Caroline's Mom Ch. 01byheryankee©
We were best friends and next door neighbors. We grew up together. Now we were both eighteen and heading off to college. Caroline was gorgeous, sexy, and my best friend. I thought of her as my sister. We told each other everything. It was me, who got her rubbers when she decided to have sex with her boyfriend. It was her, who talked Nancy into sleeping with me.
We were both going to State College together. We left, Caroline joined a sorority and I a Fraternity. I met a girl and Caroline, a guy. We double dated often and wound up spending the night with our dates in adjoining rooms of the frat house.
One morning after meeting for coffee we were talking about our respective dates. Caroline mother Rachel 38 years old, looked like my girlfriend just a little older like about 25. Her boyfriend looked like me so I started to tease her.
"You really want me, so you found a guy that looked like me."
"You shouldn't talk though Anna (my girlfriend) looks like my mom. Do you have a crush on her?"
"I have had a crush on her since I met you."
"I always thought so, especially after dad left."
"I think if you were older, mom might have done something about it."
"I think she knows and is flattered."
Then, on with campus life. Midterm exams and visits from parents. I broke up with my girlfriend and was getting horny. Caroline told me that Rachel, her mom was coming for a visit this weekend. There was a frat party Saturday night and I was dateless. Caroline wanted to go and didn't know how to get rid of her mom. I didn't want to go. I offered to keep her mom company. I told Caroline that she couldn't spend the night at the frat house because her mom would know. Caroline suggested I take her mom to the party as my date, no one would know she was Caroline's mom. And who knows maybe I would get lucky. +
"How could you say that?"
"She's my mom, and you're my best friend. I love you both."
"I think she wants you as much as you want her."
"Besides what can she say to me about spending the night in the room next to yours if she is in your bed all night."
"A little booze and some romantic dancing. You might just get lucky."
"You're talking about me fucking your mom!"
"I'm talking about my mom fucking you, she wants you she has for a long time, even if she doesn't admit it."
"She won't go out with me."
"Yes she will when I tell her your staying home because you don't have a date."
"She will even pretend to be enamored with you, so that everyone will think she is your date."
"She would never embarrass you and maybe they will play chicken."
Chicken was a game played by couples on campus at parties. A couple would get in the center of the floor and kiss passionately. The next couple would go one step further. The first couple would have to outdo the next couple. The last couple left was the winner. No girl had ever gone further than a blow job.
"Your mom won't play."
"Yes she will if I dare her to she won't back down from a dare."
Friday night I went to Caroline's dorm to meet her and Rachel for dinner. After kissing them both hello Rachel told me that she would be my date to the party Saturday night as Caroline had explained everything to her. She handed me a hundred dollars, and told me that Jeff was joining us for dinner and she would act as if she were my date tonight. Therefore, I should pay for dinner. Jeff arrived and insisted that he take his car and drive.
We went to a local roadhouse and had a great dinner. The ladies went to the ladies room and Jeff and I talked. He said that since this was my first date with Rachel who he thought was my new girlfriend. I just met that we would just park rather than go to a motel, or the frat house. I couldn't argue because I couldn't say that I didn't want to park without arousing suspicion. I figured we could fake it, and he would never know. Caroline would keep him busy.
After a little while the band began to play. Soft, romantic songs filled the air. Couples got up on the floor to dance. The dances were slow and the couples danced as closely as you could get. Rachel took my hand and led me to the dance floor. Put her arms around my neck, and molded her body against me. She then whispered in my ear.
"Make it look real, hold me as if I were your girlfriend."
I placed my arms around her held her close, my hands went to rest on her butt.
"This is a first date and first dance." She whispered.
She took my hands and moved them away from her ass. I whispered in her ear and kissed her cheek. Telling her I was trying to make it look good. Then a small peck on the lips. I noticed Caroline and Jeff on the dance floor sharing a deep soul kiss. Rachel whispered that we could fake that kind of kiss, so that it looked like a second date would be in order. I kissed her long and open mouthed. She whispered into my ear that anyone could tell the difference between what we did and when a real deep kiss was involved. She told me to do it again, and to use my tongue since we both knew it was fake. We kissed a long deep soul kiss, and I could swear Caroline gave me a wink and a smile.
I put my arm around Rachel as we walked to the car. We got in the back seat and Jeff drove us to Lookout Point. He parked in a dark corner and immediately began to kiss and fondle Caroline. Rachel whispered in my ear.
