How I Spent My Summer Vacation

The third layer was that Lourdes had to be better than the other ladies sharing my bed with me that morning.

The last layer was could she compete, could she beat, other ladies both known and unknown, as my blowjob queen?

Lourdes set a high bar. I was the recipient of her improved skill set and her competitive nature.

Post orgasm, with Kelly having taken care of Lisa's need for relaxation and Lourdes having taken care of my pressing issue the two us, hand in hand, headed to the workout room for about 45 minutes.

The two young ladies got breakfast, the newspapers and coffee delivered to the room. They also laid out our clothes for the day; printed out our schedules and got us prepped for the day.

When we got back to the suite, Lisa would eat quickly, and then Kelly would bathe Lisa in the shower, help get her dressed and then Lisa would grab a coffee at the hotel lobby Starbucks before heading over to teach classes.

I read the papers, enjoyed my coffee and had a leisurely breakfast. After Lisa left, the two ladies would bathe me and I'd be on conference calls starting at 7:30 each morning. Lourdes went to the new gym to work and Kelly stayed with me.

Kelly had been taught well; post finishing school I had sent her to two different massage schools, one run by an older, mature Caucasian lady and the other by an older Asian MILF. I wanted the best of both worlds (East and West) and Kelly did not disappoint me.

These were private schools, and Kelly had only very private lessons. Kelly was allowed to practice on the male students of the class, so she learned what a man liked when it came to massage, but the male students were not allowed to practice on her. She could practice on other females.

When the other students left for the day, Kelly stayed after for one on one sessions with the owner of each studio.

Per my instructions, everything Kelly did was videotaped and errors were pointed out to her and she was spanked for every infraction. With this as an incentive Kelly rapidly improved her skills.

The owners liked that Kelly got better too, because they benefited from her rapid escalation into the sensual arts.

Although initially reluctant, after a serious spanking session that I personally administered Kelly almost instantly came around to learning how to orally satisfy her female instructors.

I figured if I had let her go to prison she'd be someone's bitch (as in the old movie "Caged Heat") so why not have others enjoy the same benefit as she repaid her debt to me?

It wasn't like I was going to rent her out; I was training her to become self sufficient over the period of her probation period. My plans for Kelly were to use her to improve my life and the lives around me.

And just so you know, Kelly was paid $15 an hour plus overtime ($22.50 an hour) and every dollar was banked for her future. I picked up all of her costs. She was grossing over $1000 a week; Nevada has no state income tax and she had no expenses.

As far as the typical workday went, I took most of my calls in the suite. I had Kelly wear summer dresses; no panties and no bra. Her body was young and firm; going to the gym each day kept her tight.

She sat next to me as I talked on the phone, taking notes and making sure each call was recorded (and then transcribed) so that there were no misunderstandings about expectations or deliverables.

Most of the time I was on the speaker phone, and I had a floor pedal to push when I wanted to go mute. That also freed up my hands and my right hand often wandered all over Kelly.

Often her dress would be at her waist as my hands roamed.

My favorite time each morning was when she stood next to me on my right side and my hands would wander under her dress, up her legs where I would absent mindedly fondle her tight young ass while pondering the decisions I needed to make in my business.

That fondling always brought me an erection.

When that popped up, it was time for some relaxation.

****

At eleven thirty each morning, I had Kelly give me a massage.

Kelly's hands were small, but through practice became strong. Her tiny fingers allowed her to reach crevices easily and when she held my balls, her hands runneth over; when she massaged my cock, it was longer and wider than her hands could accommodate, which made her work all that much more harder to please me.

Not that I was hard to please at that hour; I wanted a hot nude woman massaging me and making me feel like a King. Yes, I was getting a bit of an ego but so what.

After initially having Kelly wax her pussy hair off, I now wanted her to grow it back. I liked the idea of her sitting on the backs of my thighs rubbing my neck, shoulders and back while her soft pubic down massaged my bare legs.

Despite my punishments, Kelly was falling in love with me.

By design, I was the only man in her life.

Who better than a beautiful young lady to keep me happy at work; to keep things light?

*****

In case you're wondering if I ever fucked Kelly, the answer is, of course I did.

How could I not?

