Something about Me and You Pt. 03

Thank you for all of the kind words you all have expressed, I'm habitually excited to see that the reaction to part two was outstanding. At the time of writing this it scores 4.82 which places it in the top 100 overall in this category and the top 50 this year! I suppose in a long winded, kind of scatterbrain way, I want to say thank you.

Now, I took a lot of the feedback you all have sent me seriously; and I think the pacing and plot of this next part really embodies the overall flavor of your suggestions and feedback. If you liked it, hated it, loved it, what have you; please let me know. This whole exercise is designed to better my craft, and the best way of doing so is to hear back from you all. Please take the time to comment or send it as a message.

And most importantly; enjoy the story!

Cheers,

Dr. Masterfield

*****

Story so far:

Part One: Michael our main character, is an associate professor at the University of Mcgill. He had, early in the story lost his mother who was dear to him, and therefore seeks therapy. His Therapist Charon had suggested he seek out a hobby that would allow himself some time to be mindful. That is where he met Sam a Transgendered woman packing some heat, who studies as a PhD student at the university. A series of events leads them to come to conflict after Michael helps her relieve herself in a bathroom. This causes a dilemma for Michael, who until this time had never considered himself homosexual. He seeks the advice of Charon...

Part Two: Michael draws a wedge between him and Sam, on account of his inability to cope with some of the major changes he is facing. Though his Therapist convinces him of what he knew already which is that he really does care for Sam, and that this fearfulness is caused by his apprehension to homosexuality. Which he did not even know existed. Embracing his desires, he seeks out Sam and shows her love, and admiration; whereby they end up dating.

Part Three: -

Chapter Nine

It had been a couple of days since Sam had moved in to the office next to mine. And Things seemed to have been going well, having her own office seemed to have made her far more productive than she otherwise had been in the Grad lounge, but her excess in work had limited the amount of time we were spending together. Only just briefly speaking to each other in the hall, or we might share a small kiss before running the various errands we had to attend. It posed an interesting dichotomy, on the one hand I honestly wanted to spend more time with her, even non sexually; I really enjoyed her company. On the other hand, I was genuinely worried about my dilemma. Was I ready to consider letting her have her way with me in that way? Honestly, I had never considered being anally penetrated in a good way; it was always referenced poorly when discussing jail or other horrible situations. That said, I didn't think I would enjoy giving blowjobs so much as I do. But that's irrelevant.

I would have to test it, I reasoned, and had thought of exactly the right way.

****

I arrived at the sex shop; I wouldn't have even known it was there had I not shot it into my navigation app on my phone. The shop was secluded, built into the back of a large building with the entrance at the back. I mean it's all very cliché, blacked out windows with bright pink neon signs on the door.

When I walked in, the harsh smell of lubricant assaulted my nose. Fitting considering that the display for some expensive lubricant was directly in front of the door. Against the far wall were shelves covered in dildos and other stranger looking implements, I'm fairly certain that one was shaped like a horse's cock... Some people's children, but I digress... There was a checkout desk on the far wall to my right, and a cryptic "alleyway" lined with black lights to my left. Through the store were various shelves that had a variety of sex toys or costumes.

The lady at the checkout counter looked down into one of those useless magazines, the ones that allegedly have the latest gossip about celebrities, the ones that should never see print. Yeah those. Her focus didn't falter either, she barely looked up as I walked in. I suppose it's because I might be described as "the safe option". Given my attire, attitude, and general mannerism there was little for people to be nervous about. No one has ever robbed a store wearing a cardigan and boat shoes.

I began to peruse the shelves searching for what I had been here for in the first place. To my dismay, try as I might, I couldn't find a Clone-A-Willy. One of those silicone molds for a penis that you send off and made into a personalized dildo. My plan was to trick Sam into making one, that way it would give me the best idea as to whether or not I would enjoy having sex with her in that way. That wasn't my only quest though, I also had read online that preparation was the key to having a good anal relationship. I grabbed a kit with four butt plugs with varying sizes, from small to large so I could slowly condition my muscles to accept such a gift from Sam. Her gift was particularly girthy after all... That left the other item, and I had checked and double checked each shelf when I looked up to the counter and to my dismay; saw it behind the counter. This was going to be an awkward conversation.

