It was time for my five-year colonoscopy.  I made my initial intake and information appointment.  At the meeting, I met yet another new Doctor at the practice.  This would be my fourth colonoscopy and my fourth Doctor.  I guess spending your days pushing things up other's asses is not as glamourous as it seems.

This guy seemed okay enough but asked several more questions than the prior Doctors had.  After fifteen minutes of questions, Dr. Jones stated, "According to your records, the prior doctors have had some trouble dilating you.  You seem to have a rather restrictive anal ring."

"What exactly does that mean?" I replied.

"It means that we should have you come by the office twice a week for the next two weeks to loosen you up some."

"How would you go about that?"

"We use anal dilators to stretch you out comfortably over time.  We'll get you started here today and give you what you need to do the rest at home."

"So, why do I need to come back by the office if I'm doing it at home?"

"We need to make sure that you're making good progress.  There's no point in doing it if it doesn't have the desired effect."

"Okay, so how do I do this?"

"My assistant, James, will be right in to go over the procedure and to help you with your first insertion."

At that moment, my cock twitched.  It was involuntary, like the way you sometimes jump a little during a scary movie.  You know, when the killer shows up in the background and takes a swipe at the heroine.  I equated it more to that than a sexual twitch, like when a gorgeous girl comes into view.

As the Doctor was leaving, he off-handedly said, "You'll need to strip from the waist down and lie on the table.  James will be right in."

Again, the pulse occurred, and this time I grew to about half-mast.  As I was in my own thoughts, trying to figure out why this was happening, James knocked and then entered the room.  

"Hi, I'm James," he offered.  "Did they not tell you that you had to be naked from the waist down?"

Clumsily I began to remove my shoes and socks as I muttered, "Yeah... yes, sorry, I was just thinking about a work thing."

"No problem, I have to get ready too.  Take your time.  You are my last appointment of the day, so there's no hurry."

With my shoes and socks removed, I unbuttoned the top of my jeans.  As I slowly lowered my zipper, James opened a plastic case that contained six dildos.  I know that's not the medical term, but I've seen dildos, and that's what they were.  They weren't veined and didn't have the flaring head, but they were dildos.

I slowly lowered my pants and underwear as I gawked at the display.  They were all smooth with rounded ends, much like a broom handle.  The smallest of them being about the size of my pinky in circumference.  As my eyes moved along them, they finally came to the largest.  Holy crap!  That monster was fatter than my own decent-sized cock.

I must have looked like a fucking idiot.  As I stood there with my pants around my ankles with my eyes as big as saucers.

James smiled as he tried to assuage my fears.  "Don't worry, you only have to get the third one in comfortably within the two week period."

"O... Okay," I stammered.

"Now, why don't you finish removing your trousers and underwear."

I did as he suggested and tossed them on the chair haphazardly.

"So, there are many positions that you can assume to make this easier.  Probably the best for you while doing it on your own is while lying on your side.  Are you right-handed or left?"

"Right," I answered as I stared at my hands for a moment like they were foreign to me.

"Okay, so lie on your left side and curl into the fetal position a little."

I did as James instructed, and once I was in place, he sat on a stool at the end of the bed.  I was beginning to feel what I imagined was a bit of the self-consciousness that women do at the Gynoclolgist.  I was looking straight ahead and waiting for the penetration to begin when my concentration was broken.

"Mr. Jones... Steven... I need you to raise your right leg up until you can put your foot on the table."

Popping out of my own head, I did as he requested, only to realize that my previously hidden cock and balls were now on full display, again.  I must have turned an even deeper shade of garnet as I now saw his face.  He was peering at my sphincter like a mechanic replacing a spark plug.

"That's good.  Now, watch how I lube up the smallest dilator.  Make sure that you use plenty of lubrication.  Cover the entire thing making sure to leave a little dollop on the end.  Next, you'll want to place a generous amount on yourself.  My suggestion would be to take your time and let yourself open up a little.  The more that you can get inside initially, the easier the entire process will be."

