Barefoot in the Park with Tiffany


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:

and here:

and here:

it started here:

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  I am in San Jose, California.  I look forward to hearing from you.


43 thoughts on “Barefoot in the Park with Tiffany

  1. Fun read. I am glad to see that she was able to flaunt her stuff out in the fresh air. Also she definitely filled out that sports bra. If this was the level of excitement from the park I can’t wait to hear about the activities and see the outfits that come from the next visit…

    • The theme for September is 80s exercise. Think Jane Fonda and Richard Simmons. I’ll incorporate some of your workout suggestions, and of course have a totally radical leotard and sweatband picked out.

  2. Wow! I am shaking my head with deep envy. That is one fortunate sissy!

    Mistress J, your commentary and description is delightful. It appears you had fun too.

      • Yes, Mistress J. I am thoroughly enjoying this post. Can’t wait to read of further sissy adventures.

        Quick question, please: Obviously, you were close by your sissy to take your fun photos. But were there moments where you observed your sissy from a slight distance? As if you two weren’t together?

        • Yes, when we were walking back to the parking lot. She was stressing over the people looking at her. I caught up to her and told her her thong was peeking out from her shorts because they were too low on her hips! She’s sooooo nasty.

  3. This was an intense visit for me. To be honest I was expecting a quiet park and did not have my legs shaved so I was freaking out that people would notice. The quiet time in the park was great once we found it and I loved stretching out in the grass.

    I would love some feedback on activities to try in the hotel room. The private hotel room helps me fall into the sub head space much easier.

    • Tiffany is a silly girl. Her leg hair is fairly light in comparison to an hairy Italian Gurl. Her white socks covered most of the leg. First time outdoor exposure is a big deal. I’d like to take Tiffany to a bar or out to breakfast for pancakes. I wonder if she’s up to it?

      • Depending on her level of comfort a fun erotic and humiliating session could involve wearing a full lingerie set under some tight feminine jeans. Bonus points for a plug and corset. The vanilla people won’t see all but the bottom will know and fell her reminders of her status.

        Pancakes and some skinny jeans with rattle plug sounds hot.

      • A fun time could be to have her dress like E is suggesting but have her use the remote vibrating plug.

        At restaurants I like to order for the bottom and make them wait for me to tell them to eat or until I have taken the food from their plate that wanted. Of course when the check comes I always make a point to tell the waitress that the other person will be picking up the check.

        If you are mean you could have her take a laxative during the meal to ensure she rushes back home.

    • Great job expanding your limits! For deep submissive head space I sometimes have my bottoms check in with me via web cam / baby monitor or text. Text prompts can range from commands to do an activity or texts they send validating they completed a task.

      I like restrictions on restroom privileges so sometimes we force the bottom to pee into a jar or cup and drink it if they have to use the restroom.

      Other ways to get into a deep head space is to watch a porno BDSM movie alone. Good luck next trip and I hope it is fun!

  4. Mistress if you need any suggestions I like to have my subs accompany my to restaurants with their panties and stockings with on and a nice remote butt plug tuck inside them.

    When at the table I insist that I order for them saying things like “he will have the kids portion, he is still a little chubby” and when the meals comes out I like to make him wait to eat until I give them permission.

    Another fun activity is to send them into the restroom or back to the car and have them remove their panties or apply a coat of lip gloss to ware as they finish the meal. Of course I enjoy controlling the plug as they try to eat without causing a scene.

  5. Not sure if the first one went thru…

    But for my men I love taking them to restaurants with them wearing panties and stockings with a nice remote plug.

    While at the table I ensure to order for them and make sure they do not eat until either I am done or picked a few portions of their meal off the plate.

    I also like sending them to the restroom to remove their panties or to apply a fresh coat of lip gloss to ware as they finish their meal!

  6. Buttercup – great comments above.

    For you and all others what hotel room activities do you think I should preform for Mistress was n my next trip? I am planning on being in the room all day Saturday so long or short activities are game.

    Thank you all.

    • Let me help kick this off for you Tiffany.

      If you do end up having a lot of time to pass in the hotel I would propose the following activities…. plug progression by inserting a different larger plug every few hours trying to work up to a target size. Repeating ridding a dildo for a given amount of time (ride the dildo while listening to a song) and play the song every hour.

      You could also do laps around the room or down the hotel hallway in heals every few hours.

    • If you like squats and you have the privacy of the hotel room try this… insert a dildo and start doing squats; see how many reps you can get in while holding the dildo from sliding out.

      Mistress can set your target rep number to work toward. A full day in the room should give you a lot of time to practice and practice does make perfect!

    • Your mistress should give you a few pictures of men, or women, and have you type up a few love letters to them. You should work to type why they should be your master and what you would love to do for them. These should be detailed and written convincingly to a reader.

      With all of the dance ideas maybe you can dedicate a dance with each letter…

    • Thank you all for your wonderful suggestions! I can’t wait to review what ones Mistress J will select from here… hopefully you will all love and approve of the next session.

  7. Am I extremely interested to know more after reading about Tiffany’s development. Is her session designed mainly as a punishment theme or is it for exploration?

    I used to love getting my boy friends to dress up in girl cloths. Love the options above and I have one to add for review:
    Give her a female washing kit (you know the kind) and instruct her to rinse herself before your visit.

    Breakfast could be more fun in some pleather pants or tight white jeans.

  8. Hey girl if you want some self bondage in your hotel look into these…

    I used them and they work great to keep you under control for a set time. Simple one is to tie your legs to a chair and use the ice lock to secure your hands and arms behind the chair. You could sit in the chair nude or in some lingerie.

  9. I have changed the theme for the upcoming visit to Tiffany’s Back to School Special. She will be a school girl having to do homework assignments and participate in PE.

    Anyone feel like helping me grade?

  10. So, Tiffany is getting horny. She keeps emailing me, fishing for hints.

    School subjects include:
    Physical Education
    Creative Writing
    Intro to Film making
    Sex Education
    Math and Science

    I have a very special gift for Tiffany arriving next week.

    • Mistress,

      Not to be pushy however we are all very interested to hear how she did and what punishments you subjected her to. I am sure it was very orchestrated by you.

      • Hi,

        I am sorry for the delay with this fabulous blog post of a fabulous experience. I had a family emergency that took me away and wiped me out. I’ll be posting it this week!

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