The Second Time is Twice as Nice

Eva went fucking nuts at the unexpected sharp pain. She opened her eyes, they filled instantly with tears and her hands reached to remove the cause.

I was expecting this and quickly pulled my right hand out from her pussy and grabbed both of her hands and looked into her tear filled eyes.

"Please Jack, it hurts, take it off of me."

I instructed her "Breathe through it, the pain will disappear in a few seconds."

Holding her hands, I quickly kissed her and she responded aggressively.

In a minute when our lips parted, I said "Has the pain stopped?" and she nodded. A few tears running down her face.

"Good girl. You're my girl Eva."

I kissed her and she responded with a groan into my mouth.

I massaged her right breast gently careful not to touch the clamp.

"Does that make it feel better?"

She smiled and nodded.

That left her left breast waiting and she looked down at her now very stiff and aroused left nipple and said with some resignation in her voice "Okay Jack, you can do the other one too."

She looked at me and I looked at her.

"Ask me to put the clamp on your beautiful breast Eva."

She looked at me and I looked back.

It was an old sales trick. Silence. To see who would cave first.

She looked at me and I looked back.

I said "The clamp is going on your nipple baby, but I want you to ask for it. Because I won't let you come unless both nipples are clamped. And I know how much you want my mouth and tongue and lips on your pussy."

She smiled and said, "Jack, will you please clamp my nipple?"

I asked her to "Please put your hands back behind your head for me" and I kissed her a lovers kiss.

She responded with a groan and lots of tongue. Her hands pulled my head in and when our lips parted Eva said "I love being with you Jack, I couldn't resist kissing you."

I smiled and said "I might spank you later" as my right hand found her breast and she groaned as I squeezed her bare mound.

Her tears had stopped flowing and she smiled at me, putting her hands back up, lifting her unbelievably fantastic breasts.

"I love your tits Eva" I said to her. "They're wonderful to play with."

"Tonight I am going to worship them. Now close your eyes sweetie" and she complied.

I spent a lot of time preparing her left nipple, and she groaned in pleasure as I licked, sucked and teased it well beyond its very aroused state. I know she wanted to grab my head and pull it to her breast put I reminded her to keep her hands up.

I used my teeth, causing some pain which Eva enjoyed even though she flinched as I gently bit down.

When I put on the second clamp she inhaled sharply but there weren't any tears. I kissed her again and she responded back with a hungry tongue.

"Your breasts are beautiful Eva. So are you." And we kissed.

I told her "Out by the pool when you are topless I'll have you wear some nipple jewelry which will grab the attention of everyone. You'll be desired by every guy and girl there. Their eyes will zero in on your beautiful breasts. You'll be the hottest female there. Your pussy will be so wet you'll need to get in the pool to cover it up."

She nodded, eyes still closed, her clamped breasts swaying slightly.

I put my right index finger up to her lips and said "Eva, sweetie, make my finger wet."

Her lips and mouth played with my finger as if it was a cock, wetting it with her saliva.

I pulled dripping finger out of her mouth and into her now wide open pussy and starting licking all around her clit, restarting her engine.

I knew she was close, oh so close as I licked and then I said to her "Let me see your rosebud honey" and she took her hands down from her head and lifted her ass to offer me a very tight clean asshole.

With my left hand I sought out her tight opening.

Her eyes closed, enjoying both the pleasure and the pain, Eva smiled and said "I'm a three hole girl for you Jack, you were the first one in my ass and you'll be the only one who ever gets in there."

Eva asked, "Did you bring lube lover?"

I stuck a finger into her dry hole and that earned a gasp but not a rebuke.

"Yes, I did" I replied. "I'll use it a bit later babe."

I pulled out of her ass and lifted two fingers to her and said to Eva, "Honey, please wet these for me" and she took them into her mouth as if they were penises and got them very, very wet.

If she tasted her bung hole on one of the fingers it didn't register on her face.

This time I pushed both fingers in without any preliminary and she yelped a bit but I was still see sawing her pussy and her cunt river was starting to flow.

With two fingers in her ass, loosening her up for later, one finger pumping her wetness, I looked up at Eva, her hands behind her head, her nipples clamped for my pleasure and her pain, and her new larger breasts swaying oh so slightly as I pumped her. She was constantly licking her lips. Punctuated by whimpers and moans.

