Daves Dilemma

Santo’s Wedding Part 14

After Colm and Jerry meet, they talk and now are ready to take the next step in whatever this was going be. This was Colm first step in his having full on gay sex with another man. He was nervous and full of anticipation at the same time and was talking about seeing his older brother Quinn and Alfonso’s older brother Santiago being fucked down.

He cried “honestly mate, old conservative Alfonso, seeing his brother Santiago getting fucked so deeply and intensely was funny to be fair. I was shocked, but he was more so seeing his older bro crying out making tons of noise, as he orgasmed repeatedly. Yeah and he was dicked out by Columbian Gonzola, which was just crazy.”

 “Santiago like my bro’s Quinn’s whole body shook as his asshole, was being hammered out, and he cried with all of the pleasure he was receiving Jerry.” He was looked opened mouth and he carried on  “yeah all Alfonso could say to himself and me for hours afterwards, was “My God My Brother Has A Pussy, He Really Has Pussy Hidden In His Ass!”  

Jerry roared with laughter and splutter “really he said what” and Colm repeated it and cracked up laughing. After a while they stopped looked at each other and Colm went on to talk some more about his Quinn’s ass taking skills. He also marvelled at Bruce’s 90 minute nonstop drilling of Quinn’s cunt.

“I can beat that easily” Jerry laughed.

“Blimey I bet you can, with that monster between your legs!”

 Do you want to see it then Colm?”

Colm nodded going crimson, which Jerry found endearing. “Come on then let’s go somewhere a bit more private shall we?”

Then he said being direct with his intent clear “but I need to clean you out though, as I will being go extra deep inside your asshole man.” He was looking into Calms eyes, checking out his response re “Colm if I am going to have sex with you and I am big, it would be better if we get to know each other properly.”

“Let’s not muck about, as you need to be cleaned out and I can show you how ok, come on lets go” and they went to a nearby room and started to make out.

“Damn Jerry you’re so big man!”

Colm blushed as he stated this whilst he was feeling his man oversized tool with both of his hands. He was gripping his thick piece of pale meat, and slowly running his hands up and down the man thick pulsating appendage. As he did so, he was thinking to himself, “what am I doing here with this guy?”

“I’m straight and loved screwing females.”

Jerry replied “yep I’m 12 inches, and I can’t get no one apart from Santos to take me so easily. This is a damn problem” he sighed looking sad and pissed off. “It not great having this size of a dick, Colm, as everyone struggles to take me inside them!”

Colm looked at him and said confidently “well Jerry I would like to try to see if I can manage it, if that’s ok with you?”

“You sure man as I am BIG?”

“Yes, I know that, but I like you a lot” he said hesitantly feeling stupid like a teenager on his first date.

“Mate thanks” and they made out some more and soon enough Jerry was playing with Colm’s firm bubble butt and started to finger him. stuffing one then two large fingers inside him. “Come on let’s get you cleaned out” he said and did so carefully.

As he did so, he noticed that Colm never flinched and he said “you have done this before haven’t you?” And the response was an open “yep to myself, as I like to be clean down there” and also I watched Santos as he takes cock nonstop in his big butt and hungry man pussy hole, which gobbled them straight into him and he was as clean a whistle.”

“Oh yeah, same as I watch him earlier after I finished cunting him out and he is bloody good isn’t he mate?”

“Yes he is fantastic and I hear that the other guy Dave is even better” Colm replied.

Then  Jerry said without thinking who he was talking to, which was potential boyfriend, not one of his pals or pickups, “yes mate the orgasms I have, when I have fuck him silly with me big prick, as I end up exploding inside his hot cunt, is fucking amazing, the best piece of tail that I have ever experienced in me life!”

Seeing Colm’s face which was neutral but not hostile, he immediately apologised and was bit flustered and said “sorry Colm that a bit rude of me to talk about fucking another guy like that in front of your face.”

“No this is you being honest, which I respect as you are being honest with me and I can deal with that. I know your dicks is going to hurt me, but well let’s try yeah?”

“YEAH!!!!!

Soon enough they kissing and cuddling in the bathroom and Jerry lubed up and with his finger entered the Colm hot tight gripping anus, which almost strangled his fingers. “Man I don’t think that I am going to fit all of this inside him, as he is so tight.” He added another, then a third finger. “You ok man? “Yes” Colm gasped.

