Losing Bets


“I’ll make you a bet,” Giovanni said. I looked over at him hesitantly. “I bet you our team will win tonight,” he said, and I thought about it, our team never wins, though.

“But our team never wins.” I said, and he smirked. “What are the terms of this bet?” I asked.

“If you win you get a hundred dollars. If I win you have to do whatever I want for an entire week. I have the house to myself all next week, and you know how I hate being home alone.” He said a wicked glint in his eyes.

“You realize that our team never wins right? So you’ll definitely lose this bet, and I’ll pocket a hundred dollars and all you get is to watch me dance off into the sunset with a hundred bucks, right?” I said, and he nodded, not looking convinced at all.

“If I win though, I get to tell you what to do for an entire week.” He said, smirking. I nodded, and we shook hands.

I am totally pocketing this one hundred bucks!


“I’ll see you at nine, okay?” Gio said, and I nodded frowning. How had I lost this bet? It was totally not even fair! I needed that one hundred dollars. Gio decided that I would spend the week with him, all night and day starting tonight, since we didn’t have school for the week. I don’t know how we suddenly won goddamn football game, but fuck everything.

I sighed and got ready to go, knowing that if I didn’t show up a little early he’d worry. Gio is funny about me; he’s always been funny about me. Gio looks at me as little shy Erik, good enough for me. I mean I am little, barely one hundred and twenty pounds, and a startlingly short five foot four. My hair is longer and blonde, and my face is slim, totally that of a girl. I’ve got pretty blue eyes, and ‘sexy’ lips according to a couple of people I hang around with.

I’m one hundred percent gay, but no one fucks with me about it. Probably because they are scared of Gio, honestly, but I’m happy with not getting my ass pounded into a pulp of blood and guts, so I’ll go with it.

Gio is tall, around six foot three or four, with two hundred and ten pounds of straight muscles. He has dark, medium length hair, and bright brown eyes, deep enough to make you drown. His cheekbones are sharp, and his skin is cocoa coloured, and beautiful. He is the exact opposite of me, in every way.

To say I’d never thought about Gio in a sexual way would be a lie, because he’s basically the star of all of my wet dreams. I keep it hidden well, though. I don’t check his dick out in the locker-room or stare at his ass when he’s standing in front of me. I may be a little guy, with an innocent look, but I’m certainly not innocent at all.

In all honesty, I’m a dirty little slut.

Okay, well I’m not a slut, because I’m a virgin, buuuut… I’m pretty close. My thoughts tell a whole different story entirely. If you counted how many times a day I thought about being pounded into something by a hot guy, you’d think I slept with everyone.

If I wasn’t ultimately terrified of having something larger than a tiny dildo up my ass, I probably would be sleeping with everyone. Buuuut… I’m ultimately afraid of big things… being anywhere near my asshole—at all. It’s probably—no it is—a really stupid fear considering I know what it feels like to take something up your ass, but I just prefer it to be small, and self-inflicted so I can control what I feel.

I sighed, and played with my hair in front of my mirror, blowing my hair out of my eyes tiredly. I bit my plump bottom lip and considered putting on some lip gloss, but decided against it, considering that it’d be a little gayer than normal for me.

I finally deemed myself fuck-able and walked out to my car and drove down to Gio’s house.

I wonder what he’s going to make me do, I thought slowly. Maybe he’ll do something sexual, but I kind of doubt it… he’s very straight. Besides, I wouldn’t want his dick in me, would I? I laughed at myself, and then sighed. Of course I want him; I’d be a retard not to. His dick is really big, so I know it’d hurt like hell… but maybe it’d start to feel good like with the small dildo I bought back in June… thinking about it had me partially hard so I had to think about something else.

He’s definitely going to make me clean his room, I know him. And he’s going to make me cook for him. And do his homework… I didn’t think it’d be that bad, so I just sighed and pulled into his driveway, and got out of my car. Gio’s got money, everyone knows it. His house is the biggest house on the block, and he’s proud of it. It’s a large brick house with four windows on the front side of the house, and one above the windows for the attic. He’s got eight bedrooms on the top floor—or rather his parents have eight bedrooms, as he reminds me every time I mention it—and two bathrooms on the top floor. The bottom floor had a living-room, garage, dining room, den, a large bathroom, and study. They have a basement etimesgut escort they renovated to be a mini-apartment for their one and only darling son, Giovanni. In his own right, Gio is kind of a golden boy, you see. He’s done a lot wrong, but his parents never seem to find out, and if they do they just don’t care about it. Gio’s apartment is nicer than my entire house, and I had spent many nights in his house because he didn’t like me walking home late at night, because of where I live.

