The Best Day of My Life

The past few years have been crazy, when you consider who I was before it all began. I've graduated college and have a fantastic job doing something I love. But none of it was what I would have expected, at least not before the day that changed my life.

My name is Harley. I was 19 years old and a freshman in college. I was pretty athletic and in great shape, but too thin to make it onto any of the college teams. No matter what I did, I couldn't pack on any muscle. You would have probably described me as wirey. 5'10" and 140 lbs of mostly muscle, with long blond hair about a foot past my shoulders. Kind of like Thor's skinny brother, Since I couldn't get on a team to make friends, I had joined a fraternity instead.

Freshmen were required to do a lot of work around the campus every month to pay for the chapter's rent. So I spent a lot of my spare time on Sunday's cleaning up at the bars on Main St after wild weekend nights when the normal staff just wasn't enough to get the job done.

Things had mostly been going great that year until the middle of the second semester. My girlfriend, Lucy, broke up with me right after Valentines day. She didn't really say why either, only kept saying something about how I wasn't the kind of guy she saw herself with but that I would be great for someone else. I would have been down, but Alpha Tau Omega had an annual tradition which sounded like exactly what I needed. Every spring they threw a special party with one of the sororities from a school across town. But this wasn't just any party. Oh no...

Each brother was paired up with a sister from the sorority and given a room to do with as they pleased. Had Lucy not broken up with me I would have taken a pass, but now that I was single I was eager to see if it really lived up to its reputation. Our chapter president, Todd, called a house meeting to discuss the upcoming event.

"Ok boys, I think we all know why we're here. Its time for the Spring Smash Bash!" Todd declared, to a chorus of cheers and howls. "But we have some new rules" he continued. "The world is changing, and we have to change with it. After all, we don't want to have any complaints that would get us shut down. In order to make sure everyone from Alpha Tau Omega and Pi Kappa Alpha is on board with what we have planned, and everyone consents to the activities, each of our brothers and each of their sisters are going to write down what they are ok with. You'll be given the letters from the sister you are paired with and she will be given yours. Each of you will get the chance to agree to what is being asked of you, or to back out."

There was a little muffled laughter in the room at this point. I kept my composure but had to agree with my brothers. It was very unlikely any one of us was going to change our minds. What college guy was going to turn down sex with a sorority girl? After the meeting was over, we were all sent to our rooms to write our letters. There were to be five of them and one would be delivered each day this week before the party on Saturday night. My excitement gave way to mild panic. What do I say? Only two girls had ever gone all the way with me and its not like we ever did anything crazy. Plus, I didn't want to scare my girl off with a creepy request. So, I tried thinking of what she might like best and made those my requests to ensure she would show up. I wrote how I liked to be on bottom, take things slow and gentle, a lot of foreplay, things like that.

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Monday morning came and there was an envelope under my doorway. It was my first letter from my match for Saturday night.

'My name is Sam' it read. 'and I LOVE oral sex. If you consent to oral sex with me, order a tequila when you go to the bar tonight. If you do not consent, order a beer.'

So far so good, I'd be happy to have her go down on me. After classes I met some of the guys from our house at The Vine, our favorite bar. Mostly because it was less than a block walk from our house. I ordered some Patron and joined them at their table. I noticed everyone else had a glass of clear liquor too. No one mentioned it or asked what anyone else was drinking, but it felt like we may have all been given the same instructions. I wondered who was watching us to see who was in and who was out. It didn't matter though, because no one was drinking beer.

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Tuesday morning and another letter under my door when I woke up. I almost choked on my tongue when I read it.

'Sam again. I've also always wanted to try anal sex. If you consent to anal sex with me, order another tequila when you go to the bar tonight. If you do not consent, order a beer.'

Was she serious? I had never had the courage to ask a girl for that before, but of course I was up for it. I only had a couple of classes on Tuesdays and Thursdays, so I went back to the frat house to study and get some homework done that afternoon before heading out to The Vine.

