I Enjoy Two Threesomes in Two Days

"But Jack, right now it's all talk."

Silence while I thought all this over.

I answered the silence by saying "Not really, I am here in Chicago with you. Kim is in LA or somewhere by herself. And we're leasing a house and planning to get married and have kids and travel the world."

I got no response. Just more rubbing with the bar of soap.

Now, don't get me wrong, the rubbing was nice and so was having Catherine behind me, snuggled tight up against me in the shower.

Catherine broke the silence with "I kind of felt we were just using you last night. Two horny women taking advantage of an available large dick."

"I had a good time honey" I replied, "But I did think I was going to actually go to sleep when you came and got me off of the couch last night."

Catherine whispered into my ear, her hands still rubbing "I'm sorry about that. Do you forgive me?"

I turned around to see a smiling Catherine, who got bumped in the belly by my erection.

"Will you forgive me Jack? What can I do to make it up to you?"

She smiled at me, knowing full well I had nothing but carnal thoughts running through my mind.

Catherine looked at me and said "I want to be open with you. I loved watching the way you fucked the shit out of Kayla the other night. Will you do that to me now?"

We got out of the shower, dried each other off and hopped into bed.

This time, we fucked like animals.

I jackhammered her in every room in the suite.

The living room had floor to ceiling windows and we weren't all that high up so I am sure some Peeping Toms saw us.

I didn't care, I had some energy back and my girl wanted to be taken, hard, and I did the deed.

I came in her twice in about an hour and in between she sucked me back to hardness.

She had pulled out her little book of Kama Sutra illustrations and we screwed in four more positions.

The pages were getting worn.

We were picking out some favorite ways to fuck.

++++

Post sex, Catherine laying by my side, snuggling, I asked her, "What time is it honey?"

"It's six Jack."

"How long do you need to get ready?"

"Where are we going?"

"Out for about an hour or so."

"Where?"

"Sweetie, would you please trust me on this?"

"Jack, I need fifteen minutes."

"Get dressed please."

I slapped her fantastic ass as she got out of the bed.

She laughed at me and said "I'd rather stay in bed with you but if you want to go out, I'll go with you."

I replied "I'll make it worth your while."

++++

At 6:35 we were on the sidewalk outside of Tiffany's on Michigan Avenue.

I told Catherine "I want to buy you an engagement ring and a wedding ring. This should take us past the just talking stage."

She smiled a huge smile, nodded and kissed me.

Then, her chin started to quiver and Catherine started to cry.

I just held her until she stopped. We stepped inside out of the summer heat and humidity into the air conditioned store.

Holding hands, I thought about this lovely woman by my side.

I loved cumming in her.

Into her shaved pussy.

She loved to suck cock. My cock.

She swallowed without hesitation.

Soon I would take her virgin ass.

I just had to be patient.

She allowed me to fuck other women.

I needed to seal the deal.

She picked out the diamond and got her finger sized.

It was a huge --- 2.5 carats.

Catherine took a picture of it and texted it to her mother.

It wasn't cheap. $60,000.

We would pick up the ring on our next return trip to California.

I called my insurance agent to get this asset insured.

I knew a little bit about Tiffany's and how the sales people earned commissions so I had picked the youngest, hottest girl I could find.

Before I said a word or spent a cent.

Her name was Jennifer and I was laying the groundwork for the return trip to Chicago when we would pick up the ring.

Catherine and Jennifer hit it off.

We invited her to join us for breakfast at the hotel so she could discuss my wedding band.

Catherine and I went back to the hotel and enjoyed some champagne with dinner.

The Langham has a quiet, refined dining room and a great menu and wine list.

For the first time we talked about getting married and being married and what that looked like.

As a couple.

As a family.

We talked about the girls and we reviewed the notes my late wife had made about them.

Were they in the right schools?

What kind of students were they; did they need help and what kind of help.

How about her parents?

Would they be okay moving?

When would we get married?

Where would we get married?

Where would we go on our honeymoon?

When should she stop taking the pill?

What did we want in our new home?

It wasn't a deep conversation but we covered a lot of topics.

It helped that we had both been married before.

We were still feeling the effects of the last three night's lack of sleep and we were back in the suite by 10.

