Caroline's Mom Ch. 07

As the semester wore on, Caroline and I became very comfortable as lovers. Having been best friends there was no awkwardness in our intimacy. She felt that she was my sexual caretaker, saving me for Rachel, her mother. We were planning on going away for the weekend to a small one bedroom cabin in the woods. It was so secluded that we could wear no clothes and never be in danger of being seen.

Rachel asked me if we could try some "kinky" games up there. She wanted to be tied up and used anyway I wanted to. She did not want me to ask permission. Then she dropped the bombshell.

"I have been talking to my roommate Sheila about you."

"And?"

"She is a virgin and thinks she is gay, but she wants to find out for sure."

"So what do I have to do with it?"

"She wants to try a man, and I have been bragging about what a great lover you are."

"And now she wants me?"

"Well not only that."

"She wants you too?"

"More like I'm curious and would like to try a threesome. But I could never do it with mom"

" That is no way to find out if she likes men."

"I want to watch you take her cherry the first night at the cabin."

"If she doesn't like it, what then?"

"Then she gets to have me alone and you can watch."

"So I spend the second night horny?"

" No I'll take care of you after the show."

"And if she does like it?"

" Then she still has me alone, and then we invite you to join us."

" Lets go to breakfast while you think about it."

We left for the Campus Diner, as we walked arm in arm, I asked her about Sheila, who I had never met. She was a petite, natural blonde beauty with amazing 32C breasts. Her ass was perfect for this 4'11" beauty, who weighed only about 95 pounds. Sheila was to meet us at the diner as Caroline and she had already discussed it. Then if I agreed we would meet tonight and drive to the cabin tonight.

We were seated at the table when Sheila entered. She joined us and kissed Caroline on the lips . . . Just a soft brush like two friends. She looked at me and grinned.

"Did you expect me to slip her some tongue?"

"No, I just can't believe I never saw a beauty like you before."

Looking at Rachel, "Am I in or out? Has he agreed?"

" I don't know. He never answered me. Well Allen?"

Sheila looked at me. And waited for my answer.

"Yes I would like to make love to you and take your cherry, but are you sure you want to do this?"

" Yes I am"

Caroline said. "I want to try a threesome."

Caroline looked at Sheila and said, "Kiss him, show him how well you use that tongue of yours."

Sheila put her lips to mine and gently licked my lips. She sucked my lower lip between hers and gently bit it, then she rubbed it with her tongue. Then her tongue penetrated my mouth and caressed my tongue in ways I had never imagined. All I could think about was how that tongue would feel on my cock.

"Okay, you convinced me. You can join us this weekend."

With that we ate breakfast, and talked about school and the professors. Sheila was a very smart and funny woman. I liked her and would ordinarily have been eager to get into her pants. But, I was apprehensive I was worried that if she turned out to be gay I would have failed as a man. As we were leaving, Sheila gave me a long intense kiss, and a wink as we parted.

"I am going to try very hard to enjoy this. "

"Sheila, you don't have to try either you will or you won't. If you try too hard, you can't enjoy it just try to relax."

After Sheila left Caroline began to talk.

"I think she really likes you, and is having trouble waiting for this weekend."

"Really?"

"Sure, she trusts you because of what I have told her."

The week seemed to take forever to pass. My last class on Friday took even longer. I thought the weekend would never come. After my last class I gassed up the car and loaded my luggage and went to pick up Caroline, and Sheila at their dorm. Both women were wearing very short miniskirts and halter tops. They looked very sexy. I packed their luggage into the trunk and they both kissed me passionately for doing that. Caroline let Sheila sit next to me, and she squeezed into the front seat too. Then they told me they had a surprise for me. They both lifted their skirts to show me they weren't wearing panties. Sheila then told me they decided they would wear no panties all weekend. As the drive began Caroline took Sheila's hand and placed it on my lap above my penis.

"Play with it, stroke it, get used to it. He has to keep his hands on the wheel."

Sheila slid her hand down lower, and began to caress my fledgling erection. Her eyes widened as she felt it lengthen and harden under her caresses. Caroline reached across Sheila and unzipped my fly.

"Put your hands inside and touch it. It's amazing how hot and hard it is, but even then it is covered with a velvet softness."

"I'm really afraid to do that."

"Don't be when a woman is holding a man's cock in her hands she is in complete control of him and it. Besides that he can't take his hands off of the wheel."

Her hand snaked into my fly. I groaned as her fingertips explored my hardness. She grasped it and pulled it out into the open, so that she could look at it. Her head bent town and I could feel her breath caress the head Sheila's thumb caressed the tip and pre-cum began to drip. As she smeared the slippery over the head, it began to throb.

