Gwendolyn
Copyright© 2026 by yfnsp
Chapter 13: More Ways to Please
BDSM Story: Chapter 13: More Ways to Please - 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
“Did you like it?” Gwendolyn wanted to know.
“Yes, it was very exciting,” I said.
“But?” She could hear my reservation.
“But I ... well, it felt like I was betraying you. I mean, when Marti was manipulating me. Getting turned on, performing for her. It helped to know you were watching. But I didn’t know what you were thinking. What you were feeling.”
“Oh, I loved it!” she grinned. “You looked so excited. And scared. Especially when you were scared. You were so helpless and so hard!”
We were finally alone together after spending an evening with Gwendolyn’s landladies, her downstairs neighbors. Marti - Dr. Martha Metzler, a professor of English literature in her mid-sixties - had used me as the object of a B&D demonstration, her other area of specialization.
Afterwards, I had followed Gwendolyn up the stairs to her attic apartment naked, as usual, watching the swaying of her perfect ass beneath the short skirt of her summer dress, knowing her pussy was bare. I also knew she had been aroused; I could smell it.
My cock was erect, of course. Her scent aways has that effect. It had only deflated briefly in the cold air on the veranda after she had freed it from the chastity device Marti had imposed before fucking me. “There’s my pretty cock!” she had exclaimed when it went from zero to two hundred millimeters in one point six seconds.
Now she was seated on her bed with me standing before her, my hands behind my back as she idly fondled my throbbing erection. She had changed out of her dress and was wearing one of the oversized tees she slept in.
“I liked what she did to you. Well, I didn’t like how she made your cock disappear so much, but it was hot seeing your balls like that. Anyway, I got really wet watching her fuck you.”
I groaned at the memory and at the way Gwendolyn’s fingernails were trailing up the underside of my cock.
“I have no desire to do that myself, but it was such a turn on to watch! It made me feel like I do when I watch gay porn. And you know how hot that makes me.”
Her hands slipped around me to fondle my ass cheeks. “Turn around,” she said.
She bent me forward a little and spread my cheeks. I could feel the cool air on my sensitive pucker.
“Your ‘boy pussy’ she called it.” She brushed her thumb over it. “How does it feel now?”
“Fine,” I replied. “A little sensitive maybe.”
She brushed over it again. I shivered.
“A little sensitive, for sure!” she said. I could hear her smile. “There would be cum in there if you got fucked by a real cock,” she said dreamily.
I shivered again at the thought. I had eaten another man’s cum for her. From her. Performing for her, pleasing her, excited me, especially as it excited her. I could just imagine how exciting it would be for her to watch a man fuck me.
She pressed a digit - her thumb? - into the tight center.
“Ooh, there’s still some lube in there,” she commented, twisting it as she pressed deeper. It felt tight, but not unwelcome, radiating tingles up into the root of my cock.
“How does that feel, baby?” she said softly, her breath warm in my ear.
“Mmm, it feels good,” I replied, a little surprised.
“Maybe I need to get you a plug. Would you like to wear a plug in your ass for me?”
“For you?” I said, stalling as I pondered, imagining walking around campus, sitting in classes, with a constant fullness back there.
“Yes, if you want me to,” I told her, not admitting the thrill I felt. “I want you to decide. I want it to belong to you, like my cock.”
She shoved her thumb deep, making me moan. She leaned forward, pressing her hard nipples into my back.
“That’s right, baby. Your ass belongs to me!”
She turned me back around and pulled me to my knees.
“Open,” she commanded.
I sucked her thumb clean. It was slightly greasy and smelled of ass.
“Make me cum,” she said. Her hand gripped my hair and guided my face between her thighs, to my favorite place in the whole world.
~~~~~
We met at the car after classes on Tuesday. “We’re going shopping,” she had told me at breakfast.
Aubrey’s Adult Adventures was a seedy looking shop on the seedy side of town. Gwendolyn had done her research, though, and it had exactly what she wanted. We wandered the aisles, checking out the variety of kinky merchandise on display. There was a whole glass-top display case devoted to male chastity.
“Look at all these different shapes and sizes,” she said. “Would you like to try them on?”
“Um, that one looks pretty scary,” I said, pointing out one with little spiky teeth inside a metal frame. I couldn’t even figure out how some of them worked.
Gwendolyn must have heard my trepidation, because she said, “Don’t worry; I don’t want it locked up. It’s my cock. I want it where I can keep an eye on it!” She gave it a little squeeze the way she often did.
“Besides, these are for bad boys who can’t keep their hands off of themselves. Or let other people play without permission.” She pressed up against me, rubbing my now hard cock.
“But you’re my good, obedient boy, aren’t you?” I could feel her hard nipples poking into me as she pushed me against the case and stretched to kiss me, melting me with her fierce possessing tongue.
After checking out all the varieties of strap-ons and a mind-blowing array of didoes, some super realistic and some in fantastical colors and shapes, we came to the butt-plug case. She picked one out, a substantial stainless steel plug with an imitation ruby in its stem.
“I can’t wait to try it on you,” she said happily while I paid the cashier, a bored looking middle aged man wearing a greasy toupee. He didn’t react to what she said, but he kept an eye on the convex mirror as Gwendolyn perused the gay magazine aisle with me in tow on our way out. She stopped and pointed out some of the more provocative covers.
“You liked that one with the cowboy,” she stated, back in the car. It wasn’t a question.
I started the car. Had it been that obvious? The size and the beauty of the man’s erect cock and the physicality of his toned body, wearing only chaps and a Stetson, had been quite arresting.
“I’ve never seen anything like that,” I prevaricated. Seeing her observing me made me aware that I had unconsciously licked my lips.
“I think I want to see you suck cock,” she said, watching me closely.
I said nothing. My face felt hot.
“That place used to have glory holes,” she told me. “Do you know what those are?”
“Yes,” I said. I’d heard of them.
“I’m going to find someplace I can take you and watch you suck. You’d like that, I think.”
“You looked like you wanted to suck Marti’s. But she stopped you. Did you? Were you going to put it in your mouth?”
“Yes...” I said, hesitating. “But that’s different,” I said. I was going to say that it was a dildo, not a cock, and anyway Marti was a woman, not a man. But it seemed irrelevant suddenly.
“Hmm,” she said with a wry smile. “Real cocks give you cum to swallow.”
I drove us back to campus so we could eat supper at the dining hall. We had both bought the semester dining pass, after all, and the food was okay, especially on Taco Tuesday.
Gwendolyn had a hand in my lap under the table, resting on my erection while we ate. A gentle reminder that it belongs to her, it’s a gesture I’ve become accustomed to. She was playing the teasing game she liked, talking about lending me to other women around us. We had played it before and found it arousing for both of us.
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