I guess if you've had sex, then you've had a first time. I think I can match almost anyone's first time with my own and come out quite a bit ahead. My first time was with my sister, Gloria. No, my first time wasn't my sister but one of her friends, Heather.
So, why did I mention my sister? Well, I was with her at the time. I guess I'd better explain.
My sis was eighteen, two years older than I was, she was a senior in high school and belonged to a pack of girls who were all gorgeous and, when they were all in bikinis at our pool, well, it was hard-on time for me, for sure.
Anyway, Gloria got in a pile of trouble a few months before this happened when she wrecked one of the family cars when she had a load of her friends in the car and they were flirting with a carful of boys and she wasn't looking where she was going. The telephone pole won. Pretty hard to blame the pole.
As might be expected, Dad, angry as can be, laid down the law to her. No more accidents unless it was clearly judged by the police to be caused by the other driver. Or, she lost her driving privileges forever. So, after a month of grounding, she got her driving privileges back.
She went back to driving her friends around as she was just about the only one who had access to wheels on a regular basis. She drove me around, too, she was always willing and, I think, tried to be a good sister, at least most of the time.
Then, one summer afternoon, she came home and ran up to her room bawling, crying her eyes out. I got up off my bed and peeked into her room. She was face down, sobbing like crazy.
"My life is over, oh, god, I'm dead."
I stepped into her room and went to the bed and sat next to her.
"I wrecked the car, oh, shit, I really did. Dad'll kill me."
"Well, don't worry about it, I'll take care of it for you," and I went down to the garage and looked. Yep, front fender caved in pretty nicely.
I was waiting in the kitchen when my father came in from the garage. Oh, he was pissed and was looking for Gloria. I stopped him and told him that I had taken my sister's set of car keys and went for a ride and crunched the fender, it wasn't her.
You can imagine what happened to me. Grounded for six months, no allowance, etc, etc.
You might also imagine how much Gloria thanked me for taking the rap for her. Yes, I got a pretty severe punishment but she would have, well, who knows, it would have been bad, really bad.
So, I started serving my six-month term and about a week later, our parents had to go out of town to a funeral of an elderly aunt that Gloria and I barely knew, so we stayed home with Gloria given strict orders that she must be in charge of me and my grounding.
She had a big sleepover for all her buddies and I didn't even know about it until I started hearing girls laughing and giggling. I walked down the hall to her room and there they were, seven, including my sister, all high school seniors, every one a looker, two redheads, four blonds of various shades and one brunette. I said hi to everyone and retreated to my room knowing they didn't want me around spoiling their fun.
I was on my computer playing games, one of my main pastimes these days, when Gloria peeked around my door and asked, "Got a minute? I want to show you something in the living room," and I followed her downstairs, turned the corner into the living room and there were the six girls who all began screaming 'surprise.'"
Naked. Sprawled all over the room, every girl was totally naked. Nude, bare-assed, starkers, if you're a Brit. Twelve absolutely beautiful breasts. Six pussies at the vee of every girl's outstretched legs. I really do believe my heart stopped for a second.
"Thank you, Davey, for taking the blame for the accident. We're here to pay you back," one of them said, Robin, a pretty, petite blond, as I remember. I think it was her, I was kind of in shock, you know.
I really couldn't speak, I just gawked. There's nothing to prepare you for something like this, it was just overwhelming. Every girl was beautiful. Every one had perfect breasts. Every pussy was shaved perfectly bare. My eyes just went from one to the next.
"Okay, girls, let's get Davey's clothes off, he's in for the best thank-you of all time," my sister said and the girls all got up and crowded around me as I was quickly stripped. Hands were everywhere on me, these girls were not bashful or shy, no, they did what they wanted. One, a redhead, it was Bonnie, she was on her knees with my dick in her mouth giving me my first blowjob as the other girls kissed me on my lips and face and neck and back, god, just everywhere, it was almost sexual overload.
My sister said, "Okay girls, one minute for each of you. The one who gets a mouthful of his cum, she's the first one he fucks. I'm pretty sure he's a virgin, so, tonight, one of you gets to be my brother's first time. Suck away. Bonnie you've got twelve more seconds. Cheryl, you're up next."
Well, if you think I lasted until the final girl was sucking me, you're crazy. It was the third girl, Heather, and I was surprised I lasted that long. The three that sucked me were masters at it. I now know that my sister and all her friends were all very experienced at sex and most had been sexually active right from the beginning of puberty.
When I cummed in Heather's mouth, I almost fainted but the noise kept me from it. The girls were cheering and yelling as Heather opened her mouth for all the girls to see the strings of my cum stretching across her mouth. They were all laughing as they stood around me, their hands everywhere on me.
"Here, Davey, you can have some back," Heather squealed and then kissed me, open-mouthed as her tongue swept my cum back into my own mouth as one girl rubbed her body on my back, another was down holding my dick and licking it like her favorite lollipop. And, there were hands and lips all over me as well.
"Look, he's still hard, okay, Heather, he's your's, remember, he's a virgin and you are his first fuck, treat him good, he's my brother, the hero," urged my sister, the only one still clothed in the room.
"Hey, Glo, when do you get naked? Let your little brother see what you've got, girl. You see his equipment, show him yours, come on." With that, my sister started taking her clothes off.
