Aunt Shirley Taught Me Pt. 02

She lay upon my body from head to toes and I love the closeness, the warmth of her soft smooth skin and the way her pleasure passage still tightly encases what remains of my erection inside her. I wrap my arms around her, my hands draped on each arse cheek. She must have enjoyed our mutual possession as much as I ... we hold that position long after the last spasm of my cock inside her.

I feel my now floppy cock slip from within her carnal hold, hear her gasp, "Oh no, it's gone."

"We can try again, can't we?" I suggest hopefully.

"Yes, soon Paul. Tell you what, I'm hungry, how about you? I was so excited that you were coming here again today that I skipped breakfast. How about I go down and get us a snack? You can stay here and recover; I'll bring it up and we can eat in bed like we're having a picnic ... a sex picnic." She giggles that lovely way she does. "Then, when you're hard again -- and I know you will be - we can simply push the meal aside and get back into it."

She leaves me alone in her bed. Within ten minutes, she is back with a mini feast. It is like she has prepared a high tea. There are little sandwiches and cakes. We sit up in her bed and sample her savoury treats until ... she spots my cock that has quietly, and without any urging on her part, responded to the sight of her naked 32-year-old body. I am at least half hard once more.

"Umm, so does this mean you're ready for more Paul?" she asks, reaching a hand to touch it, her soft fingers circling the head, causing it to expand further to fully erect again.

"I guess that's what it's saying, a, a ... um, err, Shirley." Almost coming out as an apology, I sheepishly admit, "You're sitting here totally naked and I can't take my eyes off your beautiful breasts, and these nipples that I love sucking and all that other lovely stuff down there. I can see my cum still leaking out of you, I want to be in there again."

"Oh my, you are a horny one, aren't you? What have I unleashed in you? Ok, Paul, I can see you're not to be denied. I'll clear all this away to make some room. Any thoughts on what you want to try next?"

"No, I'm happy just so long as I can be inside you."

"Hmm, you are greedy, aren't you?" My aunt clears the plates of food off the bed, placing them on the floor. I notice her pick up something from the bedside table as she returns, shuffling on her knees to the middle, gesturing with her hand for me to move aside to give her plenty of room. She positions herself on her hands and knees, "Ok, get up behind me, we haven't done doggie yet. You'll like this, the man can go deeper this way than in any other position."

I position myself as she directs, kneeling behind her, my knees between hers. I gaze down upon her lewdly spread arse cheeks that reveal her tiny anal pucker and below that, the spread pussy lips that I now know so well. "Ok Paul, when you're ready, you can see I'm still so wet ... you can either come straight in or take your time to rub your cock around my clit. It's your choice, this is your day."

I select the latter, using my hand to steer my shaft within the folds of her labia, pushing it to rub the head against her little magic button and then pulling up to her vaginal opening. I can see all of her good bits, wantonly displayed, in this position. I am a sucker for how good her wet pussy feels against the head of my cock and on only my second sweep, I concede to the temptation and slide my cock up inside my aunt once more, drawing an expressive and seemingly appreciative gasp from her. I love this new position, being able to closely watch the insertion and withdrawal of my cock in her passage, although I miss seeing her eyes and beautiful face and I can't suckle her nipples. My hands reach around under her body for my fingers to play and pinch her nipples as compensation for not being able to suckle them.

I stroke my cock in and out a few times; her earlier hand job, along with our first fuck for the day, has taken all urgency out of my arousal. I am content to indulge myself in this new sexual playground. She half turns her head around, "You can play with my arse if you want, Paul?"

This is 1963, I knew nothing then about anal play between heterosexual couples, but it sounds like my aunt might want to include this in my second lesson. She raises the hand that holds the item she picked up from the bedside table. Taking it from her, I see that it is a tube of lube. "Put some of this on your fingers and you can stick one or two inside my bum."

She must sense a moment of hesitancy on my part, "You don't have to if you don't want to, honey. I'm just trying to show you everything you should know. Some guys are into it and others not. If it makes you feel any easier, I gave myself an enema and then had a shower this morning. That's the real reason I had no time for breakfast."

