The Confidence of Flirting

tiffydoll | 07.08.2017 | Reports - Getting Real

Studying “Flirting”, tiffy practiced in front of a mirror early yesterday morning, giggling at her expressions and less-than-skilled attempts at mastering the flirting techniques described in this assignment. After about an hour of study, this sissy removed this sissy’s nightie to change into boi clothes to get ready for the Air conditioner repairman, who was due soon to finish installation on a new Carrier Heat pump/air-conditioner. Tiffy quickly put on clean pink and white lace panties, a blue T-shirt, Calvin Klein jeans and a pair of Sperry’s.

The air conditioner died after 20 years of faithful service, and two handsome young men brought a new unit for installation yesterday but didn’t finish the job. Jason, the cuter of the two, was to return today to finish the wiring and show this sissy how to work the thermostat. He arrived on time and went to work immediately. Tiffy asked if he would like some water or coffee and he said coffee would be nice, so giving him a welcoming smile (was it flirtatious?), tiffy went to the kitchen to fix a fresh pot.

Ten minutes later tiffy returned with Jason’s hot mug of coffee and stood behind him watching his muscular arms and shoulders flex as he worked. He didn’t hear tiffy “sneak up” behind him so when he turned suddenly it startled both of us and this idiot dropped the mug of coffee. The mug broke into hundreds of pieces and luckily this sissy got most of the coffee splash. “Oh, my! I’m so sorry. I will get something to clean it up”, tiffy apologized and ran for a towel, broom and dust pan. Jason was sweet and tried to take the blame. This klutz smiled and told him it was no big thing and would get him another cup in a second, then kneeled and bent over to mop up the coffee and shards of stone ware.

“Holy shit! Are you wearing panties!?” tiffy heard from behind, and realized her Calvin Klein’s must have slipped down while her Victoria Secrets had not. What to do? Better think fast! Well, the best defense is a good offense, so tiffy turned and looked up at Jason over her right shoulder and smiled, “They certainly are. Do you like them?”

“Are you a fuckin’ faggot?” he exploded. Tiffy forced herself to smile, batted her eyes, looked left, looked right, giggled, looked into his eyes, and smiled again, and replied, “Why yes, I’m a fucking SISSY faggot”, blushing. Jason just stared at tiffy and looked like he had seen a ghost…or a sissy-faggot ghost. Tiffy smiled, “Look, just relax Jason. I’ll clean up this mess and get you another cup of coffee, okay?”

Tiffy cleaned and Jason silently went back to work, then as tiffy got off her knees, Jason turned and asked, “So you are gay, right?” Smiling, tiffy said, “Well, I’m a sissy and sissies feel like they are girls. Girls like guys, so it feels like it’s natural to like guys.”

“But you damn sure don’t look like a girl”, he retorted.

Tiffy gave Jason a pretty, quick smile and looked down and said, “Well, I feel like a girl. Want me to prove it?”

“What do you mean?” he asked.

Tiffy looked up into his eyes, smiled. Lightly touched his left shoulder and said, “This sissy will suck your cock if you like.

Jason was speechless again and while he was searching for a coherent thought to form, tiffy noticed a growing bulge in his jeans. Jason stammered, “I feel funny…YOU make me feel…funny…I feel like you are flirting with me…”

Tiffy, giggled, “This sissy thinks maybe she is, and judging by that monster in your jeans, you like the idea. Hard-ons don’t lie, do they?”

“Well, look, you act like a girl, Mr. …ah…ah…”– Tiffy interrupted with a smile, “Call me tiffy”.

“Well you act like a girl…ah…Mr. Tiffy, but you look like a guy, and it doesn’t seem right to mess with a guy”, Jason explained.

“So Jason, what you are saying is, if tiffy acts like a girl and looks like a girl then you’d want to have sex with this sissy”?

Jason replied, “I guess…I mean I don’t know…you are a guy and you look like a guy…I don’t know…”

“Okay, Jason, honey, you think about it and tiffy will get you a cup of coffee…is there anything else tiffy can get you?” tiffy smiled back over her left shoulder as she walked away, wishing she had heels for a sexier walk.

As tiffy was returning with coffee for Jason, he met tiffy at the door to the kitchen, “I’m sorry Mr. ah…Mr. Tiffy, but it seems that they gave me the wrong circuit breakers this morning. I’ll have to return to the shop to get new ones. Won’t take long. Should be back in an hour, or hour and a half max”, Jason apologized.

Doubly disappointed tiffy tried to remain cheerful, “Take your time, honey, I’ll expect you in about an hour and a half. Here, I’ll walk you to the door”. Then with a thoughtful smile tiffy said, “Tiffy will be waiting for you when you get back.”

All this would not have been possible without the House’s training on flirting and the confidence it gave this sissy; and tiffy doll would not have been waiting at the door, looking like a girl, when Jason returned.


  1. tiffy doll

    Yes, when he came back tiffy answered the door in this sissy’s blonde wig, carefully applied makeup, pink nails, perfume, Victoria Secret panties (shown above), tan thigh highs, pink five-inch sling back heels, self-adhesive breast forms, a pink and violet baby doll nightie, and pink satin robe (for a little modesty). It only took about two minutes for a tent pole to appear in his jeans. Jason had no problem treating tiffy like a girl now that tiffy looked and acted like a girl. This slut flirted and teased poor Jason until he finally got to cum. He said it was the best blow job that he has ever had. Jason asked if he could text my cell, and kissed me three hours later when he left. (Of course part of that time was working on the air conditioner. –giggles)

Something to share sweetie?