The following topic of conversation is very embarrassing and very personal. It’s not easy to talk about, but I have a strong feeling I am not the only one who suffers from the issue. Warning: It may make some of you uncomfortable. I am exposing myself in this post, but I feel I need to face my demons to be able to get over them. I also feel guilty writing about this, because it’s a bit of an invasion of privacy for others, but I also feel it’s necessary if I’m being honest with myself and this blog. I wonder if someone out there may have insight to help me and others with this predicament. I feel the need to shine a light on this issue, as no one is talking about it.
My intentions were obvious this time around with Smiles. My hand was down his pants fondling him until I was pushed away with a grunt. There was no misconstruing my intentions. After being denied sex yet again by Smiles, I felt the need to consult my council.
I called Boston for his take on the situation. I explained being denied sex on more than one occasion. His immediate response was, “Oooooo. That’s not good. Something isn’t right.”
I responded, “I know, right? I just wanted to make sure I wasn’t making a mountain out of a mole hill.”
We chatted about the issue, and he told me I needed to address the issue. “Sex is an important part of any relationship, and based on what I read in your blog, sex is important to you,” he added. We discussed the best way to bring it up. The main consensus was waiting until the relevant situation arose. He suggested I don’t bring it up over dinner. If I was denied again, I should bring it up immediately to find the root of the problem.
This was the point in the conversation where I made a small confession of my own. I was worried I may have been to blame for the quantity. I explained my climaxing issue to Boston for the first time in full detail. I told him, while I’d been with Smiles a few times, I had yet to climax. This was through no fault of Smiles. This was a common occurrence for me dating back to the days I was with Broadway. In fact, I feel it was a large part of the reason we broke up. It put a lot of strain on the relationship. He took it personally, even though I assured him it had nothing to do with him. I was still quite attracted to him and still received pleasure from sex, but I wasn’t finishing.
I never was able to find the root of my problem. For a while, I hoped it would fix itself. When it didn’t I explored a number of theories. The leading one being I hardwired my brain to function in a specific way in relation to sex.
For 16+ years, my main outlet for my sexual frustrations was viewing gay porn and pleasuring myself. I wasn’t dating men, and I wasn’t exactly a lady killer either. I would go home, open the laptop, and take care of myself. I worried my brain was hardwired to react only to that stimuli.
I wanted nothing more than to “fix” this issue. For some time, I masked it by prepping myself. If I knew Broadway and I would be having sex, I watched porn before I saw him to build up a “spank bank.” I referred to this when he got me close to finishing to get me over that last hill. It worked for some time, but eventually that solution lost its effectiveness. That’s when things got really bad. I got so stressed about it, when the moment came, there was nothing I could do but think about my lack of performance. I was so wrapped up in the issue, there was no unwinding me at that point.
I had many frank discussions with Broadway on the subject. After discussing it, we agreed not to talk about the issue for some time. It was the only way I was going to be able to relieve some of the pressure I was putting on myself. Eventually it did the trick, and I had my happy ending. However, it wasn’t a 100% solution. Most of the time, I was only able to cum after he performed oral sex. A majority of our relationship, I never climax from anal penetration. The issue was still there. It was just lessened.
It wasn’t as big an issue with San Francisco because we were an entire country apart. When I was physically with him out in San Francisco, I had no issue. When we Skyped, it took slightly longer, but eventually I climaxed. After San Francisco, I slept with a handful of guys. I specifically remember it being an issue with The Trainer. I know it’s not an issue of physical attraction, because he had a body like a god! However, I had to finish myself off that time, and it took some time.
When I was dating N, it took a long time, but I almost always finished. He started noticing my “condition” as time went on. We discussed it lightly, but I think he was under the impression it just took me a little longer than most guys to finish. As I’ve said before, I had to resort to my “spank bank.” Many times, what I was imagining involved the two of us. I wasn’t even imagining porn stars. It was the two of us in different scenario/locations other than in my bed.
Over the summer, it wasn’t really and issue for me. I had no strong connection to the guys I was sleeping with. It was purely recreation and my own need to get some crazy out of my system. I had no pressure or image to keep up. I was just having fun, and it worked.
The first time Smiles and I had sex, I bottomed. No matter who I have been with, I have never finished from bottoming. It has its pleasures, but it never had that effect on me — Hence my status as a preferred top. With Smiles, there was one time when I was very close during oral sex. I was right there, but I just couldn’t close that final gap. After we had sex other times, and I still didn’t finish, I began to morph my theory.
I have a very high pain threshold. Because of this, I wonder if I am in turn cursed with a high pleasure threshold. Maybe it takes more to get me off. I also wondered if my stimulation comes from something more visual. Maybe I need to witness the penetration to climax. Again, these are all just shots in the dark, no pun intended, but I want nothing more than to figure out this enigma. However, I haven’t been able to test my theory at this point.
Smiles expressed his interest early on to work with me to figure this out. It meant a great deal to hear him verbalize this to me. I need someone who can be understanding and patient with me if I’m going to lick this thing.
