Some of my fondest memories are my initial experiences with masturbation and how – at that time – it opened up a whole new world to me. I have received a lot of inquiries from men, regarding all things masturbation. Some want to know how I feel about it; others want to know if I like it on a more personal level. And of course I get questions about my own masturbatory techniques, and curiosities about what my “first time” touching myself, was like.
My Introduction To Masturbation
I remember it well, only because when I was growing up, I was always curious about sex, and it was never seen as anything shameful to me. This might sound funny, but my first experience masturbating, was with a pillow. I would sit up on my bed, on my knees, pillow between my legs, and grind against it. I didn’t wear panties to bed, so that part was easy. The first couple of times I did it, it felt really good, but I didn’t cum. I would just enjoy the sensation of my lips and clit, rubbing against the fabric of the pillow.
My First Orgasm
To be clear, I am not really sure what prompted me; whether it was something I read or something I watched. I used to read a lot of erotica, and still do. But I also used to watch late night skinemax, so I’m sure something I saw on the telly, sent me racing to my bedroom for some alone time.
All I know, is that I slipped out of my shorts and panties, straddled that pillow, and started rubbing myself against it quite enthusiastically. I remember my clit feeling engorged and much more sensitive than normal, and it felt so good that I kept going. Then there was what I can only describe as a white hot flash the surged all through my body as my pussy spasmed. I might have screamed, or made some other surprised noise at the sensation, and then collapsed on my bed, pillow still between my legs – along with a very prominent wet spot – and fell fast asleep.
Experimenting With My Pleasure
After that first mind blowing orgasm, I knew I was onto something, and began experimenting with my hands. I figured out what worked for me, and what really got my motor running, nipples hard, cheeks flushed. But pillow humping was always my go to, when nothing else would do. Still is to this day. From that point forward, I found that I also enjoyed watching other people cum, both men and women, and mutual masturbation.
Watching a man stroke for me, and – if he’s not an orgasm denial slave – watching him cum, during a JOI session, is one of my absolute favorite activities. For me, it’s all about not just seeing their pleasure, but hearing it. I like the sound of them stroking, the facial expressions, the sounds of their moans, whimpers, and wails as they shoot off and the fireworks happen. Keep this in mind when you call me for, guided masturbation, and teasing. I’d love to chat with you about your pleasure, as well as answer any questions you might have about mine, and all the many other things that get me off.
Until next time…
Your Enchantrix Tease Mistress Brighton
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Can I be your pillow Miss Brighton? *squirm*
Oh Peter… you can’t be my pillow, no, but if you’re lucky I might let you sniff my pillow after I’m done with it. 😉
Well since Peter took the pillow, can I be the bedsheets with my mouth open and tongue out catching the juices dripping down? Great post; I’m always fascinated by how Mistresses got their start, so to speak. And joint sharing of experiences, like joint masturbation, makes for a better conversation. So thanks for sharing this. I really enjoyed reading it and look forward to sharing back someday.
Thank you bfla, I’m glad you enjoyed reading, and you should know that my juices are a special privilege. 😛
Mistress Brighton I will never look at my pillow again as just something to lay my head on when I am sleeping!I admit I have used my Pillow as something to hold on to nice and tight as I am laying on my Tummy in bed Dry Humping my Mattress Dreaming of being with a Goddess as Beautiful as you are Ms.Brighton Serving & Servicing you as your Little Sissy Cuckold!~Sissy Winks!~ 😉
Hahaha well sissy faggot maybe I will start a pillow humping revolution.
Does dressing guys in wig/bra/panty/slip/heels and lipstick get you off? This is only way I can get hard and off. If you are interested in doing this to me. Im interested then.
Yes Petey I love turning submissive men into my perfect little sissies. 😛
I’ll feel out of place if everyone sees my bra under my shirt:( if you make me wear lingerie/bra/panties/slipI’ll be a sissy. I can’t wear that! I’m a guy:( your not going to make me wear those body con sheath dresses are you ? I smell like Victoria’s Secret pink as well:( Your not going to apply that burgendy lipstick on me? 🙁
Dear Mistress Brighton,
This is a great post! Masturbation is a topic, which I enjoy discussing, because I recognize that it is healthy, and sex, in general, is healthy. It is also important to set aside quality time for masturbation.
In my case, I am into strict orgasm denial, as I am into the BDSM lifestyle as a sexually submissive male. I require guided masturbation, because my 8 in. long one-eyed snake needs to be charmed. For this I seek out the LDW mistresses, and I also have several in-person mistresses, with whom I party with, along with a couple of other submissive males.
Like you, I also enjoy watching other people (men AND women) cum, and I just love to stroke my cock in the presence of dominant women. I do, such as during the month of May, set aside a day for masturbation marathons, which can last up to 9 hours. Since I am into orgasm denial, I just enjoy bringing myself to the edge over and over again. That is sufficient to stimulate and satisfy me. This leaves my penis being very sensitive and keeps me horny.
I am also into CBT, which I find is a good supplement to masturbation. How do you feel about that? I hope to read more about your masturbation experiences. Thank you for a great post!
Wow…. i feel spoil by u mistress..
Who being your boy is very lucky. U r so nice, hot and confort.
Ouh….. your pussy juice, i very dream it…ehm….
I used to hump my pillow .Now i ended up like this .CD / TS. Tiny penis sissy bending over for a strap-on Mistress or backing up on to a suction cup wall mounted dildoe
I bet you look so cute humping your sissy pillow! Hahahahahahahah!