It started out as a playful flirty kind of thing. I'd just gotten over a divorce and now happy and relieved things were working out between me and Lisa. At first she would give me ribbons from her hair or bits of fabrics, or straps, or trinkets for me to wear at the base of my scrotum as a kind of cock collar. She joked that I was only permitted to masturbate while collared for those times when, say, work schedules etc. didn't allow us together time.
Eventually, she would call me from the law office at my work at the health club and tell me when she wanted me to jerk off for her live and on the spot. We were getting along great and having great sex at night and on weekends, so soon I was finding I enjoyed this little game of Lisa in charge. Sometimes I would have to find space in a lavatory at work or at business or sports bar rest room or something. I would then have to call or text a report to her of the "juicy details" as she called it. Other times I would wack off in the car or if I was at home while she would be on the phone or video call app and coach me with hot dominatrix dirty talk! Soon things got the point where I usually only had the urge to masturbate when and if she required it.
Since she made more money than me, I became accustomed to having her way on this and she was very reasonable and sweet and not too demanding as one might expect. But as we became more serious, she decided (and I pretty much readily acquiesced) to turn the heat up a notch.
"Call me in twenty minutes, after I get back from the lunch meeting," the text said, late in the day as she had travelled on business to the west coast.
I'd left work early and made myself comfortable before putting through the call. To please her, I fastened an old thin black patent leather watch strap of hers around the base of my ball sack.
"I'm in the ladies room. Earphones. Charlene is in the next stall. She's a close talker, so play along Ok?" So earphones meant only she could hear I guess. But what was this playtime in the women's toilet all about. Kinky indeed.
"So, honey, how's it going?" Lisa purred.
"Uh, Ok".
"I hope so. You sure?"
I could hear Charlene talking through the lavatory sounds of running whooshing water, "You talk to your boyfriend while sitting on the john?"
"Uh, no Char," the neighbor is housesitting and she is also babysitting our niece.
"Oh," Charlene replied.
"Naughty toddler," I heard Lisa murmur.
"What... who..." I inquired confusedly, remembering Lisa's comment about playing along.
"Put her on the phone," Lisa ordered sternly.
"What..."
"Just do it dear," she commanded emphatically.
"OK," I sighed.
"Now, now, Daphne." I guess this was to be her version of me being her Dave in this scenario.
"You know Aunt Lisa, doesn't like it when you come over and eat too much junk!"
"Yes," I answer in a complying tone.
"And too much juice box is not good. Did we check your underpanties today. Are you damp?""
"Uh"
"Yes! Yes what dear?"
"Yes... Aunt Lisa..." I answered submissively as I started massaging my cock out of my basketball shorts.
"And when you checked this morning, is it soft or hard?"
"Sounds like she needs more fiber," I heard Charlene giggling.
Lisa licked her lips and smiled deviously on the video chat screen, as I obediently displayed my trained swollen cock for her approval.
She went on, "And no little temper tantrums for the babysitter or Aunt Lisa will need to spank your bottom. Understand?"
I could hear the sounds of Charlene primping and zipping and flushing as I stroked my hard on. Lisa leaned back in the stall to reveal that she wore no underwear under her business skirt and had shaved off her dark bush.
"Understand what?" She laughed along with Charlene, whose voice trailed off as she left the room.
"Yes, Aunt Lisa,"
She giggles some more as I try to hold back the jism, "Charlene is gone now, so let's hurry it up!" she urged,
"Your office people... you didn't tell..."
"Never mind," she snaps, as the screen flips all dark and topsy turvy as she sets the phone down with a clinkity sound, "Now pay attention..."
"Okay."
She stands in front of me and lets me look at her curvy voluptuous as she bends over to tug up her skirt. "KIss it," she orders.
"OK,"
"Do it, so I can hear you!"
She spreads her ass cheeks slightly and giggles as she allows me to watch her golden fountain from behind. With a swish and a swipe of some paper towels she tidies herself up and envelopes her sweet ass back into her navy blue business skirt. "Had to mark my territory. Don't come all over yourself!"
She blew me a kiss, "Good boy. See you when I get home." And hung up. I almost came wondering what she told the gals in the law office about the real story behind our "baby-sitting" arrangement.
Over time, these little long distance playtimes between Lisa and I produced additional benefits, as I eventually could maintain longer, stronger erections during our actual nighttime lovemaking. Upon return from this latest business trip, she seemed much more interested in other women. She would bring up Charlene from time to time, prodding me to explain my feelings about possible scenarios involving me "pleasuing" her and her co-workers in a theoretical group session.
Things seem to come to head as she was able to get me to go along further and further with her kinky dominating role play situations. During the past few weeks, I (or we as it were) became fascinated with a new customer at the health club. Brianna Jenkins was a kind of local celebrity, a record breaking high school basketball star and current women's hoops coach over at State College. She was a fine looking six foot tall women in her mid twenties with long blonde hair with a magnificently chiseled physique. Her team always did well and she had established a great career for such a young coach. Lisa and I enjoyed following her success on TV, radio and the local papers. I explained to Lisa that my main task was to aid her in rehabbing a surgically repaired leg resulting from an injury during her playing days. A surgical scar running nearly the length of her left outer thigh profoundly marked her otherwise perfect body.
One late afternoon I put her through her paces of leg lift routines. She gradually shed her self consciousness about her leg scar and now presented herself in clingy medium short shorts as she went through the next part of the routine, face down continuing through the leg lifts.
