Gwendolyn
Copyright© 2026 by yfnsp
Chapter 14: He’s a Keeper!
BDSM Story: Chapter 14: He’s a Keeper! - 18-year old Gwendolyn was never going to have a boyfriend. She went to college planning to fuck a lot of different boys, not believing that her fantasy, a sexy boy who would worship and obey her, was possible. But on the very first day of class, she meets a boy who had worshipped her from afar. Could this be the man of her dreams? Gwendolyn is determined to test him and find out.
Caution: This BDSM Story contains strong sexual content, including Ma/Fa Fa/Fa Ma/Ma Coercion Consensual Romantic Lesbian BiSexual Heterosexual Fiction Cuckold BDSM DomSub FemaleDom Humiliation Spanking Analingus Cream Pie First Masturbation Oral Sex Pegging Petting Sex Toys Water Sports
Through my euphoric haze and over the roaring in my ears of the orgasm flooding my pants with cum, I heard Nate respond. I was gasping, trying to keep quiet to avoid attention in the noisy dining hall. I opened my eyes to see Nate focused entirely on Gwendolyn as he answered my invitation.
“I’d be honored,” he said, a glint in his eye as he spoke quite solemnly. “It would be a pleasure to fuck your beautiful girlfriend.”
Gwendolyn held his gaze in silence while her hand was working to open my jeans and reach into my boxers. She turned to me as she brought her hand back out, up to my lips, shining with my shimmering slime.
“Thank you, Gwendolyn,” I said. I licked her hand and sucked her fingers clean, drawing the notice of one or two nearby diners. It was good. It tasted like devotion.
Nate got it. “What a good obedient boy you have!” he said admiringly. “You’ve trained him very well!”
Gwendolyn laughed happily. “Not really. I’ve only had him five days,” she said. “He’s just a really sweet boy.”
She retrieved her hand and dried it on her shirt. “And when we met I found out he already worshipped me. He had been for years.”
“No, you have trained me, Gwendolyn,” I said. I wanted to give her credit. I needed Nate to truly appreciate her magnificence. “I worshipped you, but you taught me how you wanted me to express my worship and how to please you. You made rules for me and you rewarded my obedience.”
Nate agreed. “It looks like you’ve trained him to eat cum,” he said by way of evidence. “And being your cuck? That wasn’t his idea was it?” He raised an admiring eyebrow. “You’re not giving yourself enough credit. I sensed your power right away.”
Gwendolyn suddenly appeared taller, looking regal. She addressed Nate as if on high. “Are ready to submit to my power?”
“Yes, Miss Gwendolyn,” Nate said with palpable excitement. “Command me.”
Gwendolyn stood and took my hand. “Come with us,” she said.
The three of us walked together to my car. Gwendolyn held my hand all the way, but then she sat in the back with Nate while I drove.
“So this is Dr. Metzler’s house?” Nate said as we climbed the stairs to Gwendolyn’s attic lair.
I undressed on the landing and knocked for admittance according to protocol. Nate had entered with Gwendolyn and was still fully dressed when he opened the door for me. Gwendolyn was sitting on the end of the bed, also still dressed.
Nate looked me over as I walked in. I was self-conscious. My cock had deflated, but began to swell again as I stood before Gwendolyn, awaiting instructions. This was new territory for me. For both of us. I stood silently with my hands behind my back.
She could sense my apprehension, and its battle with my excitement. “It’s going to be okay, baby,” she said, stroking my flank gently, the way you might calm a nervous colt.
That helped. And so did her cat, Toby, who crawled out from under the bed and wrapped himself around my ankles, clearly preferring me over Nate.
“Put this in your mouth.” She held the butt-plug out to me. I had forgotten it. She had not; she had removed its packaging, intending to put it to use.
I got it good and wet, knowing where it was going.
“Good boy,” she said holding out her hand to retrieve it. she patted her thigh. “Lie down.”
I lay myself over her lap. I felt her spread my cheeks. My anus felt the exposure to the cool air and then the pressure of a wet finger, followed by the cool steel of the plug, opening me and then sealing itself inside. It made my cock twitch and release a bead of pre.
“Good boy,” she said again. “Isn’t he pretty?” She patted my jeweled ass playfully.
“Very fetching, Miss,” said Nate. It seemed an odd word choice, but he sounded sincere. I had a fleeting thought: does he want to fuck me?
“Okay, stand up,” she said, giving my ass a proprietary slap.
Then she said, “Come here,” to Nate.
He stood facing Gwendolyn beside me.
“Mike will undress you. Raise your arms.”
I turned and pulled his polo up and off. His chest and abs were trim and muscular, his shoulders broad and shapely. He was just a tiny bit shorter than I, but he still had shoes on. I knelt and untied them, Nike running shoes. He lifted each foot in turn, assisting me in removing them and his socks.
I tried not to think. I focused on the task at hand. For Gwendolyn, I said in my head, repeating it like a mantra. It kept me calm. I would do whatever she wanted. I trusted her.
The smell of his feet was perceptible but not overpowering. It was different from hers, that I loved to worship. I stood to unbuckle his belt. I unbuttoned his jeans and pulled down the zipper. His masculine scent was present. I was able to ignore it; it had none of the allure that Gwendolyn’s scents affected in me.
