The short, insecure girl [F] in my friend group let me [M] fuck her in a sexy Halloween costume [MF]
My high school would do a “spirit week” in the second half of every year. Each day would be themed, and people would dress up. In my senior year, Friday was Halloween-themed so people would dress up in costumes for school and a dance that was taking place later that night. I was dressed as the Flash but because it wasn’t actually Halloween, it was more of a t-shirt than an actual costume.
The girls in my friend group, however, did not hold back. They had dressed as the seven dwarves from Snow White but with a sexy twist. Each of them was wearing a beanie, booty shorts, and an oversized shirt that had the initial of whatever dwarf they were. They all looked good, but one of my friends especially caught my attention.
Giselle was shorter than the other girls standing at around 5 foot nothing. Since they had all ordered the same shirt (just in different colors), hers looked more like a dress. It covered her shorts and I was getting really turned on imagining that she had nothing underneath. Physically, Giselle was Filipina, and despite being of different ethnicities had an extremely similar face to Rita Ora. Body-wise, she had a skinny frame that matched her height- kind of similar to Ariana Grande.
Despite being the smartest person in our grade and an incredible singer, Giselle always felt insecure because of her looks. She was very pretty, but she had a lot of attractive friends, and guys (including me) would normally have a crush on them. It wasn’t anything negative about her, but the lack of attention would often make her upset. It might’ve just been the costume, but she for sure had my attention that entire day.
After school ended, most people were waiting in our cafeteria for the dance. Giselle, however, had to drop a form off at her orthodontist (she had recently gotten her braces off). She asked if anyone wanted to take the train with her and I jumped at the opportunity to spend some time with her. Luckily, my house was the same stop as her orthodontist, so I made some excuse about grabbing something and left with her.
We sat down next to each other and started talking about random things. I wasn’t sure how to make a move because this was a friend, and I didn’t want to make things awkward. Through a stroke of luck, the train itself helped me start making things flirtatious. After going over a few bumps, Giselle slid from her seat against me. Due to her being so small, she was really thrust against me and it took her a few seconds to get off.
Giselle apologized and looked embarrassed. I told her that she didn’t need to be sorry and that I kind of liked it. She seemed confused and asked what I meant so I said, “I’m never going to complain about a pretty girl being all over me.” Giselle laughed and hit my arm. She was pretending to find it funny, but it was clear on her face that she was blushing and enjoying the compliment.
As we got off the train and walked towards her orthodontist, we kept “accidentally” brushing up against one another. It was as if we both enjoyed the touch and kept moving into each other. I waited outside while she went in with the form and built up some courage. I decided that when she got out, I was just going to be honest about what I was thinking.
Giselle came out and I did exactly that. I said I didn’t think we should go out or anything (to which she agreed) but I thought she looked unbelievably good today. She got red in the face again. Then I asked if she wanted to hook up or something and she couldn’t have said yes any faster. The only problem in my mind was that we had nowhere to go. Despite my house being close, there were people there and we wouldn’t be able to just go make out for a bit.
I started to explain this but Giselle just grabbed my hand and started walking. She pulled me down an alley between two buildings and then brought me to the dumpster area out back. While someone could walk out at any time, and people living on the bottom floors would hear us, it was still much more secluded than the sidewalk. I leaned down and we started to kiss hard. We took our backpacks off and I started pinning her against the wall. Before long, I was throbbing in my pants and rubbing it against her stomach (because she was that much shorter).
While I had only been expecting us to make out for a bit, Giselle immediately wanted more after feeling my hard dick. She took off her shorts and panties completely (but you still couldn’t tell from just looking because the shirt went to her thigh) and asked if I had a condom. I hurriedly took one from my bag, popped it on, and shoved Giselle back against the wall.
As I went to put it in, Giselle’s pussy was lower than where my dick was so I lifted her and held her by the ass against the back of the building. She was so tight that it took a few minutes before we could really start fucking. But once I started pounding her against the wall, Giselle showed me a whole new side of herself. The normally composed, intelligent, and confident singer was now begging me to go balls deep in her.
The tightness made her feel incredible. There was so much stimulation on my dick coming from every direction. Despite this, Giselle was enjoying it even more and very quickly said she was close. What she said next surprised me: “Finger my ass while I cum on your dick.” It was so hot that I started fucking her even harder against the wall. I could easily hold her petite body with one arm, so I put my other hand under her blue shirt and started pushing my middle finger in and out of her ass hole. To my surprise, it felt less tight than her pussy. She almost immediately orgasmed, and it felt amazing as her tight pussy squeezed on my cock. Giselle started moaning loud and I covered her lipstick-covered lips with my hand to muffle the noise.
Watching Giselle orgasm like that got me very close and I wanted to keep pounding hard but her pussy was sensitive. I was about to ask for a blow job when she turned around and said I could fuck her ass. I was shocked. I had never done anal and never did it again after this, but she was so casual about it. I asked her, “Really?”, and Giselle said it would be fine. She told me that she uses toys on it almost every day and I almost came just hearing that.
I excitedly ripped the condom off (after asking of course) and spit in my hand before rubbing it on my dick. I don’t even think it was necessary with how much wider her ass was than her pussy. I bent my knees a bit to stick my dick in Giselle’s ass but couldn’t really thrust that way so I lifted her again. This time, Giselle’s legs were bent and out on each side so I held her under her knees and thrust up while she balanced against the building with her hands. While it felt amazing, I was getting off more on the situation. I was dominating Giselle and knowing I was in a girl’s ass turned me on more than anything. I thrusted harder and faster before filling her ass with rope after rope of jizz. It was so rough that her beanie had fallen off just before I came.
After that, we cleaned ourselves up. There was something special about knowing my cum would be leaking out her ass and staining her panties for the rest of the night. On the train back, we talked things over again and said it was fun but there were no feelings involved. We both pretended like it never happened, and our friendship only got better. I still very much have a kink for women that wear oversized shirts and find it so hot questioning if they are wearing anything underneath.
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from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/pw4l3x/the_short_insecure_girl_f_in_my_friend_group_let/
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