Karen could never forget the first time she saw her son’s best friend masturbating.
Karen was letting him stay over at her house while he in college – it was just closer and easier that way. She got more than she bargained for.
It happened a few months ago. Tom had just turned 19, and she wanted to surprise him on the midnight of his birthday with a gift while he was still watching tv in the living room.
So Karen gently and quietly opened her bedroom door with her present in hand, and softly walked towards the living room without making a sound and what she saw left her stunned: Tom was watching soft-core porn on cable. And as she quietly stepped even closer near the couch, she could see that he was masturbating.
Her heart pounded. She couldn’t believe that this wholesome young man could do something so brazen in their living room. Sure, she knew that all boys were especially horny at that age, but this? In the same house while he thought others were sleeping?
But above another else, she couldn’t believe how she felt about seeing him pleasure himself so explicitly. Karen had only been with one man her entire life, and that was her ex-husband. That’s how conservative and proper she was raised. Her favorite fantasy was to watch him masturbate while looking at her, but her ex-husband always laughed it off and was reluctant to do it because of how ridiculous he thought it was.
Now here she was, with the middle of her legs becoming wet, watching her son’s best friend pleasure himself. She was aroused and she knew it. She quietly tiptoed back to her room before she could get caught and she later did something that she NEVER thought she would EVER do she fantasized about her son’s best friend for the very first time in her life.
“This looks good,” Tom said as he went to the kitchen for breakfast.
She smiled, “Thanks. I was supposed to meet some clients this morning, but I got a message late last night that they had to cancel. My boss said I could finish my report at home, so I figured I might as well do some cooking and catch up on chores while I had the extra time.”
“Lucky,” he replied while eating. “I’ve got an exam today and it’s a real pain in the ass. But seriously, you work too hard and you should try relaxing a little.”
“If I relaxed during my free time, then who would cook and clean? It certainly wouldn’t be you,” she replied jokingly.
“Good point. In that case, just work the amount that you need and don’t tire yourself out too much.”
She playfully slapped him on the arm. “Very funny. You know, if I didn’t like you so much, I would have forced you to do your own laundry and to clean your own room by now.”
He grabbed the remainder of his food and got up to give her a kiss. “Then I guess I’m really lucky to have you in my life. I wish I could stay and eat, but I have to meet some friends for some last minute studying. It’s the only way I can be as smart as you right?”
“I’m glad we agree on that,” she replied as he smiled and left.
After cleaning the dishes and vacuuming the carpet, Karen went to her Tom’s room to do his laundry. She pulled off the pillow case on his bed, and when she grabbed the blanket, she saw something that left her as speechless as the day she caught Tom masturbating months ago: There was a photo of her underneath his blanket.
‘What’s this doing here?’ she thought to herself.
It was a photo of her in a one piece bathing suit from a summer vacation they had two years ago. The picture itself was from a photo album which she kept in the closet in the hallway. But what was it doing in his bed?
A realization had suddenly come over her. When she vacuumed his room a moment earlier, she had picked a few pieces of used tissue paper off the floor and threw it in his trash.
‘Oh god,’ she gasped. ‘Was Tom thinking about me?’
Karen felt torn. On the one hand, she felt disgusted and betrayed that her son’s best friend could do such a thing with her picture. On the other hand, she knew couldn’t really be mad at him because just a few months ago, she had watched him masturbate and then fantasized about him afterwards. And frankly, the thought of Tom masturbating to her picture made her feel inexplicably naughty, but in a good way. She even felt a little flattered by it.
Almost without thinking, Karen walked to her room to grab an even more private photo of herself, which she had hid in a drawer. It was a picture of one of the rare moments in her life that she had ever worn a small bikini, while at a private pool party with her close friends.
She went back to the room and tucked it neatly under his blanket for him to ‘use’ later.
The rest of the day was as usual. She did her work, cooked, had dinner, and watched a little tv before calling it a night. Also as usual, Karen ended her day by washing up and putting on her flannel pajamas before heading to bed. However, when she exited her bathroom, she saw Tom walking down the hallway and towards her bedroom. And by the look on his face, he had something important to say.
“Were you…did you clean my room today?” he asked uncomfortably, standing in her room.
“Of course I did. Your room didn’t just clean itself you know,” she replied casually, as if nothing was out of the ordinary.
“Well of course I know that. But my bed…did you…”
“If you’re referring to the picture left under your blanket, then don’t worry, it wasn’t a ghost that put it there- I did,” she said with a soft smile.
“Am I missing something here?” he asked. “I mean, shouldn’t you be mad at me? Aren’t you upset at all?”
“I’ll answer your question on one condition,” she replied.
“I want you to tell me why you were using my picture. And I want an honest answer.”
He paused for a moment. “Fine. Being completely honest here, I’ve always thought of you as being my ideal woman. You’re smart, classy, caring, and you’re really really sexy. I know you’re my best friend’s mom and everything, but that’s just how I feel.”
“That’s very sweet of you to say,” she replied, feeling genuinely touched by his words.
“Now it’s your turn. Why did you leave a bikini picture of you in my room?”
She sighed, “You know, a part of me wished that you would have given a vague answer because I wanted to give a vague response. But since you were so open and honest, here it goes; I’ve always been excited by the thought & sight of a man pleasuring himself. Don’t ask me why, but it just gets me going. It’s the only kink I have really. My ex rarely ever let me watch him masturbate, and on the rare occasions he did, it would only be for a quick few seconds and he would laugh it off before stopping. Then a few months ago, I saw you…you know…”
“You saw me jerking off?
She nodded, “In the living room late at night. I saw you masturbating, and truthfully, a big part of me was very aroused. And when I saw my picture in your bed today, I was flattered by it. In fact, it turned me on in a strangely erotic way.”
“All I can say is– wow! You always were cool, but when it came to the magic s-word, I’ve always thought you were a real prude because of how conservative you always seem,” he said, referring to sex.