A Little Backstory

We first need to turn the way-back machine on and turn the clock back about a year. Our sex was good, often great, and we are hitting it between 3-5 times a week. For an older couple (F49/M57) we seem to be doing better than average, and there aren’t any complaints about our sex life. We have regular PIV (penis in vagina) sex, we do oral, and handjobs/fingering, so there is a bit of variety during the week and we have one toy, a curved vibrator that pretty much just sits in a drawer because she didn’t like the vibration feeling. Our communication about sex has been fine, again, nothing to complain about.

One day, I asked her “do you have any sexual fantasies or kinks you want to explore” and she thought for a moment and said “no, I’ve never really thought about that before, how about you”. I thought about it for a moment, and I basically said the same thing. While we have both had a handful of partners in the past, we can both say that our past partners have been pretty poor partners, I was even in a dead bedroom marriage for 20 years. So thinking about anything beyond vanilla just wasn’t in our wheelhouse. We both wanted to explore new things, but we had no idea where to even begin. While I was browsing shows on Netflix one day, I came across a show called “How to build a sex room” and it sounded interesting, so we started watching it. This really opened our eyes to a world of different kinks and toys and we paused the show a LOT to discuss what we were watching. After that, we found another show called “The Good Girl’s Guide to Kinky Sex” where several couples were given a mystery box each week of toys or challenges to explore different kinks. Again, this show got paused a lot for us to stop and discuss what the couples had been given. All of this led to a handful of purchases from several online sex stores for different toys.

Interest in Anal Play

This newly found interest in new things, led me to do some reading and I came across articles about prostate stimulation and how this can give guys some incredible pleasure. Well, it turns out, the key to getting the best prostate orgasms, is getting something is as close as contact to the prostate as possible, and this means going up through the anus. Reading more about this, is when I learned about pegging. I’ll preface the rest of this by saying that I am a very sex positive person, and my fiancé really is too so when I decided to have a conversation about prostate stimulation and I explained it all…her simple response was: “Would you like to try that?“, to which I said “Yeah, I would like to see what that is about”. This easily led into a discussion about pegging as just another way of utilizing a toy for prostate/anal stimulation and again, she said “Would you like to try that?” and I may have been a little more hesitant here, but I said “I think it is something I would like to explore.

Well, being the type of person I am, I ordered a harness and strap-on, as well as an anal training kit. After a few solo sessions with the trainer products, and feeling pretty comfortable, I showed her the harness setup. I was a little surprised at her reaction, but this time, she said “I don’t think I am ready for that yet“. Ok, I get it, it was a bit of a shock since I hadn’t discussed buying it first and we hadn’t done any anal play together at this point. However, this did kick off a big increase in the use of some toys, and she began using some on me about once a week. Along with this, I had acquired some prostate massagers and had begun doing some solo sessions about twice a week. This really helped to become comfortable with inserting things, as well as teaching my body, and specifically my prostate, that these feelings were pleasurable. Over the next four months, I mentioned the pegging in passing, not asking her or pressuring her, but saying things like “I see why some guys would be into the pegging now” or “I can’t wait to see you wearing that someday“.

My Christmas Present

Now one thing that has been a small impediment to our sex life has been her 25you daughter having to live with us for the past 4 months. We have tried to be quieter and it certainly killed spontaneous activity in the living room or going to the bedroom in the middle of the day. But the day after Christmas, I dropped her off at the airport and she was going to be gone for a week. When I get home, my fiancé takes me into the bedroom and says “I have another present for you” and I see a weight bench next to the bed. A little more backstory here, we have a memory foam mattress and it absolutely sucks for certain positions as you just sink into it and it has no rebound at all. So when I see the bench there, I know this is for trying some other things out….but then the surprise comes and she says “I’m going to put you on that and bend you over the bed tonight“…oh holy hell..she is ready to try pegging!!!

The Preparation

Now, being no stranger at this point to some butt play, and several prostate toys, I can appreciate the value of good preparation. I already take daily psyllium husk capsules to aid my diet and help keep things cleaner down in my basement. We had plans to go have lunch with some friends, and when we got home I took a shower and did some extra cleaning with an anal enema. We both already know that if you are going to go play in shit’s house, you might get a little dirty, but I still wanted to be as clean as possible.

