The biggest cock I (trans) have ever taken

Brooks was tall. Really tall. I literally had to tilt my head back just to look up at his face when we were both standing. I'm a pretty small and thin girl, and I love a good size difference because it makes me feel feminine.

We met at a party and really talked about nothing important. I asked him about what he did for work, and he asked me back. I just said "I make bad decisions mostly" and he laughed.

His hand was on my thigh under the table. I don't remember when that started exactly, but all of a sudden it was happening. One minute we were talking and then his hand was suddenly there and his thumb was moving in small circles and my cock was honestly getting kinda hard.

We left together. His apartment was close. We walked and he held my hand and I thought about how my hand looked so tiny in his and how small I felt next to him and how much I liked that feeling.

His apartment was clean and organized. He seemed well put together which I also liked. He closed the door and turned to me and I was already reaching for his belt. I wanted him.

"In a hurry?" he said.

"You have no idea." I said in a desperate little voice.

I got his jeans open finally and I pulled them down and. Okay. Wow. I don't know what else to even say. I was stunned. I always expect tall and big guys to be big down there, but this was on a whole new level.

He was big. Not like "oh that's bigger than average" big. Big big. Thick, long, only semi hard so farm, but still way bigger than most guys I have been with. When I wrapped my hand around him my fingers almost didn't even close all the way. Just the fingertips were touching. I just stood there looking at it and he was watching me look at it and i'm sure he has had this exact experience a bunch of times and he almost looked amused by it.

"Still want to stay?" he asked.

"Shut up." I said.

I got on my knees. I took his cock into my mouth as far as I could, which was not as far as I wanted lol, and he moaned softly and put his hand in my hair and pushed gently. I did my best to suck him with my mouth and my I used my hand to hopefully help and he was patient while I figured out how to manage the insane size of him.

"That's good," he said. Quiet. His placed his palm along my cheek while I sucked on him as best as I could. "Really good." he said.

I was hard too. My cock was pushing against my clothes and he noticed and reached down and pulled me up and kissed me and his hand went down to feel me through my clothes.

"Can I?" he asked.

"Please."

He undressed me. Carefully. Shirt first. Then my jeans. He paused when he saw me. I'm used to the pause. I'm used to guys feeling a little uncertain when they first see that I have a cock and small tits and hips that curve the way they do. Even if they already know i'm trans like he did, I think its just a bit of a shock to them to actually see it. Most of them get over it pretty fast. His hand wrapped around my cock and stroked me once, slow, and he said "You're beautiful" and I believed him.

He laid me on the bed after. We kissed for a long time. Just making out and feeling each other all over. His body was huge compared to mine, and I liked the weight of him and the way his cock pressed against my thigh. It was so big I could hardly get over it.

"I want to fuck you," he said against my mouth.

"Yes."

He was careful and slow which I def appreciated. He used a lot of lube and went slow and the stretch was. A lot. I felt every inch going into my ass and I grabbed the sheets hard and just breathed through it and he waited for me to adjust. He kept stopping to check my face and I kept saying "keep going" until he was all the way in and I felt so full I couldn't speak anymore.

He moved slow at first. Long strokes that made my whole body roll with the motion. His hand was on my hip and his mouth was on my neck and I was making sounds I have literally never made before.

"More" I said.

"Fuck me harder"

He went deeper. Harder. Each thrust hit me hard and I could feel everything throughout my whole body.

"Touch yourself," he said.

I reached between us and wrapped my hand around my own cock and stroked it while he fucked my tight little ass and the combination of both was so overwhelming I can't even describe it. He was so deep inside me and my hand was moving so fast at this point and I could feel it building up inside me.

I came first. Hard. My cock pulsed in my hand and I shot across my stomach and even all the way up to my face where some landed on my lips and cheek. He leaned down and kissed me and we passed back and forth the little drop of cum that had landed on my lips. He moaned into my mouth and fucked me harder and harder as we kissed.

"I'm close," he said.

"Don't stop."

He came with massive pulse. I felt him pulse inside me and his load was huge I could already tell. His orgasm went on for a while, way longer than most. He finally pulled out of me and instantly I felt a river of cum dripping out of my ass.

