Posts Tagged flip

One Relationship, Two Locations

Since Monday night was spent at CK’s, as per usual, we decided to spend our Tuesday night in Hoboken. Tuesday night in the summer is a big night in Hoboken.

CK and I had begun hitting up free yoga on the pier every Tuesday after work. It was a great way to hit the reset button and recharge for a new week. I found myself looking forward to the group outdoor session more and more. We’d even begun to make a few friends in the class.

I got out of work on time and made my way home to grab our yoga mats. CK had to work a little later, so he was going to meet me on the pier. I invited many of my other friends who had hit up yoga once or twice, but no one took the bait. I arrived just barely on time and reserved a spot for the two of us. CK finally arrived a few minutes into class as we continued our poses and relaxing breathing.

Earlier that morning, we planned to attempt to go to the movies that evening as part of Optimum’s Triple Play free movie night in Hoboken. I myself don’t have the service, so I have to borrow a friend’s card and hope he has no intention of going. When I learned we wouldn’t be able to get ahold of his pass, we decided to forgo the movies. Instead, we swung by the grocery store on our way home to share a home-cooked dinner for two.

We enjoyed our food on the couch in front of the TV, relaxing for the rest of the evening. It was nice to cuddle up next to him and watch TV. It was beginning to feel like a routine. Even though we still lived in separate apartments, it felt like we were living together. We spent nearly every night in each other’s company. The only difference was we had two residences.

We’d talked about moving in together. Neither of us was thrilled with our current roommate situations. Mine were simply disrespectful and unappreciative, and his… Well, we could be here all day. Every day was a new shady dealing. He needed to get out, and his lease was scheduled to be renewed in November. We didn’t make a concrete decision we would live together at that time, but we both began entertaining the idea.

I know many of you are shocked by the timeline there. Come November, we’ll have been dating for eight months. I know that sounds like a very short time to be together before moving in together, but like I said, it was almost as if we already lived together. Not much would be different. We both agreed this would be a goal for now, not a definitive date.

When bedtime arrived, we made our way to the bedroom to get ready for bed. Things took a bit of a detour when CK began seducing while I brushed my teeth. From there, things only got better. The sex was great. We were back on our game. And, true to our fashion, we flipped. That seemed to be how things went for us. Neither was a top, and neither was a bottom. We both experienced all the parts of sex. Our sex-life was very healthy and diverse. I’d finally found my match both inside and outside the bedroom. He managed to satisfy my physical and emotional needs. I was truly happy.

I thought about all the others before him. They seemed a distant memory. None of them came close to my relationship with my Superman. Many of them treated me poorly and didn’t deserve my love. Some of them attempted to love me, but the connection wasn’t there. I didn’t regret a single one of them, for they all brought me to where I am today. Sure, I was still carrying around some of the scars, but I was a stronger man for them. Those were my battle wounds. Those were my war stories. I didn’t miss any of them, but cherished their presence in my life — Even the a$$holes. I was truly in love, and I didn’t want it to end. The road I’d taken had led me to CK, so looking back, I wouldn’t have changed a single direction.

The next night was spent apart. I was supposed to be getting my review at work, but my boss rescheduled it twice that day, and then he had to schedule it for the following day. I was frustrated and needed to take those frustrations out somewhere.

I hit up the gym to lift and swim to calm my nerves. While there, he calls finally, telling me he’s working late and probably can’t come see me. Once again, I felt disappointed. He asked if I would mind coming into the city, but I wasn’t up for that. After not hearing from him all day, I made alternate plans. I was meeting up with my old roommate for a drink. I suggested maybe we needed to spend the night apart. He agreed.

More and more, I was realizing maybe we had been spending too much time together. Small things were getting on each other’s nerves. I wondered if I was losing my individuality. Now that I was back in the gym again, I was feeling better about myself. I relished my workout time. This was something I put on the back burner after meeting CK. We both needed some “me time” every once in a while.

As time progressed, we would find that balance. We’d only been dating four months. We were still figuring everything out. But, I knew, in the end, we’d figure it out together.

