Back at school, Henry felt the weight of loneliness taking over. Laying in bed in his dorm room, on the top bunk of his bed, Henry thought of his mothers and the time they'd spent together over his last break. Soon, his thoughts floated to the bedroom, and he found himself growing hard as he pictured their interactions.
His breaths became heavy, and before long, he found his hand slipping into the waistband of his boxers, despite the proximity of his roommate on the bottom bunk. To muffle the sounds of pleasure and heavy breaths, Henry bit down on his lip as he stroked himself hard and fast until he came.
The next break he had was over Spring Break. When he found himself in bed with his mothers, each of them straddling one of his thighs, his cock quickly became hard, and precum formed on its head.
Then, Regina chuckled, "Oh, my," looking over at their son. "I think our baby boy is hard again."
Blushing, Henry squirmed slightly and covered his crotch.
"Don't be embarrassed, sweetheart," Regina cooed. "Do you want to cum?"
Looking down at the precum on Henry's cock, she didn't have to wait for an answer. Instead, she reached out to stroke her son's length again, firming him with her touch.
"Mom…" he said softly.
"Yes, dear?"
"Please. I missed you so much."
"Oh, baby," Emma whispered, stroking his hair back. "We missed you too."
"I touch myself at school thinking about you," the young man confessed.
"Is that so?" Regina asked, voice low and seductive. "And what exactly do you think about?"
"I…"
"It's okay, Hen," Emma told him, when he trailed off. "You can tell us."
"I just think about… I don't know. Everything, I guess. Making love to you… Touching you. The way you let me… Um…"
"The way we let you what, honey?" Regina asked, trailing a feather-light touch down her son's torso and stopping next to his growing erection.
"The way you let me suck on your breasts."
"Ohhh. I see. You liked that, huh?"
"Yes, ma'am."
"Good. We did too, bubby."
After a pause where they both simply looked down and smiled at their son, Emma's gaze dropped to his stiff cock, the head glistening with precum.
"Mmm," she mumbled. "So hard for us. So handsome. Don't you think, Gina?"
Emma's wife nodded and continued to smile.
"I think I'm getting a little wet, Hen. Will you check for me?" Emma asked, her voice teasing and playful.
Henry blushed and reached out to push his fingers between her folds.
"Oh, Ma… You're…"
"Mhmm."
Emma was dripping. Slowly, she rocked forward on his thigh, and when he felt the slick arousal coating him, Henry shivered.
"I think I am too, baby boy," Regina cooed. "Will you check?"
Henry repeated the motion with his other mother and found that Regina was just as damp. When Regina noticed that Emma was rocking against him steadily, she mimicked the motion and gasped softly when she felt the stimulation and friction against her clit.
"Oh, Hen. You're so warm, baby," she mewled, rubbing her hands over his chest.
Emma leaned forward, changing the angle of stimulation, and rubbed her son's abdomen. The stimulation only increased the straining of his cock, and he whimpered softly as they continued to ride his thighs.
"Do you want to watch us cum at the same time, Hen?" Emma asked, dragging her nails down his front.
When he nodded, she smiled at him and guided each of his hands to their clits. He took the hint and rubbed each of them gently, causing them both to gasp at the added sensation of his warm, gentle fingertips. After a while of working their rocking hips into a steady rhythm, Emma picked up her pace, and Regina followed.
"Getting close," Emma gasped, pressing Henry's hand harder against her clit.
Skillfully, and without prompting, Henry slid his hand forward, pushing his fingers into their centers and rubbing their clits with the palm of his hand.
"That's it, baby boy," Regina gasped. "Oh, God. That's it."
Once he curled his fingers, they were through. Emma came first, but Regina followed almost instantly, their thighs shaking and squeezing Henry's.
"Oh, baby," Regina cried. "God. Fuck. Deeper."
He pushed his fingers deeper into their dripping cunts and curled them again, allowing them to ride out their orgasms completely.
"Fuck, you're so hot," Henry finally groaned. "I need you both."
"You'll have to be a good boy…" Emma told him slowly. "A very good boy."
Henry nodded quickly, desperately, and looked up at his mothers eagerly.
"Gina? Should we give him a little test?"
"Mmm. Good idea, darling. You first."
"We're going to play a little game," Emma told her son. "I'm going to put your cock inside me, and ride you… and you're not going to cum."
"B-But… Mom, I… I need-"
"Be a good boy, Henry," Regina warned him, dragging her nails down his chest, over his nipple.
"Yes, ma'am."
