Chapter 21

The ladies discussed the rules for a few more seconds, then decided it was time to get started. I could tell the wine had made both of them more courageous than normal. So after a quick decision, Jen was to go first, Tiff was to be second and I was going to be last.

Jen rolled first, a three, and moved into an open spot. Tiffany rolled a five and had an open spot as well. Great, I was going to be the first one carded, I had no luck at all. I was relieved to roll a three and take my place next to Jen. Jen rolled again and once again managed to find an empty spot to land in. Tiffany picked up the dice nervously and rolled a six, which landed her into a red square, which by the way was instantly the colour her face was turning. Tiff slowly pulled the first red card off the top of the statement pile. Her eyes nervously scanned the words.

“Oh crap.” she exclaimed, “Can I pick another one?”

“No way girlfriend.” Jen squealed, “You read the rules. You have to answer. What’s the question?”

“Um, it says: ‘Have you at any time ever masturbated anyplace other than home?’” she read softly, barely looking up from the card.

Jen bust out laughing and squealed in delight. Tiff reached over and slapped her softly on the shoulder with a look of disgust on her face. Jen leaned in intently toward Tiff like she was waiting for the winning numbers to the lottery. Tiff squirmed in her seat, looking at the card, then back at us, finally putting it down.

“Ok, I can’t lie about this one because Jen knows better. I have from time to time, uh ... you know, done it at work.” she confessed.

Jen howled in delight and was laughing hysterically, much to Tiff’s dismay. Tiff protested saying Jen already knew about it, and it was no big deal, since apparently Jen had confessed doing the same thing to Tiff.

“Just what the hell goes on in your office?” I asked Jen.

Both Jen and Tiff bust out laughing at the same time, I think Jen was actually crying she was laughing so hard.

“Don’t tell me you never did it at work Jeff, I know guys, you are horny all the time.” Tiff shot back at me, “Anyway, it’s your turn, cause I answered truthfully.”

I picked up the dice and rolled a seven, once again landing me in a safe place. Jen then rolled, moving her piece the allotted spaces and she, like Tiff, landed on a red square. Tiff was elated, clapping her hands and laughing. Jen picked a red card off of the pile and began reading.

“Tell the other players one sexual fantasy that you hope comes true.” Jen read.

“That’s easy, it did come true, Jeff made it happen when I was with Raine. I wanted to have sex with another woman. I did it.” she smiled.

Tiffany looked at me and back at Jennifer, she looked deep in thought. Finally she spoke up.

“Nope, that doesn’t count. It’s no longer a fantasy since you actually experienced it in real life. You have to come up with another one.” Tiffany exclaimed.

Jen looked at me for some sort of help, but I put my hands up. I told her she was the one who wanted to play this game, accept what comes with it. Jen just sat there thinking for a while looking very unsure of what to say. Finally she blurted out an answer.

“I have always thought about having sex with two men at once.” she answered.

“Oh really Jen, any two guys I know?” Tiff replied laughing out loud.

Jen reached out and slapped Tiff on the arm and told her to be quiet. I could see how this game could get really out of hand quickly. And so far no one had landed on a green or “action” card yet. I reached down on the floor and picked up the box cover and turned it over. I quickly read the introduction and judging by it, felt I was dead wrong about it.

I began to get worried.

Tiff took her turn, landed on another red card, drew a question about what was the worst sexual encounter she had experienced. She went on to mention a date she had been on, and how it led to sex in the back seat of a car. Nothing really memorable, I guess you had to be there.

I rolled again and I drew a red card as well. Both ladies were overjoyed, but I got lucky and the question was to discuss how many sexual partners you had in your lifetime. Mine was easy, Susan was my first, my high school sweetheart, and then Jen. I told the story quickly, but dishonestly as I held back my relationship with Beth. The ladies looked at me in disappointment, they were hoping for much more, I could tell. I apologized telling them, that’s all there was, all the while lying through my teeth.

Jen picked up the dice and rolled a ten moving her piece slowly and there it was, the first green space. Tiffany laughed hysterically and pointed to the green pile. She was urging Jen to pick one, be the guinea pig so to speak. Jen carefully and slowly, drew a green card, turned it over and read it. She quickly put it behind her back, holding it with two hands.

“No, no, no, the game is over. I quit”, she said with a serious look on her face.