“Try another finger” and he did so he soon had 4 fingers swishing inside the younger guys asshole. Jerry at 29 was 3 years older than Colm and was bigger all over, but Colm was more than a match for him. He and Quinn had other brothers and they all looked alike. He knew his bringing Jerry home with him, would cause a massive drama, but he did not care.

Enter me please Jerry,” Colm said and added more lube to the man’s prick and then to his open pulsating asshole. “Ok now” he said and turned around and put one leg up on the bathroom chair. “Go easy please” he said. “You sure” and he nodded and his man large cock head was placed on the edge of Colm’s ass ring and he missed his hole.

“Come on let me”, Colm said and taking the full throbbing length, and place it in the right place. “Stay still” he said and pushed back like he had seen his older brother Quinn’s was  doing with Bruce, and his cherry was popped. He gritted his teeth and tried to relax and manage to take another 3 inches of the blokes dick inside him.

Wanting to lie on the bed he pushed him out of him and taking his hand he said “let’s go to bed.” And as soon as they got there, he said “let me sit on you and see if I could take more of you inside me?”

“Ok” Jerry said softly and laid on his back and was mounted by Colm who lined his ass hole with his 12 inch penis, and taking a deep breath he push himself down and was able to take some more of the thick length.

“Argh shitttttt” he groaned and lent forward and Jerry rose up and they kissed each other and were soon swapping sensual kisses, which felt good. No it felt more than good, it felt natural, and it was making Colm excited to be with this man.

They held on to each other and were making out some more, and by now 8 inches had entered Colm’s manhole, and he groaned as he was unable to get anymore of his man inside him. “How the hell does Santos and Quinn do it” he said “as they are able to take a damn good pound out.”

He was chewing his lips and winching and looked distracted. “Hey, come back to me, its ok look you got most of me inside your ass, and that enough for me, for our first time.”

“I know but I want to take all of you Jerry and feel like a bit failure to be fair” as Colm hated failing at anything he did as he was fairly competitive. “You will, don’t worry.”

“When, Jerry, as you are going home soon, and I won’t see you again any time soon will I?”

“I dunno, as I can stay for another few days, but need to book into somewhere, as I am off work until Wednesday.” “Really you can stay?” “Yes like I said I need to book a bed and breakfast place, do you know any good ones?”

“Fuck that Jerry, you can stay with me at our house with me and me 2 brothers.”

“Are You Sure?”

“Yes of course” he said and feeling so happy that his man was going to stay with him in his bed, and he instantly relaxed his hole. Colm raised himself up and off the dick and re lubed it and also squirted a generous amount inside his asshole and staring into his man eyes, he remounted him and pushed himself downwards. He took deep breaths and groaned as he was completely stuffed full.

Colm’s bubble buttock was finally tickled by Jerry wiry pubes. “Yes” he shouted. “Yes, I taken all of you inside me Jerry. Yes Fuck You Santos” he cried and seeing Jerry’s amused face he started to laugh and he said sweating and shivering “I knew I could do it, as I simply hate failing at anything. Ask Quinn my sibling, as he knows me so well.”

“Great” his lover said and let his man, his new boyfriend he reckoned, unless he read this completely wrong. And he was grasping, lifting. and pulling the younger man bubble buttocks, into his thick thighs as he mouth was biting and nibbling on his pale muscle chest and is small man nipples.

This was making Colm moan loudly as his nipples were sensitive and it was as it was link his butt hole and felt fantastically exquisite. They rock together looking at each other and were laughing and giggling as they did so for about half an hour. “Let’s change over, and with that he pulled out of him and laid on his side and re-entered him and took his time.

He nibble his neck and ears and stuck his tongue in his mouth, and Colm was tingling all over. “What is happening? I am Straight and yet I am Gay!

“Man is that what Quinn feels like when he gets cunted?”

“And when did he know he was Gay then?”

He was he thought to himself so in love with Bruce, and the look he gives him, he does adores him, and it like I’m doing now and I only known this bloke since today.” “ What you thinking about” Jerry asked him seeing a faraway look in his lovers eyes?

“Nothing” he said. “Come on yes you are, what going on inside that serious head of yours”.

