Dressed Up For Trouble

My name is Erik and this story took place during a costume party my friends and I attended a few years ago. My friend Kevin and I became best friends after we found out that we played on the same World of Warcraft server. Since then we were inseparable. We spent all day hanging out together and quested on-line even more often.

So yes we are complete nerds and we love it. In time we met even more guys in town who were into on-line gaming and our geeky posse grew. Eventually we got so into the game world we started talking about BlizzCon, costumes, the whole fantasy experience.

So finally after so much talking and planning it was Kevin who convinced the six of us to make proper costumes and go to BlizzCon and experience it all for ourselves. Unfortunately we never did make it, instead we settled for a locally organized, fan made version of BlizzCon. For a couple of weeks we were discussing costume ideas and helped each other make them if we couldn't buy the ones we wanted.

The idea was however, that we each go as one of our actual game character, which was a problem for me because it so happened that all of my characters were female. It was Kevin’s idea and he was once again the one to push that I suck it up and dress up anyways, “It’s not like anyone is gonna recognize you anyways,” he said. So for the next week all I heard was how “I look feminine like a girl anyways so I can pull it off” and that the reason I made all my characters female “was because I'm secretly a crossdresser and love women’s clothes” etc… Finally after they promised to stop teasing me, I agreed and the costume “we” settled on was that of a Blood Elf mage.

For those who don’t know what that is, it’s a long red dress with golden designs and open down the side, thigh high black boots and black gloves all the way to the elbow, elf ears and a blond wig; it even came with a prop staff. The whole thing ended up being a lot sexier than advertised and much more revealing than I thought it would be, and the first thing I did when I first tried it all on was to blush like never before and feel terrified that my friends are gonna see me like this. But, I did suck it up and that’s how I went. I was expecting the worst from this bunch of jerks when they saw me but knowing that teasing me would just make me not go, they were actually ok and didn't give me too much of a hard time.

The whole party was great and we were there for hours, since I do actually have a feminine physique and my voice was pretty high for a young guy, plus the make-up and wig covered up a lot, nothing gave me away. By the end of the night I was having a blast not even noticing that everyone we met thought I was a girl. I even got hit on once by some nerdy twenty year old. I haven’t even realized how much fun I had pretending to be a girl until much later, it felt pretty natural, I guess a lot of role-playing games have that effect.

One thing I did notice was that Kevin, who was dressed as an elf rogue, all in black and his face hidden, was spending a lot of his time staring at me; so much even that it made me feel a bit embarrassed. I couldn't see his face but his blue eyes were on me every time I looked.

As the party wound down we headed off to Kevin’s house where some of us were gonna spend the night and ended up chilling in the basement watching movies and smoking pot, most of us still wearing the costumes, especially me since I had nothing to change into. When I asked Kevin if I could borrow something more comfortable of his to wear he said sure and led me to his room on the second floor.

As we went up I tripped on the stairs and fell on my ass, not easy for a guy to walk up stairs even in small heels, especially while a bit stoned. Kevin and I laughed and he took me by the hand like a gentleman and led me to his room. Once in I said I couldn’t wait to change and he told me, for the first time that night, how good I actually looked. Standing there looking at my costume he smiled and didn't say anything for a while, but the silence made me feel uncomfortable. He then came closer and looking kind of squirrelly took my hand in his. I didn't know what to say or how to react; all I could do was blush and feel really nervous.

“You look really beautiful Erik,” he said and he stepped aside giving me the view of the mirror on his closet door as he turned on the light by the bed. He stood beside me and said “I couldn’t keep my eyes off of you all day, and when that older guy hit on you I was actually jealous.” As I looked in the mirror I had to admit I did look pretty good. With my thin build, smooth and practically hairless skin, long waves of blonde hair and the red and purple make-up that Kevin brought me accenting my green eyes and light complexion, I was stunning in the soft light.

