I Enjoy Two Threesomes In Two Days

My stories are in chronological order starting my "I Hire Monica The Maid" but if you want to know the background of this specific story, start by reading "I'm Ambushed by a Very Hot MILF!" followed by "In Hot Pursuit of a Very Hot MILF" and then "Roadblocks to Pursuing the Hot MILF" and finally "Nirvana! My Hot MILF Likes Pussy!"

These are my stories of how I reconnected with Catherine, a friend of my deceased wife.

This story picks up as Catherine (my fiancée) and I leave Los Angeles to return to Canada.

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Neither Catherine nor I brought up our spending the night with Kim in a three way until later that afternoon when we got to our hotel in downtown Chicago. Kim was an interior designer, a friend of my late wife and I had hired her in the story "I Rub an Asian MILF the Right Way."

I couldn't get us a nonstop flight to Ottawa from LAX so I thought we'd be smart to get close geographically and then meet up with Tom and Isabella (Catherine's parents) and Marie and Natalie (her daughters from her previous marriage) on Wednesday, hopefully in time for lunch but certainly in time for dinner.

Selfishly, I wanted another night alone without her parents or children around. Not that I didn't love them. But except for Saturday night in LA, we have been nonstop with other people and had not had much alone time.

But I was also being sneaky and picked Chicago as our stopping point for a specific reason as you will read.

Catherine and I were both sleep deprived from three full nights of literally nonstop sex and going hard all day with our tasks. Catherine was getting everything ready for our new home and I had taken over the ownership of a luxury car dealership plus I had other business clients to deal with.

Actually, it wasn't having sex with Catherine that wore me out, although she did do a very good job of that on Saturday night, after we landed in Los Angeles, and when we spent our first night together in my house.

Catherine literally drained my balls the first 18 hours we were in Los Angeles. It was if my fiancé had found a new lease on life and was making up for lost time by fucking me at every opportunity.

Now, I wasn't complaining. I loved having sex with her. If you saw the movie "The Wolf of Wall Street" there is a scene were Leonardo DiCaprio talks about Margot Robbie's pussy as so good it's like heroin. Addictive.

Catherine was addictive to me. Not just her pussy, but her entire being.

When we landed in LA I think she was finally starting to realize how much her life was going to change for the better and she was rewarding me for being her knight in shining armor.

I was rescuing her financially, emotionally, sexually and giving her a life she never thought possible. A new car each year. A brand new custom house she could design. A sense of recognition in the community because she was going to be married to the guy who had a fairly impressive business in town. And a loving fully devoted husband. Travel. Clothes.

She paid me back with nonstop sex and the promise of more threesomes for me to enjoy a variety sexually.

We had two threesomes already. They were fun but tiring -- the guy who pumps uses a lot of energy.

Oh and one more thing; Catherine had promised to take me in all three of her holes. I was really looking forward to being the first and only one in her back passage. I got hard just looking at her ass and thinking about how I was going to plunder it.

But starting our weekend in Los Angeles with a sleep deficit did not help me. Nor did working the long hours at the car dealership I had taken over.

What really wore me out, the tipping point, was fucking Kayla on Sunday night, and I did her all night long. In all three holes. It was amazing sex. Fucking amazing.

Not better sex than sex with Catherine. But different and still great.

Following our threesome, after a fucked out Catherine fell into a deep sleep in the next bedroom in our suite at the Hilton, I was pounding the super tight, steaming hot wet young hairless pussy of a young lady who had long sought for me to fuck her.

After my night with Kayla and Eva (read the story "I Get Rewarded for a Job Well Done"), Kayla and I had exchanged texts but owing to my business and travel schedule, I had not been able to meet with her, meaning, have a free night to fuck her senseless.

But Kayla made it clear she was interested in me; she was very persistent. When Catherine fell asleep that Sunday night at the Hilton, as our threesome died out, I took Kayla by the hand to the second bedroom in the suite and we frolicked nude in the bed.

We fucked. Serious fucking. My cock in her mouth, her ass and her pussy. Dumping loads of hot sticky cum into her welcoming orifices.

I want to be clear that I wasn't cheating on Catherine. Catherine had participated in our three way until she fell asleep. I chose to take Kayla to the other bedroom in the suite so as not to wake Catherine.