"Good boy," Emma cooed, stroking his hair back. "Now… Let's see how much you can take."
Emma slowly mounted her son, rubbing herself along the length of Henry's hard cock. After he expelled a few moans and gasps of agony, she slowly positioned herself above him, lining herself up with the head of his length and guiding herself onto it.
"Oh, Mom," he groaned, as she sank down onto his shaft. "Fuck."
Carefully, the blonde began to move up and down, sinking onto him over and over until she'd worked up a bouncing rhythm that put Henry on edge almost instantly.
"Mumma," he whined. "Gonna-"
"No, Henry," Emma scolded him breathlessly. "Hold it. Don't cum."
"Mom, I-"
"Hold it in, Henry. Be a good boy," Regina cut in, twisting his nipples between her fingers and making his back arch.
Then, Emma began to roll her hips forward, and the extra friction around Henry's cock made his thighs shake.
"Don't you dare," the woman scolded. "Not… until…" Gasping a few times before continuing, Emma finished, "Not until… I do."
Slowly, Regina moved behind her wife, kneeling between Henry's legs, and moved her arms around to Emma's front to massage her breasts. This earned a soft moan from the woman's lips as she continued to move.
"Getting close?" Regina asked, pinching her nipples.
"Mmm."
"Mommy, please," Henry cried. "I can't. Can't do it."
"Yes, you can, Henry," Regina asserted.
When Emma pulled herself off of him and dismounted, Henry nearly screamed. Her hands began to cup his balls and fondle the base of the aching base of his penis. Slowly, she slid one finger from the base up to the tip and pinched the head of it, making his hips jerk. This earned a sly smile from his mothers, who watched him squirm contently.
"Oh, Henry," Emma sighed, leaning in to kiss his pulsing shaft. "Such a beautiful boy…"
Feeling the bulge of his veins under her lips made Emma's mouth water, and she found herself wanting relief almost as much as she wanted to drag out her son's pleasure. She resisted the urge to move in for a quick finish, though, and kissed Henry's abdomen. Next, her mouth moved up to his nipple, and she sucked on it lightly as her hand reached down to squeeze the head of his cock again.
Then, she whispered, "It's okay, bubby. I'm gonna let you cum. But we're going to try something new first…"
Slowly, Emma repositioned herself on top of him, but not mounting his hips. No, she was in a different position entirely. When Henry realized what she was doing, his mouth opened slightly. As he stared, Emma hovered her crotch over his face, holding herself up slightly, and started to suck his cock into her mouth.
"Suck her clit, baby boy," Regina cooed, running her fingers through Henry's hair. "Make her cum, and she'll return the favor."
Emma hummed in agreement around his cock, then briefly released him when she felt her son's warm mouth on her clit, sucking lightly.
"Ahhh," Emma gasped. "Bubby. That's it. Just like that."
"Mumma," Henry breathed, licking her between her folders and dipping his tongue into her core, lapping at her juices and driving her mad.
"Good boy," Regina encouraged him with a smile, as she watched contently as her wife and her son performed the most erotic dance of sixty-nine she every could have imagined.
She'd done this before, with her wife, but watching the scene play out in front of her were just as arousing. She was dripping too.
When her wife stroked her back, her fingertips sliding seductively down her spine, Emma hummed around her son's shaft again, making his hips jerk up and push his length deeper into her mouth. When it hit the back of her throat, she nearly gagged, but recovered quickly and sucked harder. As soon as she felt him doing the same, she moaned loudly and licked his length from base to tip.
"Good boy," Regina smiled, moving her hand down to the curve of Emma's ass and groping it. "Good boy, Hen. Keep going. Lick her clit. Suck it. Swirl your tongue around her til she cums, baby boy."
Emma mumbled, "Mmm," and ground her clit against her son's lips before releasing his length again with a soft 'pop,' just before he came. "Stop."
He gasped in disbelief but obeyed her, struggling for breath as he licked her arousal from his lips.
"Inside," the blonde ordered breathlessly, rolling next to him, onto her back.
Again, he obeyed, body shaking from the intensity of his arousal and the electricity coursing through his veins.
"Now," she demanded, grabbing his hips and jerking them forward and pushing his length inside her.
Rapidly, he began to thrust, aching for release, but Emma stilled his hips as soon as his thighs began to shake harder and held him inside her.
She gasped, "Not yet," as she tried to control the movements of her hips. "Keep going. Almost there."
Luckily for him, just as he was crying out again in agony, Emma's walls clenched around his length and began to convulse once more, bringing her to orgasm.
