Betty, Bill and Richard 38 (High school graduates) 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.
During our second week with them, Monty took Ann's anal cherry on Monday. I got Monty's ass on Tuesday, and Bill "gave them the day off" on Wednesday.
What that meant that Ann, Bill and I were alone for one evening. Making out was easier with just three, we didn't have to explain anything or read anybody's reactions. Once the three of us were aroused from feeling each other up, I said that I wanted to go down on Betty while Bill fucked my ass.
There were no objections and we didn't waste any time. After Bill came in my ass and Betty had climaxed, Bill finished me off with a blowjob. The three of us cuddled for a while. Bill got up and tested the pool with his toe. "Cold", he said. It was late April.
"What's left for the kids?", I asked.
Bill answered me. "By the book, we're done. The appreciate each other's bodies a lot better. We saw them together but now you look at them and they look like they're in love. Each of them has had sex with the other gender. They can both get each other off."
"They sure are eager. It would be a pity to send them away now", said Betty.
"We can teach them a couple more tricks", Bill said.
"Rimming?", I asked.
"No. It's fun, but selling it is too hard. Let them find it on their own."
"You must have something in mind", Betty asked.
"Betty, can your harness be clean and available tomorrow?", Bill smiled.
Betty let out a sharp laugh. "We're gonna turn Ann into a monster!"
"Monty will thank us for it. He wanted anal before they came to us at lunch", I said. "I like it, but I had to get used to the idea. Monty wasn't even worried!"
Bill said, "I want to let Ann take Monty's butt tomorrow, and I want to find out when they have their birthdays."
We were showered and dressed before Bill's parents came home.
On Thursday Ann and Monty sat with us at lunch, which was a first. I think that one afternoon away from us made them feel abandoned. When we'd finished our food, Monty asked Bill, "What's on for tonight?" Bill answered with a question, "Did you enjoy yourself Tuesday?" Monty said, "You mean the ...", he stopped himself. "Yeah. That felt real good!" Betty cracked a grin. Bill continued, "You're going to experience something like that, but Ann will be... more involved." Ann's eyes got big. Monty scowled. "How is that poss..." It was my turn. "Have faith, Monty. All will be revealed and I think you and Ann will really enjoy yourself."
After school when Bill, Betty and I got to Bill's place, Ann and Monty were already there in Monty's car. Today they stayed in it a full minute after we arrived. I think they were still trying to figure out what Bill had said at lunch. They finally got out, and Monty looked nervous. I was getting butterflies in sympathy. We went through the house, stripped and Bill mixed us up so that Ann, Betty and Monty were making out in a triangle while Bill and I made out as a couple. Five people making out together can be awkward.
Bill went inside to get condoms, lube and tissue. Betty took Ann and opened her backpack.
Betty's dildo was the same size, color and shape that all five of us had, so it needed no explaining. The appearance of the harness put a puzzled look on Monty's face. Betty was quietly explaining it to Ann.
I told Monty that he should lay down on the exercise mat, and went to fetch him a pillow. "What are the girls doing?", Monty asked.
"Betty is teaching Ann how to wear a dildo so that she can fuck your ass", I said as casually as humanly possible. Monty's face was something to see at that point. He finally realized what the harness was.
Soon Monty was on his back, Ann was on her knees between his legs, proudly sporting a purple dildo. Bill was to their side, unrolling a condom onto the device for them.
Betty and I watched until Ann first penetrated Monty. They were making lots of noises, mostly gasps and groans, and their eyes were wide open, like they didn't want to miss anything and were trying to have a converation just with facial expressions.
Once Ann was halfway in, I realized that I was getting uncomfortable. This was a very intimate moment for Ann and Monty, and while Bill had something to do, Betty and I weren't needed. I took Betty's hand and tilted my head towards the two yoga mats at the far end of the shade. Betty looked at Ann and Monty. "We can leave them to themselves." I said, "Let's do oral stuff". Betty paused to think about it, then nodded.
Soon Betty was swallowing my dick while I ate her pussy. After both of us had climaxed, Betty and I licked each other's faces clean, then went back to check on the others.
Ann was just leaning back on her heels. Monty's dick had gone limp and a puddle was on his belly. Bill was starting to clean them up. "Where did you guys go?", Bill asked. "Didn't think you'd notice. We were just playing", Betty answered.
Ann looked around confused. "I didn't know you'd left!" Monty was still getting his bearings. "Search me. I don't even know where I was!"
