She Pegged My Ass!

For those of you who don’t understand what pegging is, its a neologism made by all-around-wonderful fellow Dan Savage, that fundamentally includes a broom handle, somel tape, and a man and lady who need to zest things up in the bedroom, however couldn’t pay for a strap-on. This is my story of how she pegged my ass for the very first time.

I’m really a gentle fellow who is aroused easily at a basic level, and that had reflected what I did and tried in the bedroom.  I used to think to myself,

“the more gentle I am with my partner and the more I accommodate them, the more they will want me!”

If you’ve never pegged before its an experience that is both startling and extraordinarily thrilling. The first occasion I was pegged it was with a young lady named Doris who had acquainted me with an entire host of new ways to approach sex.    Our first date was a thing of wonder when I discovered that she was into the BDSM lifestyle and was a domme that liked to take things to the extreme.  When I woke up the following morning from said date, I really needed to let my flatmate know that I was okay and consented to the previous evening as welts and bruises were showing all over my body.  That previous night I had been stomped, kicked, smacked, spat on and pretty much everything else you can imagine whilst being humiliated.

The funny thing was I had liked it. In fact I loved it and I could not wait till the next date when my new mistress would come again and help train me some more into the ways of the S&M lifestyle.  No scented candles or flower for her she had told me.  She was going to be harsh, cruel and insolent towards me.. and if I was to see her again I was going to allow that and more.

Over the next week she taught me so many things and I began experiences new sexual practices – sometimes being embarrassed and frightened but always being invigorated and satisfied at the end of our sessions.  Sometimes, but not often we reversed role playing and she allowed me place a gag on her.  She also allowed me to throat fuck her until she gagged.  These were all wild and wonderful experiences I had never before had,

At times she made me a human cushion by binding my hands and feet and laying me on the couch and then sitting on me whilst she watched tv or read a book.  I was not allowed to talk and interact with her until I was released from those restraints.  It was a liberating time of my life.

After two of three months into our relationship we began discussing anal sex.  I had given it once in my life to another woman there was no way you could say I was an expert in that field regardless that I had attended FemSex classes at Sydney University.  She spoke to me about dominating me and pegging me with a strap on and the idea actually had a fair bit of appeal from my point of view.  The popularity of prostate massaging in men had long sent away the stigma that men that enjoyed anal sex were all gay.  We decided that it was time to do some adult shopping at a sex toy shop to get the gear needed.


Pegged Man
Male Pegging And Chastity

When we strolled into the Oh Zone store in Kogarah, we met a lovely lady who was so helpful.  My love of indian food made me query about the best enema kits whilst Doris inspected the strap-on and lubricant sections.  After about 20 minutes in the store we both left with our package of sex toy goodies and headed for hom.

There are things that you ought to think about before any sort of anal play. Let’s face it things can get wild and you would not want to spoil it by having a nasty surprise occur mid action.  So once we walked in the entrance-way I headed for the bathroom and put to used my enema, using it a couple of times over 15 minutes to thoroughly flush myself out.  Believe me it is time well-spent and gives you confidence and relaxes you before some anal pounding.

When I left the bathroom our eyes met and we simultaneously moved towards the bedroom.  To be fair I was a little apprehensive but more excited by this new sexual experimentation into pegging.  I got undressed and lay on the bed whilst she too undressed but remained standing and began to put on her strap on that held by a panty harness.  It was a sight to be seen, especially when you know that the 8 inch dildo is soon going to be inside your rectum.

She approached me on the bed whilst with her hands she began with one to stroke the dildo whilst with the other pour lubricant onto and all over it.  The dildo was realistic so it wobbled and swayed unwieldy with each stride.  Once she reached me she poured lube on my cock and let it run down between my legs.  The lube was fucking cold – but in a nice way.  She stroked my cock that was already hard and getting harder and slowly her hand traveled down my cock and then between my ass cheeks as she gently played around my rosebud.  This was such a turn on and I could feel my dick spasming each time her finger circled my butt hole.

She then directed me to put my face down in the pillow and my ass up in the air doggie style and as I complied she added more lube around my ass.  Slowly she put the head of the dildo on my virgin hole and started to push with slow but constant pressure and before long my sphincter muscle ‘popped’ and allowed the tip of it in.  I inhaled and exhaled as she slowly slipped the entire length of the dildo into my now welcoming ass.  It felt like I need to go for a crap during this stage but I  know that wasn’t possible as there was nothing left inside me.  It was not till later that I read it is a common ‘phantom’ feeling that is your bodies reaction to having an object inserted near the colon.

She gently began to stroked that dildo in and out of me.  Heavenly f*ck. What is occurring? As she starts pushing everything starts to come alive in my body and brain: amazement, elation bewilderment, enchantment. Everything!  How is it that MY legs are the ones open and my ass the one being now pounded? How is it that I’m the one being fucked, and I’m seeing a couple of tits swinging at me from above? It was a complete bizarre sexual sensation .After I have cum, she starts to pull out.

“Gradually,” I say.

“All clean,” shersays happily.

VICTORY, I think.

Doris and I had a wicked relationship for about 6 months.  Thereafter my relationships with women were different and I always let them know that I enjoyed being pegged.  Most women are used to using their hips to accept the thrusts of me and do not put the power required to peg well.  Doris knew exactly what she was doing – I miss her still.

“Hey Eric have you made me dinner yet?” I hear from the lounge-room.

I better get this dinner sorted.  Forgot to tell you – I am a cuckolded male now – but that is another story!



Leave a Reply

Your email address will not be published. Required fields are marked *