“Well I’m a bit overwhelmed with all this” and he cried out as Jerry’s cock went extra deep inside him. “Whew!” Bloody hell mate, that’s a bit too deep fuckkkkkkkk.”

“ Sorry I can’t help it your so fucking fit man.” And he cuddled him as he continued to slot into him.

“So you got boyfriend then Jerry?”

“Nah I have few flings, but nothing serious, although I would like to settle down as it is lonely going to bed at my parent’s house by myself.”

“Ah so you still live at home then, I see ?”

“Yeah as its convenient cheap, and I get on well with my folks, they would like you Colm.”

“Really would they so they know you are gay then?”

“Yeah they would, and yeah they do know that I am gay, as me old man, caught me face timing Santos having wank, as he was stuffing a large dildo in his asshole.”

“Shit what did they say?”

“Son” my old dad said with straight face, “we don’t care who you sleep with, but please wear head phones next time, as that bloke who is showing off the dirty wee sod, is making so much noise, so he was. Even Ms Can next door would have heard the two of you sexing up!”

Jerry and Colm burst out laughing then Jerry groaned as Colm’s anal muscles gripped him, and he said “I am not going last long” he warned.

“Good neither am I” and he locked lips again and said “cum in me ass Jerry love.”

His eyes rolled back in his head as he was pummelled out and exited by a few inches and pummelled back into again and looking at his lover face concentrating on him whilst looking straight into his eyes, thus making Colm lose it, and he shot off all over the bed. He produce more cum than he had for long time.

As he did he felt Jerry unloading inside him, and he felt every squirt, as it open him up some more, and he groaned and pushed back wanting to get more of the man foot long meaty cock slab inside him.

After while of lying there Jerry went to pull out of him. “Hey what you doing mate?”

“I thought you wanted me out of you Colm?

“Are you crazy I need more of you I feel something for you” he declared.

Seeing Jerry face change, he said “sorry mate, that’s sort of too much right?  I am always doing this.”

“No its perfect” he said smiling broadly and pinching himself. “No its bleeding perfect” as my cousins who live in the east end of London tell me,” and they started to fuck again, and took it easy as they knew they would have more time to get to know each other over the next few days.

So after another hour or so of screwing Colm’s now slack stretched out devirginized ass cunt, yawning they feel fast asleep.

After an few hours Colm got up moving off the still semi hard did and went to use the bathroom. He had a piss and turn round to check out his asshole in the mirror. As he had been screwed by the man huge dick, he noted that his anal lips were all puffy and oozing cum, and he wiped as much as he could off and out of him.

“Jesus what am I doing”  he said feeling suddenly vulnerable and worried that he had made big mistake, having sex with this bloke, who was fast asleep in the bed. Maybe I should go, as this is a mistake, I not a queer, I’m not.” He was suddenly tearful, and wiped his eyes thinking what would people say.

What would his parents and team mates think of him, having sex with another bloke.

He was conflicted as he felt so good earlier especially when his legs were wrapped around Jerry thick thighs and waist, and he was being made love to as Jerry held him so firmly was looking at him so lovingly. His beard was glistening, his face was all sweaty and he had been taught well by Santos, re how to take his time and pleasure his man.

Before that it was an in and out of a number of not very satisfying sexual relationships, which was tiring.  And he was awake having heard Colm getting out of bead and he was waiting for him to come back to bed. When Colm walked back into the bedroom he switched on and Jerry sat up in the bed.

 “You ok man?” He asked looking concerned seeing his boyfriends face with his glistening eyes, see that he had been crying.

“Yeah I ere am….”

“Look come here mate” Jerry said holding him tight. “Don’t overthink it alright.”

“Let’s take one step at a time” and they cuddled and soon enough they were fucking again with Jerry so wanting to plow into him, like he would always do with Columbian Santos. However he knew this was not the time, so instead he took his time, slow drilling into him faster than slowed down, and lost another load inside him.

Before Colm had time to recovered he was being fletch out and told to “push my load out. come on be a good lad, I need my load” and he was taken aback by Jerry’s long tongue teasing his tender swollen anal lips, for long while, as his legs were akimbo , before he moved back up and entered him again, as he was slow fucking him and then upping the pace.

