Maria Fucks Her High School Friend!

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"Mmmmm, baby. You're going to like this!" I promised as I reached between my legs to guide his now throbbing member into me. He put his hands on my hips and pressed his hardness against my rosebud. He easily slid completely inside me and gasped.

"OH, Maria! This pussy is so warm, so soft." I began to rotate my hips around his cock, first in one direction, then the other. I was squeezing his cock with my ass muscles while I was rotating. "Mmmm, Maria, Maria. Holy shit, Maria, this is so hot, you're so hot, fuck, fuck, fuck!"

"Come on, daddy!" I said. "Fuck this pussy, make Maria cum for you. Show Maria how much you love her pussy. Fuck me, Josh, make me cum, make me cum, please make me cum!" If the girls around here didn't like doggy style, I was sure they probably didn't talk dirty to their men.

My talk seemed to encourage Josh. He began to slide himself into me as deep as he could go and then slide back out until he was just inside me. He was picking up speed and he started talking dirty to me. "I'm going to pound this pussy, Maria. This pussy is all mine, I'm taking all of it. I'm going to fuck you until you cum in waves for me, I'm going to fuck you until you beg me to stop."

I looked over my shoulder at him and licked my lips. "Mmmm, baby. I like the sound of that. Give me all your cock, I want all of it. Make me cum for you, Josh, I want to cum for you. Baby, please rub your hands up and down my nylon covered legs. That always drives me crazy, please Josh, do it now!"

Josh's hands moved down, and he did as I had asked. He was gently running his hands up and down my nylon-covered legs. From thigh to ankle, back up again, front, back, and all-around, Josh was caressing my legs in a way no other man ever had. I was humping his shaft as furiously as I could. I was beginning to go into sensory overload, and I knew I was close.

I looked over my shoulder again, licking my lips and batting my eyelashes at him. "I'm so close, baby, I'm so close. Maria is going to cum for you, darling. I'm going to cum, I'm going to cum, make me cum, daddy, make Maria your woman. Shit, shit, shit, close, so close, close, fuck, fuck, mmmmmm, cum, cum, cummmmmiiiiiiinnnnngggg!"

I fell forward onto my elbows as Josh continued to pound me from behind. He grabbed me by the hips again and was fucking me furiously. I knew he was going to cum again. I matched his rhythm; I was moving back as he thrust into me and moved forward as he was thrusting out. We picked up speed and he began to fuck me faster and faster.

"Maria, Maria, Maria! Fuck me, Maria, fuck me, Maria, fuck me, Maria! I can't hold it any longer, I'm cumming, I'm cumming, I'm cumming!"

He exploded inside me, filling my ass with his hot juice. I continued to ride his shaft while rotating my hips and squeezing my ass muscles. He collapsed on top of me as I continued to ride his cock from underneath him. He stopped cumming. I guided him out of me and cleaned him off with my mouth, lips, and tongue. His cock was still sensitive, and he squirmed as I licked him dry.

We lay in each other's arms again. "Maria, I almost didn't come back upstairs. I didn't think I'd have the courage to knock on your door when I did. I don't think I'd ever have forgiven myself if I didn't. You're the best fuck I ever had. No woman has ever made me feel the way you just did. I'm not sure any woman can ever make me feel that way again."

"Josh, you're getting better. I love your compliments. It's nice to know I made you feel this way. When Maria decided to explore her fantasies to be with a man, she wanted it to be just like this. If you're happy, baby, know that Maria is happy because you are."

We made love two more times that night. I woke up in the morning in Josh's arms. I ran to the bathroom to freshen my makeup. I only wanted Josh to see Maria at her best. I made coffee for us, and Josh woke up to the aroma.

We were sitting at the little table in the corner of the hotel room. "Maria?" Josh asked.

"Yes baby?"

"Is Luke coming to the reunion tonight?"

"No, I don't think he is. No, I'm sure of it. Even though that was the reason he came back, he's going to take a pass."

"I have this crazy idea. Will you be my date for the reunion? Luke will still get to be there, but we'll be the only two people who know!"

I laughed so hard coffee almost came out of my nose. Never in a million years would I have thought of something like that. "I like that idea, Josh. No, I love that idea. Yes, I'll be your date for the reunion."

....

I chose a fairly sedate outfit for the reunion. It was a cream-colored, cowl neck sweater dress, cut a few inches above the knees and had full length sleeves. While fairly form fitting, it wasn't crazy tight. I wore 3" cream-colored stiletto heels, the lowest heel height I owned. I had way more fun than I would have imagined.

Even Roger came up to me and apologized. I asked him to dance to show him I had no hard feelings. While we were dancing, I said, "Roger. You're a good-looking guy. I've heard you were the high school jock all the girls wanted to be with. If you put in a little effort, I think you could get that muscular tone back. And with a little more effort, I don't think you need to force yourself on women. Find the nice guy inside you and start treating women with some respect." He thanked me and told me he would.

I found out how wrong I was. Almost no one was anywhere close to being the same person they were in high school. Married with children, working or having their own businesses, they had all grown up. I realized how unfair I had been. Luke would almost certainly come to the next reunion.

....

While Josh spent the rest of the weekend with Maria, he did return home to shower and change clothes. I told him how much 'bathroom time' Maria needed, and he agreed it was better that way. But we had wild, uninhibited sex the rest of the time!

....

Luke had agreed to let Josh drive his best friend to the airport. I got out of his car and grabbed all my luggage. We gave each other a man hug and a fist bump. "I'll see you at the next reunion, buddy!"

"I hope you'll bring Maria too!" he said wistfully.

"Maria goes everywhere I go." I told him. Then I turned and headed inside the terminal.

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5 Comments
AnonymousAnonymousover 1 year ago

Nice story but please.pick a perspective. It's jarring when you go from first to third person in one paragraph and doesn't read well.

ShortyMacShortyMacover 1 year ago

I really like this story. It was awesome that Maria got to be with her best friend from school. Josh was lucky to and open enough to be with Maria. I’m going to give your story a rating of 10 stars. Well done.

⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️

AnonymousAnonymousover 1 year ago

Nice story. Well written, and hot. The switching back and forth betwwen Maria and Luke personas was a little jarring, but perhaps this was an accurate depiction of a transgender person, "pre transition", or perhaps a hot story about what used to be called transvestitism. I suppose that someone might enjoy dressing part time, and retain being a man part of the time also. Anyway, thanks for posting.

StrappySandalsStrappySandalsover 1 year ago

Nice!! A happy cross dresser story worth reading... Good people having enjoyable sex... 5- Stars

AnonymousAnonymousover 1 year ago

Interesting twist on the "High School Reunion" stories. Now I must patiently wait for your next story. May I offer an idea for a story line? Maria is staying at a hotel, she has gone to the bar when a false fire alarm is sounded. She is outside with everone else and spies a hunky Firefighter that perks her interest. She flirts and gets him to agree to meet her at the bar the next night. From there she is just Maria having fun with a new conquest.

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