Posts Tagged Penetration
Sexy Eyes
Posted by One Gay at a Time in Gay Dating on October 13, 2011
After seeing Sexy Eyes on the street with my roommate, I decided to make him a priority. He not only impressed me, but also my roommate. She wanted to date him . He was charming and funny and had a smile and sexy green eyes that gave me butterflies.
On my way home that night, I began texting immediately. He was all but begging me to stay in the city that night with him, but I insisted I would not let my roommate walk home alone at that hour of the night. He heavily respected my decision, but also attempted to persuade me to come back on another bus after I walked her home.
Instead, I promised we would go out the following Friday. That still didn’t satiate him. He wanted to know why we couldn’t meet Thursday. I explained I had my volleyball league Thursday nights, so I would be unable to meet up. I figured he would understand being quite the volleyball player himself.
That of course was a lie. I scheduled a meeting with a guy from OKCupid. It was an interesting scenario. The guy reached out to me originally, but after chatting a bit, I came to learn he was seeing someone. He was just looking for friends. I didn’t buy it of course, but if that’s what he really wanted, I was game. I need gay friends. We scheduled happy hour drinks for Thursday evening after work.
On top of that, I scheduled another date with a guy I met on Grindr a week prior. Between these two, there would be no time to meet Sexy Eyes.
When the OKCupid friend had to bail because of a follow-up job interview, I decided to see if Sexy Eyes was available for after work coffee. I figured we could sit and chat and get to know each other a little better.
He bit. He was extremely excited to see me. Immediately following work, I walked down to the Starbucks closest to his office. He works at a financial law firm and would not be finished for the evening. He was, however, able to step out for about an hour to chat.
The conversation was mainly dominated by him, but it was good nonetheless. We talked for about an hour before I told him I needed to head home for volleyball (my other date). Our date ended with a few smooches and a hug. I was really feeling this guy. We shared a lot in common, he was older and had a respectable job, he was very good looking, he was fun to be around… The list goes on. As I walked away, he texted me telling me he wanted to kiss me more, but didn’t want to make a scene near his office. He begged me to come back into the city after my “volleyball game.” I entertained the idea in my head, but I made no promises. Who knew how my next date would go?
I met the next guy at a bar near the Christopher Street PATH station, but that will have to be tomorrow’s blog entry, because as you may have suspected, I wasn’t quite done seeing Sexy Eyes that evening. After my second date, I went home, showered and changed, and hopped on a bus back to the city. Sexy Eyes was just finishing up his own volleyball workout as I was getting to Port Authority.
We agreed we’d go out somewhere, but made no plans. When I arrived at Port Authority, I called him to find out the plan. He told me he just got out of the shower and needed to finish getting ready. He gave me his address and told me to come to his apartment. We would make a decision where to go from there.
When I arrived, I told the doorman who I was there to see, and he let me up to the apartment. I was greeted at the door with a very nice kiss, and we chatted while he finished getting ready.
Somehow, we both ended up in his bedroom just as he finished getting ready. He sat on the bed in front of me, lifted my shirt and began kissing and licking my entire torso. It felt amazing.
Between kisses, he asked if I wanted to go out or just stay in. I didn’t need to verbally answer because I was already removing his shirt. I hadn’t had sex since Labor Day. I won’t say I was a big ball of horny, but he was a very attractive and seemed very interested in me and not just my body. I wanted him. Bad.
(Warning: The following may be graphic for some) Shortly after, he was undoing my belt and unzipping my pants. He was thrilled to learn I submitted to his request to wear briefs. I never wear them, but if a man requests it and thinks I look sexy in them, who am I to disagree? He then pulled down my briefs and opened his mouth and felt amazing. It had been a while since anyone did anything with my body besides my own two hands, so I was completely enjoying the moment.
Things got hotter, and we both ended up on the bed in numerous positions. Throughout the course of our time in bed, he started playfully biting me. I’m not gonna lie. It hurt! I went along with it because they were quick, and I have a high pain threshold. But, I wasn’t entirely into it. This was something that may have to be resolved down the road. At the peak of the passion, I was inside him, and we were both thoroughly enjoying ourselves. He finished during the act, and shortly after, I finished myself off. As per usual with the guys I’ve been with, he was impressed with my finale. Something I’ve learned to take pride in based on the reception it usually gets.
He beckoned me to come join him in the shower to clean up so we could snuggle in bed. After the shower, we laid in bed together and watched the late night news. It was getting very late, and I was constantly dozing off. After realizing this, he suggested we turn off the TV and go to bed. After all, we both had work in the morning, and he had to be up earlier than I did.
