When I was younger, I used to think that being thirty years old was the end of life. Now, at thirty-three, I fully understood how clueless I’d been. Most of my life had been pretty vanilla, that is to say, boring. I did well in school, played baseball and ran track in high school and college, married my high school sweetheart, and got a job. By the time I was twenty-eight, my marriage had ended, and I had quit my job to take up day trading. When I hit thirty, I had amassed sufficient funds to allow me to retire, so I did. It was a crazy time and certainly not the end of anything.

I spent a year traveling before finally buying a house and settling down in a modestly upscale neighborhood. The neighbors were mostly older and had kids either in high school or college. I wanted something stable and quiet, and this fit the bill perfectly. I especially liked that my new location was almost always warm, allowing my nightmares of New England winters to fade away.

Living modestly allowed me to splurge on certain things, like hosting a block party a few times a year for all the neighbors. It was always a catered, well-attended blowout, and it allowed me to stay social with most of the people on my street. Since I lived alone and had no need for a job, it was my way of being part of society. Those first two years were quite pleasant, but I had reached a point of wanting more.

I tried dating a few times, but the sting of my failed marriage was always at the back of my mind. My ex had convinced me that she was committed to us, all the while she was screwing every guy who came her way. And now I found it difficult to trust any kind of relationship with women my age. It was during this time that I became aware of other possibilities.

I had thrown another block party and we were well into the evening with everyone feeling mellow. The kegs were running dry, and some folks had started wandering or staggering back to their homes. I was inside my house collecting empty red cups, which seemed to have multiplied everywhere when I saw Emma standing in the living room. Emma was nineteen and the daughter of my neighbor three houses away.

“Oh, hi, Emma,” I said. “I didn’t realize you were still here. I think your parents left a while ago.”

“Do you trust me?” she asked.

“What? Trust you? We don’t know each other that well, so… Wait, what did you do?” I asked, wondering what was going on.

Without a word, she grabbed my hand and pulled me down the hallway. As she tried to drag me into my bedroom, I put on the brakes and asked, “Emma, what the hell?”

“Do you like me?” she asked. “I mean, like me enough?”

Now I was really confused. “Sure, I like you. You’re a sweet, pretty, college kid. Why are you asking me this?”

As an answer, she pulled me close and held her body against mine. Since it was summer, she was minimally dressed in a light tank top and tiny shorts. The feel of her breasts against my chest was quite pleasant, but my brain was still confused about why she was doing this. But that didn’t stop me from embracing her.

I started to ask her again what was going on when she stood on tiptoes and kissed me hard on the mouth. Immediately her tongue pressed against my lips and I let her in. We Frenched for about a minute, which was just enough time for her to feel the bulge of my erection pressing into her pussy.

She broke our kiss and said, “Look, this is no big deal. It’s just sex. If you want it, then take me to your bed. If you don’t, then it’s your loss.” She reached down and squeezed my cock and continued, “I’m a little buzzed and a lot horny and just one of many women on this block who want to fuck your brains out. So, what’s it gonna be?”

What could I do? I carried her into my bedroom, where we fucked each other’s brains out, twice.

This exquisite encounter turned me on to the possibilities of relationships with younger women. But it quickly became apparent that while these eighteen and nineteen-year-olds might be willing, their parents were not too enthusiastic. So while I was able to have some great sex with these older teens, there was no hope of anything more. But what it did do, was set the stage for what was to come.

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It was mid-spring and the house next to me had just sold. My neighbor, Rick, had gotten a promotion and was relocating to Texas. He told me that the buyers seemed nice and that I would thank him later. I laughed, not having any idea what he meant. A few weeks later, a big moving van showed up and spent the day filling the house with all manner of stuff. Through all the commotion, I could only see a mother and what, I assumed, was her teenage daughter. But the scene was far too busy for me to intrude.

A few days later, I met my new neighbors and got an inkling of why I might need to thank Rick. Heather was the owner and she looked to be about my age. She was a striking woman with long brown hair and pale skin dusted with freckles. She was tall, with an athletic build and legs that looked great in the shorts she was wearing. Her daughter, Niki, was built like her mom, tall and slim, and had the same pale freckled skin. But where Heather’s hair was brown, Niki’s was a beautiful shade of red. Niki also had emerald green eyes that complemented her hair color perfectly.

