r/SensualPeggingStories

Me (26F) and my fiance (29M) were sharing past experiences we'd had, turning into a game of oneupmanship. I'm a pretty small (5' 88lbs) and shy girl so he was shocked when I told him I used to fuck my exbf's ass, and even more so when I told him how much I enjoyed it.

He asked if it was something I'd still want to do and I admitted I had secretly fantasized about fucking him but was too timid to ask. I became self conscious at my over sharing when he didn't jump at the idea and was seemingly uneasy at the idea of being thought of that way.

A week or so later, he had left on a trip when he texted me that if it was something I really wanted to do, he was open to try it when he got back- with the one condition being that if he's going to let me do it, that I can't hold back and enjoy it exactly how I want it.

We spent the next few days flirting about it and speculating what it'll be like while I shopped around finding the harness and dildo. There's something indescribable about the feeling of being a girl picking out her dick that feels almost as embarrassing as it is exciting, and a sence of responsibility of what your husband is going to lose his virginity to. It's the kind of stressful fomo not felt since Professor Oak's ultimatum.

By the time he came home, I was ready to pounce on him. That night I had a bottle of Port chilled and waiting for him in the fridge. I could tell he was nervous so I reassured him I wouldn't be mad or think less of him if he changed his mind but he insisted that he was down so long as I was sure it was what I wanted. I was sure.

He was stalling by sipping the wine I'd poured him and tipped his glass to hurry him along. Being a petite girl my whole life, I'd never had anybody be so intimidated by me and this new feeling was more intoxicating than the wine. He tried to stall once more by refilling his glass- but the bottle was empty. I asked if he was ready and he gave a small nod. I returned a big smile and told him to take his clothes off while I put it on.

I had set aside my lacy lingerie to wear with my strapon and I admired myself in the mirror; a balance of delicate femininity with the masculine appendage that swang and bounced with each step. I draped myself in the doorway, giving him his first look. His eyes peeled away from my dick for only a moment to examine my outfit before once again locking back into place. Feeling his eyes on it made me wet underneath and the look of intimidation on his face was almost enough to make me cum where I stood.

I slowly walked over to the bed, his eyes never leaving my hips and I crawled into bed with him. I kissed him and asked if he wanted to touch it. He was still so shy so I took him by the hand and guided him to it, telling him it was okay and that nobody would ever find out. With that, he took it firmly in his hand and we stroked it together as he passionately kissed me. He moved himself from my lips to my neck and I moaned in approval as he worked his way down my body.

I continued jerking my fake dick in excitement until he pulled my hand away and kissed the tip of it. Had I been able to feel it, there was no doubt I'd had cum all over his face then and there. I watched as he shyly experimented with a dick for the first time. I couldn't take the teasing any more and told him how badly I wanted him and to get in his hands and knees.

I squirt lube into my hand and stroked it onto myself as I watched him nervously get into a submissive position for his first time. My heart raced as my big masculine fiance presented his ass for me and his virgin hole waited for me. I pulled up behind him, wiping the excess lube onto his bare ass.

I teased his asshole with my strapon and asked one last time if he's sure, and he told me to just do it and not to stop until I was finished. I leaned forward and kissed the back of his head, promising I'd be gentle; but as I looked down as his thick ass I wasn't so sure I could keep that promise.

He groaned in what was unmistakably displeasure as I began to push my way into him. I stopped pushing in at the sound of agony, but grabbed his hips to keep him from pulling out as well. With every whimper, I responded with positive feedback of how good he was doing and exaggerating about how close I was to being all the way in.

After about what felt like an eternity, I was finally all the way in. I congratulated him on no longer being a virgin but his face was so buried in the pillows I don't believe he heard me. I did my best to balance of my promise to be gentle and my promise to enjoy him how I wanted.

I grinded against his ass, doing everything I could to hold back my excitement; but the harder I grinded, the more he groaned and the more excited I became. I didn't anticipate his struggle to be such a turn on for me and when he pleaded that I was too deep, I told him I was close and gripped his hips even tighter. Despite his best efforts to remain quiet, by the end his agony and my pleasure were bordering on screams.

I regained composure and felt guilty about how rough I had been with my fiance, pulling out as gently as I could. I had started taking off strapon to let him have his turn with me but he insisted on keeping it on as he bent me over and eagerly sought to reassert himself as if to prove a point.

The dramatic role reversal was jarring but exciting for both of us as it didn't take long to feel his warmth hit me as he finished.

Our first time wasn't the mutually enjoyable experience we were hoping for, and neither was the second. By the third time things finally began to click, but that's a different story for another time.

When we started getting into pegging my girl wasn't really sure how to do it. Her strokes were awkward but I knew she could do it. I was like babe bend me over the bed and fuck me like you've been fucked before.

She bent over the bed and she eased the strap into me. Once she was fully in she grabbed my hips and began pounding my ass. Occasionally she'd give me a good smack. This 5 foot pawg worked my ass. I felt her push deep with a slight shake as she orgasmed.

We both ended up passing out since we had been drinking. I woke up the next morning extremely sore and had to go to work barely walking. I asked her what the hell happened last night. She just pointed at the strap and said really?

