One an only time, i was 28 she was 19. I always used to browse the craiglist ads but never actually used them. Then one night i came across one with a few pictures, no face but i immediately recognized a couple of her tattoos. It was my exes best friends younger sister, she was a little over 5ft, 100lbs or so, long brunette hair, stunning brown eyes, pretty smile, dimples, very tight body, decent sized pierced tits and a great little ass, she was a solid 10+ just unbelievably hot and well manicured, eyebrows, lashes, nails, tanned nothing out of place. I'd known her a few years and she was always a slutty little tease so i can't say i was overly surprised. I sent her a message and she responded with her rates, dos and donts and so on, $250 got me 2hrs in a hotel room, i was hesitant but figured fuck it why not, she sent me a room number and instructions.
I arrived at the hotel went up to the room and knocked, she answered the door in a lacy black bra and thong and high heels, and her jaw dropped as she blurted out "what the fuck?" and she grabbed a jacket to cover herself and asked what i was doing there, i said i was the guy and she just stared almost speechless then said she'd never done this with someone she knew, usually just horny old guys, i said we didn't have to if she didn't want to and that i wouldn't say anything, she thought about it for a minute while looking me up and down then said she'd heard things from my ex and her sister, things she'd like to see for herself then stepped back and let me in. She took the money then sat me down in a chair, got on her knees and removed my pants, i was already half way as she began sucking and fuck it felt good, she had me hard in seconds, then sat back almost admiring it and says "No wonder she missed you, this is a nice cock" then went back to sucking for a few minutes before asking if i wanted to get straight to the sex or if i wanted her to get the first one out of the way, i opted to have her suck me off first and let her do her thing as i sat back and enjoyed myself, on her list of dos and donts was warn her when i'm about to cum and don't cum in her mouth, well i felt it building and warned her i was getting there, she just kept sucking, i warned her again and again she just kept sucking, i was trying my hardest to not cum but i could only hold out so long before blowing my load and fuck me when i did it felt like a gallon of cum drained from my balls as she sucked and jerked until i collapsed in the chair, as i sat there coming down from the orgasm i apologized as she gulped it back and she just laughed and said "No need to apologize honey, i figure we go back so i'd swallow for you" . She went, grabbed a drink of water and returned and says i still have an hour and half to fuck her and asked if i needed a minute or wanted to get to it, i told her we could go as soon as she got me hard so she told me to get on the bed, did a little strip and began sucking my cock again, she got me good and hard then grabbed two packages from her bag and handed them to me, a condom and a rubber cock ring, she says "you don't have to wear the ring but it'll make your dick harder and feel even better when you cum" I slipped both on and i'd worn cock rings before but this one was certainly tighter, she grabbed my cock and ease herself onto it, we proceeded go at it for a while, thanks to the blowjob i was able to hold out, i expected a lot more overly dramatic moaning and such but it was just some hot sweaty fucking, we talked for the last 20 minutes or so and as i was about to get dressed to leave she asked if i wanted to go again, i said i couldn't afford anymore to which she said no charge she just wanted to fuck again.
Few weeks later she called me up for a hookup and we ended up being fuck buddies for almost a year until she got a boyfriend