I’ve recently been interviewing boys via Facebook and instant message about the sessions we have done. This is an interview with Sissyboy – a very hot 24 year old who first came to play with me when he was 21.Β  I asked him about his first session with me….

Andrew: Tell me what made you come over for your first session?
SissyBoy: What made me look for sex or what made me come to you?
A: Start with what made you look for sex?
S: Well I have always been very horny, even from a young age and always knew I was interested in cock, but being “straight” meant it was hard to look amongst my own group of friends. And so I started signing up to dating sites.
A: And what kinds of sex were you looking for?
S: At first I was just looking to suck some cock. I had done it a couple of time before when I was really young, and wanted to explore that side of my sexuality. I was 17. But as I got older, and spent more time trawling the internet I started to find more risquΓ© sites and leant that I really really wanted to be tied up and fucked. Also became very interested in whips, nipple clamps and other forms of pain
A: Did you do any solo play with yourself?
S: Yes I probably spent about about 18 months doing little things to myself, mostly involving putting whatever I could find up my bum. Also I loved to cock tease on web cam during this time
A: So when were you first fucked?
S: LOL. I don’t remember. I had been sticking things up my ass wanting cock for such a long time, it was never really a big thing when it finally happened. I know I had 3 guys fuck me multiple times over a pried of about 6 months I just can’t remember who was first.
A: Tell me about them…how old were they?
S: All much older between 30-40, all lived local
A: And how old were you?
S: 19-20
A: When was your first BDSM experience?
S: Well I had one guy tie me to his bed, but that was kind of uneventful, it got to the point most guys I spoke to seemed to fall into two categories. 1, the people who welcomed the idea of tying me up and using me, but I would get there suck there cock for 10 minutes then they would blow and I would leave. 2, people who just sounded way to creepy, for me to feel comfortable putting myself in that position. And then you messaged me sir πŸ˜›
A: Do you remember how we met?
S: Like it was yesterday πŸ™‚
A: I meant on which website? πŸ™‚
S: Biaustralia I believe
A: Correct. Why did you decide to play with me?
S: The phone call
A: Tell me about it
S: Well it was odd, I never usually talk to guys on the phone, but for some reason I can’t remember I decided to let you call me
A: And what happened?
S: You sounded so laid back, you where relaxed, yet confident, I don’t really know how to explain it but I just knew I had to experience what you where offering
A: And what was I offering?
S: A night I would not forget πŸ˜›
A: So you decided to come over – describe your first night
S: Do I have too? it’s sooooo embarrassing
A: Go ahead, slave
S: Well I get there a little early had never been to that part of the city before so I wanted chance to find a place to park. I messaged you to let you know I was there, you told me off for being early and to come back on time, so I want for a bit of a walk and came back 10 minutes later. Then as I tried to enter your building I found the door was locked. I messaged you, and your reply was simple, “pull it”
A: Yeah, you weren’t off to a great start
S: As I pulled the door open…… I think I turned bright red and knew the tone had been set for the evening. Up the elevator I went to your floor and then a short walk to your door. I took a deep breath and knocked on the wooden portal to an unknown abyss in front of me. I then turned around and closed my eyes as instructed. Your door opened and a blindfold was placed over my eyes
A: How did you feel?
S: Nervous. And excited
A: So what happened in that first session?
S: And embarrassed that I could not work out how to pull a bloody door….. After being pulled inside just remember you wrapping your arms around me, from behind. And then resting your chin on top of my head…………..At 6ft I’m not a short person but knowing you were at least a full head taller then me. Well it was too late for me to back out
A: But you had a safeword?
S: Yes, but when I discovered your size well I knew if you wanted to keep me there against my will there would be little I could do to stop it
A: And then what happened?
S: I was pushed hard against the door I had just entered, and striped. You spent a few minutes exploring your new property. I stood there naked, and blindfolded not willing to protest
A: And then what happened?
S: I remember a heavy weight being placed around my balls. And then I was lead further inside. I remember feeling so disorientated. I had never seen you place before so I had no idea where I was going, had been, or come from
A: We’ve played a few times – do you remember the first session clearly? or have they all started to blend into each other?
S: The others have started to blend but the first stands out
A: So what else did I do to you?
S: I was tied to your couch you, remember you were always taking photos. Every time you I changed position you would take a few shots
A: So what positions did we try?
S: I remember having my ankle cuffs connected to the weight on my balls. Loved that feeling
A: Yes, you do seem to react really well to pain. So what else happened that first session?
S: Your cock
A: What about it?
S: I remember being ordered to feel it though your pants and thinking to myself wow that’s a nice size. I had no idea just how right I was. After I was allowed to take it out and play with it, it started to grow and grow
A: The largest you’ve played with?
S: It felt as big a as a coke can
A:That’s because it is.
S: By far the biggest. I was thinking there is no way in hell this thing is going up my ass
A: Hehe…well I proved that wrong
S: Indeed πŸ˜›
A: So what were the highlights of the first session?
S: After a bit more sucking and a few more pics, you carried me to another room (just another reminder of your size). You can not ask me that πŸ˜› The whole experience was a highlight – even the mundane things were fantastic
A: So what else did we get up to the first session?
S: Like when I was lying blindfolded and restrained to your sling as you were getting stuff ready. Every sound you made was emphasised though my brain
A: What kinds of sounds?
