The Second Time Is Twice as Nice

My stories are in chronological order. I encourage you to follow along and read these stories in this order as a prelude to this one:

I Hire Monica The Maid

Monica's First Day as My Maid

Monica the Maid's Three Hole Day

I Partner with Linda, A Salon Owner

I Massage Monica the Maid

Hot and Sexy Business Opportunities

I Become a Therapeutic Instructor

The Affair Continues in Las Vegas

I Rub an Asian MILF the Right Way

Going Where No Man Has Gone Before

Cumming Where No Man Has Cum Before

That Was The Weekend That Was

I'm Rewarded for a Job Well Done

Fun in Las Vegas with my MILFs

That Was The Week That Was

I Take My MILF Lisa to Mexico

I'm Ambushed by a Very Hot MILF

The CFO Gets Her Assets Worked Over

In Pursuit of a Very Hot MILF

For background, let me share the main characters in my stories:

I became a widower unexpectedly in January. I was lonely and in pain; I made an offer my maid Monica could not refuse. She stayed on as my maid and became my part time sexual playmate. (I Hire Monica the Maid; Monica's First Day as My Maid; Monica the Maid's Three Hole Day, I Massage Monica the Maid).

Coming out of my funk, I decided to learn how to give massages and I met Susan, a bathing suit model, who was my massage instructor, and we became friends. Between Susan and Monica I came up with some new business ideas (Hot and Sexy Business Opportunities).

I met Lisa, a divorcee, who was a student of Susan's when I was a substitute instructor. We became lovers. (I Become a Therapeutic Instructor).

Lisa and I went to Las Vegas. (The Affair Continues in Las Vegas and That Was The Weekend That Was). I hired two ladies, Diana and Dana, to be with Lisa at the adult pool. Lisa arranged for my first threesome when we included her friend Michelle. (My Great Night in Vegas - not written as of this date).

After I met Lisa, and while I was casually dating her, I seduced Akiko, the lady who owned a local dry cleaners. I invited her over for a massage (I Rub an Asian MILF the Right Way). We traveled to Las Vegas (Going Where No Man Has Gone Before) where we met with Marie and Carmen.

The next day in Las Vegas (Cumming Where No Man Has Cum Before) I took Susan's virginity and enjoyed sex with Dana. On Sunday and Monday in Las Vegas (Fun in Las Vegas with My MILFs) I had sex with Dana and Sandy (a hotel food and beverage employee).

I enjoyed my second threesome in LA with Eva. She was a manager at one of my client companies. (I'm Rewarded for a Job Well Done).

Leading up to the photo shoot for CYN Suits, I spent a week between LA and Las Vegas (That Was The Week That Was).

After the photo shoot, I had a lucrative business deal close. I made a lot of money that day and a friend of my late wife re-entered my life (I'm Ambushed by a Very Hot MILF). Her name is Catherine.

Catherine left on vacation and I enjoyed sex with Cynthia the CFO, Dana and Julie, both swimsuit models.

++++

Early August

I had kissed Catherine goodbye in her hotel room upstairs. Before leaving her I sucked on the bare breast and gently bit her nipple. She laughed and kissed me with passion.

I told her I'd meet her in Montreal in a couple of days. It was 5:30am, Eastern Time, Tuesday.

I was downstairs outside the hotel lobby getting ready to board the airport shuttle for a quick trip back to Los Angeles from Quebec when my phone pinged with a text message.

The phone number looked familiar (it had an LA area code) but I didn't have the number in my address book matched to a name.

The text read: Hi Jack, just got home from vaca and I can't sleep because of jet lag. Didn't we have a fantastic night together in June? My God I get the chills thinking about how many times I came! But you didn't do the one thing I was really hoping you'd do: eat me. I've wanted you to lick my pussy since the first time we met. I know you want to. Tell you what, if you promise to eat me you can fuck my ass again. And, I'll eat pussy for you. Deal?

PS: I'll toss in another pair of silk thong panties for your private collection. They'll be nice and warm. Maybe wet too. When can we get together? I've missed you. And your big dick. Eva

I thought: Holy Shit Batman. Eva the hot sales manager is back from her two month vacation. Looking for love or just a good time? Who cares? I'm open for more of that very hot ass.

I was in Canada with Catherine, her two daughters and her parents on a vacation. Catherine and I had not yet had "the conversation" about an exclusive relationship and I wasn't going to be the one to bring the subject up. Let sleeping dogs sleep. Let me sleep with as many women as I can. Let me die in the saddle, please.

