My girlfriend and I have a really great relationship - we love each other very much and the sex is amazing. One thing I really love about my girl, Michelle, is that she is very adventurous and willing to give just about anything a try in the sack. I say 'just about' because there is one limit I haven't been able to broach - anal sex. She has not allowed me to play with much less enter her back door... yet. I see her limit more as a personal challenge to overcome, however, and have been working on her to get her to feel differently about it.

I really don't know where this anal phobia came from; we have done lots of other things that I would think were far more taboo than anal sex. Perhaps it's her upbringing at the hands of her father, a church deacon, and her mother, an upper-crust society type. They kept her on a pretty tight leash growing up and I can imagine that had something to do with her Edinakusesiphobia (the fear of anal sex).

Whatever the cause, it has definitely had its effect on her - she can't even watch porno movies where the girl is getting back-doored. Which is hard because I have to preview each movie by myself all the way through to make sure there are no anal scenes (difficult to do these days, as most of the movies have some kinda of anal sex in them someplace). Since I love anal sex that always leaves me with a pecker as stiff as a telephone pole and I usually have to find a way to take care of it. Since I don't want to cheat on her and she isn't around when I preview these movies, that means I have to spend some "personal time" with my thoughts!

We have found a few movies that we can watch together, though, and once it has been checked and found anal sex free, she feels fine to watch them with me. And the accompaniment of the sights and sounds of the video always improves our already amazing sex times. I just wish I could get her past this hang-up she has.

I have seen her pooper before - when we "69" I can see it just above (or below) me, winking at me, teasing me with the promise of unknown delights which I can only imagine. I have had anal sex with other past girlfriends and I love the feeling of a tight tunnel hugging my cock like that. Don't get me wrong - Michelle has a wonderfully tight pussy and I love being deep inside it. But anal sex has a different feeling which I long for now.

One day while I was at work, Michelle had one of her girlfriends, Jessica, stop by for a visit. The two of them had a little lunch during their visit and as they were chatting the conversation invariably went to boys and sex. From what she told me later, the conversation went something like this:

"So how are you and Steve doing?" Michelle asked.

"Oh, we are fine. He took me out to dinner the other night to this really great restaurant. He knows that Italian food is my weakness, and this new place opened up that featured Italian food. It was wonderful!" Jessica said.

"Your Mom is Italian isn't she?" Michelle asked.

"Yep. My great-grandparents came to America right after the war in 1947 when my grandma was only two years old. My Mom was born in 1969, a first generation American. I was born in 1991. So, yeah, there is still a lot of Italian influence in my family," Jessica said. "I grew up with my grandma's and my mother's cooking and this was old-school Italian - the real stuff!"

"Sounds wonderful," Michelle said. 

"It was. And Steve knows my past and he took me to this restaurant ran by an Italian family - it reminded me so much of my childhood!" she said, grinning.

"Steve really did a good job then," Michelle said.

"He did. And after we got home I showed him how much it meant to me!" Jessica said with a wink.

"What do you mean?"

"I mean I gave him a good old Italian dessert!" she said giggling. "I was his little cannoli and I let him give me the creamy filling!"

"You're terrible!" Michelle said, giggling along with her. Then they started talking about what they liked in bed and that's when Michelle learned that Jessica loved anal sex. 

"Oh, I could never do that!" Michelle said.

"Why not? It's great fun and so fucking hot!" Jessica said. The two of them talked about it and apparently getting another woman's point of view got through to her.

That night when I got home from work, Michelle met me at the door in a very strange... and very sexy... way.

"Hi baby," she cooed when I walked in the house. My sweet Michelle was dressed in a sexy sheer pink babydoll that was held together in the front with a small pink bow tie. There were ruffles along the bottom hem and underneath she wore a matching sheer panty with cute ruffles across the buttocks. Her long flowing brunette hair was gently curled and her makeup was done just the way I love it with soft red lips and mascara lined soft blue eyes. She was a beauty and all mine!

"Wh-what's all this about?" I said, eyeing her suspiciously. She wanted something - Michelle wouldn't go to all this trouble unless she did! Either she wanted something, or she did something she wants me to forgive her for!

"Can't a girl get dressed up for her husband once in awhile?" she said in her kittenish way. Yeah she is all 'little miss innocent' I thought to myself, as innocent as Jezebel!

