The Rebound

So this is the final chapter of my little saga in my life that involved Darren.....

After New York and my business trip to Boston, I went home. I would receive an email from Darren asking if we could talk. However, I stated that I would be busy during the holidays, asking if it could wait afterwards. He said he understood. However, I never reached out to him after the holidays. I don't know if I just wanted to avoid the situation or if I was still just angry about it all. My feelings and emotions were all jumbled. Additionally, I was focused a lot on my work, which was keeping me busy. Following the holidays, I was travelling again for meetings for the company I work for. One of my trips I ended up going back to New York. While I visited, I reconnected again with Mia and Alana. I ended up going out for dinner with Mia, getting to know her more. Another evening, all three of us ended up partying and had a bit of fun together at the end of the night on a more intimate level. I began to really like Mia. She was open about herself, which allowed me to open as well. It was relieving. We agreed to stay in touch with each other whenever I was in town for business.

All the while, my communication with Darren was fleeting at best. We'd chat online or text here and there. He would ask how I was doing. I kept it brief. He would suggest sometimes if I'd want to come down for a drink or workout, but I always stated that I would have to take a rain check. I had not seen him since New York. I didn't even bump into him in the building. I ended up doing my laundry at a laundromat, ultimately not even seeing him at the place we initially met. In one short exchange through text, Darren mentioned that he missed me. A part of me did too, but I didn't know what I really wanted. I had so much on the go, and now that I was somewhat starting something with Mia, I was scared to see him again in fear of the wave of feelings I might encounter.

Then I had a life-changing experience. I got a call from my company, stating that they were expanding their company and wanted me to be a project lead in the office that they were opening in New Jersey. I knew of the company's expansion of offices, but it surprised me that they offered me the project lead position at the branch office they were opening. I was excited for the opportunity that was being given to me. It was also my window to potentially beginning something longer term with Mia. The office was going to be open near the end of the summer. They provided me with a signing bonus and covered my moving fees, which was super appreciative. I told Mia of this, and she was happy for me and looking forward to spending more time, now that I would be closer. My family was sad to hear of my move across the country, but understood it was a huge opportunity for myself.

Over the few months leading up to it, I was getting my affairs in order. I ended up finding a place in New York City, allowing me to travel to the office across the river not too far from my job. I notified the property management of my current apartment of my eventual move. I made arrangements with my family to help me with the move, including getting a U-Haul to take my stuff to my new destination. Everything was a go.

It was four days from my eventual move. It was a sweltering hot and humid day. To make matters worse, the A/C in the building was down. I was working, packing more boxes. I then got a knock on my apartment door. I looked through the peephole, seeing Darren standing outside. He was wearing a tank top and short swim shorts. He had a towel hanging around his neck, wearing flip-flops. I got goosebumps seeing him outside. I was surprised to see him. I hadn't seen him in months, and we only fleetingly chatted. I had a flutter in my heart and stomach. Why was he here? Why now? I couldn't delay any longer, opening my door up.

Darren greeted me with a grin. He said hello, stating a long time, no see. I asked how he was. He said he was heading down to the pool, and thought he should stop in to say hi and see how I was. He asked if he could come in. I allowed him to come in. He noticed the boxes, making the remark that I was moving. I told him what was happening in my life and my eventual move across the country. I offered Darren a drink. He accepted, and I got a couple of Cervezas out of the fridge. Darren asked if we could talk. I agreed, saying if he wanted to go on the balcony. Darren agreed, and we made our way to the balcony.

Darren immediately apologized to me, stating that if he did anything to hurt my feelings when we were last together in New York, that he was profusely sorry for. I told of my uncomfiness of the experience we had in our little three-way tryst. I told him that old feelings and emotions from my previous relationship came back, and I felt jealous and insecure of the whole situation. Darren stated that he didn't know what kind of relationship we had. He stated that he wasn't sure himself, and might have rushed or pushed things too fast with me. He didn't know if it was a friends-with-benefits situation or we had a thing that might have been budding. I told him I wasn't sure myself. He told me that I was the first straight guy that he ever turned gay or bisexual, so it was understandable about what I might have wanted from him. I was honest with Darren, telling him that I honestly didn't know what he had. I loved the sex with him, but I didn't know if I could progress to being in a relationship.

