Posts Tagged condoms

Vintage Closet

Before my trip to Washington DC, I started chatting with a few guys on Grindr. It was bad timing for the trip to come right after “meeting” them, but it would have to do. On my way back home, I made plans with a few guys over text for dates to get to know them.

One of the guys I was talking to was a bit older. He seemed like a great guy, and he was very interested in me. Of all the guys I started talking to, he texted the most. He seemed sweet, caring and attentive. While away, he asked how the blossoms were. He genuinely took an interest in me. He was texting me like a high school girl. I wasn’t annoyed. I was flattered. We made plans to grab a drink Wednesday evening after work.

Since Southern Drawl didn’t want to go to The Breslin, I proposed he and I meet there for a drink. It wasn’t far from my office, and it was pretty centrally located in Manhattan. We set a time, and I stayed at the office to kill time until he could make it there.

He ended up arriving early, and he texted me to let me know. I quickly left my office and speed-walked the ten blocks to the bar to meet him.

I wasn’t sure what I’d be meeting that night. From his picture, he looked like a very mature man. He had white hair, and he told me he was possibly getting a haircut before we met. I encouraged him to keep his longer hair since I liked it, but it was his hair. I didn’t know which hairstyle I’d be meeting.

I walked in to find him standing leaning against the wall. It wasn’t too difficult to pick him out of the crowd, however, he looked much older than I originally expected. I invited him to follow me to the bar and ordered us drinks. I managed to snag two bar stools just as someone was getting up to walk away.

We dove right into conversation about work. We both worked in advertising at one point, so we discussed that for a while. The more we talked, the more relaxed the conversation became. I didn’t see this conversation growing into a relationship, but he was a really nice guy. There was no reason why I couldn’t share a few rounds with a nice guy. I really didn’t think we were compatible.

Somehow we got into philosophical conversation talking about life in general. He really liked my outlook on life. I wasn’t putting on a show or anything. I was just being myself. He really responded well to this.

During our conversation, he came clean on his age and informed me he was 36. That’s how old Smiles was, so it wasn’t the issue for me. He did, however, look more like he was 42. I wasn’t sure if I believed him about his age. I wondered if he was lowballing it.

We started talking about family and his family house in the Hamptons. We got on the topic of coming out, and I told him how fresh I was to the gay world. He responded well to this and told me he was new himself. He came out to a few of his high school friends, and apparently it didn’t go well. For them, it became a problem of an identity crisis. They didn’t know who he was anymore. I told him how positive my experience was coming out and conveyed my sympathy about his experience. He also told me his family didn’t know either. It appeared I was more gay mature than he was. This was a first. This was a 36 year-old man who was still living in the closet. I didn’t think I could handle that. If he couldn’t accept himself by that age, the road was only going to get rockier as we went along.

After three rounds, the time came to go home. He expressed his desire to go on a second date, and I let on that this was a possibility. I didn’t want to lead him on and seem overly zealous about it, but I didn’t want to break his spirit. We walked to the corner and said goodbye with a hug. We exchanged a few texts after that, but obviously nothing ever materialized.

It wasn’t that late, so I decided to text M.E. and see if he wanted to come over. He did, and when he arrived at my apartment, we immediately went to the bedroom. Warning: The following may be too graphic for some. We stripped each other naked and got right down to things. There was a bit of foreplay and a lot of making out before I reached for the condoms and lube. Since being with him, I had unprotected sex with someone else. I needed to keep his safety in mind. While in DC, my results came back with no STDs and HIV negative, but I didn’t want to take any chances. We had amazing protected sex that night and fell asleep in a spooning position.

When we woke in the morning, we fooled around until we hopped in the shower. There, we had sex once again. I’m always horny in the morning, so this was even better than the night before. When we finished showering, we went back to the bed and had sex there. At one point, I even turned over and let him penetrate me. I felt I owed it to him. He was incredibly excited about it. This didn’t last long because, as he told me, he had a hard time keeping an erection after he’d been penetrated. I was okay with this, being as it’d been a long time since I bottomed.