I walked to his door and before I even had time to knock he had the door opened, and he pulled me in then slammed the door shut.

“You’re early.” He said quickly and I shrugged, and watched as he smirked. “Well since you are early, you can get started early.” He said, and motioned for me to follow him. I did as he said, and he led me to his apartment, and then led me to his personal bathroom. “Change into the outfit on the back of the toilet.” He said, and I looked at him confused, and nodded, then walked into the bathroom and shut the door behind me. I walked to the toilet and picked up the clothes. “But, make sure you shave first, Erik. Shave everything.” He called and I looked at the door confused. I sat the clothes down on the counter and found a purple female razor sitting on the side of the tub with some females shaving crème. I sat on the side of the tub and wet a washrag, and wet my legs, then rubbed the shaving crème on my legs.

I slowly ran the razor along my leg, carefully trying not to cut myself. I’d never really shaved before, but I didn’t badly injure myself, so I guess I did pretty decently. After I got done with my legs I shaved my d!ck and balls, making sure to get every tiny microscopic hair. Then I did my happy-trail and my underarms, and my arms. I took the opportunity to also shave my ass, since I never really have the privacy to do it at home. Thankfully I’ve never really had a lot of hair anyway, so it wasn’t a hard task. After I was done with all that, I turned to the clothes and pick up them up and turned to the toilet.

I sat them down on the seat of the toilet and picked up the first thing, which I guess is supposed to be a shirt but it looked more like a bra. “GIO WHAT THE FUCK IS THIS?” I yelled out.

“Shut up Erik and put it on.” He said calmly.

I growled lowly, and managed to get my body into the shirt, and realized… wait a minute… “THIS IS A FUCKING CHEERLEADING UNIFORM!” I cried out, and he laughed and I could practically feel my dignity falling away.

“Just put it on, and don’t argue with me. I own you for a week, remember?” he said, and I huffed angrily. Since when did I ever lose a bet to Gio?

I sighed and picked up the next object… a black thong. “GIO THIS is,” I started angrily, but he cut me off immediately.

“Put it on.” He said, and I huffed angrily again, then took off my pants and underwear. The thong fit perfectly, and the dark colour seemed to make my pale butt look subtly bigger, and rounder. I ran my hand over it, and was startled by how soft and feminine I looked in the mirror.

The next thing I didn’t even tell him what it is, because he knew. A very, very short cheerleading skirt without the underwear things attached to them. I deadpanned, and put it on, then turned to the mirror. “Erik, now I want you to put your hair up in some feminine way, I know you can because I’ve seen you do it.” He said. I growled and put my hair up in quick pigtails. “And make sure you use some lip-gloss. There are a couple colours that I took from my mom, so you pick.” He said. I huffed, and it blew my bangs up into my eyes, but I didn’t care. I took the darkest of the colours, a deep purple colour and painted my lips with it.

I went to open the door and he stopped me, once again. “There are some tennis shoes and thigh high socks. Put them on, and then you can come out.”

I sighed and sat down on the toilet and picked up the socks, and sure enough they came right up to my thigh and the longer this went along, the more I could see myself being femme. I mean, it’s nothing I’ve not thought of before, but it’s frigging weird. After I put it all on, I walked over to the full length mirror and gasped when I looked at myself. I surprisingly looked really… hot.

Since this whole thing began I was fighting back an erection, but when I saw myself standing in Gio’s bathroom in a slutty cheerleader costume with sexy thigh highs on, I couldn’t help but get hard.

The initial shock of seeing my hairless legs, and the outline of my ass, and the way my extremely pale skin looks voluminous and bright.

“GIO WHY DO I LOOK LIKE A SLUTTY CHEERLEADER,” I screamed, slamming the door open and staring at him. His brown eyes narrowed at me, and I could see his eyes raking over my body, and it made me blush, and look away. I hadn’t noticed that he’d moved from the door… but he was shirtless, his dark skin looking beautiful under the light, and I couldn’t otele gelen escort lie it turned me on.

“Because you’re hot as hell like that.” he said, and I blushed, brushing his comment off.

“Fuck off, perv.” I said angrily, huffing and poking out my lip a little so as to pout. “I can’t believe that you are making me dress like this.” I said, keeping my arms crossed across my chest.