He laughed. I laughed. He handed me a towel and I cleaned up and we lay there for another hour just talking and his hand was on my stomach the whole time, and I just kept thinking about how big he was and how I knew this was gonna hurt the next day.

I felt it the next day. I felt it for two days actually. I texted him about it and he sent back a smiley face and I swear to fucking god I have never been so turned on by a smiley face in my life.

reddit.com
u/AryaRayn — 15 hours ago
â–² 12 r/Erotica

The biggest cock I (trans) have ever taken [F19/M21] [Hugecock] [Hot]

Brooks was tall. Really tall. I literally had to tilt my head back just to look up at his face when we were both standing. I'm a pretty small and thin girl, and I love a good size difference because it makes me feel feminine.

We met at a party and really talked about nothing important. I asked him about what he did for work, and he asked me back. I just said "I make bad decisions mostly" and he laughed.

His hand was on my thigh under the table. I don't remember when that started exactly, but all of a sudden it was happening. One minute we were talking and then his hand was suddenly there and his thumb was moving in small circles and my cock was honestly getting kinda hard.

We left together. His apartment was close. We walked and he held my hand and I thought about how my hand looked so tiny in his and how small I felt next to him and how much I liked that feeling.

His apartment was clean and organized. He seemed well put together which I also liked. He closed the door and turned to me and I was already reaching for his belt. I wanted him.

"In a hurry?" he said.

"You have no idea." I said in a desperate little voice.

I got his jeans open finally and I pulled them down and. Okay. Wow. I don't know what else to even say. I was stunned. I always expect tall and big guys to be big down there, but this was on a whole new level.

He was big. Not like "oh that's bigger than average" big. Big big. Thick, long, only semi hard so farm, but still way bigger than most guys I have been with. When I wrapped my hand around him my fingers almost didn't even close all the way. Just the fingertips were touching. I just stood there looking at it and he was watching me look at it and i'm sure he has had this exact experience a bunch of times and he almost looked amused by it.

"Still want to stay?" he asked.

"Shut up." I said.

I got on my knees. I took his cock into my mouth as far as I could, which was not as far as I wanted lol, and he moaned softly and put his hand in my hair and pushed gently. I did my best to suck him with my mouth and my I used my hand to hopefully help and he was patient while I figured out how to manage the insane size of him.

"That's good," he said. Quiet. His placed his palm along my cheek while I sucked on him as best as I could. "Really good." he said.

I was hard too. My cock was pushing against my clothes and he noticed and reached down and pulled me up and kissed me and his hand went down to feel me through my clothes.

"Can I?" he asked.

"Please."

He undressed me. Carefully. Shirt first. Then my jeans. He paused when he saw me. I'm used to the pause. I'm used to guys feeling a little uncertain when they first see that I have a cock and small tits and hips that curve the way they do. Even if they already know i'm trans like he did, I think its just a bit of a shock to them to actually see it. Most of them get over it pretty fast. His hand wrapped around my cock and stroked me once, slow, and he said "You're beautiful" and I believed him.

He laid me on the bed after. We kissed for a long time. Just making out and feeling each other all over. His body was huge compared to mine, and I liked the weight of him and the way his cock pressed against my thigh. It was so big I could hardly get over it.

"I want to fuck you," he said against my mouth.

"Yes."

He was careful and slow which I def appreciated. He used a lot of lube and went slow and the stretch was. A lot. I felt every inch going into my ass and I grabbed the sheets hard and just breathed through it and he waited for me to adjust. He kept stopping to check my face and I kept saying "keep going" until he was all the way in and I felt so full I couldn't speak anymore.

He moved slow at first. Long strokes that made my whole body roll with the motion. His hand was on my hip and his mouth was on my neck and I was making sounds I have literally never made before.

"More" I said.

"Fuck me harder"

He went deeper. Harder. Each thrust hit me hard and I could feel everything throughout my whole body.

"Touch yourself," he said.

I reached between us and wrapped my hand around my own cock and stroked it while he fucked my tight little ass and the combination of both was so overwhelming I can't even describe it. He was so deep inside me and my hand was moving so fast at this point and I could feel it building up inside me.

