My First Time Cosplaying Led to My First Time Roleplay Fucking [FM]

Considering I [M21] spent my teen years performing musical theatre, I’m surprised it didn’t happen sooner. Sure, stage work led to many of my sexual experiences, but none of them involved roleplay. No, it took my twenty-one-year-old dumb ass deciding to try out cosplay to wander down that particular road.

Here’s what happened.

In 2015, I spent the weekend at a major comic con dressed as Jack Frost from *Rise of the Guardians*. Every booth, each floor, the entire complex was packed with amazing costumes and incredible people and to this day I’m still impressed by how wonderfully kind and social everyone I met was. Literally left with stories that I’ll keep with me forever. That’s all beside the point, but if it dispels a few stereotypes for even one reader, it was worth the blurb.

My girlfriend [F18] went to a university nearby the convention center, so I made plans to visit her afterwards. Good thing, too, because after spending a weekend surrounded by gorgeous cosplay models (another con perk), I was horny as hell. She wanted to see the costume, and I hadn’t brought any other clothes because honestly Jack basically wore cuffed chinos and a bitchin’ hoodie, so when I arrived at her dorm, I just embraced the weird stares from the RA on lobby duty. Apparently, white hair is not normal for my age.

I met my girlfriend’s sister for the first time, and it went better than expected [FMF] [poppin cherries] [seduction] [Fdom, sort of]

“So you’re Carter? You’re the one fucking my sister?”

I walked in the room and I was staring at her. I knew Nicole had an older sister — Violet — off at grad school on the other side of the country, but she’d never much talked about her. I don’t know how I expected Violet to be, but it wasn’t what I was seeing. “Nicole in the shower?” I asked.

“Obviously,” the girl said, “Now answer my fucking question.”

Ivory skin, black hair, black eyeliner, black lipstick, tight leather choker. And she was wearing a high-waisted black dress that only came down mid-thigh, stopping a few inches above black mesh stockings. It was cinched tight beneath her tits, and a valley of cleavage above. To top it off, except the makeup, she even looked like Nicole, and was just as cute. Although Nicole didn’t have a pierced lip like Violet did, or so many piercings in her ears. So, like I said, I was staring. But Violet didn’t seem to mind the attention.

“Well, I’m, like, her boyfriend, but we’re taking things slow, like,” I said, taking a seat on the bed closest to the door, the one with Nicole’s luggage on it.

[MFF] Missed it by that much

This happened while I was in college with a woman, I’d been dating for close to two years at the time. We had some friends we hung out with a lot, a single guy and single girl. He was into her, but she was not into him. Thankfully, it didn’t have a negative impact on the fun we had as a group.

The girlfriend and I lived together in a small one-bedroom apartment that was part of a small complex. Next to it, was the pool that was fenced in and attached to the end unit of one of the apartment rows. It was technically closed after dark and locked up, but a good friend of mine lived in the apartment that was directly connected to the pool.

Our friends were over one night and as usual we had been drinking. It was a hot summer evening, so we decided to go swimming, this really wasn’t uncommon. However, this night we ended up skinny dipping.

My buddy spent most of the evening across the pool from the three of us. As the drinking continued so did the fun and games. Eventually, truth or dare happened.

Cheating with my Girlfriend’s Best Friend – Part 2 [MF]

Boxing Day [M24/F24]

I couldn’t sleep the entire night. Mandy was holding my hand. The guilt had taken over completely and I was just laying in my own thoughts.

At the break of dawn, I went into the kitchen. The sun was rising over this snowy paradise. I knew that soon I’d have to look into my Sam’s eyes and be conflicted with myself.
Mandy woke up first, as I was preparing breakfast. She looked at me, and came and kissed me on the cheek. I wasn’t sure what she thought was going on, but we definitely were in two different states of mind.

I coyly asked, “Mands, what did you wanna tell me?”

She looked at me sheepishly, and replied slowly, “You should know your girl wasn’t entirely faithful”

My curiosity grew, and so did my anger. I asked, “What do you mean?”

Cheating with my Girlfriend’s Best Friend [FM]

Christmas Night Fun [M24/F24]

I [M24] have been going over this multiple times before posting it. I understand the moral concerns that come with the story but please refrain from discussing your opinions with me regarding the matter.

Despite not being raised Christian, Christmas is usually a very big deal for me. Not only is it my favourite holiday, but also I love the festivities that come along with it. The decorations, the tree, exchanging presents and most importantly sharing a meal with family. Since COVID had claimed everyone’s Christmas plans, it was sad to see that I would be missing out on the usual festivities this year (2020). So I decided to invite my girlfriend (Sam) and her best friend (Mandy) over to my place and try to make lemonade out of the situation.

