My most vivid fantasies have always focused on women doing things with my ass.  I recall lovers who indulged my desires, or invent situations that I wish would happen.  I cherish the image of myself lying on my stomach over the lady’s lap.  This happens either in bed or while she sits in a chair.  I am naked but she is fully dressed.  It is a comforting feeling to offer my bare bottom to her eyes and hands, almost like being a baby.  At the same time, it is very exciting.  My cock gets really hard and my ass tingles in anticipation.  She strokes my hair with one hand, while caressing the sensitive skin of my buttocks and inner thighs with the other.  She speaks gently, telling me that I am handsome and that I have a beautiful butt.  Perhaps she says those magic words, “You’re a good boy,” while stroking my bottom.  Wow!  Those words can be very stimulating, spoken at the right time in the proper tone of voice.  What they represent is acceptance of me as a person, as a man whose vulnerability she finds sexy.  It means to me that I am safe, that the woman understands and approves of my desires.

Perhaps having my ass caressed is enough.  More likely, however, I want more.  I want her to play with my scrotum and cup my testicles in her hand.  There is a special feeling when this is done from behind.  Again, it is that sense of vulnerability.  She possesses my balls, and I trust myself to her care.  When she reaches around my waist or between my legs for my penis, the object is not masturbation but for me to feel a delicious surrender.  My body is in her control.  She is my queen, and all that she touches is in her domain.

I associate that same feeling with another position.  This involves my kneeling on the bed with my shoulders down and my ass up.  Because it is my favorite position in which to have a woman, it is very exciting for me to assume.  The idea of her looking at my ass with the same wild desire with which I look at hers is a real turn-on.  With my anus and dangling testicles plainly exposed, I feel animalistic and vulnerable.  I love it.  I imagine the lady enjoying the view and the prospect of what she might do to me.  I visualize myself bent over a chair, a kitchen counter, or a table, to the same effect.   In any case I am presenting myself.  I surrender to my lady, and she takes charge.

Perhaps she “services” me by licking my asshole, occasionally manipulating my cock and balls from behind.  I feel almost feminine, like a woman receiving oral sex and enjoying it to the extreme.  The main event, though, is when the lady applies lubricant, and lots of it, to my anus.  At first she tickles the outer ring of the hole, before inserting the tip of one finger.  She swirls the finger in small circles, bending it back and forth at the first knuckle.  Through gentle movements she relaxes the “lips” of my anus, preparing it for more intrusive activity. 

Soon I want the entire finger inside.  She plays up the moment, building up to deep penetration with teasing and sexy talk.  “Here it comes, baby.  I’m going to stick my finger deep inside.  I’m going to fuck you up the ass!”  It is important that she use words like “ass,” “asshole,” “butt,” “butthole,” “cock,” and “penis.”  Even “testicles” or “balls.”  “Oh, baby,” she could say.  “I love how your testicles hang down!  It’s so sexy to see your beautiful balls and your anus, so hot and open and inviting!”  The words allow me to imagine her perspective of my asshole, stretched open like a mouth or a vagina.

I also fantasize being anally fucked by a woman with a dildo in her hand, or a woman wearing a strap-on dildo.  I have never experienced strap-on sex, but I would love to.  It has become kind of an obsession, in fact.  These fantasies mostly involve beautiful women—absolute babes—who are gentle and loving, even if they are domineering and insistent.  Only occasionally do I indulge in more masochistic fantasies about a woman spanking me until I beg for mercy, then fucking my asshole with a strap-on dildo bigger than I could actually accept.  “You love it, you bitch,” she says as she slides it home.  “Right up the ass!”  I moan and sob, in simultaneous desperation and contentment at having my lower intestinal tract packed and plundered.  “Are you my little bitch?”  “Yes!” I cry out.  “I’m your bitch!  Fuck me!” I shout as orgasm overtakes me.  “Fuck me up the ass like the horny bitch I am!”  If I am indulging in a prolonged masturbation session with my collection of butt plugs, dildos, and vibrators, or merely fingering my anus while I jerk off, I sometimes act out fantasies like this by speaking aloud in both voices, my own and the woman’s, as she ravages my ass, treating me like a whore.

