The first time you were plugged.

My first butt plug was a very nice experience. Such a turn on to think about it. An older friend got it for me for my 18th birthday. She thankfully told me to open it later in privacy. When I opened it alone later that night, I couldn't help but laugh. strangely enough, I never even though about using it. It stayed in my closet for a good six months or so. One day cleaning out my closet I found that little pink plug still in its box. After doing some searches about plugs I figured I would try mine out. I got out some lube and started working it. This was the first time I had ever had anything substantial up my back side. What a feeling. I didn't get it in this time or the next. It was either the third or fourth time when I was playing with it that it finally happened. It was going deep. Since I had yet to get it in I was kind of determined. I remember there being only just a little bit left and so I gave it a bit of a push and it went in much to my surprise. It was very painful. I was crying and trying to get it out. But it was so lubed up that I couldn't get a good hold on it. The only thing that I could to do take away some of the pain was to turn the vibrator in it on. It finally started easing up on the pain and eventually I had a huge orgasm. Taking it out was a whole new story.

O can't wait unitl I move up in size. Would love to feel that scary feeling of being so full all over again.

The first time was by far the harsh punishment I endured. A friend of mine was sleeping over at my house, she was older by a couple of years and far more experienced than me.

She suggested a couple of games during the night and I failed both of them. The result was I had to do whatever she told me. She lubed me up and since I was still a virgin she struck her butt plug up my ass and told me to keep it the whole night. Luckily for me I had to bear it for another couple of hour as morning was very close.

She came back often and her games were always of that nature.

My first time was my husband made me wear it at home for him before we had sex and it made my pussy so wet...

My first time was also the last, my girlfriend came to my house with his new purchase and asked me to play, I was very skeptical at the beginning, but eventually you know what a girl can always get what they want. however, proved to be a game not too interesting and the next time she has always been to receive

My wife was being really bad during the week and i warned her if she kept it up she was going to have to wear one over the weekend .she fought me to the end and was wearing one all weekend

The first thing I used was a screwdriver. Now I use whatever looks good.

My first time was a solo experience with a smallish rust-colored silicone thing. It quickly learned to escape. What is sad is how much "begging" I had to do to get my husband to participate--eventually--in future plug play.

I don't remember my first time with a plug ( must be 40 years ago ) , I am an " Dirty old man " ( yes you remember that english song from previous century ??? ) here , like in day to day life where I am an " duty old man " , I only remember I have the desire and need to have the plug in and my ass wan't be relaxed because the fantasy was so strong . As result , my body have to follow my volunty and OUCH ! ! ! , it was a common medium plug I always have and use it for her now .

What I remember is the same type and brand but the large one http://www.extremerestraints.com/butt-plugs_1/classic-butt-plugs_124.html the only difference it is skin coloured ; since monthes I tryed to shove it in , but unsuccessfully one day the fantasy was so strong that while masterbating I took the large plug lubed me and the plug , put it on a chair and sit slowly on the chair , arousal was very high , and my leg muscles can't hold me above the plug long time enough , this situation was very hot and still increasing ; I was already on the edge , but wan't cum before the plug was shoved , the need to cum grows and the legs weakened , arousal increased from the tought of what happend ; loosing the fight the precum was oozing , I can't hold on and begin to sit , when the first spurt comes I sit and the large plug passed my narrowest opening , WAOUWWWWWWWWW and O U C H ! ! ! Sore ( front and back ) , exhausted and messy ( juice everywhere ) Thirty years later it is wonderfull to remind me these steamy fantastic moments .

One regret it was a solo , and not with my lover .

I like butt plugs for some solo play, don't like the idea of keeping it in while at work! But you never know, I might try one day and change my mind!

I remember my first really large plug & when it popped in I got scared and thought I was not going to get it out. I remember my heart was racing and my cock stayed hard the entire time. :'(

My first time was great. I was going out with a girl that vas very dominate and in control. I went along with it as it was new and fun. I slept over one night and when I work up the next morning she began her control with an enema and then a spanking.