The convo we had was refreshing. It was natural. It was relieving. I had the level of comfort that I had when I went down that fateful night to his apartment. I opened up and apologized to Darren about what happened later that night, telling him my emotions and feelings led me to doing something spiteful. Darren understood, and said what I do, I should do with no regrets, and I should live life doing that. We did a cheers to that. Darren smiled, and we looked out into the hazy cityline. Darren grinned, admitting that the sex with me was exhilarating and that he definitely felt alive again when he had our moments. I shied away, grinning myself, stating that I was glad that my first ever experience with a man was with him. We did another cheers, and Darren playfully shoulder checked me. We had a laugh.

We went back inside, and Darren jokes, stating he should get down to the pool before all the kids pee in it. We shared a laugh. We got to the door, standing and looking at each other. I quietly tell him that I wish he could stay. Darren tells me all I have to do is ask him. I turn and shy away from him, grinning and shaking my head. I get the same nervous and vulnerable feelings that I had from our first experience together. Darren reaches out, taking my hand. He tells me that I'm an amazing human being and that our moments we've had he can't thank me more than enough for. I look up to the ceiling, shying away again from him. I blush a bit, feeling Darren's hand rub my hand. Darren tells me that he doesn't have to go just yet. I feel his stare on me and when I look at him, I see him staring at me again just the way he did that first time. I ask him why he does this to me. He asks what does he do. I tell him that he makes me feel vulnerable around him. Darren gives me this lustful grin. I close my eyes, saying quietly that I can't. He tells me quietly that you can.

I then feel my hand being guided by him and rubbing against his crotch against his shorts. I feel his girth of a cock through it. My lips tremble. I'm thinking in the back of my mind that I can't. I wanted to move forward with Mia. Darren was reeling me back into him. My breaths are short. I soon feel my hand being guided up his thigh, reaching inside his shorts. I feel his massive cock in my hands again. I look down, and I watch as it's guided out of the side of his shorts. He rubs it against my crotch, instantly getting me hard. I tell him again I can't. Darren tells me "but you want to". He tells me that he knows that I want it, stating about how I will miss this feeling. I ask him quietly what feeling. He tells me of being dominated by him. He raises my other hand over my head, holding it against the door. We are face to face. He purposely rubs his cock all against my crotch, teasing me like crazy. He tells me that I want him. I give in, whispering to him yes. Darren instantly goes in, aggressively and passionately kissing me. Our tongues go at each other.. He has me pinned against the door. He kisses against my neck, sucking and tonguing me all around. My breaths are deep and laboured, and I moan from this. My hands reach for his swim shorts, and I tug and pull them down, exposing his fully erect manhood. I stroke it, rubbing it against my crotch area. I feel Darren's hands reach for the neckline of the old white t-shirt I was wearing. With his two hands and using his strength, I watch as he tears it completely open. He immediately attacks my pecs, aggressively sucking and nibbling my nipples. I feel his pent up angst and lust taking full control of me as I give into him.

I toss off my tattered t-shirt, as Darren reaches for my khaki shorts, pulling and breaking the button on it apart, before pulling them down. He goes in again, passionately kissing me again, rubbing his cock against my underwear. I moan under his kiss. He kisses my neck again. My breaths are deep and I feel his hands reach down to my underwear. He grabs the front of them, and I hear the tear of material as he rips the front of them open, exposing my erect cock. He rubs his cock against mine, pulling my destroyed underwear off and getting me completely naked. Darren whispers in my ear that he wants to fuck my beautiful mouth. He tells me to ask him if I he can fuck my mouth. I go along, asking him if my daddy can fuck my mouth. He whispers back, saying let me show you.

I slide down against the door to my knees. I smell the sweat from Darren's cock and balls, but I don't care. Darren tells me to open my mouth. I do as he instructs. He slaps his cock against my cheek, teasing me before he guides his cock into my waiting mouth. Darren begins to pump his cock in and out of mouth. I still remember my head thudding a few times against the door. I moan as I suck his cock. Darren tells me suck on his balls. I get underneath his cock, taking his balls in my mouth. I suck on one of his testicles, stroking his cock. The smell of his sweat infects my nose, but I'm so lost in the sex, I do not care. He raises my head again, holding me by my hair, slapping his cock against my cheeks, before shoving it again into my mouth to suck. He shoves it deep, making me gag a few times. He was forceful. He was dominant. He was in control.

