Posts Tagged top
Shout From the Rooftop
Posted by One Gay at a Time in Gay Dating on April 9, 2012
Today is a Fast Forward Monday!!!
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…
After spending the day with The Navigator at the beach and then sharing a pretty spectacular relaxing evening together, I slept great. There was a sexy naked man in my bed, and I knew just what to do with it. We fell asleep spooning each other. When I woke in the morning, I couldn’t stop smiling when I realized it wasn’t a dream.
I still had to bring myself back down out of the clouds to keep myself in check. This wasn’t going to last forever. I didn’t care. Right now, there was a man in my bed, and he needed to be cuddled.
I rolled over and pulled him close to me. He was still slipping in and out of sleep. As he woke up, we picked up just where we left off the night before. Everything we did was fun. We were constantly ribbing each other and joking around. When we ended laying face to face, I said to him, “I just want to climb up to the roof and shout, I love my best friend, [The Navigator]. Boop!” as I reached my finger out and tapped him on the nose (an homage to Super Bad).
We both laughed for some time. We continued to cuddle all morning. I didn’t care if I stayed in bed all day. I was happy.
We were interrupted by a call from his roommate. I’d already learned he was a really good friend, and he liked to placate his friends. While he was on the phone, I took out my camera and snapped a few pictures of him lying naked in my bed. I don’t think he realized what I was doing because he had his back to me, but I wanted some souvenirs to take home with me.
Turns out, his roommate wanted to go to the grocery store that afternoon. They share groceries, so he regrettably turned to me and told me he had to go with him that afternoon before we went hiking. I was very disappointed, but I wasn’t going to make a stink about it. I quickly hopped in the shower and got ready for the day while he packed up his things and got dressed. As we walked out the door, I pointed out the Marilyn Monroe portrait saying, “My week with Marilyn.”
I drove him home and dropped him off. I was already sad to see him go even though I knew it was a matter of hours before I’d see him again. I grabbed some lunch and made my way back to the pool. I relaxed with some light reading. I needed to finish off the Tickle My Tush book so I could write my review.
When most of the afternoon passed by and some noisy kids arrived at the pool, I texted him to see how he was progressing. He was on his way home, so I decided to go get ready to go hiking and make my way over to his place.
I pick him up, and we take a short drive to the base of the mountain. I grab my camera and we make our way up the trail. When we get to a decent height, he suggests we climb back down part way and hit up another trail that had a much better view. We were having fun just being together. On our way back down, he pointed out a shack along the trail: “I wanted to surprise you, but this is going to be where we live when we get married. :)” While he said this, he took hold of my arm. I knew he was completely kidding, but it was also a sweet gesture.
When we got to the top of the other trail, we had quite a view. We could see LA and Burbank off in the distance. He took my camera from me and took some pictures of me. Again, I thought this was a sweet gesture, as were many things he did. He was just very conscientious. You didn’t have to ask him to do things; he just anticipated it. I was falling for him more and more every minute, but I still maintained my mental state.
I then turned the camera on him and snapped a few pictures. I wanted to remember the great guy I met in LA. I hoped we’d remain friends even after I returned to New York. It would certainly be nice to have a friend on the West Coast. Maybe I could even come back to visit some time.
We climbed back down the mountain and made our way to Burbank. We joked about PDA. We both agreed we weren’t really into it, but at one point he casually reached out his hand and grabbed my junk while looking the other way. I pointed out to him that just because he wasn’t looking at it doesn’t mean other people wouldn’t see it as well. We both laughed and continued to joke about other things. We walked around for a little bit and grabbed some ice cream. He was cold, and I was trying to do my best to keep him warm without making him feel uncomfortable. That’s when he broke the bad news to me.
He’d already prepared me for the possibility he’d have to go to work that night at 1:00am. He was on call, and they hadn’t gotten back to him yet. He needed to go home and nap before that shift started.
My heart sank a little. He wouldn’t be spending the night in my bed again. I needed to be a big boy about it though. I drove him back to his apartment and said goodbye. We talked about seeing each other the following day since it was my last day there; I had a flight out at 10:00pm.