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“I Love You”

No matter how many times it happened, I never grew tired of waking up next to CK. The night before concluded with the most passionate lovemaking we shared to date. Everything felt amazing!

It was late in the morning, but I was still reeling from our late-night romp. I could only dream every time would be like that from there on out. Warning: The following may be too graphic for some. When I woke him with my kisses, he ran his hand down my torso until he noticed my morning excitement. He grabbed hold and squeezed, expressing his delight in his discovery. He pulled the sheets down, followed shortly by my boxer briefs. As his head bobbed up and down between my legs, I let out moans of pleasure. What a way to wake up!

Apparently, neither of us got enough the night before. We were both still excited about how amazing it was. It made me excited and hard just thinking about it. We both wanted a sequel.

He climbed on top of me, and we began passionately kissing. Of course, things escalated from there. It wasn’t long before I had him on his back, and I was deep inside him. The sex was great that morning. It wasn’t quite like the epic romp we had the night before, but it was great. We flipped, and he had his way with me.

When we finished, while we laid in the bed together, he took hold of my head and said, “[O.G.A.A.T.], I love you.” Even though I suspected it was coming, nothing could have prepared me for that moment. No man had ever told me they loved me before. I knew he meant it. I stared deep into his eyes — Deep into the eyes of the man I loved too. “I love you too, Babe,” I added. We hugged strongly and kissed passionately. It was an incredible moment, and I began to cry a little. He reacted by comforting me. I think he was a little panicked. He didn’t know how to deal with that, but that didn’t really matter. We were in love. That was all that mattered.

Because of this and the sex, we were very late for our plans to meet P on the pier. When showered up, ate something and packed our bags for the pier. P was there waiting for us when we arrived. We apologized for being delayed and hinted at the reason. She gave a giddy laugh and scolded us.

P and CK decided to hit up one of the food trucks/ice cream trucks after a while. They came back with all sorts of things and an ice cream sandwich for me. While they were gone, I played with P’s dog, Baby, and I texted the rest of my friends to see who was up for a day on the pier. A few responded explaining they’d be on their way shortly.

I told the other two everyone’s whereabouts and plans. CK asked about my sister, but I told him she hadn’t responded to my text. He was very concerned with her perception of him. They’d only met for a short while at the Hoboken Arts and Music Festival a few weeks earlier. Even when prompted, she still had no opinion. This worried him.

After some time, my friend G joined us. I also got ahold of D and his girlfriend. They were in the city for brunch, but they would join us on their way back home.

CK and I decided we wanted to have some refreshing cocktails to go with our small picnic of snacks. Just as D and his girlfriend were arriving, we made our way to the liquor store to get some prosecco. I had a great idea to mix this with a few flavors from Rita’s Italian Ice.

While we walked, CK and I discussed him meeting my parents. They were coming into the city in early June for a Broadway show and dinner. I wanted him to meet them. I invited him to the dinner a few days earlier. I explained to him my sister’s reaction to his invitation, as well as my parents. My parents had no issue, but my sister thought it was too soon. In telling CK this, I realized I made a big mistake. He immediately expressed to me, “OKAY! Now, I’m definitely not coming!”

“WHAT!?” I protested. I was not happy with that. I was very excited for him to finally meet my parents. I’d met his mother, and it went swimmingly. On top of this, he meant a lot to me. I wanted my parents to know this. They’d never met any of the guys I’d dated in the past. In my protest and explanation, I think I was able to bring him back around.

We grabbed two bottles of prosecco and made our way to Ritas. We got watermelon and mango peach ice to mix with the prosecco. We planned to make refreshing summer drinks for all.

As we walked back to the pier, he still didn’t give up on the fact my sister wasn’t joining us. He was harassing me to invite her, but because of her snarky email telling me I shouldn’t invite my boyfriend to dinner, on top of other things, I was annoyed with her. Then I checked my phone when I went to invite her and realized I’d already done so when I reached out to the others. She didn’t respond. I told CK this, and his guilt was alleviated.

