Tag Archives: Bay Area pegging

Tiffany Goes Back to School. Part 1

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New backpack.

 

The beautiful Tiffany was coming to town for one last trip before the year ended and she wanted to go all out!

Tiffany wanted to have a milestone in her education, as she feels she is getting ready to graduate into a real and true sissy slut. 

She wants to LEARN as much as possible, and who better to teach her than Mistress J?

The slut was very horny and wanted to taste real cock. I had the perfect friend in mind when she made this request, but more on that in Part 2.

Tiff was going to get a pussy wax at a local place and check into her regular hotel. She was going to have Friday late afternoon and evening and much of Saturday for homework assignments. I told her I’d come over to her hotel Saturday evening for grading and play.

I had a special gift for her, a personalized backpack, hot pink of course, and left it at the desk earlier that day. I wanted her to have it waiting for her upon her arrival. It was full of clothes and gadgets, as well as instructions for the weekend.

Tiffany had two pages of homework assignments. I won’t bore you by listing all of them, so only the highlights will be discussed. 

One of my favorite tasks, was Tiffany was allowed to only eat “kid food” that weekend. Juice boxes, mac and cheese, PB&J, oatmeal, and soups were her menu. Which she had to purchase herself.

The school subjects were:

Physical Education, Ceramics, Math, Photography, Film Making and Creative Writing.

Ceramics was one of my favorite subjects. I had high hopes for this one. I supplied her with a Play Dough kit with an assortment of colors and letter stamps. She was instructed to make pornographic images and naughty words. Grading would be on technique as well as creativity. This is what she came up with. Grade: C. Why a C? I was hoping for interesting color combinations and naughtier people.

Tiffany fared much better in the other subjects, which also translated to a fabulous grade in Film Making.

Math required Tiffany to do multiplication and addition exercises by grabbing a squishy pecker with her butt cheek, walk across the room and drop it on the chair. She really knows her numbers and has tight little cheeks.  She could cross the room without dropping a pecker! Grade: A.

Tiffany really shined in PE. She took this subject seriously. She was instructed to do arm curls with the heavy metal dildo with a butt plug in her butt. Look at this photo. What perfect form! The plug stayed in the whole time. Grade: A+.

She may have scored an A+ in Film Making, but this girl did NOT take a single still photo. I had to make still photos from the videos. Such a Bad Girl. Photography Grade: F.

Creative Writing was another area of expertise. She was instructed to write love letters to Mr D, Amber and Mike Tyson (Tiffany is a huge fan).

Below is the letter to Mike Tyson. I want to send Mr D and Amber their letters privately, then they can give a grade themselves. Please email me at mistressjstudios@gmail with your email and I’ll forward her letter.

A peek up the school girl’s skirt!

Mike’s letter:

“Mike,

Love your power and body and I can’t wait until I am woman enough to take your BBC.  I am working with my Mistress to become more mature and I can’t wait until a BBC is allowed to be put in front on my body…  My mouth and bottom would by a lovely welcoming home for you as I would take my time fully exploring your needs.
 
Please think of me and let me know what I can do to prove myself to you.”
 
What do you all think of this letter? Aside from the rather casual salutation, do you think it is worthy of a B+? 
 
I leave this post with a photo of Tiffany studying her Bible. Stay tuned for my next episode of Tiffany Goes Back to School. The school girl cuts loose and becomes a real slut. You don’t want to miss it.
 
 
 

Barefoot in the Park with Tiffany

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Our slut enjoys exercise. She also enjoys showing off her body. So what better way to combine the two than to take her to a local park for some outdoor exercise!

When she told me she’d be in town on 8/8, I started planning her outfit. Tight shorts, sports bra, gaff panty, socks and a hat were purchased. I even sprung for a new wig and tramp stamp temporary tattoo. She was going to be gorgeous. 

I picked a local park, Almaden Lake, which is near me and usually quiet on the trail, especially during the week. There is a par course and secluded areas around it. An ideal setting for sluts to display their athletic ability.

I have to admit, this session was full of mishaps, but we had fun anyway, and got some great shots.

Tiffany arrived bright eyed and bushy tailed Thursday morning. I had acquired a butt plug with rattles inside. How embarrassing to be jogging and making butt noise at the same time. Well, the plug was too big for her tiny butt hole, so she had to run with her smaller dedicated jewel butt plug instead. 

Our intention was for her to arrive at the park partially dressed, go into the ladies bathroom, change, put on lipstick and come out.  As I mentioned, this park is usually quiet on a weekday morning, that particular day the park was CROWDED! 

Nice pussy.

There were at least 10 old men playing boccie ball in front of the bathrooms, with a brownie troop nearby. The pavilion by the trail head had a group of 20 kids and chaperones. Not to mention, there were tons of walkers circling the lake. It was a beautiful day. A nice 82 degrees with no humidity. I think that was the big draw.

