Aunt Shirley Taught Me

She looked down at me from above and smiled, but I wasn't paying attention to her face, my eyes drawn to all that was revealed up under her dress. Should I blatantly stare there or discretely turn away? Will she be offended if she knows how much of her I could see ... will she tell my mother if she catches me? I didn't want to be branded the family perv kid.

She looked away again, directing her attention to the leaves in the gutter, enabling me to stare even more intently up under her dress, realising that she was wearing stockings. It had been slow to dawn on me because they were sheer flesh-coloured. Pre-pantihose, stockings were the going-out dress code for women back in the early sixties, but why would a woman wear stockings just to lounge around the house on a Saturday morning?

"Oh my god, this wasn't very smart of me to climb up here, was it? I bet you can see right up under my dress, can't you? Just as well I put on some panties today. Sometimes when it's hot, I don't bother."

What do they call that these days ... going commando?"

I only half heard her admission, my gaze now unswerving, my eyes rivetted up under her dress. I could see all the way to the tops of those stockings, see where they were attached by a thin strip of material to her underwear.

"So, I guess you had a good look, young man?"

I heard that clearly, was that her serious voice, and addressing me as young man instead of by name? Had I pissed her off by blatantly staring at all she displayed beneath her dress?

"Sorry Aunt Shirley, I couldn't help it. I looked up to answer you and it was all there ... hard for me to look away."

She was clambering down the ladder. I was now concerned that I could have offended my aunt, so I exercised discretion and nervously looked at the ground.

"That's ok Paul, it was my fault. I've known you all of your life, saw you grow from a baby. Now you've become a handsome young man, and you're 18. I need to be more careful around you ... your loins are probably flowing with raging hormones."

Why had she gone up the ladder herself when that was the reason I was here? She stepped off the ladder, turning to face me. She was quite close, much shorter than me without her shoes. She looked up at me. "I must be more prim and proper around you now you're all grown up. Have to be careful not to give you sneaky peeks like that, might get you all horny."

My aunt was very astute. My cock had sprung to an erect state within my shorts. I was embarrassed, she would only need to glance down to spot it tenting my shorts.

"Yeah, that's quite possible," I dared to admit.

I saw her eyes look down, "Oops, too late, you already have a reaction. I'm sorry Paul, better not tell your mother I let you see what you did. Would you prefer to wait a bit, have another cold drink to cool off before you start on the gutters?"

I must have been red in the face from my embarrassment, fancy getting a hard-on large enough for my aunt to notice. I mean, at 18 in 1963, a young guy just didn't say or do anything sexual in front of adult relatives, particularly one of the opposite sex.

"No, I better get started," I told her, putting my foot on the bottom rung. I climbed up, setting out to complete the task my aunt had set me as quick as possible. I tried to immerse myself in lifting bunches of leaves from the gutter and dropping them to the ground below me. But as much as I might attempt to concentrate solely on this task, my erection would not soften.

This chore up the ladder for my aunt didn't require any mental stimulation, freeing my mind to recall looking all the way up under this mature woman's dress, an image so exciting to an 18-year-old back then. Those perfectly shaped long legs, seeing them all the way from ankles to where the tops of her thighs disappeared into her panties, encased in the sheer stockings and that clasp -- what's it called, a suspender - also disappearing within her panties. I found it all so sexy. I had heard the term voyeur ... was I one now?

If only my damn erection would abate, embarrassing for me that my mum's sister had spotted it. After last night's frustrating date, I really needed to get off with my hand again this morning. I tried to convince myself that my hard-on came from the circumstances of last night, and not being turned on by looking up my aunt's dress.

Perched up high up on the ladder, I heard a sound beneath me. Looking down, I saw my aunt raking the leaves as I dropped them to the ground. Aunt Shirley smiled up at me, "Going well Paul, you're doing a great job. Thanks for coming over, I must pay you for your time."

"No, that's not necessary," I called back to her, reflecting that she already has by giving this horny teenager a good free peep show that will contribute to my sexual awareness.

I continued working, but after a time, I realised that I could no longer hear the raking sounds. I looked down to see my aunt standing at the foot of the ladder, leaning on the rake, staring up at me. How long had she been doing that and what held her interest so intently? Was she emulating what I did below her, having a good look? From where she stood, she could see up the open leg of my baggy, but short, shorts. Unlike her, I'm not wearing any underwear beneath my shorts ... not even boxers.