I just didn't do it before I broke up with Lisa, who after her summer session ended went back to stay with her parents the rest of the summer.

Broke up is too harsh a term; I did sleep with her later but the summer fling was just that. She was a fine roommate.

But we didn't go our separate ways before I hosted a dinner event at Morton's in Las Vegas for all the professors in her department, and the dean of the school of business and economics, and offered them each a consulting assignment, ongoing, for my corporations.

The catch was one I knew that they could swallow, which was that Lisa was the head of the program. In essence, she was their boss on this deal.

As Glen Frey sang in the song Smuggler's Blues, "...it's the lure of easy money; it's got a very strong appeal..."and whatever sexism there was vanished when I handed out the first retainer checks insuring that Lisa was going to get full tenure when her time came.

I take care of my ladies, and I took care of Kelly. Many times.

But I also had to get rid of Lourdes if only for a month or so. I sent her down to Mexico, had her staying at the hotels along the beach, doing some scouting for me.

****

With Lisa gone, I introduced Cindy the lady who was going to be an attorney to Kelly and Lourdes.

Kelly knew her place, low man on the pussy eating totem pole.

Cindy loved it when her light red haired pussy was licked by Kelly.

That's part of how Cindy spent her summer vacation; nude, on her back, while a pretty blonde parole satisfied her need to come with a tongue and lips that would not quit.

******

On that flight back to LA, I wasn't thinking much about business.

My brain was over flowing with thoughts of sex with young hot ladies.

I fell asleep on my jet, having consumed far more Silver Oak than I wanted to, but I needed something to help me cope with the issues I was dealing with.

I'm not making excuses for drinking too much. Nor am I trying to justify it.

I wasn't a mean or happy drunk; when I drank too much I usually fell asleep and stayed that way.

I did remember the flight attendant dimming the lights, pulling the window shades down, putting a blanket over me after she took off my shoes, socks, slacks, and dress shirt.

She kissed me on the cheek and whispered to me "Sweet dreams."

******

I woke up slowly only to discover that I had been fully undressed --- I was now nude --- and was under a nice thick blanket on my double size recliner seat.

The only lights on in the cabin were the floor lamps and the plane was still flying through the dark night.

My cock was hard, very hard, and I was snuggled up to the bare butt of a woman, one that smelled wonderful and I could tell had a terrific body because my arms were wrapped around her and were holding her more than ample breasts.

I was nut to butt. And she had a very nice butt.

She stirred and pushed her ass against my hardness and my hands moved to her nipples in response.

She giggled and said "I'm Angela; I was told to take very good care of you on this flight."

I kissed her neck and goose bumps broke out over her body.

"So you're my angel. You sure have taken good care of me" I replied.

My fingers started playing with her nipples and her ass started moving in the primitive ritual of mating.

My hands wandered south across a flat belly and soon found a hairless pussy; she spread her thighs to provide better access for my roving hands.

Did we fuck?

Oh, yeah, that entire cabin smelled like sex by the time we landed.

Angela was a screamer; a squirter(!) and her pussy was better, tighter, hotter and wetter than I had imagined it might be.

And she was a highly responsive lover, meeting my every thrust with a return and often a twist that made our fucking session highly pleasurable for both of us.

I had my hands all over her, and she loved my tongue on her cunt and rosebud. I sucked her toes, kissed her nose and with some effort she deep throated me despite some gagging.

She was amazed at my size and told me so. But she took it as a challenge for me to be inside of her three holes.

I came inside of her welcoming pussy, she swallowed without hesitation and I quickly dumped my final load of the trip deep in her dark passage as she told me how important it was for me to "go around the world with her."

Her ass was so fucking tight I barely lasted a couple of minutes. She was no anal virgin but she was tight and knew how to use that ass of hers for my pleasure.

And, after we got off the plane at Burbank Airport I took Angela across the street to the Marriott, checked into a nice suite where we fucked all night long.

I told the pilot and copilot to tell anyone who asked I was in Mexico an extra day.

I'd made up my mind I wasn't giving up my chasing pussy and if Catherine or the other ladies in my life didn't like it, they could go fuck themselves. There were simply too many women like Angela in the world for me to retire from the days of my hunting for fresh pussy.

******

Jack Colton will return soon.