It’s been almost a year since we introduced pegging into our sex life. (My idea) and we’ve had fun with it somewhat regularly. We’ve tried a mix of positions and toys to bring us both the most pleasure possible but hadn’t quite reached the orgasmic level we wanted….until last night.

Last night I loosened her up with a few glasses of wine, one of which she enjoyed while I went down on her to orgasm. Then we shifted to the bedroom where she sucked my cock for a bit before she wanted to cum again. She sat on my face, facing my dick, and rode me till she came again all while stroking me just to keep me hard. Then it was my turn.

I helped her into the harness and she made me kiss her cock before demanding that I bend over. She positioned a bullet vibe just right between her and the harness. She started slow and gentle. After just a couple minutes the pace started picking up and she started moaning. Of course I was to but I could tell her vibe was hitting the right spot. Her rhythm picked up more and before I knew it she was just pounding me. I was letting out noises I never have before. She had no mercy on me and fucked me hard until she came. And slowed her pace for a second. I reached for my cock and was dripping with precum. She picked up the pace again and I could tell from the moaning that she was gonna cum again. I kept hold of my cock and she started pounding me harder than she did the first time. Waves of pleasure came over me and her moans increased more and more. A moment later she came again and kept fucking through her orgasm. I pumped my cock just a couple times and came in my hand. She continued fucking me for a couple minutes before she came one final time. Most amazing sex I’ve had and just wanted to share.

My wife has known about my prostate play for about two years now and it is so great to not just do it in secret. She now encourages me to put in a plug for sex because she knows that it turns me on more and when the prostate orgasms start it becomes hard to cum so I can give it to her long and hard.

I love her and love that we can play together now. Unfortunately she had never fingered me and I never brought up pegging. Figured her wiggling a toy just a little or putting a vibrator against it was as close as I would ever get.

Don't get me wrong, what I have with her is absolutely mind blowing and I generally have many dry orgasms before she even has her first, but when I am with her I have to close my eyes and imagine that she is pegging me. When she rubs my taint and I feel her move the toy a little I have to imagine that it is her finger deep inside of me.

So my deepest fantasies of fingering and pegging have remained in my head. Also have fantasy of being in chastity and being made to cum inside a cage. To satisfy mu fantasies now I also play solo when she is gone and I have a lot of toys she does not know about like some dildos, a cage, and a strapon harness. Also sometimes wear her red silky underwear.

Well, yesterday she left to go to work and I was off so thought I would go all out on a fun solo session. I took a shower and sprayed the hot water on my taint and balls to loosen them up. Put some shea butter on my balls so they were soft and moisturized and not stick on the plastic cage. Put a toy in my ass, then put on her red underwear. I put a medium dildo in the harness and strapped it to the post on my bed so I could back up to it later.

I was was laying on the bed having had two or three prostate orgasms with my eyes closed when I heard something and opened them and saw her standing in the doorway. Still have not asked her why she left work early.

I was shocked. She has caught me before with a toy in my ass, but the cage, the dildo, the harness, the underwear, these were all things she never knew about. I expected to get an ear full and have to explain it all, but she never did that. She just said "What are you doing?" as she giggled and then made a joke about me looking cute in her panties and maybe I should trade all my underwear in on panties.

This was not at all what I expected as a reaction, neither was what was to follow.

I know for a lot of people the vulnerability of being pegged is a huge part of it. Well, let me tell you, you don't feel any more vulnerable than all your toys found out at once. I think she understood that and it made for a better reaction.

Then she walked towards me with a grin on her face and reached out and gave the dildo in the harness a soft stroke as she walked by it. She told me to close my eyes and she gave me a gentle tickling rubdown from my hair to my face, around my nipples over my stomach, down my legs and then to my inner thighs. I could feel my skin tingle.

Then she started to rub under my balls through her soft silky panties I was wearing.

Oh, my god, nothing feels quite like having your taint rubbed through that soft silky fabric while you have a toy just dancing in your ass.

She kept rubbing my taint with one hand and then she reached up and started rubbing my nipples with the other hand. It all felt so amazing and I just melted into the feelings, but was also wondering what she thought of the dildo and harness and if she would even mention that she ever saw them, let alone actually peg me with them.

Then she rubbed over my balls and went up further to rub my dick through the panties.

All of a sudden at once I felt her pull her hand back and jump back a little like she was surprised. Had no idea what that was about and then she put her hand back on me, but more deliberite, not gently rubbing, like she was feeling for something.

Oh fuck. I had completely forgotten that I had the cage on under the panties until she grabbed it with her hand through the panties and then she pulled them down so she could have a look. I was so embarrassed and had no idea what to say.

She asked me what the cage was for and I told her that sometimes it feels good to see if I can make myself cum without being able to touch my dick at all. She looked intrigued and wondered out loud if she could make me cum without touching my dick then she continued to rub the cage, my balls, and my taint through the panties.

A little while later she was getting worked up herself and she stripped all of her clothes off and stood where I could reach her wet pussy and rub it. I could tell that she was very turned on.

