Mature Crossdressing Stories

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Real BBW: The Wild Atlantic Way

by Litkid on Jul 31, 2019
Mature

For as long as I can remember being interested in the opposite sex, I've been a BBW lover, a chubby chaser. Curvy girls are my weak spot - big boobs, butts and bellies. As a long time bachelor, I've been able to indulge my passion for BBWs. This story is true. The names and some of the places have changed, but the hot sexy plumper action is recounted here ex...

The Two Sisters

by Jack1107 on Dec 12, 2018
Mature

Tom had been offered a partnership in a large Law Firm. He had a First Class Honours degree and was headhunted for the position. He had been flattered when he had been approached and had negotiated an excellent salary. He would start in his new position a week on Monday and had found a reasonable bed and breakfast but they could not offer him an evening meal...

My Beautiful Friend

by Acheronn on Dec 11, 2018
First Time

I can remember fantasizing about men very early in my life but my imagination only wrapped its warm lips around these thoughts briefly, never requiring my hand to help soothe my cravings away into a washcloth or all over my trembling lap into warm, spurting, and necessary blasts of pleasure...women were the rulers of my lust until I became great friends with...

My Pantyhose Mistress

by legman674 on Dec 10, 2018
Fetish

I have a pantyhose fetish. I always have. But then you know this about me, don't you? You have always known this. I know, it is no big secret. I don't know what it is about pantyhose that always turn me on so much, but ever since I was in Jr. High, I always remember getting turned on when ever the girls in school would wear them. I'm older now, more mature a...

Scoutmaster's Wife

by Magna12 on Jul 10, 2018
Mature

In my tween years, like many of you, I was a Boy Scout. Our troop went on a camping trip every month, and it was fun camping setting up tent camps and hiking in the woods. One summer, we made a week-long camping trip to the mountains. This was a big project for the troop leaders, and our scoutmaster, Mr. McIntosh, brought along two other assist scoutmaster...

Mr. & Mrs. Jones Next Door

by Cleevedreams on Apr 9, 2019
Mature

Glistening in the sunlight from the window, my cock stood erect as Rita's fingers slid slowly around the head, mixing the tear drop of precum with the baby oil she had so liberally applied. "God, Rita, just don't stop," but she did stop. She knew that I was so, so close to cumming that one more stroke of her slippery hand would open the floodgates. The onl...

Duet

by tkoberon on Jan 21, 2020
Mature

Her voice rose to a crescendo as the audience sat apparently awed by the power of the human voice. A few passages back I had sang a very fast-paced part which really took all my concentration to do well. It also contained some really high notes, straining even my tenor voice. During practice I had almost failed to give that particular passage its proper inte...

My South African MILF

by Samuelx on Mar 12, 2019
Interracial Love

Lorraine Hauser, a native of the Kwazulu-Natal region of South Africa, is loving the City of Atlanta, Georgia. The place is big but quaint, and honestly, it reminds her of her homeland of South Africa. Of course, the local Black men were nothing like the Zulus and Xhosas that Lorraine was used to bedding, but for a bit of summertime entertainment, they would...

My Naughty Babysitter Ch. 02

by Indianaboy6555 on Jun 4, 2019
Mature

My wife and I ran into a patch where we seemed to both be going different directions. It wasn't an interpersonal problem, life just pulled us that way. For example; things would come up at work that needed my attention, so I got called in. Then her Mother would call, and she'd need her there. So off she'd go, and I'd be home alone. The only saving grace at...

Ploughing Kate's Backyard

by Surferdude_74 on Jun 12, 2019
Anal

Kate and I had met time and time again in various college courses or at the odd party. We had talked about insignificant issues and might have had a drink together. We have had pleasant conversations, but I cannot say that I found her stunningly attractive. She was a good drinking pal, a kind of tomboy with her really short, light blond hair and her slightly...