As the window rolled down, wind tousled Gabriel's hair. Buildings rolled by towering above only half minded. Cars lined the street, trunks open and full of boxes waiting to be moved. People weaved in and out, some almost stepping into the road before realizing where they were. Linda cursed to herself and honked as one such pedestrian wandered too far. Her aggressive driving was not a good suit for the environment. The moment a spot opened, she took it, practically bulldozing her way between white lines.
"We're here!" She smiled at Gabriel as she unbuckled. "My little Gabby is going to college! I'm so excited."
"Mom, my name is Gabriel. We've talked about this." She did not listen, already moving toward the rear. He sighed and followed.
The trunk was stuffed with his things. Most of which he did not really care for but Linda had made him pack. She had picked his college for him too. Once her mind was made up, there was little he could do to change it. He was only her little Gabby after all.
Before either could grab a box, Gabriel noticed roving eyes. It really should not have been a surprise. The tank top let her chest do a little more than peek out and the lack of a bra did not help her modesty. Jeans were much the same, low waisted, and showed every curve of her leg. As she bent to grab a box, the back of a lacy thong rode up. All in all, it was a pretty standard outfit for Linda. Gabriel grabbed a box for himself and set off after his mother. Along with more than a few lingering gazes.
Inside the dorm was a different story with every person too engrossed in their own affairs to notice them for more than a moment. Not long and he would be free of his mother's watchful eye. He could finally put everything out of mind. After they moved everything in, he was sure Linda would leave. He just had to get through the next few hours and then he could control his own decisions.
At the front desk, Linda gave Gabriel's name and was given directions. Room five zero six, up the elevator to the top floor and then a turn. The room itself was tucked into a corner of the building. Where most rooms would have had a single window, he had two, one on each wall. There were no duplicates of the furniture either. A single desk, bed, and wardrobe marked clearly meant for one person.
"Talk about a palace," Linda lauded. "I used to have so much fun in places like this."
Gabriel did not ask how she used to have fun in a college dorm. He did not think he wanted to know.
The pair quickly settled into a rhythm. Gabriel would run to grab more boxes while Linda stayed in the room to unpack. The boxes themselves were not terribly heavy, only bulky, allowing just one each trip. Though their split duties managed to speed the whole process up quite a bit. After the boxes, Gabriel helped unpack, placing each item in its respective place. The clothes in the wardrobe, the books in their shelf. Even the bed sheets managed to get onto the mattress.
As they finished, there was a knock on the door. Linda smiled, "That must be Alison. Don't keep her waiting."
"Whose Alison?" Gabriel asked himself, opening the door.
Long, silky brown hair was the first thing that greeted him. Green eyes not too far behind along with a strong jaw and full lips. The rest of her body was not bad either. A button down that refused to show cleavage but could not hide her size. It was tucked into a simple pencil skirt that hugged her hips but split near her knee. Black stockings obscured the rest of her legs down to the modest heels she wore.
"Alison! Hi!" Linda squealed, pushing past Gabriel, and throwing herself into the woman's waiting arms. "Long time no see!"
"Not since graduation, Linda." Her voice was light and feminine. It reminded Gabriel of his mother, only with less wear. "You look like you haven't aged a day. Oh, this must be Gabriel. Linda has told me so much about you." Gabriel stuck out a hand to shake. She took it, yanking him into the now threeway hug. "You look just like your mother."
Gabriel blushed. "Um, thank you." He had never really thought about it, but it was true that he looked like Linda. Skinny, and with a long, face.
"Do you like the room? I picked it out for you myself," Alison asked.
"It's um. Yes, very nice. It's kind of funny actually. It's like I have a room for two people all to myself."
"Oh, that's because you do. One of my friends is in charge of assigning freshmen to their dorms. All it really took was to make sure you were the odd man out and voila. You have the best room I could get all to yourself." Alison smiled. She turned to Linda. "Did you not tell him that?"
"No, I wanted it to be a surprise. My little Gabby gets to have the room all to himself. He'll need it if he's going to be a lady killer." Linda laughed at her own joke.
Gabriel felt his face heat up again. "Mom, my name is not Gabby, and I'm not going to be some fuckboy."
"Oh, don't be silly, Gabriel." Alison giggled at him. "If you're not careful, you'll be a ladies man before you know what's happening. And then you'll need this big ol' room to yourself for all the girls." Gabriel wanted to protest more, but he knew it was futile. "Anyway, I brought a house warming present. It's in my car. Do you mind running down to get it with me? It's rather heavy."
"Sure, sure," he said, leaving the room.
Linda stayed behind, continuing to pull clothes from boxes. It felt nice to get away from the double takes and leering eyes. Alison was easily a match for his mother but she carried too much authority in her step. Salacious glances were punished with a scowl that could kill.
She led the freshman through the parking lot to a simple black sedan. It honked as they approached, trunk opening to greet them with a mini fridge still in the box. They each took one side, weaving back through the crowd and up the elevator. Nearly dropping his end, Gabriel's arms burned with effort. Alison appeared unfazed.
Linda fussed as soon as she saw the fridge, "Oh you didn't have to get something so expensive."
"It's nothing. The least I could do, really. I'm just glad I finally got to meet Gabriel. Trust me, if your college experience is anything like mine, you're gonna love it."
"Ain't that the truth." Linda was hugging the taller woman again, squeezing under her arm.
"Were you and Mom roommates in college?" Gabriel asked.
"Oh, yeah. All four years. You should have seen some of the shenanigans we got up to. Some of my favorite memories." Gabriel's stomach churned a little at that. He could imagine a little too well the things the two women did in their room together.
