Chapter 4: Four Can Play at That Game

Monday we all slept in and didn’t get out of the house to go to the beach until 11:00 am. We had a light lunch at a kiosk that served salads, yogurt and tacos. We played in the surf with the boys for about an hour then watched them surf. We got back to the house around 6:00 pm and took showers and the boys took us out for dinner. It was a little after 9:00 pm when we got back to the house and settled into the living room for a drink. Of course, the subject of our challenge came up. Tony was not about to let his question from the previous night go unanswered.

Cindy looked at me and shrugged so I got up and got my second drink of wine and came back and sat down and started revealing more of our adventures to the boys.

“We really had our nose to the grindstone in our freshman year of college and did not have much of a social life. We had left our high school boyfriends behind and were not particularly interested in starting any new relationships. Being in college was just too exciting and demanding. Of course, Cindy and I continued to take care of each other so the lack of male companionship was not a terrible hardship.”

“It was in the middle of our sophomore year that we started to branch out. We had settled into a routine and had some time on our hands on weekends. We started going to college parties and socializing more. We were at a frat party and we were having a few drinks and there were two of the cutest guys that caught our eyes. For some unknown reason I told Cindy that I would love to get the sandy-haired one in bed. Cindy said she would not mind having a romp with his friend. I kiddingly told Cindy she was out of luck because I saw him talking to a redhead a few minutes ago and they looked pretty friendly.”

Tony started to laugh and said. “I know where this is going. My mom never turns down a challenge.”

“You’re right Tony. That is exactly how it got started. Your mom bet me that she could get him to take her to bed before I could get Sandy Hair in my bed. The game was on. Of course like any game or bet we needed rules. We argued a bit over the rules and discarded some, but these were the final five.”

1. We could not ask them

2. They had to ask us

3. No grabbing of genitals

4. No flagrant exposure of breasts or underwear

5. We needed to get them to come to our apartment

“I am proud to say that Cindy did not get him to ask her before I got Sandy Hair to ask me. It took her a whole additional fifteen minutes. The four of us left together and went to our off-campus apartment. We had a couple more drinks and then retired for the night with our new found friends. We had two bedrooms even though we often only used one when we did not have a male companion.”

“We continued to play our little game every few weeks if we were not dating someone.”

Brian asked, “What happened if only one of you was able to get the guy to ask you to go to bed with him?”

“That did not happen very often. I have to say we got pretty good at teasing them and letting them know we were interested and all they had to do was ask. But when it did happen, the unlucky party was banned from the bedroom until he left because there was no sharing of your night’s prize.”

“And that boys is pretty much it until the middle of our junior year. Now, who is going to get me another drink?”

Brian got up and took my empty wine glass and Cindy’s. He came back with a fresh wine bottle and two clean glasses and two more beers. He poured our wine and sat back down.

Brian opened his beer and said, “I imagine the challenge stopped after you met our dads.”

“Yes, it did. Your dads were the last two men we played the challenge with until last week with you two. Your dads moved in with us two weeks later and you pretty much know the rest.”

“That must have put a crimp in the two of you getting together.”

“Well, not really. We were all flaming liberals and we told your fathers about our little affair two weeks after they moved in and they were okay with it. They gave us our time together then and even after we married them.”

Cindy was pouring herself another glass of wine when she totally shocked me by saying, “They loved to watch.” And smiled at the boys over the top of her wine glass like the sultry babe she could be.

I nearly choked on my wine and said, “Oh my god Cindy, can’t you keep anything a secret?”

“Oops, maybe that was TMI (too much information). Oh well, cat’s out of the bag now ... Cat.” As she started to giggle at her own terrible pun.

Tony the normally reserved one said, “I would love to see that.”

She just looked her son in the eyes and said, “I thought you would never ask.”

I screamed, “CINDY shut up for Christ’s sake!”

Cindy reached for the empty bottle of wine and put it back down in disgust. “Come on Cat you loved it when our men watched us make love and then they made love to us.”

I looked straight at Brian wondering what his reply would be to my next statement. “Yes, Cindy I did love it back then. But even if I did want to do it again I don’t really think Brian would like to see his mother naked or see me making out with another woman.”

I expected Brian to reject the idea immediately, after all, who wants to see their mother do that. A girlfriend maybe but certainly not your mother. Then suddenly I was not so sure. I realized I was holding my breath wondering if I would do it if he said he would like to see us together. Wonderful memories from the past flooded my mind. My hands started to tremble in anticipation and something in the back of my mind wanted him to agree with Tony ... damn it Brian say something.

