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Robert’s Yearly Exam

Category: Anal Sex
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Ok, I have been putting it off for about two weeks; I’m just was having a very difficult time bringing my self to call Dr. Steins office for my annual prostate exam. Maybe the doctor’s name will give you some idea about how much fun these exams are, would you believe ” Frank N. Stein”, pretty scary eh? I’ve got to be fair about the Doc though he is a really good proctologist, but the help he hires to draw the blood for the PSA test—- HORRIBLE at best. They usually have to stick you 3 times before the blood sample is taken, OUCH!

After the blood is drawn Dr. Stein has me drop my skivvies and lean over his, always cold, exam table. Now the really fun part, the Doc who is a fairly cheap SOB, squirts a very small amount of ice-cold K-Y jelly on his rubber gloved covered finger and plunges it into my tight constricted anus. As you can imagine, since Doc is so cheap, I am not very well lubed at all, again more pain!

We have come to the point in the exam, where I know the Doc must secretly enjoy giving pain. He finds my prostate, with much practiced swiftness, and proceeds to poke and probe the poor defenseless organ. I am on my tiptoes now trying to get away from His digital onslaught, but where can I go? The cold exam table has me trapped.

After what seems like many minutes he is finished, truth is he probably only has had his finger in my butt for less than a minute, just seems much longer due to the pain he has inflicted.

“Well Robert everything feels fine” says the Doc, “see you in about 12 months”.

After the 8th ring of the phone Dr. Stein’s receptionist Francis picks up, I inform her that I want to schedule my annual prostate exam. Francis tells me that they are using new procedures and will connect me to Doctors new assistant. “Hi this is Rebecca Jean,” the pleasant voice on the phone says to me. I introduce myself to Rebecca and ask when I might be able to drop by for my “annual torture”, trying to make a little joke. Rebecca responds with a little laugh and explains to me that the Doctor’s office is participating in a new prostate exam procedure as part of an A.M.A. study. She tells me the new exam process is looking at ways to reduce the pain and discomfort of the standard digital exam. She goes on to explain that since this is “all new and somewhat experimental” the cost of the exam will be paid for by the A.M.A.

I’m about as cheap as ol’ Doc Stein so the idea of a free checkup sounds good to me, so I tell Rebecca I will see her on the 23rd of September. “Looking forward to seeing you then, and I’m sure you will find the new exam process a much nicer experience Bye-Bye Robert.”

Some things never change, and one of those, is the wait at a Doctors office.

Oh well, I never read magazines much anyway so the wait gave me time to catch up on current events. While waiting I did notice a couple of guys, who had earlier appointments, on their way through the lobby. Must be my silly imagination but they seemed very relaxed and serene almost like they had been drugged, kind of weird I thought.

“Robert your next”, said Francis. Could be worse I thought to myself only 45 minutes behind schedule, as I walked into the lab area for the blood work.

Damn!! I was pretty pissed!! Wait till I got to see this Rebecca Jean person. So this was part of the new procedure to reduce the “pain and discomfort.” The blasted med-student, Dr. Stein had drawing blood, was the worst ever!! I had to be poked 4 times. 3 in one arm and one in the other before the tube was filled!!

I left the lab and was told to go to the room with the sign “Prostate Preparation” on it. When I got to the door I was ready to rush right in and give this Rebecca person a piece of my mind, but I had to pause. Below the sign saying “Prostate Preparation” was another saying “Private please knock and wait for entry.” I dutifully knocked and shortly thereafter a buzzing sound came from the door handle area and I was allowed to push it open.


Was I surprised when I entered the room! Rather than the harsh florescent lighting found in all doctors offices, this room was lit entirely by candlelight. There must have been 6 or 8 large candles spread around the room giving it a nice comfortably glow. Standing in the middle of the small room next to an unusual exam table was a woman. She extended her right hand and said with a very large smile, ” Hi I’m Rebecca Jean very pleased to meet you.” About this time I thought to myself “nobody like a gripe”, I won’t say anything about the bad experience in the lab. As if to read my mind, Rebecca took my hand firmly and while shaking it said she was terribly sorry for the trouble I had getting my blood drawn. “I’m determined to make sure the rest of your exam is a much better experience”, she said with a wry smile on her face.

Rebecca Jean looked great! She wore a tight white skirt that hit her about mid thigh.