Once again my brothers were there, and once again we seemed to all be drinking tequila. A few sly smirks as I put my glass down on our table. I think everyone else was starting to figure out the drink connection too. We didn't stay too long, we never do on weeknights. The place was pretty empty anyway aside from one other table. They looked like they were probably jocks, but I didn't recognize any of them.

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Wednesday morning and to no surprise there was a third letter under my door. After all I had consented to both of Sam's first two requests.

'Hi, its Sam. So I'd like to be discreet about what we do this weekend. And I figure the best way to manage that is if you wear a blindfold. After all, you can't talk about me to your friends afterwards if you don't know who I am. Is that ok? If you consent to wearing a blindfold, order a tequila when you go to the bar tonight. If you do not consent, order a beer.'

Not at all what I was expecting, but I could see her point. No pun intended. Its not something I would have picked, but I wasn't going to turn down the things she was offering me in her last two letters over it. I was no fool. So another day of classes, another trip to The Vine, another table full of my frat brothers drinking tequila in a mostly empty bar.

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Thursday morning, I hadn't gotten a ton of sleep because I was starting to get both a little excited and a little nervous. I probably would have been even more nervous had I known what was going to be in the letter waiting for me under my door.

'Sam again. I was so glad to read in your letters that you prefer I be in charge and how much you like to please your partner because it gives me hope that you'll say yes to my next request. See, I've got a thing for bondage and I'd love to tie you up. Nothing extravagant, but can I handcuff you? Pretty please? If you consent to wear handcuffs, order a tequila when you go to the bar tonight. If you do not consent, order a beer.'

Now this should have been my first clue that something was up. But at the time it didn't even occur to me that I had written all of my letters before getting any of hers and she should have been doing the same. So she shouldn't have known what mine said when she wrote this. But I was too taken aback by her request. My sex life until now had been so vanilla. Mostly missionary sex, sometimes cowgirl. A little fingering. A few blowjobs. And the night before Lucy dumped me she had me go down on her for like an hour.

Still I was 19, single and horny as hell. So you better believe I had tequila again on Thursday night. So did all of the other guys. But it was another early night. Much like the rest of the week it was just us and that other table of jocks across the bar so no reason to stay late.

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Friday morning and the final letter was waiting for me under my doorstep. I hesitated a bit before opening it because I was nervous what might be in it. After all, she did seem to be escalating things a bit with each day's request. After a few deep breaths, I opened the envelope.

'Hi Harley, its Sam again. I hope you're as excited about tomorrow night as I am. I do have one more request, I saved it for last because I'm a little nervous about asking. You might not be into it, but I really really hope you'll give it a try since you've come this far already. I think girls are so much prettier than boys, and it would just make me all wet if you would agree to cross-dress for me. Please say yes! You can just do it in the room so no one else will even see it! If you consent to dressing like a girl for me, order a tequila when you go to the bar tonight. If you do not consent, order a beer.'

Wow. I was just stunned and didn't even know how to react at first. But she sounded so excited about it. I didn't really have any kinks myself that I was aware of, but nothing was sexier than a woman who was super into what was happening. And its not like Sam was asking to shove something up my ass or anything else that would hurt. So it was all harmless, right?

I honestly couldn't even tell you what happened in classes that day. My thoughts were all pre-occupied with this last request of Sam's. What kind of dress would she want me to wear? Would I look good in it, even passable? After thinking about it I realized that as skinny as I was I did sort of have more of a girl's body than a boy's. Albeit a flat chested girl.

The Vine was totally packed that night, being the start of the weekend. Luckily one of my frat brothers got there early so at least we had a table. After my second tequila I started talking to this really pretty Asian girl Robin. Things seemed to be going really well, at first. I went to the bar to get us a couple more drinks and when I looked back I saw Lucy was there. And she was talking to Robin. They saw me looking their way, looked at each other and started giggling. I'm not sure what that was all about because Lucy was gone by the time I made my way back over there. The rest of the night Robin seemed a lot less into me than before. Had Lucy cock-blocked me? She had no right to be mad, after all she was the one who dumped me. In the end I didn't worry too much about it because I had a sure thing set up for the next night.

