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Sex with a ssbbw

I hadn't been laid in 3 years.

Sounds insane? Not really. It's easy enough to find sex as a younger gay man, but when your hairline starts to recede, and you pile on the pounds, the well starts to dry up. Being far below average in the looks department doesn't help, neither does being socially awkward and broke.

I relied on memories of the past to keep me amused during my daily ritual of self abuse, then turned to porn when the novelty wore off. Becoming more and more desperate my tastes became more extreme, often things I never had any interest in trying. Bukkake, watersports, scat, torture, incest, you name it. Eventually the porn became useless. With no other options, I started trawling the internet for sex, but the guys I received replies from were below even my newly lowered standards, and the things they wanted to do to me were just bizarre.

One night, as I was jerking off and fingering my ass, trying in vain to get off, my thoughts wandered from the erotic to the mundane. I began to think about work, what needed to be done around the house, what to have for lunch tomorrow. Suddenly a thought occurred to me.

I ran to the refrigerator and grabbed a cucumber. It was about 6 inches long, 2 inches wide and covered in little bumps. Returning to my previous position, I resumed masturbating, this time with the cucumber instead of my finger. I was surprised how easily it slid into my lubed up ass, considering how long since I'd last been fucked. This felt much better than a finger. If I closed my eyes I could almost pretend it was a dick. The little bumps provided added stimulation.

With this sensation, I was able to get off. I didn't even need porn, I just imagined I was being fucked and I was able to cum. My orgasm was more intense than it had been in a long time. Feeling satisfied, I began to drift off to sleep... suddenly I was jolted awake by an unwelcome realization. The cucumber was still inside me. In my excitement I had lost grip of it, and it was now nowhere to be seen.

I stuck a finger in and felt nothing. I wasn't sure how deep it had gone. I started to panic. How far inside could it go? With nowhere else to turn for answers I went online. My searches were not reassuring, however they did provide a possible solution. My best option was to assume a squatting position and hope nature took its course. Nothing happened, I was out of luck.

I remembered there was a 24 hour medical clinic a few towns over. Did I really want to go there? The embarrassment would kill me, but then again, so could the cucumber. Did I want to be remembered as the guy who killed himself by shoving a cucumber up his ass? What the hell would they write on my gravestone? My mind made up, I made my way to the clinic.

The inside of the clinic was dull. Beige everything. There were not many people waiting there, only a haggard looking father, his screaming toddler and a gargantuan woman with an unsettling odor. I walked towards the matronly receptionist, still unsure of how to explain my predicament.

"Can I help you sir?"

"I have... uh..." I leaned in and hushed my voice. "I have a problem with my behind."

She raised her eyebrows, "And what exactly is the nature of your problem, sir?"

"Well you see, uh, I was in the kitchen, and I slipped.. and, uh, I have... I have a cucumber stuck... you know... up there."

Her dour demeanor gave way to laughter. She quickly stifled it and cleared her throat. "That's quite a story." I could tell she didn't believe it, but it was the best I could come up with. "A doctor will see you soon. In the meantime, fill out this patient information form. You can stand if sitting is difficult."

I mumbled something under my breath.

"Sorry?"

"Sitting's not a problem. It's... uh... much further up than that."

Barely able to contain her laughter now, she handed me a form and a pen. I checked around to make sure the other patients didn't hear anything. The father was on the verge of tears, being pummeled by his offspring, the hamplanet was asleep, snoring, drool falling from her open mouth into her ample, fragrant cleavage. I began to fill out the form. I hated forms but at least it would take my mind off my bowels.

Known health conditions? None. Smoker... occasional. Drinker... light to moderate. Activity level... sedentary. Can you climb two flights of stairs without feeling out of breath? No. Are you sexually active? Well obviously not or I wouldn't be here would I? Occupation... between jobs. After what felt like hours of meticulously cataloging my failures as a human being and a productive member of society, I handed in the form. I was now alone in the waiting room. I stared at a clock on the wall. Past midnight. Never mind, it's not like I had a job to go to in the morning.

It was almost 1am when I was finally called in to see the doctor. He was younger than I expected. Tall and fit. Good looking, maybe even handsome. His bedside manner, however, left a great deal to be desired.

