Oversimplification of Amy Ch. 03

From Chapter 02: Amy and I go on our first real date, with a lot of kissing and touching. After a weekend apart, Amy freaks, and has a meltdown, so I take her in for a couple of days to help calm her. I get her calmed with a whole body massage. The second day (Tuesday) continues with this chapter after a busy day dining, bowling, running, and loving. She shows me what a charmer she really can be, and my admiration of her deepens. What will come next, I haven't the foggiest clue!

Please note that all names are fictitious, and are not meant to refer to any real person. All characters are over eighteen years of age.

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My Dilemma: Janie or Amy ... or Kathy?

Part Four, Round Two with Amy:

Amy is ready to spend a second night with me. It seems, after the active day we have had, that it might be a rather sedate evening for us tonight. My promised second massage will likely take place later to get her relaxed for sleeping. I am thinking about my off-handed promise of an inappropriate touch or two during tonight's massage, and I know that Amy is likely counting on it. But, what the hell ... how much trouble can I get into, really?

As I begin to make dinner, I am thinking about a conversation I had with Kathy's friend Tammy at the café the other day. Her motive is unclear, but I always thought that she had an interest in me, and would pursue it if Kathy were not around. So, there I sit having lunch by myself and Tammy comes in without her 'crowd' and plops her ample butt down at my table. Tammy is pretty and intelligent, but she is what you might call a shapely 'plus-size.'

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"Hello Michael, mind if I join you?" she said with a bright smile.

"Sure Tammy, no problem." I say wondering what is going on behind those dark blue eyes of hers.

She orders a light lunch when the waitress arrives, and we engage in conversation about mundane things, but I notice that Tammy carefully avoids talking about Kathy, until later in the conversation.

"Michael, have you ever heard of Jason Nesbitt?

"Um, yah. I guess so." I answer.

"Well, um Kathy knows him too. I fact because of his 'reputed size,' she asked me to introduce him to her. Jason and I went to the same high school."

"Well, he has a reputation amongst the jocks as well ... what do they call him ... the stallion?" I respond.

Tammy giggles and blushes a little. "Yes. He would make a Shetland pony jealous from what I understand."

"So, Tammy, what interest does Kathy have in Jason, and why would you be telling me this?"

"Oh Michael, Kathy was just curious, you can't blame her after all, and I don't think she was with Jason more than once ... maybe twice. But, I know that she misses you during her visit home, and will be happy to be back on Sunday." She hesitated for a moment and then said,

"Um, Michael, I was thinking about going to Silvia's party on Friday, and if you don't have any other plans, uh, I was um, wondering if you might like to go um, with me."

There it is! Her reason for trashing her friend, she wants to move in on Kathy. Tammy would be a fine date, she is attractive and smart, she has a great deal of sex appeal with her pretty face and large boobs, and she has a lot of friends, but she is just a little too devious for my taste. I told her,

"I actually do have plans for Friday Tammy, but thanks for the invite, sounds like fun, but maybe another time."

"Oh, okay Michael, Um, I just thought you might be lonely with Kathy gone, but no big deal, and as you say, maybe another time."

We talk about a few other things, but Tammy finishes her lunch quickly, and leaves with a "thank you" after I offer to pick up the tab.

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Later, dinner prep with Amy is underway, and I am still thinking about my lunch with Tammy, and her information that behind my back, my "girlfriend" fucked the guy with the largest cock on campus ... as far as anyone knows. The rumor is that he is packing twelve inches, and has been very popular with the girls on campus. I just figured that my girlfriend would not be one of them. If Tammy's informing did not help her, I might just help Amy. I may be making a decision I have been leaning toward for a while.

I start making some rice, steaming some veggies, and broil a couple of good-sized chicken breasts. Amy is helping by selecting the wine to go with it. She selects a Pinot Noir, which is a light red wine, and not a bad choice. I set her to the task of chopping the veggies after she pours both of us a glass of the smooth Pinot. Amy is almost twenty, and nearly old enough for alcohol, so her having some wine is okay with me in private. With our tasks complete to the point where everything is cooking, we two friends clink wine glasses and toast each other.

