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So I wasn't always a hit with the ladies in fact I tended to strike out 9 outta 10 times and when I didn't the ladies didn't wanna go as far as me, all us guys have been there. But growing up I spent a lot of time with my best mate to the point I could walk in without knocking and they did me dinners and everything... It was like a second home. So they went on holiday and couldn't take me which sucked but they said if I wanted to go round and feed the fish it was cool they even stocked up on food and gave me the unlock code for the TV it was awesome first thing I did was get the porn on sit back and and chill with chicken and titties all good till I spilt bbq sauce down me so thought fuck it chucked my stuff I'm the wash and decided to go have a play with his sisters undies, she was a few years older and pretty much the prudish goody goody if you said anything remotely rude she turned red. For a prude she had really nice undies though, bit more looking and hot damn a dinky little dildo just the thought of it being in her got me hot and hard I'd never thought of her that way before though so thought I'd jump in a cold shower and calm myself. Must of been in there a while and didn't bother closing the door cus I had music on and as I stepped into the hall I suddenly realised there was a bag on the floor that hadn't been there before, as there had been some recent break inside around the area I instantly turned into a wannabe action hero well naked wannabe action hero and then a bump in the parents closet.. I snuck in then lunged like an over excited deer missed the mystery person completely and landed on my head, not one of my best moments but at this point I was relieved to see it was my mates sister looking for something.
Ignoring the fact that I was butt naked I just said hi and smiled dick right in her face but she didn't turn red instead her jaw dropped and at this point I was wondering if I was about to get beat she looked shocked surprised and then she squeaked out a whispery hi and smiled. Her eyes kept switching between my eyes and my dick "I never seen one that big before, is that as big as it gets?" despite growing up together we'd never seen each other like that so I Sat myself up looked down and confused said no, I knew I was bigger than most but didn't know there were growers and showers (I'm apparently both). I suggested getting something on trying to be polite and she chirped up quick wait can we measure it? So I said "oh it's uh 9 and a half last time I checked but grows to almost 11 when it's up" with that she took my hand and helped me up. As I got to the door her top and bra flew past my head so I turned just in time to see her throw her leggings and little lace knickers. Dick shot up like a rocket so fast I thought it might pop and in a heart beat it was in her mouth and she was moaning like I'd only seen in porn but fuck me it felt great.
I Sat on the floor and she shakily moved round and used her pussy to push my head back to the floor, her pussy was so wet and sweet I popped in seconds filling her mouth and she swollowed it all. "how long till you can go again?" she said sounding like she was about to cry "uh about 5 maybe this is a first for me" I said and with that she disappeared and started bumping around in the bathroom before coming back with a condom and almost dragging me took me to her bed. She started playing with me and licking my dick like a lollipop and just like magic my dick was rock hard again. She slid the condom on then lowered herself on to it halfway down my length I thought she started peeing on me then realised nope she was coming hard and she started crying out loud "oh God yes" and started fuckin me slowly but gaining speed as she went after a few she fell to the side her pussy sopping wet and creamy I led there for a minute admiring her red hot body smooth slim with these amazing perky nipples on her juicy double e boobs. Then lent over her and slowly started sliding into her going as deep as I could until she buried her face and screaming into the bed said its to big its to big, I pulled back a bit and brushed back her dyed black hair revealing her eyes filled with tears. "I'm sorry should I stop?" don't you fuckin dare she said as she started pushing back onto me making it go back deep in her pussy as she got on all fours "try now" again I went deep and she started crying out it's to big again so she started doing the moving making sure I didn't get to deep. My balls started tightening as I watched her riding my cock on all fours her pussy gripping so tight it looked like my dick my get stuck then just before I was about to cum she fell fawards shaking and I thought I'd done something wrong and she was having a fit then like a fountain she came so hard it was gushing. I looked down and noticed the rubber had split and was now basically a cock ring, "it's broken I'll get another" you can't she said pulling me down and climbing on top it's the last one just don't cum in me. As she slid me back in her smooth pussy I could see her tits bounce with her heart beat grabbing her ass my finger slid straight in from how slick her cum had made her and instead of saying stop her eyes rolled and she whimpered with pleasure then started bouncing making my dick and finger go deeper. Between that her perfect tits and the way she bit her lip as she did her porn star moan I was ready to pop again "I'm gonna cum, I gotta pull out" but she just started fuckin harder then it happened and fuck me it felt great feeling my balls empty into her then she fell heavy to my side my dick covered in both our juice she started stroking it gave me a kiss with her juicy red lips and asked why haven't we done this sooner, jokingly I said well we're a bit young to be parents and the smile alone on her face turned me on so much I wish I could have gone again.
We led there for almost an hour just kissing and touching each other then as we went to the shower together, as we helped clean each other she started crying saying it was OK she was just feeling really good so we Sat on the floor with the shower still raining down on us. "can I ask you a favour" she asked, yeah of course I said can you put it in my ass just a little? Well I wasn't about to say no so I rubbed it on her pussy and got some spit on it then carefully pushed it into her tight puckered ass hole just the tip "stop" she cried just like that so there in the shower with just the tip I fucked her tight ass till she came "stop now, I'll finish you later" and with that we stopped got dried and spent the night together trying everything we could think of. The next day she called into college ill so we could have more fun and because she couldn't walk properly. We spent the day having fun and having her naked for most of it was amazing I'd Gone from zero to hero, virgin to furthest thing from it. We never let on what we'd got upto the only one who knew anything had happened was her mum cus she'd forgotten to turn of the one security camera and it caught us fuckin I the porch at the back of the garage.
That led to a rather unexpected situation with her asking about my dicks size and if she could see it then if she could touch it but that's for a different story.

