First Time is with My Aunt Charbybobwills069©
The following story is true. I've written it just as I remember, so enjoy a real experience I had in high school.
When I was in high school, my cousins and I were very close. My mother and her cousin, who we called Aunt Char, had grown up together and were just a year apart. My family was fairly close-knit and structured, and there was very little talk about dating, sex, or anything of that type around the house.
I was a typical male, pretty much a walking hard-on by the age of eighteen, and loved eyeing my three female cousins and my sister whenever they were around. I wasn't getting much experience with the girls at school, and had yet to get a lady from the front seat of my car into the back, but I certainly fantasized about it all the time.
When my college-age sister was around, I spent a lot of time waiting for her to take a bath or shower so I could be there when she got out. I'd be in the family room waiting, and she would walk by with a tiny towel around her on the way to her room. Once she got to her room I check to see where my mom was and make sure the coast was clear. Then, with my heart thumping in my chest I would pull a small mirror from my pocket and very carefully press it into the run under her door and check the reflection I got.
I'd be so excited that my hands would shake, especially when my sister Mary was facing just the right direction and I would get a quick shot of her pulling on her panties and I'd see the hair around her pussy. Every time I saw her cute little ass or bush I'd get a hard-on and run down to my room and jerk-off once she was done getting her bra over her nice 36-C tits. She had small areolas, but her nipples were always hard, and I was a mess.
When my cousins came over with Aunt Char to swim in our pool on the weekends, I hang around watching them in their tiny bikinis and thought about what it would be like to get one of them into my room to fuck. Every weekend was torture because I didn't want to leave and miss anything, so I just hung around like a doof.
A couple weeks went by and my cousins didn't show up. When I asked my mom what was up, she said that Aunt Char and my uncle were having some problems, but we were going over there on Saturday. I missed the eye-candy, and looked forward to Saturday, but was disappointed when we arrived and my cousins were gone. My aunt was there, drinking heavily, and keeping out of my uncle's way. They were obviously pissed at each other, and I hung around my aunt because she was always funny when she drank.
At one point when nobody was in the room but the two of us, she suddenly said, "You know, you're really cute. You've grown into a very nice looking man."
I stammered some lame response, and had no idea how to act. She went right on with a conversation about other things, but I felt a tingling in my balls and a hollow pit in my stomach.
A few days later I was at home and went to use the phone. When I picked it up, my mom was already talking to my aunt, but I listened quietly for a moment. I heard them talking about Auntie getting a divorce, and then she said, "You know, I never would have gotten married if I wasn't addicted to sex."
I nearly dropped the receiver, it was such a shock to hear something like that from her. I listed a while longer, and then hung up gently. I fantasized about her more and more after that. When she came over to sunbathe, I definitely looked at her in a different way. She had great legs, and although she was in her early forties, they led up to a terrific ass.
She came over a few times alone, and sat sunbathing while talking to my mother. On those occasions I would stay inside where I could watch and jerk-off from a perfect spot where I couldn't be seen because of the shadows inside the house.
Aunt Char got her own apartment a month later, and after she had moved in, my buddy and I helped move a couple items from her parent's house. We dropped them off, and my friend drove off with his truck and I got into my car, but it flooded and I couldn't get it to start again.
I walked back up to Aunt Char's apartment and knocked on the door. She had already had a few drinks, and when she didn't answer, I though maybe she was in back, fixing another. It turned out I was right, but she had also taken a quick shower and only let me in after peering through the peep-hole in her door.
She had on a robe, and a towel around her head. In one hand was another gin and tonic, and she just slightly slurred her words when she asked why I had come back. When I explained I couldn't start my car for a while because the carburetor was flooded, she was getting that funny attitude she got when drinking, and we laughed a bit for the next few minutes before she said she was getting one more drink before going to bed.
My dick was already hard from watching her boobs swing around inside her robe, but when she came back into the room, she had a drink in both hands. She bent down to hand me a coke, and when she did, I could see right down her robe. In fact, I could see her 34-B tits and even a bit of pussy hair.
She was just drunk enough to probably not realize what she was doing, but I kept thinking back to her saying I was cute, I wanted her so bad. I was looking at her lips when she sipped her drink, and her tongue came out and licked the underside of her glass with every sip. I have no clue what she was saying, or what I was saying, but I made some excuse to come over and sit right in front of her on the floor, hoping that her legs would part and I could look up her robe.
She almost immediately obliged, and I got a nice shot almost to her pussy. Then, she suddenly said, "Oh, I was going to do my toenails," and she jumped up, and beckoned me to follow her into the bedroom so she could paint her nails. She sat on the bed and got out the polish. I watched closely as she pulled her legs up and painted each nail.
While she moved her arms to paint them, her boobs got closer and closer to being completely exposed. I could see her nipples at times, and they were very long. They must have been almost an inch, and I wanted to lean in and suck one so bad my head was spinning.
