Story about my friend Charlie and me, having fun with a pair of my Aunt's panties and bra that I 'stole' from her bathroom. I am now a lifelong panty lover, and have 'borrowed' panties from friends' wives', my nieces', and sister-in-laws' to masturbate with.
This experience happened 20 some odd years ago, when I was 12-1/2. During that summer my mom would frequently drop me off at my Aunt Becky's house on her way to work. (She wasn't a real Aunt, just a close friend of my mom's and that's what I called her.) My mom and dad divorced the year before, and my mom had gone back to work as a secretary at an office in the next town over.
I really didn't mind going to Aunt Becky's since she had a REALLY nice house, with a nice pool in the backyard. There were lots of kids in the neighborhood, and I became friends with Charlie one of the first days I was there while I was riding my bike out in the driveway. He was my age and pretty cool, and eventually we would spend a lot of afternoons hanging out in Aunt Becky's pool, just swimming and goofing off like kids that age do.
Mostly Aunt Becky would leave us alone, but maybe once a week she would sit out by the pool and occasionally take a swim if it was really hot. Now she wasn't a young, beautiful 'hot' woman by any stretch of the imagination. She was probably in her late 40s/early 50s, kind of overweight, with short brown hair that was beginning to turn gray. What I noticed (and I found out Charlie noticed too) was that she had very nice breasts. And while she typically wore an 'old lady' one-piece bathing suit, it couldn't hide how big they were. On this particular day Charlie and me were splashing around in the pool, and Aunt Becky was sitting in the lounge, reading a magazine. She walked over to the edge of the pool in the area we were in, knelt down and bent over to grab the thermometer to check the temperature of the pool. As she did we both got a tremendous view of her cleavage from a mere few feet away! Charlie and I both stopped dead in our tracks and simply stared, and after a few seconds he elbowed me and giggled and we both dove under the water. When we came back up Aunt Becky was walking back towards the house and we both just watched her plump rear jiggle in her bathing suit.
That short event kick-started a discussion about sex. Charlie made some kind of crude comment like, 'Holy Shit, did you see the size of her tits!' and it just went from there. We began to ask each other about things we had either heard about or seen. He told me he had seen naked girls in a Penthouse he found under his brother's bed, and I told him I had heard about a girl in the grade above us who had given a guy a handjob behind the school while he played with her tits through her shirt right before school got out. We talked on and on about 'hot girls' we knew, and what they must look like naked. Of course I was hard as a rock while we talked about this, and I'm guessing Charlie must have been too, but after a while Aunt Becky came back out (dressed now, it was pretty late in the afternoon) and said it was time for dinner and Charlie had to go home.
I went inside and Aunt Becky told me to get changed and come to dinner. I grabbed my gym bag containing my shorts and t-shirt from the guest room I used and went to the bathroom to get my wet suit off. As I stripped off my suit I noticed I still had a raging hard on, and at that point in my life I had heard about jacking off but didn't really know how to do it. I just stood there, kind of toying with it and pulling it down and letting it bounce back up to slap off my stomach. While I wasn't out and out jerking off, it DID feel good. Out of the corner of my eye I noticed that the clothes hamper in the corner was open, and it was filled with clothes. As I peered in, I couldn't believe that lying on top was a pair of Becky's panties! I picked them up, and underneath was a bra! It was like I had won the lottery. The panties were tan; actually they were more of a girdle, made out of nylon. The bra was white, with full cups that were edged in lace, and the strap across the back was wide, with 3 hooks/clasps. I noticed a label, and saw that it was a size 36DD. My imagination went wild as I pictured Aunt Becky standing in that very bathroom, taking off her bra and exposing her large breasts. I imagined she had large pink nipples. (Charlie that very afternoon had explained to me how some women have gigantic nipples; I wouldn't have known because I had never seen a naked woman before, in real life or in a picture.) Her lingerie had a faint scent of perfume, and I held her underwear up closer to my face and inhaled the scent. I loved it, and the feel of the nylon of her girdle was like silk to me. Instinctively I took the panties and rubbed them all around my penis. (I guess it was instinct, why else would I have done it?) I thought I had died and gone to heaven, when my reality came crashing in with a knock on the door. Aunt Becky wanted to know what was taking so long, and told me to come to the table because dinner was getting cold. I quickly put the underwear back in the hamper, pulled on my shorts and t-shirt and went to dinner, shaking slightly as I sat down.
I looked at Aunt Becky in a whole new light all throughout dinner; she had on a white button down blouse through which I could make out the outlines of her bra. She had on light pink shorts that were just a bit snug in the rear, and as she cleaned the table I stole glimpses of her ass and could easily make out the lines of her underwear. I was perpetually hard for the next hour, until my mom came to pick me up and bring me home for the night.
The next day was a Friday (for one reason or another I remember...) and I was dropped off at Aunt Becky's at 9:00 am. It was kind of gray and cloudy and cool, not really a swimming day. After checking in with Aunt Becky, I went outside and, not surprisingly, Charlie showed up on his bike about five minutes later. I told him we should go down in the woods because I had to tell him something. He dumped his bike on the front yard and we ran through the backyard, into the woods and down the path about 100 yards to a small clearing. We sometimes hung out back there, and we had pulled a couple of logs together and cleared out some of the twigs and brush and leaves to have our own little hideaway spot. I sat down on one log and he sat across from me and I proceeded to tell him how I had found Aunt Becky's underwear the previous afternoon, and described every detail. I noticed him squirming, and a few times he adjusted himself through his shorts. After I told him about it for the third time (he couldn't get enough), he sighed and told me he was horny. I simply said, 'Yeah, me too.'
