From the Lifeguard 4 Story

After she was finally done cumming, she pulled her now flaccid penis out of my mouth and proceeded to give me a big French kiss and started sucking the remainder of her cum into her mouth. We started hugging and kissing and kissing and hugging. That was even fun.

After a few minutes of doing this, we just laid there giggling and laughing about what we had just done.

Caley then said, “You are one sick boy.”

I then said the only sensible, normal thing an eighteen-year-old boy would say after a day of sex and having his virgin ass pounded by a beautiful transexual, swapping cum, twice ejaculating without being touched…

“I love you. I want to spend the rest of my life with you.”

She didn’t laugh. She didn’t act disgusted. She didn’t even blink or say anything but continued to look me in my eyes.

I knew I had blown it. How could a human being make a decision or choice like that after only three hours of meeting someone? It was preposterous. It was insane.

Then she said the words I totally wasn’t expecting, “I love you too.”

Then she kissed me so softly it took my breath away.

Lifeguard 5

As we walked downstairs hand-in-hand looking for our parents it appeared that the party was over. We walked to the living room that had a huge couch and matching chairs. On the couch was my mother and Caley’s mother Belle. My mother was being spooned by Belle. My mother was petite (I got my height from my father) while Belle was close to six feet tall. Belle had her arm wrapped around my mother’s chest and was pinching one of her nipples. The other hand was between her legs and she had two and sometimes three fingers inserted into my Mom’s pussy. My Mom seemed to be shuddering every ten to fifteen seconds and about every sixty seconds seemed to be having an orgasm. 

Of course, I knew what her orgasm looked like as we had shared many of hers and mine as well.

This was one beautiful sight indeed.

I was so mesmerized by what I was seeing that I didn’t even notice Caley and I were no longer holding hands.

Crap, the woman I loved I had totally forgotten about as I watched two beautiful women make love.

As I started to look around for Caley I suddenly saw her slide into a spoon with her mother, sporting a hardon, again, and drive quickly and easily into her mother’s pussy. 

Basically, girl-on-girl-on-girl-with-penis.

Now I had come three times already that afternoon. Once into Caley’s mother’s pussy. Once handsfree just seeing Caley walk out of the pool. And once after getting my ass fucked for the first time by my true love Caley. Another handsfree ejaculation.

Now there was my one true love, dropping me like a hot potato and pounding on her mother’s pussy while her mother was hand-fucking my mother.

I started stroking my dick. 

It got hard again.

Ahhh, the glory of youth.

Then I heard the unforgettable sound of slap, slap, slap.

I turned and there was my Dad getting absolutely hammered by Caley’s father, Derick. 

Now I knew where Caley got her hung-ness.

Thinking fast, I did the next most natural thing- I stuck my penis in my Dad’s mouth, Gave Derick a high-five, and came like a tornado was chasing me.

I woke up sometime later and all was quiet. I looked around and everyone was in various poses of satiation.

My mother was in Derick’s arms. My Dad’s head was on his thigh. Belle was curled up next to all of them (I told you it was a big couch)...

And Caley was asleep, in my arms in one of the big chairs. How did I miss that detail?

I promptly went back to sleep.

Sometime later, my mother shook me, kind of awake, I groggily got up, kissed Caley good night, professed my love for her again in case she forgot (I’d known for a good seven to eight hours by then), stumbled to the car, fell asleep again and woke up the next morning in bed.

Was it a dream?

My ass was sore this morning.

Nope, it wasn’t.

I smiled and got cleaned up to go to work for just another day at the pool.

My parents had both left for work so nobody was there to make sure I was de-spunked before work. But today, it didn’t really seem to matter. I didn’t really need to be unloaded before work.

I got to the pool and started my daily assignments. Something must have changed in me. The girls and women dripping wet getting out of the pool didn’t get me hard like it had done just days before. I seemed to walk taller with more confidence. Maybe it made my penis project differently out of my Speedos… I don’t know, it was just different.

Yet, every time I thought of Caley I got a total rager. My dick was sore, my butt was sore and getting a raging hardon wasn’t as comfortable as in the previous days. 

On top of that, halfway through the day I realized I didn’t know how to get hold of Caley. 

What a moron!

Thankfully my total moron-ness was saved by my Mom texting me Caley’s cellphone number. Wow, what a great Mom.

She’ll fuck me and then she’ll help me pick up women. What a babe.

I texted Caley on my next break. I texted her that my Mom had given me her number (she knew). I offered a simple hello and said I’d love to talk with her later that evening. She sent a simple smile and a thumbs-up. It made me tingle.

I got home at about 6 PM.

My parents were waiting for me with drinks in their hands.

Was I in trouble?

My Mom started out by asking, “Did you have fun yesterday?”

All I could do was smile that shit-eaten grin only a dumbshit teenage boy can give and then respond accordingly, “Ah, yeah, it was fun.”

Again, what a moron. And in a fashion, they read me the riot act…

What I learned: Derick was a former NBA basketball player who blew out his knees early in his career. Instead of sports playing, he went into sports media and now runs a business with 300+ employees. Belle went to law school, practiced law with a big firm and struck out on her own as a sports agent. She represented some of the biggest names in sports that when my mother told me some of the names I was very impressed. He and Belle started dating in high school. 

Caley was starting law school that fall, at age twenty at Georgetown. Yes, she was every bit an overachiever just like her parents. And she wanted to go into media representation as a hybrid between her mother and father. She was very committed to excellence just as her parents. She knew where she wanted to go.

I was thinking, “How do my parents know so much about these people?” But again, I was too much of a moron to ask.

