A Gentle Pegging

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She loves him well with more than one toy.
2.5k words
4.42
80.3k
86

Part 1 of the 2 part series

Updated 06/08/2023
Created 10/05/2016
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This is my first story exploring the world of femdom and pegging. Please be honest but gentle with me.

*****

It's been a long month, for both of us. It's late on Thursday night when you climb out of the car. I can see in your shoulders that you are weary. You look like you're carrying the weight of the world. But for the weekend, you are mine, and I have one goal: to make you forget about life outside the walls of my house.

You approach the house, and I come down the steps and I put my arms around you. I'm tearing up with how much I love you and how much I know you've been through lately.

I hold you tightly as your arms wrap around me. In that moment, I realize with more clarity than ever before what the phrase, "The whole is more than the sum of their parts" really means. We are each strong people. But together, that strength is magnified. We bolster each other up.

By Sunday, when you leave, you will be refreshed, and renewed, and once again ready to do battle with the world. But for now, you can leave the machismo at the door. I am in charge.

I reach for your hand and pull you into the house.

You collapse in a chair at the kitchen island, and I push myself into the space between your knees. Again I wrap my arms around you, this time gently kissing your cheek. You turn quickly to kiss my lips, and our embrace tightens as we delve deeply into the kiss.

You are kissing me urgently and insistently, and I parry back with my tongue. Your hand drifts down to caress my butt through my dress. As you do, you realize that I am already wearing a harness.

You move your leg and turn me so your knee nudges what lies between my legs. You can feel that it is large. You pull back from the kiss, and just look at me.

"Dirk?" you ask, I nod.

My hands are on you, and I slide them to the front of your jeans. You are rock hard.

"We're not going to start with him. You know what's first."

It's your turn to nod now, with a new light in your eyes. The first sign that the man I love is waking up inside again.

I turn and retrieve the large stretching dildo/plug that we've come to refer to as The Truth. Because we both know that you can't handle The Truth. And that is by design. The Truth is more of a cone. Designed to stretch and train you so you can take Dirk. And my other fun cocks.

Your eyes go wide. It is 11 inches of intimidation.

"It's okay honey. You don't have to take all of it, just get down to about 'here'" I say, indicating a point about halfway down. It would still be 6 inches deep and a good 3 inches around. A serious stretch for you. But I have quiet confidence in your body's ability to relax and stretch for me.

We spend another few minutes hugging and kissing and caressing each other, before I tell you, "Go take your shower, I'll be in the living room waiting for you."

While you shower and prepare yourself for me, I switch harnesses and strap on The Truth. Dirk is on the table, waiting in the wings, so to speak.

I lift up my dress and reach for the bottle of lube I've set on the table next to my wine glass and next to your vodka. I'm sitting on the couch, adding lube to the first 6 inches of The Truth when you come around the corner, damp from your shower.

"Come over here. I'm going to get you ready for this. But first, I need you to take care of something for me."

You approach the couch, and with The Truth still strapped to me, I motion for you to go down on me.

You are slow and gentle at first. Lapping at my juices sweetly. We know that sweet isn't going to last long because you have a habit of sending me spiraling out of control so quickly. I'm moaning your name while I grasp for the hem of my dress. I want to feel your hands on my breasts.

You help me out of my dress and my bra and my large breasts spill into your hands. You gently pinch at my nipples and I feel another rush of dampness between my thighs. You lean up toward me, and pull one of my nipples into your mouth. My head goes back and I am lost.

You don't ignore the other breast - you soon pull that one into your mouth and this time you scrape your teeth on the most sensitive points. I'm not sure if I'm screaming or if it's just all in my mind. I am moments from being without conscious thought.

Your fingers are on my clit, but it's not enough. I want more. I'm past speaking, but I motion with my chin for you to get back to your job of licking my pussy as my hands go your naked shoulders and push you down back between my legs.

My legs jump to your shoulders and my hands are on my breasts as you worship my pussy and my clit for what seems like forever. Your thick tongue is relentless. It's all I can do to remember to breathe. Suddenly, you send me over the edge. My whole body is on fire as I squirt into your waiting mouth.