The next morning, we woke at the same time. He hopped in the shower while I read over emails from his bed. When he got out, I hopped in for my turn. He told me he would probably be gone by the time I got out. I was instructed to take my time and just pull the door shut behind me on my way out. I thanked him and kissed him goodbye.
That evening, it was affirmed for me the biting had gone too far. All day at work, my chest was sore where he bit me, and when I came home and got undressed, I looked like I was abused in certain spots.
That morning, I walked to work with a smile on my face. It was a good night, and I met a good man who seemed to be interested in me. Over the few months I’ve been out and single, I’ve learned my lesson not to count my chickens before they’ve hatched. Maybe I’ve become slightly jaded in the process, and this bothered me. But, this was something I needed to start doing so I wouldn’t get my hopes up and get hurt in the end.
Follow @onegayatatimeTurning Over a New Leaf
Posted by One Gay at a Time in Gay Dating on October 5, 2011
With the passing of Labor Day, summer officially ended in my book. I was sad to see it go. Like always, it flew by in no time. Its passing wasn’t all sadness, however. My favorite season was right around the corner. The changing of the leaves, the crisp air, the smell of fireplaces… all things I loved about the fall.
Just as the seasons were transforming, so too was I. Since I broke up with N, I went off the deep end. Part of this is because I never had my wild time. While everyone else was hooking up and experimenting in high school and college, I was being a good boy. I sat there and watched everyone else experience relationships and casual sex. I was asexual. Sure, I had my fair share of hookups with women, but nothing worth writing home about.
When I finally accepted myself and came to terms with my homosexuality, I found myself in a relationship right off the bat. I never had a chance to meet new guys and discover new things. Following my breakup with Broadway, I had a short window of wild time, but it was mainly filled with dates that ended with me going home alone. Then came San Francisco, shortly followed by N. This summer was the first time I was single and gay. Did I live it up? Yes. Am I proud of everything I did? Hell no, but I also have no regrets. Everything was an experience, whether it was something I learned from or something that made me a better person.
I began to look back and examine my summer. I wasn’t being true to who I am — True to myself. I don’t have casual sex. I’m a monogamist. I crave a meaningful relationship with a special guy who appreciates me, body and soul. If I kept sleeping around, I was never going to find this. I need to make a change. I thought I would be able to ease into it when I returned from Martha’s Vineyard, but I was wrong. I needed to be more drastic. I was going to be a good boy, even if it meant the palm of my hand would be raw.
I had two friends with benefits. I needed to cut them off completely. Closet was still messaging me since we last hooked up. “Hey man, haven’t talked to you on a while. Hope all is well. Don’t want to sound insecure or anything(too late), and I know you said its not a bother to text/email you, but just FYI in case that ever changes just let me know you’re lookin for something different or you’re seeing someone else. Lol feel free to lie to me, just would rather know if you’d rather me step back… I don’t want to become one of those creepers that I keep hearing about haha. Anyway hope to see you sometime, even to meet out for a drink or something. Later man.”
I originally found both my friends with benefits on adam4adam.com, so I sent them both messages on there. I lied and told them I was seeing someone, and I wouldn’t be able to see either of them anymore: “Hey dude. Sorry I haven’t hit you up. Everything is fine. I have started seeing someone, and I decided I need to stop with hookups outside a relationship regardless of that person. I think you’re a great guy, and I had a great time with you! Don’t doubt that. I just need to find a serious relationship right now, so I’m concentrating on that. I hope you understand!!!”
While the muscular weekend hookup simply replied, “No worries,”
Closet had a few more things to say: “Hey bro, its cool. No hard feelings. I mean can’t say I’m not disappointed, cause putting the physical aside, you really seem like a great guy, and I’m glad we met. Honestly, I felt weird saying it to you before, but now what the hell hehe…you’re the first guy I was with that made me think I wanna come out(not to mention my first for a few other things, lol). Obviously not saying I was in love after a few hookups lol, but I felt something more than just empty sex. I’m considering it after the holidays this year (you know, one last Christmas where the family likes me, hehe), but I’ll revisit that one later. Anyways, you’re a great catch, and I hope you find a great guy – and my offer remains open if you wanna grab a beer, just as a friend, hit me up. Thanks again dude, and I hope our paths cross again sometime. P.s. Two more things… 1. Thanks for being so patient with me in bed and all that, even though I still need to loosen up a little (pun intended), you really made me feel comfortable. 2. If you ever run into me while out at bars or whatever, cuz I’ve been in Hoboken quite a bit lately, feel free to say hi. I’m trying to gradually cut back on the paranoia part of all this.”