++++

Catherine took a bath and I laid down on the couch, still dressed.

I woke up with a blanket on top of me. The room was dark. I got up, undressed and used the bathroom before climbing into bed next to my nude fiancé. I didn't wake her and fell back asleep.

For some reason I have the gift (or the curse) of waking up each morning at 5:30. Regardless of the time zone.

I slipped out of bed and used the bathroom before getting my gym clothes on. I tried to be quiet but apparently I wasn't quite quiet enough.

When I walked into the bedroom Catherine said to me "Jack, please come back to bed with me. You can work out tonight before dinner. I got us a wakeup call for 7:30. Please honey, come back to bed with me."

She made me an offer I could not refuse.

I got back into the bed and snuggled up to her and Catherine whispered to me "Hold me like you'll never let me go."

I kissed her neck and we both fell asleep until the phone rang.

I was spooning her with a big erection in her crack and my right hand on her flat tummy.

Catherine rolled over next to me and said "We have thirty minutes before we need to get out of bed ..."

She kissed me and reached down for my hard cock, and began stroking it.

Catherine said "I tried to wake you last night but I couldn't so I covered you with a blanket. What time did you come to bed?"

I was still a bit sleepy and I told her "I have no idea."

Catherine looked up at me and confessed "I heard you fucking Kayla the other night in the other room and I was bit jealous."

Then she laughed and said, "That lasted about thirty seconds before I realized what you were doing to her. I'm not ready to have you fuck me in the ass yet Jack, so I got over being jealous once I heard Kayla scream. But she did seem to get into it ..."

I replied "What do you want me to do honey?" and Catherine said, as she stroked my very hard cock, with a smile, "Make love to me Jack. You can fuck other women Jack but you can only make love to me."

She stroked me a couple more times, teasing me to a new level of hardness, and then lowered her mouth to get me nice and wet.

Then she climbed on top of me and slipped me into her pussy.

I groaned and said "Oh My God you feel so fucking good."

God it was tight, wet, hot and bare, probably as tight a pussy as I have ever had.

"Is it tight enough for you love?" Catherine whispered as she started riding me, ever so slowly, her amazing breasts on my chest and her mouth kissing my ear. I could feel her hard nipples scratching pleasantly.

I groaned back "You are so tight" and she smiled in reply when she said "This tight pussy is only for your pleasure."

With that she lifted her head up and we kissed as lovers, while her lower lips found new and better ways to bring me pleasure.

"Let's pretend we're making a baby honey" she smiled at me.

Catherine slightly increased her tempo as her slippery fluids coated and re-coated my cock with each stroke.

She had a wicked look in her eyes and she started rotating ever so slightly on her upstroke.

I groaned at this new highly pleasurable feeling.

"Do you like it Jack? Do you like me riding you?" she laughed.

"Oh God I love it" I said out loud as her mouth sought out mine for some spit swapping.

My cock got harder and Catherine slowed down her strokes "I know this is making you feel so good lover. It's making me feel good too" as she groaned.

She was grinding her hard clit against my pubic bone.

I closed my eyes and focused on her tight pussy gripping my pole.

"How would you like to have this every morning lover?"

"Oh yeah" I replied.

My hands were on her hips, then on her back and I pulled her in for a kiss.

"You'll have to change your wakeup time."

"If you wake me up like this, I'll do anything for you."

"Mornings are best for making babies Jack. I want to make babies with you."

Having confirmed morning sex as part of our new life, Catherine picked up the pace, just a tad faster and she started twisting on my cock just a little bit more.

I groaned again and she laughed, whispering to me "Come in my pussy Jack, come deep in my pussy. Make a baby with me. Cum with me lover."

She kissed me again and I could feel the inevitable happening; my balls tightened, loaded with cum, the cum starting to make the journey north.

Sensing my coming blast, Catherine quickly picked up the pace, her strokes going faster and faster and she said, "Cum in me Jack, cum in my pussy."

We looked at each other with the look of love and her eyes rolled back in her head as she came, heavily, gushing over me.

She shook, she shuddered and she collapsed on me.

A few seconds I blasted her insides with a pent up load from being hard and then soft again for hours.

