Making Our Babysitter a Sex Student

No sex tonight. That's at least what Heidi and I thought when we left the meeting with our normal swapping partners, Juan and Donna. Since Donna's parents were a part of the meeting at the estate where they all lived, it was a formal discussion that left Juan and his wife Donna fully clothed along with me and my wife, Heidi. As we two younger couples sat through the important details of the estate plan created by Donna's parents that would benefit us all, my mind drifted to the history of the sexual encounters the four of us had shared. It started with the moonlight skinny dip cruise that established our sexual swapping. Our trip to New Orleans for the Maritime Trade show was supposed to be for business, but we found time to exploit our luxurious surroundings and engage in an unexpected orgy with a surprise guest that was gifted to us. It was "all hands on dick" for the captains and crew. We had become veteran swappers and were the best of friends, sharing our lives and lovers with gusto and exploring new areas of pleasure and sensual experience.

Juan and Donna lived in a home on the estate of Donna's parents in the Florida Keys. The parents had made a lucrative and timely entry into the real estate market decades earlier and had reaped the benefits of ownership of a large waterfront estate as well as several income properties. They shared their good fortune with their only child, Donna, and her husband and their two small children. The parents and Juan and Donna each lived in a freestanding waterfront home with plenty of space from each other. The parents were wealthy and had been very religious while raising Donna. Now in their 80s, they were less committed to their faith, but they would undoubtedly disapprove of the free sex their daughter and son-in-law shared with Heidi and me. So, we stuck to the itinerary of the estate planning discussion and put off our sexual fantasies for a time when they could be discretely fulfilled.

Juan, Donna, Heidi and I all had professional and parental responsibilities that we took seriously. Our sexual encounters went beyond the boundaries of the ordinary at times, but it was never reckless or dangerous. Juan, Donna and I were all licensed mariners with much to lose if our license to our great livelihoods was damaged or lost by behavior that became too public. Heidi was licensed as a real estate broker, so she also had something to lose if we weren't careful with our pleasure events. Fortunately, since Juan and Donna had access to luxury yachts that they managed as part of their business, we often could go offshore and anchor for a private party under the moonlight out of the public eye.

Heidi and I lived not far from Donna's parent's estate with our two small children. Since Heidi was involved with real estate management for Donna's parents, and I was an investor in Juan and Donna's charter boat business, we were invited to take part in the estate planning. Since this was an important adult conversation, we both arranged childcare for our kids.

Juan and Donna were much more than business relations and friends. Juan was a merchant marine Captain and Donna was a mariner Mate. They operated a boat charter operation that had become very successful. Wealthy vessel owners engaged their business to operate the owner's boats while they worked to be able to afford the luxurious yachts they had no freedom to spend time aboard. It took Juan and Donna far from home at times and it was a good relationship with Donna's parents that allowed the flexibility to be absentee parents with the grandparents watching over the homestead. That freedom also allowed Juan and Donna to slip away for sex adventures with Heidi and me, sometimes aboard the luxury yachts they had charge of and could use freely.

Heidi and I live a different life in the Keys. I am a Captain like Juan, but with a different work structure and schedule. I work aboard offshore tugboats and service vessels in the oilfields around the world. My work role had expanded before the visit to the New Orleans trade show so that I now oversee a fleet of many vessels working globally. It is good money and I like the schedule of 30 days on and 30 days off. When the schedule of Juan and Donna aligned with my off time and Heidi being free, it was time to cast off and set sail for a naked rendezvous.

But no naked rendezvous tonight. When our meeting at Donna's parents broke up, Juan and Donna exchanged a long glance with Heidi and me. Donna was dressed conservatively tonight for a meeting with her parents, with full length pants and a button blouse that almost concealed her firm breasts. Her short red hair and freckled face gave her an almost boyish appearance, but her lithe frame was definitely feminine. Juan was of medium build with the muscular structure of a mariner who is frequently on the move around heaving decks. He wore shorts that covered his legs to above his knees, with his wiry black hair displayed from knees to ankles and sprouting from the v neck of his pullover.

