This Hole Really Needs to Be Filled

This Hole Really Needs To Be Filled...Don't You Think?

My name is William, I'm 34, a certified medical technician for ambulatory medical emergencies. I love my job and make pretty good money. I'm white male, about 6' 2"s tall, and 190 lbs. I have a moderately hairy chest, a defined torso, not a six pack mind you, but it's tight and toned, with no flab. I belong to a gym and work out regularly, plus I play in a men's softball league. So yea, I'm in pretty good shape.

I got an almost 8" cut cock, and while it's not the longest in the world, I have been told by more than one lover that it has extraordinary girth. Many lovers have told me, it's way thicker than any other cock they have ever seen. Facially, I modestly think I'm considered better than average and I have no trouble meeting women or getting into a sexual relationship with them. I'm going through a divorce, but it's amicable, as we still get along pretty good. My wife got the house and I'm living in an apartment complex temporarily.

Apartment life is okay, but I will buy another house hopefully in the near future. There's this one unusual tenant I have seen several times walking around the complex. He's what I call a "twink boy", mid 20ish I'm guessing, obviously gay, which I'm totally cool with. To each his own, I'm not homophobic. Still, not my thing. I have never been with a man and have no desire to explore that avenue. I believe he lives 2 or 3 doors down the hall from me as I see him often. He's a little standoffish. He always stares at me intently when he sees me, and when I give him a polite hello, he seems to blush and nervously scurry away.

Last week, I was in the communal pool chilling, just hanging on the edge, as I had just finished several laps and was catching my breath. Here he comes, twink boy, walking the way he does, which seems so feminine that it's almost funny to me. He's got this unmanly gait that reminds me of a female walking and posing on a model's runway. Just too delicate if that makes sense.

Facially, he's overly pretty for a man, almost too pretty if you know the type. His longish dark black hair is parted in the middle and hangs loosely on the sides of his face, always causing him to brush it back out of his eyes. He was wearing what I assumed were a large pair of women's sunglasses, definitely not a man's pair. He had on the most scandalous skimpy neon pink bathing suit I had ever seen. The back barely covered his huge butt cheeks. It looked like a woman's bikini bottom stuffed with the biggest, plumpest and firmest butt you could ever imagine on a man. His ass was especially noticeable as he was so skinny from the waist up. Probably 5' 10"s tall and around 160 lbs. His thighs were extremely thick and toned, which made his rear end look even more pronounced.

With his matching pink flip flops, he was almost advertising shamelessly who he was and what he had to offer if anyone was interested. The front of his bikini bottom jutted forward, bulging like it was stuffed with one of those small skinny soda cans. Either this kid was really well hung, or had a semi erection, or he had stuffed something in his bathing suit. The material was so tight and stretched you could almost guess he was circumcised.

He had a little dainty gold earring, dangling low from one ear, and with his lips so full and red, I swear it looked like he had lipstick on them. As he walked towards a lounge chair, not paying attention to where he was going, instead staring at me through his dark lenses, he stumbled in a large hole in the cement that had been there since I moved in. That hole had caught my foot once before and should have been fixed, as it was an accident waiting to happen.

As he fell to the ground dropping his phone on the cement, and his sunglasses went flying, he let out a little girlish yelp. I quickly waded through the pool over to the edge to him, while he was still on his hands and knees trying to compose himself. His big butt was facing me, maybe just 2 to 3 feet from me. I saw a tattoo of a red devil with a pitchfork on his lower back, just above his bikini line. As his little bikini bottom got drawn up tight into this ass cheeks from stumbling, I marveled at how smooth and hairless his ample, well rounded, firm ass was. Not a man's hairy butt by any means, but it looked like a young girl's ass, so smooth, tender and hairless. Barely the soft whisper of peach fuzz on it glistened in the sun.

"Hey buddy, are you okay? That fucking hole. It got me a couple of weeks ago. They need to fix it." I offered.

Startled by my voice, then looking over his shoulder coyly, with his rear end less than a yard from my face, he said to me almost seductively with just the slightest twinge of a lisp, "This hole really needs to be filled, don't you think?"

As he said that, he seemed to put an emphasis on the words "this hole" and I thought I actually saw him shake his butt flirtatiously at me. Maybe it was my imagination, but I was pretty sure what I saw.