I turned to Kevin and asked what was on my mind all day “You really wanted to see me wear this girly stuff didn't you? I mean, it was all your idea,” this time he was the one to blush but he smiled and nodded. His bright blue eyes looked playful but there was something else there I didn't recognize at first and then it hit me, he was turned on. I'm not sure why since I have never even thought of a guy in any sexy way, but it made me feel good and as he moved closer for a kiss I didn't resist. It was the first time I had kissed anyone, and the fact that it was a guy and my best friend was so intense I got hard in less than a second.

I thought we would be worried about others walking in on us but we haven’t even considered it, we just kept kissing and it felt incredible forgetting about everything else for a while. After a bit Kevin pulled away and smiling he got on his bed and took of the top of his costume waving me over to him. Strangely enough I wasn't nervous anymore, so I joined him on the bed and lay on top of him as I went for his lips and started kissing again. As he put his hands on my butt I felt his bare chest and his muscles, of the six of us he was the only one to have any and a nice tan too.

He started to caress my rear with one hand and my leg with the other, all of which made me feel even more like a girl than I had already felt all day. We kissed lightly at first, neither of us having any experience at it, but eventually our tongues started sliding past each other making us even hornier.

It was then I finally moved my hand down to his crotch and felt the bulge in is pants. He moaned and smiled against my lips; he then pulled down his pants and moved my hand down over his cock. I couldn’t believe how hot and soft it was in my hand, even through the thin glove it felt hot, I squeezed it and it moved in my hand as it got even harder which made me giggle in a girly voice I had gotten used to.

We lay side by side as we kissed and I gently stroked his cut seven inch dick, until he tensed up and started coming. He quickly grabbed my hand and started pumping his cock with it cumming even more and quietly moaning with his eyes closed. As I watched him cum all over his chest, his sperm soaking through my glove and the smell of his musky cum filling the room I started getting harder myself.

After his orgasm passed Kevin looked at me still moaning and smiling and did something I hadn't expected. He took my hand with the cum soaked glove on and brought it right up to my face, his hot spunk rubbing right off on my lips and cheek and held it there making me smell the salty cum which made me even more excited, my completely hard six inch cock was now painfully pressed against his leg. I began saying something when he stopped me closing my mouth and motioning to be quiet so others downstairs wouldn't hear as he laid me on my back and reached under the dress to pull of my underwear. He started to stroke me gently as he caressed my leather boots.

After a while he lifted both my legs, placed them on his shoulders and continued to masturbate me. I closed my eyes and moaned quietly as he kissed my thighs and stroked my cock. Before I realized he was lying between my legs and finally took my cock in his mouth while stroking my balls. When I looked down at him his eyes were on me, enjoying the sight of his dressed up friend, flushed and hot, moaning, lipstick smudged.

He reached up with two fingers and put them in my mouth for me to suck which I did eagerly still tasting his salty cum on my lips. When I felt like I couldn’t take it anymore, my submissive side having taken over, I pulled his hand down toward my butt and placed his slick fingers right against my anus hoping he would do the rest. He looked surprised at first but when he saw me smiling he pushed the first finger in. I was so turned on I didn't even feel any pain and pushed myself down toward it to make it go deeper. Soon the second finger was in and he was working them in and out adding his saliva which made me moan louder.

Suddenly and very unwelcomingly, he stopped, pulled out and got up over to the nightstand where he opened a drawer and pulled out anal lube and condoms. Inside I also saw a dildo which explained how he was so good at sucking cock, he has practiced. As I waited for him to wipe off the rest of his cum off his chest and come back I pulled up my dress revealing my bare thighs and hard wet cock, and gently fingered myself since the emptiness I now felt after his fingers was terrible. I could see it all in the mirror across the room and the sight of black leather boots with heels was incredibly sexy.

When Kevin returned to bed he had a condom on and was applying lube to it, I started to say that I'm not ready for this since the size of his cock had scared me a bit, but he just shushed me and whispered “It’s ok, we’ll stop if it’s too much, ok?” He then lifted my legs, placed them on his shoulders again and slowly started to push his hot cock against my hole. At first I resisted and it hurt but as he forced his tip in and held it there I started to relax. Slowly he started pushing it in more and more. By the time his whole cock was in I was sweating, panting, moaning and biting my finger to stop myself from screaming, but I never asked him to stop, I just couldn’t and didn't even know why.

