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Calendar
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday
Sunday August 30
 
Monday August 31
 
Tuesday August 1
01
It's Too Late - You're a Sissy Whore

I'd tell you you ought to stop watching sissy porn, but clearly it's too late for you, isn't it? You're a sissy whore now. The thought of cock and cum consumes you, doesn't it? You lick your slutty lips as you think of swallowing a cock, letting it throb on your tongue as it spurts that creamy load in your sissy throat. You rub your clitty to that thought of that same cock stretching your sissy pussy as it pounds your fuckhole. Cock and cum - it's all you care about sissy. Do you need more? Get on your knees.
It's Too Late - You're a Sissy Whore

Wednesday August 2
02
I Want You to Suck My Cock

Do you know who I'm thinking about every time I stroke my thick, hard cock? It's you -- my lover. I love our moments of intimacy… our bodies pressed together as we kiss passionately. Your hands on my soft, natural tits. Our cocks rubbing against one another as we embrace. I think of you dropping to your knees as you crawl between my legs. How you lick and suck every inch of my throbbing cock. You love looking up at it just like this, don't you? See how hard it is… you want to do what I want, don't you? To have you lick and suck this cock until I cum. It's so hot for you to know you're the one who pleases me… you're the one pleasing me so much I can't help buy cum. Are you ready to make me cum?
I Want You to Suck My Cock

Thursday August 3
03
Stroking My Cock in Matching Bra & Panties

Do you ever feel like some solo trans stars repeat very similar sets over and over and over again. Where you feel the only difference is the color of the lingerie she is wearing. You know what I am talking about: "Pretty Face on a Pretty Couch Doing a Pretty Fuck!" Apparently since everyone does it, it must be popular. Well I believe in giving you more bang(ing) for your buck! Case in point... why stretch the same basic set with only a change of costume over 4 or 5 updates? We take the three different outfits and mash them into one set! Three sets in one... it's like a Triple Changer with a hell of a lot more trans woman cock! For your enjoyment: Wendy in Red Lingerie; Wendy in Purple Lingerie; Wendy in Blue Lingerie... on Couch.
Stroking My Cock in Matching Bra & Panties

Friday August 4
04
Eat Wendy Summers's Ass to Fuck Her

We both know you need to dive between my sweet cheeks to lick and fuck my tight hole. So I'm going to give you exactly what you want. This video focuses entirely on my gorgeous ass as I whisper all the nasty, perverted things I want you to do to it. I'll give you great shots of those little strings of fabric disappearing between my ample cheeks. I'll peel those panties off revealing my perfect pink hole. I'll grind my hips back as I encourage you to bury your face between my cheeks and eat my tight trans pussy. I spread my ass to let you slide that cock in my tight pussy. I tell you to fuck me hard and ram that dick deep inside.
Eat Wendy Summers's Ass to Fuck Her

Saturday August 5
05
TS Counselor: Helping Your Self Esteem

So you think you're too shy and you can't talk to attractive women? I'm not going to ask you "How does that make you feel?", because I know. I am a professional, you know. I'm really the ideal person to help you with your self-esteem issues. Relax and let me show you. I knew from the minute you walked into my office that you were curious to know what I looked like out of my low-cut dress. Believe it or not, I was picturing you naked and felt the need to wear some skimpy pink panties for our session today, I know you're hot for me, I catch you sneaking a peek at my cleavage every time I look away from you and I definitely see the growing bulge in your pants as we talk. Since we are in the bubble of physician-patient confidentiality, let's try some immersive, hands-on treatment. I'll boost your confidence in no time!
TS Counselor: Helping Your Self Esteem

Sunday August 6
06
Monday August 7
07
My Trans Tits and Cock Are Falling Out of My Jumper

My low cut jumper isn't just straining to hold in my tits... it's skirt is hiding my throbbing dick. You want me to pull back that curtain, don't you? Let my thick juicy cock free so your cocksucking lips can wrap around it? Drop to your knees and be the dirty slut we both know you are.
My Trans Tits and Cock Are Falling Out of My Jumper

