The Cleaning Lady 4

It was spring of 1992 and I was just like every other 18 year old high school boy: a virgin and horny. I discovered masturbation about 3 years earlier and I did it at least once each day. I loved the feeling of having my cock in my hand, gently stroking it, squeezing it at different pressures, going from top to bottom, and changing the speed at which I stroked.

But I wanted more. I wanted someone to see me naked. With no girls willing to take me up on the idea, my thoughts turned to a person that I would see every two weeks: the cleaning lady. Karen was in her late 30's with long dark hair and a fit body. I was 18, a hockey player and in the best shape of my life. I knew my cock may not be the biggest she had seen, but I still wanted her to see me.

Every other Thursday I would skip school in the morning to make sure I was in the shower just as Karen would start cleaning the upstairs of our home. After showering, I would always put on my robe, leaving a sliver of an opening at my belt line. I would rub some baby oil on my cock to make it hard and glisten and make it so that the tip poked out of the small opening. The first time I did it I quickly walked past her so the rush of air would open up my robe, exposing myself for her to see. It was such a turn on for me and I grew harder than I had ever been. I glanced down at my rock hard glistening cock and noticed pre-cum oozing from it. I don't know if she saw anything that first encounter, but I was hooked. I wanted Karen to see what I saw. I spent the next 13 days in a horny frenzy coming up with a plan. My plan was simple: I would gradually get more and more adventurous until something happened. What would happen, I wasn't sure and I didn't know if she would tell my Mom, scold me, or take me up on my offering.

Two weeks later, my plan went into motion. Karen showed up at the exact time as she had before. I was just getting out of the shower as she was making her way upstairs. I quickly oiled up my member, loosely put on my robe and slowly walked toward her. I could feel the cool air from our house on my cock as I moved toward her. She was looking down at a cleaning bucket, so I had to get her attention. I decided to say hi and make some small talk. As she glanced up from her bucket she paused at my waist and I knew she had seen my manhood. Our conversation was short but its purpose was served: she saw me.

Over the next month I continued my plan, each time the conversations would last longer and be more frequent at each visit. Often I would play with myself in a room next to the one she was cleaning with the door cracked open just a little bit. Later, I would even talk to her from the next room while I was cumming. Sometimes, I would sit on the stairs with my robe on, my legs open so she couldn't miss a thing. So, far she didn't act as if she was upset with my antics. In fact, she seemed to be more comfortable with seeing me as the days went on.

I spent time in between her visits reading books and watching TV shows about sex to find out how to best please a woman. I learned how to do everything from sucking on nipples to eating pussy.

Now that I had an idea on how to please Karen I became more brazen and started my seduction process. I began to set up narrow points in the hallway with chairs so my hard cock would "accidently" brush across her body. Over the next few cleanings we continued to play our game. I knew she was starting to get used to the idea of a young hard cock touching her. My plan was that eventually she would even bend down in front of me giving me full access to her heart shaped ass at which point I would stand behind her as she would slowly back into my cock as I "passed" by.

It had been just over 2 months since I started my plan, I didn't even need to stroke my cock to get it hard anymore. Every time I saw Karen I would immediately grow rock hard. I couldn't wait any longer, over the weeks I had noticed when she was cleaning something high she would let one arm hang low to keep her balance. This was my chance to actually have her touch me. So, right on time Karen showed up, I let her see me a few times and brushed my cock across her ass, and then I made my move. She was dusting the top of a chest in my mom's room. As she reached up to dust, she was standing on one leg. Her left arm was out stretched and her open right hand was unintentionally waiting for my cock to rest in it. Her hand was at the perfect waist level. I quickly fully opened my robe, moved up and inserted my cock into her open palm. Obviously, she was startled, her hand closed instinctively around my hard cock. She quickly pulled away with my cock in hand. It was then when our eyes met. I reached up with my hand and guided her beautiful face to mine. I could tell she was unsure, so I thought it would be best to go slow. I pulled her head to mine exposing her neck; I softly gave her kisses on her neck, allowing the tip of my tongue to brush across her smooth skin as I made my way to her ear lobe. She still had my throbbing dick in her warm soft hand. I gently nibbled on her ear and whispered, "Karen, you are a beautiful woman. I want to kiss every inch of your body." She responded with a deep sigh. I could tell she liked the feeling of my soft warm moist breath on her ear. I gently took her face in both hands and stared into her deep blue eyes. I leaned in and kissed her. Our tongues danced around each other, the feeling of Karen's tongue in my mouth made my cock twitch in her warm hand, which was slowly stroking me now. As we kissed I allowed my hands to explore her body and squeezed the ass that my cock had touched so many times. I started to slowly move my hands up to her shirt, grabbing the bottom of it to slide it up and off. I could barely stand not having her hand on my cock for the brief time she had to take it off in order for me to remove her shirt.