"Hmm..." I responded skeptically.

"Let me hang up your coat for you. You go on in the living room and sit down sweetheart. I will bring you a beer and your paper. Dinner will be done in a little bit... it's your favorite - pot roast!" she said so sweetly I almost went into a diabetic coma! As she came up to me I took her wrists and held her hands out palms up. 

"What are you doing?" she asked.

"Just checking," I said.

"Silly man! Come sit down!" she said taking my hand and leading me into the living room. "There, now you just sit here and I will be right back with your beer and paper, darling!" she said. 

Man she is laying it on thick tonight! I wonder what's up? I thought to myself. She came back in a flash with a cold beer and my newspaper neatly folded.

"There you go honey. You sit here and relax and I will call you when dinner is ready, baby," she said kissing me on the forehead as she left. I watched her walk towards the kitchen and just as she rounded the corner into the kitchen she looked back and blew me a little kiss.

It was about twenty minutes before I saw Michelle again. She came bouncing in as I was finishing up the newspaper. "Dinner is ready sweetheart!" she said, bubbling over with enthusiasm. She took my hand and walked me into the dining room and sat me down at my place at the table. She served up dinner and then sat there patiently until I took a bite.

"Well, how is it?" she asked. She was right, pot roast is one of my favorite meals and the way she makes it, it is even more delicious. 

"It's great, honey. Your pot roast always is the best," I said. She smiled broadly.

Once I had given my approval to her cooking, she started eating. I caught her glancing up at me a couple times - she quickly averted her eyes down to her plate when she saw I caught her.

We didn't talk much during dinner after that. We both finished about the same time and Michelle told me to go back into the living room and she would be in as soon as she took care of the dinner dishes. 

I went back into the living room no closer to figuring out what this was all about then when I first got home. As soon as she was done in the kitchen she called out she would be right there and headed for the bathroom. This was my chance. As soon as I heard the bathroom door close, I got up from the chair I was sitting in and went to the bathroom, standing in the hall to wait for her.

I heard the toilet flush and the water running in the sink; I knew she would be coming out any moment. I was placed in such a way that she would be turning away from me and heading back towards the living room. When the door opened and she stepped out, I quickly grabbed her and pushed her back against the hallway wall. 

"You have been acting very strange since I got home tonight, Michelle. All the syrupy sweetness, the pot roast, and not saying more than a couple sentences during dinner. I want to know what the hell is going on and I want to know now, Understand?" I said, forcefully.

"Okay, Dave, but can we go in the living room to talk, please?" she asked. I took her by the upper arm and marched her into the living room and I pushed her down onto the sofa across from my chair.

"All right now what is this all about?" I asked her again.

"Today Jennifer came over for a visit and we had a long talk. She told me how her boyfriend Steve had taken her to a new Italian restaurant and after a wonderful meal she and Steve went back to her place and she thanked him for the evening. Jennifer and I talked a bit and she told me how much she likes..." she paused, embarrassed to continue.

"What? What does she like, Michelle?" I asked.

"She told me that her and Steve enjoy anal sex," she said finishing her sentence. She told me about it and she seemed to really like it."

"Well anal sex can be a lot of fun. You know how I feel about it. But you never liked it," I said.

"I know. But maybe..." she said. It was as if she wanted to say something but was too afraid or too ashamed to. I needed to give her a push.

"What, Michelle, what are you trying to say? Tell me. Tell me what you want," I said.

"Dave I think I want to... try anal sex. Would you show me how it's done? Jennifer says she loves it and I know you like it. I just want to make you happy honey," she said, looking straight at me. I looked into her beautiful face, her eyes darting back and forth, her imploring look was impossible to refuse. 

I stood up without another word and took her by the hand, leading her back to the bedroom. I sat on the edge of the bed and pulled her to me. She looked so beautiful in her little babydoll, it seemed almost a shame to remove it from her. But it would have been in the way and got messed up anyway, so I reached up and very slowly pulled on the ribbon tie to release the front of her lingerie. Her babydoll fell open on it's own and I slipped my hands under it to cup her lovely breasts.

Michelle had wonderful full firm breasts - she may have been twenty-five years old chronologically, but she had the breasts any nineteen year old would envy! They were C cups with dark areolas and sensitive hard little button nipples that I loved to chew on and they loved to be chewed on! As I held her breasts in my hands I let my thumbs lightly graze over those sensitive buds and felt them instantly respond, growing harder and thickened under my touch.

