Babysitting for the Kellys

When I was eighteen and just starting college, my father was gravely ill and could not work. I knew my family was struggling financially, so I was eager to do whatever I could to help out with the family finances.

The Kellys lived down the street, and I had known them for many years. They knew of my family's plight and kindly offered me a babysitting job. Although I felt that babysitting was beneath me at that age, I eagerly accepted the position because I wanted to do my part. It turned out the Kellys were very flexible with my schedule, and they were very generous to me on account of my father's illness.

Mrs. Kelly (call me Angela) and my mother had become good friends over the years. They were always at each other's houses, usually with a glass of wine. My mother was a very attractive woman, as was Mrs. Kelly, and together they made a striking pair.

Mr. Kelly, or Mr. K, as I called him, was a good-looking, half-black (as far as I could tell), tall man who was always happy and cheerful. 

Mr. K was younger than my father, and they had nothing in common. In fact, they were more or less opposites, and thus their relationship was just normal good-neighbor small talk.

Mr. K knew I was shy and timid, so he always made an effort to engage me in conversation. As I started to become comfortable with him I realized he was not only fun and witty, but also very flirty. I could sense he was a ladies' man, especially when his wife wasn't around. I noticed that he began to give me more attention as I blossomed into a young woman. Maybe it was my imagination, but sometimes he looked at me with what I can only describe as a lustful look.

The Kellys had two adorable daughters, ages four and six. As far as babysitting goes, it was an easy gig as the girls were well-behaved. They also lived just down the street, which made it convenient.

I was eighteen and had just started dating Aaron. He was a good-looking guy who was popular with all the girls. At first, I wasn't sure why he liked me when he had his pick of the popular girls. I later realized it was because I was shy and submissive--or a slut, as guys would put it. Looking back, he was a jerk who only wanted me for sex, but at the time I was just happy to have a boyfriend.

One particular night when I was babysitting, Aaron called and insisted on coming over to the house. I knew I wasn't supposed to have anyone over, but I had just finished putting the girls to bed, and it was still early. I knew the Kellys weren't coming back for a few more hours.

Normally, I wouldn't have allowed it, but Aaron was persistent and he promised to be in and out in a half-hour. Yeah, he just wanted to come over and fuck. I was shy, insecure, and afraid of losing him, so I gave in.

The kids were both asleep when Aaron arrived. He wasted no time pulling me onto the couch and taking me. Within minutes of his arrival, we were both naked and fucking on the living room couch, just like a couple of horny teens.

"How's that babe? You like that?" As he fumbled and pushed a finger inside of me.

"Uh-huh," I replied, trying to fake my enthusiasm. My new boyfriend, Aaron, didn't seem to notice my lackluster response and continued to flail on top of me like a fish out of water. I gritted my teeth as his dick roughly plowed into me, my pussy not yet wet enough to make this at all pleasurable for me. He didn't seem to notice or care.

Aaron was always so eager to get straight to the fucking that he never made sure I was properly aroused. This was pretty much my experience with all the boys I had dated up to this point.

"Fuck April, I love your tits, they're amazing." Aaron grabbed my breasts and tugged and squeezed them hard. It felt like I was getting a fucking mammogram. He started pounding his cock into me harder, grunting with every thrust.

"Shh!" I said it sharply. "I don't want the kids to hear."

"I'm sure they're fast asleep... Besides, the TV's on. That's all they'll hear." Aaron downplayed my concerns. I still looked over his shoulder nervously towards the staircase to the bedrooms. I had a bad feeling about this, so I just wanted Aaron to finish getting his rocks off and leave.

"I'm gonna cum," he suddenly growled in my ear. "Are you close?"

"Yeah," I lied, as I was feeling uneasy about his visit. Aaron's thrusts started getting more frenzied until his body tensed up against me and he ground his hips hard against mine.

"UHHHHHHHH!" he yelled, throwing his head back. I felt him unload inside me, and I tried not to look so disinterested. Aaron looked at me through half-open eyelids to see my reaction. I suddenly clued in, threw my head back, and started writhing underneath him, as if I were suddenly wracked with a powerful orgasm.

"Oh babe, that was so good," I said in a breathy voice. Aaron grinned at me, completely clueless but satisfied.

"Hey chump, I hate to break it to you, but she's faking it." Aaron and I both froze, and panic shot through me. It was Mr. Kelly, and he was home early.