I returned to my hotel room and watched TV in my bed. I knew he was napping, but it was make or break for me to ask him if he would come with me for my ride up the Pacific Coast Highway. After debating for some time, I decided to text him: “Lonely here without you already 😦 haha. What are the chances you’d wanna ride up the PCH with me after work tom?” I really didn’t want to take that ride alone. I loved his company, but I seriously feared a disappointing answer.
The Navigator wouldn’t let me down like that: “LOL. I know. I wish I were cuddling with you!!!!! That sounds like a swell idea.” I was thrilled. I was prepared for the worst, and I got the best. I was looking forward to tomorrow’s road trip so much more now that I had my Navigator! “Marylyn Misses you too,” I added.
Shortly after that text, he requested I send him some pictures of myself. “You’re most handsome ones,” he added. “Whom are you showing me to now?” I asked. Apparently, he wanted to show off his “super long first date” to his roommate and his other friend.
I was pretty crazy about him, but reality wasn’t absent from my brain. It did, however, bring a big smile to my face to know he was showing me off to his friends. It made me feel special and gave me hope I would have a longtime friend from what started as weak Grindr banter…
Follow @onegayatatimeSo When Are You Moving Back to New York?
Posted by One Gay at a Time in Gay Dating on April 9, 2012
Finally, work sent me somewhere fun, and I was taking full advantage. I stayed out in LA, managed to have some fun, and even managed to find myself a pretty great guy, The Navigator, to hit up the beach with. After swinging by his apartment, we agreed we weren’t done hanging out.
We made our way back to my hotel. After we turned off his street, I came to a stoplight. I took the opportunity to reach over and put my hand on his leg. He immediately responded positively to my advances. He reached down and laid his hand on top of mine and gave it a squeeze. We continued to hold hands the entire way back to the hotel.
We made our way to the room, and when we arrived, we quickly got comfortable with each other. We dropped our bags and laid down on the bed. We chatted a bit before he reached over, pulled me in, and we exchanged a long deep passionate kiss. When we finally came back up for air, I said to him, “I’ve been waiting to do that all day long!” He smiled from ear to ear and pulled me right back in for another deep kiss. He was a great kisser — Not just a good kisser, but a great kisser.
Was there anything wrong with this guy? He certainly wasn’t going to make leaving easy on me. I still had to keep myself in check. This thing would have an end. I couldn’t grow too attached, or I would be in for a world of pain.
The thing I liked most about the chemistry between us was how playful we were. There was no drama. We were just having fun. Everything was so easy. We cuddled and talked and tickled and joked. I felt incredibly comfortable with him. We just seemed to be on the same page about everything. He was certainly giving me hope that I could find a guy out there who I just clicked with right off the bat.
All day long, he had been texting with his friend giving him updates on our “date” as he so-called it on the beach. While we laid there he teased his friend about how good-looking I was, but lied and told him I’d just dropped him off at home while I listened on speaker phone. The exchange between the three of us was very comical and flirtatious. He showed me pictures of the guy we were talking to, and we sent pictures of me to his friend. We all had a good laugh, and his friend asked for continued updates.
The kissing slowly turned into making out. The making out evolved into heavy petting. The heavy petting became stripping. The stripping led to oral pleasures. And finally, the oral pleasures led to me learning he is versatile, which of course led to penetration. My provisions weren’t presumptuous at all. I suspect he noticed my condom/lube purchase at CVS, and this is what gave him the courage to propose going back to my hotel room.
The sex wasn’t the most amazing because I was having difficulties with the condom, but it certainly wasn’t bad. We were passionately enjoying each other on many levels.
After we had sex, we laid next to each other talking more. We attempted to take some pictures together to send his friend, but we couldn’t keep our eyes open because the flash was too bright. After our romp in the sheets and copious amounts of cuddling, I was hungry. I remembered an In-and-Out burger down the street. It was 1am, and they were one of the few places still open, so we got dressed and made our way there to grab dinner.
We took our food back to the room and had a picnic in my bed. We talked and made plans to go hiking the following day. The whole night, all I could think about was how crazy it was I even met him. It was even crazier how we both dove in headfirst. He even mentioned being worried I might be a serial killer for the first couple of minutes in the car. After we finished eating, I jokingly confirmed he was staying. He went to his bag and got changed and broke out his toothbrush. It seems he may have been presumptuous as well in packing his bag.
