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First time having Sex while padded?


Ski4ever

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Great to hear you had such a nice experience!

Giving head while changing your male partner (or receiving head while being changed yourself) is one of the most intimate and pleasurable things to do I think. I don't like anal at all, but mouth jobs any which way are just heavenly? And if you spill some you don't have to worry about cleaning up?

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  • 3 months later...
On 7/26/2019 at 11:05 AM, Ski4ever said:

So I finally had my encounter I was waiting for.  I showed up wearing a diaper but changed into an Rearz Princess once I got there and also put in a little plug.  I then changed him into one too.  I actually gave a little head while I changed him for the first time ever which was neat.  It was kind of interesting being on the other end.  I don’t think I had ever been so hard inside a diaper like that before.  After some rubbing I undid the bottom tab on one side and he inserted a bugger plug while rubbing me on the outside of diaper, I thought I was going to explode.  After some more rubbing I teased him with my tongue on the outside of his diaper which drove him wild. Finally after about 10 min. of the big plug being in he put a ball gag in my mouth while kissing me, then bad me Lie face down and he cuffed my hands to the outside of my ankles so was face down almost spread eagle while still on my knees.  He slid the diaper to one side just enough to take the plug out.  He then asked if I was ready.  I was so hard I thought I was going to break through the front of my diaper.  He knew it was my first time so he took his time getting in and use a generous amount of lube.  Once he was in he started off slowly, the slowly progressed and occasionally rubbing the front of my diaper.  After several minutes he really started to pound me and then it happened.  I had my first hands free orgasm.  I shook and moaned for at least 12-15 seconds.  I came what felt like the most I had ever came and it all went into my diaper.  I thought I was  going to faint.  After he came inside me, he pulled out, pushed my diaper back out and I fell over and just lied there totally drained and out of breath.  I could feel his cum slowly drip into my diaper.  

Sounds like an amazing experience ive never had anle but would love to try

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  • 1 month later...

My boyfriend and I both wear diapers pretty much 24/7.

I love it when I get my hand around his dick, start stroking and he pees in his diaper while I give him a handjob. When we move on to anal, we usually take each others diaper off, and hump away. 

But, the best time for me is when I bottom and have a quite full bladder. His humping makes me wanna pee. I then always tell him to cum and pee in me, so when we’re done, and I put my nappy on again, I can pee from both ends.

We have tried it with a diaper on, but in our opinion, it just gets messy.

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  • 1 month later...

It happened again!  This time he slid my diaper sown instead of pushing it to the side.  This gave me much more room in the front which didn't feel as good as the first time because it kept feeling like it was going to fall off.   Anyways after getting on top for a bit he threw me off of him and cuffed each hand to each of my ankles so I was almost spread eagle with my ass in the air and face down on the bed.  He was pounding away but could tell I wasn’t getting off as much as last time because the diaper wasn’t right against my shaft due to it being loose from being pulled down so he started rubbing the front of my diaper after about 30 seconds I exploded i to the front of my diaper which made me shake and scream which didn’t do much since I had a ball gag deep in my mouth.  This turned him on and he came inside of me, I couldn't believe how warm it felt when he came.  He filled me then pulled my diaper back up.  I fell to the side still cuffed to each ankle and slowly pushed out his cum into the back side of my diaper while he kissed me with my ball gag still in.  Having warm cum in the front and back of my diaper was just over the top.

anyone else try anything like this yet?  

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On 1/29/2020 at 11:47 AM, Ski4ever said:

This turned him on and he came inside of me, I couldn't believe how warm it felt with a condom.

I'm confused... You mentioned him coming inside you, then there was a condom, then you were pushing out his cum into your diaper. 

Was there a really really defective condom involved?

 

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Sorry, I fixed it.  I think that was my subconscious seeping through because there have been a condom but there wasn’t because I wanted to try it without one.  I had a lot to write and I think my thoughts were ahead of what I was actually typing.

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  • 3 weeks later...

