Filling the Gap

Disclaimer:

The story is heavily based on a real situation from my life. It depicts a gay threesome, jealousy and cheating! If you are not into cheating stories, morally dubious behaviors, cumsluts, cuckolding and fucking asses right after another man, you will be disgusted, and the story is probably not for you! :)

Please remember - it's a bit different than my other stories, it's NOT a romance, it's just a sex-snippet from my life. Don't expect too much ;)

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That particular day I was bored as fuck, so I created a profile on some dating webpage. It seemed to be a bit outdated, but it offered some nice matching features. Most mobile dating apps didn't have that level of detailed preference matching.

I'd just broken up with my boyfriend and was ready to rock and roll with some new blood.

I was cleaning my apartment until late afternoon, and didn't check the webpage for several hours. After that, though, I finally opened my laptop. To my surprise, I found one message in my mailbox already. I'd truly thought these dating services were on the verge of going extinct.

The message surprised me even more:

"I read your profile. I noticed that you ticked 'cuckold' kink as one of your most-liked sexual preferences, and also 'voyeur.' I have a peculiar situation here. I'm in a relationship with my boyfriend, and we are in love, but he has this dream about being fucked by another guy right after I'm done with him. He also wants the other guy to watch us. His birthday is approaching, so even though I do not feel 100% on board with this idea, I want him to have his dream fulfilled, and have decided I will make an exception to my rules. I would like to propose that you come to our flat, and we can see how it goes. What do you say? Are you up to this?"

I was very surprised by the description of such a specific situation. Never before had I been a part of such an arrangement. It was more like a fantasy of mine. Whenever I'd even hinted at it to my previous boyfriends, they'd all given me the side-eye. If I mentioned that I would be aroused by the possibility of fucking them just after another guy, they always winced.

I knew that a lot of people found cuckolding and voyeurism disgusting, but c'mon! Some people were into scat and watersports. Were my fantasies that much weirder? My boyfriends seemed to think so. Was it because I wasn't a possessive person and could share them with another man? Was that off-putting? Maybe they thought that meant that I didn't love them enough - that they weren't special to me? I didn't know.

Should I answer him? Was it finally my chance to follow my fantasies, and to make my kink more real? And was I really mentally prepared to do that?

On an impulse, I sent him the following: "Hey, thanks for your message. I would prefer to know how the person looks before I'll go and try anything. I also do not bottom, so that's off the table. To have a fair exchange, I sent you a photo that is a bit better than my profile picture. I also attached my dick pic."

Of course, I added my dick pic as it was kind of a "standard" procedure in this kind of dealings.

I sent it and waited about fifteen minutes, having rather intense mental noise reverberating in my mind. Fuck! So I was gonna do it after all?

"Thanks for the photo. My boyfriend thinks you are hot. And nice dick too. How long is it? Looks like solid 7-7.5 inches? Very thick and veiny - he appreciates it. I sent you his pic, he is nineteen and is a sophomore in college. "

The photo he sent me was... better than I expected. It depicted a small guy with curly, light-brown hair framing his cute face and big, hazel-green eyes. He was wearing a tank top that exposed his lean shoulders, and black jeans. Really pretty boy. I could feel my dick throb only seeing his cute, almost innocent face, slender body, and these big eyes...

Innocent? Well. That remained to be seen.

Looking in his eyes, I already knew I was on board. It was too... tempting.

I closed my eyes for a second and the decision was made. No backing out.

"Yes, it's 7.5. But 8 inches as measured from the bottom part. When can I come? Send me an address."

He responded 30 seconds later, giving me the address and...

I found myself in a state of small shock: They were living in my condominium! Fuck! I may have even seen them in the local mall. What were the chances?

I did not let them know I lived that close. My fingers were a bit sweaty, as I was in a small state of shock, overwhelmed with my own eagerness. I wrote only one sentence: "I'll be there in half an hour."

I ran toward the bathroom and washed myself very meticulously, clipped my fingernails, trimmed my pubes, brushed my teeth and shaved my face. It all took me about twenty-five minutes. I dressed up in black jeans and a black T-shirt, and I was ready.

I stocked my pockets with condoms, lube sachets and I left my apartment.

My heart was beating fast as I was closing on the neighboring building. Yep, they lived in an adjacent apartment complex... I rang the doorbell near the intercom and waited.

