1. My Evolving Transition – Ch. 03


    Date: 12/29/2023, Categories: Fiction Anal Blowjob Cosplay, Gay Author: Luvagobfull, Source: sexstories.com

    ... fridge and grabbed us one of those mini-bar bottles each, and a can of JD (Jack Daniels). We sat on the edge of the bed and drank them.
    
    “Your turn,”
    
    He looked at me and handed me the KY. I felt obliged but didn’t want to.
    
    We both drank a miniature bottle of spirits from the bar before, I spread KY over his ass and inside it, before trying to fuck him, as he did me. I attempted to give Tiffany the odd anal fuck, but she told me I wasn’t good at it, so we stopped.
    
    His hole was tight, at first but it wasn’t such an effort as it was for him.
    
    “Wow, that was an effort, didn’t think I was going get it in,”
    
    I said as if I had hit a trick shot in a game of pool.
    
    “Being a little drunk can help, as long as you’re not too drunk,”
    
    he said.
    
    “Meaning?”
    
    I said, puzzled with my cock buried inside his ass.
    
    “It slows down the urge to cum,”
    
    he said. Funny, I had always thought too much alcohol made you cum too quick, I thought to myself.
    
    “Now start fucking me slowly at first,”
    
    he ordered, and I did.
    
    With every thrust, his ass sucked tight around my cock, and I could feel cum trickling out from my ass, with each thrust. Then I over exerted and I let off some gas from with my bowels, and out plopped more cum. That ran down the back of my leg.
    
    I must have then fucked inside his ass about another 10-20 times before I started to cum. I felt glad as it was tiring and straining my lower back.
    
    “Oh, fuck, oh fuck,”
    
    I groaned, as I dumped my love deep ...
    ... inside his ass.
    
    With my cock still spasming inside. Someone bashed the wall from the next room, telling us to shut up. More like
    
    “Shut the fuck up, faggots, or I’ll kick the door down and make you!”
    
    Trying to be quiet and ignore the Wildman outside, I flopped on top of him, panting like a dog in summer.
    
    Before I could do anything, Jessa had turned to his side and pushed me off him. He kissed me, before slivering towards my cock. he swallowed my cock, and sucked on it, to cleanse it.
    
    *
    
    Later, as we lay naked on my bed, and recovering, he rubbed my chest.
    
    “Where are you from?”
    
    he asked.
    
    “Out of town and interstate,”
    
    I said.
    
    “Figured as much, can we fuck until you leave,”
    
    he said.
    
    “Sounds good, but I think I might be back in a few months, once I tie up a few loose ends at home,”
    
    I said.
    
    He stayed until lunchtime that day, and he fucked my ass several times and I tried again to fuck him. In the end, he stopped asking me to fuck him.
    
    We fucked and sucked all morning, then we cleaned up. That afternoon we went clothes shopping. He picked out clothes that I would look good in, plus some make-up, only black eyeliner, and lipstick. The clothes were a bit girly, but I wasn’t complaining, he paid for them. Then we kissed and cuddled in public before he went home.
    
    I wore eyeliner when I went to the bar that night. Jessa turned up after 08:00 PM, before we returned to my motel for one last time, with a 10-pack of JD. We fucked and sucked ...