My first time having sex padded was alot of fun as when he showed up I was wearing and had wet already. He was a good daddy and changed my diaper, cleaned me up a bit down there while playing with me. I was so hard when he put a clean dry diaper on me after which he gave me a bit of a spanking over his knee and pulled the back of my diaper down while doing so. I was so excited I almost came then but he changed it up and entered me slowly and gently from behind and while he was wearing a condom I could feel him get even harder before he came so hard he collapsed as I came in my diaper. We still meet up every once in awhile

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  • 7 months later...
  • 1 month later...

As a female pegging my sissy wife has been a long time thing. Diapered or not it is still fun. As a female I enjoy anal sex immensely, so for a male I know the prostate is a super sensitive spot. To those doing it for the first time try just unfastenning one side of the diaper for better penetration. For those that make a hole in the diaper beware the gel gets messy and in that case be well prepared. I always come preparred with a tarp on the bed for protection. And there are many times when you really don't care about a poop mess either (if you like that). I have strapped on the dildo many times and rode my sissy to ecstasy and watched her have an orgasm with and without a cage. I have felt the shivers of orgasm many times and I see nothing wrong with two consenting adults having fun. I also love when my sissy does me anally in a diaper and makes me shudder with pleasure. For you first timers, just take your time and enjoy diaper sex. Take the advise from a 55 yr. old diaper lover... I am sitting here in bed with my wife after great anal sex on a holiday weekend and guys don't have fear. Butt plugs are fun also but nothing beats a real penis. If you are two gay men bless you and enjoy it.

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I have a sweet little padded sub that makes a trip into town about once a month. I've put a hole in his diaper on several occasions and came in him with no fluff to clean up. Then put some cuts on the plastic of the diaper he's in and tape another over it

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The first time having diaper sex for me was something special and it took me over 20 years to accomplish. It was something wonderful and yet so new to me. I had fallen in love with diapers around the age of 22 and never even attempted anything with my wife with diapers. That was a whole lifetime ago. let me jump to 2017. I was in diapers for over 20 yrs already and never even knew there was such a thing. I had just started seeing a woman 12 yrs older than me that is and has been a diaper lover over 40 years. We spent our first week just kissing, and rubbing, and dry humping. Four dates into this she spent a weekend at my place. I still get tears in my eyes when I think about how gentle and loving she was to me. I'd never in my life had a diaper on during sex and she asked me to leave my diaper on. I was all game for it. She opened one side of my diaper and gave me a glycerin enema. and she had a pink strapon dildo. she spread some A&D ointment on my anus and gently stuck the head of the dildo into my awaiting anus. I've had anal sex many times with men,, but this was a first for me. The sensation of the dildo made me moan and squirm. It didn't hurt because she was so gentle and I figured she must have done this many times. My god once she hit my prostate, I lost my mind ! She continued to rub my prostate until I pooped and came at the same time. The wildest thing was she knew I was cumming and hugged me from behind with the dildo still buried in my rectum. I have never felt that kind of an orgasm before. I'm sorry to say but most gay men are wham bang thank you mam'.. I needed at least a good 10 minutes to clear my head. My gf kissed me and hugged me and wiped tears from her eyes and held me tight. she told me it has been years since she has done this, the last time had been with her husband. I didn't know what to say but kiss her madly and ask her to get on all fours. She handed me a glycerin enema and asked me to do the same for her. I untaped one side of her diaper and gave her the enema and rubbed some A&D ointment on her anus. I proceeded to enter her slowly and she slapped my ass and pushed into me so I just thrust into her, she moaned and started humping my penis faster and faster. Oh my god I have never been so deep in a womans anus (I am very well endowed) and thought that I was hurting her. Then she did the ultimate !!! She released the enema on my penis and balls ! I came instantly! There was no holding back at all. This was something I can honestly say I have never in my life expected or felt. What made me laugh was that she expected everything. She came prepared. I've never pooped my bed. She had covered the bed with a tarp which was new to me. Now I think back to the first time we had sex and this to me was something special. Three years later we were married and we are inseperable. @Evelyn Dellcerro You have opened my eyes to a whole new level of love and I will be there for you to witness life as I know you will be there for me.. I have never loved anyone this much, and I never wanna stop loving you baby !!!!

