My Last Baby Sitter
Many years ago, in the mid 60's, when I was about 12, I discovered masturbation. It was quite by accident I suppose. I can't remember the 1st time actually. It just naturally came to me.... no pun intended.
Well, my folks were going out for a late night party. They actually got me a baby sitter. It was a disgusting thing as far as I was concerned. My older brother was away on a camping trip for 2 weeks in Canada. So, even through the protests, I was introduced to a girl, Lee Ann, who was probably about 18, I guess. Still in high school I guessed based on the conversation my folks had with her, as they were getting ready to leave.
I remember when my folks left; Lee Ann flashed her cute smile and sympathized with me for having a babysitter at my age. She seemed to be pretty cool, and told me to just pretend she wasn't even there. Do what I normally do. If I needed anything, just let her know.
After getting some snacks and drinks, Lee Ann and I went downstairs where the main TV was. We made some small talk for a few minutes while watching a movie I was watching when she arrived. Soon after that, she was on the phone with some friend of hers. It became quite apparent real soon that Lee Ann was a phone freak, and I figured some day the phone would permanently attach itself to her ear.
Lee Ann was not bad looking at all. She had a cute face, and soft eyes. I sneaked plenty of looks at her as she talked and giggled on the phone. She was sitting on the couch, and when she leaned forward to get some of the snacks on the table, I could steal some peeks at her cleavage behind her rather low-cut blouse. Low enough for me to see they were there. And, I liked that there were two buttons in front that told me exactly where her nipples were. That was a good indication of how big Lee Ann's tits really were.
But, it was her legs that turned me on the most. Muscular legs. She was a bit on the chubby side. Probably just baby fat. However, she was certainly well proportioned. She wore a skirt that rode up those delicious legs as she moved about while yacking on the phone.
Well, I went upstairs after awhile, and picked out a washcloth, and plucked the copy of Playboy I had hidden in my bedroom. I figured she would never notice I was looking at it since she was on a couch probably 15 feet away from my favorite couch to watch TV. I also like masturbating on that couch when I was alone enough. I remember masturbating a few times on that couch while watching Ann-Margaret movies. She was a living doll. She exuded sex every time I saw her on TV. I also masturbated watching Mary Tyler Moore. I loved the shape of her breasts, when she wore outfits that showed it more. Her smile melted my heart. Both of these goddesses had voices that made my cock twitch.
I came downstairs wearing a pair of shorts that were very loose. They were nice for reaching in the sides to squeeze my cock. Roomy enough to be able to jack off, but still have clothes on. I had the magazine with me, but it was hard for her to see that it was a Playboy, I'm sure.
I don't remember the movie that was on, but I think it had some pretty girls in it. It didn't take much for me to get turned on. So, I watched, and also looked at the playboy, flipping the pages. And, I sneaked more glances at Lee Ann. Getting all horny in front of her was a new experience for me. I hadn't started dating at all by then. I fantasized about girls at school sometimes, but I never made any real social contact with them yet.
My cock was stiff as a nail in a New York minute. I glanced at Lee Ann once in awhile, zeroing on her smooth legs. I imagined myself humping on her beautiful thighs. I looked at a picture, and looked at Lee Ann, imagining what she looked like without her skirt. I tried to imagine where her thighs met her nice butt. I could catch just a glimpse of her panties as she shifted herself to get up. She went upstairs to get another soda, and while she was gone, I pulled my cock out of the side of my shorts and jacked it hard a few times until I could hear her coming back down the stairs.
She picked up some movie star magazine she brought over, and laid back on the couch, kind of facing me. I'm certain I burned a hole right through her legs, as I zeroed in on her meaty thighs. She lit a cigarette, and while she dialed another number, she looked over at me. "What you reading?" I felt bold enough, and raised the Playboy up so she could see the cover. She smiled a devilish grin. "Ok", she giggled. "Don't let me bother you." She was casually flipping through the TV guide, and talking to another girl friend of hers. Occasionally, I could hear her whispering.
I guess I was a boy/man ahead of my time, because I sure wanted to jack off right then and there. What would she say? She seemed rather cool. So, I put my hand in the side of my shorts, and stared squeezing my cock, over and over again. I stroked it a bit, too. I snuck a look at her, and I swear she parted her legs just a bit. The darkness under her skirt only made my mind race more thinking about what beautiful sight there was to see up in Lee Ann's mystery zone.
I flipped a few more pages, and saw miss June, in the Playboy I borrowed from my friend down the street. His name was Phillip, and he's he one who taught me about masturbation. Miss June was so pretty. Her hair was very similar to the Lee Ann's. I imagined the model WAS the Lee Ann, and the Lee Ann WAS the model, posing for me.
What put me over the edge was when Lee Ann sat up, then bent over to take her socks off, still talking on the phone. She took a LONG time doing it, too. I could see between her sweet breasts as they parted inside her blouse. It wasn't like looking at the model in Playboy, but she was live. When she seemed to have a rough time with one of the socks, she shook herself to get it off. And, seeing her breasts swaying as they did about got ME off. She leaned back on the couch again, and had the magazine stuck in front of her face, the phone still stuck to her ear.
Throwing caution to the wind, knowing that my desire to be an exhibitionist must have been born in me, I started pumping my throbbing cock inside my shorts. I'm sure I was trying to be a little discreet. But, I just don't remember. I do remember glancing her way, and noticing her right leg was bent, and she was swaying her whole leg back and forth. Like a nervous habit, but later, when thinking about this, I wondered if her pussy ever got hot doing that.
I know one thing. I know that it didn't take long, and I was spurting cum inside my shorts. There was always huge puddle dampening my shorts every time I came in them. Phillip made a comment once that it looked like I was peeing my shorts when I came. That's why I had the washcloth.
My breathing must have been a dead giveaway. After I could finally glance her way again, she was still talking on the phone, of course, but the magazine was lying on her ample chest. And she was giving me the biggest, warmest smile someone other than my mom ever gave me back then.
I think she must have known what I was doing. I even heard her giggling with her friend on the phone, and immediately thought they were laughing at me. But, that actually made me feel more satisfied.
I did this one more time with her a week later. Still nothing said, but this time, I actually snuck my cock out a bit as I masturbated with my sweatpants on. I KNOW she saw that. But, she acted as if she didn't, the phone still implanted to her ear.
That was the last I ever had a sitter. The last I ever saw of my 1st audience. But, the thrill has never left me. Nor have the memories of the good sport, Lee Ann.