My First Halloween Cuckold Experience!

By: Tina's Cuck

Hello,

Hey. It's getting close to Halloween and I wanted to write in and tell the story of my first cuckolding experience that started on Halloween.

My girlfriend Tina and I were in our mid twenties and living together. She is a professional make up artist and loves cosplay. She has gone to conventions several times with her friends dressed up was various anime characters. Her costumes are always hand sewn and also very sexy and revealing. She spends weeks getting them ready each time.

As you might expect, Halloween is her favorite holiday by far. It gives her an excuse to dress up in a sexy costume and exhibit herself to both friends and strangers alike. That year, Tina had been coordinating with her friend Lauren for several months on matching halloween costumes. I didn't know the exact anime show they were suppose to be from but they basically looked like slutty Sailor Moon type outfits. It was apparently very important though that they were together the whole night for halloween because the costumes 'didn't make sense' on their own.

Lauren had invited both of us to a big party at her friend's house. His name was Jake. Neither Tina or I knew him very well... just that he was a big frat guy in college and was known for throwing 'epic' parties. We had met him once before at Lauren's birthday party. A day before the party though, Lauren got sick. She apologized profusely to Tina for not being able to make it after they had both put show much effort into their costumes.

Tina didn't blame Lauren but she was nevertheless upset that the costume she had been working on for so long would no longer work without its pair. I tried to console her and suggest that she still wear her amazing costume but Tina was convinced that no one would understand it without Lauren there with her. I asked if I could do anything. She said no initially but then got an idea with a wry smile across her face. She said that she could still wear her costume to the party if I wore Lauren's costume. Lauren and I were roughly similar sizes so it would likely fit me and Tina could make a quick adjustment to the costume if there were any issues. My first instinct was hell no. She was asking me to crossdress in a slutty outfit with a short skirt. Tina kept pleading though and I eventually accepted her request.

To my horror, it was gonna take a lot more than just putting on the outfit. First, Tina insisted that I shave my entire body completely. I couldn't look like an anime with hairy legs and arms. Luckily, I didn't have a ton of body hair. It still felt strange though shaving my entire body in the shower. Tina watched and made sure I didn't miss any spots. Then before I got dressed, Tina did my makeup and made me look as girly as possible. I knew Tina was quite skilled at applying makeup but she had never done it before on me. I was surprised afterward looking in the mirror. I didn't look like an attractive girl but I looked way more feminine. And after she put the blonde wig on me, I really looked like a girl... an extremely unattractive girl but a girl nevertheless.

Next, Tina helped me get dressed in the costume. She insisted that I had to wear panties and a bra to match her outfit. The panties at least were bikini style and not a thong or g-string. It felt strange wearing them now that I was freshly shaved. I felt the silky material directly against my skin. The bra though felt a bit more humiliating, especially after Tina stuffed it to give c-cup sized boobs. Tina giggled a bit but encouraged me to keep going. I put on the shirt which was just a white button up. And then I put on the skirt which was ridiculously short. I felt that you could see my ass if I bent over in even the slightest. Tina made me spin for her but then transitioned quickly to getting herself ready for the party.

A half hour later, Tina was ready. Our outfits looked the same but she obviously looked much better in her outfit than I did in mine. We got in the car and headed out to the party. When we arrived, the music was loud and we could hear it from down the street while we parked. At least there was no confusion as to wear the party was.

Once we got inside, we realized that the house was packed and the party was raucous. We wandered around looking for Jake and eventually found him near a keg. Jake noticed Tina first and then eventually realized that it was me next to her dressed in drag. He laughed and complimented us on our matching costumes. Tina thanked him and took most of the credit for getting both of us ready. Jake then handed us drinks and gave us a tour of his house before leading us to a makeshift dance floor in his living room. There was a DJ (one of Jake's friend) and a sea of strangers dancing in front of us. While struggling to talk over the loud music, Tina and I eventually finished our drinks. Jake then asked Tina if she wanted to dance. At first she looked at me but I just nodded and said I'd go get us another round of drinks and then come back. Jake then took her by the hand into the middle of the dance floor while I headed back to the keg.