She had a pale white lace bra on, which I quickly removed exposing her amazing tits. I slowly began kissing her neck allowing my hands to freely move across her half naked body. I took her soft breasts in each hand and slowly traced her nipple with the tip of my fingers. Karen let out a moan. I kissed my way to her now erect nipples. Replacing my finger tip with my soft wet tongue, I took her nipple in my mouth alternating between sucking and gentle nibbles. My hands traced Karen's body like a maze, gradually finding the tops of her loose fitting sweat pants. I hooked my thumbs under her waist band, in one smooth motion I slipped her pants off. Karen's moans with desire filled the empty room. All of my research and planning was paying off. I licked and kissed my way past her soft stomach to the top of her lace panties. My hands were in heaven as they meandered all over her body, eventually getting to their destination. As I slipped off her panties, I couldn't help but think what was going to happen next. I wasn't worried that I was going to cum right away, because I had played with myself shortly before Karen arrived that day. Now staring into her perfectly trimmed pussy, I thought I was going to explode.

Rather than start right in I let my hands pass across her neat pubic hair to her inner thighs. I ran my tongue past her clit to follow my hands to her thighs. I gave each thigh a wet kiss as I slithered my body to her toes. I ran my tongue down her left leg to her toes and back up to her sweet smelling, moistening pussy. I let my tongue graze her wet pussy as I moved to her right leg. As I started down her leg, she guided my head back to her throbbing clit. I ignored her pleas and continued down her leg to each toe and back up. Her hands met my head as I approached her pussy; she slowly guided me to her clit. I brought one hand up to spread her pussy lips and expose her engorged clit.

I navigated the tip of my tongue though her coarse, wet pubic hair to gently tease her clit. Then I slid up and took her entire pussy into my mouth, lightly sucking and allowing my tongue to savor the taste of her delicious juices. I brought my other hand up underneath my chin to finger her pussy as I lapped her clit with the tip of my tongue once again. I inserted my middle finger deep inside her pussy, angling upward searching for her g-spot. I felt Karen squirm as my finger found the tiny bump behind her clit. I knew I was there. I continued to massage her g-spot and lick her clit, I could hear her breathing pick up, her legs began to squeeze my head. I could feel her hands still on my head, starting to push my face deeper to her dripping wet pussy. Her legs twitched, she screamed loudly, I felt a rush of her hot juices spray in to my accepting mouth. I held still, my tongue gently resting on her clit and my finger still pressed against her g-spot. She began to convulse for a second and a third time. I glanced up from my spot, our eyes locked as she came.

She pulled my head up past her navel, tits and to her face. I could feel my hard cock make its way up the freshly made bed as my body moved up hers. As I reached her face, the tip of my cock easily slid in to her soaking pussy. I pulled back, just to allow my throbbing head to tease her lips. She began to kiss my wet face and dug her hands into my hard ass, pulling me deeper inside of her.

With each thrust I could hear the wetness of our love and the sound of my balls hitting her ass. I pulled out and slowly allowed the head of my cock to part her pussy lips over and over again. She wanted me deep inside of her and I was ready to grant her wish. I forcefully rolled over allowing her to be on top in total control.

With my cock deep inside she put her hands on my firm chest and rocked her hips back and forth. She leaned back to allow my cock to rub her clit and pumped up and down. I took both hands and grabbed her ass, pulling her up on top of me. I watched her tits bounce up and down as we fucked. Our eyes met again, and I could feel her quiver once again. My balls started to tighten. I could feel her pussy tighten around my throbbing cock. I pushed myself deep inside of her and we both came, I could feel my cum and her juices rush out of her saturated pussy on to my still hard cock.

Exhausted, she collapsed on my rising and falling chest; I could feel my softening dick slip out of her pussy. Our breathing was rhythmic, we were both drenched in sweat and cum. I had just lost my virginity to our cleaning lady. Moments later we kissed and began our dance again. We went on, every two weeks exploring, experimenting, and having mind blowing sex until I left for college.