Heidi was less casual than normal, wearing a bra to conceal the nipples of her voluptuous breasts. She wore a full skirt with a tropical print, giving her a rousing mixture of her Danish ancestry with her Florida presence. After ten years of marriage, I still feasted with my eyes at the sight of this Viking goddess. Heidi was a solid woman with broad shoulders and a sturdy frame. Her blond hair spilled over her shoulders to her full bosom. Heidi was "all in" with everything and her Danish background gave her a delightful uniqueness. Growing up in Denmark, Heidi was raised in an environment that accepted human sexuality without shame. When I met her as a mariner working in the waters off her country, she was a sensual dream come true. There has never been a sexual boundary that Heidi hesitated to cross to satisfy her curiosity about the taste of a pleasure she had not yet experienced. In our sexual swaps with Juan and Donna, we had stayed true to our promise to each other to engage in whatever fantasy pleasure pursuits we chose to explore, as long as we did that together. No secrets and no hidden agendas. Heidi and I love each other and want to maintain that love within our marriage, even as we share the physical pleasures of sex with other people.

Returning home, Heidi and I expected our two small children to be fast asleep and overseen by our long-time babysitter, Caitlyn. Our relationship with Caitlyn was relatively long. She had started caring for our children at the age of 13 and was now 18. Soon she would step out of her role as babysitter, as she had just graduated from high school and was headed for an Ivy League university with a full scholarship. Caitlyn was a complete package, with an intense intelligence masked within what most men would notice first, her sumptuous body and gorgeous face. Her Latina birth identity gave her a beautiful head of jet-black hair atop her tall and slender body. She carried not an ounce of fat on her frame that could have adorned a fashion model. She stood and walked with perfect posture, holding her torso erect with her firm breasts front and center on her slender frame. Her hips were narrow, with long legs extending from a flat pelvis that always caught my eye. When she turned, my eye marveled at the perfectly sculpted ass that swayed in a sort of pendulum harmony as she walked. I had to remind myself that this was my babysitter, and I had seen her grow into womanhood from puberty. Still, I appreciated the view, even if it was supposed to be unfulfilled fantasy.

Caitlyn might have carried a lot of baggage given her background, but she had developed into a young woman as grounded as she was intelligent. The only child of two Columbian engineers who had immigrated to the U.S. and found a lucrative position in their technical field, Caitlyn was born with a razor-sharp intelligence and hungry curiosity. She had engaged me with questions about hydraulics and mechanical leverage that I was almost stymied by because of the depth of understanding she obviously had acquired. Her personal achievements as a student, with a 4.0 grade point average in high school and valedictorian of the senior class glossed over the tragic background from which she had emerged.

Caitlyn's parents, especially her father, were party animals. They used the huge income from their work to buy flashy and high-powered toys, like sports cars and speedboats. They had just acquired a cigarette boat with enough horsepower to make the vessel fly over the waters of Florida Bay and offshore. Caitlyn's father took his new nautical power toy out onto Florida Bay to see how fast he could make it go. With the engines roaring at full throttle, the boat shot like a bullet towards the bridge separating Florida Bay from the offshore coral reefs. Even in broad daylight, he should never have been going so fast as he tried to pass through the channel under the bridge at full speed. He obviously did not see the floating work platform left under the bridge by a maintenance crew. The rocketing boat slammed into it like a cannon-fired projectile. Caitlyn's mother was sitting in front of the steering station and was catapulted like a rag doll into the superstructure of the bridge. She was dead before her body dropped into the water below. Caitlyn's father was slammed into the steering post and was severely injured, but he survived. Caitlyn was 12 at that time and had stayed home to study, which saved her life.

Caitlyn's father recovered from his physical injuries, but he never regained his mental balance. Even though the multi-million dollar settlement with the state of Florida for the negligence of the maintenance crew who had left the work platform under the bridge set up Caitlyn and her father with a secure financial life, her father took to the bottle and was depressed and distant. Caitlyn raised herself, more or less. The community around her did what they could to provide support and comfort her during her teenage years. Heidi and I were a part of that, with Heidi, especially, reaching out as a motherly comfort station. Caitlyn became a reliable young woman to watch over our children, sometimes during long periods when our business demands took us out of town or to sea.

