Have you ever found yourself in a situation, you knew many would consider wrong? No, I'm not talking murder wrong, so calm down, dear reader. I guess to tell this story right; I have to begin at the beginning of my story. A while back (no, I'm not telling you when, as for all I know, the wrong person or people are reading this) I was helping a friend move into her new place. Now, I know, helping a friend move isn't a bad thing, but it was what happened after that was, well, so to speak. My friend had a nice neighbor, a widowed father with three boys: Bobby – 20, Dawson – 18, and Elliot – 12. Now, Bobby was okay, Elliot was cute, but it was Dawson who for whatever reason caught my eye. Now, I know, you're thinking the author of this is a woman in her twenties or thirties at best. Well, my dear reader, you'd be partly mistaken. The author of this tale will admit to being over 35, but under 45. Yes, I know, a ten-year range is extreme, but I have my identity to protect. I will admit that I am female, short, 5'3", with long curly blond hair, blue eyes, and a very curvy figure, and I'm talking 40D bra size, full hips, and curvy. Some would say I'm a bit of an hourglass shape, but my sand filter could be a bit thinner.
Dawson was handsome. Any teenage girl would have been attracted to him, and rightly so. He was 5'7", slender but muscular, short brown hair and green eyes. When I first met him, we hardly talked. I'll admit, I thought he was cute, bordering on handsome, but he was a kid. However, as time progressed, and we helped my friend get settled in, we would find ourselves talking more and more, and often, he and I would be alone talking. We were helping my friend fold her clothes, so she could take care of some other things in the house, when Dawson picked up one of her bras. Now, my friend is a wonderful woman, but when the good Lord was handing out breasts, she got passed over a lot. As a full figured woman (I'm serious about my bra size being a 40D), I'm not used to padded bras. Any lady with large breasts reading this knows that we don't need to add, just support what we already have. Now, Dawson had no idea how to fold a woman's bra (his mom had passed away about five years earlier and she always folded her own clothes.) Dawson handed me this heavily padded bra and asked me to fold it. I looked at it, smiled, and said, "Now, I'm all for a good over-the-shoulder-boulder-holder."
That comment alone caused Dawson to burst out laughing so I waited for him to compose himself before I continued. "But with all this padding, it's more like an over-the-shoulder-pebble-holder."
Poor Dawson literally fell on the floor laughing hysterically. I did my best folding her bra (with mine, I just match the cups, pushing one into the other, and stuff the straps inside the cups), but the padding did make it a challenge. Dawson composed himself and had me fold my friend's undergarments. I did notice that he would seem linger on the undergarments, maybe wondering what they would look like on a woman. Once the clothes were folded and put away, we resumed other tasks in helping my friend to get settled in. At lunch, his arm brushed my right breast. I'll never know for sure it if was pure accident or an "accidentally on purpose" as I never asked. Hell, I was flattered to get the attention, accident or not.
About a month after my friend settled in, I came over to visit, have dinner, and catch up on old times. My friend became friends with her neighbor, who shared with us the loss of his wife, and how he was working to raise their sons the best he could. Dawson and Elliot were there, but Bobby was now attending college and wouldn't be home for a few more weeks. Dawson and I joked around a lot through the evening, and at some point, he touched my ass. Now, it's not like I'm a cougar or a damn predator, but I gotta tell you, it was pretty nice to have someone, hell anyone, pay any attention to me. I mean, this kid was giving me more physical action than I had seen in close to a year. His contact with me was gentle and subtle, something many men had forgotten how to do. After a wonderful dinner, and a few silly movies, I left for the evening. Dawson insisted in escorting me to my car, even though it wasn't a far walk, nor was I parked in an overly dark area. I thanked my young escort with a soft kiss on his cheek, and I swear there was heat between us.
