Back in college I was in a pretty serious relationship with Bailey a cute blonde in a sorority. She was 5’6″ 120lbs and had curves in all the right places. She was extremely sexual and although it was vanilla by nature we would literally skip class to fuck all day. Her stamina was to die for. Lucky for me so was mine. She was obsessed with my size and told me that although she had some big guys before I was by far the biggest. Even when we would just watch tv she would take out my dick and play with it just to “see it get big” as she would say. I still miss her enthusiasm.
One night she got invited out to a Halloween party with her sorority sisters and being as close as we were it was assumed I would be tagging along. That didn’t fly to well with her friend Maddie though and she gave us a verbal protest. So to make thing better for myself I bought a few bottles for us to pregame at Bailey’s apartment. It was myself, Bailey, Maddie, Sarah and Ashley. The girls were all dressed in cute matching black cat outfits. Which was just a American Appeal one pieces with cat ears with a tail. It was amazing being able to steal glances at each of there asses. I was just some random thrown together Scottish warrior. It was really just one of Bailey’s skirts, shirtless, with a scarf thrown over my shoulder pined to the kilt. Of course I wore it in true Scottish fashion.
After about a half dozen shots we were on our way. Sarah decided she was going to drive since she had the biggest car and only had one shot. So it was Sarah driving, Ashley in shotgun and Bay, Maddie and I cramped in the back seat. The party it self was lame and mostly filled with frat guys who either didn’t dress up or clearly didn’t want me there but we drank their beer and smoked their weed anyways. Bailey kept protesting to leave and convinced the girls that we could just kill the bottles back at her place and have a better night there. The girls finally came around and we hopped back into Sarah’s car.
By this point we were good and drunk/high from the festivities so Bailey and I were getting pretty handsy as we do. We hopped back in to the car in the same order and were off back to the apartment. As we got on the highway I felt Bailey’s hand slide up my kilt. She slyly started caressing and stroking my dick which quickly got me rock hard. I looked over to see if Maddie could see anything but she was too drunk to care at that point. Then to my surprise Bailey said out loud “Have I ever shown you guys Designhero444’s dick?” which took me and the other three girls by surprise. Maddie quickly perked up and said “What” and Ashley turned around and said “No, WTF why?” Bailey then turned to me and asked “Can I?” to which I gave her an “okay” nod. She then flipped up my kilt exposing my hard huge dick for the girls to see and said “Isn’t it huge?!?” while grabbing close to the base. Maddie turned away and said “WTF Bay!!” Ashley’s moth dropped and just said “Damn Bailey that’s a nice one congrats!” Sarah still driving kept trying to look using the rear view mirror just said she couldn’t see anything then with Ashley holding on to the wheel Sarah whipped her head around and just said “Nice” as she turned back to look at the road.
Bailey just kept stroking like no big deal as Ashley asked if I was fully hard when I told her I was she just said “Damn” again. Maddie was looking at this point but didn’t say anything. Then Sarah said “Alright you two put it away” So Bailey flipped the kilt back over and left me sitting there popping a literal tent.
When we go back to the apartment the conversation had already changed and we quickly went back to drinking to cap out the night. All in all we probably took 6-8 more shots over the course of 45 minutes which put us all in a state well beyond fucked up. At this point Bailey sneaked into her room and fell asleep with out saying a word. We only knew she knocked out from her loud snoring. Sarah still soberish left to meet her boyfriend at a bar and Ashley was in the bathroom either showering or throwing up.
Maddie and I sat in the living room on the couch just casually talking trying to control our drunkenness. I then asked her about her love life only to see her instantly start to cry. I panicked and immediately apologized. She just said, while wiping her tears “No, it’s ok. I… well.. can I tell you something no one knows.” I assured her it was okay and that I wouldn’t say a word to anyone. She then said “Well… I haven’t had sex since February of this year.” In my drunken stooper I just said “Whyyyyy?” which made her cry so more. I then scooted over to her and put my arm around her as she turned to cry into my chest sobbing “Why don’t guys want to fuck me?” Maddie is also a blonde but is 5’4″ 140 lbs.(maybe) with a little more curve than most for her size but still rocking a nice pair of DD. I just petted her back and said “It’s ok Maddie you’re super hot” and in my horny drunken state said “Honestly if I were single or if Bailey were cool with it, I’d fuck the shit out of you” She just stopped crying and looked up at me and said “Really…? …You would?” I looked at her and said “Hell yeah I think your hot and I always have a good time with you”
We sat in a few seconds of silence, which seemed like forever and with out saying a word started kissing hard. I reached down and pulled the top straps of her outfit down exposing her beautiful breast as she lifted my kilt exposing my already semi hard cock. She took me in her mouth and started giving me the sloppiest blowjob I had ever had. She gagged and pulled up saying she couldn’t take me all the way. I just laughed and said I wasn’t even all the way hard yet. She then stood up pulled the bottom of her one piece to the side and exposed her beautifully bald pussy. She awkwardly positioned herself on top of me and tried to slide my dick inside. I could see it in her face she was in pain but we were both so far gone that it didn’t even matter. She rode my cock hard saying she had never had anyone this big before and I told her that I loved her tight pussy. I can’t remember if she came or not but when I told her I was going to she just said “Cum in me I’m on the pill” and with that I shot what felt like a huge load inside of her. The whole thing probably lasted maybe about 5 minutes tops but all she could do was collapse on top of me and with a small sob she just said “Thank you.” All I could say was “you’re welcome.”
She then got up and went into the bathroom where Ashley was only to find her passed out in the tub with a towel as a blanket. I collected myself and walked into Bailey’s room finding her still snoring passed out. I crawled into bed and fell asleep. Maddie slept on the couch. By the time I woke up both Maddie and Ashley were gone and we never spoke of it again. I think for a long time we wrote it off as it never happened or at least that’s how we played it.
Maddie and I had one more encounter just this past year but Ill save that for another story. Bailey and I didn’t last too much longer either when she decided to quit school and move back home.
Source: reddit.com/r/gonewildstories/comments/72oapy/one_halloween_night_with_my_gf_and_her_sorority
I feel like this was less erotica and more “lol my dicks huge”. Like, you dedicated 4 paragraphs to bragging and like, 3 sentences to actual action.
Great story bro. Any pics of Maddie? Always love girls who are a tad chubby but with big tits.