Chapter 4

I picked up the hairbrush and rubbed the back of it over her ass to get it coated with oil as well. I wanted her to feel the instrument that would soon be punishing her.

I let her get used to it and as soon as she was comfortable and enjoying its touch, I raised it up and brought it down hard on her ass cheek.

“SMACK!” The sound reverberated in the quiet room.

“OH FUCK!” was her instant reply.

“SMACK!” another swat to the other cheek and now she had two red marks shaped perfectly like the hairbrush.

“OWWCH!” she shrieked again.

Then I gave Carol two back to back swats, one on each cheek and in different spots to further pinken her up.

“Now that I have your attention, slut, I’m going to heat up that ass of yours properly. I’m going to give you ten swats, then pause and check on you. I’m not going to give you a chance to catch your breath until all ten swats have been delivered. So if you need to stop before that, use your safeword.

I didn’t wait for her reply this time. I just dove right in and began. After the first ten swats, she was screaming out. I paused to allow her to catch her breath. “How are you doing?”

“G-Green.”

I immediately gave her another ten swats and again I stopped. “How are you doing, slut?”

She replied with another “Green.”

I could see I had underestimated her tolerance. “Okay, let’s not waste any more time. It’s plain to see you can take it, so I’m going to paddle you until I’m done or you cry out your safeword. I want to get on with the next part.”

I began raining down swats on her ass moving from cheek to cheek and around so that I covered her whole ass. Then when her ass was glowing bright red, I moved down the backs of her thighs a bit. That really got her attention–I don’t think she was expecting that.

A couple swats to each thigh and she’d gotten enough. “Red! Red Tommy!” As I promised I stopped instantly, without another blow falling on her tortured ass. I stood up and she slid down onto the floor on her knees. I grabbed her and pulled her to the sofa so her face and chest were on the seat. I yanked her panties off her and tossed them on the sofa next to her. I poured a bit of baby oil on her asshole and using my finger, I worked it into her crinkled ass.

She lay on the sofa back moaning and pushing back against my finger as I lubed her insides. Then I put some oil on my hand and lubed up my very hard cock. Carol had already told me she was no stranger to anal sex and, in fact, loved it. So I wasn’t worried about her being a “virgin” in that regard. She was tight, no doubt about that, but she would loosen up fairly easily once she got used to me being in her ass.

I pulled her around and made her sit on the front edge of the sofa pushing her back and raising her leg up until her feet hooked over the sofa back. With both her pussy and her ass completely open and exposed, she was ready for me now.

I placed the head of my cock on her shiny, puckered little hole. I could feel the tightness of her anus against the head of my cock. Slowly, I began applying pressure to open her up and enter her ass. Her muscles flexed and relaxed as she tried to stay calm. I continued to push on her tightly closed anal hole harder, then a little harder yet. I could feel her asshole start to spread open ever so slightly.

“Ohhh,” Carol whimpered. It wasn’t from pain, but from getting her asshole stretched open by my hard cock. She hadn’t had anyone fuck her ass in a long time and it felt a bit unfamiliar to her now. I applied a little more pressure and her tightly puckered asshole spread apart to take in my cock. My cock head slipped inside Carol’s ass and I was immediately gripped by her tight anal ring. She took a deep breath to relax. “It’s so big,” she moaned out, experiencing my cock in her ass for the first time.

I started pushing in deeper, driving my cock into her ass. I looked at her face. Her eyes were wide as I pushed my cock into her but she made a grateful facial expression as she moaned, “Oh, God it feels so big.”

Then I penetrated her still deeper, pushing through her asshole another couple inches. “Oh my God! Ohhh!” she continued moaning as my cock burrowed into her incredibly tight bunghole.

It was incredibly exciting to watch my cock slide between Carol’s beautiful soft asscheeks and disappear inch by inch into her tight asshole. Slowly her ass took my cock into its firm grip as I leaned into her to fully penetrate her rear end. I couldn’t believe it. After all the years of dreaming and more than a few late-night masturbatory fantasies, I was actually doing it. I was fucking Carol, my dream woman, in the ass. My cock was inside her rectum and her asshole had a tight grip on me.

I couldn’t stop telling Carol how terrific her ass felt. “Your ass is so hot and tight, baby. My cock feels so good inside you. I’ve wanted to fuck this sexy ass for so long.” Then finally I was all the way in.

I held myself there for a few moments, as deep in her ass as I could get, feeling the tight hug she was giving my cock and waiting for her to get accustomed to having something (me) back there. I moved an inch or two in and out to encourage her ass to loosen so we could continue.