She asked me to please start disrobing. While doing so I continued my appraisal of her. The lady appeared to be very fit; she was slim and appeared to be in good shape. Covering her legs were slick white stockings, her firm and fit legs looked great in them. I could only guess as to what color panties might be covering the absolutely gorgeous butt the tight skirt was showing off. To continue, Rebecca was wearing a snug white cotton blouse unbuttoned far enough to allow a glimpse of her white bra. Her hair was a beautiful red in color, which was a nice accent to her pale green eyes. She had on just the right amount of red lipstick and her cream colored high heeled shoes completed the picture. Oops, I almost forgot there was another thing about Rebecca I really liked. It was the fragrance she was wearing very nice and sexy, I found out just a bit later what it was.

“Robert please lie on the table with your butt as far forward as possible,” she said. Also please use the supports for your feet, they help hold your legs apart and support them during the procedure. “Here goes nothing”, I think to myself as I climb up onto the table, not knowing what is to happen next.

Gee another pleasant surprise the table is soft and comfortable to my back and unbelievably it is even warm to the touch, some kind of built-in heating system I recon. I place my feet into the stirrups, shift my self around a bit and feel pretty comfortable all in all.

“Robert do you like mellow jazz?”

Sure, why I asked?

“All part of the relaxation process Rebecca replied,” as she turned up a volume control a very smooth sax filled the room. “Some exam” I think to myself, what the heck comes next?

“Robert let me explain this new procedure to you.” “First of all my treatment will last any where from 5 minutes to about 30 minutes, depends on the patient, then Dr. Stein will see you.”

Rebecca continues with information about the procedure she is to perform.

“The AMA is doing a study about how to do a more effective prostate exam, they were amazed to find out that proper stimulation of the gland made early detection of prostate tumors over 100% more effective.” “So rather than the rude poking and jabbing that doctors are so famous for I’m going to apply the new techniques to you, so lay back and relax, and we will get started”

“Sounds like quite an improvement to me Rebecca,” lets give it a try.

Next a warm towel is draped across my groin area covering my penis; I assume this is to provide me a certain amount of privacy. Rebecca then starts wiping the area around my anus with a very warm wet washcloth; I am starting to feel both very relaxed and a little aroused at the same time, a strange combination. Rebecca then tells me if I feel any pain or if she needs to do anything differently during the procedure let her know at once, “everything is great so far” I tell her.

Now she has rolled a little wheeled table up next to the small stool she is setting on. She looks to be in perfect position to access my Southern regions. There seem to be a few items on the table she has rolled over but I can’t tell for sure because a towel covers them up.

Rebecca then reaches under the towel and pulls out a large jar of Vaseline, she deftly unscrews the lid from the jar places the lid to the side. She then dips the closely trimmed nail of her right index finger into the lube.

“Get ready for the pain,” I think to myself, and kind of tighten up my body. Next I feel the lightest little pressure rubbing around my ass-hole and over it, this continues for about two minutes and I really feel more and more relaxed. “How’s the patient doing so far?” Rebecca Jean purrs. “Very good so far” I reply my voice just a bit nervous. “Great” Rebecca says, “Lets continue.” Into the jar her finger goes again, dipping out a fair sized amount of the slippery stuff. I feel her finger again, dead center, of my anus. This time she presses a bit more working the lubrication just into the opening of my anus, my ass hole is tight but it seems to be giving in to her gentle massage. Again Rebecca dips into the jar and continues her work, I’m amazed, no pain at all and my anus, is relaxing more and more due to her expert touch. “You see Robert”, Rebecca say’s “the key is to be slow and patient with bunches of lubrication.” “I now have my finger into you about one inch and thing are going well.” She then began to just wiggle her finger around, not pushing in or pulling out, just a vibration like motion. Damn I’m a happy camper not only am I not feeling any pain but very pleasant sensations are starting to creep up through my anus right to my balls. After about two minutes of the wiggling finger Rebecca dips out more of the Vaseline, this time she coats her entire index finger with the stuff. The tip of her finger slips in easily now followed by the rest, well past the second knuckle. Her motions change now; she is slowly pulling the single finger in and out making the stroke longer until just the tip of her finger stays in my anus on the way out and all the way in as far as she can get the super slick finger to go. This long slow stroke is starting to really excite me and I can’t help the swelling of my cock, I hope Rebecca has not noticed the mound forming in the towel.