I just stared at him like a blubbering idiot, not hearing much of anything that he'd said.  My only thought was that this guy was going to stick a baseball bat up my ass.  Fortunately, in one way, my whole line of thinking had me shrunken down to child-size.  At least I wouldn't have to worry about my earlier problem.

Again, breaking me out of my trance, James asked, "Are you getting all of this, Steven?"

"Ye...Yesss!" I nearly shouted in my nervous state.

"Okay.  Now, put this glove on your right hand."  As I fumbled my way through the process, he continued, "I'm going to direct your hand a little as you apply the lubrication to your own anal entrance."

I chuckled a little at that, and so did James, which broke the ice and helped me relax.  With the glove on, I moved my hand between my legs.  James squirted a blob of lube onto my middle finger and then moved it toward my pucker.  Just before getting there, he added, "This is going to be a little cold at first.  But the more you move it around and keep contact, the quicker it will warm up."

I'm a rip off the bandaid quickly kind of guy, so I moved in quickly.  I shuttered a little at the cold.  But even more so at the fact that I'd pressed inside my entrance a little.  

"Not so quick," James uttered as he pulled my hand back a little but kept up the contact.  "Just rub in little circles for a minute with little to no pressure.  That's it, just like that," he added while releasing my hand.

The disgust that I'd initially imagined never materialized as I started to enjoy the feeling.  Again I slipped away, but this time not into the chagrin that I'd previously experienced.  My sensitive star started to reward me for my ministrations.  As I drifted further into my own bliss, I heard, "Uh-hum!"

Embarrassment engulfed me again as I started to withdraw my hand. 

James offered, "Don't feel embarrassed.  I haven't met anyone yet that didn't get a little excited, male or female.  For men, especially, anal penetration is particularly stimulating.  As we begin the insertion of the dilater, you may feel yourself beginning to enlarge.  This is completely natural, as the prostate is alongside the rectal cavity and is very sensitive to stimulation."

"Okay," I replied quickly in an attempt to keep things moving along.

"Give me your hand.  I'm going to line it up and press it a little inside.  Once I get it moving in, you will take over and press forward slowly.  The goal is only to stretch your anal ring, so you don't have to go very deep."

James pressed the smallest phallus into me a little before moving my hand into position.  Once I was in control, I pressed forward slowly.  The effect on my penis was immediate.  It grew rapidly as I eased the small fake cock into my ass.  I was enjoying myself tremendously and had forgotten all about my audience.

As my left hand made its way to my swollen pole, almost of its own will, I heard another, "Uh-hum!"

"That's deep enough," James ordered.

Fortunately, I hadn't quite gripped my prick yet and nonchalantly eased the dildo from my ass.

"Not all the way out.  You want to leave it inside about one to two inches."

"Alright," I answered as I pushed forward a little more.  My fully engorged prick jumped again as I moved forward.  James noticed my plight but chose to ignore it.  Instead, he concentrated on continuing my instructions.

"Now, you'll want to leave it inside you for about fifteen to twenty minutes at a time.  I would suggest that you do this three to four times a day.   After it starts to feel nice and loose, you can switch to the next dilator in the box."

"Alright, so when do I come back?" I inquired, looking through my spread legs.  With my dignity already departed, I kept my finger on the dildo as my prick pulsed in need.

James stared at my predicament for a moment before replying, "I have you set up for Wednesday and Friday night this week.  We can also schedule you for Monday and Wednesday next week.  With your colonoscopy scheduled for next Friday, that should be enough stretching to get you ready."

"That will work for me.  These late appointments are perfect for me.  Will I be working with you every time?"

James momentarily stared before answering, "Oh yes, I will definitely be here for all of your appointments," he smiled.

"Take your time and finish up your dilation.  I have some paperwork to complete and will be back in about half an hour.  There are plenty of paper towels over here and a sink to wash your dilator and hands.  You can lock the door to maintain your privacy, but remember that you'll have to leave when I return.  Have fun!"

