A  Great Night
▲ 14 r/SensualPeggingStories+1 crossposts

A Great Night

For a long while I have been hinting to my bride that I would love to get pegged soon. We peg once every 1-2 months and it's been since our anniversary, and I've been feeling it. We've both gotten so busy with lots of projects, and it's hard to find the time and energy to be sexy, never mind the extra vibe that pegging brings.

Last week I sent her a DM saying, after dinner we can celebrate the holiday. A few hours later she said, holiday? And I responded with a pic:

https://preview.redd.it/rlyymc3m94ah1.jpg?width=416&format=pjpg&auto=webp&s=35c978f3d6a1bdd36ff7af8f8b9c00214a2c4f16

Exhaustion from work prevented it from happening during the week, but my bride talked about weekend plans. Why don't we go to that neighboring city and pick up that thing we bought. We'll catch an early dinner, and go home and.... The implication was enough for me!

Saturday came, and we completed our tasks and made it home, and my bride made dinner. We chilled for a little while, and then I said I was taking a shower, and she said she'd join me. There was no overt 'put up the swing' or 'take out the toys' just a sort of mutual understanding. I showered quickly first, went upstairs, made the bed, got out a joynt... she came up with a mixed drink, and I lit some candles. We embraced and started to make out and get warmed up.. She stopped me and whispered, 'Did you get out the toys?" FINALLY! Confirmation my desires would be realized!

She was searching through her drawer and trying on lingerie before settling on a full body fishnet. I got out our toy bag and laid out an array of toys and lubes, a few dildos, the harness (a Strap-on-Me) that has been our go to harness for a few years, a prostate toy...

With all of the chores done, we stood in our bedroom, in the candlelight, with music playing. We embraced tenderly and kissed with increasing passion. We spent some time kissing and hugging and squeezing on each other.

As our passion started to heat up, and my grabbing of her curvy delights grew more purposeful, I spun her around and encouraged her to grab the foot board of our bed. I leaned her forward and started to kiss down her back toward her ample backside. She reached a hand back and lifted one cheek to give me a glimpse of her moistening pussy. I reach out very slowly and carefully and stroked along the edge of one of her lips, which were beginning to swell in anticipation. As I started to explore with my fingertips she whispered 'get me wet...'

We awkwardly tried to get in a good position but could not quite find it. We tossed some clothes off of the overstuffed chair we have, and I sat her down and placed a pillow on the floor for me to kneel on. I leaned in gently and breathed slowly on her most secret of places. Slow warm breaths gently on her folds- not blowing but gently emitting warmth and intent to her pussy. After a few minutes of anticipation I pointed my tongue and traced the ridgleline up and down the outline of her outer lips. She gasped, and I knew that I had her. I licked with my full wide tongue on that sensitive strip of her groin right outside her lips, which she seems to like especially, an erogenous zone that is under rated.

I went back to teasing her so gently. I pointed my tongue again, and gathered a tiny ball of moisture at the end of it, gently applied to her clit. I tried to have the tiniest bit of moisture connect my tongue to her clit, to establish contact but avoid real 'touching' with my tongue. I gently rolled that moisture around her clit as slowly and carefully as I could. Her moans increased in intensity and volume with each passing second. Normally I spent five to ten minutes eating her, and this would be a prelude leading to more direct contact but I could feel her countdown to launch building. I continue my teasing and moist contact until I felt her tense and explode into me, grabbing the back of my head and pulling me into her pussy.

I stood and stretch as being on all fours on the floor, even with my knees on a cushion, was a tough position to hold for me in my mid 50s. Her eyes were smouldering and I felt that just wasn't enough. I dropped to my knees in front of her again, and dove full faced into her now dripping pussy. She was on a chair, I was on the floor, and I could get under her in a way that is difficult to achieve on a bed. I tongue fucked her as deeply as I could. I then moved up to her clit again but with direct stimulation. She was climbing again immediately toward climax. I picked up one of my hands and inserted two fingers into her sopping pussy. I circled her clit with my tongue over and over again while I rhythmically slid my two fingers in and out of her.

I was able to get a whole 3D visual in my mind behind my closed eyes of her anatomy. I jammed my tongue into her as far as it would go, then float back up to her clit and resume my fingering. She gripped the sides of the chair as I let my fingers drift apart slightly and I could feel her sensitive gathering of nerves inside her. I went crazy with my tongue on her button, and come hithered inside her until she exploded, HARD, into my mouth and all over my face. She doesn't squirt, but there was plenty of delicious pussy all over my face.

I got up and stretched again, and she stood up on her own wobbly legs. I embraced her again, and was hugging her tightly. After a few moments she broke our embrace and pointed toward the bed. We walked in that direction and when I got to the side I stopped, and felt her come up behind me. I stayed and pulled her against me so that I could feel her pressing into my back and backside. She rocked back and forth and grabbed my hips. A nice side to side sway, and I pushed myself fully back into her.

She stopped and gently put a finger between my shoulder blades and pushed me toward the bed. I got up on all fours and stayed close to the side of the bed, then dropped my shoulders to the mattress and lay on my face and spread arms, fully exposed to her. She wet kissed and bit my cheeks one after the other. It was a feeling I hadn't felt before, a slightly new move that she repeated a dozen times across my ass. It was delightful.

She then started to swipe her tongue across my knot with fast passed while licking the rim around the edges. This is one of my favorite things in the world, the best feeling of them all, maybe. She palmed both of my cheeks and squeezed and put her face right up in there. She tongued my asshole with passion and purpose, and I was off into our space, or perhaps sub space. She reached between my legs and started to fondle my cock and balls.

Now here's a weird thing.. I've noticed that when we are having this great intimacy, it doesn't always lead immediately to a steel hardening of my cock. But that didn't mean that it wasn't one of the best feelings ever, totally erotic. I made sure to vocalize how good it felt so she wouldn't be confused, and I was starting to chub a bit. She licked and sucked, and stabbed me with her tongue. I was in absolute heaven. I held the position for as long as I could before gently lowering myself to rest for a bit.

She wasn't done, even remotely. She lifted me back up by my hips and I could feel her drizzling lube on my hole, and swiping a finger around and circling. Then I felt a toy prodding me, one of our more narrow ones. She penetrated me and I realized it must be our glass dildo, long and thin. I pushed back and she pushed forward, and we got a great rocking motion going. There is something about that position, being on all fours, that opens up your blood flow, and your energy and is highly erotic. My ass cheeks get super sensitive, and it feels like I'm electrified. She piston-ed the glass dildo back and forth and I was entering a blissful state.

She stuck to that rhythm for quite a while. My hard on strengthened and she was claiming me as hers. I was giving myself to her totally, rocking myself back into her thrusts. I was so happy, so turned on.. I couldn't help thinking the same thing over and over again... "It was the smartest and best decision I ever made, over twenty five years ago, to be with this woman."

Again, I eventually tired of holding that position, and lay back down on my face. I could hear her busying herself with toys and she inquired about the harness and I informed her of its whereabouts. I was blissing out while she put on the harness. She chose the medium sized dildo and put it in.. I stood up and caressed it with her. I motioned to the bed and she lay down spread eagled, with this new phallus jutting up from between her legs. This is always an extremely sexy sight.

I stroked her thighs for a bit and gently spread them apart. I licked up and down her dildo cock and started to sneak fingers toward her dripping snatch. I rapped my hand around the base and started to suck her toy, and gently at first lowered my mouth over it. I got the fingers on my left into her cleft, and started to stroke and out of her soaking and hot pussy. I bobbed up and down, and fingered her in and out. Her head rocked back as I gained momentum. I found myself slobbering all over her cock, and my hand was getting soaked. I kept this up for a few minutes and it was erotic as hell.

Let's get something straight though. All of this activity between me and my wife happens for me, to have no hint of homosexuality and bisexuality to it. It's completely about our love for each other, not that it makes any difference whatsoever. But I'm not pretending that she's a man, or that we're gay, it's more like she happens to have a cock right now, and I want to do everything that I can to pleasure it, to pleasure her. I want to suck HER cock, I want that experience FOR her, and for me, to 'go all the way' in what we're doing. I gobble and suck her with gusto, and we're both having an absolutely full experience. At this point I've lost count of her orgasms and can't recall when they were happening, as we were fully immersed in the experience. She grabbed handfuls of my hair and pulled me off her cock, and I gasped for air for a second.

"Get on top of me, right now!" She was laying fully on her back, and I mounted her torso, with my hardened cock between her ample tits, and bobbing near her face. I got my knees on either side of her, and reached back, grabbing the now slicked cock (and there was plenty of lube application throughout this process) and easing it between my cheeks. I didn't have much trouble spearing myself on her, already having been warmed up and spread out by our earlier games. I sunk down pretty easily and in a half dozen lifts / stroked I was impaled on her. She gasped as I rocked on top of her. At times her hands were on my now hard cock, and at times I redirected them to my knees while I rocked up and down on her. At times she would thrust up into me, other times I jammed myself down on her.

I sunk all the way down and rotated my hips in a circle while fully engulfing her cock in my ass. It was amazing, and I was so happy about how much pleasure we were bringing to each other. I asked her "Do you like fucking me?" "Yes," she replied with smoke and fire in her eyes. After a good while I lifted myself off of her and rolled onto my back to catch my breath. She got off the bed and grabbed a towel and toweled my backside and her cock to make sure it was fresh again. She stood at the edge of the bed and pulled the special pillow and got a sheet and set it all up. She had me stand again, get perfectly situation on the supportive pillow and to fall backward on the bed. That raised my ass a good six inches off of the bed and the perfect height for her. My legs were waiving around in the air and she grabbed them and got herself perfectly centered.

