Student Aid Ch. 02Student Aid Ch. 02

Brooklyn Chase

My Craigslist encounter with Jim was quite a memorable experience. In the end, Jim was nothing special to look at, but he was kind and respectful to me, which always goes a long way in my book. But the thing that stood out the most, or should I say, the least, was his penis.

He had the shortest, fattest cock I had ever seen. When I jerked him off, the entire width of my small hand almost covered his entire length. I estimated his cock at maybe four inches long when fully erect, and that was being generous.

Yet that fat little cock gave me one of the best sexual experiences of my youthful life. His girth stretched my pussy walls and filled me up wonderfully. Jim was a very comfortable fuck. No worries about bouncing too hard on his shaft and hurting my cervix. No, I could ride Jim’s cock as hard as I wanted to, and all day long without feeling any pain.

His stamina and endurance were also a big surprise. I never would have guessed that from his overweight appearance. I’m reasonably certain he had taken Viagra, as he was constantly hard, but that’s something I would never ask about. Either way, he gave me a wonderful experience.

I was also proud of myself for mustering the courage to actually meet him at his hotel. I have always been very timid, and I consider that a character flaw. I have always had a hard time speaking up and standing up for myself. I was a pushover, and the guys took advantage of this.

So about a month after that first encounter, I received a message from Jim. He said he was back in town and he would like to see me the next evening. He asked me to come by early so we could spend more time together, seeing that I lived at home and couldn’t spend the night.

The pleasant memory of our previous encounter prompted me to make an excuse to my boyfriend, and so I was knocking on his hotel room door less than twenty-four hours later.

Being late spring, I wore a short denim skirt and a cute white top without a bra. The top wasn’t see-through, but it was flimsy and thin. It was typical of me not to wear a bra back then. I had nice young, perky tits, and I enjoyed the attention of going braless.

Jim answered and immediately hugged and kissed me as we stood in the entranceway of the room. He complimented me on my outfit and how hot I looked in my short denim skirt and heels.

He poured me a glass of white wine, and we moved to a couch that was next to the window. It was early evening, and a pleasant light was coming in through the open blinds.

He didn’t seem as rushed this time, which I appreciated. As we chatted to catch up, his hand was on my bare leg, gently caressing my thighs. The wine was sweet, and I drank it rather quickly as it tasted more like a fruit drink. He quickly topped up my wine glass. The wine was loosening me up, and his hand on my leg was getting me aroused.

He mentioned that he had missed me and thought about me often over the last month. I smiled and said I also had. What I didn’t tell him was that I was thinking of him for different reasons. I still couldn’t get over his small cock. It reminded me of a childhood story about the little train that could.

He pulled out a camera and asked, “Mind if I take a few pictures to remember you by?”

“Um. I hate getting my picture taken. ” I knew from previous boyfriends that pictures meant naked pictures.

“Oh come on, just a few… You look so adorable, ” he promptly moved off the couch and began clicking before I could respond. He took a few pictures of me on the couch and then asked me to stand up and slowly remove my top.

“You want pictures of my boobs, don’t you?” I playfully teased him. I was feeling the wine now, and my promiscuous side was showing itself. Besides, I felt a little obligated as he had given me a generous gift the last time we met.

“Yeah, I love your breasts,” he responded with a big grin as he grabbed my hand and helped me stand up.

“By the window light…” he gestured towards the window.

“Not my face though,” I asked. Jim didn’t respond to my request.

I playfully began to model for him. Having my picture taken by a guy has always been a big turn-on for me. It’s great foreplay.

I’m sure that standing in the light from the window, my thin top was translucent. The more he clicked away, the more I could feel my sensitive nipples swell and brush against my top. My nipples always swell up when I’m aroused and give me away.

As I playfully swayed and began removing my top, I stopped and said

“These are private pictures, right? You’re not going to show these to anyone, are you? “

“Of course not, they are for my eyes only,” he reassured me.

“And your cock, “I giggled.

He just smiled and nodded.

Click, click, he continued as I bared my breasts like a good little slut. I tried to hide my face behind my hair or look away from the camera as much as possible. But I knew he was getting my face in his pictures.

After multiple topless poses, I dropped my skirt and gave him a view of my white high-cut panties.

“Bend over… Turn around… on your heels… “he furiously clicked away.

After about five film izle minutes of him taking pictures of me in only my panties and heels, I had enough and embraced him.

I whispered into his ear, “I’m fucking horny… Put down the camera. “

I reached into his pants and grabbed his hard, stiff cock as we kissed.

