My Unusual First Time Ch. 01

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A drink was what I needed, all right. I felt it flow through my tense body as Rose began talking to me about channeling my energy into something more positive, about how I was a good-looking guy who needed maybe a few pounds, a new style of glasses and some clothes that fit me right. It was a testament to how much I already trusted her that I only internally winced in pain about a hundred times as she very nicely picked over the carcass of my self-confidence.

The beer was halfway gone when I started to really feel it kick in. I managed to get one only once or twice a month (the drinking age was 21 then), so I had a low tolerance. It was a good feeling, but I put the glass down and didn't pick it up again that day. No sense missing out on any of this extraordinary event in my life.

"So, the way I see it is you need to stop being solitary with your desire" she was saying, "and branch out to show how you feel to actual women, girls. Not some picture. You need to let them see how you yearn for them. To make contact. But it has to start easy, with no big deal about it, right?"

Sounded good, and I was impressed with the way she seemed a natural at giving advice. The words she used were put together well. I could almost conceive of myself following through. Almost. I nodded to her and received a smile in return.

"Good. So, if you're ready and relaxed, let's go back upstairs." She drained her glass and got to her feet.

Go back upstairs? For what? Whatever it was, this seemed like we were going too far.

"How about Harland?"

"Gone on a job" she replied over her shoulder as she started to make her way up the stairs. "Back on Tuesday. But he has nothing to do with this and you won't talk about it with anyone, will you." It wasn't a question.

"I-I don't, I mean I...." was my articulately-put protest, but I don't think she heard me, since it came out like a whisper. I watched her re-enter the guest bedroom, thankful in the back of my mind that she hadn't gone into hers.

It was a big step to go up there, but I made myself do it. So, my first time was going to be with an older woman, in her home. No problem. Piece of cake. I guess I surprised myself by not rushing out the door. The rest of that beer looked very tempting, but I managed to leave it behind. In the end, it was simple curiosity that pushed me up those steps.

Rose was sitting on the bed in those Capri slacks and that man's shirt. It was white, I remember, striped with some pale blue and black lines. She wore black flats, nothing remarkable about them as I recall. Her face was a little pink, probably from the liquor. Her hands were palm down against the bed, her knees together. She wore a pleasant, friendly expression. We could be about to discuss remodeling the room.

"Have you ever seen a woman naked, other than in pictures?"

"No." That wasn't true, actually, because once when I was much younger I saw a friend's mother in the shower, just for a few moments when I accidentally went in to use the bathroom. I figured that didn't count.

"So I guess that would really get you excited, right? A naked woman posing for you?"

I just stared. This was all happening, but it really couldn't be.

Rose didn't need an answer, of course. "When you're playing with yourself do you like to be in a particular position?"

"Huh? Oh. I see. I mean, like maybe sitting down or lying in bed. Okay. I guess, sitting down." I realized suddenly that I was hard again, my cock tip brushing tightly against the vent of my Fruit of the Looms, and no doubt making a tent in the front of my Robert Hall slacks.

"Good. Then you should probably sit down in that chair" she said lightly, like we were just going to get good and comfy with each other. She didn't move, but watched as I settled into the plush fabric of the chair. It was roomy. Rose, I noticed, was now looking at my pants. The whole house again seemed quiet. You couldn't even hear traffic from up the main road. I idly remembered that my parents would wonder why I was late for dinner, but to hell with it I was 18 now and could figure out some excuse.

"We're just doing this part to get some stuff out of your system" she let me know as she stood and began unbuttoning the sleeves of her shirt. "I know how it can be, growing up with boys and men. I kind of like it, actually, that they can't keep their hands off themselves at your age. Still, it is a waste." There was a bit more emphasis in her words now, and I realized she might be getting more than just the fun of being the teacher out of this afternoon. That made me feel better.

"Slow or fast?" she asked. At my quizzical expression, she added: "Taking my clothes off, I mean. What's better for you, slow or fast." She had the shoes off now and the shirt was halfway unbuttoned down the front. She also had moved closer to me, standing maybe five or six feet away.

"Slow, I think." Like women peeled off for me every day, right? And, of course by now I'd have a preference. Slow sounded good.

