I’m thrilled you’re joining us for today’s cock stroking assignment! When you’re a member of Olivia’s Cock Stroker Academy then these assignments are part of your …. ahem …. masturbation homework.
Blog comments and your phone sex calls
Thank you to all of you for telling Mistress everything … and I do enjoy knowing all your sex secrets! I do *know* that you are excellent cock strokers….yes, even those of you that get a lil stiffy when Mistress laughs at your little dick! You too can participate in My Cock Stroker Academy!
Olivia’s private sexy photos
As you know from last week’s masturbation assignment, you get extra incentive for your cock stroking assignments.
Your masturbation assignment
Put on a rubber band on your wrist. Wear the rubber band during your cock stroking session. We will be exploring the combination of pleasure and pain. It’s not intense pain, it’s just an exciting zing that I want you to try and then report back to Headmistress Olivia.
During your stroking you will ‘pop’ the rubber band at the end of each edge.
This will be a timed stroking session called Lucky 7!
Stroke for a total of 30 minutes. You can do one long orgasm edging session or a series of shorter edges. Remember, if you do shorter edges, you will ‘pop’ the rubber band multiple times during your stroking session.
You can wear the rubber band for the rest of the day, or not, it is up to you.
At the end of your stroking session, roll the dice, if you get a 7 or a combined 7, then you will cum at the end of the stroking session. If you get a number other than 7, you will not cum. ~smiles~
Soooooo…..Tell Me all about your experiences here at Olivia’s Cock Stroker Academy! I’m looking forward to hearing all about your masturbation when you combine pleasure with just a bit of pain!
Ms Olivia
Dear Milady Olivia,
Aaron here, well lets see I could not get to the first class there for I forgot where I hid the key in me fuzzies while in Milady Gemma’s ol stocks there… but lucky for me I found it earlier this morning. Well it found me…Little did I know that some deep snoring there will loosen up fuzzies and lo and behold the darn key fell right out!!!
Luckily for me I was already fantasizing about a… ell lets just say a certain type of situation with You and Milady Gemma, and a a result a certain part of my body was already “spring loaded” so to speak”. Well there Milady Olivia, that there ol falling key hit me “member”, sprung right back up, right into me waiting fingers.
So Now I have the key to the ole stockers locks and now I can quietly enjoy your cock strokers academy… now all I need to do is find a rubber band….
Guess that it be it for now,,….. need to rummage….hmmm Why is there “Nair” and why does it have a tag that says “bookie wookie lube” in Milady Gemma’s handwriting…and what disturbs me the most is the “smiley face” she drew that has an evil grin……
Well I look forward to “be cumming” to your stroking “semenars” Milady Olivia !
Aaron “bookman”
~laughs~ Oh bookie, you crack Me up! Do TELL….did you find the rubber band? What happened with the Nair? Do TELL! I’m thrilled that you’re IN the Cock Stroker Academy and are enjoying the masturbation assignments. Coming up some Guest Instructors will be here for your cock stroking pleasure (and pain maybe) and we’ll enjoy ALL of this tease and denial! ~grinz~ Sometimes you get the sexy tease, sometimes you get orgasm denial and sometimes you get surprises! I like surprises, don’t you?
lots of fun. snapped the rubber band a few times during the 30 minute timed portion, which was lots and lots of fun. but then no 7 for me, nope snake eyes ended my lesson. thats the way it goes sometimes i guess. Still lots of fun, and I look forward to the next lesson.
FANTASTIC! Mark! I’m so glad you liked the rubber band! I like that too! I like to give a bit of flexibility in these masturbation assignments so you can make them work for YOU but still give Me control. After all, that’s the whole point of tease and denial cock stroking games….it’s the surprise, right? Awwwww, snake eyes! Poor guy! ~grinz~
Choosing to do Multi-edging was a big mistake. Funny though what happened will bring a “smile” to the headmistress. I only got seven edges in during the thirty minutes, then rolled an eleven but when it came time to stop could feel it still coming so had to go from none to a ruined orgasm. It really was not the experience I was hoping for, having to hold my little head so tight to keep it all inside. Loved this weeks pic but wish like me it was a bigger one.