We laid with each other, and I tried to finish myself off but to no avail. I had a dentist appointment to get to that morning, so I could no longer dawdle. I was already late the way it was. This was going to be a rough day. How was I ever going to concentrate on anything!?

M.E. gave me a ride to the dentist, and I gave him a kiss goodbye.

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Check That Off the List

Once again, another Friday arrived, and once again, I used up a carry-over vacation day to stay home and relax.

This post is embarrassing. It is now especially embarrassing because a few readers have commented about my promiscuous ways, but nonetheless, I will report the incident honestly and to my best ability. I, in no way shape or form, condone the following behavior. An early warning as well – this post will be graphic.

For some time, I’d been speaking to a few guys on Grindr who happened to be tops. When we both learned we were the same position, discussion turned to other options, such as bringing in a third. We were both really attracted to each other, but neither was willing to bottom for the other.

Many men dream about the threesome. Straight men fantasize about it constantly, and I assume it’s a big gay male fantasy as well. The only difference is gay men probably act on it and achieve it far more often. It certainly isn’t, however, easy to pull off. You have to organize three different mens’ schedules and also take into consideration their taste in other men. We all know how finicky gay men can be.

I woke up Friday with no agenda and morning wood. I wanted to take care of it, but I also wanted to act on my recent fantasy of a threesome. I started with one of the most promising guys who I’d discussed this with before. He wasn’t getting back to me. I began going through more than a few permutations trying to find 2 guys willing to participate who weren’t occupied with work.

Finally, I found one, and we both began to hunt for that elusive third. There were many roadblocks, and lots of waiting to hear back when questions were posed. I thought I had it all worked out, when one of the guys went dark on me. I was very disappointed because I thought I found the perfect combination. One top (me), one bottom, and one vers. When the bottom got a flat tire, it all went to $hit. All this juggling really made me realize why this never happened before.

After much discussion about who could host and who wouldn’t host, I managed to get my original group together, but not without issue. I had to ride my motorcycle into New York City to pick the bottom up. He wasn’t comfortable coming out to Hoboken alone, and the other guy wasn’t willing to host strangers. Strange to think he had no problem hopping into bed with strangers, just as long as it wasn’t his own. I rode in and picked him up. It was slightly awkward, but it all fell right into place. He hopped on the back of the bike, and we rode off to my place.

Warning: The following may be too graphic for some. We arrived before the other guy. I didn’t know the rules, but I was looking to wait for the vers guy to arrive before we got started. The bottom wasn’t so patient. He wasn’t the best looking man in the world, but he had a great body. He started kissing all over me until he undid my pants and started orally pleasuring me. He was quite good. He undid his pants as well and revealed a generous gift. He asked me if we could go to the bedroom until the other guy arrived. I encouraged him to wait since he was only a few blocks away.

When he arrived, the bottom walked to my bedroom and began to undress. I brought the vers guy into my room, and he and I began to undress. I wasn’t as thrilled with him. He looked much better in his pictures, but there certainly wasn’t anything wrong with him. You can’t win ‘em all. I laid on the bed in my boxer briefs while the other two joined me and began rubbing me all over and kissing me. I felt like a king. Everyone was there serving me, and it felt great!

Then the underwear was removed on all parties. There was lots of rubbing, kissing, sucking, etc. After some time, I broke out the condoms and lube. I was horny and ready to get started with the real fun. After using his poppers, the bottom was ready and eager, so I penetrated him while he orally pleasured the vers. Then the vers came to my side of the bed. We’d already discussed I wasn’t bottoming, but he thought I could be persuaded. I told him sorry, but no. I backed off and let him have a turn with the bottom.