She dropped a hand to her cock, and having lubed up again lined herself up perfectly at my center. A few quick strokes and she was in again. In just a few slow stroked she got all the way in, and bottomed out which my gasp indicated was just a little too far for me. She backed up to the perfect length and rotated her hips around a bit and stretched me out beautifully. She grasped my legs with her arms around them and started to rock back and forth into me. She established a perfect rhythm and started to really and truly fuck me. It wasn't 'hard' for fucking compared to what I do to her, but a good and strong pace that had me in heaven.

She gripped my cock and it was now hard as a rock. She had me lubed up there too and was rocking back and forth, fucking me so well, and stroking me in a perfect rhythm. Once or twice she allowed me to take her hands away while I enjoyed the fucking and prevented myself from coming. I looked up at her, with her smouldering gaze, looking so hot in her fishnet body stocking.

I saw her reach down and pull up on the harness a bit while fucking me. This is because in the last few months she's lost weight and the harness which was XL when we bought it, is a bit too large for her now. She had no problems adjusting manually and she pumped in and out of me with glee.

She grabbed my pole again, and I was swelled to the max. "Look at how big you've made my cock, baby." It was slick with lube and she was pumping my cock and my ass in perfect rhythmic harmony. I wanted it to last forever but you can't deny the explosiveness when it is time. I grunted, hard and loud, and launched a projectile of cum straight up in the air. I 'ugh'ed several times while I jetted out rope after rope of my cum. This kind of orgasm is so intense and so satisfying, there is nothing else like it.

She pulled out with a 'pop' and grabbed the towel again. She stroked a finger down my body and turned and went to wash herself and the toys. I stood up and cleaned myself off, and spent the 2-3 minutes coming back down to earth. She walked back in the room and I kissed her gently on the lips. She stroked my back with such affection, and it was over. We lay down together, snuggled for a minute or two, and both headed straight to dreamland.

I could not love this woman any more than I do right now. I couldn't be more thrilled at our ability to take each other to heights. She is everything, and I love it.

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u/myfreakishnature — 9 days ago
▲ 38 r/SensualPeggingStories+1 crossposts

F46/M35 My client wanted to be pegged for the first time.

I'm an escort, and as such have no shortage of sexual requests from men with unfulfilled dreams.

Recently, I got contacted by a Canadian man who was going to be on a business trip in Munich.

He asked me if I offer service with a Strap-On, which I do. He initially proposed a three hour dinner date, but when anal play is involved, dinner may be a bad idea. So I suggested a two hour date, a drink at the bar and ninety minutes of private time. For the sake of the story, let's call him Hugh. The name is redacted of course.

We had agreed to meet outside of his hotel. When I arrived, he was already waiting for me. We kissed each other on the cheeks and I gave him a hug. I had brought our toys in a briefcase. "Hey, could you deposit this in your room before we go to the bar?" "Oh, of course, let me take that." As he leaned forward to grab the case, I whispered in his ear: "If you want to take a peak, the combination is 6-4-2" and smiled at him.

He grinned. "I'll be right back". He hurried to the elevator. Three minutes later, the elevator doors opened again and Hugh appeared.

We proceeded to the bar and chose a small table by the window. "Did you like what you saw?". He blushed a bit "Actually, I forgot the combination, I'm a bit nervous". I smiled "Relax. Everything is going to be fine. I promise!" and gave him a wink. The barkeeper took our orders and we ordered a couple of Caipirinhas. I noticed him taking a couple of glances at my cleavage. "Do you like them?". He looked like a child being caught in the cookie jar. "Sorry..". I laughed. "Don't be. They will be yours in a few minutes". He gave me a sheepish smile.

We had some more small talk, then I said "Why don't you finish that and let's go upstairs". He took a long draw on the straw and finished his drink. I took my handbag and took his elbow. "Let's go".

He walked us to the elevator and we rode to his floor. I could tell he was really nervous. I caressed his cheek and said "Relax. Everything is fine". He nodded, the doors opened and we walked to his room.

As he swiped the card and the door unlocked, we were met by cool air. He had put another card in the main switch so the AC would keep running while we were at the bar. "Oh, that's clever". "Yes, I hate it when everything turns off when you leave.".

My suitcase was sitting on the bed on the day blanket. I took his hands, moved towards him and kissed him. He put his hands around my waist and pulled me closer. We french kissed and started undressing each other. As he pushed the straps of my dress from my shoulders, my dress dropped to the ground, revealing the red underwear he had requested for me to wear. He grabbed my boobs through my bra and pushed them up. "You have got really nice breast". "Why don't you go ahead and take it off", I said, and turned around. He opened the clasps of my bra, and I pushed the bra against my body as i turned around. Then I dropped it to the floor, took his hands and placed them on my tits. He squeezed them gently and leaned in for a kiss. I grabbed his butt and pulled him close, his half hard cock pressing into my panties. "Let's hop into the shower", I suggested. I dropped my panties, Hugh slipped out of his clothes, and walked into the shower.

The warm water flowed over our bodies. Hugh was taller than me, i needed to look up to him. We embraced and slipped our soapy bodies against each other. I grabbed Hugh's cock and started stroking it. His cock started growing in my hands as we kissed and Hugh squeezed my nipples. We continued this for a few minutes, enjoying each other's touch and kisses. I turned off the water and said: "Let's go play big boy", and led him out of the shower by his penis.

I dried him off with the soft white towels.

"Nervous?" I asked him. "Yeah, a bit" he nodded. "You can always change your mind and we can just have sex you know. Just tell me." "No, I want this. I've waited for this a long time, he responded. I took his hand and led him to the bed. "Let's do it then.

My briefcase was still sitting on the bed. I entered the combination, popped the latches and opened it.

Inside, a strap-on harness, three different sized dildos, lube, cleaner and condoms. "Do you want to start small?" I asked him. "That's probably a good idea" he said. I took the small dildo out and attached it to the harness. I slipped on the harness, pulled it tight and smiled at Hugh. Pulling him close, I kissed him. He flinched a bit when the dildo touched his penis and we had a laugh. We took the sauna towels from the closet and spread them out on the bed. I smiled and told him "Okay, on your hands and knees now please". Hugh did as he was told. I took the tube of lube from the briefcase and sat behind him. "just try to relax, okay?". The lid of the tube cracked open with a pop. I pushed some lube out onto my index finger and gently started massaging his asshole. I could see him clinching his sphincter. "Shhhhh, everything is fine...". Gently circling my fingers around his asshole, I grabbed his cock in my other hand and stroked it gently. Then I put some pressure on his asshole with my finger, and he immediately clenched. "Try to release it for me". "Sorry, it's a reflex. I'm trying". "Go slow, just keep trying. Imagine that you are peeing".

I added more lube to his sphincter and felt him getting more relaxed. Then, a gentle push, and as he relaxed, my finger slid in. "Good boy!" I commended him. I started to gently finger him and tried to get as much lube Inside him as possible. "Are you okay?" "Mmm, yes" he muttered. Slowly I removed my finger, slipped a condom on the dildo and generously lubed it. "It's going to be a bit cold" i warned him. Placing the tip of the dildo against his asshole, I grabbed his cock again and gently stroked it. "Ready?". "Uh huh. Try it".

I pushed gently forward towards him. He tightened up. "Shhhh, just relax.". "I'm trying" he said. "Take your time, just try to pee." He did, and as he relaxed, the tip slid right in. "Ouch!" He tightened up again.

"Good, the tip is in. Let's just stay like this until you get used to it". He nodded and said "okay, okay ".

More lube flowed from the tube onto the dildo.

"Just push back into me when you feel you're ready". I caressed his back with my hand and gently stroked him with my other hand. He was taking deep breaths and trying to relax. "Okay" he said and pushed into me. The dildo slipped in slowly, bit by bit. "Keep going" I encouraged him. With a final push, the dildo slipped in completely. "Just relax like this for a while, allow your body to stretch for a minute. How does it feel?". "It hurts,. but it also feels good". "It's going to feel a lot better very soon".

Hugh said "Okay, I'm ready". I started thrusting, gently, with small strokes. Hugh moaned quietly and tried to match my movements. I grabbed his hips and started increasing my strokes. "Good?". "Yes....yes..... don't stop".

Precum started flowing from his cock. I angled the dildo down at his prostate. "Oh god..oh....ohh..shit.." Hugh moaned. "Does that feel good?" "Yes! Oh god. Uuuh..". I decided to step things up and trusted harder and deeper into him. Hugh was holding his breath and winced with each stroke. Now the precum was just flowing from his cock, soaking the towel below. Hugh reached back to me and wanted to pull me into him? "Harder?". "YES, yes please har....aaahhh". I repositioned my knees so I could thrust deeper into him, then grabbed his hips and started pounding into him. "oooooooohhh gooooood". Hugh collapsed onto his belly as his knees gave out. "Keep going, please, please! Don't stop!" he begged. I did as he asked and kept plunging the dildo into his ass. Hugh had buried his face into the pillow and started making muffled noises. I grabbed his shoulders, pushed myself onto him and fucked him as deep as i could. Then, Hugh moaned into the pillow and started twitching violently as he screamed into the pillow. I reached under his belly just in time to feel his cum shooting out his hard cock. It was already completely soaked in precum, and now ropes of cum shot out of his penis until he collapsed. I heard a muffled "Stop!'. He turned his head sideways out of the pillow"Stop, please, stop, don't move! Please don't move!".

I obliged and laid my body on his, the dildo still buried deep in his ass. I laughed. "Just tell me when you're ready, okay?". He was breathing heavily. "Just give me a minute... it's... it's too much right now ". "It's okay, take your time", I said, and planted a few tender kisses in his neck". We stayed like this for several minutes. I ran my fingers through his sweaty hair, my breasts against his back and caressing him.

"Okay, please pull it out really slow" Hugh said. I pushed myself up and pulled back slowly. "Okay like this?"

He just muffled Mmmh Hmmm into the pillow.

