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.
I could tell by his tone that this was not a request, it was an order.
That’s when it hit me. As much as I wanted to pretend that this was no different than any other guy I had sex with, it was. He had purchased me to have sex with him! He was in control, and I was there for his pleasure. He owned me for that evening, and I was obligated to meet his needs.
I just stood there frozen for about 20 long seconds while I processed everything. There was silence as we locked eyes. He didn’t flinch, and I could tell from his stare that he was serious. For some reason, I was expecting things to move slower.
The idea that I was selling myself for sex was very humiliating, yet on the other hand, extremely arousing. I could feel the heat building up between my legs as I became moist standing in front of him.
The thought of bolting crossed my mind, but then I calmed myself with a deep, long breath.
I slowly began to strip as he stood back and watched.
As I slowly pulled off my top, I could feel my swollen nipples rub against my sweater before they dropped free, my long hair falling down in front of me as my sweater cleared my head, but not long enough to hide my breasts.
I paused momentarily before I lifted first one leg, then the other, as I awkwardly unfastened and removed my heels.
I paused and glanced at Jim with my arms crossed as I stood there topless in only my jeans. Neither of us spoke a word. I could see the bulge in his pants as he stared at my young, perky breasts as my nipples peaked over my crossed arms.
He didn’t say a word but nodded his head, gesturing me to continue.
I bit my lower lip and proceeded to slowly unbuckle my tight jeans. I slowly swayed my hips from side to side as I peeled down my jeans, kicking them free as they hit the floor. Again, I paused as I stood there in my white high-cut panties, before quickly removing them.
Jim kept his distance as I quickly crossed my arms and clenched my thighs. I stood there fully exposed in front of him for what seemed like an eternity.
He finally broke the silence, “Put your heels back on,” as he pointed to them.
I slid my feet into them and leaned over to buckle them up, my breasts freely swaying as I bent over.
He then twirled his finger to motion for me to slowly spin around so he could see my ass. He was inspecting his acquisition. For the first time in my life, I felt like a piece of meat.
Jim commented on my youthful appearance and my lean body. He reached in and got a feel of my breasts as he seemed taken by them. He then slowly ran a finger up my freshly shaved, moist pussy, sending shivers through me as I stood there frozen.
“Hmm…” from the moisture on his finger, it was quite evident that I was aroused. He proceeded to lick my nectar off his finger.
I didn’t say a word as I trembled with anticipation. He gently pushed me back to lying on the bed as he removed his shirt. I could now see just how overweight he was. A large roll of fat hung over his belt line.
I lay on the bed staring up at the ceiling as he parted my legs. He didn’t say a word; he just leaned forward and buried his tongue in my wet, pink folds. I was already wet and aroused, but when I felt his beard touch my tender pussy and his tongue rasp across my swollen clitoris, I quivered as I could feel an orgasm beginning to build.
I closed my eyes and gave myself totally over to the moment. I began to moan as his tongue worked its magic on me. I tried to keep some semblance of control, but it was no use. I got caught up in the sensations, and they carried me away like the current of a strong river as I had my first orgasm.
Jim was older and overweight, but by God, he was good. I had never had a man with a beard go down on me before, and it felt glorious. I was moving my hips in time to what he was doing and pushing myself into his face, and he pushed just as strongly back.
I could hear him breathing heavily as he was as excited as I was. He then began growling as he moved up my body to my breasts, sucking first one nipple into his mouth and then the other. He was a heavy man and his weight had me pinned down to the bed, and I liked it.
He was getting wild. He pushed my breasts together and somehow got both nipples into his mouth at the same time. It felt just awesome; I arched my back, offering him more. He was rough, and I loved that too, his beard scratching me as he manhandled my sensitive breasts.
He slid back down my body and attacked my pussy again. He growled loudly as he slid a finger inside of me. At the same time, his mouth devoured my clitoris. That was it. I went over the edge, with both hands, pulling him hard into me as I pushed my pulsating pussy into his face. I was moaning, and the waves of another more intense orgasm were firing through my body, as I arched back and let out a deep, satisfying moan.
“Oh my god, that feels so good, “I moaned as my body continued to quiver and shake to the rhythm of his fingers fucking me.