This guy was incredibly awkward. He looked like he was having a seizure. His sex was spastic and crazy. On top of that, he was very particular and insisted I use the condoms and lube he brought. While he was inside the bottom, I climbed on top and penetrated the vers. This was not the easiest sex position by any means, and it did not last long. The logistics of three people getting the same rhythm are nearly impossible. It’s obvious in porn when this happens, they are doing it for the camera and certainly not for pleasure.

We swapped positions a few times and had already gone through a substantial amount of condoms. If one thing was certain, I was going to be wrapped up at all times! Finally, I suggested we move things to my shower.

We went through a few permutations of positions in the shower before I told them I simply wanted to watch them while I took care of myself. The bottom protested. I could tell he was very annoyed by the vers and wanted me more. When we ran out of warm water, we all toweled off. The bottom needed to excuse himself. He was feeling light-headed. He made his way out to the living room in his towel.

I was left with the spaz in my room, and I wasn’t thrilled. We tried a go at it for a short bit, but I was much more interested in the guy sitting in the living room. We stopped and moved things out to the living room after closing all the curtains. The bottom was feeling better, so he was eager for me again. He hopped on the chair and asked me to go again with him.

There was something that really turned me on watching the other two guys have sex. I pulled out and encouraged the vers to join in again. I wanted to sit on the couch and finish while I watched them. The bottom wasn’t happy about this because the vers was bad at sex. All three of us were on the couch when I finally finished on my chest. The vers reached climax as well, but the bottom seemed content with stopping before he finished.

The vers guy almost immediately began to get dressed, noting he had to get back home to finish work. The bottom was going to head back in with him so he wouldn’t get lost, but the vers wasn’t willing to wait for him to get dressed. The bottom asked me to ride him back onto the city, but I told him I would give him a ride as far as the PATH. From there on, he was on his own.

We chatted a bit about how spastic the other guy was. Neither of us were thrilled with him, but it is what it is. The bottom got dressed and hopped on the back of my motorcycle. When we got to the PATH, I gave him directions for getting back home.

I sped off home. I was in need of a serious shower. Since the morning’s activities began, I felt incredibly dirty.

If you’re considering a threesome, I strongly encourage you to think it out first. Don’t just jump into it to satisfy some great fantasy you’ve seen many times in porn. If you have the constitution for it, then by all means, do what makes you happy. But, if you’re thinking twice, I strongly suggest you leave the fantasy to your mouse clicking.

There was nothing sexy about what happened. It did not live up to the fantasy I had originally dreamed of. It was awkward and at times laborious. I needed to wash away the shame and guilt I felt, but it was no use. Those would stick around for at least the remainder of the day.

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Late Night Quickie

Sunday night in LA, I took quite a blow to my heart. I tried to prepare myself for the inevitable goodbye, but I didn’t get to say goodbye. I’d driven all over LA trying to connect with The Navigator, but he wasn’t responding.

I faced facts and drove to the airport. I had no idea what else to do with my time, so I just drove to the car rental lot and returned my car. I figured I could at least use some time at the airport to blog a bit. I sat int he airport diner and ate my dinner alone.

My flight home was awful. First off, it was a redeye. I was set to land at 6:00am Monday morning. I had to go to work later that day so I tried my best to sleep on the plane. It was also awful because I was crammed in a widow seat towards the back of the plane. My airline status with United got me nowhere. I barely fit in my seat, and I wasn’t able to stretch out and walk around because the two men next to me were sleeping the entire flight.

I managed to sleep for two hours, but woke up after that. I had no feeling in my ring and pinky finger of my left had. Apparently I slept on it funny. When a fair amount of time passed, and I never regained feeling, I became worried. Maybe I had a blood clot or maybe I’d done some nerve damage. I tried to think about other things and distract myself, but I really started to get worried. I took out my laptop and did some more blogging, but even that was a challenge with two numb fingers. I was really starting to worry, but the feeling didn’t return the rest of the flight. (Four weeks and a doctor appointment later, and I finally regained feeling — I had a nerve impingement — Cubital Tunnel Syndrome).

