She was my girlfriend in high school and I had just turned 17.  My best friends parents were out of town and I told my parents that I was spending the night at his house.  My girl friend came over and we spent the night together....yes, she woke up with me as well for the first time!  She was soooo nice to me because it was not her first time so she helped 'guide' me where I needed to be.  IT was something else because it felt sooooooooooooooooo good but I was so concerned about not cumming too quickly that I didn't.  We went through a few positions and did a lot of kissing and oral but I never did cum.  I ended up going into the bathroom later and I jerked myself just a couple of times and I blew up.  This made it easier the next time because I was able to let loose with her...again and again and again...oh to be a teenage boy again!

I'll start, Arden, but I'm sure the men around here would MUCH rather hear about your first time than mine.  So it's your turn next.

For me, it was...anticlimactic.  It felt great, and strangely familiar (like I was recalling the sensation from a past life or something), but I remember thinking, "Is this what all the fuss is about?".  I had been blown before, and to me the intercourse didn't quite measure up to getting head.  So it was not a particularly special experience.  (Of course I've grown to love it more and more!)

And since I'm telling the story, I'll admit that while I was somewhat underwhelmed by the experience, she was devastated by it.  Right after I came, which didn't take long, she burst into tears.  It took me ten minutes of listening to her sob before I could understand what she was saying.  She was crying because she had dreamed about being with me since 6th grade, imagining what it would be like, and when it finally happened, it was devoid of emotion on my part.

I felt terrible.  She was in love with me, I was not in love with her, and that reality hit her suddenly like a ton of bricks that night, during our first time.  

But I only felt terrible to an extent.  Afterall, I wasn't in love with her, so my feelings could only go so far.  I didn't really care that I was "mechanical", "going through the motions", as she tearfully lamented.  It was my first time, so naturally I was concentrating on what to do, instead of gazing into her eyes.  Mostly, I was just glad to have had the experience, to be able to check off "sexual intercourse" on my list, to no longer be a virgin.

Matt

Did it right before a school dance, right when my gf of 2 years at the time was getting ready...

no awkward moments so we were both happy.

But I do have to say, as much as I wanted it to be romantic and all that stuff, I probably looked very mechanical because I didn't want to mess anything up either.

I remember all the other girls laughing & making fun of me because I was the only VIRGIN!
My pussy was super tight I could not even put a tampon in there.  I totally remember many times before the actual event took place filled with four play with attempts to open me up.  I must say when it did finally happen I thought it was no big deal, but I was not sexually satisfied until I replaced the loser who took my virginity.
Enjoy everyone!

First time in the hobby...

I was very nervous about just about every apect.  Got compounded that as a newbie I had no references and thus the provider was also nervous so had me wait in my car for about an hour.  Having no point of reference as to whether or not this was "normal," just waited it out.  When she finally got up the nerve to let me in, the time I had set aside was more than half over.  Once we got comfortable with each other, she let me know that clock wasn't ticking.  That was sweet of her, but I had somewhere to be.  Ended up being rushed and awkward, but... she was pretty, super sexxy, and much more intelligent then I had imagined.  I left intrigued enough with the idea of what it could be with better planning and research.

Where do you start?

OK, first time sex, almost!  
We had been attending the same school for several years and we were both just 16. I lived in an upstairs apartment and she lived two floors down. Mums and Dads would always go out on a Saturday night leaving her babysitting her 3 year old sister. One Saturday I saw her shopping during the afternoon and she suggested we might have a musical evening and possibly swap some disks.
Sister off to bed around 8pm and we had the music on low. We had kissed previously, but only in public and in a jokey fashion among school friends. This was our first serious kiss with tongues, and it seemed to go on forever. A feel of the (very small) breasts before asking if I could put a hand inside her panties. Answer was a breathless "OK then."
Hand and fingers got the target nice and wet and somewhat smelly, but dubious hygiene doesn't stop you when you are 16!
Her hand in my shorts, squeezing my penis and we both orgasmed at the same time, her panting and jumping around, and me shooting a huge load around her fingers. Not sex technically, but first  orgasms with someone else for both of us.
I always remember it, and so does she!

