Bitch Anatomy 101 Ch. 01

Tim nervously traced a razor around his hole and crack as he craned his neck to check his progress in the mirror. Once he was done, he grimaced as he slid the lubed up enema tube into his hole. Though tense and nervous, he was done with time to spare.

You may think Tim was preparing his tight 21 year old hole for a hook up, but the truth is he was getting ready for his side hustle. Between work and school, there wasn't enough time for anything too labor or time intensive, but filling in as a stand-in patient at the medical school had seriously helped him pay rent. Plus, he was straight as an arrow.

He had done it all. Blood tests, x-rays, physicals, and all matter of external reviews. He was far from the only one and it was cutthroat filling the openings. Naturally, he put his hat in for things a little hastily, not quite reading the fineprint...or even the large print. Hence, his prepare work for a rectal exam.

Sure enough, when he did find out what this entails, he did try to back out. He didn't like the idea of a half dozen or so med students playing around down there. But, he knew a few things at this point. First, if you canceled you were seen as unreliable. Second, he needed to make rent.

Dr. Alice had assured him they had everything covered to ease his anxieties. His upper torso and head would be on the other side of a separating sheet. He'd have headphones with soothing music on to drown out any comments. Further, one of Dr. Alice's colleagues, Dr. Sanchez, would be on hand to ensure no one was too rough with their prodding. Assured of his anonymity and comfort, he said fuck it and agreed.

He arrived at the university, checked in, and was led to the exam room. A slanted  cushion was on the table to keep his ass elevated and keep him comfortable. Dr. Sanchez did a quick check to ensure Tim had prepared correctly, thanked him, and drew the curtain.

"We'll get started in about five minutes. Try to focus on the music and relax. If it hurts or you otherwise want to stop, let me know ok?"

"Got it, thank you."

Soothing lounge music pumped into Tim's ears. He could hear muffled talking but couldn't make out any words. After a while, Dr. Sanchez reappeared behind the curtain and removed Tim's headphones.

"Ok, we are going to start now. I will be applying lubricant to your anus and slowly place my finger in to conduct the examination. Rest assured, I've done this hundreds of times and you shouldn't feel any pain. I know it may be hard, but please try to relax and do not clench."

"Got it. Thank you."

Tim took a deep breath, questioning how he ended up here and simultaneously finding the humor in it. Before long, he felt cool liquid being applied to his hole and more muffled speaking. A finger made it's way in, pushing at the edges of Tim's hole. He tried to remain calm as best as he could. It felt more weird than anything.

The finger danced along his prostate and he felt a jolt through his body. It felt...weirdly pleasant. Dr Alice told him about this and said it was normal. He bit his lip and thanked his lucky stars that his dick was pressed into the support.

Several students took their turns and Tim was now fully erect. Every force of his mind and body was focused on remaining still and not making noise. It was like they were teasing him, giving him bizarre pressure and then just quitting.

Barring any do overs, by his count he knew there was one student left. The music pulsing through his headphones abruptly stopped and another song came on. It was a pretty fast techno song and referenced how much the female singer chanting about taking it in the butt. Tim felt tense. Was this a fucking joke? He decided against saying anything,  not wanting to reveal his identity.

Unbeknownst to Tim, the students who had gone already had left. Dr. Sanchez, in a huge break of protocol, had left to take a phone call and left the remaining student alone in the room.

Two fingers entered and rushed towards Tim's prostate, as in a race against time. Finding it, the fingers curled in waves. Tim twisted his head in pleasure as the fingers went in and out, finding the spot, curling, and repeating. Then suddenly, they were removed and the normal song came on.

He heard muffled speaking again. A single finger inserted and did the exam, with a slight curl indicating it was the same person. The finger was removed. More muffled talking.

Everyone cleared out, the headphones were removed, and Tim was thanked for his participation and patience. It felt weird talking to Dr. Sanchez after what had transpired. For all Tim knew, it could have been him doing it.

After Dr. Sanchez left, Tim stood and noticed the paper sheet he was laying on was damp. His, still hard, cock had leaked. He quickly discarded it, got dressed, and booked it out of there.

He felt a weird mixture of being violated but was still glowing from the arousal. He, of course, wondered who had done it...but it was a dead end. It wasn't like the other tests where everyone saw each others faces. There was a confidentiality factor with this and he knew he would likely never know. Tim wondered if it could have been a prank.

He caught a bus and got off a few blocks from his flat. He needed a drink and didn't feel like being around others, so he popped into a corner store, procured a few tall cans, and started walking home down an alley.

With just a few steps to the end of it, he was suddenly pulled back and shoved up against the wall.

"Don't move" a voice, obviously disguised by some sort of voice modifying contraption barked. The guy felt a lot bigger than Tim, and caught off guard and scared as he was, he complied. He felt his phone lift out from his pocket, some swiping happening, a call started and aborted, and then placed back. He was hopelessly confused and terrified.

Suddenly, the stranger pulled Tim's ass into his crotch. Tim could feel a sizable bulge,  an obscenely erect cock.

"Please....no" he begged.