Her nipples must have sent their messages straight to her brain because even as I toyed with them, Michelle drew a large breath, sort of a reverse gasp, and thrust her breasts out further for me to play with.

Then I peeled the thin flimsy garment from her soft shoulders and let it fall to the floor behind her, a pink puddle on the dark wood floor. I pulled her closer to me, between my spread knees and wrapped her hands behind her, holding her wrists behind her back and my mouth sought something to suck. I homed in on the nearest nipple and inhaled it, licking and sucking on the crinkled pink morsel while Michelle moaned her pleasure.

For the next minute or two I devoured her, alternating between her nipples often so neither would feel left out. Michelle squirmed and twisted in my arms, offering her breasts up to me and relishing in the feel of my tongue and mouth on her. She loved having me lick and suck her breasts - it was on of her favorites forms of foreplay.

I began to notice the effect I was having on her by the sweet musky aroma that began filling my nostrils. Faint at first, it grew stronger the more I played until it was unmistakable. Her scent filled the room and filled my nostrils, tempting me and beckoning me to find out where such a delightful perfume came from.

Leaving her breasts for the moment I gave each a final kiss before moving down to investigate this delicious scent. I kissed my way down her belly, stopping to tug gently on her navel piercing with my teeth. Moving on down I reached her bare mons. Michelle kept herself shaved clean because she knew I liked that and she liked the way it looked as well - it gave her a hot, sexy look that she really liked.

When I moved a bit lower, I found the source of the intoxicating fragrance... my Michelle was sopping wet! Her panties had become drenched with her juices as the anticipation of tonight and the toying of her breasts had done their work. She was practically dripping right through the thin material!

"Oh my dear, you have soaked your panties right through! We will have to get you out of those wet things!" I said playfully. I looked up and she was biting a long ruby fingernail coyly as I spoke to her.

I pulled her panties down slowly until they reached her knees at which point the fell on their own to her feet.

I reached between her spread legs and fingered her dripping pussy, letting my fingers explore her thick swollen lips, trace tiny circles around her clit, and then slip into her just far enough to run my fingertip around her vaginal opening without going into it. The teasing made her hips gyrate and she tried to hump my hand, but I moved with her - I wasn't ready for that just yet! 

When I had her hips rotating like they were on a pivot, I reached way under her and, with my forearm between her legs, I stood up, turning, and threw her bodily on the bed. She landed on her back in the middle of the bed, giggling like a little girl. She automatically had her legs spread wide apart and as she lay there I stood at the foot of the bed and began getting undressed myself. 

I removed my shirt and t-shirt and dropped my pants, all while Michelle smiled. But when I got to my boxers and she saw what all this had done to me, her smile turned to one more of anticipation. She bit the corner of her bottom bottom lip as I slowly revealed what I had waiting for her. and when my cock sprang free Michelle licked her lips appreciatively.

"Oooh, Daddy!" she said, her eyes never leaving my cock. "Daddy" was her pet name for me and she called me that whenever she wanted something really badly. So I knew I had her full attention.

"Daddy first babygirl," I said, and I crawled up the bed from the foot till I got between her legs. She knew what I had come for and had placed a pillow under her hips to raise herself up for my dining pleasure. With her legs spread wide, she reached down and spread her pussy open with the thumbs of each hand, offering her wet pink interior for my inspection.

I gazed into the wondrous opening, the one that had provided me so much pleasure in the past and promised even more delights in the future. Michelle has a beautiful pussy, pink and glistening, and it feels even better than it looks. I could hardly wait to feel that warm, wet tightness holing my cock in its glorious embrace. 

But first I wanted to taste the woman-honey I saw dripping from the walls. So I lowered my face to the steaming cauldron and touched her inner lips with the tip of my tongue. The moment she felt that first tentative lick, she came alive. 

"Ohhh..." she moaned arching her back a bit. She spread her legs wider as if asking for more, so I gave it to her. I pulled my head up to smile wickedly at her and she drew a deep breath. She knew what was coming and prepared herself for it.