My anal fantasies began early, though it took years for them to reach that level of detail.  I started fingering my own anus soon after I started masturbating at age twelve.  At one point during my teenage years I carved two little wooden dildos that I varnished and then played with in my butt from time to time.  They weren’t too effective, being hard and inflexible.  If I could have obtained a butt plug or reasonably-sized dildo, it would have seen regular use.  Either alone in my bedroom or in a hidden place in the woods and fields near my parents’ house, I would get naked or just pull my pants down and lubricate my anus with hand lotion.  When particularly horny I would plunge the middle finger of my left hand deep inside, pushing in and pulling out while slapping my erect penis back and forth.  This always led to the most intense orgasms, for which I came prepared with a washcloth to clean up afterwards. 

My anal fetish was strengthened by my first serious girlfriend, whom I started seeing when I was in college.  She was several years older than me, and strong-willed, which has influenced my fantasies ever since: one of my favorite scenarios is a younger man being anally dominated by an older woman.  We had been living together for a few months when she brought in some vegetables from the garden, including one (what particular vegetable is my secret) that had never grown.  It was thin, hard, and distinctly phallic.  We were in bed playing around when I stuck it inside her vagina.  She responded favorably so I became serious and fucked her with it until she came.  When she half-jokingly said that it was my turn next, I hesitated only for a moment before expressing my consent.  I wanted to tell her to use a finger first, to lubricate my anus and open me up, a process I had learned from my long experience masturbating.  But I was too embarrassed to instruct her.  Once inside me that vegetable gave me almost as much discomfort as pleasure.  My girlfriend then mounted me, impaling herself on my very stiff cock, riding it as she moved that natural dildo in and out of my asshole until we both climaxed.

Thus began an important part of our sex life, my girlfriend inserting her fingers or some object into my anus.  She once said she thought she was really a gay man, because she wanted to fuck me like one man fucks another.  I loved being her “bottom” in bed.  It is the most wonderful feeling, physically and emotionally, to be assfucked by a woman.  Sometimes she fingered my butt while sucking my cock, occasionally with me on my back, wrists and ankles tied to the posts of her old brass bed.  I tied her up a few times, but we preferred having me in the passive role.  When she tied me up I begged her to torture me.  She would suck hard on my nipples and then straddle my face so I could lick her pussy.  She would kiss up and down my rib cage, and suck on my inner thighs, which really was a torment.  I cannot stand that—it is too intense.  So is prolonged sucking on the head of my cock, which tingles too strongly.  But as part of the action, it worked.  She would finish these bondage games by sucking me off while slipping a finger in and out of my asshole, or climbing on top to mount my cock and make us both come. 

She learned to lubricate me to make anal penetration smoother and less resistant.  Her way of asking if I wanted to be ass fucked was to say, “Do you want some lotion?”  During a slippery back rub, her fingers would gradually stray downward between my ass cheeks.  That moment just before penetration was wonderful.  I knew what was coming and the feeling that I was letting it happen thrilled me to the core.  It was a feeling of being taken, of being really wanted, focusing on the nerve center of my body.  In a book that I had bought about men’s sexuality, she read about male desire and sexual physiology.  She learned about the proximity of the prostate to the rectum, and how to give pleasure by applying pressure in the right place. 

Sometimes I resisted being penetrated but my girlfriend would do it anyway.  Mounting from behind, she held her right hand between her legs with her fingers in place of a penis.  She thrust her hips just as I did when I fucked her “doggy style,” grinding her pubis on the back of her hand.  She often came before I did when we did this.  One time when she had me on my stomach, I tried to turn, saying that I wanted to fuck her.  “I’m fucking you,” she crooned, forcing my shoulders down as she located my anus with the fingers of her free hand. “I’m fucking you.”  Eventually I learned to plan ahead, assuming she would penetrate me.  I would visit the bathroom before bed to empty my rectum and wash with soap and hot water.  One such night she hurt me.  She started to finger my anus without any lubricant, to which I protested.  “Fuck you,” she said, pumping her fingers savagely, as her other hand reached around my hips to work my cock and balls.  “I’ll do as I please.”  Thrilled by her aggressiveness, I reached an intense orgasm.  In the afterglow I even thanked her for “raping” me.  But my ass was sore for a couple days.  More than once during our years together I bled a little, having been scratched inside.  Overall though, this activity was rewarding for both of us.  Usually she was gentle and anal penetration was a pleasure—a tight, hot, and raw pleasure.  Some of my most vivid fantasies to this day are about being “taken” in this way.  I rarely returned the gesture; a few times I pressed a finger slightly into her asshole, but I sensed she did not want any more than that.  God, I did.  As I told her once, during the act, “Sometimes I want for you to be the man.”  “I know,” she replied, with a laugh.

