Rebecca rocked back and forth gently from side to side as her hand slowly caressed the bulge below the pit of her stomach. “I really don’t know how to thank you for helping me stretch my pussy,” she responded with a very straight forward but pleasant tone. “I never imagined that someone from the office would be involved in this in any way whatsoever, much less even know about it.”
“Your secret is good with me,” I replied as I pulled a bunch of paperwork out and began sifting through it. “Besides,” I said as I raised an eyebrow and looked up at her, “You did already give me the most phenomenal blowjob I have ever had in my life.”
Immediately this coy grin came across her face and her cheeks flushed just a little when I reminded her. “Yea, I did, didn’t I?” As she made the admission I noticed her nipples stand up hard on her breasts. “But Mike will never find out, will he?” she stated with just a slight bit of worry to her tone.
“Never in a million years,” I replied quickly as I handed about half of the stack of papers to her. “Take a look through these and mark up anything you find. By the way,” I continued as she took the papers from me and slowly started toward the door. “When is your trip?”
Rebecca stopped right in the middle of my office with her legs parted enough to have her short skirt pulled tight against her muscular thighs. “After the baseball game last night Mike said he was going to call his buddy today and set it up. From what he hinted at, we are most likely going to leave this Friday morning.”
“Ok,” I responded even though I was a little bit struck with the fact that my favorite fuck toy was going to be out of the office for several days. “And how long is your trip?”
“Mike has it all planned out already,” she responded as she sat down on the arm of my office chair and ground her pussy into the cushioned top. “If we leave this Friday morning, it is going to take us 6 days to get to California.”
“Wow!” I responded at her statement of time. It struck me as being a bit long because I have driven all the way to Oregon before in only 4 and a half days. And the trek to California is about 1000 miles shorter. “Why so long?” I asked in genuine curiosity.
“Mikes buddy is insisting we stop at the Grand Canyon and a few other places along the way,” she said as this odd little grin came across her face. “Could you just imagine me walking around the Grand Canyon amongst all of those tourists with a can of beer up my pussy?”
“Yes I can,” I responded quickly as I scoped up and down her long and lean body. One thing was sure; I was definitely going to miss my ‘in office’ fuck toy.
The week flew by at a rate that surprised me. It seemed like only an instant since my weekend romp with Rebecca and my sister before Thursday afternoon rolled around. As I was finishing up the last few tasks I had Rebecca strode gracefully into my office sporting a million dollar grin. She looked like she was floating on air as she sat down in my spare office chair and spread her legs wide apart. She sighed loudly as she settled back into the chair with her nipples jabbing out against the material of her top.
“Excited?” I asked as I looked over the top edge of the papers I was holding to gaze not only at her bare pussy, but at the elegant woman that was now gracing my office.
“Oh yea!” she smiled as she wiggled her hips back and forth to expel the two pool balls from inside her. “I have been looking forward to this all week!”
“I’ll bet you have,” I responded as I set one stack down to inspect the last one for the day. “So tell me, have you practiced riding any with the can inside you?”
Rebecca looked over at me with just the tiniest bit of worry in her eye before she responded. “No I haven’t,” she responded. “And that was one of the conditions for the challenge. I was not allowed to get any practice riding with a can inside me before the trip.”
“Wow,” I replied as this started to sound a little more difficult. “At least you will get some relief when you overnight.”
“Oh no,” she responded almost instantly. “I don’t get to take the can out at night time.”
“You’re kidding,” I retorted as I shuffled the papers together in an attempt to get them aligned into a nice stack.
“Oh no, not kidding. Once the can goes in, it does not come out till we hit long beach.” As she said this her nipples threatened to tear holes in her shirt.
I let out a little chuckle as I set my papers down and looked her squarely in the eye. “Scooterfish.” Instantly Rebecca’s gaze went blank as her eyes stared out at the empty space between us. “Tomorrow morning, as soon as you sit down on the bike, you will have your first orgasm. After that you will have an orgasm every five or ten minutes for the duration of the ride. Understand?”
“Yes,” she replied quietly.
“We will talk about the rest when you get back.” I said as I extended my hand towards her. “Pool balls please.” Without hesitation Rebecca reached in between her legs before producing the two wet pool balls. Taking them from her I placed them into my jacket pockets before returning my attention to her. “On the count of three you will wake up and feel fully refreshed and ready to go on your vacation. 1..2..3.” Immediately Rebecca’s eyes came back into focus and she looked at me with a pleasant smile. “Good luck on your trip tomorrow.” I said as she stood up and prepared to leave my office. “I hope you have a ton of orgasms.”
“Mmm,” she said as she stopped just inside my door before turning around. “That would be nice,” she said as a small frown came across her face, “but I have never had an orgasm on the back of Mike’s hog.”
“There’s always a first,” I said.
“See you in two weeks,” she responded as she started out the door.
“Two weeks?”
“Yea,” she said as she paused and leaned against my door jam. “Its six days to get out there, and then six days to get back.”
“Oh yea.” It felt like my chest had just been jumped on. I had not even thought about the trip back. “Good luck.”
Rebecca gave me just a little wink before she spun around and headed off with just a tiny hint of spring to her step. Her adventure was really going to be something.
The End Ch5