Mature Crossdressing Stories

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Annual Check Up

by Divawithguns on Jan 23, 2019
Mature

Was raining, windy and cold out. Bob was not in a good mood... He was not looking forward to this annual checkup. Thoughts rumbling in his head of how he's got another new Dr. Why is he getting the doctors that are close to retirement or move away? Walking into the clinic he shook his head as he was so wet from being outside. Running his fingers through his...

It Could be Worse

by beg4feather on Sep 14, 2020
Fetish

Kelly Lewis closed the door to her classroom on Friday evening, and walked down the hallway of Littleton Sr High. The petite blonde had a been an English teacher here for the past 10 years, ever since graduating from the university. She had been grading papers since the end of the school day and the hallways were now long deserted. She headed towards the old...

April's Volunteer Assignment Ch. 03

by TheScarletsin on Jul 6, 2020
Mature

It was another hot Texas day as April hopped in her car and headed to Mr. Milton's condo for her weekly visit. She was wet already just thinking about spending time with him. Today she had on a cute little sundress and lace panties and left her long blonde hair down. Just a little touch of lip gloss was all she did for makeup today, anticipating getting mess...

Mating Season

by Bob Waters on Jul 15, 2020
NonHuman

Bright light stabbed deep into my head forcing a groan from my lips as I slowly regained consciousness. I squinted against the light, trying to see past it, but it hurt. I screwed my eyes closed and tried to roll away from it. That was when I noticed I was restrained. Awareness exploded upon me like a bomb. I suddenly realized I was naked, fastened to some...

Slutty Sue The Good Neighbor

by raidernation25 on Dec 23, 2019
Mature

I grew up in a small town where everyone knew everyone else. My neighbors were a couple in their 60s the Reynolds. Mr & Mrs Reynolds were very nice people and my mother spent a lot of time at their house when I was growing up. Mrs Reynolds was very sick from about the time that I was 13 or 14 until she died during me freshman year of college. My mother spe...

Sourpuss Pt. 02

by DDDDave on Apr 14, 2020
Mature

"Big Tits, Big Dicks and Fantasy Fucking" ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) ( o ) "Andy, I need you to take care of the first floor windows when you come over tomorrow. Do you have the equipment or should I go shopping?" It was Ms. Melonosky, the neighborhood sourpuss on the phone. Recently I had started to do some l...

2nd Best Ch. 01

by Tara Cox on Mar 31, 2020
Mature

Heather Sampson tilted her head back, squinting into the bright mid-morning sunlight. This was a bad idea. What had Geoffrey been thinking? She brushed the moisture from her eyes with the back of her hand. She would never know. Just as she would never again engage his brilliant mind in debate about some esoteric topic. He was gone. A year almost, and the p...

My Cup Runneth Over Ch. 02

by Jollyjumper212 on May 13, 2020
Romance

This is the second in a series of episodes that involve mature women who share one thing in common. Let's just say they are Rubanesque in stature. One can ask with validity why a man would write such a saga. I don't know quite frankly. The thought just came to me once and I followed it taking several months off and on to complete it to my satisfaction. Let m...

Sarah's Catfight Adventures Pt. 06

by AimEnigmaClick on May 11, 2020
Fetish

Disclaimer: All girls in this story are 18-year-old seniors in high school. ----------------------------- Sarah was at home studying for an upcoming exam. She was on her computer, looking at a study guide when she received a message. "BITCH!" Of course, it was from Britney. Sarah thought about ignoring the message, but she couldn't resist. This was the...

Do Collaborations Work?

by ilovebananas on Mar 18, 2020
Anal

Being part of a business partnership can be a trying experience. I had spent many years in my industry with many a companion by my side, only for things to end up tense or tedious. Perhaps no one could ever work with me. Maybe I am just too troublesome or stubborn. Then there was Mark. He was slightly older than me, so I figured this meant he would be a bi...