"Oh oh oh, I have an idea!" Linda cheered. "Let's all get lunch together. There's gotta be someplace decent around here."
"No, no, I can't. I have some other things that need doing today."
"Well, at least let me walk you to your car then."
The pair walked off side by side, Linda guiding a hand to and inside the waist of her pants. There were a few words about going to a bar later and a promise to visit before the door shut. Then they were gone.
Gabriel flopped on the bed with a thump. Finally alone. Just himself. No Linda. He was finally free to make his own decisions. Maybe college would be as Alison said.
The first week flew by in the blink of an eye. Papers and forms filled out, classes settled, and new faces met. Being responsible for his own schedule was a little daunting at first. The rhythm came easily after only being late to class twice. There was no homework assigned yet. At least none that required more than a few minutes of effort. Friday rolled around with an abundance of free time.
His phone binged with a notification. Linda had made a new post, another selfie. Her tits were in frame, if not most of it. She was near a pool somewhere with tin lines becoming a stark reminder of her skimpy taste in bikinis. The caption read some nonsense about good weather and swimming.
Scrolling through her profile, it proved to be very inline with Linda's personality. There were mostly pictures but a few short videos snuck in too. No matter the format, her chest or ass was always front and center. Gabriel found himself getting a little bit hard, eyes tracing the curves of her tits or ass. She really did have a nice figure. Not as nice as Alison's, but still great for a forty-something woman. He thought of Alison too, his cock swelling at the memory. That first hug between them made her feel soft against his chest. His dick was getting harder now, just thinking about it. He imagined what it would be like to rub it against her ass or her tits. To have his cock buried between them. Just as his pants came unbuttoned, a sharp knock dashed away the fantasy. Sighing, he made himself as presentable as a college freshman could be and answered the door.
Alison stood on the other side exactly as he remembered save two changes. The pencil skirt was swapped for tight trousers and a few more buttons were undone at the top of her blouse. Cleavage popped through, pulling a quick look before he could catch himself.
"Uh… hi," was all Gabriel could manage. "Have I done something wrong?"
Alison laughed. "No! No. Nothing like that. I promised your mom I would come check on you from time to time. So, tada! Here I am. Can I come in?"
Gabriel realized she was still standing in the hall. "Yeah, sure. Come on in," he said, moving to the side.
She swished in, closing the door behind her. "It is nice to meet you without Linda here." Her eyes drank in the space around her, still undecorated in the way most boys left their rooms. "Kind of sterile don't you think? A little unwelcoming?"
"Honestly, I don't know how to decorate a room. I've never really needed to before."
"Linda decorated your room at home for you?"
"Yeah, you know what she's like."
Alison seemed to understand, smiling and rolling her eyes as she took a seat at his desk. "Well, I'll tell you a secret. Boys that decorate their own rooms always do better with the ladies." Gabriel blushed at that. "That reminds me, how are your classes going?"
"Fine, I guess. They've really only covered the syllabus. Only one of them is really related to my major though. Mom said they just like to stuff your schedule with gen eds freshman year." He moved to his bed, using the edge for a chair. "If you don't mind me asking, what exactly is your job?"
"Oh, admissions. I'm the Director of Admissions actually. I got the final say in accepting you here. And I'll tell you it was an easy choice." She grinned at him, giving a wink.
"Thanks, I guess."
"I mean it. I read a lot of applications. Yours stood out for more reasons than one. I can see Linda in you, you know. You have her spirit and energy."
"I've heard that before." Gabriel blushed again. "Are you two friends? Mom never really talked about you too much."
"Friends? Oh, we were a lot more than that. We had four years of wild adventures together. I can show you some things from my experience with her." A twinkle appeared in Alison's eye as she talked.
"No, I'm good."
"Oh come on, I've seen Linda's photos. And I know you have too." She held up his phone, still unlocked and showing his mother's newest bikini selfie. Face red, temperature rose. "Don't give me that look. I know you're curious. That curiosity might just help you get the girl." Alison winked again. "Come on, Gabriel, I'll show you. Your life will be so much better for it."
"Okay, what does that even mean? Are you gonna make me a 'lady killer' like Mom wanted?"
Alison laughed. "Look, it's simple. A cutie like you just needs an excuse to be alone with a girl." She stood, slowly crossing the room. "Then, you just make some small talk. Nothing too interesting though." In front of him now, a hand on his waist and leaning in close. Voice becoming a whisper. "Finally, a kiss." Soft lips pressed into his, opening his mouth as hers did.
Gabriel froze, unsure how to respond. Then she was sitting on his lap, legs over his thighs. Tongue explored his mouth as arms wrapped around his back and pulled him into the embrace. It was hard to ignore the press of her tits against his chest. She was gentle with him. Fingers twirling and stroking his hair. Suddenly, the kiss broke. Gabriel opened his eyes, only then realizing that they ever closed. Emeralds sparkled and radiated warm affection rather than pure lust. They pulled him in, comforting as his lips moved back to hers.
She leaned forward, forcing him back until he flopped flat on the bed. The makeout session did not stop. One hand held her weight atop him while the other roamed his body. First, down the side to sensitive hips, under his shirt and back up a flat stomach. He groaned as she explored, wanting her to go lower instead of higher. His own hands gravitated to her waist, pulling the still tucked in shirt free. Copying her, he moved up her back, aiming to find a bra strap that was not there.
By the time he realized why there was no bra strap, Alison was sitting up. He tried to come up with her but a hand on his chest kept him in place. She gave him a little smile before turning her attention to her blouse. A few buttons were undone already and the rest quickly followed. Tugging at the sleeves, tossing the cloth to the side, the first bare chest Gabriel had ever seen was in front of him. He wanted to reach up and touch them but she spoke before he could move.