"You seemed to like my fingers just fine, Timmy"

Tim froze as the unknown man rubbed his clothed cock all over his clothed ass. The guy was getting into it, forcing Tim into the wall with long slow thrusts.

"Imagine how good this would feel up there." He added as he wrenched one of Tim's arms around and made him feel the cock through his pants. Tim meekly obeyed and his eyes widened as he felt up close how big and meaty it was. He absent-mindedly felt it up and down.

"Just want one last look for tonight" he said as he yanked Tim's pants down to his ankles. "Mmm, yeah, Timmy boy. Imagine me all the way inside."

Tim felt a sharp slap on his ass and then just like that the guy was gone. He collected himself, still bent over against the wall with his naked ass out. His pause was broken by some asshole shouting down from their window.

"Uhhh...no...not in this neighborhood, fag! You want me to call the cops?!"

Tim tucked his embarrassingly still erect dick back into his pants and booked it fast, not slowing down at all until he reached his flat. Once there, he slammed one of the beers immediately and opened another. He tried to wrap his head around everything. He had been finger fucked and loved it. He had been sexually assaulted in public and his dick was still rock solid. He had felt up another guy's bulge like a horny slut.

He paced back and forth anxiously for several minutes before being interrupted by his phone rumbling. Unlocking it, he found a text from an unknown number.

Beneath the message "until next time" there was a video of his assailant fingering his ass at the university. The white hands ruled out Dr. Sanchez.

"WHO THE HELL ARE YOU?! STAY THE FUCK AWAY FROM ME!" Tim responded.

"Someone you know" the answer came back with an image of the cock that had been pressed up against Tim in the alley.

Tim honestly felt weak seeing it. It was so big. He had never really had a gay thought before. It was just....amazing.

"Drink it in, Timmy. When you're ready, I'll give that tight ass of yours a test drive."

"Seriously, who the hell is this?" Tim replied, feeling the resistance drain from him.

"I'll give you a hint. Someone who could tell it was your ass from the birthmark you have. Want another hint? Your ass should probably still be slick. Jam two fingers in there and send me a pic."

"Fuck you, I'm not like that!"

"LOL. Your teeny dick seemed pretty hard when you were rubbing up against me. Think I didn't see it?"

Tim threw his phone down in disgust. He thought about blocking the number, about getting out of the program, blowing the whistle. Still, he had to fuckint know who this was.

He steadied his phone on some books, climbed into bed, laid sideways, and did what was requested. Even after he had the pic, he desperately tried to recreate the pleasure but just couldn't angle it right. His mind turned to other things in the house he could use, but then he felt shame and simply sent the pic after cropping his head out.

"Good work, Tim. We were in the same graduating class. For the next hint, video time. Two fingers in your snatch, one stroking your little guy. Do not cum."

Tim shrugged off the repeated jokes about his dick. As if he didn't already know? Fuck this guy.

This request was a bit harder. He lad on his bed, head down, ass up, and got the job done with his phone recording from the nightstand. His fingers were approaching the spot now, but not quite there. He spied a container of candles he had gotten from his parents and thought how they'd feel. He moaned as he continued to pump, finally forcing himself to stop. He groaned and sent the video.

"Very nice. Can really tell you were thinking about my dick. We were in the same PE class. Still can't guess? Three fingers in your ass, two in your mouth and suck em"

Tim fished some lube from his drawer to accommodate the extra finger. He moaned into his fingers as he explored his ass, exploring different rhythms. He drooled over his fingers as he sucked. Feeling like it was going too far, he stopped and sent the video. He was so caught up he didn't bother cropping.

"Very nice, Timmy. You've won. Come get your reward." The stranger responded while also pasting in an address not far at all from Tim's flat.

"Text me when you're out front. I'll buzz you in. Don't keep me waiting."

Tim got dressed and flew downstairs. On the walk, he desperately googled the addresss, trying to find out who lived there. He didn't recognize any of the names that popped up. He stopped a few feet from the door, wondering what was driving him. Was it the mystery or the chance of more pleasure? He buried his thoughts and sent the text.

"Apt 7g."

The door buzzed and he took the elevator up. He nervously knocked on the door and waited. When it opened, his former classmate Gary stood in the door frame with a big ass grin and his big ass cock hanging out of pants.

He would have never have guessed. Gary was in his gym class senior year. He must have seen Tim's ass birthmark then...but it was and is a pretty small blemish. Gary had obviously been paying more than a little attention to him. He had talked to him maybe once or twice. He had a reputation as a bully but had never bothered Tim.

His thoughts returned to the giant dick in front of him. It was amazing. The dictionary definition of a perfect porno star cock...nine inches, thick as all hell, and a big ol cut cockhead. Below it hung two massive balls. Tim felt week again. His cock stiffened and he felt his ass clench and release on its own, like it had a mind of its own.

"Come on in, Timmy. We got a lot of catching up to do." He said as he led Tim in and closed the door.

Tim felt like he was past the point of no return. He kept eying that swinging cock, knowing that whatever Gary had planned for tonight would probably happen with Tim as a willing participant. He took one last look at the door before obediently sitting next to Gary on the couch.