"Hey Christian... Got a random question for you..." My roommate paused, looking curious. He's a young guy, only 19, and rather socially awkward.
"Ok, what is it?" He enquired as he continued his cooking.
"Have you ever been with an older woman?" I asked it without looking at him, made it seem as casual as possible. I didn't want to spook him, as young and shy as he was.
"What do you mean? Like slept with?"
"Yah. I know you've had a few girls over, but have you ever hooked up with someone significantly older?"
"Uhhhh" He was hesitant, we hadn't really talked about stuff like that, apart from a few comments about one of us having a girl over. "I can't say I have... All the girls at the University are around my age."
"Oh man, you're seriously missing out then. It's pretty amazing. They know exactly what they want and they know what they're doing." I was still keeping it nonchalant, just super casual, working towards my goal.
"Huh. Well, I guess maybe one day I'll learn that first-hand? Idno, it'd be fun I'm sure, I'm just not great at chasing girls."
"Haha so you'd do it, given the chance?"
"Well, I guess, if she was hot and not too old. I've still got to be attracted to her but the idea is kinda hot. I take it you've done it?"
"Oh hell yah, when I was your age, this older girl Cindy taught me a few new things. It was amazing..." I was nervous now, the time was coming.
"Wow, uh, lucky you. Damn that sounds great. I guess I need to find a Cindy."
Ok this is it. Now or never. "Well, funny thing is, Tanja, the Czech girl, thinks you're hot and she kinda wants to fuck you..." Tanja is my steady friend-with-benefits and she's 28. She spends at least one night a week in my bed and treats our place like it's hers. That includes walking around in next to nothing, maybe a t-shirt & panties, or leggings & a sports bra. She might have had a bit of encouragement in this from me, of course. The thought of sharing her with my roommate was a huge turn-on.
"Uh, wow, ahhhh, huh..." His nervousness was very clear, he was totally blindsided by the statement. To take the spotlight off him, I kept going. "It's no pressure, we were just talking about kinky stuff and how I used to share my girlfriend with other guys and she mentioned you. She thought it would be fun to be fucking roommates, going room to room and basically being the toy of the household. She also thinks you're quite attractive. Young, fit and innocent is a turn-on for her."
"Wow, I don't know what to say... That's pretty crazy. And you're cool with that?" He had totally forgotten about his cooking and was standing there a little stunned, looking at me.
"Haha, yah, of course. I told you I was a super open-minded guy, and come on, you having sex with her doesn't mean I'm going to have any less. Girls can go all night, unlike us guys! I think the idea is kind of hot as well. I'd be happy to share her. You'd get laid, I'd keep getting laid, she'd be in heaven, it's win-win." I was keeping it cool, casual and easygoing but inside I was trembling I was so turned on. The thought of her being the house pet was such a thrill. I loved the idea of being able to send her to his bedroom in the middle of the night or leaving her with him when I left for work early in the morning.
"Wow man, that's kind of crazy, I've never been asked something like that before. Hookups have always been something that happens when I'm drinking, I'm so awkward with girls". I could see his internal conflict. His shy, nerdy side was screaming "run!" but his horny 19 year old male side was excited.
"Haha don't worry, she'd need some drinks first too, she's actually kind of shy until she's had a few. It would probably happen late one night, after some drinks, when she's super turned-on. You'd basically get woken by some hot naked girl crawling into your bed. A pretty sweet deal if you ask me."
"Huh. Well, uh, yah, it doesn't sound too awful but wow, I don't know... I don't even really know her." Tanja had tried to get to know him a bit, even to flirt, but Christian rarely left his room and when he did, he had earphones in or a laptop nearby. It was rather frustrating for her, because guys usually liked her and Christian, while nerdy, was well built and logged regular time at the gym. His half Caucasian, half Asian features made him a quite attractive guy, although he was clueless about that fact, endlessly glued to a screen and terrible at social situations.
"Like I said, it's no pressure, I know that sort of thing isn't for everyone and I don't want her trying anything if you're not into it. She feels a bit guilty for wanting to fuck someone so young, as much as it turns her on. Just think about it and let me know. If you're down, it'll just happen sometime when she's ready." My heart was pounding. I was excited and nervous. It was risky, Christian was a great roommate, reliable and respectful and I didn't want to ruin it, but I thought this was a risk worth taking.
"Umm yah, I think I'll need some time to think about it, it's kinda crazy, never been asked something like that."