He pushed me down on the bed and pulled my panties off. He was about to attack my pussy when I softly said, “No, I need you inside of me now.” I was hot and aroused from the picture taking. I also recalled how wonderful his cock felt inside of me last time. I greedily wanted him to fuck me without any further delays. I was wet and ready.

Within seconds of my request, Jim quickly stripped and ploughed into me. It was pretty obvious that our little photo session had gotten us both hot and bothered.

His short, fat cock was just as I remembered it. I can best describe it as a bit smaller than a beer can… short and stout.

I felt him stretching the walls of my vagina as he entered me. I wrapped my legs around his fat waistline as he humped and pushed into me. His weight pressed down on me, and his hairy chest tickled my erect nipples. He huffed and puffed as I surrendered to him.

“Oh, fuck me… Yes… just like that… ” Although I was having regular sex with my boyfriend, his cock was nowhere near as thick as Jim’s. Besides, my boyfriend never lasted very long. It was more about him getting more satisfied than me. Jim was a good lover. He worked hard to satisfy me.

Jim was out of shape, and I could tell he was running out of breath. I was close to climaxing and needed more, so I asked him to roll off of me as I jumped on top of him. I lowered myself back onto his hard, thick member and rode him as hard and fast as I could. He was a breast man, and he grabbed and tugged at my perky tits as they bounced and swayed in rhythm to my hips riding him.

His cock felt incredible as jolts of excitement shot through me. I couldn’t hold back any longer as a wave of pleasure poured through me. I let out a loud moan as my head fell back and I had a satisfying orgasm on that wonderfully perfect cock.

Jim was still as hard as a rock. I am certain now that he was being helped by one of those blue pills. Most guys I’ve been with would have cum by now. I mean, he had a sweet twenty-year old fucking his brains out and cumming on his cock… what guy wouldn’t have cum by now?

I jumped off of him and knelt down on the bed over him and began sucking his cock. He began fucking my mouth, the head of his short, fat prick battering the back of my throat. I looked up at him. I could tell he was close to coming. He put one hand on the back of my head and pushed hard, making me gag while he groped my tits with his other hand.

I had one hand wrapped around his big balls, milking him while I sucked him, and the other between my legs, giving my clit a rub before inserting a couple of fingers into my sopping cunt.

“Oh, fuck, yes.” He stiffened up, pushing hard into my mouth as he pumped and ejaculated his warm sperm. I gripped his balls as hard as I could. He moaned loudly as I squeezed and sucked as much semen out as I could. Just like before, he shot an enormous load, much more than I could possibly swallow or hold in my mouth. He wasn’t lying when he told me he hadn’t had sex since the last time we met over a month ago.

Looking up, I removed his cock from my mouth and showed him his load all over my face and on my tongue. I then swallowed it all down. Jim scooped up the remaining semen all over my face with his finger and fed it to me. In return, I licked his cock clean.

His arms snaked around my ass, pulling me closer as I snuggled in. He kissed me hard as our tongues shared his taste. I couldn’t help but think how much I enjoyed having sex with Jim. He smelled nice, and he was soft and chubby to cuddle with.

As we lay in bed recovering, the hotel phone on the night table rang. James answered the phone. “Hello… yup… yup… OK… bye,”

“Everything OK?” I asked.

“Yes… is everything OK with you?” He smiled back.

“It will be as soon as you get hard again,” I laughed.

A few minutes later, there was a knock on the door. I looked at Jim, and he said, “Your surprise is here.”

“Oh, I love surprises,” I shot back, wondering if it was room service.

Jim got up and put on a hotel robe as he made his way to the door. I ran into the bathroom to wash up for dinner. I jumped into the shower for a quick wash, taking care to make sure my hair or makeup didn’t get wet.

While drying myself off, I could hear voices. I thought Jim had turned on the television. I wrapped a towel around me and opened the door, walking through into the bedroom.

“What the fuck?” I wrapped my arms around my chest, pulling the towel tighter in embarrassment and shock. Sitting on the couch with Jim was another man.

“Wha….. this is….” I couldn’t form a sentence.

“Relax. This is a colleague of mine. I’ve told him about our arrangement; and, he wondered if you’d be interested in… umm… extending the deal to him. ” I stood there, half-naked fragman izle and wet, with these two guys in front of me. I was being offered up like… I don’t know what! A hooker!

He stood up. “Look, sorry, I thought James had explained. I’ve got $200 for you, but obviously if you aren’t interested…” he let the words trail off.

