If you hadn’t already guessed it, yes it’s a lingerie sissy assignment. Make sure to refer to the previous lesson here. As always there will be two options to choose from, one meant to be easy so even the most private of sissy should be able to manage. And the other option is for those more daring or with fewer limitations. This lesson also includes a bonus assignment but more about that at the end.
Lingerie Sissy Assignment Option One
This option is for those that can’t freely buy and collect lingerie. It’s going to require some effort. Remember the creative occasion section mentioned in the lesson. Since you can’t go out and get a sexy little number or put one together in the normal manner then get creative. You can use the examples I provided you in the lesson, or come up with your own plan and design. Create a sexy look using what you already have. You can easily pick up lace, glitter, or ribbon at a craft store. No one has to know what it’s for, and then start crafting something up.
Your goal is to create a sexy look, or outfit that you would wear for me as your mistress. If you are in the gold or diamond tier please send me a photo of what you come up with. It’s not a requirement but it will be taken into consideration when reviewing your progress. Or post in EE with the description as “for sissy school”. You don’t have to include your face of course but accountability is key to this journey.
Option Two
Option two is a lot similar then one however if you choose this option I’m expecting you to put together a sexy occasion lingerie outfit for me. Wear for me an outfit you would either seduce me in or wear to suck cock. Again I would like a photo submitted, you can be wearing the outfit or simply just have it laid out on your bed. However, I need to clearly see each piece of lingerie that makes up the outfit. You can email or post on EE with the description as “for sissy school”. Don’t be shy to glam it all up!
Bonus Assignment
We are lucky to have lesson two fall on the same day as the sissy slumber party announcement! Which is a group of lovely mistresses put together by the gorgeous Ms. Ruby, and it’s no surprise that I will be present. There’s no way I would miss out on a sissy event! Read details about it here, and sign-up if you can! If you sign-up I want you to pick out cute a outfit to wear for the slumber party. Remember in the lesson I made suggestions on what to wear for a girls’ night. Once you have an outfit picked out for the event send it to me for approval. Hope to see many of you there!
Your Sissy School Headmistress,
Riley
Choose option 1 sent them to email went casual n playful since in sexy n one for slummer party
Thank you, Lexi
I love this assignment. After everyone left the office for the day, I put on my “seduce your partner” lingerie. This is what I wear when I meet married men at the local motel for regular hook-ups (I meet them on the gay chatline). I give them what they’re not getting anymore from their wives — I suck their cocks and give them my sissy man-pussy to fuck, while I’m all dressed up as their “pretty girlfriend”. I have on my sexy black fishnet nylons, my favorite pink silk panties, sexy lacy red bra (really holds my man-boobs in place) and my favorite see-through pink babydoll.
Thank you Mistress Riley for this assignment. I’m prancing around the empty office right now thinking of how sexy and pretty I feel. I’m going to have to call one of my regular married men who love treating me like the sissy faggot I truly am.
Hugs & kisses,
cdCindy XOXOXOXOX
Sounds like someone is going to get lucky tonight. Hahaha XD
EEEE such an inspiration Cindy!
Greetings from Judy’ Sissy Boudoir/ Parlor here in the American Southwest Red LIght District
Here in Farmington, NM. Well it is February 5 and it is very cold as usual as for February here
In New Mexico. Well onto the updates with what is happening in Judy’s life.
Thank you for this wonderful assignment, well during the day I would wear white Bali briefs along with a Bali 34B Full Coverage bra with tan pantyhose and white full slip.
Maybe during the afternoon, I would change into pink Bali briefs again with a Bali 34B full coverage bra along with pink full slip or teddy.
In the evening, we go with black panties and bras along with full slip or half-slip or teddy.
Always with red lipstick like a good sissy faggot I am.
Love,
Judy
Aka “The Silver SIssy”
P.S I was wondering if there is any way us sissies can get in touch each other.
Hello Judy all of that sounds super sexy! In regards to your girlies connecting a lot of sissies that are enrolled in the sissy school are already on EE or the sissy forums. 🙂
Mistress Riley,
This is very fun and i sent in my date night look and a fun lingerie one. Now just need a hot guy 😉
As someone that wears panties 24/7 i realised i only had briefs and bikinis. I made a few different purchases for some other kinds such as boyshorts, hipsters and my first thong.