"Shit," Aaron said as he quickly scrambled off me, scrabbling for his clothes, his still semi-erect cock obviously showing the signs of our recent activities. It drew the eye in a way that served only to highlight our transgressions. Mr. K's expression said it all.

I was still too shocked to move as I locked eyes with Mr. Kelly, who had now entered the room and was staring at my very naked body. My cheeks flushed, and I frantically grabbed a nearby pillow to cover myself as my clothes were out of reach somewhere on the floor. I quickly cowered into a kneeling position on the sofa and tried to cover myself with the undersized pillow. By now, Aaron had managed to get his pants back on.

"Mr. Kelly, I'm so sorry, I..." I trailed off, having no idea what to say. This was the most embarrassing moment of my life. I could feel myself turning beet red.

Mr. Kelly ignored me and turned his attention to Aaron.

"Well what the fuck are you waiting for? GET THE FUCK OUT OF MY HOUSE AND DON'T EVER COME BACK!" I had never seen Mr. K so angry.

Aaron, shirt and shoes in hand, made a beeline for the door. He didn't even look at me. Mr. Kelly and I waited in silence until we heard the door slam shut. I slowly sat up on the couch, still clutching the pillow to my naked body.

Mr. K took a deep breath and just stared at me as he calmed down.

"Does your mother know you're having sex?" He asked. I just stared at him, confused by his casual tone.

"It's none of her business," I mustered in my most confident voice. "I'm an adult." Mr. Kelly scoffed.

"Barely. What, did you turn eighteen yesterday?"

"A month ago," I stammered. He scoffed again and shook his head.

I really wanted to get dressed, but I certainly wasn't going to do it in front of him.

"My wife's not going to be happy to hear about this," Mr. Kelly said. "It's a shame, April. Angela really likes you. The girls adore you. But how can I trust you again? How do I know you won't let more strangers into my house? What if the girls had walked in on that?"

I looked down at my lap, too ashamed to look at him. I knew he was completely right. I couldn't think of anything to say. What could I say?

"I'm sorry," I sheepishly said. "Just let me get dressed, and I'll go home. You don't have to pay me."

I assumed he'd leave, but instead, Mr. Kelly sighed and sat down on the couch next to me. I sat up straighter and held the pillow tighter.

"You know, Angela's going to tell your mother about this," he said.

I closed my eyes and groaned. Of course, Mother would find out. She and Mrs. Kelly were best friends and talked all the time. And even if she didn't tell her, surely my mother would want to know why I wasn't going over to the Kellys to babysit anymore. It would all come out one way or another.

"God!" I moaned, slumping against the couch.

"I know," Mr. Kelly said. "It sucks. Especially since that sex was awful. Not even worth it."

I shot him an incredulous look. This conversation was incredibly inappropriate.

"Why don't you tell him the truth?" Mr. Kelly continued. "Why do you let him just use you like that?"

I was still shocked by the conversation, my mouth hanging open in response to his question. But Mr. Kelly cocked his eyebrow at me, waiting for an answer.

"I don't know," I said quietly. "I keep hoping it'll get better, I guess."

Mr. Kelly shook his head.

"I hate to break it to you, April. But teenage boys don't know what the hell they're doing. You're not going to have decent sex until you fuck a man."

I looked up at Mr. Kelly again, and his gaze was suddenly intense, his eyes surveying my bare shoulders and legs. The pillow was barely large enough to cover my privates. My heart started racing, and a strange feeling shot through my belly. I didn't know what to say. I felt so humiliated and just wanted to go home to bed and forget this ever happened.

"You know," he went on, brushing his fingertips over my shoulder. "I could show you what real, good sex is like." My eyes widened in shock, and I quickly pushed his hand away from me.

"What are you doing?" I asked. I scooted down the couch to distance myself. "You're married! Where's Mrs. K, anyway?"

"She's still drinking with her girlfriends," he replied. "She won't be home for hours. You know how women can talk?"

I stared at him, shocked by his proposition. Sure, Mr. K was a good-looking man, considering he was in his early forties. He was tall and looked fairly muscular. He had dark, lush hair, and a nice amount of stubble covered his cheeks. But he was old! As I was eighteen at the time, forty seemed ancient to me.

"No way!" I said. "This is way too weird. You watched me grow up, for god's sake!" Mr. Kelly shrugged, unbothered by my pointing that out.

"Let me fuck you," he said simply. "And then Angela won't have to know how irresponsible you were tonight--then your mother and father won't find out either. And you can keep watching the girls like nothing happened."

