I just discovered that if you’re using Internet Explorer as your browser while reading this blog, a lot of the text is covered up by the blog roll. Try using Firefox. It’s way much better.

My very first Christmas present to ♀ was this. Keep in mind we had only known each other for about six weeks at the time. She was, to say the least, surprised. She gave me a very appropriate box set of jazz CD’s that I had mentioned. Fortunately she didn’t toss me out on my ear. Of course her friends and family asked what I had given her. Clearly this would give some indication of the sort of man I was and would determine if I was worthy of her affection. She was, understandably, vague. When these same people asked me…I told them. For some strange reason, most of her family doesn’t like me.

Sometime after that, the dildo from the shiny pail found its way into ♀ bum. Followed a few days later by my penis (the toy had been removed by this time). She had never tried anything anal before and she seemed to quite enjoy it. She even had an occasional orgasm while getting her butt fucked. I’d fucked bums before so already knew that I would enjoy it. At some point during the activity I usually look down and think, “Holy doodoo Batman, I’m fucking this girls ass. Wow!”

We were already exploring my cross-dressing, but hadn’t yet discovered my inner sissy when the subject of me being on the receiving end of anal play came up. I can’t say for certain who brought up the subject, but I do recall she didn’t hold the toy at first. No, the first time I was penetrated was a few hours after we bought this.

On the way home from the toy store, we decided it would be best to have sex before playing around with the harness. She was concerned about figuring out how to get it on in the heat of the moment and I was worried I’d come to quick and not really get a chance to enjoy it. So we had a quickie when we got home. Not a record breaking quickie (that stands at 7 minutes for both of us to orgasm), but we were darn quick.

Once we’d caught our breath we started to play with the harness. It wasn’t as complicated as we’d thought it would be and a few minutes later, ♀ was a chick with a dick. She seemed to think it was cool. I remember her looking at herself in the mirror and swinging her hips, wagging her new found cock. I started getting excited again and even though it had only been about 15 minutes, we decided to try it out. Our choice of position for my first time was on my back, pillow under my hips and legs wrapped around her waist. She used her finger to get me lubed then added a second digit and I was ready to go. I can remember shaking with excitement as she pressed the head of her cock against my asshole and the short, sharp shock when she first entered me. She offered to stop and I said NO!

After that initial pop she slid inside easily until I could feel her thighs pressed tight against my ass. She squeezed some lube into my hand then slowly started to fuck me while I stroked myself. I had never felt such pleasure. I did manage to tell her when to speed up and it didn’t take long until I was screaming, “Fuck me! Fuck my ass hard!” I came with such intensity that two streams of my ejaculate hit the headboard behind me. I had never felt anything as intense before.

I know that playing with my bum has never been ♀ favorite thing, but in the beginning she seemed to take Dan Savages GGG advice to heart. Probably once every couple of weeks, one of us would get some anal action. We discovered that I could wear the harness and fuck her with two cocks (more about that in a later post). We bought vibrating anal beads and a butt plug. Unfortunately the base is a little small so if we want to use it for any length of time we need to use the harness to hold it in place.

Things have changed since then. Anal play continues to be a regular part of our trash talk, but in reality…not so much. at all. At first I thought it might have something to do with her first husband. He announced he was gay when they’re baby was six weeks old. I remember fucking her with a dildo then proudly showing her how I could take the whole thing down my throat (I’d been practicing so I could give her head before she fucked me). Maybe seeing me wearing a frilly nightie sucking on a big silicone cock made her think, “OMG I’ve turned another one.” She says no, but on some level…maybe. I thought maybe it was a poop issue and suggested that with a little preplanning we could deal with that. She said that she never knew ahead of time when she’d want to have her bum played with or want to play with mine. No,  it needed to be spontaneous.

So, I waited and nothing happened. Occasionally I would ask for it and I noticed that she changed as soon as she put the harness on or got close to my ass with a toy. She became distant, she zoned-out, she wasn’t there with me. Even her kisses were different and she couldn’t look me in the eye. There are a couple of positions that we both enjoy with vaginal sex that would work just as well with her wearing a strap-on and she’s passionate and connected, but as soon as that harness goes on she goes off. The final straw came over a year ago. She put on the harness, laid on her back and said “just climb on and do what you need to do.” Those words and that look on her face sent a chill through me. It reminded me of my ex’s attitude about. sex.  I’ve never felt as sexually connected to anyone as I do with my wife and I never ever want to be reminded of the bitch when I’m with ♀. So I told her that my need for anal stimulation was no longer her concern. There were a few tears, but she’s never tried to start anything.

She’s only asked for her butt to be fucked 2 or 3 times in the past year. I don’t know if that’s because she really doesn’t miss it or if she feels guilty about not returning the favour. Maybe it’s about me being resentful and not initiating it.  ♀ and I usually communicate very well so I don’t think she’s hiding anything from me. I really don’t think she knows what it is. As I said before, it’s a regular part of our trash talk, so it’s not like it’s completely forgotten.

