From the Lifeguard 3 Story

It was a fairly long walk out of the pool, first came her beautiful breasts, her thin waist and her penis…

Without touching my dick, I immediately shot my load in just one long shot.

I doubled up in pain I had ejaculated so hard.

Caley walked up beside me, held my head, kissed me and said, “Now that’s got to be love.”

And I then knew what my special opportunity was that my parents were talking about. It was Caley.

I kissed Caley back.

Lifeguard 4 Story

I was in a daze. A sex daze. I didn’t know which end was up, and I didn’t care.

I met the most wonderful person. He became a she and I couldn’t be happier. We wrapped the towels around us, grabbed a huge plate of lunch and then found a little place to sit and talk. Mostly I listened. She told me all about the choices she made, how she always felt like a woman trapped in a man’s body, but also didn’t want to give up some of the “man” in her. She was perfectly happy just like she was and didn’t anticipate changing any further.

She had me at “hello.”

She was beautiful, smart, articulate (which I wasn’t at all), and decisive all at a very young age as she was twenty-years-old.

I was so gobsmacked…

I was speechless...

I was so in love…

She finally wound down a bit and waited for me to say something, anything.

Being the articulate, caring, wonderful person I was, I said, “I’m a virgin.”

She started laughing so hard she almost fell out of her chair.

Gathering herself she said, “Alex, I saw you screwing my mother, everyone heard you and her orgasm. You’re no virgin.”

I waited a moment or two, then said, “I’ve never been made love-to in my ass. I’ve been saving myself. Obviously, for you.”

This was her time to be speechless.

“Fuck,” she said.

“Yes, please,” I said.

She looked at me. She gave me the one universal sign that told me she was interested. Her towel started to tent up. I mean really tent up. I had seen her walk out of the pool flaccid and I had immediately cum without even touching myself. When I saw the size of the tent in her towel I almost gulped.

Instead, I pulled her towel open and went straight down on her.

Her penis was extraordinary. Larger than my Dad’s but beautifully shaped and long. My ass puckered involuntarily, lovingly, as I couldn’t wait to get her into my anal canal.

I had practiced sucking dick many times on my Dad, so I knew how to do this. Caley sighed and cooed and slowly moved her penis in and out of my mouth. I wasn’t doing much thinking but I was surprised both how soft and hard her cock was. It was amazing.

After a few minutes, she opened her eyes, extracted her now fully engorged cock out of my mouth, grabbed me by the hand, and led me back into the house. I noticed as we walked by my parents and her parents that they were silent watching their totally naked children walk by hand-in-hand, hard-on by hard-on.

We walked upstairs into what must have been her bedroom. She told me to lay down that she’d be right back. I did as instructed. I may have been young, but I was not a fool.

She came back shortly with a large bottle of lubricant still sporting a massive, I mean massive hardon.

She then started giving me instructions:

“This is probably going to hurt.”

“I’m going to go as slow as I can and will be as gentle as I can.”

“As this is the first time for you, I won’t go in all the way, that would hurt you too much.”

“Are you sure you want to do this?”

I just kissed her.

Oh, by the way, I had a massive hardon too.

She pulled out a couple of pillows, kissing me all the time, stroking my penis, pinching my nipples (Oooh, I really liked that.) and just softly cooing to me.

She flipped me over onto my stomach, grabbed some pillows lifting my hips and then slowly started applying lubricant to my asshole, and slowly inserting her finger up my canal. At the same time, she was rubbing lubricant on her cock. She then started to rub her cock against my leg as she inserted two-fingers in my ass.

Ooh, that felt good as I pushed back a little into her knuckles.

The third finger went in… "Oooh, oooh, oooh."

She slowly withdrew her fingers and slid her cock against my anus.

I pushed against her cock fast and hard.

“Yow.”

Not my brightest move.

She took more lubricant and poured it on my anus and her cock.

“Aahhh, that’s better,” I said.

I let her drive. And she is an expert.

She slowly, rhythmically began moving her cock gently against my pucker point. All of a sudden, she was in! It took my breath away. It hurt but not in a painful way, just in a totally new, unknown, and sexy way.

I realized too, that she hadn’t moved anymore. She had pushed through and was just holding as I adjusted to the new sensations and feelings.

When I had finally caught my breath and began to relax, she started slowly moving inside, a little deeper, a little deeper, but never too deep. She started lengthening her strokes. Each time she pulled almost all the way out, I would tremble. I wasn’t quite an orgasm, but it was quite a feeling. “Is this what women feel?” I thought to myself.

My dick just got harder each time she pulled almost all the way out.

Her dick was getting harder, her breathing was coming faster.

Cum started oozing out of me.

Caley started moving a bit faster.

Even more semen came oozing out of me.

Suddenly I just shot my load and as I did I contracted my anus.

Caley shot her load when I did that.

I came buckets and buckets, I was howling and yowling, almost crying, I saw stars… It felt so damn good.

I was looking back over my shoulder and Caley had somehow grabbed her cock, she was pinching off the end of her cock and was crawling up to my face. She then jammed her partially hard cock into my mouth and proceeded to cum some more.

OMG

Love, love, love.

Try to swallow, try to swallow, try to swallow.

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 18-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 3-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.