I Reflect on an Interesting Year!

I was reminded of the movie Sleepless in Seattle where Tom Hanks gathers up the courage to make a phone call to ask a lady out on a date, his first one since Carter administration. When he hangs up the phone, the song "Back in the Saddle Again" plays.

That song was in my head as I fucked this very hot young lady.

Post shower, I dried my hair and shaved while Amanda dried her hair.

Taking me by my hand, she took me to the bed and said "I have a favor to ask you."

I smiled and said "Name it."

She reached into that CVS bag and pulled out a razor and shaving cream, turned to me and asked "Will you shave my pussy? I want it bare for you."

It took me forever, but I did, enjoying every moment.

When I finished I ate her to a quick orgasm and we grabbed breakfast in the hotel and Amanda told me she had to work that day at the restaurant from noon to 6pm.

But that she'd be back in time for dinner and a movie. Or dinner and sex. Or just sex, no dinner. Whatever I wanted.

I laughed and asked her if she wanted to go out or stay in the hotel or have room service.

Amanda replied "I just want to be with you, so whatever you want to do is fine with me."

She did laugh and say "Brie and Lauren are going to be really curious when they see me today. What should I tell them happened last night Jack?"

I smiled back and said "No matter what you tell them they are going to know you slept with me. They knew it was going to happen when we walked out together last night. So, tell them the truth and let them be jealous."

"But if I tell them that will ruin your chances of sleeping with them."

"Actually Amanda, it won't because they will both work harder to get me away from you. But I'm not interested in them. Only you."

As I dropped her off we kissed and I spent the next six hours in my office. Amanda was on my mind the whole time.

****

When I picked Amanda up she got in the car and kissed me.

She said "I'll tell you about work later but first I need you to drive us somewhere."

Amanda shared with me that having a completely bare pussy had her hot and bothered her entire shift. She confessed that she rubbed out two orgasms in the bathroom.

It was raining and dark, and as usual for a Saturday night the traffic sucked.

We ended up in the San Fernando Valley, North Hollywood to be exact. Parked in front of an adult store.

When I asked Amanda what we were doing there, she smiled at me and said "Help me expand my sexual boundaries Jack. Go buy some toys you'd like to see me play with. You know, the kind that you'd want to video me using on myself to remind you how hot I was for you."

Are you fucking kidding me????? I left the car running but before I went in I told Amanda to take off her jeans and her panties. She laughed but got started on it before I left the car.

I was back in a few minutes with a non descriptive brown grocery bag filled with merchandise.

I put the bag on the floor of the car behind the driver's seat and pulled out a purple plastic dildo. Handing it to her as I got back behind the wheel I said "Start fucking yourself with this and don't stop until you've come five times."

Amanda replied "That will be fun. My butt is cold can you show me how to turn on the seat warmer?"

I took care of Amanda's butt and cranked up the heater too to keep her legs warm. For some reason that adult store had socks so I had her reach back to get the out of the bag and when she did this I slapped her ass playfully which caused her to laugh.

I avoided the freeways and took surface streets back to the hotel. This gave Amanda plenty of time to work that dildo magic on that needy pussy.

Her feminine aroma soon filled the car as she worked the dildo in and out and all around her freshly shaved pussy.

Amanda had the seat back; her thighs spread and had both hands on the plastic play cock.

I had her put her feet up on the dash board.

Spread wide.

Thank God no one was on the road that night.

In no time she was in her own little world of seeking pleasure.

I loved that squishy sound as she pumped her very wet pussy with that purple plastic penis.

After her first orgasm I had her remove her bra but leave her blouse on so she could play with her titties and stay warm.

She'd only come four times by the time we got back so I parked at the top of the deserted multilevel garage next to the hotel.

The rain continued to fall.

I left the car running with the lights out and the heater on. I got a little wet getting into the back seat and Amanda climbed back into the back seat over the console.

She lay down with her head in my lap.

Amanda's constant fucking her pussy for the last 45 minutes had me hard.

I had Amanda suck me off while I played with those magnificent tits of hers and she jabbed the purple dildo in and out of her tight but now very wet twat in search of that last elusive orgasm.

She was insistent with her sucking but I wanted to torture her a bit so when I was getting close I'd pull her mouth off of me and we'd kiss.

Amanda had a serious case of penis breath but I didn't care. I tasted my cock not someone else's.

I kept her in purgatory for about ten minutes until she was begging me to come.

I said to her in a strong tone "If I let you come you know I'm going to be fucking your ass tonight."

She was sucking and she groaned and took me deeper in agreement.

That got her past the tipping point and she shook as she came, swallowing my load.

I loved how she sucked my cock. Throughout the weekend I had her mouth on my cock.

(In the mornings, between sips of coffee she would blow me. This became known to me as a Hot Coffee Blowjob, something everyman would enjoy).

As she came, Amanda collapsed with her head in my lap, licking her lips and swallowing my salty essence.

My right hand found its way to her bare wet pussy and I cupped it.

Amanda pushed against my hand, hungry for a new touch.

