How I got involved with older women.
Fbailey story number 797

Older Women, Younger Men

I never really considered older women until my birthday.

When I turned into a teenager my mother threw me a birthday party and invited only girls. There were two cousins, three girls from my class, and the sixteen-year-old girl that lives across the street. Her name was Stephanie and she was way out of my league. I was in the seventh grade in middle school and she was in the ninth grade in high school. I had seen her go off with boys that could drive their parent’s car.

It was a Saturday afternoon and the party was scheduled to last from noon until almost dark. Mom planned on giving us quite a bit of freedom.

My twin cousins, Ashley and Bethany, had turned thirteen a month before. Cindy, Denise, and Elaine were also thirteen already. In fact every girl there was older than I was.

There is a game that I had heard of called seven minutes in heaven where a boy and a girl are locked in a closet together for seven minutes. They are supposed to feel one another up. Well going in alphabetical order Ashley was up first and boy was she nervous.

Stephanie whispered something into Ashley’s ear and then pushed us into Mom’s walk-in closet, because it was the biggest closet in the house and it had a light.

At first we just stood there for probably a full minute, then Ashley kissed me and put her arms around my neck.

Ashley said, “You can feel me up if you want too.”

Of course I wanted too feel her up. All of the girls were wearing skirts and blouses so I pulled her blouse out of her skirt and reached up underneath it. She had on a flimsy bra that I managed to maul her breasts through.

There was a tap on the door and Stephanie said, “Five minutes.”

I quickly slid my hand down between her legs and cupped her damp panties. I said, “Damn, only a minute or so left. It’s going by too quickly.”

Ashley giggled and said, “Stephanie told me that we had twenty minutes. So you can take your time…but…you don’t have too. I’ve never been felt up before and I’m really enjoying it. You can poke your finger inside of me.”

I replied, “I don’t know how.”

Ashley backed up a step, reached under her skirt, and pushed her panties down her legs, stepping out of them. Then she took my hand, straightened out my index finger, and slipped it into her wet slit and down further into her hole. Wow! I was finger fucking my first girl…my cousin Ashley.

While I fingered her hole she unbuttoned her blouse and took it off, she unhooked her bra and took it off. Then she had me remove my finger so that she could push her skirt down to the floor.

She slipped out of her shoes and stood there naked. She pulled my face to her breasts and slipped my mouth over a nipple. She liked that as much as I did.

We got down onto the plush carpet and kissed and I got to feel every part of her body. We had a tap at ten minutes, at fifteen minutes, and then at eighteen and nineteen minutes. When Stephanie opened the door we were still making out on the floor and Ashley was completely naked.

Ashley got up, tossed me her panties, and then she carried the rest of her clothes out.

Her twin sister, Bethany was already getting undressed when Stephanie closed the door on us.

Bethany said, “Whatever she let you do I’ll do it more.”

The only thing that I could think of to say was, “She was just about to let me fuck her.”

Bethany said, “Just about…Good…Stick it in me. Then I can loose my virginity first! She thinks she is so cool being three minutes older and all.”

I fingered her and she was already pretty wet so I took my clothes off and got down between her legs. I gently pushed my hard cock into her willing hole. It went in easily and without causing her any pain.

Bethany then shouted out, “Oh God that feels so good! Fuck me…fuck me…cum in me…make me pregnant with your baby!”

She was holding me tightly and giggling softly so that the other girls couldn’t hear her. She smiled at me the whole time that I was pushing my hard cock into her and pulling it out of her fabulously tight pussy. It was the best feeling ever. I came inside of her three times and was still inside of her when the door opened.

Bethany rolled out from underneath me, ran her hand up her dripping snatch, showed everyone the big gob of cum and then said, “Top this, Cindy.”

She tossed me her panties and carried the rest of her clothes out while Cindy got undressed and the door got closed.

Cindy was in my class and she was really cute. I liked her a lot. I could see that she was really embarrassed to be naked in front of me. She was trembling.

Then Cindy said, “I’m scared but please don’t embarrass me in front of the other girls.

I said, “I really like you. Would you be my girlfriend?”

She smiled and kissed me letting her hard nipples scratch across my chest in the process.

She whispered, “I would love to be your girlfriend.”

I asked, “Is it okay if I have sex with the other girls?”

Cindy said, “Yes! You can have sex with any girl that you want, as long as I’m always your girlfriend.”

We kissed and we cuddled and then I felt of every square inch of her body. At the two-minute warning I gently slipped my cock into her and waited for her to recover. She still had her hymen and it caused her to cringe. Then just before the door opened I rolled us over and they saw Cindy riding my cock like a cowgirl.

She smiled as they cheered her on and she started to ride my cock for real.

She looked up and said, “Give me another minute…I’m real close…can you please close the door?”

The door closed, she slumped onto my chest, and whispered, “Please take out…it hurts.”

I rolled us onto our sides and let it slip out. I kissed her and then I helped her up and opened the door. I kept her panties and handed Stephanie the rest of Cindy’s clothes saying, “Please take care of her…I broke her hymen and she’s pretty sore down there.”