When she finished her nails, she stretched her legs out and pulled her robe up to where I could almost see her pussy while she admired her work. I still wasn't sure if she was just looking at her legs and toes, or trying to get me to make some kind of a move. She looked at me and said, "You know, I used to have really nice legs."
"Aunt Char, you still have great legs. When I see you sunbathing I always think how nice they are."
"You mean you noticed me, even at my age?"
"Sure, I think you look great. Any man would be lucky to have a beautiful woman like you to spend time with."
She smiled, and it was either a happy, contented smile, or one that said, finally, I get what I want, and she opened her robe. He nipples were still enormous, sticking out from the middle of her dollar-size areolas. They were pink-orange and bumpy, and I saw them contract and shrink while I was thinking of what to do.
Aunt Char reached over and took my shirt off, and I pulled my pants off quickly. I got back on the bed and sat cross-legged, and she just moved over and sat right down on my dick. It slipped easily into her wet pussy. I could actually feel her juices dripping down my cock and onto my balls she was so wet. I went right for her boobs, feeling them and rubbing those huge nipples with my finger and thumb.
Aunt Char was moving up and down on my cock, her head thrown over my back and breathing heavily by my ear. Then she slowed down and stopped. She pulled back from me and looked into my eyes. I almost came when she gave my dick a couple amazing squeezes with just her pussy muscles.
"Bob, this is wrong, it's all wrong."
Her voice, quivered, and I thought at that point I'd settle for just pulling out and jerking off in front of her. "But, I," I mumbled.
"No, it's not you, you are doing great, but this should never have happened, and we can't ever talk about it, we can't ever do anything like this again. Do you understand? Your first time should have been with a virgin. It should have been so special. But if you do understand, and you promise never to mention this, or talk about it to anyone, I'll still be your virgin."
"No, Auntie, I'll never tell anyone, I promise," I said. And then I begged her not to stop.
"Alright, I'll teach you how to make love to me," and she climbed off me and lay back on the bed. Auntie told me how to kiss her lips lightly, and how to nibble her neck and around her ears. How to whisper into those same ears how beautiful she was, and how much I wanted to make love to her, and then how to work my way down to her tits, and how to suck them with just the right pressure and tweak the nipples.
Eventually, she let me move down to her pussy, and she had me lick around her love box and suck on her lips and pull them gently. I sucked for a long time while she showed me how to put a finger into her now gushing pussy and massage her "G" spot until she had two fantastic orgasms.
When she was done panting, she said, "Now, Bob, I promised you a virgin. Put that big cock of yours back inside me, but try not to come right away."
I slipped my dick back into her pussy and it massaged me like a third hand. Her muscle tone was amazing, and I was about to explode when she slowly slipped away. I thought we were done and grabbed my own cock when she said, "No, big boy, I've got a real virgin for you. I want you to lick my pussy for a second, and then move down to my ass."
I wasn't too sure about that, but I sure liked the taste of her pussy. The juices were all over my face as she grabbed the back of my head and guided me down to her ass. I gave her a few licks around her hole and she wrapped her legs around my head. Then she let go, rolled over, and said, "Well, do you want to fuck my virgin ass or not?
Boy did I. I grabbed my dick and rubbed it around her pussy juices to get it good and wet, then pushed into her tight ass-hole. She told me to go slow, and I did exactly that until we had a little rhythm going.
Auntie reached between her legs and stroked my balls, then told me to tell her how much I wanted her, and to rub my hands in her hair.
"I want you Auntie, I really want you."
"No, tell me you are taking me, you WANT me," Char implored.
"I'm fucking you Auntie, I want you more than any woman in the world, and I'm fucking you up the ass!"
"That's right, Bob, take me hard," she cried as she worked her second hand into her pussy.
"I'm fucking your ass, Aunt Char, you're mine, and I'm fucking you harder than you've ever been fucked. I've wanted you for years. Every time I saw you I wanted to fuck you, I wanted to eat your pussy and suck you lips, and even fuck your ass. I used to watch you from the windows of the house and when you rolled over put lotion on your legs I used to grab my cock and jerk-off while I watched you.
That little bit of information was amazing to her, and it really helped her get off. She couldn't believe I had jerked-off while looking at her, so I kept telling her about it while we fucked. Eventually it was too much for both of us to wait any longer.
"Take me, fuck me, oh god, oh, mmmmm," she cried just as I was coming. I felt like a firecracker was going off in my head and my dick at the same time. Her ass was so tight it was almost hard for all that come to get out, but I splashed enough that it squirted out around my dick and made an even larger wet spot on her bedspread.
Aunt Char stopped moving for a while and I just lay atop her back. In a while, I pulled out of her ass and she rolled over and gave me a kiss. She sucked hard on my tongue and said it was the best night she had experienced in years. She then led me to the shower, but pushed me in alone.
While I cleaned up, she said again how wonderful it had been, and that we could never talk about it ever again, and it would be like it never happened. True to her word, she has never brought it up, and we've never talked about it. But boy, it sure wasn't like it never happened!