My balls were hanging free and, with my erection stiff and not wilting, she would clearly see much of my cock shaft, standing horizontal and hard out from my body. my short shorts tented. Even now, I recall how so many things embarrass an 18-year-old. But up the ladder, there was nothing I could do to hide it or to stop her from checking me out ... if that's what she chose to do.

My Aunt Shirley was perving up at me the way I had perved up her dress. But why ... in my naïve teenage state back then, I didn't comprehend why a 30-something woman, who outwardly seemed to have no interest in males, could be so fascinated by a teenager's hard shaft. Surely a mature adult woman would have enough men of her own age to assuage her appetite for a rampant male body, if that's where her interests lay. Because she never brought a date to family functions, the jury was still out on my aunt's sexual tastes.

I tried ignoring the fact that my aunt was standing below, staring upward intently, appearing to check out my hard-on. 'Concentrate on the leaves,' I told myself, but confused by my aunt's behaviour, my thoughts recalling last night's date and my attempted make out session with my girlfriend. The memory of getting closer to getting laid than ever before caused my cock to jerk. I do now in 2020 remember 18 as the age when my cock seemed to be hard more often than it was soft.

I had a quick feel, found to my additional embarrassment, pre-cum was leaking profusely from the eye of my cock, leaving a prominent wet spot on my shorts. I might have to stay up this ladder until my shorts dry.

Damn! I had removed every last leaf within reach. I was going to have to climb down so I could reposition the ladder to another spot to allow me to continue with the task.

"What's wrong Paul?" I heard my aunt asking from below me.

"I've got all the leaves that I can reach, I'm going to need to move the ladder."

"Ok, then come on down. I'll hold the ladder steady, I'd hate for you to fall."

I guess holding the ladder would be her excuse if I asked her why she was standing below, staring up through the gap in my short shorts ... a bad choice to wear as it turned out. I reluctantly clambered down the ladder until my feet were back on firm ground. I hung on to the ladder, pulling it away from the side of the house, moving it a few feet to the right, keeping my back to my aunt, embarrassed that she might see the large wet spot that had formed on my shorts.

Damn! Underwear would have absorbed my leaking pre-cum, but there was none in my dresser drawer this morning. Strange, because my mom, who always did my washing back then, ensured I always had clean clothing - outer and underwear.

I moved the ladder, propping it back against the house. To my surprise, my aunt slipped behind the ladder, placing her between it and the house. She stood looking between the rungs as I reclimbed, the front of my body passing in front of Aunt Shirley. I had no way to conceal my teenage embarrassment at having such an obvious and raging hard-on in front of my aunt. I climbed ... was that a gasp I heard as my body passed within inches of her face?

I diligently applied myself to the task, clearing out the accumulation of leaves from the guttering. When there were no more within reach, I looked down, Aunt Shirley was nowhere to be seen. I descended the ladder.

My feet touched firm ground and I repositioned the ladder, intending to climb back up to continue my chore. But before I could ascend again, my aunt appeared from the back door of her house. She carried a tray with a pitcher of what looked like lemonade, with ice floating, and two glasses. "Time for a break Paul, I thought you might be hot and thirsty."

"I sure am, thanks Aunt Shirley."

"Come on, we'll go drink over by the pool."

She set out to walk across the back lawn toward the pool area. I followed a few steps behind, my eyes drawn to the way her hips and arse moved so sexually in that loose summer dress. Never before had I been so aware that my aunt was this sexy. My erection had at last subsided while I was up the ladder the second time, although staying half erect. I felt it twitching as I followed her to the pool area, unable to tear my eyes away from the sexy sway of her arse.

She stood beside the table in the pool area and poured out two glasses, handing me one, "There you go, that should cool you down. Don't want you becoming too overheated."

I took the chilled glass from her and swigged down the lemonade, "Thanks Aunt Shirley, I needed this."

"Oh Paul, you've grown into quite a young man now ... it seems almost overnight. I think it's time for you to stop addressing me as aunt, Why not call me just Shirley?"