Well I hope you like my story of how I lost my virginity and just so you know it is a true story and had a happy ending.
Thanks for reading
~Nate~

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09.10.2020
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Three years into our marriage, my X-Wife and I took the opportunity that presented itself to us and expanded our sexual horizons and freedoms. The years we spent together opened my eyes to the realities of a deep trusting love. Our first encounter with a new friend who we came across on a fateful friday back in the late 90's is only part One of the open journey, we continue to travel to this very day. Priscilla is the most stunning woman I've ever encountered. Her unique, amazing beauty comes...

My First Granny Encounter

This a true and to the point off my First Granny Encounter.At the age of 24, all males are ready to play,enjoy and learn from every sexual encounter they are due to experience in there lives.This a true and to the fact lifetime experience that I had encountered in my life.I was working in construction, I was living in West OZ and the work had dried up, so I thought to my self whilst I am still young and being a single male after splitting up with my fiance of 2 yrs, I decided to hit the road...

My Recent Encounter

I am a secretly bisexual married man 60 years old living in Philly. I had some previous encounters with other bi men MWM which I prefer. On the 4th of July the wife and I went down to the waterfront to see the fireworks and while there we got involved with another couple and were chatting waiting for the festivities. We had a lot in common and he was retired from the Navy and I retired from the Army. We chatted had a few glasses of wine and he and I really hit it off. We had similar...

An Unexpected Encounter

Hi guys this is Shreekanth from Bangalore, JP Nagar 6th phase. I am here to narrate my life’s 1st and most romantic experience with a girl which I didn’t expect to happen so unexpectedly. Well to know about myself, I am 24 years old, 5.8, average built body, though not a huge dick but a satisfying size for any women. This incidence took place on Diwali 1st day when my ex-colleague named Yashaswini (name changed due to her request upon privacy) came to my house for inviting me to her brother...

After Hours Encounter

This is my first attempt at publishing a story on here so please provide your feedback! Love to know what others think of my story and any constructive criticism is accepted, but please be kind! They had been flirting with each other the entire day, and really it was only a matter of time before something like this happened. He made it seem like he was just being courteous and kind so the others around wouldn’t think anything of it. It was cold, she had to walk home, and he was being a...

My first encounter

Hi friends…m a ocasionally reader of ISS,ocassional in the sense wenevr i get chance in cyber.Its simply gr8..all share their their fantasies n real encounters..i2 wishd 2tell u guys n gals abt my first encounter.Sorry if u dint liked it…This happened wen i ws studyning in diploma…It ws my xam time..i used 2sit near window of my room to study,ther was a compound wall 10yards away frm wndow.,n ther was 3houses next to the c.wall.Aftr the xam i used to do all my collge wrk sittng near wndw.In one...

Surfing a4a led to my first gay encounter

One day I was looking at gay videos on xtube and started viewing a video title a4a encounter. Curious about a4a site, I started browsing the site looking at profiles until it said I needed to setup a profile, and so I did. I quickly setup my profile, uploaded a couple pictures and continue browsing profiles. I came across a profile with pictures that peak my interested. His profile said he was 6'0" 230lbs married black male with a 7.5 inch uncut cock and he was looking for a discreet sexual...

A Brief Encounter

_______________________________________________________________________________________________ A Brief Encounter Damn! I’m out of coffee cream for the morning. I hate black coffee. If it was a desperate situation, I could always use two-percent milk, except that it takes almost half a cup of the stuff to kill that acid taste. Cream just seems to smooth the flavour out so much better. A quick glance at the clock on the wall above shows that it’s nearly 9:00 PM. The local...

A Stocking Encounter

The man and woman sat at their table in the veranda of the hotel awaiting their food. Both eagerly excited to see what would be concocted from their initial orders from the menu. As she twirled her honey colored Pies porter in her fishbowl-sized glass, bored by her companion and the lack of their conversation, her eyes scanned the restaurant looking from one couple to the next searching for a true match made in heaven. The 5-star Tuscan-based restaurant nestled itself quietly in the center...

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