The past few months had been very busy and exciting, first Gloria, then Kim, with Trish at work and then the ongoing affair with my boss Debbie....I didn't know where I was going tog et the energy from to continue to put in long days at work....
A surprising turn of events took place a couple of months after my first get together with Debbie. She announced she was selling the company to a nationwide plumbing service company, thus leaving her free of all the commitments that owning a business brings. "It's time for me to enjoy semi-retirement, before I get too old to enjoy it," she said at the staff meeting.
Debbie stayed on as our boss, guiding the firm thru its transition to the new owners and just generally keeping anxiety amongst the workers in check. What did change was the hours Debbie worked, now doing 7-8 hours a day instead of her usual 12 or more....semi-retirement like she said...
In this atmosphere it was easy for business to continue as usual. We even got to tender for a sizeable plumbing contract in a new retirement village that was about to be built. This is where Debbie called on me to help her out, not with my work experience, but with wooing the lady in charge of the project.
This is where I got to be rather worried, asking Debbie; "So what exactly is it that you want me to do in order to help us win this job?"
"OK," Debbie started, "Ms Sarah Brixton is a widow, she's now in her late forties, doesn't have time for a full time boyfriend or partner, but word has it she enjoys the occasional fling with a younger man, preferably a well endowed younger man."
"Right, so you want me to wave my wand and you think she'll just sling this job our way huh," I said sarcastically while Debbie looked displeased at my simplistic view of things.
"No, you need to think outside the square a little," Debbie grinningly said, "think of yourself as the icing on the cake. I will make sure the pricing etc is right and then offer her a bonus, you, just to sweeten the deal for her. That's if you are up to this formidable task."
I was stunned, my boss / lover wanted to pimp me out just to gain a contract. Interesting as this sounded I wasn't at all sure whether I had what it took to be a gigolo...let alone the morality of this suggestion.
As I had just been sitting there pondering this proposition, Debbie moved in front of my seat and started fondling my now admittedly rather stiff cock. "I see your number one tool has no problems with this suggestion," Debbie playfully said as she went to unzip me.
Debbie went on; "You know how you mentioned you've got a thing for older women...how you said you liked the look of English ladies such as Penelope Keith in the old series 'to the manor born'?"
Not offering any resistance to having my cock brought out into the open and then sucked vigorously I pondered the proposition Debbie had made me, all the while she's sucking half my shaft into her hot mouth....her fingers raking my heavy balls....her usual way of urging me to cum in her mouth.
It took Debbie not long at all to bring me off in her willing mouth, squeezing every last drop from my throbbing shaft and sucking me dry with enthusiasm.....
"Yum, now have you made your mind up," Debbie asked as she licked her lips, carefully gathering the last few drops of spunk from the corner of her mouth.
"I think Ms Sarah Brixton has a bit of Penelope Keith in her," Deb said suggestively, "might just give you a good thrill, fucking a lady who reminds you of one of your favourite older women...."
"Let's hear your plan then," I said as Deb sensuously kissed my now partially softened cock, then slowly sucked one of my sensitive nuts into her mouth, her tongue licking it harshly thus sending an incredible sensation thru my body and making my dick twitch....all this on a weekday morning, in her office, with people outside her office waiting to see her. But Trish knew the drill now, if Debbie said no calls or disturbing, then she did just as she was told.
Debbie laid out the basic plan she had; "Simple, I'll invite Sarah for dinner at her favourite hotel in town, see if I can talk a little about younger men and their energy in bed. If it seems like she's up for a bit of hanky panky then I'll bring her to the room I will have booked after dinner. She'll find a young handsome, well endowed man, who will discreetly but energetically fuck her all night. In the morning she'll discover you work for the company, and with a bit of luck she'll give us the contract.... just so she can get another ride on your pleasure stick, simple!"
I must have looked very surprised 'cause Debbie looked worried, saying; "Now don't be so coy, I know you love to drill us old birds Nick, we are just sooooooo appreciative!" As if to emphasize the point she sucked my cock into her mouth once again and looked into my eyes as her tongue probed under my foreskin, teasing the hole in my knob and running the tip of her tongue under the helmet, causing me to squirm in my seat.
"OK, OK, I will do as you wish," I said defensively, as if against my will. Deep down I wasn't ready to admit just yet that I loved older women, especially ones who were hot for sex. Much like Trish had surprised herself when she challenged me to fuck her on the reception desk, only to find my big cock hard and ready to drive into her wet and willing snatch....I was finding myself immensely turned on by the prospect of making love to an older, powerful woman....the fact the firm could gain a lucrative contract as a result was neither her nor there for me personally!
On the night in question I was in room 1511, a luxurious suite on the top floor. Debbie had also booked room 1512 for herself and as she prepared me for my night of passion she told me that if I had any doubts, now was the time to bail out.
"Heck no, just bring on this horny woman," I said confidently, Debs kissing me softly on the cheek as she departed the room, heading for dinner as arranged.
At a little after 9 pm my cellphone beeped, the text message warning the ladies' departure from the dining room bringing a flutter of butterflies momentarily.