The last of the dildo slipped out, and I watched as his stretched sphincter remained slightly open for a few seconds as it slowly closed. Hugh still laid on the bed, face down into the pillow. I removed the harness, laid next to him and pulled the blanket over us. He turned to me, we pulled each other close and cuddled, exchanging kisses and looking into each other's eyes. "Are you okay?" I asked him. "Yes. That was unbelievable. I came really hard". "No kidding" I laughed and ran my hand through the big puddle of cum between us. "Seems you were saving for this, huh?". "Yeah, I didn't cum for a week before this.".

"Okay, let me do some aftercare for you now" I said. I wiped the cum from his belly with some wet wipes and removed the soaked towels. "Turn on your stomach again" I told him, "it's going to be sore for a day I'm afraid" i said, as i applied some Bepanthenol cream to his anus, gently rubbing it in. "That's okay, it was well worth it". "Well, I'm glad you enjoyed it".

We took another shower together in the time that remained. He wrote me a message the next day, thanking me for the time together. Unfortunately his business trip was a one-off, so he won't be returning again soon.

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u/No_Fee5354 — 13 days ago
▲ 35 r/sexystories+1 crossposts

Submitting to You [MF] [Strapon] [Anal]

I stood in our bedroom, the soft lamplight casting warm shadows across the walls as you stepped closer, your eyes gleaming with that familiar mix of love and wicked hunger. You wore a simple tank top that hugged your full breasts and a pair of loose black yoga pants that clung to your toned hips and thighs. My heart raced as you cupped my face in your hands, your thumbs brushing my cheeks.

“Get on your knees for me, baby,” you whispered, your voice low and commanding, laced with excitement. “I want to see you like this tonight. All mine.”

I sank down obediently, the carpet soft under my knees, my face level with your waist. My hands trembled slightly as I reached up, gripping the waistband of your pants. I tugged them down slowly, inch by inch, revealing the smooth skin of your hips and thighs. And there it was, strapped securely around your waist with a black harness, a thick, realistic silicone cock jutting out proudly. It was veined and heavy-looking, the head already glistening slightly from the lube you’d applied earlier. The sight made my breath hitch, a rush of heat flooding my body.

You smiled down at me, one hand stroking my hair while the other wrapped around the base of the strapon, giving it a slow, teasing stroke. “Mmm, look at you… on your knees, staring at my cock like you need it. God, that turns me on so much. Seeing my strong, handsome husband like this, submissive, eager, ready to worship me. It makes me so wet, baby. My pussy is throbbing just watching your eyes widen.”
You guided the tip toward my lips, rubbing it gently across them. “Open up for me. Suck it like you mean it. Show me how much you want me to fuck you.”

I parted my lips, taking the head into my mouth. It felt warm and firm, the smooth silicone sliding over my tongue as I sucked tentatively at first, then deeper. You moaned loudly, your hips rocking forward just enough to push more of it into my mouth.

“Fuck, yes… just like that. Look up at me while you suck my cock. Oh god, your mouth feels so good wrapped around it. I love seeing you like this, your lips stretched, your cheeks hollowing out. It makes me feel so powerful, so fucking turned on. I can feel how hard you are already, can’t I? My good boy, getting off on sucking his wife’s strapon.”

I bobbed my head, taking more of the length, my tongue swirling around the shaft as saliva coated it. The musky, intimate scent of your arousal mixed with the faint taste of lube filled my senses. You gripped my hair tighter, guiding my rhythm, your breaths coming in short, excited gasps.
“Mmmph… deeper, baby. Take it all the way. I love how eager you are for me. Seeing you on your knees like my little slut… it makes my clit ache. Every time you gag a little on it, I get wetter. You’re so perfect like this, vulnerable, devoted, mine to play with.”

After several minutes of your vocal encouragement, my jaw aching deliciously and my own cock straining painfully against my pants, you pulled back. The strapon slipped from my mouth with a wet pop, shiny and slick.

“Enough foreplay,” you purred, your voice husky. “I need to be inside you now. Get on the bed, on all fours for me.”

I climbed onto the mattress, heart pounding, positioning myself as you requested. You climbed behind me, your hands caressing my ass, spreading my cheeks. I heard the cap of the lube bottle click open, felt the cool slickness as you generously applied it to my hole and worked a finger inside, then two, stretching me open while you kept talking.

“God, you’re so tight… but you’re going to take every inch of my cock, aren’t you? I love this view, your ass up, waiting for me. It turns me on seeing you submit like this. My big, strong man, bent over and ready to get fucked by his wife. Fuck, I’m dripping.”

You pressed the thick head of the strapon against my entrance, rubbing it teasingly before pushing forward. I gasped as it breached me, the stretch intense and full. Inch by inch, you sank deeper, your hands gripping my hips.

“Ohhh fuck, baby… feel that? Feel how I’m filling you up? Mmm, you’re taking me so well. It feels incredible, the way your ass grips my cock. So hot and tight around me. Every thrust makes my clit rub just right… I’m going to cum just from fucking you like this.”

You started slow, rocking your hips, letting me adjust to the fullness. The sensation was overwhelming, pressure building deep inside, waves of pleasure radiating from my prostate as you hit that perfect spot over and over. My cock hung heavy and leaking beneath me, untouched.

“Harder?” you asked breathlessly, already knowing the answer from my moans. You picked up the pace, thrusting deeper, your hips slapping against my ass. “Yes… take it. Take my cock. You feel so good inside, hot, squeezing me. I love watching it disappear into you. God, you’re such a good fucktoy for me right now. This is what turns me on the most, seeing you lose yourself, moaning like that, your body shaking for me.”

The rhythm built, relentless and deep. Each thrust sent sparks through my body, the strapon dragging perfectly over my prostate, making my cock throb and drip onto the sheets. You reached around, stroking me firmly in time with your thrusts, your voice a constant stream of filthy praise.

“Fuck, yes… you’re getting so hard in my hand. I can feel you pulsing. Cum for me, baby. Cum while I fuck your ass. I want to feel you clench around my cock when you explode. This is so fucking hot, my husband on all fours, getting railed until he cums. Mmm, I love how full you feel. How desperate you sound.”

The pressure mounted unbearably, pleasure coiling tight in my core. Your thrusts grew faster, more erratic as you chased your own orgasm, your moans mixing with mine. “I’m so close… your ass is milking me. Cum, baby, now!”

I cried out as the orgasm crashed over me, my cock pulsing hard in your grip, thick ropes of cum spilling onto the bed beneath me. The contractions squeezed around the strapon buried deep inside, intensifying every sensation. You groaned loudly behind me, grinding deep as you came too, your body shuddering against mine.

“That’s it… good boy. So much cum. You feel amazing when you cum like that, squeezing my cock, shaking for me. I love you like this… completely taken, completely mine.”

You stayed inside me for a long moment, both of us catching our breath, your hands stroking my back tenderly. Finally, you eased out slowly, leaving me feeling wonderfully empty and satisfied. You pulled me into your arms, kissing me deeply.

“See? That’s what you do to me,” you murmured against my lips, smiling. “You make me so fucking turned on when you let go like that.”

We lay tangled together, the air thick with the scent of sex and the warmth of our connection.

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u/ManyTransportation49 — 15 days ago
▲ 41 r/SensualPeggingStories+1 crossposts

Getting Pegged by a Cougar

In my more adventurous days, as a college freshman, I was frequently searching the internet for kinky fun in my area. Not too dissimilar to today, but less action. I stumbled across a much older woman, divorced mom of two, with kids in high school. I was freshly 18 and had just started my first quarter at College and loved the idea of getting with a cougar as that had been a teenage fantasy of this horny boy.

Things started off great with the first time I walked into her townhouse and she immediately disrobed and got on her knees to take down my shorts and expose my quickly hardening cock. I had limited experience at this point, and the high school girl that I had been with was nowhere near as skilled as this mid forties milf. She took me to her bedroom and laid me down so she could continue sucking away at me and for the first time in my life she began touching my asshole. Just rubbing it while she continued to blow me with incredible eye contact. I didn’t hesitate or pull away so she kept going, eventually sliding a finger slightly into my ass which caused me to shoot a huge load of cum into the back of her throat.

We cleaned up, temporarily, and prepared for round two as I had mostly wanted to come over and feel her experienced pussy wrapped around me. We had an amazing time and yet again she made me orgasm like nothing I had felt before that time.

The next time I went to see her she again dropped to her knees in the entry way and gobbled away at my young cock. When we made it to her bedroom this time I noticed a dildo sitting on the bedside table. I asked her if she had been getting herself ready for me. “Not exactly” as a response had me puzzled. While I had watched a lot of porn at the time, this wasn’t something as mainstream almost 20 years ago as it is now.

She asked me to bend over the bed and she was going to lick my ass and play with me a little. I obliged and took my spot curled over the edge with my 18 year old ass in the air. she started off with her tongue slowly darting in and out of my anus, then came her finger, then two. She was kind and continued to check on me, making sure I was also enjoying myself which I was. Then I felt something much bigger than a finger, she told me to relax and she slowly started rubbing lube on me directly from the dildo I had noticed on the nightstand. It took a lot of slow motion and lubrication but she got it in. While it wasn’t a huge rubber cock, it was something enormous to my tight ass that hadn‘t had more than her finger in me before. She abruptly stopped and reached into the drawer for something else. I turned to watch her put on the strapon with that same dildo now attached. In my college boy slutty excitement I turned over and laid on my back instead so that I could watch her. Half to experience the visual and the other half to remind myself it was a sexy cougar pegging me. She stroked my cock while she pumped me harder and harder until I climaxed and cum shot everywhere.

We continued with similar evening excitement for several months. She had a boyfriend, who was aware of me, that lived elsewhere. At the time I wasn’t comfortable with him being involved (how I bet we all wish I had felt differently) so she started recording our experiences for him to watch later. I can only imagine what price I would pay to watch those exact tapes again. After some time we broke things off and I haven’t had any contact with her in over 15 years now. Absolutely crazy unforgettable times.

