This entry is part 10 of 19 in the series 2012 Nov

My grandmother’s friend Tracy is a pleasant—and very buxom—lady who has long been a family friend. Over the years, I heard quite a few stories about how “active” she was when she was younger, but recently it seemed like she’d settled into a more respectable and ladylike life as a 69-year-old widow and grandmother.

When she visits, I always take certain chances, putting my arms around her and asking her how my favorite mature woman is doing. She’s never really reacted, but about a month ago she surprised me and asked how her favorite sexy young man was doing. Then she asked if my girlfriends were putting out enough. I played along and after telling her they weren’t, I patted her on her ass, gave her a quick squeeze, and asked if she’d “gotten any” lately. She giggled and pulled away as my mother and grandma walked into the room, but she never answered. As she walked away from me, though, I realized how hard my cock had gotten as I’d flirted with her, and I found myself watching her ass sway as she turned the corner and went down the hall. I had to compose myself for a second before I was able to walk around without inadvertently showing off my erection.
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Anal Aficionado

You know how all these women go around saying that no woman really enjoys having anal sex? Well, I’m living proof that they’re wrong. The only way I can come, in fact, is by getting fucked in the ass. Nothing else will do, as far as I’m concerned.

The first time I told my boyfriend about my preference, he was thrilled. None of his previous girlfriends had ever asked to be fucked up the butt, and he was dying to plug my behind. After a few times, though, he asked me what I really liked. He couldn’t believe that I liked having his cock up my ass as much as he liked putting it there— maybe more. “Girls don’t really like anal,” he said, citing a bunch of past hookups as references.

“Well, maybe most girls don’t like it,” I told him, “but if I don’t get to take a huge cock up my ass at least twice a week, I go crazy.”

Lenny still wasn’t convinced that I really loved anal like I said I did, but he wasn’t going to put up a fight when I begged him to put it up my ass.

Sometimes I want him to bend me over and take me from behind, and other times I like when he lays me out missionary style and then pushes my legs up to my ears so he can stick his cock in my ass instead of my cunt. We always use a lot of lube, so it’s always nice and slippery, and I like it best when he pounds into my ass like a jackhammer. He can save that soft, slow fucking for my pussy if he wants to take it easy, but if he’s going to fuck my butt, it has to be hard and it has to be fast.

Take our last anal sex. I’d come home from work horny as fuck, and as soon as I walked into the house, I grabbed Lenny by the collar and dragged him to the bedroom. “I need you to plow my asshole,” I begged. “I’ve been horny all damn day, and if you don’t fuck me in the ass right now, I just might lose my mind!” I whined.

Lenny didn’t need me to say anything else. He pushed me onto the bed and hoisted me up on my hands and knees. He pulled my tights down past my ass once I was in position, then got some lubricant out of the dresser and unzipped his pants, freeing his dick. I could hear him whacking off behind me, getting his dick hard, and then I felt the cold lube being smeared over my sphincter. I was seconds away from getting the ass fucking I’d wanted all day long.

As soon as I was lubed up, I felt the fat head of his cock nudge my butt, and then he pushed past my entrance and lodged his dick deep inside my asshole. His cock is the perfect size for butt fucking, longer than most but not too thick. He never has trouble shoving his shaft into me. Once he was all the way in, he started to thrust. He took maybe a dozen slow, steady strokes, just to get his angle right, and then he started to pound me like a madman. His balls slapped loudly against my ass cheeks as he pounded his cock into me. I cried out in pleasure with every single thrust, telling him to give me more, more, more.

My body was being shoved forcefully back and forth on the bed, but it still wasn’t enough, and I started thrusting my ass back against my boyfriend’s pelvis, trying to take his stiff cock deeper and faster.

It took only five minutes before I felt my orgasm building up, and I started moaning even louder, letting Lenny know I was on my way.

I came a moment later, digging my nails into the comforter as my orgasm shook my body. I didn’t even have to play with my pussy or flick my clit or any of that shit other women say they have to do to come with a cock up their ass. The cock up my ass is all it takes to get me off.

Lenny came less than a minute after I did, and each shot of come into my ass turned me on more, until I felt a second orgasm building up inside me. Usually I don’t come multiple times, at least not one on top of the other like that, but I guess I’d been even hornier than I realized. A healthy dose of anal loving was obviously exactly what I needed that day.

