A MILF Neighbor Plays All Night

She was in search of a source of friction so she could come.

It wasn't too blatant at first, just a slight humping movement but as I drilled, the need for Janet to come increased and so did her motion on my left hand.

But before things got out of control I took my hand away from her pussy, earning me a second, louder groan and another swearword, this time not under her breath.

"Fuck Jack, I need to come. PLEASE!"

I didn't orally respond; I let my hands talk for me.

The drilling continued with my right hand, two fingers now pounding, going deep, relentlessly, into her still tiny rosebud and my left hand reached to her large left tit and her big hard nipple.

I know I have described Janet's nipples as being the size of pencil erasers.

It's not the kind you are likely thinking of, which is the Dixon Ticonderoga Number 2 pencil.

That's the kind of pencil they use in elementary school; same as when you were a kid (some things never change).

Lee Corso holds one of these when he does his ESPN Gameday appearances during college football season.

What I'm talking about an eraser that sits on top of a 10 inch pencil with an eraser that is at close to half an inch tall and a circumference of almost a dime.

Attention grabbing.

Substantial.

Meaty.

Those things could poke your eye out.

The headlights were on all the time, if you know what I mean.

Great to pull on, suck on. Play with. Tease.

I twisted that nipple, gently, not harshly, to get Janet's attention and said "You'll come when I let you come and not a second before. Have patience little Princess."

At that Janet groaned in frustration yet again and dropped her head to the sheet and now using both of her hands, started pulling on her taut large nipples, thinking that she could get herself off this way.

I knew better than that, all though I must say my wife late was able to come a few times while I played with her nipples and wasn't touching or in her pussy.

My left hand returned to cupping her pussy.

She groaned again in what would be short term relief.

In the hopes of getting me to rub that clit and pussy of hers, Janet spread her thighs even further apart, causing her torso to drop closer to the sheet.

It also caused her butt cheeks to close up but my drilling continued unabated.

I knew where this was headed and I let it play out.

Janet's midsection soon reached the sheet.

Janet continued to hump at my hand, and she was getting the desired friction with my hand trapped under her as she moved in that ancient primitive sexual motion.

She thought she could get away with it.

Being able to come on my hand; praying that I would play with her clit with my fingers.

I wasn't going to let her come.

I leaned over to the side of her face, kissed her cheek, ran my tongue around her ear which caused her to shiver and then I whispered into her ear "What are you doing Princess?"

Her eyes closed, still humping she smiled and whispered back "I need to come Jack, please let me come now."

I said in a very quiet voice "No."

"Please Jack, I'm so close. Please lover. I need to come. You've done this to me with your massage. I need to come."

"I said no and I mean it."

With that I pulled my left hand out from under her body, pulled my fingers out of her ass and quickly flipped over the petite blonde so that she was lying flat on her back.

Janet couldn't have been more surprised at my action ... she stared up at me with wide eyes.

And an open mouth.

"What did I tell you about coming? I said you could come when I let you. Not only are you not going to come, I'm going to punish you. You've pushed me to my limit Princess. Sit up against the headboard and put your hands up by your head."

Janet wasn't sure if I was serious or playing.

I was serious.

Her eyes locked on mine and she could see some fury, some anger, something she had never seen before.

Janet knew I was pissed.

Still intently watching me, she silently did what I asked her to do.

I glanced at her nude MILF body, one of near perfection and when I saw her clit still standing at attention, I said "Spread your legs."

I was no stranger to her extraordinary, enormous clit.

I had worshiped it for two days.

With my fingers, my tongue, my mouth, my teeth and my cock.

The only thing I hadn't done was to put a clamp on it ... or watch another woman satisfy her ... both were on my list.

No man had spent that much time with her naked body in years.

Her clit was literally throbbing, standing proud on top of her very puffy lips and tight, wet slit.

I was still fully tented and I wanted to come; I wanted to fuck her but that could wait.

I walked over to my little travelling massage bag and pulled out three sets of nipple clamps.

Holding them I walked back to the bed and sat down.

Opening my hand so that Janet could see the clamps in the palm of my hand, I said to Janet "You'll be wearing a pair of these as your punishment."

Janet looked down at the "gift" I was going to give her.

She lifted her wide eyes and they met mine.