When we got back, we shared our drinks with everyone in improvised vessels since we forgot to get cups. Everyone was talking and having fun. CK was fitting in nicely. I loved seeing him with my friends and how he interacted with them. He passed my friend test swimmingly. I care a lot about them, and if he could’t hang with them, it wouldn’t last. He was able to hold his own and impressed me to no end.

When the sun was going down, everyone was ready to head home, including CK and I. We made our way back to my apartment, telling each other how much we loved each other along the way.

We decided to plant ourselves on the couch and watch Immortals for the evening. We ate dinner and cuddled on the couch until it was time to head back into the city to his place. We didn’t plan for him to stay over. It was very late, but he had nothing for work the next day. Since he was close to my office it only made sense to spend the night there.

We got to his apartment and got ready for bed immediately. I brushed my teeth and climbed in between the sheets. It wasn’t long before I dozed off, but I was thrilled to be in his arms. I never got tired of sleeping with him, and hopefully, there would be infinite nights in the future we spent the same way.

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Sexual Exploration

Today is another Fast Forward Friday!!!  

Hope you are enjoying these. It will help bring the blog a little closer to real-time. If you’re keeping up with the stories chronologically, please skip down to this morning’s post first, then read this one. I think it’s a good one! Enjoy!

Back to your special edition of One Gay At A Time…

Friday afternoon, I was talking to J, one of my closest friends. We swam together in college, and I can actually say I think we’ve grown closer with each other now than we were back then. He’s a great guy and I cherish our friendship!

I recently had the pleasure of attending his wedding, but before that, we had a little chat:

He asked if I wanted to see what he bought his future wife for their honeymoon. Before he sent me a link to The We Vibe, vibrator for couples to use together, he included my typical warning message: WARNING: The following post may be too graphic for some. I thought this was hysterical, and I was proud of his level of comfort in regards to his sexuality. Apparently, he’d been dying to say that to me for some time. From there, a whole new conversation spawned.

He told me of his extensive toy bag. When I told him I owned none myself, he responded, “DUDE! You gotta get toys!” I really never saw a need for these. I was enjoying the “toy” God gave to every man I brought into my bed.

Then the conversation took a turn. “Ahhhhh, perfect time for me to ask you opinion…” he said sending me this link: aneros.com. It was to a prostate massager for men to hit their G-spot. “Thoughts?” he added. My head immediately went to the Tickle My Tush book I’d received months earlier for review. I told him to remind me the next time he was in Hoboken, I’d lend it to him. He told me, “Been looking at the Aeneros. Clearly for me, but I’m butt hesitant.”

I was proud of him for even considering the idea. The butt is a region many straight men fail to explore because it is seen as taboo. It is an entirely new erogenous zone that should be explored, even by heterosexual couples.

They’d explored this idea in the past. She was comfortable, but he wasn’t. “It’s not a gay thing — Just uncomfortable,” he typed. I told him not to be hesitant, but I also encouraged him to explore alone before engaging his future wife.

I explained to him how I’d never really explored back there myself before coming out. Of course I’d used a finger in the bathtub to see how it felt, but I could never get over the uncomfortable sensation. I never derived pleasure from that region, with the exception of oral pleasure. “I don’t really get off from traditional penetration,” I told him. “It gives me nothing. But… I have had great experience with a finger… It can be more directional and targeting, and I have gotten off from that fairly often”

He told me, “See, we tried finger like years ago — Freaked me out… Didn’t/couldn’t relax. Haven’t tried it since” I immediately added, “You need to get comfortable yourself alone first. Then, you’ll be more relaxed.”

Somehow we got sidetracked, and we began exchanging thoughts on different brands of lube. I’ve always used water-based because I care more about my sheets and don’t want stains. He suggested using a towel and explained how much better silicone is. He even went into the chemistry of it (which is his background). I knew why he liked silicone better, but when he would be on the receiving end of silicone, he might not have the same feelings about it after learning of its lingering effects.

