Jenny life goes down the rabbit hole

Jenny I in a lot of ways had given up on life. Being a single high school band teacher on the wrong side of 35, well the thought that she had made lots of wrong choices in her life had been creeping in.

Here she was directing freshman in her utilitarian pants suit, that she bought just a bit baggy for when her tummy would inebetally get bigger. But today was different her lack of panties and the bra she was wearing had changed her attitude.

The lack of panties wasn’t totally new but the bra was the first gift she had gotten from a man in a long time. The fact that he talked about how sexy she was, how he could help filll her many fantasies that she was convinced would stay that way till she died gave her the hope that the second gift waiting for her at home this Friday could change alot of things.

When she opened the first package she was a bit taken back. The bra was nice but nothing as kinky as she expected. Then the note drove it home “wear this Friday it costs more than an outfit of your frumpy clothes”.

She looked at the tag and then online. It did at over $500 the dark blue lace bra from agent provocateur made her cry. She did fnally try it on and despite being curvy her D cups looked amazing. She texted her thanks but the only response she git was “another box we’ll arrive tomorrow open it Friday after work. I need you dressed properly for our first date.” Her heart stopped. The emotions swirling around anger, fear, hope. When the box finally arrived Thursday all she could do was stare at it for hours.

When she got home she placed the box on her bed and slowly worked up the resolve to open it. Inside she found a pair of black 3” pumps, expensive black stockings, hunter green garterbelt, a hunter green bra, a black pletted skirt and a white thin sweater.

She ignored the letter and just touched the clothes they were all very high quality that made her hate her current life more. Just how soft the cotton sweater was to the point of a cloud.

The note said “I hope you enjoyed the blue bra today. I want my dates to dress well and feel amazing. I will be having drinks from 9 to 10 at the address below. Come dressed in only what I gave you. I understand if going from fantasy to real life is too much but if you do not show we will never talk again.

All of the emotions sprung up again. How dare he, I don’t want to lose him, I’ll look like a slut!

Resolve hit her shower dress and then decide. By the time she was dressed she was very turned on. The green from the lingerie radiated from her pale skin and red hair, the skirt was short but flowed nicely. The sweater was so soft but thin. Her bra was clearly seen along with her nipples. The bra cups had no padding and the lace rubbed just enough to keep them teased. Looking in the mirror she had to admit despite being curvy she liked how she looked.

Finally reaching the address she was shocked it standard strip club. Considering what she was wearing it was a big letdown. Going inside she went to pay the cover and show her ID but the girl behind the counter simply smiled and said, “ he is waiting for you up stairs”.

She walked past the women dancing and the men throwing money at them to the stairs at the back of the club. a rope blocked the was but a bouncer immediately came over and let her up. Why here what was happening she thought.

Getting to the top of the stairs a man was sitting with his back to her talking to the bartender. The girl on the stool next to him saw her and walked over. She was in her 20s nicer body but obviously not a dancer here. The clothes were too nice like Jenny’s.

“We are so glad you came!” She grabbed Jenny hand and pulled her near the man. “Sir she is here!”

He turned around and with out hesitation closed the distance between him and Jenny and cupped her face with his hands and kissed her. His hands moved so one held her head in place and the other went to the small of her back. She kissed back, he held her there controlling her the whole time with his hands be hind her.

The hand behind her head held her in place as his other hand quickly felt how hard her nipple was before forcfully going between her legs. One finger was suddenly probing her pussy. Just deep enough to feel how wet she was and to get a deep moan out oh her.

He pulled his finger out ran it around the rim of the 3 drinks on the bar then held it out for the bartender she sucked on it. “She tastes amazing sir”. Before she walked off. All Jenny could think was a woman half my age just tasted me. In that moment she knew her choice to go was the right one.

If this is liked I’ll write more!

Source: reddit.com/r/sexystories/comments/rjh31q/jenny_life_goes_down_the_rabbit_hole