"That means he is very excited and is close to chumming. If you don't want him to squirt in your hand, stop, or lets trade places. It's not right to get him that excited and not finish him."

"How do I finish him?"

"Either slide your hand back and forth or suck him. If you don't cover the tip with your mouth, he is going to squirt all over the place. Your hand and top will be a mess. We can clean that up later."

" I don't want to mess up my top."

Sheila removed her top letting me see her hard nipples and breasts. Then she began to stroke me longer and harder. Her face was very close to my dripping penis. I began to pulsate really hard. And then I erupted the first shot hitting the innocent woman on her lips, the others over her breasts and hands. Sheila unconsciously licked her lips, smiled, and proceeded to clean me up with her mouth. Caroline licked my cum off of Sheila's breasts while Sheila licked her hands clean. The rest of the drive was spent in silence as we all contemplated what had happened. After another hour had passed before we got to the cabin.

I unpacked the car and brought everything into the cabin. The women began to cook us dinner. Caroline remarked that after a long drive like that we all might want to get to bed early. She winked at me and licked her lips. Sheila just blushed. It was amazing how red her face got, but that might have been because of her fair skin. She just brushed her auburn tresses from her face and blushed some more. Dinner was quiet and included a couple of bottles of very good wine. None of us was drunk, but we all were relaxed and comfortable. The women decided to give me the bedroom with the larger bed since it looked that I would not be in it alone. Then they went to shower and change. Caroline suggested I do the same. Sheila looked at the two of us like a doe caught in headlights. I told her.

"You don't have to do this if you don't want to."

"I do want to. I think I'm going to like it. But what if ... I'm not good at it?"

"Don't worry it's like everything else. If you practice, you get better, and no woman is actually ever bad at it unless they don't like it"

With that she smiled and they went into their bedroom to shower and dress for the evening. I showered and shaved. I splashed on some cologne and waited in my pajamas for my evening guest. To my surprise both walked into the room wearing very sexy nightgowns. Caroline explained that Sheila was nervous and asked her to be present at her deflowering.

Caroline took a seat in the corner of the room. I walked up to Sheila and took her in my arms. I kissed her gently and let the intensity build as she relaxed and responded to the kiss. Slowly I brought my hand up from her waist and gently caressed her breast through the nightgown. I could feel the nipple harden as she moaned into my mouth. My lips moved to her ear and then to the place on her neck behind her ear. Then slowly down to where her neck joined with her shoulder. I then slid the shoulder straps off and watched the nightgown settle gently to the floor.

"You are magnificent, so very beautiful. Please come to bed with me and lie down on it."

As she settled down on the bed I took off my shirt and joined her. I kissed her throat and then her chest moving ever closer to her breasts. After kissing and caressing those wonderful mounds I captured her nipple with my lips. I licked and sucked on them until they were like small stones, then I gently bit them. My lips continued down lower and my tongued explored her navel. Sheila arched her back and forced my tongue deeper into her navel. She moaned and told Caroline that if all men were as good with their mouths as I was she was silly for not trying one before. Slowly I went lower and licked into her auburn pubic hair. I pulled it with my teeth and Sheila went rigid with a mini orgasm. I licked and tasted her labia which were soaked with her juices. My tongue dove into her honeypot and I drank of her nectar. My lips now reached her clitoris and I Kissed it and sucked on it. Sheila screamed in yet another orgasm, as her hands gripped my hair and pulled me tighter into her dripping womanhood. I strummed her clit with the tip of my tongue ant then bit it gently.

" I Cant wait, fuck me."

"Are you sure? I thought you didn't like men."

"Do it now please."

I removed my pants and got between her legs. Caroline walked over to the bed and told me to be gentle. She caressed Sheila's hair and kissed her gently, telling the virgin to relax. I placed the head of my dripping penis at the entrance to Sheila's virgin grotto. And slowly slipped into her moistness. Suddenly I came upon that membrane and could feel the resistance. After telling Sheila this might hurt I thrust forward taking her virginity I then waited for her to accommodate my average size. When Sheila's hips started to move I began my thrusting. Before long our pubic hair was meshing and I was as deep as I would go. The thrusting became faster and harder as she got into the rhythm, and began to climb toward orgasm. Our hips churned and we began to pound our hips together. She screamed out her orgasm, as her vagina contracted on my cock bringing me over the edge. We lay like that locked in that embrace for a short time then I got up. Caroline took 2 white handkerchiefs and cleaned Sheila with them giving us both one of them. The handkerchiefs were both stained with our sum and Sheila' to be virgin blood . To be kept as souvenirs of the occasion. Sheila then asked if she could watch Caroline and I make love.

To be continued...