I hate my ass. While the rest of my body is fairly normal and thin, I have been cursed with a stupid bubble butt that I’ve gone through extreme pains to hide for most of my life. The only thing worse than my ass is my pitifully small cock, which taps out at three inches hard and isn’t anything to brag about in the girth department.
Look, I could probably deal with my ass issues if I had any confidence about what I was packing upfront. I feel like it wouldn’t matter as much and I would at least have some added confidence with the ladies. I’ve tried everything, pills, pumps, Jeq’ing, etc. None of it worked.
The first time I had sex was a colossal embarrassment. I could tell that she was surprised by how small it was and noticing that made it hard for me to maintain an erection and the condom kept falling off. I was incredibly nervous that word would get around, but luckily it didn’t.
By 19, that had been my only time having sex. I focused mostly on my studies and computer programming. To hide my ass, I wore loose pants that elicited some comments every now and then (people calling me a poser etc) but otherwise went unnoticed.
I shared an apartment with my friend Jeremy. He was a huge stoner and played in a local band. We didn’t share many classes or interests, but we got along pretty well. We smoked up and watched movies together about once a week. He was openly bisexual and would bring guys and girls back to his room every now and then, but it was never a burden on me, with the exception of being jealous of the girls he was banging. As I was straight, I wasn’t jealous of the guys, but also wasn’t homophobic at all. I started looking up to Jeremy after hearing the moans of extacy coming from his room.
In any event, I had a date tonight! I was nervous, of course, but concealed it. Her name was Amber and she was in a few of my classes. We got on quite well and she had a nice girl next door sexy look. She had actually been the one to ask me out for drinks tonight. I didn’t think anything would happen, being the first date and all, but I already started planning on escape plans if things got hot and heavy. At most, I could eat her out and make up an excuse to leave. I figured that if I could pleasure her that way at first, my small dick wouldn’t be an issue moving forward.
I arrived early and sat pretending to be engaged by my phone while sipping on a beer until she showed up.
“Hey Ry!” I heard her say as she walked up to the table. She always called me that instead of Ryan. I kind of liked it.
We started talking and time flew by. I think we both lost track of how many drinks we had and by the time we ended up at her place I was pretty wasted and couldn’t keep my eyes or hands off of her firm C-cup breasts or tight ass while we made out on her bed. We continued like this for a while and I started fingering her while licking her tits. I was so caught up in everything that I didn’t immediately notice her undoing my belt and gripping my cock.
Then it happened. She grabbed on to it..reached around a bit as if second guessing…her hand froze for a second and then she started lamely stroking me. I could feel the disappointment as her body slightly got more tense. I tried to ignore it and moved down to eat her out.
This served two goals: it brought her sexual energy back immediately and it gave me an excuse to shift my dick away from her hand long enough to think of my next steps. Even though her reaction had stung, i was still horny as fuck and wanted to fuck her. I fiddled in my pocket for a condom and kept my mouth on her snatch while I opened it and slid it on my schlong.
She was soaking wet and ready. I slowly slid it in. It was immediately disappointing for both of us. I knew she couldn’t really feel me and the fact that she was so wet made my pinky sized dick feel like it was floating in space. I meekly tried a few more thrusts before rolling off and laying next to her in bed, quickly pulling my pants up.
“I’m sorry,” I mumbled. Unable to make eye contact.
“Hey..it’s ok..I mean, I hear this happens to guys sometimes, we can always try again later” she said, sympathetically.
This was a nightmare. Her early hesitation appeared to be because she thought I was a grower that just hadn’t been able to get it up.
“It was hard, it’s just..” why why why didn’t I just let it stand and leave.
“Wait..what, really, how” she was tripping over words to describe her surprise and immediately corrected herself, “I mean, im sorry..I mean, its ok. I don’t know what..”
“It’s ok. I’m going to go.”
“Wh..wait. Instead of leaving me hanging, why don’t you help me out with this?”
She reached over to her bedside table and produced a dildo. It was on the smallish medium side, but still towered over mine.
“You could also keep using your mouth,” she smiled. “That was amazing.”
Fuck it. What did I have to lose? This was probably the closest I was going to get for another couple of years.
I dropped down to my knees on the ground with my torso on the bed between her legs. I started licking her clit and moved the dildo slowly into her. The change in reaction was immediate. After a while she was clasping at the covers, breathing heavily, and gyrating her pussy. It made me fucking hot once again and I slid my pants down and started wanking off while I continued to suck and fuck her. Before long, she orgasmed into my waiting mouth while I came into my hand.