I was exhausted all day at work Monday. I’d only gotten a few hours sleep on the plane and about one hour in my own bed before work. When I got home after work, I was still horny from my rambunctious trip. I was on Grindr, and a cute guy from the city wanted to come over for some fun. I didn’t turn him down since he was hot and said he’d wear his jockstrap.

When he arrived, I realized he was a redhead. He also had a slight Hispanic accent. He was also quite a presence clocking in at 6’4″. He was not born in America, but had been here a majority of his life. He was decent on the eyes, but nothing you’d run to your friends about. When he arrived we went straight to my room. He slowly got undressed and comfortable until we were both laying on the bed, me in my boxer briefs and him in a jockstrap.

Warning: The following may be too graphic for some. I found the jockstrap very sexy. I’ve always been attracted to the athlete types and find locker rooms to be one of the sexiest places. They just turn me on. Always have.The jockstrap really gave him the leg up in my book. He was looking for a hot top, and I agreed to fill the position, literally. I broke out the condoms and lube, and we have a good time. Sometimes it was a little weird and awkward, but sex is never perfect! He really seemed to be enjoying himself. I did as well, but I could already tell this guy was going to linger. He was a gentle spirit. This would be no wham bam thank you man. I was going to have to sit through some pillow talk.

He started talking about his grandmother and how she is sick. He was flying home the following day to see her before she passed away. It wasn’t looking good. I started to feel bad for him, but then my emotions became distracted when he mentioned things like sleeping with her in her hospital bed. He looked like he was ready to cry, but all I could think about was this strange layout in a hospital room. I understood he was close to her, as she was responsible for raising him, but some of the things he was saying with his accent seemed very strange to me. There was obviously a cultural divide.

After we chatted some more, and he asked if he could use my shower. Now he was really pushing it! I obliged the request, but after that, he was gone.

He showered and toweled off. He began to get ready to go home. He talked about getting together again when he got back. He mentioned how heartless a lot of the other guys he’d hung out with were, and how sweet I was. He said how much he liked me. He wanted this to be an ongoing thing of friends with benefits. He told me his real name and that the name he gave me, Keith, was completely made up. Someone was a little paranoid. I felt like I found a stray puppy who wanted to follow me home. There would never be a next time, but I told him to hit me up when he got back from visiting his grandmother. After about three weeks, he did of course text, and I of course did not respond.

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No Day at the Beach

For one, I was really enjoying the company of my new friend, The Navigator. Secondly, the weather was amazing. I couldn’t have been happier to be away from the cold weather on the East Coast.

Contrary to my plan, the weather wasn’t fully cooperative. The closer we got to the coast, the cloudier and colder it got. I didn’t care how cold it was, I was not putting the top on the convertible back up. I did, however, turn the heat up. That kept us cozy while we acclimated to the new weather pattern.

We drove around for a little before finally finding a parking spot. We walked to the beach, and we spread out the blanket I asked him to bring. He sat down, and he started pulling out the other provisions he brought — A bottle of Sprite, a bottle of Absolut, and some snacks and granola bars. I think I was falling in love. He was spontaneous and courteous. I added the provisions I grabbed at the gas station to the pool.

We sat next to each other commenting on how much the weather deteriorated and chatting about some of the surfers. We were among sparse company. The only other people brave enough to hit the sand that day were the surfers we both scoped out.

We relaxed and the conversation from the car continued. He talked about his family and his background. I learned he was a Jehovah’s Witness. He wasn’t very passive in his faith either. He had the prestigious honor to attend a bible college in Brooklyn. While there, through a slip up, it was discovered he is gay. He was excommunicated from the religion and has very limited contact with his family.

My heart was breaking to hear this sad story. He was an incredible man for surviving all that, and even more impressive for his comfort telling this to virtually a complete stranger. I told him about my religion, and my new outlook on it. I told him about my conversation with my mother on Christmas Eve, even though it was nothing compared to what he went through.