Getting the fun going

We are watching some TV and she only has a bathrobe on and I’ve been rubbing her legs for a bit. I finally can’t take any more and I go down and eat her out. I figured she certainly deserves some pleasure for getting the bench and deciding it was time to try pegging. It’s the least I can do to get her off first, I also figured this would help set the mood a bit. She takes me into the bedroom, strips me down, and she heads to the walk-in closet. The lights are too dim for me to see, but I reach down and feel the dildo between her legs and I start to get excited. She rolls me over into a doggy position with me knees on the bench and me bent over the bed. She grabs some lube and starts with some light fingering action, then rubbing the dildo around my bunghole with little pushes of pressure. This is just driving me wild! She asks if I am ready and I give her the ok, and she slowly pushes it in, very gently, very slowly, it goes in and I let out a gasp. She asks if I am ok and I tell her I am fine, and she pushes it in more. She grabs my hips and starts doing some slow thrusting and grinding…wow…this feels great!

Speaking of Lube

Since i did bring up the topic of lube, let’s spend just a moment here. Your normal lube you use for vaginal use is probably going to be too thin for butt play. I have found that the two best products that work for us are LubeLife Anal or just plain Coconut Oil.

Let’s dissect things a little

Over the past few months as I have been exploring anal play and reading numerous stories and comments from people, I have seen that pegging can be different things to different people. For some couples, they enjoy the power dynamic switch with the woman being dominant and the man being submissive, which is pretty easy to see why. There are more extreme versions of this with men wearing chastity cages and the woman being much more dominant with phrases like “take my cock you little slut” and the power dynamic being much more intense. Then there are guys that are bisexual or bicurious and wanting to explore the feeling of a penis in their ass. In our case, having become no strangers to anal penetration with toys, this felt, to me, to just being a different use of a toy for my pleasure. I never once had thoughts about being fucked by a guy or wanting a real penis. This was my WOMAN, using a TOY on me, in a different way.

How was the experience?

I have to say, it felt like she had done this before. her movements were perfect, everything felt great. When I felt that I shouldn’t continue in order to not be sore afterwards, I rolled over, and we tried a different position, which ended up not working out very well, the grabbed my penis and finished me off.

For me, the whole thing was fun, exciting, pleasurable, and felt extremely intimate. For her, she enjoyed pleasing me and I heard her giggle more than a few times, indicating she was having fun. She said that she just did to me, what she would want done to her, and the experience was definitely a fun time.

Sure, as expected for the first time, there were awkward moments, there was some experimenting to get angles and positions right. We communicated great throughout the entire time to make sure both of us were comfortable and enjoying it. It was like having sex for the first time with someone, you have to expect everything won’t be perfect and it may take a few tries to really nail everything down. Since we both had similair expectations, we had a fantastic experience.

If you have got this far and are still interesting, the next question is likely to be “what does it feel like?”. So first off, it should NEVER hurt. Anal penetration should NOT EVER be painful. You should work up to the dildo size over a handful of sessions, starting with a finger or very small training plug, and working up to the size you will use during the pegging. If, at any time, there is discomfort or pain…STOP, figure it out. Is it the position, the angle, not enough lube or what? Do not continue until it feels ok. The first few times, anywhere from a few, to maybe even dozens, you may only feel the sensation of the penetration and may wonder what the big deal about it is. As your body learns that this feeling is pleasurable, you can then relax enough for the next phase. Once you start getting pleasure from the experience, you may experience an assgasm, this will be your sphincter doing involuntary contractions. This feels pretty damned good. The next one, if you have been getting stimulation on the prostate, is a prostate orgasm. A P-Gasm can feel like a whole body experience with shaking, moaning, and euphoria.

Should everyone try this?

I certainly cannot speak for everyone. There is a lot of social stigma around guys and anal play, and especially pegging. So no, this is not going to be for everyone. What I will say is that if you are open for some different ways of experience pleasure, and want to give it a try. You need to work up to it. Using prostate massagers and butt plugs can do wonders for your comfort level and pleasure level. Just the same as having anal sex with a woman shouldn’t just be “let’s try this today” and it being uncomfortable, or even painful, it is a journey that you decide to embark on and you should take the time to work up to it.

Will we do it again? I am quite sure we will. It may not be a weekly event, but it is certainly something we will incorporate into our repertoire and when we feel like it, we will try do it again.

Come join the discussion on Reddit at r/SexyFunAdvice