Now, you've earned a turn with The Truth. I pull you up closer to me to wrap my arms around you and kiss you. I can taste myself all over your lips and tongue. You're still kissing me while I am reaching for the lube.

"Honey, grab a pillow and turn around."

You don't need to be asked twice. You present your naked ass to me, and my hands are on you. One hand is on your rock hard cock. My other hand is pushing on you as I work my way to your quivering hole. I squirt a generous amount of lube on you.

I've been holding it in my hand, so it isn't freezing cold. I want to bury myself in you; not make you uncomfortable. I slide one finger in. Then I quickly add a second. And then a third and a forth. I'm proud of you. You've been training a bit in anticipation.

My whole hand slides into your waiting ass, and the sensation is incredible. You're warm and wet, and open to me. I know you can handle a good amount of The Truth.

"Okay honey. You are ready. Come on over here and sit down on The Truth"

I've worked more lube onto the gigantic toy, and I've made sure you are well lubed. Your back is to me, and I have my hands on your ass as I settle you down onto the first intrusion - the small bulb at the top.

It is smaller than other cocks we've played with, so I know it will slide in easily. I nudge my hips toward you, and put one hand on your hip. I am right. You take those first two inches easily.

It's the next several that will determine how the rest of the weekend will go. I reach for two pillows, to put between our thighs so you can sit and relax for as long as you can before leveling up.

I love filling you up. Stretching you to get ready for my newer, bigger cocks. I love seeing you slide down onto me. You make to level 4 with ease. But I need you to get to level 6 to earn Dirk.

You wiggle your ass a bit, settling down onto The Truth. I'm adding more lube, and my hands are massaging your opening, helping you to relax and take even more. You're at level 5.

"Good boy" I whisper, "you're about halfway to where I want you by Sunday."

I lean into you and caress your back, kissing you all over. I reach my hand around to your cock. I love feeling you hard in my hands. I stroke you for a few moments, my other hand on your ass and I can feel your muscles contracting around The Truth. I let go of your cock to pour more lube on the lower levels of The Truth.

You start to lift off of me, and I put both hands on the tops of your thighs.

"Not yet. You're not done yet. I'm still filling you. Stretching you. You have two more levels to go before you can have Dirk. And I need you to earn Dirk."

You settle back down, and this time you are nearly at level 7.

I gently push my hips up toward you as my hands are on your hips, forcing you down on me. Until you do it You are at level 7. You can take at least the first few inches of Dirk.

"Yes." I say. "Good boy. I knew you could do it. Just for fun, don't move. Stay there and see how much deeper I can go into you."

Your boy pussy relaxes even more at the sound of my voice, and now both of my hands are on your ass, spreading you even further. You slip another level in, and I grin. Dirk is going to feel awesome for both of us.

I release my hands from your hips and with a gentle slap on your ass, I say, "Get up. It's time for Dirk."

You slowly pull yourself off of The Truth, which takes some effort, and collapse on the couch, your hole still quivering from what I've just put you through.

I reach for my Feeldoe, our first cock, which will always have a special place in my heart. It's long and slender, but it will hold you open as I switch to Dirk.

I quickly exchange that harness for the one that Dirk is already secured to. I watch your cock twitch at the sound of me tightening the straps on the harness. Dirk is long and thick and a little bit squishy. Both of my hands gripped around the shaft don't reach the top, and my fingers barely meet.

Before I pour lube all over my cock, I grasp it in one hand and walk up to your mouth. You're lying on the couch on your side, and I nudge your mouth with my tip. You know what I want, but you still look up at me with questioning eyes.

I loosely cup your chin, and tell you "Suck my cock honey. You licked my pussy first, now you get to suck my cock."

Your mouth opens and I gently slide the tip in, being mindful to not grip the back of your head and force you down on me (because I don't like that either).

Your mouth starts going to town, working the head of my massive cock. I want to tell you to slow down; I don't want you to get lock-jaw. But watching you suck my cock is just so erotic.