So to all your readers who still think that there aren’t any women out there who really like anal sex, I hope this letter proves them wrong. If not, tell them to look me up. I’m always more than happy to prove my point over and over and over again— especially if it ends in orgasms!— S.J., Scranton, Pennsylvania

Head Over Heels for Ass

My boyfriend likes to joke that my ass is like a 24 hour deli— it’s always open. I always tell him he’s being crude when he says that, but he’s not wrong. If there’s one thing I love, it’s having Joey’s cock buried in my ass.

We’ve had anal sex in every position imaginable, but my favorite is when Joey bends me over the arm of the couch and plugs my ass from behind. That position always gets me off faster than any other, probably because that’s usually the position we end up in when the sex is spur of the moment. Most of the time we do it in the bedroom, but when we come home from a bar or a party— or the grocery store— and we just can’t wait, Joey will bend me over the arm of the couch, then rip off whatever I’m wearing and fuck me.

Last week it was after a quick trip to the mall that we ended up fucking over the arm of the couch in our living room. I’d been looking for a dress for a business dinner I had that night, and Joey had come along to buy some new video game. It had only taken him two minutes to find what he was looking for, so he’d quickly joined me in the department store. He was bored out of his mind waiting for me to find a dress, but he amused himself by checking out my ass in each and every outfit. I went through dozens of dresses, none of them quite right. They were all either too risqu or too conservative. And not a single one of them made my ass look good, at least not according to Joey. Just when I thought I was out of luck I found the perfect dress.

The sleek black bandage dress had a classy, sexy square neck. It fit me tight but not too tight, hugging my all curves from my cleavage down to my knees. And the way it wrapped around my butt, it made my ass look beautiful! When Joey saw it, his jaw practically dropped, and he really wanted to do it in the fitting room. I wasn’t about to risk getting busted in my favorite store, and I really didn’t want to accidentally destroy my new dress, so I pushed him away and told him no, he’d have to wait until later.

He wasn’t willing to wait until too much later, though, and the second we walked into the house, he was on me. I’d worn a loose dress that day, since I knew I’d be trying things on, and as soon as Joey had me bent over the arm of the couch, he had my dress flipped up and my underwear pulled to my knees. His jeans were on the floor not a minute later, and then his hands were on my ass. He rubbed and caressed my cheeks, and when he leaned up against me, needing to get closer, I could feel his erection, already as hard as steel, press against me.

The next thing I felt was his cock pushing between my butt cheeks and filling my asshole. The minute his dick nudged against me, my ass opened up for him, ready and wanting. It was an automatic response, and I loved the fact that my body knew exactly what to do when Joey was involved.

He slid into me with ease, and then he bent me further over the side of the couch, his cock sliding even deeper into my ass in the process. I buried my head in the cushions and pushed back against Joey’s groin, needing him to thrust into my ass. My boyfriend didn’t disappoint, and after he’d stretched my ass with his big cock, the fucking really began.

Joey plowed into me, and with each stroke my body rubbed against the couch’s rough fabric. When my cunt started to rub on the arm, it enhanced my arousal, and I wiggled my ass as I tried to get more of what I wanted from my boyfriend. He pumped harder into my ass, just like I wanted, and it was perfect. I felt my cunt spasm as my ass was filled over and over by Joey’s thick shaft, and I knew I’d come soon, maybe even before he did.

After a few dozen extra strokes, I came, squeezing my ass to hold Joey in place while my pussy throbbed and gushed juices on the arm of the couch. I gripped his cock tight in my ass and held it there until he started to come with me. Then he filled my ass with his come, his cock pulsing hard between my fat, round cheeks.

When we finished, I had just enough time to shower and change before leaving for my dinner. Joey tried to stop me on my way out, my new black dress once again inspiring his anal lust. I told him he’d have to wait, but when I got home from the restaurant, I was more than prepared for round two!— H.K., Phoenix, Arizona

Fitting In

My wife Veronica and I are regular readers of Penthouse Forum. Each month we read the new issue, and mark passages with descriptions of sexual activities we are interested in trying out. I am a very fortunate guy, because I have a very beautiful wife who is into everything when it comes to sex.

