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First Time Sex Stories

By Evie

February 16, 2021

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First Time Sex Stories

There's a first time for everything and nothing's quite as exciting as when you try something for the first time.

What I've collected here are my recollections of the first time I tried something related to sex or sometimes just the sexual differences between males and females.

In no particular order, here they are:

Watching a Boy Pee: #1 in First Time Sex Stories

Boy and Girl Peeing

We were having a picnic with family and friends and my little brother told our Mom he had to pee. He would've been about nine and me around twelve.

There were no public facilities so Mom told him to go off into the bushes and me to go with him to make sure he was OK.

That was fine by me as I really needed to pee as well.

Something I'd been practicing at home was peeing standing up and I was already looking forward to trying it outdoors.

As soon as Jamie and me were out of sight of the others, I told him "I'm gonna pee, too. You wanna watch?"

He nodded.

I'd learned from experience that although I could get a good stream going, it would drip down between my legs as it trailed off, so I got my shorts and panties down around my ankles and out of the way.

Leaned back, pulled my pussy up so that my piss hole was pointing straight out and let it go. What a great feeling.

Jamie was just watching so I said "C'mon, get your cock out. You're the one who needed to pee."

As I've told you elsewhere (Incest Sex Stories) I used to suck my little brother's cock when he was five and it used to get hard, so I realized that he had an erection as soon as he got it out. I figured it must have been from watching me.

Because of his erection, my brother was having some difficulty pissing so I said "maybe I can help".

I pulled his shorts all the way off, got around behind him, pressed my still wet slit into his backside, leant him back and took hold of his cock.

"OK, now just let it go," I said.

It must have worked, because I felt his dick get warm and then a stream of piss came out, at least three times the distance I'd managed.

I swished his cock like a fire hose. Best fun I'd had all day.

We got dressed and rejoined the picnic. Jamie's eyes were a bit glazed.

My First Blow Job: #2 in First Time Sex Stories

My First Blowjob

As my first cock suck took place when I was eight and it was my little brother's cock, I decided to title this first time sex story as My First Blow Job, by which I mean the first time I made a guy cum by sucking on his cock. And yes, I swallowed it down, every last drop.

I wasn't mad keen on the taste, but I've always liked salty stuff and I soon acquired a taste for it. Now I just love it.

[You can get a supplement for your guy to take that will make his semen sweeter. It's really good if you don't like the taste but you know how much he appreciates it when you swallow all his cum. Especially if you say "yum" after it. The sweetening supplement is called SemEnhance and you can get it HERE.]

I was fifteen when I gave my first blow job. It was to a friend of my cousin Mike, who was now 19 and studying at University. I was still at school.

I was hanging out at Mike's place with him and his friend Jason, just listening to records and chatting away. Mike's parents, my aunt and uncle, were out for the afternoon. I'd played sex games of the 'you show me yours and I'll show you mine' variety (OK, maybe a bit more than that) with Mike when he was 12 and I was 8, but we hadn't seen each other all that much since we got older. I rather fancied Jason.

"Look at Evie, Jase," said Mike, "Looks sweet and innocent, doesn't she?"

Jason agreed that I did indeed look sweet and innocent. "Never been kissed," he said.

Well, I certainly had been.

First of all by Mike himself in our early exploratory forays.

Then when I was 11 by Uncle Frank, who really taught me how to kiss properly. Not to mention fuck.

And more recently by two of the boys (and one of the girls) at school.

Then Jason followed up with "Do you guys want to play Truth or Dare?"

Turned out we did and turned out I was to go first.

Evie: Truth.

Mike: How often do you masturbate?

You need to understand that this was not a word to be thrown around in those days and, in fact, I wouldn't have known what it meant except that this year at school, we'd got our first unexpurgated dictionary and, in the way of schoolkids everywhere, immediately looked up all the forbidden words.

Not knowing the word, of course, didn't stop me from doing it. I'd been touching my pussy for as long as I could remember, had discovered my clit while playing with Mike when I was 8 and had been inserting things from around 12. My current favorite was a cold zucchini straight out of the fridge.

Evie: Usually twice a day.

The boys looked surprised. Very surprised.