She turns her glass around with her lip print toward me, and offers it to me for the toast, and I do the same with mine—kind of a vicarious kiss you might say. I have a lump in my throat looking down into Amy's lovely brown eyes. We both recognize the heavy romantic element to the moment we are sharing in silence as I watch her eyes glisten a little. She breaks the spell of the moment by softly saying,

"Michael, I love you! You know that I have loved you since I was fourteen. If you picked me up right now and carried my into the bedroom, I would let you make love to me. I know that you have always thought of me in only one dimension ... as just a brat ... just Janie's kid sister. But, I am much more than that! And all that I am Michael, I am offering ... to you."

I look at her for a long time, as my look of surprise melts into a loving smile with my own eyes starting to glisten. I see tears form in Amy's eyes, and I know she is worried about what I might tell her. I have to be very careful about what I say to her, so trying to organize my thoughts, I start out with,

"Amy, you are lovely person. You are smart, you are joyful and playful ... and you are quite a sexy girl. And yes, your heart is a deeper ocean that I ever gave it credit for ... I oversimplified you and I apologize for being such a fool. Perhaps I oversimplified your sister Janie too, considering her just 'arm candy' back then."

I take a breath and with Tammy's information in mind, I continue, "Hell Amy, I don't really know what love is, do you? I know for certain that I care for you ... I care very deeply for you, Amy. Let's just see how things go tonight."

Amy is riveted to every syllable I am saying as I put down my glass, I gently place my hands on her shoulders and tell her,

"Amy, I honestly do not know my true feelings for you. You are such an attractive and sweet person, and God, you are such a blast to be with! We have been at different places for so long, and I am racing to catch up ... it might not be too long honey."

Amy quickly moves her fingers to her cover her mouth to stifle her bursting out in tears. She swallows hard, clears her throat, and after many seconds gives me her reply.

"I will wait Michael..." she takes a moment to keep from crying, "...I will wait for you ... as long as it takes for you to ... figure it out. Down deep you love me Michael ... I know you do and I will..." now she does start crying, but pushes herself to finish, "...I will wait for you to ... to realize that!"

Amy bursts into tears, and then rushes to embrace me. She drops her wine glass—a thing no longer important to her—as the wine curls out of the glass, attempting to escape before the glass crushes against the floor. Her body smashes against mine as her crying echoes through my apartment.

I smooth her hair and kisses to top of her head, as bitter tears fall from her eyes. She looks up at me and her face is a sheet of salty tears. I pick her up, lay her on the couch, and give her a loving kiss on the forehead. The oven buzzer goes off, and as Amy lies on the couch drying her tears and trying to regain some composure, I quickly rescue the chicken, and turn off the burners for the rice and vegetables. A mundane task, but it necessarily interrupts a very heavy moment between us.

Each of us says what we need to say and no more, so we eat in silence, broken only occasionally by a softly spoken word or two or a gentle touch. Amy steals a chunk of my chicken with a naughty smile, and I give her a look that says, "Really Amy?" But, I know that she will always steal from my plate, it is becoming an endearing trademark of hers. When we finish, we quickly clean up and put things away and I say to her,

"Wash your face, undress, and then wrap yourself in a towel, and I will give you a nice massage."

Without saying a word, she disappears into the bathroom. Two minutes later, she reappears in nothing but a towel wrapped around her. I already have a large towel spread out on the bed for her lie on. As we approach the bed, she says,

"Turn your back, Michael!" several seconds later she says, "Okay!"

I turn around to see Amy lying face down on the large towel with her smaller towel lying across her, covering her from lower back to just below her butt. I wash my hands; get the body oil, and mounting the bed next to her start again with her neck and shoulders, expertly pushing into her muscles. She moans occasionally.

I work my way down the center of her back, then back up working the larger muscles of her back and sides. I switch to her lower legs; she is moaning with pleasure and says,

"Oh, Michael! Do you know what you are doing to me!"

I smile as I lift the bottom of her towel and seeing her growing wetness, I am safe in saying,

"Yes!"

"Michael! That's cheating!"

I laugh and continue up to her hamstrings and the sides of her thighs. I fold her towel back to work the tops of her glutes, then down further covering her sex, to work the lower portion as my hands push deeply into the larger muscles of her firm buttocks. When I am satisfied that they are well worked, I fold her towel back up ever further completely off her buttocks. She looks back over her shoulder and asks,

"Is this is going to be the naughty touch Michael?"

