Through unfortunate circumstances and inheritance i've been a homeowner since i was 19, and for the most part i'm usually single, so i've always had a couch or a spare room for a friend to crash on when they needed.
I was 22/23 when in the span of a week a friend had lost her job and had her basement suite flooded, with no job she was going to live in her car till she got her shit together but i said she could crash at my place, the spare room was more of a storage room but she was cool with the couch. She was a total knock out with big tits and i wouldn't go as far as slutty but she was a free spirit. It had been a couple weeks, she'd picked up a new job and came home one night with a case of beer a pizza and a movie and offered me a $100, i wouldn't accept the money and we carried on with our night, the movie was no strings attached or friends with benefits which ended up being how our night went, we were maybe half way through the movie and she snuggles up to me and starts rubbing my thigh then starts kissing me and suggests if i would accept rent perhaps we could fuck, besides she hadn't gotten laid in a while because her regular guy had moved so why not. She was wild in bed and gave some porn quality blowjobs, unfortunately she only stayed a few months until she found a new job and a new place and our arrangement dwindled.
There was another one when i was 28 and i was doing the couch surfing, i was doing some out of town work in this small mountain town close to where a friend had recently bought a house, my accommodations for the week were this shit hole motel, my friend had offered up a spare room and i figured why not it was better than the shit hole i was set to stay in. She was 27 average height, slim body, blonde hair blue eyes, small perky tits and a decent little ass, we'd known each other 8yrs or so and i'd tried getting in her pants but she never let that happen so i wasn't expecting anything to happen. I'd done my week and decided to stay through till sunday so we could hang out, we got to drinking friday night and the conversation turned to relationships and she eventual hits me with how she loves her new job and owning her own house but she hasn't been fucked in close to two months and there doesn't seem to be any worthwhile single guys, i was at a loss for words then she add on "did you know amazon sells sex toys? they're just not the same though" to which i responded with a cheeky "To bad we're just friends" She gave me this look then says "thats not such a bad idea" gets up and says to follow her, we spent the rest of the weekend fucking each others brains out.
The lastly was a little over a year ago. She was the daughter of a family friends friend, she was 19 and an absolute stunner, i'd met her a handful of times and we got along but i was 31 and to my knowledge she had a boyfriend. Anyway she'd taken a job down on the coast and due to our shitty housing market she was having issues securing a home and if she couldn't find a place to stay she'd basically have to pass on the job, family friend reaches out and we decide she'll stay with me till she gets on her feet. We hit it off pretty well and turned out she was single but i figured best to leave it alone, i found she wasn't shy about walking around the house in barely anything not that i was complaining. It was maybe a month after she'd moved in that we were drinking one night and she starts inquiring about my relationship status and how i didn't seem to have a girlfriend but she couldn't help but notice a few different women would stop by late at night then be gone first thing in the morning, then says she didn't see me as that type, i laughed and asked what type that was and she says the player type that has multiple women on the go, again i laughed and said i just found casual sex less complicated to which she gave me an intrigued look then said she'd never really done the casual sex thing being from a small town where everyone knows everything, i said she wasn't in a small town anymore so she should give it a try sometime and then we continued drinking, i eventually call it a night, go for a quick shower before bed and needless to say i was pleasantly surprised when she stepped in to join me, said she'd never been with an older guy before and she'd heard a few of my hookups so she knew i could go for a while