I asked her "Do you want to come now sweetie?"

I rubbed my thumb on her clit and she bucked.

And groaned.

"Oh God Jack!"

She was starting to sweat and boy, was she ever worked up. On the verge.

Eva said "I've been waiting two months for you to make me cum. Please Jack, I can't wait any more."

I gave her what she wanted, I licked her pussy like I'd never licked a pussy before.

In no time flat her hands were on my head, and she was moaning like a wounded animal.

It didn't take long, the buildup had her overheated and she screamed and shuddered and humped my tongue when she came, then gushed all over my face, my hands and the sofa.

She pushed my face away from her wet beaver.

She collapsed and I let her rest for a minute while I kissed her inner thighs before I moved up on the sofa next to her.

I held my right hand fingers to her mouth and said "Lick these clean Eva."

She did, tasting her own juices.

I did the same with my fingers on my left hand and she licked herself off of me.

Then, I moved my head towards her right breast and took off the clamp, instantly smothering it with my mouth to soothe the pain of the blood rushing back into her nipple. I did the same thing with the left nipple.

I kissed her and she kissed me back, lazily, thanking me. I held her, massaging her bare breasts. Her nipples responded to the caring attention.

I whispered to her "Was that what you wanted? My tongue on your pussy?"

She smiled and nodded. We kissed.

Eva said "I knew you wouldn't disappoint me. Thank you for licking my pussy. Will you lick it again, please?"

I took Eva by the hand into the tub. Her legs were shaking but it wasn't but a few steps.

Those extra pounds on her made her look better. Her ass was a bit more curved and her breasts, well, what man doesn't want to see larger breasts on a woman? More to see and more to play with and I knew that her breasts and nipples were already sensitive and responsive to my touch, kiss, lick and bite. Plus the sharp sting of a clamp.

We got into the tub and she laid in my arms, resting. I wasn't going to wash her hair as she just had it done, but I also knew I was on the clock. At some point her jet lag would kick in and she would be out like a burned out light bulb. One time in a restaurant the woman I was with fell asleep sitting up waiting for her dinner (true story).

I quickly shampooed and conditioned her pubic hair, something she said no one had ever done before to her. She liked it and asked me when I finished if I would do it again sometime. I said "Yes honey, when you grow your bush back." Eva laughed.

I lathered up the shaving brush and drained some of the water out of the tub and got to work rubbing the bristles all around her pubes, making Eva feel excited and aroused. I didn't think it would take too much to get her to cum again and I was right. While we were making out I ran that brush repeatedly over her clit and my other hand was playing with her nipples and she came again as we kissed.

I told her "Eva, let me get this hair cleared off your pussy before you fall asleep."

She nodded, now in a daze.

I worked fast and got her cleaned up, good enough to eat.

And I ate her again, for good measure. As she requested.

Eva went bat shit crazy over the sensitivity of her newly bald pussy.

I kept at it until she pushed my head away, saying "Enough Jack, please baby, no more tonight."

I got her out of the tub, dried her off, pulled the covers down on the bed and got her into it. It was 8'clock.

Using lotion, I massaged her neck, shoulders and back. Eva thanked me for a great night, I kissed her goodnight on the cheek and heard her say "I liked it when you clamped my nipples." In seconds she was asleep.

I pulled up the covers.

I turned out the lights in the bedroom, checked the rest of the suite and slipped in behind her and heard her gently snoring.

It had been a long day for me too, and I fell asleep in a just a few minutes.

I woke up spooning a warm nude Eva in the middle of the bed; I had no idea what time it was. It was dark outside. I detected a movement in the bed. Eva was masturbating. Very slowly. Rubbing herself.

Despite making her cum several times during our playtime together, I had not and my erection needed attention.

I snuggled even closer to Eva, my hard cock firmly between her cheeks, and I whispered to her "You're a very bad girl Eva, and in the morning I'm going to spank your ass. Now, let me take care of that for you sweetie."

I took her right hand to stop her and I began slowly rubbing her tummy, down to her bare pussy and then her right breast. And back to her left breast. Both responded to my touch and I liked the new heft of them in my palm.

