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Controlling Caitlin by Emily Tilton – Sample

Chapter One

Controlling Caitlin by Emily Tilton“You need to spank that girl of yours, Neil,” Aunt Mary said. “She’s a pretty little thing, and you two make a very cute couple, but if you want to keep her around for a while—let alone build something that might become a solid marriage someday—you’re going to need to keep her in line. She was begging for a good, long trip over your knee last night. You must have noticed how she kept interrupting you during dinner!”

Neil tried to conceal his confusion. For starters, he couldn’t tell for the life of him whether Mary had decided to make fun of him in this strange way, or whether—even stranger, really—she meant what she said. When his dad’s oldest friend, not related to Neil’s family at all, but called ‘Aunt Mary’ for as long as Neil had been alive, had started in about Neil’s nineteen-year-old girlfriend Caitlin, Neil had been sure she must be joking.

Now, though, when Mary brought up the interrupting, Neil didn’t feel so certain. Caitlin did interrupt him a lot. Surely that didn’t mean she wanted to be spanked, though? Neil shifted uncomfortably in his seat in Aunt Mary’s living room. His cock had gotten a little hard at the thought of spanking Caitlin.

“I know you think I’m joking, Neil, but I’m telling you that unless you use a firm hand with her, you’ll lose her—and the time you have with her before she breaks up with you won’t be fun, either. She’s going to keep running over you, keeping you at her beck and call.”

Mary was only thirty-five to his twenty-two, but he had to admit that she seemed as wise as a real, older aunt. Just as with the interrupting, Neil saw the truth in what Mary said. Caitlin expected him to do everything for her—to pick her up at work though she could easily get a ride with a co-worker, to stop at the store for her favorite snacks even when neither he nor she really needed anything. He didn’t really mind, of course, but still…

“I do things for Caitlin because I love her,” Neil said defensively.

“And she takes massive advantage of that feeling, all the while hoping—even though she’ll never admit it—that you’ll put your foot down.”

“And spank her?” Neil laughed uncomfortably.

“She probably doesn’t expect to get spanked,” Mary admitted. “I doubt that’s part of her family background. But I know a girl who needs her butt whipped when I see one. And then…”

Mary had lowered her voice, and Neil felt his brow crease in puzzlement as he tried to figure out why.

“What?” he asked.

“You need to dominate her in bed.”

Neil felt the blood rush to his cheeks, and he turned his head and looked out the window at Mary’s garden, unable to meet her eyes. Aunt Mary had always been known for being blunt, but she’d never referred to anything as private as this before.

“You’re embarrassed.” Mary gave a silvery laugh. Neil turned his eyes back to her then and saw how attractive a woman his ‘aunt’ was in her maturity: chestnut hair and hazel eyes; very large breasts that swelled out her light cotton sweater and showed a hint of the bra beneath. Full hips and a full backside that Neil had to confess he’d stolen a couple of looks at the night before, at dinner at his parents’ house, when he’d seen Mary for the first time in several years. She had just moved back to town the week before, having left California and an apparently fairly glamorous life behind. No one knew exactly why Mary had returned to small-town Ohio, but Neil’s parents had certainly been glad to see her, and so had Neil, who remembered her only as a beautiful, sexy, impossibly out-of-reach creature during his whole adolescence.

“Wouldn’t you be?” Neil asked indignantly. Mary fixed him with what seemed to him an appraising look. He wondered suddenly whether she had ever thought of, well, having sex with him. Six foot two and often told how handsome he was with his dark brown hair and blue eyes, well-muscled from his job as a fitness instructor, he generally had no trouble hooking up. Mary, however, was special, somehow.

“No,” Mary replied. “But then I’m older and wiser than you are, and I’ve had some experiences that make it less embarrassing for me. I want you to have the benefit of my wisdom. Not only that—I want to teach you how to take Caitlin in hand.”

“In hand?” Neil asked incredulously.

Mary nodded. “I know you’re a dominant, and I know she’s a submissive. But I think the two of you are going to have a hard time understanding one another without my help, and I worry you won’t make it as a couple unless you let me teach you how to be the alpha male she needs.”