As if his story couldn’t be more complicated, I learned his brother is also gay and struggling with his religion. He was actually finding men online and hooking up with them at rest stops until he was nearly caught by police. His brother chose to take a different route in dealing with this. The Navigator tried to suppress his homosexuality with the aid of his religious elders, but came to accept who he is. His brother was not as fortunate to have the mental confidence to know himself. He was going through conversion classes to help him become heterosexual. They were trying to brainwash him. My skin was crawling at the sound of this.

After leaving his religion, he moved around a lot. One move was for a man, but obviously that didn’t work out. He’d been in LA for roughly a year and was still settling in.

I was really enjoying his company. We took turns making trips to the restroom, and when he stood to walk away, I took the opportunity to check him out. In the back of my head, a voice was screaming, “Be careful! You’re on vacation. You can’t fall for another West Coaster!” My heart was not going to be so easily convinced. I was cautiously proceeding. I really liked this guy. If he lived in New York, we’d definitely be dating. He was just what I was looking for. A masculine man who had his life together and knew what he wanted in life.

When we sufficiently froze our a$ses off, we hopped back in the car and made our way back inland. While we drove back to Glendale, I realized I’d already used up all my condoms and almost all the lube. I would need to stop for provisions along the way, but it wasn’t going to be easy with The Navigator with me. I decided to stop at a CVS. While he looked for the bathroom, I looked for the condoms and lube. I told him I needed to buy sunscreen, which I did, but that was very low on the priority list.

When I finally found what I needed, I realized they were under lock and key. I had to push a button that made the announcement, “Assistance needed in the family planning department.” Family planning couldn’t be further from what I was looking for. The irony was killing me. As Broadway always joked, “Butt babies don’t live.” I wondered what I’d done recently to deserve this karma. It was going to be nearly impossible to pull this off without him seeing what I was purchasing.

Someone came to unlock the case, and he turned his head in an attempt to give me my privacy. That was long gone. I grabbed what I needed and quickly walked to the checkout counter. Of course, when I arrived, there was a long line. I took my place in line behind an old man and hoped The Navigator was still looking for the restrooms.

I was next in line. Maybe I was going to get away with this after all. It wasn’t in the cards for me. The old man in front of me was taking FOREVER! Every second that passed was nerve-wracking. I didn’t want him to see what I was purchasing because it may have been perceived presumptuous.

Just then, he walked up behind me. My cover was blown. I tried to hide the products in the crooks of my crossed arms, but there’s a really good chance he saw what I had. Of course, this was also the moment the next register opened up. I walked up and purchased my items. I paid, and we walked back to the car without mentioning what I bought at all.

We talked the whole ride back to his apartment. When I turned onto his street, he turned to me and said, “Sooo, do you want to hang out some more?” Without hesitation, I shouted, “Yes!” He asked if I want to go back to my hotel room and hang out, and I agreed that was a great idea!

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Lazy Morning

Today is another Fast Forward Friday!!!  

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

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


Smiles and I had a very special night together sharing dinner in my apartment. We went to be happily in each other’s arms after being away from each other for some time. I’m not entirely sure why, but I felt he’d finally come around to me.

The next morning, we woke up late. I knew I had a very light workload that day, so I was in no rush to wake up. I was also feeling frisky. I tried to seduce Smiles with a back rub. I instructed him to roll on his stomach as I lifted his shirt and began massaging his back. He commented on how my hands can completely cover his back from end to end. This was one thing my big hands specialized in, so I was content putting them to good use. I began to reach my hands under him grasping his pecs in a sensual manner.

The massage didn’t last long and the seduction failed to the grumbles of Smiles’ stomach. I should have remembered that was his first priority in the morning.

We went into the kitchen and brewed coffee while I made us steak and eggs (some of the left over beef from the night before). He continuously hugged my while I cooked. Cooking at the stove for a sexy man while he wrapped his arms around me — What more could I want?

