My best pegging experience was with my girlfriend and about a year into our pegging. Everything we had done up to this point had started good and gotten better but this time was the best.

My girlfriend had worn her strap on under her skirt while we were out running errands and teased me about the fucking she was going to give me when we got home. Then on the ride home she pulled her skirt up and pushed my head into her lap telling me to suck her cock. I did and I was very turned on when we got home.

She took off her skirt and I stripped down to the lingerie I was wearing as we made our way to the bedroom. There I sat on the edge of the bed and laid back and pulled my legs up while my gf lubed up her cock.

Then she pressed it against and pushed it into me and kept pushing till it was all the way in. Then she said “Wrap your legs around me and hold on baby cuz I’m going to fuck you like never before.” I did as I was told and wrapped my legs around her and grabbed onto the sheets and the edge of the mattress and she started fucking me.

She started slow but quickly got faster and she fucked me hard and it felt amazing. I was oozing pre cum like crazy and she orgasmed twice while fucking me. And then my cock which had been bouncing around like mad while she fucked me erupted and I squirted jet after jet of hot cum onto my belly as she continued to fuck till she orgasmed a third time.

As my gf stood there catching her breath with my legs wrapped around her she smiled and said “Wow! Looks like we both came like crazy!”

My best pegging experience was part of my best sex experience:

