As a guy, I was never a ladies man. Honestly I never even kissed a girl. That all changed that one night. I went about my usual day. Getting lectured by teacher after teacher, writing down homework I’m not going to do, go to cross country practice.. etc. It was towards the end of the day when I got a txt message from Mrs. Jenkins to babysit her 10-year old boy.
I quickly accepted in need of easy cash. She said she would pick me up around 6. At this time I was 15 and, like every other guy, horny. I wasn’t big by all means, but I wasn’t small either. I was about 5’ 6 and 120 lbs. I couldn’t use my upper body to save my life, but my legs were different. Being on the Varsity Cross Country team as a sophomore and the JV basketball team was something I was very proud about. Oh, my name is Daniel btw.
School went by slow, like usual, we ran 8 miles that day for practice. My legs killed as I was walking home. It was about an hour walk, after about 15 minutes, I see a car slow down and drive with me as I was walking. I joked in my head saying I was going to get shot (Being one of the only white people in a mostly colored school in a wana-b gangster town). I watch as the window roles down, I unplug my ipod from my left ear and lean forward to get a better view of the driver.
It was Mrs. Jenkins. Of course once she offered a ride I happily accepted. She asked if I wanted to go straight to her house and hang out for an hour before they had to go, instead of hanging out at home. I figured, sure, why not? I got in the car and looking Mrs. Jenkins up and down. She was definitely in work clothes, but I’d figure I should ask if she was on her way home from work anyway.
She responded yes with a gorgeous smile. Mrs. Jenkins was the women that every guy new the husband was too lucky. She wasn’t amazingly stunning, but definitely beautiful none the less. She’s maybe 5’4 with 36C breasts (I’ve looked through the hampers), a decent amount of belly fat, but not anywhere close to being real fat. Her ass stuck out and gave me boners whenever I would see her bend over or just give a wiggle. I thought I was crazy but I always saw her winking at me and it seemed like whenever I was near her she would do something to give me a boner.
She then asked how school was going. I replied fine, and that most of my classes were easy. She said that’s good and kept her eyes on the road. I was staring at her breasts this entire time, in her dress they looked so big, and I could see her bra through it. I could feel myself starting to harden, that’s when I took my eyes off of the prize. I could have swarn I then saw her stare at the bulge that slowly built through my shorts, then simmered back down.
We sat in silence for most of the ride when she asked if I had a girlfriend, I replied no, and she looked at me with a face just screaming to be kissed and turned back to the road. The next thing I knew I was at her house. We walked up the steps as she unlocked the front door, we stepped inside and she told me to make myself comfortable. As she walked to the kitchen I sat on the couch, she yelled out and asked if I wanted any water. I replied, yes with ice please. Then her child Owen came running down the stairs.
Once Mrs. Jenkins came back I think she noticed how sweaty I was and asked if I wanted to go for a swim. I replied, I don't have a bathing suit. She said that she didn't either, and whatever underwear I had on would be just fine. I undressed and waited outside in my boxers. Mrs. Jenkins came outside and gave me a boner right away. I think she noticed as she smiled and blushed at me. I watched as she walked up the ladder into the pool. I could tell she was shaved and my boner just stressed more against my boxers.
I hopped in the pool and stared in amazement to how sexy Mrs. Jenkins looked. I could see her erect nipples from the cold water and I knew that she knew I had a boner under the water. She asked if we wanted to play marco polo. I didn't respond and Owen got excited, screaming yes. Mrs. Jenkins went first and I didn't stray too far off as I wanted her to find me.
She yelled out a marco and I returned a polo, along with Owen from across the pool. She went over to me and I pretended to try to jump out of the way as she grabbed the bulge in my boxers and smiled at me. I looked up at her and smiled as she said that Owen won, so its his turn.
I followed her as Owen counted to 20. He yelled out a marco immediately and we both replied Polo, then swam across the pool and sat on the stairs. I sat there staring at her erect nipples as she leaned in and kissed me. I didn't know what to think as she brought her hand to my boxers and dragged my cock out of the whole it had.
She began to stroke it and I wanted to unstrap her bra. I moved my hand up and started tangling with it as she knocked my hand away, whispering "Later". She continued to stroke me harder and faster until I finally came. I told me to cover up and get back in the pool before Owen got suspicious. She let him find her and told him that she had to get going, and could keep playing with me if he wanted to.
Owen and I got out of the pool and dried off. We walked down the street to the pizzeria and I bought him a slice. I did not eat and we walked back home to watch a movie. It was some cartoon, it must have been a new one because it was only a few years ago that I was watching these same shows.
Owen ended up falling asleep around 8 P.M. I sat around watching tv, awaiting Mrs. Jenkins homecoming. I was getting hard just thinking about her. Those tits, that body. I was drifting in and out of sleep from laying on the couch for 3 hours as she came home around 11. I turned and smiled at her as she hung her coat on the rack.
I asked how her meeting went, and she just said it was like every other meeting, boring and pointless. I turned and sat normally, leaning back. She walked over and sat next to me. She placed her hand on my thigh and whispered to my ear “lets finish what we started” I smiled and as I turned to her she kissed me. She began stroking my thigh as we both moved closer to each other on the couch.
We kissed for what seemed like hours, I began stroking her hip as she moved from my thick to my crotch. I was already hard and she grabbed my dick through my jeans. I felt like cumming right then and there. I brought my hand up to her breast and massaged her left tit through her dress and bra. I used my other hand to go around her back, up her dress, and unstrap her bra on the first try, like a pro. She struggled with my belt, and I broke our kiss to lend a hand.
I finish with my belt in a second and once I looked back up she is topless. I simply smile as I lean forward to kiss her breast and use my hand to massage the other. She unzipped my jeans and brought them down, my dick was sticking through the whole in my boxers as she moved on top of me. I moved my hands to her breast and began to play with them as she pulled down her stockings.
She mounted me right away and let out a gasp as I first entered her. I was in heaven. I don’t even know what I was thinking about, not sure if there was nothing or everything floating around in my head. She began to ride me, putting me in even a higher heaven. I didn't know what to think as I let go of her breasts and she started going faster. She was moaning and breathing heavily as she rode me and squeezed her tits with both hands.
I just sat there in silence, moaning and panting. I came was too quick but I told her to keep going until she had a good orgasm. She came pretty late after me and I was hard again, she sucked me off and swallowed until I came one last time. We drove home in silence, both of us looking forward to my next babysitting job.