A good man takes care of his loved ones. That means helping them get a good night's sleep.

Kayla laid me down in the king size bed and climbed between my legs and started licking. Kayla was a very experienced cock sucker, and I noticed for the first time that her tongue was a bit longer than other women I had known. That genetic novelty worked well for me. For Catherine too.

Kayla rimmed me, then licked at my balls, getting my sack tight and stimulated, hoping that it would produce lots of sperm for me to shoot, and then she started licking at the crevice between my balls and my thighs. That area is very sensitive and very stimulating, and I got to rocket ship status fast, which I am sure, was Kayla's intent.

She hadn't said a word to me to this point; it was almost like she was so focused on getting me hard that who she was teasing wasn't important. Kayla began running her tongue up and down my cock, wetting it, avoiding the tip, just licking, and kissing, teasing me until I was rock hard.

I had my hands on her head, guiding her efforts. She gave great head. Even Eva and now Catherine would agree with me and so now I was experiencing her work ethic for the first time with just the two of us alone in bed.

But when I got hard, very hard, she looked up and smiled at me and said "Jack, I want you in my ass."

I reached down and found her stiff puffy nipples and pulling on both of them, I said "Mind your manners, sweetie."

Kayla smiled up at me and lowered her head and licked at my balls again, and then lowered her head even further and rimmed my starfish which garnered a groan out of me.

Kayla looked up and said "Pretty please, Jack? Will you please fuck me in my very tight ass now? I've been patiently waiting for you."

With that, her mouth closed over the very sensitive tip of my cock for the first time this session and I groaned loudly in total appreciation. My hands tightened around her head, keeping her on task, and her tongue swirled around my tip, over and over, and she went deeper and deeper down my shaft.

I wondered for a second if Kayla could deep throat me while her tongue was swirling around and around my cock, all the way to the base, and then could she lick by balls all the while I was deep into her throat?

The feeling was incredible and while I wanted to cum badly at that moment, I wanted to give Kayla what she wanted so I lifted her head off my now wet and very hard cock.

With a naughty smile, she got off the bed and left the room, returning with Astroglide. Kayla climbed on the bed and coated my erection, very liberally, very sensually, and then she started licking my balls again, making sure the sack was nice and tight. I was more than ready to make a deposit in Kayla. Any hole would do, but she wanted my cock in her ass and I did not want to disappoint her.

As I watched she reached back to her anus and coated her rosebud. She looked up and smiled at me and said, "I've been wanting you to fuck in the ass since the last time we were together." With that, she climbed up and straddled me, and began lowering herself on to my cock.

While she slowly impaled herself on my hard cock, she whispered to me "No one does it as good as you Jack, no one."

Kayla winced as the base of my cock, the widest part, expanded her tiny hole well beyond normal as she got close to the root but she never stopped or pulled off.

Her rosebud was so fucking tight it almost hurt. I could tell Kayla was turned on because her newly shaved pussy was glistening with dew, her lower lips were separated, ready for penetration and her little nub was stiff. Her areoles were puffy and her nipples enlarged.

I reached up and began to play with her world class tits (movie reference, Katie Holmes in "Thank You for Smoking."

I first saw Kayla's nipples that night with Eva. Kayla's pink nipples were almost an inch long, by far the longest I had seen to that point. While I had seen and enjoyed some long nipples, these were the gold medal winners.

Kayla moaned as I rubbed, teased, tweaked, pulled and twisted her nipples.

I whispered to her "Have you ever been clamped?" but she did not know what I meant so I said "Have you ever had clamps on your nipples?" and she shook her head no.

I smiled and said "Tonight you will."

She didn't respond, her attention was elsewhere --- the new and powerful sensations now coming as a result of something large and firm moving in her ass.

Kayla began to move, slowly, up and down, trying to adjust to my male log now lodged into her very tight bat cave. She was no stranger to anal sex but I felt about as big as I ever had been and having this hot blonde riding me was one version of heaven on earth.

With my left hand on her right nipple, pulling it out, causing her a sharp pain, my right hand left her left breast and rubbed its way down to her flat belly and then below it to the top of her pussy, in search of Kayla's little nub.

