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My Girlfriend’s Best Friend – Part 4 The Summer of ’77 Ends

1773 words | 1 |4.50

All good things must end, and the summer of 1977 was no different. It had been an awesome summer for a teenager living on the Central Coast of California. I had played at a lot of the festivals in the area that celebrated the local crops; the Garlic Festival in Gilroy, the Artichoke Festival in Castroville, the Broccoli Festival in Greenfield, and the Strawberry Festival in Watsonville, just to name a few. There were also a ton of community events throughout the area and even up into the South Bay, as well as openings for a few well known acts from the SF Bay area and our usual bar/club gigs. Our band stayed busy. So did my cock.

Ruth had become my favorite go-to girl on the weekends. I still saw my other ladies, but spent less time with Michelle than I had before my girlfriend, Laurie, and her best friend, Ruth, had come along at the beginning of the summer. What a sweet deal that turned out to be. ‘Dating’ one girl who I never got pussy from while fucking the other who I never really had to date. Ruth was definitely my kind of girl. Laurie, on the other hand…

School started right after Labor Day weekend. Finally, my senior year! The end of high school was only nine months away and I would be glad to say goodbye. But nine months can be a long time when you’re seventeen, and a lotta shit happened that year, not all of it good.

Ruth had become as eager for sex as any other girl I was involved with at the time. But her schedule seemed to be a lot more open to me and she didn’t have a problem if I showed up at 3 or 4 a.m. after a gig to spend the night. And her parents never seemed to mind finding me in their kitchen the next morning, even on a school day.

Ruth had become very generous throughout the school day, too. There was always before school sex, whether I spent the night or came by to pick her up in the morning. Then there was the two or three lunch periods each week when we went back to her house for ‘lunch’. And the almost every day after school sex we both enjoyed immensely. It wasn’t long before I realized that I could dump Laurie and it would likely have little or no effect on my sexual relationship with Ruth.

My band was hired to play the first school dance of the year at my school. They couldn’t really afford us, but with me in the band and one of my buddies doing the hiring, we cut a deal. There were like three guys who I considered friends back then, and Jon was one of them, so I talked the rest of the band into doing it as a local discount or some shit.

Laurie got roped into babysitting her younger twin brothers because her way hotter younger sister had already been asked to the dance. Ruth wasn’t going to go if Laurie wasn’t there. And I wanted to hang with a cute girl on our breaks and maybe for a while after.. I had pretty much burned my bridges with most of the hot girls in the junior and senior classes, so I had to look to the sophomore and freshman girls. And the freshman class of ’77-’78 at North Salinas High was absolutely fucking stellar!

Enter Kristen, a super hottie with a great body. She might not have been as beautiful as Laurie’s freshman sister Val, but she had a great ass. And I was definitely an ass man. Give me a pretty face, great ass and slim thighs and I wouldn’t even care if the girl had tits or not. And Kristen had it all.

So, not knowing (or caring, really) that Kristen was good friends with Val, I pounced on the new blood and locked her down for the night. Sure, she danced while I played, but it was my tongue that was in her mouth between sets. I guess she couldn’t resist telling her friends and Val must have told Laurie when she got home. I suppose I could have tried to seem remorseful about it the next day, but I was really getting tired of Laurie and all of her future plans for ‘us’. Shit, me and her had about as much of a future as me and Ginny. Which is to say not a fucking chance in hell!

When I saw Laurie that Saturday afternoon before heading off to a gig in Santa Cruz, she told me she would forgive me and take me back if I just called Kristen and told her that the previous night had been a mistake. I told her it hadn’t been a mistake and that I’d had a great time with Kristen. Laurie bawled her eyes out and promised me that she would have my reputation ruined. Yeah, like dating a girl for a whole summer and not getting into her pants hadn’t already done enough damage to my rep.

