[Short version](https://www.reddit.com/r/gonewildstories/comments/617lby/my_first_time_anal_experience_with_toy_short/)
I [24M] bought my first anal toy few months ago, it is a wired vibrating prostate massager, it is beginner type, about an inch in diameter at its thickest part & insertable length is about 4 inches. While the toy is on its way of shipping, I decided to try using my finger using glove, it is my first time insert something into, TBH, I feel gross, it didn’t end up good, my penis became flaccid right away & I didn’t masturbate for more than a week until the toy is delivered.
When the toy finally arrived, I can’t wait to play with it, I didn’t pick the color, it send out randomly out of 3 colors, I am good with all 3 colors, but I didn’t expecting a [pink](https://www.reddit.com/r/SexToysCollection/comments/5us7j1/my_humble_collection/) one sent to me, it is so hot, turn me on right away. I didn’t use the toy right away, instead I waited until weekend (still didn’t masturbate since last time, 1 week+). I already read something about prostate orgasm from /r/prostateplay before I decided want to explore anal, that is mainly why I got into anal play & my first anal toy. Watched some anal genre porn & browse some photos subreddit, my favorite one being /r/buttplug, prepare myself into the mood. The mood is very important, I don’t want to end up like last time.
Late evening, my sister is out, we share a same bathroom, I decided to try out the toy in the bathroom. I started feeling nervous & heart beating really fast, it is the “first time trying nervous feeling”, like first time solo perform on stage in from of people. I rim the outer butt hole with the toy, it make my already harden penis like boost harden again. I then slowly push the toy in, I immediately start feeling “oh no”, I am gonna ejaculate right away, the feeling is so strong and it is different from typical penis jerk off. I then quickly push the remaining of the toy in, within seconds, I started cumming involuntarily and I haven’t use the vibration yet. I did not even touch my penis yet or don’t even had the chance to touch it. The cum load is huge and long, it just keep slowly dripping out and I have no control at all. My mind is like frozen/paused and my whole body muscle is like shaken & exhausted. I breathe even faster and deeper. This is my longest orgasm yet, it is a whole body experience rather than just penis.
When the dripping stop, my mind also regain “conscious” and freshen, I didn’t feel guilty at all like typical penis stimulation, also never experience any refactory period after such a huge load of cum stacked on the floor like a small mountain, it is also much thicker and whiter. My penis is still in harden state and I am still very horny, I stand up from crouching while also have the toy inside me, and I start jerk off right away by stroking my penis, this time a smaller load shoot out further rather than dripping out. The deep breathe after this is like I have taken a high intensity exercise session.
This is undoubtedly my best & logest orgasm, greatest session ever, now I love to masturbate via anal more than just stroking my penis alone, and [my toys collection](https://www.reddit.com/r/SexToysCollection/comments/5us7j1/my_humble_collection/) just keep expanding, I never expecting I would spend this much money in anal toys.
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Updated.
Source: reddit.com/r/gonewildstories/comments/61f4k7/my_first_time_anal_experience_with_toy_elaborated