Hi all Here's my next and second last chapter with my ongoing fling that I had post break-up with Darren
This one is a bit complicated and I'm breaking up into two parts of this saga on what happened the second night I had with him in New York
To say the least, this was probably one the most craziest nights I've ever experienced in my lifetime besides my bachelor party
Part of this night will be told in the transgender section of Nifty. Again, when I say this was one of the craziest nights, you'll have to read it to see for yourself. I'll start though with my experience that night with Darren.
It was the second day I was spending in New York with Darren. The following morning, I was pretty sore from the pounding I took from him. I even messaged him to state that he wrecked me the night before. He apologized and stated that he would go to a drug store to find me some cream to help with the soreness.
Sure enough, he arrived at my room with some cooling cream that helped out. We joked about what he did with me. We agreed to go grab breakfast at a nearby diner, before taking in the sites of New York.
Over breakfast, we talked about life. What I wanted. What he wanted. It seemed like stuff you'd talk about if you wanted to start a relationship with somebody. However, I didn't know if I wanted to cross that threshold just yet with Darren. I even decided to retract his offer to move into his hotel room for the weekend, stating that I had booked the room on my work's tab already, which in truth I had done and could have easily cancelled. I still didn't think I could move forward with a man, especially one almost twice my age. Don't get me wrong, the sex was great with him. I wrote this down in my personal journal each time we had sex. It was a reminder of what I liked about him. His dominance over me was what made me lust and lorn for him.
After breakfast, we travelled to different parts of New York to take in the sites and sounds. We went everywhere. We went to the Empire State Building. We went to Rockefeller. Central Park. Brooklyn Bridge. The entire day, we were tourists lost in the city. As evening approached, we agreed to grab dinner again. This time we went to an Italian place. We had a great meal. We shared a huge bowl of mussels. Darren joked that this would definitely get the juices flowing for tonight, stating that mussels were an aphrodisiac. Over dinner, Darren mentioned that we should do something fun for the evening. I asked if it would involve going back to the hotel room. He laughed, stating that it eventually could, but he wanted to see if I'd want to maybe go to a bar or a club. He mentioned hearing about a few Xmas club parties going on in the city. I needed a little unwinding, so I agreed to go along with the suggestion.
After dinner, we went back to the hotel room to freshen up and have a quick drink at the bar. I dressed up in some casual clothes. A nice dress shirt and jeans. We hailed a cab, and Darren stated the club's name to our cabbie. Our driver took us to the gay district of New York, and I knew what I was in store for. This was certainly pushing me more out of my comfort zone and gave me a bit of nerves. We hopped out of the cab and went to the door. Darren apparently had already put myself and him on the guest list, and we easily bypassed the lineup.
Upon entering, we checked our coats. Darren was decked out in a red mesh tank top and black pants. The club was filled with both men and women. My guess is it was a mixed club that catered to both gay, lesbian and transgender. The house music was thumping with bass. We went to the bar, and grabbed a drink, watching the partygoers dance. Every so often we'd get a glance and a smile from men that passed us by. I guess it was their way of checking us out. We downed a few more drinks, before liquid courage gave way and we decided to hit the dancefloor. We weren't much of dancers, but we made it work. Everybody was having a good time revelling in the party atmosphere.
We went back to the bar area again for another round of drinks, before I decided to break the seal. While navigating my way to the bathroom, I was then stopped by a couple of females, one being transgender. It was here that I met Mia and Alana. Mia was the female of the two. She was a brunette Italian and had a voluptuous body for her tiny figure. Alana was the transgender once I had heard her voice. She was blonde and also had a petite figure to her. If I could compare her to somebody famous, she almost looked like the actress, Taryn Manning.
Alana had stopped me asking where I was going. I told her I need to attend the boys room. She then asked if I was here with anybody, and I told her somewhat and that I was here with a friend. All the while, Mia was staring at me, intrigued by my convo with Alana and we caught eyes a few times. I couldn't lie to myself in stating that I found Mia attractive. I had a thing for girls of European backgrounds.
