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First times: My first ever strap on experience

Thanks to Ann over at Ann St Vincent and Maurnas from Cursitivity, who did a guest blog post on Ann’s blog popping her sex blogging cherry! She went into the time she had a boyfriend request her to do anal play with him. So based on that I’m going to delve into my very first anal experience with an old boyfriend. This one’s for you gals.

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Quite a few years ago I was dating this one guy. Let’s call him Anthony. Anthony and I had dated for about a year when he asked me if I ever thought about getting a strap on. I frowned at him while we walking around in town. A strap on? For my girlfriends? He shook his head and said no, for me.

I sat down and looked at him a wee bit. You see, I knew he was bisexual. I just never really put the two together and thought he’d want me to there with him. I mean, for me, if I wanted to be with a woman I find a woman, it’s not like a man can strap on a cunt and I’d be all over that right? Yeah. So the connect really didn’t happen in my brain until he said that he would enjoy it if I got a strap on and used it on him.

We didn’t talk of it again and when I got home after visiting with him I pondered this idea. Would I be ok with fucking my boyfriend with a strap on? Would it be the same as fucking a girl with a strap on? What kind of preparation does a man need for having something shoved up his butt? Lube? Spit? A preparatory blow job? Did I need something else? Was it as easy as anal on me? I mean all one needs is spit and a penis! But men were different, not sure why I thought this. But apparently they were so therefore I was freaking out about any kind of preparation that I needed to do and didn’t know how to do.

Being that I was such a strap on virgin when it came to men, I figured the best thing would be for me to head to Oxford Street and go to the Tool Shed. Being that Oxford Street is the gay capital of Sydney and the Tool Shed had all kinds of toys, from his to hers I thought they would be the best people to talk to.

So I walk in and smile at the guy behind the counter and walk up to him. Hi he says, I start blushing, Hi I say. How can I help you, he asks me. I continue blushing as I say at a million miles an hour that it’s my boyfriends birthday in a few months and being that he’s bisexual and he’s well versed in things going in his butt and I’m not, can you help me figure out what to buy him for his birthday in strap ons?

The lad behind the counter laughs a belly laugh at my awkwardness and comes around the counter to give me a hug and tells me to breathe before I pass out.

He then ushers me towards the windows with leather strap ons as well as cloth. He unlocks it and says try on a cloth one and try on a leather one. The leather ones are more durable and better because of durability and you can clean them relatively painlessly. I try on both and the feel and smell of the leather start to get me all hot and bothered so I say I’ll take the leather one. He then says that’s the hard bit done, now the fun bit. Choose an attachment!

I sit there and stare at the display like a kid in a toy shop.

There were so many to choose from and I ended up going with bluey, who was from a lady duo in Brisbane who make strap on dildo’s for women by women. It was perfectly shaped to hit all the ladies g-spots and I figured that I could use it across the board with men and girls. Surely it wouldn’t matter where it was hitting on the guys right?

So I purchased my goodies and then took them home to try them out. I mean, that dildo was shaped rather interestingly and even though I bought it to use on him, I had to break it in. It did hit all the good spots like they said. I loved it. I was pretty sure he would love it too!

I put it away after cleaning it up until all hallows eve when I was making him his birthday dinner at his place and after our food we retired to the bedroom. I told him to go wait in the bedroom while I got ready and to put on the blindfold and be kneeling on the bed for me naked for when I got in.

Bless his cotton socks, he did just that. I do love a boy who listens to instruction.

I walked in wearing my heels, my seamed thigh highs with my garter and a lovely bra. No underwear needed, the strap on fit over my mound snuggly. It was getting warm and toasty down there!

He was waiting on the bed like I’d asked which made me grin and helped with my butterflies. I was so nervous. Which is another reason I had him put on the blindfold. Last thing I needed was for him to see me looking so unsure of myself! I told him to hold out his hands as I walked into the room. I grabbed his hands and ran them up my legs to the top of my stockings and let him finger the lace at the top while I asked him if he knew what I had as his surprise. He shook his head mumbling no as I saw his penis starting to get hard. I told him that it was good that he didn’t know and he wasn’t allowed to peek as I bent over and got out his gates of hell to place around his half hard cock before it got too hard. And if you’re wondering what those are, they are leather band that has 7 metal rings fitted along it so that it sits on one’s balls and down the shaft of the penis. The harder the cock gets, the more painful the rings bite. I know, but who said I was a nice girl?