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u/WDW-Fun — 13 days ago
▲ 122 r/SensualPeggingStories+2 crossposts

Cyber Punk rave party ended with me sitting on a guy's face while my friend pegged him [FFM]

I'm 25, I have been going to kinky munches with my friend Angela who's 32. After one munch, a group of us went to a cyber punk themed rave party. She mentioned one of the guys named Sean is coming back to her place to be dominated. She said I can come too. I said I'd think about it.

Sean looks like he's in his thirties, over 6 foot tall and had a bigger build. He didn't say much but was still easy to talk to. He really surprised us by dancing really well and sometimes doing funny dances like flossing.

The rave was really fun. I just wore a bright green shirt and a purple skirt, nothing too revealing or anything. I danced mainly with Angela and some other people in our munch group. I danced with another woman named Tina, she was curvy, had long curly black hair and we eventually made out with each other. It was only lips at first and she put her tongue in my mouth toward the end. I put my tongue in hers back. After we made out, she squeezed my cheeks with her hands yelling "You're just so damn cute!

People in our group were slowly leaving. Angela looked at me with Sean at her side and I nodded and kind of skipped toward them. It was only a 10 minute walk to Angela's apartment. Right when we walked in the apartment Sean was taking off his clothes and lying on the bed. Angela pulled handcuffs out from her bed and hooked them on to his wrists with the other ends tied to the headboard.

Angela stripped down to just a black laced thong. She is very thin, a little taller than me, and I'm 5'1. Has wavy black hair down to her shoulders, and she has very small boobs with perky nipples and small shapely butt. She went into a drawer and pulled out her strap on harness and put it on. She walked over to me, pulling off my shirt and then reaching under my skirt to pull my thong down. She walked behind me and pushed me toward the bed, I climbed on it with her still nudging me until I threw my right leg over Sean's arm, I lifted up my left leg over his head and held on to the headboard. I felt his tongue going up and down my labia, I started grinding on his face and he just left his tongue in place while I slid back and forth. He eventually used the tip of his tongue to rub my clit. His head was completely covered by my skirt. I could feel him breathing hard through his nose on to my pubic area sometimes letting out a gasp of breath through his mouth.

I looked behind and I could see Angela stroking his hard cock while she was holding the base of the dildo hooked into her strap on harness. She was slowly pushing against his ass until I saw it kind of pop in. Sean made a muffled moan into my pussy. Angela was humping him slowly at first going all the way in then out. She was stroking his shaft with one hand and playing with his balls with the other. She was whimpering too and I could hear she had a vibrator on her clit behind the harness. Sean was distracted at first but then focused back on my clit. My whole pelvis and legs were tingling until it built up and shocked me making me come. Sean knew it and took it easy until I stopped shaking and moaning.

I turned around to face Angela and give her a kiss. Sean moved his tongue up to my asshole and I nearly jumped off of him with surprise. "Not there please!" I gasped. He apologized and thought I wanted him to eat my ass by turning around. He resumed on my clit while I made out with Angela. She immediately shoved her tongue in my mouth and we exchanged back and forth for a while. Sean was whimpering more, I sat back as Angela stroked and humped him faster and faster until streams of cum shot out all over his stomach with the rest on her hand. It was a lot of cum and I was amazed how much came out of him.

The rest of the session was Angela sitting on Sean's face. He ate out her pussy and her ass making her come multiple times. I sat at the side of bed with him fingering me and rubbing my clit, making me come a couple more times.

I ended up staying the night, we all slept in the same bed. Angela's cat kept me up all night by walking all over me, I tried to push her down to lay down but she would just snarl at me. I left her apartment in the morning right away and really felt the walk of shame wearing my rave outfit back to my car during the sunny morning.

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u/Dapper_Reindeer3883 — 2 months ago
▲ 51 r/SensualPeggingStories+1 crossposts

I couldn’t sleep. We’d crashed hard after a night of too many drinks—stumbling home, tearing into each other with that sloppy, boozy urgency, then collapsing into bed. But now, hours later, I woke up spooned against his warm back, my arm draped over his waist, thigh hooked over his. My body buzzed with leftover heat, restless, and as I shifted closer, I felt myself grinding against his ass without even thinking—slow little rolls of my hips, my pussy already damp from the friction and the dirty thoughts creeping in.

 

He stirred just a bit, still half-asleep, but didn’t pull away. That sparked something wild in me. I pressed harder, breath quickening against his neck, one hand sliding low to spread his cheeks while the other snaked under him, fingers wrapping tight around his cock. God, he was already stirring hard in my grip, thickening as I stroked him slow and firm. I bent over, catching his mouth in a deep, sleepy kiss—our tongues tangling messily, my hair curtaining us in the dark. Heat flooded my chest; he was waking up now, and I wasn’t stopping.

 

I trailed kisses down his spine, hot and deliberate, nuzzling the curve of his ass while my hand kept pumping his cock in confident strokes. He shifted onto his knees, head down against the pillow, ass spreading open for me like an invitation. Fuck, that view. I fumbled blindly for the nightstand—the six-inch strap-on we’d bought as a joke one drunken night, lube cap clicking open. My tongue flicked teasingly against that sensitive spot between his cheeks, tasting him, making his thighs tremble as I slicked everything up.

 

Kisses trailed back up his spine, my small, perky tits pressing against his flushed skin as I leaned my weight over his lower back. He tried to turn, but I pushed down on his shoulders, pinning him with surprising strength. My fingers rubbed his ass in slow, slick circles, one then two dipping in just enough to tease—feeling him tense, then yield with a gasp into the pillow. He chuckled, half-surprised, half-excited, head twisting back. “Where the hell is this going?” His eyes seemed to ask, hips rocking back into my touch. The room thickened with it—our shared buzz, my hunger taking over.

 

Suddenly, I nudged the cool silicone tip against his entrance, my breath ragged as I guided it. His body jolted under me, aware now. Hands on his hips, I pulled him back, pushing harder—breaching him slow. “Fuck, I can’t believe we’re doing this… or about to…” I stammered high-pitched, half-laughing, half-gasp, thighs trembling against his as the thrill hit me.

 

I pressed forward more, feeling him stretch around it, his breath hitching as he relaxed inch by inch. We twisted for another wet, sloppy kiss over his shoulder, my nails scraping his nipples while I pumped his cock steady. His hand gripped my ass, pulling me deeper—fuck, yes. Then it happened: the resistance gave, the dildo sliding all the way in, filling him completely. He groaned low, shuddering beneath me, hips flush to mine. We froze a beat, locked—my hands working him front and back—before I started thrusting, slow at first, building that electric ache.

 

He pushed back harder, faster, meeting me with hungry slams. My breath caught—surprise, pleasure, both—as he took it from below, my grip tightening to urge him on. The slick sounds filled the room, my moans ragged in his ear, our night spiraling raw.

 

In the frenzy, it slipped out with a wet pop. Before I could realign, he rolled onto his back—legs spreading wide, guiding the tip right back to his entrance as I knelt poised above. That vulnerability in his eyes, open to me completely, it flooded me with power. I thrust deep again, groaning as his hands dug into my ass, pulling me harder, hips bucking up to match every slam—hitting that spot until his vision blurred, tits brushing his chest in our frantic rhythm.

 

We bucked and fucked until we shattered. He came first, shuddering hard, cum splattering his abs as his ass clenched tight around the dildo, groans ripping out. I slammed through it, relentless, until my climax hit—shuddering, crying out in a raw moan, kissing him deep and desperate, tongues sloppy while his hands roamed my ass and pinched my perky nipples, drawing out every tremor.

 

For what felt like eternity, we lay tangled, the dildo still buried deep, his legs splayed wide. I wriggled in his arms, smearing his cum between our sweat-soaked bodies, tits sliding slick on his chest as breaths slowed to sighs. The room reeked of us—booze, sex, surprise—and we stayed like that, spent.

 

Finally, I withdrew slowly, the slick drag making him gasp one last time. I eased off with a satisfied hum, collapsing beside him, hand trailing his cum-streaked abs, legs tangled. Lips to his shoulder, I grinned sleepily: “Told you we’d use that thing someday,” dawn creeping in around our sticky sprawl.

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u/Eroticstories3333 — 2 months ago
▲ 25 r/SensualPeggingStories+1 crossposts

Truth or Fiction

The bar was loud, a Saturday night symphony of clinking glasses, laughter, and the thumping bass from the speakers overhead. At a high-top table near the window, four friends were deep into their favorite game: "Truth or Fiction." The rules were simple. Each person shares a sexual experience, either completely true or a total fabrication. The group votes, and the person with the most outrageous true story gets their drinks paid for all night.

"All right, ladies, we're tied," Maya declared, swirling the amber liquid in her glass. "Anna, you went first with that 'mile-high club' story. We all believed you, but honestly, it's not that shocking anymore. Then I went with the twins story, which you all called bullshit on, so I'm out. It's your turn, Steph. The pressure's on."

Stephanie took a slow sip of her gin and tonic, a mischievous glint in her dark eyes. She was always the quietest one in the group, the one with the steady job and the long-term relationship, which made her contributions to this game particularly interesting.

"Okay," she said, setting her glass down with a deliberate click. "I've got one. I can make my boyfriend, Brian, orgasm from pegging him. No hands, no other stimulation. Just that."

The table went silent for a beat, save for the bar's ambient noise.

Anna, who was never one to hold back, snorted into her cosmopolitan. "No way. Absolutely not."

"You're calling bullshit on that?" Maya asked, raising an eyebrow.

"I'm calling physical impossibility," Anna clarified, leaning forward on her elbows. "I'm sorry, Steph, I love you, but men need direct penile stimulation. It's just how they're wired. The prostate is amazing, sure, but it's a 'heightens the experience' thing, not a 'finish the job' thing."

"What about you, Lena?" Stephanie asked, looking at their fourth friend, who had been quiet.