He pulled out half way, added more lube, and then let my legs down at his sides as he bent over me so that we were face to face. After we kissed for a while he placed his hand over my mouth and started to fuck me. I held on to his arms as he pumped in and out of me looking into my eyes the while time. His beautiful face looked even happier than he usually does and it turned me on more allowing me to relax. I wrapped my legs around his back and relaxed completely letting him do with me whatever he wanted, which was exactly what he wanted in the first place. I have never felt so comfortable and safe with him or anyone before.

After few more minutes of the missionary position we stopped, got up and Kevin pulled my costume off leaving me with just the boots, gloves and the wig. I knelt facing the wall with palms on it, waiting with anticipation for what was to come, leaving my butt exposed as Kevin pressed his cock with cool freshly applied lube against my hole. The relief was incredible but didn't last; soon it was burning again with Kevin fucking me hard pushing his cock in so deep it actually hurt. As I looked over at the mirror I took in the whole scene. Face pressed against the cool wall I looked like a girl, I moaned like a girl and my best friend was fucking me like a girl.

His hands on my hips were pulling me to him; I could feel his balls slap against mine every time he slapped his crotch against my round butt. Strangely, I wasn't surprised or confused, it all felt right. An hour ago I was a virgin fooling around with a costume, now I'm learning things about myself I never knew. Kevin pumped me for a bit more and when he was coming close to orgasm again I stopped him. I pulled of the condom and lying in front of him I took his cock in my mouth. I loved how hot it was in my mouth, still tasted of cum from earlier. I didn't know what I was doing but turns out I'm a natural.

Wanting him in me once more before he came I placed a pillow down and lay my butt on it pulling my legs up to my chest perfectly exposing my ass for him again. He didn't even bother with lube or rubber. With a hungry look on his face he just popped right in and continued to fuck me as I stroked my hard cock. In a few short minutes he grabbed me by the ankles and pushed my legs up hard against me as he started to slam himself against me moaning loudly, squirting hot cum inside me with every thrust. Watching his hard, sweaty chest pump and feeling his cock filling me up I finally reached an orgasm I had been denying as long as I could.

I came so hard the first squirt shot over my head and the rest drenched my face and chest. I continued to pump my cock hard as Kevin fucked me slower now loosing strength, when we finished he pulled out and literally dropped on top of me from exhaustion as I let my legs fall. We lay for a while catching our breath, Kevin’s head lay on my chest hot breath blowing across my hard sensitive nipple.

He was so tired he hasn't even noticed that my chest was soaked in sweat and cum, or maybe he just didn't care. When he did look up at me he wanted to say something but nothing came out, feeling the same way we both just started laughing with what little exhausted energy we had. Within minutes Kevin had fallen asleep in exactly the position he fell on me, all I managed to do was to pull the pillow out from under me before I too fell asleep.

Of course, what we should have done was to get cleaned up, cleaned the house and gone to sleep separately. Because when Kevin’s parents had come back the next morning and found three of our buddies passed out in the basement and the whole house reeking of weed, the first thing they did was storm into Kevin’s room and found us.............Kevin naked lying in my arms, me naked except for the thigh high black leather boots and gloves with a blond wig still barely attached, a pool of my cum between us and the smell of sex in the air, well ….. shocked doesn't even begin to describe it.

Still it wasn't so bad for Kevin, his parents were understanding enough, my parents on the other hand, when they found out what had happened they wanted me as far away from Kevin as possible. I needed to be disciplined and needed to think on my actions, and need to be away from games and computers, so as punishment they sent me off to a camp where I would work for the rest of the summer.

Well…..that trip didn't exactly turn out the way either of us had expected either ;) Read on soon in “Summer Camp Punishment”.