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This story picks up right after the first chapter. All the characters older than 18. This story is a little more front loaded with the sex, with character stuff in the back end (no pun intended). I intend to add at least 1 more chapter
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I woke up slowly and slightly disoriented. I had not had too much to drink the night before, I was nowhere near wasted, so I wasn't hung over, but I was a tad disoriented. My mind for some reason took note of the different surroundings, not my side table, not my curtains, not my bed, definitely not my bed, before it really took notice of the feel of the body behind me, the arm draped over me... It wasn't a dream, I really had slept with a stranger, a strange guy. A nice guy as the night's activities and conversation came filtering back.
And those activities. We hadn't had sex, but he had fingered me, and I blew him. I remembered that. His big cock, much bigger than mine, fatter and longer. Then I recalled wanting him to fuck me. I really wanted his fat cock in my ass? I could feel the heft of his body next to me, the heat of it. I had never slept with anyone. Heck, being stuck in a perpetual friend zone with every girl I ever knew, I had never had any romantic physical contact before last night. So I sucked his cock. And we made out. I don't know why thinking about making out seemed more intimate than me sucking his cock.
Hmmm, his cock. God, why was I thinking about his cock. His big cock. His sexy big hard cock. My god, I was getting turned on thinking about his cock. My cock, no, my penis, it didn't deserve the same term, was getting hard thinking about his cock. How I felt in my hands. How it felt in my mouth. How it tasted. His body was behind me, I was the little spoon to his bigger spoon. Maybe he'll fork me? My penis was achingly hard at that thought. Yep, I wanted him to fuck me. I didn't want to wake him, but I also wanted to... see him. Feel him? Have him feel me, yep, all the above.
I gently rolled over and looked at him in the morning light. He was still handsome. Broad shoulders, muscular but not too bulky, athletic. Like he was a natural athlete no matter what he did. He was totally sexy. Last night's post blowjob conversation came filtering back, he was 10 years older, in town on business, we didn't get into the specifics. Single, gay - obviously - but completely out of the closet. My mind flashed back to him escorting me out of the bar last night, his arm around me, like a couple. Could we be a couple? I could certainly get used to lying here with him. Kissing him, mmmmm, that was really nice. He was such a good kisser. I was thinking about him, playing with my penis in my hands when I realized how much bigger it was than normal. I could see him stirring a bit in his sleep and realized I was stroking his cock, not mine. No wonder it felt so big. I didn't stop though, it was so much fun to stroke his cock.
His eyes opened and stared straight into my eyes. I had both hands stroking his cock, looking at his face, licking my lips. He leaned in and kissed me, not too deeply, but more than a peck. His cock was full and hard in my hands. I liked that I could get this reaction out of him. He leaned in again to kiss me, this time more passionate, deeper, his tongue exploring my mouth. I let him take control of the kiss while I was still handling his cock, thinking about it, wanting it... He moved his attention to my neck, my now sensitive neck, and I heard myself moan, involuntary and guttural. My breathing quickened as I stroked his hard cock and thought about taking him in my mouth. I moved down the bed this time, he didn't have to direct me. I wanted to suck his cock.
The covers got pulled away and his cock was there in all its glory. I got down to its level and started kissing the head. It was so sexy, large, hard, and manly. I swirled my tongue around the head and took it in my mouth. Why was I enjoying this? I wasn't getting my cock sucked, but I was loving sucking his. I liked the feel of it, the taste, the act. Pleasing him. I wanted to please Derrick. I wanted to make him want me.
"What a way to wake up. I could get used to this baby," he said.
Baby? I liked that. No one had ever used that term, well, Derrik was my first... lover? Sexual partner at least. Having never even kissed anyone before last night, everything was new. Except his cock. Well, it was new, but not brand new. It was something I was trying again, and would be willing to keep trying. "Play your cards right handsome and you might get the chance," I replied. Where the fuck had that come from?
I didn't ponder the question long, instead getting back to the task at hand, exploring Derrick's cock. I swirled my tongue around the head, then swiped across the head, like I would with an ice cream cone. I got a hint of his taste as I did, a tiny bit of pre-cum leaking from the tip. I was slowly jacking the shaft, gripping it in one hand, barely able to close it around his girth as I went back to the tip of his cock time and time again. I realized that as I stroked him, I could get a little droplet to form at the tip, which I would swipe away, then coax another, repeating the cycle. Derrick let me play at my own pace, exploring his cock, taking my time, discovering new things about how he, and his cock, reacted to different things. I was trying to learn because I wanted to do this again. I wanted him to want me to do this again.