James locked the door behind him, and I pressed the dildo further into my ass.  My penis was at full mast and pulsing again as I rolled onto my back.  I grabbed my cock in my hand and began stroking it as I plunged the dildo in and out of my ass.  I have to say that it was the quickest I've ever climaxed in my life.  As I lay there with my own cum coating my groin and thighs, I drifted off to sleep.

It couldn't have been more than fifteen minutes when I awoke to James asking, "Are you decent?" as he opened the door.  

Coming to, I attempted to cover-up but had nothing to use other than my hands, which quickly became coated in my own drying goo.  I fell off the bed in my struggle, and James grabbed me around the waist to help me up.  Once I was standing, he asked, "Are you okay?"

"Yeah.  Thanks for the help," I laughed.

James started laughing at me, laughing, and we both were rolling.  In the midst of our amusement, James' hand slipped across my bare ass.  He quickly withdrew both hands as the mirth ended promptly.  The bitch of it was that it felt terrific, and my cock grew a little too.  

James attempted an apology, "I'm soo..." before his eyes focused on my growing penis.  He stared for a moment before turning around and saying, "I'll wait outside," as he shot through the door.

I stood there for a moment, trying to wrap my head around all that just occurred.  As my mind raced, I slowly got dressed and cleaned up my mess.  After a few minutes, I opened the door to find James sitting on a chair down the hall.  I walked in his direction, not knowing what to say.  I stopped in front of him, and his head was down in seeming despair.

"You didn't do anything wrong, James.  I have absolutely no complaints.  If it's okay with you, I'd like to absorb the night's events before we talk any further.  But, rest assured that none of this will be shared with anyone else.  Can we meet somewhere outside of work tomorrow at lunch, maybe?"

With his head still bowed, James replied, "I only get about fifteen minutes for lunch.  How about after work?  Maybe at McGurk's pub down the block?"

"Sure.  Will six o'clock be alright?"

"That's fine," James answered as he tilted his head up to look at me.  "And again, I'm so sorry!"

"There's nothing to be sorry about.  The whole thing was a clumsy accident.  If anyone should be sorry, it's me."  Whispering, I added, "I'm the one who pleasured himself at your place of business.  So no more guilt on your part, understood?"

"Yes."

I walked out the door with my head still spinning and wondering about my own sexuality.  I spent the night wondering if it was his touch or James himself that got me excited.  As I bungled my way through my evening routine, I decided that it was more about being touched in those places by another man.  While James was an attractive man, it was more my discovery of anal stimulation that had me riled. 

Just thinking about it all had me wanting to feel more anal penetration.  Plopping down on the bed, I stripped off my clothes and gathered the dilators and lube.  Following James' instructions carefully, I slowly inserted the same dildo into my slick ass.  I pushed it fully inside myself and then started a fucking motion.

My cock hardened quickly, and before long, I started masturbating.  Just as before, it was a quick ascension to my orgasm.  As I finished coating my chest, I started the pumping motion again.  I noticed that I seemed much looser now and decided to try the next size up.  After a proper lubing, I pressed inside.

The feeling was as intense as my first time, and I began to harden again.  This time I eased it out, deciding that my penis could use a break from all the abuse.  After washing everything, I decided on an early night and fell into a deep sleep.  It had been a while since my dreams were so sexually charged.  The interesting thing was that they were all about James.

I wasn't disgusted by or ashamed of them.  Growing up, I'd always been attracted to women, and men were always friends. It wasn't an anti-gay thing.  I was just a heterosexual guy.  I never even looked at another penis, much less thought of sticking one up my ass.  But now, after yesterday evening's events and my all too explicit dreams, nothing was off the table.

Still, in bed, I reached for the kit and grabbed the second smallest dilator.  With a quick lube, I was inserting it into my back door.  The feeling was phenomenal.  With plenty of experimentation, I realized that it was the width, not the depth, that did it for me.  With that in mind, I grabbed the next phallus in the box.  Lubed up, I lined it up and moved forward gently.