After the Santa Cruz gig, I showed up at Ruth’s. She was a little pissed at me. It wasn’t so much that I broke up with her best friend, it was how I did it. But I really didn’t know how to handle relationships at that age. Shit, to be honest, the only relationship I ever really handled well in my life was with the girl I married. And that was mostly because of her and her generosity in the wild fucking sex department. More about her later. For now…

Even being pissed, Ruth couldn’t deny the fact that she wasn’t finished with me yet. And that very night she did something that I had only done with one other girl, that one thing that most girls are super afraid to try. The big ‘A’.

My cousin, Lori, was the only girl who had let me put my thick prick in her ass. And she loved that shit. As long as I wetted her brown corridor up with a ton of her natural lube with my mouth and fingers first, as long as I went very slow until I worked myself all the way in, and if I only butt fucked her in the missionary position, she loved it. She swore she had the best orgasms that way. But then she was always a pretty kinky slut, the first of us cousins to try anything and the instigator of all of our youthful indiscretions.

Ruth and I got to fuckin’ right after she chewed me out for dumping Laurie the way I did. And she was into it! She had never taken the lead before, but that night she climbed on top of me and rode my thrusting shaft until she popped several times. Somewhere along the way I slipped out of her pussy, and on her next down thrust, my cock went up her ass. And she just kept going.

Strange thing was, I never even noticed! It didn’t feel any different to me! My dick must have had planty of her pussy juice on it and her sphincter must have been somewhat relaxed or content, but I didn’t know we were involved in anal until after we were done.

Ruth had a couple of amazing orgasms that she was extremely vocal about, fairly singing out in ecstacy when I made her cum twice in a row within seconds of each other. It was while she was in the midst of her second cum that my pleasure pole erupted and I lay back on the bed, thanking the gods or the fates or the universe that Ruth hadn’t kicked me to the curb.

When she was finally able to come down from her climactic high, Ruth flopped down on me, the side of her face resting on my chest, her hands hanging limp at my sides. I could feel the sweet dripping from her face onto my chest and she was breathing a lot harder than usual after sex.

“Wow!” she finally breathed out. “Fuckin’ incredible! I guess my mom was right.”

I still had no clue what had just happened. So I said something like, “You mean about being aggressive and taking what you need instead of waiting for me to give it to you?”

I felt Ruth’s head shake a ‘no’ on my chest as she replied, “Uh-uh. Well, I guess that too. But I mean the other thing.”

I was still confused. “What other thing?”

“Oh… let me…” she began as she pushed herself up from my chest, “let me just get your cock out of my ass first…”

Ding! Ding! Ding! The lightbulb over my head finally switched on. How could I have not noticed something like that? And it wouldn’t be the last time in my life it happened, either. I always thought that I was such a sexual expert, yet here was a sixteen year old girl who had been a virgin only about four months earlier, and now she had lost her anal virginity to me as well and yet I hadn’t even been aware of it. How’s that for making me feel like an amateur?

Ruth curled up next to me, snuggled deep in my chest and shoulder, then sighed contentedly. “Mmmm…a few years ago my mom told me that everyone should enjoy a little anal play now and again. To tell the truth, I never thought I’d be brave enough to give it a try. But when your penis slipped out of my vagina and entered my anus, it felt so smooth and the pain wasn’t as nearly intense as I thought it would be. So I just kept going. And it’s true… everyone SHOULD enjoy a little anal from time to time. God, those orgasms at the end were so fucking awesome! But now I feel really tired. Really good, but really tired. Baby, I know you usually get to fuck me a couple of times when you first get here, but I just don’t have the energy tonight. I’ll make it up to you tomorrow. Promise.”

And with another deep sigh or two, Ruth fell asleep and left me to ponder those fateful words about how everyone should enjoy some anal. I didn’t think I could or would enjoy having something shoved up my ass. Little did I know that the seeds had already been planted in my perverted little mind…

Next: the last year of high school continues

Rocky J.

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1 Comment

  • Reply Cappy ID:2pdvucf0v1

    Perfectly wonderful.
    I had a similar experience with a girl like you did with Ruth.
    I can really relate to this. Awesome!