Jason: Dare.

Mike: I dare you to kiss Evie.

Hmm... Didn't I get any say in that? It was something I wanted anyway, so I let it go.

Jason approached me a bit tentatively, put his arms around me and pressed his lips against mine then started to pull away.

I wasn't about to let that happen. I grabbed his head, pulled it tightly against mine, opened both our mouths and stuck my tongue halfway down his throat.

Fortunately, he responded immediately and we spent the next couple of minutes exploring each other's mouths, tongues and teeth.

Before pushing him away, I ran a hand lightly across the front of his shorts. There was no mistaking the erection there.

"Never been kissed, hey?" I said, grinning at him.

Mike: Dare.

Evie: I dare you to show us your cock.

Jason looked shocked, but I was pretty excited by now and wanted to move this along. Jason didn't know (or at least I assumed he didn't) that I had seen Mike's cock plenty of times when we were younger, so it wasn't such a shocking dare after all. Just unexpected.

Mike was totally cool about it. Stood up, dropped his shorts, then pulled his jocks down to expose his half-erect penis. A lot bigger than I remembered. I expected Mike to get dressed quickly, but he just stood there giving us all a good look.

I think we'd come to an unspoken agreement that there was to be no more Truth. Just increasingly challenging Dares until someone went too far.

So my voice was a bit trembly as I said.

Evie: Dare.

Mike (still with his Dick exposed and getting more erect by the second): I dare you to suck Jason's cock.

We all went very still. We knew this was the moment of truth.

"OK," I said.

Jason unzipped his fly and dropped his shorts. I got down on my knees in front of him and pulled his jocks down, confirming that I was right about his erection.

I didn't touch his cock with my hands, just grabbed his butt cheeks and slid my mouth onto his cock. I could feel the head of his cock touch the back of my throat and, fighting the gag reflex, swallowed it. This allowed me to take his entire shaft into my mouth and throat.

Jason's eyes were wide.

I decided to dispense with subtlety and started to move my mouth rapidly up and down his cock, swallowing the whole thing every ten strokes or so. I was enjoying this and, judging by his hip thrusts in time with my movements, so was Jason. Out of the corner of my eye, I could see that Mike was fully erect now and masturbating furiously.

It wasn't long before Jason was breathing heavily and then saying "Fuck, Evie I'm gonna cum. Is that OK?"

By way of answer, I grabbed his buttocks tight and pulled him hard towards me while I kept pumping my mouth on his cock.

When Jason started cumming, it was like a hose being turned on in my throat. I swallowed, kept swallowing and swallowed some more. My cheeks filled up with the excess but then I swallowed that too. My aim was to not spill a drop.

The taste was salty, but I've always like savory stuff, so that was fine.

I was aware that Mike had spurted at the same time.

We all just looked at each other, waiting for someone to speak first.

So I said "We better get all this cleaned up before Aunty Lil and Uncle Max get home."

The air smelled of sex. You can read a lot more at Taboo Sex Stories.

Insertion Sex: #3 in First Time Sex Stories

This is a difficult one for me, as I haven't been entirely truthful in my Teachers Pet autobiography.

In Chapter 16 Uncle Frank, I described how my much-loved uncle introduced my 11 year old body, with all its raging hormones, to adult sex.

I described how our first playtime ended, with me on my elbows and knees, feeling very sexy and Uncle Frank kneeling behind me, holding his erect penis and drinking in the sight of my smooth pussy and ass.

I also said that was it. Nothing else happened.

That was true enough for that first session. But we had another. I didn't include it in my autobiography because Uncle Frank was still alive and I was terrified of getting him into serious trouble for something that we both enjoyed immensely.

My beautiful uncle has since passed away, so for the first time, I'm going to tell what happened the next day...

My First Real Fuck

Uncle Frank was reluctant, but I pestered him so much the next day for us to do it all again that he eventually gave in.

I couldn't wait to get all my clothes off and for him to do the same. I touched his cock, stroked it, put the head in my mouth and sucked on it.

"Will you look at me like you did last night, Uncle Frank?". My voice was thick and husky and my smooth, 11 year old cunt was totally wet.

