Before I tell you about the experience that changed my life forever, let me give you a little bit of background.
My first girlfriend at university was called Katie. We got together in the first couple of months and were together for most of our time at uni. Although I was nervous the first time I met her family, we clicked straight away, and I regularly went back with Katie to her parent's place for weekends and holidays to visit. It was only an hour away from campus and we both enjoyed her family’s company. Although I liked her parents, I developed an especially close bond with her younger brother Joe.
When we first met, he was eighteen and in his last six months of high school. I quickly came to understand that he had been having a rough time of it. He was skinny and had grown his brunette hair out long. School can be tough if you don’t properly conform, and some of the meaner kids used to mock him for looking more like a girl than a boy.
After he told me how the other kids treated him, we talked about how he could stand up for himself more and I tried to be a mentor to him in terms of not taking shit from people. I’m a confident guy and had the philosophy of ‘fuck what anyone else thinks’, a mantra I tried to instill into him as a way of handling his classmates. I might be blowing my own trumpet, but I think I helped him develop an attitude that enabled him to get through that last year, and maybe even enjoy it.
This whole experience made us really close, and when I came back with Katie, Joe and I used to go see horror films together (which Katie refused to watch) or hung out playing Xbox while she was getting ready to go out. We used to chat about all kinds of shit, and he’d regularly message me to catch up or ask for advice.
My story picks up about fourteen months later. Joe was nineteen, had left school, and was enjoying life much more, getting more confident and seeming happier in himself. At the end of term, Katie invited me to stay at her parent’s place over the Easter break and we headed back there for the week. I always enjoyed staying there and it was nice to catch up with Joe face-to-face.
One morning, towards the end of our stay, Katie suggested we go into town for the day with her parents. We invited Joe, but he said he’d rather stay at home. The rest of us piled into the car and headed into town. We’d been there about an hour when I got a notification on my phone. According to an email from the university, I hadn’t handed in my coursework before finishing for Easter and was therefore going to get a failing grade for the assignment. I let out a string of expletives. I had fucking handed in my assignment - the admin monkeys had just fucked up again.
I told Katie I needed to head back to check on my laptop that the assignment had been uploaded properly. She offered to come but she seemed to be having a good time hanging out with her parents. I told her to stay, kissed her, and headed back to her place alone.
The taxi dropped me off outside her parent's house, and, starting to worry that maybe I hadn’t uploaded my work properly, I let myself in. I took my shoes off and headed upstairs to Katie's room, taking the stairs three at a time, rushing to open my laptop and discover my fate.
I pushed open her bedroom door and stopped suddenly. Joe was standing there in front of her bedroom mirror. He turned to face me and went pale. He had mascara around his eyes and his eyelashes were long and dark, his lips were bright red with lipstick and his long brunette hair was tied up in a ponytail. He was wearing the French maid’s outfit that I’d got for Katie for Valentine’s day.
A little white maids hat sat on his hair and around his neck he had a white lace collar. A black bra with white lace and thin straps hugged his petite frame. As I look down, I couldn’t help noticing his completely flat stomach, or how smooth the tops of his slim thighs were underneath a tiny black skirt that was bordered in more white lace. Even though he was wearing white stockings, I could tell that his legs were shaved bare.
His phone was in his hand and even upside down, I could see there was a picture of him in a sexy pose that he’d taken in the mirror just before I had barged in. He looked at me in horror before pushed past me. ‘Fuck fuck fuck!!!’ he said as he hurried out of the door, his eyes filling with tears. I heard him run down the corridor and slam the door to his bedroom.
I stood there, trying to process what I’d seen, all thoughts of my missing assignment well and truly gone. I headed down the hall and knocked on his door.
"Joe?" I said softly. No answer.
"Joe, listen, it's ok, honestly, please don’t stress." I was scratching my head trying to think of something to say. What do you say to your girlfriend’s brother when you catch them wearing one of their sisters’ sexy outfits?
I knocked on the door again and just as I did, he pulled the door open. He’d taken the hat off, and his cheeks were smudged with mascara, but he still had the rest of the outfit on, and I couldn’t help thinking that he looked really fucking sexy in it. My eyes were involuntarily drawn down to his body, taking in his feminine frame in the lingerie I’d bought Katie. “God he really does look like a girl,” I thought.
"Please don’t tell them!" he said pleadingly, "Not mum or dad, even Katie. Please!"
I tried to reassure him, "Listen, I don’t think any of them would care..."
"No!" He cut me off, "Promise! Please, no one else can know!"
I looked at him there, wide eyes full of desperation, hair still tied up in a long brunette ponytail. 'Fuck, he shouldn’t look this hot, it's Joe for god's sake!' I thought. I could feel my cock twitch of its own accord and I silently cursed it, 'What the fuck is it doing, this is my girlfriend’s brother!'
"Of course." I said reassuringly, "I promise, if you don’t want anyone to know, I won’t say anything. But honestly, I think…"
"No, please, you catching me like this is already embarrassing enough, please don’t tell anyone else."
I nodded and he slammed the door. I knocked again but when I got no answer, I thought it best to leave him alone.
Joe didn’t come out of his room the rest of that day, telling everyone else he felt ill and that he’d had to go to bed. That night I lay there awake, the image of him standing there, so pretty in that lingerie, dolled up in mascara and lipstick. My cock started to get hard again. What the fuck was I thinking?! I turned over and tried to close my eyes to sleep, but the image of his feminine frame in that maid’s outfit wouldn’t leave my mind. My cock was so hard it was aching.
In the dark, I rolled over and started kissing Katie's neck. I slid my hand into her pyjamas and ran my fingers over her clit. She moaned in her sleep, and I pulled her back towards me and started grinding my throbbing cock into her ass. She began to wake up and gasped as I slipped two fingers into her little wet pussy. I slid down her bottoms and pushed my cock into her, running my hands over her body as she turned her head to kiss me. I fucked Katie in the dark, my cock sliding in and out of her as she moaned for me, and the whole time, I was thinking of Joe, and how fucking cute he had looked all dressed up as a slutty maid.
The next day Joe didn’t come down for breakfast. When he didn’t come down for lunch, I started to think that he was going to try and avoid me the whole time I was visiting. I really didn’t want that. Mainly because he was a friend and I wanted to explain that this genuinely didn’t affect anything between us. But there was another reason too. I couldn’t stop thinking about how pretty he’d looked. I hated myself for it, but I’d cum inside Katie last night thinking of him dressed in lingerie. I needed to see him dressed normally to banish those thoughts from my head, or at least, that’s what I told myself.
I Whatsapped him a message to come down, telling him that it was all ok and that I didn’t care at all what he wore, he was still my friend. When that didn’t work, I told him that it might arouse suspicion if he was weird around me. Katie would ask if anything was up, and I might find it hard to lie to her.
That last message convinced him to come down, and I heard footsteps descending the stairs. He came into the living room where we were all sitting watching TV, telling us all he felt a little better. He sat in the armchair furthest from me and refused to meet my eye. Katie was sat on the sofa with me, engrossed in some crap show we were watching with her parents on Netflix.
I sent Joe a message.
Me: Hey, honestly, don’t worry about it, please, we’re cool.
Joe: I can never look you in the eyes again, I’m so embarrassed.
Me: Why?
Joe: Because you caught me looking like…. that!
Me: Well, yeah, but honestly, it could have been worse.
Joe: How?!
