The following is a COMPLETELY true story.
As a 13 yr old boy, I frequently spent days at my 'aunt's' house since both my mom and dad worked full time. 'Aunt Kay' was really no more than a very close family friend (someone my mom grew up with) who lived only a few miles away. She was divorced and her only son was already graduated from college, so she lived alone in a very nice home on 2 acres with a great pool in the backyard. Many afternoons Kay and I spent hanging out, swimming, sipping drinks, and listening to music. She had a basketball hoop in the driveway, and frequently we would go on day trips to parks, zoos, etc. She was a very cool lady for being 52, and we got along great. She seemed to be very much in tune with what it was like to be a teenager, and I was very comfortable sharing all my inner thoughts with her, and even discussed on occasion girls I liked. She gave me 'tips' on how to handle girls, things to say and do, etc.
On one particular Friday my parents had arranged for a getaway trip for their anniversary, and I was all set to stay at Kay's for the weekend. During the day we ventured to a nearby lake, where we swam a bit and fished (Kay was surprisingly good with a rod and reel!). On the way home we stopped for dinner and rolled in about 10:00. She told me she was going to jump in the shower and when she was done I should take one too. I told her I would be in my room getting changed and to just knock on my door when she was done.
I retreated to my room and stripped to my underwear. At 13 I was perpetually horny, and waiting for Kay to finish up I was lying on my bed, daydreaming. My mind wandered and before I knew it I was hard and absent-mindedly playing with myself through my underpants. I was shocked when there was a quick knock on the door and it opened! Kay stuck her head in and as she started to tell me I could use the bathroom, she stopped in mid-sentence when she saw me sprawled on the bed with my erection pressing against my underwear. Being a pretty bright lady I'm sure she put 2 and 2 together and figured out what I was doing. She muttered a quick, 'OH, I'm sorry. You can use the bathroom now.' She quickly closed the door behind her and I was left with a quickly shrinking erection, embarrassed beyond belief.
When I was sure she was in her room I made a beeline down the hall and into the bathroom. As I showered I wondered if I was in trouble or if I was going to get a lecture. I was truly concerned that Kay was going to think I was a perv because I was playing with myself. As I stepped out of the shower and dried off, I noticed out of the corner of my eye, piled on top of the hamper in the corner, Kay's clothes. Resting right on top were her bra and panties! Checking to make sure the door was locked, I walked over and picked them up. They were a matching set, and rather plain. Immediately I checked her bra size (I had always been mildly interested in her boobs because they were so large, I thought) and found it was a 36C. Her panties were more a girdle-type, nylon fabric, and I was shaking as I held them. My thoughts and fears of seconds earlier were erased as I entered a state of high excitement (funny how 13 yr old boy's minds work hahaha). Instinctively, I think, I placed the panties around my cock and began to masturbate with them. The feeling was incredible, and I remember thinking, 'These were just next to a woman's privates and now they are touching my dick, WOW!' I was pretty nervous about being caught, so after a couple of strokes I made sure I put them, and the bra, back exactly as I had found them.
I then scooted down the hall to the bedroom and put on a pair of gym shorts and a tshirt (my 'night clothes'). As I was dressing, my worry returned, intensely now, about what Aunt Kay would say. I tried to walk casually out into the living room where she was seated on the couch, reading the paper. I grabbed the remote and clicked on the TV and sat down on the floor.
Oh shit, I thought. Here it goes.
'Yeah Aunt Kay?'
'Paul, I'm sorry if I walked in on you like that. I should have never opened the door without you saying it was OK for me to come in. I apologize. I know you're old enough now to be allowed to have the privacy you need.'
Whew. She wasn't going to lecture me. Or so it seemed.
'No problem, Aunt Kay. It's OK.'
I thought that was it. It wasn't.
'Paul, I want you to know what you were doing is nothing to be embarrassed about. Has your mom or dad talked to you about masturbation at all?'
EWWWW. She said the word 'masturbation'. I hadn't heard anyone EVER say that word before, not even my friends (it was called, in various places and times, jerking off, jacking, whacking it, etc.). I certainly knew what it was, and my parents for darn sure had never talked to me about it, or sex in general. Nor would they. That's just not the way it was. That was taboo and hush-hush in our house.
'Uh, no' was my only reply to her question.
'Well hon, it's perfectly natural and there's absolutely nothing wrong with it. It's very enjoyable for men and women, and boys and girls your age. God meant for us to enjoy the good feelings that come from sex, and you should never be ashamed about masturbating.'
I could not BELIEVE she was talking about this. I could feel myself blushing, but I was also aroused. It was a combination of moments early playing with Kay's panties, being caught touching myself in my underwear, and now her actually talking about sex! In no time my erection was pressing against my shorts, and I tried to make a conspicuous attempt to hide it.
'Paul honey, if you have an erection now you can go in your room and take care of it. I don't mind.' I was stunned. Here was my 'Aunt Kay', cool as she was, telling me it was fine with her if I got up and went to my room and jerked off. I glanced back at her, and she was smiling a motherly type of smile.
'Really honey, I'm serious. I know how boys at your age get. Be my guest. I have plenty of things to do around the house here.'
