Shawn and his mother Jennifer sat fiddling with their phones. Shawn was scrolling through Facebook, and Jennifer was texting her sister. They were sitting in the living/waiting room of therapist Deborah Peters for their usual Wednesday appointment. They had started seeing Deborah during Jennifer’s divorce from her now ex-husband five years earlier. Shawn was thirteen when his parents’ marriage started falling apart. Once he realized what was going on it affected him more than he was willing to admit. When they divorced a year later he retreated into himself, barely spoke and often locked himself in his room for hours at a time drowning out the outside world with loud music or video games. Deborah came highly recommended, and she was able to help both Shawn and Jennifer, during and especially after the divorce was final.
Shawn had retreated so far into himself it amazed Jennifer that Deborah was able to bring her now 19 year old son back from the depression he had fallen into. Shawn had come back out of his shell and he and his mother had gotten closer in the years since the divorce. There were still some things he didn’t feel comfortable telling her, and that’s where Deborah came in.
Jennifer was also amazed that Deborah was able to make her feel better about all the shit she had gone through with her ex-husband. The first eleven and a half years of their marriage had been great, but somewhere along the line they grew apart and in the last couple of years they were barely speaking to each other and were sleeping in separate rooms. After 15 years of marriage, they filed for divorce. Jenny was able to get out a lot of her frustration talking to Deborah.
The door to Deborah’s office opened and she stepped out. Shawn and Jennifer looked up.
“Sorry for the wait,” she said, “I had a patient on the phone. So, who’s first today?”
“Go ahead, honey.” Jennifer said, patting her son on the leg. “Your Aunt and I are texting, and you know how she is when she gets going.”
Shawn rolled his eyes, “Yeah, once Aunt Patty gets started it’s hard to get her to stop.”
Deborah ushered Shawn into her office. It used to be a study, but since she decided to work out of her home instead of leasing office space, she transformed it into her office. Shawn liked Deborah, aside from the fact that he could tell her things he couldn’t tell his mother, there was also the fact that she was stunning. She may have been 28 years older than him, but she had the body of a woman at least ten to fifteen years younger. Standing at 5′ 8″, she had a trim athletic build, an impressive 40DD chest (which she tried with varying levels of success to hide with baggy or loose fitting tops), and killer legs. Shawn had never been into older women, especially women that were old enough to be his mother, but Deborah was the exception.
He plopped down on the couch as Deborah sat down in her easy chair.
“So, what’s going on Shawn?”
“Not much… actually that’s bullshit.” he said, “Deb, you don’t tell my mother what happens in our sessions, right?”
Deborah didn’t mind that her patients referred to her by Deborah, Debbie or Deb. She wanted them to feel like they were talking to a friend, not a therapist. She wanted them to speak their minds, so she didn’t mind if they swore, yelled, cried, or just generally vented. It was also part of the reason she worked out of her home. She figured people would be more comfortable in her home instead of a cold, impersonal office.
“Of course not,” Deborah said, “What you say stays between us, it’s that whole doctor/patient confidentiality rule. I can’t tell you mother anything unless I think it’s illegal, or you’re a danger to yourself or others. You know you can tell me anything.”
“Something happened a couple of weeks ago, and mom doesn’t know… at least I don’t think she does.” Shawn said, looking down at the floor.
“Shawn, what is it?”
“I saw my mother naked.” he finally said.
“And you’re not sure if she knows?” Deborah asked.
He nodded, “I came home from my friend’s house, and as I went upstairs to my room I passed by mom’s room. She’d just gotten out of the shower, and she didn’t have the bedroom door closed all the way. As I passed by, I glanced in just as she took her towel off to dry herself, and I could see everything, well most everything. She was standing in front of the window and the light was shining just right, so I could only see her in profile. But it was enough. I could see all her curves, and…”
“It excited you.”
Shawn nodded, “Yeah, it did. I mean, I’ve seen naked women before, but this was my mother. She probably didn’t close the door all the way because she was home alone and didn’t think I’d be home anytime soon.”
“Go on,” Deborah said, “What happened next?”
Shawn kicked off his sneakers and put his feet up on the couch. Deborah didn’t mind, she encouraged her patients to get comfortable while they were talking to her. Some people would actually lay down, some would stretch out like Shawn was, some curled their feet up under them. Whatever made them feel comfortable.
