Plug Date Stories

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A Sissy's Day of Fun

by sayaSky on Mar 10, 2020
Transgender & Crossdressers

Part 1 It was summer break, so I was visiting home after my first year of college. My parents were going to be gone for the next few days visiting old friends. Being by myself, I went online to a hookup app and searched for a match. In my ad, along with a picture of my ass in a thong, I said I'm a young male looking to get fucked by a top. It only took fift...

The Collar Ch. 01

by JackValentine on Sep 13, 2017
Anal

Nikki walked in the door, two bags of groceries in her arms, expecting to hear the din of the television and find her husband and kid at home. Instead there was silence. She walked through the house, with her boot heels clicking in the hardwood floors. "Todd? Anyone home?" Nothing. Laying on the dining room table was a note sitting next to a leather dog co...

Navy Nurse Ch. 20

by Bodington on Sep 14, 2020
Novels and Novellas

After the conclusion of Adrianna's 'Double Whammy Orgasm' Diana and the law student, shared some wine while luxuriating in a calming afterglow. Thus, they indulged in some pillow talk, and Diana started the conversation, "Tell me something Adrianna, when we first met you had a boyfriend named George whom I known somewhat in the Biblical sense. As a result I...

Evil Slut Bride Ch. 06

by PeterOmez on Sep 12, 2017
Loving Wives

AUTHOR'S NOTE: I write stories most people find particularly depraved. To paraphrase Frank Zappa: If you are determined to be outraged, I can accommodate you. *** When I woke up, I lay in Jenna's bed for a moment, as I heard her fiddling around in the kitchen, and I realized that this was the first time I'd stayed out all night, and since I'd left my bedro...

My First Anal Sex

by subwryter on Sep 13, 2017
Anal

4pm... One of the things I want to experience the most is anal sex. Haha, I've just admitted to myself that I want anal sex. Now it is just a matter of bringing it up to my husband. He isn't the most adventurous man. I met him at a high school reunion. I hadn't known him at all in high school but he did admit to seeing me around. "I remember you having lon...

College Days – Domination 101 Ch. 04

by oneguy4fun on Sep 25, 2017
BDSM

Joe woke up with a raging hard-on. All the teasing and torture from Linda and Lori over the weekend had a lasting impact on him. Even though they had milked cum out of his cock before he went to bed, he was still horny as ever. The milking relieved some of the pressure in his cock and balls, but it added to his horniness. His cock twitched on its own as he...

Cuckolding Sindy

by SindySuxALot on Sep 13, 2017
Transsexuals & Crossdressers

Domina Lucy Sissy Sindy sat in her room staring at her computer monitor. Her mistress Lucy had ordered her to stay in here and watch gay fisting videos. Her eyes watched the screen as closely as she could since she knew she might be tested on the content later. She was mildly distracted from the video by the huge vibrating plug inside of her sissy pussy. I...

Jessica

by TxRad on Sep 24, 2019
Toys & Masturbation

Jessie was your typical girl next door. At twenty-five she was working in the job of her dreams right out of college. She seemed to have everything going her way. Everyone liked her vivacious nature and outgoing personality. Well, everyone but her, that is. A bad breakup with her high school sweetheart during college had been the start. Following that, ther...

Poker Loser Ch. 06

by Goldeniangel on Sep 12, 2017
BDSM

Princess, You were very bad on our last date. It's time you learned who's in charge while we're together. This Friday I will have a friend drop off a package after your parents leave for work. In that package will be several items, there will be instructions for the use of each one. All of those instructions must be followed implicitly or you will be very s...

Those Shoes Double Date

by cd_donna on Sep 16, 2017
Transsexuals & Crossdressers

** Getting Ready ** It takes me three days to fully recover from great sex, even if the love session ends in an ideal sex nap like it did with Rex and Jennifer. I put out so much energy on the bed, my mind and body are slow the next day. I felt lucky that we were not able to do a double date with Mike the next evening. The plan was for a week from that nig...