After the spanking was over she inserted a butt plug and then locked it in place with a chastity device. I then had to go to school for a couple hours and get back to her place for her to unlock it and remove the plug. Upon removing the plug I was given a long and hard belt spanking.

My first was with my gf a few years ago... she had bought it one day, and when we where cuddeling that night, i felt her press something wet and cold at my ass. she told me to relax and breath, and altho it hurted a bit, it was a great feeling.

I think my first time was on a business trip. I stopped in the local adult shop and picked one up. My heart was pounding. I had never bought a sex toy. The lady behind the counter knew it was for me, but I didn't care. I drove back to the motel room like I was crazy. All I could think about was getting it in me. I almost had my pants down in the hallway. I got in the room and striped naked, lubed up and started working it in. It was a classic medium. I had a very good jo session that night. And had a chubby the whole next day just thinking about it.

A girlfriend and I and bought a butt plug for her. After a couple of times it ended up being my turn. She laid me back and slowly worked it in. Didn't even get it in all the way but it was perfect. The second time she wanted to get it all the way in so she said"quit being such a baby and take it like a man!" Then she got on top and rode me with the plug in. Ill never forget it.

I've tried using a small 1" diameter butt plug on my wife a couple times recently. She doesn't like it at all and says it hurts. I won't put it up her for more than a couple minutes and she's ready for me to take it out. She does have a small anus, even for a petite framed 22 year old. It must be the rubbery type material the plug is made from, which is not really all that slippery, even when lubed up with K-Y. I'll shop around and see if I can't find a tempered glass butt plug that's more comfortable to insert. The strange thing is that she gets colonics fairly regularly like I do, and she doesn't complain about the rather large width of the speculum. Then again, a speculum is more slippery than that butt plug she hates.

First time was by a girl. She had convinced me to try a plug and after the first time I was hooked. Just the thought of something long sliding in and out back there turns me on so much now. Never thought I would be into it.

I do not know wether this will count but i will share it any way i ahve recently started to push things up my bottom and am finding the whole experience quite pleasurable i have worked my way up to a hairbrush handle

My first Plug wa just something I made up with some tape and it wa some of the most forfilling experiences that I won't forget but now I need something more but don't won't to buy one because I have no were to hide it wah

My first was at my workplace. I found a hard object shaped like an hourglass, I got crazy thinking about the idea. I immediately grabbed the piece and with some slippery ointment from the first-aid box, slipped it in without a condom.

Now, oh, boy, as I came out of the loo and walked to my station, the speed of my walk was slow. With every step, the dildo wanted to come out, and my sexy ass sucked it in. As I came and sat on my chair, the dildo struck on my prostate and stimulated me so much that some slippery fluid oozed out of my sleeping penis and wetted my undergarment. I said bye to my colleagues and walked cautiously to my car, my anus sucking the dildo with every step of my stride.

The journey back home was very excitable. I took a turn on a bumpy road and with every jerk the anus was sucking the dildo hard. I reached home and just went straight in, took off my pants, and jerked my penis hard and vigorously to bring a great cumulative. That evening I had a wonderful relaxing nap, then went uptown almost to midnight and my anus paining a bit reminding of the pleasure again and again.

My first time was like over 10 years ago, I used one of my sisters tampons, I put it inside a comdom a then wet it so it would grow, lubed up with some vaseline, the feeling was great, painful to get in but such a good feeling, then I worked my way up to bigger things I would find at home. Nowadays I use the medium size vibrator I gave my wife, without her knowingas every time I mention anal sex to her she says she will never try it.... She doesnt know whats shes missing lol

I've always been curious about anal penetration for as long as I can remember. When I was little I would stick my sisters hairbrush up there and the occasional tampon. Then I got into broom handles and various other objects but the first actual plugging took place when I was in grade 9. I found a wooden file handle of my dads and it was the perfect shape. So my brain when straight to the what if I were to stick it in and walk around with it? Then after many walks around the neighborhood I decided to leave it in over night. It took me for ever to fall a sleep (couldn't stop playing with my self) but I did eventually but after about 3 hours of sleep I woke up and my hole was in pain. I took it out and went back to sleep. I started trying it every night for about a week until my body got used to it. Now I love it. I like when you put it in and after about an hour it starts to ache a little but all I do is start clenching on it and wow then it starts to feel REALLY good...