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Finally, it was Saturday. Spring Smash Bash day. The day that would change the rest of my life, I just didn't know it yet. Everyone slept in a bit after having a good time at The Vine the night before, and then we spent most of our day cleaning the house up for our guests. We ordered pasta for dinner and while we ate, Todd explained how things would work that night. Each of us would be assigned a room. Only the upper classmen had their own rooms, so not everyone could use their own. In each room would be any last second instructions, if any were needed based on what the couple had agreed to. I was assigned to room 1 which belonged to Marcel, the chapter treasurer.

After dinner I quickly showered and then headed to Marcel's room. As expected, based on Sam's request on Friday, there was a box waiting for me with an envelope on top of it. According to the instructions there was a tube of cream in the box for me that I was supposed to spread over all of my body hair and it would take about 5 minutes to remove it. I wasn't expecting this. It was one thing to wear a dress, but removing all my hair would be pretty noticeable to everyone else the next day. I didn't see I had much choice to it at this point though, so I got undressed and applied the cream. After 5 minutes I wiped myself down with a wet towel, and sure enough all my hair came with it. To be honest it felt really nice. I kept involuntarily reaching down to stroke my bare legs because their silky smoothness was just wonderful.

The rest of my box contained my outfit, hair ribbons, makeup and a blindfold as we agreed. And there were hand restraints in the middle of the room with chains running in each direction to the desk and bed respectively. I would have to do those last, because there was no way I could get dressed or put a blindfold on once I my wrists were handcuffed. The dress was a blue and which checker pattern and came with white stockings that went halfway up my thighs. I used the ribbons to tie my long hair into two pony tails and then sat down to see if I could figure out how to apply makeup.

I started with the bright red lipstick since it seemed like the easiest thing to use. While I was rubbing it on my top lip and then puckering, like I had seen women do on TV, I could hear the music starting in the house. Some kind of club beat, maybe MeleeFresh? A good idea as we probably didn't all want to be hearing each other's noises all night. It also meant that the girls were probably arriving and I should hurry up. I wasn't really sure how to use everything else, but I managed to brush on a light layer of eye shadow and a little blush without making a mess and then I stepped back to look at myself in the mirror. I kind of looked like a blonde, slutty Dorothy from The Wizard of Oz. And I looked good too. Maybe not completely passable, but if I was drunk I'd hit on me.

I got into the middle of the room near the cuffs and slipped the blindfold over my face. It had extra padding that made a great seal, so I couldn't even see any light around the edges near my nose. I was in pitch black. I didn't realize until I tried to put the cuffs on, but the chains were too short for me to grab both of them at the same time while standing so I had to get down on my knees. The first one was easy to get on, but it took a minute to figure out how to one-hand the other cuff around my wrist. So there I knelt, blind and completely vulnerable waiting for Sam to arrive. My heart was pounding so hard with anticipation I thought it might crack a rib. Luckily it seemed like less than a minute before I heard the door open and close.

"Sam?" I asked shyly.

"Shhhhhhhh..." was the soft reply.

Footsteps came closer to me and then stopped, followed by the sound of someone getting down on the floor. I jumped a bit when I felt a hand softly start to caress my cheek and chin, just barely touching me. As the fingers explored my face they brushed my lips. It felt so nice, I think I leaned in a bit.

Sam took that as an invitation and slipped a finger into my mouth. I playfully licked at it, and it was soon followed by a second finger. Both slid slowly in and out of my mouth between my closed lips. Each thrust I alternated my tongue. First I would stick it out so that I licked the underside of both fingers together as they pushed deeper into my mouth. Then the next stroke I would slide it in-between the two fingers. And repeat.

I had never done a role reversal like this, but I was really enjoying it and getting lost in the moment. Sam's fingers tasted nice too. They were a little bigger than I would have expected though. I didn't have huge hands, but I suspected Sam's fingers were a little bigger than mine. Was she a big girl? Was that why she wanted me to wear a blindfold, so that I wouldn't back out once I saw her?

