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First Time Stories

Experiencing a sexual encounter for the first time is a rememberable occurrence for everyone. A first time experience doesn't necessarily just stop at losing your virginity during your teenage years, it can also include unlocking a new sexuality, exploring a new interest, or adapting a change in lifestyle like swinging.

Have you ever been curious about being bisexual, gay, or want to feel what it's like to be a crossdresser? Have you ever thought about breaking the sexual normalities and considered sex toys, adding an extra partner to play with in the bedroom, or getting involved in a gang bang? An introduction into a new lifestyle like swinging can fulfil longstanding desires and liberate a relationship.

Share your first time experiences with the rest of the erotic story community by writing your encounter below.

Anonymous

Double trouble

First double penetration

This is 100% true, 100% first time, 100% awkward and 100% worth doing again!!! We decided to take a dirty weekend away together and decided to go to Port Elizabeth as we had been chatting to this guy from SH who lived there and wanted to meet and greet. W...

Score 24 24
2
2.3k Views 2.3k
688 words 688 words

Cherry picking

Watching another’s initiation

It was Nina whom C was expecting. They had shared pleasures before, well, to tell the truth, all three of us had, because she did swing both ways. A lovely, willowy girl, with a tiny waist, small breasts, and large dark nipples that formed themselves into...

Unlike some couples they were not fazed by each others sexual histories. Both of them had loads of experience before they came together however little did they realise how much more was out there waiting to be explored... It was a clandestine meeting as t...

Score 14 14
2
1.4k Views 1.4k
877 words 877 words
Anonymous

My friend en my vrou "Eerste keer"

Ek wou nog altyd sien hoe my vrou my vriend naai

Ons het 'n wonderlike sex lewe en kyk videos en ek hou da van om te sien as sy dildo ry en maak of sy iemand naai.Wel so begin ek met ha praat en vra of sy dit sal like om my vriend te naai en ek kyk en vat video.Eers was dit nee is jy mal...maar na so pa...

Score 32 32
4
2.6k Views 2.6k
525 words 525 words
Anonymous

In the beginning

Awakening Part 1

There was a time not so long ago that I was a completely different person... They say people can't or don't change... People can change, if they really want to. I am proof of that. 2021 I was unawakened... I did what I had to do... Because society expecte...

" Tricked..."

Fear....Horror...What was to follow...

It was Friday the the thirteenth, and into the agency I walked, and Annie called me over...Staring into her eyes into dark brown eyes, and her staring back into mine, and a slip of paper in her left hand and pulling me over towards herself where she was s...

Score 4 4
1
859 Views 859
2.7k words 2.7k words

At last.

Just a thought

Just some of my writing....M4F . I had spent the day at the beach and got a little too much sun, I really needed some Aloe Vera so I left my room wearing just my boxer shorts and knocked on her door. She opened it wearing just white cotton panties and a w...

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VirtualAqua

My first time! My first Encounter and playdate !

I fucked him in the passenger seat of my car in a parking lot at Tygervalley.

My first encounter. This was definitely a sexual fantasy of mine. Having sex in a car, more specifically on the passenger's seat. Woman on top of the man. It's been something I've played out in my mind several times, something that I'd masturbated to, tha...

We both had, very little time for having fun, because of our work commitments, as we both work for ourselves, her in the advertising industry, and me having my own liquor store...So, work, work it has been for the last few week, which had Easter in betwee...

Score 10 10
0
685 Views 685
948 words 948 words

Unexpected

Timeless

Had a half a day leave today. Had to tackle something family related. Anyways, got that sorted, and decided to go for a drink at a regular spot nearby. While there, bought a bottle of pickled onions. I have now and then, but my wife loves them. Couple of...

So a few years ago my cousin and his bf took my wife and I out to a gay club at first we wasn't sure what to expect or if we're going to enjoy it but we went with flow,my gosh one of the most safest and chilled vibe. Everyone is friendly and kind as well...

Score 22 22
3
1.7k Views 1.7k
282 words 282 words

" ToyBoy Weekend... "

You In The Army Now...

This was an incident which took place, while I was doing my National Service... As the saying goes there is always a first time for everything...Yes getting drafted in the Army, and thousands of kilometers from home... That was not fun...There we were cag...

Score 8 8
2
1.2k Views 1.2k
3.5k words 3.5k words

'' The Only Male In A Woman's World..."

Working in a company with only women...

My first place of employment, straight out of varsity, with my masters degree in film and media production... The name of the company said it all...I should of known after reading the brief that was sent to me... But just wanted to get into the job market...

Score 12 12
1
884 Views 884
2.7k words 2.7k words

The Teacher

College girl & New Teacher in town

It was early December when I came home from College. UCT first year felt more of a transitional period for me, making new friends, adjusting to living with a roommate, learning my way around the school and getting to classes on time. The subjects weren’t...