"Hello?"

"Yyy... Lucian here. I mean from... the dating site, my... nickname is ITgay25."

Yep, I was so creative about my nickname. My job + my sexual preference + my age. ITgay25. So inventive, right?

"Ah, yes. I'm Ander. Come in."

I went inside, my heart pumping hard; I was even panting a bit, as the situation was so new and weird for me, that I could not totally calm myself down. I even came up with a plan to tell them that I ran here all the way, to explain the hard breathing.

As I was walking down the corridor to their apartment, I forced myself to slow my pace down and took a few calming inhales-exhales.

Okay, I was good to go.

Adventure awaits!

I knocked.

The door was opened by a guy around 5'10'', so I had a slight advantage at 6'1''. He was of average build, even a bit fat around the waist, so another point for me as I was fat-free and athletic, having trained martial arts for seven years. I was also a regular at the gym.

It already gave me some confidence. As he reached his hand out, I shook it with a smirk.

He was dark blond, with brown eyes and lightly tanned skin - so my exact opposite, as I was dark haired, blue-eyed and had light skin tone. He was not ugly or unattractive, just a very normal, moderately good-looking guy - an 'OK' look.

He checked me from head to toe. Did he suspect I sent him a fake photo? No, no, no. I was the real deal. I never photoshopped myself, as I was a firm believer that it would blow up in my face the moment I'd show up at the doors of my potential date. I wasn't into being humiliated and sent away, so I preferred unretouched photos.

I went into a small corridor, and shook off my boots there. Ander was waiting, watching me attentively; he made a gesture to follow him.

I walked into the large living room where the other guy was sitting on a couch. Seeing me, he stood up.

I was actually surprised by how small he was: not more than 5'5''. Slim build, narrow shoulders, waist, and hips. Willowy and slender. He was also prettier than I expected. His eyes were light green rather than hazel, his lips were full, and he had funny freckles on his slightly turned-up nose. He was not classically beautiful, but surely very cute. He didn't look like a person who would want to have multiple cocks in his tight ass, but oh well. You never really know people, right?

I smiled and he smiled back. "Hey, I'm Lucian. Nice to meet you."

"Hey, I'm Liam. Likewise."

I shook his hand - small and fragile. My gaze fixed on his light green eyes - probably a bit too intensely - and he blushed.

Finally, I glanced at the second guy, Ander, and asked: "I don't see a birthday cake, so I suppose I will not be hiding inside, right?"

Liam chuckled. "My nineteenth birthday is in two days. It's a bit of a... planned-ahead gift."

"Got it. So... what now?"

I actually started to feel more and more confident with every passing minute. Ander was not at all intimidating. Truth to be told, I was expecting some "daddy" type, definitely a more mature and imposing person. He was rather inconspicuous, and I sensed a lot of insecurities in him.

Ander's eyes roamed over my body, and his face suddenly started to look different, as if he felt my growing confidence. He seemed now rather soured and unsure.

Was he hit by the reality of the situation?

Liam noticed that also and said, "Maybe... hmmm... Would you like something to drink?"

I darted my gaze at Ander's morose face and nodded.

"Sure... I would like tea, if I might."

I chose tea on purpose, as the lengthy process of preparing it would give Ander some time to adjust to the situation. It would be better to have him 100% on board with the threesome idea, but I wasn't sure if that was even possible. I could almost physically feel his mood gradually deteriorating, his lips set in a hard line, his fists clenched.

We moved toward the kitchen annex and Liam started to prepare the tea. I made a mistake by ogling his body too attentively, as they both noticed it. Liam blushed even more, and Ander's face became even tenser.

"So... what do you do for your daily job?" I asked Ander.

"I'm a sales manager in an office supplies company. And you?"

Yep, he looked like a salesman. His non-threatening appearance made him a good candidate for this job. He was about 28, maybe 30?

"I'm a programmer in a software development company."

"Well, you surely don't look like the stereotype of an IT guy or a nerdy coder...."

I fixed my eyes on his face, trying to assess his intentions. His lips were tightened at first, but soon he gave me a lopsided grin. Was he being a dick?

"Thanks, I take it as a compliment. I actually was working as a model for some time, during my college years. People were often surprised that I was majoring in Computer Science."

