We currently have 44660 stories with more being added every day

My Big Breasted Cuban Babysitter

Posted by: Posted on: 0 comments
1 likes 1336 views Category: Masturbation Male-Female Tags:

I am still so turned on at the sight of an older naked woman even after thirty years of my first experience with one. I hope you enjoy my story.


I have a story to tell that involves many years of living next door to one of the hottest and most loving women I have ever had the chance to know. It all started when I was about 11 years old. We lived next door to an older Cuban woman who at the time was in her mid to late fifties who fascinated me with her very large and attractive porcelain colored breasts.

When I was about ten I began to get very aroused every time Grace, not her real name, would come over to our house to see my Mom. She had a habit of not wearing a bra under her blouse and her tits were huge and they swayed from side to side with every move she made. Sometimes I could catch a glimpse down her blouse and it drove me nuts! Grace was a very small grey haired woman that stood about 4'9' but she possessed the tits of my dreams. I would always run to the front door when she came to the house so I could maybe sneak a peek. I would hang around in the kitchen trying to be really casual while Mom and Grace talked and drank coffee. My dick would get hard as hell and it wouldn't take long before I would run off somewhere to jerk off at the thought of her tits. I would jerk off just about everynight night in bed fantasizing about touching Grace's tits.

However by the time I was 12, little did I know that my fantasies would soon come true during an out of town trip my parents would take. I still remember my Mom telling me that she and my Dad were going to take a two week trip and I would be staying with Grace at her house. Grace was married but her Husband was a pilot and he was gone a whole lot. My mind raced at the thought of all the opportunities I might have to see those beautiful titties over the next two weeks. It was the second day of my stay at Graces house and I had just got home from school when my life changed forever.

I had just walked in the front door and the house seemed empty. But Grace just happened to be in her bedroom and heard me close the door. She called out and asked if it was me and I said yes it's me. She told me to come to her bedroom for a minute. I approached her bedroom door and my imagination took over. All I could think of was her tits and my dick sprang up in my pants. The door was slightly open and I could barely see her standing in front of a large mirror that was mounted on the closet door. She was dressed in nothing but a white silk slip and a massive white bra that held in her huge 44D tits. I was really nervous and my knees were weak at the sight of her.

I peeked around the door and said I'm here, what do you want? She said that she needed my help to get her bra unsnapped. It was one of those bra's that had about 10 clasps on the straps in the back. I couldn't believe my luck this was the chance of a lifetime for a kid my age. I was so nervous that I almost ran back down the hall and out the front door. But I managed to hold my excitement long enough to go in the bedroom and stand behind her. It was then that she blew my mind and said, 'honey I know you look at my titties, so do you want to really see them? I'll let you play with them all you want while your here if you promise to be a good boy for me.'

My heart was pounding and I thought I was going to pass out. So I said 'that would be fantastic! do you mean it?' She said 'go ahead and get me out of this damn thing and I'll let you do what you want with them but you have to promise to be good for me.' I said 'you bet I will!' My cock was stiff as a board and it was leaking and my underwear were already soaked at this point and so I said 'ok how do I do it?' She told me to hold each strap at the hooks and just unhook them. I grabbed the straps and it didn't take long before I had the last one undone. At that point she held the bra in place and turned around to face me. She asked me if I was ready and I said yes. Grace let the bra drop to the floor and there I was staring at those incredible big round long titties that I had dreamed about for so long.

They were so beautiful! They stretched down nearly to her belly button. Her nipples were very large and dark and they covered the entire front of her breasts. There was a huge gap between her tits and she swayed her shoulders back and forth and shook them with her hands to make them bounce for me. She took my hands and brought them up onto her tits and said you can do whatever you want but be gentle they get sore easily ok? I could have never imagined how wonderful her tits felt in my hands. They were so soft and warm and they smelled like her perfume. I couldn't even hold one with one hand they were so large. So I used both hands to cradle and squeeze the right one and as the nipple stretched due to my sqeezing I instinctively latched on to it with my mouth.