I felt pretty bad about the situation with Closet. It was obvious he was starting to fall for me, but I had no interest in pursuing anything with him. I knew I was right to cut it off when I did.
Outside of my regulars, I gave up Grindr cold turkey. I knew it would be too tempting to fall into something if they were hot and looking to hookup.
I joined OKCupid, was checking ManHunt and adam4adam.com regularly to see if there were any guys reaching out to me I’d be interested in meeting. It wasn’t easy finding a man up ’til now. I couldn’t expect it to get any easier just because I stopped hooking up with random men. None of the men I went on dates with previously showed any interest in seeing me again. Pillow and The Trainer kept giving me the runaround, so I had to learn when to simply give up and move on.
I started to wonder what was wrong with me. What was I doing wrong? Without the sex and without the happy feeling I get when I have a prospective guy I’m seeing, I started getting cranky. This was going to be a learning experience for me. I needed to not only find a man, but also to find myself. In the meantime, everyone around me would to have to watch out. I was not a happy camper…
Follow @onegayatatimeCan I See Your Press Credentials?
Posted by One Gay at a Time in Gay Dating on September 26, 2011
That time of year finally arrived — The end of summer. It’s always both a sad time and a happy time for me. I am a sun worshiper. I love the beach, and I love a good tan. It means the days get shorter, and the nights get longer, which isn’t necessary a bad thing when you have someone to share those nights with. Of course if you’ve read this blog at all, you know I don’t have that someone. However, it is a happy time for me because it means the annual Martha’s Vineyard trip many of my friends and I take has arrived. We always have a blast, and it’s one of the best crews I’ve ever traveled with. Everyone is mature and responsible, yet they still know how to have fun.
Since things ended with N, I kinda went on a whoring rampage. My time in OCMD was nothing short of scandalous. But, I was having fun. And, why shouldn’t I? I’m a single 27 year-old who is still finding himself in this new gay world. While everyone was having sex in high school and college, I was a good boy. I had my share of awkward hookups with women, but nothing successful enough to blossom into a relationship and rarely something worth revisiting again. Plus, the only way I would get better at sex was practice. So practice away I shall.
We hopped on the ferry to the island, and I fired up Grindr. I was beginning this trip with five other straight friends and ending it with ten. I knew I would crave some stimulation from other like-minded gentleman. Many of my friends were in relationships, some of which were tagging along on the vacation. I didn’t want to always be the third wheel. I made an effort to find someone to maybe sneak off on my own with.

Of course I found a few attractive men right off the bat, but pickings were actually quite slim. Many of the attractive ones happened to be on the mainland. One guy in particular messaged me. He was on the Vineyard covering the President’s vacation and had stayed on longer to cover Hurricane Irene as a photojournalist for CNN. He was staying in Vineyard Haven, where we were pulling into port around 9:00am. He could see my ferry coming in to port from his hotel window. He suggested I come by. I was definitely intrigued since he appeared to be quite an attractive man — Fit and handsome. I was also intrigued because originally he told me he was a CNN journalist in the President’s press corp. I thought it would make for an interesting story for the blog (This thing can be such a bad influence on my decision-making process sometimes!). He was a bit older, but I was on vacation, so my standards could also take a vacation. I explained to him I was just arriving on the island and would need to get settled in. Coming over for a quickie was not a solid option. That didn’t deter him. He certainly was persistent. He was waiting for a ferry, but was unsure which one he would get on due to the cancellations from the hurricane.
We arrived at our house and began unloading the car. We settled in and unpacked. I was originally under the impression we’d be heading directly to the beach, but everyone seemed to be lounging about. I inquired if I would have time to go for a run before we went anywhere. Everyone agreed they weren’t heading anywhere fast. I wasn’t really all that into meeting this guy, but at this point, there was no reason why I couldn’t. Am I proud of this? HELL NO! I was stupid and saw it as a challenge. So, I told the guy I was on my way.
In my haste, I left for the run shirtless. I hate running in a soaking wet t-shirt, so I left it behind. I wasn’t thinking ahead to the part where I would be walking into a hotel without a shirt on soaking wet from a run.
I texted him the whole way, almost getting hit by a car twice. He told me his room number and planned to leave the door ajar. He would be waiting for me in the bed. I was not really comfortable with this. I really felt like a gigolo, only I wasn’t getting paid. I explained my need for a towel when I arrived to help with the sweat from the 1.5 mile run, so he left one hanging on the door knob for me.