The way he said it, I swear, it almost sounded like an invitation to fill his hole, more than a reference to the hole in the cement. Maybe it was my imagination, but to me, there may have been a definite hidden meaning to his comment. Was this guy coming on to me?

I told him my name and also stated that I was a certified EMT, asking him in my most professional voice, if he thinks he sprained his ankle or knee.

"I'm okay, I think. My knee is bleeding a little. I'm so embarrassed. I was distracted." he giggled. "I'm Chris, but everybody calls me Chrissy. I think I'm gonna go inside and find a band aid."

After he limped off and went back to his apartment, I called it a day and got out of the pool. I went back to my apartment, took a hot shower and put on my bath robe. I was thinking of ordering a pizza when there was a knock at my door.

It was Chris, or Chrissy as he said I should call him. He was still wearing those pink bikini bottoms, his matching pink flip flops but now had on a tight yellow t-shirt, that didn't even cover his skinny waist. His feminine little torso and tummy was on full display.

"William, I'm sorry to bother you. Do you have a band aid I can borrow. I don't have any medical supplies and you said you were an EMT." he asked so innocently.

"Of course, why don't you come in and I'll get some supplies for you." I directed him.

When I came back with some anti bacterial spray and some band aids, Chrissy was sitting on the couch.

"Let me do it, I'm a professional." I laughed trying to ease the tension. As I wiped his tiny scrape with a warm soapy wash clothe, he actually whimpered like a little girl. "Come on Chrissy, that doesn't hurt does it?" I teased him.

"A little bit, but you're the expert, so thanks for saving my life." he smiled and giggled nervously. As I sprayed his knee with the medication and applied a band aid on his tiny scrape, he giggled again and said, "How can I ever repay you?"

My bath robe had drawn up to mid thigh on my leg as Chrissy boldly placed his hand on my knee. His hand was soft and warm as I felt an immediate stirring in my cock. He held it there for more than a few moments as it kind of shocked me, but I didn't push it away or tell him to stop.

"Is there anything I can do to return the favor." he said almost seductively, as he now squeezed my knee tentatively gauging my reaction. While his hand slid just a little further up my inner thigh, I was becoming aroused. I should have stopped him right then and there, but I didn't. Frozen, I couldn't help myself as we now just stared at each other, neither of us even speaking. Like they say, you could cut the tension with a knife, but my cock was swelling.

I definitely had a full erection now that had become an obvious visible tent under my bathrobe. I hadn't been laid in two weeks and I guess I was really horny. Breaking new ground, I thought to myself, that I was willing to take a blowjob if that's what he was offering. I just leaned back into the couch almost nonverbally offering my cock to him.

Chrissy boldly spread my robe wide open, exposing my erection. I saw his eyes open widely, as he just stared, fixating on my cock, "Oh Lord Jesus, you have a very fat cock. That is by far the thickest cock I have ever seen. Mother Nature surely blessed you. That is what I call a jaw breaker and a booty hole buster, but I do love a challenge." he snickered hungrily.

There have been many times in my life where I've had a "regular erection", and those rare other times when I had a "nail driver erection". You guys know the latter, when your cock is so extra hard that it is completely unyielding like a piece of granite. The type of erection that points at the ceiling, so stiff and inflexible that it resemble a merciless weapon. One of those unrelenting and unwavering boners that could put an eye out if you're not careful. That was what I had that day.

Chrissy gushed and almost squealed as he wrapped his dainty soft hands around it. Feeling it's temper and heft, he just squeezed and weighed it deftly in his petite hands. Just staring and admiring what I was offering to him, he blabbered more admiration, "I adore your big fat cock, I truly do love a challenge. I love to throat a big cock, and while yours might be difficult, please let me try." he almost pleaded.

I just sat there anxiously awaiting what would come next as he lowered his plump full lips and enveloped just the tip. He had to stretch his mouth obscenely wide so those sweet soft lips would allow entry. So soft, so warm he nursed on just the tip getting acclimated to my girth. He mewled and whimpered softly as he struggled on my thickness. Once he had mastered the tip, he slobbered down the shaft as far as he dared. When it touched his throat opening, I relished in the little gags and sputters he made. That always turned me on when a woman choked and retched on my cock, and Chrissy was no exception. I loved the little noises that he emitted as he fought to consume my cock in his throat.