I pulled down his jeans and underpants together. He shimmied his hips slightly to help and stepped out of his pants as I held them, kneeling. His cock was semi-hard, hanging over his loose balls. It was thicker than mine and uncircumcised.
“Feel his cock,” said Gwendolyn, her voice thick and low. “Get him hard for me.”
I wrapped my hand around it, feeling it stiffen and rise. I stroked it. It grew to a length comparable to mine, which had also risen, but looked straighter and blunter, with its foreskin hiding the head.
“Stand up,” she told me. I stood, turning to face her. She took my cock and, saying “Turn,” she turned me to face Nate.
She pressed our cocks together, squeezing them and stroking them briefly, stretching her fingers to keep them in contact. It was bizarre to see the two cocks together like that, especially because it felt so erotic.
Gwendolyn stood up, letting go of our cocks. She put her hands on ether side of my face and pulled it into a deep, soul stirring kiss. Then she whispered hotly in my ear.
“Thank you, baby,” she said.
Then, breaking our embrace, she issued her commands.
“Sit,” she said to me, indicating the chair that had been placed beside the dresser, the same spot from which I had watched her masturbate a few nights before.
“You can touch yourself, but no cumming.”
I left the two of them at the foot of the bed and took the spectator’s seat, feeling the plug move in my ass as my weight settled.
“Undress me,” was her next command.
Nate proceeded slowly, gently, as if unwrapping a precious gift and wanting to preserve the paper. He unbuttoned her shirt, slowly revealing her perky breasts. He paused to cup them in his hands, brushing her stiff nipples with his thumbs, eliciting a sharp gasp, before he slipped her shirt off her shoulders and let it drop to the floor.
He knelt and gripped the waistband of her leggings and peeled them down in one smooth motion. Gwendolyn lifted each bare foot in turn and Nate freed them, tossed the leggings aside, and reached for the waistband of the thong, the only cover remaining.
This he slid it down her shapely legs slowly, taking time to experience their elegant contours and the smooth texture of her skin, while he breathed in the heady aroma emanating from both the sodden fabric and her wet labia. Or so it seemed to me from my observer’s seat.
When Gwendolyn stepped out of the skimpy thong, Nate tossed it to me. Perfectly thrown, it landed on my lap in puff of redolence. I brought it to my nose with a deep sigh. The exotic perfume of her aroused and ready pussy was not just familiar, it was deeply moving, reminding me of everything I cherished most.
Still on his knees, Nate had grasped Gwendolyn’s round ass cheeks with both hands and was pressing for entry to her pussy with his tongue and lips. Gwendolyn fell back on the bed and pulled Nate up by his arms, so that his oral attack was redirected to her breasts.
“Fuck me, Nate,” she said fiercely. “Put it in me now!”
It was clear she had no interest in, nor need of, foreplay. The undressing had been more than enough. Nate took hold of his cock and, with practiced expertise, aligned it perfectly with her entrance and plunged it in, parting her passion-slicked lips and stretching her vaginal walls exquisitely, judging by her nearly pained expression and ecstatic moan.
Two thirds of his thick length having sunk into her on the first thrust, his second lunge completed the course, lodging him inside her, balls deep. She rocked her pelvis and wrapped her legs around his waist, locking him deep inside her. I watched her face reflect the ecstatic joy of being fully stretched and filled.
And then, as if by a silent signal, they began to move in synchronicity. Barely perceptible at first, the gentle rocking became a rhythmic thrusting that grew into a pounding, slapping, smacking, grunting, heaving, and moaning fuck for the ages. It was athletic and balletic, combative and harmonious. And it continued to build. It grew until it reached a climax. A scream, a sound I had never heard from Gwendolyn before, pierced the room, and all four limbs spasmed and went limp.
“No, don’t stop,” she said breathlessly, as soon as she was able.
Nate had held her fully impaled while she thrashed. He began moving in her again, this time accelerating more quickly, but with less collaborative effort on her part at first, until another orgasm began to surge inside her.
Then she raked her nails down his back and sank them into the cheeks of his ass, pulling him into her as if she could make him go deeper.
“Yes, yes, yes, yes,’ she repeated, punctuating each of his thrusts with affirmation. She was wiggling her ass in ways that made each of his thrusts impact the deep reaches of her fuck tunnel in a different spot, at a different angle. I could tell by the ragged flexing of his muscular back and ass, that he was on the edge.
“Cum in me, Nate! Fill my pussy with your cum!”
He did. With a deep guttural roar, he came, thrusting deep and pinning her deep into the mattress. I could see his ass and the root of his cock contract. I could have counted the number of ropes of cum he shot into her womb.
And she came too. I could see the orgasmic spasms that shook her as if in direct response to the force of his ejaculate. Nate collapsed, his head resting in the crook of her neck, and Gwendolyn too lay limp, sated and spent.
I had very nearly come just watching them, mostly watching Gwendolyn’s face. Her pleasure was palpable, as if my brain could receive the neurotransmissions from the pleasure centers in hers. It was such a deep connection that, rather than feeling jealous, my feelings for Nate bordered on gratitude for the pleasure he gave her.
When they had regained their senses and disentangled their sweaty limbs, Gwendolyn called me.
“Come to me, Mike,” she said. “Nate, trade places with him.”
The smell of sex filled the room as the couple disengaged. I stood beside the bed as Nate took my seat. His cock was drooping and glistening, a hint of what lay inside of my well fucked girlfriend.