This is a print version of story Road to Pegging by lov2dancecpl from

Road to Pegging

Road to Pegging
By Peter n Sharie
This is the first story we ever wrote.
We like to start off telling our story from the beginning of the road to pegging. In our story it’s about my wife using a dildo on me for the first time. We thought it would be interesting for some couples where the woman is reluctant in using a dildo or strap-on on her man, as my wife was very much reluctant up until the time of this story.

My wife and I have been married for 29 years and together for over 34. We have always been a very sexual couple. From the beginning while we were dating back in the 70’s we found so much fun in exploring each other desire's, we’ve tried all the sex positions we could come up with. Always trying new things getting many ideas from magazines, another way was reading the Joy of Sex book, we would go to Sharie s****r’s house every month to get her b*****r-in-law’s newest issue of Hustler & Penthouse magazine we loved reading the story’s. When VHS came along we would rent lots of porn. We became very energetic sexually, we being a very passionate couple for each other pleasures, with an adventurous and at times a Kinky side to us. Some of my friends were very envious of me for having such a great sex life with Sharie, as they have heard some my stories.
From the very beginning Sharie and I both very much enjoy giving and receiving oral sex, 69 our favorite. Over time Sharie and I learned what would drive each other crazy. The one for me is while Sharie would be giving me a blow jobs her tongue working over my cock and balls it would always seem that her tongue and/or fingers would find their way to my asshole. My wife would start rimming my ass, her tongue deep in my ass lubing it up. Her mouth moving up to the tip of my cock for her tongue to take my pre-cum then proceed to start rimming my ass more. Once my ass was wet enough she start sucking my cock again then she start sticking her fingers in my asshole. I would be do the same to her I eat her ass while using my fingers in her wet pussy I be switching back and forth lick some sweet pussy as my fingers fuck her ass, lick her ass, my finger in her pussy. This became a regular thing for her performing anal play on me with her fingers or tongue.

About 3 years after we were married I wanted to bring sex toys into our bedroom. My preference was a dildo or vibrator telling her it was for me to use on her, but secretly it was mostly for her to use a dildo on my ass. In hopes that she would, I went out one day and purchase a dildo for us to play with telling her it was for me to use on her. Which I did many times and she loved it, I knew she would too! The dildo I bought was a cork screw shape dildo 18inches long and 1 ½ inches thick.
As time went on I started asking her to use it on me. Sharie, as most people, doesn’t understand why a guy could enjoy anal sex being performed on him by sticking a dildo or strap-on up his ass. At the time she had no idea that anal sex preformed on a man is so enjoyable for him that it can also make a guy cum. For a longtime after I had bought the dildo I kept asking her to fuck me with it, she was always reluctant to use it. It felt too uncomfortable for her to use a toy like that on a man and that no other man had ever asked her to do anything like this. Trying to explain to her what would be the deferent’s if she was using her fingers in my ass, with up to 3 sometimes even 2 or 3 fingers from each hand at the same time so why not use the dildo? At the time part of her explanation was that her fingers are a part of her not something else, not something fake, in her own words “IT’S NOT REAL!” that was giving me pleasure. It was a very hard sell for me to get her to do this, I wasn’t sure if she ever do it or not. Hard for me to understand why she wouldn’t after everything else we had experiment with sexually threw all the years going back to when we first started dating. I even try the approach of her having revenge on me shoving something up my ass as in how I have fucked her in the ass with my cock many times.