I don’t mean to sound like this is a deal breaker for us because it’s not. We have a grrrreat sex life. It just makes me a little sad that we can’t share this. We tell each other when we’ve masturbated. She knows that anal play is often part of my solo activities, but it’s never talked about.

About a week ago, it stopped raining here and the sun came out. ♀ & I went for a walk. It was nice to be out walking, talking, holding hands . Simple pleasures that we’d missed after four months of rain. We talked about this and that and at some point during the walk the topic of interesting blogs I had read recently came up. I told her that I’d read several posts that talked about the preparation for anal sex part of what makes it special. The purchasing of an enema kit or douche, finding the time to use it and get cleaned up, maybe wearing a plug for a while can all be part of the preamble. The preparations are like an extended foreplay and not being spontaneous, needing to preplan it makes it different then other types of sexual contact.

She seemed to understand the logic in that. There were no tears or hurt feelings or resentment. It was just part of a conversation during a lovely walk in the sunshine. I actually hadn’t given it much thought after that until yesterday. I was looking in the bathroom cabinet for muscle relaxants (my back has been killing me) and there on the shelf were two enema kits that I’m certain weren’t there a week ago.

One for each of us?

cheers,

sss

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8 Comments »

1. 

   Its lovely to see that your story is turning out where you’d like it to go but just take it slow. It sounds so utterly exciting for you but it sounds like maybe she’s scared in some way. As for anal – I can’t offer much advice. My doctors have said that given my condition – it could be lethal for me. I guess what I’m trying to say is maybe she needs to really examine herself and her beliefs on all sexual subject matter. I had an experience that while not being of a sexual nature – was caused by something sexual and so caused me to completely reconsider my outlook in that way. For a time my fear and nerves actually shut my responses off because I didn’t know or understand how to cope with them. My S.O and I would have our “play sessions” and for the most part they were great but at some point therein a drop of some sort of guilt crept in or even a small fear that once we crossed certain lines we could never go back. I was really scared that after we crossed certain “ink” barriers we could never do “vanilla” again. I have very clear tastes and so does he but our culture has instilled in us certain guilts and fears that at times are uncontrollable. In waiting for her to initiate this you are being a big man and I appluad you but also – never leave her feeling as I did (do at times) that perhaps thats all you want and that the rest is “old news” I know you aren’t doing that and she likely does too but it never hurts to hear that “yes, I do love you and we can just be vanilla too but these play times are to enhance – not to supersede”

   My apologies for the long winded and rather clinical response to your simple yet beautiful post. You caused me to dig within myself and I had to share my thoughts on the matter

   Enjoy what you have. It can be ever so fragile.

   Comment by Jean — February 26, 2007 @ 6:04 pm

2. 

   wow jean, thanks so much for sharing.
   sss

   Comment by sweatshopsissy — February 26, 2007 @ 9:19 pm

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4. 

   Wow, that’s so sad, it makes you feel so good and she’s not into it. I’ve had the similar experiences: finally screwing up the courage to tell someone I’m dating about wanting to be fucked with a strap-on, only to feel shamed by them and then internalize the shame for awhile. Sometimes I feel like a pre-Stonewall gay man – the thing that turns me on is thought of as disgusting, unmanly, it feels risky to even talk about it. It can be tough. Thanks for your blog.

   Comment by rrr — February 28, 2007 @ 4:48 pm

5. 

   hi rrr;
   ♀ & I are strong…we’ll get past this.
   thanks for stopping in and commenting.
   cheers
   sss

   Comment by sweatshopsissy — February 28, 2007 @ 5:00 pm

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7. 

   This is not your problem so you shouldn’t feel guilty. Disappointed, yes. Maybe angry for the sense of an inplicit promise not honored. I also went through a problem of readjustment after I told my current (second) wife I was bi. But she eventually realized it had nothing to do with her and now accepts my admiring guys’ asses! I only wish our taste in men were less divergent.

   Our anal sex problem mostly is the cleanliness thing. She doesn’t do body solids or fluids (I’m not much on solids . . .). So several kinks of mine are solitary. OTOH, she is very anally sensitive, especially after an orgasm. One time she even asked me for finger fuck her ass after we had both come. What a sexy turn on! Watching my finger slide in and out her ass as she writhed in ecstasy! One of ther best (to me) second climaxes!

   Ahem.

   Anyway, Sometimes, when the sex is good but the options are limited, we just have to take the good (and available) and enjoy the other as we can. My wife and I really only have one hard (no pun intended) and fast rule: no outside lovers without approval. I have done lots of kinky things to myself she wouldn’t be interested in (or wanna know about): anal stimulation (including trips shopping with a dildo in my ass), pee play, and recycling body fluids.

   IMO, any sex is good. Look at it this way: she isn’t saying you can’t enjoy getting your ass filled with a size large butt plug. She just doesn’t want to participate.

   Comment by Old Bogus — May 12, 2007 @ 2:58 am

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