When I arrived, I walked right past the front desk straight to the elevator. When I go to the door, I entered the room. He was waiting on the bed for me. I removed my shoes and began to take off my shorts. He pulled me in, and we started to make out. I didn’t realize from his pictures he was quite the redhead. His entire body was freckles. He was my first ginger. Without getting into the details, we had our fun. SAFE fun. When all was said and done, I picked up the towel again and cleaned up as best I could. He couldn’t stop telling me how sexy I was and how great my body was. I don’t embarrass easily, but he was certainly making me start to blush. He told me if he didn’t get on the ferry that night, he would be calling upon me to go on another morning run the following day. I knew this wasn’t going to happen, but I humored him anyway. We exchanged a kiss, and I was back off on my run home.

Of course, the second I left for my run, everyone back at the house began speculating on my reason for leaving. I knew this was going to happen, and I could tell the second I walked back into the yard they had been discussing this. One my friends, a very loyal reader, immediately grilled me on how my run was. I saw right through her intentions, and I wasn’t going to give her the satisfaction of being right — Until now. I lied. I denied any lewd behavior on my part. I simply told them I was stuck on the other side of the drawbridge and had to wait for it to be lowered again. They bought it, and with that, I went in the house to shower and get ready for the day.
Ironically, later that night we had dinner on the beach in Menemsha. We stayed to watch the sunset and had a blast. We had no cellphone service out there because it is a remote part of the island. When I arrived home, I notice a message from the ginger mentioning seeing me on the beach that night. It was a little creepy knowing he didn’t take a ferry that day and saw me that evening. I was very grateful he didn’t walk up to me and say anything. And, of course, the following morning I had a request for a repeat, but there was no need to revisit that again.
I wasn’t on the island an hour, and I had already gotten myself into trouble. This was certainly going to be an interesting vacation…
Follow @onegayatatimeThe Closet Turns in His V-Card
Posted by One Gay at a Time in Gay Dating on September 23, 2011
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…
Follow @onegayatatimeVisit From the Closet
Posted by One Gay at a Time in Gay Dating on September 19, 2011
As I watched my roster shink over the summer, I began to revisit old friends. Adam4adam.com came back into my daily routine. I noticed I received a message from a 28 year-old guy who was still in the closet. His profile read: “Just lookin around, new to hookin up with guys and not out at all, so not really sure where I’m at right now. I do know I’m definitely extremely discreet and expect the same. Other than that, just playin it by ear.”
I knew this guy was going to be a delicate dance. His picture looked pretty good, and I was interested, so I reached back out to him. We exchanged a few emails about our current situations and talked about how fresh we both were in the gay world. I think that’s what he was looking for. Throughout every conversation we had, he stressed his need for discretion. I explained, “I spent 26 years in the closet. If anyone knows discretion, it’s me.”
We never made any plans during any of our initial conversations, but on a random Friday night, I found myself not interested in going to the bar. I had the apartment to myself, and I was bored so I hopped on a4a to check my messages. He happened to be online at the time, and I happened to be very horny, so I told him to come by. He had to shower and drive to Hoboken, but he was game.
This wasn’t my first rodeo. I was finally comfortable with these situations (not that that’s a good thing), and I realized I didn’t need to put in so much effort. When he arrived, I was sitting on the couch in gym shorts and a tank watching Jurassic Park. I poured us both a drink, and he joined me on the couch. We had casual conversation for a bit. Surprisingly, he made the first move. He put his hand on my leg when we were talking and left it there. As the conversation progressed, we stopped paying attention to the movie and began making out on the couch. Shortly thereafter, I pulled him over so he was straddling my lap, and we began an intense and fun make-out session.
When things got heated, and we were down to our boxers, I took his hand and led him to my bedroom. The boxers came off and the real fun began. We both had fun exploring the other’s body. He certainly was no Adonis, but he had a tight body nonetheless. I was enjoying myself, and he seemed to be as well.
At one point, he asked if I wanted to attempt penetration, but added a big disclaimer about his complete lack of experience in that realm. He was skeptical it was actually going to happen, and because of his comment, I knew it wasn’t. If that was going to be his first time, it certainly would take more prep. Five seconds after my initial approach, our suspicions were correct. He apologized, as he did a lot in bed. He was embarrassed by his lack of experience, but I actually found the role of teacher satisfying. I wasn’t the first guy he slept with, but I also wasn’t at the end of a long list, that’s for sure.
I often think back to everything I learned from Broadway and how absolutely patient he was with me from the start. I always try to embody that when dealing with someone new to the gay world, both in the bedroom and out.