“You can’t quit Jen, suck it up big girl.” laughed Tiff, “Lemme see the card, give it.”

Jen protested but Tiff kept it up stating that we all agreed to the game and to the rules. Jen had to read the card and do exactly what it said. Jen nervously took the card from behind her back and read it aloud. It stated that she had to kiss both the player on her left and the player on her right, on the lips, for a duration of two minutes each.

I, for the first time, burst into laughter, looking at Jen’s face. I could see the predicament she was in now.

Tiffany had gone dead silent was just staring at Jennifer, every once in a while glancing at me.

I have to admit, the sudden thought of Jen and Tiff kissing for two minutes was very arousing. Jen shrugged her shoulders, told Tiff to time her and leaned over to me. She pressed her lips to mine, softly at first, then somewhat harder. I soon felt her tongue on my lips and soon our tongues entwined in a sensual kiss.

It’s surprising at how long two minutes is when you’re being timed.

Finally we heard Tiff state that two minutes were up. Jen pulled away from me and I could see the anticipation in her eyes. She turned slowly and faced Tiff, I could tell she was nervous as hell. I agreed to keep time, glancing at the clock on the cable box. Jen leaned in and placed her lips softly on Tiff’s, and began to kiss her. For the first half minute, it was pretty much bland, not much movement. But then you could tell there was a change. I’m not sure which one of the two started it, but now their lips were firmly pressed together and I sensed that this kiss had escalated. Moments later I saw Tiff’s mouth open slightly and I knew what was going on. As they both slightly turned their heads, I could see their tongues dancing together. I glanced back at the clock and the two minutes had elapsed.

“Ok, times up.” I said.

The ladies broke the kiss, but I could tell it was an intense moment for them. They nervously looked away from each other, as Tiffany grabbed the dice to roll her turn. I noticed that Jen would not look in my direction, which kind of surprised me. After all I had saw her kiss Raine several times before, it was no big deal to me.

Tiffany rolled the dice, picked up her piece and moved five spaces, she also landed smack dab on a green square. She looked at both of us in dismay but had no other choice than to pull the card. She reached down, took the card and read its contents. She closed her eyes and hung her head. Jen reached over and took the card from her fingers and read it. I saw a nervous smile cross her lips.

“Give one person in the room a very sensual, erotic massage and you must touch every body part they have, the massage must continue for a full ten minute time period.” Jen read.

Now this was going to be good. No way she picks me in front of Jen, so I will get to see her rub down Jen right in front of me. I looked over at Tiff, who was coming to grips with her task. She looked at Jen, then she looked at me. Back and forth she went, until she spoke up.

“Jen, please don’t be mad but, can I pick Jeff?”

“Sure you can, that’s the rules, in fact I prefer you do.” Jen replied laughing.

Tiff looked over at me and gave me a “what the heck” shrug and moved over closer to me. Jen suggested I lay out on the sofa and she moved over to my chair. I did as I was told and laid face down on the sofa. Jen agreed to time the event and she told Tiff to proceed.

No sooner had she finished those words that I felt her tiny hands on my shoulders. She softly began to massage my shoulders surprising me with just how strong her tiny hands were. She rubbed up and down my back really pressing firmly into my flesh. It felt very, very good. Her hands moved down my back, to my waist line and hips. She firmly pushed the muscles back and forth in her small hands. I felt her hands leave me for a second, then they were reapplied to the backs of my thighs. As she kneaded my upper legs, I could not help the feeling I was getting, I knew my cock was hardening, but I was trying like hell to fight it. She moved down my legs to my calves and feet, making sure she covered my entire body. Jen suggested that it was time to roll over so Tiff could do my front. There was no way I could do that in the state I was in.

“That’s ok Jen, the back will be just fine.” I replied.

“You wish mister, roll over and let her do the other side.” she demanded.

I looked at Jen and saw she was determined, so I had no choice but to roll over. I now regretted wearing loose shorts, as my cock was now pushing up against them.

“Whoa, someone likes the massage Tiff. Look what you did.” Jen laughed pointing to my shorts.

I have to say this was probably one of the most embarrassing moments of my life. I was now laying face up, my cock pushing against my shorts, in front of my girlfriend and her best friend.

“Ok, continue Tiff, you still have six minutes.” Jen laughed.