My [f]irst experience as a whore, and a few other firsts [37m/28f]

I apologise for the rambling nature of this story. It happened over seven hours where I had some of the best yet also strangest sex of my life. How did this even come about? Well, I am a late bloomer. Sheltered and shy, never really garnered or noticed attention from men. Recently moved to a new city and felt a bit lonely, so I started browsing craigslist and locanto. Now, this isn't the story of the first time I became a bit of a slut, but just the first time I was paid for sex. And my, it was such a good time, I don't think I would have minded not being paid.

A couple of weeks ago I was browsing CL and noticed a fairly normal ad from a guy who described himself as fit, clean, giving blahblah, looking for a nice girl. Details were a little sparse, but he was offering $1000. It sounded a little too good to be true! Now I have emailed other ads but never ones offering a "reward". I sent him a photo of my face and one of me in bra/panties and asked if he was genuine. He insisted, but said the money would be for a few hours. I was a little worried about what that would entail (I had work the next day!) but he said he was more into oral. He asked me my bra size (32B) and height (5'2"). We exchanged a few more emails and he asked for my number. We had a short phone call, where I determined he sounded sane/safe enough, but when I mentioned I didn't drink, smoke or do drugs, he said he would be indulging in some cocaine. Now I mentioned I'm quite sheltered; I have never done any kind of drugs before. I despise smoking and have never even tried weed, let alone been around cocaine. At this point I was a little skittish, but still decided to meet him. At his place. Yep, I am not a smart girl..

I caught a cab to his place, which was in a quiet and expensive part of the city, and looked to be quite exclusive. We talked on the phone while I made the trip. He told me about his work, but then the topics got a little more philosophical, spiritual, and a little hippydippy (he's into alternative medicine, whereas I'm a health professional). Seemed harmless enough, and I was already on the way so what the hell. When I reached the address, he came down to meet me. He was quite short, but still taller than me. Looked older than I thought he would as he was very grey. He was dressed casually and had a very easy going manner. Took me into his building. We went to the top floor of a small building, with only a few apartments on each floor. It was modern and spacious inside. I was a little nervous but he seemed normal enough..

In his living room he had pushed aside his coffee table and couches, and had a big mattress with pillows. He offered me a bottle of water, but he drank from some commercially packaged filtered water. He showed me the bathroom that I could use; it was the ensuite off the main bedroom/walk in wardrobe. Damn, the apartment was nice! He also had a lot of nice suits hanging in his wardrobe. I was impressed, especially considering the recent calibre of men I had met up with online (other stories but not quite as good as this one). We started out by laying down together and doing some more talking, then some simple making out, which was nice. But then a little odd, as he would often run his tongue up along between my lips/gums. Felt pretty weird so I kept giggling a lot. He also liked to lick my face and remarked that I wore no makeup. I said I was wearing a bit but he had probably licked it off. He asked me to clarify what mascara was! We remained clothed for a while, but then he stripped down and I could see that he was indeed very fit. Defined abs, but all very lean and low % fat. He commented on my big nose getting in the way (yet his nose was quite big, so he may have been joking). He also called me fatso a couple of times. He seemed to love my breasts but said I had told him 32D (nope, I had definitely typed B in my email). Generally he kept making remarks that would catch me off guard and freak me out but I think he just had a very dry sense of humour. E.g. he'd say "let's give you a tattoo" and I would freak and say "no!" then he would say how he disliked tattoos, and I asked if he had any and he said he had a dragon or something on his belly (which he clearly didn't). Then all of a sudden he would start eating me out. This would happen in cycles. We'd be talking about how he thinks meat is really awful for you, then he'd start licking me. He was immensely talented and I came very easily. Oh, and then he started licking my asshole, which I have never experienced before. It felt a little wrong but also very nice. And then, he'd stop, change the music, and go snort a line of cocaine. He offered some to me, but I declined and he was perfectly okay with it. He'd come back, talk some more, then eat me out. Rinse repeat several times. I asked him if he liked receiving oral, and he said only if I like to give it. I do, but he didn't seem to enjoy it that much (and I thought I was more than decent). His cock was maybe about 5.75" and average girth, uncut. I've never been with an uncut guy before so I wasn't really sure how it worked. I also didn't manage to see how it went from soft to hard, as I had my eyes closed enjoying his tongue. Then he'd ask if it was okay if he put on a condom.

He fucked quite well but in missionary he kept mashing my pubic mound. I tolerated it for a few rounds (he'd fuck for a while, then withdraw without cumming, go snort a line of coke and clean up and come back for a chat). In the end I had to say something though because it had become quite painful. He also fingered my ass a little while fucking me, which again, was completely new to me. I didn't mind it, but it didn't seem to do much for me. He loved my ass and kept grabbing it, playing with it, rubbing it and biting it. I ended up with a couple of bruises, but I didn't mind. I have a love/hate relationship with my ass – all my weight seems to go to my thighs/butt and I should do more squats but I'm lazy. But he loved it! So I definitely didn't mind the attention he paid to it.

He was an amazing lover, very considerate and selfless. He ate pussy like a champ! We had intercourse maybe 3 times, and each time he'd ask before putting on a condom. Then he'd go back to talking or eating me out. But damn did he do a lot of cocaine. I lost count how many times he had a line but I would guess more than 10x, possibly 15. I don't even know how much that is or if it's a lot, but it sure seemed a lot to me. I'm not sure how it affected him, except he sure did talk a lot and sometimes he'd lose his train of thought. He only drank water throughout our session, as did I, and he drank a lot. Finally it was nearing the time I said I'd like to get home (for work the next day). It was coming up on seven hours. At this point I was thinking I didn't even mind not being paid.

He said he'd like to cum now, but for me to jerk it. I confessed to him that I had never given a hand job before. He told me to just grab on (how hard? I asked, and he said hard, as hard as I could – turns out not all guys like this hahah) and pull. At first my technique was poor and my arm was getting tired very fast. Then I recalled all the acts of wanking I'd seen, and kept it all in wrist/forearm. Success! I could do this for a while. He straddled my body and I jerked him off over my breasts. He ended up kind of cumming partially on my face, none in my mouth (though that's what he wanted), and mostly on my chest. He had a towel nearby and cleaned me promptly, then scooped me up (he was very strong!) and carried me to the bathroom. Somewhat romantic but I think he was just done with me by then :P I had a shower in the ensuite and he had a shower in the other bathroom. I had cum several times – maybe 10 or 12. I'm quite vocal but only when I actually cum and yet each time he'd ask if I came.. I think it was his sense of humour again. -_- He only came the one time, but he seemed happy enough to discuss maybe seeing me again. And then he paid me with a stack of 50s, paperclipped. I didn't count till I got home but it was all there. It was quite thrilling but I just don't think another CL experience could come close in terms of reward, safety and satisfaction. Luckily for me, he's asked me to see him again tomorrow. I'm thinking it's going to be another long day. We haven't discussed the money but I'm hoping it's the same. I quite enjoyed the sex and would do it again, but maybe not all day. He didn't feed me at all except at the end when I got a muesli bar and a protein bar, hah.

TL;DR: met a stranger on craigslist, had my pussy/ass eaten out for several hours, got bruises on my pussy from being pounded and on my ass from being bit, gave my first handjob, got $1000.

edit: typos

Source: reddit.com/r/gonewildstories/comments/32x2v2/my_first_experience_as_a_whore_and_a_few_other