My First Time Having Sex for Money

I mentioned my first meeting before here and here.

I did end up seeing M again, quite soon after that meeting. Luckily I didn't scare him away with my inexperience and inebriation!

We met at the same bar again, and each had a drink. He had been to the doctor's office earlier in the day, so we talked about his sports injury. I originally thought he would have to cancel because he had been through minor surgery in the office that day, but he was insistent that we meet anyway.

Almost the second we stepped through the door of his condo we were at it. We had the quick mumbled convo about birth control (pill and condoms!) and before I knew it I was naked, laying across his bed!

Please keep in mind how terribly, terribly inexperienced I was at this point in my life! This is certainly not what I consider an 'ideal' meeting!

He went down on me, something I had never before experienced (ahem, college guys suck at sex). I didn't know what to do, and honestly was a bit uncomfortable. When it was my turn to reciprocate I was relieved.

M was average sized, nothing extraordinary, but certainly not disappointing. The sex was average as well, lasting perhaps 5 minutes, in missionary.

We talked for a while after. I was a bit inebriated (again). He asked if I'd ever thought about getting implants. I responded that if they ever find a way to make implants pain-free I'll be first in line! Until then, there's no way I'd ever agree to unnecessary pain. I have very low pain tolerance.

We got dressed, and he walked me out. In the elevator he handed me an envelope, and said he hoped it was enough. We hadn't discussed money at all beforehand. He joked that it was probably the easiest money I'd ever make, and I nervously laughed with him.

Certainly not a terrible first time, however I learned a lot from it (when I sobered up).

Funny note: When I got home 20 minutes later I ran into a friend on my way into my building. She grabbed me and made me go out for a snack with her and a bunch a friends. The whole time all I could think was 'Please dear god don't let them figure out that I'm tipsy... or notice the economy pack of condoms in my bag!' I got away with it somehow!

My First Meeting P2

I am sorry for not continuing this post earlier. I've lost my journal from that year, and I wanted to try to remember more details. Alas, it seems to be truly gone (whaaa!), so here goes!

When he returned we sat and talked a bit longer, and then he suggested we head out. At this point I will admit I had drank (drunk?) half the glass of wine and two cosmos. Remember I was only a little froshie and the whole drinking thing was new to me, so I was definitely tipsy.

We began to walk out of the bar and down the street. At first we were heading towards the subway, but then we weren't. I didn't say anything. Next thing I knew he was holding open the door to a gorgeous condo high-rise. We went upstairs, past the two smiling doormen. His one-bedroom condo was beautiful, clearly professionally decorated.

He excused himself to the bathroom, so I sneaked a peak of the view out the window. Gorgeous. When he came out we sat on the couch talking for a bit.

Then he asked me if I wanted to go to the bedroom. I blushed horribly. I apologized and said I wasn't sure why I had come back to his place with him because I didn't intend to have sex on the first meeting. He said that was fine, then asked if he could have a blowjob.

Embarrassing, but true, I really was inexperienced with the BJ, so I said no. He said that was fine, again, and offered me a ride home.

We took a taxi to one of his properties a couple of blocks away where he kept his car. The gate's lock was iced, so after struggling with it for a couple of minutes we walked from the front of the brownstone around the block to the alley. He had a brand-new Lexus.

He drove me home, and kissed me when he dropped me off. Nearly the whole drive there he had been on the phone with his wife, directing her on packing their vacation home.

And that was my very first meeting with a real live sugar daddy!

I'm Sorry!

I love when men apologize after sex. OK, not really, because I never have any idea what to say. But afterwards, when I'm back home alone, I always have a good laugh over it. It's always for some perceived inability; not keeping it hard, not going long enough.

He's not an SD, but my current boyfriend apologized once for his lack of stamina...after going for 25 minutes! With him I actually laughed right then and there and told him just how silly he was being! Granted, he does normally go longer, but 25 minutes is certainly nothing to be ashamed of!

With an SD though I do find it a bit ridiculous. You should never feel the need to apologize for anything, let alone for something like that, where to be honest I usually am happy if you finish a little faster than normal.

One SD came after maybe 5-7 minutes and after he caught his breath apologized for it being so short. "Normally I can go a lot longer, but I had minor surgery on my throat this morning, and I think I am still a bit woozy from the meds." The fact that you were able to get it up at all should be a triumph! Don't apologize!!

And, of course, I mentioned earlier about Mr D, who apologized after his little bout of food poisoning-induced diarrhea caused us to have to call it quits. I still got money, and I got to bed a lot earlier than I had planned on! No complaints from my end!

The hardest part is what to say! I don't want to sound like I'm lying by over-doing it, but I also can't rightly say 'trust me honey, it wasn't doing much for me anyway.' I wish there was a perfect answer for this!

My First Meeting P1

I was so nervous. The whole way there on the subway I had my ipod on really loud, trying not to think about what I was doing. I nearly didn't go. I called M earlier in the day and almost canceled. In the end we agreed to meet a little later than we originally planned.

As I walked up from the subway and down the street I nearly turned back around. What was I doing? Meeting a man nearly old enough to be my father, in a bar when I was only 19!

I was relieved when I made it to the bar, but only because it was so cold outside. Once I thawed out and took a look around I realized that I didn't see anyone who looked like the picture he'd used on his profile. I started to panic. What if he wasn't there? What if someone carded me? What if I knew someone in here?

Just as I was about to leave a man sitting alone at a table caught my eye and mouthed across the room 'CB?' I nodded and made my way over.

He wasn't the man from the photo, and he later explained that it was a picture of one of his friends. He was actually more attractive, and after the first couple of minutes I felt fairly relaxed with him.

I had no idea what I was doing. I hadn't planned in advance what I was willing to tell him and what i wasn't. We talked about our families, and I ended up saying more than I should have. I'm lucky it never came back to haunt me!

He had two homes, one here in the city and one down in Florida. His wife and kids were down in Florida, and they rarely came to our city. He was here a lot for business. He was in real estate in some fashion. I wonder now how he's doing. If he managed to escape the bubble popping and all that.

He ordered me a glass of wine as I had no idea what I wanted. When it came I drank only a little of it. I didn't want to get drunk. He took this to mean that I didn't like it, so he asked the waitress to take it back and get me a cosmo instead. I felt so embarrassed!

After we had been there nearly an hour he took a phone call from his wife. He stepped outside after the intial 'Hi Honey. Yes, still at the bar, watching the game.' I wondered if she could tell, but I didn't feel any guilt.

TBC...