Absolutely true story-my Aunt JoAnne was and is the best lady in the world. We should all be so lucky.
The summer I was 13 was a bad one for me in many ways, since my parents were in the midst of a divorce. The tension and fighting was unbearable, and on several occasions I ended up spending several days and nights at my Aunt JoAnn's house. (She is my mom's sister.) It was a relief because I could get away from all the crap going on at home. Aunt JoAnn was great. It was like an oasis. She had a beautiful house on about five acres, with a beautiful swimming pool and tons of woods and stuff to explore and play in. She had been divorced about three years earlier and worked part-time as secretary, but I found out years later that when the divorce went through she got a ton of money from her ex-husband.
In any event, Aunt JoAnn was very cool, even for a lady approaching fifty. She was laid back and pretty much let me do what I pleased, partly I think because she knew what I was going through at home. Now while she wasn't an incredibly beautiful woman (she was rather 'hefty'), she did have a very fun and outgoing personality and a cute smile. And of course what caught my attention were her very large breasts. At thirteen I was perpetually horny, and at the point of this story had been masturbating daily for almost a year. I had seen a few Playboy magazines but had never seen a real girl or woman in their underwear, much less nude. That changed this one night at Aunt JoAnn's.
I spent most of the afternoon in the pool, hanging out with music blaring from the radio, drinking soda and munching on snacks. Aunt JoAnn arrived home late in the day and came around back to tell me she had had a LONG day and was tired and hot and would be joining me for a swim shortly. It was always a treat for me when she took a swim, which didn't happen often, because I got a great view of her breasts. She came out about ten minutes later in her usual swimsuit, a one-piece 'old lady' style, black with pink stripes up each side. Not terribly revealing or flattering, but her breasts stretched the fabric across her chest and her cleavage was quite visible. As she gingerly stepped into the pool, I kept staring and in no time I had an erection. I cautiously toyed with it under the water as Aunt JoAnn swam around and we chit-chatted. After her brief dip she worked her way up the steps and out of the pool. I stared at her rather large ass, which her tight wet suit accentuated. I thought it was great! She toweled off and told me she was going inside to fix dinner, and I should come in and get changed.
Dinner was uneventful. After I helped her clean up we continued on with our nighttime routine. Aunt JoAnn got on the phone for several hours (god knows who she was talking to) and I watched TV. As it got late she came into the living room and told me it was bedtime and gave me a peck on my cheek. She went downstairs to her den to watch TV and I went to the bathroom to pee. As I closed the door my eyes saw her swimsuit laying across the shower bar, drying. Not anything unusual. But as I walked in further I saw the hamper in the corner, which was full to the brim with clothes. On top were a pair of Aunt JoAnn's panties. I couldn't resist...I picked them up and I immediately got hard just from holding them. I was even more excited when I saw her bra underneath. Not even thinking, I grabbed them and ran to my room, closed the door and jumped into bed.
The first thing I did, something I had been dying to know for a while, was check out the tag on her bra to see what size it was. It was a Bali bra, with lacy cups and underwire, and pretty wide straps. She needed the support! The tag read 38DD. I was in heaven. I lay on top of the covers and slide down my pajama bottoms, freeing my hard little cock. I was pretty small then, about four-and-a-half inches hard, but I had large ejaculations (and still do to this day). I placed Aunt JoAnn's panties down in my crotch and began to rub them against my cock. They were nylon, not particularly sexy but the feeling was incredible. I knew Aunt JoAnn always stayed downstairs and went to bed late. Her bedroom was across from mine. I had no concern of her interrupting me. That was a big mistake.
I heard a quick 'knock-knock' on the door, and the door opened without me responding. Aunt JoAnn stuck her head in and started to say, 'I was thinking about tomorrow...' when she saw me there, pants down to my knees, her underwear in my hand, and a full blown hard on. I was mortified, and scrambled as fast as I could to pull the bed sheet and blanket over me. Time seemed to freeze. With each passing second I became more embarrassed and I started to cry and tremble. I didn't know what she would do and I was scared. What happened next was the last thing I would have expected.
