Betty, Bill and Richard 25 (Of Harnesses and Pegs) Teen bisex M-M-F July, 2020
My name is Richard. Betty and Bill are my friends.
The summer of our fifteenth year we had done most of what we knew that three people could do with each other two weeks after school was out. The week before Pride we were just trying to rotate between handjobs, oral sex, anal and vaginal while making sure that each of us got off once a day.
On Saturday two weeks after school was out, the three of us went to Pride for the first time. Betty had brought back a harness and a book that seemed to be about gay sex positions. All three of us had listened to an old man talk about his own experiences, living through the worst of the AIDS epidemic and a warning about the importance of condoms. The three of always used condoms together and even alone with our own dildos becase it made things easier to clean up.
Sunday each of us spent with our own parents, whom we were now close to. Mom asked if I'd had a good time at Pride. I told her yes and told her a little about the old man and his stories. Mom didn't mention seeing Betty buy a harness while she was waving at me, so either she didn't notice or thought I had been emberrassed enough. I'll never know.
Monday morning, after our parents had gone off to work, I met Betty and Bill behind Bill's house. The three of us stripped, made out and felt up each other's bodies by Bill's pool.
I noticed that Bill had a fresh 12-pack of condoms, a tube of lube and a box of tissues on the workout mat already. Betty had broght an old woven bag with a flower on it, and pulled out the harness she'd bought on Saturday. She also had the book of positions, but it seemed like that would wait.
"Did you boys keep your butts ready?", Betty asked with a smile.
"I wasn't thinking about the harness, but I used my dildo last night and cleaned out this morning. I thought I was getting ready for Bill", I answered.
Bill said, "I've used my dildo every night and cleaned out every morning since school let out. I'm ready for anything."
Betty had pulled the harness out of it's bag, and produced her dildo from the flower bag. "Richard, you answered me first", she smiled. All I could do was nod, find a throw pillow, and head towards the work out mat. I was a little scared but all of our dildos were the same. I'd just never had sex where a girl or woman was entering me.
Since Bill and I had each fucked each other and Betty in the butt, we already had something of a routine. In fact getting fucked in the ass felt better than anything else to me, but I hadn't really admitted it to myself much less anyone else.
I got the pillow under my lower back and watched Betty. The dildo Bill had 3D printed last month fit the nylon harness Betty got at Pride, which was never guaranteed but it worked. Betty put the harness on her hips and strapped it on like she had practiced, which seems likely, and dropped to her knees.
Bill rolled a condom onto the dildo, got up and kissed Betty on the lips, and then lubed the tip of the dildo and the ring of my anus. This time, Bill pushed his finger in an inch, which he'd never done before, and then Bill kissed me on the lips before getting out of the way.
When we had made out earlier, Bill and I had gotten half-hard, which was usual, but we'd gone soft when Betty pulled out the harness. I was completely soft from nervousness now, but Bill was getting hard again watching me about to get pegged (we learned the word "pegged" later).
I pulled my legs over my head. Betty used her fingers to find my pucker, and like Bill she took a little time to finger my insides a bit. She finally placed the tip of the dildo and slowly started entering me. I did a quick exhale, she backed off, I looked at her face; she seemed to decide how to go about her first effort at fucking another person as a "top", and then she started the "in a little, out a little, repeat" that she'd seen Bill and I use to get all the way inside a person's ass in two minutes with minimal pain. Once I realized how she was going to get inside me I relaxed a little: Betty was a smart and determined person.
For a while it seemed like it would take forever, and then she was all the way in and it seemed that she had done it too fast. Betty stopped when I was full of the dildo and looked at my face to see how I was doing. Since this was the same size and shape of my dildo at home, I wasn't going to be overwhelmed. The angle wasn't much different than when Bill fucked me, so I was pretty comfortable. She was close to my prostate but not quite there. I nodded and smiled at Betty. "Are you getting something out of this?", I asked. Betty nodded happily, "The base is pushing against my pussy." she said, and started moving again.
When Betty started properly fucking my ass with the dildo, she copied the movements that Bill and I used when we fucked, having watched us fuck each other and having each of us fuck her pussy and ass. It wasn't very different than the rhythms we used to get her off with our hands and our mouths.
What was different was timing and style; she started slow and picked up to a pretty quick pace, then slowed down before accellerating again. She did this about four or five times, which made my dick hard and kept it that way. Bill of course was watching all of this, knowing that he'd be on the receving end of this pretty soon, and Bill's dick was hard as a rock.
My prostate started to react to this, though the dildo was barely touching it. I thought I was going to come the third time Betty's roller coaster of a pace peaked, but instead of coming I just started producing pre-come; I barely had any most of the time. Finally the moment came when Betty was going all-out, fucking hard, deep and fast, and her face told me that she was either close to orgasm or having one, and noises that weren't language were coming from her mouth.
For the second time in my life I came without touching my dick. I think tears started coming though I still don't know why. Betty dropped onto me and was shuddering a little. I felt like I had to pee but I could wait for a few minutes; I wasn't going anywhere with Betty crashed on my chest. I put a hand on her back, not knowing what to do. Betty's breathing was slowly coming under control. I looked at Bill; he was absorbing the sight before him.
After about five minutes, Betty sat up and pulled out of my ass. "Sorry.", she mumbled. Bill used one tissue to pull the condom from the dildo, and another tissue to clean the lube from my ass. He got up to take these things to the trash can. Betty rolled onto her back and lazily took of the harness and sat the harness and dildo aside.
I finally looked at her and said, "You don't have to apologize for anything. You fucked me good!". Of course she grinned at that. When Bill got back, Betty and I stood up and all three of us exchanged sloppy French kisses.
We cleaned up the sweat and lube, got dressed and went to lunch.
After lunch, Betty put the dildo harness back on and made love to Bill's ass.