I just smile as I slide my fingers down the crease, massaging her cute little asshole with a fingertip, teasing her just a little as she moans, "Oh, my Goddd!" I let my finger explore her soft opening a while to give her a pleasurable little massage of one of her most intimate muscles. `

"Oh that feels sooo good ... Michael, you are such naughty boy!"

Satisfied with my handiwork to this point, I give each of her ass cheeks a hard slap to bring the warming blood to the surface. She gasps with each slap! I say to her,

"I will turn around again for you to rearrange yourself however you wish on your back my dear."

I hear her shuffling around, and after ten seconds, she says, "Okay, Michael!"

Turning around I see my lovely little girl lying on her back with the towel over her body length-wise, covering her from just above her breasts to just below her vulva. When she raises her arms to put them behind her head, her breasts raise a little also, exposing the tops of her areolas with her nipples just peeking out from under the edge of the towel. I smile, and adjust the towel to cover them.

"Aw, Michael! Spoiled sport, I was giving you a little treat!"

"Thank you for that, honey! You have very lovely little nips!"

I go back to work on her frontal massage, starting with her scalp and facial muscles, working my way down her neck, shoulders, and the top of her chest muscles. Since the towel exposes her sides, I continue with her arm muscles, top first then bottom for each arm. She giggles as I work her armpits a little, and proceed down her sides. I find a ticklish spot or two, and she reacts when I press into them.

"Open your legs a little, honey."

She opens them with a sexy smile, and I scrunch to bottom of her towel together to expose her hips but not her crotch. I work my way inside her hips, and her lower abdomen, the hollow of her stomach just above her pubic bone. She is moaning both from the relaxation and a bit of sexual arousal.

I work her feet and all of the little muscles, move to her lower legs, and then with more oil I move up to her quads—her large thigh muscles, digging deep into them to relax every tension point and work out the knots. Amy tells me it feels good, but her face registers a little pain from the deep pressure into her muscles.

"There! You now have a brand new massage, and since we did both sides, it should last you a little longer. Don't you think?"

"I don't know, Michael. They seem to wear off pretty fast with me, and I may need a new one before you know it!" (giggles)

"Well, truth be told, I like massaging you, so I really don't mind that they wear off so easily!"

We both laugh! I see her thinking, the wheels are turning and I know something is coming; I do not have long to wait for it,

"Um, Michael? You know what else has worn off, is um, the sp-spanking you gave me some years ago. It wore off and I um, need uh, a n-new one of those too!" She says this to me quickly and nervously or she would likely not have gotten it out.

I looked at her and she has a hopeful look on her pretty face ... one that says "please!"

Before I can answer, she pulls her towel off, giving me a good look at her naked bod. She is absolutely gorgeous with her petite curvy shape, apple tits, and pretty, but now swollen and wet pussy lips. She waits to give me a good look at her, and then the little exhibitionist moves to my dresser to retrieve my hairbrush ... the large one with the flat, hard, wooden back.

She hands it to me, lowers herself over my lap as I sit on the bed. Her pouty little ass is pointing up at me so attractively; I smooth my hand over it. I gently let my fingers slide down her crevice and across her exposed pussy (she moans softly). She looks back and up at me saying,

"Michael, I know that you took it easy on me because I was a little girl, but I have been so naughty lately that I think I um, need it ... harder!"

I go along with her little game, by saying back to her,

"Amy, you have been a bad girl, and I have no alternative but to punish you. You know that this will hurt you more than it will hurt me!" She giggled nervously at my turning around the old saying,

"Yes, Michael. If I get it hard enough, it might help me to be a good girl."

I am having trouble not laughing at my little imp, but keep a stern look on my face and stay in character as the angry father punishing his little girl.

"I am going to have to give you ten—"

"—Twenty, Michael!" she interrupts.

"—twenty strokes on your little bottom with this hard wooden brush. You have been a naughty, naughty little girl!" I almost lose it and burst into laughter, but stay in character.

As I touch the cold backside of the brush on her warm butt, she gasps. I bring my hand back, and brought the brush down on her tender little ass with a loud "THWAP!"