She laid back catching her breath while continued to kneel there with the dido in my hand like an idiot.
“Fuck…that was awesome, Ry. Shit.”
I got up and my wallet dropped out of my pants. I knelt down to get it and my stupid pants slid all the way down.
“Whoa, nice ass, Ry” she said giggling.
“Um, thanks, uh, I gotta to”
“Wait, I’m sorry! Please stay!”
I ignored her pleas and left. The humiliation and walk home sobered me up mostly as I walked the 20 or so minutes back to my flat. I was in no mood to talk, but unfortunately our front door opened to the living room and Jeremy was hanging out on the couch watching a movie.
“Hey Ryan, didn’t expect you back to early, dude! You strike out that fast, huh?” He laughed.
“Ye..no, man, it was fun. Don’t want to talk about it. ”
“Cmonnnnn man” he said in his stupid stoner voice. “Come smoke a bowl with me and let’s hash it out. You at least fucked her right? Got some head?”
I grudgingly agreed to smoke up. Fuck it. It was better than sitting alone in my room thinking about it for the next couple of hours.
“We fooled around. ”
“Nice. Like what?”
“Oral and stuff”
“Niiiice. Nothing better than a good blowjob.” He said while excitedly kicking and throwing his hands in the air like a dork.
“No, I mean, I ate her out.” I was growing annoyed with this conversation and wanted it to be over.
“And you didn’t get anything back? Who are you? Mother Theresa?” He laughed.
“It just didn’t work out? Did she cum?”
“Then what the fuck is her problem.”
“Listen, I got a fucking small dick and it didn’t work out.”
I was burning with rage but it felt strangely relieving to get that off my chest. “You happy now? You wanted to know so badly?”
He turned serious. “Shit, im sorry dude, I’ll drop it. Let’s just watch this flick.”
We continued to smoke and he of course didn’t drop it.
“Can I see it?”
“What? The bowl?”
“Your dick. ”
“What the fuck man? No. I’m not like that!”
“I’m just curious about what you mean by small. Just wanted to know if she was just being rude to my bro for no reason.”
“Trust me.” I said, with my voice shaking. There was something about him asking and me picturing doing it…like an exhibitionist feeling or humiliation kink.
“Cmon, dude, not going to tell anybody or say shit.”
Fuck it. I took a long toke and undid my pants, pulling them down and my underwear, before standing up.
“What the hell, you said you wouldn’t say anything, dick.” I said as I started to pull up my pants.
“No, no, no..not your dick. I don’t care about that. Is this what you’ve even hiding under those big pants” he said as he groped my uncovered ass.
“Hey!” I said, but made no attempt to move. Strange as it sounds, after being rejected twice sexually, it felt kind of weird having any part of my body be the focus of sexual attention. I could see his pants starting to tent. Again, that my body was producing that reaction caused a weird reaction. I actually blushed and started to get a little hard.
“Fuck” he muttered as he continued to fondle my cheeks, spreading them and lightly swatting them.
“Ryan, dude, this is the best ass I’ve ever seen..on a guy or girl. I gotta..shit…tell me if you want me to stop” he said.
“What..” I tried to get out as I felt my cheeks spread and his tongue dive into my virgin hole.
Is this what it felt like earlier to be Amber?
For a few moments, I was too shocked to say or do anything. I was now fully hard and felt amazing.
“Unnnhhh” I moaned as his tongue and a finger made their way into me.
As good as it felt, I couldn’t hold this stance forever.
“Jeremy, please, fuck, stop.”
He got in a few more jabs with his tongue before he let go. Before he could do anything else, I got onto the couch, face down with my ass pointing up at him. I couldn’t bear to look him in the face, but I wanted more.
“Please, keep going” I whined.
He quickly obliged. I could tell that this was something he had done before. Before long, he had two fingers inside of me and I was moaning harder and harder.
“Oh yeah, baby, twerk your ass for me ” he said.
I didn’t know much about the mechanics of twerking, but figured he wanted me to fuck myself on his fingers, so I quickly obliged and started moving my hips and ass all around on his fingers as he forced them in and out.
“Mmm yeah, you like that, baby?”