After I talked to Boston, after a drunk night at the bar, I discussed in length with D my issue. This was really tough for me because I am so embarrassed by the situation. It makes me feel like less of a man. He was helpful in our discussion and helped me feel more comfortable talking about it.
I also called to Broadway. I didn’t exactly feel comfortable talking to him about the details of my new relationship, nor did I think it was fair to him. But, he had experience with this issue. He knew what was going on with me, and maybe now that we weren’t together, he could help me find the key. When I told him I was being denied sex, he immediately said, “Something’s wrong! That’s not normal. You need to talk to him about it.” Everyone was telling me what I already knew, but not what I wanted to hear. In thinking I was partially responsible for the situation, I brought up my issue. Maybe he was avoiding sex with me because I couldn’t finish.
Broadway told me I needed to stop being so stupid about it. I was stressing myself out over it, and that wasn’t going to solve anything. I needed to acknowledge to myself the issue and go see someone about it. I told him I had been entertaining the idea of going to see a therapist, but it takes a very special type of therapist for such a sensitive issue. It wasn’t exactly the easiest thing to find in the yellowpages. He again just indicated I needed to talk to someone about it if I wanted to get over it. He also reminded me I needed to talk to Smiles directly about why we weren’t having sex more often.
The next morning when I woke, I sent Smiles a message detailing my desire for him to be in the bed next to me and how horny I was. He responded positively and seemed he would have been up for morning sex had he actually been there. I was surprised considering a few hours earlier I was denied.
We made plans for Sunday, and I went on with my pondering my issue for the rest of the day. Did he think I didn’t enjoy sex? That certainly isn’t the case. Even if I don’t finish, I still thoroughly enjoy sex and still get a body high from it. Did it bruise his ego to know I wasn’t being fully stimulated by him? I can assure him, it is me, not him. There were a million questions, but no solid answers.
One thing is clear. I need help. I cannot solve this problem on my own, but maybe talking about it with my therapist, Dr. WordPress, will help me face my demons head on and conquer them. Only time will tell…
On Thursday afternoon, I made plans with Smiles to go out with him Friday night. We planned to grab dinner and then go out the bars for a night on the town finally. However, that plan would have to be postponed.
Thursday night, he sent me a text explaining he forgot he had dinner plans in Brooklyn and then a birthday gathering in the West Village. He quasi invited me, but added, “That’s probably not exactly what you meant when you said night out on the town,” he added.
I suggested we simply postpone our plans one night. It was still relatively early in our relationship, so some space can sometimes help. I didn’t want him to get tired of me. I would use the time to go out with my friends since I was spending many of my weekends with Smiles or traveling.
Friday, I went out in Hoboken with my friends. He texted me to tell me he got a new phone. I was thrilled to know he was thinking of me even though I wasn’t with him (Or, at least that is what was going through my head as I read it).
Saturday morning, I woke and was feeling very productive. For quite some time, I wanted to trek down to the Financial District to check out the Occupy Wall Street movement in Zuccotti Park. I wanted to take the nice camera from work with me to snap some cool shots of the protestors. I didn’t want to do this alone. It was something Smiles and I discussed many times. I tried texting him and then eventually called him to see if he would join me. He was doing work, so he wouldn’t be able to join me until later in the day.
Since I knew he was by his phone now, I sent him a sexy picture of myself from the summer with the caption, “Wanted you to have a sexy picture for your new phone.” He responded, “Haha. Love it!”
I tried a few of my other friends to see if they’d tag along, including LES. After much convincing, I was able to get him to join me, but under one condition. I had to come by his place to smoke first. I agreed and also proposed we use up my Groupon that was expiring that day.
When I finally got to LES’s place, we smoked and got on our way downtown in a cab. The sun was setting quickly, so I proposed we just grab something quick for lunch instead of using the Groupon.
We got downtown to the Occupy movement, and we began exploring. I took many pictures and was even approached by an editor from The Suit Magazine asking me to send her some of my shots. She was looking for pictures to use in an article.
After we had our fill of protestors, we made our way to Wall Street. While walking, LES said to me, “So what’s the deal with this other guy? How old is he? What does he do?” I knew exactly what that question was. I interpreted it to mean, “What does this guy have that I don’t? What makes him so special.” It was an awkward moment, but it was bound to come up at some point. I really liked Smiles, but I also really enjoyed LES’s friendship. I didn’t want to create too many waves or hurt anyone’s feelings. When we got to Wall Street, we found they were filming Batman, and we wanted to check it out. By the time we got there, they were cleaning up the “set.”
As I was walking LES home, Smiles called. He finished work and was ready for dinner. I wanted to go home, shower, change and drop off the camera before we went out. I told him I would meet him for dinner later, and we made plans. I felt very guilty having that phone call with LES walking next to me.
After I cleaned up and changed, I met Smiles in Chelsea for dinner. We had no location picked out, and ended settling on Elmo for dinner. Conversation during dinner was great. He had a very productive work day, and I feel he let me in even more. He was opening up more and more every time I saw him. We were finally peeling back the layers of that onion.
After dinner, he proposed we go over to Barracuda. I’d never been and have always been leery of it. I’m not a fan of gay bars. They make me uncomfortable.