While she was recovering I asked her if she wanted to know what else I had in mind for her. She giggled and said "Sure."

I moved my right hand from her cunt and rubbed her flank, and then using both hands pulled her cheeks apart and said "Tonight you'll be wearing a butt plug. To open you up."

"Jack Colton when are you going to fuck my ass?"

I slapped her butt and replied "Tonight. Before midnight. Several times Amanda."

She laughed. "You'll be my first. I saved it for you."

Then my right hand roved from her ass back to her pussy and I found her hairless wet warm opening again and said "You'll be wearing some special panties I purchased."

Before she could reply my right hand returned to her nipples under the blouse and pulling on her right nipple I said "I also have some very special gifts in mind for your nipples."

Amanda laughed and said "Anything else?"

My right hand moved to push her hair behind her right ear, a very intimate gesture that made Amanda smile.

I replied "Yes Sweetie, before we go to dinner tonight you'll be deepthroating me wearing a training tool I bought for you to use. You'll be licking my balls as I come deep into your throat."

She shivered and it wasn't from the temperature inside the car.

****

Before we left the car I lubed up a small butt plug for Amanda's ass. I made sure she asked me to stick it in before I pushed it in. Amanda was complicit in this act as she held her cheeks open for me. She clenched and groaned but took it.

I rubbed and spanked her ass and she laughed.

She said she felt full. I replied "You'll be feeling a lot fuller before midnight."

I also had Amanda put on her new panties. They were Adam & Eve Vibrating Panties. Using the remote I tried it out a few times and got the response I desired.

Getting Amanda hot and bothered.

I also clamped both of Amanda's nipples after she prepared her titties by wetting and pulling on her nips for these new tools.

I left her bra in the car and made sure that anyone looking at her chest would know she was commando and had something on her nipples.

She tugged her jeans on over her new panties and I drove back down four levels through the garage to the valet.

I gave the valet the key fob and grabbed the brown bag and we headed into the hotel.

He saw the bra in the back seat and smiled. Amanda blushed.

Every ten steps I turned on the remote vibrator for ten steps, each time extending the length I had the vibrator on. By the time we got to our suite Amanda was hanging on to me just to stand up.

****

In the suite, I removed Amanda's blouse, pulling in over her head and then her shoes, socks and her jeans.

Slowly I unclipped the nipple clamps, one at a time, soothing Amanda's pain with my mouth and tongue. I loved sucking on her nipples. I also tuned on the remote back on to start the vibration going again in her pussy.

I wanted to know if the vibration would bring her off so I asked her to play with herself to see if she could easily orgasm. It didn't take Amanda long before she was creaming in her new panties.

I wasn't shy, I taped the whole thing but first I had Amanda select a mask out of the brown grocery bag that covered the top half of her face.

She played with her titties, the vibrator did its magic and Amanda slipped her fingers into her panties to play with her clit.

Before 30 seconds had gone by she was bucking on her fingers trying to cum.

When she did cum, it was hotter than hell and I mounted her on the bed missionary style after I removed her panties and fucked her to another orgasm and despite coming into her mouth in the back seat of the car not very long ago, I gave Amanda's unprotected but safe to fuck pussy a nice load of swimmers.

God her pussy was tight.

She might as well have been a virgin.

Coming into her was amazing. Fucking amazing.

I got her into the tub and ordered us room service. When the knock came, I sent her to the door nude. She gave the young male server a $100 tip plus an eyeful he wouldn't soon forget.

Hotel room service people see a lot of interesting things but I doubt if this young man had ever seen a butt plug in the ass of one of his female guests.

Before she got back in the tub Amanda got two things out of the bag from the adult store. The first was a bigger butt plug and the second was a Japanese face slimmer.

Before I pulled the first plug out of Amanda's ass to replace it with the larger one, I had Amanda play with her pussy again.

She bucked it and groaned and shook as I pushed the larger unit into her ass but there were no tears just acceptance as she spread her cheeks for me, using both hands, showing her compliance and her complicity.

She knew the fate of her ass as it related to my cock. She knew how big I could get and where it was going to go before midnight.

Once the plug was in to the hilt, we started kissing.

Amanda really, truly, enjoyed kissing me and we made out like teenagers in the warm, soapy water of the bath. As we kissed my hands roved all over her body.

I told her "You're mine, every inch and ever hole" and she smiled and laughed and just said "Yes Jack."

All this got me very hard and I put the Japanese Face Slimmer on Amanda so she could give me the quality oral sex I wanted from her.

Not that her blowjobs weren't great but her openness and willingness to trying new things was an excellent opportunity for me to be pleasured by a young twenty something woman who was hot as hell.

The plastic tubing device forced and kept her lips apart about three inches in diameter and it allowed me to stick my cock deep into her mouth and into and past the tight entrance of her throat.

Until I could train her properly to take me all the way without gagging this would suffice and I was able to go deep into her mouth and come in her open but tight throat. It was a blowjob I will always remember, despite her few tears and a bit of gagging.

After I came (it was highly pleasurable) we got out of the tub and I dried her.

