For about 5 years now I’ve kept a journal of my sex-toy experiences, and from the beginning it was prostate-oriented. I’m basically just copy-pasting it to here so I can air my thoughts in the open, in case there is any insight the community can give me.

2015
My first sex toy was the Rocks-off Naughty Boy (end of January 2015). I’d been looking at toys for a while, wondering about trying one out. Finally I decided that after the New Year I would take the plunge (what a resolution). While the selection of toys for women is quite large and there are many different varieties, men have it somewhat worse off in terms of selection. Of course the Fleshlight seemed appealing, or any kind of pocket pussy/artificial vagina, but I’d read that they require special (and usually proprietary) lubricant in able to function correctly, are somewhat difficult to clean, and are usually quite large, so I thought it best not to go down that route. I looked with interest into penis vibrators like the Apollo Hydro Power Stroker or Cobra Libre as well, but one is rather expensive and more of an investment than I was willing to make at the time, the other was again on the large side; I was looking for something a bit easier to conceal from my roommates (I’m not brave enough to let them know about that just now). That left prostate massagers, which are usually smaller and surprisingly easy to clean, requiring just soap and water. I knew I wanted something that vibrated and was waterproof; originally I was looking at the l’Arque from Adam&Eve, but seeing the true size of it in a video changed my mind. While I’ve experimented with anal penetration before, I’d never used anything bigger than my finger and the l’Arque is certainly much thicker than that. Most of the other choices I discovered were non-vibrating and work more on friction (as well as requiring at least one hand and hard to use by oneself so I understand) so the choice quickly fell to one of Rocks-off’s prostate massagers. They vibrate, are waterproof, and are supposed to be hands-free, all things I wanted. The Naughty Boy seemed to be the one to buy, it is designed for beginners, and has a nice taper near the base that I felt would probably help it from slipping out. Seeing the real size again almost put me off, but what kept me moving forward was that taper, which thankfully, is no thicker than my thumb.
After shopping around for the best price, I chickened out. It took a few more days considering if I really wanted to go down this route, if I had chosen the right product, and if I were actually ready to take this step. Finally I decided to pull the trigger. While the shipping was fast, the wait became interminable almost immediately. There was a tracking number which I checked several times a day to see how it was progressing. Thankfully due to diligent thrift store shopping, I managed to score a deal on something I’d been looking for for a while, so that managed to take my mind off my package for a day or two. Finally the day came on which I knew my package would arrive. I planned the afternoon carefully, knowing that I wanted to stay at school working on projects, leaving myself just enough time that the drive home would coincide with a visit from the mailman. I tried not to speed, getting home faster might not matter if my package wasn’t there yet. I considered stopping on the way to pick up food, but I had just done that yesterday and there was nothing I needed. I thought about my Naughty Boy all the way home, and when I got to the mailbox, it was 2:55 and the mail wasn’t there yet. Agony! I kept driving hoping to see how far away the mailman’s car was and thankfully he was at least getting close. I went home, did some cleaning, got on the web and checked my mail, checked the tracking number one more time (it was definitely “Out for delivery”), and after 30 minutes I couldn’t wait any longer. I got back in my car and drove down to the mailboxes where the mailman was busy putting the last of the mail in. Good timing! I opened my box and there was my package.
