When I was younger. My friend Joe's mom had a girlfriend. She was a single mom with a little son. One saturday, Joe told me he volunteered to babysit the lad while his mom's friend went to a office party. He wanted me to stay overnight there with him and keep him company. We were mischief teens and snooped her panty drawer finding all sorts of silky under things. We also found a long, hard plastic, vibrator, (back then, they sold them as face massagers),. We jokenly talked about how her pussy must be cavernous to be able to take the whole thing. Well the young'n went to sl**p early, and we wat... Continue»
Hello, it's been a while since I've written anything on this site. Mostly because I've been busy with school and my social life has blossomed. I know I was going to post pictures from my last story but I had no luck in finding any pictures. My old house got flooded and I knew exactly where my pictures were but there was too much mold by the time I got to them that they spoiled. Other than that misfortune, it's been pretty good.
One of the positives about having a blooming social life is that I am able to see more and more beautiful women. I have been able to sit down a talk to them and get to know them more than I ever had been before. I soon found that most teenage girls do not like bigger guys. I'll admit it that I am slightly overweight, but it's not like I'm just a blob. I work out about 4 times a week and I'm pretty muscular. Not the strongest guy in the gym but defiantly not the fattest guy. So where am I going with this? Well I guess I could say it started about six months ago at my friend Matt's house.
I never really hung out with Matt in high school but when we both went off to college, we slowly started to see each other more often. We soon became really good friends and hung out at least four times a week outside of classes. This was our entire freshman year. When we both took the two-hour trek back home we talked and decided that we should hang out more often. So soon after I got settled in and reconnected with my f****y, I asked if he wanted to hang out. He invited me to his house for swimming and a beer. His younger siblings and his dad were out camping that weekend so only his mom would be home.
It was about one o'clock when I arrived at his suburb. He had a decent sized house with at least four different cars, but when I got there, there were an additional six cars. Matt decided to invite a bunch of high school guys over for a pool party. I cannonball’d right in without looking around. When I emerged back up, it was very quiet. I turn around a see a beautiful blonde woman with a stack of towels, drenched in water. I immediately begin apologizing as she drops the wet stack of towels. I follow the towels with my eyes, and slowly gaze back up at this drop dead gorgeous woman drenched in a yellow sundress. I can see the outline of her panties and her bra. She immediately ran back into the house with Matt following right behind her.
Everybody couldn’t help but laugh at the strange predicament that we were all in. Some guys even came and gave me a high five. Everybody agreed that she was hot and I just made her look even hotter.
By the time Matt came back out 15 minutes later, people were already saying how they were ready to leave, I was still extremely excited from the mini show that went on when I got there. I stuck around a little while longer and soon Mat asked if I wanted to sl**p over, I obviously agreed and went for a glass of water. When I got in the kitchen she was there
Her name was Ann; she was about six foot, B cup breasts and a great apple ass. If I had to compare her to a celebrity, it would be Naomi Watts with her sexy little breasts and pixie cut blond hair. I walked over to the sink and turned the water on. She was startled and turned in one quick motion.
“Oh you scared me”
“Sorry” I said in a slight innocent voice.
She introduced herself and seemed really nice. She only could be in her forties because her face was just flawless. I began talking to her and soon forgot about the running water.
“Hey, what do you think this is a free water joint?” she said jokingly.
I looked and saw the sink filled with water.
“Well how about I get you a glass to put that water in?” She jokingly said.
I laughed as she turned to the cupboard behind her. She was only wearing a short sundress and when she reached with her tiptoes to reach the glasses on top, I could see the bottom half of her butt cheeks and a string squeezed in-between them. Just at the sight of this I got an instant hard on. She turned and I turned to turn the water on, but to really hide my hard dick. I only turned my shoulders to reach the glass as I composed myself. I ran the water cold on my finger for quite a while, hoping that it would tame my hard-on. Luckily it did and as I turned she was on her tiptoes again only one cupboard over putting dishes away from the dishwasher.
“Can you hand me a few plates?” She asked.