"I thought so. And real close, probably, also." Without waiting she did exactly that, stepping across the carpet to stand within two feet of my shoes. I could see her white Playtex bra front within the opening of her shirt. The tops of her breasts could just be discerned.

She said nothing for a while as she slowly unbuttoned the shirt completely and slid it off. Like I said, it was a man's shirt so it just seemed to disappear off her with a simple shrug. I didn't see it fall to the floor because my eyes were alternating between her own and the sight of her from the waist up in just a bra.

It was certainly not a sexy brassiere. It was utilitarian, it did the job. But, it did contain a well-formed pair of breasts, ones that seemed nicely in proportion with her waist and hips. Losing that shirt was a revelation, as I could now see that Rose had a classic figure, and skin that looked soft and smooth and unmarked. Her waist was not tiny but neither was it wide in relation to the swell of her hips, which curved out perfectly just under the waistband of her slacks. Her navel was a cute little indentation line that ran about an inch before curling into its opening, like an upside-down question mark.

"I hope you aren't going to be shy" Rose observed, nodding pointedly at my lap as she teasingly reached back behind herself with both hands to start on her bra clasp. This thrust her breast flesh out to where it spilled a bit over the front of her undergarment. "You need to have some relief, I'm assuming. That's what we're doing here, you know."

With that she did a slow turn to reveal that her busy fingers had opened all but one of the hooks of her bra clasp. With her back to me I had the momentary privacy to do exactly as she said and fish my straining erection out of the confines of both slacks and briefs. It filled my hand with warmth and pleasure and the urgent feeling of need; I'd have to take it easy on myself here, I knew, or this would be over in a few seconds.

With the clothes all tight against me I decided to pull my slacks down to my knees and extract my balls from the pouch of my underwear, as well. They felt very swollen, probably just my imagination. I fought to banish all worries that Rose might not "like" the looks of my equipment when she turned around again, instead opting to concentrate on getting re-situated in the chair and to watch as she opened that final hook.

Which she did in another moment or two, letting her shoulders stoop forward so the shoulder straps of the bra could slip off her arms. I could see the faint lines on her back of a bikini line, where the sun hadn't reached last season or so. I saw how nicely her shoulders were formed as she straightened back up, the bra on the floor now with her shirt, her hair resting at just the right point on her back and on those shoulders. I even liked the backs of her feet, which could be seen under her slacks.

When she turned there was little artifice or tease about it. She just presented her breasts to me as she took in the sight of this skinny teenager sitting in a chair gripping his cock. We both breathed in. I hoped she did for the same reason as I, for her tits were the stuff I dream about even today. You can use all the terms like perfectly-formed or well-rounded or what-have-you, but any man knows when an exceptional pair of breasts meet his gaze.

Her nipples weren't brown but instead light pink, with large areolas that were a darker shade. They looked erect to me but perhaps hers were always like that. They sat just a bit high on the weight of her breast flesh, seeming to point slightly upward. Her breasts had just the correct amount of droop to them, just enough to bring a nice soft shadow to the undersides. Not sag, mind you, but droop. I was in awe, being at the time more of a breast than ass fancier. More about that another time.

"You get very red" she observed. I thought she might mean my neck and face until I saw that Rose was studying my cock as I feasted on her naked breasts. "You aren't about to- -"

"No, no" I quickly interrupted. "It just gets like that." She smiled and stepped closer to me, bringing that marvelous bosom with her. She knew I'd want to see her more close-up and at the same time she wanted to appraise me, that was clear.

"Stroke it a little" she teased, and when I numbly reached out to try for one of her nipples she pulled back with a laugh. "No, silly. Your cock."

Hearing that word from her mouth was like a shock treatment. No girl ever said cock, did she? Not even grown women. It was so dirty. If I had been stroking myself right then I would have lost it immediately. I remember I actually gasped out loud.

"What? Oh, I said cock. Cock cock cock. You like that? How about cunt? Or fuck? Then there's always the ever-popular pussy."