“Rebecca I seem to be pretty well stimulated now.” “Are we about ready for the Doc?”

“Oh no, dear we haven’t even started on the real prostate stimulating yet.” She answers. She continued the long stroke of her finger, picking up the pace a somewhat. “Should take another ten to fifteen minutes and you will be just right for the doctor”

“Oh by the way Robert I noticed that you are starting to get an erection, please don’t be at all embarrassed by it.” “This procedure may just give you one of the hardest erections you have ever had, we will discuss what to do about that a bit later.” She said coyly.

All I could manage in response was a shaky, “You’re the boss Rebecca Jean”

“Now we need you to relax and open up some more so we can begin proper prostate massage therapy.” She said. With that she dips into the Vaseline jar with a finger from her other hand and smears the slick stuff all over the middle finger of her right hand never Stopping the delicious in and out motion of her index finger. Now Rebecca pulls out her index finger just so the tip of it is out of my anus, she places her middle finger on top of her index finger forming two fingers flush and parallel with each other. She pushes the middle finger in easily due to her earlier preparation. The tip of the index finger bumps up against the rim of my asshole and it stretches readily to allow both fingers to slid ever so slowly in. Rebecca continues to push until both fingers are all in leaving them to the hilt and not moving.

“How we doing Hon, no problems or pain” She purrs is a sensuous lusty voice.

“Damn Becky this feels unbelievable” I blurt out.

“OOP’s I’m sorry I called you Becky, guess the excitement is getting to me”

“You can call me anything you want Robert, these walls are sound-proof and no one can hear a thing out side of here.”

By now I have a full-fledged boner standing up under the towel, the mellow lighting of the room, the music, the smell of Becky’s perfume filling my nostrils it’s all turning into an unbelievable erotic dream.

Rebecca glances at the towel and said “ok BIG BOY, let’s pick things a notch,” with that Her fingers start a slow piston action getting a little bit faster every 15 seconds or so then slowing down then speeding up again, my anal canal is starting to get a warm glowing feeling that I can’t describe. Two or three minutes of this and my cock are starting to twitch and ache and I’m beginning to think about stroking it.

Now Becky is doing all kinds of things with her fingers. Turning them in a rotating motion, wiggling them, spreading them as much as she can against the tension of my anus—–I’m in a sensual heaven.

Suddenly she pulls them out!!

“Damn!! Don’t stop Becky that feels absolutely great!!” I yell.

“Sorry Honey we only have two more steps in the procedure and you will be done.”

“Well ok if we must, but I have to tell you this sexual tension is getting intense, the skin on my penis is tighter than a drumhead.” “Not to worry babe, we will take care of that for you later.”

“Robert in order for us to properly stimulate the prostate we have to use something besides my fingers. Studies have show that a medium sized dildo is just right for that purpose. May I continue the procedure with my dildo now?”

“YES, YES, YES I said I don’t care what you do, I just need to get some relief soon!”

Now Becky gets a gleam in her eyes and tells me to lay back and enjoy the rest of the ride, she removes the towel covering her tray and picks a pink flesh colored dildo its about 7-8 inches long and 1-1/2 inches in diameter. On the end that Rebecca holds is a round white ball that looks very much like a golf ball, she tells me that it is a golf ball it allows her to hold on the tool and do a good job with it.

I lay back now, ready, willing, and quivering with lust waiting for her tool.

Becky gives the dildo a liberal coat of our favorite slick stuff and whispers is a sexy voice,

“Get ready for the best ass fucking I can give you.”

The head of the false cock is pressed against my asshole at just the right angle for easy entry, Becky, no doubt, did well in her anatomy classes in school. She puts firm and constant pressure on the dildo telling me to relax, and push my anus against the head of the dildo

“Yeah right! Relax,” I say. I follow her instructions and WOW.

Ah perfect!!!!

The dildo starts to slide past my anal opening and eases in bit by bit. The fullness it creates as is squeezes past my prostate makes my cock jump and twitch, “Becky I have to get rid of this towel my penis its burning up”, “its about time” she laughs as she snatches the towel off me and tosses it away.

She slowly moves the dildo into me until a fair amount of resistance is felt, I think about 6 or 7 inches are in and the feeling is delicious. “Your doing great baby” she tells me.