"I guess we have to fake it, so have fun but don't go too far."
"Just make it look real."
I wrapped my arms around her and began to kiss her. My tongue entered her mouth and she moaned as if enjoying it. Jeff turned to look at us, so I slid my hand up to touch her breast. She pushed it away. Jeff went back to what he was doing, and we continued to kiss. His head went down to the front of Caroline's chest, we could see that her blouse was off and her back was bare. She was bare chested and he was kissing her tits. He looked at us and I again reached for Rachel's breast. She whispered in my ear that I could touch them only so Jeff wouldn't get suspicious. I got to feel her breasts, like her daughter she was braless. Her nipples were hard. I continued to caress them, hoping to get her hot and live out my fantasy.
A short time later we heard a zipper being opened. Caroline's head went below the seat and we heard some slurping sounds. She was giving Jeff a blow job with her mother right there. He groaned and I slipped my hand under Rachel's blouse.
"I guess I have to do something so they don't think you are going out with a cock tease" she whispered in my ear.
Her hand dropped to my lap as I kissed her and fondled here breasts. Making sure Jeff could see she unzipped my pants and put her hand inside. She moved it so it would look like she was jerking me off, but she didn't touch my cock I whispered in her ear that if her hand didn't come out full of cum he would know that we were faking it. I started to unbutton her blouse, and then her hand wrapped around my cock. She moved it slowly and deliberately. She whispered in my ear.
"If you unbutton one more button, I'll slap you and end this date. I don't really want to give you a hand job and it will be the perfect excuse to stop."
I had to decide whether to give her the excuse she wanted, or let her give me the hand job. I reached for the button on her blouse, wanting to be the gentleman. Then she whispered to me.
"If you do that you won't have a date for tomorrow."
"I know you want to cum, I can feel how stiff you are. Enjoy it you may never get this chance with me again."
Her hand continued to move slowly as I kissed her and caressed her breasts. Her lips went to my ear and she whispered that she was going to leave me a hickie so they all thought she was a very passionate woman. Her hand moved faster and faster, as she moaned, and sucked on my neck. I groaned as I came in her hand and she milked me until I was completely soft. She took a tissue out of her purse and made a big project of cleaning her hand. Then we got our clothes straightened and all went home. I kissed her goodnight at the door because Jeff dropped her and Caroline off first. I had to make it look good.
As I entered my room, the phone was ringing.
"Alan?" It was Caroline.
"Caroline, why are you calling?"
"Mom is in the shower, she told me to get you another date."
" She felt what she did tonight was wrong. I told her it was all part of the charade, and no harm was done. She admitted to me that going out on a date like a college girl was fun."
"What do I do now?"
" I'll tell her you can't get a date and aren't going. You play along with it. She will ask you to take her, telling you she changed her mind. Make her coax you."
"Are you sure she will?"
"Just leave it to me. Meet us for lunch you will see."
"I don't know. I really think this isn't gonna work."
I hung up the phone and went to bed. My mind kept replaying the date with Rachel. I couldn't stop thinking of the make out session in the back of Jeff's car. I wanted to feel her breasts again. I wanted to kiss her and have her stroke my cock. I couldn't believe that the kisses I got from her were completely faked. Maybe she did like me.
I woke about 10:00 A.M., showered and shaved. I dressed in casual but nice clothes. We were going out for lunch and I wanted to impress. But the truth was, I didn't think I had a chance. Some nice cologne and I was ready. I met them at the sorority house, and we went to a small Italian restaurant off campus. It was too expensive for most students, so we wouldn't meet any students. We sat at the table and ordered our meals and a bottle of Chianti.
Caroline started the conversation.
"Did you get a date yet?"
"No, I guess I just won't go."
"That is really sad. It is probably going to be the best party of the year."
Looking really sad. "What can I tell you? I guess I'm a real loser, and can't get a date."
Rachel couldn't let me say that.
She said. "You are such a good- looking guy, if I were younger I'd be your date."
"You were last night, and even though we were faking it, you won't go out with me again."
"I would, but you are too young for me."
"Yes, I guess I am."
I pouted and seemed to concentrate on my wine. The women decided to go to the ladies room together and left me alone at the table. They came back in a short while, looking like that had been arguing. We ate in unusual silence. The tension palpable and made the ride to their dorm very unpleasant. As I held the door for Rachel to get out of the car she asked if she could talk to me in private, and I agreed. Caroline told her mom that we could use her room for an hour, that she had some errands to run. We went up to the room and Rachel closed and locked the door. She sat on the bed and began to speak.
