I met B in a chat room while I was traveling for work. I was in a hotel in southern CA and I was online one evening just playing around, flirting, and seeing what kind of mischief I would find in general. He sent me a private message and threw out a very clever pick up line (sorry, you’ll have to wait for the Best Online Pickup Lines post to learn what it was) so I struck up a conversation with him.
He waited a polite amount of time before asking the a/s/l question, and that’s when we learned that he lived around the corner from my hotel. Suddenly, the conversation got much more interesting.
That’s also when I learned that he was almost 25 years old. I groaned. I was 40 at the time, and I was pretty strict about staying away from the younger guys (I defined younger as under 40). It’s not that the young ones aren’t cute, but when you’re cheating on the road you have some things to consider that might not be obvious to other folks. For example, I knew that this was likely going to be a one-time shot. Did I really want to waste a few hours on a guy that might not have enough experience to even find my clit? The truth is that, generally speaking, men with a little more experience know their way around a woman’s body, and that’s a plus to be sure. Sweet little B was living with his very first girlfriend ever.
On the other had, there was something kind of intriguing about teaching a young guy a few things. He had never experienced either anal or oral sex (I know, amazing, huh?) and he really wanted to try it. Just like you never forget your first sexual experience, I knew that if I did this, Baby B would never forget me. So, I agreed. I gave him my phone number so he could call and we could talk it over a bit.
I asked him how he wanted it to go, and I listened carefully. He suggested something that I had never considered before. Yes, I actually learned something really good from this young one. He wanted to come into the room and get down to business with no conversation first. His explanation was that he’d be too nervous and talking for a bit would make it worse for him, so he just wanted to get right to it. Believe it or not, I loved that! It was seriously hot…and it became my favorite way to meet someone new. There’s plenty of time to talk later, right?
So, by the time I opened the hotel room door when he arrived, his shirt was already almost off and his pants were unbuckled. Eager boy! He stepped right in and kissed me deeply and slipped my robe off my shoulders as he wiggled out of his pants. “This is what nervousness looks like?,” I thought.
His hands were all over the place – fumbling here and there, indecisive, excited, like he was trying to touch everything all at once and feeling a bit frustrated because he only had two hands. I guided his right hand down to my pussy and slid a finger right where I wanted it to be and I put his other hand on one of my breasts. He moaned and sighed heavily, as if he were relieved for the guidance. Within about 30 seconds I learned that while he needed a little help finding my clit, he knew what to do with it once he was there. I leaned back against the wall behind me and relaxed into the sensations.
Soon, he took his hand from my breast, lifted my left leg and started pushing himself inside me. “Very nice,” I thought. “A little initiative…good boy….” But then he suddenly stopped everything and said, very firmly, “No! That’s not what I want to do.” I was shocked. How do you respond to that? So I just said, “Ok. What do you want?” “I want to do the things I can’t do with my girlfriend.” He replied. I answered, “Ok, B. You’re in charge here. Whatever you want.” Then he looked at me like a little boy who had just received the Christmas gift he really, really wanted, and he said, “Really? I mean, really? Whatever I want?”
I started to wonder if he had been involved in the chat and phone conversations we had just had about an hour earlier or if that had been his evil twin. Then I realized that he was undoubtedly so nervous on the phone that he probably wasn’t listening well, so I explained it again. Yes, we can do whatever you want. Anal? Sure. Oral? How ‘bout right now?
I walked him over to the sofa and sat him down, and I knelt in front of him and took his stiff swollen cock into my mouth. I had been planning to do this nice and slow, gentle and sweet, but my now I was thinking this boy needed an experience to really remember, so I dove right in, taking him into my throat on the very first stroke, sucking him very hard and very deep, swallowing the head on every stroke. He didn’t moan; he screamed. I worked him even harder. It didn’t take him long to cum, as I swallowed it, he was just moaning, “Oh my god, oh my god, oh my god….” Ok, I’ll admit it. That made me smile.
I sat on the floor next to him and looked up at him. The expression on his face was a completely new one for me – something between amazement, happiness, fear, confusion. I let him catch his breath for a few minutes and then I started some small talk. He had told me he was going to college and that he was an English major. I was in the process of editing a friend’s novel. I had the pages all spread out over the second bed in the room. I started talking to him about it. He was genuinely interested, as I don’t think he had ever seen an unpublished novel in process, so we talked about that for a bit.
Within 5 minutes (yes, only 5 minutes) he was ready to go again. I started stroking him gently while he was still talking about the book. I grabbed some KY from the night table (in those days I traveled prepared) and started applying some to his already very hard dick. He looked confused, but I knew he’d figure it out in a moment. I stood up, took his hand, and led him over to the bed. I climbed on the bed, got on my hands and knees in front of him, and looked back at him. He smiled. “Really?,” he said. Oh my gosh. This young one really needs mommy’s approval, doesn’t he? Then he said, “What do I do?” My annoyance instantly turned to compassion. What a sweet kid. So I told him just to put the tip in and then hold onto my hips – I’d do the rest.
He slowly pressed the tip of his cock into my ass. I don’t even think he got the whole head in, and then he grabbed my hips. As soon as I felt that he had a good grip I started pressing back against him. His 8” cock felt amazingly good sliding inside me, and I remember thinking what a great lover this boy is going to be once he learns how to use that thing. I moved forward and back slowly a few times, making sure his whole shaft benefited from each stroke, but within a few strokes he had taken over and he was pulling me back onto him and thrusting inside me hard and fast with surprising force. Then he slowed down and was pounding me with long slow strokes, each one lifting my knees off the bed and making me squeal. He came hard; his fingers dug into my hips and his hands held my backside a few inches up off my knees as he had me in just the position he wanted while he came.
He pulled out slowly and slid onto the bed next to me. There was no talking this time. In a few minutes, I felt him nudge me to roll over, and he moved between my legs and started to lick that clit I had helped him find earlier. By this time, I had had enough foreplay, I came very quickly. Afterwards, he lifted up to where I could see him. He had a huge smile on his face which was covered with my wetness. I smiled back.
The next hour was filled with more play. It was fun. Before he left, he wanted to exchange phone numbers, I said no. There was no way this could be repeated again, and I wanted him to remember it exactly this way.
Maybe the young ones aren’t so bad after all.