Bashful

I think I have mentioned it before in a previous post…Nerds are great fucks! I don’t know why, but all three of the certified “Nerds” I have fucked have been off the chain!

The most recent was last week. As is often the case, I received an unsolicited comment to my profile on one of the hookup sites I use. To be honest, the pics of the guy were “Not All That”…but not totally Butt Ugly either. What caught my attention was the obvious shyness that came through during our chatting. I always try to respond to everyone and less than one percent ever result in anything… unless there is something that pricks my interest. In this case it was obvious that this guy usually looks at the pictures but does not do much more than that. Don’t know why, but I found myself wanting to see if I could bring this guy out of his shell a bit.

To make a long story short, we chatted for about 40 minutes online. During that chat I learned that he had plans to go to a dance at a local gay bar the next night with some of his friends. I had been to this monthly dance once before and determined that it was pretty lame and left after about 30 minutes. After chatting with “Bashful”, I decided to go to the dance just to check him out.

When I arrived, there were only about 70 to 100 guys there…still as lame as I remembered…so it was easy to spot him. Although his pictures on the site were recent, he is one of those guys who look a bit better in person than in photographs. He is 5’9”, probably 170 lbs, dark hair, glasses and a full beard. His hair is cut short, but he had bangs in the front, which made him look younger than his 30 years and sort of cute in a puppy dog way. Also, he is one of those white guys who could spend hours in the sun and just end up with more freckles than tan…again, kind of cute.

I grabbed a beer from the Very Friendly bartender and just watched Bashful from across the dance floor. He was with a gaggle of friends who were acting more like girls than grown masculine men. Fortunately, he was not exhibiting the same behavior or I would not be writing this post now.

Soon the dj put on a decent dance tune and several more guys hit the dance floor including Bashful. Ok… now get this…this guy is straight up Nerd…but on the dance floor…”his shit is tight!” I guess I should have told you about the best part of his anatomy…killer bubble butt with narrow hips. He had that ass moving in synch with the beat and I got an instant boner. I mean he had it poppin. He may be a Nerd in real life, but on the dance floor a metamorphosis took place… and it made think…”with a booty shake like that… he has got to be a decent fuck”

After the music changed, Bashful went back over with his friends, only this time It seems that I was not the only one that noticed his hot ass. Another guy… a hot looking Hispanic guy… was all over him. About the same time Hispanic Guy was making his move on Bashful is when Bashful noticed me standing over by the bar watching him. I could tell that he was not sure if was me or not by the way he kept looking back at me over his shoulder as the Hispanic guy pulled him into a dark corner.

After what looked like some heavy petting in the dark corner, Bashful made his way across the dance floor and stepped to me.

Bashful: “I did not think you were going to come”

Me: “I did not say that I wasn’t”

Bashful: “Did not say that you would either”

Me: “That’s me… keep you guessing” I said with a smile

Bashful: “Well?”

Me: “Well what?”

Bashful: “Are you going to make me ask?”

Me: “You bet”

Bashful: “(Sigh) Ok…well what are you thinking”

Me: “I am thinking that I like what I saw on the dance floor and I am wondering what that would feel like on my cock…but you have at least two other admires in the room so you go on and enjoy yourself…I will see you tomorrow night for an answer to my question”

With that, I put my hand down the back of Bashful’s shorts and felt his sweaty hairy ass, giving it a strong squeeze. I noticed that Bashful’s gaggle of friends had all stopped talking and were watching us intently…one of them even had her hand to her mouth (so so gay). True to form, Bashful turned red in response to my forceful gesture and the attention it created; however, he did nothing to stop me or otherwise object. After a putting on a good show for the gaggle of girls, I removed my hand and sent him back to the group.

I stayed for another beer and just watched Bashful. I think he like that because he kept checking every few minutes to see if I was still there. He seemed to get nervous when the Hispanic guy put his hands down his shorts and began to grind his crotch into Bashful. At that point Bashful looked over at me again…I grinned and gave him a look that said “Its ok”, and he seemed relieved.

They continued to mess around for another five minutes until Hispanic Guy’s put his hand on the back of Bashful’s neck trying to get him to go down on him. Bashful protested by saying something in Hispanic Guy’s ear and the guy immediately turned to look at me over his shoulder. I simply raised my beer bottle “Hello” at him. Hispanic Guy was not happy, but he put his junk back in his shorts and moved on. I finished my beer, winked at Bashful and left.

When I got home, I sent a text message to Bashful telling him that I would be at his apartment at 5:00. He was to be all cleaned and pre-lubed at that time. I also told him that I expect him to be a man and take the pain like a man. He could grunt and moan all he wanted but he was not to speak unless I asked him a question. He responded with a simple text that said,

Bashful: “Yes Sir”

I arrived at the appointed time and sent Bashful a text telling him that I was downstairs. He came down and let me in the building…I could tell that he was nervous and excited all at that same time. I followed him to the elevator, and stayed behind him the whole time so that he could not see me.