I finally broke off the convo with Alana, stating that if I didn't go, that I'd pee myself. Mia told me to come right back. It was a subtle flirt if that. When I came back, they stopped me again. I had to cut the convo short, so as not to make Darren wait and wonder where I was. They stated that I should come party with them. I told them both that as much as it would be fun, my friend was waiting for me. They understood and I moved on.
I got back to Darren, apologizing for making him wait. He told me understood. He got another drink at that time for me, and I was getting the buzz. We decided to hit the dance floor again. Nearby, I saw Mia and Alana dancing together. I saw them glance our way a few times. Darren leaned in, telling me in my ear that he saw somebody that was looking at him at the bar. He pointed out to a young dirty blonde-haired guy looking our way. He asked if we should go talk to him. I didn't know what to say, shrugging my shoulders. In truth, I didn't know if it was something that I was going to be comfortable with, but I went along with it anyway.
We walked up to him, and Darren offered him a drink. It was here that we were introduced to Tristan. Darren carried most of the conversation. From what we gathered, he was there alone as he had a bad date earlier in the night and needed to unwind. Tristan definitely owned who he was, being flamboyant and over the top bravado. He certainly was your typical twink, with a more feminine appeal to him . He had a small slim build. He was pleasantly good-looking.
We all decided to dance together after sharing another drink. By this time, I was pretty buzzed and feeling a good vibe. However, there was something that made me uncomfy with our new found friend. He definitely was the dancer. He even grinded up a few times on Darren, pulling me into grind up on the front of him. There was uncomfy awkwardness. I was hoping it was just going to be me and Darren tonight. Was it a bit of jealousy that I was feeling?
We went back to the bar for yet another drink. I decided to use the head again. On the way back to the bar, I would once again bump into Mia and Alana. Alana made a comment about noticing my "boyfriend". I told them that he wasn't my boyfriend and that we were "special friends" as I put it. I then asked if she and Mia were a couple. Mia replied stating that she and Alana were "special friends" as well. We all shared a laugh. Out of the blue, I then told Mia that I was glad I was bumping into her that night. It was another subtle flirt with the liquid courage that I had. Mia gave Alana a look with a raise of an eyebrow. It was then that she signalled to give me my phone. She punched in her number, saving it to my contacts. I thanked her, before telling her that I needed to find my friend again. Both of them gave me a smile and wink before I left them for the last time.
I got back to the bar with Darren and Tristan waiting. I was handed a shot from Tristan. At this stage, Darren told me in my ear that he invited Tristan back to the hotel and suggested we leave. In the back of mind, I had wanted to stay, in hopes of maybe bumping into Mia and Alana again, but the euphoria and buzziness of the alcohol was in me and I went along with it.
We all grabbed our coats and hailed a cab. Tristan was definitely the giddy type, stating that he was looking forward to carrying on the party back at the hotel. We jumped into the cab and headed back to the hotel. During the ride, Tristan was very handsy with Darren and myself. He gave us devilish smiles each time he touched us on our thighs.
Upon arrival, Darren went to the front desk, asking if they could get a bottle of champagne delivered to the room and left outside the door. It certainly impressed Tristan. We got into the elevator and Tristan became more flirty with Darren, stating that he hadn't had any fun with somebody as old as him. It got me a little put off he was being flirty and touchy. He then stated that he heard how I was able to handle Darren. I asked Darren if he told Tristan that. He confirmed, stating jokingly that he wanted to make sure our guest knew what was in store for him. Tristan laughed, and stated he was scared of what would be in store.
We got to the room. Tristan ogled at the sight of the room, stating that it was certainly classy. Shortly after entering we got a knock at the door. Our champagne had arrived. Darren popped it open, and poured us three glasses of champagne. We downed them. Tristan then asked about how we were going to do this. Darren then suggested that maybe myself and Tristan should get to know each other more and get showered off from the sweat and smell of the club. Tristan agreed, stating it was a good idea. In my head, I was a bit taken back. I'd only been with Darren. Now I was being thrust into messing around with a guy I barely got to know. I knew that was leading me into having my first male three-way. It was pushing my comfort level, but I went along with it cause I knew that this was probably Darren's plan or idea.