Although Caitlyn was very young at 18, she had developed an adult steadiness. She was especially engaged in pursuing knowledge to satisfy her piercing curiosity. Her intelligence, however, was a threat to many of her classmates, and she spent most of her time alone, reading and doing research on the many scientific interests she never tired of pursuing. Her appearance also seemed to make her unapproachable to boys her age, since she was simply too gorgeous! Only recently had she started what seemed like a relationship with a guy, and it made me wonder what it was exactly. Larry was the son of snowbirds from New York who were part time residents of the Keys. He was an athlete and would be attending college in the West on a full athletic scholarship to a Division 1 school. I met him when he dropped off Caitlyn to babysit one time and he struck me as a somewhat dense, but athletic young man. Caitlyn would describe him later as "a nice manhood specimen." I chuckled about that description at the time, but I would get real insight later as our relationship with Caitlyn took an unexpected turn.

As Heidi and I pulled up to our house, it was dark on a moonless night. I stopped the car in front of the house so we would not wake our children as we came in. Knowing the kids would be in bed and asleep by now, Heidi and I decided to slip into the back yard by walking between our house and our privacy fence. I was able to use my phone to shut off the motion-activated yard lights. I marvel at the technology we have at our disposal nowadays. With my phone I can control lights and our security cameras around our property. I use my phone a lot for Skype sessions with Heidi when I am at sea. With Heidi at home and me a hundred miles offshore in my cabin, we get naked and watch each other pleasure ourselves in our private porn sessions.

Trying to be quiet as we slipped along the side of our house towards the gate to the back yard and deck outside our back door, I stopped to look at my phone for the views from the security cameras covering that area. Heidi and I looked in amazement at what we saw! Sitting in a lounge chair on the outside deck was Caitlyn, and she was topless! She was reclining slightly in the chair and illuminated by the soft single light over the back door of our home. We had a full-frontal view as she raised her phone to take a topless selfie and appeared to send it off. Heidi looked at me and smiled. "Caitlyn has grown up," she whispered.

She had certainly grown up, and I absorbed the result as I stared into the live image of her topless beauty on my phone. Heidi stared with me, a warm motherly smile slipping across her face as she admired the 18-year-old beauty who had, until now, only worn the identity of babysitter. I took in the full breasts with their quarter size nipples. Caitlyn's breasts were ample, but because of her small frame and the firm flesh, they stood out huge against her slender body. They were faintly accented with a slightly lighter skin tone against the tanned body and angled straight forward. As Caitlyn lifted her t-shirt over her head to cover herself, I noticed how firm the succulent breasts were as the shirt dropped over them.

Heidi and I looked at each other with a puzzled expression. We had obviously enjoyed this secret viewing, but we were still voyeurs to a private session of someone we cared about.

"Should we tell her we saw?" asked Heidi, genuinely concerned that we might be invading Caitlyn's privacy.

"I don't know," I said. "let's just see what happens and if there is a way to explain how we saw this, we can." I closed my phone ap and we opened the gate to enter the back yard. Caitlyn looked up at us as we entered.

"I didn't hear you guys coming," she said. Caitlyn remained lounging in the extended chair, now fully clothed. The amber glow from the floodlight over the door between the deck and the house gave Caitlyn a soft hue, enhancing her beautiful facial features. Heidi and I stood looking down at our babysitter, seeing her in a new light. "The kids are fast asleep," said Caitlyn.

"We know," I said. "I checked the monitors through my phone on the way in. I switched off the motion lights with my phone so we could come in through the yard and not make any noise that might wake them up if we entered the house."

"That's quite a command center on your phone," Caitlyn quipped.

"Yes, it lets me control lots of things around the property," I said. "Sometimes we see things that might seem private to the people appearing in the screen."

"Oh," said Caitlyn. I could see the gears in her mind whirring.

Heidi had been looking at Caitlyn with her usual motherly warmth. A new wrinkle appeared in her gaze.

"We weren't trying to spy or anything," said Heidi, "but we turned on the back yard monitor as you were sending a sexy selfie."

Caitlyn was unfazed. She was quiet for a moment and seemed to be absorbing our revelation. When she started talking to us, it was as fellow adults rather than the child she used to be.