I came first. Hard. My cock pulsed in my hand and I shot across my stomach and even all the way up to my face where some landed on my lips and cheek. He leaned down and kissed me and we passed back and forth the little drop of cum that had landed on my lips. He moaned into my mouth and fucked me harder and harder as we kissed.

"I'm close," he said.

"Don't stop."

He came with massive pulse. I felt him pulse inside me and his load was huge I could already tell. His orgasm went on for a while, way longer than most. He finally pulled out of me and instantly I felt a river of cum dripping out of my ass.

He laughed. I laughed. He handed me a towel and I cleaned up and we lay there for another hour just talking and his hand was on my stomach the whole time, and I just kept thinking about how big he was and how I knew this was gonna hurt the next day.

I felt it the next day. I felt it for two days actually. I texted him about it and he sent back a smiley face and I swear to fucking god I have never been so turned on by a smiley face in my life.

reddit.com
u/AryaRayn — 15 hours ago

The biggest cock I (trans) have ever taken

Brooks was tall. Really tall. I literally had to tilt my head back just to look up at his face when we were both standing. I'm a pretty small and thin girl, and I love a good size difference because it makes me feel feminine.

We met at a party and really talked about nothing important. I asked him about what he did for work, and he asked me back. I just said "I make bad decisions mostly" and he laughed.

His hand was on my thigh under the table. I don't remember when that started exactly, but all of a sudden it was happening. One minute we were talking and then his hand was suddenly there and his thumb was moving in small circles and my cock was honestly getting kinda hard.

We left together. His apartment was close. We walked and he held my hand and I thought about how my hand looked so tiny in his and how small I felt next to him and how much I liked that feeling.

His apartment was clean and organized. He seemed well put together which I also liked. He closed the door and turned to me and I was already reaching for his belt. I wanted him.

"In a hurry?" he said.

"You have no idea." I said in a desperate little voice.

I got his jeans open finally and I pulled them down and. Okay. Wow. I don't know what else to even say. I was stunned. I always expect tall and big guys to be big down there, but this was on a whole new level.

He was big. Not like "oh that's bigger than average" big. Big big. Thick, long, only semi hard so farm, but still way bigger than most guys I have been with. When I wrapped my hand around him my fingers almost didn't even close all the way. Just the fingertips were touching. I just stood there looking at it and he was watching me look at it and i'm sure he has had this exact experience a bunch of times and he almost looked amused by it.

"Still want to stay?" he asked.

"Shut up." I said.

I got on my knees. I took his cock into my mouth as far as I could, which was not as far as I wanted lol, and he moaned softly and put his hand in my hair and pushed gently. I did my best to suck him with my mouth and my I used my hand to hopefully help and he was patient while I figured out how to manage the insane size of him.

"That's good," he said. Quiet. His placed his palm along my cheek while I sucked on him as best as I could. "Really good." he said.

I was hard too. My cock was pushing against my clothes and he noticed and reached down and pulled me up and kissed me and his hand went down to feel me through my clothes.

"Can I?" he asked.

"Please."

He undressed me. Carefully. Shirt first. Then my jeans. He paused when he saw me. I'm used to the pause. I'm used to guys feeling a little uncertain when they first see that I have a cock and small tits and hips that curve the way they do. Even if they already know i'm trans like he did, I think its just a bit of a shock to them to actually see it. Most of them get over it pretty fast. His hand wrapped around my cock and stroked me once, slow, and he said "You're beautiful" and I believed him.

He laid me on the bed after. We kissed for a long time. Just making out and feeling each other all over. His body was huge compared to mine, and I liked the weight of him and the way his cock pressed against my thigh. It was so big I could hardly get over it.

"I want to fuck you," he said against my mouth.

"Yes."

He was careful and slow which I def appreciated. He used a lot of lube and went slow and the stretch was. A lot. I felt every inch going into my ass and I grabbed the sheets hard and just breathed through it and he waited for me to adjust. He kept stopping to check my face and I kept saying "keep going" until he was all the way in and I felt so full I couldn't speak anymore.

He moved slow at first. Long strokes that made my whole body roll with the motion. His hand was on my hip and his mouth was on my neck and I was making sounds I have literally never made before.

"More" I said.

"Fuck me harder"

He went deeper. Harder. Each thrust hit me hard and I could feel everything throughout my whole body.