I dove into her sweet juice box with gusto then and the aggressiveness of my attack and the feel of my tongue diving deep into her caused Michelle to cry out in rapturous surprise. I sucked her pussy to my mouth, fastening on as my tongue began its reconnaissance, searching every soft fold and every hidden nook for pearls of her sweet juice. 

Michelle moaned and squirmed and writhed under me trying to escape the vexation my tongue and mouth were giving her, but I was determined and held her tightly. There would be no escape and no mercy for her until I had had my fill. The more I feasted on her juicy peach, the wilder and more desperate she became. Soon she was thrashing around violently, whimpering and crying and blubbering incoherently.

I knew she was getting close to an orgasm by the way she sounded and acted. So I renewed my efforts to try to push her over the edge and give her the first orgasm of the night. This was easy to do - Michelle always came easily and usually multiple times during out play times. She loved cumming and I loved making her cum so we both enjoyed the event thoroughly.

"Ohh Daddy! Oh I'm gonna cum, I'm gonna cum for you, Daddy! I'm I'M CUUUUMMMINGGG!" she cried out loudly.

She bucked and pitched around on the bed as her orgasm took over control of her body, tossing her around like a rag doll. She poured out her copious juices making the bed wet with pussy juice and sweat as she rolled around. Finally, panting and exhausted she lay still trying to control her body and slow everything down again. I let her rest for a few minutes until I saw her eyes coming back and focusing on me again.

"Oooh Papà," she cooed reverting back to her Italian, smiling at me, her eyes half-closed as the euphoric feelings of her orgasm coursed through her still.

I moved up the bed to take her in my arms and softly brush the sweat-matted hair from her eyes and hold her slowly rocking her until she was fully back from her blissful heaven.

Once she had fully recovered, she looked up at me, then sat up. "Okay Daddy, now it's my turn!" she announced, grinning. "I want to lick that lollycock!"

"Well come get it babygirl!" I said and she moved swiftly to do that very thing. She moved between my legs and with no pomp or fanfare began licking up and down the shaft of my cock like it was a popsicle. She ran her tongue around the rim and poked into my peehole, scooping up the drop of precum I had waiting for her there. 

"Yummy!" she said and went back to her work. She licked all the way down my cock to my nuts and took them into her hot mouth one and a time, licking and sucking them till the cum inside was near boiling. She licked further down tongue-bathing my perineum and almost rimming me before moving back up to the head of my cock again. I was moaning and pushing my hips up now - it was her turn to tease!

She looked up at me as she hovered over my hard, erect cock pointing at her soft red lips Smiling a little "I know what you want" look she took the head of my cock between her lips and slowly slid down the length of my cock, her eyes never breaking contact with mine. She went down on me further and further until she felt me at the back of her throat. She breathed in deep through her nose and then pushed the rest of the way down, opening her throat to take me in fully.

Michelle had just recently learned to deepthroat - another thing I had to thank Jessica for. Jessica had shown Michelle's own gel dildo, how to take a cock down her throat. And she had gotten pretty good at it, always making me crazy when she did it to me. She learned how to keep from gagging and even how to make her throat muscles "milk" my cock and coax it into giving up it's load. More than a couple times I blew my nut straight down her gullet from her deepthroating me!

But she knew we were there for another purpose tonight. She had asked me to show her about anal sex and she knew if I came now, as pleasurable as it would be, that I wouldn't be able to do anything for an hour or so. And so after a little bit of play and getting my cock hard enough to drive a ten-penny nail through an oak board, She pulled away from my cock, leaving a very sexy trail of saliva connected her lips to my cock.

"You should be hard enough now, I would think!" she said grinning. She rolled over to her nightstand. Here I picked this up today at the store. This is what Jessica uses when her and Steve play in the back. She says it makes everything a lot easier on them both," she said, showing me a bottle of lube. 

I took the bottle reading what it had to say about the product. "Well I guess if Jessica and Steve use it and like it we can give it a try," I said. 

"So how do we do this - you are the one that knows about this stuff so what do you want me to do?" she asked.

"Well I think having you on your knees with your head and chest on the bed to bring your ass up higher is about the best position for starters," I said. With that she moved into the position I said in the middle of the bed. She put a pillow under her head to hug or bite if needed and spread her knees nice and wide.