I sat down on the bus and texted Eva back: Would you be open to a weekend in Las Vegas?

She replied seconds later: When?

I responded with a couple of weekend options later in the month.

She texted: Could we do both weekends? I really want my pussy licked. By you. And I need to be fucked. Repeatedly. By you! Vegas would be a fun place for us.

I had more carnal thoughts. Two weekends in Las Vegas with Eva. This is a wet dream come true.

I chuckled and sent her this:

Yes, I'd love to spend two weekends with you. I'll set it up. Hotels, planes, limos, shows, gambling, sex. Lots of sex. I want you to go online this morning and buy 12 suits. Use promotion code Jack and they'll be custom made and shipped at no charge to your home. Put under special instructions Rush Per Jack. They should be there by Friday. You'll be wearing them at an adult pool in Vegas.

Eva answered: Why do I need 12 suits? Why do I need a bathing suit, I thought we would just stay in the hotel and fuck our brains out. And what do you know about this company?

I responded: CYN Suits is my company. You'll be with me for 6 afternoons at an adult pool in Las Vegas and I want you in a new suit every few hours. I want to show you off.

Eva writes back: I've heard about these adult pools but remember, I'm not 21 anymore.

I reply: You'll be topless by the pool. I'll hire a different hot UNLV coed to rub sun screen every day all over your perfect almost nude body so you won't get sunburned. BTW on Sundays from 3pm to 7pm they stop serving alcohol and the pool goes nude. So when the pool goes nude so will you.

Eva texts: You want to show me off to total strangers? In tiny bathing suits, then have me go topless and end up nude? Just what kind of girl do you think I am?

My reply: You're smart, funny and beautiful. You'll be the hottest female poolside and you know it. You'll be the center of attention-something you love. And you'll be with me. Being in a tiny suit then topless and then nude with men and women eye fucking you for hours will make you so horny one flick of my stiff tongue on that beautiful pussy of yours and you'll cum like you've never cum before. Plus I want to see you eating pussy again.

Eva sends: I'm wet just thinking about your tongue on my clit but can you see me before that? Like tonight? My pussy can't wait for Vegas. I want you! Now!

My answer: My plane gets in at noon to LAX and I can I meet you in Beverly Hills. At The Montage? What time? 5?

Eva closed with: I'll see you at 5pm in the bar. I'll be the girl without any underwear on. For your easy access. Be ready to lick me to death. I'll let you shave my pussy for starters. I'll have my tight ass ready for your big cock. And a wet hot very tight pussy just for you. I've been thinking about you since our night together. I got home late last night and you're the one I want to be in bed with. Safe travels. XOXO E

++++

My goal was to meet up with Catherine, the girls and her parents in Montreal on Thursday in time for dinner. It was a fast turnaround trip. I had no idea it would be so busy. And fun.

I landed at LAX and got to my LA client by 2pm.

The meeting lasted until 4 and then I met Eva at The Montage in Beverly Hills at 5pm for dinner and a long night of sex.

I checked into my suite and along the way stopped at the drugstore for a few items. Even though I was only spending one night with Eva at the hotel I emptied my suitcase and ordered champagne for the room.

Walking into the bar and I saw her first and took in the view. Her hair was styled, she was tan, she was wearing a little black dress with a pearl necklace and matching earrings. It looked like she had gained about fifteen pounds, her ass was a bit bigger and when she turned in my direction I could see her breasts had grown too.

My late wife believed that big asses meant big tits but it didn't always hold water especially with boob jobs. I knew Eva was all natural and if her tits were bigger it would just mean more for me to play with. I was looking forward to seeing them, touching them and sucking on them. Maybe cum between them.

Her smile lit up the room as we saw each other and she greeted me with a deep kiss. She held me tight and we kissed a long time, oblivious to the few people in the bar at that hour. I could feel her breasts through my suit coat and they were larger. Her nipples were erect.

Eva tasted, smelled and felt great. I knew fucking would be a lot of fun; very pleasurable and non stop even without Kayla being there.

When our lips parted we held each other for a long time and she whispered into my ear how much she had missed me, how often she had thought about me (everyday) and how often she masturbated as she thought of our one night together with Kayla (before she went to sleep and every morning when she woke up).