Stephanie said that she would get her into a nice warm bath and then she pushed Denise in and closed the door.

Denise was scared too but like Cindy she didn’t want the other girls to know. I took it very gently and opened her pussy with my fingers. Her hymen had been torn previously so it didn’t hurt too awfully much. Two fingers had her breathing harder, three really got her going, but when I slipped my cock into her pussy she moaned and called out in a louder voice, “Oh yes…do me from behind…my mother likes it in that position and I want to try it.”

She whispered that it was true so I pulled out and watched as she got on her hands and knees with her head against the door. I laughed quietly knowing that she wanted her head to bang against the door. She arched her back to make my entry easier. I slipped it back into her and pushed it in deeper causing her head to hit the door. She giggled and I picked up my thrusts causing a steady thumping on the door. We could hear the other girls giggling and making comments.

Denise turned her head and whispered, “Thank you.”

I replied in a whisper that she was welcome and then I pulled her away from the door and we snuggled. I told her that I couldn’t possibly cum again. We talked about school and we talked about Cindy being my girlfriend and being willing to let me screw other girls. Then I invited her to join us sometime for a threesome. She said that she would love too.

Elaine was naked before the door open and came right into my arms before the door closed. She dropped her panties on the pile in the corner along with the other ones.

She looked me straight in the face and said, “Look I’m not a virgin like those last four were so you can fuck me anyway that you want. My two older brothers like to stick their cocks I my cunt and in my ass while my younger brother sticks his in my mouth. Mom is pleased that they go after me instead of after her. Dad likes to make videos of us fucking and sell them to his friends.”

I looked at her seriously and asked, “Are you really a porn star?”

Elaine said, “I guess so! All I know is that I’m the family fuck hole. Even my cousins and uncles come over just to fuck me. Sometimes I just feel used.”

I said, “I can’t believe that your parents allow that to happen to you.”

She laughed in a sinister way and said, “Allow it my ass. Mom held me down so that Dad could rape me the first few times…until I got used to it and stopped fighting him.”

We just lay naked on the floor until our time ran up. Elaine was kissing my cock when the door opened and said, “Thank you” as if I had cum in her mouth.

Stephanie was the last one to enter. She was older, she was naked, and she was much better built than the other girls had been. She should be after all, she was sixteen and the rest of the girls were only thirteen. She laid her panties on top of the pile for me.

Then Stephanie asked, “So how have you enjoyed my birthday present to you?”

I asked, “Did you arrange for all of this?”

She laughed and said, “Of course…your lame ass mother was going to invite your guy friends and so I told her what I had in mind.”

I said, “And she let you!”

Again she laughed and said, “Well, we are all here aren’t we? I even got you five virgins to fuck, two of which are your twin cousins. And now…you get to fuck me…and…I know what I’m doing. I am not a virgin and I love younger men. I get that from my mother, my grandmother, and all of my aunts. They all dated and married younger men too.”

I thought about telling her that one of the girls had not been a virgin but it was none of her business.

Stephanie let me play with her bigger breasts, her longer nipples, and her puffier pussy. I had my hands on a real woman of sixteen and I liked the way that she felt. I told her that I had cum so much that nothing was left. I told her that my dick hurt and that I couldn’t fuck her.

She said, “That’s okay. I live right across the street. Come over anytime…anytime…day or night.”

She paused and said, “If I’m not there…just fuck my mother.”

I replied, “Fuck your mother.”

She hugged me and kissed me and said, “I told you that she likes younger men. You’re just what she likes.”

Stunned I asked, “I can fuck your mother?”

Stephanie laughed and said, “Yes! I keep telling you that. She can’t wait to get you between her legs.”

I was absolutely stunned. At the end of our time the door opened up and we were just sitting there on the floor talking. Stephanie looked up and said, “You five virgins drained him. He didn’t have anything left for me. In fact I couldn’t even get him hard. I’m disappointed to say the least…but he really likes Cindy and says that I can join them in bed sometime and get my fuck at a later date.”

Cindy said, “I’m his girlfriend but I don’t mind if he fucks you guys.”

Ashley asked, “How do feel about making out with other girls?”

Cindy said, “Denise and I have fooled around some.”

Denise choked and said, “You mean a lot.”

So, for the rest of the night I watched the six girls going at it. Stephanie was very good at giving the other girls oral sex and lots of orgasms. She would look at me and wink occasionally.

When things settled down I found out that they were all spending the night. I got to sleep between Stephanie and Cindy.

I came in Stephanie in the morning.

Mom fixed us all breakfast and boy were we ever hungry. I guess sex can do that to people.

After the girls were picked up by their parents Stephanie took me over to her house. Her mother was sitting in the living room wearing just a thin robe. Stephanie told her that I was there to fuck her. Her mother stood up, dropped her robe, and said, “I was hoping that you would say that.”

The End
Older Women, Younger Men
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