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2 hours ago, Transfusionelle said:

The first time having diaper sex for me was something special and it took me over 20 years to accomplish. It was something wonderful and yet so new to me. I had fallen in love with diapers around the age of 22 and never even attempted anything with my wife with diapers. That was a whole lifetime ago. let me jump to 2017. I was in diapers for over 20 yrs already and never even knew there was such a thing. I had just started seeing a woman 12 yrs older than me that is and has been a diaper lover over 40 years. We spent our first week just kissing, and rubbing, and dry humping. Four dates into this she spent a weekend at my place. I still get tears in my eyes when I think about how gentle and loving she was to me. I'd never in my life had a diaper on during sex and she asked me to leave my diaper on. I was all game for it. She opened one side of my diaper and gave me a glycerin enema. and she had a pink strapon dildo. she spread some A&D ointment on my anus and gently stuck the head of the dildo into my awaiting anus. I've had anal sex many times with men,, but this was a first for me. The sensation of the dildo made me moan and squirm. It didn't hurt because she was so gentle and I figured she must have done this many times. My god once she hit my prostate, I lost my mind ! She continued to rub my prostate until I pooped and came at the same time. The wildest thing was she knew I was cumming and hugged me from behind with the dildo still buried in my rectum. I have never felt that kind of an orgasm before. I'm sorry to say but most gay men are wham bang thank you mam'.. I needed at least a good 10 minutes to clear my head. My gf kissed me and hugged me and wiped tears from her eyes and held me tight. she told me it has been years since she has done this, the last time had been with her husband. I didn't know what to say but kiss her madly and ask her to get on all fours. She handed me a glycerin enema and asked me to do the same for her. I untaped one side of her diaper and gave her the enema and rubbed some A&D ointment on her anus. I proceeded to enter her slowly and she slapped my ass and pushed into me so I just thrust into her, she moaned and started humping my penis faster and faster. Oh my god I have never been so deep in a womans anus (I am very well endowed) and thought that I was hurting her. Then she did the ultimate !!! She released the enema on my penis and balls ! I came instantly! There was no holding back at all. This was something I can honestly say I have never in my life expected or felt. What made me laugh was that she expected everything. She came prepared. I've never pooped my bed. She had covered the bed with a tarp which was new to me. Now I think back to the first time we had sex and this to me was something special. Three years later we were married and we are inseperable. @Evelyn Dellcerro You have opened my eyes to a whole new level of love and I will be there for you to witness life as I know you will be there for me.. I have never loved anyone this much, and I never wanna stop loving you baby !!!!

You make me love you more and more each and everyday baby !!! You hold my heart in your hands 

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I guess I am the perv in the bunch here because I started young. I was in my junior year of high school and I attended an all male school, which really was to my liking being bisexual. I had met another male and we loved to play in diapers together. I remember so many times we would poop our diapers and switch and wear each others poopy diapers and would have anal sex in a tent in my backyard sounds familiar @Evelyn Dellcerro & @Transfusionelle. We made total pigs of ourselves. We were both on the swim team and would have sex in the lockers after everyone had gone home, and yes diaper sex was big then too. I do know Evelyn for about 20 years or so and she has been a true blue friend and confidant to me. Diaper sex has to be between two people that share their love and can share each other without judgement. Too many people judge and point fingers and make the diaper community look like scoundrels and perverts and the lowest form of life. I was married to a diaper loving woman for close to 30 years that had her life cut short by cancer. We did everything together in diapers. You name it, we did it. I held my wife on a pedestal and I still praise her for giving me 2 beautiful chidren and putting up with my shenanigans. But most of all I praise her for being a great woman, friend and diaper lover. I envy Evelyn and Elle for their love and I truly hope you both live a great life. I love you both and you both are an inspiration to many people here that prove to everyone that its not who you love, its how you love. I am at work now in Japan and I figured I would write this in honor of my wife and great friends back in New York.. Love you all and peace !! Junior you kick ass !!