I am amazed that she has exercised such foresight to prepare her arse for my visit when she has no idea how I might react to her offer. As it turns out, I am eager to learn everything that my aunt is generous enough to share with me, I squeeze some lube onto two fingertips and bring them to her tiny anal pucker.

She instructs me to be extremely gentle entering her arse, suggesting I initially be content to simply rim her anal ring for a couple of minutes until she relaxes. By way of explanation, she tells me, "Even though I really want to feel your fingers, and soon, your hard cock, inside my arse, you need to use a lot of lube and take a long, long time."

When she determines we are both ready, she talks me through pressing one finger in through the super tight opening, overcoming her tight sphincter. My fingertip is almost sucked in without the need to press too firmly. I add a second finger when she asks for it. All the while, I have continued slowly thrusting my hard-on into its now customary sexual home.

My two fingers wriggling around inside her anus obviously has a huge effect on her, her breathing quickens, becomes heavy, her gasps expressing the pleasure she must be feeling. Amid her gasps and moans, I hear her breathlessly suggest, "Do you want to switch now? Use your cock instead of your fingers, Paul?"

At 18 and in 1963, this was so new to me, I didn't know about anal sex the way I would later discover. "Really? I don't think it will fit? Your arse feels really tight?"

"It is, and that's what makes it so good for guys. It's up to you, you can if you want, I don't mind."

I was all for learning everything I could from Aunt Shirley, "Ok, I'm game if you are."

"Good! Pull your fingers out, and your cock too of course. You're going to have to put a lot of lube on your cock. I shouldn't need any more inside me, I'm guessing your fingers have spread it around enough in there."

I follow her instructions, smothering my cock liberally with lube. I carefully place my cockhead, fully hard and erect, at her anal pucker. There looks to be no way the head of my cock will squeeze through her tiny opening, let alone my whole hard shaft. I tell her so, "I'm not going to fit in there."

"Yes you will, Paul, believe me, honey. But you have to go very slowly, I'll push out to help you get the head inside me."

I look down on this unexpected new insertion, stunned to see the head of my cock disappear from sight, almost sucked up inside her anus, just the way she predicted. I would never have expected my aunt to know so much about sex or to participate in so many positions like a pro. Her bum's grip on my cockhead is so incredibly tight. I have got this much in, but still can't see her accepting the rest, nor being able to slide in and out of her when I begin to fuck her arse.

"Ok, so far so good, Paul. Now, give me a moment for my arse to adjust. Oh my god, you feel big, have you grown anymore?"

Does she mean that? Is she impressed by the size of my cock, or is she simply stroking my ego, building up my confidence for my sexual pursuit of Patricia? Whatever, it is nice to have my aunt on my side, teaching me everything she knows about sex.

I feel her anus tensing, gripping tight and then relaxing around my cockhead and it feels great. "Ok, Paul, I'm ready for more. You can start to push some more inside me, but slow and steady ... alright?"

Respecting the pleasures my aunt bestows on me, I follow her instruction precisely, pressing my erection forward in gentle increments, an inch forward and a half-inch back. It stretches this initial anal experience over quite some time, but finally, I have my cock so deeply embedded inside her arse that my belly is pressed firmly against the smooth cheeks of her arse.

All these years later, I remember now how I thought back then that having my cockhead inside her arse felt really tight, but when I buried my whole cock shaft too within her -- it felt unbelievably great. Aunt Shirley asks me to hold steady inside her for her anus to adjust to having my solid core deep inside. Then, she clears me to proceed in ravishing her arse, her face turning around to try to see mine, "Ok, Paul, go ahead and fuck me, just like you would if you were in my cunt."

So sexy to hear my aunt say cunt. I begin to slowly withdraw until only the head barely clings within the tight grip of her anal ring. The best thing about being in this position is how great it is to watch my whole solid erection sliding into and out of her stretched anal ring. "When you feel like you want to cum honey..." my aunt adds, "just do it. Don't hold back on my account, you go for it."

"I'm good ... for now," I assure her, content to gently slide my hard cock forward into her arse and then pull it back until the head just clings to her anal ring. The lube that I have copiously spread inside her anus works wonderfully, helping the quickening slides of my erection in and out of her bum. At 18, I had not previously thought of trying this with a woman ... I'd been more obsessed then with having my first actual fuck. Since I'd reached that milestone last week, it seems my aunt is now intent on taking me to the next level.