I moved up behind her, stroking my hard cock while looking at her firm pale ass. I ain't lying, folks... I was really getting excited now. I had been telling her for a very long time how much fun anal sex can be - for both of us. She was still apprehensive about the idea but Jessica's talk seemed to open her up to the idea. So I decided to show her what she had been missing all this time. 

I squeezed some lube from the bottle and smeared it all over my cock. Then I squeezed a good dollop on it onto my fingertips and applied it to her tight puckered hole. She sucked in a breath "Damn that's cold!" she complained.

"Don't worry babygirl, it will warm up quickly," I assured her. I smeared the lube around her hole then gently pushed my index finger inside her just a bit to get her sphincter muscle greased up as well. I could feel her tense up a bit as my finger opened her up - she had never had anything enter her there. "It's okay hon, just relax and let me get you lubed up," I said. She tried to relax after that, trusting me not to hurt her and knowing that if it got too hard for her, all she had to do is say so and we would stop.

But she was very brave and I was able to get my finger inside her and spread some of the lube all around inside her rectum. "Okay babygirl, now that you are lubed up good, I need to open you up a little bit to make room for my cock. Don't worry, though, I will take it slow and be gentle," I said. Michelle nodded her head and braced herself for it.

I began by inserting a finger back inside her rectum. It went in a lot easier this time since she was already used to it. Then I introduced a second finger into her hole. She moaned a bit as I began with the second finger, pushing back against my fingers as they worked their way deeper. I moved my fingers around inside her working her, stretching her opening larger. A third finger slid in and Melissa moaned louder. She was pushing back, humping my fingers back and forth. I looked at her and she was gripping the pillow tightly and moaning almost continuously now. She was just about ready.

Pulling my fingers from her ass, I gently took each of Michelle's firm ass cheeks in my hands and spread them. Man, I do love this woman's ass! I moved closer to her, my cock hardening. I pressed my cock against Michelle's asshole, and slowly pushed it inside. I was amazed at how warm and tight Michelle felt around my cock. She turned around and looked at me with wide eyes. I grinned at her -  we were finally doing this. She kept telling me to be gentle. I nodded. Gripping her slim flared hips, I took my sweet time as I pushed my cock deeper into her asshole. Slowly but surely, I worked most of it in there. I asked Michelle how she liked it. 

She asked me how I knew that she would like anal sex. I smiled and told her I knew her adventurous side would enjoy trying something new. I knew that if she just got past her strict upbringing, that she would enjoy this once properly introduced to it. 

Man, I couldn't believe this. I was finally fucking my sweet Michelle in the ass! She shrieked as I rammed my hard cock deep into her asshole. She cried for me to grab her hair and spank her ass as I fucked her ass harder. I did just that, folks. I couldn't believe how wild this chick was! 

I yanked her head back by roughly grabbing a handful of her brunette hair and slammed my cock deep into her shitter. With my other hand, I smacked her ass. I noticed a red mark appear on her pale white skin and smiled with satisfaction. Michelle squealed and begged me for more. I kept smacking her ass while drilling my cock into her ass hole. Now, this is what I call a wild ride!

As I fucked her for all I was worth, she reached between her legs, rubbing her clit like she wanted to rub it off her totally. She furiously fingered her clit and pussy as I pounded into her backside, driving her face into the pillow and causing her to cry out in sheer unbridled lustful joy.

Before long the combination of my cock stretching her asshole and her own fingers tearing at her clit brought her to a mind-blowing orgasm. She raised up on one hand and threw her head back screaming her orgasm and I blasted her asshole with my own. I came, flooding Michelle's asshole with my cum. As I squeezed my cock out of her widened asshole, she groaned loudly and collapsed on the bed. I fell to the bed next to her just as spent.

A little while later, I lay on the bed, watching Michelle walk around the bedroom looking for her panties. She couldn't find them because I had accidentally tossed them into a corner behind the dresser! She gave up after a few minutes of looking and sat down on the bed to talk about what we just did. For a moment, I was nervous about it. However, Michelle was down with it. She said she never knew how much fun anal sex could be and she loved that I took it easy and was so gentle and caring about it. 

Then she moved closer and gave me a big loving hug. "But the next time we do this, I want you to not be so gentle and caring. I want you to fuck me silly, Daddy!" she whispered lustfully in my ear.

Hot damn, my Michelle was one hot and kinky girl. Did I luck out or what?