“She turned and went back to the bathroom and I snuck back downstairs and made a show out of making noise and letting her know I was home. I heard her bedroom door close after that.” Shawn said, “I kept replaying that moment over and over in my head.”
“And how do you feel about that?” Deborah asked.
“A little guilty. Like I said, mom thought she was alone, and certainly wasn’t expecting me to be peeping in on her. And she’s my mother.” He finally looked up. “I shouldn’t be perving on my mother like that, right?”
“Well, it’s not like you planned it, right?” Deborah said, “It was an accident. You had no idea she’d be coming out of the shower at that exact moment.”
“Well at least not that time.” Shawn said.
“Meaning?”
“I tried to see her again, and I did, a few times.” Shawn said, “I went out of my way to listen for her in the shower. I was determined to see her naked again. Part of me knew it was wrong, but part of me wanted to see her again, the part of me that wanted to see her won out.”
He sighed, and looked up at Deborah, she wasn’t judging him, he could tell that just by looking at her. She was patiently waiting for him to tell her the rest of the story.
“First time was last Saturday.” he finally said, “I usually sleep in, but I had to pee, so I got up and went to the bathroom, and that’s when I heard the shower in mom’s bathroom running.”
Jennifer’s bedroom had an attached bathroom, while Shawn’s didn’t, so he had to use the bathroom down the hall from his room. Due to the way the upstairs was set up, he could see into his mother’s room from the hall bathroom.
“The door was ajar again, and I heard the water shut off. I stayed in the bathroom with the lights off, peeking into her room. Again she came out into the bedroom to dry off. I was able to get a somewhat better look, but because of the angle she kept moving out of my line of sight.”
Shawn adjusted his position on the couch, his dick was getting hard, and he was trying to adjust it without being obvious about it. If Deborah noticed, she didn’t say anything.
“Then again last Tuesday,” Shawn continued, “Again the door was ajar and I snuck up and peeked in. Unlike the other two times where she came out of the bathroom without the towel wrapped around her, this time she was drying her hair. I was mesmerized by the sight of her body. I mean I guess I sort of always knew mom had a nice body, I saw her in her bathing suit when we went to the beach or swam in the pool in the backyard, but that was a one piece and not a bikini. This was the first really good view I had of her body. She’s got the most perfect breasts I’ve ever seen, and she doesn’t look like she gave birth to me all those years ago, she’s… oh god, I can’t believe I’m talking about my mother like this.”
He again shifted to try to surreptitiously adjust his growing erection.
“But her body, it’s just perfect. She stopped in front of the mirror and stretched, and I could see everything. It’s like she was admiring herself, she even smiled a bit, turning one way and then the other, turning all the way around and looking over her shoulder at her reflection. I saw her from all angles, and I…”
He couldn’t finish, his dick was fully hard, and this time there was no way he could adjust it without being obvious about it.
“You got an erection?” Deborah asked.
Shawn nodded. “I left before she could see me though. The same thing happened again on Thursday. She came out with the towel wrapped around her, then took it off to dry herself off. I was mesmerized watching her breasts jiggle as she moved. I looked at her butt when she bent over to dry her legs. Then she did the same thing she did on Tuesday. Admired herself in the mirror. But then…”
Again he had to adjust his rock hard dick. Again Deborah didn’t say anything as he quite obviously adjusted himself.
“…then, she started… she started touching herself.” Shawn finally said, “She turned around and looked at herself from behind. She reached behind her and grabbed her butt, squeezed it a couple of times, and then turned around as she ran her hands up her body, and grabbed her breasts, and squeezed them as well. Then she… she… she put her hands between her legs, and started… I can’t believe I’m about to say this. She started masturbating.”
He stopped again and got up and walked over to the mini-fridge Deborah kept in the corner of the room with various refreshments for her patients. He grabbed a soda, took a swig as he walked back over to the couch and sat back down.
“I couldn’t believe what I was seeing. The more she touched herself, the more excited she got, she started moaning and groaning, moving one of her hands back up to her tits… I mean her breasts, and squeezing and pinching her nipple. I couldn’t help it, and I…”
“You started masturbating too?” Deborah asked. Shawn nodded and took another swig of soda.
