Part three is another 'real life' event that happens multiple times in the spring, summer and fall in my current world. All of the characters in this story exist in some form around my neighborhood and it's fun putting them into my stories. The every day vanilla events and conversations are real, so are the thoughts that I have in the story on all things relationship and sexual.
We are all in our upper 50s (except when indicated).
In the pervious chapters we've entered a month of denying our climaxes and working on stamina, while my neighbor Jill and I had entered into a somme-submissive contract. Mel and Jill had a girls trip and I've already been in multiple positions with Camilla, the dark-skinned influencer next door.
I also want to note, part of my fantasy is I'm expressing these ideas while my wife has similar thoughts (since we really don't share in real life) My hope is in the end it's like "Escape (The Piña Colada Song)" where they each go looking for an affair and find each other...and neither is pissed.
So rather than the usual tropes around betrayal and cheating, I weave things together that eventually work themselves out, sort of...
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Mel woke late the morning after the girls trip to Galena, meeting Gladys, making out with her, being denied (since it is denial month in the neighborhood) by Jill and then spanked against her will.
Gladys took Mel over her knee, cuffed her and spanked her to tears, Jill left to assure Mel would come back, thus giving Jill higher status in Gladys fold of Mistresses and Masters (Grand Mistress).
I was waiting with coffee, having been freed from my chastity cage by young neighbor Camilla then tested my resilience, bringing me to the brink of orgasm time and time again, my cock entering her mouth and pussy repeatedly.
Camilla then trained me to use masturbation to repeatedly climb to the brink, pulling back before ejaculating, pausing and continuing the stroke. Camilla slipped next door just before the ladies returned, Mel quivering in the passenger seat on the way home having her boundaries tested.
I suggested a bike ride to Mel.
We needed space from the neighborly acts, knowing Brian was returning home to Jill and last night after Mel passed out in bed, I fucked Jill, turning the tables on our game of dominance she had turned on me.
The past week she had me as her submissive, a game I wanted to explore further, not my preference when it came to bedroom power dynamics. I fucked Jill so hard last night I knew I reclaimed Master status, playing the game both seemingly switch dommes. I had signed a contract that had me scurrying over when the word "BUST" was texted to me, and would then train me by introducing her brand of restraint, punishment with a hint of pleasure.
"Why not," Mel said with limited enthusiasm for the bike ride, her will broken last night, Gladys had started a little girls tryst, Gladys laying hands to the the married woman's bare ass. "We can stop at several places like you have always wanted to do."
"Seriously?" I said excited, Mel liked to get to a destination, turn around and get back, only taking advantage of the work out not stopping at the establishments with bike themed names that served food and drink. "Awesome, I'll pack my wallet."
I'm nearly 60, she was in her early 50s and in decent biking shape. Together we could go 15, 20 or 25 miles making it a leisurely ride. Mel liked it for exercise though she didn't exactly power through for time. We could do a mile in about 5-8 minutes and had several routes that we would pass places called "The Sag Wagon", or "Pedal's fork", as well as through newly developed areas with everything from food and drink, to antique shops.
Similar to my jogging observations, you encounter people biking in tight clothes, good shapes (generally) and great attitudes. The fresh air and movement generates good vibes from everyone you encounter, and my sexual imagination while riding bikes kicks into full gear. Wearing sunglasses it is easy to lear down the shirt of an oncoming female bike rider giving them a nod or generally saying "Hi!" to just about everyone.
My mind likes to tell itself stories moments after your pass, or get passed. The fantasies I've imagined are numerous, We've encountered people I swear would be so interesting sharing a drink with at a local establishment and today's the day Mel was up for that possibility.
Iowa has a "Race across Iowa" called RAGBRAI, where thousands of bikers spend a week on the road riding, camping, and cavorting. Six stops from the Missouri to the Mississippi river, sweat, spandex, exercise and booze. We're getting to the age where it's now or never, and that idea certainly sparks fantastic ideas of tent sex, mixed couples, drunk singles and group sex.
I do not possess a bike shirt or tight shorts, Mel and I simply get into workout gear and head to the bike path loading up the bikes on a hitch carrier. We got water, I packed my wallet, and the usual first aid and bike repair things (Like I could repair something on the road).
Mel was very distant.
I do bring a blue tooth speaker for music while we ride and once I got that set up we took off. I stay just behind her, letting her mood dictate the pace while keeping the music in ear shot of her pretty backside. No helmets, we figure we don't go fast enough, a mistake I know, Mel having a decent pace for a change.
