I pulled her hips back into my crotch as I groaned "OH YEAH!" as my semen exploded into her most intimate of holes, coating the slick insides for the first time as I came in relief and satisfaction, thrusting over and over, pumping until I finally collapsed on her sweat covered back, pushing her to the satin sheets.

I'd just "analized" Natalie, my summer girlfriend. The professor at UNLV. Miss Prim and Proper.