I’d tried my best to time the shipping and so far had succeeded. I had the entire weekend to myself in which to play around without concerns about privacy or making too much noise. Opening the package and taking the toy out, I could see it was bigger (longer) than I had thought it would be. Thank God for that taper at the base! Originally I thought there was no way it could fit in correctly, but the diagrams on the box were telling me I was wrong. After washing the toy, powering it up, learning how it worked, making sure I had lotion and soap on hand, I hopped in the shower ready to play. The insertion wasn’t difficult, I’d done that before with different objects. There was resistance before full insertion, I was definitely pressing against something, my prostate I hoped, and I found quickly that it took some work to keep the vibrator in place. I started out standing, which worked well enough if I kept my legs together, but I had to be careful moving around the shower and bending over was risky. The vibrations didn’t seem very intense to me, and I could feel them primarily at the spot where the Naughty Boy was penetrating my anus. My rectum definitely felt filled, but I had no idea if I was hitting the prostate with the tip of the vibrator or not, and while I was hard, I didn’t feel like I was receiving much stimulation. I tried adding more by running water over my penis with the shower head, which helped, but not much. The sensations I felt most were the vibrations at the anus and the sense of being filled, much like feeling the need to poop immediately, which before too long did not help as my reflexes were telling me to do just that and made it harder to keep the toy in. Several times I took the Naughty Boy out, cleaned it, added more lotion, and inserted again but always with the same result. I was not having an easy time keeping the toy hands-free, neither were the vibrations stimulating the perineum much either. I tried a new position as well, laying down in the shower as well as I could and crossing my legs, keeping them as far under me as I could, but that made it harder to keep the toy in I found. The best option I found was to clamp down as hard as I could on the toy with my anus, readjusting a few times. Unfortunately after a while the hot water ran out so after turning off the shower I decided to help things along with my hand, at least this time. Masturbating with the vibrator inside me definitely felt good, I don’t know if I’d consider it better than without, but it was definitely a different experience. I tried to let go and moan (difficult for me), but it was still forced, and I couldn’t relax much with the toy inside me for fear that it would come out. When I orgasmed, which didn’t take too long, most of the sensation again was around my anus, not my penis, and I didn’t feel that the orgasm was significantly more powerful, nor did I ejaculate more than I normally do. I thought maybe I had done it wrong.
I did almost manage to squeeze the toy out during orgasm and removed it the rest of the way after I was finished, turned the water back on (cold!) and cleaned off the toy and myself. I was meeting some friends for drinks so I left for that soon after, but couldn’t get the Naughty Boy out of my mind and was still thinking about it the next morning. I could definitely feel a tingling ache in what I supposed was my prostate, and my anus was a bit sore. I had several strong erections over the course of that day and night, and following morning, more often than has become usual in the past few years. In reading the directions on the back of the box, perhaps I hadn’t quite been using the toy correctly yet anyway, and I was certainly determined not to give up that easily. My anus was still somewhat sore the next morning, but I supposed that to be natural for my first time, and I longed to try again as soon as I felt I could handle it.
The second day I considered waiting because of the soreness of my anus, but I couldn’t put it off. I tried not to vary the routine too much, except starting out sitting down in the shower this time. My anus was still sore and very clenched that day and it took several tries to get the toy in. I sat directly on the toy and tried moving around, but I did not feel any different than I did previously. My eventual solution was to masturbate normally until almost ready to come, then switch to stimulation with the shower head. My orgasm was again pretty good but nowhere near earth-shattering or as amazing as I had hoped. The toy, perhaps due to less lotion than the day before, was dry coming out and somewhat hard to remove.
The third day, my anus did not feel sore, unless I clenched it hard. I switched from hand lotion to some personal lubricant that I had bought a while before and didn’t like. It seemed to work out well with the toy, and besides that I didn’t change anything from the previous day, with much the same results. Most of the vibrating was centered around my anus, but I was however getting more used to having the toy inside me. It occurred to me at that time that the inside of my rectum and prostate as well probably didn’t have nerve endings, so it might not be a fluke that I couldn’t feel any sensations from the toy that way. As it was though, I couldn’t say that I noticed any difference in my prostate, or that the vibrations were doing much for me.
I continued using the Naughty Boy every week or so, but still didn’t quite get the hang of it. My routine became to masturbate with it inside while in the shower, then when I was close to coming I would use the shower head to go the rest of the way. I did find that the bullet vibrator inside it was very nice by itself on my penis though. I was thinking of the Cobra Libre still! While in bed I would insert my erect penis into a sock to catch anything that might come out, and then tie another sock around that just below the head of my penis, then slip the vibrator between the two, leaving both my hands free. I found it to work well if I masturbated normally until I was just about to come, then apply the vibrator. I could still then lose the orgasm if I didn’t bear down on it, but by moving around and concentrating, I could keep myself just below the threshold of inevitability, and would keep that up as long as I could stand it. Even pushing myself over the edge, everything about my orgasm was drawn out a little and I found that I really enjoyed the sensations I was getting, even if the bullet vibrator wasn’t powerful enough to get me there on its own.