When we realized penetration wasn’t going to work, we moved back to foreplay. After we both finished, we cleaned up and laid next to each other talking. I wasn’t thrilled with this. I wanted to have sex, not a long dialogue about being a closeted gay. However, I’d never be so rude as to say that or scoot him out the door. He was fresh, and I needed to be gentle with the delicate situation. I was also trying to find someone I could call on regularly for sex instead of random new guys all the time, so I didn’t want to do anything to mess this up. We talked for a half hour before he realized how long we’d been chatting. We got dressed and went back out to the couch to watch TV.
He sat down and I laid my head in his lap. It felt very comfortable, and I certainly didn’t mind that. He pet my head while we talked and watched TV. Eventually I fell asleep in his lap until he woke me to tell me he was heading home. I apologized for dozing off on him, but he was actually quite delighted it happened. I walked him to the door and kissed him goodbye.
He was a really down-to-earth guy and a big sweetheart. I liked him, but not enough to want to date him. And, the whole still in the closet thing was not something I wanted in a relationship.
Going forward, I was still searching for my unicorn, but in the meantime, he would become my go to on those lonely horny nights…
Follow @onegayatatime2 Can Play That Game
Posted by One Gay at a Time in Gay Dating on July 29, 2011
N and I were talking sporadically, but it was almost as if we weren’t in a relationship. He was working in the city that day, and sent me a text message asking what time I was heading in. I was getting in the habit of waking up and getting to work earlier. I still didn’t have my appetite and wasn’t eating breakfast in the morning, which bought me more time. I was also enjoying the distraction of work that kept me busy. I told him I would be heading in at 8:30. He said he wouldn’t be ready by then. I didn’t have to be in at a set time, so I waited for him.
Finally, at 9:15 he emerged from his apartment. Had I known he would take so long, I would not have waited, especially if I knew what was to follow. The conversation on the walk was very distant and awkward. We spoke as if we were already broken up. Most of the time, he was buried in his phone. Maybe he was on Grindr, but at this point, I didn’t care. I was too, and I was getting bites. When we were half way to the PATH, he pulls back and says, “Wait! This is telling me the bus is a better option for me to get to work.” Apparently we wouldn’t be going into to work together after all. I waited around for an awkward five-minute walk. He mentioned his need to stop at the ATM but would also needed exact change. Since I’m the overly generous person I am, opened my wallet and handed him a bus pass. He commented, “You would have this in your wallet.” Not even a thank you. I felt like one of his discarded used tissues. I allowed him to take advantage of my generosity, and I hated myself for it.
Before we headed our separate ways, he told me he was going to watch the fireworks with his family at his aunt’s house that night and would probably be staying there. We would not see each other that night.
While watching TV on the couch, I began to get horny. I decided to text the man I had sex with a few weeks earlier. He was a good lay, and I figured why not? I texted, “Hey man. Wanna come over?” He responded pretty quickly. He was out with friends but would stop by later. He added, “I not a whore or anything either, but I had fun last time with you.”
This is also the exact moment N texted me asking what I was up to because he was on his way back from his aunt’s house. In my passive aggressiveness, I told him watching a movie and chatting online. In the meantime, I texted the man from Grindr and informed him I would have to cancel and apologized. I got no response from N, so I asked if he was just checking up on me or if he was interested in hanging out. When N replied telling me he was just checking up on me, I immediately texted Mr. Grindr and told him to get his ass to my place and apologized for the confusion.
When he arrived, we went out to the balcony to hang out for a little bit and smoke. At this point, he started asking a lot of questions about N. When I asked him “What gives?” he explained someone meeting many of my descriptors had been texting him for some time now. He spoke up because when we met the first time, I was upfront and told him I was involved with someone. At this point, he offered to show me the messages he received. It was really none of my business what the exchanges were between them, but I graciously accepted the offer. What I saw next was just the dose of reality I needed. N had been asking this guy to hook up many times, even sending him pictures of his dick (with his face in the shot). So much for just talking! The icing on the cake was he was messaging him that night. He was playing back n forth between the two of us. That was the ultimate slap in the face. While he was sitting there in front of me, N was still texting him.
I knew better than to leave notifications on my phone when Mr. Grindr came over. I had a feeling N would text again, and I didn’t need a distraction. I was horny and was annoyed with N’s games. Mr. Grindr and I had an extensive conversation about the situation at hand. I apologized profusely for bringing him into the mess and came clean about using him just for sex. He actually was a good guy and I started to look at him as more of a friend than just a hookup. He didn’t need to tell me about N’s sexting, but he did. I greatly appreciated his candor.
