Did you get porked for Christmas?
Little Timmy was good all year long. His letter arrived in August, because he was so sure that Mistress Lena Claus would have something wonderful for him. Well, he was watched during the year , wearing his panties and enduring long sessions of orgasm denial. He was a wonderful frilly sissy.
Naughty Timmy gets sissified
After working with Timmy on his feminization, he began to wear full sets of women’s lingerie under his business suit. Mistress Lena Claus heaped small penis humiliation on him regularly. He was never allowed to orgasm, but it seemed to make him more anxious to be considered all- woman. Timmy knew his tiny dicklet would never please a woman, but a woman was not who he wanted to please! Since he wasn’t allowed to cum, Little Timmie was instructed to use a prostate massager to milk his prostate.
Bicurious Christmas for Timmy
Denying his ability to cum, left Timmy feeling so feminine. He had been fantasizing about sucking cock for mistress, but she had other ideas. As the clock struck twelve, Mistress Lena Claus appeared to Little Timmy. “I have been watching you, Timmy.” “Since you have been a good sissy, I will grant the wish you have fantasized about.” She snapped her fingers and they were transported to a gorgeously decorated bedroom. Little Timmy was dressed in full feminine garb. His eyes grew wide , as a tall handsome stranger stood in the middle of the room. Mistress Lena Claus said, “Go ahead Timmy, I know you want to bend over and have that cock stuffed deep inside you like a holiday turkey.” When he felt the glorious penetration inside his anal canal, Mistress Lena Claus said, “Merry Christmas and many more butt- fuckings!”
**Enjoy Mistress Delia’s holiday blog on December 26th. https://www.begformistress.com/2014/12/caught-masturbating/**
Oh my poor Timmy lol. He had a lot of Holiday surprises for Lena Clause. From a good milking to being totally transformed into a sissy. I know that Timmy loved every second of it and begged for more. How can he ever top this Christmas, all of his dreams and fantasies came true. Great post Ms Lena
Timmy did get quite a surprise for Christmas, didn’t he Miss Cooper?You know what though, I can probably do one better than that next Christmas. We’ll see how Timmy does in 2015!
Ummmm…little tiny timmy seems to have had a wonderfully full-feeling xmas! Hope she enjoyed her gurl time. vanilla had a lot of DP time at the holiday party…and got a new present from her mistress, more ink! another dirty tattoo.
Oh Vanilla, where did this one go? Somewhere unmentionable?
Just above vanillas neatly trimmed pubic hair on the left…a Playboy bunny with the words horny fucktoy under it. Still a little sore, took a lot of ink to fill in the bunny, but vanilla gets horny just thinking about it.
Ms. Lena –
Love this post 🙂 I think tiny timmy had himself a wonder-full (LOL) Christmas! This is why I LOVE winterfest. It is such a great time to discuss the holiday transformations, milkings, and more for slutty sissies!
I wonder what 2015 will hold for tiny timmy? LOL
Ms. Delia
Ms. Delia,Timmy may wake-up to find he’s become all- woman from the waist down!The more he gets stuffed, the more girly he becomes.
What a lucky little pet Timmy is Ms. Lena and thank you for sharing this tale with us, as part of the Kinky Winter Wonderland adventures! I love how Timmy embraced his sissy side with the feminization and humilation you provided… but I think it’s the introduction of your Strap-On that really makes this a special tale… I mean, who doesn’t love a stuffed bird during the holidays? 😉
You are sooo right Ms. Christine. A humble, stuffed bird is the best!
Oh my, Timmy got so much stuffed in HIS stocking! Will you be MY Lena Claus? I like to have nice big things sliding down my chimney too!
Excellent story, Ms. Lena! I especially loved the part about orgasm denial making our lovely Tiny Timmy eager to please and be much more girly than ever. I hope Timmy does get many more butt-fuckings in 2015! 🙂
Timmy is my best sissy-girl to date. The orgasm denial is definitely working. I may begin to use extended periods of chastity next.
Little timmy was the happy stuffed boy for the holidays. It makes me wonder what will happen to little Timmy in the frigid cold winter months that we are about to enter. Will Timmy get an even bigger cock in 2015? Will little timmy ever get to have a full cummy? I guess only time will tell if Timmy will ever get to cum again…. XOXOXO
Simone, Timmy may not get to cum again. Mistress may just decide things only go IN him and don’t get to cum out :)!!!
Little Timmy learned a very valuable lesson. It’s good to want things. And more importantly…serving a Mistress is all about her pleasure. I can imagine the look of shock and excitement on his face as you sprung that Christmas surprise on him. *laughing* Here’s to many more happy butt stuffings!
Yes, Miss Violet, Timmy was a little humiliated to say the least. He is getting used to being “stuffed” on a regular basis.