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?"
This question made me laugh. Why were men so insecure about their size? This I never understood, but then again, I'm not a man. "I'll tell you honestly, in the realm of real men, some are longer, some are thicker, but the real trick isn't the wand they carry, it's the magic they make with it."
Dawson looked at me like I had just spoken French, so I continued, "Sex is more than just physical intercourse. It's the touching and kissing. If you're in a hurry, your partner will know it. But, if you take your time, you can make your partner feel like a goddess, or a god depending on your preference."
"Goddess," he quickly said. "I don't do boys."
I smiled and said, "That's fine. I personally don't care what people do as long as it doesn't bother me."
"What do you mean?" he asked, his hand now on my hand that was resting on my thigh.
"I mean, gay, straight, or bi is not my business. If a man loves a man, and they are happy, then who am I to say anything. Same with women."
"Have you ever been with a woman?"
Shit. I know this is a lot of guys' fantasy, but really, why do they always ask? "Yes."
"How was it?" Another honest question, but I was beginning to wonder what was up with this kid's questions.
"Different," I said. "And before you ask, the answer is 5. Each one different, and no I won't tell you anything about any of them. Oh and if you mention this to anyone ever, I will deny it."
None of them were my friend, in fact I don't think she knew as it wasn't something I bragged about with. Dawson quickly said, "Oh god no. I'd never tell. I just didn't think you had. I mean, most women haven't."
Great, now he thinks I'm a freak, or maybe not, as his hand was now slowly going up my arm. "Most of us call it 'bi-curious' and that's all it was, exploring the other side. Overall, I like men."
He smiled for the first time that I could ever remember that evening. His had was now on my shoulder, and sliding back down my arm, but now his fingers were brushing against my breast as it went down. "I'm glad to hear that."
I glanced at the movie and there was a guy performing oral sex on a woman. She was moaning loudly and I won't lie, between the stupid movie and this kid's touch, I was getting aroused. I smiled and said, "What else do you want to know?"
I guess he decided the time for talk was over as he leaned in and kissed me softly on the lips. I could tell he was nervous, as he didn't even try to put his tongue into my mouth. "That."
I smiled and kissed him again, forcing my tongue into his willing mouth. I felt his breathing increase and his heart race, or maybe it was mine. This kid was holding out on me as he could kiss. He wrapped his arms around me and it was then I could feel his erection. I had no intention in doing anything on the couch, and even though he didn't share a room with his brother, I wasn't sure if that was a good idea, so I stood up, took his hands, and asked, "Which room?"
He bit his lip nervously and said, "Mine?"
"Do you have, um, protection?" Again, I'm not a whore, but how do I know if this kid is a virgin?
"Yeah," he said. "My dad told me to have some on hand at all times, you know, just in case."
I was starting to feel a bit set up. I mean, older woman, younger man. 'And here's to you, Mrs. Robinson. Jesus loves you more than you will know. Wo, wo, wo.' "Does your dad know about—"
"No!" he snapped. "I mean, you're a beautiful woman and all but, no, my dad has no idea."
"Have you ever done this before?"
"Yeah," he said smiling. "I'm not a virgin."
Thank God! I mean, I'm not against deflowering a virgin, but it just makes my job so much harder and I will get so little out of it. "Lead the way."
Turns out his room isn't next to his brother's, but next to the bathroom. It seems the architect who designed this unit was thinking. The bathroom was a buffer between the two rooms. Dawson's room was what I expected from a teenage boy. Lots of posters of beautiful women in tiny bikinis on cars, or on the beach, with a few movie posters I recognized. He had a full size bed that wasn't made, but other than that, his room wasn't a complete mess. He had the overhead light on, but then he flipped on the lamp on his bedside table, turned on the radio, and turned off the overhead light. This gave the room a softer, somewhat more intimate feel. I'm not sure which one of us was more nervous. I mean, it's been years since I was with a younger man, and he was by far the youngest in terms of age gap I'd ever been with. He walked over slowly to me as a slow song played. He took my hand and surprised me by asking, "May I have this dance?"
Okay, I won't lie, I was totally flattered. This kid was trying to seduce me. I nodded and we put our arms around each other and slowly moved to the music. I put my head on his shoulder and we danced to the music. I could still feel his growing arousal pressing into my stomach, and my own sex becoming moist. I felt his head move and when I looked up; he leaned down and kissed me, this time with much more force than before. Our tongues danced in their erotic coupling, and I knew this kid was no virgin. He danced and kissed me to his bed, then pushed me down. I won't lie; it made me giggle like a silly schoolgirl. I scooted back onto his bed as he slipped my shoes off my feet. Then he crawled next to me, and kissed me again. He looked deep into my eyes and whispered, "I've only been with one other girl. She knew how to kiss, but she never let me do much else. Will you teach me how to, ugh, go down on a woman?"
I had to take a step back and wrap my head around what he just said. So, intercourse wise, he wasn't a virgin, but in the other areas, he was. "Are you willing to listen and do exactly what I tell you?"
"Yes," he said, reminding me of an eager puppy who wanted me to throw a ball for him.