One day my wife and I (especially I) were feeling exceptionally horny. It was a Saturday and we had a free afternoon to have one of our extended “sexcapades.” We started by lying down in the bed on our sides facing each other, giving sensual massages that began at the shoulders, but which quickly progressed to me fondling her big smooth breasts and caressing her inner thighs and her rubbing my chest and working downward. Soon we were pretty much giving each other handjobs (but with no intention of finishing that way)- just me teasing her aroused clit with my middle finger and her softly pulling my already stiff cock through her index finger and thumb. I then turned onto my back and she climbed over me and started kissing my neck and gently biting the base near my collarbone, all while still caressing my cock. Continuing downward she moved her lips between my pecs and moved to either side, licking and gently nibbling my nipples. Moving further down, she arrived at the base of my cock, but moved to either side and licked the creases of my groin to tease me. She moved back toward my now hard cock and started by just licking the underside of my shaft, starting where my cock joins my balls and going upward, stopping before reaching the head. Then she focused just on the head of my cock, licking it from the underside to the top again and again and moving her tongue in circles over it. By this point the tip of my dick was leaking pre-cum and she eagerly licked it up. After doing this for about a minute, she looked up at me and said in a soft sexy voice, “I'm gonna suck your dick SO good!” I answered, “Yeah? Then DO it already! Suck my dick like you mean it, you little slut!” She quickly said, now in a much louder voice, “OH YEAH- I am gonna suck you like you've never been sucked before!” Then she went to town on me. She took my 8-inch cock in her mouth down to the hilt and pulled it out again, then repeated this again and again in rapid succession, getting it slippery wet with spit. She switched back and forth several times from aggressively sucking and licking just the underside of the top half of my shaft, to taking me in all the way and I could feel the head of my cock hit the back of her throat. As she continued blowing me like she couldn’t get enough, I said things like “OH YEAH, swallow my cock like that!”; “Tastes good, doesn't it?” “DAMN, that's so hot- you really know how to suck a cock!” She was giving me the blowjob of my life! But, since my wife has performed so much awesome oral on me, she knows when I am about to blow my load and as I got nearer to that moment she slowed down gradually and gently pulled away, letting my pulsing cock exit her pursed lips with a smack. “Oh no,” she said in a scolding tone, “not yet- you'll have to wait- there is still more we need to do!” She had gotten me so intensely turned on that all I could say was “what do you want to do to me now?” -“Oh, I’M not gonna do anything else to YOU,” she stated plainly, “at least not yet,” she said with a sly smile, “for now- I want YOU to do ME!” As she said this, she nodded her head slightly downward glancing with her eyes toward her lower body, and I got the hint. At that point I didn’t know everything we were going to do, but she definitely didn’t have to ask twice. I sat up and she took my place lying down, moving to the edge of the bed with her legs hanging off. I immediately went down on her as eagerly as she had done on me- eating her out with vigor. I used my tongue like a pro on her swollen clit, enjoying the taste and texture. She was shifting her body and moaning with delight, and I slowly stuck a finger in her expanding pussy- she was already so wet it slid in easily. I stuck another finger in and curled the two fingertips upward repeatedly to stimulate her G spot, all while still licking her vigorously on the outside. Within a couple minutes, she was screaming “THERE! DON’T STOP!” and then “AH, AHH, AHHH, AHHHHHH!” My wife loves oral as much as I do, so she knows how to enjoy the pleasure, and I know how to eat pussy as well as she knows how to suck dick, so it wasn’t but a minute longer until she was screaming yet again “YES! YES! YEESSS!” and came a second time, just as violently as the first. When her ecstatic writhing lessened a bit, I backed my tongue away and pulled my fingers out slowly, allowing her to lie there for just a moment and bask in the sheer bliss that I had given her. However, I have always reveled in my ability to give my wife multiple orgasms in quick succession during every “sexcapade”, so I didn’t wait long- as her body was still spasming I leaned above her and whispered in her ear “now, I’m gonna fuck you like a whore.” With her still hanging off the bed I lifted her legs up and gradually pushed my engorged raw dick into her. Her warm wet pussy was ready and took all 8 inches of me, and she groaned and squealed in ecstasy. I started slow and deliberate, pulling and pushing almost all the way out and back in for half a minute. She was still recovering from her last time, but managed to say in between her shallow breaths, “give it to me!” Then I held nothing back- I shoved my dick into her as far as possible. I leaned my lower body strongly on hers so the area right above my cock rubbed against her clit, and I thrusted like a porn star. She was barely fully recovered from the oral but was already starting to climax again, and I yelled at her “you LOVE it like that! don’t you, you slut!”; “take it! TAKE MY DICK!”; “you LOVE it when I pound your pussy hard!” She came again with “Oh my God! OH my God! OH MY GO-O-ODD!” After her third time, I wanted to switch positions, so giving her barely a moment to recover, I pushed her back from the edge of the bed and swung her legs up and flipped her over. She got the hint of what I wanted next, so she lifted her body up and got on her hands and knees. I then got behind her on the bed and did her doggy style, driving my rock-hard dick balls-deep into her and even increased the speed of my thrusts, and she came twice more with louder-than-ever screams of “AHHH! YEESSS!” I had long ago learned how to hold back so that I could last as long as I want without climaxing, in order to please her