He opened my robe completely as he fell to his knees never slowing down his homage to my cock. "Oh God Daddy, I am in love with your cock. I need it in my throat so badly. I never want this moment to end." he blurted out quickly as he went straight back to work.

I allowed him to go at his own pace for a few minutes, still gagging on it each time he went deep. He was determined to push it into his esophagus, and sucked it so good and so deep, over and over, until he finally pulled away. Slobber and drool covered his lips as he gasped for air and stared into my eyes not quite defeated, but waning somewhat. A single tear rolled down from his watery eye.

Staring at my hairy chest, he just blurted out, "You are so fucking sexy Daddy." as he leaned in and sucked on my rock hard erect nipples. Sucking so gently on each nipple, I really enjoyed this as it was not something that anyone had done to me before. I didn't realize how sensitive my nipples could be as he gently nibbled on them, sending little electric shocks through my body.

I held the back of his head firmly to my chest, encouraging his nipple play. It felt delicious and so personal to have him suck on them. My wet cock head was poking into his stomach and smearing my precum on his torso. This twink boy knew how to orally please a man. To say that I was enjoying his oral manipulations was an understatement.

After a few minutes of this he abruptly pulled back and stood up. Chrissy yanked off his t-shirt and squirmed out of his tiny bikini bottoms. When he did, I couldn't believe how big this little sissy boy's cock was. It was definitely longer than mine, probably close to 9"s. Not nearly as thick, but nothing to be ashamed of at all in the girth department either. Perfectly circumcised and rock hard, it bobbed and weaved as he knelt back in front of me.

"Don't worry Daddy, I know you're all man. I don't expect any reciprocation, I just want to be naked while I service you. It makes me feel sexier. This is all about you." he asked almost hoping he wasn't disappointing me.

I didn't say a word as he went back to work on me. Chrissy lowered his head and gently drew one of my balls into his mouth. He gurgled it around and massaged it with his tongue so gently. Not playing favorites, he alternated from one testicle to the other for several minutes. I inched forward on the couch giving him better access to them as he seemed completely absorbed and lost in his efforts.

My cock was aching now, so needing to be sucked some more as I gently pulled his mouth off my balls and brought it back to my cock. He actually winked at me and said, "I know, sometimes I get carried away, but I'll get serious now. Your throat belongs to your cock and that's where it's going."

Chrissy plunged his pretty mouth straight down on my cock until it punched again at his throat. He did gag just a tad, as I felt his esophagus expand and the head broke through momentarily. It was so tight yet so velvety smooth as I entered his tight gullet. His lips were so far down my shaft that barely an inch was left when he pressed down again and mashed those plump lips hard into my groin. He had it deep in his throat now, all the way to the root and held it that way for probably 30 seconds. Nobody had ever been able to do this to me before and I began to moan.

He repeated this over and over for the next few minutes as I fought the pleasure trying to hold out. It was an act in futility as I felt that familiar itch in my balls start to overcome me. I knew I couldn't hold out much longer as his mouth was so warm and tight. Chrissy never stopped or varied his rhythm, just a slow steady swallowing motion over and over until I just couldn't hold back anymore and started to spurt.

I watched intently as I saw his Adam's apple gulp down my first volley. It bobbed up and down in unison with the spasms in my cock that released a torrent of cum. Shot after shot, Chrissy gulped my seed down like a hungry slut, making gurgling noises in between his gulps and swallows. I must have fired 8 volleys into his hungry stomach as he ingested every single drop. Finally pulling off, as he knew I was spent, he smacked his lips obscenely and swallowed any residual cum in his mouth. With a glazed look in his eyes, he just stared intently at my still 100% erect cock. "My God you cum a lot." he blurted out, obviously delighted with the volume of sperm I had just fed him.

Chrissy, still between my knees, sat back on his haunches, just alternating his staring between my face and my still fully erect cock. "Does it go soft after sex William?" was all he said.

I just laughed and said, "Sometimes it does, sometimes I need to cum twice before it goes down." That brought a mischievous smile to his face.

"William, would you fuck my ass for me? I'll give it to you good. I promise, I'll give it to you real good. Am I pushing my luck?" he almost pleaded.

No woman had ever let me take their ass before. Not because I didn't try, I surely did, but they always said, "no way, you're way too thick", or they would make a feeble attempt and give up. It was on my bucket list. I was still horny as hell with a full blown erection and the first thought that came to my mind was, "when in Rome".