"You seem to be a couple who share a lot with each other," Caitlyn said as she sat upright to gaze into our faces. "I've noticed sometimes that you seem very at ease with sex when you talk about it. I wonder if I could ask you for some advice."

I could see Heidi's motherly instincts drawing her into conversation with this young woman who was so recently a child. Heidi sat down facing Caitlyn.

"Of course, you can ask us anything," said Heidi as she leaned in toward Caitlyn and placed her hand on Caitlyn's knee. "Where I grew up in Denmark, sex is considered a normal part of being human. It's normal to be curious and puzzled about it at times. Peter and I have a very open attitude about sex and would be flattered if you would let us give you advice on any questions you have about sex."

Caitlyn looked as serious as she was beautiful. "I'm eighteen years old now and feel like a woman. I'll be going to a college where I'll be in a mixture of people who are much more experienced at sex than I am, and I feel like I don't know anything about it!"

I was still standing, looking down on the two women facing each other with looks of real concern on both their faces.

"I'm having sex with Larry now," said Caitlyn, "but I don't really understand things the way I want to. Larry won't even let me look at his penis for more than a few seconds. I want to know how it works!" Caitlyn sounded strangely more like an engineer talking about trying to grasp a mathematical concept than about how a dick worked from a pleasure perspective.

Heidi is not an engineer, but her motherly instincts wanted to resolve Caitlyn's problem. "What do you mean when you say you want to know how it works?" Heidi really wanted to help.

Caitlyn responded like an engineer. "I mean I want to look at a penis and see how it gets ready for sex by becoming erect, how it looks from different angles at different times, and how it feels. Larry is so quick to come, I don't really get a chance to study anything."

I felt odd as the male observer watching two women talking about observing a penis. I stood silently, watching my wife's wonderful, good nature being drawn into a lesson on sexual mechanics. It was fascinating and funny as it was riveting.

Heidi leaned in a bit closer to Caitlyn, who was sitting erect in gorgeous splendor as she stared like a begging puppy into Heidi's eyes. "So you want to learn about the anatomy of sex as well as experiencing the pleasure from it?" asked Heidi.

Caitlyn smiled slightly, revealing a warm crinkle around her eyes and mouth that melted the expressionless engineer's face she usually presented. "I want the pleasure," she said, "but I also want to understand what makes it happen. That's what I mean when I say I want to know how it works."

Heidi looked at me with that warm beauty that made me love her so much. She was a voluptuous woman with a huge appetite for sexual discovery and a Mama Bear who wanted to teach her cubs to hunt.

"Peter, show Caitlyn your penis," Heidi commanded.

I had been a silent bystander to this drama until now. I felt like a member of the audience being called on stage to take part in a magician act. I apparently didn't respond quickly enough, for Heidi reached over to pull my belt loose, snap open my pants and pull my shorts and underwear down. There it was in a moment of unexpected revelation - my naked dick in front of the babysitter.

Caitlyn looked on like a college student in a lecture hall. She stared at my dick as Heidi reached in to caress my balls and put her hand around my flaccid member. She stroked it softly. Caitlyn moved her head closer to get a better look. I began to rise to the occasion as the teacher and student peered at the lesson of the day.

"Peter has a rather thick penis," said Heidi as she rolled my foreskin back from the tip and worked her hand back and forth. "He is circumcised, so the foreskin on the tip of his penis was cut off after he was born." Heidi drew my foreskin back to show the unshrouded tip of my penis. "Most men now are not circumcised, so they have more foreskin."

It is correct that I have a circumcised, thick penis, but it was bizarre to look down on my wife slowly stroking my dick as her young student leaned in closer to absorb more details of my stiffening dick. I drop of precum appeared and Heidi used this as a lesson point.

"See that," she asked Caitlyn, squeezing my dick as she stroked upwards to make the precum hold at the tip. Heidi looked at Caitlyn to make sure she was getting this real lesson in the mechanics of penal stimulation. "That is precum," said Heidi as she swiped her finger over it and dabbed it up. "It's the start of the juices flowing for a penis," said Heidi and she brought the finger to her lips and licked the precum appreciatively. "It has a distinct taste. Slightly salty and a taste of things to come."