First time in the hobby. (50 years later!)
I was in a hotel in El Paso with an early morning flight next day. I was waiting to cross a road to go to a Burger King when a girl of around 25 stopped me and said "Hey honey, give you a good time if you can take us back to your room." She had a small child about 4 years with her and when I looked puzzled she said "Don't worry, she will sleep ok." I then asked when she had last eaten anything but she just looked away. I insisted they come with me to the Burger King and the child ate more than I did. After we had eaten we went back to the room and sure enough, after a warm shower the little girl went straight to sleep on one of the two queen beds. I wasn't very comfortable with this, but was again assured that it was ok, she was a full time provider and the little girl would sleep soundly. I suggested we use the bathroom to clean up and we both had a cuddle in the shower which set things going nicely. Slipped quietly into the other bed and she started with a great bbbj. I reciprocated with a daty until she was 'ready'. A cover on, then straight all the way in until we both had muffled orgasms. An early bbbjcim under the bed covers before breakfast and we parted friends after my hearing her life story.
I have seen her many times since, whenever I am in El Paso, and we have a great friendship with really wild and uninhibited sex.

First kiss, first sexual experience, first masturbation experience, first orgasm, first provider sexual experience, first oral experience....    Where's a gal to start?

My first sexual experience was HORRIBLE!  I mean really and truly horrible.  I am almost embarrassed to tell the tale but here goes.  My best girlfriend's parents were out of town so she gave me the house for the evening.  I was 15 and extremely inexperienced.  My boyfriend and I sat on the chaise lounge in my girlfriend's mother's bedroom watching The Shining and chasing a 12-pack.  How romantic right?!?!?  As the booze took over we somehow made our way to the floor in my girlfriend's bedroom.  All I remember is him on top of me and then us putting the rug in the washing machine.  Next, I call my best guyfriend to pick me up and my boyfriend leaves in a separate car (later found at his ex-girlfriend's house).  It couldn't get much worse than that.  Do I get a pity high five?!?!?

THANKFULLY, my CURRENT sexual escapades are truly worth writing about!!!!!!

First time was in a massage parlor in Brooklyn, IL (across the river from St. Louis), on my 27th birthday.  I'm hardly a hermit, but for some reason I never got past the heavy petting state at that point in my life.  I was in the city for a conference, and a cabbie recommended a strip joint in Brooklyn.  It was far more explicit than those I had visited before, and I figured that the "massage parlor" next door likely provided extras.  I was there with a large group, but returned by myself a few days later.  After warming up at the strip club, I went next door and did the deed.  The masseuse was nice enough, but it ended up being far more mechanical and less sensual than I had imagined.  In hindsight, I should have told her I was a virgin - it likely would have been more fun.

My first time outside of the hobby was somewhat unremarkable. 17 years old, girlfriend was 22, blasted off after about 2.5 seconds...

First time in the hobby was more ridiculous than anything else. Hell, I didn't even get inside of the gal! I was perusing the CL ads and found a local girl advertising. I called her up and set up an appointment and drove the hotel. She keeps me waiting in the parking lot for 20 minutes or so before she finally decides I can come up.

I get up there, and am nervous as hell. I have no idea what I am doing in the hobby. I am guessing she didn't either. She sits there asking me what I want. I felt like I was being interviewed. I didn't want to get too explicit in case she was LE, and she wanted me to come out with it in case I was! She asked for my ID, then finally decided to go ahead. She was so nervous that her hands were shaking. I should have just run out.

Then, the upselling. Oh, crap. Is this normal? Will I expect this from every provider? What else will happen? I didn't bring up any more money, so upselling was not going anywhere. We finally end up on the bed and she will only go for a HJ. Really? I finally get her talked out of most of her clothes, and she is going for a HJ and getting me out of there. Once the deed was done, I ran for the hills.

Luckily, my experiences since then have mostly been great. I am convinced that most of the worlds beautiful and interesting women live in San Diego, and have had the pleasure of meeting many of the best providers here. Love you all!

Moves in, that is. Never posted, never hobbied, sticking my toe in the water you could say.
Since I don't have the story you're asking for, I'll share the other.

15, and in the guest bedroom of my friend's house; she wanted my virginity and I didn't. Match made in heaven there! After a good make-out session, we got down to it and she helped me in..
Things were going great and I was really starting to get into it.
The family dog was observing the activities without our knowledge, and decided to check things out a little closer.
By closer, I mean that he came up and pressed his cold wet nose against the back of my balls.

I screamed in terror.
She screamed in pleasure.
Attempting to get away from the dog's nose made me thrust violently into her and triggered an orgasm.
I think she remembers it more fondly than I do.

Toss in the weather (this winter notwithstanding), and why would any man ever leave??

MC

Still am, every time.  She was young, me, not so much.  She was an agency girl, but she knew her stuff.  Kind, led me along fine, we both ended up having a great time.    

Money doesn't change the fact that every first date, paid for or not, is still the first date!!!  'Course, if it was someone like you, that would have changed quickly!!!....anyway, its why I like to find a lady and stick with her as long as we both click.  "new" is nice and fun, but "repeat" is easier and often more rewarding.  IMHO only, of course.