By Kendra Holliday | February 17, 2013 at 3:20 pm
Here is a roleplay date I did the other night that is too racy for FetLife…
I’ve been friends with this couple for five years, and we had never done anything sexual. It was just about at that point where I decided they were too much like family to get sexual with, when they asked me out on a date.
After a quick recalibration, I said YES.
They could have taken me to dinner and an art show, but nooo – Capn Marrrk and Bianca know how to court a kinky lady!
They staged an elaborate roleplay scene that went on all week!
Starting on Monday, they took turns texting me.
She pretended to be my bratty older sister and said things like, “Dad has been in such a bad mood ever since you and Mom moved out. :(”
He would text me things like, “School called. They told me you skipped class. You’re in big trouble, Missy!”
For our date Friday night, they requested I wear a t-shirt and jeans, no bra, striped socks and a backpack. (I love that I’m 40 and can still play games like this!)
Friday night, I eagerly got ready for my date and headed over to their house. On the way there, I got a text from Marrrk – I mean, Dad. It said, “Sorry Hon, I have to work late, but your sister is home.”
When I got there, Bianca greeted me at the door. She and I were wearing matching rainbow shirts!!!
Right away, she was in character.
We sat down on the couch in front of the fireplace and she said sweetly, “I miss you, Sis! I’ve had so much to tell you! But first – look! I snitched whiskey from Dad’s cabinet!”
“OMG,” I said, “He better not find out or we’ll get in BIG trouble!”
We giggled and she poured us each a tumbler. We sipped it and talked. Then she pulled out a stack of porno mags.
“Look what I found under Dad’s mattress!”
We flipped through them and speculated on the women, why Dad had the magazines, and what we looked like compared to the girls on the pages.
“I have to tell you something,” Bianca confessed. “The other day I saw Katie naked in the locker room and it made me feel all funny. Do you ever get that way with girls?”
“What do you mean?” I asked, pretending to be naive.
“It’s a tingly feeling, like the one I get when I think of my history teacher Mr. O’Brien. Only it happen when I think about girls, too!”
“Gosh I don’t know – looking at these pictures gives me a funny feeling,” I admitted.
“Do you mind if we practice kissing?” she blurted. “I’ve been practicing on my pillow and it isn’t anything like a person. I want to be ready for boys – or Mr. O’Brien, if I ever get the chance,” she said slyly.
I feigned surprise, but agreed.
We kissed for the very first time. It was wonderful!
She was so lovely and sweet. We were tentative, and started touching each other.
All of a sudden, Dad came walking through the front door, wearing a suit and tie and carrying a briefcase!
There we were sitting on the couch kissing, with his porno mags splayed around us, and his whiskey sitting out!
Right away, he was angry.
“What the hell are you two doing?!” he barked.
We tried hiding our glasses and the magazines, but his eagle eyes quickly took in the scene.
Grabbing the glasses, he thrusted them at us. “You want to drink my whiskey, then DRINK IT. ALL. RIGHT NOW.”
We choked down as much as could. It burned our throats and made our noses sting.
“MOVE OVER,” he commanded, and he squeezed in between us on the couch.
Grabbing the magazines, he started flipping through them. One of them was the Hustler magazine I was in. Opening it to that page, he pointed at my pic and said, “LOOK at these women. They’re all WHORES! Do you want to be a slut like that?”
“Well why do you have those magazines, Daddy?” my sis asked a little belligerently.
“Because I have NEEDS!” he exploded. “Your mother left, that whore! And do you know what? You’re turning out just like your mother.”
With that, he stood up and started unbuckling his belt.
“You know what?” he said heatedly, “Since you’re just like your mother and she’s not here anymore, it’s time for you to take on her wifely duties.”
We stared up at him, open mouthed.
He muttered, “I masturbate, we’re related, so being with you is just an extension of masturbating. And it’s time for you to learn a lesson!”
He pulled out his thickening cock.
= CUE THE PORN MUSIC =
“But isn’t that wrong?” we protested.
“NO,” he said definitively. “This…is Georgia. So this is perfectly okay. Now get to it!”
So we started taking turns sucking his dick, pretending to be reluctant.
He continued to be bossy and aggressive, stripping off our clothes. Once we started getting into the sex, we kindof fell out of our roles, but every once in a while we’d say something that fit the scene.
He ordered me to go sit in a chair and watch him fuck my older sister. I acted like it wasn’t fair for me to be punished like that. “How come she gets all the attention!” I whined.
It was SOOO hot watching them fuck. He laid on the couch and she rode him reverse cowgirl. Her ass looked amazing as she moved back and forth, his hands gripping her smooth, white cheeks. She was very vocal and passionate.
Then they let me come back over and they took turns eating my pussy. Then I ate her pussy. We were all cumming like crazy. My pussy got super swollen, pink, and wet. The swelling made it tighter and brighter, it was just incredible. The fantasy was so hot, the real people were so hot, the setting was so hot…!!!
They worked me over and tried to get me to squirt. I did a little, it was so intense and yummy. I haven’t squirted properly since my hysterectomy. I need more practice!
His cock was awesome. He fucked me good, too, from behind. They were both so fit and sexy. She was so gorgeous. I loved her shapely back and waist and how her ass bloomed below it. Her breasts were perfect. She was like a Greek goddess.
After we all came at least twice, we lounged about on the couch together. He stroked my underarm hair, which felt really nice. She stroked my head hair.. I was in heaven…
Then, they revealed a special surprise.
Standing up, they went over to the laptop sitting on a shelf in the corner and pulled off a little cover on the web cam that was hiding the light.
“Guess what? Your partner Matthew was watching the entire time!”
WHAT! THE! FUCK!
Stunned, I leapt up from the couch and approached the lap top for a closer look.
Sure enough, there he was, looming and glowing on the wavy screen in his wifebeater, smiling.
EVERYONE KNEW HE WAS WATCHING THE SCENE EXCEPT ME.
I didn’t know it, but they had asked him if he wanted to witness our date, and he said sure.
I was just so surprised! I didn’t feel betrayed or anything, but it was quite a surreal twist on an already unusual night! Do you know that video of the woman who can’t believe she had her wisdom teeth surgery already? THAT’S what I was like staring into the camera! No way! Huh?!
He took pics and video of the threesome, that superspy! Here is one of them, I’m on the left:
It was a crazy fun mindfuck night. I spent the night with them, it was so sweet. And I was so grateful my partner was supportive of my fantasies coming true!