“Aw, Erika—Erik, you look hot.” He said.

“Fuck you!” I cried out, looking away from him as my face flamed red. He doesn’t understand how bloody embarrassing this is.

“Erik, you’re gorgeous, don’t be embarrassed.” He said, and took my hand and turned me to face him, forcing me to look at him. I could barely meet his eyes, but I advert my eyes and kept them locked on the suddenly interesting wall of posters. “Erik fucking look at me.” he said, and put his hand on the side of my face and forced me to look at him.

“This is embarrassing.” I muttered and he put his hand under my chin, and then tilted my head up, so I was looking straight at him.

“I want you.” he said, and I jumped, my mouth dropping a little. “I figured that if you looked and felt like a girl it wouldn’t be as weird for me, you know?” he said, and I blushed, my arms suddenly feeling really cold.

“G—Gio, don’t fuck with my head, man.” I said, and he sighed deeply, and then slammed me against the wall hard. I couldn’t help but make a startled moan as he pressed his jean-clad erection against me. “Fucking hell, Gio what are you—doing…” I trailed off moaning as he attacked my neck with his teeth.

“I’m marking you,” he growled in my ear and bit down softly on the lobe of it. I moaned and bit down on my lip and turned my head for him to have more room.

“Fuck!” I gasped out as he suddenly turned me around and pressed his dick against my ass. Fuck, he feels big.

“God, Erik, you are so fucking sexy. Your ass looks wonderful. I know you aren’t a tranny but hell, you’d make a damn good one.” He said, and I blushed, and pushed my ass back into him. “God that ass, babe, you have amazing ass. This skirt gives me the best view ever.” He said, and grabbed it in his hand, kneading it in his palm. “So firm and soft, did you shave your ass? Fuck that’s hot.” He said.

I nodded and bit my lip. Gio touched my shoulder softly, and I turned around to face him shyly. “Erik, I don’t want to force you into having sex with me,” he said slowly. “I want you to have sex with me because you want to. If you don’t want to, then we can just hang out and stuff. I really want you though.” He said, and I bit my lip, blushing brightly and thinking. I’ve always had a crush on Giovanni, I’ve always had dreams about him bending me over and fucking me hard, bending my body in ways I didn’t know it could bend…

“W—will you be gentle?” I asked him slowly, shyly, whilst looking away from him. I felt my face flushed bright red, and my mind was spinning. He feels so fucking big, holy shit. It’s going to kill me. He’s so hot, though. His hair is falling just the right way, framing his dark face, and his eyes darker than oblivion, tracing over my body, making me hot and shy.

“Of course, Erik.” He said, and I gnawed on my lip for a second before I looked at him hesitantly, feeling his larger hands on my sides, holding me close to him, as if he was afraid I’d run away like a scared puppy—granted I wanted to do that.

“T—then we c—can, but you h—have to be gentle.” I said, and he nodded, and kissed me on the lips softly. I moaned into his mouth and sunk into his warm body, my arms wrapping around his shoulders as I stood up on my tippy toes. His hands were rubbing my hips, getting dangerously close to my round ass.

Our lips moved together in sync, while I felt a little shy, but I loved feeling his lips, hands, and his body against mine. I moaned as he bit my lip rougher than I was used to. I couldn’t lie; I love the feeling of him rough housing me a little. It was a nice change of scenery from the way he treats me like porcelain, and it made me feel sexier, hotter, my skin burning in just the right way. He grabbed my ass in both of his hands, and lifted me up, and I wrapped my legs around his waist, his hands playing with my ass.

He slammed me back against the wall, and I moaned, my tiny d!ck rubbing against the silky material of the thong. He rubbed against my ass, and I moaned again, my body feeling like it was on fire. “Haaa… Gio shiiit…” I whined out, pulling his hair roughly as I lost control and came…all over myself.

“Christ, Erik, your sensitive.” He said, laughing in my ear as my body shook. He bit down on my neck hard, and I gasped. “You can get down on your knees and suck my dick,” he said, and I blushed deeply, getting down on my knees in front of him as soon as he let go of me. I felt the stickiness of my cum in the front of my panties, but I didn’t want to even bother with them, so I just focused kızılay escort on unzipping Gio’s pants and taking them off him. When I saw his dick, hanging down in my face I almost choked.

