Fantasy Sports Punishment

My two college roommates and I were in a fantasy football league, in addition to league bet we had a side house bet where the loser had to do something embarrassing and every year the stakes seem to grow. The first year, the loser had to rent a tuxedo and take a greyhound bus back home, our second year loser had to wear a pink dress to the fantasy football draft, and this year loser had to buy a maid costume and act as the maid for 24 hours.

I had managed to not lose the first two years, but lost in epic fashion this year, making three straight years there was a different loser. As much as I didn't want to dress as a maid, Mike and Jeff fulfilled their bets and it was my turn for a day of embarrassment, at least I didn't have to leave the house. Being a poor junior in college, I didn't have much money to spend, so I found the cheapest maid costume I could find.

The costume arrived and I pulled it out of the package, it was a lot smaller than it looked online; I tried it on and covered much less than I expected, it barely went to my thighs and if I bent over, well, a lot could be seen. I figured no big deal, I'll just put on a pair of bike shorts for added coverage. I took another look at myself in the mirror, thought I looked ridiculous, and headed downstairs to face my punishment.

Mike and Jeff were already downstairs playing video games when I went down. Both started catcalling and teasing me as I walked down. I was a little embarrassed and wanted to run back upstairs, but a bet is a bet.

"Whoa, what do we have here, this isn't what we agreed to," Jeff said while looking me up and down.

"What are you talking about asswipe, this is the bet, I'm in a maid costume," I replied giving a little twirl I immediately regretted.

Jeff reached out and tugged at the bottom of my bike shorts, "These, they're not part of the costume, you can't just be adding pieces."

"He's right you know, tsk tsk, the bet was a maid costume, not maid costume plus some of your normal clothes," Mike said.

"Are you guys serious? This fucking thing barely covers me."

Jeff let go of shorts and leaned back and smiled, "Not our fault you bought too small of a costume, besides on your small frame your ass almost looks like a woman's."

They were right of course, I'd demand they do the same, the humiliation is part of the bet. I pulled off my bike shorts and tossed them on the couch and glared at both of them, "Are you happy now?"

Mike pulled out his best attempt to do a high cultured accent, "Oh maid, there appears to be some dirty clothes on the couch, please pick them up."

Sigh, this was going to be my day, I went and picked up my bike shorts and returned to my room upstairs. I could feel their eyes on me when I went up the stairs, very self aware they could probably see my ass as I trotted up the stairs.

I headed back down stairs and again Mike and Jeff catcalled and whistled as I came down the stairs. "Fuck my life," I muttered in embarrassment as my two friends continued to whistle and laugh.

Mike seemed to take great glee in ordering me around, "tidy this place up, we don't want it to look like animals live here. And from now on, you'll need to show us some respect, we can't be having the help getting too comfortable and uppity."

"What the fuck are you talking about, this wasn't part of the bet, you guys are dicks," I said with an audible eye roll.

Jeff sat up a bit, "he's right, maids should be respectful and we shall be addressed as sir or we'll have to extend your punishment."

I let out a loud sigh, "Very will sir, where shall I start?"

Mike looked around, "The floors, they need a good vacuuming and then you can get on your hands and knees and scrub them."

"You can't be serious, I have to scrub the fucking floors?"

"Tsk, tsk, we just talked about this, please show us respect."

"Yes, sir" I grumbled and headed to pull out items to vacuum and scrub the floors. They weren't wrong, our floors were filthy, but they were always filthy. We were males at college, we didn't waste time cleaning, but whatever, lets get it over with. I leaned over to plug the vacuum, I could feel the breeze hit my bare backside and hear more hoots from Mike and Jeff. I blushed a little embarrassed but tried to ignore their jeers as I started vacuuming.

I could feel both of them watching me work, getting entertainment out of ordering me around. Jeff apparently found it fun to point out the spots I missed, "don't forget the attachments to get under the couch, leave no dust bunny behind," he said.

I looked at Jeff and gave him a fake smile, "Yes sir," and proceeded to use the vacuum hose to get under the couch. I had to get on all fours so I could get the vacuum hose alway back to the couch, again aware my backside was out for all to see. I sensed their eyes watching me, making me a bit self conscious.

I grabbed the bucket of soapy water and got on all fours and started scrubbing the floor, starting on the opposite part of the floor where Mike and Jeff sat playing video games. I worked my way to couch scrubbing as I went. I had expected Mike and Jeff to move, but they just lifted their legs to the coffee table giving me access to the floor, sighing in annoyance, I started to scrub floors underneath their feet.

