Zesty Older Womanbyhotpup©
Note: This story is dedicated to the older women who help young men lose their innocence. Not only do they teach the art of oral, anal, and fucking but also a little about life.
Crash! The window shattered into a thousand pieces as shards of glass flew everywhere. I couldn't believe how hard I had struck the baseball with my bat. It seemed to fly in slow motion toward her window. As soon as the window shattered the other guys ran off like scared rabbits.
Frozen in place, I just stood there. We had been playing baseball in the vacant lot since I was eight years old. For most of those eleven years our neighbor lady had watched us from that window. This was the first time any of us had broken any of her, or anyone else's windows. As the ball hit the window I saw her scurry aside getting out of the way just in time.
Then she came back to the window and pointed an angry finger at me and motioned toward her front door for me to come over. Gloria was a good friend of my mother's so I knew I had to go over. I was trembling as I walked over. She was known as the neighborhood bitch by the younger generation. She had earned this reputation by yelling at us for cutting across her finely manicured lawn and other such terrible things that showed that she liked to have a nice home and neighborhood.
She was no beauty queen but had aged well. To us she seemed like an old lady, after all, she was 41 years old. She was a bit stocky but not what I would call fat. She had light brown hair and hazel eyes and stood about 5'3" and weighed 140-150 pounds. While she had great D cup boobs and an average sized ass everyone noticed how long her fingers were. We had never seen fingers that long.
So, timidly I went to her door. She let me in with out a word and walked toward her dining room where the window that I had broken with the best line drive I had ever hit was. Firmly she asked, "What do you have to say for yourself young man."
"I'm sorry Mrs. Yates I never thought the ball would fly that far." I looked down and saw the ball laying amongst the remnants of the window.
"You were wrong. Now look at this mess. What should we do about this?"
"I guess I need to clean it up and figure out some way of paying for the window."
"That sounds fair. The broom is in the kitchen closet." Not wanting to stay there any longer I hurriedly grabbed the broom and swept up the glass. She held the dustpan for me and I noticed that she wore a very sexy scent of perfume. I shook my head to get that thought out of my head.
When I thought I had gotten every piece of glass and retrieved my ball I asked, "How's that Mrs. Yates?"
"Well, it looks as if you got it all. Come back tomorrow after school and I'll tell you how much you owe me." Seeing an opening I headed for the door and ran straight home. All night I waited for the phone to ring as I expected Mrs. Yates to tell my mother what I had done, but it never did. Checking my finances I had only $5.00 that I could give Mrs. Yates. I hoped that she could take payments.
Stuffing the $5.00 into my pocket I hurried off to school the next morning. The day seemed to drag by. Only one good thing happened the whole day as Candy Peacher agreed to go with me to the Spring Dance. My friends asked what happened with Mrs. Yates and I explained that I had to go to her house after school.
They harassed me about how much trouble I was in. Putting up a brave front I laughed them off. In truth, I was scared of Mrs. Yates and had no idea how much a window cost. I knew it would cost a lot more than $5.00 though. I knew in my heart that she would have to tell my parents as there was no way for me to pay her.
Not wishing to aggravate her anymore I went straight to her house right after school and made sure I walked up her sidewalk not touching one blade of grass. Again, she let me in and walked to the dining room. She was almost smiling as she pulled a piece of paper off of the table. It was the bill for the window. Coolly she said, "See the new window you are paying for? I need $159.50 to pay for it."
I reached in my pocket and pulled out the money. "All I have is $5.00 but I can make payments."
She grabbed the bill from my hand replying, "How old are you?"
This question seemed odd to me but I answered, "I turned 18 last October."
"That means I might get paid in five years with everything a high school senior has going on. That just won't do." My heart sank as I knew she was right.
"Can't we work something out?"
She paused acting like she was thinking things over then said thoughtfully, "You still owe me $154.50 and minimum wage is $2.65 which what they would pay you at the taco shack. That comes out to 60 hours of work you owe me. Does that sound fair?"
She had me by the balls and she knew it as did I so I replied, "Yes, Mrs. Yates."
"I want you here everyday after school for two hours, unless you make advance arrangements to take a day off, until the debt is paid. Be clear on this you will do anything I ask of you, I mean anything." She smiled an evil smile as she finished speaking. What had I gotten myself into?
Meekly I spoke, "That sounds ok Mrs. Yates."
"Call me Gloria as we will be working VERY closely together in the next few weeks. How about getting to work and begin to pay down your debt." I agreed and soon she was having me doing very mundane jobs around the house. I cleaned off the dusty top of the refrigerator, swept out the garage, and pulled some weeds. Everyday she seemed to get a little friendlier and smile a bit more.
On my fourth day of working for her I noticed how sexy she was for the first time. She answered the door wearing tight fitting jeans and a V-neck top that displayed her ample bosom enough that I thought with some effort I might catch a glimpse of one of her nipples. The first half hour went as usual as I moved some stuff around in the garage. Then, she wanted me to put some things on a high shelf which required a ladder to get to.