When we arrived, I learned he knew two of the bartenders. I had met them before as well. They were both very good-looking and pretty unforgettable. They were at Smiles’ birthday gathering. Barracuda wasn’t anything like what I expected. I was expecting a flashy club like seen, not a dive bar. I immediately felt more comfortable.
That is until a tall overly friendly black man came up behind me and started feeling up my chest with his arms around me. He was a feisty one, and I wasn’t interested. I made that pretty clear by my extremely uncomfortable facial expression. Smiles on the other hand was playing ball. I assumed it was a friend of his, until I learned he never met the guy before. This was just Smiles being his charming self.
Because I wasn’t completely comfortable, I drank a little more excessively than I should have. On top of that, Smiles’ ex arrived. I had no problem meeting him and talking to him, but I did have a problem when Smiles said to me, “I hope you don’t mind, but I’m going to steal away with [him] for a minute. I haven’t seen him in a while, and I need to chat about some things.” Based on the interaction, I wasn’t worried that he was going to do something with his ex. I was more annoyed I was being ignored in a place I’d never been before where I wasn’t completely comfortable and knew no one else.
I entertained myself by watching the bartenders cutting off the tall black man because he was being obnoxious to everyone at the bar. However, for me, the drinking continued — In excess! I drank so much, the bartender started giving me free drinks. I drank my face off. I was hurt and p*ssed. This little chat went on for a long time. There was some flirting and maybe Smiles wasn’t 100% over him, but I was okay with that. It’s natural. I wasn’t okay with being ignored! When the conversation ended, Smiles said to me, “How come you’re so quiet?” What the hell was I supposed to say to that? — “I’m quiet because you just ignored me for the past half hour?”
Next thing I know, when I woke up in his bed, the first thing I noticed was I was naked. I never sleep naked. The second thing I noticed was some lube on my backside. I couldn’t for the life of me remember anything about the night before. I don’t remember much after that. I don’t remember getting my coat from coat check. I don’t know how we got back to his apartment. I don’t remember climbing into bed.
I racked my brain to remember anything from the night before. The only thing I could conjure up was a flash of about ten seconds of sex with him on top of me. It was a very scary feeling! I’d blacked out before, but never have I blacked out sex. I was the only one ordering my drinks all night, but I couldn’t 100% rule out the possibility someone roofied one of my drinks.
I never mentioned to Smiles my panicky thoughts. There is no chance in hell Smiles would have done that to me, so I wasn’t worried in that respect. I knew he would never take advantage of me. I was probably pretty lucid in my drunken state, if previous history has anything to say. I was worried I may have done something to embarrass myself. I decided to play it cool and pay close attention to how the rest of the morning progressed…
In unrelated news, I came across this video from my fellow blogger, http://www.ty-curious.com/. He shared it with me, and I think it’s spectacular. Totally safe for work! Hope you like it! Take the time to check out his blog too. Great guy!
He described his drunken night involving too much Patron and a lost iPhone. He hadn’t had a chance to track it down, so I offered my assistance to make some phone calls for him. He was grateful, but had it under control. While he described his night, I described my time out in the sticks with no power or technology. “Yeah… It was a real Amish paradise,” I said.
Once again, I had to facilitate plans with him. He typed, “Okay. Off to go get food. I’m starved.” I quickly replied, “What are you doing later?” I knew it would be difficult getting ahold of him the second he signed off for the day. It’d been a while since I’d seen him, and I was anxious to do so. “No plans, although I may go back to the bar tonight for a Halloween thing,” he declared. I wish he had the same desire to see me to invite me without provocation, but I’ll take what I can get. “Wanna try to get together later?” I asked.
“Jump on the bike and come over and have brunch with me,” he finally stated. I explained the bike was snowed in with a dead battery, but I told him I’d meet him for brunch. I quickly made my way into the city to meet him at the Christopher Street PATH station. I arrived well before him and waited for him to show. I couldn’t call to find out what was keeping him, so I tried to occupy myself with my phone.
When he finally arrived, I wasn’t greeted with a kiss. I could have initiated the situation myself, but again, I was still in the mindset to play a little hard-to-get. We walked to a nice brunch spot neither of us have tried before, Barbuto. It was great. We got a nice seat next to the kitchen, which in most situations is a bad thing, but in this case, was entertaining.
Smiles ordered a beer after wavering between that and a bloody mary to help cure his hangover, and I ordered a glass of red wine. We took the time waiting for the food to arrive to catch up with each other. He was a little quiet, but I had plenty of stories to tell from my time home. We talked a bit about his family as well, and I started to get a better picture of the dynamic going on there.
Our food arrived, and we were both very pleased with the results. After we paid our tab, we decided to walk around a bit since the weather was so gorgeous. We walked to Doma Coffee Shop to grab coffees while we walked around. We had no plan for our day. After we grabbed caffeine, he turned to me and asked what I wanted to do. I told him I was just happy to be out, and it didn’t matter to me what we did. We started to walk around aimlessly. When we came upon Pleasure Chest sex shop, he suggested we pop in. This wasn’t the first time walking into a sex shop with him. I was game.