A few days later, my friend called me in a panic. Her parents were in a car accident, and the nice widower neighbor was going to drive her the five hours to the hospital, but they needed someone to stay home with the boys. I knew Dawson was a responsible boy, but Dad just felt better if a responsible adult was there with the boys, just in case. Now, I'll admit, I thought this was a bit odd, a father wanting a woman he hardly knew babysitting his sons, but I quickly agreed. I arrived to find my friend nearly hysterical and the neighbor trying in vain to calm her down. She was really close to her parents and the fact that they were hurt, and she now lived so far away, was more than she could handle. I had brought an overnight bag assuming I'd be sleeping in one of their respective apartments and shooed them off assuring them everything would be fine.
The kids and I decided on having pizza for dinner, it was easier than trying to figure out what a teenage, and a near teenage boy would want to eat. After dinner (two large pizzas later ... damn could those boys eat), we watched some movies until it was time for the younger one to go to bed. Of course he protested and insisted his dad let him stay up later than he really did, but this argument ended when I called his dad and confirmed the truth. I'll give the kid this; he held his ground until he realized I really did call his bluff. I was told the older one could stay up until midnight as neither had school, but the younger one had just gotten a bad grade on a test and lost the privilege of the later bedtime for this weekend, but it would be revisited depending on my report upon his return. Once Elliot was settled and asleep, (he lasted all of ten minutes), I watched a movie with Dawson. However, neither of us found any interest in the film, so I handed Dawson the remote and let him pick a film. After some channel surfing, he found a movie he liked. It didn't take me long to see why.
Now, again, I'm not a predator or a cougar, but this kid found a film with lots of sex, bordering on soft-core porn. I figured if it bothered me too much, that I'd just go to bed early. That's when Dawson asked, "Have you done that before?"
"What, sex?" I asked.
"Well, yeah, I mean, no," he started to blush. It was so cute. "I mean, what she's doing, or pretending to be doing."
On the screen, a woman was performing oral sex on a man, or at least, that's what we were led to believe. I'm never sure with some wannabe pornos how much they actually do versus how much they fake. "Oh, yeah. I've done that."
He gasped and asked, "Did you, ugh, I mean, that is, ugh, did he-"
I had to stop him before he died of embarrassment. "If you're asking if I swallowed his seed then the answer would be yes."
Dawson's face went white. Perhaps I had been to blunt with him, and suddenly I was afraid I had guessed wrong when he asked, "Does it taste gross?"
I had to keep from laughing. That had to be the most honest question I'd ever been asked about that. So I smiled and said, "Truthfully, it depends on the man. Some have a more pleasant taste than others do. I've been told it's the same with women."
Dawson's face went from white to red. Okay, I knew I crossed a line, and tomorrow, when his dad came home, I was going to be banned for life for talking to his son like this. I was about to go to bed and end my night when he asked, "Hold old were you when you did it the first time?"
"Sixteen," I said. Not something I was proud of, but why lie?
His hand was now on my leg, and he said, "Please don't go to bed just yet, I have more questions but I want, well, I want a woman's opinion."
I smiled. Suddenly I knew anything we talked about would never get back to his dad. "Okay, ask away."
I turned so I was facing him instead of the television, folding my left leg under me, and turning my entire upper body toward him. He smiled nervously and asked, "Have you been with a lot of men?"
Ouch! Not a question I liked answering even when I'm in a committed relationship. I mean, I'm not a whore, but I've had my share of one night-stands and short-lived sexual relationships. "Well, that's kind of a personal question. But I will tell you that I've been with enough men to know what I like."
"I didn't mean to upset you," he said.
"Oh, you didn't," I said. "But, you have to be careful when you talk to a woman about her sexual past."
"Okay," he said. "Is there anything you don't like?"
Now this was an honest question that a boy curious about sex should ask. "Well, for me personally, I'm not into physical violence. Some women are, and trust me when I say; they'll tell you if they are."
"Have you ever been tied up?"
Whoa! Where did that come from? Then I looked at the television and saw it, the woman was bound spread eagle on the bed and the man was having sex with her. "Ah, yes. It's not something I do the first time as that is something that takes a lot of trust."
His hand slipped up my thigh a bit like this was information he really wanted to know. Then he asked, "What was the biggest you've seen?"
.... There is more of this story ...