I immediately complied seeing that the dishwasher was ground level and the rollers were broken. I got down on my hands and knees and started reaching back to the dishes. As I turned to give her the first dish, my eyes immediately went to under her dress where I saw just a little bit of the front of there underwear. I looked back up at her and saw that she was preoccupied with rearranging things at the top cupboard. I sat there for about three uninterrupted minutes looking at her fit sexy thighs flex as she was constantly on her tiptoes. As the dishes were running out, I realized I had to stop looking before they were all gone. I luckily looked away when there was only one dish left. I handed the last one up to her and stood up quickly, trying to make a dash for my friend’s room. As I was just about to leave the kitchen she called out
“Thanks hon. that was a big help.”
I couldn’t help but to smirk at her usage of big while I was running away with a big one myself.
Matt and I stayed up until about ten. I was only slightly buzzed but Matt was just hammered. He passed out as we tried to watch Blue Mountain State. Matt was passed out on the bed and when the show ended I got up and decided to get ready for bed. Matt’s house is two stories with three bathrooms. His room is at the top of the stairs and I could see that all the lights were out from downstairs. I decided that it was a better idea to use the bathroom upstairs. I went down the hallway and heard running water. I didn’t bother to turn on the lights since there were little nightlights lining the halls for his little siblings. I kept walking towards the water and heard it coming from a closed door. I was a well-trained expert on creeping, as can be seen on my previous post. I quietly opened the door and found Matt’s parents bedroom. It was decent sized with a queen-sized bed. I closed the door behind me and began to look around the room a little and saw where the water was coming from. His parents had their own bathroom inside of their bedroom. I sneakily walked over to the slightly opened door and saw Ann in the shower. I had another instant hard-on at the thought of Ann bathing her soft body. I couldn’t make out her body that well in the distorted glass that was on the shower. I was happy, but not satisfied. I looked in the clothes hamper and saw the two sundresses that she wore earlier that day. I picked both of them up and out came her black thong. The thong was barely there. It just looks like some defunct piece of clothing. I took them and threw them in my pocket. I walked around her room a little more and found a walk in closet. I figured I’d look around in there a little bit to see what sexy things this MILF would wear.
I only took one step in the closest and heard the water turn off. My heart began to beat faster and I was in a state of panic. I looked in the closet and two racks of clothing one on top of the other. I saw a slight gap that I swore could not be seen unless you spread the clothes apart. I quickly dodged into the clothes rack and crouched just as the bathroom door flung open. I kept the closet door slightly open so I could see an opportunity to leave. I got into position and could see most of the room and a full mirror on the other side of the closet. I saw Ann walk out of the bathroom about a minute later completely naked. I dropped my jaw flabbergasted at the sight. She had the perky nipples that were just the right size to be sucked. She had a nice landing strip pussy and I could make out every detail of it.
She had a towel with her but she just flung it onto the bed. I saw her walking towards the closet. I could hear my heart beating out from my ears. I knew I was caught. She flung the door open and tried the light. It didn’t turn on.
“Damn, I told Richard to change the light bulb before he left this weekend.”
I silent sigh of relief. I was saved. She continued to look through the racks of clothes blindly. I however became accustomed to the lack of light and saw her every move. I saw her grab a pair of underwear from a dresser across from where I was. I leaned forward and could see her perfect little butt hole and saw her pussy peaking out from the bottom.
She turned and began to look at the clothes rack above me for a nightie. I could tell that she was struggling without the light and saw an opportunity to do something I always wanted to do. As she looked above me I leaned forward slightly and sniffed the air right around her pussy. The sweet smell filled my nose and I almost came in my pants right there. She continued on and soon found the nightie of her choice.
She went out to the full mirror and posed naked for about five minutes. She began to do stripper like moves and she even got really low. Like her ass touched the carpeting so low. She sexily put on her nightie and underwear and began to go to bed. I finally thought that I would be able to leave. Just as she was going to bed, I saw her reach over and grab what looked like some sort of sl**p medication. I saw her read the bottle and count out two pills. She turned off the light and went to bed.
No more than five minutes went by and she began snoring. I waited another five minutes and decided it was time to get up. I knew from experience that in order to be epically sneaky, no matter what you do, you have to keep an ear on the person. I zoned into her every breath and timed it up perfectly in order to choose my next movement.
