My Beloved Jenna Goes Bonkers On Me

This assistant, Tina, led Jenna and me into an examination room, where Tina ordered me to take off all of my clothes, bend over, grab my ankles, and remain still. As I did this, I heard Tina opening cabinet doors, taking things out, putting them on the counter, and generally being up to what I could only assume was no good.

"Which would you like me to use," I heard Tina say.

"Bengay should work fine," replied Jenna.

"Bengay it is, for this unfortunate lad. By the way, how did you break him so thoroughly? I'd like to break my girlfriend like this, but it hasn't worked yet."

"It wasn't hard," said Jenna. "He's just a natural sissy. I don't know whether it was nature or nurture, but it's completely ingrained in him. He used to try to dominate me sometimes, and was even pretty good at it, but I could tell that what he wanted was to be dominated and humiliated, and I was right. He's never put up any fight at all, except for the occasional crying and pleading when he's in pain from the paddle or an especially large cock."

"You're so lucky," said Tina.

"Maybe so, maybe so," said Jenna, reaching around me and giving my penis a few love-squeezes. "Let's do this, though. The poor boy will cramp up in that position after too long."

I snuck a glance over my shoulder, and saw Jenna pull a large buttplug out of her purse and hand it to Tina.

"Eyes down, at the floor!" Jenna yelled angrily.

I looked away, and sure enough within another moment I felt the Bengay-greased plug entering my bottom.

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I lay on the examination table face-down, now alone. Tina and my sweet Jenna had tied me firmly to the table and left the room, telling me that I needed some alone-time with the Bengay-greased plug up my ass, before my doctor ex-girlfriend, Sam, would see me.

The Bengay was excruciating, especially since my asshole was already sore and chaffed from having been roundly sodomized the night before by Jenna's and my apartment manager, who took special care to pull his dick all the way out after each thrust, before ramming it good and hard back up my aching sphincter.

Despite all these negative and dire aspects of my situation, there was the upside that my erect penis was comfortably pinned between my stomach and the examination table, allowing me to hump the table, albeit in a limited and constricted way. I was dreading Sam coming into the room, and this dread was making me want to cum, but I couldn't move quite enough against the table to get myself off.

I continued to try, though, and that's when the door swung open and Sam walked right up to me. Because of my position, I could only see her feet and legs.

"Well, well," she said. "I see on your intake form that you complained of sore buttocks, from a recent beating; and a sore anus, from an ass-fucking, which I assume was just the latest of many; and that you requested a pain-relieving cream for your anus. I also see in Tina's notes that she applied a certain cream to the large buttplug which she then inserted into your bottom, and which I can see now is well-seated in your anus." She tapped the base of the plug with her fingers. "Is the cream helping, and do you have any other concerns or questions for me today?"

Goddamnit, it wasn't a pain-reliever, and she fucking knew it. I tried to calm myself down. And then I noticed something. Despite Sam's cold demeanor, I sensed that she was aroused. I could most definitely smell her arousal as she stood close to me. Damn, she smelled good.

"Sam?" I said in a meek and groveling voice. "Would you please call Jenna in here?"

The reason I was asking for Jenna was that, if I was left alone with Sam for much longer, I was going to tell Sam how great her pussy smelled, and ask her to let me lick it. But I didn't want to do that; it would be a violation of Jenna's trust. We weren't in an open relationship. (Unless you consider the numerous men Jenna had invited over to brutalize me, but hey, what's a dozen guys up your ass.)

"No," said Sam. "She told me she was curious what would happen if you and I were in this room alone for a while. I think she wants to test you."

Sam then began squeezing and massaging my sore buttocks with her latex-covered hands.

"Poor baby!" she said. "Your ass is such a wreck! So many, many bruises and welts."

I think she was actually trying to help on some level, but my ass was so deeply bruised that the massage hurt greatly.

I was still pretty sure that I could smell Sam's arousal, and couldn't help myself any longer: "Sam?" I said "Would you let me do something to you?"

Sam stopped kneading my buttocks and stepped back from the table.

"You had better not be about to come on to me," she said. "If so, you're even more pathetic than that buttplug in your ass says you are. Here you have a great girlfriend who loves you... I don't know what to say, other than you'd better not disappoint her, you dipshit!"