While I was pondering this, my two new friends exited my mouth and left it lonely. I bit my lower lip in a playful pout of disapproval. I could hear the sounds of movement, and then a zipper. Sam must have been getting undressed. After a few seconds it got quiet again and I could feel her getting closer to me. When something brushed against my lips, I assumed we were going to play some more. So I opened wide to allow Sam's fingers in.

What entered my mouth was not a finger.

It was a cock! A rock-hard cock.

What the hell was happening?

My mind started racing. Did this guy go in the wrong room? Did he not realize I was a man? I had to stop him. Had to let him know I wasn't who he thought I was.

But its really hard to talk with a throbbing cock in your mouth, sliding in and out and in and out.

I tried to pull back a little so I could speak, but he grabbed my pigtails like handlebars and kept me in place.

"Where are you going baby?" he asked. Then pulled my head towards him, pushing his swollen head back into my tonsils.

I was completely vulnerable and helpless. With my arms cuffed and me down on my knees I had no leverage to stop him. My mouth was his toy, and play with it he did. Using my pigtails to guide me he slowly rocked my head back and forth on his cock. All the way in, most of the way out. But never letting his head escape my lips.

In

And out.

And in.

And out.

Each stroke was just long enough to catch my breath, but never long enough to get a sound out to let him know he had made a mistake. He just kept rocking my head back and forth, dragging my tongue along his dick in each direction as he enjoyed his 'date'. It was definitely bigger than mine. I was decidedly average. I couldn't tell how long he was because the whole thing didn't fit in my mouth. But he was easily thicker than me, and so incredibly hard. You could have put up drywall with this cock. And the rhythmic dance in my mouth continued.

In

And out.

And in.

And out.

I was starting to drool, because he never kept the head of his cock out of the back of my mouth long enough to both breathe and swallow. So I had to choose breathing. All that spit was just making it easier for him to slide in and out of me. He started getting deeper with each stroke. Never forcing himself down my throat, but always testing its limits to see if he could slide in easily.

As much of a panic as I was in to stop this, there was just nothing I could do. Its not like his cock tasted terrible, it was actually kind of nice just like his fingers were. With an extra bit of saltiness every time a drop of precum leaked out onto my tongue. And he wasn't hurting me or anything, he seemed to be being very careful to take things slowly and easily while still remaining in complete and utter control and he thrust in and out of my mouth. But the point was I wasn't gay, and so it was wrong for him to have mistaken my mouth for his date's.

So I realized I had two choices. I could either try to fight what was happening even though that would be futile. Or I could help get it over quicker since it was happening whether I liked it or not. I resigned myself to the latter.

Every time he rocked me forward, I leaned in myself rather than making him pull me in. And I began sliding my tongue in and out of my mouth along the underside of his cock in time with each stroke.

"Mmmmmm" he moaned, clearly enjoying what I was doing.

Soon he wasn't guiding me at all, I was just bobbing up and down on his rigid dick all on my own. Swirling my tongue around the head as I sucked. And even though he wasn't the one pushing my limits anymore, his head was getting closer and closer to sliding into my throat with each attempt. I was so caught up in the moment that I was actually pushing it harder all on my own. At some point I think I completely forgot that I didn't want this and was just trying to get it over, and instead started trying in earnest to actually give a good blowjob.

All the while he kept letting out the occasional moan which let me know I was doing it right.

Thrust after thrust kept dripping that delicious salty discharge into my mouth. And as each stroke pushed into the back of my mouth, I started being able to take the tip of it into my throat without gagging. Still not the whole head though, he had a large mushroom tip and I think it would have gotten stuck down there if I tried to force it too hard.

But I kept bobbing up and down, my mind completely gone and my body slobbering on his cock on pure instinct. Every stroke out, more drool ran down his shaft towards his balls. Every stroke in my tongue slide out and tried to scoop at least some of it back up. As I started having more success getting a little bit of the tip in my throat with each stroke his moans got louder.