Darren tells me to get up. He kisses me deeply and passionately again, before he leads me to the couch. He positions me facing the back of my couch, telling me to bend over. I turn, watching Darren get onto his knees and prying my ass cheeks apart. I feel his tongue drive into my hole. His tongue tickles my holes. I gasp and breathe deeply. I grab the back of my couch. I feel his tongue lick it profusely. I feel his saliva moisten it. I hear and feel the spit against it.

Darren, stops and tells me to ask him to fuck me. I do as he commands. I quietly say him to fuck me. He tells me to beg him to. I beg him to fuck me, turning to him looking at him and saying it. He looks at me lustfully. I watch as he spits saliva into his hand, moistening his cock with it. He spits more saliva into his hand, prying my cheek open and rubbing it all over my hole. He gets me to spread my legs wider. I watch as he holds my cheek and guides his cock against my moistened hole. I feel his head press against it. It slowly slides inside me, albeit a bit more on the sorer side as I'm not fully lubricated inside. I gasp as it goes in. Darren then begins to pump me. He does two short pumps before driving it deeply on the third. I gasp and moan as he does this. He continues to do the same repetition, hitting my g-spot each and every time on the third pump. My moans echo through my apartment. I'm sure my neighbors might have heard me, given that my windows were open. Darren changes the pace, starting to fuck me faster, and taking his cock out fully before driving it back into me. The barebacking he gave me was intense.

Darren stops midway, taking me by the hand and leading me now to the couch itself. He sits down, telling me to get on top of him but in reverse cowboy style. I follow his instructions, positioning my hole over his cock and lowering myself down on it. Darren begins to pump his cock upwards into me. I hold myself in this position, feeling his cock hit my g-spot each time. I start to bounce my ass on his cock, and get a good unison going together. My cock flops around and I stroke it a few times, getting for fulfillment from the experience. Both our moans are echoing throughout the apartment.

Darren tells me to get off of him and lays me down on the couch. He gets onto the couch as well, raising my legs on his shoulders and propping my ass in the air. I watch as he guides his cock into my hole again. He begins to aggressively fuck me fast and hard. He takes his cock out a few times, slapping it against my hole before driving it back in. The rush of blood to my head with the heat makes everything euphoric. Beads of sweat cover our bodies. My cock keeps rubbing and hitting my stomach with each of his pumps. I don't need to stroke it, for as Darren finally drives another hard pump deeply into me, I feel my cock convulse and I reach orgasm. I loudly moan, watching my cock spray my cum onto my stomach and a bit onto my chest.

As this happens, Darren reaches his peak, pulling out of my ass quickly. He moans loudly, stroking his cock as white streams of his cum rained down my chest, neck and around my mouth. I taste his sweet saltiness on my tongue. Darren collapses on me. kissing me passionately, not caring that he's tasting his own cum on my lips and tongue as well. He lays on top of me. We are a sweaty mess. We lay with each other for a while, before Darren suggests we cool off.

I suggest to him that we should hop in the shower to cool off. He agrees and we head into the shower. I throw on the water. Cold water rains down on us. It cools our skin. We wash and clean each other off with soap and bodywash. Darren pulls me in and gives me a kiss. We embrace and hold each other as the water rains down on us. We kissed again, our hands rubbing and caressing each other's bodies. It doesn't take long for us to get in heat again. Our cocks rub against each other, getting semi-hard again. I squeeze Darren's ass cheeks. I feel Darren's finger rub against my sphincter. This gets hard in no time. I am ready once again for him. He quietly tells me that we should go to the bedroom. I agree with him.

We hop out of the shower, towelling each other off, before wrapping towels around our waists. We entered my bedroom. Boxes are piled against the wall where my double bed awaits us. It's early evening. The humid and hot air still permeates throughout. I lay down on the bed. My hard-on pokes from beneath the towel. I unwrap my towel, laying naked on the bed. Darren grins at me as he unwraps his towel, unleashing his beast of cock. He gets on top of me and we begin to make out again. We rub and dry hump each other, our cocks rubbing and touching. He passionately kisses me. I wrap one of my legs around his butt, while squeezing his other ass cheek with my hand. Darren works his way to my neck, kissing and licking me, the bristles of his moustache brushing against my neck with each kiss. He works his way to my chest, sucking and nibbling my nipples. I moan and gasp in pleasure. He continues on his journey down to my bellybutton with kisses, before getting to my crotch area. Darren remarks about how beautiful my cock is before kissing and licking the head of my cock. It drives me wild, and I moan and breathe deeply as he does. It doesn't take long before he fully engulfs his mouth on my cock, and begins to suck me off. I moan louder. I loved watching this dominant man go to town on me. It was like he was making love to my cock with each suck and stroke of it.

