Betty, Bill and Richard 21 (Betty's first anal) Teen bisex M-M-F July, 2020
My name is Richard. Betty and Bill are my friends.
The summer of our fourteenth year, the three of us started with sexual experimentation and a year later we had become good at making out, masturbation and oral sex. We each had a dildo, us boys had accepted ourselves as bisexual and right at the point where we expected to start vaginal and anal sex, Betty had asked to loose her virginity to her Dad, with the result that each of us three had lost our virginity to our parents.
During the following week, after school, Bill and I had each finally had vaginal sex with Betty.
The first Monday after school was finished, Bill and I had anal sex with each other.
Tuesday morning we started with a long make-out session and felt each other up. No matter what else we experienced, that never got old for us. We got in a triangle and used our hands to bring each other to orgasm before lunch, and after lunch we reversed the triangle and did oral sex.
Wednesday morning came and started with the make-out session. When we pulled apart for a minute, Bill asked Betty if she was still using her dildo on her ass. "Every night!", she beamed. "I used the syringe to clean out my ass before I came here this morning."
Betty and I didn't ask Bill why he'd asked his question.
"Go get the condoms and lube", I told him.
"I'm getting condoms, lube and tissue", he muttered as he headed into the house.
I picked up the throw pillow I'd had under my ass the previous week when I got fucked, offered it to Betty and gave her a comic questioning look. Betty smiled and nodded enthusiastically, so I dropped in the middle of the exercise mat.
Bill came back with the condoms, lube and tissue, which I took from him.
Betty was on her back with the pillow under her ass. She looked at me and said, "Why not doggie style?" "You and Bill can see each other's faces this way, he can penetrate deeper, and you can kiss easily", I answered her.
She was contented with that. Bill was on his knees beween her legs, and I saw a problem. "Betty, pull your knees up to your chest for a minute. I need to take care of Bill here". I told her.
I kissed Bill for a second, grabbed his ass with one hand, his dick with the other and did a raunchy kissing number on his nipples for a minute. I heard a sharp intake of air. I started sucking on his dick while kneading his ass. That made a groan come out of his chest. After half a minute, Bill was hard. I put a condom onto the guy, then lubed the tip.
"Betty, try to put your toes behind your ears. You're presenting your ass to Bill as a gift here." I said. She did so with a little giggle. I put some lube on her ass and got out of the way. Bill started penetrating Betty's ass more slowly as he had done mine. She's more delicate and I might accept more pain than her, so I agreed with his approach.
All I could do was watch. Bill wanted all of his dick in Betty's ass, but didn't want to hurt her. Betty was happy to work with Bill to make this happen. Betty was losing her anal virginity to Bill right now. Bill and I had each been fucked by our dads. Betty's dad had fucked her pussy, but left her butt to us boys.
Eventully, it looked to me like Bill was all the way in. He'd pause his movements, her eyes were opened wide. Bill asked Betty how she was doing. Betty answered "Full." Bill then said, while looking at Betty, "Richard, kisses".
I kissed each of them on the lips, and got out of the way again. Bill moved forward and gave a long, solid kiss to Betty, then pulled back a bit. He thrust in all the way again, and I knew that the slow build-up to a proper fucking was underway. He got a good rhythm going in a minute, and kept it going for quite a while.
After a while they both got mean looks on their faces, like they were fighting something together. I took that to mean that Bill was about 2/3rds from coming. In a few minutes Betty was making steam whistle noises and Bill was moving fast, making quiet grunts. I knew that there wasn't much waiting left.
Finally Bill froze, and had that look I saw when he took my ass. His eyes were closed and he was fighting to control his breathing. He rolled off of Betty and onto his side. Betty pulled the pillow from under her lower back and put it under her head.
"Sore?" I asked.
"A little." Betty said. I should be able to take you after lunch."
I kissed her. "Something to look forward to."
I took the box of tissues over to Bill, the fallen hero. I wrapped the condom in tissue and cleaned his dick up.
"When you're ready to move, we'll clean you up and go to lunch."
After lunch I fucked Betty in the ass while Bill handled condoms, lube and tissues.