Betty, Bill and Richard 33 (Senioritis) Teen bisex M-M-M-F-F July, 2020
My name is Richard. Betty and Bill are my friends.
We spent the summers of our fifteenth and sixteenth years learning most everything, with some exceptions, that two boys and a girl can do to each other sexually.
We were typically nude behind Bill's house, by his pool, every weekday from the time we were old enough to be left alone. It started with skinny-dipping. Bill and I started jerking each other off soon after we started getting erections. Betty watched us and played with her pussy.
Our private time the end of the school year was about an hour and a half each weekday, after school but before our parents got home. By April it was warm enough that we could hang out by Bill's pool.
On this particular day, a guy we knew from swim team, Monty, had come to talk to us at lunch with his girl, Ann, in tow.
Monty had estabished that we were having sex together, first from rumors and then by getting it from us directly. He'd told us that Ann and himself were having sex, when Ann stopped the coversation, because we were in a school cafeteria and she didn't want her sexual life story to be public.
Betty, Richard and I generally didn't talk about our sex lives at school, either.
Bill had suggested that we all meet after school, which we did, and we walked to Bill's house together. We didn't talk while we were walking. I had a knot in my stomach; the three of us had never had anyone else join in our sessions. It had been two years since we'd lost our virginity to our parents, and none of us had been with another person since that day.
I took off my shoes and socks as soon as we arrived, and cuffed my pants. Betty and Bill followed my lead.
Monty paused and looked at us, nodded at Ann and then they did the same. I think Monty thought that we had some rule about being barefoot.
Bill set it up. "I can tell you how it works for us, what we've done that worked and what didn't work, but first we need to find out why you came to us and what you came to us for."
Monty was just as nervous as he had been at school, but Ann had calmed down.
"The two of us have been having sex since last fall, and it's been pretty good", Monty looked at Ann for agreement. Ann nodded doubtfully. Betty later said that she took a cue from that.
Monty continued. "Ann doesn't seem to get excited. I mean, I open her up with my fingers, and she says it hasn't hurt since the first couple of times, but I think she's just waiting for me to finish".
Ann was looking down like she was ashamed. Betty took Ann's elbow and said, "We don't need to stand. Let's sit down on the pad."
Bill's parents have an awning, of shade or shelter or whatever, where there's a ten foot square Yoga-type pad. Most of our sex happens on it because it's softer than concrete and it hoses down easily. In this case, it's good for five people to sit cross legged and talk.
Bill spoke up to catch Monty's opening and decide where to go with it. "We should be able to help you get Ann to climax, if that's what you want." Ann looked up at Bill in wonder. Bill continued, "We aren't the only people having sex in the school, so I wonder if that's really what you came to us for".
Monty was looking at Bill like he was magical or something. "I thought that Ann climaxed when I did?" Bill looked a little sad. Betty was looking at Ann like she was sorry for her. "Women don't get off from intercourse. Vaginal or anal. Women need something different", Bill said confidently.
I thought I'd seen women get off from intercourse twice over the past three years, so I thought was possible, but really rare. I didn't interrupt.
Bill sighed. "If Ann has never had a climax, she wouldn't know what was missing, and she couldn't tell you what she wanted; she doesn't know. So we can teach you to bring her to a climax and both of you will be happier." I thought Bill was repeating himself. Maybe Bill did, too. He kept going. "So after that, what did you come to the three of us for?"
Now, Monty was kinda red. "You guys are bi, right?" Bill nodded. "Us boys have jerked each other off, blown each other and had anal sex together." "We've both masturbated Betty to orgasm with our fingers, we've gotten her to orgasm with our mouths, we've made love to her breasts, had vaginal and anal sex with her, and she has strapped on a dildo and had anal sex with us boys."
Monty and Ann had fantastic looks on our faces.
Bill finally added, "A couple of years ago. Betty and a woman performed oral sex on each other, so Betty is a qualified bisexual, too".
I thought I could contribute. "Bill's parents will be home soon, so all we're gonna get done today is talk. During the school year, when the three of us get home, it doesn't matter which home, we usually strip, all three of us make out and feel each other up. After that we have some kind of sex, but we make sure that all three of us get off".
Betty said, "That's till school is out for summer. In the summer we only come here, to the pool. We always make out and feel each other up, 'cause we really love each other and we don't want it to be just a quickie. We'll make love, one way or another, in the morning, have lunch, and then do something else in the afternoon. We spend weekends and evenings with our parents."
Monty and Ann couldn't speak.
Bill prompted them. "You asked if we were bi."
Monty found his voice. "Right. Um, I guess Betty and I need to go back to making out and feeling each other, and if I can get her off I think we'd both be happier. Anyway, about the bi thing. I was thinking about, uh, trying stuff with a guy..."
"What stuff? I can have Richard kiss you right now." Bill was playing.
Monty had turned red again. "I was thinking oral and, uh.." This was difficult for Monty. " I guess maybe anal. You guys do that, right, does it hurt?"
Bill answered him, "We know how to manage the pain; it's no harder than being sore when you haven't worked out in a week. We can also teach you how to clean yourself out." Monty's eyes popped open at that one; I don't know if he had thought about that.
