My first time wit the old babysitter
Introduction:
This is a true story. It starts slow but does pick up the further you read
Let me introduce myself. My name is Brian. I’m like 5 foot 7 inches tall and weigh around 120 pounds. I am told that I am good looking. We lived in a nice suburb near Chicago. I am an only child and both my parents worked. My Dad had just received a big promotion at work and we were about to move about 90 miles away to be closer to his job. They had already bought the new house but since all my friends were in my old neighborhood, they let me stay at the house until it sold. My only job was to make sure I cut the lawn and I cut the lawn for our elderly neighbor who was in the hospital. It sucked because it would take like 4 hours to cut both lawns and it was a hot summer.
Being a typical teenager, I got up at the crack of Noon. It was about 95 degrees out with high humidity. Unfortunately, I had been procrastinating and I hadn’t mowed the lawn and people were coming to look at the house the next day. So the first thing I did was throw on gym shorts and a tee shirt and then turned the air conditioning on in the house.
When I was about half-way done with our lawn, I decided to take a quick break and cool off a little in the house. I walk in the house and its like 90 degrees in the house. The air conditioning wasn’t working. Great. So I figure there was no use sitting in the hot house and went back outside to finish cutting the lawn.
It was so hot and humid that my tee shirt was so soaked with sweat that I finally just took it off. I finished cutting our lawn and then I went next door to Mrs. Kendall’s house to cut her lawn. Just after I started cutting the lawn, I hear a woman calling my name. I turn off the mower and turn around and standing on the porch of Mrs. Kendall’s house is an older woman around 30 with a sexy tight two piece bikini. Her legs were long and tan and her breasts looked like they may burst out of the bikini top. Of course right away, a bulge starts to form in my shorts. Luckily I was holding my tee shirt in my hands and was able to hide my excitement.
She asked me if I was Brian. I told her I was and asked how she knew that. She said don’t you remember me? I’m Cheryl. I still had a confused look on my face. She goes on to say that she is Mrs. Kendall’s daughter. She told me that when she was in high school, she used to baby sit me. That’s when I remembered her. But she was much more of a woman now. I hadn’t seen her in like years. I thought she had gotten married or something and moved to California.
She then said to me, you look tired and worn out. Why don’t you come inside the house and I’ll give you some lemonade. I follow her into the house and I am immediately hit with a cold breeze – her air conditioning was working. And it was working real well since I noticed Cheryl’s nipple start to poke through her bikini top. She didn’t seem to mind that I was staring at them. She then motions for me to sit down at the table and she gives me a glass of lemonade and puts out some cookies.
I tell her this is nice. The air conditioning at my house doesn’t seem to be working. I start drinking and eating while Cheryl goes on to tell me that she will be staying at the house for a few weeks while her mother is in the hospital and that feel free to come on over anytime until the air conditioner is fixed.
I then say, that I better get back to the lawn. Cheryl said to just wait one minute. Your shoulders and back look like they are getting a little red. She offers to put some sunscreen on for me. I said no, that’s OK as I start getting up from the chair. She said nonsense and has me sit back down. She rubs some sun screen on her hands and then begins to apply it to my shoulders first and then down my back where she even has one of her fingers go down below my elastic waist band but it probably was done on accident. . She then tells me to stand up and from behind me she starts applying it to my chest and stomach. It started feeling awkward and sensual as she continued to rub my chest and stomach. She leaned in a little and I could feel her tits poking me in the back. Luckily I was still holding my shirt to hide my erection. Then she reaches down and has her finger tips go below my waistband in the front. Not very far only like an inch or something but its obvious she is doing this on purpose. She then starts putting sunscreen on my legs. Which really wasn’t necessary since I had a nice tan base on my legs. She goes down to my ankles just above my socks and goes all the way up my leg. She moves my shorts up a little so now she is putting sunscreen on untanned areas. I finally said, I have to finish cutting the lawn and then go out the back door and start up the mower and begin cutting the grass.
Once I was done with the lawn, I was spent. As I was pushing the mower back over to my house, Cheryl opened the door and said come on back here after you put the mower away. I come back a few minutes later. I am very hot and drenched in sweat. She said to me since it is still hot out, why don’t you hang out here for a little while until it cools off outside. She hands me a paper towel to start wiping off the sweat. She then says, why don’t you go in the bathroom and take a shower and get all that sweat off you. This way you will be more comfortable. That sounded like a good idea so I said sure and head toward the master bathroom. Cheryl said she will bring in some fresh towels.