I stared at her in amazement. Until this moment I would of course have no idea that a soft spot in my libido would be a pretty girl talking dirty. How would I know, since no girl or adult female I'd known had ever said such things aloud. With Rose speaking like this it was all I could do not to groan out loud in lust.

Rose couldn't help but bust out giggling. "You should see your face" she laughed, and soon enough she had me laughing as well. I must have looked very goofy sitting there with it all hanging out and getting this crazy look of shock on my face, it's true. She reached to touch my face quickly as we both quieted down, then told me I was sweet, and then asked if I wanted her to pose any particular way.

Did I ever. But right now I was so screwed up between laughter, lust, embarrassment, a half-a-beer, and the overall strangeness of these events that I wasn't exactly at my best in the speaking intelligently department. Plus, in the midst of our laughter I had quickly flashed on my friend Edward, wondering if he knew I was still at his brother's house. That was a worry. I couldn't tell Ed about this, not ever.

"The reason I ask is, well Danny, you look close to, you know, at least to my eyes, and since this is your first time I'd like it to be as you want, once I get the rest of my clothes off. You know?" Her voice was a bit distracted, as her gaze was on my stiff shaft and the swollen balls beneath, in fact Rose looked like it was all she could do not to grab it (or was that my wishful thinking?). "It's no big deal if you can't wait, just go ahead and finish. But if you slow down I'll pose anyway you want me. I know you must have favorites. Like in the magazines."

"It's only that you're so beautiful, Rosemary" I said sincerely. "I can't believe you're doing this." Idly, almost unconsciously, I ran my fist up and down my dick, feeling a drop of precum smearing on my fingers as I excruciatingly caressed just the glans for a moment.

"I'm just the first naked girl you've seen in the flesh, is all" she replied with a friendly grin, bringing her breasts down to within a foot of my face. I could see the dimpled skin surrounding her protruding nipples, inside the darker rings. Yes, I believe she was finding this quite enjoyable, teasing me, teasing us. "Only I'm only half nude. So hold on."

Rose slid out of the Capri's more quickly than I expected, kicking them away so I could see her white panties and smooth, long legs. I noticed she was touching her breasts from time to time as she made a show of turning this way and that to reveal her sexy bottom encased in those panties, and that she steadily watched me play openly with my erection while doing so. My cock was alive with nerve endings, making it feel positively huge in my fist. I had never seen the head swell larger, that was true. It still amazes me that I held off in coming – I'd seen more than enough to cause it, for sure.

I liked the way the vee of her panties was darker than the rest of the material, which meant there was actual honest-to-god pubic hair under there trying to peek through. I tried to imagine what her vagina would look like.

She walked over to the side of my chair to first bend forward and tease me with those luscious tits again for some moments, then turning to bend in the opposite direction, bringing her underwear-clad backside close to my face. I could see the division of her ass cause the opaque cotton to adapt to her shape as it stretched over her roundness. "Oh, Rose" I recall saying.

"Is that what you like, Danny?" she asked, craning her head to look at me even as she held that position. I nodded. "You want me to take the panties off?" I groaned in agreement and had to completely stop my self-pleasuring for fear of going off that second. "Right here, like this? Or maybe on the floor?"

"On the floor?" I muttered. My head was in a daze. I think all of the blood in my body was elsewhere. My eyes were burning holes in that underwear.

Without answering Rose gently got to her knees on the carpet and moved herself inside my legs. She my slacks down to my ankles. Her touch was like a fire on me, even though all she used was her fingertips, and those barely grazed my skin. For a moment while she pulled my slacks down her pretty face was in front of and beneath my leaking penis, and she took that moment to appraise me from that angle.

"You have to go home in these" she mused aloud, meaning the slacks, speaking almost to herself as she drew first one leg and then the other over my shoes and out from under them. She tossed the slacks behind me and then was turning before I knew what she was doing, getting into an all-fours position facing away from me.

I could now open my legs freely and needed to, for Rose backed herself in close and used her calves to move my shins apart. I was presented with her backside, not two feet away from my raging hard-on. Above it was her long back and the pretty profile of her face as she strained to look back at me. She had an almost mischievous expression.

"Is this good?" It was a purposely-leading question. This was the most sexualized moment of my life and it was about to reach its peak. What could be better? "Good" was not the word to use.

