Bad Times, Good Times
This Story is written in first person perspective, but these events are purely Fiction!
Written By Jimmmy D.
At the tender age of 14 I had my very first sexual experience, I’m sure I’m not the only one that dreamt of having sex with my Baby sitter. Her name was Sherrie, she was about 5’8” and about 140 lbs, and she was 19 years old. She had a huge butt and equally voluptuous bosom, with her pinkish red hair, and very low cut revealing shirts she captured my attention as a newly pubescent boy. I had not yet sprouted my pubic hairs, but I had however been getting erections, not only for the durations of time that I had to piss, but, in a sexual way as well. I got my first erection, and thus entered the realm of sexuality one fateful summer day.
I had just woken up, around noon, my mother and father were at work, and my babysitter, Sherrie, was in the kitchen cooking lunch. I wondered through the living room, she had discarded her jacket and her shoes at the end of the sofa. I strode into the kitchen past the stove where Sherrie stood frying eggs.
“Why are you cooking eggs for lunch?” I asked her perusing the selection of drinks in the refrigerator.
“Well, you haven’t had breakfast yet, so instead of lunch, I’m going to make you brunch.”
I selected a bottle of orange soda, popped the lid of, and proceeded to suck the contents out. I moseyed over to Sherrie and leaned on the counter, facing her, watching he fry the eggs. She was wearing a spaghetti strapped tube top, it was loose and her breasts were practically spilling out. I watched her chest as a bit of grease spit out from the pan, and went into the fire. Sherrie jerked her arm back to keep the eggs from burning, and in that instant I saw her right tit pop out of her shirt. I was marvelous, it was large and round, it had a nipple just the perfect size, and that lovely nipple was bright pink, and just begging for someone to suck it. Sherrie noticed her tit pop out, but she wasn’t quick to cover it up, she walked toward me and sat the frying pan on the counter, on a small metal plate. She pulled her top outward and eased her breast back in to proper placing, she looked over to me, and noticed a growing bulge in my pants. At the time I was but a small boy, and I assure you all my extremities were in proportion. My little 3 ½ inch erection protruded from my boxing shorts. Sherrie chuckled and pointed to my groin. Noticing quickly what had happened I slapped my hands over my cock and tried to force it down.
“Don’t worry,” Sherrie started “I know that kinda stuff happens to all little boys.”
I sighed a bit and relaxed, letting my erection swing free. We ate lunch and the day proceeded regularly, around 9 pm my mother and father arrived, Sherrie left, and she came back the next day.
The next morning I woke up earlier, around 10 am and found Sherrie cooking breakfast. When I stumbled into the kitchen I saw Sherrie again cooking, this time frying shredded potatoes, today she was wearing small cotton shorts, they were so tight, and were up on her ass cheeks. Not know the proper etiquette of the sexual ideals I walked up behind her and smacked her ass. She jumped and screamed. She turned to me and smacked me in the face.
“Sorry.” she said pulling my face up to her to see if she had done any damage, “That’s a reflex, I’m so sorry.” she continued.
I sucked it up, “I’m okay, don’t worry.”
As she was leaning over me, examining my face, I was doing my own examining. I could see down her blouse, down to her chest, barely restrained by her bra. Her breasts were swinging about, tantalizingly, nipples hard and ready for my mouth. But I withdrew. We ate our breakfast and started playing Texas hold’em, this is what we often did to pass the time. Some how, I don’t remember, I got Sherrie into a game of strip poker, of course you all know how strip poker is played. As I often did, to win the games, I cheated, and this match of poker was no different, except that one of us, if not both of us, would be naked in a matter of minutes.
First had I had pocket Queens, and Sherrie was a terrible bluffer. I took her on each and every hand and won. Rather it was my luck, my cheating, or of Sherrie’s own accord I beat her over and over.
Starting with her socks, and moving to her jacket. I lost my shirt and my socks in a mismatched hand, I had a 7 and a 2. I got her down to her Bra and pants, he breasts, even though strapped back, were still gargantuan to me, they jiggled and swayed whenever she made the slightest movement, and her skin looked simply soft as silk, I wanted to touch her, to test my assumption.
This next hand was vital, this hand would lessen her apparel, she would discard her shorts, and be in no less then a bra and her panties. I was dealt a 8 of spades and 9 of hearts, the river let flow, a 6 and 5 of hearts, and a 9 of spades. I was actually starting to sweat, and Sherrie was as well, her skin was glistening, probably because the thermostat was so high. Anyway, the next card laid down was a 2 of hearts. I had a pair of nines, and nothing better, I was hoping for another heart, for a flush. I laid down the next card, ace of hearts. I laughed inside myself for a moment, and I laid down my cards, knowing full well I was about to see a great sight. Much to my dismay though Sherrie laid down, 2 9s, her 4 of a kind beat my flush. Regretfully I pulled off my pants, and was just down to my boxer shorts.