I get in the shower and it did feel nice rinsing the sweat off. My penis was rock hard which is force of habit. I usually jerk off in the shower but didn’t now because it didn’t seem right. I hear the bathroom door open and I hear Cheryl say that here are some fresh towels for you and then shuts the door. After a couple more minutes, I complete my shower and I take the towels Cheryl left and begin drying myself off. As I was just about dry, I begin to realize that my shorts, boxers, and shirt are not on the floor where I left them. The only thing I could think of is that Cheryl took them, but why.
I then wrap one towel around my waist and step out of the bathroom into the bedroom. I see Cheryl is in there making the bed. She asked me how I felt and I said fine. I then asked her where are my shorts at? She said that when she brought the towels in she noticed that they were all sweated through – which was true – so she put them in the washer. They should be ready in about an hour. Cheryl, said in the mean time why don’t you just lay here in bed in the cool room and just relax. She thanked me for cutting the lawn and she walks out of the room and closes the door.
I keep the towel around me and lay down in bed. I must have fallen asleep right away. I then start having this weird dream. In this dream, I am laying in bed and I feel this hand caresses by ass and then I start feeling a warm breath on my kneck along with more kissing. Then, in the dream, I feel a leg touch my leg. I then begin to realize that this isn’t a dream, this is really happening. I open my eyes and I see this hand rubbing my chest. I jump for a second but Cheryl, who has her arm around me says just relax everythings fine. I then realize that the towel is open and my penis is sticking straight up. This is the first time anyone has ever seen me completely naked and erect. Its decent size. I measured it once with a ruler and it was like 6 inches.
I then roll over on my back and there is Cheryl who is also completely naked laying next to me. I am in heaven. I had never seen a naked girl before – yes that’s right I was a virgin. I continue rolling over until I am completely facing Cheryl. She tells me that if I was uncomfortable about this that she would leave. Of course I tell her that its fine. She also said that we don’t need to do anything more then I am comfortable doing. I only say OK since I am not entirely sure what she had in mind.
She then pulls me closer and begins passionately kissing me. I had kissed girls before but that’s really all I had done. She then pushes her tongue into my mouth. I clumsily do the same to here and it was really erotic and I could feel my penis growing larger. I then move down and begin kissing her neck. With my one hand, I start squeezing her breast. She said to do it gently and focus on the nipple but dont pinch to hard, just squeeze. I try to follow her instructions and she begins to moan a little and said oh baby that’s the way. hmmmmm. I still cant believe that this is happening. I then move my head down and start sucking on her tits. I alternate left and right and she continues making loud sounds which are turning me on even more.
She then pushes my head down between her legs. I couldn’t believe it. I was eye to eye with a real pussy. She then takes my hand and puts three of my fingers inside of her. She starts rubbing herself and I can feel my fingers getting wet. She moves her hand back and forth and said yeah just like that. She then lets go of my fingers and removes her hand but leaves my fingers in her and I keep doing what she was doing and she starts squirming some more and it is getting so wet and hot in there.
I then get adventurous and without being prodded. I pull my fingers out and place my face over her pussy and shove my tongue in there. I start moving my tongue back and forth which was driving her crazy. I then feel this, for lack of a better word, a hard piece near the top and as I touch it and start flicking it with my tongue, Cheryl goes crazy and grabs my head and pushes it as close as can be which then causes my tongue to go deeper inside of her. The more I do the more juices that keep flowing out and I start to think that I think I am giving her an orgasm. She screeches a couple times and then finally grabs my head and pulls me up toward her head.
We begin kissing again. My tongue which is soaked with her pussy juice is now being fed to her as we keep swirling our tongues inside of each others mouth. She pulls me close to her and now my penis is at full attention around her waist.
She then says to me that she wants to feel me inside of her. But she also said if I wanted to stop that we could stop. My head on my shoulders was not doing the thinking anymore but the head between my legs was and he said go for it. I told her it was OK. Don’t stop.
