The best orgasm I've ever delivered was with "Her Delight."
Her Delight was discontinued years ago and if memory serves, it was due to it being a bit too large both in length and girth and having unnatural "friction ridges" (in addition to production issues). If you aren't familiar with the device, it was a dildo that would attach via the CB-2000/3000 rings, posts and spacers to fit over the penis so that traditional sexual intimacy could occur without actual sexual contact with a sub's cock. Her Delight could be held on with a locking pin or locked on. The base was hollowed out to accommodate the sub's penis. It's basically a male strap on with the intent being to torment a chaste sub by removing the cage portion of the device only to replace it with Her Delight, have some sex, and then put the cage back on.
I'm not tiny by any means, although I'm definitely not huge either. I often got the "it's a good size" comment along with references to an actual penis being far preferable to any form of artificial dildo or vibrator.
I purchased her delight as a bit of a novelty and T was willing to entertain me and give it a go although she had reservations about the size. T mounted me and within 2 thrusts I could tell something was different. Every in and every out had her body quivering as it passed through her. Her eyes were clenched tight. Her breathing was heavy and erratic, coming in the form of heaves and abrupt gasps. Moans and sounds I had never heard before freely flowed out from the depths of her bosom. She bit her lip. T always liked to pin my wrists down during sex. This time around she gripped each wrist with a death clench and would repeatedly lift and slam then down against the bed. I could feel my heart beating in my palms and my hands began to tingle.
T is normally quite talkative during sex. She would verbalize her fantasies and talk about what we're "going to do," and this would assist in her arousal. She's also a bit self-conscious about letting go and being loud during her orgasms so she would try to hold in her non-verbal sounds. That wasn't happening now. Nothing that left her mouth was close to qualifying as a word. The sounds were loud and primal, ranging from squeals of enjoyment, gasps of desperation, deep moans, and grunts that almost seemed like she was hurting. When there were no sounds, I could see her biting her lower lip.
She came several times, each time coming to a rest with it deep inside her. A few moments later she was back to grinding away. As we entered the home stretch T began to slam my wrists against the bed over and over in rhythm, gradually building in pace. I could feel the whole bed rocking and pounding against the wall like a cheesy sex scene in a bad movie, slam, slam, slam, slam, slam, slam. Finally, she braced, arched her back, let out a war cry, and ejaculated violently all over my stomach and chest, soaking the both me and bed. T quickly dismounted, kissed me, and sprawled out.
I left for the bathroom to clean myself up. T's grip had left bruises on my wrists. My parts were sore from the plastic pins poking me (I would later trim them) and the tip of my penis felt almost bruised from being pressed against the inner wall of Her Delight. I was very aroused by now and very happy I got to T have a much more extreme orgasm than usual. I returned to the bedroom and she was asleep, sprawled diagonally on the bed, and snoring. This surprised me a little since we had only gone for about 25 minutes and usually we would continue things on for hours. I let her sleep and watched TV until I got tired and went to bed.
I woke up feeling T's hand on my penis. She had woken up very early. I looked at her and she was glowing. Her eyes were very alive and there was a huge smile on her face.
"Did I fall asleep last night right afterwards?"
"Yes, you did."
"Did you play with yourself after?"
"No, but I wanted to."
"Good boy. I'm so sorry... I've just never felt like that before, it was amazing," she said as she arched her back and stretched.
From here on I could tell T was holding back the "full truth" a bit as she realized there may be implications and she danced around with her words. I was grateful that she did this to try to protect my feelings.
"So it was good?"
"Well... let's just say it was different."
"But different in a good way, right?"
"Definitely! Definitely good... but, I still think I prefer a real cock."
"Your orgasm said otherwise," I said with a grin.
"Well... it's just... I couldn't help it, having an orgasm that hard..."
We used Her Delight a few more times with the same result each time but then stopped and I don't remember why.
I suppose I could look back and say that this was an emasculating experience that planted the seeds of insecurity, etc., but it would be a lie. The truth of the matter is that like most men who aren't hung like a porn star, I've always been insecure about my size and in the back of mind I had always been curious just how much more pleasurable things would be for her if I was larger. This just served to verify those concerns and I continued to do the best that I could do in response, e.g. work on endurance, aim, cunnilingus skills, finger dexterity, etc. It wasn't really all that big of a deal to me since my insecurities were fairly realistic.
Did I find it emasculating? Sure, but this was well after I was conditioned to get aroused by being dressed up as a fur sissy. Oh, a dildo that is larger than me gets her off harder? This was small potatoes.
In all honesty, I guess I just don't really mind having my male ego completely crushed. Having an intact and functioning male ego hasn't ever really done anything positive for me, and if anything, it has done me more harm than good.
I wrote about Her Delight in the past in this post: http://furcissy.blogspot.com/2012/01/discontinued-ds-product-her-delight.html