Then on one hot summer night we were watching X-rated movies. So hot we had the windows open while we were laying on the couch together totally naked as we watch the porno. Lying there in the spooning position playing with each other while watching the action on the TV. I had the back position Sharie in the front of me which gave me a free roaming hand. I rub her up and down the front of her playing with her pussy, rubbing her tits. I have one eye on the TV watching the action while sucking and licking her neck which drivers her crazy. Sharie reaching around the best she could rubbing my legs, ass or cock. If my cock wasn’t in her hand it was between the cheeks of her ass. Seemed that night both of us were horny as hell more than other nights. Don’t know if it was better than average porn movie along with a hot summer night but we headed for the bedroom. Not waiting till the end of the movie. We hit the bed and a night of hot sex started.
Soon we were in our usual 69 position Sharie was giving me a great blow job as her finger were fucking my ass. As always I was using the dildo in her pussy and a good finger fuck in her ass. She cum’s big-time when receiving both oral and anal sex at the same time she had an intense orgasm. Once she does cum a few times she has me pull out the dildo. As always I did but this time without thinking too much about it I threw her the dildo.
I said “My Turn! Fuck my ass with this honey.”

To my surprise she reaches over grabs it. Sharie started teasing me by rubbing the tip of the dildo around and around my hole. Sharie started slowly pushing the head into my ass. My ass already lubed & loosen up by her finger fucking, my ass took it in very easily. She was sliding it in and out of me, deeper and deeper a little at a time. I could feel the ribs of the cork screw dildo popping in and out of my ass enjoying it immensely. Sharie could tell as I was moaning and moving my hips up and down along with the rhythm of her hand that was fucking my ass with the dildo. She seeing how much I was getting off on it she started fucking me harder and faster. With the pleasure of my ass being fucked so much not realizing it but I had stopped everything I was doing to her. I was just laying there still in the 69 with her.

I was moaning like crazy couldn’t help but say
“aaah… aaah Honey this is awesome honey keep fuck my ass, aahhh fuck me!”

Sharie says playfully “Sure thing baby, using a dildo is much easier than using my fingers in your ass.”

I started giving her a titty rub with both my hands, her body started rocking side to side on top of me. I guess this was enough for her, seemed like she was enjoying this she was letting out some soft moans.

“Sharie this is so good, you ok?” just had to ask, I didn’t want her doing this if it was too uncomfortable for her.

With a sexy chuckle she answers
“I’m fine, seeing what this is is doing to you, I LIKE IT! I love seeing this up close, makes you ass VERY SEXY”

Sharie working the dildo in my ass while sucking on my balls one at a time letting them pop out of her mouth. She started to roll off the top of me as she pulled out the dildo she then gives my ass a slap saying…

“Roll over get on all fours”

I got down on all fours then she got behind me between my legs. She reaches for the bottle of lube then opens it. Putting a big squirt at the top of my ass I jumped as I could feel the cold lube running down between the cheeks of my ass. Sharie laughing

“Little too cold for your hot ass? Let me warm it up for you honey”

Sharie rubbing the lube up and down the crack of my ass teasing my hole with her fingers along the way rubbing just the outside of my asshole massaging my anal passage... I squirmed with desire for her to use the dildo again.

“Please fuck me again with the dildo”

“In time” she replied giving me another soft slap on my ass.

She then slipped a finger into my ass working it in and out, then a second, and then a third moving them in a circular twisting motion deep inside me, pushing deep as far as her fingers could go. This went on for a couple minutes.

In a kind of a sweet but teasing way she says
“You like this don’t you baby?” With a Hard Deep Thrust shoving her fingers into my ass before I could answer.

“UHHH, Yes I do”

She gives me another Hard Deep Thrust!

“UH the best ass fuck you ever gave me” I answer very submissively.

“mmmm good baby, I’m enjoying giving it to you”

Later I found out why she was enjoying it so much it was the way I became very submissive to her.

With a harder slap on my ass
“NOW! Put your head down, spread your legs and stick your ass up in the air!"

I did very quickly. As I knelt there head down ass up feeling totally under her control I heard the cap again of the bottle of lube I naturally looked back at her and I seen her adding lube to the dildo.

“TURN AROUND Peter don’t look!”

I then could feel the dildo at the hole of my ass she was moving around in circles then up and down between the cheeks of my ass.

“Are you ready for more Dear?”