"I want you to go to the party tonight, so I am going as your date. Last night was wonderful but I felt very uncomfortable doing those things with you. Don't expect me to do that again. But then I did like it and I don't want to be pressured. If I decide to do anything with you it will be on my terms. I'll be your date tonight. Now please kiss me before I change my mind." I walked up to her, encircled her with my arms, and brought my mouth down on hers is a very gentle grateful kiss. Her hand went to the back of my neck and pulled me tighter, and her tongue invaded my mouth. Her hips ground against mine and she groaned softly.
"That's just to keep you guessing." Her eyes looking mischievous.
That afternoon was one of the most confusing and exciting times in my life. I wasn't sure how to behave, and I was sure Rachel had something planned. The clock seemed to take forever to reach 8:00 that evening. I headed for their dorm. They we dressed like twins. Both in crop tops and short mini skirts. I took Rachel and left Jeff to pick up Caroline. She put her arm around my waist as I put mine around hers. We appeared just to be another campus couple. The walk to the frat house was leisurely, and almost romantic.
As we walked into the frat house, someone handed both of us a beer. We took them, and sat together on a small divan. We talked quietly, as all the guys seemed to be checking her out. I told her that they all considered me lucky, because she was the hottest woman at the party. She smiled, and kissed me deeply, and guided my hand to her breast. As she whispered.
"Lets really make them jealous" . Just then Caroline and Jeff showed up. Rachel looked right at Caroline and took my hand to guide it under her top. I felt her bare breast and hard nipple under my hand. She then kissed me deeply. I didn't know what was going on between the women, but I knew I was getting the benefits of it. I pinched her nipple and she moaned. She slowly put her hand on my lap and rubbed my hard cock. Her lips went to my neck and she sucked and bit leaving me another hickey. The music turned to a slow dance and she dragged me onto the dance floor. Her arms went around my neck and my hands went to her ass. She ground her hips into me as we swayed to the music.
The DJ announced a game of chicken the winning couple getting a weekend at the Hyatt in the honeymoon suite. It included dinner and drinks. Caroline told Rachel she was going to win, and explained the rules. Rachel said she would win. I told Rachel that there would be no faking, everything happened out on the dance floor with everyone watching. I said I did not want to play. Rachel told me that she had to win, and that if I helped her the honeymoon suite would be ours for the weekend. She also said she would not exactly be a blushing bride there. I asked her if that meant that we would have sex. She told me it might happen on the dance floor during the game.
The rules of chicken are very similar to seven minutes in heaven . . . Except the action happens on the dance floor, one couple at a time. The next couple must outdo the previous couple or quit. This continues until one couple is left. That couple is the winner.
Only four couples joined. The first kissed deeply and groped each other fully clothed for seven minutes. The second couple did the same things and then removed her blouse and bra. He sucked on her nipples. The third couple was Caroline and Jeff. The kissing and petting continued until he ate her to orgasm on the floor. The walked away smiling, and Caroline dared her mother to beat her. Caroline then winked at me. We walked onto the floor, and I immediately kissed Rachel deeply. I caressed her breasts and bared them for all to see. I kissed Rachels' nipples as my hand reached under her skirt to caress her mound. After undressing her completely I licked, and sucked her pussy to orgasm. Rachel knelt before me, kissed, and licked my cock. Then time ran out.
The first couple quit. The second couple did everything done before them. The girl also sucked him to orgasm. As she finished, she showed everyone her cum- filled mouth, then swallowed. Jeff and Caroline did that, then she got him hard again and fucked him on the dance floor.
I wondered what Rachel would do now. She reached for her purse and brought it onto the dance floor with us. Rachel kissed me and began the buildup to what her daughter had done. I didn't think we could win or for that matter that she would fuck me. It was not long until I would up on top of her with my dick hilted in the hottest wettest snapping pussy I had ever encountered. Rachel stopped me as I neared climax. I was sure she was quitting. The she reached into her purse and removed a tube of KY jelly. She greased my cock up and told me to fuck her ass. I buried my cock in her ass and fucked her until I came, squirting the last few drops on her ass and back. We won.
"I guess since you've had me already there is no reason that I shouldn't spend the night>"
"Where is your room? You better have plenty of energy left. I haven't been laid in a year." I took her hand and led her to my room.