She pulled the panties off of me, rubbed the cage, and then she said: "Now I see what this is for." and she undid the harness from the bed post. I was so excited in anticipation and then disappointed when she started to strap the harness to me over my cage. Seems she thought the whole reason for the harness was so I could fuck her with it while I was caged.

I figured at this point best to just go along with it for now and maybe she would catch on, but she just started stroking the dildo and licking it trying to excite me enough to cum in the cage.

Then she told me to stand up and she got on her knees and started sucking on the dildo very passionately. It was hot to watch, but not so much that I was going to cum from it. Five minutes later she realized that was not going to do it and she stopped and looked up and asked if she was doing something wrong.

I told her that it was OK, but just not going to push me over the edge. She looked disappointed and then she said "OK, then you are going to have to show me what to do better." as she started undoing the strapon from me.

Then she really shocked me when she put it on herself and said "OK, now you can get on you knees and show me how you like it."

I kneeled down and she put both hands on the back of my head and pushed the dildo towards my face saying "Open up!". I complied and she slid it slowly into my mouth.

I had never done anything like this with her before and it felt embarrassing and turned me on at the same time. I took half of the dildo into my mouth and started to slide it in and out of my mouth. I had not been thinking of the toy in my ass, but now my prostate started to feel really good and I couldn't help but start to moan.

It was such a turn on that I just forgot myself and started sucking on the dildo, licking the shaft, and slobbering all over it, moaning the whole time. I put my hand between her legs and felt that she was dripping wet so apparently it was turning her on too. I grabbed her ass and started pulling her towards me as the whole dildo slid all the way to the back of my throat and then I started long slow strokes all the way in and out of my mouth.

She said "Wow, I never thought that you could teach me how to give a better blowjob.". I figured what the hell and I said "Well, maybe you could also teach me how to do you better.". She replied with "OK, I will. You lean over the bed and I will show you how I like to be fucked."

I leaned over the bed and felt her pull the toy out and then I heard the squirt of the lube bottle. Then I felt the head of the dildo press firmly on my hole. She kept steady pressure on and and it slowly started to slide in. She grabbed my hips and pushed it all the way in and I let out a loud moan of pleasure. I had used a dildo on myself before, but it never felt like this. Her thrusting it slowly in and out while she held my hips was intoxicating. It felt better that I ever dreamed possible.

This went on for about ten minutes and then she pulled out of me and told me to lay on my back on the bed and close my eyes. I could hear the lube bottle again and then felt her rub my taint and over the cage. She kept rubbing lower and I was lifting my hips off the bed and rocking them. Eventually she slid a finger in me and started to rub my prostate like she had been doing it for years. I couldn't believe that she was finally fingering my ass after wanting it for years. She gave me to dry prostate orgasms and then hopped off the bed and went over to the drawer where we keep our toys.

Next she got on her knees on the bed between my legs and lifted my legs up, one on each shoulder and she scooted closer to me and started to slide the dildo in my ass. It was amazing and she kept a slow and steady pace and played with my nipples.

By this time I was just a quivering, moaning mess and having one dry orgasm after the other. Then I heard a vibrator turn on and she put it against the cage while she fucked me slowly. It was the most intense feeling I had ever experienced and in a few minutes I could feel my dick and balls get wet from the cum coming from inside the cage. She just held the vibrator on the cage and continued to pump the dildo in and out of me and the orgasm just went on and on for minutes.

When she stopped I was covered with sweat, cum, and lube and exhausted laying on my back and she went to the bathroom to take off the strap-on and wash it.

When she came back she said now it was her turn as she handed me the strap-on and told me to put it on.

I fucked her the same exact way that she fucked me and held the vibrator against her clit until she couldn't take any more.

Now all of my fantasies have been fulfilled and it is time to come up with some more.

Firstly I’ve always been somewhat interested in my own ass whilst occasionally watching pegging and sissy porn.. never acted on any of it!

It’s started one sexual session with my wife and we’ve been together 11 years! I randomly had a plug I usually use on her in my hand and I was very drunk whilst she was orally destroying me! I slipped it her and she rolled with it. Slipped it in and I came from the bj pretty quick from there! A few weeks went by and it was never discussed!!

Randomly on a Friday, she gets wine drunk out with her friends at a late lunch whilst I’m at work and starts texting very ovulating induced filth! Random pictures and sexual messages! When I got home I showered straight away and went I. To the bedroom to find her naked, plugged and soaking wet waiting!!

I always eat her out first because I enjoy her taste… but before I could she knocked me to the bed and began giving me head.. very quickly she had a finger inside me, followed by lubed plugs and a big beaded plug followed by the dildo I usually use on her!! Pink and 7inches long.
Within minutes I’d cum in her mouth and she proceeds to sit on my face and cums on my face!! All whilst making me go a second time! In the cool down she suggests getting a strap on! And in my extravagant ending I said “go for it”

2 weeks later I receive 3 pictures with her wearing 3 different dildos from 5 inches to 9 inches! 1 vibrates!!
I get home to the same situation as previous! Except this time she pegs me and I erupt instantly! It felt incredible.. she didn’t stop she made me cum again 10 minutes later!!

Life has not been the same since!!