Bag Boy

By BeastoftheBOX

Original link: https://www.lushstories.com/stories/milf/bag-boy.aspx

Tags: MILF, First time, virgin, oral, surprise

Added: 02 Jun 2011 Views: 35271 Avg Score: 4.46

Loosely based on a true event
This story takes place the summer before my senior year. I was 17 working at a local grocery store as a bag boy. I'm about 6'1 or so, a little overweight, and short black hair. At the grocery store I worked at it was required to ask ever customer with a buggy if they would like help out to their car.

It started out as a normal day, I was working 12-4 on a unusually hot day in june. It was just a few minutes before 4 and I was ready leave. When a rather hot older lady came through the line. She was about 5'5 and had nice, large boobs. She was wearing a very low cut short that showed off her amazing cleavage.

"Paper or plastic, ma'am" I asked half starring down her short.
"Plastic fine" she replied.

After I finished bagging her items I asked "Would you like any help out to your car with your groceries ma'am?"

"Only if you can take them home and put them up for me too." she replied
"Well I am getting off any minute now" I said jokingly.

As we were walking to her car, she said something that caught me completely off guard. "I don't mind waiting until you get off work, if you will come home with me to help put these up. I will make it worth your wild"

I was speechless after that, wondering if she talking about what I hoped she was talking about.

"I...gu...guess I could." finally stammering out.

She just laughed at my response and nothing else was said about it.

I finished loading her groceries and went back inside. A few minutes later I was told to go home. It was a good thing to, because all I could think about was what just happened. When I exited the stored I didn't expect to see her sitting there in her car. She waved me over to her car

"Are you ready to go or do you need anything before we leave." she asked
"No I don't need anything" I replied trying to figure out if she was being serious.
"Are you going to get in or walk to my house?" she asked sarcastically.

I walked around and got into her fairly new looking silver BMW. On the drive to her house she asked me questions about where I went to school, my age, and if I was a virgin. She was happy to hear that I still was and said that that was about to change.

When we got to her house I helped her carry her groceries in and put them up, which didn't take to long. We went into the living room and sat down chatted a little more about random subjects.

She then looked at the clock and said "well if we are going to do this, we need to get started before my husband or daughter gets home."
I was wasn't sure what to say so I just kept quiet.
She moved closer to me and started to rub my leg and asked "what's the most you done with a girl?"
"N...ot much" I said shuttering from her touch.

She giggled and moved her hand onto my crotch. Then unzipped my pants and pulled my dick out. It was hard as a rock (it's only about 5 inches long). She stroked me for a little bit then kneeled before me and took it in her mouth. It took less than 2 minutes before I was cumming in her mouth. She swallowed it all with no hesitation.

"Have you ever seen a pussy?" she asked
"Besides the Internet? No." I replied.

She then stood up and pulled her sundress up over head and stood there in front of me completely naked. My dick got hard again almost instantly. I reached up and grabbed her beautiful tits and squished and squeezed them. She let out a tiny moan.

"I guess that means you never eattin' a pussy either." she said "well you have to learn sometime." she then proceeded to push me down, so I was now laying down on the couch and lowered herself on to my mouth. Her pussy was the best thing I had ever tasted. I had watched quite a bit of porn and read how to eat a girl out, so I sort of had an idea of what to do. After a couples minutes of she started to rock her hips, pressing her pussy harder onto my face. Then she orgasmed and had to hold onto the couch to keep from falling over.

After a minute or two she said "that was great for your first time eating pussy." still trying to catch her breath.
"Thanks" I replied licking her juices off my lips.
"Now are you ready to fuck your first pussy?" she asked seductively.
I just nodded stunned by what she just said.
She lead me back to her bedroom. She laid down, her legs spread. I just there for a minute and admired her. I positioned myself with dick ready to insert it in her pussy. I pushed it into her and was surprised to find that her pussy was actually very tight for a 36 year old who had given birth to a daughter. Since I was a virgin and that was the first time I had felt a pussy I almost came instantly. Then we heard a gasp at the doorway, I turned to see Rachel, a girl I in my grade that I went to school with. That's when I realized my dick was still in her mom. The shock of seeing Rachel and fucking my first pussy was to much for me and I came into her mother's pussy. It was one of the biggest orgasms. It seemed like I just kept shooting stream after stream of cum into her warm pussy. The whole time I was just starring at Rachel, trying to figure out what was going on.

The first words that were spoken came from her mother. "Great Rachel you made him cum, he just put it in to." she said mad at her daughter.
"Sorry mom, just surprised to see him fucking you. When you sent me that text that said you meet a cute teenager I didn't think you would mean him."
As they were talking I realized that my dick was still in her pussy, I slowly pulled it out and it made a wet popping noise. They both laughed at this, as I tried to find some clothes or something to cover up with.
Her mother spoke up and said "don't worry about covering up or being embarrassed."

I was still embarrassed because I was just caught by one of the hottest girls in my school fucking her mom and she saw me cum inside her.

"Well since you're already full of cum do you care if I have a go at him?" Rachel said.

To be continued...