~giggles~ Awwwwww! You want a bigger photo of the Experienced Mistress just like you want a bigger penis? Now, that there is FUNNY, I don’t care who you are! I’m laughing so hard I can barely type!
BTW, I’m thrilled that you did in fact, give yourself a ruined orgasm. I’m fine with accidents during your masturbation assignments at the Cock Stroker Academy but you must stay within the spirit of the cock stroking homework. In your case, a orgasm edging ending in a ruined orgasm is a teachable moment, wouldn’t you say? ~grinz~
Thanks to a new stroker academy photo I was UP to speed and stroking very quickly. I didn’t go into the session planning for multiple edges or taking my time for one long one. At about the 1/2 way point I thought I was going to get through almost all of it without a snap, but I was wrong. I quickly went to the edge and from there on out, every few minutes found a sharp snap to my left wrist. The first few didn’t seem to make any difference, but then I found myself not stroking with my left hand at all. In a long stroking session I will switch hands many times, but once there was some pain in my writst, I stopped stroking with that hand. I did not lose my erection at all (thanks to the photo I think).
To wrap it all up I rolled my 2 six sided dice. I chose 2 normal dice instead of a 20 sider because I know full well the odds were better for an orgasm. No dice. 8. maybe next time.
~grinz~ Ohhhhhhhhh you cock strokers make Me smile! I love the rationale you used to try and maximize your chance of having permission to cum at the end of your cock stroking session!
So tell Me, I know you like spanking on your bare bottom, what did you think of the wrist snap? I like to find creative ways to give the experience of My control and your submission from a distance in these general instructions so I always like feedback to see how the instructions are working. Did you like the snap?
Oh and I’m very thrilled that you’re enjoying the Private Reserve photos of the Headmistress of the Cock Stroker Academy! ~grinz~
It was very different than a spanking. Give me a swat on the ass and I will instantly get hard. Give lots of smacks on my ass, and I will get hard. The only time I lose my erection while getting spanked is sometimes if I’m giving myself a spanking. Someone else, regardless of the pain, I stay hard.
The wrist snap was very different. It hurt, sure. But it also stole my focus. The pain in my wrist made me not want to think about that hand when I was stroking, I think. In one way it seems strange, but pain isn’t always the same pain for me. Clothes pins on my nipples for example will take my erection away very quickly. So I think the snap was sort of similar, but not prolonged enough to “distract” me. I could go right back to stroking and arousal.
everyone is wired different, but I guess I’m not a pain slut…just a spanking slut 🙂
What a wonderful description of the differences inherent in the love of fetish pain and other sensation play! You are absolutely right in your description of erotic pain. In fact, you’ve given Me an idea for a future blog post because NOT all pain leads to arousal! Pain play is much like erotic humiliation in that it is very specific and takes a certain amount of experience to ask the questions to know what to do.
I knew that the wrist snap would steal focus and for some, that’s even more arousing. Thank you so much for leaving your comment because feedback allows Me to do a variety of Cock Stroker Academy masturbation assignments that DO surprise you!
Oh and I had to laugh when you said you’re a spanking slut…..~grinz~ ya THINK?
Dear Headmistress, ive just find out your new blog and i want to join your cock stroking academy since i love playing with my dick a lot and i want someone to control it because its got a little out of hand in here. lol. what are the requirements for the admission mistress ? today i will do the assignment and by the end of the day i will surely sent you the report on how this homework. have a nice day mistress 😉 xoxo
Wonderul asif! Welcome to Olivia’s Cock Stroker Academy! You’re a member when you start doing the masturbation assignments. Report back here on the blog or give Me a call! Remember, for the password to the private photos, you’ll need to send an email. ~smiles~ Happy (or not) stroking!
…and then you ring a bell and we all salivate, right?
hmmmmm, reading that tommie I can’t tell if you’re joking or being cheeky!