He slowly nodded, but his grin slipped, his eyes becoming rather cold. He was not happy I mentioned modeling because Liam's gaze was now upon me, with some kind of new curiosity, as if he was trying to imagine me doing some naked shots amidst beautiful scenery.

I met his gaze. I must say, I had trouble tearing my eyes from Liam's slender figure, and they were both well aware of that.

Ander could not hold it much longer: "So. I can see you already like Liam."

I hesitated, as he looked miffed, even hostile.

Should I change my behavior? Show him my more cocky side? It would definitely annoy him. He had no problem with showing me his bad mood, even though it was he who had invited me here. His attitude was bordering on being rude, and I was not gonna let him walk over me. For sure, antagonizing anyone was a short-sighted method of dealing with people, but since he'd said it was a one-time birthday thing anyway, should I even care?

So I narrowed my eyes a bit. "Well, he is very attractive."

Liam chuckled awkwardly. Predictably, Ander clenched his jaw even more. "Good, so I guess it won't be a hardship for you..." His voice became rather bitter.

Liam glanced toward me and smiled softly.

"No. But will it be a hardship for you?" I asked, eyeing Ander. If he was going to be a dick, then I was also going to give him some attitude.

Liam turned his head toward Ander and looked at him with a bit of fear in his eyes. Was he afraid that his boyfriend would back out of the arrangement? It looked like it. The boy's fear was a form of compliment toward me, as he evidently was interested in me... staying.

But I underestimated Ander's determination, as he put on a weird grin. "Well, not at all. I promised him a special gift for birthday. I'm all for making my boyfriend happy." After saying that, he moved toward Liam and embraced him, kissing him passionately while I watched. He probably thought it would put me off, but it did not.

I actually moved two steps closer and started to watch them rather intensely, which was noted by both men.

"Shall we... proceed to the bedroom? I'm ready to watch the first part of the show," I said in a husky voice.

Liam broke the kiss and asked "What about your tea?"

"It can wait. Go ahead. Bedroom."

Ander probably hadn't been t expecting this level of eagerness on my side, but apparently he was not going to stop. So, I followed them to a big bedroom with a... really big bed. King-size bed! Nice.

They were kissing still, and soon started to undress. I was not going to be left behind, so I took my shirt off. Ander and Liam turned their heads around and looked at me. They were probably not expecting me to have such large tattoos on my body. I could see even more fire in Liam's eyes, and even less of it in Ander's, who looked very annoyed.

Ander was in no hurry to take his shirt off, probably because of his waist fat. Liam, on the other hand, was more than eager to get rid of all of his clothes. Soon I could admire his slender, ballet-dancer-like body, very lithe and wiry. He had a small dick, not more than 4 inches, but it was something I actually loved in my bottoms, as I could do miracles with small dicks, swallowing them and deepthroating easily.

What was even more exciting was the fact that he had a butt-plug in his ass - and a funny one! It had a long pink fox tail, hanging now between his slim legs! So... he was a bit of naughty boy after all. Good!

"Wow, nice!" I expressed my admiration and grinned widely. Liam winked at me.

The boy was a masterpiece! Seductive yet simultaneously innocent looking. My dick was tenting my pants, so I was not going to pretend there was no urgent problem there.

I unzipped my pants and my dick popped out, bouncing a bit for them to see. I was always content with my impressive girth, which gave my dick an even more imposing and thick look, beyond its 7.5 inches of length. I knew 7.5 inches was not considered a monster dick or a 'porn-size' dick, but I was pretty content with how it looked, thanks to a large mushroom head, thick veins, and overall 'massive' look.

Liam's pink cheeks became almost red. He was ogling my dick very intensely, and then I saw his small, neat cock become even harder, sticking out like a tiny pink steel rod, almost as if it wanted to say hello to mine.

Hello, little one, you are a cutie!

We were looking at each other as vehemently as if we were about to start some crazy rut fuck like wild animals. My pulse spiked higher than during my last Muay Thai training, and I could actually hear my heart beating in my ears.

I was always head over heels for cute twinks and femboys, absolutely loving to fuck their small and wiry bodies, to rock them into the mattress, and Liam was like my dream come true: a beautiful, horny twink. Horny for me. And he was. His eyes bored into my face as I smirked, stroking my dick with obvious intent. I already had a plan in my head.

