Your New Life in Submissive Servitude

You're just a normal college student. There's nothing particularly interesting about you or your life. That isn't to say you don't have friends though, and that also isn't to say that your friends can't sometimes be total dicks. Every week you and your friends gather to play games, eat food, shoot the shit, and anything else you can all think of doing that would be fun or interesting. The interesting activity today was a game of poker, and the one who got out first had to participate in "The Ultimate Dare" as your friends called it. Just as your luck would have it, you went broke first, and the burden of the dare falls on you. Your friends had always mentioned how you have very feminine proportions, and that if you were to dress up as a girl nobody would be wise to it at all. So they decided that your punishment for losing was to go down to the local sex shop in the sluttiest outfit your friends could concoct and buy the largest dildo you could find.

The outfit they picked out for you was brutally degrading; plaid miniskirt that barely covered your ass, tight black panties that squeezed your cock harder than you ever could, black crop top that had "beauty" written on it in pink and covered in glitter, black thigh highs, a pretty pink choker, a small handbag to hold your things in, and to top it all off they got a female friend to do your makeup, and much to your dismay she did a bang up job. You couldn't take 10 steps without feeling the skirt ride up and show your ass off to every passerby within a 10 foot radius. Your face was more red than a stop sign, and your heart was being so fast you could swear you were going to die. You knew deep down that if you didn't come home without the prize your friends would never let you live it down, and maybe they'd have you do something else that would be even more embarrassing. You shook your head and continued making your way down the street towards your destination. After what felt like an eternity you finally made it to your local sex shop: Loveless.

As you walk inside the store your nervousness increased tenfold. Darting your eyes around the story you saw couples, single women, single men, all of which were walking around and picking up items like it was a clothing store. You felt more than out of place here, and that was plain as day on your face.

"Can I help you, mam?" A voice spoke from behind you, causing you to jump.

You turn around, and in a panic stutter out in the most feminine voice you could muster, "I-I'm fine, th-thank you..."

And as quickly as she appeared she walked away, seemingly believing that you truly were a girl.

As you began to collect yourself, you started to wonder why you put on a fake female voice, it's like anyone would judge a boy for wearing an outfit like this nowadays, especially in a place like this. You finally managed to calm yourself down and began walking around, looking for the treasure you sought after (although calling it a treasure may be a bit inappropriate).

You walked over to a section labeled "for the risk takers". You were astonished by how girthy some of these could be, and also impressed that someone could take these at all. The idea of putting one of these inside of you scared you, but slowly you began to ponder just how good it might make you feel. The idea of putting something this large and thick inside of you made your heart race, and it made you cock hard.

You snapped yourself out of those delusional fantasies, and grabbed the 20 inch model called "The Stallion". As you held it in your hand you began to study it. You slowly positioned it like a pornstar would when giving a handjob, and began to put your mouth on it. However, before you could even pantomime the action you had the mysterious feeling you were being watched. You quickly turned around to face the stalker, but you failed to see anyone. Coming back to your senses you remembered your mission and began to head for the counter to pay.

You hand the dildo over to the cashier who scans it and plops it into a paper bag with no markings whatsoever. At the very least nobody will see you walking home with something like this. She turns to you and says "that'll be $51.24." A visible look of shock took your face. $50 for a dildo like this? that's outrageous. Regardless, you fork over the cash and take your prize and your receipt, stutter out a goodbye and go on with your day.

However, as your heading for the store exit you feel a hand on your shoulder holding you in place. A man leans down and whispers in your ear "meet me behind the store. I know your secret." And just like that he walks off. All the nervousness that left your body before has crawled right back to you.