We looked at all the toys in the place and even asked one of the workers there to explain one of the feminine toys to us. We had more than a few laughs as we perused the store.
We spent the rest of the afternoon walking around SoHo looking for hats to replace the one he lost. I was happy to spend the day with him. We did some shopping for other things while we searched for hats. While I was checking out to pay for the flannel shirt I picked up, I could see in his eyes he was exhausted. He was fading fast. He suggested we go back to his place to take a nap. I myself wasn’t feeling very sleepy, but I rather liked the idea of napping with him.
We got back to his place and climbed into bed. I put on my new flannel and got comfortable. Surprisingly, I passed out rather quickly. He, on the other hand had a hard time falling asleep.
Warning: The following may be too graphic for some. After about an hour, we were both awake. He turned to face away from me, so I decided to make a move. I engulfed him in my arms and spooned with him. After some time passed, I gently began caressing him all over and slid my hand between his thighs. I began massaging him until he turned his head back to kiss me. It was on — FINALLY! Things only got more passionate from there. It wasn’t long before he pulled out a condom, put it on me, and climbed on top. I was finally getting my turn as top dog (even though I was on the bottom). The sex was good, and I enjoyed having sex facing him with the lights on. However, once again, he finished, and I wasn’t able to.
Embarrassment came flooding in. I was very attracted to him, and I enjoyed the sex, but something underlying wasn’t allowing me to relax and fully enjoy the moment. I was very close, but I just couldn’t get over that last hump (no pun intended). This wasn’t the first time this happened, but it certainly didn’t make it any easier to deal with.
After sex, we both showered and cleaned up. He had plans to meet friends at his favorite restaurant to say goodbye to a bartender friend who was leaving for another restaurant. I was a little curious why he didn’t extend an invitation, but I didn’t want to dwell on it. We made some progress, and I wanted to concentrate on the positive. I was doing my best to play hard-to-get, but I really liked him. I wanted this to continue. I wanted to get to know him more. I wanted to be closer to him physically. I wanted him.
We got dressed and walked towards the PATH and Extra Virgin, where he was headed. When we reached a crossroads, we said goodbye with a quick kiss and went on our separate ways.
Later that night, I got a message from him complaining about having to go to the bar to see if his phone was found. I sympathized with him and wished him luck.
When he got back from the bar, he messaged again to tell me he had no luck. I felt bad for him, but selfishly, all I could think about was how hard it was going to be to get ahold of him without a phone. The next couple of days would pose an interesting challenge.
After breakfast at the hotel, we got back on the road to my great-aunt’s house in Mount Vernon to drop off the keys and make our way home. It was surprisingly fast.
I was really disappointed I never got to chat much with the bride. It’d been years since I’d last seen her, and we only speak on the phone about once every four or five months.
During the whole ride, I had a lot of time to think. For me, this is deadly. When I have time to think, I crawl up into my own head and start digging around where I shouldn’t be digging — This is why I lead such an active lifestyle. Thinking depresses me.
A lot of thoughts about Smiles were going through my head. I was a little hurt and upset my advances were rejected in the morning. I also was very disappointed I didn’t get to grab brunch with him. Overall, I guess you could technically deem the weekend with him a success, but I still wasn’t thrilled. I was on unstable ground. I had no idea where I stood with him, and it was getting to me. As usual, I was over-thinking everything.
When we got back to Hoboken, we stopped at the grocery store. I decided to call Smiles to see if he wanted to come over that night. I wanted to make him a nice home-cooked meal since he never cooks for himself. We always go out for dinner or order take-out. He agreed to come by. I also had ulterior motives. I wanted make-up sex for Saturday morning when I was denied.
That evening, when he got off the PATH, I hopped on the motorcycle and rode down to pick him up. I was happy to finally get him out on the bike. He’d been on one before, so it wasn’t as exciting as the first time I’d taken motorcycle virgins on the bike, but it was nice to have him so close to me. We rode back to my apartment with his arms tightly around me. I thoroughly enjoyed it.
I started us off with some artichokes while the fillets finished grilling and the rest of the meal finished cooking. I made more food than the two of us could possibly finish. When we had our fill, I cleaned up, and we made our way to my bedroom for the night. He asked if he’d be spending the night. “Of course you’re spending the night! Did you think I was going to kick you out now?” I responded. “I don’t know. Some people need their rest before Monday morning,” he said. I reminded him the size of the California king bed and assured him he wouldn’t disturb my slumber. If anything, he would enhance it.
Warning: The following may be too graphic for some. I started getting frisky. After not getting any the morning before, I was even more geared up for some great sex. We undressed each other and jockeyed for position once again. I wasn’t making the same mistake again. I made sure I was in position to top this time. When I pulled out my night-stand drawer to get a condom and some lube, he made a comment about the large dinner and not sure it was a good idea. I surrendered, and we decided to use alternate methods. He climbed on top and used his hand behind his back. I was impressed with his ingenuity and his willingness to try alternate methods. However, it wasn’t quite enough for me. It felt great, but I couldn’t quite get over the final hump, as is my issue often.