The meal was sumptuous. I was pleasantly surprised how much cooking I’d picked up watching my family on Christmas day. As we ate, we put on the TV (weird trivia about myself, but I cannot eat without any background noise), and turned on the Office. Sam [F23] wasn’t a huge fan so she concentrated on her food, but Mandy [F24] and I were able to bond over the show. Just like myself, it was her favourite sitcom. Sam didn’t seem to mind and she often encouraged me to be close to her friends. It had not been the easiest few month’s for us, but even through the rocky roads, we somehow made it through.

[F]ucking Ex Girl[f] riend Wildly In Lucknow

Fucking Ex Girlfriend Wildly In Lucknow

This happened a month back when I went to Lucknow for some office work and there I met my old ex. It was the starting week of Aug 2017 when I went to Lucknow. I landed there at around 8 am and went to Clark Avadh, as my booking was there. I had a meeting in the afternoon. So after check in, I took bath and went out to get some cigarette. While I was standing at a nearby shop getting my stuff, I saw someone nearby who looked very familiar. I went forward and tried to get a better glance. It was gauri my ex girlfriend. We were in long distance relationship around 10 years back, things didn’t work out at that time and so we broke and were no longer in a relationship. Also, we didn’t try to connect through any social media site.

I was in doubt but thought to give it a try and called her name. The moment she turned back, I and she were like statues and kept staring at each other for next 2 minutes.

I broke the silence and said Hi…

Friends Meeting Each Other [ffm] [fffm]

I graduated college this December and thought it’d be a great idea to have all of my friends and family together for a low-key graduation party. The three most important guests were my best friend from high school, Sarah, my college best friend, Megan, and my boyfriend, Justin. They had never spent much time together in the past and I was kind-of nervous about them meeting at my grad party. They’re all so important to me, I was really hoping they’d like each other! It turns out that my worries were very unnecessary.

Once all three of them got to my house, I did my introduction and everything was going as planned. They were all being polite and seemed to be getting along really well. Now, I must admit, I am bisexual and happened to have small crushes on both of my girl friends. Having all three of these insanely sexy humans in the same room was making it difficult for my mind to stay out of the gutter. Sarah tried to take off her sweatshirt and the shirt underneath came up a bit revealing a lace bra. We all blushed and I noticed Justin staring as well. But we moved on and pretended it didn’t happen. Later on, I thought I saw Megan giggle and brush her hand past Justin’s dick as she walked by. I thought it was just an accident but even if it wasn’t, I couldn’t blame her. His cock is quite large, and it was definitely obvious through his jeans.

First time fingering my girlfriend!

Okay so we met on facebook on day one exchanged numbers and talked for a little bit. The next day we met we sat behind Circle K for HOURS just talking getting to know a little about each other. Nothing too juicy there but the next day, day three when I went over to her house it was just her there and we were talking like normal but that quickly escalated to making out. Soon I had my hand in her shirt feeling her amazing tits. By that time I was rock hard and wanted more! So I unbuttoned her shorts and stuck my hand down her pants and instantly felt that she was soaked. As I started to play with her pussy she pulled my cock out of my basketball shorts and started stroking my cock I was in heaven fingering her soft tight pussy feeling her juices all over my hand I started to pre cum! Next thing you know her dad pulls into the driveway and im left running out the back door hopping a fence with my cock out hard as a rock LMFAO

My FWB’s boyfriend encourages her to invite me over. [MF]

*
skips to sex

I generally have to travel for work no more than Monday through Friday, but not that long ago, I had the “joy” of having to stay through, and work through, the weekend. Nothing crazy, just a normal 8-9 hour shift on Saturday and a bit more on Sunday, but enough to thoroughly disrupt my routine and take me away from my then-girlfriend, now fiance.

What was worse is that although I have permission to sleep around a little, my former FWB in town had just gotten a boyfriend. I hung out with the two of them once some time before this story, and although my former FWB was flirtatious and even handsy, there was nothing to indicate what was about to happen.

Anyway. It was Sunday and since we had started early in the morning, it was early afternoon when I was finished with work. I texted my fiance to just talk, but she was busy with some homework, so I texted my former FWB to see if she and her boyfriend wanted to hang out again, but he was busy with his own stuff so I said, NP, I’m going to go and work out, let me know if you two want to meet up later or something.

My straight bodybuilder friend and I have the same kink! You won’t believe this!

I bought an old mansion and converted it into a modern, state of the art private gym equipped with a full spa & other amenities. Getting the place together wasn’t easy or something I could do alone so I hired people to help with odds and ends.

Jeremy was a friend I met at another gym in town and I promised him a free membership to my gym if he helped out with the opening. He was one of the people who helped unload, build, and position all of the equipment. He was around 5ft 8in and 240 pounds of pure lean muscle. Jeremy looked like he walked right off the cover of “muscle magazine” and at 25 he was well on his way to being a professional bodybuilder in no time.

Out of the 9 guys I’d hired to work for me Jeremy was by far the most reliable and enthusiastic about seeing the gym open so we spent a lot of time together. On most nights, when everyone else had gone we would talk for hours sharing beers, joints, workout tips, and stories about anything.