S: The clicking of the camera, the bang of metal, the splash of water, the thud of footsteps – and many sounds I could not translate
A: Was that your first time in a sling?
S: Yes
A: How did it make you feel?
S: I did not spend much time thinking of the sling it’s self to be honest, more interested in trying to work out what was coming next
A: And what did come next?
S: Toys!!!!!!!!!!!!
A: What kinds of toys?
S: Lots of toys, all different shapes and sizes. Mostly metal A couple of butt-plugs too. And they kept getting bigger. And bigger. And bigger
A: Did it hurt?
S: Not at first but as you started to reach my limit yeah. But it hurt sooo good
A: Any toys in particular stand out?
S: Not in the first session, just the sheer size of them was amazing (our second session was when you introduced me to my favourite)
A: Yes, it was the cactus, wasn’t it?
S: Yes πŸ™‚
A: Describe the cactus
S: It’s too good for words
A: Give it a go πŸ˜‰
S: It’s a metal toy about the size of an average cock, worth lots of bumps. And when I say bumps I mean bumps. Not like when you get “ribbed” condoms and the ridges are barely a millimetre high
A: How does it feel?
S: It feels so amazing. I can not give it justice
A: So what happened after the toys?
S: Well after some big toys and a bit of amyl ( my first time) it was time to get fucked πŸ™‚
A: What did you think of the amyl?
S: Really enjoyed it. It helped me relax so I could take bigger toys and it gave me a nice high too
A: And then you got fucked?
S: Yep πŸ™‚ To be honest, I don’t remember the fucking in much detail, because once that monster was inside me, I was gone. My mind left my body, and was of in a world my pleasure
A: Didn’t stop you from moaning lots
S: I always moan πŸ˜›
A: First time being fucked by a guy you’d never met before? Or seen before?
S: First time fucking a guy I had never seen before yes. But I didn’t care. It felt sooo good
A: Describe the fuck
S: I was happy to just lie there and take what you wanted to give me
A: And you took it well
S: It was by far my best fuck at that stage and remains to be by far the most memorable ever
A: How were you secured in the sling?
S: I had ankle cuffs clipped on to the sling and – what are those things my hands were in called? The long sock like things
A: Leather gauntlets
S: Yeah and my hands were inside leather gauntlets attached to the sling
A: And how long did the fuck go for?
S: Not long enough πŸ˜› I really don’t know my mind was on another plane I have no idea how much time passed. I just know I did not want it to end
A: And when it did? what happened?
S: I wanted more πŸ˜›
A: Did anyone cum?
S: I did πŸ™‚
A: Good orgasm?
S: After you fucked me you put a string of very large anal beads in my ass and started to masturbate my cock. God it felt so good. Every time I got close you would slow down or do something else. You must have kept me on edge for about five minutes – and then when you let me cum you pulled the beads out just as I was cuming. God it felt amazing
A: So what happened after you blew?
S: You asked if I wanted to meet you
A: And what did you say?
S: I said yes, but the idea of getting kicked out with out meeting you was hot too
A: When did I take off the blindfold?
S: While I was still in the sling, after I had cum
A: And I was disappointingly nice, huh? πŸ™‚ Some boys would prefer I was a really evil guy even when they aren’t wearing a collar
S: LOL. First thought was OMG he’s a nerd, but I didn’t mind
A: I prefer adorkable to nerd. πŸ˜‰
A: And then what happened?
S: I understand why boys like the whole mean guy thing, but your so awesome at what you do I would not have it any other way
A: And then we jumped in the shower and that’s when I discovered you were a total DILF. πŸ˜‰ Do guys get turned on by the fact you have children and normally fuck women? The whole ‘fucking a straight boy’ experience?
S: I don’t normally tell guys I have kids. When I was younger, guys seemed to like to play with the inexperienced “straight” guy πŸ˜›
A: How old were you that first session?
S: 21
A: We’ve played quite a few times since then – what has been some of the other favourite things we have done?
S: Everything πŸ˜›
A: Good answer, but let’s get specific
S: Candle wax, bigger toys, nipple clamps, fisting attempts, and last weeks electro was really fun. And some group fun
A: Yep. Talk about that
S: You doubled the amount of guys that had fucked me in one night πŸ˜›
A: How did it happen?
S: There were 4 guys including you and you all had turns fucking me πŸ˜›
A: And you didn’t know it was going to happen, did you?
S: I knew it was going to be more then one but I had no idea how many
A: Did I tell you that? I thought I told you it was probably just going to be you and me
S: LOL. Yeah you told me πŸ˜›
A: Damn. But you liked it anyway. And you never saw them until afterwards. It was annoying for me because one guy make you moan louder than the other three – and it wasn’t me. Thomas just seemed to hit the right spot, right?
S: Mmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmmm. Maybe πŸ˜›
A: I have your face on video tape – you loved the whole thing, but you REALLY loved the cum. Why?
S: I like the taste, but it’s also kind of a reward it means have done a good job pleasing somebody
A: So what’s left on your list of things to do?
S: Few things πŸ˜› A gang-bang (10+), want to do more with electro, long term bondage, more pain, few other things
A: Let’s try and make that happen πŸ™‚
S: Now? πŸ˜›
A: Well perhaps some of Soxster’s readers might like to volunteer for that. thanks for sharing your story
S: You’re welcome sir, any time.

And yes, the photo above is one I took during a session.Β Β  πŸ™‚