The title of the Craigslist ad read, "Student Aid."
The ad was brief but to the point. It read,
"Gentleman in town on business and would like to meet a college student over eighteen. Very discreet. Please, no escorts. "
At the time, I was about twenty and my family was hurting for money. My father had been in poor health for years and had been unable to work. My mother was struggling to keep the household afloat. I was at a local college as I could not afford to go out of town. I had an old beat-up car that was costing me more than it was worth. I had a part-time job, plus I was babysitting, and still, I could not make ends meet. Times were tough.
Although my family was struggling, we all hid it very well. My friends all went away to college, drove nice cars, and had designer clothes. They had no idea of my family's struggle, and I never spoke about it. I never even told the guys I was dating. Without being asked, I did my part to help out as much as possible.
I had heard about Craigslist, and I did browse the personal section on occasion. I found it amusing as most of the ads were quite provocative. I never dreamt of responding. I was raised in the church with religious morals, and besides, I was too shy. I read the ads strictly for entertainment purposes.
Yet there I was one morning staring at this ad on the computer. It had caught my eye, and somehow I felt it was written for me. Maybe because the author referred to himself as a gentleman, or maybe it was the fact that he was looking for a student and not an escort? Maybe it was my craving for adventure? Or maybe it was because I was broke.
Suddenly, the act of responding to a Craigslist ad wasn't so farfetched. I had never done or even contemplated doing anything like this before. That morning, I was too frightened to respond to the ad, so I walked away and left for my classes.
That Craigslist ad was in my head for the rest of the day. How bad could it be? It said he was from out of town, so nobody would ever know. I was already having occasional sex with one of the fathers I was babysitting for, and he was paying me more than the going babysitting rates for sure.
Besides, six months earlier, I had sex for money with an older man. I stumbled into that adventure when I was waiting outside the movie complex after being stood up by my boyfriend and a man propositioned me out of the blue. I was pissed at my boyfriend and had no plans for the evening, so I accepted his offer. It turned out to be quite rewarding.
I wondered if I could do it again.
The ad did say "a gentleman." I wondered how much money he was talking about. Am I even worth much money? I'm not a sexy hooker, just a normal-looking student. I wondered if...
I was trying to convince myself that this wasn't that bad of an idea. After all, it was just sex, and it would only involve a couple of hours of my time. I tried not to think that there would be an exchange of funds.
I decided that if the ad was still up when I got home from classes, I would respond. It doesn't hurt to ask. I wasn't committing to anything, right?
Sure enough, the ad was still up when I got home. I cautiously responded to the ad, just asking for more information. I mentioned that I was a twenty-year-old college student that had fallen on hard times. Within minutes, there was a response to my inquiry. Oh My God, my heart rate picked up as I now realised that this was real.
The man seemed very nice in his response, and we ended up exchanging numerous messages over the following day. The more we corresponded, the more comfortable I felt. He introduced himself as Jim, and I reluctantly told him my real name... a dumb move on my part.
We exchanged pictures, and he seemed pleasant enough. I wouldn't say he was attractive, but on the other hand, he wasn't repulsive either. He looked to be in his late forties or early fifties. He also had a short beard. I had never been with anyone with a beard before. Most of the boys I had been with hardly had any whiskers.
Jim said he was in town only for a couple of more days, so I agreed to meet him the next evening in the hotel lobby for a drink. I made it clear that this was just a meeting, no promises or commitments, just a drink. He agreed and said he would be very respectful of my wishes.
I didn't sleep all night. I was nervous and scared. What am I doing? Does this make me a prostitute? Imagine if my father found out. He would be horrified. So much for my religious upbringing. What was I going to wear?
It was a Wednesday evening, and I had spent hours getting ready for my date. I told myself it was a date to ease my mind and calm my nerves. I tried on several outfits, but in the end, I decided to forgo a skirt and just go with my tight skinny jeans and a nice tight sweater. He did ask for a college student in his ad, so I wasn't going to dress like a call girl and show a lot of skin. I dressed just like a normal twenty-year-old student... like myself.
