Authors note: Welcome to my latest story. This is my first entry into this category and on that note, a brief disclaimer. If you're not familiar with my style, I take my time, building the story before I deliver what we're all here to read. If you're a fan of shorter 'stroke' tales, then this story most likely will not be to your liking. Having said that, let's get to it. Lovecraft68
While watching Tammy fidgeting in front of me, I began to feel a little edgy myself, but for an entirely different reason. Whereas the adorable little brunette in front of me's heart was no doubt quickening due to nervousness, mine was from excitement. For the last couple of weeks, I had wondered if it would come to this, if my cute little coed maid was going to ask a big favor of me. In fact, just last night I had laid there in my bed, stroking to the image of those huge brown eyes looking up at me, while she tentatively took my cock between those perfect lips. Those same lips that were not only perfect for sucking cock, but for putting on an irresistible little girl pout, the kind of pout I lived to see.
I forced myself to play it cool, sitting back in my recliner, sipping at my glass of Jameson's. In the meantime Tammy sat in the other recliner across from me, her hands folded in her lap, looking around evasively, trying to get up the nerve to ask me. Swallowing the smooth whiskey, my eyes wandered down from her long curly black hair, big doe eyes and sweet little mouth, to the less than ample swelling of her tits. Like the proper young lady she was, Tammy wasn't wearing anything revealing. Her white button down blouse was tucked in snuggly, but because her breasts were small wasn't showing much. That was just fine with me though. Not only did I enjoy pretty little tits, but loved girls who didn't dress like sluts. It made it that much hotter to see what they had.
My gaze trailed down from her chest and wandered down past her lap to look at her long well shaped legs. Tammy was wearing a black skirt that was just shy of knee length, but because she was sitting had ridden part way up her thighs. A few days ago however, I had gotten a much better look at what Tammy was hiding under boring clothes. Obviously not expecting me to be home, she had come over to clean wearing a pair of denim cut offs and a skimpy tank top. She seemed self conscious as she puttered around the office while I was pretending to be typing. The sight of her smooth white thighs had me hard at my desk and when she had bent over, I found myself staring at the sweetest little heart shaped ass I'd seen in quite some time.
The grey tank top showed off her little tits very nicely. She had been leaning over in front of me, and I had been so mesmerized by the sight of the tops of her perky little tits, I let myself get caught looking. I looked up to see her staring at me and was preparing to give her an insincere apology, when she had straightened up and apologized for dressing inappropriately. She explained she had gone jogging and having lost track of the time came to my house without changing so she would be done before I came home. Shifting gears I gave her a wink and told her, "Trust me Tammy, you have nothing to be ashamed of"
She blushed and gave me an nervous giggle that made my cock twitch and caused me to imagine all the other cute little noises I would love to hear her make. My eyes made their way down her shapely legs and ended at her feet. Tammy hadn't come to clean today, and instead of the sneakers she normally wore, was wearing a pair of black sandals. I took a moment to imagine those soft feet with their pink toe nails resting on my chest as I...
I snapped my eyes back up to her face and lowering my glass, smiled at her.
"I'm sorry Tammy, you seem nervous so I figured I would let you take your time."
"Thank you." Looking down at her legs where she must have seen me looking, she tugged her skirt down towards her knees. "Sorry about that."
"About what?" I asked, hoping she would give me another of those preciously innocent answers.
Looking away from me, Tammy didn't disappoint.
"My skirts a little short and...."
"Please," I waved my hand at her, "First of all that skirt is far from short and honestly," I gave her a deliberate once over. "You certainly have the legs for it, so why not?"
Tammy blushed furiously.
"I....umm, thank you I guess."
"You're absolutely perfect," I told her and meant it. She couldn't be more perfect if she tried and the fact she wasn't made her all the sweeter.
"I don't know about that." She said, "I'm nowhere near as pretty as some of the girls at school and the way they dress," she shook her head. "I could never show that much," she laughed, "Then again maybe that's because I don't have that much to show."
With an effort I avoided asking her to let me be the judge of that and instead took another sip of my drink before replying.
"You know, that's what I like about you Tammy, you're modest."
