Your first time...

I was reading about Sins of the Flesh's first time as a pro and as any of the ladies who have met me, I like to ask questions. So I guess the question of the day (inspired by SoF) is what was your first time like? I guess for guys you have to differentiate between a street walker and an escort.

First time in the hobby was a graduation gift from a friend, I been hooked ever since
This is more efficient lol

Went to a rub and tug on my 18th birthday with some of my graduation money for "massage". She stripped down and began the tug...I think I lasted 90 seconds. I've been hooked ever since.

As long as I can remember, I've always had a fantasy for older woman. Back in high school and college, I used to get "40+" & "50+" magazines to jerk off too. Many years later, I started reading the personal ads on Craigslist for entertainment. I remember ads for a gal named Christy who offered "amateur psychology" out of her trailer out east. Smoking hot woman around 50....her pics drove me crazy. Freshly divorced and no longer in a committed relationship, I finally worked up the courage to call.

Looking back I cringe at all the stupid mistakes I made, I was definitely a rookie. But she was beautiful and sweet. That afternoon I was able to live out my sexual fantasy. There have been other since then, but she was my first and best. I'd love to see her again.

Growing up I had quite a number of experiences with women who were sex workers -- strippers and streetwalkers mostly (we didn't call them "escorts" back then). That's because my grandfather was a booking agent for burlesque dancers and I would often go with him to theaters across the midwest and hang out backstage while he was talking with the managers there. This was long after burlesque was out of fashion (and before it came back) and all of these places were porn theaters or strip clubs at the time. I got a bit of action, without realizing that my granddad set it up with the girls there.

Anyway, my first time I knew surprisingly little about the actual call girl scene, and I literally picked up the Yellow Pages (this was in Ft. Lauderdale) and picked an agency at random and made an appointment. I lucked out, and they sent a very beautiful, sweet, professional lady who gave me everything I paid for. Since then I've read stories about ripoff joints and scams and upselling -- and encountered my share -- so I was really lucky that the first one went well.

My first time was a bp girl ... I didn't know better a yr ago lol .. Answered ad for upscale incall I picked her up and wow very sexy i thought, drove to incall and she said here we are got room opened door and I think I remember the place had green carpet lol I turned to her and said I thought u said upscale location .. She said I didn't know it was gonna be this bad she said I can lay my coat on the bed and I thought I better get this done it was a pleasant experience and she was a cutie we used up the 30 minutes and I had a blast except for the location

God, my first time with someone who I "rewarded" for their efforts was for some pretty decent head in my '85 T-bird in Philly. I was young, in grad school in a bad part of town and I saw all the "street walkers" every night and I was curious just how hard or easy it was....

I pulled up beside a lady, and asked her if she needed a ride. She jumped in, asked if I was Law Enforcement (that seems to have changed little) and when I said no, she said drive on.

I asked where too. She asked what I wanted. I said sex. She asked if I had a place, I said no, no place except my car. She said a blow job was $50 (I think, might have been $20). I pressured for more, but she clearly did not want to go to the trouble of sex in a T-bird.

The BJ was good.

Been banging once in a while ever since.

Most memorable before the internet was a young street walker, absolutely gorgeous, great natural breasts and fabulous body. We found space for sex in that t-bird. Incredible body, perhaps the finest woman flesh I ever had. But she was aiming for "California" and I suspect she made it, except she was dumb already then. Her snatch was smelly and already way back then, I learned to recognize the dumb ones by the smell.

Quality takes care of their body.. Period. I cannot stand a smelly snatch.....

Before the internet days of matchmaker.com , at least 15 years ago--maybe 20, the Pitch had a matchmaker section where you could place an ad for a legit date. After a couple of bad ones, I noticed some ads in what was the escort section. After a bunch of phone calls and asking lots of questions, one woman nicely answered all my questions and asked me what I was looking for. She set me up with her sister who was just beginning in the business.

"Danielle" showed up. Very cute, slender/hard body and still the most perfect set of implants I have ever seen. Perfect size for her body and perfectly shaped. I saw her weekly for three years until she married one of her clients and moved to Georgia.

She was highly professional. She went to the gym every morning for her two hour workout and made two to four calls in the afternoon. Always returned your messages and never was a NCNS. She always arrived looking like a business woman in a skirt and jacket. She quit advertising after several months and only saw her regulars. She saved her money and invested well. No drugs or bad habits. She lived simply. She probably retired with a paid off mortgage and a hundred fifty thousand in cash in three+ years.

