Chaperone Stories

1,440 results
Orientation
Length
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Infinite Scroll

Melissa Makes Friends

by mjar65 on Sep 13, 2017
Group Sex

We've known Melissa for quite a few years. She was more Annie's friend to start with but we socialise together every once in a while. I like Mel. She is quiet, though not exactly shy. I honestly don't know whether she even has boyfriends or lovers - that's how quiet and straight Mel can be. She is small in height and a little plump but she carries it well a...

Bachelorette Party Chaperone Pt. 02

by KingBandor on Nov 12, 2019
Loving Wives

Chapter 7 "What the fuck?" I exclaimed as I tapped on the video thumbnail to start it playing. My hands were shaking so severely that the screen was bouncing all over the place. "What is it?" TJ asked as he leaned over my shoulder from the seat behind me. "Another video?" "Yeah, looks like it," I mumbled. It looked as if this video started where the prev...

Cathleen Encouraged Ch. 02

by nocluescooby on Sep 12, 2017
Loving Wives

This is the continuation of the story Cathleen Encouraged. To fully understand the background leading into this installment I suggest reading Part 1 first. * Cathleen awoke early the next morning. I didn't sleep all night in anticipation. She went straight from our bedroom to the bath. While she showered I made breakfast for us. Cathy exited the bathroom...

Service with a Smile Ch. 01

by dirtynaughtythoughts on Apr 24, 2018
Fetish

The phone in my office rang at about 2pm. It was usually a quiet part of my day in my job as Guest Relations Director at the high end luxury hotel I work for. "Ryan. We need you down here in the banquet room ASAP. We have a situation." It was our day shift manager -- Liz -- on the other end of the line. "What's wrong?" I asked. "One of the speakers at t...

The Hijab Hunter: Saudi Girls

by Samuelx on Sep 12, 2017
Interracial Love

When everything is wrong, just follow your own instincts. Those are the words I live by. In case you're wondering who this is, the name is Halima Osman. I was born in the town of Minneapolis, Minnesota, to Saudi immigrant parents. I'm five-foot-nine, large-breasted, wide-hipped and big-bottomed, with an hourglass figure. I have light bronze skin, light brown...

Getting Carried Away

by John_Spivey1966 on Sep 2, 2017
Erotic Couplings

The text message came through at 7:00 in the morning. "I'm going to be in town with the kids and would love to see you." The "kids" were the children from Carrie's school where she served as principal. "I'd love to see you but don't you have to chaperone?" "Not this time. They have more than enough." "Lunch?" "No. Hotel." Carrie and I had been friend...

The Full Moon Party

by Ozimandickus on Sep 16, 2017
Erotic Horror

It was late in the afternoon when the ancient bus dropped the three girls at the market place. They loaded up with supplies for the party. Lots of bottled water. A couple of bottles of the strong local rum, to get them in the mood. Some fruit. All three were 18 years old, on their gap year before starting college. Mel was a tall blond, whose slender waist m...

A Keen Sense of Obligation

by b7ffh1 on Dec 2, 2019
Exhibitionist & Voyeur

Trigger Warning: This story is set in 1970's Alabama and some the characters and institutions have racist and/or sexist views that are unacceptable today. *** At the end of WWII, two friends from India, Srikanth and Pramod, were studying engineering at Oxford University in England. Because of their talent, they came to the attention of the right people, an...

Second Romantic Lead

by bellydance on Sep 14, 2017
Erotic Couplings

I've told you the story of the night I waited so long to fuck my wife and then, when she returned home and I made love to her, I discovered – I knew – that, just before – perhaps minutes or just an hour or less before – she had been unfaithful to me. That didn't make me want her less. On the contrary, I wanted her more. My lust, already great from the long...

Awe & Shock

by barabajagal001 on Sep 3, 2017
Erotic Couplings

"I had a wonderful time tonight, Natalie," a tall, handsome man was saying. Natalie smiled up at him, but she wasn't feeling it inside. "Mmhmm," she agreed politely. "It was certainly something. Give me a call sometime. I'd invite you in, but I'm afraid I've got an early meeting tomorrow." "Oh. I see," he said, obviously disappointed. "I'll see you soon."...