"Hey Sweetheart" the girl behind the counter said, not looking up from her magazine.

"Hi... I was wondering if you could grab me one of those-" I pointed.

She looked up, finally, and turned to see what I was pointing at. Pulling it off the shelf and slapping it down on the counter, the tough plastic making a clicking sound on the wooden surface.

She looked at me more closely, and squinted her eyes slightly.

"Wait..." she said puzzled, "Do I know you from somewhere?" She continued.

"Well I just have one of those faces-" I said in a vain attempt to diffuse the situation that was going south very quickly.

"No really, I've seen you somewhere before..."

Then it clicked for me, I did in fact know this girl. Once I had taken a better look at her, it was clear. Her name was Clarissa Nascimento, an old student of mine who had failed microeconomics 101 with me. She had been furious; she lost the scholarship that was paying for her tuition due to the shot her GPA took... As a result, I figured she had ended up here. I could only hope that she wouldn't...

"If it isn't Dr. Masterfield..."

Shit-

"Ms. Nascimento, how are you?"

"I always knew you were a little anal retentive..." She said flatly.

"Look, I'd just like to buy these items and you'll never see me again" I was actually a fair bit nervous about the encounter.

Before I could do anything, her phone came from beneath the counter, I saw small red lights blink on the base of the camera lens. Shit.

"On the contrary, I hope to be seeing you often." She said laughing.

I leaned into the counter, "Delete that. Now." I said with an undertone of aggression.

"I would be careful with your tone Michael; you wouldn't want to add an assault charge to being a pervert would you?" Clarissa said pointing to the surveillance camera.

Fuck.

"What do you want? Obviously, I can't change your grade; this was more than a year ago." I said, with as much contempt as is possible.

She stood up straight, though she was not very tall, I am around 6'2, she is closer to 5'10; I still managed to feel tiny in comparison. Her Hazel eyes tracking across my body, darting quickly from top to bottom as a predator might size up their prey.

"You're going to do exactly as I say, or I'll post this picture anonymously all over campus, and email it to every student and prof. in the university."

It was actually very possible she had retained access to the student database; meaning she could in fact send out a mass email...

I stood there in perturbed silence for a moment.

"What do you want me to do?" I asked, defeated.

"Well, Michael, for starters..." She said as she walked past me and locked the door, setting the sign to closed. Then turning to face me again, "Why don't you start by taking off your shirt."

****

I was virtually naked now, but for my boxer briefs, she led me down the corridor to the left of the entrance. I couldn't see much because there was little light except for black light that emanated from small disks set into the floor. Kind of like reverse pot lights. Until we reached a room, the door was set into the wall, so if you didn't know it was there, you probably would overlook it. Clarissa looked me up and down again, before pointing towards the door with her head.

The room was about as dark as the hallway, I turned to look at her but she swiftly shut the door behind me. It was at that moment; I realized the door didn't have a handle from the inside...

"Hey! Let me out of here!" I kicked at the door to no avail.

Clarissa didn't answer, but I could hear muted laughter come from the other side of the door disappearing as the distance between her and I mounted.

Then silence, the music that was ever present in the hall seemed muted, I could hardly hear it, the walls must be considerably thick. It also didn't help that in my haste to disrobe earlier, I didn't think to grab my cell phone.

The room was small and bare, I looked around for a little while as my eyes adjusted to the darkness. The only furniture to speak of was a foam chair and what looked like those pads for scrubbing floors, so to prevent your knees from getting sore on tiles. The far wall from the door was a huge mirror, it looked as though it hadn't been cleaned in some time, given the number of hand and fingerprints left all over its surface, I noticed what looked like a small crack, no, a hole in the mirror, it was about three inches in diameter. I tried to look through but to no avail, it was also made from a mirrored surface, and a bright light from the other side reflected too harshly to see through. From the other side of the room I could hear steps, slow, and then a loud metallic sound.