Darren then works his way to my balls, licking and flicking his tongue against them. He then hoists my butt, before licking my taint. It drives me wild. He then gets to my waiting hole again, stating how beautiful it looks, just waiting for him. He begins to lick and kiss my hole. I gasp as he does, stroking my cock to further my pleasure. He stops, coming back down on top of me and passionately kisses me again. He whispers in my ear that he wants to fuck me. again. I tell him that I want him to. He asks if there is something he can use as a lubricant. I tell him to grab the Vaseline from the bathroom cabinet.

Darren goes and retrieves the Vaseline. He scoops out some, propping my butt up again and rubbing it all over my hole, fingering some inside of me as well to get me fully lubed up. I watch as he grabs another finger full, rubbing it all over his cock. We fully get onto the bed, my head laying against my pillow. Darren raises my legs, positioning his cock against my hole. He slowly slides into me. I gasp as I feel his cock fully inside of me again. He bends down and kisses me passionately, slowly beginning to pump me with his cock. I feel every inch of him inside, his head of his cock constantly hitting my g-spot. My moans are drowned out from our kiss. I hear Darren's moans drowned out as well, as he works up the pace. He pulls away, as I gasp and moan; my hands gripping the sheets. He pulls out, slapping the side of my ass with his cock, before shoving it deeply back inside. I curse and swear each time that he does this.

Darren pulls out and tells me to turn on my side. I do as he says. Darren spoons me from behind. I feel his cock slide back into me as he starts to fuck me from a spoon position. He moves my leg forward, allowing him to drive his cock deeper inside of me. I feel even more pleasure as he does this. I stroke my cock as he does this. My loans are loud. Our sweat is soaking the sheets below us. I feel the sweat from his chest against my back. I hold my leg for Darren, feeling his forearm grip around my neck. He kisses my ear and neck, driving his cock hard into me. We both moan from this, enjoying every second.

Darren tells me to lay flat on my stomach. I roll onto my stomach. Darren gets on top of myself completely, spreading my legs. I feel his hands spread my ass cheeks open, before I feel his cock slide inside of me again. Darren drives his cock inside. He works up the pace, going hard and fast. We are a sweaty mess again. He raises my head, kissing my neck. I turn and kiss him on the lips. He tells me my ass is so fucking good. His forearm goes around my neck. He drives his cock even deeper. His balls slap my ass cheeks. All the while my cock is rubbing vigorously on the sheets below. I'm getting to my breaking point. I'm gasping, telling Darren I'm gonna cum. Darren tells me to ask him to cum inside me. I do this, telling him over and over to do so. I then use the magic word that gets him to release: "Cum inside my daddy". I feel my cock convulsing and I blow my load on the sheets moaning loudly. Darren follows suit, moaning loudly, as I feel his cock ejaculating his warm load into me. We both gasp and breathe deeply. I lost count of how many times we orgasmed in just that session.

Darren rolls off of me, pulling myself into him to spoon with each other. He kisses me again, and just holds me for a good while. He jokes with me, asking me if I'm sure I don't want to leave town. We share a chuckle together. We're a hot mess again, and we agree to jump into the shower again for a cool off. When we get out, I strip off the sheets, and we lay down again on the bare mattress. Darren spoons and cuddles me. The sun has gone down. We lay with each other, soon passing out and falling asleep with each other.

I woke up in the middle of the night. Darren is still laying next to me. He is fast asleep. I think to myself about what this man did to me. How he opened up a side I didn't think I had in me. How he changed me. I look at this muscular athletic beautiful body from the moonlight shining through my window. His massive manhood lays against his thigh. Just looking at it got me semi-hard again. I wanted him again.

