[FM] I finally pegged my boyfriend

My first post here described the first time I rimmed and fingered my boyfriend, Henry. After that incredible evening, we occasionally incorporated anal play into our rotation of sexual fun, but it was not an everyday occurrence. I think we kind of wanted it to remain special – something rare for when we wanted to switch around our usual power dynamics. I didn’t post this story immediately after my first story because I didn’t want to give you all the wrong impression. Nine times out of ten, Henry takes the lead in the bedroom. Whether he is bending me over my desk or pushing me to my knees, we are both usually happiest when I am submissive and he is dominant. So, when I’m pegging him or fingering him, it’s a fun and rare change of pace.

In the months after I first explored Henry’s ass with my tongue and fingers, we made a plan for preparing him to take a full strap-on. We continued having me digitally stimulate his prostate during blow jobs and slowly started periodically incorporating anal plugs during otherwise traditional penetrative sex. Because of the amount of day-of and long-term preparation required for full anal, we knew we had to take it slow and plan in advance. We had purchased all of our required tools the day after our first rimming experience, but we hadn’t had a chance to use all of them yet. One by one, the only toy to remain was the sleek, curved, silicone dildo and its accompanying harness. We chose it for its slightly bigger size compared to the average American penis. Henry’s instinct was “larger is better,” but I was too nervous as a beginner that I would accidentally hurt him.

One beautiful Saturday morning, I woke up to the sun shining through my bedroom window, birds chirping softly, and Henry laying on top of me between my legs, his already-hard cock placing delicious pressure against my clit. “Good morning, beautiful,” he whispered.

I smiled up at him and rubbed the sleep out of my eyes. “Hey there, big boy,” I murmured as I ground my pelvis against him.

He kissed me and then trailed down my neck, leaving ticklish bites until I squirmed away from him. We wrestled gently, Henry undeniably having the upper hand, until he slid behind me to spoon, his still-hard dick pressing against my ass. He planted a series of kisses against my cheek. “Today’s the day, baby,” he told me.

I turned my head slightly, raising the one eyebrow he could see. “The day for…?”

“You’re going to peg me today.”

I laughed lightly but could feel my underwear dampen at the idea of it. “Oh am I?”

“Yuuuuup,” he popped the P, “but I need some time to get ready.”

He snuggled closer despite his words, not wanting to leave the warm cocoon of my comforter. I pressed my ass against him and rocked gently up and down. Henry’s hand not incapacitated by supporting my head slid down my body and slipped under the waistband of my panties to press firmly on my clit. I moaned, my hands gripping the arm under my head. I peppered kisses on his arm as he whispered in my ear. “You’re so beautiful.” “I want to make you cum.” “Do I make you feel good, baby?” “I can’t wait to fuck you.”

Henry removed his hand from my panties to slide his boxer briefs down, pull my panties to the side, and angle his cock against my pussy from behind. He slowly slid up and down my vulva, covering himself in my slick juices, before pushing the head of his cock into my cunt. “Ohhhh fuck,” I moaned.

He moved his hand to grip my hip and pushed into me to the hilt. He paused for a moment, letting me adjust to him, and kissed my shoulder. “You feel amazing,” he whispered.

I squeaked out a moan, not awake enough to formulate a coherent response to his sweet dirty talking. We rocked against each other slowly, Henry’s cock only moving out of me an inch or two at a time. “I’m not going to cum right now,” he murmured, “this is all for you baby.”

I turned my head slightly to look at him, confused. “I only want to cum when you fuck me later,” he explained, “but I want YOU to cum on my cock. Now.”

I bit my lip shyly and nodded. He grinned and scraped his teeth against my ear, biting lightly as he began to fuck me in earnest. I reached my hand behind me to grab his ass and help him thrust into me, harder and harder, my moans getting louder as he picked up the pace. I let up a stream of curses as the familiar sensation of a G-spot orgasm grew in my lower belly. I was so close, but I couldn’t quite get there. Henry sensed my frustration and resumed his encouraging whispers in my ear. “You feel so fucking good, baby. You are so fucking sexy. I love the feeling of your tight cunt. Can you cum for me? Please?”