I didn’t care one bit. I was thrilled to be sharing my bed with such a great man. I only wished it was for a longer-term basis…
Follow @onegayatatimeSettling In
Posted by One Gay at a Time in Gay Dating on March 30, 2012
Yesterday I was shocked to receive a comment telling me I’ve been nominated for the TMI Award. I was pleasantly surprised from this great honor.
Id like to thank sensiboutique.com for blowing my mind with this great award.
The TMI Blog Award honors those blogs that discuss everything in detail and do it well. These bloggers aren’t afraid to discuss their most awkward, embarrassing and intimate experiences with honesty, humor and little to no filter.
Here are the rules
- Thank the person who presented you with the award.
- Link back to the blogger who presented the award to you.
- Share an awkward, embarrassing and intimate story in 250 words or less.
- Copy and paste the blog award on your blog.
- Present the TMI Blog Award to 5 – 10 deserving blogs.
- Let them know they have been chosen by leaving a comment at their blog.
Back to your regularly scheduled (oversharing) program…
After yet another failed date, I tried to see what other fish I could snag. It’d been a few months since my last relationship, and I was hungry for something real. It’d been even longer than a few months since I had that.
I was spending a lot of time on Grindr, Manhunt, Adam4adam.com, and OKCupid searching for Mr. Right while trying to convince myself to ignore Mr. Right Now.
I started to chat with a few guys, but work had other plans for me. I was being sent out to L.A. for a few days. I’m certainly not complaining, because this is one of the best places I’ve been sent to date. I even decided to extend my stay while I was out there. I told my boss I would be staying through Sunday night and coming back on the redeye (on my own dollar of course). The few guys whose interest I peaked would have to be patient and wait until I returned to the East Coast.
I chatted with my roommate before I left for L.A. I was debating how to spend my time out there. I knew I wanted to bask in the sun end get a head start on some color. But, would I be consulting Grindr while out there, or would I be using the time to find my center once again? A big part of me noticed I was getting out of control again, but another part of me asked, why not? I was single I could live it up. I decided I would make a game-time decision.
I landed a few hours ahead of the rest of my team. This was by my own design so I could relax by the pool for a few hours before digging in. It was one of my better ideas recently, because when I landed, the weather was gorgeous. After two short hours, I got a text from the team they’d arrived. I met them at the conference room, and they all commented on how I’d already gotten some color.
I continued to work the rest of the evening, and we went out for dinner after a longs day’s work. I had fun with this team. It wasn’t the usual stuffy crowd. This crew had level heads on their shoulders.
The next day, we presented like rock stars. I told my team how great they did and how I was going to use them as a case study going forward with all my other teams.
After we all went out for a spectacular lunch, I said goodbye as they all jetted off to the airport. For me, it was back to the pool.
While I laid there, of course I pulled out my friend Grindr. I wanted to see the talent in the Glendale area (where my hotel was). I managed to find a decent amount of guys and even started chatting with a few of them. Of course, against my better judgment, I decided to have some fun. I found a guy who was looking for fun as well, and I told him to come by. He happened to be driving through the neighborhood, so he obliged.
I made my way back to my room and waited for him to arrive. When I heard a knock at the door, I greeted a man who I can only guess was some sort of Armenian type. I really had no clue though. He had a decent body, and we got right down to business.
Warning: The following may be too graphic for some. We made out a bit until he laid back on the bed with his legs in the air. I pulled out a condom and gave him what he was asking for. He certainly liked it — I could tell because he continued to tell me how much he enjoyed it. He was a good bottom, and I had a good time. After some time, he finished all over his chest. Shortly after, I added to the fun as a smile crossed both our faces. I handed him a towel and he cleaned up in my bathroom.
As he dressed himself, he mentioned how nice it was to have a good top around. Apparently, the Glendale area had too many bottoms and not enough tops. I wasn’t sure if this was a good thing or a bad thing for me concerning the remainder of my trip.