I walked into the bathroom. Tristan was giddy. I was a bit shy and nervous at first. Tristan began disrobing. His skin was vanilla white. He had no hair whatsoever on his chest or for any part of his body. He had bright pink nipples, one of which had a small hoop piercing on it. He stripped down out of his pants, revealing his already hard package behind a bright red speedo type underwear. I slowly began to strip down, taking off my shirt and unbuckling my pants. Tristan soon became naked, taking off his underwear, revealing his hairless area. He was already hard. The head of his cock was bright red, standing out from his white skin. He was probably no bigger than myself in size. Tristan then began to help me with my clothes, sliding my pants off, before pulling down my underwear. He made an "oooh" referencing my cock that was semi-hard.
He walked into the shower, turning the water on. The water sprayed down from the shower. Tristan invited me in, stating "not to be shy honey". I walked in behind him. I let the water hit my skin. Tristan grabbed the soap, and began soaping himself up, scrubbing all his crevices and parts of his body. He turned to me, and started to soap me up as well. I felt his soapy hand reach down to my cock, and began to stroke it, getting me fully hard. Tristan giggled, stating that eventually I'd warm up to him. I shook my head smiling, but again I was still a bit uneasy. Tristan would reach for the shampoo, and lathered his head with shampoo, along with mine. It was getting pretty steamy in the shower. We didn't notice that all the while, Darren had snuck in and was already in the jacuzzi tub with a glass of champagne. Tristan started to massage my head with the shampoo, and I would reciprocate the favour. We washed off the shampoo under the shower. Tristan then noticed Darren was in the tub, and made the comment that we had a guest that was watching us. It was then that I noticed him as well. Darren stated to us to not let him stop what we were doing. Tristan asked him what we were doing. Darren responded that we were getting better acquainted with each other, though he didn't think we were fully there yet.
Tristan turned to me and stated that I think he wants us to give him a little show to warm him up. He began to rub his hands on my chest and abs. He then asked what I would say. I went along with it, stating that we should oblige him. Tristan then reached for my face and brought me in for a kiss. I felt his tongue slip into my mouth, and I tasted the liquor breath from him. It wasn't pleasant but it was tolerable. I felt his hand reach down and stroke my cock as he kissed me. Under our kiss, I heard him moan. I decided to pull him in closer, as our kiss got a bit deeper. I grabbed his tight little butt, letting our cocks rub against each other. He moaned even more.
Tristan pulled from our kiss and began to kiss down my neck and down to my chest. He sucked on nipple, before kissing my abs and getting on his knees. He immediately took my cock in his hand and began to lick and suck it. Tristan moaned in pleasure as he began to suck me off. I gasped and breathed deeply. All the while, I watched Darren as he watched this other guy pleasure me. He gave me this lustful look. I could see his hand was motioning in a way where I could guess that he was stroking his cock under the water in the tub. I moaned, as Tristan sucked on my cock. I caressed his head, pushing him down, purposely trying to gag him a bit.
He stopped midway, getting back up to kiss me again. He whispered in my ears, asking if I could return the favour. I obliged him, kissing on his neck, before working my way to his chest and his stomach. I eventually got to his cock, licking around the bright head of his cock. Tristan moaned loudly as I did this. He was definitely the feminine type bottom, as his moans were more of a high note. I eventually licked up and down his shaft, before taking his cock in my mouth. He gasped and moaned louder. In between, he would say "yes honey". I deep throated him a few times before getting up again and kissing him.
In the corner of our eyes, I would say Darren emerged from the tub, wet and dripping from the water. His cock was full erect and hard. He put down his champagne glass, before coming into the shower and joining us. He told us both that now that we're acquainted, he can get to know us more intimately. Tristan remarked about how big Darren's cock was, holding it in his hand and stroking it a bit.
