r/SensualPeggingStories

I had been seeing this girl for about few weeks and we had met twice. She is 5’6 tall, dark complexion and exotic looking figure. One day, she told me she was going to Gurgaon to meet a friend before heading back home. I told her I would drop her home. She dropped a message when she became free and then i left for her place.

When I reached, she came outside wearing a green salwar suit, and she looked absolutely gorgeous. We got into my car, shared a hug and left.

She asked if she could smoke a cigarette in the car, and I said yes. I also offered her some vodka that I had left from my last trip. She offered me a drink too, but I declined since I was driving. As she smoked and sipped her drink, we sat parked near a cigarette shop, talking and laughing.

She started playing with my hair and flirting with me. I took the hint, held her hand, and gently pulled her closer. I could feel her breath on my face. I looked into her sparkling eyes, and then I kissed her passionately.

We made out in the car for 10-15 min but as it was public spot and she was getting late, we decided to move. We were on our way to her home. She was still playing with my hair and kissing my cheeks. I was holding her thick thighs.

After a while, I was about to take a U turn under a flyover when she unbuckled her seatbelt, leaned closer to me, and gently kissed my earlobe. Without waiting further I placed my hand between her thighs and started rubbing her pussy over the salwar.

She had her tongue inside my ear and was pulling my head to the left while i was trying to check my right side to take a U turn. It was a tough situation but i managed. Just when I took the u turn and we were on the right way, i started rubbing her pussy crazy. She started licking me like an animal.

We were doing 50kmph when she removed her salwar and panty and placed my hand over her wet pussy. She said NOW ITS EASY FOR YOU TO DO IT. I was blown away by this move.

I was so turned on that i couldnt hold it so i parked in a dark area with a moving traffic. I asked her to spread her legs and without saying anything i bendover to lick her wet pussy. All of a sudden i felt her one leg moving over head and pressed in a way so that i cant lift up my head. So i stayed and obeyed her decision. I kept on licking while she was keeping an eye outside. I kept on sucking her juice and playing with her clit while kept on squeezing my head with thick thighs.

I felt my dick was about to burst so cqme up, lowered my pants, pushed her mouth over my dick. She sucked me without any question. She did for good 10 min and then said i have never done something like this in my life and i am fucking horny.

Her mother called and we started moving again.

As she was wearing her lower I asked if i could smell her panty and take it with me? She took the moist panty in her fist, told me open my mouth and put it inside. OMG. I could feel her taste her smell. She was delicious and smelled exotic. I kissed her and dropped her OFF. This has been my wildest oral experience so far.

Just had my first experience WOW I’m 23 and had been curious about pegging for a while after seeing stuff online. Last weekend my boyfriend and I were hanging out at his place and I finally brought it up. He got really shy but said he was down to try. I ordered a small harness and dildo that arrived the next day. We waited till the evening when it was just us. I put on some cute lingerie and had him get on all fours on the bed. I took my time with lots of lube and my fingers first until he was relaxed. When I finally put the strap-on on and started pushing in he let out the hottest moan. I went slow at first then got a nice rhythm going while reaching around to stroke him. He came so hard it surprised both of us. After I cleaned us up we just laid there cuddling and he kept saying how good it felt. I think we’re definitely doing this again soon.

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!

I’m 23 and I’ve been teasing my roommate for months about how cute he looks when he gets flustered. Last night I finally decided to do something about it. I came home from my shift wearing a short black skirt and thigh-high socks, and I caught him staring again. I just smiled and told him to come to my room if he wanted to stop pretending. He followed me in without a word. I pulled my harness out of the drawer and watched his eyes go wide. “You’ve been wanting this, haven’t you?” I asked while I stepped into the straps and tightened them around my hips. He nodded, cheeks burning. I made him strip and get on all fours on my bed. I took my time lubing him up, sliding two fingers inside while he whimpered into the pillow. When he was shaking I lined up the strap-on and pushed in slow. He gasped so loud I had to cover his mouth. “Shh, you’re okay,” I whispered, rocking my hips until I was buried all the way in. I started thrusting, nice and deep, enjoying every little sound he made. Every time he tried to reach for his cock I slapped his hand away. “Not yet. Good boys wait.” I kept a steady rhythm, grinding against him until his legs were trembling. When he started begging I finally reached under and stroked him while I fucked him harder. He came so fast it surprised both of us, spilling over my hand while I stayed inside him. I pulled out gently and kissed the back of his neck. “Next time I’m not going easy on you,” I told him. He just nodded, still catching his breath. I think my roommate is officially mine now.