"Your turn, Gabriel," Alison cooed. "Take off your shirt for me." He sprung up, fighting with the hem then his shirt was gone too. They meandered about each other, silently comparing his flatness to her voluptuousness. He explored the soft skin and curves, just as she ran over the few bumps that passed for muscles on his body.
She could feel him hardening underneath her. Hips slid up and down over his, humping through his thin sweatpants and underwear. It was impossible to hide his boner even if he wanted to, drawing his attention away from the odd wrinkles in Alison's waistband. A simple touch of her chest was enough to keep it out of mind.
Thumbs hooked his waistband, pulling as Alison slid off of him. Kicking his legs free, she had him completely naked. Gabriel was rock hard, the horniest he had ever been in his life. Laying her hand on top, his cock came just past her palm still hidden by fingers. For a second, he thought she might mock him for his smaller size. Yet she curled around his dick, massaging gently and leaning back in for a kiss.
They sucked at each other, her thumb working in circles around his head. He groaned into her mouth. The hand stroking her back stopped then began to move down. Brushing over a button, a moan came from between their lips. Not wanting to stop the kiss, he fumbled at the button, barely managing to pop it open. It was a simple matter to push down.
Her tits were amazing, but what came from between her legs was nothing like any of Linda's photos. It flopped out with a meaty slap against his stomach. Gabriel froze, gathering his confidence to turn his head down and look. Precum already soaked the tip, smearing as it dragged. All in all, her cock was twice as long as his with balls to match already swollen with cum. Alison chuckled, realizing what distracted him.
She stood and took a step back, letting the cock wave from side to side in front of him. "What do you think, cutie? Ever seen a cock like this?" The freshman shook his head, eyes still locked on the twitching shaft. "This is what made Linda cum more than anyone ever had. You can touch it if you want."
Gabriel looked back up, meeting her eyes and finding only encouragement there. With a little courage, his hands came to rest on her thighs before sliding to her shaft. The feeling of warm flesh filled his palms. It was strange holding someone else's cock. Yet as soon as he touched her, Alison groaned with pleasure. More than just holding it, he wrapped fingers around the girth and stroked. Suddenly, it jumped. A single hard pulse shot a stream of precum onto his stomach. There was more precum than he had cum.
"Let's not make a mess," she chuckled. A condom came from her pocket as she finally kicked her pants away. "You know how to use one, right?"
Gabriel nodded, taking the plastic square. He had never actually used one on himself, let alone another person. A health class demonstration was really the only experience he had. With shaking hands, he peeled it open and rolled down her shaft until there was nothing left to unfurl. It went right to the base, leaving cum heavy balls exposed. It leaped as he finished. A thick spurt of precum trapped inside the latex confines.
Alison did not wait for an invitation to roll him onto his stomach. She grabbed his hips, yanking him back until only his chest was left on the bed. With a deft step, her legs were between his and her cock laid neatly between his cheeks. His eyes went wide as she lined herself up with the pucker. He felt her press forward and then slip off, never pushing inside, only teasing.
"Say it, Gabby." The use of that name made him cringe. A part of him wanted to stop right then and there. But her cock was still between his ass cheeks. Alison leaned forward, letting her tits press against his back as she whispered, "Ask me to fuck you." All at once, he wanted her again. Her voice was honey sweetening everything she did.
It was only natural that he groaned, "Fuck me."
She did not waste a moment, shoving inside in one easy thrust. Stretching open, he could feel the head spread him before plunging deeper. Gabriel was amazed at how easily she slid in. For a moment it was uncomfortable. Her cock stretched him wider than ever before. Yet the longer she stayed inside him, the more he wanted.
"You're so tight," she said, kissing along his neck and shoulders. Her hips drew back and then forward, repeating in a slow and steady rhythm. "I can't believe you've never been fucked before."
A mellow, pleasureable drone came over his body. It faded for a brief second when Alison paused to reverse direction but returned in force as she drove herself in and out of him. He moaned with every plunge of her cock, feeling it press into his body, and whimpered with each withdrawal, leaving an odd sense of emptiness. When the cock was completely inside, the balls came to rest over top his own, eclipsing them with more than physicality.
Alison straightened, leaving a coldness on Gabriel's back. She traced her way down his sides until she cupped his ass, squeezing as she fucked him harder. He gasped, cock twitching as Alison massaged his hidden cum button. Pinned between his stomach and the bed, neither of them could see his precum turn from a few drops to a steady stream. He sucked in a deep breath and suddenly forgot to exhale. His own dick pulsed, doing its best to spurt as much cum as it could. He tried to exhale, only managing a shaky moan instead.
"Oh, Gabby," Alison purred.
She stopped moving, cock still buried inside his ass as he shivered and spasmed underneath her. Fingers curled, dragging the sheets out of place. Breaths came short and stuttering as a new stain formed under him. Alison let out a laugh that sounded more like a giggle, slapping his ass and making him jump. It was the final assault he needed to finish cumming. A final exhale turned into a moan as the futa resumed thrusting and he trembled around her cock, squirming with every thrust.
Her own cock twitched, still contained in latex. At a certain point, she began to shiver too. Cock pressed against his cum button, driving him into a new level of bliss. He gasped and groaned every time it tried to push deeper, even though there was nowhere left to go. Another few thrusts and a wave of pleasure washed over her. Suddenly her hips were a blur, pounding into him without the gentle consideration of only a moment ago. There was a pause, cock stretching and filling him to the brim. She growled and held him in place as she came.