Armed with this new information, I began looking at products again, this time with the intention of buying a penis vibrator. Actually, despite its price tag, I had already decided on the Cobra Libre. I agree with the reviews that I’ve watched and read in that it does resemble a futuristic racecar, added to that the name which is unassuming for a sex toy but does suggest something sleek and powerful, and I do find the Cobra Libre to look very attractive and appealing, especially with its several different color schemes. It’s nice that so much thought was put into things like design, and even though aesthetics don’t (or shouldn’t) really matter when performance is what one is after, I could wish for even more color combinations. My personal favorite is white/blue, I just think it looks beautiful. I started looking at the original version because there were several online going for a sale price which was a little easier to swallow than the full $130 price tag, and while the white/blue option wasn’t available, white/black was and I could live with that. Still, I wasn’t satisfied yet. I knew there was an updated version out that addressed the two major flaws of the first unit, mainly its troublesome touch-sensitive interface and vibration power. Unfortunately, the Cobra Libre II is only available in black/red and all-black, no white/blue combination out there, and no sale price either. It was a bit tough, but I decided that aesthetics didn’t matter as much as functionality, and paying the full $130 price was worth it to get the extra ease-of-use and updated motor of the newer Mk.II model. I bought in March 2015.
Using the Cobra Libre II for the first time was definitely an experience I’d never had before, and much better than repurposing the bullet vibrator. There was actually a nice suction effect keeping the head of my penis securely inside, and the sensation was not localized to one place like with the bullet. I tried all the recommended ways and positions of using the toy and found them all to work well. There are 11 different settings, but I didn’t get far enough to try them all out; I found the vibration speeds to be so very intense that I didn’t last as long as I thought I was going to. In fact, at some point I’d like to purchase the original Cobra Libre as well, to experience some of its milder vibration settings. Most importantly though, it was definitely a hit with me from Day One. I still remember that first time, alternating between laughing in exhilaration and surprise at the pleasure I experienced, and moaning uncontrollably with the way it made me feel.
The Cobra Libre II has proven itself to be a reliable toy, though I did get used to it a bit more, and it no longer makes me come almost immediately. I’ve learned how to use it in many different ways, and can last over an hour or as short as a few minutes, depending on how I feel. I also tried the Hot Octopuss Pulse III Solo, which is definitely a different sensation, though using it hands-free is a bit more of a chore: I found the best way is to slip it over my penis with no lubrication, then cover everything with a sock to constrict it ever so slightly. The Pulse III is a bit less hassle when it comes to preparation and cleaning, but still the Cobra Libre II works better for me.
The masturbation sleeve seems to be the most popular sex toy for men, and I did want to try one or two, to help me learn to last longer when thrusting. After careful research I chose the Tenga Flip Hole Red, for its superior ease of maintenance, and wasn’t disappointed. I discovered a way to insert it in my chair wedged under the cushion so that I have a natural hands-free thrusting position. It works well for that and I can usually last 20-30 minutes if I want, but all the bumps and ridges give far too much stimulation during my orgasm, and I don’t find it enjoyable. I’m considering buying the new Tenga Flip Zero series, or a different brand if I can find something reasonably easy to clean up.