"You probably noticed there's no door handle in that room." It was Clarissa's voice from beyond the wall.

"Let me out of here!" I screamed.

"Calm down Michael, I will, you just need to do something for me first." She sounded like she was very pleased with herself.

"And you're going to delete that picture you have of me..."

She was quiet for a moment yet, though her presence in the other room was noise enough. She was considering her options I wagered.

"Alright, if you do what I ask, I'll delete the picture and let you go, in fact I won't even tell anyone you were here."

"I won't even need the picture when I'm done, I'll have gotten everything I needed.

"Alright... What do I have to do?" I asked, sounding utterly defeated.

Just then, a hard cock poked through the rubberized barrier in the hole, it was huge. Bigger than Sam's in fact. It was mocha colored like the rest of Clarissa but for a light pink head that rested out from where her foreskin would be. For whatever reason the two-tone nature of it kind of excited me. Gnarled veins ran up the top and side, like the roots of an ancient elm.

"Suck my cock, and you can go."

I was in a way hoping to hear her say that. I didn't expect her to be... well trans, when I walked in earlier. But a part of me wished she were, I mean she is a beautiful woman through and through. Her skin a dark shade of copper, her eyes a piercing hazel, her breasts were large and perky, and she had an ass that rivaled Nikki Minaj... At first, I figured I was developing a fetish for trans women, but I have to think now, that it's more than that. I feel the need to worship them... A deeper burning desire to please them, something I have never felt before...

I walked up to the wall, and grabbed her veiny cock in my hand, it was thick and very hard. Like the difference between aluminum foil, and carbon steel. The warmth was intense, and I could feel it throb in time with her heart beat, which was pretty quick; she must've been excited.

I stroked it gently, I could hear her groan from the other side of the wall. It wasn't until I lowered myself to face this monster that I truly understood the size of it. As I continued to stroke it up and down slowly, I placed my other hand on it. I put my two hands together to measure this goddess's pole, One... Two... Three... and two fingers. Now my hands are not very slender either, this thing must be at least eleven inches long.

"See something you like baby?" She asked heartily, heavy with pleasure.

While it may be my fantasy to suck on the cocks of trans women, obviously, it was her fantasy to have me suck on her cock. The act of submission before her, must've gotten her so bothered because she was already oozing precum. I figured she must have played this over and over in her head while she rubbed herself off at night.

I imagined it were me sucking her off in the early hours of the morning, nursing on her morning wood. Feeling that big dark meat pulse inside of me. Damn I too was pretty hot about this.

While I didn't like the feeling of being coerced into sucking her dick at first, I had to admit the degradation was something I was coming to enjoy. Submitting before such a virile mistress such as her, it got me so excited I could think of nothing else but having her blow her load into me. I licked the underside of her head, placing my lips greedily around the tip. I slurped hard making such a lewd sound, taking in quite a lot of precum. Which she had in great supply.

Her pre was an interesting flavor, while Sam's was well bodied but a touch salty, Clarissa's pre was actually sweet, tasting almost like rosewater. Glossing over the fact that I had just compared pre cum in the way one might describe a fine wine... I had better things to do after all.

I sealed my lips around her cock head, and worked my hands in unison up and down milking out every drop of precum she was willing to give me. I couldn't believe it, but before long, I had accrued a sizeable puddle in my mouth, I let it rest in the middle dip of my tongue, just savoring the sweet nectar from this goddess. My cock was hard in my shorts, the head poking upwards and out of my underwear. I thought what was the worst thing that can happen, and began to rub my slick head with my fingers.

I figured I had teased this cock for far too long, I started to feel her buck her hips slightly through the gloryhole. She was impatient. I started to slide my lips down over the rough surface of her dick. The thick veiny member was pretty tough to take in really, each vein felt hardened, as though I had climbed a mountain each time, I would come up over one. They also provided a strange sensation, I could feel her pulse while I sucked over them, her heart beating fast, bringing tons of fresh blood to her cock. I could only fit less than half of her cock into my mouth, about five inches, which was more disappointing for me than her I wagered; since I was having a hard time keeping up to the steady flow of pre that coated my mouth in its ecstasy.