I got back onto my elbows and knees and pointed my pussy and asshole at my uncle.

I even got my hands between my legs and opened my little cunt lips so that he could see more of me.

I could hear my uncle breathing hard. Then he said "How would you like to feel my cock pressed up against your pussy?"

All I said was "yes."

Uncle Frank approached me on his knees. Then I felt the end of his cock touch my open lips. I instinctively moved back so that he was now a little bit inside me. I thought it was the best feeling I'd ever had.

"Is that OK, Evie? It's not hurting you?" He sounded worried. But then "I can push it in a bit further if you like."

"Yes please. Do it." I was so wet that all I was feeling was pleasure.

Until suddenly there was pain. Not a lot, but Uncle Frank's cock was definitely pushing against some resistance. I'd had enough sex education to realize that it was my hymen and that we could stop now and I would technically remain a virgin.

I didn't want to remain a virgin.

It was my decision. Totally my decision. Before I could lose my nerve, I thrust backwards. Hard.

And felt my uncle's cock burst through. The pain was sharp, but short-lived. More than made up for by feeling a cock all the way inside my vagina. It felt warm. Probably had some blood on it.

I was feeling exultant. Bold, liberated, womanly.

"Fuck me, Uncle Frank," my new bold, liberated, womanly personality demanded.

And he did.

I hadn't had a period yet (though I did shortly after, on my 12th birthday) so my gorgeous uncle, my first real fuck came inside me.

Lesbian Sex: #4 in First Time Sex Stories

I've covered this elsewhere. It was with Carole, my beautiful Jamaican born roomie at Teachers Training College. You can read all about it at Lesbian Sex Stories.

My First Anal: #5 in First Time Sex Stories


I'd Been Told I Had a Nice Ass

By the time I was 21, I'd had a lot of sex. For those days anyway. Sucking my brother's cock at 8, fucking my Uncle Frank at 11, playing sex games with my cousin Mike, giving a blow job to his friend Jason, having lesbian sex with my roomie Carole.

And lots more.

But I'd never had a bum fuck. Or "anal sex" as they called it in the magazines. Some magazines anyway. Most people pretended there was no such thing. Which is weird, because people have been doing it forever and for many cultures was one of the few reliable forms of contraception available. Anyway, as I said, I'd never had one.

Unbeknown to me that was about to change.

Carole and I were treating ourselves to one of our occasional nights out. As impecunious teacher trainees, we couldn't afford much and sharing a bottle of wine over a pub meal was about as luxurious as we ever got.

So that's what we were doing, while checking out the local talent. Carole was gay, and I'd just discovered I was bi. There was good-looking guy sitting at the bar drinking Scotch and chatting quietly with the pretty little blonde barmaid like they were old friends. Maybe they were.

He was beautifully dressed in designer jeans and an expensive looking jacket, the sleeve of which didn't quite cover an upmarket watch (which I discovered later was a Rolex Submariner with the blue face). Carole noticed me looking at him.

"You can't fancy him," she exclaimed. "He's old. The barmaid's cute, though."

"He's around 40. That's not old."

"Twenty years older than you. He could be your Daddy."

Mmm... I decided to hang onto that thought. To be honest, after the young geeks at school, I was ready for a bit of sophistication.

He noticed me looking at him and smiled. He smiled back, said a few words to the barmaid and sauntered over to our table.

"Mind if I join you ladies?" he asked politely.

"Of course not," I said, trying to look sophisticated, "but won't your girlfriend object?"

"Not at all. She's an old acquaintance. I'm a friend of her Dad. Known her since she was a baby. Anyway, she's not really into men, if you know what I mean."

I looked across at Carole. "Your cue, I think."

My First Butt Fuck

To cut a long story short, I ended up at Colin's place with both of us naked in front of a roaring fire.

Emma still lived with her parents, so Carole took her back to our flat. We didn't have a fireplace, but the naked part was the same. Carole told me all about it later and how she'd got to use the double dildo she'd been given as a gift just a couple of days ago.

Colin was an incredibly skilled lover and had already made me cum three times just with his mouth.

He loved me calling him "Daddy".