Neil swallowed nervously. Yes, he had fantasies like that. But when he hooked up with Caitlin, it wasn’t very much like those fantasies. He’d only had sex with her three times, since she lived with her parents and his roommates were always around his apartment—and they didn’t have enough money for hotel rooms. Each of those times had just been him on top and her below with knees spread and raised. She didn’t even seem to be that into it, frankly.

“Like… what would I do?” Neil asked in confusion. “I mean, give me an example of how I could… the thing you said—take her in hand.”

“I think you should start with a spanking. And then I think you should tell her to take all her clothes off and to get ready for fucking.”

“Jesus, Mary! Come on!” But Mary looked back at him intently, as if to say You know that you want to fuck your girlfriend, Neil. Don’t deny it. He went on, a little lamely, “We don’t even have a place where we can… you know, do that kind of thing!”

“You can do it here, if you want,” said Mary.

“And you’ll go out?”

“Maybe, maybe not. I may even watch on my closed-circuit video setup. But that won’t change anything. You’ll fuck Caitlin in my guestroom, and you’ll do it whenever you feel like it. I’m going to teach you to be a guy who tells his girlfriend when she’s going to have sex, and then makes good on the promise.”

Neil felt torn between the desire to tell Mary that she was crazy and the desire to ask her to tell him more. Closed-circuit video? To watch him have sex? The idea that she would provide her guestroom as a place where he could have sex with Caitlin as often as they wanted—not as he wanted, because that was stupid and sexist, wasn’t it?… Well. That idea definitely appealed to him. Even if Caitlin didn’t seem to like sex very much, Neil definitely did.

But this stuff about being a dominant, and spanking his girlfriend, taking her in hand, sounded wrong. Didn’t it?

“I think,” Mary said, “that you’re probably having a knee-jerk reaction to my advice. I think that knee-jerk reaction is coming from all the things you think you’re supposed to feel about your girlfriend.”

Neil felt his mouth twist to the side. He certainly couldn’t deny it.

“Let me show you something, then.” Mary got up from her chair. “Follow me,” she said.

Mystified, Neil stood and walked behind her, once again admiring her full backside in her gray woolen skirt. Now that she had gotten him thinking about spanking, he couldn’t stop wondering what it would be like to bare a girl’s bottom and bring his hand down hard upon it, in punishment. She led the way to the other end of her house, where the bedrooms opened off a softly carpeted hallway. Mary opened one of the doors, and Neil saw what must be the guestroom: the place where I’m supposed to take Caitlin, for fucking. The very act of watching the room come into view seemed to make him hard, because of the way Mary had spoken of how sex should be for Neil and Caitlin. Was that what Mary meant about showing him?

But the arousal that he felt on thinking about the room suddenly got much, much greater, because to his shock he saw that the room wasn’t empty. There was a naked girl inside, lying over a high-backed wooden chair, with her bottom to the door. Her backside seemed to be covered with a mess of curling red marks. On top of her back, neatly curled just above the place where her bottom-cheeks began, lay what seemed to be a broad leather belt.

“Say hello to Neil, Annie,” Mary said in a stern voice Neil had never heard her use before.

“Oh, Miss Mary,” said the girl, who turned her head, but apparently wasn’t allowed to rise from her position over the chair, so that Neil could only see a little bit of a tear-stained cheek and her wavy blond hair hanging in a curtain around it. “Please, don’t let him see.”

“Annie,” Mary said even more severely. “Do as I’ve said, or I’ll have to whip you again.”

Neil gulped. “That’s al—” He was going to say alright. Frankly, he felt so funny, seeing the naked Annie, whose pussy—whose shaved pussy, Neil noted, remembering how many times he had thought about asking Caitlin to shave down there—he could see peeping out between her slim, milky thighs.

But Mary cut him off. “No, Neil,” she said, “it’s not alright. Annie is a very naughty girl, and she needs clear directions and firm guidance in minding her manners. I’m going to have to whip her again, and put a big butt plug in that disrespectful bottom of hers, if she doesn’t obey me.”

“Hi, sir,” said Annie.

“Um, hi,” Neil said. Why had she called him sir? He felt a little off-balance with the strength of his arousal, and he felt he shouldn’t be there. Part of him felt that, at least, while his rock-hard cock seemed to sing a different song. He needed to think—maybe if he could get out of there and think about all this, it wouldn’t seem like he… like he wanted Caitlin to be over that chair, with her bottom covered in pretty red welts telling a tale of how she had learned a lesson about interrupting him. “I have to go—” he began.

