Caroline's Mom Ch. 01

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.

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.


"I have had a crush on her since I met you."

"I think if you were older, mom might have done something about it."

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. +

"She's my mom, and you're my best friend. I love you both."

"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."

"You're talking about me fucking your mom!"

"She won't go out with me."

"She will even pretend to be enamored with you, so that everyone will think she is your date."

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.

"Yes she will if I dare her to she won't back down from a dare."

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.

"Make it look real, hold me as if I were your girlfriend."

"This is a first date and first dance." She whispered.

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 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.

"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.

"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."

"If you do that you won't have a date for tomorrow."

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.


"Caroline, why are you calling?"

" Why?"

"What do I do now?"

"Are you sure she will?"

"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.

Caroline started the conversation.

"No, I guess I just won't go."

Looking really sad. "What can I tell you? I guess I'm a real loser, and can't get a date."

She said. "You are such a good- looking guy, if I were younger I'd be your date."

"I would, but you are too young for me."

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.

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.

"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 always thought so, especially after dad left."

"I think she knows and is flattered."

"How could you say that?"

"I think she wants you as much as you want her."

"A little booze and some romantic dancing. You might just get lucky."

"I'm talking about my mom fucking you, she wants you she has for a long time, even if she doesn't admit it."

"Yes she will when I tell her your staying home because you don't have a date."

"She would never embarrass you and maybe they will play chicken."

"Your mom won't play."

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.

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.

I placed my arms around her held her close, my hands went to rest on her butt.

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 guess we have to fake it, so have fun but don't go too far."

"Just make it look real."

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.

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.

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.

"I know you want to cum, I can feel how stiff you are. Enjoy it you may never get this chance with me again."

As I entered my room, the phone was ringing.

"Alan?" It was Caroline.

"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."

" 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."

"Just leave it to me. Meet us for lunch you will see."

"Bye Alan."

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.

"Did you get a date yet?"

"That is really sad. It is probably going to be the best party of the year."

Rachel couldn't let me say that.

"You were last night, and even though we were faking it, you won't go out with me again."

"Yes, I guess I am."