Bend Over Boyfriend – Female On Male Strap-On Dildo Sex

Bend Over Boyfriend or Pegging – The sexual act of female on male anal penetration with a strap-on dildo.

Having a strap-on dildo slipped up your bottom can be an intensely pleasurable experience when it’s done well. But, like other forms of anal sex, it could be an unpleasant and painful experience if done without preparation. As the strap-on dildo receiving male partner in a straight relationship, ‘unpleasant and painful’ is not high on my sexual wish list, so preparation and doing it well seems the ideal way to go.

When I decided that I would quite like to try pegging I was concerned that asking to be bent over and taken up the bum with a strap-on dildo might have implications about my sexual orientation. I’m pretty sure I’m straight but I didn’t want to put any doubts in my girlfriend Sophie’s mind, as I suspected ‘possibly gay’ wasn’t something she was looking for in a long term partner. Internet research shows this is a pretty common fear.

The question Is my boyfriend gay – he wants me to do him up the bottom with a strap-on dildo? turns up time and again on advice forums. My answer to this question is as follows:

If a man chooses a woman as his sexual partner, he is clearly not gay. It is the sex of the partner you choose that indicates your sexual orientation, not the sexual activities you choose to perform.

Looking at it another way, lesbians may go down on each other but that doesn’t mean every woman who wants her boyfriend to go down on her is a secret lesbian.

With my ‘maybe gay’ concerns eased, I broached the subject with Sophie while we watched a porn movie that I had cunningly selected for it’s strap-on content. The fact that she bore a passing resemblance to the dildo wielding dominatrix in the movie gave me the opportunity to suggest tentatively that I might quite like to try that. When she had stopped giggling Sophie conceded that she found the idea of bending me over pretty exciting even if slightly hilarious. Result!

We needed practical information on getting started but ‘Being fucked up the bum with a strap-on dildo’ was something I was uneasy about discussing with my friends at the local pub, or enquiring about at the library. Likewise, Sophie wasn’t keen to ask her mum. And, according to her girl friends, none of them has ever indulged in any form of anal sex. Never. Ever. Honest.

But the internet is ever-friendly to kinks and fetishes of all kinds, so armed with information from Wiki and impatient to get started, Sophie went shopping for pegging toys at Lovehoney selecting the Sportsheets Blush Harness and Dildo Strap On Set which is not too scary for beginners and we would both highly recommend.

Pegging In Practice – Getting Down To It

In the time since we started pegging we’ve tried lots of different toys, lubes and other stuff. Below is a list of those we like and some tips for beginners:

  • Choose suitable size dildos to begin with

    We started with the Sportsheets Blush Harness and Dildo Strap On Set which was ideal as the dildo wasn’t too big and not too cocklike. Bigger dildos can be added to your collection, as the harness can accommodate various sizes by using different retaining rings.
  • Consider a Strapless strap-on dildo

    These offer an exciting alternative to harnesseses offering sensation for both partners and no time lost adjusting straps. Instant action!
    However they may be a difficult for the female to keep in, particularly if she is very wet or if it’s one of the heavier vibrating dildos.
  • Experiment with anal toys

    Try this solo or as a couple. There are plenty of anal sex toys of all shapes and sizes, including slim anal dildos and a whole world of butt plugs of various sizes to help ease the passage to larger toys.
  • Use lots of anal sex lubricant

    Anal lubricants are thicker and stay on the strap-on dildo better than ordinary sex lubricants. We like Sliquid which is thick and slippery and is more discreetly presented than the graphically named, but good Lubrifist
  • Desensitising lubricants

    The subject of desensitising lubricants is much debated. Anal sex should not be painful, if it is then you have probably not partaken of enough foreplay. However, we both find that there may be a a slight initial discomfort in any anal penetration, so a little desensitising lube can be useful.
  • Take it slowly
    As for any anal sex the key is to take your time over it, particularly in the early days. Start with anal foreplay involving fingers, small dildos or butt plugs with plenty of lube before moving onto the main event and then, once pegging proper, allow the receiving partner to set the pace at least until you are up to speed.

Sex should be fun. It’s ok to laugh sometimes if you feel faintly ridiculous wearing a strap on dildo, or are bent over waiting to be pegged. Check out our Pegging Blog and then Bend Over Baby! and enjoy yourselves.

Chris & Sophie