My pussy is dripping wet again as I watch you take more of me into your mouth. You're trying to suck and hollow your cheeks, but Dirk is very large, and you're struggling to find suction. You take as much of me as possible, swallowing more cock than you've ever swallowed before. I am beyond impressed. My hips are slowly thrusting myself deeper into you without even thinking about it.

Until I am on the verge of squirting again, and I have to pull back. I'm having a hard time breathing again because I am so aroused.

I pull my cock out of your mouth and gently slap your lips with it. I want you to beg for me to fuck you.

"Mistress. Please. I want your cock in me. I want to feel you sliding into my boy pussy"

"You've serviced me well. You deserve Dirk now"

I lean you back on the couch. My eyes stray to my ropes that I've tucked into the corner of the living room. I decide to hold off until tomorrow. Tonight is about you and me and my cock, Dirk. Tomorrow can be for kinbaku and restraints and teaching you about patience and who is really in charge.

For now, though, you're on your back, my beautiful blue Feeldoe sticking out of your ass.

I pour a generous amount of lube onto Dirk. You watch as I stroke my cock. Yours is still turgid and pulsing. I know how badly you need to feel me filling you up; I don't make you wait too long.

I slide the Feeldoe out and nudge my tip at your entrance. You're stretched out enough that I easily slide the tip in. Dirk is less solid than my other cocks, so I really do have to keep my hands on it to guide it into you. I watch as I manage to slide inch after inch into you.

"Good boy. Relax. You're halfway there. You can take more. I know you can."

One hand is gripping my cock as I slide it into you, and my other hand moves to your cock. You are twitching as I fill you up. Even as I grasp your cock, you gasp. You weren't expecting that stimulation and it's pushing you closer and closer to an incredibly intense orgasm.

I add more lube to my cock as a pull out an inch or two and then push back in. Your head is back and your eyes are closed. You are just letting me fuck you. My thighs are against your legs as I again push my cock deeper into you.

I'm almost balls deep when I see you wince. I don't want you in pain, so I pull back slightly and the tension leaves your face. I nudge forward half and inch, and I see I'm at your threshold. I make a note of the depth, and I pull out halfway.

Your eyes fly open and you watch me as I thrust into your boy pussy, making sure to not probe too deeply. You arch your back as I fill you completely.

Again I add lube to my cock, and this time to yours. You are so close.

My hand is on your cock, my slick hand quickly sliding up and down as my cock pushes and recedes from your boy pussy.

I'm so wet I'm about to squirt again.

"Cum" I demand, as I increase my pace of both my hand and my cock.

In moments, you erupt, the power of your orgasm forcing me deeper into you and intensifying.

My hand remains on your sticky cock, gently squeezing every milliliter of cum from you. My cock is still filling you.

You shudder with the intensity of it all. I slowly pull out when you are ready, and with my cock still strapped on, I lean over to cover you with me in a hug. I love you.

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9 Comments
Client8Client8over 2 years ago

I'll agree with the comments so far: assertive yet considerate and loving. I am surprised, however, that no one had the issue 8 did with calling her strapon a male's name, i.e., Dirk. I'm tots bisex, but ... a bit uncomfortable with wifey implying that she pretends she has a real cick. Just my hangup I guess, and a bit hypocrit since i like transgen to woman stories with them penetrating a str8t male. Good story in all.

AnonymousAnonymousabout 4 years ago
Maybe switch or oral service your holes

I tend to think if a woman is aggressive, she will expect him to give her all the attention she can take.

AnonymousAnonymousalmost 7 years ago
And after tearing his sphincter muscle badly

Did he make it to the hospital or did he bleed to death? Because after you describing the size of the toys, there's no doubt she ripped him up badly and that he would have been bleeding profusely. Really nasty, horrible abuse.

AnonymousAnonymousover 7 years ago
Than You

Thank you for providing a story that is not only erotic, but loving and romantic. It is refreshing to see a pegging story that isn't about breaking a man, but shows that pegging can be hot and romantic.

PhillallPhillallover 7 years ago
Great story

Great first story very loving and enthusiastic I enjoyed it immensely please continue maybe double dildo in her ass also

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