Cum erupted inside. Balls tightened as she pulsed, emptying herself in a torrent. Rubber stretched with each hard throb. More and more hot cum poured into Gabriel heating him from the inside out. All he could do was wriggle and writhe as she emptied herself into him. She collapsed on top, tits squished against him as she panted over him. Somehow it was relaxing to feel someone completely expend themself in him. Even if he could not say it, he enjoyed it.
Alison stayed inside him, balls still pressed over his, humping ever so slightly to milk out the last of her orgasm. After a long while, she stood. Gabriel groaned as she withdrew. Especially so when the bloated condom was dragged out. It swung down, hanging in a wide bulb of sloshing batter. Gingerly, Alison pulled until it popped free with a loud snap and with a practiced ease, tied the end into a tight knot.
She tossed it in his trash can on the way to his desk, where she sat back down with a satisfied smile. Legs spread, the semi hard cock bounced in the air. An unavoidable white sheen covered the whole length.
"See, Gabby. I told you I could teach you a few things." Gabriel glared up at her, still stuck on that nickname. Alison saw and just laughed. "Oh, don't look at me like that. You loved every second of it." He could only blush and lower his eyes. "Well, we'll try again soon. I've got a few more things I can teach you."
Gabriel started to object but she was already standing and dressing. By the time he made it back to his still wobbly feet, she was at the door.
"I'll come back next week. See you soon, cutie." She winked and was suddenly gone.
It took a moment for him to recover from the shock. Alison had whisked her way into his room, fucked him sensless, and was already gone It felt like a dream. Though the proof was still on the bed. Sighing, he decided the laundry could wait. He needed a shower more than anything.
From the outside, Gabriel looked like a normal college boy, if a little introverted. He attended lectures, did his homework, and even posted in the silly online "discussions" that his professors graded. On the inside though, he felt like an entirely different person. Alison had made good on her word. Every week, she would drop in on him. Sometimes she even brought food. A welcome change from the mediocre dining hall.
She taught him things that he would never learn in a classroom. It was simple anal for the most part. A straightforward railing until they both came and usually followed with a healthy dose of cuddling and small talk. It quickly became the highlight of his week with almost nothing that could top it. If nothing else, it was better than the solo jerk sessions he was accustomed to earlier.
When Friday rolled around again, he was already naked, waiting for Alison's knock. The sheets were freshly laundered and the room was as tidy as it could be, with only his books in a pile. The knock came right on time. He called out for her to enter. Only a moment later she was walking in the room, the outline of her cock already straining her pants. A slight smile creased the corners of her mouth. With a shimmy of her hips and flash of her hands, the clothes fell to the floor, purse alongside them.
Her arms around him, pulling him into a hug and a kiss. He reached down to stroke her cock, moving from base to tip like she taught him. Her breathing deepened, hips swaying to rub her cock against him. The tip was already slick with precum.
Alison was the first to move them apart, a hand caressing his cheeks as she pulled away from his lips. "How about we try something a little different?" She grinned mischievously. "I brought you a present I want you to try." She reached down to the purse to grab a small box with a box on top.
Gabriel had it open in less than a second. Inside was a velvet cushion with a metal object. One short and shiny with a jagged end.
"What is it?" he asked.
"It's a prostate massager." Alison said, pointing to the silicon curve. "A friend of mine got one. Now he can get off in a heartbeat and he swears he'll never touch his cock again."
Gabriel looked down at it with a mix of confusion and apprehension. "Is this... safe? I've never worn one before."
"Oh, don't worry. I have some experience with this kind of thing. They're perfect. Just be sure to clean up every once in a while." Her hands moved to his already hardening cock. "Let's get you locked up before we mess around. It'll help you learn."
She stopped his experimentation with a simple command. "Turn around and bend over the bed."
Gabriel did as he was told, presenting his ass. The tip of the massager pressed against his hole, stretching it but not entering. It danced around the rim, teasing and threatening to pop inside but never going in all the way. Tiny bit by tiny bit, it inched inside only to retract in favor of taunting. No matter how hard his rear clenched, Alison made sure to press it in that small increment further. Just as he came to the widest part, she pressed steadily. Unconsciously, Gabriel did all the work. He squeezed, enjoying the new sensation and pulling it deeper until there was no more to pull.
At first, he did not know what to expect. The pressure on his prostate was there but that was all. Pushing out, the massager moved, relieving the pressure as it went. As soon as it stopped pushing, it was dragged back in, starting the process over. Slowly, Gabriel relaxed into it. The bed was a comfortable place to relax and he felt at ease with her there too. The stimulation began to seep through his body in a wave, starting in his ass but radiating outward. Before long he was sighing, his own cock twitching with the need that could not be satisfied.
"Are you enjoying that?"
He moaned. The words would not come and all he could do was nod. The massager pressed in deeper, stimulating his cum button with more vigor than before. The next wave of sensation went through him, making him shudder and gasp. He wanted to speak. Wanted to tell her that she was doing something incredible but he could only babble. That was enough though. She understood.
His head was still down on the bed as she jumped beside him, cock inches from his face. Pre-cum dripped onto his lips, licked up with a moan. It only encouraged her. Her hand brushed through his hair, guiding him into her crotch. Automatically, Gabriel began to roll and lick at the tip. Precum poured out of her.
Gabriel did all he could to keep up with the flow. He gulped it down and was refilled just as fast. It dribbled over his lips to streak down his chin. Each drop hit the bed below with a soft thump. The massager still pressed against his prostate, jostling as he rocked and bounced his head. Every jolt made him groan around the meaty slab. His own precum escaped his cock in a small rivulet. Nothing compared to Alison's deluge. Still, he could feel his dick throbbing.