With a groan, I moved my hand to slap my clit lightly but rapidly. It was enough to tip me over the edge. Calling out Henry’s name, I shuddered and tensed, my body moving against him without any conscious effort on my part. I could hear and feel his triumphant, rumbling laugh as he slowed down and pulled out of me, giving a long lick up my neck as he did so. He ended the lick in a kiss to my jaw right below my ear. “I love making you feel good,” he whispered.

I could only smile and pant at him, incapable of sentient thought. “Go get cleaned up,” he said, smiling, “I’ll make breakfast.”

He playfully swatted my ass as he got out of bed, making me yelp. I let myself lay there for a moment, waiting for the flush to leave my skin. Finally, I got up to use the bathroom and clean myself up.

In the kitchen, Henry was in high spirits while making pancakes. His boxer briefs hung low on his hips, hugging both his round ass and his no-longer-hard cock in the most delicious way. I padded up to hug him from behind, my arms looped casually around his waist and my lips placing soft kisses on his back. “So I’m finally going to peg that fat ass today, huh?”

He dropped down low and ground his ass against me as he came back up. “Yes the fuck you are, baby girl.”

I grabbed a firm palmful of his ass and then went to set the table. After breakfast, I cleaned up while Henry went to wash up in the bathroom. I took my time, wanting to give him some privacy to prepare. Our extensive pegging research indicated the necessity of copious usage of the detachable shower head, and I didn’t want to rush him and risk an accident later. Eventually, I made my way to the bedroom and opened the bedside table. Nestled there amongst our lube, other toys, and some expired condoms from my pre-IUD and monogamy days was the strap-on. It rested there, shimmering lightly as the morning light glanced off of it. It was the most beautiful fucking thing I had ever seen.

I put a dark towel down on the bed, stripped naked, and watched a couple assembly tutorials on YouTube as I slid my legs through the harness, tightening it across my belly and around my upper thighs. I looked down at the silicone cock standing at attention on my pelvis and gave it a couple rubs. Everybody with a vagina, no matter what they claim otherwise, has wondered what it would be like to have an erection. As I stared at this plastic extension of myself, I got more and more turned on. I jerked the dildo lightly and stared at myself in the mirror hanging from my closet, loving the view. I felt powerful, somehow. Was this how people with dicks feel every day?

I heard Henry’s footsteps and felt his presence at the doorway. “You look so fucking sexy.”

“Yeah?” I asked, giving him a slow 360.

He blew out air through his teeth, his eyes raking up and down my body. I finally turned and faced him head-on. He was still damp from his shower, rivulets of water sliding down his skin parallel to the dark happy trail leading down his belly and disappearing into the tufts of soft hair hidden by the towel wrapped low around his hips. If I was starting to get wet before, I was absolutely dripping now. “You’re not going to chicken out on me, are you?” I teased, swinging my fake cock from side to side as I prowled towards him.

Henry’s anticipatory smile was dazzling as he dropped his towel to reveal his own, very real cock standing at attention. “Absolutely fucking not. You could eat a goddamn picnic off my asshole right now.”

“Oh yeah? Let me see that picnic table then, boy.”

He climbed up on the bed on all fours, tilting his ass towards my face. He reached one hand back and spread his cheeks for me. “Feast on me, bitch.”

I cackled and dropped a few quick slaps on each cheek before walking around to pull out a small bottle of lube from my bedside table. Then I resumed my sentry position standing at the bottom of the bed. Mimicking his actions against my vulva earlier that morning, I pulled his ass back against me and bent at the knees to slide the dildo up past his balls to rest it under his dick. I kissed his back and slid my right hand around him to jerk off our cocks together. My left hand then pushed his shoulders down against the bed, his ass tilting up more at this angle. I let go of our dicks to grab one of Henry’s wrists in each hand, pulling them to rest on his lower back. Holding them there with one hand, I knelt behind the bed and lowered my face down to begin licking him slowly.