She cries out in pain, with each successive blow. I try for a good clean slap from the brush, but I start out easy so I don't hurt her. After five blows to each cheek, she is starting to cry, and after a few more, she was sobbing loudly and profusely as she kicked her legs and tried to cover her bottom with her hand. Her pretty ass was absolutely glowing at the halfway point, and I could feel the heat. She was crying inconsolably, with her hands held together on her back.

"Michael! Stop ... please! It hurts too much!" She is now crying a hard as it is possible for her to cry, with sobs and hiccups interspersed. The girl was in true agony at her own insistence. After those first ten strokes, I see that her little bottom has sustained more than enough damage, and forego any further "punishment.'

I toss the brush onto the bed, reach back for a bottle of lotion with a lot of aloe, and slowly massage her damaged butt. As I release her hands and she uses them to cover her eyes still crying hard, trying to recover some semblance of composure. I had taken it so easy on her when she was sixteen, that all she felt was the arousal and not much pain.

I think we both underestimated the amount of pain a hard wooden hairbrush can deliver with only ten strokes. When she is able to speak, she says,

"Oh Michael, it hurts sooo much ... I didn't think it would be so bad!"

She gets up and straddles my lap facing me with her legs around me and then she throws her arms around me sobbing hard into my shoulder. I can feel myself starting to get harder with her pussy resting on my bulge. I have both of her ass cheeks in my hand, and the other one on her hip trying to console her. I am still massaging her butt, with my middle finger naturally slipping down between her cheeks and onto her sopping pussy lips. I massage her with my finger and slowly slip it into her.

She pulls back a little to look into me, and framing my face with her tiny hands and her lips close to mine, she softly and quietly says,

"Michael, please fuck me!"

I can feel her shudder a little after she says that to me. I detect a little nervousness on her part, and maybe a little embarrassment for being so bold telling me exactly what she wants. Amy is a good girl, but I have never heard her use the 'f-word' before. She is telling me exactly what she wants, leaving nothing in doubt.

She massages my cheek with her hand as her other one gently cradles the back of my head. As I look at this tiny girl with her red, somewhat puffy wet face, my heart goes out to her. It's as if all of the confusing feelings I have had for her over the years finally click into place. I know exactly how I feel about her.

"You know that I love you Amy! You even said it ... and I do!"

Her chin starts to tremble as she begins to cry again. I adjust my cock, which is starting to become very uncomfortable. She notices, and moves to pull my briefs down and off with my help. She straddles me again, and massaging her little ass, I use two fingers to spread her inner pussy lips. I am amazed at how tiny her opening is, as I start to work the tip of my cock into her.

I work about half of the tip into her slowly as she winces a little at the thickness of it. Being inside her soft tight pussy for the first time ever, is the most incredible feeling. She starts to wiggle her ass on my hard thick shaft pushing down further as it gets comfortable for her to do it. It is not long before she shudders into a nice little orgasm.

"Oh-my-God, Michael, you fill me up so much ... It um, hurts a little!"

She pushes me back on the bed still partially impaled on my cock, she pushes down further onto my shaft. Finally, I get most of it inside her tight little vagina. She is leaning forward supporting herself with her hands on my chest. I can see her little tits jiggle as she moves up and down.

"Oh Yes!! Michael!! Oh-my-God!!" She is almost screaming and she continues to ride me.

I pick her up and place her on the bed on her back as I begin to stroke smoothly into her. She pushes her tight strong form up against me, matching my strokes exactly. She becomes very vocal as she tells me exactly what she wants and how she wants it! Our mutual efforts to fuck each other continue, with precision as I hold her through about three orgasms, and building to one of my own. I grab her hips as I get close, and thrust hard and fast as I explode inside her, with more intensity than I have ever felt with any woman.

I just can't let go of her ... I have to hold her as tight as I can as is push into her. I do not want this to end, and she is convulsing wildly from her final orgasm as I come inside her sweet, warm little pussy. I am out of breath, breathing so hard. All I can manage to say is,

"Oh ... my God ... Amy ... Amy ... oh ... God!"

She has gained her composure more quickly than I did, and giggles as she replies,