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.