I opened my mouth wide and took the head in my mouth, enveloping it while I let my tongue move across the spongy head. I was a virgin, not a monk, so of course I had watched porn, straight porn, and where I once imagined myself on the receiving end of a blow job, here I was on the other side, and I had no idea how those women could do what they did. I could barely fit a few inches in my mouth, and they were able to swallow monsters. Derrick was big, huge by my standard, but not quite the size that I would see in some of the videos. Still, I tried to recall what they were doing, not so I could imagine it, but rather so I could emulate it, do it... I wanted to please him, worship his cock, make him want me to do this again and again.
Thinking back to some of the videos, I recalled there were some blow job ones where the girl would work the shaft, kiss it and lick it, all while making eye contact. Hmm, I may not be able to take him deep, but I could do that, so I did, sliding down further, my head nestled in his crotch in a position where I could look up at Derrick's face as I played with him. I had no idea how sexy I would feel, holding this massive tool in my hands, licking him, kissing it, while also looking up at my handsome lover. "You are so handsome, so fucking sexy," I told him between swipes of my tongue at his cock head, my hands jackign his shaft. "I want to do things with you that I never imagined in a million years I would want to do. I want you to do things to me that I definitely never imagined wanting anyone to do to me," coming as close as I had yet to admitting I wanted him to fuck me.
I got a smile and a satisfied groan out of him as I went back to work, licking the shaft, kissing it, working my way down until I could tend to his balls. Heavy, full, I kissed them, licked them, took one in my mouth as I looked up at his face. How were his balls so big? I had them too, but they were nothing like this. I wanted what was inside, I wanted him to cum, I wanted to feel him cum in my mouth, so I moved back up, kissing my way up the shaft until I was at the head, trying again to take it in my mouth. I got a little more comfortable, able to take a bit more, working the head of his cock in and out, drooling on it, keeping it wet, getting it sloppy. I was stroking the shaft, gripping it tighter, wanting it to release.
I kept going like that, trying to make as much eye contact as I could, alternating engulfing the head of his cock in my mouth and pulling back, licking and kissing the shaft. I realized I could get a good reaction as I licked just under the head, where the skin came together and firmed a neat line, leading back to the opening in the tip. I could work that spot, licking it with the tip of my tongue as I stared up at him, watching him watch me. Sometimes he would release this animalistic sound, primal but also pure pleasure, and that would really make me smile and redouble what I was doing. How could being in such a subordinate position, literally sucking someone cock, make me feel like I was in control, powerful.
It was so hard, so hard and thick as I took the head of his cock back past my lips, working it as deep into my mouth as I dared. I moved to swirl my tongue around the head again, savoring the feel of it. I released my grip around the shaft a bit and I felt a surge, an eruption from Derrick's cock in my mouth, flooding it with his searing hot seed. I was swallowing as fast as I could, like drinking from a fire hose as he filled my mouth. I kept my lips clamped around his cock head, suctioning what I could. I was able to taste him, though not savor it, but as his spams diminished, I didn't have to swallow as frantically, so I could take the time and marvel at how much I liked his seed. I looked up at Derrick, seeing him leaning back, breathing a little heavy. I got that reaction, I did that. I licked my lips, getting the last taste of him, making sure I didn't miss anything, and I could feel myself beaming. I was almost giddy. I felt powerful. He told me I was sexy last night, but I didn't feel it then. I did now. I felt sexy.
I worked my way back up his body, taking my time, kissing my way up, inch by impossibly sexy inch. So manly, strong, sexy. He wanted me. This sexy, handsome man wanted me. Well, I was going to do whatever I could to make sure he kept on wanting me. I loved feeling like this. I finally landed back in the crook of his arm, resting my head on his chest, And I could still feel the smile on my face. Derrick tilted my head up and moved in for a kiss, and he saw the smile, which got me to blush. I could feel the burning in my cheeks, but he just pulled me to him and kissed me. I didn't want to stop, so I moved a little higher, straddling him and positioning myself to attack his mouth with gusto. Why did making out with him feel so hot. I could feel his hands roaming across my body, gripping me tight, one big hand on my back holding me, another cupping my ass, feeling it. I knew I had a nice ass, I was a runner and I've had it mistaken for a girl's often enough, and I loved how it fit in his hands. And when I felt a finger teasing my crack, well I fucking LOVED that. I guess I loved it too much because all of a sudden I was cumming, my cock trapped against his body, convulsing, spurting. He never stopped kissing me, and I just fell back into kissing him, my eruption pleasurable, to be sure, but not all that important.
We finally disengaged and I went back to my now familiar position, lying in the crook of his arm. My own hand idly playing with his abs, feeling my sticky emission covering the area. That was all me, I had made sure not to spill a drop of him when he came in my mouth. The idea entered my mind that maybe I could maybe just reach down and coax his cock back to life, but I decided against it. Last night I had never had a moment where I thought of myself with a man, and now it was all I could do to keep myself from grabbing his cock.
"That was amazing Chris," he said. "I thought you told me you had never done anything like that before."