"Thank you, Rose" was my only way to answer.

"You're welcome" was the cheeky reply. "Are you comfortable? Ready for me to roll my panties down?" I swear, with such words coming out of her to accompany the scenery, I cannot imagine how I withstood it!

I had already drawn myself as close to the edge of the chair as possible and still be defined as sitting; any more to the edge and I'd fall off. Before me and below me was the nice, rounded set of ass cheeks of a woman I could fall in love with in a heartbeat. Above that were her eyes, watching me. In my hand was my aching cock. And, I was about to see in the flesh that which I had never beheld, the private areas of this same woman.

And, it was 1964, and I was in my 18th year. My whole life ahead of me.

Supporting herself with one hand, Rose used the other to reach back and draw the cotton fabric down over the skin of her buttocks. She brought her thighs together to facilitate this. Soon I could see the dark division of her crack, held tightly together as the panties continued to be pulled down. My heartbeat was pounding in my chest and ears. Rose continued watching me, though it must have been uncomfortable having to keep her neck like that.

Once she could no longer push the panties down, owing to the awkwardness of her position, she reached under with that same hand and began pulling them off from below. Now, I had jerked off to many poses like this from behind, imagining that the model was spread open so I could see it all, but of course no such thing was ever shown in those days. Imagine how I felt, as the panties were finally slipping down to her lower thighs and Rose's legs were opening just for me. Plus, she was looking right at me as she did it.

I stayed my hand just long enough to get a good look at the pucker of her anus, nestled within her luxurious, deep crack, and then the pretty pink lips and opening of her vagina below it. Rose arched her back as best she could, as I furiously renewed the stroking of my prick, her movements causing the whole of her private areas now to part to my eyes. I saw her pussy open like an orchid blossom, I swear, and her asshole muscles working to reveal a quick view of its dark tunnel. And then I was coming. Uncontrollably.

I sprayed thick white cum in the air, some of it landing as far up as Rose's shoulder blades and hollow of her back, some of it all over my own thigh and knee, but most of it arcing across the whole of her magnificent ass. Rose made an "Oh" sound a couple of times, I remember, but otherwise just held her pose.

I, on the other hand, am sure I made inhuman noises of joy as all the tension in my body emptied onto her. Ropes of cum clung to the cheeks of her ass, spurts of it sprayed directly onto her asshole and drooled down onto her exposed cunt, still more streamed onto her upper thighs, with the last of it hitting the carpet beneath my spurting cock. It seemed to go on forever, and don't we all wish it could.

After it subsided, I felt a strong, nearly overpowering urge to sleep. That was new to me, probably because it was the first time an orgasm had literally wrung me out like a rag. Usually I'd feel energized after a good climax.

The next few minutes seem a blur, as Rose helped us both clean up. First she got me to my feet and dragged us to the bathroom, where she seated me on the toilet and wet a small towel in the sink, under warm water. This she gave to me and, without a word, stood facing the sink, presenting her backside to me once more. This woke me up.

I took my time gently removing every trace of sperm from her thighs, vagina and rear hole, as well as her back and ass cheeks. It was great for me to be able to study her like this, a real anatomy lesson, and Rose squirmed a bit more than I would have expected from simply being washed. As well, there was a definite funk in the air that was apart from the smell of my own jism, and it dawned on me this was my first scent of female arousal. A new world was opening up, as they say.

It was when she had rinsed out the cloth and turned to kneel before me that Rose spoke again. "I want you to remember not to tell anyone. Also, you can depend on me to be available whenever Harland isn't around if you feel the need to jerk off. We must get that out of your system. No magazines, remember." She said all this as she gently cleaned my cock, balls and thighs of any remnants of my orgasm. My equipment was very limp, but I still appreciated the feeling of having her face so close to my body there, and the gentle touch as she cleaned me. It was very comforting and sexual.

I couldn't believe my ears, though. What was the catch? Was this really happening? And by the way, who would believe me if I did decide to tell? As Rose finished cleaning me off I simply said "Thank you, thank you" for lack of anything else coherent to express my feelings.