Needless to say, with Sherries flesh looking so good, with the glistening of the sweat, and the swaying of her breasts I soon engaged my penis in an erection. Not missing a beat Sherrie slapped the head of my erect penis, startling and flustering me. Now was my chance, it would seem like a retaliation, not just a deep hope of her bosom, I reached forward and pulled at her bra. With great tension is snapped. Sherries breasts spilt on my face, covering my head fully, she fell forward and fell into a laying position atop me. I was soaking up the moment of my triumph, I had my head nestled between those two gigantic breasts, it was so soft, it was like velvet flesh. Not wanting the moment to end, I seized my opportunities as they presented themselves, I threw my arms over her and held her down on me, making it seem as though I was trying to wrestle with her. She forced me off and tried to climb to her feet, but I held onto her ever tightly, as if my life depended on it. After a second or two I began to slide downward, I forced my fingers down into the waistband of her shorts, and thusly de-pants’d her. She had no underwear on, and I had a clear view from between her legs as she fell spread eagle on the couch. Her pussy was wet and dripping, she trimmed her pussy hair ever so slightly, as to make it as tidy as possible. Her pussy lips was slightly loose, obviously she wasn’t a virgin. I also took up this moment to look to her ass, it was a wonderful sight as well, as I’m sure you can imagine. Taking the next step, a chance of my childlike attitude, I threw myself on her, burying my face in her pussy. It smelled sweetly, and I got a lovely dose of her juices on my face, wetting my nose in her pussy I was in heaven. It didn’t last long however, she pushed me off of her and ran into the bathroom very quickly. I went to my room and got dressed, shortly after my parents arrived home. Sherrie left, and I went to bed, thoughts of her sweet pussy still lingering in my mind.
The next morning I awoke even earlier, as to start off and set my next plans into affect, to get even further with my sweet Sherrie.
Little did I know what would be happening to me, as soon as I left my room.
I stepped from my room, still rubbing the sleep from my eyes I didn’t noticed the deathly important sight, dancing right in front of me. I move into the kitchen, as I did every morning, and arrived back in the living room after selecting a can of grape soda. I pop the top and start to sip at it. I spit my soda out in disbelief, Sherrie is sitting on the fold out couch, naked and spread eagle, her pussy still as wet and fine as I remember.
“What’s going on?” I asked her, startled.
“This is what you wanted? Right?” she said in a very seductive voice.
“Yea…” I moaned, a bit of drool dribbling down my chin.
“C’mon then.” she said, spreading her legs even wider.
I was out of my clothes in a few seconds, brandishing my hairless, hard, little cock at Sherrie. I was about to start jabbing her in the pussy when she stopped my, I had my cock pressed lightly on the lips of her pussy. She reached up and squirts a little lube on my hot little cock. As I poke and prod her pussy she seems not to feel my little unit jabbing into her pussy. I fucked her for a good minute or two, after that she actually asked “Are you in yet?” [laughs] just kidding. But seriously, she seemed not to noticed my tiny cock, so he turned over doggie style, and I rammed my cock into her asshole. I knew I got it, her body quivered violently, as my little tiny cock sent surges of pleasure through her body. As I push my cock in deeper I meet my groin to her ass, and push in as deep as I can. I could feel something up her ass, it was obvious what it was, she was getting her shit pushed in, by my small 14 year old cock.
I continued to fuck her, and she continued to enjoy it, going fast as first, then going slowly. We resituated our self, I laid back on my back, and she impaled herself on my small cock, if you can call it impaled. She bounced up and down, up and down, I came in her asshole two times by now, and was still ready to blow another load. We continued back in doggy style and I kept fucking her. Not only was my cock short, but it was skinny too, perfect for anal sex I suppose, it didn’t stretch her asshole out what-so-ever, so she wouldn’t have to deal with that much pain, if any at all, I bet she took shits bigger then my cock. Finally I came on more time and collapsed on the bed. I watched Sherrie, as Sherrie sat, still in doggy style, looking rather constipated.
“Help me out, will you?” She asked me, moving her huge ass slightly closer to me.
I don’t know how, but I knew what she meant, I push my finger into her asshole and stretched it out slightly, along with my 3 loads of cum, she released a huge load of shit. I caught it in my hands, not wanting to drop it on the bed, and I stood up.
“What should I do with it?” I asked her.
“Um… toss it in the toilet.” she said, reaching two of her fingers into her asshole.
She must not been to the bathroom all day, it seemed very heavy. I carried it into the bathroom and placed it in the toilet, and flushed it down. I sat on the toilet, releasing my own bit, when Sherrie came in. I finished up and Sherrie got on her knees in front of me. She started sucking my cock, she puckered up her lips, as though she was sucking on a straw from McDonald’s, I was moaning in pleasure when my mom burst into the bathroom.
As she started shouting I accidentally shot my load, straight at her . It landed on her chin, her bosom and on her stomach, and I think a little got into her mouth….
Wow, a nice day of fucking, followed by a blow job, then being discovered fucking my 19 year old babysitter with my 3 ½ inch, 14 year old , hairless cock…. And I got to shoot a hot load of cum on my angry mother