She said, "Jack I'm still so hot and bothered and I didn't want to wake you."

I replied "Having a bare pussy means you'll want to play with yourself more."

I nuzzled the side of her face and slipped my left hand under her neck so I could play with both of her tits at the same time.

Her larger breasts filled my palms nicely and her nipples responded to this unexpected attention in the middle of the night. As did her pussy.

Eva stretched and then rolled over giving me better access and we continued to kiss like this until I detected that her pussy was sopping wet. I rolled on top of her and literally jack hammered her to two quick orgasms before I deposited a large load inside.

I could hear a smile in her voice when she whispered "That should keep me until morning lover."

She fell right back to sleep and so did I.

The worst way to wake up in the morning, based on my experience, is to be scared to death when a 6.9 earthquake shakes the shit out of your house at 4:31am in the morning. That was my morning wakeup call in January 1994 when the Northridge earthquake hit.

A far better way, and one of my favorites, is to wake up is to have a beautiful, hot chick sucking on your cock and licking your balls as the cobwebs leave your head and your dreams go back to wherever dreams go until they come back again.

And so it was one very pleasant early August morning as I lay naked in the hotel bed in Beverly Hills while a nude Eva lay between my splayed legs, licking me back into shape with the goal of climbing on board for a ride.

I liked looking down at her dark hair, manicured nails, long pink tongue, with her breasts swaying as she did her magic.

She was in a great mood, having been licked to orgasm twice plus being rubbed with the shaving brush before falling asleep and having gotten some good sleep. Plus she took a load of my swimmers in the night after cumming twice from my pounding. If she didn't like cleaning her dried juices off of me, she didn't say anything.

While she licked, kissed and sucked she told me that she had been thinking about being at the pool nearly nude and nude and that it would be a rush.

Eva being Eva, she wanted to know all the details so she could manage the situation.

I had her stop for a second and said "Come up here honey."

She climbed up between my legs and we kissed good morning. She wrapped her hand around my cock and continued to stroke it, on automatic pilot. It felt great and I preferred her mouth but this was better than nothing.

I told her, "You have to trust me on this. I would never put you in a position where you would be hurt, embarrassed or frightened. Sweetie, its a pool and I always get an air conditioned Cabana so you have a choice of being in the sun, the pool, at the bar or in the shade. Not everyone will be topless, but you will be. And when the pool goes nude, you'll be nude too. And you're going to love it. Every minute. Plus, I'll make sure you don't sunburn. Whomever I pick is going to love getting their hands all over you."

I asked if she had gone on line and ordered her swimsuits and she laughed at me. "Do you think I would hesitate to go shopping if someone else was paying for it? I was on that website two seconds after you told me about it."

Eva asked about the girls who would be rubbing oil on her.

I told her "I found a dynamite young lady who loves to hang out at the pool. You'll like her and she is a lot of fun. She loves rubbing oil on girls. And you can rub oil on her or maybe I will. But it would be hotter if you did it. You'll be turning heads for sure."

I was thinking specifically of Dana but I could also invite Sandy (the room service gal from the hotel). Or I could hire someone else. Dana and Sandy liked eating pussy and liked to be licked. I knew they would both like Eva.

All three of them wanted to be around me. And I liked each of them for different reasons.

I laughed and said, "Enough with the questions, show me what you remember about deep throating honey."

Eva gagged a bit but overall she did a good job and she swallowed my load when I came.

I didn't hold her head down and force myself into her throat because I knew she would, with more practice, get there on her own.

She showed me she chugged it down when she gave me a kiss. So what if she had semen breath? It was my semen.

While I loved getting head, I also needed coffee and asked Eva to please order coffee and breakfast for us from room service.

She came back to bed and I gave her a quick back rub and then proceeded to spank her ass for masturbating without permission. Eva laughed and laughed but I got her cheeks red and when I finished I massaged her fine ass. She loved it.

I climbed back into bed and Eva gently stroked me as I laid in the bed, and she spent some time licking my balls.

I reminded her she was going to go to the door when room service came, and while I preferred she be nude, I would allow her to wear a towel around her waist. "Its good training for your time at the pool."

