The first time I had sex was with my Aunt Ellen. I was 12, and she was 41. My parents went on a trip for four days and asked my her to stay at our house to watch my sister and I. I had never really fantasized about my Aunt, but more than once I had tried to look down her top or up her skirt. Even though she was over 40 and fairly plump, I remember that she had nice big boobs that jiggled when she walked, a sweet round ass, and was very attractive overall. Her husband had died about 3 years earlier, and although she was very attractive she had not started dating again and I'm sure had not had sex in over 3 years. At 12 I was really starting to get interested in girls and spent alot of time jerking off and fantasizing. Little did I know that my dreams would come true that week!
The day that Aunt Ellen arrived and my parents left for their little getaway, things were pretty normal. My Aunt and sister and I had dinner together and caught up on things. Aunt Ellen lived a few states away in the Midwest, so we only saw her a couple of times a year. After dinner, Aunt Ellen had some wine while my sister and I took our baths and got ready for bed. It was a humid summer night and after tossing and turning for a couple of hours, I got up and went into my parent's bed (theirs was the only room in the house that had air conditioning back then). Aunt Ellen was already asleep, so I quietly slipped under the cool covers and fell fast asleep myself.
Sometime in the middle of the night, I awoke while having a vivid wet dream. In my dream, one of the cheerleaders at my school was letting me feel her pussy. In my half awake/asleep state I slowly realized that my young cock was rock-hard. Then, as I came to my senses I realized that it was poking at something warm and squishy -- the crack of my Aunt Ellen's ass! She was laying with her back to me, and somehow her nightgown had worked itself up above her waist. It was then that I discovered that my Aunt Ellen was not wearing any underwear and my rigid cock had happily poked out of my boxer shorts, wedged itself between her legs, and was now prodding at the area between her anus and pussy. My precum had already made the whole area slippery. She was still asleep, and I was frozen in fear that she might awake and find my cock between her legs. I laid still for what seemed like forever, hoping that my cock would soften and I could pull away. But no, it stayed right there throbbing happily against my Aunt's warm, plump folds.
While I was trying to decide what to do, she suddenly stirred, shifted on her pillow a bit, drew her knees up and arched her back slightly towards me. I held my breath until I was sure she was still asleep. But then I had a new sensation -- the new position she had shifted into had caused the tip of my cock to move directly into the juicy opening to her cunt. No longer in control, I pushed forward slightly and felt the head of my cock slip between her pussy lips. I can still remember that incredible feeling -- the first time my cock touched sweet soft pussy flesh. Completely forgetting that the pussy I was entering was my Aunt Ellen's, I pushed forward a little more and without warning starting squirting cum into the opening of her cunt. I immediately pulled back in horror and shot my remaining streams of cum on her ass and the bed. Quietly, I slipped out of bed and hurried to my room where I laid awake worrying about what would happen to me the next morning when Aunt Ellen discovered dried cum all over her ass and pussy.
In the morning I was a nervous wreck. I tried not to make eye contact with Aunt Ellen when she summoned me downstairs to breakfast. To my surprise, she made no mention of the night's events and acted as if she was completely unaware that I had even been in bed with her. Was she too embarrassed to talk about it?, I thought. Finally, I decided that she had slept through everything, had not noticed the cum and went straight into the shower unknowingly washing away the evidence!
All that day I couldn't stop thinking about what had happened. After an uneventful dinner, Aunt Ellen was again having some wine and watching a movie as my sister and I went off to bed. I had no chance of sleeping, as I laid in bed playing with my cock and trying to get up the courage to get in bed with my Aunt again. After about 2 a.m., I crept into her room and once again slipped quietly under the covers. As I cautiously moved closer to her, my hard cock brushed against her naked butt cheeks. Was her nightgown pushed up above her waist again, I thought? No -- as I lightly slid my fingers from her ass up her back to her shoulders it was clear that she had gone to bed totally nude! Seizing the opportunity, I carefully reached around her and cupped one of her huge tits in my hand. The feeling of her large, soft boobs and her hard nipple in my palm made my cock throb even more. I gently squeezed her tits while my cock once again probed between her cheeks. Just like the night before, she shifted again and gently pushed her ass and pussy back towards me. I thought that maybe in her sleep she was subconsciously aware of a cock pushing between her legs and involuntarily shifted to allow it entry. Once again, I felt the head of my cock probing her juicy pussy opening. This time, though, I pushed forward slowly until my entire length was inside of my Aunt. I held it there for a moment, savoring the feeling of her large, warm cunt. Then, I lightly cupped her tit and began gently moving my cock in and out of her. Before long, I could feel myself ready to cum again. Thinking quickly, I decided that it would be too risky to cover her ass again and if I quickly pulled out and came in my hand I might wake her. I pushed in as deep as I could and pumped my seed deep into my Aunt's womb. At only 12, I didn't know enough about the risk of pregnancy so I innocently and happily filled Aunt Ellen with my semen. Slowly, I let my cock soften a bit then I carefully slid it out of her and went back to my room.