Two first times; the first street walker was my 19th birthday in Orlando, FL. I had seen this woman walking down Orange Blossom Trail. She was black, attractive and to me she looked like Lt. Uhura from Star Trek. I finally decided to get it done and pulled up next to her, she asked if I wanted a date, a date?, I guess so. She got in and we drove to a seedy motel around the corner. For $40 she got undressed and started sucking. I was so excited that I had to stop her almost at once. She got out a condom and the job was done very quickly....too quickly. I saw her a couple of other times but it was not like the first time.

Another first time was also in Orlando. A friend had gotten kicked out of Nuclear Power School and he was depressed. We wandered the area for most of the night and we went by a massage parlor. He said that he would pay. She was blonde, very attractive, and wearing a little tiger skin pattern bikini underwear. I had to cover the tip and there was no massage. We went right into it. Much better but still not like the first.

Years later when I was traveling cross country I had the phone number of a service in Indiana. She arrived (don't remember what she looked like at all), she got paid and we did it. A lot of the fun was gone after Europe.

I was working at a ranch in Nevada. I was 19 and had only been with one other man. Picked right out of my first lineup I went to the negotiations. Of course I was oblivious to the fact we COULD negotiate. (there was no tutorial or explanations of how much or such) So when the gentleman offered me $ I accepted not realizing I had the option to say no or to ask for more. It was quick and slightly disappointing as he was far more interested in the product for his funds verses us both enjoying the hour. In his defense my skills were incredibly lacking due to little to no practice.

My first foray into the hobby was at the Kit Kat Guest Ranch in Nevada. I saw Caressa Kisses the spoksmodel and pornstar. It was an afternoon of pure delight. I thought I had died and gone to heaven. It also was the most I have ever paid for a one hour date lol

Reading some of these is starting to make me feel like a late comer (or is that cumer) to this little hobby world.

At least I can still go back and read my first time... and about all the mistakes I made.
Still can't believe that I was so afraid of having a "Hair Trigger" that I thoroughly cleaned my "gun" right before seeing her, and then forgot to reload it.

Well that is unless you count back when I was in high school... (Yes MODs... we were both 18 )
My girlfriend and I was walking around Indian Springs Mall (how many remember the Fun Factory?) when she sees this purse at Spencer's that she wanted.
She whispers in my ear that if I got it for her she would suck me off right there... funny how I can remember that it cost $20.80 with tax.
(I remember because I had to "borrow" a nickle from one of the fountains)
She kept good on her promise and we went downstairs and in back of the escalators is where she sucked me off, no swallow, but I remember "painting" the wall quite nicely.
In retrospect it is cheaper now... because back then it only took about two minutes for her to finish me off... lmao
But then again... back then it only took about two minutes for me to recoup too... youth is so wasted on the young!

Reading some of these is starting to make me feel like a late comer (or is that cumer) to this little hobby world.

At least I can still go back and read my first time... and about all the mistakes I made.
Still can't believe that I was so afraid of having a "Hair Trigger" that I thoroughly cleaned my "gun" right before seeing her, and then forgot to reload it.

Well that is unless you count back when I was in high school... (Yes MODs... we were both 18 )
My girlfriend and I was walking around Indian Springs Mall (how many remember the Fun Factory?) when she sees this purse at Spencer's that she wanted.
She whispers in my ear that if I got it for her she would suck me off right there... funny how I can remember that it cost $20.80 with tax.
(I remember because I had to "borrow" a nickle from one of the fountains)
She kept good on her promise and we went downstairs and in back of the escalators is where she sucked me off, no swallow, but I remember "painting" the wall quite nicely.
In retrospect it is cheaper now... because back then it only took about two minutes for her to finish me off... lmao
But then again... back then it only took about two minutes for me to recoup too... youth is so wasted on the young! Originally Posted by ElumEno

That girl was a keeper!

Great stories! Thanks for sharing everyone. I am enjoying the responses and looking forward to more!

I know exactly where that was in Indian Springs, having worked there for several years. I would well imagine that was a bit more of a dicey situation risking getting caught, than when I was there in the mid-late 90's.