The shelf was higher than I thought. It couldn't be reached without standing on the very top step of the ladder which made me extremely nervous. She volunteered to help me by steadying me on the ladder. She would hold on to my legs so I wouldn't wiggle around so much. It didn't sound like it would help at all but I agreed to give it a try.
Climbing up the ladder I reached the top step as she put her hand on my leg and handed me the camping lantern she wanted up there. Suddenly, both of her hands were on my legs just below my ass cheeks. She was squeezing my legs tightly. Somehow, it did make me feel more secure. It was a struggle but I finally reached high enough to get the lantern into its place.
The worst part for me was always coming back down the ladder as there was nothing to hold onto. This is where Gloria's hands felt real good back there. Starting down I noticed that she hadn't budged. As I got three steps down her hands slipped to my ass and began caressing it. Pretending to ignore what she was doing I took another step down. Now, she began kneading my ass cheeks. Then I heard her go down two steps so I followed suit.
She took one more step down so she was standing on the floor but was still clutching my ass. After I stepped down another two steps my ass was right in front of her face. Gloria reached around me and wrapped her fingers around my hard shaft as she buried her face in my ass. I couldn't move, and didn't really want to. Seductively she purred, "Remember, I said you would do anything I asked when you were here?"
"Yes, Gloria I remember that very well."
"Then, I want you to turn around right now." Stunned at the boldness of the request and equally turned on I carefully held onto the ladder and faced her. I was now only a couple of feet off of the floor but still didn't want to fall. Leaning back against the ladder I waited forever for her to make the next move (about three seconds). Her hands found the button and zipper of my pants and deftly undid these and pushed my underwear and pants halfway down my thighs.
My eight inches was stiffer than I can ever remember it being and was pointing directly at her full lips. Wasting no time she grabbed the base of my rod with one hand and my balls with the other. Gently she stroked her hand up and down on my shaft as she sucked the head into her luscious mouth. Before I knew it she had swallowed my entire prick into her mouth. She swirled her tongue all over the underside sending a chill up my spine.
She was vacuuming my cock in and out of her mouth like a well oiled machine. I held on for dear life to the ladder as I knew I would move around too much and cause it to fall. But, somehow I stayed put. I was at her mercy until she said otherwise. For a brief moment she let me go as she pulled her blouse off over her head. Knowing she was half naked turned me on but I really couldn't see anything as her head was in the way.
The heat was rising in my groin and I warned her I was about to cum. She only seemed to suck harder. Letting out a loud grunt my spunk flooded her hungry mouth. She calmly swallowed it down with not so much as a little gag. Removing her mouth she backed up a step or two and used her hand to continue to jack me off.
She aimed my cock for her melon sized boobs which she was now giving me my first look at. They were wonderful orbs that seemed to stand out from her chest. She pumped until I splattered a load onto each breast. She wiped my cock head off with her finger and licked it clean.
Gloria reached down and picked her blouse up from the floor. Tugging my pants a little she helped me off of the ladder. Smiling broadly like the cat who ate the canary, holding up her tits she nonchalantly said, "Come to my bedroom I have a couple of things I want you to clean up back there."
As I struggled with my pants I realized I didn't know where her bedroom was as I had never been to that part of the house. It was a large four bedroom home. Jogging from room to room I looked for her. First, I found the den then both of her kid's rooms. There was no risk of them or her husband catching us. The kids were both off at college and her husband was working from noon to 8:30. Finally, I found her room at the end of the hall and there she was standing beside the king sized bed.
She was now wearing matching bright blue bikini panties with garter belt and stockings and black stiletto heels. The hard-on in my pants was now already back at full size. My eyes were glued to her erotic frame. She knew what she was doing as she commanded, "I won't permit those filthy clothes in my bed so, strip and lay down in the middle of the bed face down."
Now I had no doubt the best was yet to come so I dropped my clothes in a heap near the door. Running over to the bed I nearly dove into it. This was her game so I waited for her move. Hot breath suddenly hit my ass at the same time as her hands grasped both of my butt cheeks. She didn't mess around as her tongue was sweeping up and down my ass crack furiously. I felt a poking at my anal opening; it was her tongue.
This was a totally new experience for me. Her hands expertly worked on my ass cheeks pinching, pulling and squeezing them as she tried to get her tongue further inside my bowels. Before I knew it I found myself pushing my ass harder against her attack. I didn't know that I could cum from having someone work on my ass like that before but sure enough I spasmed as I felt a jolt go through my body.
Having accomplished getting me off without touching my prick she moved away. She took a seat against the headboard. For a moment all I could do was stare at her cum covered tits and wonder how she had managed not to let the gooey stuff get wiped off when she kissed my ass. Teasingly she gave my side a small kick to get my attention. Seductively she urged, "Come here and clean my boobs, come nurse on my boobs." Gloria had me lay sideways across her chest so that I looked like a baby nursing on his mommy's tits. Wrapping her arms around my back to cradle me into her bosom I devoured the salty spunk from her titties and continued sucking and kissing for everything I could. Working overtime I moved from boob to boob. She had a tight grip on me that got tighter and tighter. Suddenly, she pulled my face up to hers and gave me a deep passionate soulful kiss. High School girls didn't kiss like this.
