Sissy is a Temp Pt. 05

Story Info
He helps a horny woman overcome her fear of men.
1k words
4.62
3.8k
1

Part 5 of the 10 part series

Updated 12/16/2023
Created 12/05/2023
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Dear Reader,

My short vignettes tell of weak pantywaists who are ruled by strong women. The delicate femboys wear pretty lingerie and revel in girlish pleasures. Horny doms ravish them and feminine happiness turns to erotic jubilation.

Sincerely,

Whippet_Darling

---

Earlier in this story my employment agent, Mistress Lindsey McCorkle, found a temporary job for me with a sex therapist named Doctor Anna Furbank. She was treating a female client, Clarice, who yearned for sex with men but feared their aggression. I was helping her to be more assertive in bed. After I licked her pussy to an earth-shattering climax Mistress Clarice begged me to screw her.

Mistress laid back on my bed spread her legs and shouted, "Fuck me, Sophie! Please fuck me!"

She obviously wanted me to mount her. However, I had never been on top of a woman before and I was frightened. Besides I was dressed for girl-on-top sex in a pink sissy maid outfit, dainty chiffon petticoats and white garter stockings. When I did climb on Mistress Clarice my weenie went limp.

"I'm sorry Mistress," I said despondently.

"Oh, you poor sissy," replied Mistress sympathetically. "What can I do to help?"

"Well, Mistress, spankings always turn me on."

"Very well, Sophie," she said. Then Mistress sat on the edge of the bed and I lay face down across her lap. She put on a hard leather spanking glove that Doctor Furbank had given her and commenced smacking my rear end. The spanking was too gentle to arouse me though.

"Harder please, Mistress. Pretend that I'm a man who's hurt you."

My suggestion must have set her off because the soft strokes turned to a violent thrashing. The wild pounding brought forth a delightful stinging pain in my fanny. As Mistress continued the punishment, tears came to my eyes and I began sobbing joyfully.

"Wow!" said Mistress elatedly. "This is really empowering!"

The hurt had become difficult to bear though and I begged, "That's enough Mistress! Please stop!"

"Not on your life, Sophie!" she replied. "Remember, you asked for it."

I loved her assertiveness and my dickie grew hard as she inflicted more suffering. The pain morphed into a glorious feeling of sweet surrender. Euphoric girly bliss followed and I climaxed jubilantly, spurting my sissy cream on the floor.

My orgasm had been wonderful but it occurred without permission from a woman. So, I apologized profusely to Mistress Clarice. She was cross, too, because intercourse would now be delayed.

---

I had been preparing dinner for Mistress Clarice before the romantic interlude in my boudoir. So, we went downstairs and I served her my chateaubriand and sauteed vegetables with Bearnaise sauce. She enjoyed the meal with Veuve Clicquot champagne that I had chilled beforehand.

After she finished eating, Mistress said, "Sissy Sophie, spanking you made me feel tremendously powerful and in charge. Now I want to do more. Do you have any suggestions?"

I had lots of erotically charged ideas but I described my favorite one to Mistress. Back in the boudoir I fetched a silicone strap-on from my drawer of sex toys. Then I showed her how to buckle it around her waist and thighs. Finally, I demonstrated the pulsing clitoris stimulator which delighted her.

"This thing is cool! she said as she set the vibrator on high.

Then she commanded, "Get in position, Sissy!"

I happily knelt on the bed and raised my skirt and petticoats to expose my bottom. Mistress got behind me and unsnapped the crotch opening of my shapewear.

She placed the tip of her phallus against my sissy hole and pushed. Women have ass fucked me so many times that I'm wide enough to handle almost any strap-on. Mistress penetrated me without any problem and the shaft felt marvelous inside me!

She reached around and fondled my breasts as she pounded my back side. I could sense that Mistress was getting excited because she began moaning and her breath became jagged. Then without warning she climaxed in frenzied ecstasy and sunk her fingernails into my my back.

I expected her to stop but the orgasm only seemed to fuel her passion and she continued fucking me. Mistress sternly reminded me not to cum and proceeded to have two more magnificent orgasms herself. Then she abruptly withdrew the strap-on from my behind and rolled me over on my back.

Mistress straddled my thighs, grabbed my throbbing cock and wrapped her thumb and forefinger around it. Then she said, "Doctor Furbank told me to squeeze your dick during intercourse so that you don't cum before I finish. Am I doing it right?"

"Yes, Mistress Clarice," I answered, "but you've got to clamp down more tightly."

She applied more pressure and then lowered her hungry pussy onto my throbbing cock. Mistress road me hard like a jockey near the finish line. Then she experienced two more exhilarating orgasms complete with ear-piercing screams.

"That was so much fun!" said Mistress as she dismounted me and lay on the bed.

Then she added, "I've never seen a penis squirt. So, jill off for me, Sissy."

When she released her grip on my weenie I began stroking it and I indulged in my favorite rape fantasy. I was strapped onto a bondage bench and two topless women in miniskirts were abusing me.

One woman was fucking me with a pink jelly dildo and the other had my face pressed to her pussy for cunnilingus. Sweet feelings of feminine helplessness permeated my being and I soon climaxed in a spasm of girlish joy. My sissy jizz sailed across the room and splattered on the wall.

"Awesome!" exclaimed Mistress.

Then, the satisfied woman lay next to me and whispered, "I love giving orders in bed, Sissy. Thank you for being such an obedient girl. Now, when can I see you again?"

---

That concludes Sissy Sophie's adventure with Mistress Clarice, but his employment agency has already found a new temp position.

Your comments, questions and discussions are welcome.

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4 Comments
Whippet_DarlingWhippet_Darling4 months agoAuthor

Dear Anonymous,

I appreciate your feedback and I'll be sure to put sissy spankings in future installments.

Sincerely,

Whippet_Darling

AnonymousAnonymous4 months ago

A lovely story once again! The spanking scene I found really enjoyable. You really are working at a quick pace, I must say.

By the way, sorry for not responding to your reply to my other comment; it is a bit difficult to keep track of these things.

With apologies I beg to remain,

Sincerely yours,

S.

Whippet_DarlingWhippet_Darling4 months agoAuthor

Dear woodseaves,

Thanks for your comment. Sissy Sophie wanted to continue working at Doctor Furbank's sex therapy practice. However, the Doctor's regular sissy assistant returned from vacation. So, Sissy Sophie had to look for other employment. In Part 6 he interviews for a job as a sissy waitress. I hope you'll like that one, too.

Sincererly,

Whippet_Darling

woodseaveswoodseaves4 months ago
Super Sissy Sophie story

Brilliant story, and nice the way the posted a little piece at the time. You should make this temp job permanent. With her wonderfully accommodating pussy, Sophie is an absolute delight, irresistible to a woman or a man

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