"Jack ... I'm sorry ... you don't need to put those on me ... please honey ... I learned my lesson ..."

"Princess, you will be punished. Now, play with your right tit and make that nipple big for the clamp."

"But Master ... " and there was a short sob, a sharp intake of air.

I thought she would start crying.

But I didn't waiver.

Janet understood I wasn't going to let her off the hook.

I said nothing, I kept a poker face and Janet lowered her right hand and started playing with her right breast pulling on her nipple, just as I had instructed.

She kept her eyes on my face.

She was hoping for a reprieve but very soon understood it wasn't coming.

Both of Janet's nipples got big and hard and then I said "Get it nice and wet for the clamp Janet."

She licked her fingers and pulled and teased her nipple until it was glistening.

"Hold your titty out for me."

Janet's eyes turned fearful as she did as she was told.

Smiling at her, using the "starter" clamps, the ones that were covered with black plastic to keep the pain to a minimum, I pushed open the clamp to its fullest and placed it at the base of her proud right nipple.

Janet looked down, her eyes filled with trepidation at what was sure to be a new kind of pain for her.

I let go of the clamp and it stung her breast as it did pinched her nipple at the base.

Instantly, Janet yelped like a puppy and tears formed in both eyes.

I quickly leaned in and we kissed.

Our tongues met and Janet groaned in pleasure, her hands pulling my head into hers.

My goal was to kiss through the pain but Janet had another goal ... to come.

My hand massaged her left breast while we kissed, kneading the nipple and pulling and tugging at it.

When our lips parted she whispered like a co-conspirator to me "Jack, that was like electricity running from my tit to my clit."

I looked down to see her more than fully elongated clit rising higher than ever before from the top of her slit.

I smiled at her and I brushed what remained of her tears away.

"So, you like the clamp?"

She smiled and said "Yes Master. It hurts in a very good way. Can I say something to you?"

"Sure."

"I love you Jack Colton. I really do."

I smiled at her, not knowing how to respond.

I loved all of my princesses, but I was married to Catherine.

Janet knew that.

Janet knew that the best we could do was fuck once in a while.

But not right now, because it wasn't safe.

I didn't want a pregnant girlfriend.

Unless something changed.

I wasn't sure what that would be.

She whispered to me "I wish I had met you when I was in college, I would have grabbed you and never let you go!"

I kissed her lightly on the lips in thanks and then Janet whispered "Anywhere you want it Jack, anytime and anyplace. You just let me know and I'll be there to take care of you in every way. I love you Jack."

Our tongues met and played and I moved my right hand to between her legs, fully cupping her bare pussy again.

Janet groaned into my mouth and started to slowly hump my hand, still searching for her orgasm.

Her clit was huge!

And was it ever sensitive.

I pulled my hand away and she ended our kiss with a groan and a breathless question: "Will you clamp my other titty please Jack?"

I smiled at her and we kissed again.

I liked kissing Janet and she liked kissing me.

She said "I like it when you punish me."

I smiled and said "Keep ignoring my instructions and I'll keep punishing you."

"I will Jack" Janet laughed, following with "I think I might like you spanking me."

"When?" I asked her.

"Oh, I'm sure I'll push your buttons sometime soon and you'll be spanking me before you know it."

"I'll spank you and then make you go to the pool so everyone can see what your red ass looks like."

"Is that a promise Jack?"

I smiled at her and we kissed again.

She really was something special.

This was the kind of woman you would take to a tropical island and she would stay naked until it was time to get on the plane.

If you asked her to fuck another guy she'd do it in heartbeat just to please you.

If you wanted her to lick pussy, she'd do that too.

She wasn't just a good time girl; she was college educated, smart, articulate and nice.

But she was like so many MILFs I had run across since my wife passed; Janet had been ignored sexually and now, set free from a jerk of a husband, was making up for lost time in the sex department.

With me.

I had some vague plans in the back of my mind for her that I wasn't sharing with anyone at the moment.

Personal plans not business plans.

Ideas as to how I could satisfy my carnal needs.

I recognized the problem I had with Janet: I simply could not keep my hands off of her.

One long night and one full day of nonstop touching and sex with her and I was an hooked.

I was quickly becoming addicted to Janet.