I had barely recovered from my wonderful orgasm when Jim pulled me off the bed and pushed me to my knees in front of him. Gathering my composure, I lunged and fumbled with his belt buckle.
Jim helped me unbuckle his pants, and I pulled them down, revealing a short but fat, throbbing cock. If I had to guess, his cock was no longer than four inches, but what he lacked in length he made up for in girth. The head was purple, huge, and looked ready to burst. He put his hand on the back of my head and just stuffed his hard cock past my lips and into my mouth. There was nothing smooth or sexy about it; he was definitely out of control.
Jim put both his hands behind my head and started pumping his cock into my mouth with abandon. He was stuffing that thing in and out of my mouth, literally fucking my face. Fortunately, he wasn’t long, and I was able to take his entire length in my mouth, although his girth did stretch my mouth.
I’m good at giving head and love doing it, but he wasn’t giving me a chance to slow things down to show my talent. I wrapped my tongue around his shaft and sucked as hard as I could, but he was just pumping away like a madman. I just kept rolling my tongue around his shaft and head as it slid back and forth while he fucked my mouth. I wish there were a more polite way to put it, but there just isn’t. It’s what was happening.
His breathing was hoarse as he moaned and pumped away like a machine until, without warning, he blew his load. He clutched my head tight as he shot blast after blast of his load into my mouth. I began to choke and gag as he held my head tight, not allowing me to pull back and breathe. His thick semen was gushing out of my mouth as I loudly moaned in protest. He finally eased up his grip on my head and I was allowed to breathe. I continued to suck and swallow as fast as I could, but to my surprise, he started pumping again, not losing a bit of his hardness. When the spasms of his orgasm finally weakened and he had spurted out all of his semen, he finally slid his semi-hard cock out of my mouth.
That was one of the biggest loads I had ever experienced. I was a mess. The makeup that I had spent hours applying was all smeared. There was semen all over my face and dripping down from my chin onto my breasts. This guy must have been holding his load for months.
I grabbed the bedsheet and wiped my face clean as best I could as Jim fell onto the bed. I then pulled his pants all the way off and crawled up his body, positioning myself on top of his belly. I leaned in and gave him a sloppy, cum filled kiss. I wanted him to taste his semen on my lips.
It was blatantly apparent that he had a thing for my young, perky breasts, so for the next thirty minutes or so, I swayed and tormented him with my breasts. I even told him to lick his sperm off my breast.I don’t ever recall having my tits suckled, pulled, kneaded, pinched, and sucked as much.
With him being older and so out of shape, I was beginning to wonder if he would ever get hard again. Maybe this was all his body had… Maybe it was time for me to leave?
Even if he did recover, I wondered if he could satisfy me with such a stocky cock. Honestly, with him being so out of shape, I thought he wouldn’t last more than five minutes before he either ejaculated or passed out from exhaustion.
It wasn’t long before he proved me wrong and I felt his manhood twitching. I reached down and supported his cock in my hand, squeezing and pumping it back to life as my breasts lapped his face. I couldn’t get over how short and fat his cock was. I had seen many cocks, but never one like his. I kind of felt sorry for him.
He was now rock hard again and grabbing at my hips to ride him. I held back momentarily and mumbled something about a condom. He looked at me with his glazed eyes and urgently said,
“No, just fuck me… quick.”
“But…” I was interrupted by his loud, stern voice, “I SAID, JUST FUCK ME…NOW.”
Sensing his urgency and too timid to make a scene, I guided his stout cock to my wet opening. Then, with one quick motion, he thrust his hips upwards and stabbed his cock inside of me, burying it in my quivering wet pussy. I sensed that this wasn’t going to take long, and my plan was to withdraw before he ejaculated inside of me.
He was thick, and he stretched me open in the most delicious way. To my surprise, it felt wonderful. With my hands on his chest, I started to leisurely ride him, enjoying the feel of how his fat short cock filled me. I ground my hips into him hard, trying to engulf as much of his cock as possible. His short cock wasn’t reaching deep inside of me, but his thickness was giving me much more pleasure than I anticipated. I was surprised at how wonderful it felt. Most of the time, I have trouble with large cocks as they can be painful, but Jim’s cock felt very comfortable. I could have ridden him all night long.