As he did so Colm was relaxed and slack and ejaculating twice more and was pulling onto his boyfriend’s big beefy meaty buttock, and in doing so ensured that his full 12 inch meaty length was fully inserted, into his open relaxed now over distended ass channel.

Jerry looked at him his mouth devouring his and he said “I am gonna go bit harder, you ok with that?”

Colm gulped and shiver looked into his man eyes and said “yessssssss” and felt himself shooting off his load ,and then experiencing the intensity of having his man’s large cock inside his manhole. All of his earlier worries and concerns had gone like puff of wind and now all he was concern with, was bring his boyfriend.

“Hmmmmm hell my boyfriend” and he grinned and said “em Jerry I like you a lot?”

“Yeah and I Ilke you a lot as well Colm, as does he” he said referring to his cock which was throbbing inside his man’s accommodating devirginized hot anal passage, that tighten around his full throbbing length.

“Nah fuck I really like you a lot and want to see you properly like if you up for it of course?”

“Of course I am up for it Jerry, you don’t have to ask!”

And they were kissing each other hungrily and touching each other so intimately and were rocking and pulling at each other and could not take their eye off each other. And Jerry was deep fucking his boyfriend going harder and holding  both of his bubble buttocks in one big hand, and the other was holding on to Colm’s soaking wet dark hair.

His beard and Colm’s stubble were rubbing again each other, and for the younger guy being on the receiving end instead of being the one doing the fucking, and his having sex with another guy, this was all new to him, yet felt so natural and fine that his body was super receptive to being fucked.

And soon enough he had another anal orgasm and cried out loudly “oh fuckkkkk Jerry, oh fuckkkkkk!” Jerry in turn started going hard and heavy and forgot that his boyfriend, “yep my boyfriend, that sounds nice” only hours ago was an anal virgin. He was hungry for him and started long dicking him he was slamming into his man now open over receptive manhole.

In response Colm was huffing and puffing with pure erotic moans and groans opening himself up and pushed back against his man to gain every inch of him. He was shafted long and hard for long time, orgasming like crazy and the bed was rocking violently, and he was crying into Jerrys mouth and started to chew and suck on his thick neck.

And the way that his body was taking him in, and his legs and a #rms were pulling the bearded Jerry’ bigger manly body into him caused him to get lost on the moment. Jerry in turn plunge and lunged even deeper into the Quinn’s now devirginize butt hole and he lost control pummelling and punching his prick hard and heavy, into him for over an hour.

In doing so he felt the guy orgasming multiple times both anally and spewing his thick creamy white spunk all over both of them and brought him off for the third time in as many minutes.

Colm felt weak, vulnerable, wanted, and loved, as he could see that this man was someone that he wanted to see a lot more of. He really hoped that his big brother Quinn and their brothers Ryan liked him as well. It was important to him that they did as he adored his siblings.

He said to himself, “now I can see why Quinn like taking Bruce’s prick in his asshole as I was judgemental dick head disrespecting him like that. I don’t know though that I would like Jerry fucking around with anyone else though, as I would not be able to handle that at all, it would kill me!”

He loved his older brother so much as they were close and also Ryan as well, although he was not sure how Ryan would take his two younger brother being fucked in butt by these twos big dick guys Bruce and Jerry. Colm sighed erotically as he felt his asshole passage spasming, and at the same time Jerry yelled and shouted “Immmmmm Cummmminngggg fuckkkkkkkkkkk babe I love you man!”

Colm’s body was slick with sweat and he was so turn on, much more than he thought he would be as this was sex on a whole different level. Forget all of those cliches and negative stereotypes that he and his hetero mates and society had about gay men having anal sex.

As far as he was concerned, they could take run and jump as this was the best feeling ever. The way this man made passionate hard love to him and owned him, man this was so good, that he would bottle it and sell it if he can.

He was going to speak to Quinn and apologise to him for what he said earlier and tell him how good it was to receive the dick, but for now it was all about him and Jerry, and he was taken aback by the hot man over intense, body shaking, love making skills, This was all new to him.

“Thanks Frank the wank he giggled and cried out in full submission “ah Jerry man what are you doing to me love” and they fucked for long while, before they fell asleep in each other’s arms.

To Be Continued