My tongue slid up and down over his hole, spit gathering, but refused to enter him. I knelt down further and angled my head up to lick and nibble at his balls. I felt rather than saw his cock twitch as I slobbered all around his most sensitive areas, loving the involuntary physical reactions. Henry’s breathing got heavier, and he let out a couple whispered curses. Finally, I licked back up to his asshole and shoved my tongue in. He bucked against my face once and then stilled. Smiling to myself, I punishingly penetrated his ass with my tongue. I planted my lips around his hole as I slid my tongue in and out, applying light nibbling pressure with my lips as I did so. Somehow, his shoulders relaxed into the bed more, his low groans encouraging me.

I grabbed the lube with the hand not holding his arms in place and began to squeeze some onto the dildo’s tip. After spreading it across the head with my thumb, I palmed the lube down the length of the dildo, all the while swirling my tongue around his hole. I felt ready. And, judging by his moaning, Henry was just about ready too. After placing one final kiss on his hole, I released his arms from my left hand’s grip and placed more lube on my right hand’s fingers. Slowly, I inserted them into him, pushing in lube as I dropped it into his hole with my left hand.

Henry pushed his ass back rhythmically, fucking himself against my fingers as I lubricated him. Reluctantly, I pulled out and stood up straight. His asshole was glistening and lightly stretched open, waiting for me. I placed the tip of the dildo against his hole. “Are you ready, baby?”

Instead of answering, he pushed himself back, coaxing just the dildo’s head past the tight rim of his asshole. I stood still, waiting for some kind of sound or sign that Henry wanted me to continue. “Fuuuuuuuck,” he moaned.

We both stood there a moment, letting him adjust to this new object that was bigger than anything else we had inserted in him thus far. My hands wandered up his sides, stroking his skin softly and encouragingly. “You’re doing so well, baby, I know you can take it,” I murmured.

He nodded to give me the go-ahead, his hands coming up by his head to grip the sheets, every muscle in his body tensing. “You’ve got to relax baby, or it’s going to hurt,” I said, rubbing his back, “Can you take a big breath in through your nose and out through your mouth for me?”

I heard Henry acquiesce and saw some of the tension leave his shoulders. “Ok I’m going to push in more now, alright?”

He nodded, still not saying anything. Slowly, I pushed about half of the dildo into him. The strangled moan that left his mouth was something other than human, and it lingered in my ears like a beautiful, reverberating note. I squeezed his hips to hold him in place and prevent myself from slipping in deeper. “Are you ok, baby? Do you want me to stop?”

“NO!” He half shouted, making me jump, “Don’t you fucking dare stop. Just go slowly. Please.”

Smiling to myself, I slowly pushed deeper into him. His right hand slapped the bed and grabbed the sheets again, a stream of curses falling from his lips. I left my silicone cock docked there for a moment and then pulled out gently, leaving only the tip inside. “Is it enough lube?”

He nodded, his face still scrunched up in a combination of pleasure and pain. “Anything else I can do to help?”

He shook his head. “It feels weird. Like I’m full. It’s – it’s really good. I think I’m ready for you to start moving.”

I placed another kiss between his shoulders, my nipples gently brushing against his lower back. Slowly, I pushed the dildo in to the hilt, my pelvis kissing his round ass as I bottomed out. Henry’s exhale-moan was music to my ears. I gripped his hips again with both hands as I started to move against him, my body thrusting slowly but firmly. Some primal instinct clicked and my movements began to feel natural – this made sense. Fucking my boyfriend like this made sense.

My pace quickened, and with it Henry’s moans took on a life of their own. They turned into strangled yells punctuated by the sounds of my pelvis slapping against his ass and the slippery noises coming from his tight hole. My hands shifted to his cheeks and gripped them up and out to provide more room for my dildo. I must have been holding his ass painfully tightly, but he clearly loved it. His ass pushed back to meet my thrusts, not quite twerking but not simply moving forward and backward.