"I don't know, I've called you aunt all my life. I would find it strange to just call you ... err, Shirley."

"Please try Paul. So, sit down, tell me how you've been. Your mother tells me you have a new girlfriend, is that true? I want to hear all about her and how your is life these days. Is it serious?"

"Well, I'm serious Aunt ... err, um, Shirley. She is my first ever girlfriend."

"So, is she nice? I'll bet she is, my sister has raised such a perfect young man, you are such a gentleman. I can't imagine you dating any girl who was not nice."

"Depends on what you mean by nice. To me, she is beautiful, and smart too."

"Well, that's a couple of good attributes to start. You said you're serious, do you think she is too?"

"She seems to be, we've been going out for three months and she never says no when I ask her out."

"So, three months steady, how is the sex?"

I was taken aback by my aunt suddenly asking such a direct question. This was 1963. I appreciated her being interested in my life, but that was too personal. I think my mouth was open.

She took my silence as a no, "Don't tell me you're not having sex yet, Paul?"

My aunt's direct question caught me completely by surprise, coming straight out with it. Was it any of her business ... perhaps she was asking on mom's behalf? If I chose to answer, should I tell the truth or make up something to get her off my case? "Err ... well, we've only been going out for twelve weeks."

"What does that mean, that's not an answer Paul?

"Well, I think maybe it's a bit soon."

"So, you and she haven't yet, have you tried?"

All morning, I had thought of little else but trying last night. I squirmed in my chair. Only 18, I felt uneasy discussing my sex life -- or lack of - with my aunt. I can't recall ever having any long and meaningful discussions with her, I wasn't about to have my first centring on sex.

"I ... err, um, I don't think I want to say."

"Why not, is she a virgin then?"

"I ... err, um, I think she might be," attempting to answer my aunt when I saw her frown at my hesitation.

"You don't know, haven't you two even talked about sex, let alone do it? And what about you, are you a virgin too?"

"I only think of women being virgins, Aunt Shirley, not males."

"Hmm, in a way that's true. I mean, young men don't have anything on their bodies to be broken or torn apart, but I think our society classes as virgins if they haven't had their penis inside a woman yet."

Was I blushing red from her very direct questioning ... a woman 14 years older than my tender 18 talking about my penis? She didn't let up, "So, if you've never done it with a girl before, you wouldn't have experience to read the signs. We females can be confusing creatures at times, your girlfriend might want to have sex with you and she's waiting for you to make the first move."

She seemed to be goading me into what she wanted ... to reveal my sexual experience. "I might not know much about sex yet Aunt Shirley, but I reckon I'd know if she was ready. I mean, I thought we might have started last night, I tried nearly everything I could and she still stopped me."

Her eyes sparkled at my revelation, "Did you now? Tell me how you tried?"

I was still hesitant, what was the point of telling her? My instinct was not to, but seated opposite me, she looked keenly interested, so I did. "We went parking in mom's car after seeing a movie, my girl was wearing this new bra. I figured she might have bought it specially for me to see."

"And touch too, eh Paul?"

"Yeah, possibly ... it was really soft and transparent, I think it was nylon."

"So I guess that you got your mouth on her breasts ... or at least on her nipples?"

"Only through the material of her bra."

"Did she seem to like that?"

"Oh, did she? Yeah, she was breathing heavy and making all these soft sounds."

"Like purring?"

"Yes, something like that."

"That does sound like she was really into what you were doing. Was that the first time you'd been able to get your lips on her breasts?"

"Yeah, it was ... sad, eh, and I'm 18? I've never had more than one date with any girl previously."

"Never mind, you're just a late starter. So, you managed to suck her nipples ... what else?"

"You're a very curious aunt," I would prefer not to tell her, but she had a way of questioning that was very compelling, making me feel like I needed to answer truthfully, "Well ... I, err ... I put my hand up under her dress."

"While you were still sucking her nipples?"

"Yeah!"

"Umm, that is such a familiar and typical male move ... I guess some things don't change." She said that almost wistfully, like she was reminiscing. "I couldn't count how many times that's been tried on me."

"Oh really!" I was genuinely surprised by her admission, but with hindsight maybe I should not have expressed that surprise so openly. I recall raising my eyebrows ... did that imply to her that I didn't think she would know that much about males?

