14 years ago I posted a couple of stories from my first sexual experience, which…
My Boss's Sister
I stopped by my boss’s office. I needed to get an approval for a purchase req but the bitch wasn’t in.
One might think I was being kind of harsh referring to my boss like that, but the bitch hates me. I know it. She knows it. Probably everyone else knows it, too.
I didn’t find my boss there but there was another woman there instead. I told her who I was looking for, and she told me her sister had just stepped out but she’d be back soon.
Oh great, I thought, the bitch has a sister.
The woman asked me if I wanted to wait or what. I figured there was no point in waiting, so I gave the woman my name and told her to let her sister know I had stopped by.
“Oh, it’s you,” she said disdainfully.
I suppose I should have just let that pass, but I couldn’t help rising to the challenge. “What do you mean by that?” I asked.
“By what,” the woman asked, as if she didn’t know.
“Oh, it’s you,” I repeated, using her same tone and inflection.
“Oh, um nothing,” the woman demurred.
“I don’t believe you,” I told the woman. I took another step towards her. “You don’t even know me,” I told her. “You don’t have the right to judge me.”
That having been said, I just turned and left.
It was about fifteen minutes later when the woman was walking by and she saw me in my office. She stopped and poked her head in the door. “Hey,” she said, “I’m sorry about that. You were right. That was unfair of me. I don’t really know you.”
I was still fuming a bit over what had happened before. “That’s right,” I told her, “I don’t.”
“Yeah,” said the woman, “well fine. Sorry then,” and then she turned and left.
The day was over and I needed to pick up some food on the way home so I stopped by the store. I’d just paid for the groceries and I was about to leave when who should show up coming into the store but my boss’s sister. “Hey there,” I said. “Hey, now I have to apologize. I was a bit brusque there when you poked your head in my office, but I was still a little ticked off.”
The woman smiled and I liked it when she did that. “Well, you were right,” she told me again. “I didn’t know you and I still don’t, or rather,” and here she smiled again, “I don’t know you yet, but I think maybe I’d like to get to know you better.”
“Yeah?” I said suspiciously. I still wasn’t sure I trusted her.
She stepped up to me and then she stroked a hand over my arm. “Yeah.”
Well, that was all it took. Soon, we were on our way to my place, and on the way, we talked.
The woman told me she was just in town for a few days to spend some time with her sister. She smiled at me. A few days of her sister was just about all she could take she told me, and right then and there, I knew I liked her even more.
“So,” she asked playfully as we got to my place and I closed the door behind us, “are you as much of a dick as my sister says you are?”
“I don’t know. What do you think?”
She rubbed her hand over the front of my jeans and she smiled again. “I don’t know,” she said. “It seems like you might be an even bigger dick than she says.”
“Well, there’s only one way to find out,” I told her.
She smiled again. Damn, I loved that smile. “I was thinking pretty much the same thing,” she told me, and then she was opening my belt and she was pulling down my jeans.
As I stood there in my foyer, I watched this woman drop to her knees and then she was pulling down my underwear and then she purred. “Oooh,” she moaned as she wrapped her hand around my shaft, “you are a lot bigger dick than my sister said.”
I moaned as that woman slipped her mouth around my shaft and then I moaned again as she sucked me hard.
I just kept on moaning as that woman sucked on my cock. I moaned again. If she didn’t watch out, this woman was going to get a mouth full of cum. Of course, I thought, maybe that was exactly what she had in mind.
The woman pulled her mouth off my cock and her hand jacked my slippery shaft. “Do you want to cum for me?” she asked. “Do you want to cum really hard?”
“Oh yeah,” I groaned. “I want to cum really hard.”
She smiled at me again, and I couldn’t help thinking that the only thing that could make that smile look even better was to see that smile even as my cum dribbled from her mouth, but then she asked me the question.
“Do you want to put it in my mouth or put it in my cunt?”
That was a very good question, and yet as much as I knew I wanted to have her suck me off, I knew I really wanted to slip it in her cunt, and that was exactly what I told her.
“Oooh,” she purred, “I was hoping you’d say that.”
And that was how the two of us ended up in my bedroom, each of us undressing the other and then I was pushing that woman down on my bed even as I mounted her body and even as I slid myself between her thighs.
She looked up at me and she smiled again. “Come on,” she purred, “I want you to do it. I want you to fuck me.”
That was all I needed to hear. I pushed my cock up against her cunt and I could feel just how wet she was. She moaned as she felt my cock press up against her pussy. I knew she needed to be fucked. She needed it bad.
She moaned as her cunt took my cock and then she just kept on moaning as I kept fucking her harder and harder. There was no doubt about it. She loved my cock.
There also was no doubt that she was going to cum. She was moaning almost constantly as her pussy took my cock. Her hands worked her tits and then she would moan again. She was going to cum.
The woman moaned again and then she gasped as my cock pushed her over the edge. Her hands wrenched her tits and her fingers tweaked the nipples and she moaned again. She was cumming so fucking hard.
“You’re making me cum,” the woman cried. “You’re making me cum.”
I knew that. Damn, I loved the way her cunt squeezed my cock. She was cumming so fucking hard.
And still, even as she continued to cum, I couldn’t get that image out of my mind, the one of her smiling through her cum-covered face.
As her pussy relinquished its hold on my cock, I slid myself out of her cunt and then I straddled her body. I pushed my cock between her tits and almost immediately, she seemed to know what it was I wanted to do. She pushed her tits together and she took my cock between her fleshy mounds.
She looked up at me and she smiled again. “Come on,” she coaxed me, “do it. Fuck my tits. I want you to do it. Fuck my tits.”
The next time I pushed my cock past her full, round globes, she sucked the head of my cock into her mouth. She grinned at me as she released her hold on my cock. “I know what you want to do and I want you to do it. I want you to cum on my face.”
I groaned again even as I pulled my cock back between her tits, and then I pushed my cock between her tits again. Again, she sucked on the head of my cock and again, she made me moan. I didn’t know if she meant it or not, but if she kept sucking on my cock like that, she was going to get my cum on her face whether she wanted it or not.
I knew she was frigging her clit even as I fucked her tits. I heard her moan and I knew she was nearly as close to cumming as I was. Or maybe, she was even closer.
I shoved my cock back between her tits. Damn, I loved her tits almost as much as her smile and then she sucked on the head of my cock again. That was all it took. My cock erupted and I sprayed a load all over her face. I heard the girl moan even as I creamed her face with another burst from my cock. Oh damn, this was just so good.
I kept cumming and cumming and even as I did, so did she, too.
By the time I finished cumming, the girl’s face was covered with my cum and I loved at it and so did she. She ran her tongue over her lips and she purred for me. “I lo
ve the taste of your cum,” she told me, and then she smiled, and I knew I was right. Her smile looked even better when her face was bathed in my cum.