We stopped and just enjoyed each other’s bodies laying next to each other before we both cleaned up and hopped into bed.
When I woke in the morning, I snuck quietly into my bathroom to shower so he could fall back asleep. If he wanted, I was going to let him sleep as long as he wished and just pull the door shut behind him. However, he had a few things he wanted to get to Monday morning, so he joined me on my morning commute.
We casually walked to the PATH and hopped on. When the time came for him to get off, we exchanged a quick kiss. A lot was going through my mind before that. I was a little afraid to do it because I knew all eyes would be on me as soon as he got off. However, I was the one who initiated it. It was subconscious, but I wasn’t going to let fear of others’ reactions rule my actions anymore. I didn’t care who knew I was gay anymore.
I rode the rest of the way to work not making eye contact with others. I wasn’t 100% comfortable in my own skin, but I was still growing with every day. Things were progressing nicely with Smiles, and they could only get better with added confidence.
Things were finally starting to look up for me. I met Sexy Eyes for coffee, and we really hit it off. On top of that, I spent the night in his bed. The compatibility was there on both the emotional and the physical. We both shared active lifestyles and had a lot in common. I was really enjoying the idea of dating him. He seemed like a great guy. Aside from Sexy Eyes, Smiles also showed an interest in continuing to get to know me. We only met for a short period of time over a drink, but he was willing to take more time to learn more about me.
Even though I saw Sexy Eyes twice that Thursday, they were both unplanned dates. We had a planned date that Friday, and I saw no reason to cancel it.
I spoke to him throughout the day to make sure we were still on. He had volleyball again that evening. He invited me to join. In fact, he strongly encouraged me to do it. It was open gym play, and he wanted to play with me. I was very intimidated because he had been playing the better portion of his life. I’m good, but I’m completely amateur. I’ve never had any formal training and have only played recreationally. That doesn’t go to say I wouldn’t play with him in the future, but I wasn’t thrilled with the idea of jumping into that just yet. I’d only just met him (I say that as I am now thinking in my head about how we already had sex).
After work, I went home and relaxed for a bit. He was occupied until about 10:00, so I watched some TV until it was time to shower and get ready. I hopped on a bus into the city to meet him for dinner and was running a little late. I thought since I was late he’d be ready by the time I got into the city. That wasn’t the case. When I texted him to tell him I was at Port Authority, he told me to come up to his apartment until he finished getting ready. I walked up to his apartment and arrived just as he was finishing up.
He answered the door, and we exchanged a kiss. He pulled back quickly and scolded me for not having a close enough shave. I get irritated if I shave every day, and that day was an off day. He complained about his face being sensitive and fear of breaking out. I partially understood, but a larger part of me recognized he was just being a prima donna.
I sat casually on the couch which he finished up. I felt very relaxed and comfortable with him. I was constantly joking with him and making witty comments. It was fun verbally sparring with him. That is alway something I enjoy.
Finally, it was time to go to dinner. We talked about the different options since it was already 11:30. I defaulted to him since it was his neighborhood, and I didn’t even know what would be open at that hour.
We ended up at the Renaissance Diner in Hell’s Kitchen. We sat outside the restaurant and chatted while we waited for our food.
I noticed a trend with him. Every time we had a conversation, it was monopolized by him. He was interesting to listen to, but he was also 75% of the conversation. It wasn’t easy to get a word in edgewise. The conversation was also heavily interrupted by the judgmental comments he made at every passerby. If he wasn’t ripping their outfit to shreds or looking indignant because someone glanced at him, he was ripping apart their walk or the way they looked. He was being entirely over judgmental, and it didn’t look good on him. He even made a comment about how I dress “straight.” He informed me my polo was a bit too loose. “You have a nice body. You should show it off more with a tighter shirt,” he noted. I thought my shirt was actually quite small, and I had no interest in dressing “gayer.”
The meal drug on for some time. It was getting late, and I either needed to go home following dinner, or I needed to get up early the next morning because I was going back to my college for alumni weekend. Finally, after dinner and the endless cup of tea he ordered, we got the check and walked back to his place.
When he told me to get comfortable and ready for bed, I determined I was spending the night. We hopped into bed under the covers, each in our underwear, and turned out the lights. We started kissing and cuddling until he pulled me over and rolled me on top of him.
At that moment, he informed me “tonight it’s your turn,” meaning, I was going to bottom for him since he bottomed for me the previous night. I made a hard stance and informed him that would not be happening. I told him I don’t do that just for anyone, and I have to be dating a guy for some time before I’m going to give that up (since I really get nothing out of it on my end).
He was NOT a happy camper. He even got out his phone to go over the semantics of what I originally said on the subject. Apparently, in a text, I said, “I only bottom for a guy I’m dating.” I guess in his mind, after coffee and two dates, we were dating — Not the case with me.