Just the same, my jeans were super tight and showcased my small ass as well as a cameltoe on the front. My sweater also fit tight and defined my braless breasts nicely, including my pokies. I went with a pair of three-inch high heels to give my legs some length. It was a casual outfit, but sexy all the same.
For reference, I stood at 5'4", weighed 105 lbs, and my bra size was 34B. My hair was a natural light brown and was long and wavy.
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I arrived at the hotel and texted him from my car before going in, so he could meet me at the door. I was too timid to go walking through a hotel lobby looking for him.
As I got out of the car, I paused to contemplate what I was doing. I was nervous, but in a way, I was also excited. This was a new adventure for me, and the thrill of meeting a stranger and the possibility of having sex with him in his hotel room was very erotic.
The thought of being paid for sex was very taboo and such a large contrast to my religious and sheltered upbringing. I never thought of myself as sexy or desirable in any way. Why would anyone pay me for sex when they could just as easily pay a sexy call girl?
It occurred to me that we didn't even discuss money. It was like if I asked about the money, it would really make me a prostitute, so I never asked or mentioned it. The thought was too dirty, too disgusting.
It also occurred to me that we didn't discuss exactly what he was expecting from me. I should have set some rules or boundaries. This was all new to me, and I was too timid to negotiate the sexual and financial details with a total stranger. The lack of details made it less dirty and also gave me the option to back out. Besides, I might not be his type and the night might end after a drink.
"Hello April, nice to meet you," he said.
Damn, I shouldn't have given him my real name. I don't think I'm very good at this.
He motioned in the direction of the hotel bar, and we walked towards a quiet seat in the back.
As I moved through the bar, I could tell he was checking my ass out. Being on the slim side, I have always had a nice firm small ass. My skin-tight jeans and high heels surely accentuated my ass. Every guy I have dated told me I had a nice ass.
We sat down in the bar and began some small talk. Jim seemed like a nice man, not like anything I was expecting. I suppose I had preconceived ideas of what a man that propositioned young women on Craigslist would be like.
I did notice he kept looking at my breasts as we sat there. The more he looked, the more my nipples swelled up. My pokies were pretty obvious, I suppose. Overall, he behaved like a gentleman and was very polite.
Physically, he wasn't much taller than me in heels and was definitely overweight. He was not my type at all, but then again, I wasn't planning on dating him. He could have easily passed for any of the men from the church. There were no red flags, and he gave me no reason to run.
After a couple of drinks to calm my nerves, he asked me if I would like to go up to his room. There was a pause. Oh wow... he wants to have sex with me. The question somehow caught me off guard. I'm not sure why, but it did. I took a deep breath and timidly nodded discretely.
In the elevator, he put his arm gently around my waist. This was the first time he actually touched me. My heart was beating through my chest. I could not believe I was actually going through with this. My mind was racing with all kinds of different scenarios as we walked down a long hallway. I prayed he wasn't a serial killer or some sexually deviant individual.
He stopped, opened the door, and I hesitantly walked into his hotel room. I heard the door slam shut and locked with the latch behind me. There was no turning back now.
I couldn't help but notice the king bed was huge and the central focus of the room. The room was dimly lit, and there was soft music playing in the background. There was no doubt about what was now expected of me.
I was a bit startled when he immediately embraced and kissed me. He obviously wasn't wasting any time. He ran his hands over my body. Squeezing my ass and then brushing my tits with particular attention to my now fully erect nipples poking up through my sweater. I could feel a slight bulge in his pants as he pressed against me.
My mind was racing with all kinds of thoughts. What on earth had I gotten myself into?
I had convinced myself that this was like a date and now we were going to have sex. I kept telling myself this was no different than with other men I had been with. I knew what men wanted and I would engage in the sexual act, as I had done many times before.
Then he pulled away from our embrace, stepped back, and said, "Strip for me," in a firm voice.