"Touch yourself," he said.

I reached between us and wrapped my hand around my own cock and stroked it while he fucked my tight little ass and the combination of both was so overwhelming I can't even describe it. He was so deep inside me and my hand was moving so fast at this point and I could feel it building up inside me.

I came first. Hard. My cock pulsed in my hand and I shot across my stomach and even all the way up to my face where some landed on my lips and cheek. He leaned down and kissed me and we passed back and forth the little drop of cum that had landed on my lips. He moaned into my mouth and fucked me harder and harder as we kissed.

"I'm close," he said.

"Don't stop."

He came with massive pulse. I felt him pulse inside me and his load was huge I could already tell. His orgasm went on for a while, way longer than most. He finally pulled out of me and instantly I felt a river of cum dripping out of my ass.

He laughed. I laughed. He handed me a towel and I cleaned up and we lay there for another hour just talking and his hand was on my stomach the whole time, and I just kept thinking about how big he was and how I knew this was gonna hurt the next day.

I felt it the next day. I felt it for two days actually. I texted him about it and he sent back a smiley face and I swear to fucking god I have never been so turned on by a smiley face in my life.

reddit.com
u/AryaRayn — 16 hours ago

A "straight" guy didn't find out I was trans until we were naked in bed

That is the first thing he said after he found out. His hands were still on my waist, our lips were still wet from kissing each other, and he was looking up at me from between my legs where he had just been kissing his way down my stomach. His fingers had just gotten to my underwear for the first time and that is when he felt it. Usually I am a little more proactive, but this time I guess I just got carried away a bit.

"Yeah," I said. "Seriously."

His name was Adrian. Met him at a rooftop party I went to with my friends. It was honestly kinda off the chains so far as parties go. There was a lot of degenerate behavior going on. We hit it off pretty quickly at the party and he is the one who approached me in the first place. I wasn't sure if he could tell that I was trans or not, but I guess I need to accept at this point that people can not in fact tell.

I mean I know what I look like. Long hair, short dress, slim waist and legs, small boobs. I look like I was born as a girl.

He came up to me and said "I was trying to think of something smooth to say, but I couldn't so I am just going to tell you you're beautiful and hope that works."

"It works," I said. I actually appreciate that kind of approach. It feels honest.

We talked for an hour or two. He was funny. A little nervous, but authentic. Which I liked.

When he kissed me at the end of the night as we were leaving, his hands went to my waist and he pulled me in and I felt everything. He felt fit. I could tell he had more muscle than it looked like. He wasn't bulky, just lean.

"Come back to mine?" he asked.

So I did. That easy. I'm not the hardest girl to get into bed with I won't lie.

This tends to be the part where things always get… Potentially messy. I have been kicked out of people's apartments before. It sucks, but I deal with it. I'm not gonna play victim.

We were on his bed. He took my dress off, slowly and sensually. He was kissing my neck, my cheeks, the tops of my small boobs. His mouth finally found my nipple and they are super sensitive so it made me press into him and I was already getting hard at this point. He was working his way down slowly. Kissing my stomach. Getting ready to take everything off.

I put my hand on his. I needed to tell him. I could feel in my chest that he didn't already know, and it would be wrong of me to not disclose.

"I need to tell you something first." I told him.

He stopped. Looked up at me. "What is it?"

"I'm trans," I said. "I have a cock."

That's when he said it. "What the fuck are you serious!"

He seemed shocked enough that I kind of felt bad for him.

I nodded. I always get this weird feeling in this moment. Shame mixed with nervousness mixed with anticipation. It is hard to explain if you haven't experienced it. I never know which way it is gonna go. Sometimes it blows up.

He sat back stunned. He looked at me. All of me, lying on his bed in just my underwear now. I could see the shape of my cock through the fabric. It is honestly crazy we went this long without him knowing.

"You're so pretty though" he said. He seemed sorta disappointed.

And then he pulled my underwear down.

I was fully hard now. Pressed up against my stomach. He stared at me for a second, and then he wrapped his hand around me and I stopped breathing.

"Is this okay?" he asked.

"Very okay."

I'm happy this one worked out. I think a lot of you guys would be surprised how often guys don't care. Ask them in public and you get a different answer, but in private? Whole new world.

