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The Sketchbook

"A short story about a single gay man falling for a trans woman and the internal confusion he feels."

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Author's Notes

"This is much shorter than most of my stories. Any feedback that you have is always appreciated."

It was strange seeing you like this. Your parents were excited to see you home, and I was certainly accepting of your change. Here was this twenty-one-year-old woman. You dressed like a bit of a dork, but it was an interesting quirk of yours. You had on a red converse, leggings under your knee-high shorts, and a 3/4 length ball tee with a rich red flannel that matched the converse. It was extra-long and draped down your legs almost as long as your shorts. Your curly red hair seemed darker than before and was now shoulder length. Adorning your thin nose was a black thick-framed pair of eyeglasses that I swore you probably didn't need.

I was still used to seeing the red-headed boy that had grown up asking if he could mow my lawn for spending cash, which I was helpless to say no to. You looked... good after the transition. Perhaps it was because I was thirty-six, and just didn't fully understand the whole Trans thing yet because I couldn't stop seeing that boy. I was gay, and probably should be somewhat educated in my community, but I was fairly closeted most of my life. I'm not your 'typical' gay man I suppose.

I like many of the stereotypical man things. I watch sports. I hang out and drink with the guys. Like all men, I too secretly gossip about all the girls after you leave. My voice was never effeminate. From the surface, you would think I was straight, which is why I still occasionally have a well-intentioned friend offer to hook me up with a great girl. I just brush it off like I do in my sort of gruff way and tell them I'm just not interested in relationships.

The lines in my face were starting to become more pronounced. I had sandy blonde hair, my facial hair coming in even lighter. This made me look far older than I really was. I had grown in a thick mustache at this point. It covered my mouth nicely and I felt like it made me harder to read. I had shaved my beard off after catching Parks and Rec when it was first airing and seeing Ron, thinking, now there's a look.

I attended the neighborhood barbeque that we hosted every summer. An event that everyone in the block attended every year. It went on for ten days, centered mainly in the local park. We had permits for fireworks and everyone pitched in baked goods and games, the money going to pay for the party with any excess going to the charity of the association board's choice.

I wandered out to take in the sites. There were kids riding on the little Ferris wheel that they had paid to bring in, and some throwing darts at a board to win some stuffed animals that we would more than likely see at the thrift store by summer's end. You were over by the lemonade stand paying for your drink. I could see some of the confused looks by some of the neighbors. They knew you but couldn't quite place your face. With some, it would click, and they would carry on, with others I watched you smile as they would say, "welcome to the neighborhood, you must be the nice young lady that moved in with her husband over on Mullberry." You would play along a little before eventually stating plainly that you were the Foster's daughter Rachel. I thought it was a beautiful choice, but my mind still went to Richard when you were brought up in conversation and I would have to correct myself.

You saw me and walked over, confidently.

"Hey, Mr. Harrison! How are you?'’

"Oh, hey kid! I'm doing alright. Still out mowing lawns?" Mr. Harrison? I'm thirty-six, not sixty, I thought.

"HA! No!" You giggled a lot more. You seemed happier. "I actually wasn't looking for work or anything I was kind of hoping you would take a look at my car? You're kind of a mechanic, right?"

Kind of a mechanic? I thought. I have Master's degrees in both Mechanical and Computer engineering. Yeah... I'm a mechanic.

"Uh, yeah sure thing whenever you have time, I guess just let me know."

"Is right now okay?" you stared at me with those same eyes you gave when you came begging for work.

Whatever, I was more of an introvert so may as well leave. People saw me already.

"Sure thing, lead the way, kid."

You brought me to your car. It was a Camry just a few years old. The indicators were all lit up on your dashboard. Did you ever bring your car into a garage? I plugged my computer in first crossing my fingers hoping I wouldn't have to tell you that you would have to buy another crappy used Camry. The computer led to revealing the real issue. There was some mass failure with the sensors on your car. I reset them, and the lights turned off, but some came back on. Taking a brief look under the hood, it looked like you took care of the car after all. Ruling out mechanical issues, I bet my money on the sensors.

"It looks like a sensor issue."

"Oh no... how expensive is that? I don't really have a lot of cash now."

"Oh no worries, a sensor isn't that expensive. In fact, you don't HAVE to get it changed, you'll just need it before getting your car inspected again. I reset them so at least most of the lights will stop flashing at you."

"Thank you so much! You're awesome!"