It took all my self control not to look back up in his eyes, but that comment brought the smile back to my lips. It was crazy how much I liked pleasing him. "Well, this was my second time after all," I playfully offered, "I just needed a little practice. A little experience."
"I'm glad I could help," he playfully tossed back my way, "if you like... we could have dinner tonight and afterwards, have a bit more practice. You know, give you more experience..."
A date? He asked me on a date? I turned to look at him, his piercing blue eyes looking back at me. God he was good looking. I laid my head back down and went back to lazily playing with his chest. "I would love to," I replied.
We stayed like that for a while. It just felt... comfortable. But I, well, we, were a bit sticky from my eagerness, so we eventually moved to the shower, which led to more kissing, more of me exploring his strong body. The shower, like the rest of the suite, was expansive. There was plenty of room for the two of us, but we still managed to crowd one corner. We soaped each other up, more feeling each other's body than trying to get the other clean. We kissed, a lot, and I tried very hard not to spend all my time trying to coax his cock back to life. Still, even no where near hard, he was so much bigger than mine.
We also chatted playfully, he was sweet in the way he would compliment my body, he told me I had a great ass, liked my legs, my flat belly. He asked about my workout routine, and suggested that maybe some time we could go for a run. He was talking in a way that implied we were going to see each other again, not just tonight (and tomorrow morning I assumed), but more often and further out. Dates. Multiples. Weekends, not just this one.
We dressed after the shower and getting back into the clothes I had worn the previous night, the idea of the 'walk of shame' entered in my head. Why would they call it that? I wasn't ashamed. Of course, it was easier for a guy, I was in my slacks and shirt and I looked like I was dressed normally. Sure, maybe jeans would have been better, but Friday work casual was just fine for Saturday morning. We discussed me getting an Uber, but Derrick made a point that he needed to know where I lived in order to pick me up, so I agreed to let him drive me home.
Ashley. Shit. That was the first time she entered my mind. One of my best friends from college, we split a place for the summer while we both had internships in the city. I wonder if she would think Derrick was hot. Of course she would. Jesus, why was that the first thing to pop in my mind about her? I had for a brief second a thought about trying to be with Ashley when we were freshmen, but I got friend zoned just as fast and stayed there. I knew a bunch of guys she had dated over the years, and she would definitely think Derrick was hot. That brought a smile to my face. Of course, I had also been with her and other girls (I was the designated safe friend zone guy for all the girls I knew) enough to know how they talk when they are together, and in those conversations, I would have definitely been peppered for all sorts of details.
Finding my phone I noticed it had kind of blown up with texts and calls. 'Where are you,' 'are you OK,' 'call me...,' that sort of thing.
I texted back a quick, 'all OK, be home in a bit, sorry about not responding earlier, and put my phone away.'
Derrick and I headed down and got in his rental, a much nicer car that the few times I would travel and rent a car, and he offered a stop for coffee and maybe a bite. My internship didn't pay a ton, and I rarely went out for coffee on weekends, but I agreed. How much could it cost? He drove like he knew where we were going, and he did, apparently, since he pulled up to the valet at a nice cafe that I had no idea existed. The valet opened my car door and Derrick came around to escort me into the cafe, his arm around my waist without a care in the world who was watching. I had never been on a date, so walking with someone on my arm, well, on someones arm to be more accurate, was brand new, and compounded with the fact it was a guy, a hot older guy, I was a bit sheepish. But Derrick's confidence bubble seemed to include me, so I let him steer me forward.
Apparently, he had been here before since the host seemed to, well not know, but at least recognize him, and we were quickly seated. I was given the menu and the prices were what I might spend for what I would consider a pricy dinner out after work, not a spur of the moment Saturday brunch. I am pretty sure my expression showed my shock.
"OK Chris," he interjected, "I do not mean to be presumptuous, but I know you are still in school and on an internship. I have no idea how much it pays, if anything, nor am I asking. I am going to assume we have different financial situations. Maybe we don't, maybe you have a massive trust fund. I don't need to know. I like this place. Order whatever you want, it is on me. And dinner tonight is on me. And brunch tomorrow. And any other meal or drinks or date we have in the foreseeable future. I do all sorts of things, eat at all sorts of places, from expensive all the way down to hole in the wall. What is important to me is that they serve good food. And, while you are with me, that you like the place as well." He reached across the table and took my hand and continued, "I like you. We are just getting to know each other, but I like you. A lot. I am not trying to impress you, but assuming you like me as well, you are going to have to live in my world at least some of the time we are together. I want to get to know more about you, and I want to come live in your world some of the time as well... But while we are living in my world, let me take care of you. No expectations, you don't owe me anything, but I can afford things like this."
