Anonymous

We really apologise for the tardiness of this response. We’ve got so many to answer that it’s frankly tough to get through them all! ;A; We decided to pick a group of characters and split them between us, just to not make it repetitive. And, as a quick reminder, this is for the playable characters only!

Haytham: I honestly think his first time ever was with Ziio, and it was very nice, slow and sweet. I think his first time would be one of those rare times where he’s very vulnerable instead of the sassy, suave, evil!Bond-like Templar we know him to be. 😛 Just imagining him doing it for the first time with Ziio makes me wanna cry tbh. If someone can write a sweet erotica to this, that would be great…

Connor: Ah yes our sacrificial virgin. >:D Now he’d fumble his first time and would ask his partner a lot during sex for some guidance, lol. I always imagine his first time to be with someone more experienced, and the experienced person having their way with him a little too much (rope darts to be included in the session). ;P

Ezio: Uhh…alright…MY first time….was..with……ehhhhhhhhhhhhhhh…
I think it was with Cristina Vespucci? I try very hard not to remember any memories of her–I don’t think my first time was even that great.

– Signore Ezio

Aveline: It’s sad that we don’t know who she married because I think that would be her first time although she probably fooled around for a bit with, say, Gérald (no penetration though) and maybe even Patience. ;D

Edward: I think his first time was with Caroline and during their wedding night to boot. I think it would be very sweet but a little awkward because they’re both virgins. And I can totally see Edward finishing way faster than he wanted, so he’d try to make it up to her by pleasing her in other… ways. ;D

Adéwalé: Likely during the time he escaped and joined the pirates. I can imagine the pirates bringing him to a brothel and paying for him to spend the night as part of his “initiation.” He’d be really nervous and likely charmed the, well, panties off the lady assigned to him when he offered to “service” her instead.

Shay: He likely lost his virginity early, maybe when he was around 15, with an older and experienced woman. Maybe it was a woman separated from her husband he met in a tavern who wanted to have a taste of a young inexperienced fellow. The woman probably wanted to have her ego boosted due to her separation and Shay was very much willing to do the part. He’d be very willing to let her take the lead.

Shao Jun: I can imagine her first time as part of her “training” as a concubine although it’s most likely not with another man, but with an experienced (and likely older) woman in the harem. I have this headcanon that when she joined the Assassins she was likely celibate for several years, so considering that she never had sexual relations with the Emperor it probably took her a while for her to use what she learned.

Evie: I think she’d be so nervous about it. A lady like her that’s so self-controlled would probably have a hard time letting go during intimate moments and she has to be coaxed by a gentle lover who has much patience (lucky for her Henry certainly fits the bill ;D). I think her first time would have her crying, too, because she’d get so overwhelmed by the emotions.

Jacob: Despite his reputation as the wild scoundrel I think his first time would be rather nerve-wracking for him. Yes, pretty much like Evie he’d be nervous, but he’d bury it under so much false bravado. He’d pretend that it’s not his first time, for instance. His face would be all bragging and smug, but his actions are a whole different matter. I can see his hands shaking and certain nervous ticks (like chewing his bottom lip and his eyes blinking faster and more often) would be really obvious.

~ Signora Paola

Desmond: Probably sometime after he left the Assassin compound and began traveling around, he met a girl on the road and she was his first. Both of them were nervous, since they weren’t sure of what they were doing, but Desmond took the initiative and made sure to give his girl a very good time. Lots of giggles, sweet kisses and reassuring smiles, that’s how it went.

Altair: I assume his first time was with Adha. Both became close friends and eventually their attraction couldn’t be denied. I believe it was her that seduced Altair into his first night with someone. She danced for him and he couldn’t contain himself with her. They lay down and began exploring and teasing each other bodies, discovering what the other liked.

Arno: I have a feeling Élise was his first and that it was a very romantic session at that. They both planned it so they could have a trip together, without no one to bother them. Arno would take the reins making sure she was satisfied before his found his own release. He would also whisper reassuring things to her, because he’s a sweetheart and she deserves that.

Arbaaz: He looks like he has much confidence, but probably got very nervous his first time, that I like to think was with Pyara. He probably seduced her and then, when the time came, got all nervous, only to be assured by her that he was doing it very well. His hands would tremble at touching her skin, but his actions get bolder as she reacts to his touches and kisses.

~Claudia

Oh my gosh, I think I disagree with my fellows. Unsurprising, given my “secret” Templar sympathies…

Desmond: I think that he lost his V quickly after escaping the farm, possibly with the first willing girl who wanted to take him for a ride. I expect she taught him quite a bit before they parted ways.

Arno: In this I actually concur with my fellows. Arno’s world was Elise, and I suspect until well after his death, there were no others.

Haytham: Given his travels and his upbringing, I suspect Haytham lost his virginity to a paid professional. Love was never really something he had in his life after his father died and his mother became distant. Until he met Ziio, I don’t think he saw women really as people because he’d never really known any strong, independent women.

Shay: I think Shay lost his virginity well before he became an Assassin. He grew up on the docks, which meant he had access to lots of booty, and I don’t mean the treasure sort. Given how adorable he is, I think he probably didn’t have to pay, though his first tryst was likely, again, with someone who shared her favours freely.

Aveline: I honestly think Aveline likely didn’t lose her virginity until she was in a long-term, stable relationship. In playing Liberation, she was very married to her work as an assassin, and never had time for romance and other sorts of pursuits. But I think romance would be important to her – there’s no ‘scratching the itch’ for Aveline.

Adewale: As a sailor and a gorgeous, strapping ebony god, I think Adewale had a harem in every port of call. But I think his first time likely happened while he was still a slave, and perhaps not entirely sought after.

Jacob: He was drunk and probably doesn’t really remember his first time. He just woke up beside her in a pool of vomit.

Evie: Wedding night with Henry.

Ezio: With the first girl he was able to charm with a cheesy pick-up line.

I’m afraid I don’t know Altair well enough to have an opinion.

~Rosa