When she did relax her ass a little, I began moving my hips back and forth. Starting slowly, I pulled almost all the way out until just the mushroom head stayed inside. Then I pushed slowly forward deep into her ass again. A few long slow strokes later and I felt she was ready for fucking.

She still had an incredibly tight asshole. Fucking her ass was beyond belief. I looked at Carol’s cute ass as I fucked it, admiring its beautiful shape and curves. As I pulled back from her asshole, her anal ring hugged my cock tight and stretched outward until I fucked back into her. Her ass was so hot inside and it felt so good. “My God, honey. Your ass is so fuckin’ tight. I dreamed about this day of fucking your beautiful asshole.”

I could have stayed right there forever with my cock inside her ass and been perfectly happy. It was as close to heaven as I’d ever been. Once I felt she had been “sized” properly, I began fucking her hole a little faster and harder. My cock was moving in and out of her ass like a piston in a car engine. She was taking it like a pro. It was hard to believe that my neighbor and my mother’s best friend–a woman I had always pictured as the consummate lady–was such an accomplished anal expert!

But there she was right in front of me and there was no denying how good she felt. I knew there was no way I could keep this up long. I was too aroused fucking my dream goddess in the ass.

Knowing that my time in this anal Shangri-la was limited, I decided to push my luck and see if I could really make this hot sexy incredible woman mine after all. Could I convince her that I was more than just her neighbor? Could I prove I was enough man to handle her in all her moods and keep her under my control and command?

I believed I could, otherwise, I wouldn’t have started down this path. The last thing I wanted to do was get myself into something that was over my head. I was trying to prove I was capable of being the man she needed–making a fool of myself by biting off more than I could chew was not going to get me the girl!

No, I was sure I could handle her needs and give her what she wanted so much. All I needed to do now was convince HER of the same. So I decided to go all-in. A quote from my high school history course comes to mind. It is a quote from Virgil: “Audaces Fortuna Iuvat (Latin) - Fortune favors the bold.” I was going for broke!

“Now, you told me you love a good assfucking. So I’m going to show you what good assfucking’s all about.” I shoved my hard cock back in Carol’s asshole hard slamming my balls against her ass.

She moaned out loud. “Ahhhh...”

I pulled out almost all the way then slammed her ass again. “Oh FUCK, Tommy!”

And then again I backed out and let her feel my full eight inches move in and out of her asshole. The friction her tight fuckhole was causing as my cock rammed her over and over again was unbelievable. I kept going, shoving my whole length in and out of her ass as fast as I could.

“How’s that feel, Carol? Do you like my cock up your ass? Do I make you feel like a slut?”

“Oh yessss ... fuck me, baby, fuck my slut asshole!”

I was all too happy to grant her request and reamed her asshole good and proper while I continued to coax and taunt her into begging for more. “You like getting fucked like a cheap whore, don’t you? Tell me, whore, tell me how much you like my big cock up your tight ass.”

“Ohhh! Oh my God! Yesss ... Fuck me, Tommy!”

“Fuck me, baby, harder! Yeah, fuck my whore asshole! Oohh ... Oohh ... Oohh...”

She was screaming in delight as my cock plunged in and out of her tight hole like I was drilling for oil in it. I was driving her lust to the limits as my hard cock pumped in and out, and my balls slammed against her asscheeks.

“Oh, God!” Oh my God! Yess ... fuck me, Tommy! Oh, please fuck me...”

I slammed into her ass again. Carol’s breathing became heavier and more ragged–I could tell she was lost now in her own lustful delirium. She started clawing at her tits pinching and tugging at her nipples. She was losing control totally and could only think of my cock fucking her ass. She was enjoying this buttfucking and didn’t want it to stop...

“Ohhh! Oh, fuck! Ohh! Don’t stop! Oh, please ... Ohh...!”

“Feels good up the ass, doesn’t it?”...

“Yes! Oh God yes! Ohhh! Ohhh! ... Fuck me! Fuck my asshole! ... Harder! Please, harder!”

She was desperately pleading for me to ram her asshole harder and harder. I don’t know how she was able to handle the brutal fucking I was giving her asshole as it was, but she wanted more. I knew she had to be on the verge of an orgasm, she was literally out of her mind as I was slamming her ass.

“Oh my God! Oh my God! Oh my God! Fuck me ... Fuck me, harder, Tommy! Ohhhh!...”

I figured it was time to help her over the edge. “Play with your clit, whore. Play with your clit and fingerfuck your nasty pussy while I fuck that ass!”

She did as I said, adding yet another layer to her anguish. “Ohhh! Oh my God, Tommy, please...”

“That’s it, Carol, just let yourself go. You like this, don’t you? You like acting like a filthy slut, don’t you?”

“Oh God, Yessss...”

Yes, you like being a whore. But whose whore are you?”