"Sit there", he barked at me, gesturing to a chair. I obliged. "So, you have a cucumber stuck up your ass, huh? How the fuck did that happen?"

"Well, you see, uh, I was in the kitchen-"

"Yeah right. You were fucking yourself with it, weren't you?"

"I don't know what-"

"Why didn't you just buy a fucking dildo?" He interjected.

Good question. I didn't have an answer.

"You're a fat piece of shit. How much do you weigh?"

"What? Uh... I'm not sure... I haven't been to the doctor in a while."

"I'll weigh you after I'm done fishing this shit out of your ass. I bet you weigh a ton! Now, strip naked, go over to the bed and lie on your side." I did as he asked.

"Not that side! Turn over you stupid faggot!" I turned to face the wall.

I heard a glove snap. The doctor walked over to me. He lifted up my leg and held it in place. With his other hand gloved and lubed up, he stuck a finger in me. He had the coldest hands I'd ever felt. After a minute or so of aggressive probing he announced, "Yup, that's pretty far up." Well, tell me something I don't know. "Lie on your back, legs up." In this new position, he applied some more lube, and resumed fingering me. I wasn't quite sure what he was doing at this point, but I didn't dare ask. I felt another finger go in, and then, after a while, another. To be honest, I was beginning to enjoy the experience a little. The doctor started laughing. At first, I couldn't work out why. Then I realized he was laughing at my dick. I'm still not sure if he was laughing at the size, or the fact it was hard. Possibly both.

I'm not sure how much time had passed before he had his entire hand inside me. The experience was frightening and painful, yet exhilarating. Being fisted was something I'd considered before, a long time ago, but it was far too daunting. Not that this was fisting. It was some medical procedure. Sure seemed a lot like fisting. His pace had slowed considerably. Gradually, he pushed his arm into me, deeper and deeper. I didn't know how much more I could take. I wondered why he hadn't given me any painkillers or sedatives. He was almost up to his elbow when a grin lit up his face. "That's got it!" It took me a moment to work out what he meant. He was talking about the cucumber! I let out a sigh of relief, followed by a screech of pain as he began to pull the object out of me. After he was done, he leaned down and whispered in my ear, "You're a submissive little faggot, aren't you?" All I could do was nod, and sob.

As I lay on the bed exhausted and in pain, I noticed daylight streaming through the window, and wondered to myself what time it was. "Sit up!" I sat up on the bed and winced. My ass hurt like hell, and I was still crying. Undeterred, the doctor began to fondle my man boobs. "You've got bitch tits!" He exclaimed mockingly. "Better schedule you in for a mammogram. Wouldn't want anything to happen to these puppies." Continuing to fondle my breasts with his right hand, he grabbed a handful of stomach fat in his left, digging his fingers in and twisting a little. "Get on the scale fatty!" As I stood up and made my way over to the scale, he slapped my fat, sore ass.

"Almost 200 pounds! And you're what, 5 foot 5?"

"5 foot 7!"

He looked me up and down. "Nice try, you short, fat piece of shit! Anyway, that puts your BMI into the obese category. Or to put it in terms you'll understand, you're a fucking blimp!"

Obese? I didn't think I was obese. A little chubby, maybe. It's not like I needed a wand to wipe my ass.

"We need to put you on a diet! No more big macs, no more donuts. Just salad." He put on another glove, and went over to the waste disposal. He was getting something out of there. Was it- no, it couldn't be.

It was.

He hastily rinsed off the cucumber and handed it to me. "Eat it, fat boy."

I looked at the vegetable with apprehension. It smelled faintly of shit, and was slippery with lube.

"EAT IT!"

I did as he told me. It didn't taste any different to a regular cucumber, but nonetheless, I felt like puking by the time I was done.

"Hey fat boy, your dick is hard again!" And it was. He proceeded to measure the length of my erect penis. "Not even 5 inches! Good thing you're a faggot, you'd never satisfy a woman with that thing! Now get dressed, I'm sick of looking at your disgusting bloated carcass."

He told me to schedule a follow up appointment in two weeks. I went back to the receptionist's desk and noticed a different woman. Young, blonde, and with a mischievous grin on her face. She stared at me for a few seconds. "You poor thing," she said. "I think he likes you."

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