Lena bit her lip, a thoughtful expression on her face. "I... don't know. I've heard stories, but they're always just that....stories. Like urban legends of the bedroom. I'm with Anna, it seems unlikely."

Stephanie just smirked, taking another sip of her drink. "So, that's two votes for 'bullshit.' What about you, Maya?"

Maya studied Stephanie's face. There was no hint of a lie. No nervous tic, no darting eyes. She was just... calm. Confident. "I don't know," Maya said slowly. "You look awfully sure of yourself. I'm going to say... true. But I'm on the fence."

"Doesn't matter," Anna said triumphantly. "It's a majority. You lose, Steph. Better luck next time. Your round."

Stephanie's smirk didn't falter. In fact, it widened. "I'm not losing. And I'm not paying."

"What are you talking about?" Anna asked, exasperated. "We voted. It's the rules."

"Exactly," Stephanie said, pulling out her phone. "And the rules say the person with the most outrageous true story wins. You don't believe me. So, I'll just have to prove it."

Her fingers flew across the screen for a moment before she held it up, showing them a text message sent to 'Brian ❤️'.

*Hey babe. You know that thing we do? The one you love? My friends don't believe it's a thing. How about you come pick me up and we give them a live demonstration? Drinks are on me if you do. 😉

A moment later, three dots appeared as Brian typed back.

On my way. Give me 20.

Anna's jaw was practically on the table. "You're kidding. You're not actually going to... in front of us?"

"A bet's a bet," Stephanie said with a shrug, finishing her drink. "And I'm thirsty."

Twenty minutes later, Brian walked into the bar. He was tall, with kind eyes and a look of easy confidence that didn't seem at all fazed by the three women staring at him with a mixture of shock and morbid curiosity. He kissed Stephanie hello, his hand lingering on the small of her back.

"You guys really don't believe her?" he asked, a grin playing on his lips.

"Scientifically speaking, it's a stretch," Anna muttered, but her bravado was clearly fading.

"Well," Brian said, pulling a credit card from his wallet and placing it on the table. "Let's run the experiment. Start a tab. A bottle of tequila. The good stuff."

The ride back to Stephanie's apartment was thick with a strange, electric tension. The usual drunken chatter was replaced by a nervous, anticipatory silence. Stephanie led them into her spacious, dimly lit living room.

"Okay," she said, her voice business-like. "Brian, you know the drill. Get comfortable. Ladies, make yourselves at home. Try not to spill anything."

Brian disappeared into the bedroom and returned a moment later wearing only a soft-looking robe. He moved with an easy grace, completely at ease with the situation, which somehow made it even more shocking. He lay down on the large sheepskin rug in the center of the room, propping himself up on his elbows.

Stephanie went to a sleek wooden chest by the wall and opened it. Inside was a collection of toys, neatly arranged. She selected a harness and a sleek, curved silicone dildo in a deep purple color. She methodically fastened the harness around her hips, her movements efficient and practiced. There was nothing timid about her.

She knelt on the rug behind Brian, and the three friends found themselves holding their breath.

"Ready?" she asked softly.

"Born ready," he murmured back, his voice already a little husky.

Stephanie squeezed a generous amount of clear, slick lube onto her fingers, warming it for a moment. Brian shifted, spreading his knees slightly, giving her better access as he settled onto his forearms, his back a long, trusting line in the soft lamplight. The three women on the sofa were statues, their eyes wide, their glasses forgotten. Stephanie circled his tight entrance with her lubed finger, the motion gentle but deliberate. Brian let out a soft sigh, a sound of pure surrender, as she slowly pressed inside, first one finger, then a second, scissoring them gently to prepare him. His head hung low between his shoulders, his breathing already deepening into a rhythm of anticipation.

Seeing he was ready, Stephanie withdrew her fingers. She positioned the head of the purple silicone dildo against his slicked hole. Her hands came to rest firmly on his hips, her grip possessive and steady. She pushed forward with a controlled, relentless pressure. Brian's back arched as the head breached him, a sharp intake of air hissing between his teeth. Stephanie paused, letting him adjust, her thumbs stroking small circles on his skin.

"Okay?" she whispered.

"Okay," he breathed, his voice tight with pleasure.

She began to move, her strokes shallow at first, just rocking her hips against him. Each small thrust pushed the curved toy deeper, and with every inch, Brian's quiet sighs turned into low, guttural moans. The room was silent except for the soft music, the slick sounds of their joining, and the raw, vulnerable noises coming from Brian. Stephanie found her rhythm, a slow, deep, rolling motion of her pelvis. She wasn't just thrusting; she was grinding, angling her hips to ensure the silicone curve pressed firmly against his prostate with every pass.

The change in Brian was immediate and visceral. His arms began to tremble where they supported him. His cock, which had been semi-erect, began to harden until it was standing rigid, flushed and dark, pointing toward the sheepskin rug. A bead of clear fluid gathered at the tip and dripped onto the wool below. He was completely lost in the sensation, his body rocking back to meet her, silently begging for more. Stephanie understood his language perfectly. She increased her pace, her thrusts becoming longer, more forceful, driving into him with a powerful, hypnotic cadence. The slap of her hips against his ass filled the room, a primal counterpoint to his escalating cries.

"Steph... fuck... right there," he gasped out, his voice ragged. "Don't stop."

She had no intention of stopping. She could feel the tension coiling in his body, the way his muscles were locking up, the frantic, desperate edge to his breathing. She shifted slightly, changing the angle just a fraction, and that was all it took.

Brian cried out, a raw, broken sound of pure ecstasy. His entire body seized, his back bowing into a taut curve as the orgasm ripped through him. His untouched cock pulsed violently, and a thick, forceful jet of semen shot out, splattering onto the rug. It was followed by another, and another, as his whole body shuddered with the force of his release. He collapsed onto the rug, his limbs giving out, breathing in great, heaving gasps.

Stephanie slowly withdrew, unbuckled the harness with practiced ease, and lay down beside him, stroking his sweat-dampened hair.

The three friends on the sofa stared in stunned silence. Finally, Anna let out a long, slow whistle.

"Holy shit," she whispered, her voice barely audible.

Maya just shook her head, a look of awe on her face. "I stand corrected. Very, very corrected."

Stephanie looked over at them, a triumphant, loving smile on her.

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u/bri_guy94 — 30 days ago
▲ 3 r/SensualPeggingStories+1 crossposts

Amateur Pegging

I’ve been kissing her in the hotel room and I’m already hard, nervous and excited. She tells me that I ‘can go now’ so I go downstairs to the hotel bar, I sit down, have my drink, try and relax, and wait for her name to flash up on my phone, the notification that I’ve to go back upstairs where she’s going to waiting to peg me.

We’ve been talking about this kink for months, I’m going to sit in the bar and she’s going to be wearing lingerie upstairs. Honestly? I think that I’m looking forward to it more than her, I want to give her the power and the control, I want to get fucked by her and I want it to be on her terms, her say so, I’ve been wanking off to pegging porn since before I’ve met her but she’s the only person I’ve felt comfortable sharing even the idea of this with and tonight it’s going to happen and I cannot, fucking, wait. But for now that all I can do, wait, I imagine what she’s going to be wearing, the black lace, her stunning figure, the shape of the strapon, it’s all going to be surprise to me and then her name pops up on my phone saying:

“You can come up x”

When I go upstairs she’s stood at the end of the bed in black lingerie wearing the strapon. It’s not massive but my eyes are drawn to it. I start to walk toward to her, she tells me to stop and take my clothes off. Only when I’m completely naked does she allow me to get to her, I kiss her and touch her and my hard dick is touching her strapon. She sits me at the end of the bed and sucks my dick, I’m so hard, and turned on. She then lifts my legs up and sticks her tongue right in my ass and slides a finger in my ass too, teasing me for what’s to come.

She reaches for the lube, and rubs it over my dick and then tells me to rub it all over her strapon and she starts to press the tip of it against my ass and I throw my head back as she gently presses it in more and more, sliding it back and forth. It feels amazing and she looks amazing. I’m obsessed with her fucking me, she starts fucking me deeper and harder and before long I’m relaxed and grabbing her by the waist and pulling her deep into me as far as she can go, I feel like it’s coming out my throat but as she’s fucking me she’s also wanking me off and all these sensations are about to send me over the edge. I tap out and tell her I need a break. She lets me catch my breath for half a second but before long she’s told me to turn around and get on the bed and get on all fours. I do as I’m told, and I wait for her to start fucking me again.

Then she tells me to pass her her phone so she can take pictures and videos of me, I feel so exposed but I don’t have any control at all now, she’s fucking me hard, making me pay for every time I’ve slapped her or choked her or spat on her. She’s making me pay, and I love it. Turns out there’s a fine line between getting fucked hard and tapping out, plus I’m now desperate to cum in her so we switch it and it’s my turn to have her legs in the air.

If you’ve made it this far, head to my profile to watch the video and pics

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u/NoJuggernaut4979 — 20 hours ago
▲ 38 r/sexystories+1 crossposts

Friends with Benefits: Part 1 [M27, F36]

Let me tell you about a time I hooked up with a friend. Well... the first time we did.

We met at work. We had always flirted with each other, but it was just a work/boredom thing. However, as we got to know each other better, we would stay later and later at work talking, arguing, and flirting. It was always fun... and we became pretty good friends. He had a reputation for going through a lot of girls, but he was clear when we hung out that we were just friends. It felt... different when we were alone together, but I figured I was looking too much into it.

One night he called and asked if I would come up to his place and hang. He said our other work friends were going to be there too, but that he wanted to do a fire and have some drinks. I was in the middle of something, but I agreed to go hang out.

I got up there about 20 mins late, and was surprised that it was just us there. He walked up to my car and when I got out, I asked what was up. He said that everyone else bailed, but if I wanted to chill it was a beautiful night and he already had a fire going. I was down, so he and I hung out and talked for a few hours next to the fire under the stars. Once the fire got low, he asked if I wanted to watch tv in the house, because it was getting chilly. I wanted to keep hanging out so we went in.