There was a gentle squelching sound that filled the room to mix with the futa's moans. He bobbed up and down, taking her cock as deep as it could go before raising until it was only touching his lips. From his close position, he could not tell just how much of her cock was actually getting inside him. All he knew for sure was that there was more outside his mouth than in.
"Good boy, cutie! Good boy!" Her fingers ran through his hair in gentle strokes. They curled and tightened, fixing him in place. She gasped as her hips pushed up against the barrier at the back of his throat, forcing him to open wider before slipping free. A cough forced his lips apart, spraying half swallowed precum and spit on the bed and Alison's crotch. The force behind his head increased. It drove him forward even when his throat resisted. Inch by inch, cock sank into him despite the sputtered attempts at protest.
He could not help but to gag. His body tried to expel the cock, but the firm hand held tight. Desperate to breath, Gabriel forced himself to swallow, feeling the meat push down his esophagus. It took several moments of fighting before he was able to relax. When finally he did, it was not from choice but exhaustion.
Slowly, the pressure lightened. She let him draw back at an agonizingly slow pace, finally allowing him to fall away, panting and gasping. His vision swam. The room was a whirlwind of colors and dizziness. Gabriel tried to focus but, distracted by the massager keeping him on the edge and the new found soreness in his throat, there was no such luck. Her cock bobbed inches from his face still dripping precum. A sudden twinge shot a thick rope of clear fluid that slapped his cheek with a wet squelch.
"You're so cute with your tight throat stretching all around me. My little cutie, turning into such a slut."
Gabriel blushed hard. He wanted to complain that he was not her slut but somehow the words died on his tongue. Her thumb rubbed across his cheek, wiping away precum before pressing to his lips. They parted without prompting. Before he could stop himself, he was already licking the digit clean. The massager eased its way back and forth as he sucked. Her salty flavor coating his tongue while his own stained the sheets below.
"You can't deny it." Alison laughed with a pleased grin. "You love being a whore for me." Gabriel blushed harder but knew she was right. The little part inside of him that wanted to object stayed silent. Her smile grew more genuine. She stood, waltzing over to his desk to turn the seat around. Legs spread as she sat. They left her still hard cock jutting into the air, dripping in his slobber. A finger curled to beckon. "Come here, cutie. Crawl. Kneel in front of me."
The command was more than enough to get him moving. He dragged himself off the bed, immediately sinking to all fours. The massager shifted inside him, teasing with every motion. Unyielding, he crawled. It was a short distance to cross but the display was clear. He obeyed her. When he reached her knees, his head lifted to look up at her. Her cock was wide enough to obscure her face, forcing his focus back as it twitched above him. Never had he felt more subservient.
A leg rose up and over his shoulder. It hauled him into her, pressing his face against her sodden shaft and balls. "Good boy." The praise made him feel good as he rocked into her groin. Her cock swayed above him, dripping precum into his hair. It made him want her even more, but he could not figure out how to ask. He would not need to. "Put your hands behind your back. Clean my cock until I tell you to stop."
His hands were gone before he could even think about it. The task was easy enough. His lips sealed around the top and he began to lick down her shaft. Every bit cleaned away to leave it shiny. He wanted more, licking and nuzzling to find it. To his delight, she started to moan as her cock twitched. It seemed to please her when his tongue swirled at the base, extra sensitive and tender.
As he reached the tip again, there was a sudden taste. Precum, hot and fresh. He was quick to lap up the liquid and search for more. Mouth opened wide around the tip and sucked gently. It earned a pleased sigh and he continued. Soon enough, there was more. It drizzled into his mouth in quick streams. Each time he got one, there was more coming. The flavor was comforting. It felt right and tasted right too.
The sound of Alison's phone buzzing filled the room. She sighed as she reached for it, tapping the screen. "Hi, Linda."
Gabriel froze when he heard that name. A quick glare from Alison told him to keep going. He could not hear the other end beyond a few muffled noises that were once words. He kept licking, groaning at the salty taste that kept flooding his mouth, pulling his attention away from the conversation.
Alison laughed into the phone. "Oh, he's in good hands." Another pause. "Yeah, he is definitely learning." She leaned forward and looked down at Gabriel. Her eyes locked onto his with a grin. "What are you talking about? I'm with him right now." Gabriel shuddered but kept sucking. He could not help it. "Why would you ask that? Of course, I'm showing him everything I said I would." Her grin turned into a laugh. "Well, that's your fault for missing him so much."
Gabriel did not understand what his mom wanted with them, but Alison seemed to be pleased. So, he kept sucking, the hot liquid coating his tongue and the roof of his mouth. His throat opened up, eager to swallow it down.
"Oh, you want to talk to him?" Alison shook her head with a chuckle. "Of course, he's right here." She put the phone on speaker.
Just as Linda said, "Hi, Gabby!", the leg around his shoulder yanked hard. He rocked forward, sputtering and gagging as his throat was stretched to the max. A mix of precum and spit flowed out passed his lips, undoing all the cleaning work he had just finished. There was a moment of silence from Linda. "Alison, you bitch! Are you making him suck you off?" she yelled.
"Well you did tell me to show him the ropes," the futa retorted, dragging Gabriel back and forth.
Gabriel blushed as his mom started to curse in the background. "That's not what I fucking meant and you know it!"
"Ooh, don't you want your boy to get a little slut training?" Alison giggled. "Don't worry, I won't tell anyone you're encouraging me to whore him out." Her hips started to rock into him. "Besides, he loves this."
The other end got even louder. "Alison, you said you would go easy on him! That's my son you're talking about!"
"Yeah, yeah, I will." Alison kept taunting her with giggles. "I'll send you some pictures when we're done. Bye, bye!" Linda shouted something before the line went dead. It started to ring before she turned it off, tossing it onto the bed with a sigh. "So, shall we finish?" Gabriel was sure it was more a statement than a question.
