Betty, Bill and Richard 34 (The First Touch of Ann and Monty) 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 day in late April, Monty and his girl Ann had come to us to talk at lunch. That was too public for the topic, so Bill had brought them to his house after school that day.
We found out that they'd been having sex but they had a couple of problems. First, Monty was using his fingers on Ann to get her wet but she had probably never had an orgasm. She didn't even know what to ask for and was probably blaming herself because she wasn't really enjoying sex.
Second, Monty was interested in trying sex with a guy. We slowly got him to admit that he wanted to try pretty much everything that guys can do with each other. Monty knew that we were bi as well as sexually active, and he seemed to be jealous of what we were experiencing.
Third, and this was harder to get out, Ann wanted to try lesbian sex. She was so upset when she told us that we thought that Monty or somebody else was railroading her into it, but she was only upset because she was afraid to talk about it.
Bill had talked to Monty about how to prepare for anal sex and sent him and Ann home with a drug store shopping list, having started the 3D printer to make a dildo for each of them.
This story begins the day after that.
At lunch, when Bill, Betty and I finished eating, the three of us talked about how to handle this. It appeared that our threesome would be a fivesome till about mid-June, when we would have to send them off, hopefully much happier than we had found them. I mentioned that they could meet another bi couple at Pride if they wanted to continue, but that was outisde of our plans.
We quickly agreed that we could get them to strip with us and become comfortable with each other's bodies that evening. They once made out when they first dated, but they needed to learn to keep making out, and they could probably spend more time feeling each other up. They were rushing to have sex and had forgotten what fun the simpler things were.
"Monty can learn to feel up a guy and get felt up by one, and likewise Ann with you, Betty", I said. She nodded back at me.
Bill had a couple of ideas for the rest of the time we had. I'll detail that in a bit, but he wanted to coordinate with Betty and myself beforehand.
When lunch period ended, the three of us were agreed on the plan for after school.
When the time came, we didn't see them outside the school, but trusted that Bill's place was easy enough to find.
When we got to Bill's, there was a red Volkswagen Golf out front, and Monty and Ann got out of it. They looked nervous again, but at least now they looked happy.
Bill let is in through the front, and we dropped backpacks, shoes and socks inside the front door, and continued out back.
Betty had her shirt and bra off before we could say anything to our guests. We told them that we hang out naked, but Betty with her boobs out was something they weren't prepared for. Bill quietly spoke, "We kinda got used to this, and we're not used to having guests." Bill then got a bit louder, addressing Ann. "Us three guys were on swim team, so we know what Monty looks like. I'll bet you're beautiful under all that. Please join us!" That was Bill's idea of being diplomatic. It wasn't perfect but I wouldn't have known what to say. I had my shirt off and was taking off my pants and underwear.
Ann looked at Betty, then saw what I was doing, saw Monty take his shirt off, and finally took off her shirt. She paused again, saw that Betty and I were naked, Bill's shirt was off and he was pulling down his pants, and Monty now was taking his pants off. Now Ann took off her bra, stopped to make sure we weren't making fun of her, and finally took off her pants and underwear so that all five of us were naked.
Bill went to Monty and put his hand on Monty's shoulder and quietly spoke instructions into his ear. This took about a minute, which of course caused the rest of us to try and eavesdrop. Monty nodded and went to Ann. He touched her shoulder and stopped so that they were at arm's length, facing each other. He gave a long look at her face, let himself look at her boobs and legs. He was smiling. She was still stone-faced and looked frightened. Monty winked, then blew her a kiss, and she finally smiled.
"Stand still for a minute", Monty told Ann, and he slowly walked in a circle around her, stopping to give a good long look at her profile, and again to look at her back, her shoulders and her hair. When Monty was back in front of her he reached out and ran his fingers through her hair, touched her chin and opened his mouth to start kissing her.
Bill said, Betty and Richard, come let them have some room. Betty and I joined Bill and the three of us began our makeout session, feeling each other up, while Monty and Anne learned to make out and caress each other's bodies properly.
I don't know how long an "Ann and Monty" makeout session should last, but as for Betty, Bill and I, ours seemed longer and more purposeful than normal.
When we broke apart and Bill gently seperated Ann and Monty, all three of us guys were half erect and both girls were sporting aroused nipples. Ann and Monty were self concious, but Bill, Betty and I knew that this was the point of a good makeout session. "Whatever fancy things you learn about sex and being lovers", Bill told them both, "never forget how to make out and caress each other".
Bill then boldly kissed both of them on the lips, and said, "Now, Ann, Betty is abducting you and Richard and I are taking Monty."
Bill and I led Monty by the hand to the big workout mat at one end of the shade. Betty had unrolled two yoga mats at the opposite end.
Bill told Monty to lay down in the middle of the workout mat and gave him a pillow for his head. Bill layed on his side on one side of Monty and I was on the other. Bill kissed Monty full on the lips with no warning. Monty tensed up like he'd had an electric shock, then forced himself to accept it. Eventually Bill opened his mouth and then Monty got the idea. Soon Monty was making out with a guy for the first time.
I glanced at Betty and Ann; the noise Monty had made had caught their attention, but now Betty was making out with Ann.