Was she a siren, luring me to a crash?

Or was she the real thing, genuine?

Was it just the lure of easy pussy that had me by the short hairs?

Or was it something more?

Janet had a big set of hooters so I needed to be careful not to brush up against the clamped nipple.

I pulled away from her and said to her "Do you want to try another style of clamp?"

I had in mind the alligator clamp, the one with metal teeth.

Was I turning into a sadist?

Was this for her pain or my pleasure or both?

Janet shivered for the second time when she saw what I had in mind.

I could literally see her tilt her upper body away from me.

Janet asked, with a just bit of fear in her voice, "Can we just use the one you picked for me this time? Please Master."

"Sure" I replied and as I looked down at her left tit, I took in her left nipple.

It was standing proud, waiting, just waiting, for the pain device.

I leaned down and sucked on the large hard nip.

I ran my tongue around her nipple and pulled on it with my teeth; not biting down just using my teeth to pull on it.

Janet groaned at this unexpected treat, this pleasure.

Her hands went to my head, holding me close as I sucked.

I suckled for a long minute and then, without warning, I quickly clamped it and heard another yelp.

More tears.

We kissed again.

Janet groaned again into my mouth and she pulled me in for a long kiss.

The clamps were making her hotter and hotter.

I ran my hand down between her legs and rubbed that huge clit and she groaned into my mouth.

But I wasn't going to let her come, as bad as she wanted it.

I could have fucked her right there and I would have, despite Catherine's instructions.

But I was a good and faithful husband and I passed on the opportunity to fuck Janet senseless.

There was a light knock on the door.

"Keep your hands up, by your head" I said as I got off the bed to see who was interrupting.

I had to arrange my shorts; my hard on was quite evident.

Janet laughed and said "I really wish you would let me help you with that condition ..."

I laughed and said "Me too."

As I turned to the door I noticed she was trying to hide her nude body with the covers.

"Janet."

Her eyes looked up at my face.

She smiled.

"Stop."

She did.

I quickly took a few steps to the bed and kissed her and then I whispered to her: "I want you naked. I always want you naked. And spread those legs, let me see your pussy and that big clit of yours. You have a fantastic body and you're going to be showing it off."

Janet's face blushed but she smiled and we quickly kissed and then she nodded and replied, "Yes Master. Thank you Master."

I closed the door to the bedroom and found Dorrie waiting in the hallway, wanting to come into the suite.

Dorrie was dressed in one of those white terry cloth robes you find hanging in the closet in your hotel room.

And she had a bag about the same size as you would use to take your things to and from the gym.

****

As I closed the door to the hall behind her, Dorrie reached up and pulled me to her for a kiss.

Dorrie was a very good kisser and I knew she liked kissing both boys and girls.

She knew I liked to watch her kiss girls, and I liked watching when Dorrie played with them too.

"Hello Master. Catherine wants you to go back to your suite now. She sent me down here to take care of Janet tonight."

I nodded.

"I wish I could help you with your, eh, situation, Jack, but I can't" Dorrie said as she stroked my hard on through my thin shorts.

I smiled and said "I understand."

What Dorrie was doing felt damn good but she was under instructions from Catherine so...

I asked "What's in the bag?"

Dorrie smiled and said "Remember that night in Las Vegas when you babysat Lourdes and me? I saved all those toys you bought because I knew they would be useful on a rainy night. And here we are."

It had started to snow towards the end of our day at the ski resort and was raining, with thunder and lightning, here in Sedona.

I chuckled in response as I remembered that night which is my story "An Interesting Evening in Las Vegas."

Dorrie looked up at me and said "Would you please undress me Jack?" and I slipped the soft white robe off of Dorrie.

She was so fucking good looking nude she took my breath away.

She was a knockout with clothes on too.

Her bush was starting to grow back and I reached down and I felt the soft downy hair Dorrie giggled and whispered "Careful Jack. If we start playing you might not make it back to your suite. I don't want Catherine mad at me."

I nodded; I didn't want Catherine mad at me either.

It's tough being the king when you have a queen to answer to.

If anything, Dorrie had gotten better looking and into better shape than the last time I had been naked with her.

Maybe it was getting the divorce going, moving to Las Vegas, working out, I wasn't sure.

"Have you been working out?" I asked Dorrie.