Ander also put down his pants revealing his hairy ass that held no appeal whatsoever, at least for me. His dick was a bit under 7 inches, so not that much shorter than mine, but far less thick. He had a semi, and obviously was not happy about that and... NOT being happy about the level of hardness is not a good thing, as you all probably know. Nervousness is like... cold water.

So, I decided to take some action. Standing a bit behind Ander, I gestured toward Liam -- showing with my hand and mouth that he should probably help his boyfriend to become... a proud man again.

Liam obviously got that, as he lowered himself over Ander's body and took his dick in his pink, soft mouth, still wet from their kisses. I positioned myself a bit to the side, not wanting to lose the nice view. I smiled toward him encouragingly, and he obviously could not answer, sucking Ander's dick, but his eyes gleamed to me with a cheerful gaze.

I could feel we already had a connection and a delightful chemistry.

As I was out of Ander's sight, he finally managed to get an erection. Only then did I decide to get on the bed, already completely naked - and went behind Liam's ass.

Ander eyes widened in horror. "Hey! I'm the one who is starting..." he almost growled.

"Of course, of course! I'm gonna lick him a bit to prepare for you..." I smiled almost submissively, but there was no submission in my eyes. It was a challenge.

I lowered myself and made a long trail of kisses over the pearly-white skin of Liam's slim back. I made long, lapping moves with my tongue, and slowly grabbed the handle of the butt-plug. I made a couple of small moves, simulating fucking his ass, and after that, I slowly took it out. Only then did I notice the mirror on the opposite wall of their bedroom, in which I could see Liam's face and his lips sucking Ander. His gaze was on me, and he was blushing.

And of course Ander's eyes were angrily fixed on me, but, oh well. Was his bad mood my fault? He invited me there. That was not my problem and Liam was obviously consenting... So, I lowered myself even more and kissed his round, firm, springy ass cheeks.

Yep, very attractive ass, I was planning to soon plunge in.

At that moment, I already knew. I was 100% on board with this weird threesome-cuckold thing.

My fantasies were about to happen in real life.

Looking at Ander, I slowly covered Liam's skin with open-mouthed kisses. He watched me with narrowed eyes. Finally, I spread the boy's buttocks and glanced at his clenching, pink hole, glistening with a bit of lube. So, he was already nicely prepared!

I slowly licked over his pucker, circling it with my tongue, tasting a bit of cherry from the lube. Liam reacted very agreeably; he even pushed his hips back a bit to let me have better access. My tongue went inside his ass, and was poking at his loose hole, teasing and caressing him. Liam made a small moan, and then Ander said through clenched jaws:

"Ok, I'm ready. I will fuck him now."

I straightened up with a wide grin.

Liam surprised me, as he just made a 180' turn and was now facing Ander with his rear and me with his face, on all fours. Our eyes met, and he smiled at me. He seemed to be in the perfect mood for fun, kinky sex.

"I wanna suck your dick now..." he said, but Ander snapped again:

"Hey, we didn't agree on that, Liam!"

"But I want to... please, Ander," he pleaded, looking over his shoulder to his boyfriend.

Boy, wasn't he eager to have his both holes filled up? And I was about to fill the gap... in their relationship. And somewhere else, preferably.

Ander went red, but finally nodded. He spread Liam's ass and lined up his dick with the boy's hole. I observed him and chose the moment to insert my dick between Liam's tempting lips: when Ander pushed his dick inside! Yes, Liam moaned loudly in response to this double invasion, having been filled from both sides simultaneously, and he went to work very eagerly on my dick, taking me surprisingly deep and without choking.

Yeah, he was rather skilled at that, which I could appreciate, as I'd spent countless hours training myself on controlling my own gag reflex to serve my twinks the best way I could. I was often praised for my skills by them, so it was worth the effort.

Liam was equally skilled, and I could feel a bit too much pleasure... It was going to end way too quickly, but I was not that sad as I had a short restart time. Every so often I needed only ten, and occasionally even five minutes to become hard again, and I could fight through the feeling of oversensitivity without losing my erection.

So, I didn't care that much if I came too quickly, and he was good at this. Too good to deny myself a quick and intensive eruption in his sweet, hot and skilled mouth. I always loved having orgasms (Duh! So obvious! Who doesn't?) and was never restraining myself from that. I was never really a believer in edging. Only a full-power orgasmic blast was satisfying for me.