“Lets stroke slow and easy for a while until you get use to it”

“Ok” I say my voice trembling and my heart pounding in my chest. Damn it feels sooooooo good!! Becky Jean knows exactly what do, her experience in giving these procedures tells her exactly how to arouse my prostate to the max.

I have to say it I can’t hold back. “Please, please, please Becky Jean FUCK ME, Fuck me good!!!!!!!!!!!!!!!!!!

“I’m going to give you just what you want and need now baby,” she purrs. The super slick dong slides in and out of me at just the right pace, massaging my prostate, causing me tremendous pleasure. Now my anus is starting little contractions adding to the pleasure, I feel that I will come soon without even touching my dick; I’m amazed at that possibility!!!

“Becky, BECKY, BECKY!!!!! Please stop.” I yell.

She stops immediately.

“OH Robert what is wrong” she asks, “Am I hurting you?”

“NO, NO, NO,” I reply, barely able to talk. “This is the most exquisite sensation I have ever felt and I’m going to come very soon”

“GREAT that’s exactly what we want you to do, then you will ready for the doctor,” Rebecca jean tells me with a huge smile of self-satisfaction.

“Rebecca I have a little suggestion that might be helpful to your procedure if you don’t mind me bringing it up?”

“Robert I am always looking for ways to improve my technique.” “What do have in mind?” She asks with a twinkle in her eye.

“I think this will reduce the strain on your hand quite a lot and add to my stimulation.” I say. “Please stand up, hike your skirt up, and then move in close to me.”

“Robert this is a very unusual request from a patient, but I will do it in the interest of improving my medical technique, lets give it a try”

Becky is standing now her skirt pulled up, the crotch of her black silk panties exposed, noticeably wet with her juices. “Now Rebecca position your self so that round ball on the end of the dildo is pressing against the upper area of your pussy just about where your clitoris is located, the silk panties should feel very nice with the pressure of the ball.”

Rebecca needed no further instruction…she placed the ball on the end of the dong firmly against her sopping panties and started to grind and push. Of course you know all that grinding and pushing was being transmitted directly down the dildo into my ass which now is totally melting with passion, the sensations in my prostate moving right into my balls and my cock. I closed my eyes for a few moments allowing my total sexual sensory system to focus on all the different pleasures I was receiving, then I opened my eyes a bit to notice that Becky’s eyes were now about half closed. Rebecca’s face had the look of total sensual bliss, her red lips spread as her tongue licked them in an uncontrolled sexual dance.

I could take no more!! I grabbed my turgid cock and started jacking-off like a man possessed. After no more than dozen strokes a sharp smack was felt on my hand, shocked I released my throbbing dick immediately and look up to Becky.

“You naughty boy, don’t you know that will make you blind?” she laughingly said to me.

“I guess that’s why my eyesight has gotten steadily worse since I’ve been about 12 years old I replied”

We both laugh as she snatches up my prick with her free hand she starts stroking my aching dick at about the same pace I had been, then Becky tells me, “that’s my job, not yours!!”

Rebecca continued to bump, vibrate, and twist the ball on the end of the dildo into her swollen clit.

I’ve had it I can take no more.

I EXPLODE, cum streams from the head of my cock as Becky continues to work on me, now very slowly and tenderly moving up an down my twitching member I feel waves of intense pleasure course through out my body, my ass clenches and pulls at the dildo increasing my delight. I quiver and tense for a few more moments, and feel completely spent. Becky is motionless now allowing me to calm my sex-racked body. She waits a full two minutes and then ever so slowly pulls the hot dong from my slippery anus, her left hand gently holding my softening penis.

“That was just perfect Robert you should be just right for the doctor now, but there is one small problem”

Barely able to speak, I ask. ” What kind of problem Rebecca Jean?”

“That change you asked me to add to my procedure, that rubbing of the ball against my pussy has me just as aroused as you were a few minutes ago. I was about ready to cum when you went off like a rocket; I had to stop the stimulation of your ass then, for fear of going too far, so I never quite had my orgasm. Can you help me with my problem?”