Finally pegging my shy coworker after months of teasing I’m 23 and work at a small office where this one guy has been blushing every time I talk to him. He’s quiet, always keeps his head down, but I’ve caught him staring at my legs more times than I can count. Last night we stayed late finishing a project and I decided to stop playing around. I was in a tight skirt and boots from the office, and once everyone else left I just leaned against his desk and told him to follow me into the conference room if he wanted to do more than stare. He hesitated but came anyway, cheeks already red. I locked the door, pulled my small harness and dildo from my bag, and watched his eyes go huge. “You’ve been wanting this, right?” I asked while I stepped into the straps. He nodded without saying anything. I had him bend over the table, pulled his pants down, and spent a few minutes working lube into him with my fingers until he was shaking and whimpering into his arm. When he was ready I lined up and pushed in slow. He gasped so loud I had to remind him to stay quiet. I started thrusting steady and deep, gripping his hips and telling him how good he felt. Every time he reached for his cock I moved his hand away. “Not yet,” I whispered. I kept going until he started begging under his breath, then reached around and stroked him while I fucked him harder. He came hard all over my hand, legs trembling. I pulled out gently, cleaned him up a little, and kissed his shoulder. “Next time we’re doing this at my place,” I told him. He just nodded, still breathing heavy. I think I have a new regular now.

I lounged back on the couch wearing a tight shiny black latex dress that hugged every curve of my body. 

My long legs were crossed as I watched you kneel naked in the center of the room. My three girlfriends Lila, Sophia, and Raven sat beside me, all of us dressed in strappy lingerie with wicked smiles on our faces. The thick black strap-on between my thighs bobbed slightly as I shifted, already glistening with lube.

"Look at him," I purred, my voice low and honeyed. "Our little virgin slut is trembling already. How badly do you need this, pet?"

You swallowed hard, eyes darting between the four of us. "Goddess… please."

I smiled, slow and predatory. "Please what? Use your words like a big boy."

"Please Goddess… take my pegging virginity."

The girls laughed softly, delighted. Lila leaned forward, her breasts brushing my shoulder. "He’s so polite. I want to break him first."

"Not yet," I said, raising a hand. I stood up and walked over to you, the thick head of my strap-on brushing against your cheek. "Tonight you belong to all of us. But I’m first. I’m always first."

I grabbed your hair and guided your mouth to my cock. "Get it nice and wet, baby. Show my girlfriends how eager you are to have your tight little ass ruined."

You obeyed beautifully, sucking and licking with desperate enthusiasm while the girls watched and teased you.

"Look at him go," Sophia giggled. "Such a hungry little cocksucker already."

When I was satisfied, I pulled you up by the hair and bent you over the ottoman. I pressed the fat head of my strap-on against your virgin hole and paused, letting you feel it.

"Beg me, pet."

"Please Goddess… please fuck me."

I pushed forward slowly, savoring every inch as your body opened for me. You gasped and moaned, fingers digging into the fabric. I bottomed out and held still, buried to the hilt.

"Mmm, there we go," I cooed, stroking your back. "All the way inside you. How does it feel having Goddess stretch that virgin ass?"

"So full…" you whimpered.

I started thrusting, slow and deep at first, letting you adjust while I teased you mercilessly.

"Listen to those pretty sounds you’re making. My girlfriends are watching you take every inch like a desperate whore. Doesn’t that make you throb?"

Lila and Raven moved closer, running their hands over your body, pinching your nipples, stroking your locked cock.

"He’s dripping already," Raven laughed. "Pathetic."

I picked up the pace, fucking you harder, the sound of skin slapping filling the room. Every time you got close, I slowed down or stopped completely, edging you cruelly.

"Not yet, baby. Good boys don’t cum until all four of us have had our turn."

Sophia took over next, sliding in with one smooth thrust while I held your head in my lap, making you look up at me.

"Tell her how much you love it," I ordered.

"I love it… fuck, I love it so much."

One by one they used you. Lila was rough and fast, Raven teasing and slow, Sophia deep and punishing. I watched with satisfaction as they took turns wrecking your hole, your moans growing more broken and needy with every thrust.

When it was my turn again, I pulled you onto your back, legs over my shoulders, and fucked you face to face.

"Look at me while I ruin you," I whispered, pounding deep. "You’re never going to be the same after tonight. This ass belongs to us now."

You were shaking, babbling, completely lost in pleasure and desperation.

"Please Goddess… I need to cum…"

I smiled sweetly and leaned down, biting your ear.

"No, pet. Not tonight. You’re going to stay denied and dripping while we all take turns using you again… and again… and again."

I kept fucking you through your whimpers until I was satisfied, then pulled out and let the girls have their second rounds while I sat back and watched, stroking your hair.

"Such a good little pegging toy," I murmured. "Welcome to your new life, baby."

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.

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.

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.

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.