AMA - 29M 4-years Anniversary

[JimmyKarlo]

Its now about 4 years while I am sneaking around on GD. And since this is kind of an anniversary I would like to take the change to open up my AMA.

Please feel free to ask and I will be as hones as possible.

Cheers!

[xxyyzz]

when was the first time u tried anal nd how was ur experience give a brief

[JimmyKarlo]

Uh, the fist time anal was during high school times. With my friends that time we stated to fool around and got into putting things in your ass and also putting your cock into each other’s ass. It was no fucking, but for me it felt really good and I liked getting my ass filled somehow. One of my friends had a quite thick cock and could not put it in the first time, but I was so curios that I managed to train a bit at home with my still limited experience at that time, that during another occasion he could slip it in - it even made him cum and I felt so stretched and good. This was for sure the starting time.
In total there were three guys: one liked to put things in my ass and to also stretch me, with one I we wrapped it into a kind of competition to wrestle on the floor and grab and suck each others cocks…looser got the ass filled. Here also no real fucking, just putting it in as humiliation and of course I lost quite often. And there was the third one with the nice big cock simply putting it in*. I never had any guy experience afterwards.

*fun fact: later he had a gf, quite a small one and she complained about his way too big cock and that she barely can take it :P

[PlayfulCurious]

What was your longest time in chastity?

What was the best sex in your life and why?

Describe a perfect session that would fulfill all your dreams and desires.

[JimmyKarlo]

What was your longest time in chastity?
I am still a beginner and the longest time so far is a about 12h. I started around noon and managed until midnight. Also this was the first time I kind of went out with the cage to be around others. Amazing experience.

What was the best sex in your life and why?
The best sex was with my ex after we broke up. I was back in town and we had a couple of cocktails and went to her place. We were so horny that we directly jumped on each other. She was so dominant that evening and made me lick her feet and ass and pussy before I was allowed to fuck her. She wanted to get fisted by me, since I have larger hands than she has -- in the past she did some solo fisting from time to time, but she wanted to get something bigger. So we also used her thick dildo, her hands and finally mine. In the end she wanted my cum in her so I fucked her wide open pussy with everything I could -- she started fingering my ass and then she asked me, if I would like to have some toy too -- and I was like "hell yes!". She asked which one I would like to have and I told her that's here choice. She chose her still wet biggest dildo and shoved it into my ass and fucked me while I was fucking her. She started rubbing her clit and had a massive orgasm which made me came so hard too! Still with the dildo inside, she allowed me to lick her used and open pussy clean from my cum. It was the best, rough sex we ever had.

Describe a perfect session that would fulfill all your dreams and desires.
Uh there are many dreams and desires where I have fantasies for, but lets got with this one: Since I like worshipping my ex she kind of knows my kinks and messaged me one day, that her husband would like to fuck an ass and that she would offer mine -- she's not into anal at all and as far as I know, never let anyone fuck her in the ass. But to make her husband happy, she tought of me.
She told me to be prepared, since her husbands cock is really thick and she even has troubles sometimes with her pussy fucking him (although she likes big and does some solo fisting from time to time). So I plugged myself with my inf. plug and waited for her to summon me to her place that evening. She texted me and I went there, plugged and cage of course. I had to stay in the room naked while those two where fucking. She had my chastity key on her ankle braclet and I could see his massive cock and her really fighting but enjoying it. I was just sitting in the corner preparing my ass with a big dildo to be ready. They fucked for a long time, she came a lot and her pussy was filled with his cum and she was completely exhaused and done in the end.. but he was still full of energy and ready to cum another time. She just layed there on the bed barely away with her legs spread and he told me its my time now -- I was so despread and horny and in quite an emotional state seeing my ex in this situation. I had to get doggy on the bed with my head infront of her cum leaking read swollen pussy and my ass up in the air. He did not even used a finger, but just put his tip on my hole and slowly started pressing.. he was so hard and thick and at the point when his tip entered me I was again leaking a lot. He went balls deep in me after a while and I could feel his balls touching mine. My ex gave me some of her pussy juice from time to time while he fucked my thight asshole for quite a while. At some point I felt his cock getting even harder and he was about to cum. I felt his cum squirt into me, although he came already a couple of time in my ex. He pushed back my plug into me and told me to get dressed and leave them.