I had several other girlfriends before I got married, but only one was very fun in bed.  She was a virgin when we met, and it took her awhile to relax and enjoy herself.  The good part was that she was very passionate and wasn’t opposed to trying new things, being unprejudiced by past experience.  I introduced her to oral sex, both ways, and she became a pretty talented cocksucker.  She even sucked down my ejaculations and squeezed out the last drops, licking my cock clean.  She was also the first woman I fucked up the ass.  Of course, being on the receiving end of anal play is more important to me, but I really enjoyed taking her virginity again.  It was an incredible experience, opening her up and slowly working my cock into her asshole.  Wow!  She came before I did, moaning and crying out in her extremity.  I made just as much noise when I let go, squirting a big load deep inside her rectum.

Lovers discover things about each other in mysterious ways.  One day, she commented that it seemed unfair that I could penetrate her but she could not penetrate me.  She wanted to know what I felt when I fucked her.  What a moment!  I shyly told her she could have that experience.  She asked how.  I said that she could insert a finger into my anus.  So she tried.  Her fingers were so small that one did not do much for me at all.  But I had opened up about one of my deepest desires.  The way she discovered my secret desire is one of my fondest memories.

This second serious girlfriend was also the first to lick my anus.  This came about because she begged me to tell her what she could possibly do to please me more.  (I think I looked up at that moment and silently thanked God!)  Rather than specify, I told her to do whatever I did to her.  Every time I gave her oral sex I licked her anus at great length, so I knew she’d get the idea.  One night soon thereafter I was bare on the bed with my ass up in the air.  She had already licked my butthole once, but this was the first time she really concentrated on it.  Approaching from behind, she spread my buttocks with her hands and flicked her tongue around and inside my anus.  This went on for a considerable length of time.  I became more and more excited, as the pleasure radiated outward from my butt to the rest of my body.  Without touching my cock or balls, she brought me to the point of impending orgasm.  Realizing what a unique experience it would be to reach orgasm through analingus alone, I told her to continue.  I sensed that even rubbing my penis slightly on the sheets would trigger ejaculation.  But I let the release emerge solely from the contact of her tongue on my asshole.  Even then I knew it was a special moment that I would always treasure.  Never again have I reached orgasm in just that manner.

I had several short term relationships with women, some of whom I cared for deeply, though none of them really pleased me in bed.  I knew better than to reveal my anal desires to most of these lovers, sensing the narrow limits of their sexual interests.  One woman I did tell, when we were both drunk, clumsily scratched the inside of my anal sphincter.  The relationship was already troubled, but this made me feel victimized.  There was another woman who was sweet and very pretty but a rather dull lover.  One night when I found myself unable to come, I deliberated over asking her to stick a finger up my ass.  Of course I could not put it that way, as she didn’t like explicit language.  But was there any good way to admit my need?  I finally told her directly.  “There is a way you can help.  You can penetrate me anally.  With a finger.”  She was not happy with this development.  She obviously thought the act was disgusting, but would only say that she would not like doing it.  She asked if I had ever had sex with a man, which made me angry.  I told her that anal pleasure had nothing to do with sexual orientation, that the idea was a stereotype.  At one point she offered to do it with a condom on her finger.  I later brought up her suggestion, asking if the offer was still good.  It was, she said.  It was not sexy at all.  I masturbated furiously with her condom-wrapped finger motionless inside my anus.  By focusing intensely on happier memories I managed to get off.

After years of relationships not working out, I met a wonderful woman whom I married within two years.  She was a virgin when we met so I initiated her slowly.  Anal fingering took her awhile to contemplate.  She had very little understanding of sex anyway so the idea that a straight man wanted his butt poked was not easy for her to accept.  I was patient even when her preconceptions and stereotypes led her to ask if I’d ever had sex with a man.  No, I hadn’t, and I had never been interested.  I had always fantasized about women fingering my butt, I said, and I had lovers in the past who really liked doing it, not just to please me, but because they got off on it themselves. 