His head bobbed, eager for her cock again. It was easy to forget how big she was. She pushed into him with a slow ease that he had no choice but to accept. Cock sank into his throat as she kept thrusting until there was nothing left but balls slapping against his chin. She pressed harder, forcing just a little more and his nose wrinkled against her crotch. The leg crossed behind his head. Thighs pushed against the sides of his face, locking him firmly into her crotch.
The massager pressed back into him. It pushed in just deep enough to make him feel something different. Suddenly, his rear clenched and the massager slid against his prostate. His cock twitched and shook as the trail of precum thickened and turned white. Cum spilled from his cock. Tremors spread through him, shaking every muscle. Alison pulled back just a bit, the cock easing out of his throat only to pop back in a moment later. Ass flexing on reflex, the aneros drove itself into him in perfect timing. Each small thrust into his mouth resulted in another twitch that kept his orgasm continuous.
"Oh, did you just cum?" Her voice was mocking, knowing the answer. "You just can't help it can you?" Another thrust and he gagged around her. "Was it from sucking cock or was it from being fucked with that massager up your ass?" Her laughter filled the room as he bucked and moaned. His whole body shook from the pleasure.
Alison began to fuck him earnestly. Her moans filled the room with each thrust as she picked up pace. Her voice rose to a growl as she slammed into him as deep as possible over and over. He gagged and sputtered but kept taking it, squealing as his orgasm refused to stop. She slammed into him with reckless abandon. He was helpless as he felt her cock swell. Balls pressed to his chin. Alison groaned at her peak before spraying the inside of his throat with a torrent of seed. Hot cum shot down his throat, heating him from the inside out.
Gabriel was overwhelmed. Cum pumped into him over and over, filling his throat to its limit with each powerful throb. The leg around his head relaxed. He pushed back, letting her cock slip from back into his mouth, only to realize the limb was still behind him, stopping him from going any further. A single pulse flooded his mouth with cum. There was barely a second to savor the delicious taste before another jet bulged his cheeks. He swallowed, trying to keep it all inside him in vain. Each staccato gush filled him just before he could take the one before it. Cum dripped from the corner of his lips to roll down his chin.
When her cock finally softened, it slipped from his lips with a sloppy pop. She let the leg drop, allowing him to finally sit back and look at her, the chastity cage still twitching. "See, you're a natural!" Alison smiled as she leaned down, kissing him on the lips. Her tongue dashed into his mouth for a moment, tasting herself inside him before they broke apart again. "You even learned how to deepthroat. My little cutie," she cooed, kissing again.
He broke the kiss this time. "What was that with my mother?"
"Hm?" She feigned innocence.
"You said 'you told me to show him the ropes' to my mom. What did that mean? Why did you put her on speaker? You wanted her to know that I was giving you a blowjob!"
A grin split her face. "You really don't remember, do you? Well, let me remind you." Gabriel frowned but she just laughed and continued. "It was during move-in day." He thought back, frowning more. "Do you remember when we went to get that fridge from my car? Then me and Linda left pretty soon after that. Well, we went back to my place and had a long chat about your future here. She said that she owed me for getting you admitted and for making sure you got this room all to yourself. The first thing she offered was you."
The words hung in the air. Gabriel felt his cheeks heating with a blush. "Mom...?" The words were almost a whisper. "I don't..." His thoughts were muddled, head spinning with confusion. "Why would she...?"
"Because your mom loves getting fucked more than anything in this world!" Alison's smile was wicked and pleased at the same time. "And she wants you to be just like her and she wants me to show you how. I'm willing to do it, too. In fact, I did you a favor by making sure you got the room by yourself. It's because I want you to be my personal little slut while you're in college." Gabriel gasped, mouth working but not responding. "There's nothing to be ashamed of. You're already loving it. And you are my little slut, aren't you?" There was no response, so Alison just leaned over to kiss him again. "Good boy. My slutty, little cutie." A hand reached out to brush his hair back. "Now, clean yourself up and I'll leave you to get some rest. You look worn out."
With a final peck on the lips, she left the room. He did not realize just how tired he was until the door closed and he melted into the floor. It was a challenge to stand even for a quick shower to wash the remaining sludge off his face and clean the prostate massager.
Checking his phone, there were half a dozen missed calls. All from Linda. All ignored as he crawled into bed. Sleep came easily with a last thought for the fact that his mother had sold him out for sex. Not only that, but she was actively helping Alison turn him into a whore.
The next week passed in a blur. It was hard to focus on class knowing what he knew. Linda called him again and again. At least twice each day. Every time he simply let it ring and go to voicemail, recording apologies and excuses. He ignored them all. Oddly, there was no such apologia from Alison.
On Friday evening, Alison came exactly as she always did. He knew better than to trust the professional attire she always wore. If the door opened, she would be on and in him until she decided it was enough. With a heavy sigh, he stripped off his clothes in a hurry and pressed down on the handle.
It was the same grin that had greeted him on their first night. "Hello, my cutie." She leaned in for a kiss that was not returned. Instead, he let himself be pushed back into the room until she broke the kiss again. "What's wrong? Is this because of what I told you last week? Has your mother been calling?"
Gabriel shrugged, looking to the floor. "She's called every day."
"And what did she say?"
Gabriel sighed again, relating the short messages that Linda left. She just apologized for something she did not think was wrong. Promising to make it up to him. That she was sorry for not being more honest with him.
