Back from an incredibly action-packed trip to the Big Apple.
New York was a total whirlwind and I enjoyed every second of it. Definitely needed the R&R partnered with plenty of good food and entertainment. It also felt amazing to get lost in a new city and welcome the anonymity. I realized just how much I needed to get out of LA and out of the constant search to find a life partner.
I had sex in New York City. TWICE.
I think I outlined my sinister plans briefly in some of the last entries. Besides the sight-seeing, I had planned to hook up with Terry and Jay, two of my old friends from Staten Island. I know Jay has gotten some mention in this blog, mostly because I gave him a blow job eight years ago and has never forgotten it. He's been on a quest to reclaim me once more and though I flirted back, I never really took him seriously. His best friend Terry, on the other hand, formed a very courteous friendship with me and for all intents and purposes, we were extremely platonic. He'd tease me about Jay and we'd all have a laugh. It wasn't until a few months ago that Terry began to confide in me about his deteriorating relationship with his girlfriend Melissa. He finally broke up with her, as I had mentioned a couple entries ago. We made mention of my visit and it came out that he wouldn't mind hooking up with me, too. So now I had two guys after me.
Nothing I can't handle, right? I recalled my old slut techniques and put my game face on. It would be very easy to make these boys Eskimo brothers.
The easy part is that I didn't have to do too much lying. Terry and I began to master a plan to see each other. He was aware Jay was anxious about my visit and he said he didn't care if I hooked up with Jay again. In fact, he insisted I did if nothing else, to boost his best friend's crumbling self-confidence. Terry and I chatted for several weeks about my trip, and he'd always remind me to make sure to make time to see Jay, with a little smirk on his face (well, the emoticon did at least haha!). I reluctantly agreed. My trip-mates offered up the living room in the suite and the race was on.
Thursday evening in New York City. After a breath-taking trip to the Statue of Liberty, I was ready to see Terry first. He met up with us near Battery Park and we had dinner. Terry's a nice guy but he's very quiet and reserved. He wasn't very talkative and you could tell he was a little nervous. It was painfully obvious he was there to meet me and have sex. A few rounds of whiskey at the local Irish tavern and I was ready to go. Back at the hotel, Terry waited for me in the living room, fiddling with his phone as I took a nice, long, hot shower. Once the New York City grime was off of me, I was ready to sex this incredibly taciturn Staten Island boy. My friends giggled in the main bedroom as I shut the door and said goodnight.
I turned off every light off in the living room with extreme patience. Terry turned off his phone and settled under the covers. I dried my hair the best I could and slipped in next to him. The room was nearly pitch dark. We laid down on our sides, facing each other. The sexual tension had taken several months to boil over and here we were, laying in bed. The silence was unbearable so we just started making chit-chat, like we always do over FB messenger. We talked about our broken love-lives and how ridiculous Jay could be. We never once talked about our attraction to each other. It wasn't until I mentioned how fun my trip had been so far that Terry said he was having a good time, too. I raised an eyebrow in the dark and nudged myself closer. "I guess it could always be better..." I trailed off as I settled even closer still to him. He took my hint and scooted closer so that now we were almost touching noses. "How could it be better? What would make it better?" he asks in a whisper, his voice dripping with that New York accent. I angle my face so that our lips are mere inches apart. I don't even whisper, I breathe the words to him: "I think you know how. Maybe if you made the first move and not me." He laughs softly to himself and I can feel the tickle of his breath. "You mean this?" and he breaks the spell. He kisses me hard. We go at it, kissing and kissing. He's about the best French kisser I've had in a long time. I lose myself just kissing his mouth, his face, his ears, his neck....he counters with bites and kisses all over my body. He makes me come once with his fingers, slowly and quietly. I can't let my friends hear me screaming! :) Eventually, I pull down his shorts and suck his dick with a renewed sense of purpose. I'm going to make Terry grateful he ever met me. He chokes on his words, unable to tell me how much he loves the work I'm doing on him. A few seconds of deep-throating and suddenly he's not so shy. He thrusting his hips, fucking my mouth violently, harshly whispering if I like sucking his dick. All I can do is make a few wordless groans before I pull away breathless. Terry grabs a condom and tears the packet open. He orders me to get on top and I finish myself off in a matter of minutes. He turns me over on my stomach and effortlessly fucks me from behind. I remember he once told me it was his favorite position. He comes almost instantly. We clean up, put our clothes back on and settle back into bed. We stay up a little longer, chatting about how great it felt to release all of our tension on each other. He flings an arm over me and we fall asleep. Terry doesn't snore. I hear him start to breathe softly, rhythmically. He's sound asleep. Eventually I fall asleep, too. Sated and incredibly happy.
The next morning, we sit up in bed and watch the news about the Empire State Building shooter. He puts on his street clothes back on and says goodbye to my friends with a hug. I walk him downstairs and bid him farewell with a kiss on the cheek, right in-front of the doorman of our hotel. Yeah, I'm shameless. It gets worse.
****
Fast forward to Saturday night. My last day in New York. After a trip to a Mets game and Central Park, my stomach was churning with the reality that I would be seeing Jay in a few hours. We had spent all day texting, planning out where to meet. With Terry I was as calm as a cucumber...and I like him more than Jay....why am I so fucking nervous?! 8 pm rolls around and Jay tells me he's waiting for me in-front of our hotel. My heart is pounding as I tell him we'll be right there. I give one last furtive glance at the girls and tighten the grip on my shopping bags. Heeeeeere we go! And there he is. Jay. He walks up to greet me with a HUGE grin on his face. "Hey there!" I squeak and give him a hug. OH GOD, am I really going to do this tonight? Yikes.