I hesitated, started to get up, realized I had a huge erection she would see if I stood up, and sat back down. She got up and went into the bathroom, and I took the chance to half walk, half run down the hall. I went into my room and shut the door. I fell on the bed, breathing hard, and my hand went under my shorts to my cock. In 10 seconds there was another knock on the door, and this time Kay waited to open it. I sat up and put my hands in my lap, and said shakily 'Come in'.
Kay opened the door a crack, poked her head in and said, 'Mind if I come in for just a sec?'
'Sure, OK' I said.
She walked in and sat on the edge of the bed. I noticed 2 things: first of all, she smelled great after her shower. REALLY great, even though it was probably just 'old lady' perfume or soap or something. Secondly I noticed that her nightshirt (which was flannel and down to her knees, nothing very sexy) was not buttoned to the top and I could see a bit of cleavage. She was holding a bottle of Johnson's Baby Oil in her hand.
'I don't know if you use this or not, or Vaseline, but it makes masturbating for a boy very pleasurable. I could show you if you'd like.'
'Show me?' I wasn't getting it.
'Yes, show you. I can make sure you are doing it correctly so that you get the most pleasure out of it. It would be our little secret, hon of course. I could just be your teacher this one time, and I'm sure from now on you'll have a lot more fun when you do it by yourself. OK?'
I was shaking. And horny. I wasn't sure exactly what she was saying (was she going to watch me and give me tips, or actually do it to me?). Either way sounded REALLY good to me.
'Uh, OK' I squeaked.
'Great!' She was bubbling with enthusiasm. 'Well then, let's start by just taking off those shorts.' I hesitated before slowly sliding them down my legs. I sat back on the bed, covering my dick. I was embarrassed, scared, and nervous - I was a whole bunch of things.
'Don't be shy, sweetie. Here, hold out your hand.'
I did, and she squirted a puddle of oil into my hand. She put the top back on and told me she would be right back, to go ahead and get started. I was confused, but laid back and spread the oil all over my erection. She was right, it felt GREAT! She returned a minute later with a towel and washcloth.
'Forgot these. Thought we might need them. I see you started without me.'
She sat on the edge of the bed. I was lying length-wise of course, my head on the pillows. She sat facing me, with her rear about even with my stomach. She crossed her right leg over her left at the knees and leaned back on her right hand, which was inches from my thigh.
'So how does that feel? Good?'
'Oh my God yes.' I said. I was quickly entering 'The Zone' and any of the weirdness of the situation was evaporating.
'Would you mind if I showed you a few things?'
I just shook my head. As if she were teaching math or baking a cake, Kay proceeded to give me tips on how to vary my strokes, increase/decrease pressure, accentuate focus on the head of my penis and how to couple my stroking with testicle play. She was like an expert! She never touched me, just talked to me about how to do things. After about 10 minutes I was ready to come and she could tell. She said, 'Hon, don't ejaculate yet. Slow down for a bit, and if you can wait I'll help you finish.'
I stopped and looked at her. She said, 'Let me finish you, honey. Would you like that? It will be my special treat for you.' I shook my head again, speechless.
She reached down and unbuttoned a button on her nightshirt. Then another. And another, 'til they were undone halfway down. I could see the waistband of her panties, and 3/4 of her breasts were visible. They sagged quite a bit, but they were the first real naked ones I had ever seen.
She smiled at me and reached over to the night table, grabbed the baby oil and squirted some in her hand. She rubbed it all around both her hands, warming it, and then she non-chalantly leaned over and took hold of my erection with both hands. She worked it like an expert, and as she leaned close to me her head was inches from my chest. Her fragrance was wonderful. She whispered to me, 'You can touch my breasts if you want, Paul'.
I reached down with my right hand and found her tits. They were soft and warm, and as I made contact she sat up to give me better access (and a view of what I was touching) and she sighed softly. 'Mmmm, your hands feel nice, hon.' I rubbed and caressed and squeezed her tits, feeling her hard nipples run across the palms of my hands. HER hands sped up, and in moments I was on the verge of coming.
'That's it baby. Go ahead and come. Make yourself feel good.'
She pressed close to me, and leaned over. She kissed my forehead as she stroked me to orgasm ('backhanded' by the way...). Her breasts were in my face. As I unleashed my come. I felt the wetness spread up to the middle of my chest and leaking down between my legs, and a puddle of come forming just below my bellybutton. I had come more than I ever had before, at least 5 healthy squirts. As Kay slowly sat up she chuckled and said 'You got me!' She lifted up her arm, revealing the side of her nightshirt with a large wet spot of come on it.
'Go ahead and clean up, Paul. Then we can talk.' She tossed me the towel while she picked up the washcloth and wiped off her hands.
She stood, buttoned her nightgown up, leaned over and gave me another peck on the forehead and left with a smile. We ended up in the living room 5 minutes later and (with the TV off) had a long talk about how tonight was special just to us, and no one else must know. We remained very close through the years, and she would occasionally ask me, in a very light-hearted and kidding manner, how often I was 'doing it'. We were never intimate again, and the last I heard she was living in New Mexico with a man she met on a cruise. Today she is probably 75 or so.