Alison growled at the last message. "Sounds like someone is sorry to get caught selling out her son." Her voice softened. "Don't let her get in your head. You are better than her, Gabriel. That's why I picked you." Gabriel tried not to smile at the compliment. "It's time for you to make a decision."
His eyes snapped up. "What kind of decision?"
"Well, I was going to wait until the end of the semester to give you more time but in light of your mom lying to you, I think it's better to ask now. So… Do you want to stay or do you want to stop?"
He blinked, not knowing what to say. Alison was quick to clarify. "Either you choose to be mine and we keep going like this, or you stop now and go on about your life as a regular college student. It'll be like none of this ever happened." He looked at the key hanging around her neck. It seemed like the whole room was holding its breath as he decided.
The words came out before he knew they were there. "I... I want you to stay."
Alison was not smiling. Instead, she looked to be studying him. "Are you sure? I'm not going to force this on you. If I was, then you would already know. But you need to make this choice by yourself, so I am going to make sure you understand what you are getting into." She reached out and ran a hand through his hair. "If you choose now, there is no turning back. You will be mine to do with as I please. Do you understand?"
Gabriel felt a little fear creep into his heart. He had not thought about it quite like that before. Now, he was realizing just how much control she wanted to have over him. How much control he would give her. There was only one choice to make. The decision seemed predestined. "Yes."
The smile that filled the room was as wide as a sunrise. "I knew you were my kind of boy." He could not help himself. He reached out for her, wrapping his arms around her waist and pulling her into a kiss. Her tongue pushed into his mouth. She pushed back at the same time, sitting him on his bed and grinding herself into him as they made out. The feeling of her hips on him was a new one. His legs spread reflexively, letting her grind herself into his groin. Hands slid down her back. Panting breaths came through her nose. Teeth grazed his lip, pulling at the sensitive skin with a pain that made him moan.
Fingers groped at shirt buttons, half undoing, half just pulling in the flurry. Before he could finish, Alison was back in control. She pushed him flat on the bed. Her mouth was over his chest, teeth scraping over nipples and making him shiver in pleasure. He gasped and moaned with every kiss. She worked her way down the length of his body, laying a trail of kisses from his chest down to his hips. The final peck came directly on top of his dick. It twitched. Precum appeared on the top, ignored as Alison straightened and backed away.
She undid the last buttons that Gabriel had missed, holding the shirt together in a mockery of modesty. "Want to see what I've been wearing for you?" There were no words to reply. His eyes were glued to the exposed breasts as the fabric peeled away. He felt his dick twitch and strain. "What do you think?"
Gabriel wanted to answer but there were no words that came to his mouth. The outfit beneath was black, lacy lingerie. The bra, if it could be called that, did nothing to support her chest. Embroidery wound around in patterns of flowers that drew every gaze to her barely obscured nipples. The bottom half certainly fell short of any practical use. A matching flower eclipsed the center oriented so that a petal pointed down to guide the eye. There was a thin strip of cloth needed for structure before parting into a nothingness that her cock poked through. It stood straight through the crotchless panties, bobbing as Alison swayed her hips for him.
"Mhm? Nothing to say? Make sure you get a good look." His eyes locked to her groin as she strutted towards him. The length bounced with each slow step. Precum already dripped from the end in long glossy strings that hung in the air. As she reached him, her cock touched his stomach, smearing the natural lubricant. "Tell me if you like it."
Words spilled from his lips without thought. "You look amazing, Alison. This is perfect."
The smile that followed his words was far more genuine than he expected. "You're so sweet, cutie. Linda was right about how cute you are." There was an odd note of satisfaction to her voice that confused him but he did not have time to think on it. The hand he reached out was batted away. "No touching until I say so." She leaned over and pressed her lips to his again. He groaned into her mouth at the feeling of her cock pressing into his stomach. Tongues pressed together, tasting each other with abandon. She broke the kiss as suddenly as she had started it. "Stand up."
His feet had barely touched the ground before she was calling him back to her with a curled finger. Laying back on the bed, her thick cock stretched across her stomach past her navel. The few drops of precum it boasted before had turned into a stream. They ran down in a brook, staining skin in a shiny streak until they disappeared into her crotch. Gabriel felt his mouth water. He licked his lips and swallowed, eyes fixed on her. The sight of her arousal made him want to do anything for her. To please her in any way that he could. He knew what she would want but still asked.
"May I suck you?"
There was a giggle before she replied. "Of course."
Her thighs spread, giving him room to crawl up between them. His tongue licked up the line of precum that stained her belly. A saltiness that made his stomach clench. He wanted more and followed the viscous trail to its source. There, he started slow, licking around the head of her cock. She moaned above him as his tongue fluttered along her glans, lapping at the fountain of precum pouring from her. It was not the first time that he had tasted her but it still felt so sweet.
Her precum was addicting and he did not want to stop swallowing it. Each drop went down his throat with a moan. He was addicted to the taste of her arousal, desperate for more of it. Her cock inched deeper into his mouth, threatening to gag him with each stroke. But he wanted more. Needed more. He took as much of her into his mouth as he could and sucked, relishing the precum flow on his tongue, swallowing it in a greedy gulp.
He pushed forward to take her deeper but was stopped. A hand pushed him back and forced him to nurse only the tip of her cock. "Not so fast. We've only just started." She rolled her head back, giving a long groan. "I'm so close to cumming." The hand tightened on his head. For a moment Gabriel thought she might pull him all the way down at once. Not that he would object. Instead she pressed him back until she popped free of his lips. "Get on top," she commanded. "All at once, cutie. Ride me like a good slut."