He stroked my cock, slow, looking at my face while he did it. I could feel his hand shaking a little. Nervous. Maybe even confused. I think he was surprised by how much he wanted this.

"Can I suck on you?" he asked. Straight guys always ask. I'm not sure why.

I nodded yes and he lowered his mouth on to my cock and started to bob up and down. It was clearly his first time with a cock. I felt his teeth and then he overcorrected and went too wide. I didn't mind. I love being a guy's first. He just wanted me to feel good and he was doing his best and figuring it out as we went.

I put my hand in his hair. "Use your tongue more. Yeah. Like that." I said to him.

He moaned around me and the vibration felt good.

I was close to cumming embarrassingly fast. I think the situation kinda turned me on extra. I pulled him off and he looked up at me.

"I want you to fuck me now" I told him.

He stood up and took his clothes off and he was hard. Really hard. He put on a condom and I told him where the lube was in my purse and got on my stomach.

He was really slow at first. Almost too careful. I had to push back against him before he got the signal that I could take it.

"God, you're tight," he said as he slid the tip of his cock into my ass.

"And you're going slow" I giggled.

That is when he stopped going slow.

He fucked me face down on his bed. With one hand flat on my back holding me down. I reached around under myself while he fucked me and stroked my cock in time with his thrusting.

When I came, it was all over his sheets. I moaned loudly. He felt me tense up and squeeze his cock tightly with my ass and I think that is what set him over the edge. He started cumming and he thrust all the way into my ass and unloaded while inside of me.

We lay there for a while. Sticky. Breathing hard.

"I've never done that before," he said.

"Done what?"

"Any of it. All of it." He paused. "You're really hot. I just want you to know that." he told me.

I rolled over and kissed him. That was sweet of him to say. I slept over that night.

The next morning, his roommate saw me coming out of the bathroom in his shirt and he just nodded at me, completely unsurprised, and went back to eating cereal. Adrian turned bright red. He may have done something new last night, doesn't mean he is fully comfortable with it yet. I'm not judging. It takes time.

I still have his shirt. He hasn't asked for it back. I honestly don't think he will.

reddit.com
u/AryaRayn — 1 day ago

A "straight" guy didn't find out I was trans until we were naked in bed

That is the first thing he said after he found out. His hands were still on my waist, our lips were still wet from kissing each other, and he was looking up at me from between my legs where he had just been kissing his way down my stomach. His fingers had just gotten to my underwear for the first time and that is when he felt it. Usually I am a little more proactive, but this time I guess I just got carried away a bit.

"Yeah," I said. "Seriously."

His name was Adrian. Met him at a rooftop party I went to with my friends. It was honestly kinda off the chains so far as parties go. There was a lot of degenerate behavior going on. We hit it off pretty quickly at the party and he is the one who approached me in the first place. I wasn't sure if he could tell that I was trans or not, but I guess I need to accept at this point that people can not in fact tell.

I mean I know what I look like. Long hair, short dress, slim waist and legs, small boobs. I look like I was born as a girl.

He came up to me and said "I was trying to think of something smooth to say, but I couldn't so I am just going to tell you you're beautiful and hope that works."

"It works," I said. I actually appreciate that kind of approach. It feels honest.

We talked for an hour or two. He was funny. A little nervous, but authentic. Which I liked.

When he kissed me at the end of the night as we were leaving, his hands went to my waist and he pulled me in and I felt everything. He felt fit. I could tell he had more muscle than it looked like. He wasn't bulky, just lean.

"Come back to mine?" he asked.

So I did. That easy. I'm not the hardest girl to get into bed with I won't lie.

This tends to be the part where things always get… Potentially messy. I have been kicked out of people's apartments before. It sucks, but I deal with it. I'm not gonna play victim.

We were on his bed. He took my dress off, slowly and sensually. He was kissing my neck, my cheeks, the tops of my small boobs. His mouth finally found my nipple and they are super sensitive so it made me press into him and I was already getting hard at this point. He was working his way down slowly. Kissing my stomach. Getting ready to take everything off.

I put my hand on his. I needed to tell him. I could feel in my chest that he didn't already know, and it would be wrong of me to not disclose.