I rubbed around her pussy, stimulating the blood flow, then licked my right thumb, getting it nice and wet before I placed it on her aroused clit.

Slowly, oh so slowly, I started to rub her hard nub, while she began to move around on my erection, in search of greater pleasure.

I removed my left hand and said to Kayla, "Play with your titties for me while you ride me" and taking my hand off of her clit, I began to lift her torso off of me and then I let her ride me down.

This got her started fucking me and after she got the hang of it, I didn't need to lift her and so my hands found their way back to her nipples, where I pulled, twisted and squeezed them, causing Kayla to gasp and groan at the pain and the pleasure, and then, while her blood filled nipples bounced with her thrusting, I returned my attention to her now bigger than ever clitoris, which stood proud above her parted hairless wet pussy lips.

Kayla was worked up but the orgasm she was hoping to achieve wasn't coming so I had her lean back, her hands on my legs, which exposed her entire torso to me, especially her shaved pussy.

Using my hands, I proceeded to penetrate her with my left hand, and with one finger quickly found the soft pad of Kayla's g spot. I began massaging it, softly, teasingly, as Kayla started to rotate on my cock.

She started to oh and ah, and her rotation picked up speed. She began licking her lips, her tongue running around her mouth.

I wet my right thumb again and started back on her clit, which seemed to grow larger before my eyes.

I could feel that it was very stiff. Stiffer than before.

This kind of assault on Kayla was new to her and the sensations were a first for her. On those nerve endings in her ass, on her g spot, and on her clit.

If I could have clamped her nipples at this point I would have, because they looked so inviting and tempting I know they would have added positively to the sexual sensations Kayla was enjoying.

It only took a few minutes before Kayla came and she came big. Not a gusher but she started humping my thumb to make sure that every nerve ending in her clit got massaged and rubbed.

I just let her ride and then she collapsed onto me. I held her for a few minutes rubbing her back and then had her dismount from my still hard cock.

I slapped her ass and told her "Get on your knees" and then left the room, returning with the nipple clamps.

Kayla sat up on her haunches with those almost inch long nipples standing out proudly on some very firm young breasts.

I came up beside her, standing next to the bed and bent down and kissed her.

I tasted a bit of my ass but I didn't care; it was my ass.

She loved kissing me and her hands went up to hold my head to her mouth.

My hands went to those magnificent tits.

I manhandled them.

They were big and firm.

Young tits, great for playing with.

I pulled my lips away and said, "Wet your nipples for me sweetie" and she did.

"Now play with them, make the nice and big, as big as you can make them. Pull on them honey."

She smiled at me and did as she was told, seeking my approval.

I think she knew what was coming.

"That's great Kayla, now put your hands up behind your head and push your titties out for me."

Kayla did, with a smile.

"Good girl."

Kayla's tits were large firm and had tan lines in all the right places.

With my left hand, I took hold of both of her hands, and with my right hand, I clamped her protruding right nipple.

Before she could move a muscle, before she could utter a syllable, my mouth was on hers, stifling her cry of pain.

She responded by an aggressive kiss, with dueling tongues, which continued for a full minute until I pulled away.

Our lips separated and still holding her hands up, I looked at her and she had a few tear streaks running down the side of her face.

With my right hand I brushed away her tears and kissed her again.

She smiled at me.

I glanced down at her beautiful firm right breast, now nicely adorned with a gold clamp.

For a minute or so I massaged her right breast, avoiding the nipple and the clamp.

She said "That feels good Jack."

I dropped her hands and the left one immediately went to her left breast, covering it, protecting it.

We kissed again and I said to her "Kayla, move your hand honey, let me see your beautiful tit."

She took her hand down, her nipple now unprotected.

I looked at her left breast and found a larger, highly aroused nipple, waiting to be clamped.

Kayla looked at me as if this was no big deal.

"Did that hurt?" I asked in a low voice.

She smiled and said softly, "Yes, but so does having your big cock in my ass" and we both laughed.

I kissed her and she kissed me back, lots of tongue.

Her hands went around my head and she pulled me to her.

We kissed for a long time; all the while I fondled that bare breast.

When our lips parted I said to her "Kayla, honey, please make your titty ready for the clamp" and she wet her nipple, and held her breast out as an offering and I clamped it.