I had one hand on her cock stroking in time with my ascension up her shaft, my mouth sucking hard to keep a good pressure, and my tongue doing small circles along the base as I moved. When I would reach the crown of her beautiful cock, I would hold myself there and stroke furiously for several pumps, just to get another taste of that sweet, sweet nectar.

I had a hand on my cock pumping furiously, I caught myself moaning into her cock on more than one occasion. She relished this situation, I could hear her moaning through the wall, our lewd behavior causing a veritable orchestra of sex. Her long, hard cock spasming releasing a jet of precum every pump I made, my mouth coated in her sweet, sticky, harmony of pleasure.

"Is this all I had to do to get better grades? Shit, baby you can suck mami's cock anytime."

I pushed her cock as far into my throat as I could, and she grunted in response. I think I liked the idea of a gloryhole; I was able to pleasure her at a pace that I allowed, I mean sure she was "forcing" me to suck her off, but I was in total control of the situation. Her pleasure was literally and figuratively in my hands.

That excited me, I imagined her and Sam on a couch, me sucking them off, switching in time, back and forth. Not unlike what I was doing now, Up and down, up and down, more and more precum filling my stomach. It had excited me so much I quickened my pace slightly. Stroking myself furiously, I was getting close.

"Ugh, yeah, suck that dick you slut." She said, her voice husky with lust and desire.

A wave of heat hit me all of a sudden, I didn't just feel like a slut, I loved it.

I was stroking her as furiously as I was myself, I knew she was as close as I was. I gripped onto her head with my lips, my tongue circling the tip in quick motions.

"Oh, Oh, Oh, shit, you fuckin' slut I'm gonna' nut in your mouth!"

I opened my mouth, leaned my head back and jerked her off onto my tongue, each blast covering it completely. I had to swallow twice per rope of jizz that filled me, even then I over flowed down my mouth. Her cum running in two streams out the side of my mouth. I came shortly thereafter, exploding straight up onto the mirrored surface.

Once she had blown her load and I swallowed best I could, I returned to nursing on that hard cock. Taking every last drop she was willing to give me. As I sucked gently, I felt her cock soften in my mouth. I heard a click, and the door opened.

Chapter Ten

I waited at the front desk, of the store for a few minutes. There were some napkins on the counter, so I used them to clean myself up. When Clarissa walked slowly out of the hall and into view. I couldn't help but feel overwhelmed by her beauty. She was in her bra and underwear, her flaccid cock resting silently up towards her pubis. She had the rest of her clothes bundled in a heap she carried under her left arm.

"Mhhhmm" She exclaimed, her eyes doughy and even a touch affectionate.

"Baby you sucked mami's cock like no one else" She continued.

It was one thing hearing those things in the glory hole, but now that I was face to face with Clarissa, it felt different somehow. In some ways better and in some worse. How did I feel about being her "slut"? I knew I enjoyed it when I was taking her cock into my mouth, acting as a slut as it were; but now... I don't know.

I also thought of Sam... I didn't feel so bad previous because I felt as though I was being forced to suck her off, but I still wanted to suck her dick afterwards... Even now, there was little but morality keeping me from kneeling in front of her and sucking it again.

In the meantime, Clarissa had walked behind the counter, and was leaning on her elbows. Her large, sexy breasts pushed together like that made me shift my pants. Because I was uncomfortable... Yeah.

"Here-" She said as she showed me while she deleted the picture of me.

I couldn't help but feel a bit sad really, that picture gave me an excuse to live out my fantasy with yet another beautiful trans woman, now I wouldn't have such an opportunity.

"Look at you bab' you're so cute when you're confused" She said teasingly. "I might take you anotha' round with this dick, so you can show me what you're really made of."

"While I would love that Clarissa, I-"

"Shit, you think I was askin' you?" She said half laughing half very serious.

"You'll suck this dick whenever I damn well want you to!" She continued.

"Well I won't... You've got nothing on me now." I said puzzled.