I felt Mike shift his legs from resting on coffee table to resting on my back as I scrubbed, "what the fuck man, I didn't agree to be furniture."

"No lip from the help," Mike snapped back, as if irritated I dare challenge him.

"Yes sir," I grumbled and resumed cleaning the floors, Mike's feet resting on my back..

"Oh maid, can you get me a beer?" Jeff asked in a sing-song voice.

"Get me one too, and why don't you have one yourself and take a quick break, you've earned it," Mike chimed in.

I didn't really want to get them beer, but getting off my hands and knees sounded good. I reluctantly stood up and started to head to the kitchen when I felt a smack on my ass, it was Jeff, that bastard.

I returned with the beers and started to sit on the couch, "Whoa, what are you doing? The help doesn't sit on the couch," Mike exclaimed.

"Where the fuck am I supposed to sit, the floor?"

"Yes, right here on the floor between me and Mike," Jeff said pointing at a spot on the floor, "Here you can use a pillow for comfort."

"How gracious of you," I said sarcastically and lowered myself onto the pillow between MIke and Jeff as they played video games. I suddenly felt Mike put his leg over my shoulder, almost using me as an ottoman. Jeff, feeling left out, slung his leg over my other shoulder. Great, now I had to drink my beer with a leg in my way.

Mike gently tapped his empty can against my head, "Oh maid, I'm empty, more beer, and be prompt about it."

"Yes sir," I said as I pushed Mike's and Jeff's leg off me, "you know you guys could help me out."

"Nah, this is funner, and I'm empty too," Jeff said as he handed me his empty beer can.

I stood up and this time Mike took the opportunity to slap my ass as I headed to the kitchen. I returned with the beers and resumed my spot on the floor between Mike and Jeff who immediately flopped their legs back over my shoulder. The cycle repeated a few more times and I was starting to feel a little buzzed. I was returning with another round when Jeff patted the spot on the couch between him and Mike, "Ok maid, you can sit on the couch, but don't get too used to it."

I squeezed in between Mike and Jeff on the couch, they were both taller than me. I was 5'7 and 120 lbs and Mike and Jeff were both about six feet tall with athletic builds. I felt rather small sandwiched between the two as they continued to drink beer and play video games.

Mike set his controller and looked over, "How about we watch a movie" he suggested and without waiting for a response started broadcasting from his phone to the TV. Jeff and I felt a little surprised when he started playing porn on the TV, this was not an activity we normally did together.

"I don't know about this," Jeff said cautiously, it was clear this wasn't planned by the two of them.

"Oh lighten up you prudes, we've all seen porn," Mike responded.

There were no further objections and we sat there watching porn together, me in my silly maid costume felt very exposed. I concentrated on not getting erect knowing my costume wasn't hiding anything. Being so close to Mike and Jeff I was aware of them shifting and glanced over and both were gently rubbing their bulges over their clothes. The battle was lost and to my horror my own erection was now sticking out the frilly bottom of my maid costume.

My new predicament was not lost on Mike, he looked down at my crotch, "Oh look at that little guy, he's excited to say hi."

My cheeks flushed, little guy? At about five inches I considered myself average, but looking at the size of the bulges in Mike and Jeff were sporting, I felt like I didn't measure up. Being exposed as it were, I didn't want to join in gently rubbing. I was just buzzed and horny enough to not run away in embarrassment.

I felt Mike again stir and this time was lifting up his hips and slid off his jeans and boxers, "I'm not going let you be the only one getting fresh air."

Jeff looked uncertain, "you guys are freaks," he said in a less than convincing voice, but even more telling, he didn't leave and continued to sit there gently stroking himself. It wasn't long and Jeff too stripped off his jeans and boxers, his hard cock pointing straight up.

Mike and Jeff were stroking themselves with me in the center, I still wasn't sure about touching myself but at this point I found myself watching them and not the porn on the TV. Mike and Jeff weren't sporting pornstar cocks, but both looked a few inches longer and much thicker than me, with Mike's maybe being slightly larger. What was wrong with me, there was a beautiful MILF being railed on TV in front of me and I'm watching my friends stroke their cocks and comparing sizes.

"Ohhh Maid," Mike sang out while stroking his cock giving me a look.

"No fucking way, I'm not touching your cocks," I snapped back.

Much to my surprise Jeff who had seemed reluctant with all this suddenly chimed in, "Why not? We're not going to tell you and you are here to be our maid for the day, beside you can't keep your eyes off our cocks."