"I need to tell you something first." I told him.

He stopped. Looked up at me. "What is it?"

"I'm trans," I said. "I have a cock."

That's when he said it. "What the fuck are you serious!"

He seemed shocked enough that I kind of felt bad for him.

I nodded. I always get this weird feeling in this moment. Shame mixed with nervousness mixed with anticipation. It is hard to explain if you haven't experienced it. I never know which way it is gonna go. Sometimes it blows up.

He sat back stunned. He looked at me. All of me, lying on his bed in just my underwear now. I could see the shape of my cock through the fabric. It is honestly crazy we went this long without him knowing.

"You're so pretty though" he said. He seemed sorta disappointed.

And then he pulled my underwear down.

I was fully hard now. Pressed up against my stomach. He stared at me for a second, and then he wrapped his hand around me and I stopped breathing.

"Is this okay?" he asked.

"Very okay."

I'm happy this one worked out. I think a lot of you guys would be surprised how often guys don't care. Ask them in public and you get a different answer, but in private? Whole new world.

He stroked my cock, slow, looking at my face while he did it. I could feel his hand shaking a little. Nervous. Maybe even confused. I think he was surprised by how much he wanted this.

"Can I suck on you?" he asked. Straight guys always ask. I'm not sure why.

I nodded yes and he lowered his mouth on to my cock and started to bob up and down. It was clearly his first time with a cock. I felt his teeth and then he overcorrected and went too wide. I didn't mind. I love being a guy's first. He just wanted me to feel good and he was doing his best and figuring it out as we went.

I put my hand in his hair. "Use your tongue more. Yeah. Like that." I said to him.

He moaned around me and the vibration felt good.

I was close to cumming embarrassingly fast. I think the situation kinda turned me on extra. I pulled him off and he looked up at me.

"I want you to fuck me now" I told him.

He stood up and took his clothes off and he was hard. Really hard. He put on a condom and I told him where the lube was in my purse and got on my stomach.

He was really slow at first. Almost too careful. I had to push back against him before he got the signal that I could take it.

"God, you're tight," he said as he slid the tip of his cock into my ass.

"And you're going slow" I giggled.

That is when he stopped going slow.

He fucked me face down on his bed. With one hand flat on my back holding me down. I reached around under myself while he fucked me and stroked my cock in time with his thrusting.

When I came, it was all over his sheets. I moaned loudly. He felt me tense up and squeeze his cock tightly with my ass and I think that is what set him over the edge. He started cumming and he thrust all the way into my ass and unloaded while inside of me.

We lay there for a while. Sticky. Breathing hard.

"I've never done that before," he said.

"Done what?"

"Any of it. All of it." He paused. "You're really hot. I just want you to know that." he told me.

I rolled over and kissed him. That was sweet of him to say. I slept over that night.

The next morning, his roommate saw me coming out of the bathroom in his shirt and he just nodded at me, completely unsurprised, and went back to eating cereal. Adrian turned bright red. He may have done something new last night, doesn't mean he is fully comfortable with it yet. I'm not judging. It takes time.

I still have his shirt. He hasn't asked for it back. I honestly don't think he will.

reddit.com
u/AryaRayn — 1 day ago
â–² 149 r/gonewildstories

A "straight" guy didn't find out I was trans until we were naked in bed [FM]

That is the first thing he said after he found out. His hands were still on my waist, our lips were still wet from kissing each other, and he was looking up at me from between my legs where he had just been kissing his way down my stomach. His fingers had just gotten to my underwear for the first time and that is when he felt it. Usually I am a little more proactive, but this time I guess I just got carried away a bit.

"Yeah," I said. "Seriously."

His name was Adrian. Met him at a rooftop party I went to with my friends. It was honestly kinda off the chains so far as parties go. There was a lot of degenerate behavior going on. We hit it off pretty quickly at the party and he is the one who approached me in the first place. I wasn't sure if he could tell that I was trans or not, but I guess I need to accept at this point that people can not in fact tell.

I mean I know what I look like. Long hair, short dress, slim waist and legs, small boobs. I look like I was born as a girl.

He came up to me and said "I was trying to think of something smooth to say, but I couldn't so I am just going to tell you you're beautiful and hope that works."

