Michelle's First Anal Adventure
by Master Jonathan
Copyright© 2022 by Master Jonathan
Romantic Sex Story: Dave has been wanting to get Michelle into anal sex but for some unknown reason she has been against it. One day after she talked to her best girlfriend she decided that tonight is the night...
Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa Consensual Heterosexual Fiction Anal Sex Masturbation Oral Sex .
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 it’s 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. For 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 if 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 “little girl” 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. She stepped lightly out of them and I picked them up to inhale her musk once more before tossing them aside.
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