His candor was not only shocking but it scared the hell out of me.

"Are you blackmailing me?" I blurted it out.

Mr. K just gave me a devilish grin.

And just then, as if I wasn't embarrassed enough, I felt a gush of fluid pour out of me and onto the couch. As I looked down, I saw a large stain on the couch as Aaron's recent deposit poured out of me.

I looked up, hoping that it went unnoticed, but Mr. K just shook his head as he stared at me, waiting for my response. How much worse can things get?

I took a deep breath and went silent. My mind raced as I actually thought over his offer. I really didn't want my mother to know, and I especially didn't want my strict father to find out. How humiliating and degrading would that be? Besides, I could really use the money that countless more babysitting sessions would bring.

Mr. Kelly noticed the worried look in my eyes as I continued to think things over. I knew he had me. I couldn't think of a way to get out of this situation.

A couple of months ago, I had sex with Jeff, another father that I babysat for. That worked out fine, so I thought, how bad could this be? Besides, it would be just this one time.

"April," he said gently, placing his hand on my leg. I tried not to flinch.

"You don't need to be scared, hon. Like I said, I want to show you a good time. I'm going to show you how a real man pleasures a woman." I felt him move his large, warm hand up my bare thigh.

I couldn't believe the situation I had gotten myself into, let alone how Mr. Kelly was speaking to me.

I said nothing, but my body visibly relaxed as I loosened the death grip I had on the pillow. Mr. Kelly noticed and took that as a sign to proceed. He grabbed the corner of the pillow I was clutching and snatched it away. He threw it across the room onto a chair and turned to stare at my nakedness.

I was kneeling at the end of the couch with my arms crossed, trying to cover up as much as possible. My hardened nipples were peeking out around my forearms. The entire situation had aroused them, and the sudden cool air made them rock hard.

Mr. Kelly said softly, "That little dick doesn't deserve you."

He reached his hand out and unclenched my crossed arms. My arms slowly dropped in a sign of submission. He then reached for my right breast and softly massaged it, his thumb brushing over my nipple. I inhaled sharply as I saw the intense look on his face. It felt surreal. I couldn't believe this was happening. On the other hand, his touch already felt a hundred times better than the way Aaron had mauled my boobs.

Yeah, it feels good, doesn't it?" Mr. Kelly asked me. I gave him a small nod.

"Sit back," he said. "Relax."

Resigning myself to the situation, I repositioned myself into a sitting position and leaned back against the couch. Mr. Kelly began to gently caress my breasts. I closed my eyes as he continued to feel me up.

"You do have the most beautiful breasts," he remarked.

I couldn't help feeling a sense of pride at the compliment, especially coming from a mature man. I knew I was blessed with nice breasts--nice round, perky B-cups.

My eyes were closed, so I didn't realize Mr. Kelly was about to kiss me until I felt his lips brush against mine. He startled me, and I pulled back just enough to break contact and look at him. He paused for a split second, then moved in for another kiss. I had accepted my fate and found myself surprisingly relaxed. I moved my lips against his, returning the kiss.

Mr. Kelly pushed his tongue into my mouth as he continued rubbing my breasts, applying just enough pleasure to really turn me on. I felt myself getting wet--a rare occurrence with Aaron. He suddenly pinched my nipple, and I moaned into our kiss.

"You're a much better kisser than him," I murmured softly.

"We're just getting started, hon," he replied with a smile. "Lie down." 

I did as he asked, although I was a bit reluctant about what was coming next.

Once I was settled, Mr. K knelt by the couch and started running his hands up and down my body. He felt the curves of my thighs and hips, his fingers brushing dangerously close to my pussy. I anxiously squirmed under his touch. He bent over and took a breast into his mouth.

"Ohhhh," I said softly, closing my eyes again. His mouth sucked on my tit while his tongue teased my nipple. I found myself putting my hand in his hair and pulling him more tightly against my breast. I was so distracted by what he was doing to my breasts that I didn't realize his hand had traveled south and was pushing in between my legs.

I gasped as I felt a long finger sliding into my pussy. Mr. K let my breast fall out of his mouth and moved close to my ear.

"Do you feel how wet you are? That's how wet you should always be."

He pumped his fingers at a slow and steady pace, gently stretching me open. I was amazed at how easy this all felt. Whenever Aaron fingered me, it was an awkward and slightly painful experience.