He started to pout and was getting very combative and confrontational because I wouldn’t bottom for him. “Whatever. It is what it is,” he exclaimed. I laid there for a minute, and finally said, “Do you want me to go?” He replied, “Where are you going to go? It’s 2:00 in the morning.” I told him I would go wait in Port Authority for the next bus back to Hoboken. He said, “If you want to go, go, but I’m not asking you to leave.” That was a clear indicator I should have gotten dressed and left, but selfishly I needed sleep. I had alumni events the next day, and spending the night standing in Port Authority was not something I was interested in. Instead, I curled into a ball and laid as far to the edge of the bed as possible with my back facing him.
When I woke in the morning, it was a half hour before my alarm was set to go off. I quietly got dressed and was ready to walk out the door. I wasn’t sure if he was awake, and I didn’t know how to address our current situation. I was willing to give him a second chance if he was willing to be understanding on the topic. I stood over him to see if he was awake until finally I reached out and touched his leg. He jumped up and I said goodbye. He picked his head up to give me a kiss and said, “I’ll talk to you later.”
With that, I left. There was no way in hell I was going to be the one to make first contact. He treated me like a common hookup and demanded I give it up to him when he knew I wasn’t comfortable with that. Granted he was willing to do it for me the night before, but that was a choice he made. I did not force anything upon him.
On my walk to the bus, I played around on Grindr, answering my messages and seeing who was awake to pass the time. Ironically, this is the last time I would be on Grindr for some time, but I needed something to distract myself from the sh*t-show I was living.
Of course he never called or texted after that morning. It just proved to me it wouldn’t have been a good relationship, and I was happy to get out when I did. I didn’t need that kind of drama in my life, and I certainly wouldn’t miss it. Over the course of twenty-four hours, the relationship between us completely soured, and I would have to go back to the roster to find a more suitable candidate…
Just when you thought you heard the last from N, he’s made his way right back into the blog. You certainly weren’t the only one. We hadn’t spoken in a while. I got tired of his constant insinuations I was a whore. I was finding myself, and he was certainly not someone who should be judging me. I was over him, but I still wanted his friendship. But, if that meant dealing with the harassment I was receiving, I didn’t need his friendship that much.
On a random Thursday night at 12:30am I received a text from N. This is the conversation that ensued:
N: “Wanna go out? Cmon! Lol. I just got in from dinner with French coworkers.”
Me: “What!?”
“Lol. I took tomorrow off.”
Me: “Haha. Me too.”
N: “Hahahahah. Let’s gay bar. Lol. Jk. N’ play with men.”
Me: “Haha. Where’s your boy?”
N: “My boy?”
Me: “Yea.”
N: “He’s home. I just said I wanna play. Not hookup.”
Me: “I wasn’t saying that.”
N: “I’m not a slut.”
Me: “I didn’t say you were. Don’t put words in my mouth.”
N: “Can I put something else in your mouth instead?”
Me: “Lol. I’m not a slut. Haha.”
N: “I bet. ;)”
Me: “Okay. Maybe a lil”
N: “Pig”
Me: “?”
N: “Joke”
Me: “You at home?”
N: “Yup.”
Me: “Not going to the bar, but I’ll hang on the balcony if you’re down… Bored…”
TIME PASSES
Me: “Ha! Waiting for a better offer?… Haha”
N: “STFU. I’m smoking with my roommate.”
Me: “Enjoy.”
THE NEXT MORNING
N: “God, I was wrecked.”
Me: “Any interest in a trip to the gym uptown?”
N: “I’m going into work in five. Taking a cab. Or else I would.”
Me: “I thought you took the day off?”
N: “I think I’m going there from now on. I saw your old roommate there Wednesday.”
Me: “I know. Don’t change your gym for him. He’s not gonna blow you in the sauna…”
N: “Okay. I wasn’t changin’ for your weird unattractive ex-roommate, or for a sauna blowjob. But thanks for looking out.”
Me: “Any time.”
N: “Jerk.”
He may have gotten his jibes in, but I certainly didn’t stand there and take it this time. I started out playing along to try to show him the comments didn’t bother me. I thought if I played along, maybe they’d stop. I was wrong. That’s when I realized I needed to throw it right back at him. It seems to have worked. At this point I needed a break. His drunk texts may have been sober thoughts, but I wasn’t playing that game! It just proved to me once again I was the guy who conveniently lived across the street. Only time would heal that wound.
That entire week, Closet was texting me asking for sex. That Friday night I was free, and once again, I was home alone. I told him to come by.
This time, when he arrived, we went straight to the bedroom. We chatted while he took his shoes, shirt and pants off, but that didn’t last long. He lunged for me on the bed and was immediately on top of me, passionately making out. We stripped each other of all clothing and enjoyed each other’s company immensely.
Then, out of nowhere, he informed me he had been doing some preparation that week and asked me to try penetration again. I knew he was a virgin to this and it would certainly be a learning experience for him. I debated if I wanted the responsibility of being his first. He was a really nice guy, and we were having fun. In the five seconds I thought about it, I convinced myself, “Why not?” We were both here just to hook up. Why shouldn’t it be educational as well?