"No, I think I'm being honest."
"No," I shook my head. "You're being modest because you're quite an attractive young lady."
I paused and felt my cock stiffening as Tammy's face turned even redder and putting her head down, she looked up at me through her long eyelashes and asked, "Really?"
"Really," I nodded. "And I'll tell you what, maybe it's because I'm older, but I find a girl who leaves something to the imagination far more desirable than a girl who dresses like a slut, it's like they're advertising what they think everyone wants." I gave a mock sigh, "I guess I'm just a sucker for a good girl."
Unable to resist starting the game a little early, I gave her a sly smile and asked, "Are you a good girl Tammy?"
"I like to think so."
"It must be hard to stay a good girl no?"
"I'm not sure what you mean."
"Well look at you, you must have guys hitting on you all the time."
"Sometimes." She shrugged, "But they're not like you, they'd rather chase the girls that dress slutty."
"Because they're easy." I told her. "They don't have to do anything to get them; those bad girls just give it right up."
Tammy frowned and started looking around again, obviously becoming uncomfortable with the conversation. Speaking of uncomfortable, my cock was bending painfully in my pants, but I had to keep my legs crossed so she wouldn't notice the bulge in my jeans.
"Well I guess that's what guys want."
"Not really." I told her. "Some guys think good girls are more fun, especially when they finally decide to be bad." Giving her a wink, I asked, "Doesn't your boyfriend like when you're bad?"
"I don't have a boyfriend; we broke up a couple of months ago."
Even more perfect! Her not having anyone would be one less excuse if this went where I hoped it was going.
"Oh, that's too bad," I said, hoping I sounded sincere.
"Yeah well, I guess he found the bad girls more fun and dumped me for one."
"His loss Tammy."
"I suppose." She sighed. "He said I wasn't good at being bad, but he said it a lot cruder than that."
"Oh." I said and paused, my mind racing.
Tammy was only nineteen and definitely seemed like the shy type, was it possible....?
"Was he your first boyfriend?" I asked, trying to sound casual.
"First real boyfriend." She nodded. "I went on some dates in high school, but Robert was my first...." She stopped and her cheeks again turned red.
As much as I relished her embarrassment I got her off the hook and asked, "Did you guys date long?"
"Six months." She said. "He was really sweet in the beginning, then after we..." she looked away and I was going to say something else, but she finished. "When he got what he wanted, he didn't stay around."
Oh goddamn! Tammy wasn't more than a couple of months removed from having her cherry popped! Most men my age would be turned off by her inexperience, but my cock was throbbing so hard it was beginning to ache. Although I enjoyed a woman who knew her way around the bedroom as much as any man, what I lived for was girls like Tammy. Young and sweet, more girl next door cute than out right sexy, and most importantly a good girl. Easy women had their place, but there was nothing hotter than making a good girl bad, especially if they didn't really want to.
For me it was more about the thrill of watching those big eyes and trembling lips as they forced themselves to do whatever I asked. I suppose in the end it was much more about taking their innocence as it was about taking their bodies. In front of me, Tammy had gone back to looking down at her hands, probably wondering how she had gotten herself into an embarrassing conversation and still trying to work up the nerve to ask me for the favor I knew she needed. Rather than ask more embarrassing questions, I decided to let her sit and let her wonder why she'd said as much as she had.
In the meantime, I thought back to the first time I had experienced the game of Sweet Reluctance as I had come to call it. It happened five years ago when my company had to make some cuts. I was asked to trim two people from my department and one of them was a twenty one year old intern named Susan. I waited until the end of the day and asked her into my office. As she sat there looking like she was ready to burst into tears, I explained how sorry I was, but I had to let her go. Susan began begging me to reconsider, telling me how her family was on the west coast and if she lost this job, she might have to move back home.
I genuinely felt bad, Susan was a good employee, but had the least seniority of the group. As she sat there, her head down, I found myself, as I had many other times, checking her out. Susan was a petite little thing, barely five feet and a hundred pounds soaking wet. Despite her small stature, her body was well proportioned. Her tits were on the small side, but looked just right on her, and she had a cute little ass that I enjoyed looking at on days when she wore jeans to work. That day she was wearing a red sundress that showed off her tits and slender, but well-shaped legs quite well.
