The night that I'd just had with Megan and Amy sure didn't turn out quite like planned, but I'd still quickly call it a success. My intention had been to do both of the girls at once, but doing Megan while the other girls watched was just as good.
I sat around at the next morning, saving my energy and waiting for the afternoon to roll around. I already had another date set up. On the list I'd made of women that I was determined to sleep with, it was already time to go for number four.
My target was Dee, the mother of my friend/lover Mindy. Since Mindy was on my list, she was shocked to find out that her mom was on there too.
The truth is that I had always found Dee to be attractive. She had a fuller body than her daughter, but still had a slender waist. I think part of what drew me in was that she tried hard to look pretty every day. She had shoulder-length dyed blonde which was usually pulled into a tight bun, and she always had bright red lipstick on.
We lived in the southwest part of the United States. It was getting chilly and heading towards winter in a lot of places, but it was another perfect day at home. The sun was out, and it was probably around eighty degrees.
I found Mindy out sunbathing by her parent's pool in a little polka dot bikini, which couldn't have worked better for what I had in mind. She smiled at me, but I knew she was on the defensive today because I was going to try to fuck her mom.
"Hey beautiful, mind if I join you?" I asked.
"I suppose not, stud."
I slid off my shirt and shorts to a reveal a Speedo which could barely contain my massive package. It forced my dick to snake halfway around my leg. In fact, one thing I had to concentrate on was not getting an erection, because I knew it would pop out of the tiny cloth.
"You're shameless, you know that?" Mindy said when she saw my bulge.
"I suppose I am, but it looks pretty good, doesn't it?"
"It looks fucking gigantic, if that's what you mean."
I sat down in a lawn chair next to Mindy for a few minutes and talked, then made up an excuse to go indoors.
I walked into the kitchen and Mindy's mom had her back to the door, doing dishes. She was wearing a green housedress with red jewelry and, currently, a red apron.
I sat my book bag down inside the kitchen.
"Ma'am?"
She turned to look at me and instantly dropped the glass that was in her hand. It shattered to the floor.
"Slippery!" she announced, and went to grab a broom to clean it up. I knew the real reason that she dropped that glass was the sight of my Speedo-covered log.
She knelt down to sweep it up with a hand broom, and I took a step towards her so that my member was right in her line of sight. I tried to act oblivious, and she tried to act like she wasn't flustered by it.
After she cleaned the mess up she turned to me again. "Did you need something, Nick?"
"Maybe some juice, ma'am. It's hot out there."
Her eyes kept shooting from my face to my crotch. "Okay, but remember to call me Dee."
She poured me a drink and I went back outside for a while. This was already a fun game for me, and I was lucky that it hadn't made me hard yet.
I sat by the pool with Mindy for a while, and then made some other excuse to go back indoors and found Dee getting food ready to take out to the grill that was by the pool.
We talked for a few minutes about nothing in particular until she said, "Nick, you might find me attractive and that's okay, but aren't you embarrassed?"
I really wasn't following what she'd said. "Embarrassed about what, ma'am?"
"Most boys would be embarrassed walking around with an erection like that."
"Dee," I started, and left a long, pregnant pause, "I'm NOT erect right now."
"Are you being serious?" She looked at my sausage again with wider eyes.
"If something gets me going, Dee, my dick gets way bigger than this."
Nobody said anything for a second, but she kept looking at me. I smiled at her, maybe a little nervously. I wasn't sure if what I was about to try was going to work. I told her in a serious tone, "I know I shouldn't be this open with my friend's mom, but I have a photograph of it if you want to see me hard."
She didn't say yes, and she didn't say no; she just stood there looking at my body. She had a vacant look, and I couldn't tell what she was thinking. I went to the backpack I'd sat against the wall and pulled out some photographs.
"Here's me hard," I said and showed her a picture of my erection.
"My God, it looks so huge. I can't believe an eighteen year old boy can have such a cannon."
I moved closer to this sexy older woman and put my hand on her shoulder. "You can't really see any perspective in that one, though. Try the next picture."
I had a nervous lump in my throat. She flipped to the photograph behind that one.
"Mindy?"
She was looking at a photograph I'd taken of her daughter on her knees playing with my cock. In the picture Mindy had both hands wrapped around my shaft and my large cockhead was in her mouth. She was looking up at the camera with her big, bright eyes.
"See how big it is?" I said. "There's probably room for two more hands on my dick."
Dee didn't say anything; she just started thumbing through the pictures wide-eyed. She gasped at the one with my dick all the way down Mindy's throat.
Eventually she asked, "Is this in my bed?"
"Yes, that was my idea."
She kept slowly flipping through the photos.
"God, I can't believe how big your dick is. It looks like your hurting her."
"She was loving it, Dee. Your daughter begs me to fuck her with my giant cock."
Eventually, she got to the last photo. It was of her girl on Dee's bed, covered in cum.
I moved the hand that was on her shoulder to her waist and said, "I always shoot gigantic loads of cum like that, and one of your daughter's fetishes is how she loves it when I blow my load all over her."
"Like mother, like daughter," Dee said, and then covered her mouth embarrassed like she didn't mean to say it.
"Really? Well I bet you've never been showered with a load half that big."
She didn't say anything. She knew I'd just indirectly insulted her husband, but she also knew it was true.
Through the kitchen window I luckily noticed that Mindy was coming back into the house. I grabbed the pictures and put them back into my backpack, then went to the bathroom to calm down for a minute. My dick had just started to swell, and I wanted to make sure I didn't get an erection yet.
By the time I got back outside, both women were out there. Mindy was sitting the picnic table by the pool while her mother was grilling.
Dee had changed out of her dress into a bathing suit. It was a somewhat modest blue one-piece but it was low-cut enough to show some nice cleavage.
I tried to read what Dee was thinking, but she wasn't giving me any signs. I didn't know if she was aroused, indifferent, or upset with me.
While she was serving the food onto our plates, she said to both of us, "Maybe I shouldn't do this, but I made some margaritas if either of you kids wants one."
We both eagerly accepted the drinks, which were mixed strong. I thought that maybe this was a sign of her interest because I didn't think that Dee would normally give us liquor.
The afternoon had passed and the sun was starting to set as we ate. I think both girls had a couple of drinks too quickly with the meal. I tried to pace myself, but I had several as well.
As we ate I felt Mindy's bare foot slide into my lap and start massaging my penis. She smiled at me. She used her toes to start kneading my balls.
Then, though, I felt another foot start sliding across my length. It was Dee! Mother and daughter were both looking to work me under the table, and neither realized that the other was doing it.
This went on for a minute, and for the first time I was being pushed towards a full erection and my massive dick strained out of my trunks.
Both women realized they were touching bare skin now and started rubbing it faster. Then, suddenly, their feet touched and both instantly realized what was happening. They both pulled their feet away and tried not to show it on their faces. I knew, though, that this was the first point where Mindy realized I really was going to fuck her mom.
"Have you heard from Dad?" Mindy asked her mom, obviously trying to remind her that she was a married woman.
Dee's husband traveled a lot on business and was gone for days, and sometimes weeks at a time.
Dee didn't answer, and she did get a guilty look on her face, but I also soon felt her foot slide back onto my hard on.
We had another round of margaritas. The sky was getting pretty dark and the girls were getting pretty drunk.