“I don’t think you should go anywhere, Neil,” Mary said, “until you let me try to show you who I think you are, and what I think you need. I think maybe you should stay, and learn.”

“What?” Neil said, looking nervously at Annie’s pretty, bare bottom, and feeling his heart again beat faster when he noticed the bare cleft of her pussy, where he also saw now what he thought must be a little bit of Annie’s own arousal, glistening on the pout of her pink inner lips. What did that mean? he wondered. Did the girl like being whipped?

He turned his eyes back to Mary’s face.

“In my years away from here, Neil,” she said. “I learned a lot about myself. One of the things I learned was how to tell when a guy is a dominant, and when a girl is a submissive, even when they don’t have the slightest clue, consciously, that they are.”

“You keep saying that,” Neil protested, “but I don’t have any idea what you even mean.”

“I’m hoping you’ll let me try to change that. I want to suggest you do some reading tonight, but before I let you go I want to make it completely clear to you that I really think you need to take Caitlin in hand, for both your sakes. Annie here is a lot like Caitlin. She’s a brat, who sometimes interrupts me and other people. More important, she forgets to do her homework for her college courses. Today I’m punishing her because she did very poorly on a test.”

“Is she… your girlfriend?” Neil asked.

“No,” Mary said. “She’s just a naughty girl who needs someone to take her in hand. I met her in a café a couple of weeks ago. She’s heteroflexible, as we call it these days, but she thinks she’d like to meet a guy who could spank her the way I do. Don’t you, sweetheart?” Mary called over to Annie.

“Yes, Miss Mary,” Annie said politely.

“I’m afraid Neil is taken, at least for right now, sweetheart,” Mary continued, “but you’re going to suck his cock anyway.”

“What?!” Neil said.

Mary turned back to him. “This is where I’m hoping you’ll find out that you’re a dominant, Neil. Annie, take the belt off your back and bring it to me, on your knees of course.”

“Oh, miss, please don’t make me suck a cock,” Annie said. As she spoke, though, she reached her hand back to take the belt, and then she slid off the chair onto her knees and turned around to face Mary and Neil. The sight of the pretty, naked girl, about Neil’s own age he thought, her tiny breasts heaving a little bit as she breathed very quickly and her face wearing an expression of helpless arousal, made Neil again want to stop the whole strange scene so he could just think about what it meant that his cock was as hard as it had ever been. His eyes refused to stop taking in Annie’s shaved pussy and the way she held the belt in hands clasped in front of her midriff, imploring Mary’s mercy.

“Nonsense, Annie,” Mary said. “How are you going to become a good cocksucker unless you practice? Come here this instant and give me the belt, then ask Neil politely if you may unbutton his fly and uncover his cock.”

“Really,” Neil said, feeling his resistance growing very much weaker as he watched Annie begin to crawl toward him, her brow furrowed in a look of submission, as if she knew she would be whipped for not giving Neil a blowjob, “that’s—”

“I have a feeling you really do want your cock sucked by my pretty Annie,” Mary said. “I hope you’ll be honest with yourself, and with me.”

“But… Caitlin…”

“If you take my advice, Neil, Caitlin’s going to be the one sucking your cock soon enough.” Mary sounded so very sure. Caitlin had never offered, and Neil had never asked. He pictured her where Annie was, giving the belt with which Mary had punished her back to Mary, coming to kneel in front of him.

“I… have to go,” he said. “I just remembered… I have to be home.”

Annie looked up at Mary. Mary sighed. “I guess you’ll have to kiss my pussy instead, Annie.”

Neil couldn’t suppress a little gasp at that.

“Yes, miss,” Annie said.

“You don’t want to stay and watch, Neil?” Mary asked.

Oh, did he ever, but it was just all so… strange.

“No, thanks,” he said, trying to sound suave, as if he’d seen so much live girl-on-girl sex that he couldn’t be bothered.

“Do me a favor,” Mary said, “and read an article I’m going to email you a link to, once I finish Annie’s lesson.”

“Okay,” Neil said doubtfully. He couldn’t say he was a big reader, and he felt fairly thoroughly freaked out, now that he had managed to resist the strange temptations Mary had placed in front of him, but what could it hurt?

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