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After 100 Days In Chastity I Came With The Best Orgasm Ever

Our Readers Fetish Life

Pup Jackson | 1989 | 162 cm | 48 kg | Washington (U.S.)

I had the urge to be so submissive and want to do all these things like degradation, humiliation and a general willingness wanting to serve someone.

Pup Jackson on Tumblr

Photos by Pup Jackson | The Shackler | Boundand | NanoBitez

sadOsamHow long have you already been living out your kinky side and how did you came to that?

Pup Jackson: I started exploring my kink side about 3 years ago and discovered my “Jackson” identity shorty after that. My journey to discovering this side of me was challenging at times with understanding why I had the urge to be so submissive and want to do all these things like degradation, humiliation and a general willingness wanting to serve someone. After joining some apps like recon and tumblr I started chatting with other kinksters who were very helpful in helping me understand different kinks and proper safe ways to experience these things. Pup play and bondage were my first two things that helped me open up and from their it turned into acceptance and then I started my tumblr where I felt accepted and embraced.

sadOsamWhats especially important for you there?

Pup Jackson: What is important to me in the kink community is to feel accepted, play safe and spread what I have learned to new people looking to get into it or sharing stories with other kinksters.

sadOsamDo you have special sexual and fetish preferences?

Pup Jackson: Yes, so I have many identies in the kink community. I identify as a Gamma Pup to my wonderful Alpha Nano Bitez, a slave boy, and my newest adventure into the ABDL community as a little. However I still prefer to be a slave puppy. Things like chasity, diet control, workout control, humiliation, degradation and being tied down and stored away until I’m needed are the scenes that really excited me and get me deep into headspace. Straight jackets, sleepsacks and other restrictive things that can keep me from moving or having control would also be some things that I enjoy and would be in one all the time if I could.

sadOsamWhat kind of guys do you like?

Pup Jackson: Typically I go for dominate guys who are very Good at controlling a situation. I do have a thing for slim to medium built guys but if the person has a great dom personality and is very good at it in a scene then that’s more my type. You can be a super pretty boy with nice built body but if you’re not very dominate in the bedroom I will loose interest in the person, vanilla isn’t my style.

sadOsamWhat was your hottest experience until now?

Pup Jackson: My hottest expirence hmm…. that’s a tough one as I have had many great experiences, however if I had to pick one it would probably be my first play session with my Alpha. I had been locked in chastity 100 days (not by my alpha as he wasn’t at the time) we met in Chicago for a weekend of fun and a get to know eachother a bit more since we had met the prior month. The scene started with him tieing my legs and arms in a pup like position so I had to walk on my knees and elbows, once in head space some Pup play followed by being laid on my back and edged some. My alpha then rolled me over and did some impact play with floggers and other implements. Once I was nice and ready he then proceeded to mount me and fuck me really hard. It was in that moment that he was fucking me both of us not breaking eye contact while in our Pup hoods and him stroking my bone that I had a deep connection with him and then I finally came after my 100 days of being in chastity with the loudest scream and best orgasm I have ever had. Then right after that my husband proceeded to fuck my alpha which still to this day is really hot to think about.

sadOsamAre there things/dreams you want to experience once?

Pup Jackson: I have so many!!! Currently the one I’ve really been trying to figured out and experience is to be a full service slave boy for at least a weekend if not a little longer. Being restrained and stored, made to sleep in a cage, be used multiple times a day with no pleasure release, shackled and made to cook and clean, just all that and maybe some more naughty stuff thrown in there that I’m missing.

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