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3 hours ago, philmydiaper said:

I guess I am the perv in the bunch here because I started young. I was in my junior year of high school and I attended an all male school, which really was to my liking being bisexual. I had met another male and we loved to play in diapers together. I remember so many times we would poop our diapers and switch and wear each others poopy diapers and would have anal sex in a tent in my backyard sounds familiar @Evelyn Dellcerro & @Transfusionelle. We made total pigs of ourselves. We were both on the swim team and would have sex in the lockers after everyone had gone home, and yes diaper sex was big then too. I do know Evelyn for about 20 years or so and she has been a true blue friend and confidant to me. Diaper sex has to be between two people that share their love and can share each other without judgement. Too many people judge and point fingers and make the diaper community look like scoundrels and perverts and the lowest form of life. I was married to a diaper loving woman for close to 30 years that had her life cut short by cancer. We did everything together in diapers. You name it, we did it. I held my wife on a pedestal and I still praise her for giving me 2 beautiful chidren and putting up with my shenanigans. But most of all I praise her for being a great woman, friend and diaper lover. I envy Evelyn and Elle for their love and I truly hope you both live a great life. I love you both and you both are an inspiration to many people here that prove to everyone that its not who you love, its how you love. I am at work now in Japan and I figured I would write this in honor of my wife and great friends back in New York.. Love you all and peace !! Junior you kick ass !!

Phil you are a part of this family and you mean a lot to me. Eve trusts you with her life and I see why. You gave her a thumbs up and you knew me for only about an hour. You were with her during hard times and good times. You are the rock we lean on in times of need. We all love you here.. Make it home safe and I am keeping Jade company. Don't work too hard baby love you !!

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  • 5 weeks later...

Okay now dont laugh at me. I am still the beginner here. I have a boyfriend and we have sex regularly when he is at my house. I first tried diaper sex with him about 6 months ago. I have to admit it was something I really never expected to be so intense and enjoying. We tried it with the diaper open on one side and I have to tell you it is something for my diary. My bf loved it also and we just laid in bed cuddling for hours and letting our diapers soak up all the love. I have to admit a prostate orgasm is very fierce and my legs actually shook. It is something that I recommend to those that havent done it.To my loving aunts @Evelyn Dellcerro & @Transfusionelle Love you both for the opportunity to enjoy such a loving and fun enviroment and for the constant barrage of hugs and kisses !! Now when do I get my own tarp ?

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42 minutes ago, amorfraldaJR said:

Okay now dont laugh at me. I am still the beginner here. I have a boyfriend and we have sex regularly when he is at my house. I first tried diaper sex with him about 6 months ago. I have to admit it was something I really never expected to be so intense and enjoying. We tried it with the diaper open on one side and I have to tell you it is something for my diary. My bf loved it also and we just laid in bed cuddling for hours and letting our diapers soak up all the love. I have to admit a prostate orgasm is very fierce and my legs actually shook. It is something that I recommend to those that havent done it.To my loving aunts @Evelyn Dellcerro & @Transfusionelle Love you both for the opportunity to enjoy such a loving and fun enviroment and for the constant barrage of hugs and kisses !! Now when do I get my own tarp ?

Our dearest Jason, I and Eve are reading this post right now and hugging each other and laughing at the same time. You are our joy and pleasure !! There is nothing you can do wrong in this house. We are so happy that you and Johnny are having the time of your lives and enjoying each others love. Its not everyone that gets to watch a boy turn into a loving man and you sweetie have a spot in our hearts !! You know where the tarps are sweetie, just make sure you clean them off and dry them. We love you so much !

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My wife & I have had sex while diapered more than a few times. Usually, its after we both have been diapered for a while and the diapers have bulked up and are nice and squishy. My wifes favorite to get off having sex in a diaper is for me to take her from behind. We poke a hole in the diaper and use packing tape or duct tape to seal off the gel / padding and then i take her from behind. We both cum from this quite easily and clean up is very easy. I have been pegged while wearing a diaper by my wife with her feeldoe and it takes some doing as far as us both getting off. When we enjoy ourselves this way, I'm 100% of the time locked in chastity under my diaper and if she hits my prostate just right, after about 20 or so minutes ill explode into my diaper thru the cage which feels amazing but definitely plays tricks with emotions in a good way as i feel good as i was able to cum but a wee bit humiliated as i was taken from behind and didn't get to cum in what i consider a normal way. It's honestly all about scene and role play. Any way it happens we are certain to enjoy ourselves and love doing it!