"It works," I said. I actually appreciate that kind of approach. It feels honest.

We talked for an hour or two. He was funny. A little nervous, but authentic. Which I liked.

When he kissed me at the end of the night as we were leaving, his hands went to my waist and he pulled me in and I felt everything. He felt fit. I could tell he had more muscle than it looked like. He wasn't bulky, just lean.

"Come back to mine?" he asked.

So I did. That easy. I'm not the hardest girl to get into bed with I won't lie.

This tends to be the part where things always get… Potentially messy. I have been kicked out of people's apartments before. It sucks, but I deal with it. I'm not gonna play victim.

We were on his bed. He took my dress off, slowly and sensually. He was kissing my neck, my cheeks, the tops of my small boobs. His mouth finally found my nipple and they are super sensitive so it made me press into him and I was already getting hard at this point. He was working his way down slowly. Kissing my stomach. Getting ready to take everything off.

I put my hand on his. I needed to tell him. I could feel in my chest that he didn't already know, and it would be wrong of me to not disclose.

"I need to tell you something first." I told him.

He stopped. Looked up at me. "What is it?"

"I'm trans," I said. "I have a cock."

That's when he said it. "What the fuck are you serious!"

He seemed shocked enough that I kind of felt bad for him.

I nodded. I always get this weird feeling in this moment. Shame mixed with nervousness mixed with anticipation. It is hard to explain if you haven't experienced it. I never know which way it is gonna go. Sometimes it blows up.

He sat back stunned. He looked at me. All of me, lying on his bed in just my underwear now. I could see the shape of my cock through the fabric. It is honestly crazy we went this long without him knowing.

"You're so pretty though" he said. He seemed sorta disappointed.

And then he pulled my underwear down.

I was fully hard now. Pressed up against my stomach. He stared at me for a second, and then he wrapped his hand around me and I stopped breathing.

"Is this okay?" he asked.

"Very okay."

I'm happy this one worked out. I think a lot of you guys would be surprised how often guys don't care. Ask them in public and you get a different answer, but in private? Whole new world.

He stroked my cock, slow, looking at my face while he did it. I could feel his hand shaking a little. Nervous. Maybe even confused. I think he was surprised by how much he wanted this.

"Can I suck on you?" he asked. Straight guys always ask. I'm not sure why.

I nodded yes and he lowered his mouth on to my cock and started to bob up and down. It was clearly his first time with a cock. I felt his teeth and then he overcorrected and went too wide. I didn't mind. I love being a guy's first. He just wanted me to feel good and he was doing his best and figuring it out as we went.

I put my hand in his hair. "Use your tongue more. Yeah. Like that." I said to him.

He moaned around me and the vibration felt good.

I was close to cumming embarrassingly fast. I think the situation kinda turned me on extra. I pulled him off and he looked up at me.

"I want you to fuck me now" I told him.

He stood up and took his clothes off and he was hard. Really hard. He put on a condom and I told him where the lube was in my purse and got on my stomach.

He was really slow at first. Almost too careful. I had to push back against him before he got the signal that I could take it.

"God, you're tight," he said as he slid the tip of his cock into my ass.

"And you're going slow" I giggled.

That is when he stopped going slow.

He fucked me face down on his bed. With one hand flat on my back holding me down. I reached around under myself while he fucked me and stroked my cock in time with his thrusting.

When I came, it was all over his sheets. I moaned loudly. He felt me tense up and squeeze his cock tightly with my ass and I think that is what set him over the edge. He started cumming and he thrust all the way into my ass and unloaded while inside of me.

We lay there for a while. Sticky. Breathing hard.

"I've never done that before," he said.

"Done what?"

"Any of it. All of it." He paused. "You're really hot. I just want you to know that." he told me.

I rolled over and kissed him. That was sweet of him to say. I slept over that night.

The next morning, his roommate saw me coming out of the bathroom in his shirt and he just nodded at me, completely unsurprised, and went back to eating cereal. Adrian turned bright red. He may have done something new last night, doesn't mean he is fully comfortable with it yet. I'm not judging. It takes time.

I still have his shirt. He hasn't asked for it back. I honestly don't think he will.

reddit.com
u/AryaRayn — 1 day ago