1. Caught!


    Date: 12/21/2023, Categories: Cross-dressing, Author: BadDog9

    ... day.
    
    “Sorry, I’ve been thinking about wearing my teddy and stockings since I left last night. I had to come over,” Nathan greeted me with an excited grin as I climbed out of my truck.
    
    I chuckled at his excitement. “No problem, hun, come on in. We should probably talk about last night anyway.”
    
    “It was the best night ever! I’m so glad I decided to talk to you,” Nathan exclaimed, running to the gurl room.
    
    “Do you think I need to shave again?” Nathan called from the gurl room as I leafed through my mail.
    
    “I doubt it, but it would probably be good to get some practice if you want,” I answered, turning around to find Nathan standing in my kitchen naked, and already hard. I instinctively licked my lips while staring at his tantalizing tool. I couldn’t help but, laugh as I stared at his over-excited organ.
    
    “So, you’re okay with everything that happened last night? No regrets or anything?” I had to ask.
    
    “Oh no, I’ve wanted to do it for so long, it was the best time ever. I felt so good when I left here. Mom even asked what I was so happy about this morning. Of course, I couldn’t tell her and I started getting hard thinking about it. So I had to wait until she left the room to get up from the breakfast table,” he giggled.
    
    “Okay, I just wanted to make sure you’re okay with everything,” I smiled.
    
    “I’m more than okay. You make me so horny,” he said, crossing the room to pull me in for a kiss.
    
    The feel of his warm smooth flesh caused an instant reaction in my ...
    ... pants as our lips met for a long slow kiss. Memories of my own initial forays into dressing and exploring sex with men flooded my mind as my hands roamed over Nathan’s young body. His excitement was perfectly understandable to me.
    
    “Dan, will you fuck me tonight? I want to know what it feels like,” Nathan said, pulling his soft lips away from mine.
    
    “Are you sure you’re ready for that? You should take your time and not rush things,” I cautioned, at the same time wanting to bend him over and slide my cock deep in his cute little virgin ass.
    
    “I’m sure, I’ve been thinking about this for a long time and I’m ready to find out what it’s like,” Nathan insisted.
    
    “Okay, but we’ll need to get you prepared first,” I agreed with a raging hard-on threatening to tear through my jeans.
    
    “Really? Okay just tell me what to do,” Nathan beamed like a kid on Christmas.
    
    I sent Nathan to run himself a hot bath while I retrieved my enema bag and some lube from their hiding place in the spare room. I joined Nathan in the bathroom and explained how to fill and use the enema bag. For the first time, I saw fear and indecision on his face as I explained the process of cleaning himself out.
    
    “You don’t have to do this, if you’re not ready,” I assured him.
    
    “No, no, I’m ready,” he insisted, not quite as enthusiastically as before.
    
    I left Nathan to his preparations and went to shower myself. Unlike Nathan, I did need to shave again as I was already quite stubbly. It was difficult not ...
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