"Oh my god!" the blonde woman screamed while riding my dick in the late May morning. Usually, it would be my girlfriend in pleasure on top of me, but today it was her mom enjoying my thick nine-inch cock.
"FUCKKKK!!!!" screamed Mrs. Shaw as she convulsed in an orgasm before collapsing on my chest.
I took over and started pumping my cock into her, causing her to moan in pleasure.
"Yessss... Don't... stop... fucking... me... Cole," escaped out of the blonde MILF's mouth.
Deciding to really take control, I flipped over with Mrs. Shaw now on her back. Her eyes wide in surprise as my dick never left her pussy. Grabbing her hips, I started to really pound away eliciting non-stop moaning from my girlfriend's mom.
My mind drifted to how I ended up with the gorgeous blond MILF now below me on my girlfriend's bed.
I started dating Bailey Shaw back in early December with both of us being juniors at Clear Falls High School in California. Her being a cheerleader and me a linebacker and third baseman on the football and baseball teams, respectively. We had both turned 18 earlier in the school year, me in mid-September and her in early November.
Bailey is 5-feet, 5-inches tall, around 120 pounds with blonde hair that goes down about to the middle of her back, sparkling blue eyes along with perky D cup breasts and a nice round ass. While I, Cole Webb, am 6-feet, 1-inch tall, 215 pounds, brown hair that is kept short and of course a nine-inch penis that had just over two inches in width.
The first time we had sex was on Christmas Eve. It was her idea for a Christmas present since our relationship was so new. She dressed up in a sexy Mrs. Claus outfit that accentuated her D cup breasts perfectly. Thankfully her parents were out at a Christmas party that night. If they were at home, they would have heard their daughter's screams of pleasure as she took my large dick for the first time.
Ever since then we had tired as many times as possible to have sex. If we couldn't get enough alone time then she gave me either a blowjob or handjob and I ate her out or fingered her to orgasm.
Like all the others I had slept with before, Bailey could take only about half of my cock. The difference between her and the others was that she loved getting stretched out by my cock. It wasn't until she got back home from spring break our sex life really took off.
She and her family, that includes her older sister Claire whom just finished her junior year in college, went to Miami in the middle of March for spring break and also visited her brother Ben, who had started a job out there in January.
Bailey's sister ended up taking her to a sex shop for the first time as an 18th birthday present during the trip. She picked up some big toys that has helped her not only get used to my size in her mouth and pussy but also pleasure herself when I'm not around to do so.
It was a Saturday night in late April when Bailey was finally able to take me balls deep in her vagina for the first time. Since then, we have had a bunch of mind blowing sessions together.
The first week that school had ended for the summer saw us have sex four times during the week thanks to her parents being out of the house. Her Dad being at work during the day and Mrs. Shaw heading up to Berkley to visit Claire since she wasn't coming home and taking a few summer classes instead.
Bailey then started her summer job as a lifeguard at the local pool the following week but was going to have Tuesdays and Wednesdays off. Myself decided to clean pools during the summer in the high-class neighborhoods we lived in thanks to connections my dad had from his work with a bunch of the people.
One of my clients was of course the Shaw's. I scheduled it to always clean their pool on either a Tuesday or Wednesday each week depending on Mrs. Shaw's schedule. While doing my job, Bailey would lay out teasing me in one of her tiny string thong bikinis that she got in Miami during spring break that her sister also helped her pick out.
By the time I had completed my job, I had a raging hardon seeing my girlfriend rubbing tanning oil all over herself and splayed out in the sun teasing me. She would give me a blowjob out by the pool that saw her take about eight inches of my dick and eventually get my first load either down her throat or on her chest. We would then head to her bedroom or the shower for a hot fuck session before I headed to the next house to clean their pool.
This Wednesday would be different. I walked into The Shaw's backyard a little disappointed I wouldn't be seeing Bailey this week for our weekly sex session. Her Dad had taken her to Los Angeles for campus tours of UCLA and USC.
I headed to the pool house and was in there for about 10 minutes gathering everything I would need for the job. About 15 minutes later, I walked back out the door and was stunned to see the blonde beauty Jennifer Shaw lounging in one of the beach chairs.
She was wearing a small blue bikini that barely contained her enhanced D cup breasts. From what I could see the bottoms were just as skimpy with just a small, thin piece covering her slit. Mrs. Shaw was an older spitting image of Bailey with blonde hair, blue eyes and 5-feet, 5-inches tall.
She eventually saw me just standing there holding the cleaning supplies.
"Hey, Cole. How are you doing today?" the mature blonde said.