I maneuver myself so that my penis is right outside her pussy. I begin rubbing her from the outside because I read something stupid to not just shove it in here. Unfortunately, with all the sexual excitement and my inexperience I rubbed it a little to much and then I feel my orgasm coming on and I lean forward and shoot the thickest whitest streams of sperm that I have ever shot in my life. After what seemed like a whole minute of cumming, I realize OMG she is going to think I am such a loser and I start crying and apologizing to Cheryl. She said, Brian, just relax. I’m sure this was your first time its natural. Now come over here. I lay down beside her and I feel her grab my penis. She said, just what I thought. She said at my age, I should be ready to go again in just another minute or so. She then moves down and takes my penis into her mouth. It was an unbelievable feeling. I could feel her tongue swirling around on my penis moving her mouth back and forth and up down the shaft. I then feel myself getting bigger already and harder. I feel her licking and slurping some more and she said to me, lets do this again.
Cheryl rolls over on her back and get between her legs. She said you don’t have to run around the outside just slowly push it in me. Just relax baby, you’ll be fine. I get into position but I have a hard time maneuvering it into position and I cant get it in there. She then reaches down and grabs my penis and said let me help. She slowly movers my penis into position and puts it right at the entry hole. She tells me to push forward real slow. I think to myself that this is it. My very first time my penis is going inside a girl. I lean forward and I can feel the heat coming from there. She tells me that when I feel resistance. Stop pushing for a second and then continue pushing. As I begin entering her it feels so warm and slick inside her I run into resistance a couple time but keep following her instructions until finally I am all the way in. We are completely one person now. Instinctively, I pull back a little and then push it in and I continue this thrusting back and forth. As I’m doing so I notice Cheryl breathing increasing and I can feel it getting wetter inside of her. She then wraps her legs around the back of my thighs which pulls me closer and I think even deeper inside of her. She wraps her arms around my back and we begin kissing. I then start feeling constriction around my penis. As I thrust back and forth inside her this constriction is undescibeable. I begin thrusting faster back and forth and she is now in sync with me thrusting back at me. She then give out a scream and pulls me as close to her as possible with her legs and arms and I feel her pussy start squeezing my penis as she screams. I can feel my orgasm building. I cant hold back any longer and I let loose. I try to keep thrusting as I am orgasming but her pussy is strangling my penis trying to pull every ounce of sperm out of it. I then collapse onto her. It was nothing like jerking off with your fist.
A few minutes after ejaculating in her. I am still on top of her and still in her. Suddenly, my head on my shoulders takes over and I pull out of her and lay back down on the bed next to her. She could tell I was a little upset and asked me what was wrong. I told her that we didn’t use a condom so theres a chance you could get pregnant. That’s what they told us in health class. How could I be so stupid. She then calmed my worries and told me its alright and that she was on the pill and there was nothing to worry about. She then asks me if I enjoyed it. Of course, I told her I did because I DID. I then sheepishily ask her if we could do it again and she told me sure. We ended up fucking for most of the night. I must have come inside her like seven or eight times. With each one feeling better then the next.
I learned a lot from Cheryl over the next few weeks. Things I was able to use that made my future girlfriends very satisfied. But towards the end of summer, our house sold and I moved away. My mom heard from some of our former neighbors that Mrs Kendall had died and that her daughter went back to California.
Fast forward four years. I am on Spring Break of my Freshman year of college. I decided to spend the week at home. I wake up and come down into the kitchen to make some lunch and see my mother at the kitchen table crying. I asked her what was wrong. She slides an envelope over to me. I open the envelope and it has a picture of a little boy. I then start reading the letter and its from Cheryl. Apparently she had separated from her husband a few years ago and after her mother died she went back to her husband in California. I think to myself. Wait a minute, she never mentioned any husband. I continue reading the letter and Cheryl tells my mother that I had sex with her during the summer and nine months later, Cheryl had a baby. It was the splitting image of me
Cheryl’s husband was divorcing her and he claimed this kid was not his since it did not look like him or any of the other kids. I had to go down and get a DNA test and luckily for me, it was determined that I was not the father. But Cheryl’s husband was not the father either. Apparently Cheryl was having sex with someone else beside me. Later I find out my friend Tommy came over once and Cheryl seduced him and had sex with him one time. It turns out Tommy was the father of the baby. I feel bad for Tommy but thank God it wasn’t me.