This time my anal ring felt truly stretched, and it was amazing.  I took my time and watched as the semen leaked slowly from the tip of my cock.  While I wasn't a participator in anal sex, I'd heard of people, male and female, climaxing from that alone.  Picking up the pace, I wondered if I could do that.

As I pushed deeper, I could feel my entire rectum opening up.  Between that, the anal ring stretching, and the prostate stimulation, I was getting close.  I was right there, but it wasn't until I closed my eyes and imagined James fucking me that I began to cum.  I felt my juices land all over my groin, abdomen, and chest as I continued the penetration.

It felt so good that I kept it up for another minute or two after my climax began to ebb.  As I cleaned up the dilators, I laughed to myself.  Realizing that I was already on the third size after the first day.  I wondered how much would I be able to take by next week?

After a shower and breakfast, I headed to work.  Stuffing my kit into my briefcase, I was thinking of a late lunch in my locked office.  I worked non-stop through the morning with two thoughts in mind.  The first was how I would approach James about some anal stretching in my bed.  The second was getting the next size dilator into me so that I was ready for James.

At one-thirty, I ate a quick salad for lunch and then posted a 'do not disturb' note on my door before locking up.  It wasn't unusual for any of us to do the same, especially when we were on an important call.  With the door locked, I quickly stripped from the waist down and prepped the third phallus.  

I propped my feet on the desk and dabbed some on my exposed anus.  Easing it inside, I found that I had to spread my legs further apart to gain full entry.  Once I got going, I felt myself loosening a little.  With that one still buried deep, I lubed up the fourth.  I figured that a quick exchange would work best.

I slowly withdrew number three and had number four at the ready.  The switch worked well, and I could get about half an inch of the fourth inside easily.  Leaning back and relaxing, I began putting on some pressure.  As the fourth grudgingly entered my anal ring, my penis started leaking as it pulsed.

The feeling was electric.  It had been some time since I'd felt that level of stimulation.  If I'd have even touched my cock at that point, I'm sure that it would have exploded.  But the best was yet to come.  I was only inside about an inch, but as I progressed deeper, I rubbed against my prostate.

With my entire rectum stretched further than it had ever been, I was already on fire.  With that first touch of the prostate, I understood why so many guys were gay.  I pushed it to the hilt and shuddered as my penis sprayed everywhere.  In the aftermath, I pulled up my underwear to hold the dilator in place because it felt so good.  

I spent the rest of the afternoon with a hardon while enjoying the fullness in my bowel.  When it came time to leave for the day, I reluctantly removed the false prick.  I was unsure if it would stay lodged inside when I walked and didn't want any surprises.  

As I walked to McGurks, I thought of what I should say to James.  My mind ran many scenarios as I neared the pub.  When I opened the door and saw him sitting at a table in the corner, it hit me.  It was the look on his face that did it for me.  He seemed determined and ready to protect himself should I threaten his career.

When he saw me, I was already headed his way.  Even so, he rose, saying, "Mr. Jones, over here," while he directed me with his waving hand.

His stance and was firm, as was his demeanor.  But, it all fell apart when I shook his hand while saying, "Hi James.  Would you like to fuck me?"

He quickly pulled his hand away and fell back into his chair as I sat in mine.  James shook his head back and forth, attempting to comprehend my question.  I simply stared at him while he tried to gather himself.  Finally, he stuttered, "Wha...why would...huh?"

"Are you gay, James?"

Still looking at me like I had four heads, he whisperingly answered, "Yes, but why?"

"You inadvertently changed my world last night.  I was a simple heterosexual until yesterday.  Never knowing of the pleasures of anal penetration or the touch of another man.  Now, I know it was unintentional on your part, but it still changed me.  So, before I go out in the big gay world, I'd like to offer you first crack.  What do you say?"

James finally cracked a smile then replied, "Big gay world? Really?"

"Hey, I'm a newbie.  Cut me some slack.  So, are you in or out, literally?"

"It would be against the rules for me to fraternize with an active client.  If we do this, it would have to wait until after your colonoscopy."

