I’m writing about a Halloween party where I wound up having sex with a guy with the biggest, scariest penis I could have imagined.
My name is Rachel and believe it or not, one of my best girl friends is named Monica. Monica was having a Halloween costume party and she had literally invited over 100 people.
I decided to go as a pink pussy cat. The movie Legally Blond had just been in the theaters and I thought Reese Witherspoon looked so cute in her costume.
I’m a blond with a nice figure and nice legs and I figured that my costume choice would let me really show off all of my features.
I like what nature gave me. I’m 5 feet 3, 103 lbs, with 34B-24-33 measurements. I have a cute baby face framed by blond hair. I’m popular with guys because of my looks and also because I’m sexually adventurous. I started having sex during the summer between 8th grade and my freshman year. By my junior year, I had enjoyed sex with over 40 different guys.
I went to the party fully expecting to hook up with somebody. I really wanted to get laid that night.
My costume did exactly what I wanted it to. The high cut hips made my legs look so long and sexy, and the cheeks of my firm as were barely half covered.
I got a lot of compliments about my costume from both girls and guys. The girls thought it was cute, the guys were admiring me in a different light. I was having a hard time identifying all the guys at the party because they were wearing costumes or masks. But I was pretty good at recognizing voices. I was trying to decide which cute guy I would hook up with. Did I want to fuck a guy I had already been with or did I want to find someone new?
I started talking with a guy dressed as a monk from the middle ages. He was Monica’s brother’s college room mate. His name was Chris and he was 20, so he was 2 years older than me. He was funny…more than funny, he was hilarious. He got into character for his costume and told me that he came from a monastery in Italy where they stomp their own grapes, not to make wine but because it felt good between their toes. It helped distract the monks from having homosexual thoughts about the local goat herders. He also said the monks in his order worshipped cats, especially pink ones…at least that’s what he thought the head of his order meant when he said “Let us give thanks for the blessing of the pink pussies.” It was like having a conversation with Robin Williams. I knew I had found my guy for the night.
I invited him to accompany me to the pool house. Monica’s family is rich so they have an outdoor pool. The pool house has an indoor hot tub, a sauna as well as a number of changing rooms. The changing rooms have padded benches so they make good make out rooms.
It didn’t take us long to slip out of our costumes. The pool house was a little cool and the combination of cool air and lust made my normally small pink nipples really pop out. Chris admired my firm young tits and alternated sucking both nipples. As he was doing that he slipped my panties down to expose my nicely manicured blond pubic patch. Unlike a lot of girls who just have a big patch of course hair, I have the kind of pubic patch that actually has a pattern where it looks like two cowlicks that sweep toward each other. The hair is soft and fine and very light. He told me it was lovely. I thanked him and asked if he was ready to see my actual pussy…my pink pussy. He laughed and gently guided me onto the bench.
I spread my legs and let him explore my pretty little vagina with his eyes, then his fingers, then his tongue. My pussy is quite pretty. The lips are small and delicate and pink. I’m also really small and tight. Even so, I like large dicks. Not that I can’t enjoy a small dick, but big ones are visually exciting. As I soon discovered, I had reason to be very excited about and frightened over Chris’s dick.
He slipped his boxers off and revealed the first 10 inch penis I had ever seen. Until that moment, I considered big to be 7 1/2, maybe 8 inches. His penis was a big around as a pole vaulting pole. I was amazed and a little scared as I fondled and caressed it. The head was big enough to completely fill my mouth. There was no way I could take any part of the shaft into my mouth. How would my little pussy take this?
I soon found out. I leaned back so that I was in a half sitting, half lying down position. I looked down and watched the massive penis approach me. I used one hand to spread my little lips and the other to guide his penis into me. He was so gentle. He gentle nudged the head into my vagina until the head had disappeared inside of me. Then he waited for me to tell him to go a little further. It took several minutes for him to completely enter me. It was uncomfortable but not unbearable. Once my pussy had swallowed his entire penis we just stayed like that, getting used to each other’s bodies. He said I was so hot and soft and sensually tight. Of course he was filling me more than I had ever experienced.
He began fucking me with short gentle strokes. Then he used longer strokes, pulling almost all the way out and plunging deep. It didn’t take long for me to have the first of 3 orgasms. When he came I swear his penis seemed to swell up even more inside of me. He just kept throbbing and twitching. I could feel the powerful jets of cum shooting into me.
I got on top of him and rode him, each time pushing down hard to make sure I was milking his entire shaft. Then we went at it doggie style. He came two more times for me and I must have come a half dozen more times. Once we finished fucking we just laid there in the missionary position. We weren’t trying to come again, we just loved having our bodies entwined. His penis was in me but it was only half erect. We finally returned to the party.
That all happened several years ago. I now attend the same college he does and we hook up for sex often. Monica was dying of curiosity so she propositioned him one night. He took her up on it and they both had a great time. I knew he would love being with Monica, she’s a drop dead gorgeous brunette who looks like Angelina Jolie. She is also one of the sweetest girls, most gentle girls to walk the earth. I love her like a sister. We recently had a threesome – Chris, Monica and me – which I will tell you about some time. Oh yeah, there’s the threesome I had with Chris and Monica’s brother Ben. That’s another story too.
Thanks for letting me share my Halloween fright nite story.
– The End –