I loved how cute you looked Brittney really well done! You certainly passed being a hot seductress. 😉
Dressing up in something sexy for a session trying to seduce you! That’s what I call the perfect assignment!! I’ll make my way to the local Fredricks of Hollywood this coming week and send a jpeg of my selection.
Yay! I know what you pick is going to look super awesome! Can’t wait to see what your going to seduce me with 🙂
I chose option 2 and loved it! I emailed you my photo, I couldnt create an account on EE it keeps having errors 🙁
Yes, I got your pic and well you know my reaction but still Dayummmm! When creating an account it will still need to be approved so it’s possible it still went through despite the errors, it’s being updated and worked on recently so make sure to check back in a few days 🙂 Cause I know everyone would like to see how great you look!
Lingerie and being sexy are a bit out of my wheelhouse but it was interesting to try something different. Went with option 1, and now I’m kinda interested in getting something a bit sexier when I can afford it.
Thank you, Cassie, it’s always great to try new things and I’m happy that you stepped out of your comfort zone a little bit just to give it a try. And very grateful it piqued your interest to try it some more a little down the line. <3
It’s so hard to decide! I don’t want to flood your inbox, so I will just try to pick a favorite ensemble. What a fun assignment.
I’m happy to see as many as you would like me to see Maxie <3 I could pick my favorite!
This was a very fun assignment???? I choose option two! I wore a pink corset with attached garters and red stockings. I send you a photo. I’m not entirely satisfied with the result and the garters push a lot on the stockings, but I hadn’t much lingerie choices.
Than you, Mistress Riley, for the great lesson and assignment????
I loved your pic thank you, Julie!
I’d love love love to do this!!!! Done this alone long time ago but wasn’t
as fun as I thought ????, it would be great if my married girlfriend and her girlfriends would have me get measured fitted and kept in bras as well trying on dresses with them telling everyone.
It’s super fun to get dressed up but definitely more the merry sometimes. That sounds like a super fun idea Carli, totally get where you are coming from.
Miss Riley,
I love this assignment, to be fair finding a sissy who doesn’t want to wear sexy lingerie might be a challenge. The fact that you make the lessons available to a variety of sissies; some may have access to loads of lingerie to choose from, to someone who might be starting out or doesn’t have the freedom to dress as often; everyone can participate as the are able. I think my favorite part of this lesson is that you are choosing a sexy lingerie outfit with someone else in mind. Wearing pretty lingerie is one thing but to be thinking about how someone else might enjoy seeing you wear it for them is an added bonus.
Thank you again Mistress Riley for another wonderful assignment!
I was fortunate that I ordered some lingerie the day before the assignment occurred. I was hoping for a sexy occasion and it made reading the assignment a lot of fun but also had me second guessing until it arrived. Yesterday I tried it on and it was the most amazing feeling I’ve had in a long time and made me really excited to post! I picked out a sexy teddy that is black with sheer parts with white laced trim along the bottom. It came with a white laced hairband, white cuffs with black bow ties, and a white neckpiece with a black bow. I feel like a really naught maid. I have some lacy black pantys to go with it and some heart shaped leather garters with black thigh highs. Also, I have some black velvet high heels. I love it so much! I hope you approve!
That sounds super, super sexy Minerva, especially the black velvet heels. I bet those look stunning! Would be happy to have you serving as a naughty maid at my place. <3 <3
So this one was fun for me because I can’t buy/hide my sissy wear. I took a pair of all jeans and made them into daisy dukes and yes you guessed it, an old plaid button down that I took and tied into a knot. Humiliating? Yes. Fun? Yes!
I’m so happy you enjoyed it, Lacey. Thank you for creating something fun 😀
So. Much. Fun! Thank you for helping me with my option paralysis, Ms Riley – you helped me find something that really made me feel good about my body. Just miiiight have gone overboard with all the crazy strappiness but in the end I like the bondage-y vibe.
Your recommendation of the sheer robe totally made the look. Hope its OK I put the pics on EE 🙂
I LOVED THEM, great job Krissie you looked HOT!