Betty, Bill and Richard 37 (Monty gets his wish) Teen bisex M-M-M-F-F July, 2020
My name is Richard. Betty and Bill are my friends. By the end of our senior year, the three of us had been having sex together for a couple of years.
One Monday in late April, Monty and his girl Ann had come to us for some help. By the end of that week they had learned how to make out again, which they'd forgotten. They both experienced same-sex oral play, and Monty had learned how to bring his girl to orgasm. We took them to a dance on Friday.
Now we started our second week with them. On Monday, Monty took Ann's anal cherry. Bill had told me what Tuesday was going to be, but the other's didn't know.
After school Tuesday we all headed straight to Bill's house, and soon we were all out back and naked. Bill had again taken a minute to get condoms, lube and a box of tissues.
Bill had me make out with Monty, while himself, Betty and Ann made out standing in a triangle. I thought to myself that Bill was becoming a lady's man, but that's not what was going on. All of us were feeling each other up. I enjoyed the feel of Monty's butt, shoulders, pecs and hair. Monty was getting comfortable with putting his hands on me, and when he got his hands to my dick and balls, I decided that he had an idea of what we were going to be doing today.
When we all broke up our make-out sessions, Bill looked at Monty and said, "I hope you're ready, 'cause this is your day." Monty confidently said, "I'm ready."
Bill nodded at Betty. Betty took Ann by the hand and gave her some instructions.
I handed a throw pillow at Monty and told him to put it under his ass. Monty went to the middle of the workout pad and layed down with the pillow under him.
Bill and Betty sat in the chairs where I'd been with Bill the day before. I got on my knees between Monty's legs.
Ann was next to us on her knees. She kissed Monty a nice big wet one, then she looked at me. I was half erect and gently stroking myself. Ann took a second to screw up her courage, then kissed me while grabbing my dick. Monty's eyes got real wide watching this. Ann then took my dick in her mouth while stroking my balls, and in a minute I was completely erect.
Ann backed off and opened the packet, then rolled the condom onto my dick. Next she lubed the tip, and told Monty to roll back. Monty did this, having watched Ann do it yesterday. Ann lubed his rosebud now, said "You're ready", and kissed him again.
I put my head against his anus and started pushing gently. I was thinking that he'd be delicate, scared or vulnerable here but he'd been using his dildo every day and there was minimal resistance. After I was in an inch, I slowed down and then got into the "in a little, back a bit, repeat" that we used when it was somebody's first time. It went quickly with Monty; I was all the way in after less than a minute. I noticed from the corner of my eye that Ann was smiling and had a hand on her pussy. "How are you feeling?", I asked Monty. He just smiled and nodded. His dick was half hard and if he was sore, it wasn't showing.
I used all the discipline I had to start fucking him nice and slowly and to keep a steady pace. He probably would've been happy if I'd gone faster but I wanted this to last. I pulled back a bit and put his feet on my pecs. Monty seemed a little surprised but kept smiling. I went back into the steady pace and watched him close his eyes. After another minute or two I noticed that his dick was completely hard, and I wondered if he was going to come from being fucked without touching himself. His hands were on his ass at the moment.
I started to push harder and try to get in deeper now, and picked it up just a little. His eyes opened a bit and a noise came out of his throat. I kept up with the deeper pounding for a minute, then I slowed a tad and was pulling out a bit more before slamming home. I couldn't do that forever but he really liked that. Thirty seconds of that and I went to a normal fucking motion but faster than before. I could see how we were going to get where we were going, and I was concentrating on trying to get him to come.
Something in the back of my head said that we didn't have long and I wasn't going to be able to control anything soon, so I pulled his feet up over my shoulders and leaned way forward. Now I started pounding as hard, deep and fast as I could. This I really couldn't sustain and I knew that I didn't have a lot of energy left in me. Monty's eyes popped opened, and his smile was replaced by a look of surprise. He moved his hands from his ass to my ass, pulling me into him. Soon Monty let out a yell, and his dick started coming as his ass clamped down on me. "Goooall!", I thought to myself. That's when I came into the condom. I suspect that it was twice as much as normal. Monty let go of my ass and went limp. I stayed suspended over him for maybe a half a minute, then I backed off and let his legs down as I pulled out of his ass.
Like a pro, Ann pulled the condom off and cleaned me off a little with tissues. I just nodded, and when she was done layed down on my side next to Monty, opposite Ann. Ann cleaned up Monty's ass, then gave Monty a big French kiss. "I love you." he said to Ann. She smiled and took the condom and tissues to the trash can.
Monty rolled towards me and said, "That felt incredible!". "You were really ready and you really wanted that, didn't you?" I said. Monty just grinned and kissed me, big, wide and sloppy.
Ann came back and put a hand on his chest. He smiled up at her. I got up and went to the outdoor shower and cleaned up. As I was drying off, Monty and Ann soaped the hell out of each other, made out, then rinsed and dried.
When everybody was dressed, everybody kissed everyone else. Bill told Monty and Ann to take Wednesday off; they were fully capable of making love without our help, and Betty, himself and I had to make up for some lost time. Ann and Monty didn't argue with that, and everyone went home for supper.