Grabbing a small bottle of baby oil I videoed Amanda rubbing it all over her body, until her tits, tummy, ass, legs and bare pussy were glistening.

Reaching into the brown shopping bag from the adult store I set a stand up dildo on the carpet in the living room floor and said to Amanda "I have three of these, this is the smallest. You're going to fuck yourself until you come. After you've come the first time you'll get dinner but not until. I'm videoing this so I can watch you when you're at work. Be the girl next door who is casting to be a porn star."

What I didn't tell Amanda that was that she'd be fucking either me or a dildo until she left on Monday morning.

Amanda performed for two hours that night, all the next day and Sunday night too.

I took her ass later Saturday night after I pulled out that larger second butt plug.

I had her on the bed in the second bedroom of the suite, on her belly, her ass raised and well lubricated.

Amanda screamed in pain as I initially entered her but the butt plugs had opened her up and she quickly began to match me thrust by thrust.

She was tight, but I was able to last having come several times since picking her up at work.

After I unloaded into her bowels that first time she cleaned me with a warm towel and sucked and teased me back to size and had me take her again and again and again in her ass in different positions throughout the weekend.

The hotel room smelled of shit and sex and sperm and neither of us cared.

****

At breakfast on Sunday morning I got to know Amanda.

This was after she rode me to an orgasm before sunrise. I fell back asleep only to wake up with her mouth on my hard cock.

We worked out again and we fucked in the shower.

She had graduated from Cal State LA in December and was hoping to start her graduate program at UC San Diego with a travel course.

I asked her when the course started and how much it cost.

Amanda pushed back not wanting to share the information but I finally got a date and an amount out of her.

And some details on the trip and the Masters program.

She had to work Sunday from noon to 8pm.

Before I took her over to the restaurant I gave her two Ben Wa balls.

Amanda raised her eyebrows and I smiled and said "You'll be hot all afternoon."

It was pretty fucking hot watching those shiny steel balls going into her tight pussy.

It helped that my tongue and fingers opened her up.

Ben Wa balls always got a better reception after you've eaten the lady to an orgasm or two.

I also inserted the larger butt plug back into her ass, just as a reminder to what I was going to be doing after she got off work.

While she was behind the bar at the restaurant feeling those steel orbs move with every motion she made, I connected with the professor running the trip, got the list of what Amanda needed to do and I arranged to have a check in his hands by Tuesday morning to cover the cost of her going.

It was dark and the rain was still coming down when I picked Amanda up after work. We were going to go back to the hotel but Amanda was so worked up she asked me to drive to an empty area of the parking lot where she pulled down her jeans and thong panties and asked me for permission to cum.

She wanted us to go into the back seat again so we did. We made out like we were in high school and she asked me to please eat her.

I said I would eat her if she played with herself for me first.

Amanda rubbed out two quick orgasms, the pent up sexual frustration of 8 hours of two steel balls ramping up her sexual desires.

I licked her to a third and she kissed me in gratitude, Amanda tasting her own juices again.

Back in the hotel we sat in the living room of the suite and I told her what I had done, and that she had until Friday to get ready for her trip because the plane was leaving LAX on Saturday.

Amanda's chin quivered and then she burst into tears, climbing onto my lap, just sobbing.

We spent the night in that suite, fucking like there was no tomorrow. On Monday morning I took her to the bank and made a cash withdrawal so she would have money for her trip and also to take care of her travel preparations.

At the same time I made arrangements for Amanda to get $4000 a month on the first business day of each month for the next three years.

She was stunned, but I just told her "You've been so kind to me; the least I can do is get you through your Masters program. Maybe into a doctorate."

We kissed goodbye in the parking lot. We both had tears but we were starting new chapters in our lives. We vowed to stay in touch.

About a week later I got a very long letter from Amanda that she had written on the plane. She wrote that her younger sister had been in my wife's class and that she had first met me when she was in the 8th grade when she was 12. She'd had a crush on me ever since and thanked me for everything (she underlined the word everything). And, if I ran into her parents or her sister around town, well, that I knew how to keep a secret because there are some things a girl didn't want their parents or their sister to learn about.

Each month on the first business day of each month Amanda would email me a note telling me where she was and how she was doing. It was always good to hear from her. I always responded back with a short note wishing her well and to let her know if she needed anything to please just let me know.

I kept those videos a secret and watched them often.

****

Two weeks later I took Brie and Lauren (the two other bartenders that Amanda worked with) to Las Vegas.

I made reference in my first story "I Hire Monica the Maid) to taking two women from the same company to Las Vegas and how I facilitated these two to reveal their attraction and affection towards one another.

I did fuck both of them, numerous times in all three holes but we never had a threesome.

They liked one on one sex, not two on one sex.

It didn't matter to me; I achieved my goal of fucking them both in all three holes.

But that item, a threesome, a Bucket List item for me, was soon to be checked off.

Catherine and the girls came home and we had a quiet night that New Years.

We were in bed by 10pm.

But I took Catherine three times that New Years Eve.

She loved it. And wondered what had come over me.

In a word, Amanda.