Although this could never get boring, I wanted to try a new angle to apply more pressure to his prostate. I slowed down and pulled out, Henry letting out a light whine of protest. After tapping his ass gently to nudge him forward up the bed, I climbed up on the bed behind him on my knees. I replaced my hands on his cheeks to spread them and slowly but relentlessly sunk the entire length of the dildo into his hole. His moan was the loudest one yet. “THERE. RIGHT THERE.”

Emboldened, I pulled almost all the way out and then slammed back into him. He gasped out something between a groan and a shriek and tipped his chest even more into the bed. I did this a few more times before settling back into a pounding rhythm, my dildo aggressively, punishingly stretching him. I moved body up his body more so that I could tilt my pelvis down and press harder against his prostate. All the tension began to leave Henry’s body as I massaged him from the inside, each of his strangled groans going straight to my ego. I released his right ass cheek to reach around and stroke his cock roughly.

The sensations almost seemed to much for him – I had never before heard the kinds of noises that were coming out of his mouth. Fucking him wildly and straining with exertion, I felt sweat drip down my back and slide to where the harness rested across my hips. My pussy was dripping wet, the pressure of the harness across my pelvis providing a modicum of delicious sensations down and onto my clit. It wasn’t enough to make me cum, but it was certainly enough to provide another incentive for me to fuck Henry harder. Suddenly, he spoke his first coherent words in ages. “Oh my god I’m going to cum. Please don’t stop I’m going to cum. Oh my fucking god I’m cumming don’t stop fuck yes fuck!”

I kept my pounding and jerking rhythms consistent through his orgasm, feeling his cock twitch in my hand and knowing that he was spraying rope after rope of hot cum onto the towel below us. Finally I slowed, my hand sliding up his dick to feel the last remnants of cum dribbling out from his tip. Henry bucked as my palm slid across the sensitive head of his penis, and I chuckled, kissing his side before bringing my hand up to lick off the cum I had gathered there. He indicated for me to keep still and shifted his body forward to slide the dildo out of his ass with one final groan. Completely spent, he collapsed onto the bed to the side of the towel.

I, however, wasn’t quite finished with him. I gathered up the towel and wiped the lube off the dildo before tracing my fingers lightly across his back. “I’m going to clean you up a bit, baby,” I whispered.

He grunted his assent into the bedspread. Gently, I pulled one of his hips to tilt him slightly, and lightly wiped the towel against his cock to gather the final drips of cum before they dried. I then let his hips rest back on the bed and used the towel to swipe up some of the remaining lube from around his hole. Content with my work, I kissed my way from his thighs, past his cheeks, up his back, and to his shoulder. I gently let myself fall on the bed next to him and draped an arm across his lower back. Henry sighed happily, exhaustedly, and pulled me closer for a deep, lazy kiss. “That was so fucking sexy,” I whispered, “You have no idea how turned on I am.”

Even completely exhausted, those words perked Henry up. “Yeah?” He asked, a grin spreading across the one side of his face that I could see.

“Yeah,” I grinned, nodding enthusiastically, “I am so fucking wet right now.”

He raised his eyebrows in encouragement. I turned to lay on my back and let my legs fall open, one of my knees propped against his body. He leaned closer and sucked gently on my neck, too tired to help with his hands. I didn’t mind one bit – he had just hosted a silicone cock in his ass for the first time, and he had earned some rest. I lazily fingered myself, remembering the sounds Henry had made not even five minutes prior, and then brought the wetness from my cunt up to help lubricate as I rubbed my clit. I came after a couple seconds of calculated pressure, encouraged by his warm mouth sucking and biting my neck gently.

I turned toward him as he finally moved for the first time, gripping my wrist and bringing my fingers to his mouth. My tongue came out to grace my lips as I watched him suck my wet fingers in his mouth. He made a light face and I giggled. “That has to taste more like lube than pussy,” I laughed.

“Yup, big miscalculation on my part.”

I kissed him softly, and his lips parted to allow my tongue to gently explore his mouth. We lay there for a while, neither of us willing to move yet. Exhausted, drained, and blissfully happy.

Source: reddit.com/r/gonewildstories/comments/gq6ozg/fm_i_finally_pegged_my_boyfriend