Eventually she came to enjoy giving me anal pleasure, for her own sake as much as mine.  I have found the queen of my heart, and she now owns my ass.  She knows the ways to please me, like bending me naked over her lap as she sits, so she can stroke my bottom like a baby.  She stands me against a wall, ass out so she can spread my cheeks apart with her hands and lick my balls from behind (one of my favorite sensations) as well as my butthole.  She has bent me over the kitchen table, chest out flat supporting my weight as she approached my anus, penis, and dangling testicles from behind.  Best of all, she takes me on the bed, on my back while I masturbate, or favorite of all favorites, on all fours with my head and shoulders pressed down on the bed, ass in the air as she satisfies my deepest need.  Occasionally reaching around to stroke my cock, she kisses my buttocks, sometimes biting them hard enough to make me gasp in a wonderful mixture of pleasure and pain.  She also makes me gasp in joy by spreading open the space immediately around my anus with her fingertips.  She licks around the perimeter to tease me, and then hits home, lapping wildly on my dark hole while I lose myself in pleasure, moaning and crying out her name.  She is the only woman who has actually worked her tongue inside.  She starts alternating a fingertip, poking inside to the first knuckle, using her saliva for lubricant.  A little tongue, a bit of finger, a little more tongue, then the finger goes in deeper.  She invented a trick that I hadn’t thought of—she licks the ring of my anus around her inserted finger, which combines the pleasures of penetration and rimming.  That really sends me.  She has finger fucked me while I masturbate to orgasm, or rimmed me until I do the same.  She uses the lubricants I buy, and knows to find my prostate a little ways inside and then towards the forward wall, towards my belly.  She usually just uses one finger, but has worked in two, three, even four inside at once. 

Another thing she likes is to mount me from behind, rubbing her mons against my tailbone, which feels really good because I have some lower back problems, but also really sexy.  She can easily reach orgasm doing that, or by spreading my ass cheeks and grinding her clitoris against my anus.  I love that because it feels like the phallic power has totally transferred over to her.  She thrusts like I do when fucking her, and makes circular movements much like I use for variation.  And she admits to loving all this.  She tells me I have a beautiful ass and that she loves fucking me.  Though she isn’t as verbal during sex as I would like, she does thrill me sometimes by describing how open my asshole is, or by asking if I know what she’s about to do.  One time while fingering my butt she said that my asshole was just like a vagina, which really got me!  For all this, I’m grateful beyond belief.  I’m lucky to have a woman who likes to give me what I crave, as much for her own pleasure as for my own.

My wife won’t use sex toys with me, though, which I regret.  I sometimes think I will have to seek satisfication of this desire outside my marriage.  Once in awhile when my wife is not around I get out a butt plug or a dildo and KY jelly and fuck myself, fantasizing about being anally ravished by a woman.  Sometimes, before or during masturbation, I look at pornography involving female-on-male anal sex. There’s a lot available online, and I’ve amassed a large collection of videos, photos, artwork, and stories of analingus, anal fingering, dildos, and pegging.  There seem to be a lot of people like me who love the idea of women fucking men up the ass.

I can’t complain too much, though, because my wife is so passionate and unabashed about intercourse, oral sex, and anal play.  The fact that she loves my ass is enough to make me eternally grateful for my good fortune.  She fulfills my fondest desire, to have my anus penetrated by a slender womanly finger.  I long to bend over and reach back with my hands to spread my butt cheeks.  I so want to be seen, to have all my private parts in clear view and in my wife’s total command.  I love the anticipation.  I even like the clicking sound when she opens the tube of lubricant, knowing that in a moment she will be spreading that cool gell on my hole.  She knows that I want her to talk to me, so if she feels like being verbal she’ll say something like, “Do you know what I’m going to do?  Do you know what I am about to do?”  To which I humbly say, “I know what I hope you’re going to do.  I hope you’re going to insert a finger into my anus.”  When she does, when my wife slides her finger inside me, parting the sphincter’s warm tender tissue, all is right in the world.  My craving is satisfied.  I am truly alive, complete, safe, and loved.  And when I ask her if this is what good boys get, if good boys get fucked up the ass, if she’ll always finger my butt, and she says yes, you’re a good boy, my good boy, and your ass is mine, then I don’t need any more.  Any more than for her to slide that finger out and let me fuck her until she’s come a few more times, so I can ejaculate onto her breasts, or her face if I get the nerve, or for her to finger my butt until I squirt, allowed to focus on my own pleasure as I fulfill the dream of my boyhood and manhood alike, to have the woman I love and who loves me deep inside me, as much in my heart as inside that passionate, desperate orifice that gives me almost as much joy (and frustration) as the cock and balls that are my pride and joy.