We sat at the kitchen counter and ate while we chatted a bit about what we had to do the rest of the day. I also caught Smiles up on some of the events going on around the world since he didn’t have cable and wasn’t the best at staying informed.

After breakfast, we returned to my room. I needed to get ready for the office, and Smiles needed to get dressed to head home to begin his workday. We started to make out a bit until I pulled him towards the bed. “Do you want to have sex?” he asked. I giggled with a big grin and replied, “Of course. Why do you think I was trying to seduce you before? I always want sex.” That was also my subtle way of letting him know I wanted to have more sex.

During the summer of 2010, after my breakup with N, I was having a lot more sex. I decided to be more economical with my condom purchases and bought a forty pack. I kept them in my nightstand drawer next to the bottle of lube I purchased. Smiles had been in the drawer before, and I’m sure he’d noticed the quantity. But, he never said anything about it until now. He made a comment on how many I had. “Does it intimidate you?” I asked. He simply replied with a “No.” I then gave a not so subtle comment hinting about how I’d like to have more sex. “Well, we could just use them all, and then there won’t be so many,” I exclaimed. Apparently, our conversation about the state of our relationship gave me the confidence to speak my mind when it came to our relationship going forward.

Warning: The following may be too graphic for some. I was already on my back with him on top of me, so I could only assume he wanted to top this time around. I topped the last time, so I only thought it fair to receive this time. I slipped the condom on him as he made a comment questioning whether I was doing it right. “[Smiles]. This isn’t my first condom, obviously,” I quipped.

I lubricated myself and laid back. I hadn’t thought much about my inability to finish with Smiles in quite some time, but I was going to try a new technique this time around. I was going to completely relax and try to enjoy every minute of it. I usually derive no pleasure from bottoming, but for some reason, this time it was working. He felt great, and I could tell he was enjoying himself as well.

I was getting very close as I pleasured myself while he penetrated me. Just as I was about to climax, he said, “I going to cum.” I quickly responded, “Me too.” And with that, as close as I was, I was a mile away from finishing. In that split second of him distracting me, I lost it. I could feel my muscles quivering just before he said anything, but it was gone. Now, it was top of mind, and I knew it wasn’t going to happen.

Smiles would have been so happy. He’d wanted to make me finish for so long, and he would have been the first to do so from topping me. Alas, it wasn’t meant to be. When it didn’t, I could see him looking into my eyes with compassion. The sex was great. There was no pain or awkwardness. I wanted to show him how much I enjoyed it, but I couldn’t. My mental block got in the way once again.

After we relaxed and kissed a bit, he suggested we clean up in the shower. He was getting ready to hop in, and I told him I was coming in with him. My shower has two shower heads and a seat. Everyone that has seen my shower has made sexual comments about it, and I was going to finally get some use out of them.

I wanted to have some more sensual time together, and when I hopped in, Smiles began to wash me. I was very turned on by this. When he finished, I tried to do the same for him, but he wasn’t interested. He rinsed off and hopped out of the shower to dry off. I watched him as he toweled off, and immediately got extremely aroused. He put lotion on his face with his towel on the floor while I pleasured myself in the shower at the sight. When he left my bathroom, I beckoned him to come back in the shower and help me finish. I wanted him to be a part of it. He climbed in and I pressed myself against his back while I tried to finish. Once again, failure.

When we ran out of hot water, we hopped out. He finished applying lotion and brushing his teeth while I masturbated on my bed. I needed to finish somehow or work was going to be hell for me! He came and joined me in the crook of one my arms while I pleasured myself. FINALLY, it came. I thought of him dropping the towel in the bathroom, and it set me off. I was disappointed it wasn’t a direct reaction to something Smiles did, but I was relieved he was there to witness that it was possible and that my climax was something pretty special 😉 .

We quickly finished getting ready and walked to the PATH with my roommate chatting the whole way. The conversation wasn’t as free-flowing between us as much as when it was just the two of us. I wondered if Smiles had issues with PDA and public discussion. It just felt a little awkward.