He looked at me for the first time once we were alone in his apartment. I did not say a word… just motioned for him to turn around so that his back was to me. In one motion, I grabbed his kaki shorts and yanked them down to his ankles… he was not wearing any underwear. I then lifted his t-shirt half over his head, but not off. I told him to brace himself against the wall with his butt sticking out.

I made him stand there like that while I took off my shoes and shirt. I purposefully took my time undoing my pants, making sure that my belt buckled clanked a few times and that he could hear me lower my sipper. At this point there was a slight tremble in his legs.

Bashful jumped slightly as I reached to feel his hole. It was indeed well lubed. More for show than anything I loudly spat in the palm of my hand and rubbed on the fat head of my cock. When I placed the head at Bashful’s puckered hole, the trembling in his legs became much more pronounced as the anticipation of the pain began to unnerve him.

Me: “Relax Bashful… and let me in… ok?”

He shook his head “Yes” and steeled himself for the entry of my cock. I rubbed the head of my cock up and down his hole a couple of times before pressing the head in at the center of his hole.

Bashful took the head of my cock with a loud grunt. I waited for him to adjust a bit… he was panting heavily as he dealt with the pain. I pulled the head out, and then pushed back in again… this time going a little deeper. Again Bashful grunted and started to pull away.

Me: “Come back here… don’t run… take it… you are a man… take it”

In response, Bashful not only came back, but I guess he decided to get all of the pain over with at once because he rammed back hard on my cock…literally skewering himself on my cock…with that Bashful let out a loud

Bashful: “AW Shit!”…”AW Fuck That Hurts…Sir”

Me: “I said NO TALKING”

And with that I pulled almost all the way out and shoved back in hard. Bashful grunted and grunted but he did not talk any more.

When It seemed that he had adjusted to the pain, I found an nice steady fuck rhythm. For a bit, the only sound in the whole apartment was the sounds of my thighs and balls slapping against Bashful’s ass and his grunts and moans that were in time with my thrusts.

I fucked Bashful like this for a good ten minutes…until his whole was completely open to me and he could feel pleasure instead of pain. Then I pulled out of him and put him on his knees and made him suck my cock…ass juice and all. He was hesitant at first, but took my cock into his mouth started sucking. I put my hand on the back of his head and began to face fuck him. This… he could not handle so well. After the third deep thrust into his throat, Bashful came off my cock and sprinted to the bathroom which fortunately was close. He just made the toilet as he threw up.

I waited outside the bathroom for him as he went through the dry heaves. To his credit, he quickly took a hit of mouth wash and then came back out into the hall way…dropped back to knees and opened his mouth for more throat fucking. I was impressed with his willingness to go right back at it…but the whole mouthwash thing reminded me of his Nerdiness.

After the throat fuck, I moved Bashful to his bedroom (bed made…everything in its place with labels…yeah…labels). I put Bashful on his knees with his chest down on the mattress. I lined up my cock and by this time he was so open that I did not even use my hand to guide my cock in. I fucked him steadily like this for another ten minutes, then flipped him over on his back. I pressed his legs back against his chest and power fucked him hard. Bashful just stared at me with a sort of dazed look in his eyes and his mouth and beard still wet with excess saliva from the face fucking. He did not make a sound in this position… he just stared and kept gripping my biceps with both hands…sporting a six inch hard-on that jumped each time I bottomed out in his ass. He felt Amazingly good!

I was soon ready to cum but I did not want to breed him on his back. For some reason I tend to cum harder and longer in doggy style. I put him back on his knees and , gripped his narrow hips and started pounding him balls deep. This angle must have been better for working his prostate because he was by far more responsive in this position than any other.

I had picked up the tempo and was building to unload in him when I felt his body convulse. I thought I knew what that was, but at that point I was too focused on dropping my four day load to care.

Within about ten more strokes, I passed that point of no return and I relaxed into a GREAT SHOOT! You know the kind that just seems to keep flowing and flowing and flowing out of you. With each pump more and more endorphins are released and you have the completely satisfied feeling. When I pulled out of Bashful, a river of very thick white cum trailed out of his very open hole and down his balls.

At this point, Bashful collapsed on the bed exhausted. I went into the bathroom and retrieved a damp wash cloth and came back to clean Bashful up a bit. When I had him turn over on his back, I could see that the convulsion he had at the end was exactly what I thought it was… there was a huge wet spot under him where he had shot his load while I fucked him in the ass.

After cleaning up a bit, I retrieved my clothes in the hallway and got dressed. Before I left, I looked in on Bashful… he had gotten under the covers and gone to sleep. At about 10:00 PM that night I received a text from Bashful

Bashful: “Please use this cumdump again Sir”