I was fighting conflicting feelings, suddenly I wanted to feel what their cocks felt like, but didn't want to look eager

"Go on, stroke Jeff's cock," Mike commanded me as I sat there still fighting my internal battle.

"Fine, but this is one time thing, and no telling anyone I jacked you two off," I said and leaned over and grabbed Jeff's cock. His cock twitched at my first touch, I could feel the heat radiate from his cock and was surprised by the weight of it. I started working it slowly up and down, his breathing quickened.

I could see precum start to ooze from the tip of Jeff's cock. I worked my hand back up to the head and spread his dripping pre cum around his head and used it as a lubricant. I could feel my dick twitch back and forth with excitement as I worked Jeff's cock.

"Fuck, that's it, keep working that cock," Jeff groaned out in encouragement.

I started picking up the pace, stroking his cock and faster and faster. I reached over with my other hand and started playing with his bag balls, gently rolling them in my hand while my other hand continued to stroke and pump his big cock. I could veins in his cock pulse as I worked his magnificent cock.

"I'm close, keep stroking my big cock," he gasped. "Ohhh fuck here I'm going to cum!"

His cock felt harder and I was now furiously stroking his cock trying to work that cum out, I felt his legs start to quiver and then a geyser of cum erupted from his cock splattering on his chest. I continued to work his cock as more and more ropes of cum shot out, I felt my hand getting covered in his hot sticky cum. He finally stopped cumming and I continued to gently stroke his softening cock, cum still trickling down his fat cock.

Mike stroking his cock looked over, "Fuck that was hot, my turn."

"Yes sir," I said meekly. Inhibitions were now lost, I wanted to grab Mike's cock and work it the same way I worked Jeff's. I reached over and grabbed Mike's cock, my hand still covered in Jeff's cum. I gently worked Mike's cock, working a mix of Mike's precum and Jeff's cum all over as lubricant, gliding my hand up and down. Jeff's cock was big, but my having Mike's in my hand confirmed what I thought, Mike was bigger and thicker. His cock felt so big and powerful in my hands, it sent a small shiver down my spine.

I cupped his balls with my hand, slowly tickling them with my fingers. I slowed my other hand and moved it up to his bulbous head, playing gently with it and running my finger softly on the ridge. I felt him let out a gasp of approval and continued circling and teasing his cockhead with my finger before putting a firm grasp back on his shaft, giving him a gentle squeeze.

"Oooooo fuck," he moaned, his body starting to squirm.

I now felt I had control, working his cock, adjusting tempo, working him into a frenzy only to slow down to gentle pace, not letting him cum. I could feel his cock throb in my hand, almost aching for release. I again picked up the speed, up and down I worked.

"Please don't slow down, I need to cum," Mike begged, but again I slowed up taking the power away from him and gently played with his cock, tickling the head waiting for him to catch his breath, enjoying every moment of his cock being in my hand.

Again, I slowly started building up the pace, working my hand faster and faster over his large shaft. Mike continued to squirm and moan but he was now intent on cumming and taking charge, "Work that cock, get that cum out," he growled.

I strengthened my grip on his cock, stroking faster and faster, my own breath increasing as my heart rate jumped. I could feel my cock twinge with excitement as I worked Mike's cock. Suddenly Mike shifted his Hips his cock now pointing straight at me, he grabbed my head pulling it over his cock, me now looking straight at his huge cockhead. I moved my hand from his balls to his shaft and now both hands were working in unison, pumping his big cock.

"Get ready, oooh fuck, I'm going to cum," he gasped out. His whole body and grip on my head tensed and ropes of cum started shooting out, hitting me directly in the face. I could feel hot sticky cum dripping down my face. A large glob hit my lips, instinctively I flicked out my tongue and licked cum splashed on my face, it was bitter, salty, but a hint of sweetness to it.

I couldn't take it anymore, my cock was aching and I reached down to give myself relief and one or two gentle tugs was all it took and I shot my load all over my stomach. I felt him relax and let out a sigh and lay back on the couch, a look of ecstasy on his face. I finally released his softening cock and sat back on the couch myself, breathing heavily.

Breaking the silence Jeff sang out, "Oh maid, this won't do at all, there is a huge mess of cum on the couch you'll need to clean up."

"Yes sir, but fuck, give me a minute here," I said still out of breath. We all three chuckled a bit relaxing in our post nut glow.