I bend over him, bringing my face to his crotch area and his flaccid cock that laid there. I slowly and quietly run the tip of my tongue along the side of his shaft. I watch to see if there is any reaction, but I get nothing out of Darren. I decided to run more of my tongue on the side of his cock. I hear Darren's breathing change only slightly, but feel his cock becoming semi-hard. I up the ante, carefully bringing his manhood up to my mouth and begin to suck the head of his cock. I hear his breathing changing, becoming a bit more deeper. I finally engulfed his cock in my mouth, sucking Darren off. Instantly he comes hard inside my mouth, and I hear him begin to moan. I feel fingers rub through my hair. Darren comes to, watching me suck his cock. He moans and breathes deeply, as I take advantage of him.

Darren motions my body to get on top of him in a 69 position. I follow his guidance, and continue to suck him off. I feel my cock being motioned and I feel Darren's mouth enclose over my cock and begin to suck me off. Our moans are muffled as we suck each other's cocks in 69.

Darren stops me, and motions me to come on top of him. He begins to make out with me passionately. Our hard-ons rub against each other. Then out of the blue, Darren whispers in my ear to take advantage of him. I initially thought he wanted me to go back down on him, but he stopped me, shaking his head. He brings me back down again and whispers in my ear to take advantage of him. He said that I started it, and I need to finish it. My naivety was not following, but he then whispers that he wants me to top him, following it up by telling me that he wants me to fuck him. I tell him I don't know if I can. He tells me that I can and that I will. He tells me to take all my frustration and emotions from New York out on him.

Darren pulls me in again for a deep kiss. I don't know what to think. This beast and hunk of man is giving in to me. He shocked me by offering himself to me. Though he was a dominant top, it seemed he was versatile as well. I begin to kiss his neck, and work my way down to his nipples on his chest. I suck and bite on them, gently pulling them with my teeth. I kiss down his abs and back down to his waiting cock again, where I tease him with my tongue all over it again. Darren gasps, just watching me do this. I take a deep breath and prop up Darren's butt. I gently pry his cheeks open and through the strings of asshair, I see his hole. I lick all around his hole. I hear Darren gasp and say that's it. I watch Darren grab his cock, slowly stroking it and pinching his nipple with his other hand. I begin to lick and suck on his hole voraciously, the strings of hair tickle the top of my mouth and tongue. I hear Darren saying "yes baby", breathing and moaning deeply. He finally gives in, saying to fuck him.

I reach over to the nightstand, grabbing the vaseline. I rub some on Darren's hole. I take some and rub it all over my cock. Darren turns over and gets on all fours. He looks back at me. I take a deep breath, prying his ass cheeks open, exposing his hole again. I press my cock against his hole. Darren grabs onto the headboard of my head. I feel my cock slowly slide in, the hairs of his ass clinging to my cock like tentacles from an octopus. Darren breathes and gasps. Finally my cock slides right inside of him. Darren grunts and moans. Darren turns to me, telling him to fuck him like how he should be fucked.

I take his cue, gripping his ass and begin to pump him deeply. Darren grunts and moans, telling me just like that. My balls slap against his butt each time. I slap his ass, and Darren "yes, just like that". I start to pump him harder and faster. Darren moans even more. His ass is so tight, almost like a virgin. I hear the slap of Darren's cock hitting his stomach each time I pump him deeply. I start to moan and breathe deeply. I start to lose control, and pump faster. I feel myself getting close to orgasm again. His tightness of his hole brings me quickly to hitting the breaking point. I tell Darren I feel like I'm going to cum. Darren says it's okay if I want to creampie in his ass. His words trigger me, and I cannot hold it any longer. With one final pump, I feel myself cumming into Darren's ass. Darren grunts and moans loudly and I follow suit. I counted about ten times I orgasmed. I pull out my cock from Darren's ass, and oozes of my cum are pooted out of his ass.