He was also very realistic about what transpired. We both treated it very transactional. He didn’t stick around afterwards or linger. He realized we were both there to satiate the animal within, and when we’d had our fill, he peaced out. He was a body, and I was a body. That’s all. I never knew his name. I didn’t even have his phone number.
I never would have thought I could have this mentality when I think back a year ago. I was telling N nearly a year before this how I don’t think I could ever have emotionless sex. I always thought I would only have sex with passion and love back then. I wasn’t thrilled with my transformation. I would have preferred to stay the same, but I’d already realized how enjoyable sex can be.
Follow @onegayatatimePR Independence
Posted by One Gay at a Time in Gay Dating on March 23, 2012
I had a lot to think about since PR left. Was he really what I was looking for after all? I learned things the hard way over the past few relationships. I’d stayed with too many men for too long after I saw the writing on the wall. I didn’t want to repeat past mistakes.
Was I jumping the gun? Should I give this a shot? There were so many questions and no answers.
I began to build a pros and cons list in my mind.
I didn’t want to lose a great guy, but I was so tired of wasting my time with guys who just weren’t a fit for me.
CONS
He enthusiastically showed me pictures from his ski trip with his buddies in which everyone dressed in drag. They went all out with wigs, heels and bras among other things. I had a strong feeling I was not going to fit in with his friends. He also was a big fan of gay bars. He went on and on about his desire to go to Griffin in NYC on Sunday nights. It is apparently a huge gay party everyone on the scene knows about — News to me. This is not my thing, but I’m not made of stone. I would be willing to be flexible, but if this is the norm for him, we were going to differ greatly. Sadly, he may be “too gay” for me.
We are both tops. I am willing to play ball with a guy I’m in a relationship with, but I get no pleasure from bottoming. That’s not to say he wouldn’t also be willing to trade positions. But, if we both prefer it, it’s probably going to become a problem down the road for us. This was a very frank conversation we needed to have to establish expectations.
I wasn’t thrilled that he didn’t have a full-time job. I wasn’t writing him off because he was unemployed. He was in a long-term relationship with a man, and when that situation changed, he needed to find something. He fully realized what he was facing, but I just don’t know if I’m cut out to date another guy trying to get back on his feet. I put in a lot of work emotionally supporting Smiles until things ended. I really don’t want to come off as elitist at all, but I also wasn’t thrilled with the jobs he was applying for. I never did ask if he went to college, but I got the feeling he didn’t. I wondered the financial stability we would attain if we forged a long-term relationship. He was applying to jobs that I could have done over summer break from college. They had odd hours, and there was a good chance we’d see even less of each other.
PR was a good-looking man, but he wasn’t something you would double-take. I was attracted to him, but some of his physical attributes left something to be desired. I know he was making an effort to get back into the gym, as evidenced when we went together, but was that just because of me or because he really wanted to be in shape. I worried he may be habitually lazy.
Lastly, he was moving back home. Home was at least a half hour drive away, and I don’t have a car. This was going to make seeing each other even harder. I wanted someone who was going to be around when I wanted/needed him.
PROS
PR is only a year older than me. Finally I found someone in my own dating pool. We could share many pop culture references and understand them fully.
He is one of the sweetest guys I’ve ever met. He always had my best interests at heart and took great care of me. He was chivalrous and loyal. He exhibited many of the qualities I really look for in a man. It seemed I’d finally met my match in the dedication department. I knew I could trust him to be faithful and love me for a long time.
He was passionate in the bedroom. Recently I’ve put more emphasis on my needs in the bedroom. I took a major back seat with Smiles in the sack. I needed someone who could truly exhibit the passion I required between the sheets. He certainly fit the bill.
He is easy-going and always up for a good time. I could spring a fun trip on him, even a day-trip, and I know he would be onboard. I lead a very active lifestyle and need someone who can keep up. I had a feeling he could.
Overall, I was leaning towards the cons pile. It seemed to be the stronger argument. They seemed to outweigh the pros this time, and for once I was going to trust my gut.
I had a hard time deciding what to do. I spoke with Boston on the phone, and he told me I would be ill-advised if I went out with him on Valentine’s Day misrepresenting my true feelings. I thought I would have been breaking his heart if I called the night off. I thought it better to go out with him and tell him some other time I didn’t think things were going to work out. He told me I had a tough decision to make, but I needed to deal with it delicately. My friend D told me I shouldn’t cancel on him the day before Valentine’s Day. He suggested going on the date and explaining things later. He was worried PR made plans already, and I would be ruining them completely.