The next morning, it was the same thing -- a normal breakfast and no mention of the previous night. I spent the third day of her visit eagerly anticipating her last night with us. After bedtime, it was business as usual. At about 1 a.m. I could wait no longer and I crept into bed with Aunt Ellen. Again, I found her completely nude. But this time she was sleeping face down with her knees pulled up underneath her and her ass sticking up under the covers. Odd sleeping position, I thought, but perfect for giving me easy access to her big warm pussy. With her in this position, instead of laying down beside her I carefull pulled the blanket and sheet up over her back, exposing her ripe ass. Then, I got into position on my knees behind her. Just as I was about to slide my cock into her pussy opening, I had another thought. In the dim moonlight, for the first time I could actually see her round ass and gaping cunthole. I moved my face closer to get a good view. I could smell her pussy juices and see her cuntlips glistening. Some boys at school had once told me that guys like to lick women's pussies, so I decided to give it a try. Cautiously, I tongued her pussy lips then pushed my tongue inside of her. At first it tasted strange and new, but after a while my saliva mixed with her juices as I gently sucked at her cunt. As I buried my face in her big, sloppy cunt I could smell her asshole near my nose. I found the smell of her ass very erotic, and so I moved up and tongued her asshole. After I had satisfied my appetite for pussy and ass, I got up on my knees again and positioned my bulging cock between her butt cheeks. The entire area was soaked and slippery from my licking and sucking, so I slid my cock up and down her crack a couple of times then pushed forward. As I felt it enter my Aunt, the feeling was a bit different -- somewhat tighter and not quite as soft. I surmised that the difference in feeling must be due to the different position Aunt Ellen was in this time. It felt fantastic anyway, so I pushed in deeper. As I gradually slid my entire cock in, I heard Aunt Ellen let out a low, soft moan. I stopped as my balls pressed against her mound, terrified that she might wake up. After a few moments of silence, I was sure she was still sleeping. As I cupped her ass cheeks with my hands and started to pull out a bit, I discovered why she felt different this time. I wasn't in Aunt Ellen's pussy at all -- my cock was buried deep in her asshole! With all the slippery wetness, this new position, and my lack of experience, I had accidentally pushed my cock into her asshole. It was much tighter than her cunt and just as much fun to fuck, I thought. In my young mind, I worried that maybe boys weren't supposed to stick their dicks in a girl's (or in this case a mature woman's) ass. But the feeling of my Aunt's tight ass gripping my cock as I pushed in and out of her soon made me forget those worries. I became completely lost in the moment, seeing her round ass cheeks bobbling in front of me as I pushed into her. Soon I forgot all caution and began slamming my Aunt's asshole, watching her body lurch forward and jiggle with each thrust. With a few last thrusts, I held my cock deep in her and shot stream after stream of cum deep into Aunt Ellen's bowels. As I finished spurting, I held onto her ass to steady myself while I caught my breath. After several minutes of remaining still, my cock was still rock hard and buried to the hilt in my Aunt's ass. Her ass was gripping the base of my cock tightly, preventing it from going soft. While I was contemplating what to do about this, I felt my Aunt's ass flex and squeeze my cock even more several times in a row. This got me eager for another round. Throwing caution to the wind, I began to move in and out of her ass again. With her bowels full of my cum, her asshole was much more slippery than before and I pumped in and out of her very easily. As I fucked my Aunt's ass, suddenly she raised up on her hands, spread her legs more and arched her back. Shocked and surprised, I knew she had to be awake. I stopped suddenly and started to pull out. But before I could, she pushed back towards me and engulfed my cock with her asshole. As I remained motionless, my Aunt Ellen was assfucking my cock! In disbelief, I watched my 41 year old Aunt knowingly and eagerly slam her ass back into my engorged cock. Soon, this was too much to take and somehow she could tell I was ready to cum. Before I knew it, she pulled away from me, swung around quickly, and took my cock in her mouth. As my cockhead pushed through her lips I was already starting to shoot. Most of my cum went down my Aunt's throat and the rest dribbled out of her mouth, down her chin, and onto her big pillowy tits. She sucked the last few drops out of my softening cock, then scooped the cum off her chin and tits, put it in her mouth and swallowed. I fell onto the bed, totally and completed in bliss while my Aunt Ellen rolled over and put the covers back over her. After a few moments, I wasn't sure what to do so I crept out of the bed and returned to my room.
The next day my Aunt Ellen left after my parents returned. She gave me a knowing smile as she got into her car. I saw her several times after that, but we never discussed those nights. Also, I never had any more sexual contact with her until almost 20 years later. But that's another story....