I was drawn from my perusal of her body, when Susan said the three words that have inspired more porn movies and erotic stories than any other; "Please Mr. Daniels? I'll do anything!"
Initially I didn't think of her statement in that way. I was at work after all, and Susan was a bit of a wall flower and had a reputation as being very sweet, certainly not the stereo typed secretarial bimbo. I shrugged and replied that I really wished I could help her, but I couldn't see what she could do that would affect my decision. Susan had then left me open mouthed when she repeated her statement and standing, slid the straps of her dress down far enough to expose the red bra she was wearing. I almost went with my first reaction which was to tell her to please put her dress back on when the look on her face stopped me; she looked scared.
It dawned on me that she didn't want to have sex with me, that she truly wasn't the type to do such a thing, but she was so desperate that she would be willing to. My eyes dropped to where she was still holding the straps of her dress and I saw her hands were shaking. As I continued to stare I realized with a start that my cock was hard. I wasn't sure where it came from, but I proceeded to tell her to not just undress for me, but to do it slowly. She did as I asked, just as she did everything I asked of her that afternoon. Every time I told Susan to do something, she would hesitate and her lips would tremble. I didn't push and would wait; eventually she would do it, but reluctantly.
Whenever she would pause and get that look on her face, my cock would twitch. Even better were the small whimpers she would make while sucking my cock, or when I bent her over my desk. The entire time I was having her cater to my whims it was her hesitancy that had me as hot as the actual sex. When we were finished I honored my half of the deal and let someone else go instead of her. I ended up having sex with her on two other occasions, but neither time was the same. I figured out it was because she was less nervous and more confident. It occurred to me that the only thing that had led me to enjoy the first time so much was her reluctance.
I did the smart thing and told her that we couldn't carry on and she seemed fine with it. In fact our little deal turned out quite well. Susan has since moved up in the company and is doing quite well for herself and I discovered a new passion, because, after that I was hooked. Over the years I have constantly been on the lookout for a chance to 'help out' a struggling young girl. These situations didn't occur often, which made me savor them even more. Because they were so rare a year ago when traveling for business, I went to an escort service and requested a young girl and specified she had to act nervous and demure.
The girl showed up and looked, and admittedly acted perfect. The problem was even as she looked up at me and pouted when I told her to blow me, I kept coming back to the fact that this girl made a living selling sex and it was just that, an act. So unfortunately my fetish for corrupting sweet young women was very rarely fulfilled. Two weeks ago however, I had begun to get my hopes up. I had met Tammy six months ago through a friend at work who recommended her when my long time house cleaner had to return to Florida to take care of an ailing parent.
From the first time I met her, I was in absolute lust. Tammy was everything I fantasized about, cute, sweet, shy and absolutely adorable. Many were the nights I lied there playing out my little games with her in my mind, cumming to the image of her submitting that perfect little body to me. Usually I wasn't home when she cleaned, but several times I'd arranged to be so that I could watch her. Once she had been upset about something and unable to resist those sad brown eyes had asked if she wanted to talk. It turned out to be something minor, some issues with school, but at one point her lips were trembling and I yearned to see them trembling elsewhere. To sit back and watch those big eyes get even bigger as I guided and coaxed her to please me.
I had no desire to be rough or forceful to these little waifs. In fact even from the first time with Susan I found it more exciting to speak to them softly and soothingly. I gently encouraged them to do my bidding, urging them to be a good girl for me. That wasn't to say I wouldn't throw some demeaning remarks in here and there, but I never physically pushed them. At any point if they wanted to stop I would tell them they could, but what a shame it would be that I couldn't help them. I made sure to go out of my way to tell Tammy that if she ever needed anything I would be more than happy to help. Sadly, I had come to the conclusion that my fantasies would stay just that, the girl seemed to have her shit annoyingly together.