It was 10 a.m., the temperatures were going to get warmer and we were on the late side of missing the heat, and for Iowa the humidity wasn't bad. Many bikers were getting done and the usual array of serious bikers, recreational (like us), joggers, families were out in force. We loved the community of people that did value fitness and recreation, moving from a smaller town a year ago where who was quite sedentary.
Mel kept her promise and we stopped at the first real establishment we encountered, a converted house that had a wine feel. We found a small table outside in the shade of the large maple trees and the sever got me a beer and Mel a glass of sparkling wine.
"Bubbles, of course" I said, her summer drink of choice on a patio Mel staring off in the distance, then turning to me her eyes wanting me to ask something. I found her stoic, distant presence interesting. "What went on yesterday?"
"Nothing and everything," she paused first and said, surprised I cut to the chase at the first stop. She was fast to bed last night, though she had no idea I went next door and took Jill forcefully minutes after she fell asleep. "Do you remember me talking about Iyndia several months back?"
"Your Chemistry lab partner?" I said, of course remembering her tale of lesbian experimentation. "There was also Christy, Jazz and April if I recall."
"Correct," Mel confirmed blankly, not wanting to retell or revisit those stories. "Do you remember why I brought all of that up 28 years into our marriage?"
Her tank top was open and I looked at her 50 year old cleavage, it was inviting, I sipped my bourbon while Mel licked the rim of her wine glass after her sip.
"I remember you mentioning it while we were dating also," I felt the need to add, something a guy doesn't forget because, well, of course I would have loved to have a pay off watching such things. It never happened in our 28 years. "Those types of feelings had resurfaced, right?"
"Correct," again the confirming blunt statement, I felt the next sentence was going to be the meat of her thinking. "I'm drawn to Jill."
"I see," I thought, not surprisingly watching the little touches, the kisses, they're going out a couple times recently, Jill delivering sex advice for our bedroom. "Did something happen yesterday?"
"Do you trust me Donnie?" Mel stared at me before continuing. "Do you trust me if I make overtures to Jill?"
I thought about it for a minute. She's interested in the woman I was having an affair with currently, playing around with the object of my wife's desire, oh and Camilla be sent over to please me.
I wanted to quickly say 'yes' contextually, thinking if I could play around with Jill, why should she and the 'what ifs' were delicious to think about. "Are you think...."
"I kissed her and made out with her friend to please her," Mel said cutting me off, downing her wine and getting up. "Let's make some more progress on the trail. You think about your answer again, and please tell me your real thoughts at the next stop."
"Understood," I said, almost as if Mistress Jill was in my presence. I noticed my cock was hard. We were both getting involved with the same woman, and how hot could all of this be?
We hit the trail, a 20 something hottie coming on the trail at the same time, riding with us for several miles, getting my attention pedaling just ahead of Mel, her fine ass on the seat. I got a good look at her cleavage in the sports bra, blonde hair tucked in her helmet when she passed us.
She said "Hi" with a nice smile, the outline of my hard cock had to be evident on my seat if she were to look in between my legs.
Our pace didn't match hers at first, Mel's usual sauntering didn't match the young woman's pedal pumping, she pulled away slowly and I got to stare at that ass for a good while. My mind raced about the trust question, where should I take it, total transparency or did I angle to bring the reality of my sexual dealings with Jill closer to the fantasy?
The next stop rolled up quicker than I anticipated and was were dismounting at the "Shag Wagon", a reference to the bus that picked up bikers on RAGBRAI that could keep up. Mel pulled up, and announced she had to use the bathroom. I found a table on the patio and was startled by someone brushing my shoulder...
"I'm sorry!" the young voice said, and in a moment I was looking up into the eyes of the sensually young woman who passed us on the trail then she asked. "Did your wife leave you?"
Must have been the nervousness of bumping into me, I replied without thinking, "Bathroom". And she giggled at her clumsy question on the way to her seat with another 20something young lady.
The first responded back "Have a great ride."
'I'd ride you,' I thought, going to the gutter just before Mel sat down.
"Your thoughts?" Mel asked.
"About young, blonde hottie over there," I blurted out in a bad joke, getting Mel's disappointed, but 'this is what I married', look. I plowed forward.
"Mel, I trust you implicitly that at the end of the day we're together, truthfully I've trusted to this point that even if you'd dipped your toes in the 'lady pond' over the past 28 years you've come back to me each night," I stopped, semi-happy with my response.
"Jill's hot," Mel said, lobbing a direct statement in my direction. "She's occupying a lot of space in my head, and I'm obsessed."
"I've got eyes," I replied, demonstrating my non-directness. "I can't say I haven't had a thought or two about her, especially after she kissed us both the other night. Did you say something about you and a friend of Jill's making out?"
This struck a cord.