Something like this, or similar ones including chastity, my ex, anal, feet worship.. all would be perfect

[PlayfulCurious]

Would you give a longer period of chastity a shot?

Even with someone else controlling the keys?

Do you still have regular contact with your ex?

[JimmyKarlo]

Would you give a longer period of chastity a shot?
Absolutely! I try more often to keep it as long as possible, but still don’t feel fully secure to wear it during daily business and I can not stand the full night yet. I am working on it. Especially during weekend etc.

Even with someone else controlling the keys?
Especially then! Did not have the experience so far, but I really look forward to it. Many of my fantasies gather around having the key controlled by another person. My ex, sone of my female friends, or flatmates… many ideas on that.

Do you still have regular contact with your ex?
It depends, we basically text from time to time like every half of the year, maybe Christmas and birthdays. Not too often though, and it’s nearly almost me who starts texting.

[Josh.white97]

Based on your fantasy above, do you like threesomes? MxMxF? Have you ever had any?

What is your extent of exploring with other men? Does a woman need to be present / involved? Would you be turned on with a man if he was helping you explore your fetishes?

What is your top fetish? What is your ideal way to act on it, if you could choose any way with no consequences?

What is your favorite toy or item to penetrate yourself with? Do you like having men cum in your ass? Do you prefer women to penetrate you?

Have you ever been double penetrated or would want to? What about getting penetrated turns you on so much?

[JimmyKarlo]

Based on your fantasy above, do you like threesomes? MxMxF? Have you ever had any?
Unfortunately, I never had any threesome, but I would be absolutly open to it and would love to try! The best would be as a cuckold/slave also as bi-part, but I would also would go for a simpler one to fill the holes of the lucky F together with my M mate.

What is your extent of exploring with other men? Does a woman need to be present / involved? Would you be turned on with a man if he was helping you explore your fetishes?
Basically it all started with male-only. During high-school three male friends of mine, we played and fooled around together and this lead to different things with them: one loved to put things in my ass like pencils or other toys, another one we had a game to grab/suck each others cock, looser gets the cock of the other in ass (we never fucked), and the third one was just curious how it feels to put his (quite fat!) cock into my ass. It was really a good time -- I really enjoyed it, but of course I could not show it.
But now, somehow its much more a turn on, if a woman is involved. Not sure about a single guy...

What is your top fetish? What is your ideal way to act on it, if you could choose any way with no consequences?
Puh, top one probably anal (closly followed by heels). If it would be without any consequences, I would love to hook up regularly with couples or even guys to get my ass fucked. Plus some femdom involving wearing plugs etc.

What is your favorite toy or item to penetrate yourself with? Do you like having men cum in your ass? Do you prefer women to penetrate you?
Favorite toy so far, besides my inflatable plug, was a about 6.5cm wide long black dildo. Unfortunately I lost it during moving, and I was not too well trained at that time, but as soon as I was warmed up I loved to ride it under instructions from online partners or in former times via video chat with my ex gf. For fucking now, I like my 5cm suction cap dildo -- good size for different styles, but could be bigger.
I had cum only a couple of times in my ass -- from my initial high-school friend play around (as described above). It was never real fucking, but some of them simply cum in my ass after a while and I could feel their cock pulsating and the warm cum in me or when it was dripping out. I felt so slippery and used afterwards.
My ex gf used a dildo a couple of times on me, it felt amazing! I love having women penetrate me, I really enjoyed it! Nevertheless, I would also go for a good cock!

Have you ever been double penetrated or would want to? What about getting penetrated turns you on so much?
Double penetrated in terms of two cocks in my ass... it never happened, but I tried with smaller dildos and its definitly a good stretch! If it would be two cocks... that would be amazing! I would definitly give it a try!
For me getting penetratated gives away the responsibility and control about what happens and when it happens and when I orgasm. I really love the feeling of simply enjoying what happens.

[Josh.white97]

Do you think you could ever date a guy? If he allowed you access to play with women as well?

Do you like penetrating others anally? Or just like receiving ?

When you date girls, do you often tell them about your desire to be penetrated by dicks?

Would you want to try cuck play? And either have your gf be fucked by another man or her watch you get humiliated and penetrated by another man?

[JimmyKarlo]

Do you think you could ever date a guy? If he allowed you access to play with women as well?
Most likely not. I am not really attracted to guys -- except getting fucked by a nice cock. The other way around like a women that allowes me to get fucked by a guy sure would work. I thing for a relation ship I definitly need a woman.