first, but I figured that 5 times was enough for my wife now (yeah, “selfish me,” huh? Ha ha!) As her body was writhing violently, I slowed down to allow her a short break and I pulled out without coming. I started to flip her over onto her back again so that I could ravage her in spread eagle and finally finish inside her as I love to do. But now this is where things got even hotter- she stopped me and pushed my hands away. “No,” she stammered, catching her breath, “no, wait.” I was thinking she just needed a little longer to recharge before we kept going, as she often does when I fuck her as good as I had just done, but I was in for a bit of a surprise. She continued, “Now I want to fuck YOU as good as you just did me!” Since we had done it before, I immediately knew what she meant, and her reaching for the nightstand drawer confirmed it- she pulled out the strap-on. She favors one that has a slick three-strap black harness that firmly holds a thick 6-inch-long purple dildo. She quickly slipped it on as I was thinking to myself how lucky I was. I asked enthusiastically “Yeah? Are you gonna fuck me with that? Where do you want me?” She answered erotically “get in the position I was just in- I wanna fuck your ass doggy-style.” I wasted no time complying- I got on all fours and offered up my ass to her willingly. She spread a good amount of lube over that big dildo and started rubbing the tip of it up and down between my ass cheeks. I was so turned on that my cock never even faltered a bit, and I wanted that dildo in my ass so bad. “DO IT!” I shouted at her, “C’mon- FUCK ME!” She pressed the tip against my hole and slowly pushed with a little more force. I really enjoy anal play- sometimes using a butt plug when I fuck my wife, and she had pegged me numerous times previously, so I am not nervous and my hole yielded without too much resistance. Still, even though I am experienced at taking it up the ass, that first entrance is always a bit shocking right at the beginning. After the tip was in she moved backward and forward slowly a couple times to ease it in more and more. It started to feel better and I was starting to moan. When she had it about halfway inside me, I just said “Go deeper.” She kept easing it in further until it was about two thirds inside, then three quarters- I felt the tip lightly brush against my prostate and it made me shiver. “Oh yeah,” I moaned, “that’s it- keep going.” She was now grasping my hips firmly and pushing in and pulling out at a medium pace. I was starting to REALLY enjoy it now. Then, to my surprise, she stopped, pulled out of my ass, leaned forward a little and said “I wanna fuck you on your back! Turn over!” I thought it was so hot I immediately obeyed and assumed the position she had been in first when I fucked her before- on the edge of the bed with my legs raised. She slid the dildo back into my now enlarged hole a little less than halfway. “Oh yeah!” I said again as I felt it slip inside much easier now that my man pussy was warmed up. I was so sexually eager that all I could think about then was how I wanted that thing farther inside me. She read my cues and now shoved that big phallic beauty all the way into my tight hole as deep as it would go. “YES!” I said a little louder, “that’s good!” She increased speed and started thrusting hard and deep on each stroke. Then, when I thought it couldn’t get any hotter, she grabbed my cock firmly with her hand. By this point, my dick was oozing a steady stream of pre-cum, so it was easy to jerk me off smoothly, and she started stroking me fast. “Oh yeah!” I said even louder, “Oh God!” Then, when I still thought it couldn’t possibly get any hotter, she started talking dirty, “Yeah? You like that, don’t you?” And I immediately responded to her talk- “Yes! I love it!” We answered back and forth –“Yeah? Do you love it when I fuck you like this?” –“Oh God yes, I love it!” –“You’re my little bitch, aren’t you?” –“Yeah, I’m your bitch, use me!” –“Your ass is mine!” –“Yes! I love it when you fuck me in my ass!” –“Your hole is so tight!” –“Yes, stretch my hole!” –“Take this! Like that! All the way!” –“Oh God! Open me up! Fuck me harder!” She was now thrusting like a porn star too and I was taking that big purple dildo so deep and hard, losing myself in utter bliss as she rammed it in me, hitting my P-spot over and over and over and stroking my cock like crazy. –“YES!” I was now shouting wildly, “YES! OH GOD! FUCK ME! POUND MY ASS! FUCK ME HARDER! OH GOD! FUCK ME!” Then, in a moment of pure magic, with my wife hammering my ass mercilessly with that magnificent strap-on while also manually servicing my cock like no tomorrow, I came like I had never come before in my life. From that prolonged prostate milking, I sprayed my splooge like a million-dollar money shot from the nastiest porn film imaginable- my long, rock-hard, throbbing dick exploded huge jets of thick jizz that shot farther than I thought was possible. The first burst hit my chest near my right nipple, then the second burst landed on my chin just below my bottom lip, then the third flew past my head and landed on the bed behind us. My balls pumped out a few more bursts of warm milky cum from my still pulsating cock that covered my chest and abs and dribbled slowly out the head of my cock, forming a small pool of jizz in and around my belly button. I felt like my heart had stopped and I had died for a whole long minute and just lay there gasping and spasming. When I had sufficiently recovered, I looked up at my wife who was smiling proudly. We didn’t have to say anything- we just stared each other in the eyes and knew that what we had accomplished was our sex masterpiece. I shivered in ecstasy as she pulled out of my gaping hole. Then, in the sexiest way ever, she got on her knees and took my cock in her mouth one last time to suck up the cum that had dribbled down my shaft. Then she rose slowly, dipped her fingers in the pool of cum in my belly button and licked it off her fingers. She stood up further, leaned over me, and licked my chin, moving her tongue upward to bring that shot of cum to my mouth. We kissed and shared that salty blob of jizz. It was a perfect ending to the best experience of my life.