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Once I had those on him I straightened up and grabbed his head. I told him to open that pretty little mouth of his. He complied, so I lend down and traced his lips with the tip of my tongue. I told him to keep his mouth open as I let my spit fall into his mouth and then told him that he wasn’t allowed to swallow my spit. That was his lube.

I’m not sure if he realised what was coming next but I did grab his hair and stuck my dildo in his mouth. I told him to suck. I heard him moan audibly as he started to suck. All I knew is that I was having too much fun watching his cock battle the rings I placed around it. It was beautiful to watch it try to bounce and realising that it couldn’t. It started to take on this pretty pinky/purple colour that made me rather happy.

I told him to stop sucking as I pulled my now wet and dribbly strap on out of his mouth and told him to shuffle over on the bed so I could lie down.

Once I was on my back I told him to take off the blindfold.

He did and once he saw that I actually had a strap on and it wasn’t some dildo I was shoving in his mouth his grin was worth the anguish I’d caused myself figuring all this out.

I told him that I did all the work I was willing to do and that now it’s his turn to show me how much he loves his new birthday present.

I told him he had to ride my cock. No lube but his spit. So if he felt the urge that there wasn’t enough lube for his arse, he had to stop riding and make sure that he lubed it up again. I was going to lie back and watch the show he was about to put on for me. I told him that if I enjoyed the show I might relent and take off the rings from around his cock.

As I laid there with my hands on his thighs teasing his cock in the rings and watched him lower himself onto my dildo. I was rather shell shocked that this whole thing was happening and that I seemed to be doing an OK job of it all according to the look on his face. The pressure mounted on my hips as his butts touched the tops of my thighs and his eyes rolled back in his head. I was so amazed at watching that whole dildo slide into his arse. I mean, wow. Is that what a vagina looks like for guys? It made me salivate a bit and pump my hips to make sure I was totally up inside him. Balls deep. Oh I totally felt that shit!

Score one: strap on and I may have just had a mini-orgasm at the look on his face.

And then he started to move and all those nerves I had about thinking I had no idea what I was doing evaporated as I watched this beautiful man ride me to give himself pleasure. It was amazing. I now understand the draw that men have when a woman rides his cock. Just being able to sit back and watch someone use you for their own pleasure is just.. well, words escape me.

Suffice to say that I had those rings off his penis after about 5 minutes of him riding me and I had him on his hands and knees as I gave up on the spit for lube idea and grabbed the nearest lube and pounded his arse until he came. And then I told him to lie down because I was going to ride his face until I also came, which took all of a few seconds because I was so wet and horny from doing him.

And that, my dears, was me losing my strap on and arse virginity to a boyfriend for the first time.

40 Comments

  1. My god, I haven’t lived!
    Sharn, I need you to be my kinky mentor. See that? NEED. Yep.
    I’m also bowing down in the presence of greatness, I’ve had bi bfs/fwbs before but they have NEVER asked me to fuck them with a strap on. And right now I’m wondering why not?!?!?! Sheeeesh, the rejection! πŸ˜›

  2. That is an amazing first time! Oh my god! I’m pretty jealous. But now that I have used strap ons, I really love the feeling of a man on his knees in front of me sucking my strap on. I’ve never had someone ride me before but it recently occurred to me that it was a thing I could have. Now I am anxious to meet someone to try it out.

    • I love strap ons too! They are wicked good fun! As you can see, I think I did OK for my first go all those year’s ago πŸ˜‰

      You should try it! I loved watching!

  3. I must admit that this sounds amazing! Savannah has had fingers up there and I have a prostate massager for a time or two, but….I am thinking that I want Savannah to read this (but at the same time, I worry that she might like it a bit too much. πŸ˜‰

    Sharn, you have such a fantastic way to weave in a little bit of sexy torment to insert every ounce of pleasure to the story-telling. Simply perfect.

    • Thank you Will m’dear πŸ˜‰

      I hope she reads it and has just so much fun for her first time with a strap on!

    • Why thank you!! πŸ™‚

      Not sure about brave, but I knew he liked to bottom for me, so I knew I could push him in that direction.

    • You’re welcome. This really was my nervous first time trial. I got better over the years. You’ll love it! The power is amazing. X

  4. Hi sharn…my dream is someone like you…strapon and sex toys is frobbiden in my country.i wish meet you soon…

    • Hi Ali,

      Thanks for your comment. Sorry to hear that you can’t have things like that in your country, that would totally upset me if I couldn’t access all my various toys freely.

      Welcome, by the way.

  5. For religius beliefes in my country it is hard to find a female like you or speak about strapon,femdom or bdsm,even…

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