"Now, baby," Regina told him, sensing her wife's muscles tense up through the climax. "She's cumming."
"Fuck!" Henry screamed, moving wildly within her. "Mom!"
"Oh, God, Henry. That's it, baby."
He didn't stop until they both were spent.
Despite how hard he tried to sleep beside them, Henry found himself thinking back to the first night he'd been with his mothers sexually.
He remembered too vividly lying in his own bed, stroking himself painfully while listening to the noises coming from his parents' room as they made love to each other. They weren't exactly quiet. He was sure they didn't know how their moans carried through the house and found their way to his ears at night, and he was grateful for it. It was his only release, to lie there, pleasuring himself, imagining being a part of their close. Intimate relationship. He longed to be with them, to lie next to them in their bed. To make love to them both.
The louder their moans became, the harder he had stroked himself, desperate for orgasm. On that particular night, though, a sound coming from their bedroom stilled his hand: the sound of Regina sobbing. His heart sputtered at the noise and instantly began to ache. On top of that, the emotion of fear flooded him. What could possibly be making his mother cry? There had been very few times in his life that he'd seen or heard her cry, and it terrified him. What had happened? Just as he was about to tuck his still-raging erection away and get out of bed to check on his mothers in their room, the sound of sobbing ceased. He waited and listened for several minutes before his heartbeat slowed and the sweat stopped dripping from his brow. When he was sure that the crying had stopped, he tried to shut his eyes and settle back into bed, but once his fears were calmed by the silence, his thoughts had floated back to his mothers, and the noises that had come before the sound of sobbing.
Henry had whimpered in his sleep, feeling the ache of his hard-on straining against the tightening fabric of his boxers. He tried rolling onto his side to see if that would relieve some of the pressure, but it didn't help. In fact, it made him even more uncomfortable, so he returned to his previous position of lying on his back, reluctantly put his hand back into his boxers, and began to stroke himself again. It was slow at first, but he quickly picked up the pace, at least until he heard Regina cough from the doorway.
And that had been the beginning of it all.
Now, he really was in bed with them, all three of them naked and lying in each other's arms, exhausted from their orgasms. It suddenly seemed so surreal, like he was dreaming.
Finally, after sitting uncomfortably with these thoughts for what seemed like hours, Henry did fall asleep between them.
In the morning, both women noticed that he was somewhat sullen and withdrawn.
"Henry?" Regina asked softly, putting her hand on his shoulder. "What's the matter, sweetheart?"
"Hmm?" he answered. "Oh, I'm fine."
"Henry…" Emma chimed in. "Tell us what's wrong. Is it just that you don't want to go back to school?"
"No, I…. I'm just… It's nothing."
"C'mon, Hen," Emma sighed, her hand bumping Regina's as she rubbed his back. "What's up?"
"I just… I feel like I'm… Like you two have such a great relationship, and I'm just encroaching on it, you know? Like I don't belong. You have such a great marriage, and maybe I'm just… getting in the way…"
"What? Henry, no!" Regina cried, wrapping her arms around him from behind. "You have always been and will always be a part of this family. We would both be broken without you."
"Yes, but… I'm your son first, and I know that. Maybe I'm just not supposed to play whatever other role it is I'm playing. I feel like I should just… let you have your marriage. Like maybe this was a mistake. Like I should have just listened when you both told me no the second time."
"Do you regret what's happened between us?" Emma asked carefully, moving beside him and looking into his eyes.
"No! Of course I don't. I just want you two to keep having the wonderful marriage you've had all these years. I don't want to get in the way."
Regina quickly asserted, "You're not in the way. You're a part of us."
With a sigh, Henry lowered his head into his hands as he rested his elbows on the table.
"We love you," Emma told him. "So much."
"Are you sure this is okay?" Henry asked, his eyes watering.
"Yes, we're sure," Regina assured him. "We want you too."
Henry's doubts were mostly eased by his mothers by the time he went back to school for the rest of the semester, but his loneliness grew as soon as he found his seat on the train back to the campus.
Just a few nights in, when his roommate was out, he video called his mothers from his laptop.
"Hey m-" he started, but his voice quickly dropped off when he saw that both of them were sitting on their bed in their bathrobes.
"Hi, darling," Regina said brightly as she smiled slyly. "You've got great timing. We both just got out of the shower."
Henry thought he might be drooling as Emma smiled too and slowly loosened the tie of the bathrobe and pulled it open enough for him to see a small strip of skin that reached all the way down to her panties.