I was one step away from the door to the hallway and decided to see how asl**p she really was. I opened the door and knocked very slightly. No answer. I knock a little louder. No answer. I knock liked it was an emergency. No answer. I suddenly saw another opportunity
I walked over to her bed stand and saw her bottle that she just took two pills from. It was in fact for sl**ping. I looked closer at the label and saw that each dose was for 200 mg. and that the recommended dose for women between the weight of 115-150lbs. was 200 mg. I, being the mathematician I am, came to realize she took twice the necessary dosage. I looked at her and saw a very calm snore pattern take place. I reached to her shoulder and began to rub it slightly in gentle circles. Her breathing stayed the same. I continued to become more and more aggressive and still the same breathing. I rubbed her shoulder strap down and still no difference. I started to move to the other side of the bed. She started to move. I duck down.
Afraid I was caught I crouched for what seemed like forever. After forever and more, I heard her begin to snore again. I looked up and saw that she flipped sides and she was now facing the bed stand. I creped over and saw her loose shoulder strap and her shoulder crunching her breasts so that it looked like she had the biggest cleavage ever. I very steadily moved her strap down her arm and soon had it at her elbow. I then focused my attention on her breasts.
I looked closely and decided my next point of entry, almost like a rubric’s cube. I saw that her now strapless shoulder side was probably the easiest access. I very gently moved her garments down. I became very uneasy about this because with one flinch, she could have woken up. I continued to pull her top down with no avail. Finally she moved ever so slightly and I saw the mother load.
Her now puffy nipple was looking right at me. I was already hard from all of this anticipation, but now I was just about to come in my pants. I began to make little circles around her nipple and saw it transform into a very pointed nipple. I was so happy I began to rub my pants a little. She started to move again and still afraid, ducked down, but I, now less afraid. I almost instantly came back up and saw that she moved to lie on her back. I looked and saw her nipple still peaking out. I began to rub it again.
I continued to rub her nipple and my dick and was soon ready to come. I needed something to put me over the top so I kneeled and leaned over her body and stuck my tongue out. I was now very scared. I just grazed her nipple with my tongue. I looked to see any life. Nothing. I reached back down and put my entire mouth around it and began to suck ever so slightly. I could feel my orgasm coming on fast and was soon cuming profusely in my pants. I sat back with a sigh of relief and looked down and saw I came a little in my hand. I decided to leave my mark and put it on her nipple and her nightie. I leaned over to give her nipple one last kiss and walked back to Matt’s room.
As I was walking I realized what I had done. I couldn’t believe it that I just sl**p m*****ed my friend’s mother. As I walked passed Matt’s room, unmoved from where I last saw him, a sense of pride came over me.
I passed out in Matt’s room and woke at about eight o’clock. I looked around and saw Matt still passed out. I decided to go to the bathroom downstairs. I walked down the stairs and heard crispy bacon being made. I got to the foot of the stairs and now smelt the bacon. Mesmerized, I walked to the kitchen and saw Ann cooking.
“Good Morning there, how did you sl**p?” she asked as she walked over to me.
“Fine thanks.” I replied monotonously, “How about you?” I asked as a personal joke.
“I slept great!” She exclaimed.
I smiled and began to walk towards the bathroom.
“But…” she stated, “ I could have slept better if there wasn’t some k** creeping around my room last night.”
I looked back stunned. She walked all the way over to me and held out her nightie with my semen stain on it. I panicked and tried to lie about it.
“What is that?” I asked scared.
She walked all the way over to me and reached at my crotch, she the reached in my pocket and pulled out the underwear. I was caught.
“Listen k**, I don’t know what to do in this situation because I’ve never been in this situation before. How about we handle this between us and only us as adults?” she asked.
“Of course.” I stated with relief.
“I now have to do something about his however. See I’m in a bind” she began. “I can’t tell Matt because he won’t like you anymore, however, I can’t just let you go off the hook. Do you see where I am going with this?” she asked.
I dumbly stated “No.”
“Let me give you a hint” she said. And with that she lunged at me and grasped the back of my head while she threw her lips onto mine. She passionately kissed me and began to stick her tongue down my mouth. I started kissing back and she pulled back. Dumbfounded I looked back at her with a mixture of confusion and excitement. All she said was
“I want an affair.”