“Of course Rebecca Jean I will do anything I can,” ……………I looked down at my totally spent dick still being gently held in Becky’s left hand. “I’m afraid that poor guy might take a while to rise to duty again”

“Not a problem at all sweetie, I have everything under control”

Next thing I know Becky bends over and give my spent cock an open mouthed kiss right on its head making sure to get a good taste of my cum which coats it, “you rest little fella you did a fine job,” she says to my penis then straightens up licking the rest of my cum off of her left hand. Rebecca then pulls her skirt up a little bit higher hooks a thumb inside the waistband on both sides of her black panties and slips them off in a flash. Becky comes to the end of the table where my head is, bends over my face and places a wet passionate kiss on my lips, forcing my willing mouth open with her tongue, I suck her tongue into my mouth tasting both her mouth and my cum at the same time I’m intoxicated by the sheer brazen act of this bitch in heat, we kiss non-stop for about a minute and she pulls away.

Becky then takes the black silk panties she pulled off just two minutes ago and places them close to my rather large nose, “baby take a nice deep breathe.” I do just as commanded exhaling first deeply to clear my lungs and then sucking into my lungs deeply the pure essence of this woman. “My God Rebecca Jean the aroma of your sex mixed with your perfume is ambrosia to my nose your pussy must taste marvelous!!”

“Most men love the fragrance of CHANEL #5 especially when it’s mixed with a little pussy nectar, and yes I do taste great”

As fast as a jockey mounting a stallion Rebecca swung onto the table, her head facing my feet she placed her long fit legs one on each side of me kneeling on her knees. As if my face were a saddle she lowered herself onto it for a ride.

I grabbed her firm silk covered thighs and dive between the swollen, lust engorged lips of her pussy. The smell of her panties does not do her justice I plunge my nose and lips into her lapping like mad and filling my nose with her fragrance. Her juice runs in torrents and I truly have never tasted anything so good.

“Oh Robert honey that is soooo soooo good but please, please, please lick my clit now. I was just about ready to get off few minutes ago I MUST COME NOW!!!”

If Becky commands I must obey. I scooted down a little bit with my head to get a better angle of attack at her clitoris, then I gave her all I could, licking, sucking, biting with my lips all focused on her clit and the swollen lips of her pussy. Rebecca then started riding my mouth with the upper area of her pussy, BAMN she went off like an air raid siren giving out a shriek of pure animal joy. Even with the partial sound barrier her beautiful thighs provided, the scream hurt my ears!! When a man eats a pussy he gets a very gratified feeling when he can feel the contractions and pulsations, right on his mouth, tongue, and face of a woman he has brought to a wonderful orgasm. Man was I feeling gratified! Rebecca Jean had just gotten off big time and I felt very good about it.!!

Becky Jean then kind of collapsed on me gasping for breath trying to regain some energy to get up. I couldn’t lick the lovely lips of her pussy anymore because of the way she was laying on me, but as the honey of her pussy juices trickled out I scooped it up with my fingers and licked it off with my tongue. I always say “waste not want not!!”

We got up on shaky legs and were cleaned up and fully dressed in a few minutes; Rebecca Jean called Dr. Stein on the intercom. The doctor came briskly into the room in just a few seconds, flipping on the florescence overhead light. He had a concerned look on his face as he asked Rebecca what took so long for my prostate preparation; he said we had been in the room for about 40 minutes when the average time is about 15.

“No problems what so ever Doctor” Becky said ” We finished the prep in about 10 minutes and then started talking about our grandkids, and things I’m sorry we just didn’t know where the time went” “Oh heck Rebecca that’s fine Mr. Bender is the last exam today and we want to keep our patients happy.”

“Your certainly right there Doctor, there’s nothing like a happy patient,” Becky said as she turned to leave the room giving me a sly wink and licking her lips!!!!

To this day I could not tell you what the Doctor did to me after Rebecca Jean left the room. I didn’t care; I just felt too damned good!!

I checked with Francis on the way out and asked how much longer the AMA study was going to last, she replied “Oh about six more months,” she said.

“I Feel I should do my part in helping medical science progress Francis,” how about putting me on the schedule for a prostate exam at the end of each month it you don’t mind”

“I don’t see why we can’t do that for you Robert,” Francis had a knowing look on her face and gave me a little grin. “See you on Oct-31st at 3:30, Bye”

Seems like Halloween took a very long time to get here, but as I stroll up the sidewalk to Doctor Stein’s office I have bounce in my step and a silly grin I can’t get off my face. Hell that damn Med-student may poke me a dozen times to get my blood I don’t care. I have a 1/2 ounce bottle of CHANEL #5 in my back pocket that is guaranteed to get me all the treats I want and maybe a few tricks just for the fun of it!!

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