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5 hours ago, amorfraldaJR said:

Okay now dont laugh at me. I am still the beginner here. I have a boyfriend and we have sex regularly when he is at my house. I first tried diaper sex with him about 6 months ago. I have to admit it was something I really never expected to be so intense and enjoying. We tried it with the diaper open on one side and I have to tell you it is something for my diary. My bf loved it also and we just laid in bed cuddling for hours and letting our diapers soak up all the love. I have to admit a prostate orgasm is very fierce and my legs actually shook. It is something that I recommend to those that havent done it.To my loving aunts @Evelyn Dellcerro & @Transfusionelle Love you both for the opportunity to enjoy such a loving and fun enviroment and for the consta nt barrage of hugs and kisses !! Now when do I get my own tarp ?

All me and Jade can do is laugh at that one. If you want I will get you a tarp with your name printed on it !!  You are Evelyn reincarnated as a teen. I'm so happy that you anf Johnny are doing so well together and wish you many years more. You are both great kids and just do what you do Jr. Keep them aunts happy and keep your bf smiling. Love you.

26 minutes ago, gmcchamp99 said:

My wife & I have had sex while diapered more than a few times. Usually, its after we both have been diapered for a while and the diapers have bulked up and are nice and squishy. My wifes favorite to get off having sex in a diaper is for me to take her from behind. We poke a hole in the diaper and use packing tape or duct tape to seal off the gel / padding and then i take her from behind. We both cum from this quite easily and clean up is very easy. I have been pegged while wearing a diaper by my wife with her feeldoe and it takes some doing as far as us both getting off. When we enjoy ourselves this way, I'm 100% of the time locked in chastity under my diaper and if she hits my prostate just right, after about 20 or so minutes ill explode into my diaper thru the cage which feels amazing but definitely plays tricks with emotions in a good way as i feel good as i was able to cum but a wee bit humiliated as i was taken from behind and didn't get to cum in what i consider a normal way. It's honestly all about scene and role play. Any way it happens we are certain to enjoy ourselves and love doing it!

Diaper sex really rocks my friend. Its all about being happy.

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  • 10 months later...
On 12/10/2018 at 3:02 AM, DiaperHappiness said:

Based on my first time experience I would just go slow and be as relaxed as possible. On my first diaper-boi date we both found it much more relaxing and rewarding by just simply wetting ourselves as frequently as possible and then we enjoyed a most wonderful moment of rubbing our very soaked diaper fronts together until the joyous moment of squirting our rich penis milk inside our pee soaked diapers. We then exchanged diapers and that rather started up and new but slow relaxed moment of playtime...giggles:girl_happy:

sounds awesome

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  • 1 month later...

first time i had sex in a nappy i was with a mtf trans lady who loved guys in diapers and being bred. i met her at a London ageplay munch we went back to her place. she made sure i got breastfeeding play first then my nappy had been pulled to one side and she gave me oral sex. then i slipped her knickers off I licked her cock/clit. i felt her rubbing my penis through my nappy with breed me eyes so I penetrated her bum and had anal sex then she ripped my nappy off and we had anal sex again in the shower where i came inside of her this time. after we came out of the shower she diapered me up again and i spent the night there.

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  • 2 years later...

I was 17 years old and had my first gay sexual encounter and I was diapered for the first time too.

This is how it happened we had a few beers and we got naked playing with ourselves soon after the second beer I really very  badly needed to pee and I couldn't keep my erection. I told him I was going to use the bathroom. He said he wanted to put a diaper on me and have sex with me before I used the bathroom.

Right then he took me to the bedroom took a big diaper from his closet and opened it on the bed and he said there was a waterproof mattress cover on his bed under the sheets gently got me lying on my back on the diaper and diapered me.

I was squirming having to badly pee as he was putting a condom on. Between my legs he took a finger under the elastic leg cuff of the diaper lifted it up then put his erection through the gap touched my butt then he pushed into me and started having sex with me.  Having sex with a full bladder my need to pee worse and worse  every thrust hitting  my bladder I was squirming dribbling uncontrollably his 4th thrust a few thrusts later I lost bladder control peeing in a gush emptying my bladder I was still peeing when he jizzed but the emotion of literally losing bladder control feeling warm wetness spreading in my diaper during sex was mindblowing.

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