Recently Veronica marked off a letter about anal sex. Actually, we had been attempting to have anal sex for months, but every time we tried it, Veronica would call it off, saying that my dick was too thick for her. Every time I ate her pussy, I would put two fingers in her ass and fuck her with them. She always had great orgasms that way, and my hope was that, with repeated sessions, her ass would get used to being opened up and we would be able to have satisfactory anal sex.

Veronica and I are into threesomes, which we participate in regularly with a friend of mine from work named Craig. Once, after another unsuccessful attempt to take my dick in her ass, Veronica said, “You know, I bet I could take Craig’s dick in there. It’s shorter than yours, and thinner.”

“Yes,” I said. “I noticed that whenever you gave him a blowjob, you can always take his dick in all the way down to his balls.”

“Would it be okay with you if we had Craig try to fuck my ass?” she asked anxiously.

“Sure, why not? Anything that gives you pleasure, babe. And I’d like to see it too.”

Craig came over the following week, and I explained to him what Veronica wanted him to do. He couldn’t believe it. Craig had often commented on what a great ass Veronica had, and now he said he’d like nothing more than to fuck it.

Veronica went in to take a shower, and when she returned she was wearing a sheer baby doll nightie that really showed off her big tits and shapely ass.

I kissed her as Craig began to fondle her tits. As we ran our tongues up and down her body, Veronica started to pant with desire. I unsnapped the front of her nightie, and Craig pulled it down over her shoulders. As her breasts came into view, Craig immediately began tonguing them. My tongue was busy as well, licking her pussy and asshole.

Veronica was soon very close to orgasm. We stopped and placed her on the couch on all fours. Our cocks were already rock hard, but Veronica expertly sucked our dicks to make us as ready as possible.

Craig got behind her, and I spread her ass cheeks apart and told Craig to fuck her. His dick slipped easily into my wife’s asshole. She let out a gasp and begged him to go further. He plunged his cock deeper into her anus. She humped her ass back onto his pole as he fucked her harder.

I moved around to Veronica’s face so she could suck my hard prick again. She was moaning and saying that it felt so good to have a hard cock in her ass. I stuck my dick in her mouth, and she sucked it as she never had before. I had my prong so far down her throat that my balls were resting on her chin. The harder Craig fucked her ass, the deeper she sucked my dick. Her voice was muffled by my rod as she gasped out that she was coming. As her ass rotated on Craig’s prick, he tensed and shot a load of come up inside her, while at the same time I shot my wad down her throat.

What a great threesome! Veronica told us she loved it and wanted to do it again very soon. I told her that just as she had become excited enough to take my whole cock down her throat, I was hoping that eventually she would also be able to take it in her ass. We will definitely keep trying.— F.C., Camden, New Jersey

Biracial Birthday

I am a thirty eight year old widow with four children. When my husband passed away six years ago I was forced to go back to work. Since then I have worked myself up to the position of administrative assistant at a fairly large manufacturing plant.

Between working and raising my children, I don’t have much leisure time. I do enjoy bowling, and I belong to the company bowling team. It was through the team that I met Tim, a tall black man who works in the shipping department. We slowly developed a friendship, but though I did sleep with him once after a party, we did not become lovers.

My birthday is in January, and this year when it came around I felt the need to celebrate in a special way, one that would assuage my unsatisfied physical needs. So, throwing caution to the winds, I decided to visit Tim.

I rang his doorbell, and I could see the surprised look on his face when he answered the door. He obviously wasn’t expecting anyone, as he did not have on a shirt or socks but he invited me in without hesitation. He took my coat and we went into the living room and began some small talk.

Finally, I just blurted it out. “Tim, it’s my birthday and I want you to do me.”

He didn’t need a second invitation. He took me by the hand and led me into the bedroom saying, “So the white lady has finally decided to let the black man do her again. Well, all right!”

In the bedroom he didn’t make a move, but stood by the door watching me as I undressed, placing my clothes on a chair. I began to feel self conscious, but I wanted him badly, and however he wanted to play it was okay with me.

When I was naked he still didn’t move. I walked over to where he was standing and knelt in front of him, then opened his pants and took out his semi hard penis.

“That’s good, white lady,” he said. “Taste the black man. Lick me.”