With that, we headed inside to my bedroom. As we did, I glanced at my phone. I had three text messages from N asking if I was feeling better, asking how my chatting was going, and finally asking again what I was doing. Mr. Grindr looked at me and asked if it was N. I said yes as I put the phone down and lunged at him.
We had sex and it was good, but we needed to take a break. When we did, we discussed things again, but the conversation was more about the relationship between he and I, not involving N. He even asked, “Should I tell him to come over?” I loudly protested how bad an idea that was. I don’t know if he meant in the sense of a three-some, but I thought me meant more to confront him on his indiscretions. I told him it wasn’t my style to make a public spectacle of things. That type of action was not proper, not matter how much N was playing games.
At that very moment, Mr. Grindr got a text notification. He said, “That’s one of two people. Either my roommate or him.” I told him he didn’t need to look for me, but if he wanted to look for himself, that was his business. He looked, and sure enough, it was N asking him to hang out still. I got GREAT satisfaction out of this. Not only was N home alone with just his hand, but after trying to manipulate both of us, I got the guy. The two of them never had the opportunity to meet. Both were closeted and had roommates. They had nowhere “safe” to hookup.
Mr. Grindr’s morals kicked in at this point, and he decided it best if he went home. I tried to convince him to stay and chat further (and also finish what we started), but it was no use. He insisted on leaving. If I wasn’t feeling guilty enough for dragging him into this mess, now I felt downright awful. As he left, I walked to the window to watch what he did. I was curious if he was going to try to meet N. He walked to the corner of my street, looked at his phone, and looked toward N’s apartment. He paused a moment as I said out loud to myself, “Don’t you dare!” Just then, he turned and walked home. “Good boy!”
After about a half hour, I responded to N’s texts. I told him my appetite was returning and the online chatting was just Facebook. I then played dumb and followed up with, “Did you need something?”
The next morning I woke up to a text from N saying, “I wanted to see you.” What a prick! He didn’t want to see me. He wanted to get off! And, he didn’t care if it was Mr. Grindr or I. This cut deep, but my anger provided a sufficient band-aid for the time being. To me, it was his worst transgression. Even if they never met, he had every intent to do so. He even went as far as covering his bases by texting me should their plans fall through again. It was over. We were done. I do not stand for anyone treating me this way. After 26 years of single life and tormenting myself, I wouldn’t stand for this behavior! I deserve better! This was the wake-up call I needed, but this was just the beginning of my transformation back to my old self.
Pride Parade
Posted by One Gay at a Time in Gay Dating on July 25, 2011
The next morning, N woke up to me staring him in the face. I don’t know what I was looking at, but I was definitely looking for answers. When he opened his eyes, his expression said it all. It was as if he woke up from a bad dream, only to find it was reality. He kept blinking and closing his eyes and then looking back into mine. I’m sure he saw the pain that was there. I could tell he wanted to be anywhere else but there at that moment.
Neither of us said anything for a few moments until I broke the silence. “Can we talk about what happened last night?” He nodded in agreement and sat up in the bed. I kind of ambushed him before he even had a chance to wake up, but what could I do? It was all I could think about, and I wanted answers.
We talked about why he was so secretive about dinner with his friends. He denied being secretive and said he was completely upfront with me. When I pointed out a few discrepancies in the story, he brushed them off as details lost in confusion of planning for ten people. Then I addressed him kissing the guy. He flat out denied it still. He told me he didn’t know the guy and it was a peck on the cheek in passing. The body language between the two from what I saw would say otherwise, but I gave him the benefit of the doubt. I said, even if it was just a peck in passing, why were you talking to him in the first place? Why did you both have your phones out? Was this a guy you met before I arrived at the bar. (The man he kissed was Asian, and sure enough, that Monday, an Asian man friended him and wrote on his Facebook wall. Coincidence? Maybe. Maybe not.)

Here, he pled complete ignorance. He told me he had no idea who the guy was and couldn’t remember talking to him. He said he had a dream about talking to a bouncer about music and couldn’t remember what was reality and what was a dream since he was so drunk the night before. I knew this was bullsh*t. In my mind, I took a big step back. This was the ultimate betrayal of trust. We weren’t exclusive, but at this point, if he couldn’t be straight up with me, what did we have? Now, even more so, I felt like I was just a convenient booty call who lived across the street.
I explained how everything looks from my perspective. He stayed home the day before to primp his hair and his body, and donned sexy underwear to a gay club. What was he expecting to happen? He didn’t know I was going to meet up with him until he was already at dinner, so it wasn’t for me, and I pointed he never did that for me in the past. Was he opening the possibility of going home with another guy that night? He told me he shaved his body because he doesn’t like to take his shirt off with a hairy body and said the underwear was just a coincidence. He is a bad liar, so he stumbled over the underwear part. I had him figured out, and he didn’t know how to handle it.