Tuesday August 8
08
Fluff Friday Compilation Jul 2020

This compilation features 5 dirty-talking short masturbation clips formerly available as my Fluff Friday videos from July of 2020.
Fluff Friday Compilation Jul 2020

Wednesday August 9
09
Trans Counselor: You Want Cock

As your counselor I sometimes need to challenge you -- and it's very clear you're avoiding a fundamental truth about yourself -- you want cock. In today's exercise, I'm going to help you accept that part of you. With a few mantras and some waggles of my thick transsexual cock we'll get you sucking cock in no time. I'll have you masturbate as I make you repeat how much you want cock. How much you want to lick and such it. How much you crave cock and cum… I'll even condition you by rewarding you with my sweet load of cum.
Trans Counselor: You Want Cock

Thursday August 10
10
Wendy Summers Oils Her Feet, Tits & Cock

Lots of ladies use baby oil to aid in accelerated sun worshiping, but, being the resourceful trans woman that I am, I have come up with another, much more erotic use for this slick liquid. Since I love to pamper my feet with luxurious, sudsy baths and treat my toes to pedicures, I figure I can save my porcelain skin from sunburn and use the oil to treat my feet to a little much-needed rubdown. As I rub the slippery solution on my feet and feel it slide between my toes, I start to wonder what other parts of my body could benefit with a little extra lubrication. And, being the creative trans woman, that I am, I know exactly where to apply this liquid for maximum pleasure! Peeling off my clothes and dripping oil into my hand makes me feel some below-the-belt tingling, and I can't wait to allow my soft hands to make their way across my slightly quivering body. Looking at my glistening breasts and shiny, hard cock, I'm incredibly turned on...and I need someone to rub some oil on my back. Are you in the mood for a little mutual massage? And don't worry, if you submit, you're guaranteed a happy ending!
Wendy Summers Oils Her Feet, Tits & Cock

Friday August 11
11
Wendy Summers Cumshot Compilation 5

You love seeing my thick cock spraying my juicy load of cum! So it's time to swallow a heaping serving of my sweet & sticky cum. This video's compilation features some of my finest trans cumshots from 6 of my fan favorite videos. Featured are the cumshots from "Be My Bitch or I Tell Your Wife," "PSA: Benefits of Eating Cum," "TS Counselor: Confronting Your TS Porn Addiction," "Spiking Your Cup With Cum," "I'll Tell Everyone You're a Faggot," and "Loser Cocksucker." So get that dick out and jack to these tasty cumshots again and again.
Wendy Summers Cumshot Compilation 5

Saturday August 12
12
Satin Sheets

There's something sexy about laying on Satin Sheets... how they glide over your body just like how cum-covered cocks can slide past one another when frotting? The shiny, silky smoothness just feels so sinful. It gives me a devilish idea -- want to join me on these sheets? I will slide my smooth body all over yours until we're both slick with precum and our cocks are shiny. Want to freak in the sheets with me?
Satin Sheets

Sunday August 13
13
Monday August 14
14
Tuesday August 15
15
TS Counselor: Accept Your Small Penis

As your counselor, I sometimes have to help you confront some hard truths. You've told me how your ex-girlfriends have told you they couldn't feel it when you tried to fuck them. You've told me how women have laughed when you drop your pants. You need to accept that your small cock will never please anyone. It's time that you accept that the only choice you have in front of you is to be a cocksucker. It won't be so bad choking down dicks and becoming a cumguzzler. I'll even ease you into it by letting you suck my dick, loser!
TS Counselor: Accept Your Small Penis

Fuck Me. I Want Your Cock.

I am fucking aching for it. I want you dick deep inside my ass --your hands on my hips pulling me back on your throbbing dick. I'm dressed in my sexy red baby doll. Since I don't have you here, I'll use my black glass dildo. I'll slide it right into my tight asshole. Stretching it open and loosening myself up like the little bitch that I am. But before I'm done I'll be riding this dildo like I want to ride you... My tits and my cock bouncing as I bring us both to orgasm.
Fuck Me. I Want Your Cock.

