About my blog...

A collection of stories, pictures, thoughts ideas and more that are of interest to feminine and sissy males. I am open to submissions and guests posts on the blog. to email me just see my profile. Hugs...sissy terrie
Showing posts with label Mature Monday. Show all posts
Showing posts with label Mature Monday. Show all posts

Monday, March 16, 2026

Serving Her Friends

A little piece of Mature Monday flash fiction...

"Don't worry, they can all keep a secret" the Mother-in-law said as she assured her sissy cuckold son-in-law.  "Besides, look how long Janet has known about you and accepted you, and she hasn't said a word.  What's it been, nearly three years now?"

The sissy nodded in agreement, but expanding that circle of friends with two more was a big leap of faith for him.   He wasn't sure he could go through with it, but at the same time, didn't want to disappoint his Mother-in-law, with whom he'd enjoyed many intimate moments.

"Look, you have to trust me.  You know I love you and I love showing you off.  Do it for me" she said.  Then surprisingly added "Tell you what, you won't have to wear. your chastity cage.  They don't need to see that."

The sissy cuckold found some relief in that.  His mother-in-law approached him and gave him a soft kiss on the lips.  "Thank you" she said.  The kiss coaxed a smile out of the sissy.

Shortly after the women arrived an hour or so later, the sissy was introduced in a pretty bra and panty set and some stockings.  The women were welcoming and almost astonished at the "male" in front of them.

Perhaps not being kept in chastity wasn't as good an idea as it seemed a little while ago.  The humiliation was bad enough being seen like this, but now the sissy wasn't able to hide his excitement as his little clitty grew in his panties.

The woman's eyes seemed fixated on his crotch and the little bulge there.  He could feel it worsen and eventually knew that he had likely spotted his panties.  The orgasm arrived just a few moments later.

A couple of the woman smiled, one put her hand over her mouth but "Mom" just got up and put her arms around her sissy son-in-law.  

"It's okay honey" she said. "These things happen.  It's all good."

Love,

sissy terrie 👄 
 

Monday, March 9, 2026

Boudoir Photography

With a women's maturity often comes an increase in one's libido and sexual self confidence.  Part of it is accepting their beautiful bodies just the way they are.

The reluctance to be seen and even photographed at various stages of dress or even nudes slowly diminishes.

Pictures to be shared in just their bra and panties...


Showing their cleavage...

And their willingness...
 

All three of these ladies look delicious, and would be well served by many a submissive male.

Love,

sissy terrie 💗 

Monday, March 2, 2026

Mature Monday - Premiere Edition

A special thanks to my sissy friend Laci who in a comment on one of my Two For Tuesday posts suggested I launch a "Mature Monday" series featuring beautiful mature women of "a certain age."   I'm not sure what that age might be but I've always been fascinated by older, smarter and authoritative women.  Though my own loving Wife and Mistress is somewhat younger than me, She is certainly smarter and more authoritative than I am!

I'm certainly open to suggestions as I move forward, also pictures, ideas and stories that deal with mature women.  I'd like the series to deal with the general FemDom, Female Led, submissive sissy, etc. theme of this blog but at the same time I'm not closing any doors.  My "editorial board" (me) and the Ultimate Owner (UO) - my Mistress,  obviously have the final say.  The UO checks on the blog once and awhile and would certainly let me know if anything showed up here that She didn't approve of.

So here's the premiere edition of Mature Mondays, featuring some lovely ladies who are beyond their formative years, fully comfortable in their likes, desires, needs and personalities!

Naturally, these beauties are likely to reflect my own fantasies when it comes to women, lingerie, sensuality and kinks.  My first featured beuaty obviously loves full and complete lingerie ensembles and foundation garments.  She's not afraid to make herself comfortable on airline flights (note how she's kicked off her heels) and seems to have an air of confidence about her.  She's more than just a stewardess here and perhaps it's even her own private jet.   Love that dominant look of hers. 


I always love pictures of women primping in front of the bathroom mirror.  It's a common cuckold-related theme, a depiction of a wife getting ready for the real man in her life.  The picture takes on added eroticism for me when she's a woman probably beyond her fifties.  This one has the sexual confidence to continue cuckolding Her husband for as long as She wants to.  Perhaps She's even taken on a virile young Bull to satisfy Her insatiable desires.  And yes....I love Her corset.


My final entry doesn't need much explanation.  She's clearly the Head of Household, The Disciplinarian, The Boss, etc.   She clearly wears the pants in that house.  The picture captures Her Dominance perfectly.  I also see plenty of love in that picture.  After all, isn't that what it's all about?


 Hope you enjoyed!

Love,

sissy terrie 💗💗💗 

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