Do you like penetrating others anally? Or just like receiving ?
Mainly I am into receiving anal, either via strapons or dildos or a real cock. But, I would also return the favour of course. Not sure, if I could fuck a guy, but for women absolutely. Although, I never had the chance to really fuck anyone anally myself. Same holds for toys I guess. I once or twice put my cock into the ass of one of my friends (see questions/answers above), and I also cummed by accident, but simply because I was so horny.

When you date girls, do you often tell them about your desire to be penetrated by dicks?
I never had the chance so far. With my ex I got into anal play -- she did not took anything up her ass, but after she found out that I like it, it was definitly part of our play. Although I liked it rough and big and the stretch of the toys, we did not reached this specific topic at that time. But since we did also some video chatting where she simply watched me fuck my ass while she masturbates, one might have come to this topic at some point. Generally with the girls I dated its always an development and find out what we like each other and see where it leads.

Would you want to try cuck play? And either have your gf be fucked by another man or her watch you get humiliated and penetrated by another man?
Absolutely! This is one of my favourite fantasies. Being locked up and my ass filled with a plug or dildo while watching her getting fucked by a big cock, barly handling the massive thrusts he puts into her holes. Kissing her hands and feet while she enjoys herself, and licking her used pussy afterwards... simply wow. And also then kind of swapping, when she watches me getting fucked by a nice big cock, trying to be a good sex toy as she is. Absolutely a dream!

[Josh.white97]

What about anal turns you on so much?

Could you ever date a girl monogamously with no contact with a guy ever again?

Would you prefer some sort of polyamorous situation with a guy and girl to fulfill all your needs?

Could you be a sub to a guy if it’s just purely sexual?

[JimmyKarlo]

What about anal turns you on so much?
I think the main reason is to loose control and be fully submissive especially if its done with a partner and one is in the hands of the respective other. Plus: it really has some complete new feelings, even if one does it alone using toys. For me anal really gives the extra kick and satisfaction. I can jerk off by my self, but at some point I carve to have my ass filled and this feeling only grows until it get satisfied.

Could you ever date a girl monogamously with no contact with a guy ever again?
Yes, maybe, that this is possible. I think, if we have a good swing in sex life it might not be necessary, but who knows. If she keeps my ass busy, then most likely yes, haha. But it might happen still in the end to spice things up, if she also would be into it as well. Could be that she likes to get fucked by another cock, or she would like to see how well I can take it as well.

Would you prefer some sort of polyamorous situation with a guy and girl to fulfill all your needs?
Maybe this would be something interesting. Probably I would go for a fixed girl, but not sure about a fixed male partner, that might be strange for me and in general. Fixed girl to build up a nice relation ship and then maybe something more flexible like random guys from bars or other hook up for various adventures like she getting fucked, or I get fucked.

Could you be a sub to a guy if it’s just purely sexual?
Not sure in the end. If its only about getting fucked this could be. Simply a guy with a nice big cock, who trains my ass and I simply show up and get fucked this might actually work. Although, I think I have to be quite horny in the end to really push me in this direction.

[Josh.white97]

What advice would you give to someone looking to try receiving anal penetration for the first time?

What is your ideal woman looking like? What does an ideal man you’d like to play with look like? What about cock size?

Describe your own body

Do you like rimming or just penetration?

[JimmyKarlo]

What advice would you give to someone looking to try receiving anal penetration for the first time?
From my current experience: enjoy the ride, lube and excitement. Don’t be afraid if it gets messy from time to time, it’s normal. Be creative and don’t put pressure on yourself. Enjoy and listen to your body. Exploring alone gives some experience as well.

What is your ideal woman looking like? What does an ideal man you’d like to play with look like? What about cock size?
Woman: natural, a bit sporty, long hair and nice legs with nice finger and toe nails, with an sexy attitude.
Man: not too interesting in his body, but similar as for women, sportive, but his cock needs to be big, thick and not too long maybe with a nice curvature for the special kick

Describe your own body
Normal and tall guy, bit sporty, average cock with curvature

Do you like rimming or just penetration?
I’m in for receiving rimming and penetration, giving rimming I only like for women. Not too much into fucking a guy, but would go for it if in the mood. Women always.