Having never been to his place, I didn't know that he only had a TV in his bedroom, and the only place to sit was on his bed. He laid down and said to make myself comfortable, so I leaned back and we started watching YouTube. While we were watching we were talking and just enjoying our conversation, and he started complaining about his shoulder hurting. I had mentioned to him before that I was good at massages, so he asked if I would rub his back and shoulders. I say "sure."

I start rubbing his back and he asks if I'll use some oil on him. I say "sure" again, and he gets up to grab the oil from his bathroom. When he gets back, I tell him to strip down and start massaging him again.

I actually am very good at massages... so I'm not surprised when he starts moaning a little. What does surprise me is when he grabs my leg and starts rubbing it and gripping it. I ask if he's okay, and he says yes, and that it feels amazing.

I'm slightly buzzed and turned on, but I keep my focus and continue massaging him while he continues rubbing my legs and the arch of my feet. I can't help but notice that he's very aroused... and has to keep adjusting himself. We're talking the entire time just about random stuff, and he asks me to massage his hips and butt. I say okay, and make a joke about not doing his whole ass... just the top, and he laughs and we keep talking. He then asks if I'll massage his chest... so I say yes, and he flips over. I start massaging his chest and we start playing a game of truth or dare.

It starts off dumb and we're both mostly choosing truths. I'm playing coy for the most part and he's teasing me for continuing to choose truth. I say that he's ALSO choosing truths... but I choose dare to spite him. He dares me to kiss him... which throws me off. I panic a little, but decide to do it because it's just a kiss. We kiss and he nips my lip. I push him a little, and I keep massaging his chest, laughing at the bizarre twist the night seems to be taking. I switch back to choosing truth because I'm a chicken shit, and we just keep talking. He asks me to massage his stomach and sides, so I move down his torso. We stopped playing the game pretty much, but mid-conversation he dares me to take my shirt off... I raise my eyebrow at him, but comply since he's only in boxer briefs... in my buzzed-mind it makes perfect sense. He tells me he likes my bra, and I tease him that he likes what's in my bra, and we both laugh and keep talking.

He has had a raging hard on for a while... but I'm trying to ignore it and keep doing my thing. He asks me to massage his stomach harder, so I push harder, and he groans LOUD. I keep going and he puts his hands on my hands, and dares me to give him a hand job.

I pause, and he just looks at me... I don't see any guile in him... just lust, so I agree and tell him to take off his boxers.

He says he doesn't want to be the only one naked, so he tells me to take off my pants. I do, and I start on his dick. I'm stroking him and playing with the head, when he dares me to kiss the tip. I stop what I'm doing and he kind of whines and thrusts into my hand, so I put my hand on his stomach and ask him what he wants this to be. He says he just wants some fun, but he couldn't resist me tonight. I don't know what to think... so I say okay, and put my lips on the tip of his dick, and lick it.

He basically jumps out of his skin and I tell him to let me do this. He settles and lays back as I start to lick his dick... around the head, along the shaft, and as I start on his balls, he puts his hands on my head and tells me they're sensitive and to be gentle.

I lick and suck them... spending my time working them, as he groans louder and louder. I reach lower and start massaging his taint as I have his balls in my mouth, and he lets out this groan/growl. I move to his shaft and up to the head and he grabs my hair, and pulls. I look up at him with his cock in my mouth, and he pushes my head down. I take that as a pretty solid hint that he's ready and start to suck him in earnest, as he guides my head with his hands tangled in my hair. I continue until I am deep throating him and I linger with him bottomed out in my throat, swallowing and massaging him with my tongue. He moans and starts to throat fuck me... making me gag and choke on his cock... slapping my face with his dick and stroking himself when I need a break.

I can tell he is close to cumming, but he tells me to stop. Surprised and (slightly) pouting, I look up at him, and he leans over to his night stand and pulls out a dildo and what looks like climbing gear. I sit up and ask him that that's for.

He asks if I've ever pegged someone before, and I say no. He then asks if I'm dominant in bed, and I tell him that I've never had to be.

Then he asks if I would peg him.

I say I don't know how, but that if he helps me, that I'll do it for him.

He tells me to get up and puts the strap-on on me. He tightens the straps. Then he grabs some lube and hands it to me.

He tells me that I need A LOT of lube, and he lays on his back in front of me, putting me between his legs. I've done anal before, so I know we need a lot.. applying it on/in his asshole, and on the dildo.

I'm super worried about hurting him, so I start with my fingers. I circle his hole... dipping my finger in and out, applying pressure as I penetrate him. He moans softly, moving his hips to take my fingers deeper. I make slow, long strokes and his cock starts leaking precum. I stop to lick his tip... savoring his taste, and rub the dildo up and down his crack.

I tease his ass, pushing the tip in slightly before pulling back. Swipe, push, pause... I repeat that a few times, and then push the head in. He gasps, and I keep pushing past the resistance slowly until he takes the entire thing. He is gripping my thighs... and I ask if he's done this before. He tells me that the girl he's seeing is into it, and this is his second time, but his first time with this toy.

I start moving slowly... getting him used to the girth and length of the dildo. I'm completely enamored with watching his ass swallow the dildo over and over. He's super vocal, and is begging me to go faster... moaning my name and begging me to fuck him. I smack his ass and circle my hand around his cock and balls, squeezing slightly as I pick up the pace. He's in a frenzy and I go a little faster and deeper. He's gasping and moaning, and I watch him coming apart. He starts REALLY moaning. Saying it's weird that it feels so good, his voice cracking on the words.

I'm soaked watching how good it's making him feel. I keep going faster and faster because I'm really getting turned on. I'm going at it completely focused on his ass and the pleasure it's giving him. Then he says, "I dare you to jerk me off." I ease off squeezing his cock and balls and start stroking. He goes absolutely crazy... almost screaming in ecstasy.

He's gripping my thighs HARD and I just know it's going to bruise. Then he asks if he can cum, and I freeze. No one has ever asked me that before... and I didn't know what to say.

He asks me what's wrong and it kind of breaks the trance I'm in. I lean over and kiss him deep. I tell him sorry and that I want him to cum for me, but I want to swallow it. He bites at my lip again and says "good girl." I reapply lube and start fucking him again, and within minutes he says he's ready.

I pull out and lean over to suck him, taking him deep in my throat and working my tongue as he cums in my mouth. He cums for a long time, and is twitching in my mouth as I keep sucking him.

He starts shaking and says I can stop if I want to, but I start massaging his balls instead... hollowing out my cheeks sucking more vigorously... overstimulating him. He grunts starts shaking harder... putting his hands on the side of my face and telling me he is done. I suck and lick him one more time before moving away.

I lay down next to him and he says, "that was fucking amazing. We have to keep doing this." I laugh and agree.

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u/myfreakishnature — 14 days ago
▲ 37 r/SensualPeggingStories+1 crossposts

I got pegged in a tent on a mountain (MF)

So I don't have anyone else to tell this to but I had a crazy experience a few days ago and I wanted to tell someone.

Ok so my wife (35f) and I (35m), one of our things we like to do is pegging. Specifically, pegging on vacation in new places. Every hotel, every Airbnb, in our cruise ship cabin... we love to peg in new places. My favorite so far was in the window of our skyscraper hotel room in Vegas looking over the strip. Well, until now.

See, we took a vacation into the mountains. We went for a hike. Before we left, she had me insert my remote control buttplug, and she told me she wore her remote vibe. We went out to the trail, and hiked several miles, each of us playing with the controls on each other's vibrators. Really fun stuff. After not seeing another soul on the trail for over 3 hours, we set up our camp in a cute little spot with a view for dozens of miles down a mountain valley. We erected our tent, and I fully expected to take a rest and maybe cook some food, but as soon as our tent and air mattress were ready, she wanted to fool around.

Right there, on the side of a mountain, she bent me over, lubed me up, and went to town on me in the tent, with the flap wide open, the mountain air in our lungs, and my silly little prostate groans echoing softly across the treetops. There was no foreplay. That was accomplished in the hike with our remote toys. No, she dropped her pants with the quickness, and demanded I do the same. She brought a vibrating strapless. She called me a good boy over and over. Neither of us touched my penis. We never even ate dinner. She pegged me, I didn't cum, we both fell asleep with our shirts on and pants off after at least an hour of pegging action. We both woke up cold, after the sun had dropped, snuggled in the tent. We ate some uncooked food while cozy and giggly under the blankets, and quickly started to fool around again, with a romantic missionary creampie. Lots of eye contact and kissing. She said she looked up at the stars thru the tent window while I came inside her. Amazing.

We woke up the next morning together when the sun crested the horizon and hit our tent. Without a word said, we started making out, touching each other, and before I knew it, she was sliding that incredible vibrating strapless into my butt. We spent another hour or so working together on stimulating the ever loving hell out of my prostate, while enjoying the sounds of nature, our animalistic groans breaking the quiet for nobody else to hear. It's hard to explain the tranquility of being railed to a hands-free orgasm by the love of your life while being surrounded by such natural beauty. It contrasted so heavily from all the man-made places I had been buttfucked in before. There wasn't a picture of a sunrise on the wall, there was a real sunrise. The smell wasn't a "mountain morning" Glade air freshener, it was the real thing. On our sides, spooning style, without ever touching my penis, she pegged my butt until I spilled my seed all over our air mattress. As I came, she giggled and called me her good boy.

We cleaned up, had some actual food, and hung around that area enjoying nature for the rest of the day. We tried to have regular sex again that afternoon, but I couldn't get my dick hard. Instead, she sat in a camping chair while I ate her pussy and she smoked a joint, gazing over the land. We were able to have penetrative sex one more time that evening, but neither of us came. We were both pretty exhausted so we just fell asleep together in our blanket pile.