"So you're in figuratively.  It's now about when you'll get in."

"You're crazy!  You've never even tried this, and you're propositioning someone that you only just met last night.  Are you always this direct?"

"Not always, but this is something that I'm pretty sure that I'll enjoy, and I don't want to waste any more time getting started.  So, let's do this," I added as I stood.

Walking away from the table, I turned to James and said, "Come on.  Get the lead out of your ass," then chuckled at my use of words.  As I exited the bar, I waved down a taxi and opened the door just as James reappeared.   He saw me slide into the cab and ran over to lean inside.  

"Didn't you hear me about the rules of my work?"

Grabbing him by his shirt, I jerked him inside and kissed him to throw him off balance.  It did the trick, and he sat down and closed the door.  I gave the cabbie my address before turning back to James and tentatively kissing him again.  A few minutes later, we were at my apartment building.  I led James by the hand, and as we entered my home, I led him straight to the bedroom.

Once there, I stripped myself as he did the same.  We fell onto the bed with me on the bottom and rubbed our bodies together.  Our hardons rubbed all over as our hands and lips wandered.  It wasn't long before I had my legs spread, inviting him to take me.  James got the hint and slid down between my legs to lube me the old fashioned way.

This was another first for me as he flicked his curled tongue against my star.  I was moaning like a dog in heat as he licked his way inside.  I shot all over myself as he continued to burrow deeper.  When I couldn't take any more, I pulled him up by his hair and begged.

James lined himself up and popped the head of his number six sized cock inside me.  I growled wildly as he continually pushed into me until he couldn't go any further.  It felt like an anaconda was parked in my guts, and the feeling was overwhelming.  He stayed in place as our faces met, and our oral onslaught began.

Our tongues dueled for some time before he eased back a little and started a slow, comfortable screw.  I don't know how he lasted so long, given that I felt every vein of his cock, as it moved back and forth.  All I know is that when he finally came, I thought it would come squirting out of my nose.

The way his prick filled every inch of my rectum, his cum really had nowhere to go.  But, I have to say that the warmth and lubrication that it brought were both welcome surprises.  His climax brought about a relaxation that I'd not felt in some time after sex.  I held him to me as we melded into one.

It was so weird that I truly knew what my partner was going through for the first time in my life.  Being a man and having a man as a sexual partner was so freeing.  I didn't have to wonder whether it was good enough or whether he'd actually cum.

James was still at about half-mast as I moved my hips up and down.  He sucked on my nipples as he gradually hardened inside me.  The titillation, if you will, was much stronger than I would have imagined.  I'd never had anyone suck on my nipples before but was enjoying it immensely now.  Feeling his growth, I grabbed his shoulders and rolled us over.

This was a position that I imagine a woman would love.  I know of one of my exes that reveled in the cowgirl.  As I rode James lazily, it seemed to give me a feeling of power over him.  Like I was in control of his pleasure and mine.  In this position, I could rub his cock firmly against my prostate, which was magnificent.

James' hands moved to my chest as I guided his manhood in and out of my wanton hole.  With the continual friction on my prostate, I began to tremble as James' fingers pinched and pulled on my distended nipples.  With moments I shot several streams of cum from my pulsing prick.

As my semen coated James' abdomen and chest, he seemed surprised that I'd cum so easily.  Even though he had to help hold me up as I climaxed, I never stopped my movement.  I had become obsessed with anal sex very quickly, which made me think that I'd always been gay.

With the contractions from my orgasm, I finally began to see some of James' semen leaking around his shaft.  The extra lubrication made my ride even more enjoyable, but it was time for him to take over.  Slowing my up and down motions, I gently turned to face away from James.  I reached back for his hands and placed them on my hips as I moved onto all fours.

James took the hint and knelt behind me to pummel my slippery tunnel.  By far, this was the deepest penetration that I'd had, and letting him take me like that felt somewhat slutty.  But I was embracing it along with this whole new phase of my life.  As I felt another climax build-up, I imagined what it would be like to be a real slut.  I wondered if James could help me out with that.

