Let me start at the beginning. I was 17 and my friend Desmond’s Mom needed to go out of town for a weekend.
For some strange reason she agreed to let me stay over, while she was gone. In order to prevent us from throwing a huge party she also left his older, bitchy sister, Leslie in charge.
What that really meant was that Leslie’s 6’4″…225 pound boyfriend Brent, would be in charge. But the truth was – as long as Desmond and I stayed quiet, they didn’t care what we did.
On Friday evening, we waited a solid hour before we put our plan of pot and beer into play. We were each about two beers in when Brent showed up. Much to our surprise when he walked in the door, he gave us a case of beer and told us, “I hope this buys your silence, we’ll be in Leslie’s room…”
After about three beers apiece later, we decided it was time for us to break out Mary Jane. Between the beer and the weed, things started to get a little fuzzy.
At some point Brent and Leslie must of gotten into a fight because Brent suddenly left – yelling out, “Fuck You…Skinny Bitch!”
I can testify that Leslie was both skinny and a bitch. I don’t think she weighed 100 pounds, dripping wet. And at 5’8″, her skinniness was the first thing you noticed.
So Desmond and I did what any 17 year old pot smoking kids would do: we kept on doing what we were doing.
At some point, he and I fell asleep. At around 2:00 in the morning I woke up, needing to pee.
As I was walking to their toilet, I heard a moan come from Leslie’s room. Thinking that her argument must have really torn her up I went to see if she was okay.
What I walked in on, my young, drunk and stoned-self was not prepared to see. Thank goodness I had been asleep long enough to remember what I was about to see, and realize.
I guess at some point after Brent left, Leslie called her friend Kat.
The moan I heard had come from Leslie all right, cause Kat had her face buried in Leslie’s pussy licking it like the world depended on it.
At this point I noticed 2 things. Leslie had pierced nipples, and I no longer had to pee.
It was clear that Kat knew her way around the female body. As she was eating out Leslie, Kat used one hand to rub and pinch Leslie’s A cups. After what seemed like a few minutes Leslie had a major orgasm. From there Kat worked her way up Leslie’s body until they kissed.
After a few minutes of kissing Leslie, then worked her way down to Kat’s pussy. As she was eating out Kat, Leslie started sliding her fingers in and out of Kat’s puss. After a few minutes of this Leslie then slid one her now lubed fingers into Kat’s ass.
When she did Kat let out an approving moan. After Kat had her O, Leslie said, “Put on that strap-on and fuck my brains out.”
“I thought you’d never ask,” came the reply.
Then Kat did exactly that.
To this day I don’t think I’ve ever been as hard as I was watching them from the shadows. After what must of been about 4 or 5 orgasms in about as many positions Leslie said, “No more, my pussy needs a rest.”
To that Kat replied, “Well then why don’t you lick my asshole, then fuck it with that dildo?”
To my surprise Leslie did just that!
I had seen this stuff in porn before, but never in my wildest dream did I think I’d be 8 feet away from it.
Kat was doggie-style while Leslie pounded her ass with a dildo.
I’m not sure why but as I started stroking my cock I noticed that Kat still had that strap-on on. As she came, I made a mistake. I, too moaned.
And Leslie for the first time looked at the door where I was standing!
Busted, I wasn’t sure what to do. Then Leslie surprised me one more time!
“Jake get your ass in here!”
I did as I was told.
“Jake this is what’s going to happen. You are going to put this lube on your dick, then stick your dick in my ass. If you don’t do this I’m going tell your Mom that you were smoking weed all night.”
As she was saying this…Kat had moved so that she was laying on her back.
As I walked up, Kat handed me the lube while Leslie sat on Kat’s strap-on putting it in her pussy.
After I lubed up, Leslie grabbed my dick and said, “Yeah, that’s enough lube, now get behind and stick that dick in my ass.”
So that’s what I did.
Since most all of the girls I had fooled around with were my age, I had never fucked a girls ass.
I let her reach around and grab my cock and guide me in. After a few minutes I was all the way in and could feel her anus tighten around my package.
“Go slow at first, and listen to me. When you hear me getting into it – speed up, but don’t go too fast until I tell you to do so.” she said.
It took a few minutes for me and Kat to get our fucking synchronized, but once we did Leslie went nuts.
As I was fucking her, I reached around and rubbed her tits, playing with the piercings and pulling her nips.
After about fifteen minutes, I knew that I was about to blow my load. “I’m about to cum,” I moaned to Leslie.
Leslie must of been close as well, because she said, “Cum in my ass, I… want… you… to…fucking…cum…in…my…ass.”
And with her words I did.
Then I pulled out my cock and moved to lay next to Kat.
After Leslie regained her composure she looked down at me and said, “Thanks for that, now get out and shut the door!”
Realizing that I had served my purpose, I got up, walked out and closed the bedroom door. I went back out to living room and after a while fell back to sleep.
In the morning, Leslie came and sat next to me and sternly whispered, “If you ever tell another soul about last night – I will tell your Mom about your pot use, mark my words!”
As a 17 year old, that was all the blackmail I needed. However I think waiting 18 years is long enough…
Via: https://www.lushstories.com/stories/voyeur/oh-what-a-night-1