Bill threw out the condom and tissues and casually sat on the edge of the pool, then jumped back away. "Still too cold", he said.
Ann and Monty stood up and held hands, moving towards the outdoor shower. Monty asked, "Betty, where can Ann get a harness like that?"
Betty smiled. It seemed that Monty wanted some more of what he got today. "I got mine at Pride; that's in mid June. If you're brave enough to go into an adult bookstore you can probably get one sooner, or find someone over 21 to get one for you, but they'll know you're into pegging".
Monty was slowed down by the prospect of letting anybody over 21 know what he liked, but eventually he said, "So it's called pegging. I guess that makes sense".
"That peg is hard to miss!" I said. "Bill and I enjoy it, too."
Bill was dry from the pool and started to get dressed. "While you're still here, Ann and Monty, when are your birthdays?"
Monty answered first. "I turn eighteen in mid-May". "Mine's June 5th", said Ann. "Why?"
Bill was smiling as he said, "We have had a birthday tradition for the last couple of years. It's called a sandwich, or a human sandwich or a sex sandwich. On your birthday you get to be in the middle. So Monty, you might want to be inside of Ann while one of us is inside of you, and Ann, you can have one person in your pussy and another in your ass, however you want it. I guess you could work oral into it; the details are up to you."
Monty's mouth was opened. He looked at Ann, who was smiling. "Lots of possibilities! I'll need till June to figure out how I want to work it!", she said.
Finally Monty said, "Okay, What's on for tomorrow?"
Betty answered that, "We're going to the Advocacy center to work on Pride posters. You get to meet more people. Maybe somebody that's over 21 that thinks everybody should try pegging!" All of us laughed at that.
So that was the end of Thursday.
Betty, Bill and I dropped our sessions with Ann and Monty down to three a week till Monty's birthday. The day Monty turned eighteen, he decided that he wanted to be inside of Ann while Bill was taking Monty's butt, and there were no objections. Ann got a pillow under her head. Betty put a condom onto Monty's dick, and backed out. Bill took his place between Ann and Monty's legs. I put a condom onto Bill, used the lube on Bill's tip and Monty's bud, and went with Betty to be out of the way.
While Monty the Birthday boy was finding out how the middle of a sandwich feels like I started playing with Betty's tits. She grabbed my dick and soon we were on the yoga pads giving each other handjobs. Betty and I had formed a bad habit of wandering off while the others were having sex.
After lunch that day, Bill and I bought a new workout pad and one double yoga pad. It had become hard to clean the, uhm, "love" off of the big pad, and when two people tried to use the two yoga pads, somebody ended up on the concrete between them.
After Monty's birthday, our sessions with them were only twice a week. We were going back to being a trio, and they'd gotten most of the "help" that we could have given them.
The last day if high school, without telling anyone, I showed up in Birkenstocks. Guys never wore sandals to our school, but I figured I'd never have the chance again. A couple of teachers gave long hard looks at my feet, but none of them said anything.
Right before lunch I passed Monty in the hall. He was wearing sports sandals! We hi-fived.
By that day, we were only seeing Ann and Monty once a week at Bill's house and randomly at the Advocacy center. Betty, Bill and I just worked on posters, but I think Ann and Monty were on two committees.
I later found that on June 4th, Ann had called Betty at home about Ann's birthday.
We got to Bill's after our parents had gone off to work. Betty showed up with her school backpack, which is an odd thing for a woman with a diploma.
Bill had already brought condoms, lube and a box of tissue out. Ann and Monty pulled up and joined us. Ann indicated that her, Betty and Monty should make out as a trio, and Bill and I as a couple. So the making out and feeling people up began. Now that we had the summer to ourselves, we took our time and enjoyed ourselves.
When we broke apart, Bill asked Ann what she wanted from us for her birthday.
Ann grinned and said, "A BMW, of course!", which got us all laughing. Ann said that first, she wanted Bill and I to bring her to orgasm with kisses, fingers and performing oral sex on her till she came. Monty looked surprised, Betty was smiling. All that Bill and I could do was nod. Finally grabbed Monty by the wrist and pointed at him with her other hand, "Then, I want this boy in my pussy, while Betty takes my ass with that dildo harness." Ann was grinning like she'd announced an Oscar winner. Monty was finally smiling. He could wait till we got his girl off with that king of a game plan.
We headed to the workout pad and Betty went to grab a pillow.