We were seated in a quiet booth in the back, very visible so there wouldn't be much an opportunity to fool around like we did before in the dark booth at the steakhouse. But there was plenty of time to be spent naked in the hotel suite so we sat close together like lovers and whispered a lot and we were constantly touching one another.

Eva confessed she had a bra on but she wasn't wearing panties and she took my hand and put it on her thigh so I could remember what I had missed for the last two months.

I moved my hand up her thigh until I ran into some fur.

Eva put her hand on mine and said, "That's far enough Jack. If you spend much more time there I'll cum and you know how wet I get. But you realize that your first job tonight after we get naked is to shave me, right?"

I responded with "I'm looking forward to it" and then I kissed her. "But would you mind terribly if I played with your pussy before I shaved it?"

Eva looked at me like an adoring fan and laughed. She said "I approve your priorities Jack."

I kissed her and whispered into her ear "I get a great deal of pleasure making you cum sweetie."

Eva shivered knowing she'd be cumming soon.

She told me all about her trip and we laughed at some of the miscues and things that happened. We kissed a lot between the laughs and I was having trouble keeping my hands to myself. Only the fact that we were in plain sight of most of the bar and restaurant kept me in check.

Eva told me that she was glad to be able to take everyone on a once in a lifetime trip but she'd rather do it with just one person next time. "Maybe we could do it next summer Jack?" she posed.

We'd finished a bottle of champagne and I looked at Eva and asked "Are you hungry or would you rather have dinner later?"

She looked at me and said "I think I can afford to skip a meal" followed by "Let's go get naked."

By the time we got to our floor I had unzipped her dress all the way down the back, was rubbing the top of her ass and had taken her shoes off. By the time the door of our suite closed behind us Eva was naked except for her bra and thigh highs. Her dress was on the floor.

We kissed as I massaged her bare back and ass cheeks rather leisurely and she groaned into my mouth.

I loved having my hands on her. She loved it too.

I soon found her rosebud and put my finger tip on it and pushed gently.

I swear she began humping my leg like a puppy!

Eva's ass felt good - very good - in my hands and she loved the attention I was paying to it. I vowed to give her my Grand Canyon massage before checking out the next morning.

As we kissed I reached and unhooked her bra allowing her breasts freedom. I gently pulled the bra off of her, momentarily breaking the fighting going on between our tongues. Her hard nipples could be felt through my suit coat, dress shirt and tee shirt.

The only thing she had left on was her black silk thigh highs.

Eva was starved for physical affection. I was amazed that the once so in control sales leader was like silly putty in my hands. Moldable. Pliable. Had the alpha female surrendered to an alpha male?

I broke our kiss and said to her, "Eva, I'm going to enjoy you being naked until I leave tomorrow morning. I've got some surprises for you tonight."

She held me tight as I continued to rub her fine ass and her bare back and she responded "Jack, whatever you say is what I'll do. You can do anything to me. I just want you to make love to me." She kissed my neck and my face and then found my mouth again.

I ran my hand between her legs and detected some moisture.

I found her clit in the hairy forest and she moaned into my mouth.

"Baby, I'm going to shampoo your bush before I shave it all off. You'll be bare as I can get you."

Eva kissed me, smiled at me, then turned to go into the bathroom, her fantastic ass sashaying as I watched her. Her ass was white, we call that a cottontail in the swimwear business. But the rest of her, with the exception of her strap marks, had a nice tan.

I took off my suit coat, loosened my tie and called out, "When you finish in there please come and undress me."

Being a nice guy I hung up her dress and her bra (34D) in the closet. I put her shoes I there too.

Eva was back in a couple of minutes. She lifted her hands up over her head, giving me the full frontal monty. Her larger breasts were white, untanned and swaying. Her large brown nipples were taut, puffy and aroused, ready to be sucked. I could now see her full bush. Fur. The aroma of her sex reached my nostrils.

She smiled at me and kissed me and without saying a word, took off my clothes and hung them up nicely in the closet. I just watched getting more and more aroused, which I am sure was Eva's plan. She put on quite a show for me, kissing me as she took off each piece, the result being when she kneeled to take off my briefs, the last piece of clothing I had on, I had a large erection waiting for her.

I put my hand on her head and said "Eva, kiss him hello. He missed you."

With that, Eva gave my cock a deep French kiss to end all French kisses. I didn't want her to stop, my God she gave great head, but I had other plans so I pulled her up and kissed her deeply, even though she had a slight penis breath. It was my penis after all.

