Mature Teacher Stories

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Ackerman Street

by Sputnik57 on Sep 12, 2017
BDSM

Mart Tranter was an odd-jobbing chancer who scraped a living through the few jobs he held down, he lived on his wits and charmed himself into situations; he liked short-term tenancies as he believed the change of outlook to be the best way in life was to move on, and his lowly budget would not entertain a mortgage in this area or any other. It was with relie...

My Sweet Young Asian Yoga Student Ch. 01

by call_me_or_dont_call_me on Nov 20, 2018
Erotic Couplings

We had met at the grocery store. "OMG it's my yoga teacher Mike" your sister squealed, "You need to meet him!" and she ran up to me and gave me a kiss on the cheek. I was tall, white, slim, grey hair at my temples and in my beard. I was wearing a dark suit and a big smile, my hand almost on your sister's ass while she pecked my cheek and hung her arms ar...

The Adventures of Sister Margaret Ch. 06

by Pgup on Sep 12, 2017
Sci-Fi & Fantasy

The days in Leverton were a lot like being on a continuous vacation – one day blended into the next so it was easy to lose complete track of time. So it was, on one morning as I sat down at the breakfast table, I was really surprised to hear the teachers talking about graduation and that it was imminent. That was my first indication that the year was half ov...

A Wonderful Summer Ch. 2

by GoddessInSC on Sep 16, 2017
Mature

A few weeks past by and I saw still seeing Joe. We hardly had time together, but when we did, it was great. Since Joe was known well around town we were never permitted to be able to just go out and date. We did, however, spend marvelous nights at his cabin. The Fourth of July was fast approaching, and I didn't expect to be able to spend it with Joe. Surpri...

3's: Teacher-Student Relationship

by Dhc000333 on Dec 11, 2018
Mature

Reunion It's been five years since I started teaching and every year it keeps getting harder. Administration always adding some new program or new way of teaching, that I cannot seem to get behind. My co-workers complain to me so much, their ramblings have become incessant chatter to my ears. The joy of being a hardworking Black male whom listens. The stud...

High School Futa Ch. 09

by ToSexorNotToSex on Mar 23, 2020
Transgender & Crossdressers

Author Note: All characters are above the age of 18. --- Before she could make a decision about the whole Pornhub deal, Emma had one thing to take care of. A wager she'd lost. It had been a few days since everything kind of converged, and Emma wasn't particularly busy. So, in between making light-hearted fun of some "ugly" pictures Lindsey took of herself...

An Unforgettable Teacher

by ilovebigandmature on Sep 17, 2017
Mature

I don't know why I'm this odd, but I don't seem to like the girls my age who are crazy about me, every time I masturbate I only think of mature women from about 35-55, those big boobs and beautiful meaty asses. There is only one thing important to me, she was sensual, so beautiful. She had the best attributes among residents in the school, Mrs. Sharifah. I l...

My Friend's Hot Mom who was also My Teacher

by shekar01 on Jan 15, 2018
Mature

My Friend's Hot Mom Who Was Also My Teacher Hi guys. This is Sachin from Pune. I have written in this story about how I fucked my friend's hot mom. I was 18 years old back then. I had a friend named Vaishnavi. She and i were very close friends. Her mom was a teacher in my school. Her name was Rohini. She used to take biology for my section.(vaishnavi and m...

Silver Fox & Barely Legal Twink

by puzziboi on Mar 30, 2020
Transgender & Crossdressers

Jim O'Connor was straight as a board. The 60 year-old with the crew cut white hair and stubbly face voted Republican, owned several guns, drove a Dodge Ram pickup, and was a retired high school teacher & baseball coach. In fact, the married father of two adult daughters with four grandkids had amassed 19 consecutive winning seasons as head coach. His record...

Me and My Teacher

by juhohelle on Jul 6, 2020
Mature

The year was 2006, and I had just graduated from my high school in Bangkok, Thailand. I had decided to go out for a few drinks with my friends, when I bumped into my former Design Technology teacher, Ms. Michaela Gillespie. Ms. G. Was a forty-ish, red-headed English woman with prominent features, a curvy womanly figure and a fondness for wearing g-strings wi...