Reddit mentions of Trinity Vibes Anal Training Set

My warm up routine is less vigorous then it was before I started anal play so I'll give you both the advanced anal warm up and the how to get into anal play for beginners lesson.

My warm up:

• Lube up fingers and massage the outside of my anus (after being turned on from having other kinds of sex). I typically use a gel water-based lube like Sliquid Organics Gel for this.
  
  
• Insert this butt plug slowly while holding a vibrator on my clitoris to help me relax. I'll wear this plug for at least 15-20 minutes.
  
  
• Remove the smaller red plug in the link and insert a slightly larger and straighter plug with more lube applied. Wear this for 10-15 minutes.
  
  
• Remove larger plug and apply silicone based lube (lasts longer than water based) to my asshole as well as my partner's cock.
  
  
• Have anal sex (a vibrator is held on the clitoris during this time to maximize pleasure).
  
  
• Profit from orgasms.
  
  It takes a good bit of work but its more than sufficient for me so that I don't feel any pain from anal. However, since you are knew to this its going to take more work.
  
  For getting into anal the first time you really have to start with lighter anal play. Anal sex itself is a pretty advanced form of anal play and someone who has never done anything to their ass is in no way prepared to really enjoy anal sex. To start just become accustomed to having your anus touched. This can be done by lubing up a finger and massaging the outside. Analingus is another great way to do this, just make sure you shower beforehand and wash yourself really well.
  
  Try incorporating genital play with anal stimulation. The sensation is really weird to someone who hasn't experienced anal stimulation before so you have to pair anal stimulation with genital play to help teach the brain to associate the anal stimulation with pleasure. A vibrator on the clitoris works well for women, or a blowjob/handjob paired with anal play works great for men.
  
  When your partner is comfortable move on to inserting fingers. Use a lot of lube. The best lubes are thick gel water-based lubes, or silicone based lube. Water-based feels nice and is compatible with most toys. Silicone lube won't be compatible with all toys but it lasts a lot longer so it works really well. NEVER use any "anal lubes" such as "Anal Ez" that have numbing agents. These are really dangerous since they numb you so you can't feel pain. Pain is a sign that you are causing injury so by shutting of your body's pain response you can hurt yourself without knowing. Anal play is NEVER supposed to hurt. If it is it means you are doing something wrong (not enough lube, not relaxed enough, going too fast etc.) and you need to stop and slow down.
  
  If your partner can take one finger comfortably you can move slowly to two fingers or try using butt plugs. I highly recommend you get a good set of silicone butt plugs in graduated sizes. This is the one I use and its a great starter set. The first two plugs are good to start with (the last one is huge and I've never managed to accommodate more than 80% of it). Start with the first butt plug after having warmed up with fingers. Wear it for awhile and play with the genitals. Most people I know who like anal play have found that wearing a plug acts like a force multiplier for orgasms making them stronger.
  
  When you have mastered the small plug you can try the medium. Always use a lot of lube and insert very slowly. Since the plug is tapered it works as a good training tool to help you learn to relax and voluntarily control those anal sphincter muscles. As a general rule of thumb the medium plug of this set is a good thing to wear for a bit before you take a penis of average girth. For a girthier partner you may need to work up to the biggest plug before attempting anal sex.
  
  After you've done your whole warm up and you've become very accomplished at relaxing those sphincter muscles you can apply more lube and try anal sex. Make sure the receiving partner is in control of depth, speed and intensity. If that person says stop or slow down the penetrating partner needs to do so. As always stop if it hurts. Incorporate genital play if you can, by either rubbing the clitoris (or using a vibrator) or rubbing the penis if the receiving partner is male.
  
  I hope this is a good guide for you to give things another shot. Best of luck to you and your partner. Feel free to ask questions for clarification if needed.
  