When we got to his stop, I gave him a peck on the lips to say goodbye. I thought about that morning all day. I was happy to finally finish with him in the room, but I wished it came at Smiles’ hand. I think it would have been an ego boost for him and a big step forward for the two of us. However, it was progress — Baby steps. This something I was going to conquer, hopefully with Smiles’ assistance.

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Collection of Men

After all the drama of the week and the mindless hookup, I was ready for change. I wanted to be more present. I accumulated over 60 phone numbers of men in my phone, but had only met 9 of them at that point. I needed to fix this ratio. I needed to go on more dates and have less hookups. I also needed to find myself again.

My roommates and I decided to hit up our favorite bar. We were going to put their new connections with my favorite bartenders to good use. Once again, we had a blast, and on the way home we had a very interesting conversation.

I got into a debate with my male roommate about the perils of unprotected sex. He insisted the worry was greater for straight couples, as a baby could be the end result. I begged to differ. While bringing an unplanned child into the world can be very stressful, it certainly isn’t the end of the world. HIV can be just that if not detected and treated. It can be a life sentence just from a few minutes of pleasure. Regardless, we both agreed the perils of unprotected sex were not worth it, but we agreed to disagree about which was worse.

The conversation switched to Grindr. Both roommates couldn’t believe how easy it was for me to “meet” a guy and turn it into something more. My male roommate was jealous how easy it was to find sex, and my female roommate was jealous because of the sexy men I was talking to. I explained how both were a double-edged sword. While I had no problem finding a hot man to come over for sex, I had a very difficult time finding a man who was interested in a monogamous relationship. It is nearly impossible. I still have hope for upstanding men out there who are interested in other men, but they are becoming somewhat of a unicorn.

The next morning, while passing through the city on the way to the beach, I pulled up Grindr. Much to my surprise, my old college roommate popped up. I remembered him telling me he lived in that neighborhood, and I did know he was gay. But, I never thought about him popping up on my Grindr. When I first came out to friends, I contemplated coming out to him. He respected me enough in college to tell me early on about his homosexuality. Since I was comfortable with myself then, I thought it was only proper I told him. We talked about meeting up for drinks to catch up, but it never came to fruition.

I decided to have a little fun. I messaged him and told him I knew him. He started asking a lot of questions, and I answered them all truthfully. It was taking him a LONG time to figure out who I was. I even told him I lived with him in college. I got very specific, and he still wasn’t getting it. He started guessing names, but still wasn’t getting it. FINALLY, he figured out it was me.

We both had a good laugh. It took him from Midtown Manhattan all the way through Queens to Long Island before he figured it out. We talked about his suspicions and our interactions living together. Sophomore year we shared a room. I told him I even looked at porn with him sleeping in the bed a few feet away. He asked questions about the logistics of that, and I explained the bathroom was right next to our room, so he would have never caught me “in the act.” Also, he always slept facing the wall, which turned out to be very convenient for me! “If I only slept on my right side!” he responded.

We chatted about it some more and he joked, “I’m not gonna lie. With those big hands and your huge feet, I definitely snuck a peek here and there when you were in your boxers back then.” He was embarrassed, but I thought it was hilarious. I was also very flattered. I referred him to my blog to catch up on my gay life so far. He said he was going to read it and then realized, “This conversation is going to end up on there, isn’t it?” I told him of course it would. He suggested I leave out some parts, such as him checking me out, but I explained those were the best ones.

I was happy to reconnect with him and we chatted a bit more. We joke about the gay resident director for our living quarters. He had a crush on my roommate, while I suspect his boyfriend had a crush on me. His boyfriend is a police officer in the local city and followed me home on more than one occasion just to say hi. We had some more good laughs and agreed we need to grab a drink together soon.

I was happy to be fostering better relationships on Grindr, as opposed to the unsubstantial ones I currently had. I needed to work harder at it, but I still had hope of finding the right guy. I will have to date half the city, but in time, Prince Charming will find me…

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