Then two weeks ago, I overheard her on her cell phone telling someone she didn't have enough money and could they give her some more time. I was dying to ask her about it, but part of the game was letting them come to me and despite my obsession, I let it go. Three days ago when Tammy came by to collect the fifty dollars that I paid her to come by an hour twice a week, she seemed upset and I asked if everything was okay. Tammy shrugged, and then caused my hart to skip a beat when she told me that because she had worked on the books the first part of the year, her financial aid was not covering all of her next semester and she needed a thousand dollars. Now to many a grand may seem like a lot to pay for a piece of ass no matter how young and tight it was, but I made damn good money and my opportunities to indulge were few and far between. I had no doubt that if the time came, Tammy would be worth every penny.
As excited as I was I kept my cool and asked if she could get it from her parents. She had said they were barely getting by and she had only been in Rhode Island for less than a year and didn't know anyone well enough to ask for help. I was so desperate to get to her, I almost broke my rule and offered, but I thought about how much better it would be when she came to me. Since then it was hard to concentrate on anything except the image of Tammy naked and whimpering on my bed while I showed her how to be a bad little girl. When she had called this morning and asked if she could come by and talk to me tonight, it had been everything I could do not to lock my door and jerk off in my office. I held off however, as I wanted to be horny all day so that cute little Tammy would receive quite the load when she earned her favor.
Speaking of that favor, it still hadn't been asked for yet. Tammy was still looking down and much as I enjoyed anticipation, my cock was not only throbbing, but I could feel a wet spot in my underwear, from its dripping. Putting my glass down on the table next to the recliner, I cleared my throat. Tammy looked up at me and smiled nervously and not wanting her to lose her nerve I prodded her.
"So as much as I enjoy talking to a cute young lady, I doubt you came by for small talk." I paused as she nodded and then continued, "You mentioned on the phone that you needed to ask me something?"
"I...well," Taking a deep breath seemed to force the words out, "Mr. Daniels, you know how you keep telling me that you like me and think I'm doing really well with my life?"
"I do and I mean it," I smiled at her, "You're really on the right path Tammy, it's good to see, and by the way, call me Josh."
"I'd feel kind of funny." She shrugged, "It's sort of disrespectful."
"Not at all," I waved my hand. "'Mr. Daniels' makes me feel old so I think Iwould rather be disrespected."
"Okay," she gave me a coy little smile, "But you don't look old at all."
"Thank you, but I'm sure you're just saying that," I sighed. "I'm old enough to be your father."
"You look a lot younger than my dad." She told me, "He's already going bald, and you have such nice hair."
I laughed and made a show of running my hands through my still thick black hair that had only a few grays along the sides.
"Tell you what Tammy, if you need a favor, you're off to a great start; you know what they say about flattery!"
Tammy giggled and a thrill went through me, oh how I loved little noises like that.
"So I guess I should tell you that you have really pretty blue eyes then?" she asked. "Would that help?"
Not as much as pouting while you ask if you can suck my cock would, I thought, but out loud answered, "Only if you mean it, if you don't then its teasing and it's not nice to tease Tammy." Because God only knew she's been teasing for months.
"I do." She nodded. "I like blue eyes. So umm, now that I flattered you," she laughed nervously, "I kind of need...."
"What else about me do you like about me?" I interrupted.
"Oh, I..." she stopped as I caught her gaze and winked at her.
Tammy's eyes widened and she licked her lips nervously. The sight of the tip of that pink tongue sent a thrill through me as did the fact that I was pretty sure she was trying to figure out if I were joking or not.
"Well, I think you're very nice. You're always smiling when I see you and..."
"Who wouldn't smile at the sight of such a pretty young girl?" I asked, trying to keep my eyes focused on hers.
Tammy looked away and started to blush again.
"See, like I said, you're always really nice."
I laughed softly, at what was a pretty good recovery on her part. I knew I was in danger of pushing too hard, but couldn't resist one more try.
"I don't mean personality, I mean appearance, you like my hair and eyes, anything else?"
Tammy shook her head.
"I'm not sure what you mean Mr... Josh."
"You know what I mean Tammy." I told her, then putting my finger up continued, "Tell you what, you said you needed to ask me something, but it's my house and I'm going to ask you something first okay? I mean fair is fair right?"