“Yes please honey”

Slowly she started fucking me again little by little pushing the dildo into my ass then back out again. Giving me a little at a time then pulling it completely out beginning to just teasing me with it up and down my ass. Being in the doggy style position I couldn’t see Sharie but I could tell she was getting off, enjoying the fact of how much her teasing me was driving me crazy with desire. I too am enjoying the tease. She was taunting me with a dildo, how cool, such a turn-on for me.

“Peter your nice ass so shiny from the lube it’s so sexy. With all you taken so far it’s still a tight ass… looks so good… I never realized how much I would enjoy fucking you”

Sharie reaches down between my legs with one hand rubbing my balls then grabbing my cock, jerking me off a little. While the other hand still using the dildo in my ass. I’m really enjoying this doggy style it was fun but I still wanted to be fucked deeper.

“Oh yes baby please keep fucking me! GO Deeper! Please”

“Deeper? BUT Baby! How I’m enjoying teasing you, watching you squirm for more this is so much fun”

I could then feel the dildo slip from my ass completely. With my head down, legs spread wide, my ass up in the air I was feeling very vulnerable to her first time ever.

“Honey please don’t stop, keep fucking my ass” I begged her I was so turned on.

Sharie taking the dildo and bouncing the tip off my hole then I felt some slight pressure.
Then in one hard swift motion Sharie shoved most of the dildo deep inside my ass.
I wasn’t ready for that I screamed into the pillow then moaning with pleasure.

“OH Babe Fuck me”

She then leaned herself forward placing a hand on the middle of my back pushing me down and holding me down. I know I could have pushed her off of me but I didn’t want too I was loving it. I so enjoy it when we get ruff during sex but this time it was ALL her. My ass being pounded hard by her finally.

“Oooooohhhhhh yes yes harder Sharie keep fucking me”

Sharie talking sassy, talking down to me
“Peter! Keep fucking you like this baby? Deep? Hard and fast HUH baby? Is this what you want? Is this how you like it? You’ve waited for THIS! Am I good? You Having fun?”

“Uh huh” I whimper “It's so good”

“That’s Good! It’s fun for me too. Your ass so exposed so obedient to me I love it”

My ass up in the air squirming around backing into the dildo. I was getting fucked hard dildo going deeper and faster, no stopping this time no more teasing from her I was getting a hard ass fucking. What a turn on it was well worth waiting for, the both of us having fun. Few times she reach down with her other hand giving my cock a few good jerks.
I was getting close to cumming, Sharie could tell as she grabs my cock feeling all the cum oozing out.

“Are you ready to cum baby? A Good ass fucking going to make you cum baby?”

“Yes, you’re going to make me cum”

She stops, then bossy like
“Roll over on you back, I can’t believe you’re going to cum by an ass fucking? I want to see this!”

I rolled over onto my back. Kneeling next to me I looked up into her eyes, with a smile she was looking down on me with a sultry look in her eyes. Without her asking, in showing my submission to her I put my legs up in the air making my ass more accessible to her. Sharie starring into my eyes she started rubbing the dildo up and down my body. She knew what she was doing, putting herself in control, I knew it too because she was in control. The dildo going up and down my body she roll it around my nipples, push my cock and balls around with it just looking down at me not saying anything. As I looked up at Sharie with my legs up, ass exposed I was feeling totally vulnerable to her again then a sense of humiliation came over me laying there waiting for her to start again. I was so turn-on by it.

“Let’s really see if I can get this rubber cock to make this real cock cum” Slapping my hard cock with the dildo.

She reaches down between my legs with the dildo in her hand, inserted the dildo back into my ass! She pushed a little deeper, gently moving the dildo in a shallow circular motion, stimulating my ass so much! She was rubbing my cock and balls with her other hand.

“Ok Peter let’s see you shoot, let’s see you’re cum fly”

Getting a nice long slow deep fucking now with the dildo I wonder how long it would take me to cum for her.
She leaned over to me.

“Kiss me baby” she said

I reached up to her we kiss passionately... Her tongue was inside my mouth, then mine in hers. ...., we started kissing each other’s neck. Her beautiful tits hanging there swaying by the movement of her arm shoving the dildo in me. I reached for them started sucking on her nipple. She places her hand behind my head pushing me closer as I sucked her nipples with her fucking my ass.