Instead of leaving and shutting the door, Aunt JoAnn came in and sat on the edge of the bed. She hesitated a moment, then leaned over and took me in her arms and told me to calm down, that she wasn't upset. She held me until my tears finally subsided, which wasn't for several minutes. Finally I sat back, and she looked at me and smiled. She told me we should talk about this, and that she promised not to scold me. Aunt JoAnn told me that all boys my age are curious about their bodies and what I was doing was completely natural. She went onto say that she knows a lot of people have hang-ups about masturbation, but her belief was that if it feels good and no one gets hurt than it is fine. She told me that when her girls were about my age she sat down and talked to them about sex and masturbation, and actually explained to them the best way to do it. I was listening in amazement as she talked so calmly about what I had been doing.
She asked me if my mom or dad had ever talked to me about sex, and I shyly told her no. She said it's nothing to be ashamed of, and that she would be happy to answer any questions I had. I was still too nervous to say anything, and she asked if I had ever seen a girl naked. I said no, and she said that it's perfectly natural for a boy to wonder what a girl looks like without her clothes on. She told me how when she was twelve she was obsessed with seeing what a boy's penis looked like until she and her best friend spied on her brother getting changed one day. She told me how it made her excited and that her friend had taught HER about masturbation. I was at this point not only becoming more at ease, but also aroused, thinking about Aunt JoAnn as a little girl, masturbating.
She patted my knee and told me that I could feel free to masturbate in private whenever I was there, but to keep the door closed. She promised not to walk in without me answering again. As she got up to leave she picked up the panties I had been playing with off the floor, and she asked if I had enjoyed rubbing them on myself. I shyly replied yes, and she told me that she would show me something if I promised not to tell anyone. I wasn't sure what she was talking about, so I said sure. She stood in front of me and lifted up the hem of her nightshirt, slowly, until it was up to her waist, exposing her panties to me! As I mentioned, she was a big woman with an ample stomach, but the sight of her in her panties was amazing. She smiled at me and said that it would be OK to masturbate just this one time with her there, that she would actually enjoy seeing me feel good. I kicked back the covers without thinking and my cock sprang forth. My hand was on it in a second. She smiled and told me not to say anything. She lifted the nightshirt up and over her head, leaving her standing in front of me in just her panties. She had no bra on! Her breasts were everything I imagined, and I was completely amazed at the size of her areolas; they were easily bigger than silver dollars, and her nipples were standing out in the middle of them. I was tugging pretty good on my cock, just staring and stroking, when Aunt JoAnn sat back down on the edge of my bed, still smiling. She reached toward my cock and gently nudged my hand away, and she held the finger of her other hand up to her lips and made the 'shhhhh' sign. She then reached down and slowly stroked me with her left hand, and her right cupped my testicles. My hips began bucking shortly after she started, then I let out a moan and a sigh and she instinctively stroked faster, which caused me to ejaculate. I made a huge mess on my stomach, and one shot of come actually reached the base of my neck.
'That was good, wasn't it sweetie,' Aunt JoAnne said. I just nodded and smiled. Using her nightshirt as a towel, she slowly wiped all the semen off my body, returning at the end to my cock for a couple more small strokes. She reminded me that it was our secret. She kissed my forehead and walked out of the room. I will never forget her standing up, nightshirt in hand, huge breasts swaying, and her tight underpants showing off everything.
The next morning I woke up, wondering if I had dreamt the whole thing. I dressed and went out to breakfast and Aunt JoAnn greeted me with a cheerful good morning. Over orange juice and pancakes she reminded me again how what happened the night before must remain our secret and I promised her it would.
Over the remainder of the summer I stayed with her on several more occasions. She did become more free about leaving her door open while changing, although I never saw her vagina or pubic hair. I masturbated every chance I got. There was never a repeat performance but Aunt JoAnn and I maintain a strong relationship and friendship to this day. A few times I have sought her advice on girlfriends and sexual matters.