I put a towel down on the sofa and had her sit down on it and I gently spread her thighs. I said "Close your eyes and lay your head back. Put your hands up behind your head. Don't open your eyes until I tell you to. If you violate my instructions I'm going to spank you."

Eva smiled at me, kissed me and replied "Yes Jack. But I might misbehave because I want you to spank me" she laughed.

Her head back, her arms up behind her head, her large white breasts with those highly suckable pebble sized nipples raised for my viewing pleasure, I started in on Eva.

I took off her thigh highs one at a time, each roll of the fabric generating a kiss on her soft, tender inner thighs and down her legs. Eva responded by spreading her legs wider and her aroma got stronger.

I sucked on her toes which got her laughing, her breasts jiggling.

Eva wanted my tongue on her pussy but I was going to make her wait. Maybe even beg for it.

By the time I removed both thigh highs her slit was visible through the dark bush and I began kissing her tanned toned thighs from the inside of her knees down to the crevice of her thigh and torso. She loved it, telling me how good it felt.

Eva tried to spread her thighs wider with each kiss and lick but she had reached her maximum. She reached her hands to my head to pull me into her pussy but I resisted, kissing then licking just above her pubic hairline on her belly while my hands gently teased the inside of her thighs without actually touching her pussy.

"Put your hands back up sweetie" I told her. "Lift them up."

Her slit glistened and opened. Her clit started to rise. Eyes closed, she licked her lips and whispered "Jack, please lick me, lick me now."

"Not just yet baby. I need more time with your beautiful body. With your beautiful pussy."

I continued to resist her. And I pulled back a bit and started running my hands through her untamed bush.

Much like a hairdresser would untangle unruly hair.

Eva began to hump my hands and her clit peeked out as her lower lips opened a bit more.

"Do you trust me Eva?" I asked her as she started to groan.

"With my life Jack" she gasped, her eyes still closed. Licking her lips.

Between my kisses all around her pussy but not on it, I whispered to Eva "Play with your titties for me sweetheart. Like you do when you think of me."

Eva started rubbing her breasts.

"Now pull on your nipples for me Eva" I told her, as I continued to run my fingers through her bush as I watched the show.

Her eyes were still closed, she started pulling on the firm erect nipples and continued to rub her breasts. She ran her tongue around her lips.

She asked me again to please lick her pussy and I said "Not yet but soon. Very soon."

While I continued to play with her dark moist mane and my kisses turned to little licks around her forest, I asked her if she had been a good girl.

She licked her lips and said "Jack, except for my fingers I have been faithful to you. So I have been very good Jack."

I said "Do you want me to take a little lick baby?"

Eyes closed tight, tongue licking her own lips, her response was "Please Jack, please lick my pussy. Please lick me Jack."

In anticipation of my tongue her pussy started to flow, her hips moved forward towards my mouth and I bent my head down and took a big slow lick from the bottom of her slit to her now hard clit.

Eva's hips bucked and she groaned "Oh my God Jack, please don't stop, please don't stop. That's the only thing that has touched my pussy besides my fingers in two months. PLEASSSEEE JACK."

I slowly assaulted her steaming cunt with my tongue, taking it very slow, still teasing her. I knew that she was close to coming so after just a few licks, I backed off and let her simmer. On high.

I eased my index finger into her slightly opened wet lower lips in a gentle probe and Eva gasped at the welcome intrusion.

I kissed her tummy again and licked her belly button while my finger soaked in her hot oven. I was tempted to rub her clit with my thumb but I held off.

I said "Now wet your nipples baby" and she did. She licked her fingers and rubbed her moisture on her sensitive nipples.

With my right hand occupied at and in her pussy, with my left hand I grasped a brand new nipple clamp I had placed under the sofa within easy reach.

I told Eva "That's good sweetie. They're nice and wet now. Stop playing with your nipples, keep your eyes closed and put your hands up behind your head."

"Good girl" I continued, "now push your titties out at me" and she complied, her back curved, thrusting her chest out.

I said "You're a good girl Eva."

I leaned forward, my right index finger now firmly encased in her hot, wet baking oven, diddling her and I took her right nipple into my mouth.

Eva bucked forward at the unexpected pleasure and a loud groan escaped her open mouth.

I suckled and teased her beautiful nipple until it was as large and aroused as it was going to be and then I pulled my mouth off the wet protruding skin and with my left hand, put the clamp on the wet firm nub.