"I'm not used to this, any of this." I thought better of gesturing around the restaurant, partly because I didn't think it would look good, but partly because I didn't want to pull my hand away from his. "That stuff about 'I've never done any of this,' well, that includes this. I've never been on a date. I've tried, but after a few minutes of what I would plan out to be a date I would learn I was in the friend zone. I don't go to places that look like fancy gardens with fresh flowers and people drinking champagne," which looking around, there were more than a few tables with ice buckets full of champagne and it looked like a walled garden in a very expensive estate.
"Fair enough," he replied, "but I got where I am by seeing what I want and then going after it. I am going after what I want," he punctuated that last word by squeezing my hand a little tighter. "I haven't scared you off, have I?"
I looked into his eyes, those sexy blue eyes, took in his handsome face. What, 12, 16 hours ago I would have thought someone was crazy for saying I would find a guy attractive, handsome, sexy. Sure, I could admit George Clooney and Ryan Renolds were handsome guys, but I didn't find them sexy, they never stirred anything in me. Derrick stirred something in me, and I liked it. "No, you haven't scared me off."
"Good, can you look at the menu and not look at the prices?"
"Not really," I honestly answered.
He reached across the table and took the menu from me. "Tell you what, tell me what you would like to have for breakfast and I'll order for you. I am not trying to be controlling, I just want you to be able to enjoy your brunch. Coffee, espresso, cappuccino?"
"Coffee."
"Cocktail, mimosa, wine?"
"I am not used to day drinking."
"Juice?"
"OJ would be nice."
He worked through a number of options and got me what I had to admit was the best tasting omelet I had ever had in my life, delicious coffee and the freshest orange juice this side of an orchard. This breakfast may have been the best meal I had eaten all year. Over the meal, we talked a bit more, he was in finance, and was in town checking on some investments his company managed and meeting with clients. I didn't probe too much but I surmised he was doing well, very well. We talked about family, and he didn't ask, nor did I really think about how my family would react to me dating a guy. Were we dating? I mean yeah, this was a date, and tonight was a date, and he was talking about being in town through the next weekend, but were we dating? Was I gay? I pushed that all away. He talked about his folks, dad was a doctor, mom was a professor, and how he had grown up a multi-sport mid-tier athlete in a liberal enclave and when he came out to his folks, it was no big deal.
"What do you want for dinner," he pivoted to at the end of the meal. "Steaks, seafood, Italian, sushi, something else?"
I had had sushi with friends, so I figured that was a safe option. I knew how expensive steak places could be...
"Perfect. Look, I do not want to be presumptuous, but were you thinking about staying over tonight?"
"Um. yeah," I embarrassingly admitted, blushing a bit in the process as I thought about being with him again.
"I was hoping you were. May I be so bold as to suggest you pack an overnight bag..."
"Makes sense."
"Swimsuit to lounge by the hotel pool tomorrow? Not that we will do that, but at least it is an option."
"OK," I agreed.
"Look, if you want to do something, if you have somewhere to go, previous plans, just tell me. If you want to hang out with friends, tell me, if you want to bring me along, tell me and I'll be there. I have been gay for ages. You have been gay for less a day, if you even want that label. He reached across the table and took my habd as he continued, "from what you have told me, everything about what you and I are doing is new for you. I have no desire for you to freak out, get scared, or overthink things. I will go as slow as you want me to go. But know this my dear Chris... I have no desire to go slow. I went up to you because I thought you were sexy. The fact you have no idea how sexy you are, well, that makes you even sexier. What I am hoping is that by the time you see yourself the way I see you, you will have the same opinion of me as I do of you."
I squeezed his hand a bit and took a deep breath, staring into his beautiful eyes, admitting to him what I was admitting to myself. "You are... sexy, handsome... You have pushed buttons and pulled levers inside of me that I never knew existed. I don't need you to go slow. Yeah, I am sure that things will freak me out, but I have not regretted a second of time since I saw you looking at me in the bar."
We continued chatting a bit and he paid the bill without even looking at it, and ushered me out toward the car, his arm wrapped around me, my body leaning into him. When we walked in, his arm was more loosely draped around me, now, I felt like I was glued to him. I liked it. It also made me feel weird, but no one was looking at us. The weirdness was all in my head, so I tried to push that away and just concentrate on what felt great, and this felt great. I didn't even freak out when he turned me and kissed me. In fact, I leaned into it, wrapping my arms around his neck and letting him really kiss me.
The car pulled up and I reluctantly disengaged. It was a little comical that Derrick went to hold my door open but found the valet already there. I slid into my seat and as he got in, leaned across for another kiss before we took off. We chatted a bit as he headed to my place, talking about Ashley and my internship. When we arrived I wasn't sure if he was planning on walking me in, but I think he sensed it wasn't time to push that issue, so we said our 'so longs' in the car, had another sweet kiss and I headed off home, for at least a few hours.
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