She got me hard in no time and then the expected knock on the door came.

I asked her "What's it going to be?"

She got off the bed, kissed me and with a now pink behind answered the door to a woman with a very nice voice who didn't seemed phased at Eva's nudity. While the server was taking items off the cart and putting them on the table, Eva came back into the bedroom and I handed her a hundred dollar bill for a tip.

The woman asked Eva if everything was alright and Eva said, with a straight face, "My boyfriend likes to spank me."

The woman was very pleasantly surprised to hear that (I'm sure she was intrigued) and thanked Eva for the nice tip.

Eva fed me breakfast in bed and we both stayed nude. I got a little adventurous and put some strawberry jam on her nipples and licked it off.

After I finished I had her get the shaving gear again and a towel. Under the pretense that I missed some hairs the night before I shaved Eva's beautiful pussy again, this time on the bed. She loved the attention and after I wiped off the remaining shaving cream I saw how wet she was and I told her she needed to masturbate for me. I videoed it.

It was pretty fucking hot, it sure got me hard to see her playing with herself and cumming on her fingers.

I said to her, "I like it that you put a few pounds on. You added them in the right places." She kissed me in appreciation. I am sure she was thinking she would be embarrassed when I saw that she had gained weight.

She returned the favor by giving me a hot coffee blowjob which got me harder; then she got up on her knees, doggy style and asked me "What are you waiting for honey?"

I smiled and said to Eva "I want you to spread your cheeks for me sweetie and ask me nicely to fuck your ass."

Eva laughed and said "Jack, I want your big hard cock in my ass this morning. Can you help me out by scratching my itch?"

I lubed her up with three fingers and then did my cock. I took it slow into her ass but within a minute I was balls deep.

Eva had some tears running down her face and her hands were gripping the sheets but she smiled and said, "Its good Jack, its only my second time so go slow but go ahead."

Even though I had come not too long before I stroked in and out for maybe five minutes before I blasted her insides and she laughed, reminding me "If I need for you to come quickly, I'll just have you fuck my ass because you don't last too long in there."

I laughed too, she was right. I told her why I came so quickly "Its so fucking tight Eva, it drives me crazy."

We cleaned each other up in the shower and I left her naked in the room putting on her makeup.

I told her "If you want to add a few more pounds before Vegas we can get you bigger tops." I nuzzled up to her neck and rubbed her breasts and pulled on her nipples.

"I like these bigger breasts on you. More for me to look at and to play with. And you already had a fantastic ass that is even better now. Don't you dare think about getting a boob job."

She smiled at me; we kissed each other goodbye and I drove to my house to check on things.

I hadn't been gone but a few days but it seemed like forever.

Eva texted me that she got so hot from my fondling she rubbed another one out in the bed thinking of us fucking. She said I would rather seek your forgiveness than permission. She promised to add a few more pounds in all the right places before Las Vegas.

I replied with a happy face and a message: next time video yourself rubbing one out and send me a copy. And I'll be spanking you in Vegas.

++++

I spent the rest of my day in my home office on the phone with clients.

Monica was in Mexico. I fondly remembered the days when she was at the house cleaning in the nude, starting her day by giving me a BJ, swallowing my load, then at some point taking a pounding in her welcoming pussy and before she left, letting me make a deep deposit in the ass. I missed her cooking too.

Catherine texted me to make sure I was going to meet with her ex husband and I replied that it was a go.

She replied that she wanted to know how it went.

I texted: I will let you know once our meeting is over. In the meantime, don't worry about anything and just relax and have fun. I'll be there tomorrow in time for dinner, please pick a nice place for us.

At 3pm I disengaged from my business stuff to meet with Catherine's ex, Rick. We met at a nearby Starbucks.

He remembered me. And going to dinner with our wives. I didn't remember him but each year I had met almost all of the parents in my wife's elementary school classes and I appreciated his thoughtfulness.

Rick said "I am sorry to have heard of your wife's passing."

I thanked him.

We got down to business when I told him "I'm dating your ex wife and we're probably going to get married."

I followed that up with "I wanted to talk to you about it short term and longer term if that is okay."

First I mentioned that the girls wanted to spend time with his folks before they returned to California and was that possible.