It’s long, hard, and thick, the skin looking velvety, the tip poking out, dripping pre-cum a little, and I immediately leaned forward and licked the tip. Immediately, the best taste I’d ever tasted enveloped my senses. “Uhhh Erik yeah, suck me baby.” He said, and I blushed, taking his d!ck down my throat. I wasn’t sure I’d be able to do it, but in the end I took over half of his big, hard dick in my mouth.

I bobbed my head on him, slowly, sloppily, and he sighed, noticing I didn’t know what to do. “Can I take control babe?” Gio asked, and I nodded, and he immediately weaved his fingers through my hair, and started slowly thrusting in and out of my mouth. I gagged but didn’t protest as he slowly started picking up the pace.

He slowly eased over half of his d!ck down my throat, and I got the hang of controlling the gagging pretty fast. I couldn’t help but moan every once in a while, while he was fucking my mouth because I loved it. I loved feeling vulnerable to him for some reason. My d!ck is hard as a rock, straining against the thong and my palm because I was trying to keep from coming again. This entire thing made my body go fucking haywire; I couldn’t tell you anything about me right now. I had never felt so sexy or slutty in my life, granted this is only the first time I’ve had sex, or done anything slutty before.

At this point my body is as foreign to me as Lebanese. The feelings running through me are foreign, as well, and they are controlling everything, controlling my body, my thoughts, and my pleasure. I’d never felt this good in my life, and he hadn’t even fucked me yet.

As if sensing my train of thought Gio grabbed me by my arms and threw me through the air, and I couldn’t breathe… until I landed on the soft bed. “Fuck!” I whined, propping my body up with my elbows as I watched him come over to me.

“Ready?” he asked me softly, crawling on top of me. I nodded, not thinking about the pain, only thinking about how good it would feel to be full, to be used, and to be his slut.

…Hell, he’s turned me into his slut, and I’ve only been here what, an hour and a half?

He pushed my legs open and moved the thong to the side, and I didn’t even bother with being embarrassed, at this point, he’s seen every inch of me and made me come in them, I mean honestly, hiding it would take more effort than I could give at this point. The entire time I’ve been fighting letting completely go for fear of embarrassment, while fighting for embarrassment. I mean, Gio has known me since kindergarten, we shared a cabin at summer camp and we had shared everything since, I guess that I hadn’t thought that I would share my virginity with him too, but honestly I love this even though I’ve been fighting it.

Instead of blushing when he pressed a cool, slippery finger against my asshole I moaned, and opened my legs wider. I’m not going to fight against it anymore, I’m his fucking slut, and I might as well just accept it. I saw an evil glint in his eye, and felt him push the finger in, and I moaned loudly, already wanting more.

One finger turned into two, and soon he was scissoring my asshole with his fingers, preparing me for him. When he was done he looked down at me, and kissed me softly, pulling my lip into his mouth to bite it. “Babe, do you want me to use protection?” he asked, and I swear I thought about it before I shook my head no.

He’s not got any STD’s I hope; I think but don’t say it. I’m sure he’d never put me at risk like that, and he’d never do it to himself either. I didn’t really understand why I immediately said no, before I really thought about it, but I didn’t have time to think about it because he had grabbed my thighs—I secretly hoped that it’d leave finger sized bruises so I’d not be able to ever forget it—and pressed his tip against my tiny little hole. As he pressed in, he kissed me softly, trying to distract me.

It didn’t fucking work, because the farther he pushed his d!ck in me, the more it hurt. I let out a tiny cry of pain, and willed myself to relax around him. The more I tense the worse it’ll hurt, I try I chide myself, but it didn’t really work. Gio was careful with me though, he slowly, very slowly made his way into me, pressing loving, sweet kisses all over my face, neck, and lips.

“Fuck,” I whined, biting down on my lip and felt a few tears slip out of my eyes. Gio stopped moving and kissed me softly, and I let out a sigh of relief. Fucking finally all the way in, I thought to myself. Slowly I relaxed around him, and he pulled back away from my lips to nibble on my ear.

“Ready for more?” he asked me, and I mentally freaked out.

“You aren’t all the way in yet?!” I cried, and he chuckled and shook his head no.

“I’m only in about half-way, babe.” He said, and I started whimpering but nodded, nerves wracking my body. I felt him inch in a little at a time, and I forced myself to relax. He pulled my thin body up a little and stuck his arm under me, then pressed down a little on my stomach, and pushed more in. This time, I didn’t feel nearly as much pain.

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