I grabbed her by the hips and pulled Catherine down so my swimmers would go deep, as nature intended.

I swear I pumped her for five minutes it felt so fucking good.

Her wet and hot lower lips were like a vice grips on my steel pole.

When I was done she laughed and smiled then kissed me and said "Jack, I want to please you like this every day."

I laid there, she her head on my chest, I could feel our fluids dripping out of her pussy.

After a few minutes of savoring the closeness, Catherine got off of me, and pushed my legs apart, kneeling between my thighs.

She looked up at me and said "My, what a mess we have here. Did I make this? I guess I need to clean it up."

Catherine lowered her head and lifted my still aroused dick with her fingers and began to lick it clean of our combined juices, all the while she was lightly stroking my penis.

Her tongue was just as talented as her pussy. Her fingers and nails were merciless in their quest to pleasure me.

Her fingers danced at the tip down to my balls, which soon tightened as she teased me.

Catherine had that gleam in her eye. I knew that look, the look of a woman on a mission.

It didn't take but a few minutes for me to recover and she lifted her head up and said, "I want you in my pussy again before breakfast Jack."

Smiling, she said "Take me from behind honey."

Catherine assumed the position, head down and ass up, on her knees, her legs spread for me.

I climbed up behind her, pushing her legs further apart and pushing down on her lower back to line up my penetration.

Smelling her ass odors, I reached for her bare pussy.

It was still sopping wet and she groaned as I rubbed all over her pussy and found her clit coming out of hiding.

"Stick it in Jack, please. Don't tease me. I want your cock now."

I grabbed my cock with my right hand and targeted her lower lips, pushing in slowly, deliberately, forcefully, only to feel Catherine shudder in a small orgasm and then she lifted her head up off the pillow and groaned "God I love your big dick!"

Her ass shook again from another small orgasm and in response with a single thrust I went balls deep into her waiting female furnace.

I groaned, acknowledging how good she felt, the insides of her pussy gripping me tight, oh so fucking tight.

She groaned again at the penetrating intrusion of my hard love muscle.

My hands went to her hips as I started with the in and out.

All the way out and all the way in, balls deep.

Keeping control of the pace of my thrusting with my hands on her hips, Catherine began pushing back at me, fucking me back.

She reached underneath to rub her pussy as I pumped.

I licked my right thumb and rubbed all around Catherine's exposed and winking rosebud.

She responded, laughing and grunting as I picked up the pace of my pounding, "Don't get any big ideas back there. But I like it Jack, it feels good."

I pumped her to her third orgasm of the short morning as I stuck a wet finger deep into her rosebud.

She bucked at the invasion of my finger and I said to her "That's the finger my wedding ring will be on. When you look at my wedding ring I want you to think about my cock in your ass, pleasuring you."

She groaned again in approval.

As a second finger joined the first in virgin her anal cavity, Catherine moaned a deep low growl of intense pleasure and she started to fuck my two fingers, all the while my hard cock was see sawing in and out of her dripping, hot pussy, controlled by my hands on her hips and in her ass.

I swear her pussy got hotter as I pumped.

Catherine was on fire and when my third finger ever so slightly entered her asshole, really starting to stretch her, she came again on my cock, shuddering and shaking, her fingers rubbing her clit as fast and furious as I have ever seen a woman masturbate.

Her whole body went stiff as she came and the loud moan that came out of her was nothing I have ever heard before; a combination of a woman in heat and a wounded animal.

I had her legs spread and her feet were wrapped around my calves in a position of total openness and submission and the only way she could escape my double penetration was to collapse on the bed, face first.

She begged me to stop. That the pleasure was too intense, too much for her.

I lay on top of her heaving body as she gasped for air. I pulled my three fingers out of her ass on the way down but my still hard cock was lodged deep inside of her. I kissed the side of her face and her ear, licking it to get a reaction out of her and she chuckled.

It took her a few minutes to recover from her orgasms.

Catherine started laughing as only a lover can and said "You hit a home run Jack. Back to back orgasms for me. That has never happened to me before. How many fingers did you have up my ass? That was incredible. What an amazing feeling. No wonder Kayla wanted you in her ass. I'm starting to see why you want to fuck my ass."