The pegging went pretty well. It's kind of funny, my wife went through 18 years with me, being very turned off by anal. When she did finally come around just a few months back, she really didn't have much trouble, even though it doesn't really turn her on. With me, I was really turned on with the idea of getting pegged because my wife is so not kinky, and this was basically the kinkiest thing I've seen her do. So, I was ready, but insertion did not go nearly as quickly or easily as it did with her. We started with the butt plugs over the weekend. I bought this butt plug set. For both of us, the small was very easy, and didn't provide enough of a "neck" to stay in by itself. The large was too big for us to even think about using. The medium went in pretty easily in my wife, but for me it took a few minutes of easing. It wan't bad or anything. I just had to have her go super slow, and I did have to have her pause a couple times when it hurt a little. It did fuel that age long argument that men are actually wimpier than women. I like to counter with the argument that she has bigger poops!

Anyway, the plugs went well, so when we got back home, I ordered the Tantus Bend Over Beginner Kit. We have Amazon Prime, so we got it in two days. Unfortunately, the day it came, my wife was super tired, so that day broke out 5 day streak. I was thinking that maybe the spell was broken, but she was able to pick back up the next day and that's when we tried it out. So, the small dildo slid right in and we quickly moved on to the medium. We did have to go a little slowly, but it was easier than the plug. It wasn't long before she was pumping away.

As for the overall experience. I'll say that it does feel good, but also can be a little uncomfortable at times. There were some moments where I had to kind of force myself to stop thinking and reprogram what I register as pleasurable... if that makes any sense. For me though, the real pleasure is in seeing my wife strapped up and taking control. She is actually very sexually reserved. I would say she is on the lower side of the libido scale, she almost never masturbates on her own (probably fewer than 5 times in the past 18 years), she doesn't like to dress sexy (even though she really has the body to do so), she doesn't get turned on by anal, and she wasn't really interested in pegging except because I wanted her to try it with me. And, she is not what anyone would label as "kinky". So to see her getting into it and telling me she wanted to see me cum as she stroked my cock at the same time was really the mind blowing part. So, as with many sexual encounters, it was probably 20% physical pleasure, 80% mental.

In the end (no pun intended) her response was that it was "actually pretty fun". Not the most enthusiastic response to a sexual experience, but not too bad either.

(This is the part where I reveal my childish nature.)

Man, that was a long one...
^^^that's ^^^what ^^^she ^^^said

May i suggest the following. We went for this set because it offered 'upgradability' (no pun intended). They're cheap, and you can pick the one you like! We're not going near the large one, because it is SIGNIFICANTLY larger than the medium. They're also 100% silicone, and made by a pretty reputable company. Water based lube, or coconut oil (I've seen this recommended a lot, but we haven't tried it).

http://www.amazon.com/dp/B003156GFE/ref=pe_175190_21431760_3p_M3T1_ST1_dp_1

Get a set of multiple sizes and ramp up slowly. You're going to want to start small. I know several folks who have had success with this. Whatever you buy, make sure it has a flared base because butts (gross as this sounds) tend to suck stuff up. You don't want that trip to the ER, I promise.

I think it depends on the person.

If you look around on Amazon, there are some but plug sets that do both (in other words, have very thick bases, e.g. https://www.amazon.com/gp/product/B003156GFE/ref=oh_aui_detailpage_o01_s00?ie=UTF8&psc=1). Be aware they may not stay in as easily.

Butt plugs are a great way to start experimenting! The rule is always do what makes you comfortable. To help use lots of lube and start small. Amazon has some great sets for beginners. ALWAYS make sure if you are buying something to put in your butt it is 1. flared at the base, and 2. check the size. LOTS of photos can be deceiving without a scale.

On lube: silicone based lubes can break down your silicone toys. I find it best to always use a water based lube, like this. You can also use a condom on toys to keep them cleaner, not let the lube damage your toys, and make cleanup easier.

Hope this helps!

http://www.amazon.com/Trinity-Vibes-Anal-Training-Set/dp/B003156GFE

I'm pretty sure this is the set we have (I've only used the small and medium ones so far). So yes, looks like it does.

If you don't want to, then don't.

If you are only worried, start with a training kit
and take as long as you want.

As a Bonus, remember there is an old saying,
"what's good for the goose is good for the gander."
If he's not willing to do the same training, then he is
probably not that into it either.

Oh Amazon gets a bad rep, but sometimes it can work out. I just randomly found some other things like this and this