It’s been about two weeks since coming back from NYC. I’ve been there and back and rarely have anything worth writing about, but this trip was something else. Although I am a little embarrassed by this story, I’ve swore to myself that I would not have any regrets for my life-style. So I hope you guys enjoy, it’s as true as I can remember.
One of my guy “friends” from NYC offered to fund a little vacation to the Big Apple as long as I spent some time with him and brought along my friend D. She is so hot and has the greatest set of tits I have ever seen.
He took us out to eat at this Sushi place and of course (for me) it was getting boring.
We got to talking and decided that we should start hopping from bar to bar. I really love the bar scene and was hoping to meet some other guys.
We went bar hopping. It was very wild. I was dressed in one of my tightest black mini-dresses and tall knee-high boots. My dress is sheer and my lingerie is plain to see. I even had on my black lacy thong! It seemed to being doing the trick cause every guy wanted to buy me a drink. Of course our buddy was sticking close to D. There was going to be some hooking up. I didn’t really care, but I promised not to leave her alone with him until we got back to our suite.
So I’m getting really horny watching these two making out all night so, I start flirting with some of the local talent. I’m really enjoying them trying to talk me into leaving with them. At one point, I had about eight drinks in front of me at my table. I didn’t spend a dime that night. I had to slow down, because I was getting really tipsy.
That’s when I was approached by this darling older man. It was well after midnight. The older gentleman bought me a Martini with three olives. If you know me at all, you know I love Martinis, very dry. He was white, a local, a little overweight and slightly balding; he was smoking a cigar and smelled like Old Spice. He seemed harmless though and it was kind of fun talking to him. I love his New York accent. He had great jokes and was teaching me about whiskey. He even got me to drink a Boiler Maker. I never drink stuff like that.
I started looking around for my friend, D and couldn’t see her anywhere. Feeling a little guilty, I figured I’d find her. The restroom was somewhere in the back so I thanked the old guy, gave him a hug, and went to locate my friend. It only took a few steps to realize that I may have made a huge mistake drinking so much. It had to be that damn Boiler Maker. I went over to the bathroom, but there was a huge line and I had to pee so bad, I thought I was going to piss myself. Next think I know, I’m standing outside behind the bar. Fuck-it, feeling silly and smashed, I decide to relieve myself right there.
I hiked up my dress, squatted (panties pulled over) and went for like five minutes straight. It was so intense and wonderful; I remember I had this real shit-eating grin on my face. I was feeling no pain.
I was still giggling when I started tipping backward. I was unable to do anything but laugh as I was looking up at the night sky. My eyelids seemed very heavy and the city sounds were so surreal. Just a little rest, I thought. Rest my eyes.
I remember feeling a cool gust of wind blowing up my skirt, bringing me back to reality. Then I felt a pair of rough hands rubbing thighs and then my hips and then my sides. And then roughly cupping my breasts and firmly pinching my nipples.
I was blinking my eyes and turning my head trying to make out where I was. I was getting accustomed to the darkness when his tongue started to dart in and out of my pussy lips. I could feel that my legs were resting on his shoulders. He had me tipped up for better access.
I don’t know if it was the alcohol or if I was slipped something but I couldn’t move and decided to play as if I were still asleep. I wasn’t scared as much as I was drunk.
I was thinking that my dress will need dry-cleaning. Then I closed my eyes.
Then the world seemed to turn, and my face was full of tweed. I must have been flipped over onto my belly. At least he had the courtesy of keeping my face off the alley ground. I spent hours putting on my makeup.
He lifted my skirt past my waist and was working the waist over my tits. He was breathing very heavy when he lifted up, my ass onto my knees. Then, he pushed his fat cock into my wet pussy. I guess I just slept through the foreplay! Shit, I’ve never been this out of it!
Now, my dress was riding way high against my shoulder blades, my tits were hanging out and my thong was gone but he was tightly holding on to my hips and pumping his cock into my pussy like a mad dog. I was still limp and getting pounded like a rag-doll. It didn’t take long before he pulled out and began rubbing his sloppy cock on my ass-crack. I was expecting to feel his hot sperm shooting onto my naked ass. Instead, I felt him spread my asshole open and jam his huge cock in. He must have lubed it with my pussy juice because it went right in on the first try!
It went all the way to his hairy balls. At first, it really stung like a son of a bitch. I couldn’t scream or even breathe. He definitely wasn’t circumcised because it really started to glide!
After a few minutes, I was able breathe again and I had mobility again. Instinct kicked in. I reached my hand down to rub my clit while I pinched a nipple with my other hand. I was moaning, now. He began pounding even harder. I heard him say something like "I knew you were faking". I tried telling him that I was really fucked up, but could only grunt. My throat was really dry and raspy. He didn’t want to hear it.
It was so intense that I had to bite down on his jacket. Then it occurred to me, it smelled like Old Spice and cigars. Was this the nice old dude?!
I was too far gone to care and couldn’t do anything to stop it at this point. He was breathing heavy, maybe hyperventilating. He lost his balance and fell forward onto my back with all his weight!
He crushed the wind out of me while shoving his extremely thick cock deep into my ass.
As he catches his breath, he says "sorry honey", and leaves his cock shoved deep in my asshole. I was belly-down in my expensive dress and boots but now I was coming; hard!
I guess he could feel me tense up because he started really grunting and his dick started to spasm. I could feel my little asshole fill with hot cum. Then it starts oozing out of my hole, drip down and onto my pussy.
We laid there for a couple of minutes until he rolls off of me.
I manage to get up on all fours. Thinking he’s coming over to help me up, he walks around in front of me. He reaches out with both hands and cups the back of my head and jams his nasty cock into my mouth. I can taste my own pussy and ass fluids mixed with salty cum for a brief moment. Then he starts hammering my throat until he’s going to break my jaws. I’m now on my knees with my pussy and tits fully exposed. I’m trying to pull his hands away but they are locked on like vices. At this point I’ve got tears in my eyes and he’s like a crazy man. “Look at me, honey”. “Yes, that’s right”. Then he unloads. I have to swallow or choke. How much does this old dude have left??
As he pulls out, now he helps me to my feet. I can bearly stand so he helps me pull down my dress. He took his jacket back and adjusts his trousers.
It was indeed the old “gentleman” that I spoke with earlier. He handed me my purse and tried to kiss me on the mouth! I think he kind of understood at that moment that I was not pretending to be drunk or playing games. He started apologizing to me then and was saying something about being a widower. He hadn’t been with anyone since his wife. She had never let him do to her what we did. He looked at his watch and asked if I was alright. I said don’t worry about it, I’d be okay.
With that, he was gone. I bent over and immediately began throwing- up my vodka, whisky and beer. All mixed with salty, creamy cum.
I stood by the back door of the bar trying to wipe off some of the drying cum that was starting to harden on my thigh and started looking for my bra and panties. I found my bra, but the clasp was broken. I had to tie it in a knot. My panties were nowhere to be found. Why do guys like to take them? Trophy?
I tried to get back into the bar, but found that the door was locked. Was I going to have to walk around the block to get back in? Luckily, a couple guys came out. I was about to give up. They looked at me like I was going to get lucky. I just said “don’t even try it”! I walked right past them and back to the bar.
There was D. She didn’t even realize that I was gone! She was like "What’s up girl. You about ready to head out? It’s last call".
My favorite panties were gone (probably a souvenir), I had cum dripping from my asshole, and my mouth and throat felt kind crusty. At least he didn’t paint my face and neck with it.

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