“I was more turned on than I’d ever been in my life, and that included when I lost my virginity to Alicia Miller last year.” He said, referring to the girl he had lost his virginity to a year earlier, a couple of months after his 18th birthday. “Hearing mom moan and groan and watching her hand move faster and faster between her legs just pushed me over the edge, and then she… she… you know…”
“Had an orgasm.” Deborah said, again finishing the thought that Shawn was having trouble saying himself.
“Yeah, she cried out, her body shuddered and she collapsed on the bed. She was breathing heavily and mumbling ‘Oh my god’ under her breath. I quietly made my way back to my room and finished myself off. It was probably the most intense orgasm I’d ever had. All I could see in my mind’s eye was my mother’s naked body.”
“Did you feel guilty about watching her?” Deborah asked.
“That’s just the thing,” Shawn said. “This time I didn’t. Hell, I didn’t feel guilty on Tuesday either. The first two times I felt kind of guilty. But the last two, not so much. I got worried that she would catch me so I stopped after that, but then something happened this past Sunday.”
He took another drink of soda finishing off the bottle, adjusted his erection again and took a deep breath.
“I woke up around 9ish I guess, and I had a case of morning wood. I figured I should take care of it, so with visions of mom in my head, I started masturbating, and the one thing every guy dreads happened. She walked in on me. I didn’t even realize it at first, I was so into the fantasy going on in my head, until I heard her gasp. I looked over, covered myself up, and turned away from her. She turned away, apologized and left the room. The funny thing is, I didn’t lose my erection. In fact, I got more excited when I realized she had just seen my dick… erm I mean my penis for the first time. I was actually able to finish, and had another pretty intense orgasm. I cleaned up and went downstairs a few minutes later. We both acted like nothing unusual had happened, but I knew I’d have something to talk about today.”
“If that hadn’t happened, your mother walking in on you I mean, would you have told me about your peeping on her?” Deborah asked.
“I don’t know,” Shawn said. “I wish I could have seen her at least one more time, but the last couple of days her door’s been closed. Maybe if I had caught one more glimpse.”
“You said the ‘fantasy going on in your head’ when your mother walked in on you. What was the fantasy?” Deborah asked after a moment, chewing over everything Shawn had told her.
Shawn fiddled with the empty bottle, debating how much he wanted to tell Deborah about the fantasies he’d been having about his mother.
“Shawn,” Deborah said, “What was the fantasy you were having?”
Shawn took a deep breath, glanced out the window for a moment, then back down at the empty bottle. “That I was having sex with her.” he said quietly.
“Would you care to elaborate?”
What he really wanted to do was run to the bathroom and rub one out, but he just adjusted himself again, but couldn’t bring himself to look at Deborah or say anything.
“Shawn, I understand that it can be kind of embarrassing, but you’ve been coming here for almost six years now. You’ve told me a lot of things that you haven’t been able to tell your mother, and I’ve never told her anything that you’ve told me. I’m not going to start now.” Deborah said.
“It’s not just embarrassing,” Shawn said, “It’s just that I don’t know how to elaborate on that. I mean do you want specific details? Plus the fantasy changes a little every time, it’s not like a video where it plays back the same every time.”
“Shawn, I’ve haven’t said anything before, but I notice you keep adjusting yourself.” Deborah said, “Is talking about this getting you excited?”
“Yeah,” he said, still not looking up. “It’s actually really uncomfortable.”
“It looks like it,” Deborah said, “It actually looks like you’re in a little bit of pain.”
He nodded, he had the worst case of blue balls right now.
“Well then go ahead and relieve yourself.” Deborah said.
“What? Right here? Right now?” Shawn asked, finally looking up, a shocked expression on his face.
“Sure, why not?”
“Well I figured masturbation was kind of you know… a private thing.” Shawn said, “Not like something you do in front of someone else. Especially not my therapist!”
“Shawn, you’re uncomfortable and in pain.” Deborah said, “I don’t want you to feel like you have to hide anything from me.”
“But this is…”
“Just another form of stress relief.” Deborah said, “Everyone does it, although not everyone admits to it. Hell, I do it. Your mother does it, your friends do it, doctors, lawyers, police officers, firemen, the guy who works at the burger joint down the street, Jake from State Farm.”