I pulled my still hard dick out of her now sopping pussy and it flopped down on her crack. Instinctively Catherine pushed her cheeks together, somewhat trapping my erection between the firm flesh.

"That feels nice Jack, don't stop."

I had one eye on the clock because I knew we had to be downstairs to meet with Jennifer at 9am and we needed an hour to get ready, dress and pack.

I picked up the pace; essentially I was searching for a quick way to cum on Catherine so we could get going.

More than once I paused as my tip was poised over her rosebud ... She didn't say no but she didn't say yes.

I needed Catherine to say yes; to invite me in.

I held off penetrating but continued to rub my cock in her crack.

It didn't take but a couple of minutes of thrusting before I squirted all over her ass.

It was a big wet load, despite me having just cum.

She had a great ass and I was continuously complimenting her on it.

Cumming on it was a fine way to show my approval.

Catherine smiled at me and said, "Let's get in the shower and please make sure you get all of you off of me sweetie. I don't want to have a sticky back on the plane ride."

++++

At nine we were down in the restaurant meeting with Jennifer.

We discussed wedding rings for a short while.

Rings were a far bigger deal to Catherine than they were with me.

Keeping a close eye on the time, when there was a lull in the conversation I started asking about Jennifer's background.

It turns out that she was a photographer and had taken the job at Tiffany's to pay her college loans back.

From the look on her face Catherine was curious where I was going with this but she didn't interrupt.

After I learned about Jennifer, I said "We have this bathing suit company and instead of paying a bunch of freelancers to take photos, would you consider coming to work for us full time? I need to see your portfolio and we can talk about it when we come back to pick up Catherine's engagement ring."

Jennifer had questions and I did my best to answer them, including salary and benefits. I wasn't sure she needed to relocate but she would have to travel.

We left the hotel at 10am for O'Hare.

On the way Catherine asked me about hiring Jennifer and I replied "At the hotel, you probably bring in a number of items from suppliers that are too difficult or too time consuming to make."

She nodded.

"I've discovered that these photographers we hire are simply not reliable. Don't get me wrong, they take beautiful shots. But, they say they'll show up, and they don't. They cancel at the last minute and they all want more money than they are worth. Getting the proofs back is an ordeal. So, when I travel I meet people who want to engage their passions and I pay them a good wage. They tend to be hard working and they bring new ideas into the company. So, that is why I am interested to see Jennifer's portfolio."

Catherine nodded and then I added "I want you by my side during these interviews because I value your opinion. You're a good judge of people. Will you do that for me?" She smiled and kissed me, replying "Of course, I'd be honored."

She had her hand on my thigh and she was starting to get me hard.

Maybe we should have spent another night in Chicago.

The window was up behind the driver so he couldn't see or hear us and Catherine whispered to me "Do you want a quick blowjob honey?"

I would have loved to but we were almost to the terminal and I kissed and thanked her for the offer but I had to turn her down.

She pouted for a second and then said "Wait until I get you alone tonight in the hotel!"

I responded with "It's time for me to shave you again" and she laughed.

My phone pinged as I received an email from Dana and Julie on their plan to travel the world and sell CYN Suits.

I briefly reviewed it and then replied to them that I wanted to build the US business first; then go international. So could they revise their thinking by targeting the US market geographically for three months, then go international for a month, then repeat the cycle. I told them I had in mind buying a bus that we would brand and doing events in first and second tier cities all over the US. These two would produce the events, and we would bring along the support teams.

They replied they would redo their plan and would I give them a week? I said yes, we won't start the US stuff until January when we would go to the freezing Midwest and that they should plan their first trip overseas for two weeks in late September. I wanted them to head to Australia, Tahiti and Hawaii.

After we went through security at O'Hare, we stopped to use the bathroom before heading to the gate.

We switched off watching our bags and when she was finished, Catherine came up to me, wrapped herself around me and gave me a big kiss.

Her PDA (public displays of affection) were getting more numerous and frequent. I wasn't complaining.

I noticed she was turning heads everywhere she went.

Catherine was a classy lady but I was really liking her showing her affections towards me when she felt comfortable. And each day she was feeling more comfortable.