He had a beautiful penis. I considered myself quite the connoisseur by now, and in my expert opinion, one of the finest I'd seen. Not huge, but proportional, very clean lines and, most important hard as the proverbial rock.

I was on top of him, and about to impale myself. Which I did. Sank down until it was all in. We were both smooth shaven, so very skin on skin.

Colin was grasping my buttocks with both hands. Then I felt one hand move and a finger touch the entrance to my butt-hole. There are a lot of pleasurable nerve endings there and I shivered with both pleasure and anticipation.

"Do you like that?" he whispered. I nodded. Said something like "mmm...".

Colin put his finger in his mouth and sucked on it. Gave it to me to suck on as well.

Then returned to my butt-hole, rubbed all around it with his now wet finger and started to slide it in. A strange but enjoyable sensation. I did the sharp intake of breath thing.

"Have you ever done anal, Eve?" Colin asked. I shook my head.

"Do you want to give it a go?" Yes I did. A first time for everything.

"Preparation is the key." Colin slid out of me and told me to get down on my elbows and knees, doggy style.

He disappeared into the bathroom for maybe half a minute and when he returned he was holding a blue plastic syringe and squatted down in front of me to show it to me. His cock was still hard and erect so, not being one to waste an opportunity, I started sucking it.

He sort of rolled his eyes but explained that the syringe was designed to deliver a load of lube directly into my ass to make it as slippery as my cunt. They were exactly the words he used. I always find talking dirty a huge turn-on. Not for everyone I understand.

Any way, Colin somewhat reluctantly removed his dick from my mouth, rubbing the outside of the syringe with his hand so that it was not just loaded with lube but slippery itself.

He moved around behind me. "Spread your ass cheeks," he commanded, "You're going to love this."

And I did. I used both hands to spread my cheeks for Daddy and he pressed the tip of the syringe against my hole, then slid it all the way in. It was about 7 inches long and he depressed the plunger as he withdrew it. I could feel the lube coating my anal passage and it felt wonderful.

Along with the syringe, he'd also brought out three butt plugs of different sizes and now inserted the smallest. It slipped in fairly easily and Colin/Daddy worked it in and out a few times before replacing it with the next size up. It was an interesting sensation. Not orgasmic but certainly enjoyable. Sort of naughty too. It brought back a memory of how I'd let my cousin Mike press his cock up against my eight year old bum hole and how naughty we felt doing it.

Now Daddy was inserting the biggest butt plug. There was a moment's discomfort, then my ass seemed to suck the whole thing in. It felt pretty good.

"Ready for the real thing?"

"Yes, do it," I said, spreading my cheeks as much as I could.

Daddy pulled the big butt plug out and before my sphincter could close, pushed his cock hard into it.

Now, that did hurt, but the pain was definitely mixed with pleasure. He kept pushing and pushing, until I felt totally filled up.

"Oh. My. God. Daddy's got his cock in my ass," I cried out. "Fuck me in the ass, Daddy. Please do it. Now."

He thrust in and out. "God, Eve baby, you're so tight. I'm going to cum any second."

I could feel him squirting inside my ass as, with a final thrust, he finished and was still.

I was an anal virgin no longer.

I think I'd better stop here.

I've still got more first time sex stories to tell you, so I'll probably continue in the next post.

See also:

Incest Sex Stories

Threesome Sex Stories

Group Sex Stories

About the author

I was the Head of English at a prestigious private school in a capital city in Australia. I have been a teacher all my working life but took an early retirement at fifty. I have one son and two daughters. My son and one of my daughters are happily married and my younger daughter is in a stable relationship with her girlfriend following several temporary ones over the past few years. I have grandchildren.

My children think I am boring. I think my students admired me, perhaps some of them even loved me. They thought I was unadventurous.

My fellow teachers thought I was safe, dependable and conservative. Possibly sexless.

I am none of these things. I have done so much that my children, my students and my co-workers could not possibly imagine me capable of. I look at my children and think what safe, boring lives you have had. I cannot tell them what their mother has done with her life, but I don’t want to die with no record of it, as if it had never happened.

Sometimes I think I’m like that old lady in Titanic. You know, the one who turns out to have been Kate Winslett when she was young.

This is my story.

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