In the end, I finally decide I just don’t want to go. I am so tired of pretending with guys. I need to be more honest. If I feel a date is going south, I need to speak up and stop being so damn polite. I decided to tell him my feelings, but I also did it as a coward. I sent him a text…
Follow @onegayatatimeMy Adult Book Report
Posted by One Gay at a Time in Gay News on March 21, 2012
Warning: The following may be too graphic for some. It is of a sexual nature. Proceed with caution!
A few months ago, the fine folks at Tickle Kitty approached me. It seems bestselling author and sex educator, Dr. Sadie Allison published her fifth book, Tickle My Tush: Mild-to-Wild Analplay Adventures for Everybooty. They offered to send me her latest paperback that helps men and women learn the true pleasures of the under-explored “seat of love” for review on my blog.
I enthusiastically accepted the offer, and anxiously awaited its arrival in the mail. I wasn’t entirely sure what I was getting myself into, but how bad could it be? I’m gay. If I had an aversion to anal play, I’d be a very lonely man the rest of my life. Maybe I could learn a thing or two from the book as well.
I wasn’t the only one anxiously awaiting my new book. My roommates were also waiting with bated breath to see what the book was all about. When it finally arrived, we all passed it around paging though to see what exciting new tips we could learn. After we’d all had our fun like immature high school students in the locker room, I took the book back and began reading it.
Tickle My Tush is a light-hearted fun look at anal sex for mainly heterosexual couples, however, a homosexual man can learn a lot from this book. Dr. Sadie covers a lot of material in this quick read — The 14 chapters of this book cover everything from safety and heinie hygiene to toys, strap-ons, and positions of pleasure. And, Dr. Sadie takes a light-hearted approach by using playful language instead of some complicated medical jargon no one understands or uses.
This book does a wonderful job removing the stigma from anal play/sex. I can think back to when I was first experimenting with homosexuality, I wanted nothing to do with anal play. I watched it in porn, and it really just seemed like something I didn’t need. I could think of many other things I could do to satisfy my sexual urges. It was something I saw as overwhelming and uncomfortable. Frankly, I was scared of it. If you find yourself in that position, reading this book will answer a lot of the questions and will clear up a lot of the misconceptions you may have.
What I really like about this book is that it pushes straight men to open their minds and their bottoms to the idea of anal play with their female sex partners. I enjoy sex, and even as a “top,” I enjoy many of the pleasures my bottom has to offer. Having your prostate stimulated for the first time is a mind-altering experience. Many straight men don’t realize the potential their bottoms have for pleasure. I would hope books like these remove the stigma and open their minds to anal play. This book also removes the stigma for women to explore. It takes away the idea that enjoying anal sex makes you dirty or a slut. It’s simply exploring all the pleasures you body has to offer.
As you read, the book certainly gets more adventurous. It starts with safety, hygiene, anatomy and the basics and moves through finger, oral, genital, toy and strap-on pleasures.
One of my favorite chapters is 6: Sensual Booty Massage. It has always been something I’ve enjoyed. “As an often overlooked erogenous zone, those two cheeks are always eager for sensual arousal from kneading, squeezing, kissing, licking, spanking, gentle biting, father-light touching — or simply calming moments of warm-handed stillness. Why stop at the cheeks? Lustily arousing the hips, waist, small of the back, inner thighs and A-spot can add thrilling new dimensions to your lovemaking.” Some are tried and true methods I’ve been using forever, and some are a few new methods I’m dying to try.
Some of Dr. Sadie’s advise is spot on! One of my favorite parts of the book acknowledge the problem I have relaxing during sex. It’s the root of my inability to climax at times. Her best advice — UN-focus.
This book is a great read for the anal play beginner. I can think back to the guy who inserted himself with great force inside me with no preparation whatsoever. I ran out of the room in pain. I can think of the virgin who allowed me to penetrate him for the first time and how scared he was until he learned how much he loved being penetrated. I’ve been with a few newbies in my days, and there is a lot they can learn from this book. On top of it all, the illustrations that ensue are purely erotic. I think they are my favorite part of the book!