Brian leaned forward and I could sense his hesitation, “Mom, I know you love Cindy in a way that I do not think I will ever truly understand. All I know is that it is right for you. That you need to be intimate in a physical way just tells me how deep that love goes. Would I like to see two beautiful women who are so much in love, make love? Sure I would. The fact that you are my mother and my best friend is your lover and Cindy is your best friend and my lover makes our present situation highly unusual. We have formed a very special bond between the four of us that I am sure will last well past this two-week vacation. If you are willing to share that moment of love between you and Cindy with Tony and me I will be forever grateful.”

I could not immediately think of anything to say. I looked at Cindy for guidance and all she did was smile and shrug her shoulders. I cleared my throat and all that came out was, “Okay I guess I can do that.”

Cindy got up and gave me her hand. I stood up next to her nervously holding on to her hand when she said, “Give us about 20 minutes and then come up to my bedroom. We will be waiting for you.” Without another word she led me up the stairs to her bedroom.

Cindy closed the bedroom door and came to me and we embraced. I hugged her tightly not knowing what to do next or say. Thankfully Cindy took charge and kissed me and said, “Get undressed honey.” She broke our embrace and went to her closet and brought back two dressing gowns and handed one to me. I laid the dressing gown aside and started to undress as I watched Cindy do the same.

When we had undressed and had the dressing gowns on we went to the mirror and brushed our hair and adjusted our make-up. Cindy got in the center of the bed and sat with her legs tucked under her and supported herself with one hand as she leaned slightly toward the headboard while facing the door. I was on the bed beside her on my knees and sitting on my heels with my back straight and hands folded in my lap. I caught myself holding my breath and had to command my lungs to breathe as I watched the door in anticipation.

Cindy patted me on the back and said, “Relax honey the boys will be here in a few minutes.”

It could not have even been two minutes when we heard a knock on the door.

I took a deep breath as Cindy said, “Come in.”

Tony and Brian entered looking a little nervous but excited at the same time.

Cindy pointed to the two side chairs she had in the bedroom and said, “Sit down and relax.”

The boys quickly retrieved the chairs and placed them next to each about four feet from the side of the bed and sat down.

We got up on our knees facing each other and embraced and started to kiss. At first, it was just gentle pecks on the lips and neck. I was very aware of the boys watching us, especially Brian. I could not help but glance at Brian to see if he showed any sign of being uncomfortable or disgusted as he watched us. He was leaning forward with his elbows on his knees and his hands folded and smiling. He even smiled and winked at me when he caught me glancing at him. Cindy could tell I was still a little nervous and when I glanced at the boys for the third time she put her hand on my cheek and turned my face toward her and passionately started to French kiss me. That got my full attention. I held her tighter and my hips pushed against her. Cindy was always the more aggressive one in our lovemaking but once I became aroused my body would telegraph my needs to her.

I felt Cindy run her hand up my side and cup my breast. She fondled my breast for a few seconds then put her hand on my shoulder and pushed the dressing gown off my left shoulder and down my arm to my elbow exposing my breast to my son and Tony. She again cupped my breast and ran her thumb across my nipple. I reached between us and undid the tie on her dressing gown and pulled it open as she leaned forward to take my nipple into her mouth. As Cindy was leaning forward sucking and cupping my breast with her breast hanging down, I reached under her and grabbed both breasts and started to pull on her nipples. Her dressing gown hid what I was doing from the boys but I am sure they got the idea.

Cindy reached inside my dressing gown and cupped my mound and expertly thumbed my clit. Instinctively I spread my legs a little more for her. My body started to shake as I pressed myself into Cindy’s hand. My dressing gown slipped off of my right shoulder. Dropping my arms straight down I let the dressing gown slide off my arms. I was totally exposed to the boys from the waist up and I hardly noticed them. I just wanted Cindy to make love to me. Cindy used her free hand to undo the tie on my dressing gown. It fell away and I was totally exposed.

I felt her hands gently push on me to let me know she wanted me to lay down. I lay down with my legs slightly parted, my feet toward the headboard. Cindy straddled my hips and started to grind on me as she removed her dressing gown and threw it aside. Cindy lay down on top of me and whispered in my ear. “I bet our boys both have lovely hard-ons right now.” I reached around and gently slapped her ass and quietly mouthed the word, “Hussy.” I heard her giggle and call me a “Floozy.” As she kissed my cheek. I had not really thought much about the boys since Cindy started to play with my pussy. I looked over just in time to see Brian adjusting his erection. Tony seemed mesmerized by his mother’s butt as she was grinding on me. I pushed up with my hips so we had better contact as we rubbed our mounds together.