"If a man doesn't bother to get you wet, he's not worth your time," Mr. Kelly said, as he added a second finger inside of me.

"Ahhhhh." I involuntarily bucked my hips upward, forcing his long fingers even deeper inside me.

"You like how I finger you, April?" I took a deep breath and nodded.

"Please, Mr. K." I responded in a submissive tone.

He smiled. "You want me to make you cum?" My heart was racing now. Aaron had never made me cum. At that age, I'd rarely had an orgasm that wasn't self-made.

"Please, Mr. K," I repeated as my arousal began to show.

He shoved his fingers as deep as he could into my pussy and used his free hand to start rubbing my clitoral area. I tilted my head back against the throw pillow, arching my back to increase the pressure. It took only about thirty seconds of rubbing my clitoral area before my pussy walls were pulsing around Mr. K's fingers.

His fingers easily slid in and out of me. My love juices were flowing like never before. I could hear the slurpy sounds his fingers were making as Mr. K began to assertively finger-fuck me and stimulate my clitoral area at the same time.

"Oh, my gawd," I moaned as I felt an orgasm quickly building within me. Mr. K had me moaning and squirming on the couch as he continued to relentlessly stimulate me. I felt his fingers curl up as he found my G-spot.

"OOOHHHHH!" I cried out as the orgasm washed over me. I began to quiver and shake uncontrollably. I reached down and grabbed his hand, first trying to get him to stop, then pushing it deeper inside of my hungry, wet pussy. 

"Oh fuck...." I collapsed back onto the couch, my face flushed and breathless.

"Oh April, you look so beautiful when you cum," Mr. K said as he slid his fingers out of me and held them up to my lips.

I instinctively sucked on his digits. I could taste my juices, but there was also a slight flavor of Aarons's sperm. He watched as I wrapped my tongue and lips around and in-between every finger.

Mr. Kelly then leaned over and kissed me.

"Are you ready to get fucked now?" He said it in a casual voice.

I reluctantly nodded. After all, this was Mr. K, the man down the street. He was friends with my parents. I found it difficult to accept his frankness. Did he just ask me if I was ready to get fucked?

I had a sinking feeling; this was going to go terribly wrong.

Mr. K stood up and started taking off his clothes. I watched him, fascinated by his toned chest and abs. He had so much chest hair--I wasn't used to seeing that, but I realized right away that I loved it. Mr. K was right. Aaron was just some dumb boy, but he was a man.

I tried not to let my eyes bulge out of my head as his pants and briefs came off. He already had an erection, and his dick was so fucking large. It was way bigger and thicker than Aaron's. I suddenly got nervous again. I flinched a little as he walked back towards me with a dick in hand. He gave it a couple of strokes, as if it wasn't large enough already.

"I don't think it'll fit," I said worriedly. He gave me a reassuring smile.

"Trust me, hon. It will." 

Mr. K slowly lowered himself over me, one knee brushing against my thigh as he climbed onto the couch. I was suddenly aware how much larger than me he was, how much stronger; his chest and shoulders were intimidating. I knew I couldn't stop him, even if I wanted to. I wasn't sure I wanted to. He was heavy--much heavier than Aaron--but his weight felt good. I loved the feeling of being trapped by this naked, sexy man.

He brought his hand to my face and gently stroked my cheek.

"I feel terrible admitting this, but I've wanted to do this to you for a while." He paused. "April, if you haven't noticed, you have developed into a hot young woman with a fantastic body... and the way you dress... Well, it's hard for a man not to notice, hon."

I felt that fluttering in my belly again. My initial perception of how Mr. K had been looking at me was dead on.

"You have? Please be gentle." I pleaded. 

I was determined to get this over with as quickly as possible and hopefully forget that this night ever happened.

Mr. K smiled before nudging my legs apart and positioned himself over me. I couldn't believe I was laying naked with my legs spread before him. I felt his cock poised at my entrance as he casually moved it up and down the length of my labia, lapping up my juices for lubrication. The head of his cock found my opening, and it easily popped inside of me. Mr. K slowly began pushing it in.

"Oh!" I exclaimed. I'd been expecting it to hurt, but it hadn't so far. He took his time and slowly eased himself in. With every gentle push, he would pause, giving me a chance to adapt. Before I knew it, he was all the way inside of me.

"See?" He asked. He stilled, and I realized he was completely inside me. I was amazed at how easily I stretched to accommodate his length and girth.