There are a few things in the book I disagree with on some level. For instance. in regard to the question, “Do you really need an enema before anal sex?” Dr. Sadie says no. But, after a few of my own horrific experiences, I HIGHLY RECOMMEND IT.
Overall, I must say, I didn’t learn a whole lot from this book I didn’t already know. That is because the first guy I slept with was a very good teacher, and I have a curious mind that has been satiated by experimentation. But, not everyone is as lucky as I am. If I had this book from the start, it certainly would have made for many less awkward situations. The thing I most learned from the book was anatomy. In fact, I often refer back to it to make sure I am giving my man the most pleasure I am capable of.
Dr. Sadie does an excellent job giving you the basic tools you need to be confident, succeed in anal play in the bedroom and know you can enjoy the untapped pleasures your bottom holds. She gives you invaluable tips that help get you in tune with your partner. She answers a lot of the embarrassing/uncomfortable things that may arise with anal play so that when you encounter them in the bedroom, you can proceed past them without the interrupting the fun. So buy it — Read it — And for heaven’s sake, try out all the new things you learn with someone you feel truly comfortable with. You’d be surprised what exciting new experiences you can unlock.
Follow @onegayatatimeNot Tired of Me Yet?
Posted by One Gay at a Time in Gay Dating on March 16, 2012
Apologies for all you who got my draft post sent out today. I didn’t realize I had it scheduled for release before finishing it. Please disregard! And apologies for the late post today.
Back to your regularly scheduled program.
So last we left off, my Grindr friend/neighbor, who I will now call PR (short for Puerto Rican), and I were making out on my chair in my living room after a night at the bars and some Cluck U chicken.
I’m sure you’ve been wondering what happened next. Well..
After some making out, I grabbed his hand and led him to my bedroom. We had our fun letting our hands explore the other’s body. Things escalated from there until we finally dozed off for the night. He wasn’t the sexiest guy to enter my room, but we certainly had a good time together. I really enjoyed cuddling and making out with him, as well as many other things we experienced that night.
When we woke in the morning, we didn’t get out of bed. We spent a majority of the afternoon laying there spooning and cuddling and just talking. I really liked how frank he was about things. He didn’t sugar coat or try to impress me. He was being real. This is a quality I seek out in men. It’s very important.
After some time, he asked the question I knew was coming, “Soooo, are you a top or bottom?” I told him I was a top. I quickly learned he too was a top. This, of course, was followed by a long awkward pause on both our parts. I wondered in the back of my head if he was convertible. He told me it was nine years since the last time he’d done it. That left a glimmer of hope that he had done it in the past, however, nine years is a long time! Maybe this was doomed before it even got off the ground. Maybe we were simply sexually incompatible. But, I liked him. I wasn’t ready to walk away from it just based on this.
After more chatting, we started to fool around some more. Warning: The following may be too graphic for some. We orally pleased each other for some time. He felt so good. Finally, we finished ourselves off laying next to each other. It took some time for both of us. When we did, he mentioned how it takes him a long time to finish. I kissed him strongly. I told him how good it was to hear him say that since we both shared that “malady.” I was happy he was understanding.
Around 1:00, we finally got out of bed. I offered to make him breakfast. I cooked up some of my homemade sausage, eggs, avocado, English muffins, coffee, etc. This was serving as our lunch and our breakfast. We watched some TV on the couch while we ate.
Finally, he decided to head home and get ready. We made plans to go out for dinner that night. I had a Living Social I was ready to burn up at Trinity, a nice restaurant on the Hoboken waterfront.
Around 6:00, I met him on the street corner between my apartment and his friend’s apartment where he was staying for the time being. We took a leisurely stroll towards the waterfront, talking the whole way. When we arrived at the restaurant, it was closed for a private event. We decided to go elsewhere rather than wait for dinner because we were both starving. He wanted to go to East L.A. for margaritas. It sounded like a good plan, so I agreed on that.