I think tommie’s making a cheeky joke. Pavlov would approve.
I bet I could make pavlov drool! ~grinz~ I think you’re right Forrest and will get Ms Catherine to give him a *smack*….~laughs~
I loved this assignment. It played on my sensory fetish so nicely.
I love to edge and doing multiple edges during the half hour seemed, well just right. I got in five edges. Snapping the elastic each time made for an interesting sensation. Having edges that provide wonderful feelings that usually last a bit for me, followed by the sting of the snap made the edge sensation stop suddenly was interestingly different.
Then the moment of truth and luck. Well luck was with me rolled a 5 and a 2 and yea I get to cum. Of course I was not really ready to release at this point, I really love to edge, so I continued to follow the edge/snap for another 5 or 6 edges before I allowed my self to orgasm. And what a great one it was too.
YAY! I’m so glad you love the stroking assignment Forrest! We share a love of sensation play! I too, loved that snap while combined with the masturbation. It gives a bit of control while you’re doing the Cock Stroker Academy masturbation assignment on your own. YAY and you rolled the dices that allowed you to cum with the permission of Mistress! While I surely do love orgasm denial and chastity games, I also love when you cum and tell Me what an explosive orgasm it is! Thanks always for your thoughtful, interesting and fun comments!
being cheeky will get me spanked, right?
~laughs~ I just wrote that in a comment to Forrest! I said I would tell Ms Catherine but on second thought….. stern Mistress voice: Come here tommie and bend over for Mistress! ~grinz~
Just want to recap..Milady Olivia… that was a very amazing and unique experience to try that with the dice and the rubber band. I never really tried edging before like this. Once way back when with my ex/gf she had her fun with me doing this but no rubber band, about stroking and edging..what she would do instead was to apply pressure to m nipple with one hand while stroking with another, and as she felt me get closer to orgasm, she would “pinch” deeper on the nipple and twist.
The pain was exquisite, and she did not let me cumm until later, after I orally pleased her to her “repeated” satisfaction.
Sorry for the late reply… still getting wiped out at end of the day..this dang chest cold was fun enough…but the coughing is so much happy happy times, for the next couple of weeks (sarcasm there).
But the rubber band brought back a enjoyable memory for me, i a weird way… guess that means I am growing or something…oh by the way thankfully hit a 7. Never thought I would cum like that !
YAY! You hit a 7! Go bookie go! You know the cure for virtually ANY ailment is masturbation! ~grinz~ I love hearing that this brought back fond memories! Thank you so much for sharing that. I too, love the nipple play (for My nipples and for others) … it’s a great way to experience both pleasure and pain…just a little or a lot depending on how sensitive your nipples are! ~smiles~ I know you’re still under the weather, but get mo better soon!
I know I’m a little late to this but I want to share my experience as you instructed. I liked this assignment greatly. I have always enjoyed some pain with sex and find that I get more aroused with some CBT or nipple play. This assignment just fed my fantasies of serving you as a submissive. Of course I didn’t roll a 7 and was denied. How cruel like, and a Mistress can be.
Thank you so much for your comment subthomas! YAY! You liked the masturbation assignment in the Cock Stroker Academy! I’m happy to hear that….even though the dices were apparently against you since the said “no orgasm today” after your stroking session! ~smiles~
Again back here way behind trying to catch up..i think this was a great idea. I’m not sure what edging is but when we have our first call i hope to get caught up. So i hope u don’t mind but i had to change the assignment a little..instead of the rubber band on my wrist i alternated between my cock and balls. LUVED IT!!!! Guess i may enjoy the pain a little more than others. I hope the change doesn’t get me in trouble…or do i…i don’t have dice so in my mind rolled a 5..lol guess no cumming this time!
~grinz~ Thanks for your comment scott and I think it’s just fine for you to change the assignment….after all, these are general assignments and the mileage of each individual will vary. ~smiles~ Each of you has unique ways to express your erotic needs, desires and THRILLS! For Me, pain play is LOTS of fun! 🙂