"No problem. I'm going to head back to the party for a little bit. Tell your parents I said hi."

It felt weird saying that. Here you were twenty-one, an adult that was starting to intrigue me, and it dawned on me as I did the mental math that I was closer in age to your parents. Plus, I mean you were a woman now. Kind of. No that's not the right way to think about it. You WERE a woman. But if you were, what was I now?

"Well, I was actually hoping to ask you one more favor?"

"Yeah if it's the car I can order the sensors. They're really cheap and I have the extra cash so just consider it a gift."

"Oh wow, thank you, but I was actually hoping I could borrow your time for an art project. I only have a year left of school and I'm trying to put together a profile and I was hoping you would pose for me?"

This had my attention.

"Oh... sure."

"Thank you so much, Mr. Harrison! I promise not to make it weird or anything. They're only shown typically to other artists, or if I am looking to get work, I can show off selections of my past work.''

"Okay hold up just one moment. First, please stop with Mr. Harrison. I'm only thirty-six. We could bump into each other at a bar. And second, what's this with not making it weird now?"

"Well, some of the pictures... I kind of... I need some nude poses." Your face blushed, the red in your hair bringing out the red in your cheeks even more.

"HA! Well, I suppose I can do that. I mean it is a little weird but you're an art student. I've dabbled in nudity before. I did some nude posing in college. Once I was in a nude production of Peter Pan. It did not receive good reviews."

I never joked like this, what the heck was going on with me.

You were giggling uncontrollably at this, "You stole that from Parks and Rec!"

"I like to think I made it a bit funnier."

"Wait wait wait wait wait... is that why you have a mustache??"

No one had seen through that before.

"No," I lied. Blushing was hard for me at this age, but it showed through as more of a hot-faced sweat.

We finalized the plans and we decided you could come to my house. Even though you were an adult, you felt awkward around things like this and your parents.

I set aside some white sheets and pulled my couch and chairs out so that you could choose the best setting to sketch. I dragged all my lamps into the living room to give you some lighting options.

You sat down and positioned everything the way you wanted. The first few sketches were quick warm-ups of my face and a general outline of my body. I stood mostly for these, changing stance from time to time as you scratched away at your paper. Once your warm-ups were complete, you asked me to sit down on the couch facing you. You directed me to set my legs apart slightly. I had on a button-up and some dark jeans with a pair of Nikes. You asked me to undo the top several buttons so that my chest was visible. You sat on a chair, folding your legs up underneath your butt, the pad on a stand in front of you, your posture trained.

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"Okay so to not make this weird and to establish a separation I'm just going to refer to you by the subject when asking you to move around."

"Yeah, whatever you'd like, kid."

"And also," your voiced wavered slightly but picked up confidence, "YOU can call ME Rachel," you adjusted your glasses to punctuate this, "not kid."

"Sure thing, Rachel," I emphasized.

"Okay so if the subject would please sit still."

I obeyed while you sketched away for twenty minutes. It seemed an eternity. I hadn't sat this long since I was a kid, growing up listening to hymnals being monotoned in church. The scratching of the paper was soothing to hear, and I watched you as you drew me. You had an intensity and focus that I had only ever seen in myself. You knew how to lock in and get in the zone and surrender to whatever it was you were doing. You were caught up wholly in drawing at this moment and if your hair were to light on fire you would likely not know it.

"Okay, so if the subject would please remove his shirt."

I took it off, taking care to fold it and place it gently on the side table.

"If the subject would also remove his shoes and socks please."

I removed them, placed each sock in its corresponding shoe.

"Now I would like the subject to lay on the couch and hold your body straight. Now act like you're sliding off the couch, so your back is pressed into the cushions. Perfect, thank you. Now first try hands in pocket."

I adjusted accordingly. You furrowed your eyebrows and crinkled your nose.

"Hmm, would the subject please lift his arms above his head and hold his hands together behind his head?"

I adjusted myself again.

"Perfect, thanks!"

You started sketching again, to me the true art being how you approached drawing. You were mesmerized, possessed, the pencil moving you more than you are moving it.

During this time, I couldn't help but think. Looking at you stare at me with that intensity. I looked back at you. You had always been lithe. Your arms were toned. The shape of you was exactly what I liked. I couldn't help but think of you still as that boy and it stirred up in me a strange arousal, knowing the situation I was in.

"If the subject could flex his muscles for me... For accuracy of course!" 