Tiffany was a bit self conscious of her slutty shorts with well padded gaff, so we opted to park near the entrance to the trail right from the road, bypassing the lake entirely. In the car, she changed out of her sweats, but kept her pussy cat shirt on. We than proceeded to the trail eager to try her skill on the par course. That day, it seemed like every single retired person was walking their dog, not to mention the amount of bicyclists too. Holy moley.

I noted she was visibly worried, and she told me she feared her boy clit would poke through her shorts, and cause mayhem on the trail. I opted for a secluded spot off the trail and by the stream. She relaxed a bit and we did some warm up stretches.

Downward facing tramp.

Caught up in the serenity of the stream and surrounding trees, Tiffany was inspired to do some yoga. Downward dog was her favorite pose, as it showed off the tramp stamp and tight butt nicely.

I wanted the slut to do some Prancercise in the grass. Tiffany can be a bit of a diva, and almost cried because her new white socks got a little mud on them. Sigh.

Run Tiffany, Run!

I was irritated by her drama and made her play fetch. She liked the doggie pose so much, she needed to be treated like one!  I threw the ball to her and she brought it back to me in her mouth like a good puppy.

Tiffany is as fond of running as I am, so we headed to a different spot where she could show off her fine running form. Look at that stride! Look at those boobs! Those legs! Such a graceful runner!

Summer isn’t complete without baseball. She did a few laps around the ball field and ended with some sexy stretches. Did I mention the grounds crew was out getting the field ready for the afternoon little league game? Well, they were, and they gave our girl a few encouraging whistles.

Why did she feel more comfortable with the grounds crew than the folks at the park? She’s a whore that’s why. She’s always looking for attention.

Put me in coach, I’m ready to play. Today…

I decided she could go to work without release. That should teach her! I am the boss, and I control her cum.

You can read more Tales of Tiffany here:

https://wp.me/p67dIy-HW

and here: https://wp.me/p67dIy-Ha

and here: https://wp.me/p67dIy-FN

it started here: https://wp.me/p67dIy-D9

Intrigued? Contact me.

Mistress J Studios is a sex positive studio that provides a safe place for personal expression. Nude male photography, male and female submission, cross dressing and gender exploration are welcomed and encouraged here.

My email is mistressjstudios@gmail.com.  I am in San Jose, California.  I look forward to hearing from you.

 

Pegging for Newbies! Bliss is butt a short drive away.

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I have these undies in red.

Mistress J enjoys working with newbies, and she especially likes taking a man’s ass virginity.

I get many inquiries from men who have never experienced the joys of ass play, but are dying to try. “Come on over.” I tell them. Let me pop your cherry! Bliss is butt a short drive away…

First, give yourself an enema at home. A clean butt is good manners.

How to I go about stretching out a virgin ass? The most important thing is to take my time. Why rush, the journey is fun. I start with a gloved finger and lots of silicon based lube. I tease the rosebud with circular motions. As I feel you relax, I gently slide the tip of my finger in. 

I have a good grasp of reading my guest’s bodies. I can usually tell when they are relaxed enough for penetration. I tell them to listen to their body. Some days the mind is willing but the body isn’t, it’s important to honor this.

The lube is applied and my fingertip is slowly warming up the back door. When I feels it’s time, my finger slides in. I give you a taste of all of my fingers. Next, I move on to my vibrating butt plug. After enjoying the cool vibes, I decide what you might need and can handle next.

Some butts need the slut machine, which is my Hitachi capped with a prostate adapter. This provides a fab warm up to a dildo. The dual speeds are guaranteed to make you squeal with pleasure. I love using this toy on seasoned as well as virgin butts. It’s a favorite of mine and my friends. I invite you to try it.

Now, this next part determines how slutty your virgin ass is. Do I need to use my smallest dildo, or can I start with something bigger?

Most of the time we start with my smallest burgundy strap-on. I keep 4 cocks mounted and ready to go. My harness of choice is the Terra Firma with buckle by Stormy Leather.  While I often start with the slimmest dildo, there have been a few butts able to start 1 or 2 steps larger. In fact, this happened yesterday.

Doggie style. A self portrait.

I like to have my guest take my cock on all fours while kneeling on my chaise lounge. I love the view, and it’s such a good height. Sometimes, this angle doesn’t work well for a virgin butt. I find having my slut lay on his back on my massage table with his legs up is a fun and easy way to slip in. Plus, this really is the ultimate roll reversal. I get to be the man, and he takes it like the little bitch he is.

I feel I am a fabulous butt-fucker. I suggest if you are curious about being pegged and are a newbie, you can’t go wrong with me.

Paul was a butt virgin, now he’s a regular. He takes my biggest cocks and begs for more. This is what he had to say:

“Getting pegged was such an intense feeling. It made me crave it bigger and deeper.”  And trust me folks, he does.

So many men started out with my small dong, now they crave the biggest things I have. And I am always adding to my collection.

Intrigued? Contact me.

Mistress J Studios is a sex positive studio that provides a safe place for personal expression. Nude male photography, male and female submission, cross dressing and gender exploration are welcomed and encouraged here.

My email is mistressjstudios@gmail.com.  I am in San Jose, California.  I look forward to hearing from you.