My First Gangbang

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My First Gangbang
For as long as I can remember, I have always enjoyed wearing women’s clothing. When I was in fifth grade, I started wearing pantyhose under my pants during the winter. By the time I was going into the seventh grade, I had learned that, not only did I enjoy wearing pantyhose, I also liked playing with peckers too 😉

As you may imagine, I became VERY popular! Pretty soon, there wasn’t a sleepover in the neighborhood that I wasn’t invited to 😉

I quickly developed what would be a lifelong obsession: semen. And no matter how much I got, I still wanted more! The feel of it squirting into my mouth…or dripping from my face after I’ve sucked a guy off…trickling from my ass after taking a hot load (or two!). Even had a group of guys that used to squirt into my pumps and make me walk around in them. Every step I took made their cum squish through my toes 😉

Well, every year since I was about 5 years old, I have dressed up like a woman for Halloween. It started with Princess Leia when I was 5. Then, it was Snow White. Then, it was Cinderella. I was getting older and my costumes were getting a little more adult. I was 14 and had told my mother that I wanted to be a “hooker” for Halloween. My mother LOVED the idea! My Mother had gotten pregnant with me shortly after she turned 13 and although she had a 14 year old son, she did not look 27. In fact, at 4’10’ and 90 lbs, she was more often mistaken for my sister than my mother!

She took me shopping and while I had been dressing up in women’s clothing for several years at that point, I did not have any of my own lingerie. So my Mother to me a lingerie store, bought me a black garter belt, a black pair of stockings, a pair of lacy black frilly panties and my own bra!

Then, we went to a clothing store. We looked at skirts and I picked out a few that I liked, but my Mom said that they weren’t slutty enough and that my skirt should be WAY shorter 🙂 Wasn’t going to argue with my Mom! She bought me a super short black miniskirt, and a short sleeve, red blouse.

We got home and I don’t know who was more excited, me or my Mom! It was only 3 or 4 in the afternoon and my Dad was at work until 10. We went straight to the bathroom and she started showing me how to put makeup on. While I had had an experience with a couple of cousins, it was really these interactions with my Mother that taught me how to paint my face up like a slut!

Everything got uncomfortable when we went to try on my skirt. My Mom got on her knees, grabbed my pants as well as my underwear, and pulled them down…I WAS AS HARD AS A ROCK! I tried to hide it from my Mother, but she told me that it wasn’t anything to be ashamed of. “Come here,” she said, “let your Mom have a closer look.” I stepped toward her and she got on her knees. I wanted her to suck my cock SOOOOO bad! She took me into her soft hand and began caressing my cock and balls. “That’s a good boy,” she said playfully. Then, SHE STOPPED! She said that she was my mother and that I was her son. I said, “Yeah, no shit…that’s what makes it so hot!” No matter how hard I tried, my Mom would not give in 🙁 At least, not for a few more years!

A few nights later, it was the big night…Halloween. I had put on all of my makeup…put on my outfit and wig. My Mom was helping me practice walking in heels 🙂 At 7 o’clock, my Mom drove me to my best friend John’s house and we went out trick or treating. As soon as we hit the street, a car drove by and yelled, “Hey baby! How much?” Haha!

As I went from door-to-door, I was telling my friend which houses I had had sex with guys in. As I pointed out house after house, my friend said, “Is there a house in this neighborhood that you HAVEN’T had sex in?” At one of the houses, the homeowner recognized me, told me that his wife was out of town and that he was having some guys over later if I wanted to swing by. He told me that I should keep on my hose and heels cuz the guys would like it 😉

My feet started hurting due to my stiletto heels and I told John and we headed back to his place. We had gathered quite a crew of our friends and when we got back to his house, there were 14 guys. John’s mom knew that her son and I were lovers…she even knew that I liked to wear pantyhose and high heels while we did it 😉

While I was no stranger to the thrill of having cocks in my mouth, I had never played with more than 2 at a time. The closest thing I had ever done were after school circle jerks at John’s house. We would all get comfortable in the living room, groups ranging from 5 to 15 guys, John would throw in a porno, and we’d all jerk ourselves off. When we came, we would shoot on a cracker on the table. The first one to cum had to eat the cracker…I was ALWAYS stroking to cum first!

I didn’t like the fact that 90% of the cum landed on the table and not my mouth, so we started using a tortilla 😉 Pretty soon, guys would just put their cocks in my mouth right before they came! They knew I loved that hot, gooey stuff!

Anyway, John’s mom had brought down a pitcher of orange juice and cups when we got back from trick or treating. John got into his dad’s liquor cabinet and took out a bottle of tequila. Soon, everyone was loosening up and things were getting frisky! Guys were putting their hands all over me…I was putting my hands all over guys…you know, fun shit!

I said that my shoes were killing my feet and asked if anyone would like to massage them…ABOUT HALF A DOZEN HANDS WENT UP!!! I had one guy massaging my right foot, and another one massaging my left foot. Then, cocks started getting pulled out and I started reaching out and giving the guys a friendly pull 😉

I got down on my knees and was IMMEDIATELY encircled by 6 guys…all stiff…all horny! One of my buddies laid down on the floor, slipped under me and began rimming my hairless asshole while I blew the guys. As I worked the 6 dicks in front of my face with my soft mouth and hands, as my buddy furiously tongued my pink, puckered, tight asshole, as two of my buddies started caressing, massaging, tickling, kissing and sucking on my succulent feet and toes…I thought…”Wow! I’m having sex with 9 guys at the same time” 😉 For someone that had never had sex with more than 2 guys at once, I think I was doing a pretty good job!

As I was working over all of the cocks and trying to make sure that everyone was involved and having a good time, the door opened and John’s mother walked in…WITH A PLATE FULL OF COOKIES!!! It was actually kind of surreal as she walked in, the guys, completely naked and erect and working my mouth and ass with their poles, grabbed a cookie and said, “Thanks Mrs. So-and-so.” She saw that I was the only one that was bottoming and told me that if I needed anything, a drink of water, a sandwich, anything, to let her know.

It took me almost two hours, but I made all 14 guys cum! When I was done, I went upstairs to shower all the spunk off of me, when I bumped into John’s mom in the kitchen. I was completely naked at this point…and she asked if I wanted a beer…HELL YEAH! We sat at the kitchen table, drinking our beer and she asked me what it was like to have sex with that many men. She told me that, with as much work as she has to put into making her husband cum, she could not comprehend how I went for 2 hours with 14 guys. I said with a smile, “That’s why God gave us energy drinks!

It was close to midnight and I got a text from the guy that had invited me to his place. His said his party was starting to get exciting. I told him where to pick me up, jumped in the shower, threw on some makeup, put my hooker outfit back on, and I was off to party with some older guys! You can imagine the look of surprise on my face when I walked into his house and down to the living and found 17 naked men! What’s the best way to top off a gangbang? With another gangbang, of course 😉

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