In the other room, there was a big crowd around the keg and it took me several minutes to get to it and pour three drinks. I then struggled to get back through the crowd to the living room to find Tina and Jake. Once I got there, I walked around the periphery of the room and eventually found Tina and Jake on the far side near a window. Jake was behind Tina but had his arms around her while she gyrated her ass into his cock. I had seen Tina dance with friends before but this was perhaps more spirited than usual. I handed them their drinks and they briefly stopped humping each other to take a few gulps. I tried to talk to them but we could barely hear each other. They eventually handed their drinks back to me and Tina used her hands to signal that she was going to dance more with Jake.

I meekly walked away and found a table in the corner to put their drinks on. As I sat against the table and finished my drink, I watched as Jake positioned himself in front of Tina, put his arms around her, and started dry humping her to the music. Tina looked back at me and I gave a thumbs up not knowing how else to respond to the situation. She then smiled and turned her focus back to Jake.

I continued to watch as they danced for several songs in every possible position. Eventually they grew tired and separated. Tina found me in the corner and Jake went off to welcome some other visitors who had just arrived. Tina leaned against me to say something in my ear over the loud music but was quickly surprised to feel my partial arousal under my skirt. Tina teased me and called me a creep for watching so intently. I confessed that she looked incredible dancing and it was hard to take my eyes off her. She reached down and grabbed my cock over my skirt and said that I better calm down or I'll have an embarrassing tent in the front of my skirt that everyone will see.

Tina then turned, pressed her ass against my crotch, and started to dance slowly to the music. I held her waist and she leaned her head back against my shoulder so we could continue talking. Unfortunately, Tina's rubbing against only made my erection harder. Tina laughed and asked if I wanted her to keep dancing with Jake. I confessed yes. Tina laughed and then asked what if Jake wanted to do more than just dance. I asked what she meant and Tina told me that Jake offered to give her a personal tour upstairs later. Again, I wasn't sure how to respond but Tina kept grinding her ass into my cock. She then said that my cock felt like it was saying that she could take the tour. I tried to resist but I unfortunately she pushed me over the edge and I started to cum in my panties at that second. I apologized and pushed Tina off. Once she realized what had happened, she started laughing instantly. She said she knew that I was a horny perv but didn't know I was that horny. I struggled to cover myself but luckily the cum just covered the inside of my panties and didn't show on the outside of the skirt. After regaining her composure, Tina said that she would take Jake up on his offer of a tour since I had already managed to relieve myself. I accepted Tina's decision but asked what I should do. She said she'd tell Jake that I got sick and had to go home. I nodded and then meekly left the house and walked back to the car.

By the time I got home, Tina had texted me a couple times. The first time said she was heading back to the dance floor with Jake. Then next text said they were getting drinks again before heading upstairs. I took off my costume and cleaned off my makeup but got increasingly anxious because I didn't hear again from Tina until several hours laters when she finally arrived home in a taxi. When she got inside, she immediately headed to the bathroom and got in the shower. I followed desperate to hear any more details about the rest of her night with Jake. Before she told me anything, she said she was still astounded that I came on myself on the dance floor. I apologized and admitted that I was completely embarrassed. Tina replied that my absence was good though because it gave her Jake more confidence to pursue her. She explained that they danced more and his hands were everywhere on her body including under her skirt. She said she tried to play coy but eventually couldn't resist and started making out with him on the dance floor.

Then after lots more dancing and kissing, they got another round of drinks before Jake brought her upstairs. Once they got to his bedroom, Jake sat on the edge of his bed while Tina gave him a brief strip show taking off her costume. As she did, Jake pulled his pants down and revealed his cock to her. Tina said she felt incredibly slutty and instantly got on her knees in front of him and starting sucking his dick. Eventually he pulled her up and she sat down on his wet cock cowgirl style. She then rode him for several minutes as they continued fondling each other's bodies and making out. He then picked her up, spun around, and dropped her back on the bed in missionary position with her legs around his back. Tina said he felt incredible and she orgasmed at least four times. Then at the end, Jake pulled out and shot his load across her chest.

Afterwards, they both caught their breath. Tina eventually got up and cleaned his cum off with some paper towels. They kissed some more as she got dressed and then she called a taxi to bring her home. As she finished her story, I had a hard erection once again. Tina noticed and said she'd take it as a sign that I should meet Jake again. I said yes and started to jerk off in front of her. She continued to shower with a smile on her face.

- mahmiss@tutanota.com

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