Grace said, 'that's it my good boy suck it gently, suck my booby's baby.' She spoke softly in Spanish too. I managed to get the entire nipple in my mouth and I sucked it in like a newborn baby. There was so much flesh that all I could do was occasionaly grope and squeeze at the other tit. They were so big that Grace laid the other one over my shoulder as I sucked her. This went on for about ten minutes and then Grace said I wasn't going to do this but maybe you would like for me to get undressed and lay on the bed naked and touch myself for you? Would you like that Honey? I said yes I would if it's ok? She said ok, sit down on the bed and I'll do it for you. She asked me if I liked to look at naked women. I said yes a lot! She said she liked to look at naked women too and that she used to get paid a lot of money to have sex with an older neighbor lady back in Cuba when she was a young girl. That was such a turn on to me! Back to my story, Grace stuck her thumbs into the waistband of the slip and her panties and worked them down over her wide chubby hips. Her belly was real flabby but I didn't care a bit. As her bushy grey pussy revealed itself I thought I was going to orgasm in my pants. My dick was hurting it was so hard.

I was staring at my first naked woman aside from my Mom, and she was absolutely beautiful to me. All I could think about was jerking off and as I thought about it Grace lay down on the bed on her side facing me and said there is something wrong I'm naked, you need to get naked too ok? I was so excited I told her to help me. She reached over and pulled me down next to her and said ok let's get these pants off. I want to see your hard cock. I had never let anyone see me naked and yet here I was with soaking wet underwear in front of this awesome old naked woman. Grace said don't worry it's ok, I don't care about you being wet. It's normal to do that. She said I'm wet too. I thought that smell must be her pussy but I wasn't sure. It turned me on to smell her. So she undid my pants and pulled them off quickly along with my underwear. Then she pulled my shirt up and off. She told me I had a nice young cock and then she told me to rub it for her. She wanted to know if I knew how to masturbate? I played dumb and said what's that? She said that it was something I could do to make my penis feel really good by myself.

She then said I can show you how to do it if you want me to? I said ok, I'd like to know how to do it. I think she knew that I had been jerking off for a while but she played along. It was amazing to feel her soft hand on my dick. She took my cock in her left hand and began stroking it gently at first but she started going faster and faster. Grace asked me how does it feel do you like it? I replied yes I love it, it feels so good. She said good I thought you would like this. As she pumped my dick she put her other hand on her pussy and began to slide her fingers back and forth along her hairy crack. It sounded kind of squishy as she played with herself. Grace began to moan softly and she started with the Spanish again. I didn't know what she was saying but she was obviously enjoying herself. She kept jerking my dick and told me to suck on her titties some more. So I did just that. I began to lick all over them and gently bite her nipples.

She started to quiver and moan louder and all of a sudden she arched her back and she screamed. I heard a noise like she was peeing. I could really smell her pussy now and Grace orgasmed very hard and some liquid gushed out of her pussy onto the bed as I sucked and squeezed her tits. The smell of her pussy was awesome! It kind of scared me but she never missed a stroke while jerking on my cock. I could feel an incredible orgasm building myself and I said I'm going to shoot white stuff cause I didn't know what to call my sperm. Grace said good, go ahead and do it. I guess my secret was out! I grabbed one titty as she rubbed my dick against her other. She stroked it really fast and all of a sudden I shot the most intense load of this white stuff that I ever had right onto her tit and nipple. Damn it felt great! There was a lot of it.

I was exhausted after that all I could do was lay there while Grace rubbed my dick and balls. We lay there for at least another hour before we got up and cleaned ourselves up. I asked her if I could kiss her mouth and she said of course you can sweety that would be really nice. So I learned how to make out that day too. Over the next two weeks we invented new ways to have fun. My favorite way to masturbate was to lay on my back while Grace straddled my face with her monster tits while holding herself up on her hands and knees. I would jerk off like mad and suck and squeeze her big bouncing tits until I orgasmed. This is still my favorite way to jerk off with my wife. Grace and I became very close over those two incredible weeks. We would always wind up masturbating naked together every night before bed. I learned how to rub her clit to get her off with my fingers. When it all began I had no interest in her pussy at all but I soon learned that a woman's pussy is an amazing and beautiful part of her anatomy even if Graces was 60 years old. To this day I love to masturbate while looking at very mature and even elderly naked women and I owe it all to Grace. Grace and I did other things when I was about fifteen but it went well beyond masturbating so that is a story for another website.



You must be logged in to post wall comments or like a story. Please login or signup (free).

Other Stories You May Enjoy