Shawn had to laugh a little bit at the last example, but he had to admit she had a point. He was going to run to the bathroom when his session was over and rub one out while Deborah and his mother had their session anyway. Plus, it felt like his cock was about to rip through his underwear and jeans.
“Hell, they wrote songs about it. The most popular one was literally called I Touch Myself.”
Fuck it, if she didn’t mind, then he didn’t. He’d actually fantasized about Deborah a few times as well when he masturbated, so why the hell not? He chucked the empty bottle into the trash, got comfortable on the couch and took one last glance at Deborah. She smiled at him and nodded.
He undid his belt and unbuttoned and unzipped his jeans. He took a deep breath and lifted his hips as he pushed his jeans and underwear down, and his cock sprang into view.
Deborah’s eyes went wide. She wasn’t sure what she was expecting when she encouraged Shawn to masturbate in front of her, but she wasn’t expecting his cock to be so big! If she had to guess just by eyeballing it, she guessed he was probably 7-8 inches long and about two inches in diameter. She felt a tingling in her pussy, and casually crossed her legs, she figured she might have to rub one out herself later.
Shawn grabbed his cock, closed his eyes and started slowly stroking himself.
“Tell me about your fantasy of having sex with your mother.” she said quietly.
Shawn called up the way most of his fantasies started, “Well I’m watching mom, she’s just come out of the shower, she’s pulling her towel off and I can see every inch of her body. She’s drying herself off, looking at herself in the mirror. I’m watching her tits jiggle as she moves, I realize what a great ass she has as she bends over to dry her legs. She’s done drying herself now and is admiring herself in the mirror, smiling. I take my clothes off as I’m watching her and my dick is already hard. I start stroking myself as she lays down on the bed and starts playing with herself. I walk into the room and she doesn’t seem surprised or upset that I’ve just walked in on her, or that I’m naked and openly masturbating.”
Deborah now found she was the one who was adjusting herself, she squirmed a bit in her seat and uncrossed and recrossed her legs, fighting the urge to pull up her skirt and plunge her fingers into her tingling pussy. She wasn’t sure what she expected would happen when she encouraged Shawn to masturbate and tell her his fantasy about his mother, but she didn’t expect herself to get this turned on.
“She invites me to come closer and sits up. She looks at my cock and takes it into her hands and smiles up at me. ‘Is this for me?’ she asks, I smile and nod. She says ‘Thank you baby.’ and takes my cock into her mouth.”
Shawn was full into the fantasy now, almost forgetting that he was openly masturbating in front of his therapist, using the terms he only used in his fantasies and with his friends.
“She starts sucking my cock and it’s the best feeling in the world.”
“Have you ever had your… experienced that before?” Deborah asked, unbuttoning the first couple of buttons on her blouse.
“No, not yet,” Shawn said, “I’ve only had sex with two girls, and neither one of them wanted to go down on me. They just wanted to fuck.”
“Go on,” Deborah said, unbuttoning another button, and fanning herself.
“She’s still sucking my cock, and I reach down and gently squeeze one of her tits. She looks up at me and I can tell that she likes what I’m doing, but she doesn’t stop. In fact she starts going faster, and I put my hand on her head and control her pace making her go even faster, until I feel like I’m going to cum.”
Shawn’s hand moved faster, and then slowed down as he controlled the pace of his masturbation to match what was going on in his head.
“She asks me if I want to fuck her and of course I say yes. She moves up onto the bed and opens her arms to me and says ‘Come here and fuck mommy.’ I crawl onto the bed, and mount my mother, sliding my cock into her soaking wet pussy. She’s been waiting for this. She wants this as much as I do. I look her in the eyes as I slide all the way in. She says ‘I love you so much, baby.’ and I say ‘I love you too, mom.’ She says, ‘Now fuck me, show me how much you love me!’ So that’s exactly what I do. I start fucking her…”
Deborah got another button undone on her blouse, and along with a generous amount of cleavage the edges of her bra were also visible. She gently ran her finger along the exposed flesh, her breathing increasing as she became more flustered wondering what she’d unleashed, but unwilling to stop it.
Shawn’s hand increased speed on his cock as his fantasy continued to play out.