Bill pulled away from Monty, and then watched as Monty made himself relax enough to smile. Bill was "driving", and I was paying attention. We used some very similar teamwork to bring Betty off many times in the past.
Bill kissed Monty on the right temple, and then I did the same on the left.
"Monty, close your eyes", Bill said softly. Monty complied.
Bill kissed Monty on his right closed eye, and again I took care of the left.
Bill and I each put a hand on Monty's pecs and held them there.
We worked our kisses to Monty's ears and his shoulders.
Bill let go of Monty's right pec and put a wet sloppy kiss there, which made Monty gasp. Bill ignored this and then started nibbling on Monty's nipple with his lips. When Bill backed off, I kissed Monty full on the mouth, opening mine and working Monty into a good sloppy French kiss, satisfied that now Monty had made out with two guys.
Now I took my turn on Monty's left pec and nibbled his nipple, the same as Bill had, then I sat back for cues from Bill.
The kissing was over for today. Up to this point we would've done the same thing if our subject had been scheduled for either manual or oral happiness. This was our first time on Monty, and the first time that Bill and I had teamed up on any guy, so oral would wait till another day.
Bill started stroking Monty's right butt cheek, and I followed along on the left.
We continued slowly down Monty's thigh to his knee and then outside his calf. Bill stroked from Monty's ankle and just held his foot, while I followed along on the left. We only held his feet because we didn't want to tickle him.
I noticed that Monty was completely erect now, and not self-concious at all.
A glance at the girls told me that Betty was just moving off of Ann's breasts and stroking the girl's ass cheeks.
On the ride back up Monty's body, Bill skipped the inside of the ankles and shins, so we were gently stroking the inside of Monty's thighs. Bill moved up so that he was sitting on his knees looking at Monty's dick, and I moved up to the same spot on the opposite side. Bill and I each put one hand on Monty's pec's again. Bill finally grabbed Monty's penis, while I cupped his balls. Monty let out a sigh.
Bill let go of Monty's right pec for a second, leaned over and kissed Monty's lips first, then his left nipple, then took Monty's dick in his mouth for a second, causing another noise to come out of Monty. The mouth on the penis thing wasn't in the plan but I dind't fault Bill for it. Bill then put his hand back on Monty's pec.
At last Bill tightened his grip on Monty's dick and started slowly stroking. Monty groaned at first and then got comfortable to enjoy the attention. I loosed my grip on Monty's balls, and moved my hand around, stroking Monty's inner thighs and balls, then gently cupping his balls, gently squeezing. I also played around with Monty's pecs and nipples, now that Bill didn't have a hand free for that. I was still just the accompaniast; Bill was the main act.
I had brought myself or Bill off many times over the years, so I knew how to read Monty's state of being pretty well. Monty had less than two minutes left in him, from my experience.
I reminded myself that this was his first time with a guy, and it occured to me that only the day before he had first approached us. He was trusting us a lot to let us do this.
I moved myself up and kissed Monty on the lips, then I kissed Bill, and put my hands back to work on his pecs and his balls.
Now I felt his balls tighten up. "Now", I quietly muttered to Bill. Bill just nodded as Monty gasped and then came all over his chest.
While Monty got his breathing under control, we noticed squeals and other noises coming from the girls. All three of us guys stood up to get a view.
Ann was on her back rolling her head back and forth with her eyes closed, moaning like she was having a nightmare. Betty was on her knees to one side of Ann. One of Betty's hands was pinching Ann's far nipple. Betty's other hand was furiously working Ann's pussy, and Betty's lips were clamped down on Ann's closest nipple.
"I've never seen her like this!", Monty said quietly.
"Basicly, what you want to do is treat Ann the way that Bill and I treated you today", I quietly suggested.
Bill and I shared big wet kisses with Monty and each other before helping him clean up in the outdoor shower. Once Bill and Monty were dry, they put on some clothes and took a towel into the house. I wasn't then clear on what the towel was for.
After they went inside, Betty helped Ann stand up. Ann looked at me and looked self concious again. "We're naked together all the time, and you're beautiful. Let's get you clean and dry, and you can get dressed", she smiled at me, weak though that line was.
Betty helped her under the shower, and Ann got brave enough to feel Betty's breasts and ass while they were showering in front of me, so maybe Ann was coming to grips with nudity.
I was offering towels once they'd rinsed off, and Bill and Monty came out of the house with something wrapped in the towel. I gave Bill a puzzled look. "Two dildos, as promised", Bill told me.
The girls got dressed and all five of us went into the house. Betty and I were putting on shoes and socks while Bill helped Ann and Monty load one dildo each into their backpacks. "If you want to hide these from your parents, go for winter sweaters. You'll have all summer to come up with another hiding place", Bill offered.
Their backpacks taken care of, Ann and Monty put on their shoes and socks while Bill took the towel back outside.
Monty looked at me, "We're going to the drug store for ear syringes and lube. We should both be able to clean out and try the dildos before bed tonight". "Good plan", I responded. "You don't need to be an expert by tomorrow but you should get comfortable before we try that stuff".
When Bill got back, all of us exchanged kisses.
Monty and Ann headed to their drug store while Betty and I headed for our own homes for supper.