Sissy Husband Pegging Party Pt. 04

Finally, Saturday had arrived - the day of my first sissy pegging show, where my Mistress wife would peg my sissy ass while her girlfriend (and our neighbour) Diana watched.

My Mistress explained how she had planned for the evening to go.

Throughout the evening, I would not be called by my name, only by Sissy.

She and Diana would meet for a drink before she brought her to our house. I was to strip down to my red lace thong, fit my usual condom and rubber band onto my sissy clit and wait for them to arrive. When they arrived, they would go into our lounge for a glass of wine. I was to wait 10 minutes then come down stairs, greet Diana as Mistress Diana and stand in my thong facing her and answer any questions while my wife went to strip and get into her strapon harness.

As the evening arrived, I waited in trepidation and excitement, my sissy clit already leaking precum.

My Mistress wife phoned me to let me know they were on the way and would be about 10 minutes.

I waited nervously upstairs in my spare bedroom. This was a big deal. Although I was well accustomed to my Mistress's pegging I had never had sex, nevermind pegging, in front of anyone else - especially not a friend and neighbour.

Finally, I heard our front door open and the two girls chatting and laughing before their voices faded as the went into our lounge. I watched the clock as the seconds and minutes slowly counted down. At 10 minutes, I took a deep breath and slowly walked downstairs.

I opened the door and walked in to stand in front of Diana.

Diana smiled at me and said "Hello... erm, Sissy. Long time, no see - wait a minute, never seen like this!" and blushed and giggled like a teenager.

I replied "Hello Mistress Diana. It is really great to see you again, especially like this!" I also blushed, like a gurl.

Diana's mouth dropped open as she took in my nakedness and my red lace thong.

My wife then added "Don't be shy Sissy. Give us a twirl and let Diana see the goods!"

As instructed I slowly turned around, allowing Mistress Diana to ogle my body from all angles.

My Mistress then announced "Right. I'm going upstairs now to get ready. Mistress Diana, feel free to ask Sissy anything you like but, please, no touching - well, not yet!"

After my Mistress left, Diana looked me up and down, with a knowing grin. She even licked her lips as she stared at my lace thong. She then asked "Sissy, is that a condom on your sissy clit? Why are you wearing one if you are going to be pegged?"

I answered "Mistress Diana, when my Mistress started pegging my sissy pussy, I got so excited that I left precum and cum pooled everywhere. Although I readily cleaned that up with my sissy tongue, Mistress decided it would be easier for me to wear a condom, secured with a rubber band, to collect my emissions. So far, that has worked very well. After I have finished leaking, Mistress removes the condom and pours the contents down my sissy throat."

Diana looked shocked at this revelation and asked "So you REALLY swallow your own cum? How deliciously kinky!"

I replied "Yes Mistress Diana, I love to swallow my own cum."

She then smiled at me "Well Sissy, all these years I've known you two I had no inkling that you two, and especially you, were so kinky. It is just so wild!"

My wife then opened the door and came in. She was naked except for her strapon harness and its snapon dildo.

Again Mistress Diana's jaw dropped and her eyes tracked over Mistress's body, lingering on her harness and the always erect dildo. She said "Wow, Mistress. It is bigger than I imagined. It looks quite realistic with the colour and prominent veins. No way could I take it in my pussy! How does Sissy manage to take it in her sissy pussy?"

Mistress simply replied "She has had a LOT of practice."

She then turned to me and said "Right sissy. Time for you to get on your hands and knees on the floor in front of and facing Mistress Diana."

As I assumed my position, Mistress turned to Mistress Diana and said "Mistress Diana, as you want to see how to peg someone, I won't just ram Sissy's pussy. I'll demonstrate how to start with a virgin sissy pussy and how to build up your pace."

She then positioned behind me and picked up her bottle of lube and explained "This is lubrication. Unlike our pussies which lubricate themselves, sissy pussy needs frequent lubrication to reduce risk of tearing. I pour some over my shaft and then insert some more into her sissy pussy, usually with my finger. You can get applicators, but I prefer to use a finger, or two. Sissy also likes that initial stimulation from my fingers coating the inside of her pussy. With a virgin sissy, you can spend as long as you or she want. Its all part of the fun!"

Mistress then lubed my sissy pussy as she had described. I moaned from this initial stimulation.

I looked into Mistress Diana's eyes and licked my lips. Mistress Diana sighed and said "Oh fuck. This is so hot!"

Mistress then explained "Once her pussy is lubed up, you can start penetration. Start by just easing the tip of the dildo head in, nice and slowly. With increasing pressure, the head will pop through and you can slowly increase the depth. I like to go all the way in, then pause for a minute or two to allow her pussy to relax. "

Mistress then demonstrated exactly as she had described. Although my well worn pussy no longer resists initial penetration, I acted as if I was still a sissy virgin, moaned and then flinched at the initial shaft head breaking through. Mistress Diana saw my reaction and said "Fuck!"

Mistress then slowly pushed in until she was fully in.

After a pause, Mistress then slowly pulled out until only the head remained inside then slowly pushed back in to full depth again, then continued back and forth, explaining "Mistress Diana, as you can see, you can now gradually build up a slow penetration and pull back sequence. Take as long as you like. Sissy will enyoy it all."

Mistress then gradually built up the pace, until eventually she was ramming her shaft in and out of my sissy pussy. She grabbed my hips and pulled me onto her. She then reached around to play with my nipples, whilst pounding into me, explaining "Sissy really enjoys me playing with her nipples when she is close to cumming."

By now I was breathing heavily and moaning with each thrust and then cried "Mistress, can I cum, pleeeease?"

Mistress replied "Not just yet, baby!" and continued to plough harder and faster into my pussy.

I started to scream " Oh fuck, Mistress. I really need to cum - PLEEEEESE! "

Mistress then finally said "Now you can cum!" and I immediately screamed and exploded into my condom, pulsing over and over. I thought it would never stop pouring from my clit!

Mistress then cried out as she also orgasmed and collapsed onto my back flattening me on the floor.

I looked up to see Mistress Diana with one hand an her left breast squeezing hard and her right hand thrust deep between her legs, rubbing furiously and calling out "FUUUCK! I'M CUUUMMMINGGGG!" and started to spasm with an intense orgasm.

This made my sissy clit start to pulse cum again in a second orgasm.

After several minutes of us all lying collapsed, Mistress slowly climbed off me and said, "Well Mistress Diana, that is how you fuck a sissy pussy!"

Diana laughed out loud.

Mistress then said " Mistress Diana, as a special treat you can feed Sissy her cum."

Mistress Diana replied "Ooooh Mistress, yes please!"

I knelt in front of Mistress Diana and she reached down, peeled the condom off my limp clit, raised it to my open mouth and tipped the copious cum into my mouth.

I swallowed the cum, licked my lips and said "Thank you Mistress Diana, for feeding me my sissy cum. It was delicious!"

See Sissy Husband Pegging Party - Pt. 05 for the next instalment.