Olly Jackson | 1996 | 168 cm | 51 kg | Bangor (UK)

When I started to gain more confidence, I started making videos, and found that I love the camera, and the idea of people watching me is very hot!

Olly Jackson on Twitter


MasterMarc: Hi Olly. You’re the first very kinky FEMALE-TO-MALE transsexual we do an interview with. You’re a nice, submissive boy and you love to live your kinks. When have you realised that there is more than vanilla and to be used hard in sex is a big turn-on for you?

Olly Jackson: I think I realised that I love kink around the age of 18, when I started exploring my sexuality more. Watching different kinds of porn was definitely an influence in this, as when I see something new, I want to try it immediately to see if I like it! Luckily at that time I had a long-term partner, so trying new and exciting things in sex wasn’t scary at all as we trusted each other a lot, so I was able to explore kinks and fetishes to my heart’s content!

MasterMarc: You’ve been a lucky guy with a partner who was ready to explore your kinks. A trustful environement helps a lot to open new gates. What have been your first steps and how have your desires developed?

Olly Jackson: My first steps into kink were fairly vanilla compared to what I like now; I believe it was just basic bondage with handcuffs! I just love the feeling of being helpless and entirely for someone else’s use. While I definitely still enjoy that, I’m excited by other kinks and sexual activities too, such as spanking, choking, being degraded, and wearing a collar. That leads into probably my biggest kink, which is puppy play. It’s something I’ve only discovered fairly recently, but I’ve absolutely fallen in love with it and can’t wait to do more with that community.

MasterMarc: Can you tell us about the attraction puppy play has for you? Why do you love to act as pup?

Olly Jackson: I love the praise aspect. While I do love being punished and degraded, being praised and being called a good boy or a good pup just really turns me on like nothing else. I also love the loss of control; when I’m told to do something, I have to do it. Puppy play is something that can exist outside of sex as well; it’s not just sexual, it can be very affectionate and intimate. If a partner calls me “pup” casually, it makes me incredibly happy to know I’m their pup both inside and outside the bedroom.

I don’t think of myself as ever having really been a girl; only that for 16 years, I believed I was a girl, but then I finally figured out that that wasn’t me.

MasterMarc: If the fetish conquers also the live outside the bedroom it becomes really great. I understand you totally. Some pups would say that petplay is a role game, but which includes a lot of your own personality. But it isn’t the biggest role you’ve ever played. Probably it is too simple to say, but it was your role as girl, a fact documented by your body but a role because your feelings have told you something different.

Olly Jackson: I don’t think of myself as ever having really been a girl; only that for 16 years, I believed I was a girl, but then I finally figured out that that wasn’t me. I’m just a guy who happens to have been born with a vagina and breasts! I’m a lot more comfortable in myself now that I look the way I want to, with more masculine features, a low voice, and a flat chest. Everybody I meet sees me as the man I am, and that’s very important to me.

MasterMarc: I understand that it is important to you to be recognised as that what you feel, but i can imagine it wasn’t a easy time to reach this point. Have you ever had any doubts and how has your environment reacted?

Olly Jackson: It definitely wasn’t easy! As soon as I realised that I was transgender, I didn’t have a doubt in my mind that I was male. For the first couple of years after I came out, my parents still treated me as a girl – I don’t resent them, as it’s a hard thing to go through, realising that your little girl is actually a boy. They’re absolutely fantastic now though, and were very supportive after my top surgery. High school wasn’t much fun after I came out, because teenagers will pick on anybody different! But since I’ve been at university I’ve really become confident in myself, as even though my friends know I’m transgender, people there have ONLY known me as a man and never as a girl.

MasterMarc: You’ve told us about your partner who was up to try new sexual things and to explore new kinks together. How was it with your trans-sexuality?

Olly Jackson: They were also transgender so it was totally fine! I’m bisexual, and have had both male, female, and nonbinary partners from all walks of life. Since that first kink experience I’ve been with a lot of people who have never had sex with a transgender man before, including a lot of gay men who loved it. It’s always a risk I take, as I never know quite how someone will react when I tell them I’m transgender, but on the whole it’s been good experiences. Gay tops love fucking both my holes; at the end of the day, I’m a guy who just happens to have a bonus hole to play with!

MasterMarc: At the end you are a boy with three holes. That’s definitely not uninteresting. Would also be perfect for a foursome with three tops. 🙂 Or what do you think? Btw. how do people react when they see your vagina, a word most of the guys are not able to spell?

Olly Jackson: Haha, no it’s definitely an interesting factor for me! I’ve had several threesomes and really enjoyed them, I love the feeling of being used by one guy so being used by two is even better! I’d definitely like to try a foursome, three tops fucking me would be amazing and I’m sure I’d enjoy it a lot.

I’ve never had any complaints about my bonus hole! Several guys have even said they prefer it to fucking my ass, as we don’t need to spend time prepping or using lube, we can just get straight down to fucking 😉

I like my vagina, especially now that a few years on testosterone has made me grow down there!

MasterMarc: Hehe, that is really an advantage. But what is your relationship to your own vagina? I am just asking because you feel as a man, and at the end there is something which is showing you that something has got wrong with the nature as you have been born and that there is still a female body?

Olly Jackson: I like my vagina, especially now that a few years on testosterone has made me grow down there! Every transgender person is different in their beliefs and feelings about their body, and the way they think about it, so I definitely don’t speak for everyone in the trans community – but I believe my body is male. I know that sounds odd! But since I am male, and my body belongs to me, therefore my body is male. It just happens to have a vagina. And since that vagina is mine too, it is also male!

