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It was early October now and hoodie season, as I liked to call it, was upon us at last. The time of year I loved the most, when it was starting to cool down, but it wasn’t too cold, just comfortable.
It was the time of the year when you could go out just wearing a hooded sweatshirt and I loved being able to do that!
A few months had passed since my first encounter with Kendra. My ass had made a full recovery by now since a pretty decent amount of time had elapsed. I hadn’t made any effort to be back on the bottom just yet though, and I had not yet seen Kendra since that first time. Well, I actually had seen her plenty of times at the club, we bumped into each other pretty often.
We just hadn’t slept together since our one night together.
But now my mind was recalling our conversation that first time we ran into each other at The Raven, about a week after we had sex… walking into the club with Lisa at my side, we were making our way towards the bar, pushing through the crowd. I said hello to a few of the other girls I knew, as we brushed by them.
Suddenly about halfway to the bar, I felt a hand on my back and turned around to see Kendra standing over me with a big smile.
“Hey there, Jay… how’s your ass feeling?”
I laughed, “It’s been better! Expecting it to make a full recovery soon.”
“That’s good to hear. Do you think we could spend some more time together again… like real soon?”
“I don’t know Kendra,” I said honestly, “I loved the way you made me feel… but I think I need a little while before I go back to being a bottom for anyone.”
“I see… that’s okay. You know where to find me when you’re ready for more,” she said winking at me.
She then leaned in and gave me a kiss on the lips, before turning and walking away. I glanced over at Lisa, who was grinning evilly at me.
“I see you ran into your ‘friend’ Jay… going home with her tonight?”
“Shut up,” I said, giving her a playful shove.
“I told her it’s going to be a while before I bend over for her or anyone else for that matter.”
“Aww, well that’s a shame,” I heard Holly’s voice from behind me, “Cause I was really looking forward to getting another shot with you.”
“You and a few other girls in this club,” Lisa joked.
We spent the rest of that night drinking, dancing, and having fun. I didn’t hook up with anyone that night, but Holly went off and hung out with a couple of guys. Lisa wandered off at some point as well, and I hung out at the bar with Jen, who I had not yet gotten the chance to call, as I had promised the previous time I was there.
My mind returning to the present, I realized that I’ve actually been spending most of my time at the club talking with Jen lately… and don’t ask me why, but we haven’t slept together yet.
Every time we run into each other and begin talking, gradually getting a nice chemistry going between us, something would always seem to interrupt. Maybe it’s just bad timing, or maybe bad luck… I don’t really know, but tonight I decided this was going to be the night I hook up with her, one way or another.
I had been sitting at home in my apartment that Saturday night, finishing up dinner. I decided to make my way to The Raven and see if Jen was there. But I thought I’d give her a call first before heading out the door. It rang twice, and she picked up, with a cheerful voice.
“Hey Jen, it’s me Jay.”
“Hey, what’s up buddy?”
“I’m heading over to The Raven tonight… you going to be there?”
“Well, I wasn’t originally,” she said. “But if you’re going to be there, then sure.”
I laughed, realizing that she was probably just as desperate at this point to hook up with me, as I was to hook up with her. Like I said, we had been trying to find the right opportunity for a while now, things just kept strangely getting in the way.
“Great, I’m heading over there now… see you soon?”
“You betcha,” she said.
We hung up, and I grabbed my car keys, heading downstairs to the car. I had no intention of getting drunk tonight… I was just hoping to spend some time with Jen, and hopefully get a chance to have some “fun” with her as well.
Arriving at the club, I parked my car and quickly made my way inside. I had only gotten to the front door of the club, when I heard a familiar voice calling my name. As I quickly turned, I saw Jen running towards me. When she reached me, she threw her arms around me and gave me a big hug and a kiss on the cheek.
“Looks like you beat me here,” she laughed.
“Yeah, but only by a minute or so! Let’s go inside, I’ll buy you a drink.”
I took her by the hand and led her into the club, through the crowd and towards the bar. One or two beers wouldn’t render me incapable of driving home tonight. So I bought Jen a vodka, and myself a beer and we started talking about the past week. It felt like minutes had passed, but before I knew it, I looked at the clock and noticed it was 11:30 already.