"Yes! Do you think I wouldn't know anything about what guys do? Paul, you and our family can make whatever assumptions you want about me and my sex life. Just because I choose to never bring a man to any family events. That doesn't mean I'm celibate?"

I rushed to apologise for fear of offending my favourite aunt, "I'm sorry! I didn't mean..."

Her words stopped mine, "Don't worry, your reaction is the same as the rest of the family, you all assume I know nothing about men because I'm never seen with one. You'd be very surprised how much I know about men and what makes them tick. I might tell you one day. I am very aware of what's going on whenever there is a man around me ... even you, my dear nephew. Like knowing that you had a solid useable erection when you were up the ladder before. Do you want to tell me where that came from? Your penis was even leaking some pre-cum too. See, I notice all those things."

I knew she had got a glimpse, she couldn't miss it, thanks to me not wearing any underwear. Should I tell her, admit to my aunt how much I had seen of her earlier? "I ... err, I ... um, got hard when you were on the ladder. You spoke to me from up there and looking up, I couldn't avoid seeing up under your dress. To talk to you, I couldn't look anywhere else."

"How far could you see ... all the way up?"

"Yeah, all the way."

"Oh, how embarrassing! Could you see up to the tops of my stockings, Paul?"

I squirmed in my chair some more, hesitant to admit. I didn't want to be labelled a pervert within the family, "Yes, I could."

"What about my panties, Paul, could you see all the way up to the tops of my legs, could you see my panties?"

"Err ... yes I could, only just!"

"What colour do I have on today?"

"Pink!" I answered, perhaps too quickly.

"Umm, so you did get to see them. Did you enjoy having a good look?"

I avoided eye contact, looking down at the glass in my hand, mumbling "Yes!" unable to look at her.

"So, being able to see what's up under my dress made you hard, did it?"

"Umm hmm!" nodding my head affirmatively, raising my eyes slightly, looking for her reaction.

"You got that hard despite me wearing panties? Imagine how hard you might have been if I wasn't wearing any? Seeing under my dress must have really turned you on?"

Oh, how should I answer that? I didn't want to make her angry. I chose the truth, "Yes it did."

"Were you turned on by what you could see because it was my bits, or were you looking and thinking whether it would look like that under your girlfriend's dress?"

How to answer that too? Which is the right answer, I don't want to offend my aunt? "No, I think I got hard because it was you."

"So, seeing all the way up my legs, the tops of my stockings and a glimpse of my pink panties got you that hard, eh?"

I kept my head lowered, embarrassed to admit that I had looked and that some harmless patch of bare skin, stockings and underwear could cause such a reaction. It's not like I could see her pussy in the flesh, "Yeah!"

"Don't be embarrassed Paul, I told you I know a lot about males and what turns them on. I'm not at all surprised ... in fact, to tell you the truth, a woman my age feels good to get such a reaction from a young healthy man like yourself."

"But you're my aunt ... my mom's sister. That's not right for me to get so turned on just from seeing under your dress."

"Oh, don't go down that path Paul, society sets some very harsh standards. What harm is there in my letting a nice young man like yourself have a little peep here and there. I'm a woman -- I think I'm very feminine -- and I like to think that I am still attractive on the wrong side of 30. You are a horny young man, anxious to get started on a lifetime of sex. What could be more natural than that?"

"You're the one I'm trying to protect. If it doesn't worry you, I guess it shouldn't bug me."

"So Paul, you explained why you got a hard-on earlier, but that was a half-hour ago. Why are you half hard again now?"

"How do you know I am?"

"I saw the shape of your penis in your shorts when I handed you your glass, I'm guessing it's about half erect at the moment. I haven't flashed you again."

Should I admit to her? "I ... err ... I, um, I guess I got turned on from walking behind you, following you over here from the side of the house."

"Why, what was arousing about me just walking, I was covered."

"I liked watching the way your dress swirled around your legs as you walked ... you have perfect legs ... and the shape of your bottom. I mean, I couldn't see it like I would if you were in a bikini, but I like the way it moves when you walk."

Did all that come out of my mouth? I was basically a shy kid at 18 so for me to pour forth all the thoughts I had as I watched her body move was extraordinary.