MasterMarc: That is a very good point of view and I think this self-confidence is important to have. So you will not do any surgeries in this body region?

Olly Jackson: Having confidence in myself and my body is incredibly important to me, so thank you! I’m not sure yet; my mind might change later on in life, and I’ll be able to ask for more procedures if I choose to, but right now I want to keep my vagina. Later in the year I will be asking for a referral for a surgery called a clitoral release, which will make my dick (what I prefer to call my testosterone-enlarged clitoris!) stand out more. I definitely want to keep the hole – why get rid of something I like!

MasterMarc: You’re really open with this topic and even in your Twitter can see you with breasts. How important is it for you, that you are such an outgoing person and is it the reason why you’re doing porn now?

Olly Jackson: Very important! I started putting up nudes on Tumblr and Twitter so I could feel better about my body – I already knew at that point I was going to have top surgery to remove my breasts, but I also knew there was nothing wrong with feeling good about myself. When I started to gain more confidence, I started making videos, and found that I love the camera, and the idea of people watching me is very hot! A huge part of the reason I do porn is to spread some of my confidence. I know I’m incredibly lucky to feel good about myself in this way, as body confidence is a huge issue in the trans community, and a lot of trans people genuinely hate every inch of their bodies. If I can show that you’re allowed to feel sexy, you’re allowed to feel wanted and desired; if I can help trans people to take control of their sexuality, through porn, I’ll be incredibly happy.

There’s quite a common misconception that all gay trans guys are bottoms, but this definitely isn’t true.

MasterMarc: I think in this point you have a big advantage compared with other transexuals without your self confidence. Would you say that as Trans Boy you’re a natural born bottom boy? And what is the attraction of dominance?

Olly Jackson: For sure, as my confidence has allowed me to go to Spain to film with Boynapped, and I’ve met some amazing people there!

There’s quite a common misconception that all gay trans guys are bottoms, but this definitely isn’t true. Trans guys can be tops, bottoms, or versatile, just like cis guys. I know trans guys who are exclusively tops, and won’t bottom for anyone! Personally, dominance for me is about pleasing my sub. As a submissive, I like to please my dom – I guess I’m just a pleaser! I want to create an environment where my sub can be however he wants to be, with a dom perfectly suited to what he wants and needs in that moment, whether that’s an intimate and caring dom who tells him he’s a good boy and he pleases me, or a dom who makes him feel used and only there for my pleasure.

MasterMarc: Is this need of dominance just a sexual desire or includes it more?

Olly Jackson: I think it’s definitely something a little more. I like to feel looked after, like I’m not totally alone and looking after myself – there’s someone there, at the very least looking after my sexual desires. I can’t be dommed by a random stranger – there needs to be at least a tiny bit of connection there, a little bit of trust, because I’m giving them my body and letting them use it for both of our pleasure. I have a huge amount of respect for guys who can do random Grindr hookups, especially when they’re kinky! My favourite kind of sex is when I’m being dominated by someone I’m close to, as we can push boundaries even further, because there’s that level of trust.

MasterMarc: Trust is the base of good sm and for me SM cruising is definitely not something i’m into – normally 🙂 . What means for you “a little more”? Are you a slave type if you find the right dom?

Olly Jackson: By “a little more” I mean it’s about that trust and care aspect, not just sex. And I’m not much of a slave, I’m not really into the 24/7 servitude stuff – I really like to have my own time to focus on myself and not be at someone’s beck and call, but I can fall into a submissive puppy state of mind when I want/need to, and be totally willing to submit to my dom when we’re in a sexy mood.

MasterMarc: Now you’ve really to tell us about your hottest experience you’ve ever had as submissive.

Olly Jackson: Oh man! That’s a really hard question… I’ve had quite a few experiences that stick out in my mind as exceptionally hot. But the one I’m choosing was with an ex boyfriend. He had been visiting friends abroad for a week, and as we lived together, I missed him very much… and I really missed sex. We were sexting and sending nudes to each other all week… sometimes even in public, like he would tell me to go to the bathroom and send him sexy pictures. When he came home, I picked him up from the airport late at night, and he didn’t even wait to get home to start touching me, he was playing with my dick (clitoris) on the car ride home… I had to try hard to not be distracted from driving, I was going crazy for his touch! When we got into our bedroom, he told me to strip and put on the new underwear he’d bought me, an Armani jockstrap that’s still my favourite. He told me to sit on the bed, and that i was only allowed to make pup noises, then he fucked my mouth. Then he flipped me over, tied my wrists to the headboard, and fucked both holes until he came in my ass, all the while he was calling me his pup, his good boy, and I still wasn’t allowed to make “people noises” – and I loved every second of it. After that he sucked me off until I came too. It was probably the best night of my life.

MasterMarc: Sounds like a great night. Are there still some fantasies and sexual practices you would really to try in the future?

Olly Jackson: Absolutely. I would love to try rope play, I think it looks really beautiful when done properly, and if I meet someone who’s into some more extreme stuff… well, I wouldn’t say no to trying some more out-there stuff. I’m pretty adventurous and I’ll try anything once.

MasterMarc: I am sure you will find guys to fulfil your desires and dreams as you seem to be a strong guy who knows what he wants. We wish you a lot of luck and fun for your kinky life as private person and in front of the camera.

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