I was wild about his big black member. I put it in my mouth and began flicking my tongue around the head. Then I lifted his penis and licked his testicles. I felt him stiffen, but his face remained expressionless, so I put him back in my mouth and began moving him in and out. I was not surprised to feel myself getting moist. My breathing was becoming rapid and I actually started to get off on the feeling of his cock moving in and out of my mouth.

“It’s my turn now, white lady,” Tim said finally. He took my hand and motioned me up and onto the bed. He gently pushed my legs open and inserted a finger inside me. After moving it back and forth a few times, he withdrew it and put it into my mouth. “Lick it off, baby,” he said. “Taste yourself for me.” I had never tasted myself before, and the thought of what I was doing made me even more excited.

Opening my legs wider, Tim put his two hands under my bottom and placed his thumbs between my thighs. With his thumbs he spread my vulva, then leaned down to place his tongue on my clitoris. As he flicked his tongue back and forth I could feel vaginal fluids begin to run down my thighs. He began licking the fluid from my legs, making long passes with his tongue from my thighs across my vaginal opening, ending just above my clitoris. I moaned and spread my legs apart even more. He began to probe my vagina with his tongue, until I felt I couldn’t wait any longer. “Please come inside me now,” I said.

Instead he rolled his tongue like a straw and placed it around my clitoris, moving it back and forth as though my stiff little nubbin was fucking it. I couldn’t hold back any more my body stiffened and I cried out as I climaxed.

“You’re ready to feel the black man inside you now,” Tim said. He reached over to his nightstand and removed something from the drawer. It was a tube of K Y jelly. He put some on his fingers and then proceeded to apply it to my fanny. He also put some on his penis.

My heart began to race. I had never had anal intercourse. I had heard that it was wild, but I wondered if it would be painful. I also wondered how he would enter me, as I was still lying on my back. I didn’t have to wait long. He took hold of my ankles and, seemingly without effort, rolled me onto my stomach. “Pull your knees up under your belly,” he said, “but leave your shoulders down on the bed.”

He knelt between my legs and I felt his penis begin to push against the opening of my fanny. I tried to relax as I felt his stiffness probing my rectum. It felt good. Gradually he pushed harder, and I moaned with a new pleasure as the full length of him slowly filled my back tunnel. Then he began to move out, and I thought he was going to take it away, but instead he rammed himself back in, causing me to gasp with delight. I was more relaxed now, and I could really feel all of his fullness inside me.

Now he began to move out and in with a regular rhythm. I pushed back at him, meeting his thrusts, and again I could feel the vaginal fluid running down my legs. I was going to climax! When I did, my muscles tightened and Tim emptied his seed into me. With each ejaculation, I could feel his penis pumping his sperm into my clutching behind.

When he pulled himself out I thought we were done, but he put his hand on the small of my back to indicate that he wanted me to stay in position. I felt him slide his cock back and forth over the cheeks of my ass, and to my astonishment it soon started to get hard again. A moment later I felt him mount me once more, but this time he slid himself into my vagina, which was wet, open and ready. He pushed himself all the way inside me, and then paused as he spoke into my ear.

“Happy birthday, white lady,” he breathed. “This is a special birthday fuck, and I’m gonna give you a stroke for every year.” He pulled his hips back slowly and then shoved that iron hard dick all the way inside me again. “One,” he said.

I couldn’t believe this. He held himself still again for a moment while I squirmed with anticipation, then pulled himself out and rammed back in again. “Two,” he said. I was already panting and moaning. Then, “Three” and “Four.” My breasts shuddered with the force of his thrusts, and I knew I would come long before he got to thirty eight!

At twelve I climaxed. At nineteen I climaxed again! At twenty three, I was crying with joy, and by the time he got to thirty I was coming almost continuously, unable to control the waves of passion suffusing my twisting body.

“Thirty eight!” he said finally, and pulled out of me, his still hard ebony flagpole standing tall. I slid my knees out from under me and lay there exhausted on my stomach, panting and moaning with bliss. If I had ever climaxed as many times in one sex session, I couldn’t remember when.

As I began to dress, Tim took my panties and said he’d keep them until I told the world about how good the black man was. He gave me a copy of Forum and told me that when he saw a letter in there about us, he would give me back my panties.

So I hope you will print this letter, because I’d really like to get my panties back!— L.I., Mason City, Iowa