Early the next morning, we packed up our stuff and hiked back. Hiking after getting butt fucked was interesting to say the least, and my wife had to stop twice because unexpected creampie leaked while she was taking awkward steps. Overall, I would rate pegging in the mountains a 10/10. You should try it!

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u/myfreakishnature — 6 days ago
▲ 22 r/SensualPeggingStories+1 crossposts

First time getting pegged

My (35M) first time getting pegged was with my wife (39F). She surprised me with a strap on and got dressed up all sexy. It started with her pushing me down and holding me there while she edged me. While edging me, she kept rubbing the strap dildo against my cock too.

After a long while of teasing and edging, she lubed both of us up, and started to fuck me in missionary position. She went slow, letting her cock stretch me. After a bit of slow movements, she started speeding up and getting me real close and then stopping. She was loving toying with me while I moaned and turned into a brainless little slut.

After a bit of her teasing, I ended up straddling her with the strap on in my ass. I started to ride her, with my cock hitting her tits. I fucked her hard and quick. As I continued to thrust myself on her cock, she played with my nips and cock. Teasing both. After a while, she stopped touching my cock giving it no attention and focusing on my nips and thrusting into my ass.

Finally, I couldn’t take it anymore. I moaned the loudest moan I had ever made, my eyes rolled into my head as my cock started to convulse. My prostrate had an orgasm, which set off an orgasm in my cock. I ended up having the biggest cum shot I’ve ever had, shooting cum onto her hair, face, tits, and stomach. She hugged me close and we sat in the mess for a while while she gave me aftercare.

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u/[deleted] — 30 days ago
▲ 16 r/SensualPeggingStories+1 crossposts

Stress Relief & Satisfaction [F29/M29] [Stress Relief] [Pegging] [Femdom Experiment]

The front door slamed shut with a thunderous crash, the sound echoed through the empty apartment. Camilla stormed in, her jet-black hair a disheveled mess framing her flushed face, her green eyes blazed with a mixture of anger and pent-up frustration. The day at the office had been a nightmare, her boss pushed her to the limits, leaving her body and mind craving release.

Her heels clicked angrily against the hardwood floor as she strided towards the living room where Ethan was sprawled on the couch, lazily flipping through TV channels. He looked up at her approach, his blue eyes widened as he took in the sight of her fury.

“Rough day?” he asked, setting the remote aside and rising to his feet.

Camilla scoffed, her full lips curled into a sneer. “You could say that. That son of a bitch just loves to make my life miserable.”

Ethan steped closer to her, his tall frame dwarfed her petite figure as he pulled her into a tight embrace. She melted against him, the warmth of his body soothed her frazzled nerves.

“Well, I’m here now,” he murmured, his breath hot against her neck. “Let’s forget about today, okay?”

Camilla’s hands slid up his chest, her fingernails grazed his skin through the thin fabric of his t-shirt. She leaned into him, her lips brushed against his ear as she whispered, “I have a better idea.”

Ethan pulled back slightly, his eyes searching hers. “What’s th........”

“Shh,” Camilla pressed a finger to his lips, silencing him. “Just trust me.”

She took his hand, lead him toward their bedroom. The air was thick with tension as she pushed him onto the bed, her eyes never leaving his. Camilla climbsed onto the bed, straddled him as she began to unbutton his jeans.

“Camilla, what are you—” Ethan started to protest, but she cut him off.

“Hush, baby,” she cooed, her fingers deftly unzipped his fly. “Tonight, I want to give you something special. Something you’ve never experienced before.”

Ethan’s eyes widen as realization dawned on him. “Camilla, are you sure? I mean, I’ve never—”

“Shh, darling,” she interrupted him again, her voice low and sultry. “Just relax and let me take care of you.”

She sliped her hand into his boxer briefs, her fingers wrapped around his already hardening cock. Ethan’s breath hitched as she began to stroke him, her touch firm and confident.

“You’re so hard for me already?” Camilla purred, her eyes gleamed with desire. “I love how your cock responded to my touch.”

Ethan moaned softly, his hips arching upwards to meet her hand. “Camilla, please…”

“Patience, baby,” she chided gently, her thumb swirled around the tip of his cock, spreading the precum that has started to bead there. “We have all night.”

Camilla shifted her position, knelt between his legs as she tugged his jeans and boxers down, freeing his cock. She took a moment to admire him, her gaze traveled from the base to the tip of his throbbing member.

“You have such a beautiful cock, it makes me forget everything when I have bad day,” she murmured, her voice filled with genuine admiration. “So thick and hard for me.”

Ethan let out a shaky breath, his cheeks flushed with embarrassment and arousal. “Camilla…”

She leaned forward, her tongue darted out to lick the tip of his hard cock. Ethan’s hips jerked upwards, a low groan escaped his lips.

“Easy, baby,” Camilla soothed, her hand wrapped around the base of his shaft. “We’re just getting started.”

She took him into her mouth, her lips slid down his length until he hit the back of her throat. Ethan’s hands fist the sheets, his body trembled with pleasure.

“Fuck, Camilla,” he gasped, his head thrown back against the pillows. “That feels so good.”

Camilla humed around his cock, the vibration sent shockwaves of pleasure through him. She bobbed her head up and down, her tongue swirl around his shaft, her cheeks hollowed as she sucked him deep.

Ethan’s breath became erratic, his hips thrusted upward to meet her mouth. Camilla allowed him to set the pace, her hands gripped his thighs as he fucked her mouth.

Just as he was about to cum, Camilla pulled away abruptly. Ethan’s eyes snapped open, a look of confusion and frustration crossed his face.

“Camilla, why did you—” he started to protest, but she placed a finger over his lips, silencing him.

“Trust me,” she whispered, her eyes sparkled with mischief.

Without another word, she rose from the bed and walked towards her wardrobe. She opened it, rummaging through the contents until she found what she was looking for.

“There you are,” she murmured to herself, a sly smile played on her lips.

Ethan watched her curiously, wondering what she’s up to. Camilla turned back to him, hiding something behind her back.

“What do you have there?” he asked, his curiosity piqued.

“Close your eyes,” she instructed, her voice low and husky.

Ethan did as he was told, his heart raced with anticipation. Camilla climbed back onto the bed, knelt between his legs once more.

“Open your eyes,” she whispered.

Ethan opened his eyes, his breath catched in his throat as he saw what Camilla was holding.

“Where did you get that?” he asked, his voice a mixture of shock and arousal.

Camilla smirked, held up the strap-on dildo. “I’ve been curious about this for a while now. So I ordered one online a few days ago.”

Ethan’s eyes were fixed on the dildo. “When did you plan to use it?”

“Tonight, as I was driving back home.” Camilla replied, her voice firm. “Only If you’ll let me.”

Ethan’s gaze shifted back to her face, his eyes searched hers. He could see the desire and determination in her eyes, and it sent a jolt of electricity through him.

“If you’re sure,” he said finally, his voice barely above a whisper.

Camilla smiled, leaned forward to press a gentle kiss to his lips. “I’ve never been more sure of anything in my life.”, Camilla said teasefully.

She reached for the lube on the nightstand, she then asked Ethan to spread his legs apart and upwards so Camilla could access his asshole. He did so without question. Then she applied a generous amount around his asshole and then she slowly inserted two of her fingers inside his ass with lube. Ethan let out a little moan and tried his best to relax.

Then Camilla applied generously to her dildo and then asked him " Are you ready baby?".

Ethan nodded in response. Camilla then slowly inserted the dildo inside his ass,  Ethan let out a loud moan. Camilla knew the pain he's going through right now because his face showed it all. But she moved her hips slowly.

Once she felt that Ethan got used to her thrusts she started to increase her phase while holding onto his legs.  Ethan let out another loud moan. Camilla then started to peg him more vigorously while jerking off his cock with one hand.

She could see Ethan was almost reaching his climax. Camilla decided to increase the tempo even more while jerking his cock with fast pace.

" I'm cumming baby" Ethan let out a loud moan while cumming all over his chest. Camilla stopped pegging his asshole but kept jerking off his cock even after he came. Ethan pushed Camilla's hand away from his cock while saying "Camilla stop or you'll kill me."

Camilla then laughed and she said " Oh I'm not letting you go away that easily my sexy fuck. I was just getting started."  She then walked to her wardrobe and got something and came back to the bed.

She then showed Ethan a blue pill. " What's that?" Ethan asked. Camilla then replied "This is a stamina pill which will help you fuck me even harder than you ever before." She replied. Ethan then took the blue pill and swallowed it down and then Camilla got on top of him while he's still laying on the bed after she saw his cock got hard once again. She then inserted his cock inside her pussy and started to ride him.

Ethan's cock got even harder after taking the pill and very much energetic. Ethan then held on to Camilla's breast and squeezed them hard. Camilla let out a moan while looking down at him. " Harder baby" Camilla commanded. Ethan then grabbed Camilla's ass and started to bounce her up and down on his cock. Camilla let out long moans and her pussy is dripping wet.

Ethan then rolled her down and positioned himself behind her while she's on her fours. He then inserted his cock in her asshole and started pounding on her vigorously. Camilla let out moans while Ethan was pounding on her ass. He kept on fucking vigoursly for about 5 minutes straight before asking commila which position she wanted to get fucked next. She wanted him to fuck her in the missionary.

Ethan then turned Camilla on her back and inserted his cock back inside her pussy.  He then started pounding on her pussy. Ethan sucked on her nipples and bit on them at the same time. Camilla's eyes rolled back and she was already reaching her climax. " Fuck me harder baby" Camilla said. Ethan started pounding her even harder.

Ethan kept on pounding her pussy for about another 5 minutes.  Camilla was already reaching her climax and she knew that the pill was working well on him. So she wanted to make the best out of it.