But, in the present, he was taking care of my needs quite magnificently.  As my contractions initiated, James' grunts became more audible.  It wasn't long before we were both peaking and collapsing onto the bed.  He made a feeble attempt to raise off of me, but I quickly moved my hands to his ass and held him in place.

As he gradually shrank inside my used sphincter, I pulled him even tighter to maintain that feeling.  I was beginning to understand women's frustration with men and their inability to stay hard longer.  I really was becoming a needy slut.  I blurted out, "James, do you have any friends that could come over and fuck me some more?"

"Wow, you are crazy!  Take it from someone with a little more experience and give your ass a break.  I know that you love anal sex, but the rectum wasn't designed for never-ending fucking.  You will already have some pain tomorrow just from what we've done tonight.  Especially since this was your first time."

"I know that you're right, but I can't seem to get enough.  How about if I suck your cock for a while and see if I can get you hard again?"

"No guy, gay or straight, is going to turn that down.  Let's see how you do," James voiced as he rolled onto his back with legs spread.

I quickly flipped over and moved toward my prey.  James was shaved below which, was always a pet peeve of mine with women.  Nothing ruins the mood faster than a piece of hair stuck in your teeth or your throat.  It doesn't have to be baby smooth, but a close trim is a welcome sight.

Drawing on the things that I always enjoyed, I licked lightly across his scrotum first.  The light shudder and rising goose-bumps told me that I was doing good.  As I always did with women, I took my time and enjoyed the taste and feel of him.

It was quite a different experience, but it excited me since I knew what worked for me.  James was mostly soft at about two inches until I sucked the head into my mouth and stretched him.  As I sucked his tool in and out of my mouth, I could feel it grow.  With his tool headed in the right direction, I headed in another.

Licking my way down his semi, I moved a hand up to keep it company.  I let my tongue drift over his sack and reveled in the smoothness.  As I traveled further south, his legs parted and lifted.  With better access to his pucker, I lapped and tickled his entrance with my curled tongue.  Between my fingers on his helmet and my tongue in his ass, James was getting back to tumescence.

"Okay, you got me there, you nymphomaniac.  Now come and ride your prize," James breathed as he pulled my head out of his crotch.  I slowly sat up and slid him inside me.  This time I was a little sore but had no intention of telling him.  Besides, the incredible feeling as I slid down his manhood was more than enjoyable.

This was to be a slow, comfortable screw since it would likely be our last for at least a day or two.  I may have been a newbie at being gay, but I was far from new to the dating scene, and I know people.  James will likely feel immense guilt after tonight and try to keep from seeing me again.  With that in mind, I was getting all the cock I could from him until then.

I lucked out with him as my first.  He was so worried that he caused all of this, that he'd do almost anything I asked.  Plus, I believe that he really like me and was attracted to me. 

This time I felt an all-encompassing fire that spread from my rectum forward.  My prick was stiff as it bounced gently against his abdomen on every downstroke.  James seemed to be enjoying himself as he cupped and pawed at my breast.  Occasionally flicking and pinching my nipples, but never touching my cock.

My climax spread slowly.  Not the normal violent orgasm that most men had.  I kept riding him as I felt it reach the tip of my cock and a couple of short bursts emptied the last of my semen onto his belly.  I wasn't done, though, and kept going waiting for his orgasm to fill me.

I started to grope his nipples in return, and they seemed quite sensitive based on his response.  Each time I pulled or pinched, James jerked a little harder into my sensitive hole.  As I escalated the pressure, he began to moan and roar.  His hands left my chest and grabbed my hips as he jerked wildly. 

Within moments he was again cumming inside me, and I felt the warmth of his juices filling me.  When he finished, I lay down on him and kissed him hungrily.  Now that we were done for the evening, my hope was to keep him from ghosting me later.  I wouldn't know if it worked until tomorrow night at my next scheduled Doctor's visit.  But for now, all was good.

Maybe tomorrow night, I'll get him to fuck me at his work.