Betty looked at Bill. "My turn!", she said. Now, looking at Ann, Betty said, "From where I'm sitting, it looks like your boyfriend is going to learn to make out with you like he did when he first met, and we're going to teach him to feel your body all over and make love to your tits. How do you feel about that?"
Ann looked at Betty like she was a space alien. Even Monty had never talked to her like that. After Ann had a minute to digest what she'd been told, she slowly answered, "I think that will be good. You think I'll enjoy sex more?"
"You're gonna want a lot of it, trust me", Betty said. "Now, your boyfriend wanted to talk to us because we're bisexual. Bill and Richard here are going to give Monty some French kisses, they're going to suck him to orgasm and teach him to suck them to orgasm. They're going to teach him to clean his ass out, how to work a dildo into his ass slowly so he's ready to take a dick, and they're going to teach him to enjoy being fucked in the ass. Monty will probably fuck both Bill and Richard in the ass before we are done with him."
There wasn't a question, so Ann didn't have to respond. She slowly thought through all that, then nodded and said, "I think that's what he wants. If he doesn't like it, at least he will have tried it and he'll know, but me enjoying sex and Monty trying bisexual stuff aren't the only reasons that we came to you".
Betty thought about this and asked Ann, "Would you like to try having sex with a woman?"
Ann looked frightened, but she gently nodded her head and looked ready to cry when she finally answered, "Yes".
Betty looked at Monty to try to read him, and then turned back to Ann. "You don't have to do it for Monty or me or anybody else. I won't let you do anthing you don't really want."
Ann shook her head, "No, Monty didn't ask me to do this. I want to do it. I'm upset because I've wanted this for so long, but I was afraid to even ask anybody about it."
Betty kissed Ann and held her close. "You're gonna be fine. Nobody here is gonna hurt you".
Monty finally wasn't blushing. He was standing up by now, his arms limp at his side, watching Ann and Betty hold each other. I got up and went to Monty and kissed him. I kept my arm around him while we watched the girls.
"She's hurt, I don't know what from, but you didn't hurt her", I told him. "For the rest of the school year you two are going to come here for about an hour after school. We're gonna back it up and teach you how to make out and feel each other up. If it's warm enough we're going skinny-dipping."
Bill joined us, talking loud enough to get answers from Monty but not loud enough to disturb the girls. Bill asked Monty a series of quesitons: Is Ann on the pill? Has Ann given you a blowjob? Have you eaten Ann's pussy? Have you had anal sex with Ann? Richard kissed you a minute ago; was that the first time that a boy kissed you? Is Ann your first girlfriend? Are you Ann's first boyfriend? Have you had sex with anybody else? Has Ann? Did you have any jerk-off buddies? No, seriously, dude? What's the biggest thing that's been put into your ass?
"Plunger handle," Monty answered confidently, then he turned that famiar red color.
Bill slowed way down. "Splinters?"
"My Dad taught me how to take care of tool handles, like axes and hammers." Monty said defensively.
"So?", I asked.
"I got a new plunger for my bathroom, sanded the paint off and smoothed it on Dad's lathe, drilled a quarter-inch hole, put in linseed oil, closed the hole with a poplar peg, then rubbed more linseed oil all over the handle. It looked really good once I put it into my bathroom. Anway, when I wanted to play with anal, I put a condom over it and slowly worked it in. When it started to hurt I stopped, but after a minute it felt so good..."
"That you had to jerk off?" I offered.
"Yeah," Monty said. "The rubber plunger will degrade someday, but that handle will be good for 200 years."
Bill interrupted this conversation. "I'm going to show you what you need from the drug store, and I will print each of you a proper dildo. Hide it with your winter clothes if you don't want your parents to find it."
"Print a dildo?", Monty asked.
"Bill has a 3D printer", I told him.
Bill took Monty inside. A week before, Betty had measured our dicks and averaged the numbers, as she had done now for three years in a row. Bill took a model for a penis-shaped dildo, with balls on the back end, and scaled it so it would be close to the size of our dicks. Since we'd been growing pretty quick as teenagers, the first three dildos he'd printed when we were fourteen weren't doing it anymore. Bill changed the job so it would now print two dildos, one for Monty and one for Ann.
I heard about this later; I was outside with the girls. Bill showed Monty the kind of lube he needed to get from the drug store, the ear syringes that himself and Ann needed to use to prepare for anal sex, and made sure that Monty was wise about condoms.
Ann was clearly feeling better and was opening up, maybe for the first time because she'd gone from frightened into chatterbox in less than ten minutes. Betty made sure that Ann was on the pill, talked to her about the Safe Space at school, the Advocacy Center, and told her about Pride and the dildo harness that Betty had. That made Ann blush.
Soon Bill and Monty came back out of the house.
Bill's parents came home and said hi. They were surprised to see five barefoot teenagers by the pool so late. Bill introduced Ann and Monty. Betty and I had usually gone home for supper this late in the day. Ann quietly asked Betty if she'd loose Monty if she found a girlfriend. Betty responded by asking if Ann would keep Monty if he found a boyfriend. I still don't know what that was supposed to mean.
Bill and Monty asked Ann to make some notes because Monty wasn't sure he could remember everything Bill had told him. Ear Syringe, Personal Lubricant and condoms, for both Monty and Ann.
We agreed to meet the next day after school. Bill said that the dildos would be done by then, and all of us went to our homes for supper.