Could I? Between the two of them, that would be… uh, a lot of money. Fuck, it was tempting. That was something like over two months of part-time work.

Still, a bit confused and humiliated, I couldn’t find my words, “What… are you… do you want to join us?” As soon as the words left my mouth, I realised it sounded more like a proposition than a confusing question. I was just trying to make sense of the situation, as I had no idea what they were thinking.

He looked at Jim.

“I don’t mind a threesome,” Jim said.

The other guy smiled. “If you’re up for it,” he said to me, “then I’m OK with that.” I was still in shock as I looked at Jim smiling at me.

I could see Jim was nursing a hard-on, and the other guy was showing signs of excitement too. Oh shit, this was moving fast. I was now blushing and embarrassed as I sounded like a cheap hooker.

“OK… but… you have to wear a condom,” I said in a hesitant tone.

“I don’t have any… But I’m very clean… honestly, “he shrugged his shoulders.

I didn’t really know what to say or do. Remember, I was very timid back then and I always avoided confrontations.

Picking up on my hesitancy, “I’ll give you $300…” he said.

“Um… OK,” I shrugged, thinking, wow, did I just negotiate a great deal?

“Paul,” he said, as he started to unbutton his shirt.

Jim must have read my mind as he handed me another glass of wine and put his arm around me. I don’t think I ever drank a glass of wine so quickly.

Jim held me in his arms tight, making me feel secure and protected. He then spun me around and hugged me from behind. As he held me, he began nibbling on my neck. I let my head fall back onto his shoulders. I could feel the towel loosening up and starting to slip. Paul stood there in front of me, watching as Jim slowly tugged on my towel, letting it fall to the floor.

Jim was holding me from behind and running his hands all over me as I surrendered to him. With one hand, he was rubbing and pinching my erect nipples, while with the other he was running his fingers up and down my wet, bald, and swollen vagina. He was showcasing me to his friend Paul.

“Holy shit,” Paul muttered in approval.

I reached behind me and slid my hand inside Jim’s robe, grabbing his cock as Paul watched me stroke it.

Jim moved me onto the bed. He began kissing me hard, his hands on my tits, pulling at my nipples. I pushed his head towards my groin. He kissed my stomach before burying his head between my legs, his raspy tongue finding my hardening clit. I groaned as he started to tongue my lips, making slurping noises as he got to work. His short beard roughly rubbed my pussy in the most wonderful way.

I couldn’t believe this was happening. I was on the bed naked with my legs spread as Jim was licking me and Paul was watching. I began to thrash about in pleasure.

Paul pulled off his boxer shorts and I got a good look at him. He was about thirty. He was taller than Jim and in better shape, with quite a well-defined body. His cock looked nice, long, more than a mouthful. His balls were shaved. He looked at me, perhaps waiting for permission.

As I stared at him, I licked my lips, and he got the message. Paul slid onto the bed next to me, feeding his cock into my mouth. Jim’s tongue was deep inside me, along with one finger, and I moaned around Paul’s shaft. He was hard, really stiff inside my mouth. I ran my hand up his thigh and cupped his balls as I began to take my second cock of the day.

“She’s good,” he said, looking down at Jim. Their eyes were locked in agreement.

I started to cum as James pushed two fingers into me, pumping his hand in time to his tongue fucking me. My mouth gripped Paul’s cock, and I pulled at his balls as I boiled over into orgasm. My chest went red, my nipples hard. Paul reached down and caressed my tits, flicking his fingers over the nipples. He began to thrust it into my mouth. I slurped my tongue around the head and shaft, and I began to stroke his shaft as Jim continued to bring me off with his tongue and fingers.

I was concentrating hard on Paul when I felt Jim shift. Then, I felt his cock against my pussy lips, rubbing the head over my clit before he pushed hard into me. I was all for a rough fucking. I took Paul’s tool from my mouth.

“Come on, you pussy, fuck me properly,” I goaded Jim.

He gripped my knees and spread my legs, his thick cock filling my cunt and his thumb rubbing my clit. I took Paul back in my mouth. He thrusted against my lips and teeth, deeper than Jim had done earlier. I felt him tense. I looked at him with my best begging face, squeezing his testes and pumping hard, my mouth tight around his shaft.

“Fucking hell…” Paul grunted and flooded my mouth with his cum. I tried to swallow dizi izle it all down, but I had lost my focus. I was on the edge of another orgasm as Jim was now banging me for all he was worth. There was too much going on. I moaned with pleasure as I tried to swallow Paul’s semen, but most of it dribbled down my chin. Paul stroked some more cum into my mouth, then used his finger to scoop the overflow into my mouth.