Tristan and myself would take one side of Darren's body, as he rubbed on his chest. Tristan took Darren's cock in his hands again, stroking it, before going in for a kiss to him. I watched as Darren kissed him. Part of me liked it, but part of me was jealous. I reciprocated, rubbing Darren's large balls and kissing on his neck. Darren then suggested to us that we give some more attention to what our hands were busy with. Tristan moaned and giggled, turning to me and giving a wink before he made his way to his knees. I would join him. I watched as Tristan stroked Darren's cock, before sticking his tongue out and licking around his head of his cock. I would follow and flick my tongue against Darren's large testicles.
Darren used both of his hands, rubbing his fingers through our hair as we teased him. Finally Tristan decided to go in, engulfing his mouth around Darren's cock and started to suck him off. I followed by taking my mouth around his ballsack. Darren let out a huge moan. He was definitely liking the double attention he was getting, but I wanted to get in on the action of his cock. I switched my attention from his balls and began to lick the underside of his shaft, as I saw that Tristan couldn't fully engulf his cock. Darren moaned even more, praising us for the attention his cock was getting and stating that we needed to take care of his cock for him.
Tristan pulled Darren's cock out of his mouth, taking a break and suggesting I give it a try. I grabbed Darren's cock from him, going voraciously at his cock. It was part anger and jealousy that made me so aggressive. I wanted to take his cock on first, but it seemed Darren was giving more attention to Tristan I felt. Darren enjoyed it, moaning in pleasure. He would take his cock out of my mouth, before slapping me and Tristan's face with it. We stuck our tongues, so we could touch it. He would then shove his cock into my open mouth, before pulling it out and shoving it into Tristan's open mouth. Darren then stated to us that we should get out and go to the bedroom. We obliged, as we got up and we all headed to the bedroom.
Darren instructed me and Tristan to get onto the bed. We figured he was ready to fuck us, but it seemed that wasn't the case just yet. Darren went to his suitcase. He reached in, pulling out a long double ended dildo. Tristan remarked with an "Oh my god!". Darren stated to us that he wanted us boys to get our holes ready for him. He pulled out a bottle of lubricant, squirting a large amount of it on both ends of the dildo and stroking both ends to ensure it was fully lubricated. He instructed Tristan to get into doggystyle position on one end of the bed, while telling me to lay on my back in a way where my legs were in the air. He squirted lube against both of our holes, rubbing it in and slipping one finger our holes to get inside lubed up. Tristan moaned when Darren's finger slipped inside of him. Finally, he positioned one end of dildo by Tristan's hole, slowly sliding it into. As he did, Tristan let out a squeal and moan. He followed by taking the other end of the dildo, sliding it into my lubed hole. I moaned as it went. He took one hand of ours each, putting them on the middle of the dildo to ensure we had grip and to not let it slip out of us.
He instructed us to work in unison and fuck each other with it. I started to feel the dildo fuck me. Tristan certainly knew what he was doing, grinding and moving in a way where we both were feeling the pleasure from it. He moaned loudly, and I joined in. In the corner of my eye, I watched Darren, stroking his cock with the lube and slipping his cock ring on. He stroked his cock again, before walking over to Tristan's end of the bed. I watched as he positioned his cock in front of Tristan. Soon his moans were muffled as Darren began to fuck his mouth with his cock. Darren cupped his head, guiding him down on it. Again, I was jealous of the fact that our guest got the attention first, but I was lost in the sex.
Soon Darren pulled out of Tristan's mouth before coming over to me. It was awkward for me, but Darren guided his cock down over my mouth. I was forced to suck upwards on his cock. It was tricky to do, but I did the best I could. All the while, Tristan's twink moans drowned out my muffled moans. As Darren pulled out of my mouth, he said that he was ready to fuck us.
He pulled the dildo out of mine and Tristan's ass. He told Tristan to turn around and suck my cock. Tristan followed suit, taking my cock in his hands and began going down on me. I watched as Darren positioned himself behind Tristan, his cock in his hand. He guided himself into Tristan's ass. I heard Tristan's muffled moan, before he took my cock out of his moan, and let out a loud twink moan.