There was silence; I tried to think of a quick cover-up line to convince Sam that I hadn't been about to come on to her, but couldn't think of anything. So, I chose the honest route:

"Sam", I said, "Thank you for stopping me. You're right that I was about to come on to you. I got horny all of a sudden. My penis was rubbing against the table, and... I'm a guy, and that means I'm an idiot sometimes."

"Well," she said, "I guess it must be difficult and confusing to be a sissy. But just remember to be good to Jenna. I like her very much; we're becoming friends. She cares about you, and I'd hate it if you screwed up yet another relationship. 'Kay?"

"OK, Sam, I think you're right, and I'm glad we had this -"

THWACK!

THWACK!

Sam clubbed me twice with a long, hard object, possibly a yardstick.

"Sam, please," I begged.

THWACK!

Sam then pulled the table towards the center of the room so that she could walk around in front of me.

"Look at me!"

She had her hands on her hips and looked very serious.

"Since you like being humiliated, let's see how you like this."

She then reached under her skirt and pulled down her panties (she wore cotton granny panties with a floral pattern, which I always thought was sexy and adorable), pulled them down over her shoes one at a time, and then held her panties - yes, definitely wet and fragrant - up to my nose, then rubbed them back and forth across my face.

"Sam, please - "

She slapped my face, then deftly placed her panties over my head, so that the dampened crotch area was right against my nose and mouth.

She left the room, and soon returned with Jenna. As they walked in, they were in mid-conversation:

"... but my advice is you should forgive him. Of course it's your call, but I must say that he tried and struggled not to come on to me."

Jenna then spoke: "Michael, can you hear me? What do you have over your head? Sam, did you put your underwear over poor Michael's head? And... that's a really BIG pair of panties for you to have on your head, Michael! Sam, is your ass really that - "

Then there was a pause, during which Jenna I can only assume was assessing the size of Sam's ass.

"Yes, you do have a big shapely ass, you sexy girl! Very shapely and plump, just like Michael likes, and now he has your big wet panties right over his face! Sam, what an idea! Michael, be forewarned that you'll be wearing MY underwear on your head a great deal of the time from now on. Like, after I've been out for a run and haven't showered. Thank you so much for that idea, Sam. Now, Michael, as far as your coming on to Sam - which is pretty pathetic given that you're tied to a table with a plug up your ass, but nonetheless - I'm worried I'm going to have to keep you in a cage or something. Which I'm not that into, but seriously, I need to do something. Now, Sam is vouching for your more-or-less good intentions, but I want to hear it from you: Are you mine? Can you be faithful to me? I can't beat the answer out of you - your ass is so raw that you'd start bleeding if I hit you. So, I'm asking you, girlfriend to boyfriend, can I trust you?"

This was all extremely confusing.

"Jenna," I said, "I love you, and... of course I'm yours! But I've been getting fucked a lot, and now I have Sam's underwear over my head - I'm just really confused!"

"Hah!" shouted Sam. "He's confused. I think we already knew that."

Sam pulled her underwear off of my head and went over to the counter. "You need some more of that pain-relieving ointment, I do believe."

Don't, I thought, don't, don't, don't, really please don't pour Bengay all over your panties, especially if you're then going to shove your wadded-up panties up my ass. That's a very unnatural thing to do.

THWOOOP! went the buttplug as Jenna pulled it roughly out of my ass.

Sam then asked Jenna, "As far as shoving this up his ass, can I just kind of push it in using my whole hand, or is he not that stretched out?"

"He's not that stretched out. I want him to maintain at least a moderate level of tightness, so that it will always hurt when men fuck him. I always want to be able to see that pained look he makes when a men pumps into him; he's so adorable with that look on his face. So, you'll have to shove your undies up there using your fingers, not your whole hand."

How comforting.

It took a while but finally was done, at which point Sam, now completely bat-shit crazy with her enjoyment of this process, began writing severely degrading things, which she said out loud as she wrote them, all over my ass and back with a felt-tip pen.

"Sam," said Jenna, "I think you might've gone completely around the bend! You know what? I think you need some release! Let's untie this bitch, flip him over, and make him lick your pussy!"

"We'll have to call in Tina," said Sam, "to take notes for Michael's medical file."

TO BE CONTINUED.