Leaving boyhood (Part 1)

Is it his first kiss?

Is it the first time he gets to peek at his sister's or mother's nakedness?

Does he lose his boyhood the first time one of his cousins touches his manhood to see what it feels like, and he in turn gets to touch her womanhood? Is he still a boy after feeling his best friend’s older sister's beautiful large breasts and then suckling them softly for her first time and his, almost getting caught by her dad?

How does one determine when boyhood ends and the man he will eventually become begins?

My Story

For me, I believe it was the summer I turned 14.

Reflecting back to that time, I'm sure some of it is exaggerated, most of it is true to my memory, and none of it will ever be forgotten. It still makes my body shiver and my mind race with the details.

The Job

As I recall, it happened like this...

I lived in a small town and worked for a local grocer over the summer, delivering groceries to people in the local area. I was only 13, so I didn't have a car yet, but the grocer had a bicycle with a basket on the back. I would put the groceries in the basket and deliver them. Most of the people I delivered to were either handicapped or used home delivery for convenience. I would also deliver to some business owners who didn't have time to shop or were maybe just too lazy.

The reasons for the deliveries aren't really important or relevant to why I'm recalling this for you...so let's move forward.

Anyway...

I would get the orders, sack the groceries up in paper sacks, and deliver them to their house or place of business. I was usually paid in cash and told to keep the change. Sometimes it was a check, and the person would give me a few dollars for a tip.

It was a fun job, and I got plenty of sun riding around town in my tank top and shorts. Riding around on that bike that summer with the sun on my back and legs was a great way to get a tan. I usually rode without the top until I got to my destination, then I would put my shirt back on to avoid complaints from the older patrons. Riding the bike was also a great way to develop my legs, which helped me for baseball and track later on.

First Deliveries

The first few deliveries I made were pretty uneventful. I would bring the paper sacks full of groceries into the house or wherever they wanted them. They would ask me about my family (since everyone knew everyone else in town). I would ask for the money, they paid me, gave me my tip, and I would say, "See you next time" or "Goodbye" and leave.

The first time I delivered groceries to Miss Watts' house, it was nothing to write home about. I knocked on her door, she came to the door, smiled at me (she had a great smile), held the door open, and told me to put the two grocery bags in the kitchen. I did, asked how she was (I was always a polite kid), she said she was fine, asked how much she owed me, paid me, gave me a nice tip, and out the door I went. I had two other deliveries to make, so I was in a hurry, still in boyhood, not really noticing anything about her.

The Rainy Day

A week went by, and I had her address again on my list. Making sure I had everything on the grocery list, I put the bags on my bike and went to make the delivery. Before I left, I noticed that I only had two deliveries to make, and hers was last. I didn't think much about it at the time, but as I got ready to leave, my employer told me that I could leave for the day since things were slow, and the weather looked like it was getting ready to rain (which it was looking really bad outside).

I had only worn my shorts and tank top that day since it had started out pretty warm. But as the day progressed, the clouds came in and it cooled off, but it wasn't bad yet. Anyway, as I made the first delivery, the weather came in quick. The rain started pouring down, and I was getting pretty soaked as I headed to my last delivery, Miss Watts'.

It was a little over a mile to her house from my previous delivery, but by this time it was pouring, and I do mean coming down "cats and dogs." Luckily, the store owner had a cover for the basket, so the groceries weren't getting too wet, but I was. By the time I knocked on her door, I was soaked through and through.

The Encounter

I hope everyone is staying with me.

I didn't get an answer right away when I knocked the first time, so I knocked again. As I waited for her to answer, I started to shiver, standing there soaked to the skin as it had cooled off significantly.

Finally, the door opened, and my eyes must have widened. Miss Watts stood there, barely covered in a buttoned-down negligee robe, holding what appeared to be a glass of wine. I could clearly see most of her body underneath the robe, but she didn't seem to be aware or concerned about what she was showing.

Miss Watts was about 5'6" tall, a few inches taller than me. I found out later she was 28 years old. She had no tan lines that I could see, her breasts were practically staring at me, and I could almost make out the outline of her clean-shaven lips below her waist.

I'm sure I was gawking, but as I stood there shivering, I felt a warmth come over me. I wasn't sure if it was nerves or what, but my adrenaline was racing.

She asked me to come in out of the rain quickly, holding the door open for me. As I walked through the door, one of the bags ripped open. Great! I tried to keep it from ripping all the way open but couldn't. She reached out to catch the sack as it fell, leaning in on me, her glass of wine spilling over the top of the sack. I lost my balance and both of us fell—grocery sack, groceries, her, me, and the wine glass—to the floor.

As we fell, everything slowed down. Her robe got tangled in my hand, and she fell sort of backwards, so the robe was coming with me as she fell. The robe fell between us, and she basically fell on it on the floor, completely revealing her nude body at this point. As she tried to get up, it basically fell off her arms and hands. I was in shock.

Of course, I had seen nude women in magazines. I had even seen my mom a time or two in the bathroom or her bedroom (but it was my mom), and I had seen the girls at school in the locker room (through a peephole in the wall), but this was the closest I had been to an actual naked woman. I wasn't sure what to do.

The Fall

I came to a sitting position with part of her robe underneath my hand, and she fell into a kneeling position right in front of me with the rest of the robe behind her.

I wasn't sure what to say or do.

She started laughing!!

She had somehow managed to close the door at the same time that she was trying to help me, so there was nobody else to stare at us (thankfully).

When she started laughing, I just started laughing too. I didn't know what else to do. As she laughed, her chest jiggled up and down.

I'm sure I was staring, taking all of her in, even while laughing. Her head went down as she laughed harder, her hair covering her face and most of her chest. Then her head went backward as she laughed even harder, uncovering herself again. Her arms were behind her back, her hands on the floor, and her legs were on top of each other with her feet to my right.

The paper bag was ripped in half, soaking wet, and the groceries had spilled between us. I was shivering, laughing, and gawking—not really sure in what order, only that all of it was happening at the same time. I leaned forward, trying to pick up some of the spilled groceries and put them back in the bag, trying not to stare at her nakedness, but not having much luck at that.

She looked up at me and realized the wine glass had spilled most of its contents on me. She was still laughing (naked), and she started to apologize for spilling the wine on me. I was so wet anyway that I hadn't noticed it at first. I looked down at my clothes and saw a reddish or purplish stain on the front of my shirt. I didn't spend much time looking at the stain, though, as I had a naked woman in front of me and her chest was jiggling.

Time Stands Still

I looked down towards the floor and followed her feet up to where I could see her bare lips where her legs came together. Time seemed to stop for me. Everything started in slow motion from that point on.

Curiosity and Connection – Where Couples Journey Into Desire

Dive into a realm of exciting encounters and lively community connections. Join SwingTowns and start your adventure with unforgettable parties and joyful experiences. Register for a free account now and meet local swinger couples near you. Let the journey of endless fun and exploration begin today!

“Swingtowns.com has been one of the best places for meeting like-minded and fun party people. I’m always looking to meet new people and this site never fails.”
- PoundnSand