“It’s getting late,” I begin saying as Anadolu Yakası escort I looked over at her, and she smiled.
“I’m glad you invited me to hang with you Jay… but… I have to admit, I was honestly hoping we would be doing a little more than just talking.”
“Oh, is that so,” I teased.
“Yes, that’s so,” she said, climbing off of her seat and sitting down on my lap with a sexy grin.
She draped her arms around my neck and leaned in real close, and I could feel her warm breath on my face.
“Wanna dance?” she whispered to me in a seductive voice.
I figured it would be a good way for the two of us to get ourselves nice and worked up, and so I agreed. We both stood, and I took her hand once again leading her out to the dance floor. There was a heavy bass pop song playing over the radio, people grinding against each other and a few people making out and being quite hands on with each other.
With Jen in front of me, her ass pointing out slightly towards me, I started grinding with her to the music. The bass was pumping and it was easy for the two of us to get into the vibe. She turned around and we were now face to face with each other. Three songs later, and the DJ had started playing a slower song. I’d heard it before, though I had no idea what the name of it was… it seemed like Jen did though.
“I love this song,” she said, excited. She draped her arms over my neck, and I pulled her close as we started dancing. As we danced in a circle around the floor, Jen stared deep into my eyes and I felt the energy starting to rise between the two of us quickly.
I took the lead, and moved in, pressing my lips to hers. They were so soft… and she was wearing what I believed to be some sort of cherry lipstick. Our tongues tangled together, as we began making out, and I felt her hand grabbing at my cock.
She rubbed me through my pants, until I was as hard as I thought I could get. Breaking that kiss, she started eagerly kissing, sucking, and biting at my neck. I groaned now as she gently bit and parted from my neck after a few long seconds.
“I want you,” she whispered. “Right now.”
“Let’s go then,” I said.
Wasting no time, the both of us started rushing off towards the staircase that would lead us down to the basement. We were rushing, hopeful that nothing would come up to interrupt us this time.
We got downstairs, and chose the nearest, open room, locking it tight and embracing one another tightly.
Making out once again, I felt her fumbling with my belt and I pushed her towards the bed. She sat down on the edge, and smiled seductively up at me.
“I’m going to suck your cock.”
“You don’t have to tell me twice,” I joked.
She pulled my pants, and boxers down, around my ankles and took hold of my cock. In a firm grip, she began stroking me with one hand and massaging my balls with the other. I moaned, growing more stiff by the second.
Jen gave the tip of my shaft a lick, teasing it for a few painfully long seconds with her tongue. Once she felt like she had teased me enough, she started sucking on the tip only. After a few more moments, she slowly slid her wet, silky lips down over my shaft until my balls were pressing up against her chin.
I took a handful of her soft hair, and started moving her head up and down over my cock. The sucking, gagging noises, filled my ears and I leaned my head back, enjoying every second of this brilliant blowjob.
She stopped just momentarily to look up at me and ask, “whose topping?”
“Oh,” I said, “I uh… I’m on break from being a bottom if that’s okay with…”
“That’s fine with me baby, I just want to feel your big cock inside of me.”
I loved how interested she was in pleasuring me, the idea that she mostly just wanted me to fuck her, rather than the other way around or both ways, made me even more aroused. She had swallowed my cock whole, once again, and was really going at it now and I had given myself completely over to her. I laid back on the mattress, my arms above my head as Jen continued to orally please me.
I heard the wet popping sound of my cock sliding out of her mouth again, and she came up to kiss me on the lips.
“I want you to fuck me, but first… are you okay with going down on me?”
That I didn’t mind, I wasn’t looking to get fucked in the ass, but I loved to suck a nice tranny cock as much as I loved to have mine sucked.
“Gladly,” I smiled.
“Good… cause I am dying for some good deep throat action!”
“Oh, is that right?”
“Totally… Lisa told me your pretty good at deep throat.”
Laughing, I took her by the arms and turned her over onto her back. With me on top now, I kissed her on the lips and then smiled down at her.
“Just lay back and relax, and I’ll show what I can do,” I said.
I started kissing my way down her whole body, over her breasts, stopping briefly to lick and suck on each of her nipples before continuing. I kissed my way down her belly, Anadolu Yakası escort bayan and to her thighs. I stopped just in front of her big cock, which was by now fully erect.