I learned that Heather’s husband had died the year before, but fortunately, he left them financially comfortable. They decided to move to get a fresh start and to allow Niki to attend the private all-girls high school in town. Niki had dreams of becoming a graphic designer, and the school had just such a program. I also learned that Niki would be a sophomore in the fall and planned to join as many sports as she could. They seemed like a nice enough pair and I was happy to see them join the neighborhood.

I made a point of being very friendly with Heather, offering to assist her with odd jobs around the house. After a few months, we even tried dating, but while we made good friends, nothing clicked romance-wise. Fortunately, after the breakup, we were able to remain friends and we still talked almost every day. Life had settled into a comfortable routine that within a few months was destined to be upended.

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It was late January, and Heather and I were having coffee near her pool. Something was on her mind and since we remained close, I wanted to see if she felt comfortable enough to confide in me.

“Penny for your thoughts,” I offered, to see if I could ease her tension.

I saw her smile as she replied, “Is it that obvious? Sorry for being so distant, I seem to have a lot on my mind.”

I took a sip of coffee and reached out to touch her hand. “I’m a good listener if you’d like to talk about it. Sometimes a different perspective can help.”

She took a deep breath and said, “Babies. All I can think about are babies these days.”

“Ah yes, the coming spring and babies go hand in hand,” I said, completely misunderstanding her point. “Are you thinking of having another? A little brother or sister for Niki?”

The look on her face told me I was way off the mark. It looked like a mixture of horror and sadness rolled into one. I surely had misstepped but had no idea how, so I simply sat waiting for her to speak.

Finally, she laughed and said, “I guess I should explain. I met Niki’s father, Paul, when I was just sixteen, and within three months I was pregnant. Niki was born when I was seventeen and her dad did right by us and we got married on my eighteenth birthday.” She paused to freshen her coffee and add another dollop of cream. “As young as we were, it was a good marriage and we both adored having little Niki. Paul did very well working at his dad’s company and we prospered chasing the American Dream. Paul’s dad was a firm believer in life insurance and helped us purchase a large policy to cover both of us. My father-in-law wanted to make sure his granddaughter would be well provided for if the worst occurred.”

I was beginning to see where this was going and why she was thinking about babies.

Anyway,” she continued, “I’m getting off track. As you know, the worst did happen and I collected a large settlement, and here we are.”

“And you’re worried that with Niki turning sixteen soon,” I said, interrupting her, “she may have a similar experience and get pregnant. I can’t say I blame you for being concerned.”

Heather looked at me and smiled wistfully. “It’s a tricky line to walk with your daughter to try and explain why it would derail her future if she got pregnant now, and not make her think she was a mistake that ruined my life. Nothing could be farther from the truth. But how to clarify that with her?”

“That’s a heavy load to bear,” I replied, “and not something I have any life experience with. But if it were me, I’d approach it by explaining that you want her to have unlimited choices. And one of those choices is when to have children. But if an unexpected pregnancy were to occur, then a big choice is made for her and that will affect and possibly limit her future choices. Better to be safe now and keep all her options open.”

She looked at me for a long time before saying, “You will be a great father someday. I hope you get the chance. I’ll try that approach and see how she reacts. If fit blows up in my face, I can always blame it on you!”

Two weeks later, Heather threw a huge, catered, sweet sixteen swim party for Niki. All of her friends from high school attended, and from what I could hear it was quite a success. I was invited but chose to only make a brief appearance to give Niki her gift. Everyone was making so much noise she pulled us into the pool house so we could hear each other. When she opened the small box, she found a solid gold heart pendant inscribed with her name and the words ‘sweet sixteen’. It hung from a fine gold chain, and she squealed with delight.

“Put it on me, please?” she gushed. “It’s so pretty!”

I undid the clasp and she held her hair aside so I could drape the delicate chain around her neck. The feeling of her warm skin on my fingers was electrifying. The pendant hung just above the vee of her breasts, which I suddenly realized were barely covered by the tiny bikini she wore. I felt my cock lurch at the view.

I stepped back and said, “All done.” And hoped she did not hear the tremor in my voice. She looked down and fingered the small heart before turning to face me.

“Thank you, Bill!” she gushed. “This is my first real piece of jewelry and it makes me feel all grown up.”

She stepped forward and gave me a big hug, and I felt her small breasts press into my chest. I loosely hugged her back, fearing if I squeezed too tight, she would feel an unexpected lump pushing into her crotch. She gave me a quick kiss on the cheek and ran out to the pool to show her mom the gift.

I waited a few minutes for the swelling to go down and made my way back to the party. I found Heather so I could say my goodbyes. We talked for a moment and then gave each other a farewell hug.