Wednesday August 16
16
Thursday August 17
17
Making a Special Protein Filled Breakfast for You

You already know that I’m a perfect trans partner, but it can't hurt to give you a little reminder! After a spending a passionate evening with you, as much as I love to wake up in your arms, I thoroughly enjoy making you a little breakfast in bed. I unleash my inner domestic goddess, wrap myself in a flimsy silk robe and head to the kitchen to work my "MILF-in" magic and whip you up a little something special. As I arrange some sweet fruit, I can't help but put together a cheeky arrangement that reminds me of you! And, while on chef duty, I get a surprise as I spy you walking in to get a taste of the trans treats I'm preparing to help you start your day. I get distracted from my wifely work when I spy your morning wood and I can’t help but give you a little show of my own - especially since I can feel my own cock tingling with anticipation. I make the most of the succulent strawberries and ripe cantaloupe and give you a little trans woman showcase to go with your meal - and I don't care what people say, I think there's nothing wrong with playing with your food! I'll make sure you get your 5 servings a day - not only of tasty fruit, but of this tantalizing trans woman as well! I'm serving up a little morning pick-me-up that’s even more eye-opening than a cup of coffee!
Making a Special Protein Filled Breakfast for You

Friday August 18
18
You're a Dirty Gooner for Trans Cock

You just rub and rub and rub. Mindless jacking your dick to transsexual cock like mine. You want to see a cock like mine bulging under that dress; under that skirt. You imagine the panties being pulled off and you just goon harder. So pathetic. Stroking and rubbing and all you see in your mind is my trans cock. You'll never get one you know… you’re too busy jacking your dick -- gooning mindlessly. You'll never go get a cock like mine because you can't stop jerking. So you watch these videos. Thinking about my cock, my balls. Imagine tasting the precum. Imagine my cock throbbing in your throat. Imagine tasting that cum as it sprays. So go on… goon like the dirty loser you are. Buy this video and jack that dick to my cock and my cum. We both know you will.
You're a Dirty Gooner for Trans Cock

Saturday August 19
19
See My Unicorn Horn

My new unicorn pajamas have reminded me how much kinship I feel with unicorns. Like a unicorn, I'm a bit hard to catch. A girl like me is a Rarity, so you ought to try to catch me when you get the chance. I've got a special "horn" which you're going to love. You won't need a virgin to lure me in... just your open and willing mouth. The bulge in my shorts is growing at the thought of your lips wrapped around my shaft. My horn is revealed and I know you'll do your best to claim it for your own. I won't cum rainbows, but I think you'll enjoy the reward for finding me.
See My Unicorn Horn

Sunday August 20
20
Monday August 21
21
Be Wendy Summers's Cockslut

When I look at you, I know exactly what I want from you. I want you to be my little cockslut. I want you to kneel before my sexy transsexual ass and wrap your lips around my thick juicy cock. I'm going to wrap my stocking-covered legs around you neck and hold you down until you swallow down on my throbbing dick. I'll tease you by dressing in my sexy thigh high stockings and garter belt. Teasing you with my soft natural tits. I start rubbing my cock through my panties describing exactly how I'm going to make you lick and suck it. I point out how I'm so excited my trans cock is leaking my precum through my panties before pulling them down revealing my thick, throbbing cock. So... will you be my cockslut?
Be Wendy Summers's Cockslut

Tuesday August 22
22
Be My Sissy Slave

Oh Mistress knows how weak you are. Deep down you know you're a sissy slut but you're just too scared to give into those urges. But Mistress has a plan… do you see this collar. You have no choice from now on. You're now and forever my sissy slut slave. Mistress will take charge of everything. Your only purpose your only thoughts are of cock and cum. You're meant to drain balls, drain cocks and Mistress will make you do it. I'll make you get the sissy tits you know you need. I'll make you dress like a slutty whore and take you to the gloryholes. I'll make you suck and fuck every guy there. A cock in your throat, a cock in your ass, a cock in each hand. There's no going back… you'll drain all of their balls getting your sissy pussy bred and your throat fucked raw with cock and cum. That's all you've truly wanted isn't it? Let Mistress take charge.
Be My Sissy Slave

