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What is Pegging? (A Guest Post by my Favo(u)rite Lover)

What is pegging? Thursday Girl and I attempt to answer this after we have spent a week of exchanging emojis and planning how to make our next fuckfest extra memorable and special whilst pushing the boundaries of our CIS hetro female / male identities.

Usual stuff. “Try anything once”.

“Can I peg you?” asks Thursday Girl late that Wednesday night before the deed using a social app, mind you, not just saving up the sensitive question to ask to my face on a Thursday.

“Yeah, right babe”, reply I. “Try anything once”. followed by thoughts on how to attach various vegetables to her genitals. 

“I have a budget” she consoles me. “We can spend money on this”.

Thursday comes and we find ourselves at the best sex toy shop we know, (again). Honestly they should give us discount vouchers. Both of us have that glint of new experiences to come which shall enhance our sexual lives, make us laugh and probably result in laundry.

The young lady behind the counter is as bored and professional as ever. Let us call her “YLBC”.

Let us call me, Thursday Boy “TB”. Yup you got it, Thursday Girl is “TG”. & off we go…,

YLBC : If you are here for the swinger party on Friday, you are too late. It is sold out.

TB : Oh no thank you, we did that last week and she left a terrible mess on the towels. 

TG : We are here today for strap on dildos.

YLBC : So which one of you is going to peg the other?

Young lady behind the counter sweeps her limpid eyes over us with the jaded experience of a true retailer with repeat custom. She has heard asked “What is pegging?” before. She has answered “What is pegging?” before.

I let her question sink in. Oh! Perhaps I could have a strap on dildo and have two cocks. The potential stretches out into a multiverse of opportunities. Puff, my fantasies disappear before they even get a face and Thursday Girl with voice slightly raised declaims :

TG :  I am going to peg him.

Young lady behind the counter glances at me and asks the obvious.

YLBC : So have you been pegged before?

TB : No, this is my first “try anything once” being pegged experience.

YLBC : So I shall show you the starter kits.

Few minutes later, (no product placement) we leave the store with a box which contains a harness kind of thing in fake leather which is supposed to fit over Thursday Girl hips and waist attached to an inverted triangle with two pockets one facing inwards to her body which can hold a small vibrating cylinder (lithium short life batteries included) and one other pouch facing outwards away from her body in which she can insert either of two pieces of plastic.

We get back to the bedroom.

Thursday Girl struggles to get the harness thing on. I feel we are losing the buzz and help her get back in the mood. 

TB : There my love I think that is just about right.” Even though it is pinching the bottom of her buttocks and I have never seen her lower stomach look the same. One other thing…

TB : I think it it may be the wrong colour.

Thursday Girl looks down at her new plastic dick, which (no product placement) does not really look like a dick but just a piece of eight inch plastic and notices that it is definitely not the same colour as her skin. She looks quite crestfallen.

TG : I don’t know what is happening. It looks so small. I expected more girth.

TB : Don’t feel emasculated darling, it is a question of your viewing angle. You are really great. Except of course the angle thing. Yup. The angle thing is a bit weird.

Thursday Girl now has a bit of plastic attached to a harness around her genitals which is perpendicular to her body. 

TB : I think you should have your tendons checked. It is not very healthy to have a hard on which is perpendicular to your body. Don’t you like how I go up and slightly to that side you always moan about. I am having more fun so far than her and suddenly feel guilty for dashing her self-esteem.

TG : Maybe the bigger one will be more erect. 

The starter pack contains two pieces of plastic, neither of which look like dicks so as not to freak out CIS males. One is thinner than a doctor finger checking your prostate and the other is possibly, just possibly as girthy (lovely word) as my own veined splendid cock.

TB : yup try the other one.

A few minutes of adjusting straps and fumbling and then monster which in no way looks naturally skin coloured is in the pouch.

TB : do you want to do this in the raw or are you going to put the little vibrator thing in the inwards pouch?

TG : oh yes.

She turns on the little vibrator thing and with all the alacrity of someone who has quickly stuffed drugs into her vagina during a sweep search and manages to get the cylinder into the harness. I think it is about stomach muscles and breathing.

TG : It is not in the right place. It is just moving on my stomach not my clit.

TB : I have been trying to tell you perpendicular dickhead that nothing is in the right place.

We really enjoy these moments and fall around the bed laughing at our stupid one off expense until she falls over a pillow and slighty bends the 8.5 inch colour of dead white person piece of inflexible plastic.

TG : Do you think I broke it?

TB : Did you ever use it?

Time goes past. And the moment has arrived. 

TB : So how do you want me? All four doggy? Lazy doggy? Over the kitchen counter on tippy toes? Remember you are shorter than me.

TG : Can we do lazy doggy first?

TB : Try anything once.

TG : Do you want some muscle relaxant?

TB : I never do drugs……. but we have olive oil in the kitchen on the counter.

TG : Oh babe! Sweetie, I have lubricant left over from last Friday swinger party gig.

The first little pop when her piece of plastic attached to a vibrating cylinder which is nowhere near her clit is really more psychologically a part of giving her something than pleasure for me. 

“OH!” I say. Then try to go through a catalogue of noises and grunts until she tells me I am distracting her. Then I feel this bit of plastic rummage around behind my prostate and her things push against me. I hope I fuck her better than she fucks me.

TG : This is really weird. All the movements are different. I am kind of tired.

She has given up giving after three minutes of my taking. I am not going to let her feel bad about it. I am not that kind of guy to enjoy letting her know I am disappointed. 

TB : Are you finished yet?

TG : No. I am not. I just thinking I could take the little vibrator thing out

TB : And put it in my ass? it has no string it will travel up my rectal passage and give me revolving naval syndrome. That is a real thing. Look it up on Wikipedia.

TG : You are not taking this seriously

TB : I did not know we were supposed to. If you wash yourself off in detergent I may give you a blowjob and get you at a better angle than perpendicular.

Thursday Girl is looking really crestfallen and emasculated and I am really feeling like I have been a shit head.

TB: Sorry babe. I am sorry. It has never happened to me before. It has never happend to you before either.

We both have the dignity left to laugh ourselves into a coughing fit. I should have squeezed her out during that one if she had managed to stay in.

I decide to do one of my special moves. After passionate kisses I maneuver her onto her back where her perpendicular colour of death plastic dick no longer looks lame in need of surgery but is ready to do something useful for the amount of money we spent on it.

I look her straight in the eye as she lies below me and decide I am going to cowgirl her, well CIS boy cowboy her in one straight thrust. 

TB : Would you like me to put on your bra?

TG : We did that two weeks ago.

TB : Do you think I am pretty?

TG: Yeah baby fuck me.

TB: You are not wearing your socks.

TG: You are the one. Fuck me.

TB: You want me?

TG : Be my bitch.

TB : That is inappropriate language

TG: I am role playing

TB: Do you have those muscle relaxants?

TG: I never had any. I was lying to you.

TB: Are you ready ?

And with one deft movement I straddle my lover, putting a piece of inflexible plastic through my rectal passage and all erogenous zones.

What is pegging? Do not let anyone pretend there is no erogenous tissues connected to “ass stuff”.

And about two seconds later I damage a section of my colon.

TB:  Ahhhhhh

TG : Yeah baby. I feel so lazy give it to me.

TB : No, I have seriously hurt myself.

TG : Oh fuck you ok?

I spent the next few days using a walking stick and I must admit the emoji selection between Thursday Girl and I changed a little bit. The following week we met the young but professional lady at the sex shop and asked about feather dusters.

Try anything once.

Be careful the first time.


Other Butt Stuff:

Anal Sex

Strap-On

Pegging the Palace Guard


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