Chapter 1: Chapter 1
It was decided. "Something has to be done for the boy," Karen thought to herself, sipping some chamomile on the living room couch. "He's 19, and he doesn't even masturbate yet. Where is poor Max going to end up if this continues?"
Max was her roommate: a kind, intelligent, but deeply insecure young man, with whom she had developed somewhat of a maternal relationship with. They had spent many long nights together, him venting his overwhelming emotions (he was easily overwhelmed), her offering patient understanding, and a soft, ample bosom to cry into. Karen reflected on the many times she had held him, his head resting against her breast, while she gently stroked his hair and cooed comforting whispers into his ear, until the weeping finally stopped and he drifted off to sleep.
Often, in these comforting sessions, Karen had noticed a tent form in Max's pajama bottoms, his cute little stiffy straining against the fabric. But she knew (he had unthinkingly divulged this to her while talking of something else) that he had never had an orgasm.
"He's probably too inhibited to experiment, the poor thing," Karen thought to herself. This, among many others reasons, led her to this decision: she would take on the responsibility of guiding Max through his first orgasm, teaching him how good his body could feel.
Karen looked over the edge of her teacup, at Max's bedroom door. "Okay," she thought, quietly psyching herself up, "I'm going to go in there, check on him, and offer him comfort and support like I always do. But this time, I'll offer him my breast for real, encouraging him to suckle and relax, while I stroke his hair and cradle him like usual. Then, when he's completely relaxed and zoned in to the suckling, I'll tell him that it's time to learn how to orgasm. I'll massage him through his pajamas until he's hard (if he isn't already), and then I'll gently pull it out, and guide him to completion, as he suckles. Of course, I'll be encouraging and understanding the whole way through, and I'll tell him how proud I am of him when it's all done."
She put the cup down, and took a deep breath. Saying all this was one thing, but doing it was another. She stood up, arranged herself for a moment in the mirror, and walked up to Max's door.
She knocked. "Max, honey, are you awake?"
"Yeah, actually..." Max croaked from inside. He had clearly been crying. "I couldn't sleep... Could you hold me for a while, Miss Karen?"
A perfect opportunity. Karen quietly exhaled through pursed lips. "Now or never," she thought to herself. "Just make him comfy like you always do, and everything will work out fine. It's hard, but he needs you now more than ever. No one else is going to do this for him. Now go!"
She put her hand on the knob, turned it, opened the door, and walked into Max's room.The sight that greeted her made her heart stop for a second. Max was on the bed, his face red from crying, his eyes wide open, he looked like a child having a nightmare. Beside him, on the nightstand, was a steaming mug, and next to the mug, a sheaf of papers strewn haphazardly across the table."Oh, honey, what's the matter?" Karen asked, coming to a stop in front of him, and putting her hand on his shoulder. "Did you have a bad dream?"
"No, I can't even sleep." He sniffed, tears brimming in his eyes again. "I don't know, Miss Karen. I'm feeling so many things, it's just like this big tangle, I can't pull it apart. I... I..."
"Poor dear," said Karen soothingly, tenderly pulling him into a warm embrace. "I've got you now," she whispered into his ear, "just let it all out, honey. I'll cradle you all night if I have to, it's okay."
Max doubled over, clutching at her sweater, burying his face between her breasts, and let out a long sob. Karen held him patiently, a soft, sad smile on her lips, as she rocked him back and forth, rubbing circles into his back.
After what seemed like an eternity, he pulled away, sniffling, and looked up at her. "How do you feel, Max?" she asked, leaning down to kiss him on the cheek he had raised. "Any better?"
"Much better, thank you, Miss Karen," he replied, smiling weakly.
"Now, let's see if we can't get you to sleep," she cooed. "I'm going to cradle you until you fall asleep, okay? So settle in," she said, with a loving smile.
For a moment, he looked so happy she was afraid he'd start crying again. He happily settled in to her embrace, shifting around to be more comfortable. "Thank you so much Miss Karen, I don't know what I-"
"Shhhh," she said, gently placing a finger on his lips. "Don't say a word, just let me take care of you, okay? Now, close your eyes." He closed them, smiling like a baby.
She took a long, deep breath. "You can do this, K," she thought to herself.
"Take a deep breath honey, just try to relax and feel good. Here, suckle on this, it'll help you get nice and cozy..." Without disturbing Max, she slowly pulled up one side of her sweater, until her right breast came spilling out onto Max's face, suddenly surrounding it with her soft, warm flesh.