"Good," I said. "Have you ever had a woman go down on you?"
Okay, I was pretty sure I knew what his answer was going to be, but I wanted to know what I was getting myself into. He blushed and said, "No. I've wanted to, but most girls say it's too gross."
I giggled, then said, "It is something that takes courage to try, and practice to master. Let me show you."
With that, I pushed him onto his back, and while I kissed him, I began to unfasten his pants. I could feel his nervousness growing, but he made no effort to stop me. I reached in and touched him through is boxers, then looked into his eyes and said, "If you don't like something, or want me to stop, I will. I won't force you to do anything you don't want to do, or don't want me to do."
He looked at me like I just sprouted three heads, but then he realized what I was trying to do. "If I didn't want this, I wouldn't have kissed you in the living room."
"Just as long as you know you have the power to stop this."
"Yeah, like I'd exercise that," he said sarcastically.
Well, you can't say I didn't try to warn the kid or give him an out. Maybe it was wrong to tell him this while my hand was on his member, but hell, I was aroused and I wanted to teach this young buck a thing or two. I kissed him then moved down, kissing him through his clothes, to the still covered member in his boxers. I kissed his penis through his boxers and heard him gasp. I smiled, as I knew, he was mine. I grabbed the top of his boxers with my teeth, and slowly pulled them down, letting my nose brush his firm erection. I swear he nearly lost it there. I grabbed his pants and boxers and pulled them down in one smooth move. I must admit, I even impressed myself with that move. I kissed up his legs, switching from one side to the other until I was back to his hips. "You may hold my head if you wish, but don't force me down as it may cause me to gag and you don't want me to vomit on you. I guarantee you, that's a mood killer like nothing else."
This is where having a sensitive gag reflex sucks. Most men think every woman is Linda Lovelace and have trouble understand why some of us can't fully take their entire cock into our mouth. As for me and my abilities, if I can control the show, I never leave a man displeased. I'd tell you to ask them, but then, I'd have to tell you who they are and I'm so not doing that, so you'll just have to take my word for it. I started by kissing the tip, licking the sweet, sticky substance that was there. Dawson gasped. I wrapped my lips over the tip, and slid my mouth down about half way down. I looked up and saw his eyes roll back into his head as he moaned. That's when it hit me. I slid up and asked, "Will we wake your brother?"
He looked at me and realized the logic of my question. "No, he sleeps like the dead. Dad's run the vacuum by his bed lots of times and he never wakes up."
"Good," I said. "Because if you're going to climax in my mouth, I want some warning so you'd better tell me so I can prepare."
His mouth fell open, and all I could hear was a squeak. I smiled wickedly and resumed what I had started. I slipped his firm cock back into my mouth and began to slide my head up and down. I felt him grow thicker and longer in my mouth as I worked my magic. I used many the tricks I had learned over the years including dragging my teeth gently along the sides to cause sensation, without harm, licking the head and teasing the hole, and fondling his balls with my free hand. I heard him moan, softly at first, then slowly growing louder. He'd whisper my name, but mostly, just moaned. Now, I really didn't 'need' him to tell me when it was going to shoot, but I like it when a man makes noise. He did not disappoint though, and soon I heard, "Oh God! Oh fuck! I'm going to blow!"
And with that, I felt the warm sticky liquid fill my mouth. It tasted sweet and salty. I swallowed it down until he was fully drained. I licked him clean, then kissed the head softly and smiled. It took a few minutes for him to get his bearings again, as I crawled up next to him. Now sure, I was willing to call it a night and try to sleep (yeah right) but I was pretty sure, he wasn't. I whispered in his ear, "You my young lover, have a sweet, salty taste, and was very enjoyable."
That must have been the trigger to snap him out of his euphoria, as he was on me like a starving animal. I gotta give credit where credit is due, that boy knew how to make an impression and take advantage of a moment. His kisses were deep and passionate. We're talking, curl my toes and straighten my hair kind of passion. He quickly removed my top, with a minor bit of help, removed my bra, and began kissing his way to my breasts. This only required minor instructions, where to kiss, and when to be gentle. I slipped his t-shirt off as his hands started to go south to remove my pants. He slipped off my jeans and soon I was laying there in just my pink thong panties (yes ... I really wear those and it wasn't just for this kid.) He smiled when he looked at those and asked, "Are those for me?"
"I'll never tell," I said smiling. It never hurts to keep them guessing.
He kissed the edges of the panties, then my sex through the fabric. "Wow! You're so wet! Is that from me?"
BUSTED! He now knows how much he had excited me, so again, why lie? "Yes Dawson. All because of you."
He looked at my panties as if I was wearing a locked chastity belt and he had lost the key. Finally, I said, "Take them off of me."
His hands were trembling as he slowly removed my panties and dropped them onto the floor. Damn it! I forgot he doesn't know what to do. "Touch me gently. Use your fingers and your lips."
Slowly, his hands went up my legs as he placed his body between them. Soon his head was there at my sex, and he was looking at me, at it. First, he gently traced my lips with his finger and I gasped. He stopped and I said, "Don't stop."
"But I don't want to hurt you," he said.