We both prepped, and I began slowly. VERY slowly. He of course winced at first, but soldiered on. I was impressed. After a while he really enjoyed himself, but then all of a sudden he asked to stop. He said he felt the need to urinate. He ran into the bathroom but nothing. He came back, and we began again. He apologized once more and said he had to use the bathroom. Again, nothing. He came back perplexed. I explained it was something he needed to get used to feeling. I was possibly pushing on his bladder or prostate. The whole time we were hooking up, I was slightly distracted. I kept thinking about how much he felt like a kid. He is older than I am, but he certainly felt like the much younger student. It was a strange dynamic. I barely knew what I was doing. How was I teaching someone else?
We began again, and he started to relax and enjoy himself. By the time we finished, he was enjoying himself full force. And thus, a bottom was born!
We laid there and chatted a bit. I got us glasses of water while we talked. After some time passed, we both showered, got dressed, and I gave him a kiss goodbye. I didn’t want to get in too deep with him, but for the time being, we were having fun. I wasn’t going to stand in the way of that. I had a feeling as well, this wouldn’t be the last time I saw Closet…
Saturday, I woke up fairly later in the morning. N was still sleeping in my bed, and Boston was still sleeping on the couch when I started to make breakfast. I fried up some frozen homemade sausage patties and eggs. In the meantime, my two favorite men woke up and joined me in the kitchen. I brewed a pot of coffee, and we sat and ate. Boston and I planned to go into the city for the day. He hadn’t been to the city in ten years. He is in music school and asked to check out the original Steinway store to play on some of their finest pianos. We invited N to join, but his plans included shaving his back and getting a haircut.
When breakfast ended, N and I went into my room and fooled around. I was horny since we didn’t do anything the night before and hungry for real sex. But, N wasn’t 100% cooperative. “I feel bad that Boston is out there alone right now. Ya know, we could let him watch,” he said with a wink and a smile. I just laughed it off and continued with my heavy petting. (I did feel bad for Boston because he got out of the shower and all his clean clothes were in my bedroom.) When I finally realized it wasn’t going to happen, we stopped. N went home to get ready for his day of primping, and I showered to get ready for the city. (I would later come to find N accusing me of hooking up with Boston at this point)
When Boston and I arrived in the city, we came upon a street fair. We walked around and got lunch. Following, I showed him some of the major attractions. It was really nice just relaxing with Boston and walking around the city. He started to feel like a little brother. Finally we arrived at the Steinway and Son’s a half hour before they were about to close for a recital. Boston sat at a few of the pianos and blew me away with his talent. I told him if he ever wanted to impress a guy, he should take him to a piano store and it would be in the bag.
We also stopped into to Saks to visit one of Boston’s old friends. We said hi, and he invited us to a house party and a drag show at a bar on the lower east side, Drom.
On the walk back to Port Authority, we passed a few of the pianos sprinkled around the city. I made Boston sit and play after The Naked Cowboy finished tinkering in Times Square. He ended up being filmed by the man in charge of documenting the project. Overall, I’d say it was a good day for Boston.
When we got back to Hoboken, we got dressed to go out and went to my friend K’s for a bbq. We were skipping the house party, but were going to meet them at Drom.
Likewise, N had plans for the night. Originally, he told me he was going out to dinner with friends and they didn’t know if they were staying in the city or coming back to Hoboken. To me, this meant straight friends. I figured i received no details because he wasn’t out to his- fellow diners. I was wrong. As the day went on, I received more details. He was going to dinner with eight gay men, and then it evolved into them going to Industry, a gay bar.
I asked him if it was an issue if we met up at Industry until Boston’s friends went to the lower east side. He told me to come. When Industry had a long line, they decided to go to Ritz, not my favorite bar. Boston and I finished at the bbq and headed to Ritz. On the walk there from Port Authority, I expressed my concerns about N and the night. I told him how shady it felt since he was being somewhat secretive. When we arrived, N’s phone was dying. I tried calling and texting to no avail. We went into the first floor and couldn’t find him anywhere. We tried upstairs to no avail as well. Finally, he texted me back. He was outside to smoking and trying to find us.
When he finally came back in, he was a drunk sweaty mess. I was way too sober to be there. I get very uncomfortable in gay bars for some reason. So, I ordered four straight vodka shots, two of which were for myself. He began to grind his ass in my crotch, and I liked it! This was the first time we could dance together and not create a total scene. A good portion of the night from then on is a blur for me. I got very drunk so I could tolerate the heat and the club and have blacked out a few bits.
When Boston got a text from his friends, we decided to leave. N told me he was coming with us. I was very pleasantly surprised. Boston and I went outside while N said goodbye to his fiends. When ten minutes passed, and he didn’t come out, I went back into the bar. As I was walking up the stairs, I noticed him talking to someone. Men were passing between us going up and down the stairs, but just then I saw him lean in and kiss this man. My heart shattered into a million pieces. In that millisecond, I felt my world crumbling around me. I know it was just one little kiss, but the fact that he was talking to another man, exchanging numbers and kissing broke my heart. I was crushed.
I didn’t know what to do other than run. I turned and sped down the stairs. He must have seen me at that instant because he chased after me. He tried to spin me around by grabbing my shoulder, but I flung my arms into the air and shouted, “Don’t touch me!” All that went through my head at that point was how many other guys were you grinding on and kissing before I arrived at the bar? We never had the exclusive conversation, but at that point, he was sleeping in my bed almost every night. We were in a relationship, even if it wasn’t defined.