Fucking my aunt's arse, I find in comparison, it is so much tighter there than my recent foray into vaginal sex revealed. Having already cum twice, I feel no urgency to finish quickly, despite the incredible tightness of moving inside the dark confines of my aunt's arse starting to hit the peaks for me again. She urges me to go for it whenever I want, but I'd like to try getting her off before my own release?

As raw and inexperienced as I was then, I had the presence of mind to try playing with her clitoris. I take one hand off her hip, sliding it down her belly, lower still, to her labia where I source out her budding little clit. She is extremely wet there, enabling me to silkily stroke her. She moans appreciably.

Now caught up in the sexual heat surrounding her tightness, I never miss a beat, pumping my erection into her arse. This first anal event is hitting the highs, no doubt I am going to cum again. But how about my aunt, is she getting close? My fingers have her cresting, judging by the sounds emanating from her lips, her breathing heavy, her gasps and moans are that of a woman about to orgasm.

Oh my god, she better cum soon, I can't hold this back. She adds voice to the twisting gyrations of her arse, exhorting me, "Oh, fill me, Paul, pour your sweet cum into my arse."

I need no further encouragement to cum, her expressive urging is the catalyst for my cock to settle in deep, abruptly ceasing all thrusts to spasm in the tight confines of her rectum, spurting successive blasts of my cum deep inside my aunt's body. Her arms are trembling as she struggles, on hands and knees, to hold the combined weight of us both upright.

I think I get about three cum spasms inside her before her arms give way and she tumbles forward, flat onto the bed, dragging me down with her, my erection held tightly within the grasp of her arse, where the dregs of my cum continue to seep inside of her.

Concerned that I may be too heavy to be laying on her back, I ask, "Should I get off, are you ok?"

"Don't you dare move. I like the feel of you there." She turns her head, trying to see my face, "So honey, what did you think of your first anal sex, did you like it? It's different, isn't it?"

I guess I come across as sounding enthusiastic, "Oh yes, but very good. I can't believe how tight it is in your arse. Doesn't it hurt you?"

"It did the first time I tried it, but I've become accustomed to it now. So long as the guy isn't oversized, I can cope with it. You're a good size, Paul, women are going to like having sex with you."

"Is that it? Are you all done with me?"

"What makes you think that?"

"Oh, just the way you said that women are going to like having sex with me ... it sounds like you're suggesting your work is done."

"I certainly didn't mean it that way, Paul. I am sure we can get away with a few more hours before I send you home to your mom."

"Oh, that's good."

"Honey, you are insatiable, are you still wanting more?"

"Not immediately, but I'm sure I will ... like in about a half-hour."

She laughs at my youthful exuberance, suggesting we have a shower together, "We need to clean your beautiful cock, Paul. As clean as I made myself inside before you arrived, you have been in my arse."

We have that shower and return to her bed. As young and excitable about sex as I am back then, it did take nearly an hour before I was ready for more. We whiled away the afternoon enjoying slow, languorous sex.

What a day I have with my aunt. She seems determined to ensure my knowledge of all things sexual is thorough; I believe I am a good attentive pupil. As great as my day with Aunt Shirley has been, I have a date with Patricia. We are going out to dinner. What if I actually get lucky tonight with my new girlfriend and she removes all resistance? Will I be able to get it up after my aunt has drained me?

That evening, Pat and I have dinner in a nice restaurant and afterward, I park mom's car in what has become our favourite taillight alley location. Of course, we come together for an immediately passionate tongue kiss the moment I turn the engine off ... I am pleased with how our relationship is developing. No awkward moments now, no hesitancy in when to start kissing, as on our first few dates. She seems to enjoy the intensity of our kisses as much as I do.

Of course, my hands begin to roam all over her body, particularly now that I am emboldened by my aunt's lessons. But still, each time that my hand gets close to her clothed pussy, one of hers snatches mine away. I'd expect that, after several months dating, we'd be progressing toward full on sex, so I am disappointed this night that she isn't even allowing me to get as close as I had two weeks ago.

When our lips part to come up for air, she stares deeply into my eyes, a serious look on her face, whispering, "I have my period."