"Yea, Chrissy, we can try that. I've never successfully done it before, but you do have a particularly fetching rear end. Are you sure? I would love to try. You think we can make it work?" I asked secretly smiling to myself as this was uncharted waters for me, but still loving the idea.

He just nodded his head with those glazed eyes listening to me. "Follow me Chrissy." as I stood and walked to the bedroom with him in tow, both of our cock bobbing up and down as we walked.

Chrissy might not be a woman, but he did have an ass and thighs that most women would kill for. I was thinking I would love to watch my cock go straight up that big firm butt. I just knew it would be incredibly tight. I grabbed a bottle of lotion from the bathroom as he sat patiently on the bed.

"Get on your knees, buns up kneeling. Put your face and shoulders deep into the mattress. Spread your knees wide for me and scoot to the edge of the bed until your feet are hanging off." I now aggressively directed him.

As he got into position, I was amazed at how perfect his twink butt looked. It was truly fucking spectacular. Absolutely breath taking. I can honestly say it was the best looking ass I have ever seen in my life. So feminine, so sexy, so pretty, so toned, it was just incredible. Not a single hair on it, not even around his little pink starfish of a sphincter. Perfectly smooth and inviting. I wished I had my phone with me so I could have snapped a quick pic of it.

I had originally planned to just grab his hips and try to fuck his sweet ass, but it was so inviting to look at, that I wanted to play with it for a bit. I knelt on the floor behind him and touched his tiny sphincter muscle gently. Chrissy moaned and involuntarily spread his knees even farther apart, allowing more access if I dared. Both encouraged and curious, I felt myself lean forward and do something I never imagined doing in my wildest dreams. I kissed his perfect girly ass. I put my lips between his cheeks, very close to his little rose bud and kissed gently. He smelt nice, like a woman, like he had perfumed that area.

I kissed again, tentatively at first. A kiss here, a kiss there and his cheeks gyrated passionately welcoming my warm kisses. I was curious and gently kissed his little puckered sphincter. When I did, it twitched, like it winked a me. I kissed and licked it some more, and I watched little spasms quake in that ring of muscles. Chrissy just purred and moaned as I got more definitive in my oral manipulations.

I openly licked and sucked on his little button as it was rocked with spasms and opened up to me, still winking repeatedly. I was enjoying teasing his ass and got serious about it, now slurping and slobbering all over his tiny hole. I bit gently all around between his cheeks, which made him moan and whimper. I reached up between his legs and softly squeezed his balls. They were shaved so smoothly and felt so feminine. I slowly stroked up and down his amazingly long cock, as Chrissy now began to buck his hips in unison with my strokes.

This was so out of character for me, but I just couldn't stop. I continued to massage his balls and stroke his cock so slowly. Feeling the cum dripping out of his cock head, I massaged and smeared it into his shaft as a lubricant. Chrissy moaned loudly. Still sucking and licking on his sphincter, I was loving my power over him.

Chrissy finally spoke, "God Daddy, stop teasing me please and give me that fat cock of yours. My butt is screaming on the inside to be fucked." he literally begged me.

Coming out of my trance, I regained my composure and stood behind him. Getting some lotion on my index finger, I started to lubricate his tiny hole. I smeared a generous dollop on his little muscle ring and started to insert my index finger. Once in to the second knuckle, Chrissy shuddered in delight. I worked it around for a few minutes, just teasing him as I knew he wanted more. I then removed it and inserted 2 fingers repeating the sawing motion as I twisted them gently into the walls of his tight silky smooth bowels. Chrissy was absolutely purring now.

"Please Daddy, please, give me that cock now! Quit teasing me." he begged.

I stood and placed the tip of my rock hard erection against his tiny sphincter. I gently pushed but it wasn't going in. A combination of him being too tight and me too thick. I pressed on until finally the head just popped in. Chrissy groaned and mewled as I broke through his barrier.

He pushed back onto my cock ever so slowly. Gobbling it up one inch at a time til I was firmly planted to the root. I loved watching his sphincter muscle just open up and expand to let my thick cock invade him. The feeling was incredible as his bowels were so tight and warm. The walls of his butt felt like velvet, softer and smoother than any pussy I had ever fucked. His tight rectal canal felt like it was sucking on my cock so hard. I grabbed onto his wide hips firmly and started to stroke in and out.