You had me flex my arms first, sketching out the muscles. I wasn't big, but working with machines and various things in the engineering field added with light exercise left me looking strong. After the arms you had me flex my chest, then my stomach.

You finished up the first sketch and looked at me, breathing in through your nose, then out again rapidly.

“Okay… if the subject would please remove his clothes.”

I began pealing the layers off. I hesitated at the boxers, considering this a line I was crossing. I had thought about it and you were an adult capable of making her own decisions, so I removed them, tossing them aside with my other clothes.

You giggled a little.

“Sorry about that. I can be a professional.” You blushed. “Now would the subject lay down across the couch, raising one leg up.

I did as commanded and posed. Out of habit, I raised a hand under my head for support and you didn’t protest the change.

I noticed the speed of your drawing had significantly decreased at this point. You were taking your times tracing the outlines carefully, getting the perspective ‘just right.’ I sat there in torture and even though it was this beautiful woman that was before me it was your eyes that finally did it.

My erection rose, a slow throb that eventually stood completely full.

“Oh! Uhm…” your face was redder than your hair at this point. “If the subject would please remain in the position he was instructed to be in so as to maintain the integrity of the drawing...”

“I’m sorry about that. I was thinking about... football…” I lied.

You giggled, “it’s okay. I understand.”

I chuckled at this but realized I probably shouldn’t have by the way you looked. I suppressed my erection and attempted to put on a more serious face.

You kept drawing; the scratch of the pen had now become deafening to me. After the eternity had ended, you finally put the pencil down.

“Okay, finished. Would you like to look?”

I walked over, placing my boxers on first, and looked at the artwork in front of me. It was amazing. The warmups were better than any cave painting I had ever attempted, and the actual drawings looked like they could have been a black and white photograph.

“Oh my god, that’s fantastic, Rachel!”

“Thanks, Al.”

When you said my name, it sends a shiver down my spine. I placed a hand on your shoulder, knowing I could pass it off as trying to be reassuring and physically affectionate but knew you would easily call bullshit because of how introverted I typically was. You didn’t though. You let me leave it there, even those few seconds past when it was appropriate.

“So, what are your plans after…” and before I could finish saying art school you turned around and kissed me. It wasn’t this deep kiss; it was this soft little peck like you were afraid I was going to push you away.

“Oh my god, I’m so sorry about that I don’t know what overcame me I just…” I grabbed you, lifting you up and kissing you back.

This was new territory for me entirely. Was I still gay? Was she straight? What the hell is happening in 2019? Finally, I just thought fuck it and decided to go with the flow. The only part that made me queasy about any of this was the age difference. I kept pushing it out of my mind, but it kept knocking on the back, threatening to deflate my growing erection.

There were no words. I was already nearly nude, and you had been sketching me for over an hour. I began tearing off your clothes as your skin flushed red. You had on this plain little white bra and panties that matched. My own prejudice made me think you would be this sex maniac, but here I was tearing into you and the more I looked the more innocent you seemed. I was the depraved old thirty-six-year-old creep and you were just the cute little art student.

I pushed the thoughts out as you started to let your hands wander more. You pushed the boxers back down, using your foot to push them past where you couldn’t reach without leaning. You were shy even to the last moment to go near my cock.

I picked you up, placing you on the couch where you had just sketched me. Removing your underwear, you revealed yourself to me.

“You look beautiful, Rachel,” I said to you.

You blushed and grabbed at my hair.

My cock entered your ass slowly, working you up to be able to fit the size of it in. I was no Yao Ming, I packed the standard six inches, but six inches in the rear feels like a lot more than you would think having been there myself in past relationships.

You bit your lower lip and let out a soft moan. You kissed at my neck as I gently began rocking into your hips on the couch.

“Oh fuck, oh yes, don’t stop,” you called out, edging me closer to release.

I kissed you again, plunging deep into you and emptying my hot cum all over your insides. I kept myself inside as we laid there panting in a hot sweaty mess.

We cleaned up and got dressed without any words. I wasn’t sure what to think. I had always thought of myself as a gay person, but this was different. I liked this. I had always shunned relationships but against all odds, I thought to myself that maybe there could be something here.

“Thanks for… well, thanks for everything… I uhh… bye!”

You ran out. Your shyness made me want to drag you back again for round two. I watched you saunter away and imagined the repercussions of asking you out on a date. What your parents would say to me at the next neighborhood watch meeting.

Worth it, I thought.

 

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Written by lolwriter89
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