Now, I can't honestly tell you that I'd never dreamed about how my sister might look naked. Sure I have.
And, as I was being pulled down to the floor by Heather, I saw her for the first time. At the time, I never dreamed that I would see her naked many times after that but that's later on in the story of that weekend.
Now on the floor, Heather straddled me as one of her friends took hold of my dick and held it steady as she lowered herself onto me as the others 'oohed' and 'aahed' their approval.
"Fuck him good, Heather, he's our hero and it's his first pussy, make him enjoy it," one of the girls urged on.
She began rocking up and down on me as my hands were drawn to her breasts, oh, yes, heaven. Then, the other girls all knelt around and were rubbing and massaging me all over as they took turns kissing me.
Then a girl on each side squatted down and took each of my hands and put it palm up on the rug, raised up my middle finger and lowered down for me to finger-fuck them both as Heather gave me my introductory fuck.
Another girl, Dawn, bent over me and dropped one of her generous breasts right down, her nipple touching my lips as I eagerly took it in and sucked. Never, never, had I dared dream of such a sex feast as this. Every minute it went on, the girls were getting more and more into it, getting turned-on themselves.
"Hurry, Heather, I want to fuck him next," said Bonnie, a petite and very curvy redheaded friend of my sister that I had jacked-off dreaming of many, many times in the past. Now she wants to fuck me. Oh, heaven.
I began to moan as the intense pleasure radiated out across my body from my cock deep inside Heather. My muscles tensed, my hips arched up and I felt the pulsing spurts of my cum drenching her insides.
The girls were cheering.
"Look, he's cumming, my little brother's cumming," my sister gushed.
"Oh, look, he's not a virgin, now, he just filled Heather with his cum," yelled Bonnie.
Heather got up off me, knelt down beside me and kissed me, "I'll always remember this, Davey, I was your first fuck."
I looked at her and said, "I can't wait to do it again, Heather," and got another kiss and a promise, too.
Bonnie now knelt next to me, bent over and began sucking me as the others just kept rubbing me, kissing me, licking me, even my feet, sucking on my nipples, oh, I was just eaten up by all these girls.
"Mmm, nice and hard, you want on top or me on top?" she asked.
"Let me do it this time. I think I'm going to need some practice doing it myself," and the girls all laughed.
So, Bonnie laid down and spread her legs as I decided to try out oral sex on a girl to see what it was like. After all, her pussy was right there and, yes, it looked delicious.
I bent down and kissed her right in the middle of her slit, she knew immediately what I was going to so and she reached down and opened her pussy lips for my tongue to probe up into her.
"Mmm, oh, Davey, you're making me feel really good, you're learning fast," she moaned as I licked and tongued her.
"Oh, your little brother's a pussy-eater, Gloria, I'll let him eat mine anytime he wants."
I tried to see who said that but it was one of the girls behind me. Oh, well, I'll find out sooner or later, I'm sure. There was a hand up under me stroking my cock which was pointing down as I ate out Bonnie. There were also kisses and licks given to me on my back. What a payback.
"Mmm, ooh, mmm, oh, man, you better fuck me before I go crazy, get up here," Bonnie moaned and pulled me up between her legs.
I got the end of my dick right where I'd been licking her and started to push inside. I went right in and began going back and forth. Oh, was this good. And there were four more girls. This was going to be a hell of a weekend.
My hands were massaging her generous boobs as girls huddled around, kissing and licking my back, leaning over me and french-kissing me, their hands everywhere on me, they just never let me alone.
Bonnie was moving around under me, really adding to what I was doing and, yes, it was feeling really close again. She seemed really into it, too, and began to moan and move about more.
"Mmm, oh, yes, that's so good, mmm, oh, oh, UUH, UUH, uh, um, um, mmm, mmm," and Bonnie pulled me down and covered my face with kisses as I arched into her, delivering my cum deep, deep inside her. I dropped over her, almost dizzy with happiness, supremely fucked and pleasured more than I ever even thought possible.
As I lay there over Bonnie, my cock still inside her, the other girls kissed and licked on me, their soft hands just everywhere over me, never leaving me for a second, just keeping me completely stimulated like I'd never imagined possible. It was truly heaven.
Bonnie and I kissed for a few more minutes, then I rolled off her and immediately, Cheryl was over me sucking my dick. Her pussy was beautifully framed between her thighs, a glint of moisture as I got up on an elbow and kissed it and swept my tongue up along the groove.
She swung a leg up over me and dropped down, mashing my face with her wet pussy, then scrubbing it all around on me. I had the middle finger of each hand in a pussy, no idea who's, and before long, Cheryl began to moan and rub harder as she trembled and shook through a strong orgasm.
Cheryl got up and stood over me squatting down as she held my cock and pressed me up into her, then began rocking back and forth. I was in a position to see the rest of the room and my sister was sitting in a chair, her legs over the arms, fingering herself in and out as fast as she could.
The other girls, five of them, were all crowded around me, their tongues licking me and their lips kissing me as I began to hear a level of excitement, heavy breathing, little whimpers as the girls got more and more excited, surely doing something that was breaking all their sexual boundaries by far. You could cut the feeling of sex with a knife.