She smiled and nodded "Julie has been training me. She's tough but the results speak for themselves."

I kissed her softly and said "Keep at it sweetie. You look great."

Dorrie beamed in appreciation as I took in the sight of her flawless body.

But I remembered quite vividly the last time I had seen Dorrie naked.

It was in Beverly Hills, the night I took her virgin ass, coming in it three times.

The first time she was tight, oh so tight, and there was some mild protesting punctuated by her moaning and groaning as I slowly penetrated her virgin rosebud.

Dorrie had used a thin dildo up her ass before but it had been a long time and she confessed it was nowhere near the size of my erection.

There was some fear in her eyes as my cock grew as she sucked me to hardness prior to me penetrating her for the first time.

I can't tell you how many times I had to stop my thrusting before I was finally able to impale her fully; all the way in, balls deep.

In addition to the moaning, there were tears, she was gripping the sheets with her balled up hands and she begged me a few times to take my cock out of her ass.

I had told Dorrie "Once I start I don't stop."

I used plenty of lube, and Dorrie knew it was going to happen.

She knew I was going to fuck her ass when she surrendered her panties to me two nights before.

That was part of the deal; part of becoming a princess and Catherine had made all of this clear to Dorrie.

After spending a wild night in Beverly Hills with her, I had flown Catherine and Dorrie up to Las Vegas in our private jet where we spent the night on Saturday after spending all afternoon at adult pool.

On Sunday morning, Dorrie was out the suite by 6am for her first photo shoot.

Dorrie had been measured for a couple of suits when we were at the factory, but she had no idea how small the suit was that she was going to be wearing for the photo shoot.

One of the cool things we were able to do for our models was that we could quickly get what we called "plastic casts" of each model using thin white plastic.

This allowed us to have a mannequin for each model and we could play with the material to custom fit the model, even though the model was long gone.

So, all Saturday afternoon, the designers at the factory were using FaceTime to show me what they had come up with.

I started reducing the amount of coverage so that in the end, the suit left nothing to the imagination.

The top covered only Dorrie's nipples.

Actually, not quite.

Most of Dorrie's areoles were covered by the cloth, but not all.

I knew right then that this would be a best seller.

As for the bottoms, well, Dorrie might have as well have been nude because I wanted the suit not just tiny, but sheer and white, and so once it was wet, it was see through.

It left nothing to the imagination.

Dorrie would be showing a major camel toe as soon as she slipped the bottoms on.

She didn't know any of this until she had her hair and makeup done for the early morning shoot at another location.

We had created six different suits for Dorrie, and the Jennifer, photographer started with the most conservative.

The Jennifer would text me a photo or two after each set.

The shots got more and more revealing.

Catherine liked what she was seeing.

Late on Sunday morning we met up at adult pool.

Dorrie didn't have a chance. She had no sooner walked into the cabana when Catherine had Dorrie and Lourdes get in the pool and then walk around showing off.

In their see-through when wet bathing suits.

Dorrie asked if she could please have a glass of wine before getting in the pool and Catherine agreed.

I pulled Lourdes aside and asked her "How many times did you make Dorrie come?" and I didn't get the answer I wanted.

No wonder Dorrie was still nervous.

So, after one glass of wine, Catherine had them in the pool, splashing one another and then they took the walk of fame around the pool.

Conversations stopped.

Heads turned.

All eyes were on Dorrie, who I have to admit, was fucking hot in that bathing suit.

Lourdes was just arm candy for Dorrie.

Once back at the cabana, Catherine had Lourdes put lotion on Dorrie and Dorrie got to put lotion on Lourdes.

About 1:30pm, Catherine had Dorrie take off her top and walk around the pool with Lourdes.

Catherine warned Dorrie about keeping her hands down, away from her body, so that all the men and women could enjoy the sight of her large, firm breasts.

When the pool went nude and alcohol free at 3pm that afternoon, Catherine had Lourdes and Dorrie naked.

The two of them were pretty worked up and were the center of attention that afternoon.

Before we left the hotel for the airport, Catherine asked Dorrie to put back on the bathing suit for the flight home.

Our trip back to Santa Monica was short, but Dorrie was so worked up she asked us for permission to masturbate in the tiny bathroom.