Darren would fuck Tristan hard, shoving his cock deep into him. I heard the slap, and Tristan moaned loudly in between stroking and sucking my cock. Darren was quite forceful, telling Tristan to suck my cock good. I was caught up in the sex, but again in the back of mind I was wondering why our guest got his chance first.
Darren would stop midway, before getting onto the bed, sitting in an upright position. He told me to face away from him and get on top of his cock. I followed his guidance, getting on top, and guiding his cock into my waiting hole. I was eager to ride Darren. I felt him easily slide into me. Darren gripped my sides, before beginning to shove his cock upwards into me. I moaned in pleasure, letting him take advantage of my ass.
All the while, Darren instructed Tristan to suck my cock while I rode him. I watched as Tristan took hold of my cock again, beginning to lick and suck the head of my cock. I'm sure I may have pre-came twice in his mouth, which Tristan approved in moans.
Darren then instructed Tristan to fuck my mouth. Tristan stood up from the bed, before putting his cock to my lips. I opened my mouth, letting him fuck my mouth. My moans were muffled each time Darren shoved and hit my g-spot a few times. Tristan moaned as well, cupping my head and shoving his cock as deep as he could into my mouth.
Darren then told me to get off of him and lay on my back. He then told Tristan to get on top of me in a 69 position,before telling us both to suck each other's cocks. Tristan followed suit, going down me again, while I took his cock in my hand, and sucked upwards. I caught in the corner of my Darren getting behind Tristan again, shoving his cock into his loose hole. Tristan let out another twink moan, as Darren started to fuck him hard again.
Darren picked up the pace more, fucking him hard and fast. I would intermittently get my cock sucked here and there from Tristan. He was stroking more than sucking, as he became overwhelmed with pleasure. He started to dirty talk, telling Darren to "fuck me hard daddy". All the while, I continued to suck and lick Tristan's cock.
Darren then asked Tristan over and over again if he was going to cum. Tristan's breaths were getting deep and heavy, and I heard through the moaning and breathing that he was going to cum for Darren. Darren then asked him if he wanted him to cum in his ass. Tristan let out a moan of yes. Darren asked again to cum for him. It wasn't long before I tasted Tristan's pre-cum, and it wasn't any longer before I felt my hand begin to pulse as I held his cock. Tristan let out a final moan, before I tasted the saltiness of his cum hit my tongue. At the same time, Darren let out a moan, shoving his cock hard into Tristan's ass. I figured that he had cummed in his ass.
Unfortunately for myself, Tristan seemed to forget about myself. He had stopped going down or stroking me right before Darren and himself had cummed. As Darren pulled out his Tristan, Tristan then decided it was a good time to push Darren's cum out of his ass. A sizable goop slid out and down his taint, which Darren told me to clean off. I obliged him unwittingly as to just please him, licking his cum that slid onto Tristan's taint. Tristan giggled and moaned from this.
Darren suggested we take a break before another round, but I felt humbled by the fact that our guest had gotten first dibs on Darren, and Darren got off from him rather than myself. To add, I didn't get off myself from the experience. I decided to make up an excuse, stating to Darren quietly that I was a bit exhausted from the whole experience and needed to get some rest. He suggested that he could whip up some caffeine or get an energy drink for myself, but I lied, stating that I needed to sleep and that I didn't mind if he wanted to continue on without me.
I think he knew I was a bit put off, and maybe the experience wasn't what I had hoped for. Regardless, he said he understood if I needed the rest and that I could ring him when I was ready the next morning. I agreed, as I put my clothes back on, though it wouldn't turn out that way the next day.
As I left his room, for the first time I wasn't happy with my experience with him. I was pleasured but not to the fullest. Maybe I wasn't into the three-way with another guy. Maybe it was my past feelings and hurt that came up again with my previous relationship. Was I having strong feelings for Darren? Was this just all a rebound and I was moving too fast?
My night wasn't done however. When I got back to my room, I pulled up my phone, and thought of the number I pulled from Mia. I thought of calling her, but decided to send a text instead. What happened next was something I will share on the transgender side of Nifty.....