Colin is my best friend, he’s one of the lads, he also has a nice tight pussy to fuck.
I was 13 years old and my friend Colin was 11.
But Colin wasn’t what he appeared to be, I knew the truth, but my parents didn’t, Colin used to be Coleen, he’s transgender, he looks, dresses, acts and talks like a boy, but he’s actually a girl, with all the girl parts.
I met Colin at my new school and we quickly became best friends and hung out all the time, even sleeping over at each other’s house in the same bed, he told me early on that he was transgender and it didn’t bother me at all because I liked being with him, to me he was a boy just like me.
One night I was sleeping over at his house, we were laying in bed together and I just randomly got an erection, it was impossible to cover up because it was clearly sticking right up under my shorts, Colin saw it and we both had a laugh and giggle about it because it just got hard out of nowhere, Colin asked if he could see it so I pulled my shorts down a little and showed it to him.
“Does it hurt when it happens?” he asked.
“Nah – Just feels rock hard and a little uncomfortable.” I replied.
Colin desperately wanted to be a boy, and have a cock, he nervously asked me if he could touch it, just to feel what it was like, “Sure.”, so he reached across and took hold of it, my cock twitched and swelled a little in his hand as he grabbed it, then he moved his hand down, rubbing my hard shaft, and it felt good, happy shivers went through me, “Ooah.” I gasped momentarily.
“Did I hold it too hard?” he asked, thinking he’d hurt me when I gasped like I did.
“No – No.” I replied.
He slowly kept rubbing it, examining it, I threw my arm over my eyes because it felt so good, Colin had no idea what he was doing to me, I was trying to block it out and not let it make me feel that way, but I couldn’t, my cock was ultra-sensitive and I could feel myself about to nut…and then I did, “Ooah – Oah – Oooooah.” I suddenly ejaculated, shooting a long stream of semen up in to the air, it came back down and splatted all over his hand.
Colin immediately sat up looking shocked, but smiling an intrigued, “What was that?” he asked, taking his hand off my cock and looking at the white sticky goo all over his hand and webbing between his fingers, “You made me come.” I replied.
I spent 10-15 minutes doing my best to explain to him what had happened, why it happened, what semen was, what it does, where it goes, and he was fascinated, “Do it again.” He said, but I couldn’t, not that quickly, he just wiped it off his hand then we laid back down in silence.
Something had changed between us in the moment, Colin’s eyes were looking at me in a different way, it made me feel a bit uncomfortable and my heart beat got faster, “Want to see mine?” he asked, breaking the awkward silence.
“Yeah – Okay.” I replied, I’ll have a look, I’ve never seen a pussy before.
He was wearing boxer shorts just like a boy and he pulled them down to his knees then lifted up his long baggy t-shirt, and there it was, no balls, no cock, just a smooth curved bump between his legs with a line down the middle, out of all the things I could have asked, for some reason the first question that came out of my mouth was, “Where does your pee come from?”
He reach down and pried apart his flaps with his fingertips, revealing the bright pink innards of his pussy and pointed to where it came from, “There.” He said.
As he was showing me his pussy I got another erection and my mouth got full of saliva, I had to swallow it to stop myself drooling, but it was pretty clear that his pussy was getting me all worked up and turned on, “Can I touch it?” I asked, it was only fair seen as he had touched mine.
He said that I could so I reached across and rubbed my hand over it, it was very warm, silky smooth and like squidgy sort of like pressing your hand on a balloon it had that kind of bounciness to it, “It’s nice.” I said.
Colin frowned, “No it’s not. I hate it. I want what you’ve got.” He said.
“I like it. It feel nice.” I replied, still rubbing it with my hand, then I ran my fingertip up and down the crack, I saw his clitoris and sort of teased it with my fingertip, “What’s this for?” I asked.
Colin gasped from me stimulating his clit, he seemed very surprised by the way me touching it made him feel, I kept moving it around and messing with it and Colin kept gasping, I laughed, “Does it tickle?” I asked.
“Y-Y-Yeah.” He stuttered in response through his gasping.
I kept messing with his clit and he kept gasping, we both started laughing, he told me to stop but I wouldn’t because it was too funny, then he rolled over towards me and we starting wrestling and play fighting on the bed, and as we were doing that, our privates made contact.
We both felt the same sudden jolt go through our bodies when it happened and we froze still for a minute, Colin looked down and the tip of my hard cock was pressing in to the crack of his pussy, he reached down and took hold of my cock but left it pressed in his crack, then he started to move his hips forward and back.
My cock was sliding up and down his crack, squashed between his spongy folds, and he was lightly pushing himself downward, my cock sinking further in, “O-ugh.” He moaned, we look at each other right in the eyes and knew what was about to happen, Colin suddenly pushed himself down very hard on my cock and it went inside of him, “Argh-Oah!” – “Oooah.” We moaned and groaned together.
He started to ride my cock, but slowly, and a tear ran down his face and he looked at me with great confusion, he so desperately wanted to be a boy, but at this very moment, he was happy to be a girl, it was like he didn’t understand why having my cock inside of him made him feel so good, it made me feel pretty damn good as well.
Eventually we rolled over and I got on top of him and fucked him in the missionary position, thrusting my cock in and out of his pussy felt so good, and he was moaning like a girl, “Ungh – Ooh – Ung – It hurts – Ungh!”
I was fucking him deep and hard, stretching his innards with my hard cock, I offered to stop because he said it was hurting but he told me “No.” – “Keep going.”, so I continued and eventually, after maybe 20 minutes, I ejaculated inside of him.
We then laid side-by-side recovering and getting our breath and energy back, Colin was staring at the ceiling and he didn’t say a word to me for over an hour.
Then he turned his head to the side and looked at me, when I looked back at him, he smiled and rubbed the side of my face tenderly, then he leaned in and kissed me on the lips and slowly rolled himself over and on top of me.
Then he reached down and found my cock, which of course was fully erect again, he inserted it in to his pussy, and while laid down on top of me he started rocking back and forth fucking my cock, and he kept kissing me, I loved how tight his pussy was around my cock, I was getting my cock fucked so good.
We fucked all night until dawn, then fell asleep until the middle of the afternoon.
Colin still wanted to be a boy, and he was still my best friend, a friend with benefits, a friend with a pussy, a friend who liked riding my cock because he didn’t have one of his own.