“mmmm feels good keep sucking” she moaned

Sucking and licking her nipples I started moving up to her neck, I kissed and nibbled on her lovely neck and her ears, this drives Sharie crazy.

She was moaning
“Aah mmmmm so niceeeee……”

The good ass fuck now turned into a passionate ass fucking with Sharie getting even hotter. Being on my back, my arms free I started rubbing Sharie body where ever I could reach giving her some pleasure now. Kissing her neck, continuing to fondle her breasts... I wasted no time moving my hands down to her legs. I begin massaging inside of her thighs while my lips on her neck as I tease hers. My hand makes it to her pussy, tracing her pussy lips with my finger… as I spread her lips open I could feel how hot and very wet her pussy is. I put 3 fingers in her wet pussy moving slowly around inside of her. I couldn’t believe how wet she was Sharie was really turned on. Could it have been the ass fucking she was giving to me or of my submission given to her.
She moans loudly and pushes her hips forward against my hand. Her hips moving to the rhythm of my fingers going into her wet pussy the deeper I went the more her hips pushed. Just as I moved my hips along with the rhythm of her hand shoving the dildo in me. We both were getting off fucking each other. I worked my mouth up to hers gently licking her lips, her tongue meets mine we go into a passionate kiss

She whispers in my ear.
"After you cum baby I want you to make love to me...please… I want to feel you cock inside of me."

My hand rubbing her tits….
My other hand working over her pussy deep inside her….
She’s getting off as she starts working the dildo faster fucking my ass….
Both of us in intense pleasure,
Our wet lips pushing hard into each other….
Both of us moaning with pleasure….

I whisper into her ear
"Aah Sharie I just have to taste you!"

I remove my fingers from her wet pussy move them up to our mouths. While kissing her lips and our tongue teasing each other’s tongue I then added my fingers to our mouths with the juice of her pussy.

“Let's share your juice, Taste your pussy”

“Glad too” She said

She put one of my fingers completely in her mouth… she closes her lips begins to suck on my finger gently to get all her pussy juice from it. Wildly our lip’s, our tongue’s licking the pussy juices from my finger’s as she continues to fuck my ass like crazy. I can’t take much more I feel it coming I going to shoot my load.

“I am going to cum, OH baby I’m going to cum!”

“I got to see”
Sharie leans back to see as she does she stops using the dildo I SCREAM!

“Dam!! Fuck! NO Sharie don’t stop keep fucking me I’m cumming”

I’m moaning loud, My cock erupting, spewing cum all over my stomach, some of it shooting all the way to my chest.
My hands grabbing on to the bed digging deep into the sheet and mattress. It’s an intense orgasm. Moaning louder

“Sharie keep fucking me!... Sharie keep fucking me!....”

“MMM YES shoot baby, you are cumming! I’m not touching your cock” she chuckle’s “shooting loads, all from a good ass fucking”

Sharie still pounding my ass with the dildo seemed like every thrust in my ass another load shooting out of my cock. Sharie a few times reaching out catching some of the flying cum it was almost like a fun game for her.

Then it was over my body sinks, my legs fall Sharie hand still between my legs with a grip on the dildo working it in my ass.

“Sharie please enough… I had enough stop, please!”

“No No dear first lick your cum off my hand”

I started too, then she scoops up more with her figure “Lick more.” She commanded

She pulls the dildo from my ass she falls on top of me, we kiss passionately. Sharie saying

“I’ll give you few minutes rest then it’s your turn to fuck Me! Peter”

That was over 25 years ago. Over the years we’ve collected many anal toys of different shapes, color, sizes and some vibrating ones. Used them many times on each other we had lots of fun. The one toy we never bought was a strap-on she says she would feel funny wearing one. In the beginning it took me 3 years to get her to fuck me with a dildo now it took me 25 years to get her to finally agree to a strap on.
Good things are worth waiting for, that’s in Part II

Story URL: