"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."
"Haha no stress, let me know, or if it's easier, just don't answer and I'll take it as a no".
"Ummm yah, I'll have to let you know." I took that as my cue to split, giving him some space and a chance to mull things over. He had reacted well though, I was afraid he was going to get super uncomfortable or that it could cause problems between us, but I had gotten a good vibe.
A short while later, I heard the door to his room close. I gave it a few minutes and slowly walked by, careful not to let any floorboards creak. Just as I suspected, I faintly heard heavy breathing and some quiet creaking coming from his bed. If I wasn't mistaken, my teenaged roommate was getting himself off and I was pretty sure I knew what he was thinking... I crept away, back to my room, to think dirty thoughts. Not 5 minutes later, I was startled by a ping from my cell phone. A text message. From Christian. "I'm in" was all it said.
A week later, Tanja was over for our usual, weekly "date night". Food, a movie, some beers and of course some no holds barred fucking. She was about three beers in when the movie finished and we started fooling around on the couch. Tanja's got a rock hard body, sculpted from endless hours of running, hiking, skiing and working out. It's always a pleasure to play with. I was enjoying touching it as I stripped her down, revealing her tight stomach and toned legs. I worked extra hard at teasing her, kissing down her legs and squeezing her ass as I caressed her. I pushed my face between her legs and kissed her clean shaven pussy through her panties, while massaging her ass. A few beers always got her turned on, but I wanted to add extra fuel to the fire. I nibbled her pussy and teased her with my tongue through the thin fabric, until she dragged me up, on top of her and close enough to kiss me.
I slipped a hand between her legs as I kissed her, stroking her pussy and pulling the fabric of her panties to the side. She grabbed my head with both hands and kissed me desperately while I slipped my fingers inside her. Her gasp as I penetrated her was a thrill and I curled my finger up and around to start stroking her g-spot, which she rewarded with a deep moan and a renewed frenzy in her kissing. I pushed my hand up her shirt and slid it up to find her breast. I played with her nipple, immediately getting her attention and then moved my mouth down to start sucking and licking it. I was going all out, her nipples were so sensitive that it drove her wild, especially when I took it between my teeth and gently bit down. Her hips started bucking as she desperately tried to fuck herself with my fingers. This poor girl was so wet and so turned on. I slid up her body and kissed her neck, excited for the next step.
"So I've got a surprise for you..." I whispered in her ear.
"What? What are you talking about?" She barely paused in her thrusting, trying to force more of my fingers inside her pussy.
"Christian wants to fuck you..." That got a response. She stopped suddenly, pulling her head back to look at me.
"Christian? You mean your roommate? The young guy? I don't think he's interested." She had returned to moving her hips, craving more pleasure. "Can't you fuck me already?"
I had bent the truth a little when I talked to Christian. It wasn't Tanja's idea to fuck him, it was mine but when I had proposed the idea to her, she was game for it, the idea of roommates also appealed to her. Sadly her attempts to flirt had fallen flat, he was too shy and absorbed in his headphones on the rare occasion that he left his room. Even her parading around in very little clothing had mostly just made him shyer and quick to return to his room (probably to get off, I was guessing...).
"Yah, we talked, after a few drinks one night. He's shy but loves the idea of fucking a hot older woman. You just need to take the lead..."