I got into this in stages. Late fall of '01 I was in my mid-20s and I had an on/off thing going with an ex-GF mostly for occasional quick booty call hookups. But I was looking to end it as I was only in it for sex and she wanted to get serious again. Despite pushing myself out there in the civvie dating world otherwise I wasn't making it past 2nd base with any chick and essentially hadn't had been with a new girl in over a year. The itch had been building.
I had some mild success on occasion hooking up with girls I'd find on yahoo chat rooms, so one late saturday night I was up late feeling lonely and horny as usual looking for action. I was IM'ed by a woman who was surprisingly forward about wanting to get past the usual bullshit and just want to straight up hook up that night. She sent me a few pics and I saw a hot blonde milf type with big tits- similar to the current porn star Carolyn Reese. Not my typical type but certainly hot and was happy to please. Lucky day! Then she hit me with a price tag of around $250 or so for the 'service'. I wasn't a random hook-up I was a potential client! Due to the mental stigma I still had about escorts and the fact I couldn't quite swing that cash at the time I politely backed out. While I didn't get lucky with anyone else that night the thought that a few bills kept me from getting laid in that moment and how my itch could be scratched so conveniently stayed with me big time.
So I spent a month or so doing a little research - finding early sites, articles, LJ's and of course TER about all this. I searched ads online and my world opened up. I played a little fantasy time even picking out some girls in ads that I'd love to see but I held back. The stigma still loomed. Then I was w/family out of state for the holidays. I was hoping to hook up with another ex, a spring romance woman I'd seen 18 months prior but stayed in touch with for the odd hook-up, but she flaked on me. (I'm still bummed I never got to see her in a carnal fashion ever again, I'm fairly sure a number of escorts I seek out now are surrogates for her or certainly her type... ahh those brown eyed brunettes). So my older brother who was no stranger to the ways of escorts and I somehow got on this topic. He clarified a few things for me and assured me of certain safety tips and then offered to hook me up with a UTR girl he sees. An Anna Kornikova look-like he claimed. I was so horny I didn't think, I just said yes. He set it up for the next night but sadly the Kornikova girl wasn't available and he booked another UTR girl he knew instead. The problem was, sweet girl and all but she was fairly far from my type. But he went to the trouble and talked her down to $150 or so for me so I felt obliged to go through with it. Problem is, I had first time nerves, it's just before New Year's, dead of winter in the midwest, super cold in a cheap motel that refused to warm up despite the heater and I'm with a girl who's not turning me on. We cuddled under the covers and talked for a while. She took off her bra showing some ample boobs which got me hard and she gave me a CBJ for a while. Between that, some boob fondling and a final HJ I got a manual release. Normally 2nds or even 3rds aren't a problem for me, especially back then but it was still freezing, I felt all weird about everything with the setting and I just ended it there. I cleaned up and we talked a while longer and that was that. My brother returned to pick her up and that was that. I have since repaid him by starting me down the path by turning him on to TER in the last few years which i was surprised he didn't know about!
Soooo technically that was my first provider. But my first full service provider would happen about 5-6 weeks later in early Feb '02. After starting to budget for this hobby appropriately and doing TER research I set a date with a provider named Lady Melissa, great body, great reviews, great rate and I was in the mood for a redhead. Sadly she cancelled last minute and thanks to various circumstances at the time I was never able to reschedule with her (she'll always be the provider that got away.. LOL) before I took a hobby break in late summer '02. So worked up, and disappointed I used the wrong head, ignored TER and called up a hot looking chick named Sonia on vipcityconnection. Big mistake. Bait and switch. A half hearted massage and several attempts at upsell later and the girl was out the door and I was fast getting a case of blue balls. I'd been cash and dashed. Argh. My review of this incident is still up for those who care.
I'm amazed I stuck it out with all these bad/semi-bad experiences but the positive reviews of others for the good escorts spurred me on and hey the little head wants what the little head wants. The idea of getting laid without the usual courtship hassles and alieviating things when I would have civvie dating dry-spells was too tantalizing to resist.
So my first real FS, great time provider was a girl by the name of Stefanie who advertised mainly on That Mall.com at the time. (She was later known as Julie on satinsleepers). A week after the Sonia incident I set this up on email. She came to my place (I favored outcalls then) and was exactly what I was looking for. A perfectly pretty, petite, brunette college girlfriend fantasy chick. Jack. Pot. She was sweet and sexy. I recall she a student or recent grad who did this very part time to help with the bills. We chatted, moved to my bedroom where upon removing the sheets turned to find her already topless. The sudden nudity shocked me for a few seconds which made her giggle. She was limited on kissing, a few LFK teases at best but I spent most of my time on those perky B's anyway. We stripped to our underwear where she gave me a really outstanding massage, nipples grazing my back and all. Nowadays I'd probably try to speed things up but then I as happy to drink it all in and get a little pampering. She turned me over, we lost the underwear, gained a condom, and after some mutual grinding, fondling and groping she simply said "Mmm, come here!" rolling me on top of her and guiding me home. We fucked like this a long time. Slow then fast, building a great rhythm. She was so tight, the way she clung to me. That body, those moans, the fantasy she represented to me... it was so hot. So intense. I lost it hard and then we cuddled and fondled lightly in the afterglow. No time for seconds.
While I've had some really hot times with other escorts since, a couple of which I really connected with, Stefanie was the only one where I got the honest school crush on for a little while. I got over this later and never let it get me carried away thank goodness but I can't deny she really was a fantasy fuck/fantasy girlfriend type for me. I remember meeting a friend for dinner right after that 1st session and he could tell thing had just gone well for me with a chick. I was wearing a shit-eating grin and a flushed face. The whole dinner while we talked about a mutual project, I that light headed high, butterfly stomached, warm chest feeling. Despite the fact it was a pay-for-play date I'd just had I didn't care in that moment, I just embraced feeling so good.
I saw Stefanie a couple more times that spring. (Part of an minor escort spree I went on from Feb- July that year, ending when I got a new GF for a while) Sex with Stefanie was always hot, always intense, although I was disappointingly, unless you were a little aggressive, she was usually was a 1 shot per date girl. And despite a nice ass I never got to go doggy with her. My own lack of pacing but hey, regrets, regrets. Despite this she was always amazing to me, though it never was as 'special' as that first encounter. She appeared to retire (or at least go very UTR) by the mid '00s. Great girl, great time, fond memories, I still think of her sometimes. Hope she's doing well wherever she is