Then Charlie had a brainstorm; he said that I could sneak in the house and see if the underwear was still in the hamper, and if it was I could stuff it in my shorts and bring it down into the woods and we could look at it together. I told him I would get killed if I got caught, then he said if I did then he would ride home and sneak into his brother's room and look under his bed to see if he had any dirty magazines there. That sounded great to me. So off we went, agreeing to meet back in the woods in 30 minutes. I went in and found Aunt Becky on the phone in her bedroom, talking while she was knitting. She didn't even notice me. I casually went into the bathroom down the hall and closed the door. The top of the hamper was down, and I wasn't hopeful, but when I lifted it up found it full to the top, with the same panties that were there the evening before. I grabbed them and the bra, and shoved them into my shorts and underwear. My dick sprang to attention, and I peeked out the door before making a beeline down the hallway, across the foyer and then dashed across the lawn to the woods.
I had to wait another 15 minutes before Charlie finally came back carrying what looked like a catalog. When he got closer I saw it WAS a catalog, and he said when there was no dirty magazines under his brothers bed, he saw the Sears catalog by the front door and grabbed it. He said there were pictures of women in their underwear inside, and he said I could look if he could see the bra I was holding.
The next 10 minutes or so were kinda weird; two very, very horny 12-year-olds looking at pictures of women in their underwear, and handing a bra and pair of panties back and forth for inspection. It was beginning to get awkward until Charlie finally asked THE QUESTION: 'Do you ever jerk off?' I didn't, and told him so. I told him I sometimes had wet dreams of hot ladies and I woke up feeling really good, but had never really done it to myself. He laughed and said it was AWESOME and he spied on his brother doing it about three months ago and that's how he learned to do it. He went on to say that he REALLY felt like doing it right then because he was so horny and wanted to know if I would mind. I was of course very, very curious and told him no, it would be ok, and then he said maybe I could try it too. Strangely my nervousness seemed to melt away and was replaced by this almost animalistic horniness. I had never felt so aroused in my life, before or since. I told him that ok, maybe I would try doing it too.
Charlie lifted his butt up off the log he was sitting on and yanked his shorts and underpants down in one swift motion. His cock was very thin and long, and very hard. He had a bit more pubic hair then I did, and I noticed his balls hung very low. He was holding the panties and I had the bra and the catalog open to pictures of middle age women in girdles lying on the ground in front of me. He took the panties and made a fist and began sliding them up and down his erection. He lifted up his t-shirt and exposed his belly, looking down at his cock and what he was doing. With his shirt up, pants down around his ankles and jerking off with Aunt Becky's panties he was quite a site. He sighed and told me how unbelievable it felt, and that I should try. I couldn't wait; I stood up and quickly lowered my shorts and underwear before I chickened out, and mimicked his up and down motions-at least I thought I did. After several seconds Charlie stood up and said, 'No, no, no, not like that. Here, let me show you.' I thought he was going to SHOW me. I couldn't believe it when he stepped slightly behind me and off to my side and grabbed my cock and began stroking it. I was shocked momentarily, and then got lost in the pleasurable feelings of his hand on my cock. He obviously knew what he was doing, and I mumbled something about us being queer, and he said it's not if you just use your hands, and told me to just pretend he was a girl giving me a handjob. I relaxed and let him jerk me off for a few seconds, but I tensed a bit when I felt his erection pressing against my hip. Then he said he had an idea: If I put on my Aunt's girdle he would pretend I'm a girl and would 'pretend hump' me and then I could do the same to him.
I didn't know what to say. But he kept egging me on, and I finally said ok, what the hell. I kicked my shorts and underwear all the way off and we both giggled as I slipped on the panties. They were big on me, but my erection got even firmer as I felt the material press against my cock. Before I knew it Charlie was behind me, and I felt his erection press up against my butt. It slid easily up and down my ass crack, and I could feel how hot his cock was right through the girdle. He grabbed my hips and was groaning and grinding very fast, and after about one minute he grunted and cried out that he was 'going to shoot.' I turned around and his hand was flying up and down his cock, and then he shot out 3-4 streams of semen that plopped onto the ground making little white pools. His hand also had a few globs of semen on it, and he wiped it on his thigh. I was amazed at seeing him shoot his semen all over and also the look on his face as he orgasmed. After seeing all that and how good he said it felt, I wanted to try too, and I stepped out of the girdle and told Charlie it was my turn. He hesitated at first and then said, ok but hurry up because he was then afraid of someone catching us.
He leaned forward with his hands against the trunk of a large oak tree, and kind of stuck his butt up in the air, laughing. I imitated his motions of a few minutes earlier, and easily found the crack of his butt and began sliding my cock up and down the nylon material. I found that the harder I pressed, the better it felt, and the harder I pressed the closer my whole body got to Charlie's. I held onto his hips for leverage and my chest was pressing against his back, the front of my thighs pushing against the back of his. Before I really knew what was happening I was coming, ejaculating like no tomorrow. As I did I pressed my cock even harder against Charlie's butt, and imagined it was Aunt Becky's ass that was making me ejaculate like that. When I was finished I had quite literally soaked the entire back of the girdle with my come, and Charlie was disgusted by it. We decided to hide the panties and bra in the hollow part of one of the logs because I was afraid to put them back all covered with semen and maybe getting caught.
Charlie and I had several other encounters that summer that I will share in other stories. One involved his little cousin Monica.