2016
Off and on for years now I’ve been chasing the elusive prostate orgasm, and so far I have succeeded twice. Both times I was in the shower and I think both times was with the Rocks-off Naughty Boy inside me and the Cobra Libre II providing a little extra stimulation for my penis. I’m not entirely sure exactly how to describe everything I felt, except for a few things: the sensations I was getting from my prostate were very deep inside me, I didn’t know how deep! It is a bit like a sharp pinching sensation at first. At some point I would feel very warm inside, but then all over, to the point where I would start sweating. There was a terribly slow build-up to the orgasm, very different from masturbating traditionally where there was a distinct sensation of going over the edge; the prostate orgasm was more of a very slow ramp up and ramp down, lasting perhaps 5 minutes or longer. I can feel my prostate contract rhythmically, along with my PC muscles and my anus. Lastly, my other muscles would contract, especially those of my wrists and hands, where during the orgasm my fists were so constricted that I couldn’t move my fingers apart. Both times I was able to achieve prostate orgasm I was alone for the day and taking a long shower, and both times were hands-free experiences sitting on the Rocks-off Naughty Boy. Necessary, because once the prostate orgasm starts I’m moaning quite loudly and usually yell myself hoarse. There have been a couple times where I have gotten close, but either my penis came first due to too much stimulation with the Cobra Libre, or my prostate massager has run out of batteries. I’m still working on a foolproof formula, though my own self-control is also essential. Not too long ago, I bought and read through Charlie Glickman’s book The Ultimate Guide to Prostate Pleasure, which has been a good source of encouragement (May 2018).
I’ve tried a few different prostate massagers, the first was just an upgrade to the Naughty Boy by getting what is regarded as the best bullet vibe on the market, the We-vibe Tango. It’s longer, definitely more powerful, and rechargeable. It’s also pink, and I’m glad to finally have something to break up the monotony of black toys. One of my prostate orgasms came from using this bullet vibrator in the Naughty Boy. But I wasn’t satisfied, and finally invested in the Lelo Hugo (in ocean blue). I had it for a few days before it started malfunctioning and I had to get a replacement, which just arrived. Although the reviews I’ve read for the Hugo say that the battery lasts for 2-3 hours, I’m lucky for it to last 1.5 and so far hasn’t done the trick. I will say that it is better designed for hitting the prostate, definitely stays inside of me better, so I can walk around a bit and should be able to move about in the shower without it slipping out. So far however, it hasn’t given me the results I’ve read about in others’ reviews, though I hope this will change with practice and time.

But it hasn’t yet. In fact I bought the Aneros Helix Syn just a few months later (July 2018) because I was frustrated with the batteries running out in the other toys. I’ve been avoiding the Aneros line because it didn’t have batteries and I thought it was supposed to be used by pulling it in and out by the handle. It turns out that’s not true, thankfully, it’s designed to rub up against the prostate and moves using just the internal muscles. The more I think about my two previous prostate orgasms I think that they were achieved through friction rather than vibration and that sent me toward the Aneros. It was slow going and honestly frustrating that I haven’t been able to consistently achieve mind-blowing prostate orgasms, when it seems like all the reviews out there for Aneros, Lelo, etc, say that I will. Aneros thankfully has a very good community and entire walkthroughs dedicated to achieving just that though, so I copied down a lot of useful information and the most important thing I learned is not to get discouraged. Their information turned me onto ID Glide lubricant which is fantastic, lasts a long time and is thick enough to do the trick, though I could wish it was a bit thicker. Thankfully it’s cheap, too, compared to what I’ve been using before. I’ve tried several different types of Sliquid as well as the Aneros Sessions lubricant (made by Sliquid), and was unimpressed with its viscosity. I think that there must be something wrong with how they were all stored because the first few bottles of Sliquid I bought were very thick and stuck onto the butt toys very well, but the ones I’ve bought in the last year or so have been incredibly watery and pretty much useless. I tried to soldier through with what I had, I tried using hand lotion (it gave me cramps), and though I approve of Sliquid’s mission as a company, I have had to turn my back on them, at least where it comes to anal applications. ID Glide is the best anal lubricant I’ve tried so far (that is water-based and so safe for use with my silicone toys), lasts for hours at a time, which is necessary because to date I have had the Aneros inside me for 3-4 hours at one time and still have not quite gotten the hang of everything yet.