Camilla then asked Ethan to fuck her ass now.  Ethan then pulled out from her pussy and then inserted his hard cock into her asshole in the same position. Camilla let out a loud moan while he started fucking her asshole. Ethan kept on sucking her nipples. " I'm so close baby" Camilla moaned.

"Cum for me baby" Ethan replied. Camilla felt her body tensed up and shivered as she came. 

Ethan kept on fucking Camilla senselessly as he held on to her hair roughly which made Camilla shed tears but loved it. Ethan fucked her for about another few minutes straight before cumming inside her asshole.

Ethan collapsed on top of her, exhausted but satisfied. Camilla wrapped her arms around him, holding him close as they both caught their breath.

“That was… intense,” Ethan panted, his heart was racing from the adrenaline. Camilla laughed, ran her fingers through his hair. Ethan then said , " well, you said you were gonna surprise me right?"  Camilla chuckled. "Yeah, and I hope I did." she replied.

Ethan raised an eyebrow, a sly grin spreading across his face. “Oh, you definitely did. But don’t think this means you’re getting off that easy. I’m not done with you yet.”

Camilla pushed Ethan and said with a grinn on her face , " Oh you're not done with me are you? What are you gonna do huh?" Said while she held on to his cock and squeezed her grip.  " Well, let me show you," Camilla smirked.

She then straddled him and placed her hand on his neck choking him and her other hand on his cock. " I can see through your bluffing you motherfucker, I can see that you body is exhausted but I don't think your cock is done yet."  Camilla said.

Ethan looked into her eyes and said " well, what are you waiting for?."

Camilla smirked and said " Oh you just wait and see."  She inserted his cock inside her pussy and started bouncing up and down. Ethan then held onto her breasts while she was riding his cock. After a few minutes Ethan said " I'm about to bust the load." 

Camilla stopped midway into her fucking and told him " You're not gonna cum till I.... SAY.... SO.... "  Camilla replied.  Ethan looked at her with a surprised look and said " What do you mean? I'm close baby I don't think I can hold anymore."

Camilla kept on riding his cock with a new found vigor and said, " Don't make me repeat myself, Boy."  Ethan tried to hold on but he knew he couldn't hold on much longer. 

Camilla saw from her boyfriend's face that he was about to cum. She looked up and said with a smirk " Oh you wanna cum that bad huh? "  Ethan nodded. 

Camilla leaned down on his cock again and started jerking off.  " Cum for me baby.  Cum all over my face."  She said while looking into his eyes. 

" As you wish."  Ethan replied while cumming all over her face and on her neck.  Even after he finished, she didn't stop jerking off his cock. She kept going till his cock became sensitive, and she didn't even care.

She kept on going and going till Ethan pushed her away and said " Baby, you're killing me here.", then  Camilla let out a chuckle and said " Well, you deserved this for your earlier behavior."

Ethan just looked at her and said " Whatever you say babe.",  Camilla smirked.  She then kissed him on his lips and said " Clean my face up."  Ethan took a towel and started cleaning her face. 

Once he finished cleaning her up she asked how it was.  Ethan just smirked and said, " It was amazing, I never expected you to peg me and take control over me like this."

Camilla then said " Well, I was tired of getting fucked every day and I wanted a change."

Ethan chuckled and said, " You succeeded in that part. I never felt so good in a long time."

Camilla smirked at him and said " That's what I wanted to hear."

Camilla and Ethan were both laying down on the bed, naked. They both were exhausted but satisfied.

Camilla looked at Ethan and said "I want some cuddles."   Ethan said " come here." Camilla went into his arms and cuddled.

“Okay, we definitely need to do this again,” Ethan murmured, pulling Camilla closer to him.  “Absolutely,” Camilla agreed, snuggled into his embrace. “I’m thinking we make it a regular thing. Like, once a month maybe.”

Ethan raised an eyebrow, his eyes glinting with amusement. “Oh? And what makes you think I’d agree to that?”  Camilla reached down, her hand wrapped around his  cock and giving it a gentle squeeze.  “Because I know you loved every second of it,” she whispered, her breath hot against his ear. “And I know you can’t wait to feel my dildo inside you again.”  Ethan groaned, his hips bucked involuntarily at her touch. “You’re a wicked, wicked woman,” he muttered, but there was no denying the desire in his voice.

“Maybe,” Camilla purred. “But you’re the one who’s going to be begging for more.”  She began to stroke him slowly, her fingers dancing along his length.  “Just think about it,” she continued. “Once a month, you’ll get to experience the kind of pleasure you never thought possible. You’ll get to feel what it’s like to be filled, to be stretched, to be taken to the edge and beyond.”  Ethan’s breath hitched, his cock twitching in her hand.  “And you know what the best part is?” Camilla asked, her voice low and sultry. “The best part is, you’ll get to cum more than once. You’ll get to keep going, and going, and going…”  Her hand moved faster, squeezing tighter.  “…until you’re a panting, begging mess,” she finished.

Ethan was already hard again, his body responding to her touch despite his exhaustion.  “Fuck,” he breathed. “You really know how to make a guy weak in the knees.”  Camilla laughed softly, her lips brushing against his neck.  “That’s the idea,” she said. “Now, tell me you want it. Tell me you want me to peg you again.”

Ethan groaned, his hips thrusting up into her hand.  “Fuck, yes,” he hissed. “I want it. I want you to fuck me, Camilla. I want to feel your dildo inside me, stretching me, filling me.”  Camilla’s heart raced, her own desire reignited by his words. 

“Good boy,” she purred, giving his cock one last squeeze before pulling away.  “Now, let’s get some sleep. I gotta wake up early tomorrow."  As they drifted off to sleep, tangled in each other’s arms, Ethan knew that he would never look at sex the same way again. And he couldn’t wait to see what other surprises Camilla had in store for him.

THE END.

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u/[deleted] — 1 month ago

I got pegged by a tinder date

I recently got broken up with and figured I start putting myself out there. Well I downloaded good old tinder. I’m pretty standard good looking 6’2 185 almost a six pack and take good photos. I start swiping away. No matches for the first few days but on day 3 I match with over a dozen girls. It’s a Wednesday and make small talk with them. I try setting up dates for the weekend but get ghosted by most of them. One girl I match with Abby. We start talking and are vibing I give her my number and she text me. We go back and forth for a bit and I got to save her number in my phone, but I accidentally call her. I hang up right away thinking I caught it in time. A few minutes later she calls me back and says it’s pretty ballsy for me to call in this day and age. I role with and say I’d rather talk to you in the phone than text. We swap relationship history and we both are just getting out of relationships. I am horny and hint around at a fwb situation and she says she’s open to it. I say we grab drinks Friday night and she agrees. I roll up to the bar and order a drink to calm my nerves. She walks in and omg she is drop dead gorgeous and we hit it off immediately. Lots of flirting and flirtatious touching on both ends. I say why don’t we take the party elsewhere and she says her apartment is right around the corner. I say ok. We get to the elevator and we instantly start making out. We are tearing at each others close as we get to her door. We run to the bedroom I throw her on the bed and we both get naked. I go down on her and taste her sweet hairless pussy and she grabs my face and pulls me in deeper as she’s cumming. She then lays me down on the bed and hood on my dick and starts bouncing. It feels great and she’s getting into it. I flip her around missionary and pull her hips up and fuck her hard. Flip her over and give it to her doggy style. She begs for a break as she’s cum twice and she lays on my chest. Both trying to catch our breath. I start rubbing her firm ass and going lower to play with her pussy some more. She says stop it’s sensitive. I’m a little disappointed as I still haven’t cum. When I’m with a girl for the first time I have a hard time cumming due to nerves. She start stroking my dick and giving me a slow handjob. It’s nice but we start talking. She loves what we did and wants some more later. She talks about the stuff she likes and how she’s been with girls. I ask what does she like to do with them. She says fuck them. I figured she meant oral but she starts talking about grabbing a girls hips and sliding her strap on into her. I was like that’s hot. She asks if I want to see it. I say sure, she reaches over to the nightstand and pulls it out. I let out a nervous laugh and say that’s hot. She puts it back and we talk some more. She says that I haven’t cum yet. I tell her it’s hard for me to the first time. She takes it as a challenge and drops down to give me head. She starts sucking my dick and I’m hard as can be but can tell I’m not going to get there. I tell her it feels great but it’s probably not going to happen. She says she knows a few tricks and slips a finger in my ass. I’ve never had anything in my ass before but omg it feels great. I start moaning and she slips in another. My dick is leaking at this point. She sees me squirming and asks if I like it. I say hell yeah. She asks if I trust her and I say yeah. She says hang on I wanna try something. She gets up goes to the nightstand and grabs the strap on. She puts it on and tell me to trust her. I was like no way in hell. She says just go along with it. She put him dick in her mouth and I say ok. She grabs a bottle on lube and lines up my asshole. She places the tip at the entrance and slowly starts to push it. I yell ouch! And say no way. She tells me to push out and it will be easier. She lines up again and the head pops in. It still kinda hurts but she holds still and says relax. I get used to it and she pushes farther in. After 6-7 pushes she says she’s all the way in! I’m surprised that I can take the whole thing and she asks if I’m ready for her to start fucking me. I nod my head. And she is looking me deep in the eyes and starts moving in and out ever so slightly. After about 30 seconds she asks if I want her to turn it on. I said what do you mean. She says this, reaches down and it starts vibrating! I was shocked and it felt amazing. I let out a moan I didn’t know I could make. She smiles and starts to move faster. I can feel the head pass over my prostate over and over again. It’s like nothing I’ve felt before! I look down and I’m harder than I’ve ever been. She starts stroking my dick and after a minute or two I start erupting into the most intense orgasm I’ve ever had! Cum flying everywhere and some even hit my forehead. She slows down with a big smile on her face and says told you I’d make you cum. She pulls out takes it off and lays with me. I’m still seeing stars and she says just wait until morning when we do it again! We fall asleep but there is much more to cum….

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u/myfreakishnature — 15 days ago