I never really had a plug or anything, but one of my girlfriends said she's gonna get me one lols, but i have put things in the back before. I've tried pens, q tips, and even a tampon . they were enough to drive me nuts. I wonder how a plug is gonna treat me..

Technically, my first 'plug' wasn't a plug, but the handle of my duster. Wasn't very wide, but reasonably long for a newbie, and was the perfect shape for tickling the old prossie. When I ordered my first proper plugs, the Liquorice Dip 'S-M-L' starter pack, I found I could easily bypass the small thanks to my experience with this duster handle. Now, I only use the large.

My very first objects were Q--tips (with soap) but afterwards anything with a rounded tip, such as certain types of plastic pens. The somewhat later enema/douche nozzles, but my main objects were a set of anal plugs that I made myself out of carved and sanded hardwood. I've always found that the plugs for sale in sex shops were far too large, especially in diameter, so I thought it better to make a set of my own. Since I didn't know anything about handling plastic or other composite materials, I used beechwood that I carved, turned and /or sanded int various shapes and diameters.These were then varnished several times with a high gloss, clear varnish which gives them an inherent softness of surface.

In addition it was possible to drill holes in the end parts, enabling string or straps to be threaded through which can then be used as harness/restraint. The strings also serve as safety should a plug inadvertently slip up past the sphincter. This has never happened, but it's a safety measure much like the large flanges on many commercial plugs.

It was quite fun thinking up the shapes and sizes. I still think most factory made plugs are much too large to be pleasurable.

The first time for me was when I was 16 and my girlfriend and I were playing Doctor and she had me get up on my knees and I felt her spread my cheeks and put baby oil on my butt and then she slowly entered my rectum with a douche nozzle. It felt really good. It was then that I discovered anal pleasure.

I was in my early teen age, and I used the handle of an interesting looking tooth brush. Didn't have any clue what to use around to 'make it easy to slide in' so I used something that goes with a tooth brush.... tooth paste. Trying to seat on a seat with that in me was quite an experience.

My boyfriend was very very interested in anal sex, and I was too, but I didn't want to seem too eager lest he think he could get it out of me without making it "worth my while".

He's quite sizable, so I was afraid of going straight into anal sex without being primed. I thought he would just use his finger, but he had a plug and he used that after lubing me up with his finger.

That was a really really good day. We now have quite a collection of plugs, in differing sizes and materials and it's sort of a surprise which one he'll pick on a given day.

My first plug was only about 3 years ago. My boyfriend was giving me the usual spanking and suppository treatment, and then I felt something strange go in after the last suppository. Something much bigger. Once he plopped it into place, he patted my bottom and said," this'll help you keep those suppositories in. Hopefully, you'll be a good girl from now on." Well, I was hooked from that point on!

My first time with a butt plug was a wonderful experience. My best friend and I went to a sex store for the first time. We kind of dared each other to buy one, which we each did. We then went back to her house, for her parents were away for the weekend. That night we again dared each other to insert them. First she bent over and I inserted hers and then she put mine in me. What an amazing night!

Like many of you, I started out with a hairbrush handle when I was younger then progressed to my boyfriends fingers and then when I turned 18 my boyfriend took me to a sex shop and we picked out some butt plugs together. My favourites now are my inflatable vibrating one and a glass icicle. The glass feels so nice inside and a little heavy. But at the end of the day nothing for me beats pumping up that butt plug until I cant take anymore and then turning on the vibration full speed...ahhhhhh 😃