He tried to calm me down on the street, but I was making a scene. I didn’t know what to do. When I get heated I get loud. He asked me to have a conversation and stop shouting, but I couldn’t be calm. I couldn’t be rational. I was enraged. Somehow, he managed to calm me down and convince me it was just a peck on the cheek in passing. Out of my inebriation, I let it go, and we went to the next bar. I felt awful. Boston was standing across the street witnessing this whole scene uncomfortably waiting for us to meet up with his friends at Drom.
In the cab ride, I decided I would pretend it didn’t happen for the night. Boston was only in town until the morning. I would deal with the situation later. I needed to entertain my good friend.
Boston lost his ID the night before, so when we attempted to enter the bar, the bouncer was not cooperative. Finally, when I shoved $40 into his hand, he let us in. After we each paid the $12 cover (on to of the $40), we came to realize Boston’s friends already left. The scene was dead. When I realized there was no chance in hell I was going to have fun the rest of the night, we grabbed a few drinks, and I volunteered to go on the hunt to find Boston a man to have fun with. We asked him what his type was. He explained. Then, N asked him if he was a top or a bottom. (This really had no relevance to the situation, and I think N took advantage to satiate his own curiosity.) When Boston was reluctant to elaborate, N said, “I’m a total top, but I love it when he puts his dick in my ass.” This was news to me. Especially since it never really fully made it there. It was just confirmation he was pumping Boston for information because he had a crush on him.
At one point, N and Boston walked to the bar to get drinks while I went to the restroom. Days later, Boston recounted for me the following exchange: N firmly gripped Boston’s ass and said, “How do you get an ass like that? So tight and firm. I’d really like to put my dick in there.” Had I known this happened that night, I would have left the bar with Boston and that would have been the end of it.
When we were all thoroughly exhausted and bored, we hopped in a cab back to Hoboken. No sooner we were in the door, and N was passed out face down on my bed in his underwear. This raised a whole new red flag in my brain. He was donning the sexiest underwear I’d ever seen him wear. His back was freshly shaved, his chest was cleanly shaved and he had a new haircut. All those are fine, but who was he expecting to see his underwear at a gay club. He spent the entire day getting ready for this night out. He never spent that much time primping to see me. Everything was starting to add up. From the business trip I took on, N was quickly distancing himself and seeking relationship freedom.
I went back out to the kitchen to chat with Boston. He immediately said, “OK! What happened!? What did you see!?” I explained to him the kiss, and in typical fashion, he dealt me the truth. He explained how N manipulated me that night as he watched from across the street. He told me to trust what I saw and trust my own instincts. We talked for at least another hour after that.
N’s phone was sitting there the whole time as well. I picked it up and was about to look through his Grindr messages because I wanted to find the closure I needed to tell him it was over. I couldn’t trust him anymore, but if I had proof, I would be able to get over it myself. Boston convinced me how bad that idea was. I put the phone down without pushing a button. To this day, I still regret not looking. It’s completely out of character for me to not trust someone and read their phone, but it would have delivered me the closure I needed.
At that point, I was exhausted. Physically and emotionally. That night I was delivered a heavy blow to the gut and needed to sleep to forget about it even for one instant. Boston went to the couch, and I begrudgingly went to share my bed with the man I had seen kissing another man. I laid down with my back to him and tears streaming down my face. I was crushed by what happened. I had no idea what to do. I still had very strong feelings for him, but couldn’t turn a blind eye. It isn’t who i am. I’m no one’s fallback or second best. However, I did know it was certainly not going to be a fun morning for him either…
I struggled with covering this topic so early in my blogging, but it fit in the timeline now. While I never get deep into specifics, if you are uncomfortable with the topic, I suggest you stop reading further through this post…
Something that always scared me was losing my gay virginity!
I mean, I’ve seen penetration in porn more times than I can count. Still doesn’t mean I had any clue what to expect. I was also never one to play around the back door — Never really an area of thrill for me, so it remained neglected. You also hear stories of girls popping their cherries and the pain they felt — I had a feeling that it would be similar for a guy.
I can’t recall how far into the relationship we were when penetration finally occurred. A little over a month maybe.
We decided to spend a night at my place. It wasn’t planned or anything we discussed specifically ahead of time. It just sprung from the passion of the moment. He took charge since this was my first time and obviously not his.
He was a very good candidate to take my V-card. Well hung, but not something that scared the sh*t out of me.
I tried to just relax. I have to say, it went much smoother than I expected. No searing pain. An interesting feeling having your prostate poked for the first time, I must say. This is where the pleasure stemmed — not the actual insertion itself. It certainly wasn’t my favorite part of sex (I love foreplay most) but still enjoyable. I felt closer to him than ever before. The care in his eyes made me feel at ease.
The next morning, we flipped, and he let me have my way with him. Big weekend for me! Two firsts in a matter of hours… I definitely enjoyed this more than receiving. While this became the typical horizontal arrangement, we shared all aspects of sex with each other over time.