Pleasure and Pain (part 3)

It was my turn again and I was nervous as Hell. I didn’t have much choice though did I? Not if I wanted to win that hundred thousand. With only a moment’s further hesitation I clicked on the card and watched it turn over.

I visibly sagged with relief when I saw it said pleasure.

“There you go Justin,” Jillian said supportively as she clapped me on the shoulder.

I rolled the dice. 2. Crap. Well I suppose any number on a pleasure card was better than pain.

“Have a player of the opposite gender give you a nude back massage. You must lie on your stomach and they must sit completely nude on your butt. This activity lasts for one minute.”

It may have only been a 2, but it didn’t seem so bad.

I looked at the three girls. Jessica was still the only one that was completely clothed. I needed to change that.

“Jessica,” I said pointing at her. “I want you to give me the massage.”

“You just want me out of my clothes,” she said with a smirk as she started to undress.

I watched raptly as she first removed her shirt and then her bra, exposing her fantastically large knockers.

Then she slipped out of her skirt and panties before kicking her shoes off. She did it all so fast that I didn’t really had a chance to appreciate her nakedness before she told me to lie down. I guess there would be plenty of time for me to stare at her later.

As I lay down, I was careful not to bang up my swollen nuts on the hard wooden floor. I rested my head on the back of my hands as I felt Jessica sit on my ass.

Her pubic hair tickled and scratched my butt as she wiggled around looking for a comfortable position.

I felt my dick start to stiffen again. This was not a good time to be getting a woody. Being crushed up against the floor the way it was, it had no room to grow.

“Ready, and go.” Jennifer started the clock and Jessica started my massage.

I’m guessing she didn’t have much experience giving massages, but it felt nice just the same. Just the idea of a hot naked girl rubbing her hands all over my body was quite pleasant. And the fact that she was starting to rub her groin back and forth along my ass only heightened my pleasure (and hers I’m sure).

As she worked, her hands crept from up near my neck down towards my lower back and then to the top of my ass. When she started to gently knead the top of my ass cheeks I felt my dick begin to stir again. I was beginning to wish that we had a couch in here. For the last 30 seconds of the massage, I had to split my focus between the pleasant sensations that Jessica was causing me, and not getting a boner. I was actually relieved when it was over and she got off of me as my dick was really starting to hurt. It seemed just my luck that even my pleasure cards would bring me pain.

After Jessica had gotten off me I stood up myself. That’s when I felt the unmistakable sensation of liquid running down my butt and the back of my thighs. Jessica’s pussy had leaked all over me! I suppose I wasn’t the only one who had enjoyed the massage.

Jillian was already at the computer clicking on her action card when I walked over.

“Pleasure again,” she said as she rolled the dice. She got a three, and the words appeared.

“Make out with the player of your choice for 30 seconds. No groping is allowed.”

She looked at me hungrily for a second, and then turned to my sister. “Get over here Jennifer!” she demanded.

“What!?” Jennifer startled. “You want to make out with me?”

“Yeah, baby,” Jillian said huskily.

Jennifer’s mouth opened and closed like a fish, but no sound came out. She was totally flabbergasted.

All of a sudden, Jillian burst out laughing. “Oh, I can’t believe you fell for that,” she screamed as she clutched her sides. Tears were streaming down her face she was laughing so hard. “You should have seen the look on your face; it was priceless!”

“Yeah, yeah, very funny,” Jennifer responded, no real anger in her voice. She was too relieved that she wouldn’t have to kiss Jillian to be too angry.

“So who do you really want to kiss?” Jessica asked.

“Isn’t it obvious?” Jillian said as she wiped her tears away. “The man with the magic tongue,” she said indicating me.

I blushed at this reference to what had happened earlier. I guess she was hoping that I could use my tongue to bring as much pleasure to her mouth as I was able to bring to her pussy. I hoped so too. I hadn’t had all that much experience kissing, but by all accounts I did a decent job. Granted, I was kissing girls my own age, not someone older like Jillian who was bound to have more experience than me.

“Alright, Justin, show her what you got,” Jessica said as Jillian strode over to me.

As Jillian wrapped her arms around my waist, I put my hands around her upper back, which to my consternation was still covered by her shirt.