Soon, we were back on track. I asked him if he had a tub. I explained: “Some day… take a bath…  warm water… and relax. Lay back in shallow water with your back on the bottom of the tub, legs up on the brim. Gently penetrate with your. It takes A LOT of getting used to. You need to feel like your pushing out to allow things to gently come in. You’re going to feel like your going to sh*t yourself… You probably won’t. It’s a natural urge you need to combat. It’s def. awkward — No question about it. It’s just a matter of getting to know a part of your body you’re not used to engaging.” I told him the book I was lending him would talk all about it.

He responded, “Fair enough. Makes sense too.” I told him I would bring the book to his wedding in a week. He asked if I could please wrap it up before doing so. I joked at the idea of simply putting it in the box of cards in hopes his mother was the first to get to that. He added, “I appreciate this. You have a hell of a lot more experience than I do.’’ I replied, “Yes and no.” I reminded him how I was never really a bottom, but I was certainly exploring that a lot more in my current relationship. “Clark Kent and I have a very healthy flip relationship,” I supplemented.

He retorted humorously, “Didn’t say you were an expert (I do read you blog), but you know a hell of a lot more than I do.

I thought back to my first time. “It was very different and awkward. It took a lot of getting used to. And, when someone told me about the push thing, it got a lot better. And, then when I read it in the Tickle My Tush book, it confirmed that for me. She describes it very well,” I detailed.

“You know this is goin’ in the blog right?” I asked. “It won’t say J — Just a male friend. But, I’m very proud of you!” He responded, “Hmmmmm. Go for it. This is J. You don’t have to keep it anonymous. I’m not scared. I don’t mind. Just give me a heads up right beforehand. A healthy sexual appetite and willingness to explore are healthy things.”

“But again… I’m very proud of your willingness to explore without worrying about social connotations. This is definitely a longer conversation I want to share sometime,” I added. We agreed to revisit this topic again when we both had more time…

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Superman Returns

Sunday, I made plans with my Superman — My Clark Kent. I was very excited and could hardly wait.

I barely knew him, but I could already tell we were quite a match. On top of that, we weren’t even done the first date before he planned to see me again. It was his suggestion for us to catch The Hunger Games Saturday morning while we had breakfast.

I texted him and invited him to come over to Hoboken. We would take the motorcycle out for a ride before the movie. I ran a lot of errands that morning in anticipation of his arrival later in the afternoon. As the day progressed, the weather looked like it would cooperate less and less. The sky was covered with clouds and the wind picked up significantly. It looked like it would rain any minute.

I texted CK and suggested we hold off on the ride, and I just come into the city to see the movie. It would make things less complicated, and it would give him something to look forward to in the future.

He agreed with the new plan. I met him at his apartment with plenty of time to catch the movie. He suggested we hit up the rooftop since I didn’t get to see it the first time I was there. How could I say no to that? When I got to his apartment, we went directly up to the roof. We spent time checking out the sights, cuddling and taking pictures like we’ve been a couple for a year already. I was crushing hard!

We sat and talked, and he suggested we catch a later showing so we could relax and not have to rush to the theater. I wasn’t going to object to anything at this point. I was so happy. I was just going to go with the flow.

We finally made our way to the theater. He insisted on buying my ticket. I protested since there was no reason I couldn’t pay for myself, but he continued to insist. He wanted this to be his treat. I relented, but was sure to pick up the tab for the pretzel bites and soda.

We made our way into the theater and got great seats. Almost immediately, the PDA began between us. It wasn’t gag yourself PDA. We were simply holding hands or caressing each other’s arms. It was my kind of PDA. I was quite enjoying myself!

When the movie was over, we made our way to the street and discussed the film while we walked. This was his second time seeing the movie. He expressed interest in reading the book, and I strongly encourage him to. I was already part of the way through the second book in the series of three.

We held hands while we walked and at times put our arms around each other. I could hear a lot of people making comments, and some even began to shout or hoot and holler at us. A few of the comments were jeers and a few were shouts of support. This was not something I was used to, but it was something I would have to learn to shrug off. I’d walked through the city being affectionate with other guys before, but it never gathered this type of reaction. At one point, CK acknowledged the comments, asking, “Are they still honking at us?” I told him I thought so, and we kept walking. Frankly, I was a little surprised by it all. We were in midtown west — Smack dab between Chelsea and HK, two of the gayest neighborhoods in NYC. I had a feeling a lot of the commenters were out-of-towners, and many of them were young guys.