As we embraced, she spoke over the din, “That was a wonderful gift you gave Niki. It was something her father would have done, and I never even thought of jewelry. So thank you for being so thoughtful.” Then she kissed me on the cheek and leaned closer to whisper in my ear. “I think my daughter has a bit of a crush on you. But I know you’ll do the right thing and be gentle with her emotions.”

I promised I would be careful and made my way back home while my brain replayed the feel of Niki’s warm body in my arms.

About three weeks after the party, I was in the attic putting away some boxes. I’d opened the windows to get some ventilation and happened to look down into Heather’s backyard. Normally, her eight-foot privacy fence blocked the view, but from up here I could see everything. I saw Niki and her older girlfriend Becca in the heated pool swimming laps. Both teens had similar trim athletic builds, and I knew both were on the school’s soccer and track teams.

I saw them climb out of the pool and walk over to where their towels lay on the chaise lounge chairs. I expected them to towel off, but what they did instead nearly gave me a heart attack. First Niki, then Becca, stripped off their bikini bra tops. I guessed with the tall fence, they felt that no one could see them and they were free to soak up the sun and avoid tan lines. Both had fantastic bodies and their breasts were no exception. Niki’s boobs looked to be about a small B cup, while Becca’s were closer to a C.

I pulled up a crate and settled in to enjoy the show. I decided looking at naked boobs was more fun than lugging heavy boxes around. I almost jumped off my seat when I saw Becca hook her thumbs into her bikini bottoms and skim them down to her ankles and kick them aside. Her back was to me and I was transfixed by her firm, toned ass. Niki was right behind her, dropping her bikini bottoms and adding them to the pile. Niki’s ass looked even better than Becca’s and I was praying that they would turn around.

The next few minutes were right out of a porn movie as they slathered sunscreen on each other. I could spend pages describing the sight, but suffice to say, it was very erotic. By now my cock was out and I was stroking slowly, enjoying the view. Finally, they were finished, and my patience was rewarded. They each grabbed a chair and turned it around to face the sun. Then they laid down and I finally got to see them full-frontal. Both had full bushes that seemed to perfectly match the hair color on their heads. Niki’s bush was bright red and appeared to be very soft and fuzzy. Becca’s pubic hair was pure blonde and appeared to be less curly. They both settled into their chairs to relax.

As they dozed, all kinds of impure thoughts bounced around in my brain. I was stroking faster now, eager to gain some relief. I decided that while Becca was beautiful and had killer tits, my preference was for Niki. Something about her compact breasts, curvy waist, and her amazing red hair just hit all my buttons. So, I focused on her body and within ten strokes I was spraying the floor with jizz. As I sat there in my post-orgasmic bliss, I realized that I could develop real feelings for Niki, despite the fact she was only sixteen. But just as quickly, I dismissed the thought as ridiculous and got on with my day.

Life was good and was about to get better. It was now early spring and I was out in the garden when Heather came over to say hello. She told me her mother had taken ill and needed help, and she was leaving that night to go take care of her. So close to the end of the school year, she wanted to avoid disrupting Niki’s scholastic routine. Would I be willing to watch Niki for a few weeks until she could get back?

“Are you sure about this?” I asked. “It might set some neighborhood tongues wagging.”

“I’ve known you for a year and feel confident Niki would be safe with you,” she replied. “As for the gossips, they’ll just have to get over it.”

“How does Niki feel about it? I mean wouldn’t she prefer to stay with one of her girlfriends?”

“Staying with you was Niki’s idea. Two of her girlfriends have sisters already sharing their rooms, and her other girlfriend has an older brother who I don’t trust. Besides, Niki still has that crush on you, so there’s that.” She gave me a big smile and winked.

“Well then I’d be honored to babysit your daughter, and I do hope your mom is okay.”

“Oh, god, don’t use the word 'babysit.' Niki is already on my case saying she’s sixteen and old enough to take care of herself.”

Niki showed up a few hours later, suitcase and backpack in tow. Just in the month since I’d seen her at the birthday party she seemed to have matured. By all measures, Niki was striking in her appearance. I know youth has a stranglehold on attractiveness, but she was an exception even to this rule. She was tall, standing about five feet seven inches, and probably weighed no more than 115 pounds. Up close, her long red hair seemed soft and as fine as silk. Her pale ivory skin was lightly dusted with cute freckles, and her eyes were a wonderful shade of emerald green flecked with gold. I could see that one look at her and...