Jen was about seven and a half inches long, and a bit on the thick side as well. Nothing I couldn’t handle though, as I was definitely used to this by now. I dove right in, wrapping my lips around her member, licking and sucking. Up and down my head moved, I cradled her balls and massaged them for a few moments… I was trying to build a fire before going into what she really wanted.
She moaned, writhing around underneath of me, and feeling her move around made me more eager to please her. Finally, I took her to my throat, delivering what she had been waiting for this whole time.
I suppressed my gag-reflex, something I had gotten a lot better at doing recently, taking her as deep as I could manage. I could feel her warm balls against my chin, saliva running down them, as I started the swallowing motions that would drive her crazy.
“Oh god,” she moaned loudly, “Lisa was right… this feels great!”
I continued for a few moments before gasping for air as I came back up, spit running down my chin. I waited about three seconds, before taking her once again and holding her there for as long as I could manage.
“Oh fuck… that’s so… fucking good,”
Again, I popped back up for air, and again I went back down, swallowing her whole. Two minutes of sucking, stroking and deep throating, and finally Jen cried out in pleasure. Her body tensed up underneath of me and she quite vocally announced her impending orgasm.
I felt the hot load shoot against the back of my throat, and I swallowed it all, it was quite a lot of cum, but I took it all. When it was over, I came back up, breathing in oxygen as though I had been suffocating. I was gasping, but still managed to smile at her as she pushed herself up into a sitting position.
“That was amazing, Jay,” she said happily.
“I’m glad… you liked it… now,” I replied between gasps.
“Now, I want you to fuck me like your life depends on it,” she ordered.
I wasn’t protesting, I had been waiting for this chance. I grabbed her legs, lifting them up and causing her to fall back again, both of us laughing as she fell.
Holding her legs high up above her head, I moved my face up close to her asshole. I began to lick up and down the crack, pushing my tongue into her hole and lubing her up nice and good.
I gave her another lick up and down her crack, this time going all the way up to her balls. I then licked her balls for a few moments, before moving back down towards her asshole.
“Oh Jay… I want you so bad,” she moaned.
I was done with the foreplay, and I was ready to get this show moving. I pulled my face away from her behind, keeping her legs suspended in the air and grabbed a bottle of lube that was sitting on the nightstand next to the mattress… someone must have left it after their last session in this room.
After getting my dick nice and lubed up, and applying an extra amount to Jen’s asshole, I pressed the tip against her hole and leaned in close to kiss her on the lips. In missionary position, our lips locked together, I gave a push and felt myself slide right into her.
Jen dug her nails into my back, moaning into the kiss as I pushed inch-by-inch deep into her tight asshole. Once I was all the way in, I stayed still for a few moments before the kiss broke, and Jen started moving her hands up and down my back.
“I’ve been waiting for this,” she whispered into my ear. With that, I started thrusting in and out of her, slowly at first.
Gradually, as she started moaning louder, I increased my pace, fucking her harder and faster. Our sweaty bodies slapping together, our breathing becoming heavier… I loved the way her ass felt around my cock. I began to get tired of leaning on my hands and my arms were starting to hurt.
I decided it was best to change positions now. Rolling over onto my back, I pulled her over on top of me, so that now she could ride my cock. Up and then down she bounced on my cock, her own semi-erect penis flopping about as she did. She cupped her breasts, moaning as she moved up and down, up and down over my shaft.
I felt her asshole starting to tighten around me, and I grabbed her erection and started jerking her.
“Oh yeah,” Jen sighed, then ordered, “Fucking pound me Jay!”
With my feet flat on the bed, my legs bent, I began thrusting upwards, fucking her as hard as I could manage. I pushed up into her and lifted my ass up off of the bed, holding that position for a few long seconds. Apparently, she really liked that, because Jen suddenly, and quite randomly, cried out in pleasure and started to cum.
She shot her load all over my stomach and chest, and there was a lot of cum. It had all been completely random too, I just assumed however that I must have hit exactly the right spot by doing what I had done.
“Holy escort bayan shit,” she cried, out of breath. “That was fucking amazing!”