“Sometimes at this point, things change. Sometimes I pull out and cum all over her tits and face, and then go back to fucking her because in my fantasies I can cum over and over again. Sometimes I throw her legs over my shoulders so I can fuck her even deeper and cum inside her. Sometimes we change positions, like now. She’s getting up on her hands and knees so I can fuck her from behind. Doggy style. I slide my cock back into her, grab her hips and start slamming my cock in her.”
His hand was practically a blur on his cock now, she could tell he was close. Despite that she undid another button on her blouse revealing more of her bra. She ran her finger across her exposed cleavage, and under the edges of the bra. It was taking everything she had to not rip her clothes off and jump on the hot young cock that was just a mere five feet away from her.
“She’s screaming at me to fuck her harder, and I oblige slamming my cock into her as hard as I can. She’s yelling and screaming my name, telling me that she’s going to cum and she wants me to cum with her. We’re almost there… we’re so close now. And… oh fuck!”
Shawn’s hips jerked and a thick stream of cum shot out of his cock at least two inches in the air and landed on his stomach, it was followed by a second, equally thick stream that landed right next to the first one. He was groaning quietly as he continued to stroke his cock. His body jerked again and a third stream erupted from his cock and landed just below the first two. Shawn’s hand slowed down and two final weaker jets of cum oozed out of his cock as he tried to get his breathing under control.
Deborah quickly collected herself and buttoned her blouse back up. Shawn opened his eyes and held his hand up, covered in his cum.
“Holy shit,” he gasped, and looked over at Deborah, “I guess I got a little carried away.”
Deborah handed him a box of tissues.
“It’s okay,” she said, having managed to pull herself back together, “You obviously needed that. Do you feel better now?”
“Actually, strangely enough, I do,” Shawn said as he cleaned himself up, tossing the soiled tissues in the garbage. He stood up as he pulled his pants back up. “It felt a little weird telling you my fantasies while you were watching me masturbate. But it felt liberating to tell somebody that. I could NEVER tell mom that. Especially not with my dick in my hand.”
“That’s what I’m here for.” Deborah said, offering him a smile. “Look Shawn, there’s no shame in fantasizing about your mother. You’re not the only person who does, a lot of boys your age have fantasies about their mothers. Contrary to popular belief there’s nothing wrong with a healthy fantasy life, no matter who or what you’re imagining. A lot of people tell me that keeping their mind occupied with a fantasy, sexual or not, helps them get through the day. Doesn’t matter if they’re working, walking the dog, going shopping, at the doctors, or waiting in line at the bank.”
Shawn sat back down and kicked his feet back up on the couch. “Really? So I’m not some sort of a freak?”
Deborah laughed, “No, you’re not a freak. You’re a normal teenager. Can I ask how often you masturbate?”
“I dunno,” Shawn said, “I don’t actually keep track of it. If I had to guess maybe 4-5 times a week, usually right before I go to bed. Sometimes first thing in the morning if I wake up with an erection. On rare occasions I might do it twice a day.”
“Do you always think of your mother?”
“Not until recently,” Shawn said, “Usually it’s one of the two girls I slept with, sometimes both of them and me, sometimes it’s some celebrity, or even just a beautiful girl I saw that day. Sometimes I imagine I’m a porn star and get to fuck… I mean have sex with some of my favorite female porn stars.”
“You can say fuck if you want to.” Deborah said, “Do you watch a lot of porn?”
He nodded, “I got a couple of my favorite sites saved on my phone. When I masturbate before I go to bed I’ll watch a video or two for inspiration.”
“Well, I think that’s enough for today.” Deborah said, “But I think we’ll need to talk more about this next week. And maybe, write down any fantasies you might have for our next session, okay?”
“Okay,” Shawn said, pulling his sneakers back on. “I’ll try to remember to do that.”
They exited the office. Jennifer was on her phone, playing Candy Crush.
“Ready for me Debbie?” she asked.
“She’s all yours mom.” Shawn said.
Jennifer got up and Shawn gave her a hug. She hugged him back.
“I love you mom.”
“I love you too, baby.”
He held the hug a moment longer and let her go, giving her a kiss on the cheek. Jenny ruffled his hair and followed Deborah into her office. Shawn sat down on the couch, pulled out his phone, logged onto Deborah’s wi-fi and watched some of his favorite YouTubers while he waited for his mother’s session to end.