"That was nice, now let's see how you are at eating pussy," she whispered in my ear. As she laid down all of the way on the bed I ran my hands all over her stockings and panties. Eating pussy was one of the things I liked best but found too many of the high school girls I had dated thought of it as dirty and didn't even give me a chance. Once Gloria was fully laid out I found the clasps of her garter belt and undid them.
Anxious to taste her snatch I hooked my fingers in the sides of those sexy panties as she raised her ass off of the bed and pulled them right down. The full shiny pink lips invited me to her beautiful pussy that was covered with thick brown hair. The Heat seemed to rise from her core like a furnace as I got closer and closer.
Her slash was soaked with her love juices. The aroma was pulling me in. Forming my tongue into a scoop I began licking up her long slit. Her juices seemed to flow freely right into my mouth. She was bucking her hips in my face; I knew what she wanted.
Not one to disappoint I scooped up her juices one more time then found her clit with my tongue and gently flicked it with the end of my tongue. She bucked me harder, so I licked her clit harder. She continued to buck her hips in my face so I sucked her hot button into my mouth. I sucked it hard as I ran my tongue all over. I was doing something right as she pounded the bed with her fists.
Letting up for a minute I checked out her slash and it was again gushing with her juices. Hurriedly, I scooped up her sweet juice into my mouth before clamping back down on her clittie with my lips. Gloria appeared to be really having fun now as she dug the spiked heels of her shoes into my back as her pelvis convulsed all over my face.
"John, it is time to fuck me now," she implored as she held out her hands for me to climb up her body. As soon as my face was near hers she licked her cunt juice off of me. Feeling my cock near her opening she thrust her pelvis up and captured it on her first try. That magical cunt seemed to swallow me up as I found myself buried up to my balls before I knew what was happening.
It was so warm and tight in Gloria's pussy and I could feel her use her muscles to milk my cum out of my cock. She dug her heels into my butt and met me thrust for thrust as I rammed in and out of her. I admit I had no stamina and came in no time. But, Gloria was just as hot and came quickly as well. I rolled off of her and she noticed the time and told me to leave but to get my ass back the next day when we would share new experiences.
At school the next day I almost didn't keep my secret a as I almost told my best friend Aaron Berrybush. I decided not to tell him as he wouldn't believe me anyway. Little did I know that a few months later he would fuck Felicity Peacher, my Spring Dance Date's mother. So, I kept it to myself and made it to Gloria's house in record time. She answered the door in her robe and said, "Strip and come to bed." Again, she was way ahead of me as I hurriedly got naked. When I got to her room there she was laying face down on the bed totally nude. I just had to say something. "Oh my God, Gloria, you are a very sexy lady and your ass looks fabulous."
I thought that I had sounded a little stupid and blushed but Gloria simply responded, "Well, then, get over here and kiss my ass."
"Yes, ma'am," was all I could say as I eagerly climbed onto her bed and moved over to her nice ass. Tenderly I ran my hands all over the rump getting to know her twin pillows of pleasure. Then I gave her ass little butterfly kisses all over before moving on to full fledged passionate licking and kissing. Her crack seemed to be calling to me so I listened and dove into it my tongue caught the edge of her hot rosebud so I tried to shove it in.
Meeting with some resistance I continued to work on her asshole and finally got the tip of my tongue inside. It wasn't long before Gloria was ready for more as she handed me a tube of lubricant. Never having butt fucked a woman before it was still obvious what I was to do with the lube. I smeared the stuff all over my cock and shoved a couple of fingerfuls up her rectum.
My aim was true and my head popped right in as Gloria squealed softly. Then I gave it a push and my goodness was it tight. I didn't think it would go any further. Her muscles seemed to relax so I pushed again and moved an inch or so. Grunts of pain were coming from both of us. Gloria begged me not to stop. With each stroke I seemed to be getting deeper and deeper. At last, I was all of the way in.
We stayed frozen in place for about a minute like a dirty statue allowing each other to get used to the sensation we had created. Slowly, I pulled back. Then slowly I pushed back in. Now, with each full stroke the speed increased along with the feeling of pleasure. Before long all memory of pain was gone and I was pumping in and out of her strong and hard. Her hips moved sensually to the rhythm of my strokes as she moaned encouragement. As I came closer and closer I felt her hand playing with my balls and her clit. All at once I erupted inside of her as I felt a dribble of her cunt juice run down my balls.
This was the most energy I had ever used in any activity and boy was it worth it. For the next hour we laid there and made out as we were too worn out for much more activity. We kissed passionately and she allowed me to kiss her boobs again but mostly we just caressed one another.
We continued until my debt was paid four or five nights a week and occasionally on the weekends. We did continue after I was paid up we called it interest on the bill. But gradually, we faded apart as I took Candy to the dance and later met Betty and married her. But I learned tricks from Gloria that I will always be grateful for.