Even now, after time has passed, I get emotional writing this and thinking about his mindset. I was obviously more invested in the relationship, but I had no idea the extent. The first morning he woke up in my bed, we talked about how much fun we had the night before and how compatible we were. However, he jokingly added, “Just don’t fall in love with me.” I should have heeded those words, and it’s my fault for falling for someone who was not as emotionally available.
The NYC Pride Parade was back, and this year I was much more comfortable with my sexuality. Last year, I got trapped in the middle of the parade with my parents — my worst nightmare. I couldn’t wait to get out of there. This year, I made an effort to attend.
We all woke up late that morning and I felt sick, which threw a wrench in our plans to catch the tail end of the parade before Boston hopped back on a bus to Boston. We grabbed breakfast in Hoboken, and I became very ill, spending a fair amount of time in the restroom. I was only able to eat half my sandwich. I had a lot to drink the night before, so I chalked it up to a hangover.
Afterwards, we journeyed into the city. We walked around a bit, and then said goodbye to Boston.
N asked what I wanted to do and told me he wanted to grab drinks. He contacted some of his friends he knew were in the city. Finally, two coworkers responded, so we decided to grab drinks and lunch with them.
As we all entered the bar, older creepy men were checking N out. One of N’s coworkers pointed out we were both given the up downs. I was a little creeped out by it, but N thrived on the attention. That really turned me off. I was starting to see a side of N I had never seen before, and I didn’t like what I was seeing. At one point, I went to the bathroom. I knew I would be the topic of conversation while I was gone. When we were walking to dinner later, N pulled me aside and told me they asked if we were dating. I wanted to ask him what his response was, but I wasn’t feeling myself. No words came out. He then gave me a peck on the cheek. We were in Chelsea for Pride Weekend. This is the time he could be very affectionate and open, and the only sign of affection I received all day was a tiny peck on the cheek. The guy from the night before got more action than me.
As the day progressed, I became less and less attracted to N. The way he reacted to some of the more disturbing stories recounted at dinner really threw me for a loop. We ordered dinner, and of course, I couldn’t eat it. Between the alcohol and the emotional turmoil, I felt awful. At one point, one of N’s coworkers mouthed across the table, “Are you okay?” I told him I was just really tired from the night before.
When dinner ended, N wanted to continue drinking. It was Sunday night, and I was beat, as were his coworkers. Begrudgingly, he agreed to come back to Hoboken and back to my apartment. When we were one block from my apartment, N reached down and held my hand. It was a very romantic gesture, but too little too late. As we came in sight of his apartment, he released my hand. This romantic gesture lasted all of thirty seconds.
When we got back to my apartment, I decided it was time to tell him about my blog. It was his right to know, and I needed to know if it upset him before I continued. He was shocked to hear about it, but told me he didn’t care and wasn’t going to read it. So, to all my faithful readers, the show goes on. I also came clean about the extent of my relationship with the 40 year-old. I did this because I lied to him about the interaction, but was truthful in my blog. I wanted him to hear the truth from my mouth, not a computer screen. This upset him immensely, which I couldn’t understand. It all happened before I met him. However, he apparently had some background information about this man and was holding it against me. I tried to defend myself, but he didn’t want to hear it. It bothered me that he was so upset, but I couldn’t undo the past.

At that point, we started to watch porn. The computer was out, and I suppose we needed to break the tension. I never did this with Broadway, but I was open to the idea with N. However, he got overly excited by this. He started about how he’d love to be a porn star. Once again, I was losing the attraction to the man in front of me. This was not the guy I fell for. I still had no idea what happened to cause the switch, but something was very different with him.
All of a sudden, we were interrupted by the sound of fireworks. We completely forgot about them. We ran to the balcony to watch. In the middle of all the explosions, I burst out with, “So are we exclusive?”
The next few moments were a blur, but I do know the gist of answer was no. I could understand if we weren’t exclusive up to that point, but I couldn’t fathom not being exclusive going forward.
When he explained his lack of interest in a monogamous relationship, I asked him if he has been sleeping with any other men since he met me. He told me of one guy he hooked up with after our third or fourth date. They exchanged blowjobs, but when this other man told him he was kind of in a relationship, N decided it better to be just friends. (This is also one of the guys he and I were possibly going to meet up with earlier that day.)