As Paul groped me and watched, Jim continued to fuck me in different positions. I was on the cusp of another orgasm when Jim pulled out.

“Let Paul fuck you,” he commanded. I lay back, spreading my legs. The wine was hitting me now as I felt the room spinning.

“No, you get on top.” Paul was hard again, so I did as Jim said, taking Paul’s cock into my sodden, wet vagina. At first, his cock felt different than Jim’s, or my boyfriend’s for that matter, but at this point, I was too hungry for cock to make any comparisons. I leaned forward, my tits in Paul’s face, and he sucked and bit on them.

Jim positioned himself behind me. I felt him work a finger into my ass. I moaned at the sensation of having Paul’s cock inside of me while Jim was fingering my ass. Because I am petite, I have always been hesitant about anal sex, and to be honest, I had only done it a few times at this point in my life.

I felt Jim withdraw his finger and then, without warning, I felt his cock begin to push against my anus.

“No, please don’t do it… oh”. Jim ignored me as he held me firm from bouncing on Paul’s cock and continued to push and feed the head of his cock into my ass. Paul was now holding me firm as his cock twitched and pulsated inside of me.

“Oh…FUCK…” I cried in pain as I felt the head of Jim’s cock pop inside of me. I just froze as I overcame the pain of Jim stretching me. He held me tight from behind and, with multiple slow and small thrusts, he was inside my ass.

This was the very first time I had been double penetrated.

I could feel Paul’s cock against the head of my vaginal walls, and Jim was up against it, too. It took me a minute or so to overcome the pain, but then something came over me…

“Oh, yes, you fuckers, fuck me…” I couldn’t believe what was coming out of my mouth. I was being too sound and feel like a cheap hooker. I mean, what kind of girl has sex with two paying men and performs double penetration? It certainly wasn’t supposed to be me. I was raised in the church! I was a good person. What has come over me?

Paul was happy to let Jim’s thrusts do all the work. He pounded into my asshole as hard as he could. I felt his hands on my hips and Paul’s hands on my tits. I was covered in sweat. The room was thick with the smell of climax and cum.

The encroaching darkness outside filtered into the room, making it all the more animalistic. I came, again and again. I kept telling them, “Fuck me harder… more… more…” I could feel my cunt and ass holes being stretched. My clit was on fire. I needed Paul’s semen in me to cool me down.

“Come on you fucking bastards,” I urged them on. I was playing the role of a prostitute, and I liked it. It felt very liberating. The shy, conservative, and timid girl had lost all control… My inner slut had finally been unleashed, and it exploded out of me.

Paul began to thrust up hard against me. I could feel Jim getting close, his cock twitching inside my back passage. I drove down hard against them both.

“Fuck…. me….. fuck…. me….. fuck…. me….. fuck…. me…”I was on the verge of another orgasm when I felt Jim slam his cock in deep, and he pulsed as he released his cum into me. His breath was hot and heavy against my neck as he leaned against me, spent.

Paul’s grip on my tits tightened as he lost control and his seed flooded my vagina. I pushed down hard on him, desperate to drag that last orgasm out of my tired and well-used body.

I felt Jim’s dick slip from my ass and I drove down against Paul’s cock, once, twice, three times. That was it; a powerful orgasm racked my body. My legs turned to jelly and my face was burning hot. I collapsed onto Paul, sweaty skin against sweaty skin. My ass and cunt felt alien, like they didn’t belong to me.

I shared kisses and cuddles with both Paul and Jim as we lay in bed, totally exhausted. After about fifteen minutes, both men started touching me. I sensed it would be wise if I made my exit before they got hard and started up again. Remember, I suspected Jim was on Viagra, so he could probably go all night.

I got to my feet, my legs barely holding me up. Paul jumped up to assist me. The wine and the sex had turned my legs to rubber. I could feel the combined juice of the two men dribbling out of me as I headed for the shower.

Paul adjusted the water temperature and then stepped into the shower with me. He held me from behind as we both washed and soaped the sex from our bodies. The warm water felt wonderful as it cascaded over me. Paul’s hands were all over my breasts and ass. I could feel him getting hard behind me. His cock was pushing into me. To be honest, I had enough sex for one evening, but Paul persisted. It occurred to me that he was paying me a lot of money, so I thought it best to just bend over and let him take me. After all, I wanted him to be happy with me. So there I was bent over, ass up in the air as Paul gave it to me doggie style in the shower.

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