Darren kneels up and kisses me, before whispering in my ears "my turn". He pushes me down onto all fours again. Darren is still hard and I don't believe he came. He grabs the vaseline, rubbing it over his cock. He grabs a wad of it and smears and rubs it quickly all over my hole. He hurriedly prys my ass open again, shoving his cock against my hole. It easily slides in, and I gasp and moan. He fucks me hard and fast. I'm still hard from fucking Darren's ass, and now he's inside of me. He lifts me up into a teaspoon position, kissing and sucking my neck, before turning my head around and kissing me. He grips his forearm around my neck, continuing to pump me hard. I moan and grunt loudly now. My emotions come over me. I don't know if it was a combination of sadness or complete enjoyment from Darren fucking me, but I began to cry a bit. I grab my cock and jerk it uncontrollably. I tell Darren that "I want my daddy to cum in me again". I feel him really pick up the pace. I cry to him over and over to cum in me daddy. I hear Darren moan and grunt, and with one final pump I hear him let out a grunt and cry as I feel his cock pulsate in me for the last time. At the same time, I feel myself cumming again, spraying whatever I had left in me onto the mattress below. I cry and moan out, reaching orgasm. We are both breathing deeply.

We both collapse down on the mattress. I feel Darren's cum oozing out of my hole, running down my thigh. I am exhausted. I just lay in his arms. We are still breathing deeply. He just holds me there. I feel him kiss the top of my forehead. I end up falling asleep in his arms.

It's near dawn, and I come to. I wipe my eyes, but see that Darren is not there. I get out of bed, thinking he might be on the balcony possibly. I throw on a pair of underwear, walking out to my living room. I look around, but Darren is nowhere to be seen. I see a chair in front of the door to my apartment, as a way of blocking anybody coming in. I see a note left on my small dining table. It was from Darren. It was a simple message: Good luck in New York! It was fun! Remember, no regrets!

I smiled, reading his note to me. This final night with him was incredible and memorable. I would never forget it in all my memories in life. I knew it was time I moved on from this fling that I had.

When I arrived in New York, I would start my life out there. It was there that I once again reconnected with Mia. My weekends involved herself, and I would end up going on more frequent "encounters" as she had put it, though I thought of it as dating. We'd party with Alana, and we had our nights of all of us canoodling with one another. As a show of appreciation to Alana, I helped fund her vocal cord surgery, giving her a more feminine voice. Mia thought my kindness was super nice, and she soon mentioned about us becoming exclusive.

All this while, I never heard from Darren from either email or text. I thought about messaging him just to see what was up, but I decided against it. After dating Mia for a few years, I decided to take our relationship to the next level and proposed to her at Rockefeller Center. She naturally said yes.

We wouldn't get married until two years later, agreeing to tie the knot back in my hometown. It was the first time heading back there in years that I was coming back to my stomping grounds. When our plane landed, thoughts of Darren came about again. My curiosity was to whether he was still living there at the same apartment and if the gym was still open.

When doing a tour of my city, I decided to take Mia back to my area that I lived in. I purposely passed by the gym to which Darren owned. However, I was surprised to see that the gym was shuttered down, now turned into a wellness spa. When I took Mia back to my apartment building, when I was showing her the lobby and apartment listing board, I looked for Darren's last name but it was nowhere to be found. It seemed as though he had moved from the building and likely closed up shop for his gym.

Out of curiosity that night, I went onto social media to see if I could find him. I was able to find him through Insta, discovering that he was travelling throughout South America. Some of the pictures he had on his profile showed as though he was living the life out there, showing off the places he explored. I was tempted to add him just to be a friend, but decided against it, closing the chapter once and for all.

The night before we were about to be married, Mia said that we should air everything out on the table now. It was almost like a confessional of sorts. We both shared everything with each other. I told her of my night with Darren before I moved to New York. I felt a bit guilty, saying that we were somewhat starting something prior to myself moving there. Mia then said something that brought a smile to my face. She said to live with no regrets. She would go on to share that she had on again/off again flings with a male co-worker of hers before I came to New York, and had a casual fling with a female before we became exclusive. Our little confessional was relieving to say the least, and I discovered things about my future wife I would never think of.

I would get married to Mia, celebrating with friends and family. It was a wild party and it was an even wilder wedding night with her. We enjoyed the honeymoon phase of our life after getting married, still having fun with each other for a good three years. Finally, we settled down and we eventually had our first child. Our second followed two years afterwards. I look back at everything that happened in that wild, crazy and tumultuous time in my life. My mind wonders where and what had happened to Darren. He's likely probably a senior by now. I thank him for the time that we had with each other, and thank him for realizing that in life, we need to live it, and live it with no regrets.

Thanks to the readers of this saga and their compliments. I may potentially share a couple of encounters involving Alana and Mia and the trysts we had together, given some requests I received. This is barring permission from my wife of course....till then, no regrets!