I ran my hands over his hairy chest as I began riding him faster and harder. I just love hairy chests, and he had lots of hair.
He was running his hands up my body, aggressively playing with my breasts as I moved on him. I was into it as much as he was. He pulled me down to him to suck my nipples. He rubbed his face all over my swollen breasts, squeezing and sucking on them. He grasped my hands and moved them to my breasts, and then started to squeeze and tease them, using my hands under his. He made me feed him my tits. I did, and after a few moments, he let my hands go and I put one hand behind his head as I fed him, first one breast, then the other, into his hot, hungry mouth. He was definitely a breast man, and he devoured my pearl white, firm breasts like no one ever had.
He was also rough; he bit and sucked hard, practically taking my whole breast into his mouth. I screamed in pain and pleasure as he mauled my super sensitive nipples.
He was getting too rough, so I sat up, pulling a nipple out of his mouth with a pop. I was still riding that fat cock and was having trouble keeping focused on what was happening to my body. The sensations were just too much for me. I always lose perspective during good sex.
Baby, play with your titties for me, show me how you like it… twist those nipples of yours.”
Geez, what is it with this guy and my breasts? They were now swollen and sore. I never had my breasts mauled like this.
I sat up a little straighter, bringing my hands to my breasts and began to gently knead them, squeezing and pulling on my nipples as he watched.
He was moaning with pleasure. He had his hands on my hips and was meeting the movement of my hips with hard thrusts of his own. I looked down at him, and his eyes were riveted on my breasts and what I was doing to them.
I placed my arms back behind me and leaned way back. I threw my head back and pushed my pussy on his cock. In this position, he could see his member sliding in and out of my tightly stretched pussy.
I was extremely flexible back then, and I wanted to really make a show of it. I laid all the way back, moving one hand down to my pussy and starting to gently rub my clitoris while moving slowly on his dick. I noticed a wall mirror next to the bed, and I could see that he had noticed it also. We were both catching glimpses of each other in the mirror.
He moaned, “Oh God,” put his hands on my hips, and started to thrust so hard that he was bouncing me into the air. A few moments later, he stopped, supporting my hips hard, forcing me to stop moving as well. I could feel his cock pulsing at the opening of my pussy and knew he was extremely close to losing it.
The head of his cock was the only thing in me at the moment, so I could feel him swelling as he fought back his orgasm. I didn’t want it to end either, so I didn’t move a muscle as he struggled to control his twitching cock.
When he was finally back in control, I slowly leaned back again until I was lying back on his knees. I didn’t move. I just squeezed his cock with my pussy, contracting and releasing at a slow, rhythmic pace. I started to play with one of my breasts and, with my other hand, rubbed small circles around my hard, sensitive clitoris. I’m certain he could see his cock deep in my pussy as I played with my clit.
I was moaning loudly now, totally excited. It really got me off thinking about him watching my pussy stretch as his cock moved in it.
I started to slide back and forth on him slowly. I’d move back until I could feel the head of his cock just ready to pop out and then just as slowly slide back onto him. It was an agony of pleasure. I was so ready to orgasm, but I was trying to draw out the moment.
I pulled back one time, and his cock popped out of my hungry pussy. I could feel his eyes feasting on my stretched open pussy before, with a slight movement of my hips, I engulfed his hard cock again.
My nipples were huge and swollen, and my pussy was starting to quiver as I continued playing with my clitoris. My clit was totally swollen, looking like a rosy pearl. On another stroke, I let his cock slide out of my pussy, gripping it and rubbing it over my engorged clit. It was driving me crazy. I slipped his cock back in and pushed myself onto him until he was submerged in my pussy once again.
Suddenly, he sat up and lifted me off of him. I felt so empty and moaned in disappointment. Swiftly, he jumped off the bed and pulled me to the edge of the bed, spreading my legs wide. He then just plunged his cock deep into me as I let out a deep gasp.
He was out of control, pumping away like a madman. I watched his soft belly jiggle as he fucked me. My orgasm had been building for so long that I couldn’t stop it even if I wanted to. I was into it before I even realised I was there. I came hard, and he continued pumping away. Every contraction of my orgasm wetly clamped down on his hard, driving cock, and I was thrashing about and screaming out my pleasure as he continued to fuck my pussy. I felt like a prisoner pinned to that bed by his cock in my pussy and his weight. It felt wonderful.