"Oh! Ok!" I acknowledge, giving a head nod too, trying to indicate that even this mere male of 18 has some understanding of such things. So, those four words of information have politely swept aside my expectations of getting my fingers, even my cock, anywhere near her pussy tonight. Perhaps just as well ... my fingers may have been up to it, but my overworked cock may have had trouble rising again.

At this stage of my story, I should advise readers of today who are under 60, that not many young women used tampons back in 1963, not as they do today. Most were guided by their mother's advice into using thick sanitary pads that were secured by a special belt, with pins, that went around the waist and under the crotch beneath the panties. Most young women were very self-conscious to have a man feeling around anywhere near there. I knew nothing of that stuff back when I was 18, but I learned about it as my sexual emergence got into full swing.

More intense kissing ensues in the darkened car, but I keep my hands above her waist. I see no reason why having a period should deter me from getting hands, fingers and lips on her bountiful breasts. My fingers start unbuttoning her blouse, I meet no resistance. Parting the two sides, I find that Patricia is wearing that bra again, the one I presumed she bought specially to tease and tempt me. A thin nylon covering on each cup, just transparent enough that I can make out the dark shape of her nipples.

One hand gets busy, massaging her left breast, feeling the nipple harden beneath my arousing touch. I switch to the other nipple, feel that stiffen too. I peep at her face, see she has closed her eyes to better enjoy, absorbed in the pleasure my massaging palm is bringing. A sweet sigh escapes her lips, I bring mine to hers to resume our kissing, pressing just enough for her to part her lips. My tongue slips in, finding hers, twisting and entwining together.

This is good but I want my lips on her nipples. 'Don't blow it now,' I advise myself as I dare to slip a hand inside the opened blouse, sliding it around to her back, hoping I can manage to undo a bra clasp one-handed. I actually used one of my mom's bras yesterday to practice this manoeuvre, examining the catch, hooking and unhooking it over and over.

My roaming fingers find the catch in the back. So far, so good ... she must be able to feel my hand and know what I'm trying to do, but our tongue kiss continues with no sign of her stopping to remove my roaming hand. There's the clasp, now can I actually get this undone one-handed? Have I set myself too ambitious a target?

Suddenly, I feel the two parts of her bra in back separate in my fingers. I let go of both sides and slide my hand back to the front, without lessening the intensity of my lips and tongue at hers. The bra in front is now loose and so easy for me to slip my hand under the left cup, my palm is actually on Patricia's breast -- and nipple -- for the first time.

She pulls her lips away from our kiss and I dread the worst. I look to see her eyes are open again. She is watching me closely, no sign on her face of how she might react. Which way will this go? My palm never lets up on massaging her breast and nipple. Patricia closes her eyes once more, laying her head back against the top of the front seat. I take this as approval. My hand pushes the front of her bra above the breast I am warmly fondling. I see her nipple for the first time, but rather than simply stare, I elect to pursue it with my lips and my face closes on her breast, my lips wrapping around the hardened nipple, sucking it into my mouth and using my tongue to paint its surface.

She sighs again, loudly, and in response, brings her hand, the one that had been resting on my shoulder, up to the back of my head to hold me steady at her nipple. I crazily suckle at her nipple and she seems to love it. Has she ever had a male kiss her nipple before? I expect not. I am making progress. After spending the day with my aunt, I am elated.

Emboldened, I switch sides and apply my lips to her right breast, meet with equal acceptance. I really get into the breast play, deciding to use my fingers next to caress and stroke the nipple that is being ignored while my lips suckle the other.

She is sounding quite breathless after the minutes of my breast play tick by, similar to how my aunt sounds when she's about to orgasm. Is Patricia close to cumming, even without my being able to touch her pussy? I have perused many books in the library in trying to educate myself on sex ... I read that some women can actually orgasm without being touched, but it's rare. Have I found one of the rare ones?

I don't know how long Patricia let me feast on her nipples ... I know the windows fog up. I am guessing at least a quarter-hour before she raises her head from the seat back and looks into my eyes. At the same time, using her hands to prise mine from off her breasts. "That's so nice, Paul, I really like what you're doing, but you know we can't go any further, and it's only going to become harder to stop if you keep that up."