Anne Makes Him a Man

"Oh? What's that?"

"Well, I heard Dad and some of his friends one time talking about fucking women in the ass. Dad said he and Rachel do it all the time. You ever let a guy put his dick in yours?"

"Anal?" I asked. "Sure, a few times."

"Doesn't it hurt to have a guy fuck your ass?"

"Not if either of us use enough lubricant. And sometimes it's tighter back there than some women's pussies."

"I dunno, your pussy was pretty tight," Pauly observed. "And fucking hot."

"I haven't had a man in awhile," I quipped.

"A sexy woman with a nice tight pussy AND good at fucking like you? Damn, baby, guys who don't want to get you in bed must be on the pipe!"

I grinned, then got back to the subject of anal sex. I could tell by the gleam in his eye that he wanted to try that too.

"If you want to feel what anal is like sometime, I'm willing to help there too," I added. I'd said "sometime," assuming he'd be worn out from all the sex we'd had already.

Wrong again, Anne.

"Can I fuck your ass now?" Pauly asked. "I'd really like to feel what it's like when Dad does it to Rachel."

Pauly wasn't totally hard yet, but he wasn't completly soft, either. I figured if he wanted to fuck me in the ass, he needed a good hard on to get the job done.

Even though I am probably one of the handful of women that love anal sex, I hadn't had it in ages, so I was definitely willing to get a hard cock in the backdoor again.

Especially Pauly's cock. If he could fuck my cunt so well for his first time, I had a feeling he was going to be equally good in my ass, if not better.

I dipped down and took him in my mouth again, performing the deep throat he had loved earlier to get him going.

"Damn you can really suck cock!" he panted as his erection grew in my mouth. "Jesus, Anne, you are one hot woman!"

When Pauly was completely rock hard, I withdrew my mouth from his cock, then reached into the bedside drawer for the K-Y that had still yet to be used.

I put some over Pauly's very healthy erection before giving him the tube and, flipping myself over, instructed him on lubing up my asshole.

"Lube me up good, baby. Then we can fuck."

Once he had greased my asshole with the K-Y per my instructions, I reached back and helped Pauly slowly guide his throbbing prick into my ass.

He wanted to bury his entire cock in my ass right off, but I told him he couldn't plunge into a woman during anal as opposed to fucking a pussy; he had to slowly enter her ass so she would get used to his cock in it and it wouldn't hurt her.

"Ohhhhhhhhh..." he moaned when his dick was eventually halfway up my backdoor, "Your asshole is sooooo tight...baby, this feels reallly gooooood."

"Fuck me, Pauly," I encouraged, my ass fully enjoying his (at least) seven-inch cock in it. "Yes, baby, give me some more cock!"

"More?" he asked, pushing in a little further.

"Yessssss!! Fuck my big ass real good, baby. Give me more of your cock! Pauly, fuck me!"

I could hear his pants increase and his moans grow louder as he pushed deeper and deeper into my ass, then begin to thrust in and out of my chute at a good pace.

"That's it, baby," I said. "Fuck my big ass just like you did my cunt! Fuck me, Pauly!"

"Fuck!" he called. "This feels so fucking good, Anne! Ohhhhhhh shit...I never thought I'd ever fuck a girl in the ass..or that would be so fucking hot!"

"Oh fuck, Pauly! Fuck me like a whore!"

Pauly sped up, fucking my ass harder to the point the bed was shaking again. But he felt so good!

I then felt myself about to cum for whatever time that afternoon; Pauly had made me cum so much that day, I'd lost track of how many orgasms I actually did have.

Or maybe I'd also cum so much because it had been so long since I'd actually had a good, hard fuck. But whatever.

For anyone that is curious, anal sex really does give the best orgasms, and I was about to have my most intense one of the day with Pauly pounding in and out of my asshole.

"OH FUCK! Fuck me, Pauly!" I screeched at the top of my voice. "Fuck my ass! Fuck my ass with that hard big cock of yours! Oh, God, Paullllllllly! I'm going to cum! FUCK MEEEEEEEEEEEE!!!!"

Grabbing the sheets and putting my head down so it wouldn't bang into the headboard of the bed, I screamed out my climax, putting Pauly into an even more ass-fucking frenzy.

"Pauly, fuck me!" I cried again. "Fuck! I'm cuuuuuummmmmiiiiiiiiiiiiiiinggg!!!"

"I'm right behind you, baby," he finally called. "I'm going to cum in this tight asshole of yours!"

"Ohhhhhhh yeaaaaaaah, Pauly!" I called back. "Cum in my ass, baby! I want to feel your hot cum fill up my ass! Cum for me! Fuck me!"

It was all the encoragement he needed; Pauly exploded a large load of cum deep into my bowels, filling me to capacity with his creamy seed and groaning in ecstasy when he did so.

When he finished filling my ass with his hot semen, we collapsed back onto the bed.

"Fucking incredible," he moaned. "I never heard of women cumming while getting fucked in the ass, though."

"You need to get out more. Anal sex makes the hottest orgasms," I grinned. "When a woman cums during that, you know you're doing it right!"

"Really? You liked it?"

"Baby, I loved it," I said, then kissed him. "You can always come here for more of it if you like."

We then laid back on the bed, still naked, and talked for awhile before hearing a car door slam.

Pauly's father and his father's girlfriend had arrived home and it was almost dinnertime.

I hadn't even realized we'd been having sex for so long! I guess time really does fly when you're having fun.

And his dad would no doubt be looking for Pauly; the last thing we needed was him finding his son naked in bed with me with a little of Pauly's cum leaking from my ass!

We then got out of bed and Pauly put on his shorts while I took some tissue and cleaned off my cunt and ass before putting my own clothes back on.

Pauly then thanked me for letting him know what sex with women was really like and said I'd make "one really hot sex ed teacher."

I told him there was more where that came from and to drop in anytime he got horny again.

"I'll keep that in mind," he said while I walked him to the door. "You are one hot fuck, Anne. If you get another boyfriend, he's is going to be lucky!"

I could say the same if Pauly ever got a girlfriend. Provided she liked sex to begin with of course.

But since the day we had fucked that first time, Pauly and I have gotten together for more sex several times before he left for college that fall, with Pauly getting hotter in bed each time.

Then when Pauly got his winter break from school later that same year, his father and now-stepmother were away visiting her parents and Pauly still didn't have a girlfriend.

He was so alone over at that house by himself.

Naturally, I offered my company to Pauly during his school break...for a "price."

Not that he complained; he not only shared my bed every night that week, we also ended up fucking and sucking in every room of my house and every possible position.

After that, Pauly became my very own private stud every weekend and break he had. We even spent a weekend together when I visit his campus, staying in a nearby motel.

And four years later, he now 23 and I 40, we are now living together, both of us with good jobs and discussing marriage.

And the sex is hotter than ever between us.

Funny how things worked out for both a guy who wanted to experience sex for the first time and a horny older woman who fantasized what he was like under those tight shorts!

I knew I took his virginity all those years ago for some reason...