"We miss you," Emma told him, leaning back slightly and allowing the garment of clothing to fall open even more.
Regina nodded in agreement and followed suit, leaning back, but pulling her own bathrobe open completely, exposing her breasts.
Casually, she asked, "So, what have you been up to, handsome man? You look awfully tired."
"Just haven't… uh… been sleeping much…" Henry replied honestly, eyes wide as he watched Emma open her bathrobe as well.
"Why not, dear?" Regina questioned with a smirk.
Masturbating all night, he wanted to tell them, but he couldn't bring himself to say the words.
"I, um… I don't know. Just stressed, I guess."
"We wish you were here," Emma said softly, sliding her hand down Regina's front, over her breasts, and into her wife's panties.
As soon as the tips of Emma's fingers brushed her clit, Regina sighed and leaned her head back, shutting her eyes.
"Me too," Henry told them, nearly drooling at the sight of Emma pleasing his other mother.
When Emma pressed her fingers harder against Regina's clit, the woman moaned softly, which made Henry's cock twitch.
"Mom…"
"What's the matter, Hen?" Emma asked him playfully. "You gettin' hard already?"
Even though they'd seen him hard over and over again, Henry still blushed at this, made uncomfortable by the playful teasing. He didn't know what to say, so he shifted uncomfortably on the bed and bit his lip.
"It's okay, baby," Regina said softly. "Tell us what you're thinking."
"I want you," he finally blurted.
"Yeah? How?" Emma asked with a grin.
"Doesn't matter. I just… need you both…"
"You wanna be inside us, Hen?"
Involuntarily, Henry whimpered. The noise was soft, but both women heard it clearly through the speakers of their own laptop.
"You hard for us, baby boy?" Regina cut in, when her son did not reply. His blush grew brighter, so she added, "Why don't you show us?"
Slowly, Henry slid his pajama pants down to his ankles, revealing a large bulge in his boxers.
"That's it, Hen," Emma encouraged him. "Show mommies how big you are, bub."
He was shy but obedient as he pulled his boxers down, allowing his length to spring free.
"Oh, sweetheart," Regina breathed, staring at the screen. "You're so perfect. So beautiful."
"So sexy," Emma added. "So big."
Blushing, Henry shifted uncomfortably once again, not knowing what to do next.
"It's okay, bubby," Regina cooed. Just watch and do whatever you want to."
The young man nodded, leaning back slightly against the pillows as he watched Emma fasted a strap-on around her hips.
"Oh, fuck," Henry groaned, as the blonde positioned herself between her wife's legs.
As soon as Emma pushed the toy into her lover's core, Henry gripped his length forcefully and stroked hard, his head falling back against the pillows. Just then, hearing his grunt of pleasure, Emma turned to look at the camera to find her son stroking his shaft and squeezing it hard in his fist. Because his laptop was between his legs, his penis was easy to see, large on her screen, and she could see the precum forming on the tip.
"Regina," Emma whispered, nodding towards the screen of their own laptop.
The brunette's mouth watered when she saw what her wife was gesturing at.
"Oh, Henry," she moaned. "Such a good boy."
"Tell us what you want to do to us, Hen," Emma commanded, licking her lips.
"Want… Want to fuck you," he grunted between strokes.
"What else?" Regina asked.
Emma pushed back into her, moving the toy inside her wife's core, making her moan.
"Wanna be inside you, mom," he finally managed, staring at them as they fucked.
"I want… you to cum… inside me, Hen," Emma told him, slightly breathless from the effort of her heavy thrusts.
"Please," Regina whimpered. "Just want to taste your cum."
"Unnng," Henry moaned, jerking harder. "Want you so bad."
"I want you to bend me over the table," Emma told him. "Want to feel your balls slapping against my ass as you fuck me."
Again, Henry groaned in response.
"Wanna feel…" Regina gasped, "…your dick… pushing against the back of my throat."
"Oh, God."
"Emma, yes," the brunette whimpered, feeling her lover speed up her movements.
Then, Emma lifted her leg slightly, shifting the angle of her thrusts and hitting just the right spot inside Regina's center, giving Henry a better view of the penetration at the same time.
"Mom," he gasped. "Fuck."
Regina echoed, "Fuck!" with the next thrust, and that was enough for Henry to spill himself all over his hand and abdomen.
Luckily for both women, when they heard him grunt loudly, they looked just in time to see his cum spurting out and covering him.
Regina came shortly after, and once all three had come down from their high, they decided to fall asleep on the call together.