[M]y first time anal experience with toy [Elaborated]

[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.

[M]y first time anal experience with toy [Short]

If you never have any backdoor experience, the first time is incredible, at least for me. I start cumming involuntarily once I have the prostate massager first inserted, and I haven’t turn on the vibration yet. The load is huge and long, it just keep slowly dripping out and I can’t control it. This is my longest orgasm yet, it is a whole body experience, my mind is like frozen/paused for a while, and my whole body muscle is like shaken & exhausted. Also I never experience any refactory period after that, I am still in harden state and horny mood, I jerk off right away by stimulating my penis, this time the small load shoot out further rather than dripping out. The deep breathe after that is like I have taken a intense exercise session.

My Weekend in Philadelphia Pt II [MF] [Bondage] [Femdom]

I was under the impression a blindfold was simply deployed to steal my vision and keep me on edge, to anticipate what was coming next, or where Miss Janet was in regards to me, or what toys she had at her disposal. It did all of that, of course, but it absolutely heightened my senses elsewhere with my sight gone.

They bit hungrily, craving the thin flesh of my hard cock and bound balls. All told, Miss Janet informed me that she placed 18 total clothespins on my head, shaft and balls. Her praise kept me focused, not wanting to complain verbally or groan in anguish.

She flicked the clothespins with her forefinger and giggled when I would moan or try to wiggle my cock and balls away from her strikes. The second I settled into a pain on one specific pin, another would get flicked or pulled. I didn’t care to use either safeword, even with the current pain, I feared it might get worse. Still, as if Miss Janet could read my mind, when something really started to burn, she would place a vibrator of some sort on my adorned cock and make me forget all about the decorations.

How we enjoyed our Valentine’s night (with notes by partner) [FM]

D (32M) and I (40F) have been dating for almost 10 months now (*D: 10 months tomorrow!*), so this was our first Valentine’s day together. We were both very excited! We had some weed that we had decided to save for the occasion. We had bought each other presents, and went to a Japanese restaurant near my place. We had a very nice dinner but were quick to leave the table once we were finished eating, because the fun was going to happen back home.

About a week ago, D had sent me a message, role-playing a patient making a doctor’s appointment for a checkup and a prostate exam (*D: our first REAL role-play*). So we had made an appointment for after-hours on the 14th, at exactly 10pm.

Back home, the evening started with opening a bottle of wine, smoking weed, and D doing his nails. He likes wearing nail polish when we’re together, and he looks really cute that way. We opened our presents. D got me an amazing vibrator, something I had never seen before! It feels so good. And I got D a prostate massager.

[FM] [restraints] [bondage] [vibrator] Well, You Asked For It (My first erotica)

A gag was in his mouth, rubbery and tight. He could taste the rubber.

She had put a blindfold over his eyes, a cloth that he could see nothing through. She had led him on all fours, nude, to a spot in the room. Clasps went over his ankles, cold, and two more, soft and padded, at his knees. A bar bolted to the ground kept him from closing his legs, or opening them wider, and kept him still. She had gently put his hands through padded cuffs and raised them above his head, attaching a rope to the ceiling. He had went to straighten, to sit back on his legs, but she had held him in place.

A moment later, a bar was placed on his back, keeping him in a dog-like position, his hands keeping him from dropping and the bar keeping him from rising. He was immobile, halted.

She had laughed, a tinkling chuckled, and nibbled his ear, then. She had given him medicine, as she had done for a while now, that kept his penis erect and hard for hours, but the nibble had sent even more blood to it. With a nip, she walked away, and come back a moment later. “I think we’ll try something less involved, tonight.”