When the metal closed on her sensitive bud she inhaled sharply but there were no tears.

I massaged her left breast, avoiding the clamp.

Kayla kissed me again and I took her head into my hands and we kissed like long lost lovers.

"You're a good girl Kayla. You have a fucking great body. I can't wait to see you topless at the pool in Las Vegas. You're going to make a lot of women jealous and a lot of men very horny."

By now my erection had shrunk a bit so with my hands, and without a word, I directed Kayla to revive my cock with her mouth.

Kayla gave great head and I responded to her lips, mouth and tongue accordingly.

She didn't mind that my cock had just been deep in her bat cave.

I looked at her and said in a low voice, because I did not want to wake Catherine, "I want to cum in your ass now sweetie" and she smiled at me and assumed the position, head down, ass up and legs spread wide for my access. Her beautiful, clamped tits swayed under her.

Getting up behind her, I poked her without preamble or additional lube and drove all the way in with a single firm stroke.

She screamed into the pillow and reached back with her hands to signal me to stop but before she could do that, my balls were slapping against her wet pussy lips and my hands holding me inside of her so she couldn't pull away.

She shook for a long time as she accepted this long, large and rather sudden semi-expected invasion of my cock into her tight asshole.

Her hands gripped the sheets. Her knuckles were white.

Kayla lifted her head slightly and I could see tears running down the side of her face.

"Oh my God Jack what was that?" Kayla asked as she turned her head to look back at me.

"I took you like Eva sweetie, plenty of foreplay and when it was time, when I was ready, I took you. To be in you, fast and deep."

With that I pulled out a few inches and then I slammed back in, driving deeper if that were possible.

Kayla screamed again, her ass and shoulders shook and I could hear her crying.

Sobbing.

This can't be good I thought.

What happened to the young lady I was riding a few minutes ago, the one who enjoyed my cock deep in her ass?

I didn't want to be an asshole about this (no pun intended) and it wasn't my intention to cause Kayla to cry so I pulled out, quickly.

When I did that Kayla lifted her head up and said "What are you doing Jack? I want you to fuck my ass! Stick it back in!"

With that she reached behind her with both hands and pulled her cheeks apart.

"Stick it in Jack, fuck my ass!"

Her hole was still enlarged, but shrinking, waiting for my cock.

I slammed into her, all the way in, as deep as I could push.

Kayla shook and this time, she moaned.

I had struck some nerves deep in the dark cavity that caused her to react in a way I had not expected.

Over and over, I pushed in deep, sometimes pulling all the way out and re-entering her winking hole, going balls deep with single strokes.

I am sure that I went into previously unclaimed territory with my deep thrusting, and each time I earned a nice groan or maybe it was a grunt, out of Kayla.

My balls were continually slapping against her wet bare pussy.

I took her ass in four different positions over the next half hour or so before coming deep into her dark hole.

As we switched positions I had Kayla suck me back to hardness.

The first time she sort of looked up at me with a "Really?" face but I just nodded and she smiled and licked, sucked and kissed my cock until I was groaning.

I knew it was dangerous to keep clamps on nipples for too long so at one point I interrupted my humping and relieved those glorious nipples of the pain I had caused.

Kayla loved it when I sucked her nipples when I took the clamps off.

Kayla came twice as a result of my pounding of her ass mixed with her fingers furiously rubbing her clit.

After I poured, literally, into her dark tunnel, I had her clean my cock with a warm washcloth and do quality assurance work on my shrinking cock with her lips and tongue.

That tender activity returned my erection to rocket ship status and I spent the rest of the night fucking her hairless pussy and her mouth.

Kayla was great at head and had worked hard on improving her already impressive deep throating since our night with Eva.

I was able to get my prick down Kayla's throat without her gagging and I held her head to my crotch as I exploded down her gullet. I was pretty sure I felt her tonsils on the top of my cock.

Finally, about 3am, she asked me to stop, no, begged me to stop, a dazed look on her face of someone who had truly been fucked out.

I had come in her ass, her pussy and her mouth. I have no idea how many orgasms she had but she looked wiped out.

I took her by the hand, got her into the tub, and gave her a quick quiet bath. I washed her pussy and her rosebud. She was almost too tired to kiss me.