Shaking my head I answered, "I'm doing well Mrs. Shaw. I wasn't expecting to see you today. Thought you had gone with Bailey and Mr. Shaw down to Los Angeles for the campus tours."
"I was supposed to go but forgot I had an optimist appointment that was. I called to reschedule but it would have been next month until they could get me back in a new appointment, and I really need to go to get new sunglasses."
"Oh, well that sucks you couldn't make the trip with them. Do you know how the USC visit went yesterday," I asked as I started to get to work checking the PH balance of the water.
"She liked it and said that she has a good chance of making the cheerleading team if she decided to try out. I know Tim would love if she went there with him being an alum."
"That's good. Mr. Shaw would love another Trojan in the family," I said while trying to hide my growing erection from seeing Mrs. Shaw's hot body.
I had seen her around before in a bikini at different pool parties over the past few summers. But those bikinis were a whole lot more conservative compared to what she was in today.
It also didn't help that she was rubbing in tanning oil into her body that she kept in amazing shape for someone close to 50. Bailey had mentioned before that her mom went to the gym at least five days a week to help stay in shape.
"He definitely would. Don't mention it, but Tim wasn't happy that Claire didn't go to USC but instead choose Cal," she said while oiling up her taught stomach.
"Well, Cal is a good school It could have been worse and Claire could have gone to UCLA," I said with a slight smirk.
"He would have been fine with Claire going to UCLA as he could use it as an excuse to still go to a USC sporting event. Tim was more worried that she would turn into a super liberal hippie in Berkley. Thankfully that hasn't happened or he would be upset about that all the time," Mrs. Shaw said as her hands were now rubbing oil over her thighs and down her leg. "Don't mention what I just said to Bailey or Time, it can be our little secret."
"My lips are sealed," said I as I made a zipper move over my mouth.
"I knew I could trust you. Don't mind me as I catch some rays. Just go about your business cleaning the pool," she said before laying her head back while her body shined in the tanning oil.
Thankfully I was able to keep my back to her for most of the time or she would have seen the outline of my semi engorged cock in my shorts. When I was nearly done, I heard Mrs. Shaw call my name.
"Cole, can you help me out over here?"
"What do you need help with," I asked as I turned my head towards her. What I saw made my cock go fully hard.
Mrs. Shaw was now lying on her stomach with her bikini top untied. Her full, round butt was also on full display. What I had thought might be a thong bottom at most was actually just a string running between her cheeks.
"Do you mind rubbing tanning oil on my back so I don't burn?"
"Uh... sure. I can do that for you. Would hate for you to get sunburned back there," I said after regaining my composure.
"Time wouldn't like it either," said Mrs. Shaw with a wink.
I readjusted my cock as best I could in my shorts and walked over to her. Grabbing the tanning oil bottle off the side table, I squirted out a decent enough in my hands and started rubbing it in beginning near her neck while standing squatting on her left side.
"Umm, that feels good and you really know how to use your hands. Maybe I should hire you to give me massages instead of going to the spa."
"I'm sure we can negotiate a good price," as I worked massaging and rubbing in the oil in her middle and lower back.
Once I got to her hip, I skipped over her butt and went to her thighs and started working my way down.
When I was about to the back of her knees, Mrs. Shaw turned her head and looked at me. "Cole, you skipped over rubbing the oil into my butt."
"Oh, I didn't want to overstep my bounds with you."
"Don't worry about that. If I wanted my butt to be red then I would have Tim make it so when he gets back from Los Angeles tomorrow," she said with a slight smirk.
"Okay," I finally got out after being stunned a bit by her comment. "Let me finish your legs and I'll take care of your backside last."
"Good," Mrs. Shaw said as she turned her head back. At the same time I saw her wiggle her butt a little to tease me.
After finishing oiling her legs, I squirted more oil into my hands and was about to start rubbing it into her ass. Right before I touch her, she said, "You can straddle my legs when you rub in the oil. That way you can make sure you get every inch covered. I don't want you to miss a single spot."
"Okay, I'll do that," I said as I got up and straddled the beach chairs and her legs.
Starting at the bottom of her butt, I slowly started massaging the oil into her backside. Mrs. Shaw started moaning slightly once in a while as I worked over her incredible ass.
Just as I thought I was finished rubbing the oil in, Mrs. Shaw turned her head slight and said, "Make sure to get between the cheeks. That area can get burned too."
Taken aback a little, I followed her instructions and started to rub my oiled hands between her butt cheeks. I felt my fingers rub the thing string between her cheeks along with the outside of asshole.
Mrs. Shaw pushed back slightly, and my thumbs were pushed against her barely covered pussy.