We take Jay back to our hotel room and chit-chat a little as we put our stuff away. I pack a little since the next morning we're set to flight back home. I can tell Jay is nervous but not as bad as Terry. Jay can artfully keep conversation with 3 girls and laughs at our jokes. We settle on drinks around the corner at Duke's. I'm going to need a shit ton of alcohol if I'm going to convince myself to hook up with Jay again.
At the bar, things aren't so bad. Jay is extremely talkative and asks all sorts of questions. I slam down two whiskey drinks and quickly feel my blood warm up. Jay rubs my right knee under the table as he talks to the girls. His hands send shock waves throughout me. I stay quiet and feel a pleasant ache settle in my pussy. Okay, I'm ready.
Back at the hotel, Jay is relentless. When the girls are not in the room, he pulls me close and kisses me passionately. My head feels light. I know I can't let them see. I beg him to just wait a few more minutes which he answers with a frustrated sigh. I distract him by telling him to wait for me on the fold-out bed as I pack my clothes for the trip home. I can feel him staring at me, like he's stalking prey. That familiar ache pools between my legs. Oh God, do I want him too!? We try to talk but again, the sexual tension is so thick you can cut it with a knife. Once I finish, I settle on the bed with him and reward him with a few kisses. I whisper at him to keep it PG as my friends are in the next room. He promises to keep it clean but it doesn't last long. He's pawing at my breasts, biting my bottom lip and pressing his erection against my thigh. Finally, one of the girls tells me the shower is free and I leap out of bed. Jay groans but I tell him it's worth the wait. "Oh come on! You've waited 8 years...you can wait 8 more minutes!" As I get ready for my shower, I look at myself in the mirror. After all the making-out with Jay, my cheeks are flushed pink. I think I want him. I think I want him to stop waiting.
After my shower, we get down to business immediately. I turn off all the lights and slip in next to him. Jay is on me instantly. And he didn't stop for hours.
HOURS. Yes. HOURS.
I can't possibly transcribe it all. As I explained it to Terry, who asked for all the sexy details the next afternoon, Jay took me on a nearly 3 hour Staten Island Ferry ride to Poundtown.
Every single position you can imagine: legs on his shoulders, arms pinned down, doggy style, me on top, you name it. Oral, masturbation, biting, choking, hair pulling, his teeth torturing my nipples and so much intense fucking. Oh God. The fucking. Slow, fast, soft, hard. He has the most unyielding dick ever. He never stopped fucking me. I swear, he had a rock-solid erection for nearly three hours. And he only allowed himself to come once. I lost track of my orgasms after I hit 10 or 11. He teased me relentlessly with his dick, pulling out almost all the way and making me beg him to put it back in. Then he'd cruelly thrust it back in, much to my delight. I've never felt a cock that skillful INSIDE of me. It's like he could read my mind. I came so much and so hard, I'd drift in and out of consciousness. I pleaded for him to let me rest but he'd just whisper in that rough New York accent, "You think we're done already? I haven't even gotten to the hard stuff yet." I'd whimper to let me suck his dick at least and give my sore pussy a rest, but he'd say no. I run my hands all over his back, sides and the strong muscles of his upper arms as he's holding himself up to fuck me savagely. I'm a human puddle of emotions, my brain feels like scrambled eggs. All I can concentrate is the pounding he's giving me in my vagina. Each orgasm is like a crashing wave, one on top of the next. At one point, I can feel tears welling up in my eyes. My mind is shattered with pleasure. I'm mumbling something stupid about Chris, who is all the way back home. I'm feeling like I'm going to burst into tears, as I sob that he hasn't texted me at all since I've been on my trip. Chris didn't even wish me goodbye! Jay's eyes widen and he looks a little panicked. I must sound idiotic, so I brush the tears away and laugh that I'm losing my mind with all this sex. We go at it for a few more minutes before he finally wills himself to ejaculate. He collapses on top of me and I run my fingers through his soft, brown hair. My legs feel like jelly. Dear God, Jay is the goddamn devil. We talk for a little. He says I'm his ideal girlfriend and strokes my face, tracing his fingers across my eyebrows: "Don't let any man tell you that you're not beautiful" he says softly. My heart melts. Now I feel bad for being so mean to him over the last 8 years. We fall asleep together. I hear him snore a little before he settles into a deep sleep.
The next morning we're up at 6 am and I walk Jay to the elevator. We say goodbye and kiss. I thank him for a great night and he grins. The elevator dings and the doors slide open. I kiss him on the mouth one last time, just like in the movies. Our lips softly part and he slips away from my arms. He looks at me one last time as the elevators doors close. He looks melancholy. I must've looked the same.
The good thing is that this is all just sex. Terry and I agree to keep being friends and we've been fine, texting and messaging about our fun time and what to do about Jay. I've tried to text with Jay very little, so as to not get his hopes up. They're all in New York and I'm very much in LA. The trip also made me realize that though I like Chris a lot, the fact that he's so busy is not working for me. He doesn't seem special enough to wait for. And that's fine. I'm glad I realized this now and not 2 months from now when he potentially might be moving away.
Great trip to New York. My confidence has been boosted and my endorphin level is at an all time high. Back to work tomorrow and to feel the crash. But for now, let me have my dirty little secret memories :)
Me looking extra gross while hanging out at Dillon's with Terry...
I would post a pic of me and Jay but I didn't take any, so here's one of him back in July during his softball tournament. His facial hair was more intense when I saw him Saturday, as he's now growing a play-off beard:
Two guys after me....gosh, I should just pack up and move to Manhattan.
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