When we got away from the crowds, he commented how he liked how I was into the hand holding. “Not all guys are into it. I’m glad you like it,” he added. I told him I liked little signs of affection, but I wasn’t into the far more obvious public displays. I told him I’m not much for making out in public.

He also mentioned the idea that had we planned better, I could have brought clothes to wear to work the next day and spent the night, however, he was happy we weren’t taking things for granted. He was happy with the pace of things, even though he wouldn’t have been opposed to sharing his bed with me.

We stopped by Pinkberry on the way back to his rooftop as per his request. We ordered ice cream and shared spoonfuls with each other as we walked up the street. When we got back to his place, we headed straight to the roof.

We laid on one of the outdoor couches together and got comfortable while we ate our ice cream. We talked for a while before we ended up making out. Things stepped up to the next level when he undid my belt and began orally pleasuring me with one eye on the door. It was risky but I wasn’t fully exposed. I liked his passion and excitement. I’d finally met my match in terms of a decent, normal guy with a healthy sexual appetite.

After some time, he asked, “You wanna continue this downstairs in my apartment?” I told him I was totally game, and we descended the stairs.

Warning: The following may be too graphic for some. It wasn’t long before we were both naked in his bed. There was significant foreplay before he asked if I wanted to penetrate him. I was completely engulfed in our passionate romp and nodded my head in definitive agreement. “Yes! Like no other!” I added.

Then, I’m not sure how things switched so quickly, but as I was grinding on his backside, and stopped to put on a condom, he turned to me and said, “Can I f*ck you?” A long time ago, I made a rule for myself I would not bottom for a guy unless we were in a relationship. It wasn’t something I really enjoyed, so only special guys would receive the privilege. I had very strong feelings for him. I wanted to share something special with him already. I could hear A’s voice in my head telling me no sex until the third date, but that voice in my head was no comparison to the passion of my other head. After all that thinking, I said, “Yes.”

Like that, he started making out with me, and he had me on my back. While we were making out, I set the open condom down on the bed. He was already putting it on. I thought he was going to top me after I topped him. I didn’t realize I was giving up my position first. I was a little disappointed, but I let it happen anyway.

I told him it was a very long time for me since any guy had been inside me. I told him he’d have to go VERY slow. He began to slide in when I gripped his leg and implored him to stop. He told me to relax and just hold it there, but I insisted he pull out. I needed a break before we could continue. I know he thought it would be better if he simply held it there, but I was being painfully stretched. He wasn’t exactly a small guy — Quite the opposite. He pulled out, and I could see the disappointment on his face. He thought that was it, but I wasn’t giving up that easily. I just needed a second to relax again. He began kissing me in a caring way. It was as if it was his way of saying, “I never want to hurt you again.” When I regain composure, I directed him to begin again. Delight spread across his face at this news.

This time was much easier. He slid in with no problem, and began gyrating. It’d been some time since my prostate was stimulated like that, so part of it was discomfort and part was unexplainable pleasure. I never finish from bottoming, but I always have a full-body experience. I rarely can walk afterwards — Not because I’m so sore but more so because my legs go limp.

He continued until he was close, pulled out, ripped off the condom and shot all over my chest. It was very hot to watch him explode with gratification. He expressed how great everything felt, and we both laid there incapacitated. He told me how awesome he thought it was that I would flip so readily and let him top me. I told him I thought it was the best way for any healthy relationship. Both partners get to experience it all. Even though I didn’t always enjoy bottoming, I found it to be the ideal situation.

We cuddled for hours after that. We even dozed off for a period. When I woke, it was two am. I checked the schedule for the next PATH and made sure I was on it at 2:30. I said goodbye to him with a very passionate kiss, and we talked about when we’d get to see each other next. It was clear I couldn’t get enough of him. Now, the question was, did he feel the same way about me?

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