I Caught My Trans Roommate Watching Me… Then He Asked to Try

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Hi 18plushome, Let me tell you about my college roommate Jeff. When I was in college, I lived off-campus pretty much the entire time. Eventually, I got an apartment a couple of miles away from campus with a fellow student named Jeff.

Jeff was a pudgy white guy, the same age as me (21), about 5'5" and 180 lbs.

We both happened to have been looking for an apartment at the same time and got the suggestion from campus housing to look at this complex nearby.

It was great! Affordable, comfortable, and with enough space for both of our crap.

Two bedrooms, each with a private bathroom, and shared kitchen/laundry area, dining room, and living room.

I got some furniture for our dining room. Jeff got a couch for the living room.

We got a TV for the living room, and I had my own TV and computer in my room. Jeff had a computer in his room.

I wired the apartment for internet access. I noticed that there was something unusual about Jeff, but I wasn’t quite sure what it was right away.

I mean, he seemed to be pretty average. Short dark blond hair and kind of a roundish face made him look a little younger than he actually was.

And then I figured it out! Jeff was a trans guy!

You have to remember, this was a few decades ago, before being LGBTQ+ was so openly accepted.

So once I figured it out, I just took it as a given and didn’t mention it to him, as I didn’t want to make anything awkward between me and my new roommate.

A year goes by of living together, and we of course get more comfortable with each other, even becoming friends.

At some point, we of course talk about his being trans; he had started transitioning when he was 13 and started on T at 16.

He didn’t eat my food and cleaned up after himself. So he was cool with me.

We got a good chuckle off of that one. Little did I know how comfortable we would get with each other.

One day I’m in my room, the door closed, leaning back in my bed, watching porn (this is back when VHS was a thing) and stroking my dick.

When I’m hard, it’s difficult to miss. I’m Black, about 5'7", and my dick is just over 7" long. Jeff knocks on my door! I very quickly pull my pants up and stop the tape.

I yell out so as to try to seem like I wasn’t just jerking off to porn. “Yo! What’s up?”

Jeff opens the door and says, “Hey, were you watching porn?”

“Yeah.”

I tense up. Fuck! I just got busted masturbating for the first time in my life!

“Can I borrow some?”

I let out a huge sigh of relief! I thought he was gonna be mad, thinking that I was disrespectful because I wasn’t using headphones or something. I started laughing. “Um, yeah man, sure. What do you want?”

Well, he kind of hesitated with a puzzled look on his face. “What were you watching?”

I got up off of my bed and sat in my computer chair and let him sit on my bed.

I pushed play on my VCR remote. It was a video of a chubby white girl sucking a huge Black cock.

Jeff said, “Does that actually feel good?” He looked at the screen and what the girl was actually doing to the man’s dick.

I said, “Well, not really. That’s mostly for show.”

“Well, where does it feel good?”

I was kind of at a loss. “Well, you see, that part, right below the head? Around there.”

“Where? Show me! Come on, you’re not shy!”

He looked directly down at the obvious bulge still present in my sweatpants.

I looked him in his eye for a second, just confirming what I thought he was asking me.

And then I pulled out my still-erect Black cock. “See, right here, this line around my dick — that’s where I was circumcised.

Anything above that line feels good, but it feels best right around here,” as I circled my thumb and index finger around the crown of the head of my cock.

Jeff stared at my dick almost hypnotically. “Can I suck it?”

“You wanna suck my dick?”

“Yeah, I just wanna see what it’s like. Tell me what feels good.”

And he proceeded to get off of my bed, kneel on the floor, and engulf my dick in his open mouth.

“Whoa, slow down a little bit. Yeah, like that. Now use just your lips. OK, pull it out a little bit and use your tongue.” And Jeff proceeded to give his first blowjob to his first Black cock ever.

I leaned back with my hand on the back of his head. After a few minutes of sucking, he stopped, popped my cock out of his mouth, and said, “Do you have a condom?”

Of course I did! I stood up, took off my clothes, and picked up a condom.

Jeff stood up, hesitated for a minute, then slid down his pants and boxers.

He had the hugest clitoris that I’d ever seen in my life! It was almost as big as my thumb! Jeff got up on my bed on his back and laid back with his thighs open, knees bent, and his heels almost together.

“Go slow, it’s been a long time since anything has been in there.” He kept his shirt on, which I thought was odd.

I got up on the bed, rolled on the condom, then placed the head of my cock just inside the lips of his slick cunt.

With his right index finger and thumb, he began stroking his erect T-cock (he told me later that’s what he calls it).

I slowly moved the head of my cock up and down his slit, then began moving it into his pussy.

“Easy,” he said as he put his left hand on my chest to slow my forward motion.

“You sure you wanna do this?” I asked him while looking him in the eye.

“Oh yeah, definitely!”

And slowly I began stroking back and forth inside him. After a couple of minutes, I was fully buried inside his pussy.

In another minute, I exploded into the condom, grunting into his shoulder while fully pummeling his pelvis!

I had his legs hooked around my arms, his knees almost up to his ears!

His arms were around my back, and he kept repeating, “Just keep fucking me! Just keep fucking me!”

When I finally came down from my climax and withdrew my cock from his slick cunt, I noticed his T-cock was still so erect, so I started sucking it.

I gave my first trans man blowjob (but not my last). I treated his enormous clitoris the exact same way that I imagined it would feel on my cock.

He seemed to let out a really deep shudder every time I sucked his clit into my mouth, held it there, and ran my tongue up and down the underside of his shaft.

In a minute, he was grunting and gripping the back of my head, forcing his cock into my mouth as he orgasmed!

I tried to make sure that my lips covered my teeth while flicking my tongue over the sensitive head.

After what seemed like an eternity of him not breathing, he sucked in a deep breath as if his lungs were screaming for oxygen!

“OMG! I have never cum like that before in my life!” he said as he took in deep breath after deep breath. I rested my head on his inner thigh while he caught his breath.

“Hey… I hope this doesn’t change anything between us or nothing.”

“Nah, as long as you’re still cool with me bringing girls over,” I responded.

He laughed. “Of course! Maybe you’ll let me watch now.”

We worked out some ground rules about nudity, openly masturbating, and borrowing porn.

If the bedroom door is closed, knock. If it’s open, come right in. Nudity is allowed everywhere if we’re home alone.

Crank one out anytime you like, just make sure you don’t jizz on the furniture and you clean up after yourself.

As for porn, if one of us is watching, the other can watch too, even if they don’t feel like participating.

One day I came back to the apartment and Jeff’s room door was open. He was sitting in his chair with his back to the door. I came up to his doorway. “Hey, what’s — “

He turned to me with a really intense look on his face. His pants were around his ankles, and he was masturbating furiously! Before he could even get the words out, I dropped to my knees between his legs and started sucking on his

He needed to cum badly! After a few minutes of him gripping my head and bucking against my mouth, he grunted and exploded, slamming his thighs together against my head in the most intense climax ever!

Is like i will stop here, the story is getting longer and my body is shaking as i’m writing this… I might send the complete story to you later, and please remember to keep me anonymous.

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