Does Your Boyfriend Bend Over & Spread?

Lawrence Carvell Tests the Joy of Strapon Sex

Slip into someone warm

A Quick History of ‘Pegging’

In 1988 sexologist Carol Queen tentatively released her first (Bend Over Boyfriend)video of her and her lover demonstrating their preferred sexual pastime.  It involved Carol strapping on a dildo and lovingly penetrating her male partner in his arse.  For many, this was quite a revelation.

Strapon dildos had been used for lesbian lovemaking but this was different, this was a fetish that challenged many ideas about the boundaries of sexual intimacy.  Most of all it was a direct challenge to the idea of sexual roles in a relationship.

Anal penetration was commonplace amongst gay men of course, but the notion that a straight guy would ‘bend over’ for his girlfriend to penetrate him was rather new.

So, what is it that gay men had discovered that was so exciting that it has made its way into almost 3 out of 10 bedrooms in the UK and the USA amongst hetero couples?

It was, of course, that clever little prostate gland, a walnut-sized gland located between the male bladder and the penis, the prostate sits just in front of the rectum.  The prostate is very amenable to squeezing and stroking and many guys enjoy having their prostate ‘milked’.

Because the gland is involved in the guy’s production of semen and in the actual sensation of cumming, the prostate has a lot of sexy nerve endings

Pegging with a strapon can, with expert skill give a massive orgasm or ‘assgasm’ to a straight guy.   The clue here is in the ‘expert skill’ because it is an art that needs to be learnt and practised to get the best result.

strapon sex
Strapons come in a variety of stylish colours

My Pegging History

The first time I was ‘pegged’ was as part of a fun sexual relationship with an enthusiastic lover who enjoyed playing with toys.  This led her, naturally, to strapon play.   But, simply enjoying something does not automatically make you ‘expert’ at it.

We actually followed along with ‘Pornhub’ videos to try to get the technique working correctly.  We had a laptop next to the bed and copied the movements of the couples performing on the screen.  I know that a lot of people use YouTube to follow tutorials on fixing a dishwasher so learning to peg was merely an extension of that.

I think there is space on YouTube for a video ‘5 great hacks for anal penetration with a strapon.

As it was, I ended up feeling that there was more to pegging than we had achieved in our strapon play and I felt very slightly disappointed about the experience.

So this is why, this Summer, I found myself trembling with anticipation in a South London dungeon waiting to have my butt cheeks spread by Mistress Wildfire.

I chose Mistress Wildfire for this project because I felt she had the right attitude to pegging.  On her website, she talked about ‘pleasure’ rather than ‘submission and humiliation’. 

She described ‘pegging’ as something that, if done correctly, could be pain-free and totally satisfying.  This appealed to me because I wanted to learn how an adventurous hetero couple could introduce the technique into their bedroom for fun and variety. The final deal clincher was that she says she enjoys ‘pegging’. If you enjoy something you will take pride in doing it really well.

We chatted a lot about the ‘role reversal’ in pegging.  This is what appeals the most to me as a hetero man who has always taken the responsibility for a sexual ‘performance’ as part of his God-given role in sex.  A guy can never totally relax when he is orchestrating both the seduction and the penetration.

How nice it would be, then, to pass the ‘heavy lifting’ to the woman.  How nice to submit to the satisfying weight of a woman who is penetrating you.  Especially if that woman knows how to connect perfectly with your prostate.

mistress wildfire pegging expert
Mistress Wildfire – Pegging Expert.

Physically, Mistress Wildfire is everything one could wish for in a strapon lover – blonde, curvy, lithe and beautiful with a mysterious European accent.

Her dungeon is well equipped, with all the tricks of her trade and provides a compelling backdrop for the main event.  A willing slave could pass many happy hours here with the latest bondage gear. There is even an elegantly designed headrest to receive a golden shower. 

Ms Wildfire likes to relax her clients and is an experienced hypnotherapist who can calm the fears of a newbie slave to accept higher levels of pain and so gain more from a session.

Certainly, her voice relaxed my arse and, with liberal quantities of lube, she slipped her cock inside me with grace and skill.

Much of the secret to anal pleasure is in the lube. Whether you are in your own love nest or a professionally equipped dungeon.  Lube is not something to compromise on, use it often!

My own session had 2 main parts and an interlude.  She started by penetrating me from the rear.  I lay on a leather bench with my arse in the air and she gently penetrated me with a small strapon.  This got me used to the feel of her body and let me feel very well connected to her.

We then had a break where I lay on the floor and she sat on my face, a total pleasure for me, she is a beautiful mistress with soft skin and a lovely sexual perfume.

Finally, we came to the main act, this was the moment of truth, would I get the famed ‘assgasm’? would I experience the joy of penetration?

Set in the middle of the dungeon was a leather sex swing set hip-high with straps and manacles.  I climbed in and my legs were spread and my ankles secured.  Approaching me from the front this exquisite mistress parted my butt cheeks and ever so gently inserted the tip of her cock. It was larger than the first dildo, she said my arse could handle it, I totally submitted and felt it enter me.

 The sensation of role reversal was extraordinary, I was no longer the active lover, I had no responsibility for my erection or my control.  Mistress Wildfire had taken all the responsibility for this sexual ride.

As a lover, I am noisy and enthusiastic, and I threw myself into the spirit of the session pulling the cock further into me and telling her to ‘fuck me harder’ as many women had called out to me in the past. It seemed to come quite naturally 🙂

I wondered if this is a natural reaction to penetration, the things I said as she butt-fucked me sounded just like the things women say to men when they are penetrated.

The more she fucked me the more submissive I felt.   She then teased my cock with a vibrator to ‘edge me’ closer to assgasm.  She told me I could only cum with her permission and so we hovered delightfully around the point of no return for what seemed like an eternity.

Finally, I came and it was overwhelming. Everything contracted and I shot out a copious amount of cum as spasm followed spasm.

So is the ‘assgasm’ real?  Yes, it is.  It is a different feeling from a regular male orgasm whether from penetrating a woman or receiving a skilled blow job.  It was in a sense ‘transformative’ as if I had suddenly seen a different side to sex.

Talking the whole session over with a male friend he asked an obvious question. Did I feel less of a man for being fucked in the arse? I don’t think I did at all. I have a strong male sexual identity that can stretch itself to experiment in a traditional passive role. In fact, when I penetrated my regular female partner a few days later I felt I understood better her participation in our ‘traditional’ sex.

If having a fabled ‘assgasm’ is on your to-do list then I can highly recommend getting your cherry ‘popped’ by Mistress Wildfire in London or someone else you find convenient to where you are based.   

Once you have had it done properly you can better explain to your regular partner what you want her to do and you can then explore what works best for you.

Lawrence Carvell