I instead, was one directionless smart ass teenager with nothing to offer on that scale. Yeah, I knew how to program and make money, I was a hard worker and a relatively good person, good sex included, but what plan did I have?

Caley did like me, but she was a person who needed a good and strong partner.

My heart hurt. They were right. I didn’t know anything about Caley other than she was amazing, and that if I was going to be part of her life, love wasn’t the only thing I had to be able to offer. In some ways, that may have been the easy part.

My mother fed me some dinner which I hardly noticed. I went upstairs and, trembling a little, I called Caley.

She answered, “Hello Alex!”

Her voice was so beautiful and I totally succumbed and became hypnotized by everything she was saying and telling me. I listened, I talked a little, she laughed at some of the jokes and then she was gone as she had some friends coming over and had to run. She told me to call her again.

Oh, I was so in love.

The next day was just another lifeguard at the pool day. I only had a couple of raging hardons thinking about Caley, but overall controlled myself pretty well.

As I was leaving I remembered that my parents weren’t going to be home until late as they had a fund-raiser event. I was on my own for dinner and entertainment. I jumped in my car and was about to leave the parking lot when I saw Jill, the pool manager, pull the hood up on her car. I pulled over and asked how I could help. She asked if I had any jumper cables. I didn’t but if she would wait, I’d run home and get the ones my Dad had. As we only lived a few minutes away, I returned in less than ten minutes. I got her car jumped and it had a good strong charge pretty quickly.

Jill asked, “How can I repay you?”

I did my “aw-shucks” teenage boy goofy impersonation.

Then she said, “You hungry? Let’s go grab a burger. Follow me to my house so I can change clothes.”

I had on flip-flops, a pair of shorts over my Speedos and a decent t-shirt so I was good to go to a burger joint.

She had her swimming suit on, fitting her quite well I must say, so I understood why she wanted to change. So like an obedient kid, I followed her to her house. She told me to come on in and grab a cola in the fridge while she changed.

Jill lived in a cute house and was single as far as I knew. She was very attractive and always really nice and very professional to me. She was kind of like an older sister. She taught school then would run the pool for the city in the summer. I’d known her for a number of years since I was on swim teams and this was the best pool in town. I swam a lot of meets at the pool and in the summer she was always there.

I heard the shower running and thought nothing of it.

I was just kind of looking around just kind of waiting when I felt a tap on my shoulder. I turned, and there was Jill, buck fucking naked in all her luscious female splendor.

At least this time I didn’t cum in my pants.

She grabbed my rapidly enlarging penis with her right hand, reached around and tugged at my shorts and Speedo simultaneously with her left. A helpful wiggle by me and my shorts and Speedo were at my ankles in no time at all.

She immediately went down on my dick as both of us moaned, “Oh my god.” together.

She was sucking hard and marveling at the size of my dick mumbling between sucks. 

That’s when my conscience got the best of me. I’d just fallen in love not two-days before. Caley was the most beautiful thing, so different than anyone I had ever met or was ever going to meet assuredly. I couldn’t imagine doing anything to screw up that relationship.

So, I pushed Jill off my dick, grabbed my shorts and Speedo and rapidly pulled them off with my flip-flops and t-shirt, then pulled Jill onto the couch (yep, a not so big couch this time) and immediately stuck myself in as far as I could go.

She yelped (oops), then started moaning and groaning and meeting every thrust I could muster. She came in about two minutes but I had just got started. I started sucking on her nice sized tits…

I pause here. Yeah, Jill was like an older sister. But I was a teenage boy and had been lusting after her for years seeing her bounce around the pool, and I mean bounce. I really, really wanted to fuck her. I just never, ever thought I’d have the chance. And, I was going to pound her fast long and as hard as I could.

And she was willing and able…

Now, back to the story of our Intrepid Lifeguard.

Jill came a few more times and about ten minutes in I was ready. I wanted to show her what I was made of, so I pulled out and hit her with eight to nine ropes of substantial teenage ejaculation.

She was panting a bit and trying to get her wits about her, so proceeded to eat the cum off of her breasts, neck and everywhere else. And if that wasn’t novel enough I proceeded to stick my cum covered tongue deep into her mouth.

She started sucking my tongue in between grunts of, “Fuck, fuck, fuck.”

I was still hard of course.

I proceeded to flip her over the arm of the couch and pushed my tongue straight into her anus sending another jolt through her body. I learned later nobody had ever done that to her. I spit on her anus (actually she was so lubed up from her vaginal flow her butt was already slick) and slowly pushed my cock into her back canal. I found out later she had never allowed anyone to do that to her before.

She knew immediately she’d really been missing out.

Within a minute or two she was squirting all over the place. She had an incredibly foul mouth that seemed to be in tempo with my penis going in and out of her rear end. Wet and noisy, what a great combination.

A few more minutes later, she gave a big shudder, and started articulating, “Nnnggggg!”

At the end of this declarative statement, she basically passed out, which fortunately coincided with me emptying my dick innards outward into her rear innards. 

Whew.

That was okay. 

She was breathing heavily, but breathing.

I pulled my dick out her butt with a big, “Sllluuuurp.” Followed by Jill expelling some gaseous sound. Being a gentleman I won’t go into that.

I gently laid her on the ground.

I covered her up with a blanket, put a pillow from the couch under her head, wiped myself off with a kitchen towel, and left to get a hamburger and fries as we’d first intended.

After a double hamburger, fries, and a shake I headed home. I got there at about the same time as my parents. They greeted me and told me that Derick and Belle had invited us all over for the weekend and that Caley was going to be there as well.

Oh, and by the way, my older sister Ashley was coming home from Med school and would join us as well.