It was the 3rd time she had pegged me with this on, although the others were good. This Time we did it standing, I was facing the wall with my hands on it and bent forward slightly, this is a 11x2 inch strap on, as usual the difficulty is getting the head in. Once she achieved this, it was a wonderful feeling. She moved deeper every trust after pulling back a little. Once she started the pegging it was like an out of body experience, my cock was so hard and it seemed my whole body and being were one. I was absolutely at a sexually high at a place I had never been before and unaware of were it was going, after some time I of enjoying this hight, without any idea it was coming i started shooting my load. It should be noted that for guys, after we get off, we change, the desire is all but gone but not this time, It was an added bliss and I was still peaking. I am not into men or their dicks but at this point I would had done about anything she requested as well as sucking a man's cock.

It was my first time getting off without my cock being touched and never had I been so aroused to such a point. She says it was a huge turn on for her. I believe her, she brings up the subject constantly.

Many years ago during a one night stand ! We’d gone back her house and were in bed, I have no idea how it come about but I was on all fours on the bed, she told me what a nice arse she thought I had but followed up by saying the strangest of things ! “ I wish I had a dick right now she said “ “ I don’t want to hurt you “ she then said while stroking my ass cheeks! Enjoying this I just stayed where I was, the next thing I knew a dildo I’d used on her very wet pussy suddenly started to enter my arse ! I don’t know why but as I said “ no what are you doing ? “ I stayed still and before I knew it I had a rubber cock sliding in an out of my ass ! The sheer thrill, the fear of anyone knowing and the general naughty nature of what was happening had me so turned on I came within no time as her other hand reached round to my stiff throbbing cock 🍆

My best pegging experience was on our anniversary day we had a very fancy dinner while he was cross dressing. Yeah, he is a sissy hubby so I had him locked in chastity for few weeks now and had a vibrating buttplug in him when we were out I started playing with him since the start of our dinner. Turning it on and off making him beg me to stop that thing in his ass. When we were in cab heading home I turned it on and kept it on till we reached home. His facial expressions were arousing me a lot and as soon as we reached home I didn't wait a second to bring him down. He removed my heels and his and started worshipping my feet and then I made him come on his knees and he started licking my pu***. I dragged him into the hall and sat on the couch and I sat on his face he licked me like this was the last time we were meeting. I made him bring my strapon the largest one(10inches) and lube. He stripped himself leaving him with chastity and a buttplug only I teasingly removed his buttplug and applied some lube on the strapon and we fucked for hours in all the positions which are good for pegging ( Doggy, cowboy, missionary, etc). We both had multiple orgasms and at last we had a nice shower

My massage therapist and I were very close and even though she never worked for free and I always had to pay her for a massage which was fine with me because she was great it massages. She also like fucking me with a strap on so I paid her for an hour massage but instead she was going to give my ass a good screwing. She flopped me over her massage table sideways and with a 9 inch cock pushed it up my ass and fuckez me for the entire hour with both of us coming over and over again. Both of us were exhausted and that was the first time I’ve ever been fucked for that long. I had at least two prostate orgasms and she told me that she had multiple orgasms from the base of the dildo rubbing against her clitoris.

I've only been “pegged” twice; both times by my late wife. First time it was during a 69, when she shoved her dildo in me dry and without warning; I shot off instantly. Second time she asked me; it was well lubricated from me getting her off with it.

Afrer my wife suddenly passed away, I have “sat” on it a few times while dressed; the last time leaving it in for the entire night until morning.

I enjoy the feeling of being “filled”. I would probably let another woman peg me, but I have no desire at all for a guy to do it. (Although I love crossdressing, I’m still strictly a heterosexual male when it comes to sex).

My favorite fantasy right know is to be pegged by a beautiful wonan with a strap-on while I'm dressed and while giving it to another beautiful woman at the same time.