With the permission granted, he rose over her. On his knees, her cock was still long enough to poke at his dick. Gingerly, he guided the stiff rod between his legs, sitting back until it prodded at his rosebud. A normal person would have been intimidated by its size. Not Gabriel. He let it prod him, stretching just a little. His dick strained against the air, leaking precum. She felt so good inside him and he wanted more of her. The rest of her dick ached to be inside him, needing it to fill him like they both knew it was meant to be. He did not need her to tell him twice. He leaned forward and pressed his lips to hers, tongue probing between them. As he kissed her, he felt her cockhead slip deeper, spreading him wide.
The moment his ass touched her hips, a familiar shiver crept through him. It was the same feeling he had known the very first time she had fucked him. The sensation that his ass was meant to be filled with her, the same way that his mouth was meant to suck her. All his holes were made to serve her, to be used and taken by her however she would want. She could have asked anything of him, he would have given it to her. He wanted to please her. Needed to make her happy in any way he could. Anything that she wanted was fine with him so long as it was in service to her.
He moaned into her lips, feeling her cock twitch inside him. It felt so good to be filled. In this position, her dick went even deeper than it ever had before, pressing into his prostate with a constant stimulation of pleasure. A fire burned in his gut, threatening to erupt at any moment and drag him over the edge. Arms wrapped around him, pulling him down. One hand went to his neck while the other found his back. It was all he needed. The cock in his ass filled him too much and the kiss was all the more that it took for him to cum.
A squeak escaped him, voice too hoarse to make more than a sound. He could not stop cumming even if he wanted, dick jerking uselessly. Cum squirted from his cock spraying Alison's stomach before slowing to a thick dribble over his own balls. Gabriel felt his muscles spasm and lock as he held her deep inside. It took everything he had not to collapse on top of her, every muscle shivering from the force of his orgasm.
Alison held him up, kissing him and grinding into him. Her thrusts were gentle but each made her cock press deeper into his prostate and extend his orgasm. The pleasure felt so good that he was torn between wanting it to end and never wanting it to stop. "Good boy," she whispered in his ear. "Take it all." Each word was punctuated by another thrust, stretching him a little more. Her hands kneaded the soft skin of his ass. A finger teased at his hole as she thrust again. Pleasure flowed into him with every movement, the orgasm going on and on and on without seeming to slow.
But there are no pleasures in life that never end. Even the best of things must eventually come to a stop. His muscles relaxed and the orgasm eased, going from a raging inferno to a small flame that smoldered with each movement. It would be a while before the blaze fully died, but it had faded enough to let him think again. His arms fell by her sides, feeling her body beneath his fingers. He pushed himself up on the shaky limbs, only able to prop himself up on elbows.
The smile Alison returned was pure triumph, her eyes shining with the glow of a hunter that had just caught their prey. "Very good boy. I'm proud of you."
He smiled back at her. "Thank you." Leaning down, he kissed her again and felt her tongue meet his. Her moans were louder than before, more urgent. He understood. He had cum but she had not yet.
Gabriel managed to sit up, looking down to where their bodies met. Her dick filled him with a thick pole, stretching him open wider than he had ever been before. He tried to lift himself from her but his thighs betrayed him. Just as he crested her cockhead, they gave out from under him. Rather than stop, he simply let himself drop down. The sound of her breath caught and the look on her face was pure pleasure as he filled himself. With newfound determination, he raised himself again. The slide back down was just as good as the first time, the feeling of fullness in his ass so wonderful that he wanted to cum again.
With weakness left from his orgasm, gravity pulled him down before he could manage to fully rise. Still he tried to keep going. A slow pace, it was not a lot, but he kept riding her. She looked a mix of pleased and amused. "Such a good boy," she said, smiling. "Keep riding me. Keep fucking your ass with my cock." A hand cupped his cheek. He turned to kiss her palm. "Yes, cutie. You're doing great. Show me how much of a slut you can be." A moan escaped him at the praise.
Her hand abandoned his cheek for a grip on his hip. She lifted him up with an ease that made him feel just as light as he looked. For a moment he felt a rush of air over his stretched hole before being dropped back onto her dick. The speed picked up, going faster and faster until he could not tell up from down. His entire existence became the feeling of her stretching him. The pleasure of having her inside him.
He was not sure when he started cumming. It just happened. Another orgasm struck him, as if the first had never ended and just came back to claim him. A small part of him tried to worry that it would be too much, that he might not be able to handle another. Another part of him just did not care, enjoying the feeling too much to care about anything else. Dick spurting in the air, the cum dripping down his balls, he continued to ride her, too blissed out to do anything else but feel her fill him.
For a moment he thought that was it, that there would be nothing else to come of it. But it was not over. A sudden heat in his belly surprised him. His head swam with sudden delight and he felt her dick pulse inside him. More than just cumming, it felt like Alison was emptying into him, filling him with the same ecstasy that he had been enjoying the entire time. He felt her balls contract, pressing to her body, the last of her seed spurting inside him.
It seemed to go on forever. There was a moment where he thought it would never stop. And then it was done. Her cum was still inside him, leaking out around her cock, but she was finished. Arms came around him, pulling him to her. "Good job, cutie." The words were soft, more of a murmur than a proper voice. "That felt amazing." He smiled at her, leaning into her embrace.
"Thank you," he said, more happy than he knew how to explain.
"Of course, baby. Of course." She held him tight for a moment before pressing on his shoulder. "I have to get cleaned up, cutie." Gabriel nodded but still took a moment to disentangle himself. It felt good to be so close to her. When he finally rose to his feet, he felt the last of her cum leak out and drizzle down his inner thighs. He would have to clean himself as well. A sudden quiet click made his head turn to Alison standing a few feet away, tapping on her phone. The distinctive sound of a message being sent rang out and Gabriel did not care.