“Unnhh yeah…fuck…oh yeah.” I moaned.
I couldn’t believe that my ass, which had been something I’d hidden for years, could be the object of so much pleasure for me. I also couldn’t believe that me, a straight guy, was bent over getting fingerfucked by my bisexual roommate.
Suddenly he stopped.
“Mmm, Ryan, this is fun and all, but I got to get my nut. Can I fuck you?”
I heard his shorts drop and felt the warmness of his cock pressed against my ass.
We both knew I wanted it. What did this make me? Was I gay? I didn’t think so given the pussy I’d sucked on earlier. Maybe it didn’t matter. Plus, Jeremy was a good guy. I knew he wouldn’t put me on blast.
“Ok” I finally said.
“Great!” I could hear the smile in his voice. I could hear him rummage through a drawer and come back with something. I felt cool liquid being smeared into my hole. Jeremy came around to my head and said “want to lube up my dick to make sure it won’t hurt you?”
It was faux-compassion. I knew he wanted me to touch his dick. I got into a sitting position and took hold of it. I was no good at eye measurements, but it felt massive to me. I dutifully rubbed lube all over it, feeling myself getting hornier and hornier.
“Let’s take this to my bed” he announced as he grabbed my hand and let me in there. He guided me to the bed and had me lay down on my back with my legs over his shoulders. As he shuffled around, his dick nestled next to mine. The size difference was almost obscene. He looked down smiling.
“Nothing to feel bad about, Ryan. Sex is about mutual pleasure. If you’re not big enough to please ladies, you have to consider that you have something big and beautiful enough to please men.”
Had he said this to me at any other time, I would have gotten mad. But, there was a certain truth to it in our current situation. I had not been able to pleasure Amber with my dick, and here stood Jeremy with his dick about to fuck my ass which he had passionately tongue fucked.
“Please fuck me” I whimpered.
“You got it ” he grinned as he slid his member inside of me.
His big mushroom head slipped into me quickly. I gasped and bit my lip as he continued to slide more and more in. It was uncomfortable, but to his credit, he was taking his time. After what seemed like an hour, I felt his huge balls nestle against my ass.
He began pumping in and out pretty slowly, allowing me to get used to the feel. The feeling was indescribable. I felt like my entire body pulsating with electricity and all my nerve endings were firing on all cylinders.
“Mmm fuck yeah, your ass is so tight, babe” he groaned in between pumps. Again, I felt weirdly proud of how my ass was driving this guy, my friend and roomate, so crazy.
His pumps started intensifying and he started leaning heavy onto my legs as he picked up pace. At this angle, his cock started really brushing against my prostate and I went absolutely nuts. My eyes rolled back and I lost sight of time, place or anything else as my insides exploded with pleasure.
I let out some huge moans that I’m sure our neighbors could hear, but I didn’t care. I found myself wailing like some crazed slut in a porn, begging him to fuck me harder and telling him how good it felt.
“Holy shit, holy shit” he started huffing and puffing, slamming his dick into me as hard as he could. I reached down and started jacking myself off and came within a few strokes, the cum flying between us and onto my face.
“Fuckkkkkkk” he moaned as he straightened out, pulled his cock out of my hole and shot load after load of his cum all over my dick, balls and stomach, before collapsing next to me in bed.
Looking back, I would have expected my post orgasmic feeling to be one of disgust or regret. It was the opposite. I felt completely satisfied sexually. I didn’t feel awkward. As if out of reflex, I lazily laid my head on Jeremy’s chest and absent mindedly played with his softening dick.
My ass felt wide open and I could feel cold air entering. It was a weird feeling and wondered if this is how girls felt after being fucked for the first time. Not to say that I now considered myself a girl, I still dug chicks a lot. Still, Jeremy had opened a whole new dimension of sex to me and I was eager to explore it further.
“Fuck, that was hot. How is your hole, dude?” Jeremy said after catching his breath.
“It’s ok, I think..” I said with a hint of humor.
“Cool. You want to sleep in here?”
“Yeah, I’d like that.”
“Alright! Come here!”
We settled into a spooning position with me being the small spoon. I felt his warm cock resting in my crack and smiled. His hand draped over me and he gently caressed my nipple.
I figured we would probably have a talk tomorrow. But for right now, I felt completely fulfilled and fell asleep in his embrace, betting that I’d wake up to his morning wood poking me. I couldn’t wait.