Wednesday August 23
23
Thursday August 24
24
I Fuck Him to Steal His Keys

I may no longer be with Morgan, but that doesn't mean I can't use him. I want his car and I'll do whatever it takes to get what I want. I hatch my plan by shaking my sweet ass and rubbing my soft tits all over him. I'll slide down between his legs and suck his dick until it's hard enough to slide deep in my ass. I'll let him use my sweet fuckhole until he sprays his load all over me. Then, as he starts to doze off, I'll grab his keys and take his car. He gets what he wants and I get what I want.
I Fuck Him to Steal His Keys

Friday August 25
25
You Can't Stop Your Sissy Urges

Oh Sissy… it just started with buying sissy videos but now you just can't stop. Every chance you're alone you dress up and mindlessly rub that clitty. You love being a slutty sissy don't you? Getting to wear pretty things… thinking about cock. Oh you love the thought of cock… sucking it… taking it in your sissy pussy. Mistress knows why… this is what you were made to be. A naughty sissy dressing up and rubbing your clitty. So embrace it -- Mistress will tease you with her tits and cock and make you repeat how much you love cock and cum as a sissy. Let's face it -- you'll never stop. You're made to be a sissy.
You Can't Stop Your Sissy Urges

Saturday August 26
26
Holes Are Meant to be Filled

Webster's Dictionary defines a hole as: an area where something is missing. TS Milf Wendy Summers has a hole that's certainly missing something: your hard cock. But since you're not there with her, Wendy uses her glass dildo to pound her bubble butt. This mature transsexual raises her see through lingerie before ramming her toy deep in her ass. With moans and screams, Wendy shows she can make do with what she has, all the while dreaming of your dick buried in her ass... Do you want to make her dreams come true?
Holes Are Meant to be Filled

Sunday August 27
27
Monday August 28
28
Wendy Summers is Your Slut

Admit it! You've dreamed of having a girl with a nice hard cock just waiting for you. Lounging around to satisfy your every sexual desire. Guess what? You've hit the jackpot. Whether you want to gobble down on this thick throbbing dick or lick my tight fuckhole, I'm ready for you. Some get over here and grab my sweet ass while my hard dick plows your throat. From tit to toe I'm built for pleasure and I'm here to please you. So what are you waiting for? Get over here!
Wendy Summers is Your Slut

Tuesday August 29
29
Filthy Faggot, You Can't See My Cock

You're such a pathetic little faggot. Quit lying about liking me because I'm a girl. All you care about is the cock inside my panties. Admit it! You don't give a rat's ass about my feminine curves or my soft tits. All you care about is that I have a cock. Well guess what you little dicklicker? You're never going to see it. Beg all you want for my dick, you won't ever see it. I'm saving it for the real men, not some dick licking pussy like you. I'm going to remind you what a little fucking faggot you are... begging for cock. Admit it. You don't want my dick. You want a man's dick... and I won't show you mine until you chug down a load of man chowder from the studs you really crave. I bet you'll even buy this video even though I don't get naked because you love been made to think about sucking cock. You're such a loser!
Filthy Faggot, You Can't See My Cock

Wednesday August 30
30
Thursday August 31
31
Wendy Summers is Your Trans Stepmom

There's nothing I enjoy more than taking some time for myself, and when my husband told me he was going out of town on business, I looked forward to some well-deserved "me time". After work, I got home, put on my favorite silky robe and settled in with a steamy romance novel. Unbeknownst to me, you, my 20-year-old stepson are in the house and heard the soft moans coming from my lips as I was reading my erotic tale. Hoping to satisfy your secret MILF fantasy, you snuck in to see me, overcome with the naughty words passing before my eyes, reaching under my robe and stroking my rapidly-hardening cock. When I do notice that I've got an audience, I can't help but act out what I've been reading - and I can tell you're turned on by this bodice-ripper coming to vivid life by the growing bulge in your pants. But surprise, I have a cock. It turns out you love special tgirls just like your old man! Relishing in the attention, I tease you, revealing the lacy lingerie that I'm wearing under my robe and caressing my soft skin and curvy body. This serves as chapter one in our own sexy story and our mutual masturbation leads to a very happy ending! I wonder if our illicit encounter will remain our kinky little secret?
Wendy Summers is Your Trans Stepmom

Friday August 1
 
Saturday August 2