Just when I thought my orgasm was over, I rolled into another one and he continued to pump. I couldn’t believe his stamina. He must have taken Viagra to have that much stamina and staying power. Most younger guys would come when I did, and most of the time I’d be left wanting more. Not this time. This guy was an animal.
He bent down and snatched one of my nipples between his teeth and roughly pulled on it. I moaned in pain and pleasure. He twisted the other one around in his hand, pulling on the tender meat of my pale white breast. That set me over yet again, and finally, during this orgasm, he lost it too. I knew he was close when he let go of my nipples and started to pump away at my pussy even faster. I could barely speak in the state I was in, but I did manage to say.
“Don’t… cum… inside of…”
Suddenly, I could feel the hot streams jetting deep into my pussy, and he continued thrusting away as he came, grunting his pleasure.
When he finally calmed down just a little bit, he pulled his penis out of my pussy and moved up to my head, sliding it into my willing, warm mouth. This time I slowly started to perform oral. He seemed to enjoy it, but I guess he was pretty much done. His cock kept semi-hard for a while as I played with his balls and tried every trick I knew, but he had shot a couple of good loads and as much as he wanted to, his body refused to give any more.
I pumped his shaft gently while wrapping my soft tongue around him, but after a couple of minutes, he pulled his soft cock out of my mouth and walked over to the bathroom, closing the door behind him.
I lay on the bed contemplating what had just transpired. I was rather proud of myself in that I had the courage to actually go through with this. Although Jim had given me an unexpectedly good fucking, I felt a tingle of arousal.
Through my half-closed eyes, I caught a glimpse of my used, red pussy in the mirror. Something clicked inside of me. I reached down and started playing with my clit again. I spread my lips open and slid two fingers into my stretched-out pussy while my thumb gently rubbed my still swollen clit. With my other hand, I rolled a nipple around just like Jim had done.
I heard the bathroom door open, but I ignored it. It only took a few minutes before I quietly came back again while watching myself in the mirror. I moved my hand and could see my pussy clenching tightly closed and then relaxing open as the contractions of the orgasm coursed through my body.
Jim was standing at the foot of the bed watching me and made a comment about me being such a nympho.
Just as I was regaining control, he walked over to me as I lay spread out before him. He rubbed and squeezed my breasts for a few moments while with his other hand he vigorously rubbed my pussy, sliding a couple of meaty fingers into me. He finger fucked my cum soaked pussy and I instantly had another orgasm. The thought of being purchased by a stranger for sex was too much. I was in a heightened state of arousal. I wanted more.
As I lay there recovering, he inserted his cum-soaked fingers into my mouth, and I licked and sucked them clean.
As we both lay there naked and resting, I wasn’t sure what to do or what was expected of me next. I asked him if it was time for me to leave. He just smiled and asked if I wanted to spend the night. I wanted to, but I couldn’t as I lived at home. I told him I could stay for another hour or so if he liked. He said he would love to spend more time with me. His thoughtful response was all I needed to hear. I told him I wasn’t leaving until we had sex one more time. I wanted more of that chubby four-inch cock.
I snuggled in his arms as he continued to gently play with my breasts. He did love my breasts.
After about an hour or so, I detected some movement. I reached down and began playing with his limp cock. I have always had a thing for watching limp cocks come back to life, so I was eager to watch and help. I was more than happy to slowly suck him and give him a proper blow job.
Once he was good and hard, I told him to fuck me doggie style before I left. He obliged.
When it was time to leave, he pointed out the gift he left me on the dresser. I liked that he called it a gift and that he left it on the dresser as opposed to handing it to me. I discreetly collected the gift and placed it in my purse without even looking at it. I didn’t want to look at it or count it until the next day. This way, it seemed less related to sex. Well, it did in my mind.
He was relatively generous with his gift, which surprised me. I have always had a low sense of self-worth and the idea that he thought I was worth so much was very good for my confidence.
Overall, he treated me well, and I enjoyed the evening. I could see how some women could fall into the habit of doing this sort of thing.
About a month later, I met Jim again.
Student Aid Part 2 will follow soon.