I still had not finished myself yet though, and I did not intend on stopping until I had made sure we had both gotten ourselves off. Continuing to thrust in and out of her, with her bouncing up and down on me, she started moaning and panting once again. Her dick grew hard again, and she started stroking herself in rhythm with my thrusts.
“Cum for me baby,” she whispered, squeezing her ass around me, “Cum inside of my ass for me… I want to feel you filling me up now.”
With her request made, I felt my body begin to tense up, my balls burning with hot cum just waiting to be freed. I groaned, calling out her name, semen bursting from the tip and pumping deep into her loosened asshole.
I felt my fluids dripping out, running down my shaft and over my balls, as we stayed in that position, kissing intensely. Finally, she collapsed on top of me, both of us covered in sweat and we lay like that a few moments more.
She rolled off of me onto her back, and we both sat up, wiping the sweat from our faces.
“I had a lot of fun,” she said laughing.
“So did I… I’m really glad we finally got to do this.”
I gave her a kiss, got out of bed and started to put my clothes back on. Jen rolled off the mattress on the other side, searching for her panties and looked over at me as she slipped into them.
“Are you coming next Friday?”
“Here?” I asked, unsure of where she meant.
“No, to the bonfire that we’re all having at Rob and Annie’s house?”
Rob hadn’t said anything to me just yet, but that didn’t mean I wasn’t invited. When Rob would throw parties of any sort he almost always waited until the last second to let me know, it had been that way since we were teenagers, throwing high school parties.
“I’m sure I’ll be there… he hasn’t said anything to me yet though.”
“Well, I hope I get to see you there… maybe we can hang out some more.”
“That would be fun,” I said pulling my shirt over my head. I walked over to her, pulled her into my arms and gave her a kiss on the lips. We left the club together, hand in hand, and I gave her a ride back to her place before making my way back to my own apartment.
***
As I figured, Rob sent me an e-mail two days later, inviting me to a bonfire he was having at his house that coming Friday.
Details: Starts at 8:00. Beer, food, music, and fun. At Rob and Annie’s house. Byob.
At the bottom there was a personal note asking everyone it had been sent to, to reply with their decision as to whether or not they would be there. I clicked reply, and cracking my knuckles, I began to type my response.
Count me in bro! I’ll be there for sure. We should party the way we used to back in the day. I’ll bring the Jack Daniels and it’ll be just like old times.
I clicked send, and logged off of my e-mail account. Back in high school, and during our college days, Rob and I use to party almost every weekend together. Back then, we drank a lot of whiskey, and whenever we would drink, we always got pretty wild. It was a lot of fun, we never got violent, or did anything that would result in anyone getting hurt.
We just drank, got sloppy drunk, and had fun. I still drink whiskey to this day, I’m just not as heavy with it as I had been back then. I was definitely craving a night where we could kick back and have the same kind of fun we use to have back then. Maybe we would surprise the girls with how funny we could get when we were that messed up.
I received a response from him a few minutes later.
Dude, I’m down. Bring the whiskey and we’ll show everyone how the class of 2006 parties.
It was on then! This Friday night was going to be a lot of fun, I knew it would. I doubted there would be any sex involved, since I had a hard time usually getting hard while I was drinking whiskey… unless I was on the submissive end. If it was with someone like Lisa or Holly… or even Annie, I would be okay with being a bottom. It had been a few months, maybe it was about time for me to get back into it little by little.
***
Friday night arrived, and excited beyond belief, I quickly got ready before making my way over to Rob’s place. I threw on a white t-shirt and covered it with my black Philadelphia Flyers hoodie, honoring my city’s Hockey team. Upon arriving at Rob’s house, I was met at the front door by Annie, who looked quite happy to see that I had made it.
“Hey Jay, it’s so good to see you,” she said happily, leaning in to give me a big hug. I embraced her back, and she gave me a kiss on the cheek.
“Thanks for the invite, I really have been looking forward to this.”
“It’s no problem,” she said, welcoming me inside.
This was actually the first time I had been to their house since they first moved in together a few months back. I remembered when Rob had told me that they were getting a place together. He had been very excited about it, and I was happy for the both of them. I would have helped them move, but I had been so busy with work at that time, I just couldn’t get any time off to pitch in the extra hands.
Rob didn’t hold it against me though, and instead, his brother wound up helping them with everything he had to do.
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