I couldn’t understand his rational. If he didn’t want to be “the other man,” why was he willing to seek out another man himself. What we had was pretty great, but he was leaving the door open for himself. If something better came along, he would upgrade. When I expressed this to him, he asked, “Upgrade to what?” I immediately responded, “A better situation.” It was so simple to me, how could he not understand that? I felt so used! He explained he wasn’t seeking out other men, but that didn’t make it any better. I already couldn’t trust him, and I had a pretty strong feeling he was lying.
I felt awful. Like someone stabbed me with a knife. Before the conversation, I knew what his answer was going to be, but hearing him say no broke my heart all over again. I was a shell of a human being.
After we finished talking, we went inside and had sex, and I finally got to have my way with him — All the way this time, not just the tip. It was pretty good too, but ended quickly due to N’s lack of experience.
In my mind, things were beginning to end between us. It’s almost as if that night was our breakup sex. I was pleased to know I got it in at least once before we broke up. I don’t know why, but it felt fulfilling. That’s how I knew it was over. I lost the emotional connection to the man who days earlier I was falling in love with.
Follow @onegayatatimeYour Cheating Heart
Posted by One Gay at a Time in Gay Dating on July 22, 2011
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…
[twitter-follow screen_name=’onegayatatime’ link_color=’00ccff’
“Are You My Boyfriend?”
Posted by One Gay at a Time in Gay Dating on July 18, 2011
After a rocky weekend with N, including him losing his phone and not finding a replacement, I had to start a new work week. I had a big pitch coming up for work and would have to travel to Denver. But, I wanted to hang out with my man before taking off.

I get myself in the habit of buying Groupons and Living Social deals in hopes of cheaper nights out on the town. When I am seeing someone, I tend to buy more because then they become excuses for us to go out to dinner or enjoy something fun and not have to spend a lot of money to do so.
The night before, we planned to use one of my deals at a local spot, Clinton Social. It would be a nice dinner date before I flew off to Colorado for 2 days. It was also nice because it’s where we went on our first date. We had a blast that night and found how much we had in common. Now that we had gotten to know each other, the chemistry was even stronger.
In the evening after work we met up at my apartment and walked to the restaurant. We sat in the back where only one other table was occupied. It was nice having semi-private dining. I get self conscious sometimes about people gawking at two men sharing a meal. I was free to not care. Every once in a while I would put my hand under the table and rub his knee. I wanted him to know how much he meant to me. We talked about our workdays and a few other things while we shared an appetizer. When our meals came, we dug in like two ravenous animals. We both enjoyed our meals and fed samples to each other. It wasn’t quite as romantic as when he cooked for me, but it was really nice dining with such a sexy man. When we finished and paid, we scooted out the back door and walked back to my apartment.
The walk back was very hot, so when we arrived at my apartment, we were both very sweaty. We decided to share a shower. I was still feeling romantic from the dinner date, so I suggested we share a bath instead. I have a very large whirlpool tub, and we’ve talked about using it before. Since it was recently cleaned, now was the perfect time. We hopped in and surprisingly both fit pretty comfortably. After a while, I squirted some body wash into the tub so we would have a bubble bath. We played with the bubbles for a while until we both had enough. We toweled off and hopped into bed.
That night, we finally had full sex for the first time. Since he was so willing to try the first night we met when we came back to my bedroom, I thought it was time I finally give it up for him. Of course it wasn’t without complications. It had been a long time since anything had gone on back there for me, so breaks needed to be taken. Of course condoms are never fun either, but they are always necessary. Once things got more relaxed, we finally found a groove, and I could tell he was starting to really enjoy himself. It was a good night. I felt we were growing much closer every day. After we were both good and sweaty and both substantially pleased, we stopped.

After a few minutes of laying there, N turned to me and blurted out, “So are you my boyfriend?” I didn’t know what to say. A large part of me was thrilled. I had never had a “boyfriend” before since the only other man I had been with romantically didn’t let me call him my boyfriend. However, another part of me was skeptical. We were only dating for a month and a half. Were we there yet? To me, it didn’t particularly matter. No other man mattered to me then. I wasn’t seeing anyone else. And I’ve learned to lose titles a long time ago. All this went through my head over the course of about two seconds. Right then, I said to him, “Do you want me to be?” At that point, I think he realized his verbal diarrhea. The thought was going through his head, but he didn’t really mean to say it out loud. He responded, “I don’t know.”
I decided to let that conversation die. Obviously he wasn’t ready to fully have it, and I didn’t feel we needed to discuss it yet. It was getting late and I still had to pack in the morning, so we dozed off to sleep.
Follow @onegayatatime