Wow, he was so scared. "If you do, I'll stop you and tell you how to fix the problem. But please, do that again."
The looked up at me confused for a moment, then said, "This?"
His finger traced my lips again and I gasped and moaned. "Yes."
He smiled up at me, knowing he was on the right track. He leaned in and gently kissed them. Wow, were his lips soft. After countless number of soft kisses, he licked the outer lips, then slipped his tongue inside. That made me both jump and moan, but he knew it wasn't a jump to escape, just a reaction, a reflex if you will. I'm not sure how long he licked the inside before he slipped a finger inside and resumed the licking of the outside. I was starting to think this kid either had great instincts, or had done this before. I knew after a few minutes I'd have help guide him, as he seemed to be stuck. I reached down and said, "Here, lick me here."
The first time his tongue touched my clitoris, I nearly exploded. I fought to control my climax so he could actually learn a thing or two. Luckily, his inexperience worked in my favor, and I was able to direct him on how to perform oral sex on a woman. I had him lick, suck, and even nibble my clit, but the nibbling took several tries before he understood how to do it without hurting me. He also discovered that two fingers would derive more pleasure, but he at least asked before he tried. Once he had a rhythm down, I was putty in his young hands. He worked me carefully until suddenly, I felt a minor pressure on my anus, as a lone finger from his other hand touched and teased it causing me to climax like nothing I'd ever experienced before. My body tensed up, and had his shoulders not been between my legs, I might have crushed his head with my thighs. My body bucked and he just worked me and enjoyed the ride. I think I had two or three orgasms before he stopped and mounted me. He kissed me hard and entered. Okay, I'll admit it, he was no virgin. No virgin could have entered me like that. Forceful, powerful, hard, and passionate, without hurting me, or himself.
I moaned into his mouth as we moved. I'm not even sure when he got the condom on, as I never saw his hand move, nor did feel them leave me, but I didn't care. He filled me with each thrust, and I was meeting him, bringing my hips up to deepen the sensation. He held me tight and even though he moved with force and purpose, he did not move with speed. Maybe that was why I climaxed again, and again. Though, my climaxes did encourage him, I think my saying things like, "Faster! Faster!" and "Don't fucking stop!" didn't hurt either.
Soon, we were fucking like two mad people. He was on top of me, then I was on top of him, then doggie style, and more. We were all over his room. By the time this young stallion had finished with me, we had christened every piece of furniture he owned, smoked a full box of condoms, and then some. I finally needed some sleep so I gathered my clothes and slipped into his father's bed, sleeping naked and well fucked. I woke up a few hours later, showered quickly, and dressed. It was then I realized I had lost my panties. I knew they were in his room, but the question was this, do I ask for them back or let him keep them? I decided to let him keep them if he wished since I could always buy more. I walked out to make the boys breakfast when my cell phone rang. My friend called to tell me her parents were fine, but they had car trouble and would be gone one more night. I could either stay there with both boys, or if Elliot wanted, he could stay at a friend's house since he had been good for me so far, and Dawson could stay home alone. I knew that if Elliot chose to leave, Dawson would want me to stay here with him, and I really wanted to go home. Plus, if Elliot were gone, it wouldn't look right for me to stay.
Elliot wandered out first. I said, "Your dad just called. His car broke down and won't be back until tomorrow. He said you can stay at a friend's house since you were so good for me yesterday, but you have to tell him whose house you're at, and have their mom or dad call to make sure it's okay."
Elliot smiled and started calling friends. After two phone calls, he found a friend whose family was not only willing to let him stay the night, but would keep him until Monday and make sure he got off to school. He called his dad, then started to pack. Dawson stumbled out with some serious after sex glow, and sex hair. I told him Elliot was going to spend the night at a friend's and would be gone until Monday, and he could stay home alone for the weekend. Dawson called his dad, and disappeared into his room. I made Elliot breakfast while he got dressed and packed. Dawson returned with a small smile on his face then said, "What's for breakfast?"
I was curious by what his father had said, and what he told him, but I just smiled and said, "Bacon and eggs. How do you want your eggs cooked?"
"I like over easy, but I want to shower first."
"Go ahead. I showered before I dressed."
"Do you always shower in the morning?"
"Yeah," I said. "Makes it easier for me to style my hair."
Elliot came bounding out and Dawson disappeared. I heard the water start for the shower so I cooked the bacon, and made Elliot some scrambled eggs. Dawson and I both liked our eggs over easy, so I waited for him to return before I made ours. I also made some toast, and soon, the three of us were having a pseudo family breakfast. Elliot had just finished when a knock came from the door. Elliot ran to answer it, and was greeted by a boy his age, and an older woman I assumed was the mother. She came in, introduced herself as Mrs. Edenton, and was more than a bit surprised to see me there, with Dawson in the house. I explained how their father didn't feel comfortable having the boys home alone, and wanted to know a responsible adult in the home. We agreed it was more to keep the boys from killing each other than anything else.
Once Elliot was gone, I went into their father's room and started to gather up my things when Dawson walked up behind me and began kissing my neck and fondling my breasts through my shirt. "I want you," he whispered.
"I can see that," I said.