That night, he had plans to go see a movie with one of his friends. His friend wasn’t getting back to him, so he asked if I wanted to go instead. It wasn’t a movie I was looking forward to seeing, but I had no plans and was enjoying spending time with him. I agreed to go. We talked about many other things over dinner, including the other gay date we were sitting next to. The two guys were younger and we could tell it was a date by what we saw and heard. It was very cute to see — Not something you see every day in Hoboken.
When we finished dinner, we started walking down the street towards our apartments. He decided against the movie since he was tired, so we agreed to just stay in and watch TV instead. I’d never seen the Paranormal movies, and he liked them. We decided to make a Paranormal Activity marathon night of it. We snuggled on the couch the entire night. I was very happy being in his arms, and he in mine.
When the movies were over, it was late. We decided to just go to bed, and I asked him to stay the night…
Follow @onegayatatimeGray Hairs
Posted by One Gay at a Time in Gay Dating on February 17, 2012
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…
That night following my breakup with Smiles, I went home feeling some freedom. I’d already gone on a date and hooked up before breaking up with Smiles. But, now that it was official, I felt I could do whatever I wanted.
It’d been a while since I had some good, wild, crazy sex. I was horny. I had three months go by with only a little bit of lovin’ in the bedroom. I was hungry for a good man and a good time.
I was very cautious of history not repeating itself. I was not going to let myself go wild like I had after breaking things off with N. I didn’t need to do it now like I needed to do it then. But, that didn’t mean I couldn’t have a little fun.
I pulled out Grindr and began my talent search for the night. I wanted to find a good time one-night stand type. Any guy who wanted to hook up with me the first night he met me would not be a guy I wanted to date. Yes! That is exceptionally hypocritical of me, but it’s my love life, and I make the rules.
I found an old friend on Grindr while I was searching. He was a guy who came over to my apartment one rainy night shortly after breaking up with N. We were both staunch tops at the time, so we just fooled around a bit, but he had a great body and was a lot of fun. Even though we didn’t have penetration, we managed to find other creative ways to ensure the other fully enjoyed himself.
We chatted a bit, and he told me he missed me. I explained why I hadn’t been around as he told me he was hoping I’d hit him up again for a fun night. I told him to come by, and I would surely show him another good time. He tried to convince me to come to his place, but I insisted on hosting. I just felt more comfortable in my own bed.
He came by, and we laid in my bed just talking for a little bit. He had on many layers, and I slowly stripped a few off so he would be more comfortable while we laid there. Eventually, we started making out, and I rolled him on top of me.
Warning: The following may be too graphic for some: I stripped him down to his briefs and fully appreciated his body. He was an older gentleman, but he certainly kept in shape. Everything was still tight and sexy. I hoped I would be in such good shape when I was older. Ironically it was that night I learned he was in his last year of his forties. I had no idea he was so old. I was shocked in fact. It didn’t change the fact that he was a sexy specimen of a man, but it kinda flipped my mentality on end. Up until this point, I thought the forty-year-old was the oldest I’d been with. He looked a lot like Ulrich Alexander Fox.
Regardless, he had a great d*ck and an amazing ass. I was ready to have some fun. I recalled his position as a top only, so I knew there would be not penetration again, but ironically enough, he volunteered, “Maybe sometime I’ll let you inside me.”
I was completely caught off guard. I replied, “Really!? Why’s that?” “Because you’re sexy, and I really feel comfortable with you. Maybe some day.” I asked if he ever bottomed, and he told me it’d been many many years since he’d last done it. I felt privileged. I was getting the ego boost I needed to get me back on my feet. It couldn’t have come at a better time. Here was a guy who was looking forward to another romp in the sheets with me, and we’d never even had full intercourse. Maybe I was better in the sack than I gave myself credit for :).
I had a lot of fun with him that night. He went down on me, and I finished like a pro. He commented on how he wished he still got as hard as I did and was able to shoot like I can. I then, with jello legs, helped him finish as well. He certainly deserved that after the fun night I was having.
Afterwards, we laid next to each other and just talked for a while. It was then I learned he was actually black. I’d noticed he wasn’t a white guy, but I wasn’t sure what his background was. I had nothing against this at all. I’d just thought maybe he was of Middle Eastern descent or possibly Egyptian. I also learned he was adopted by what seemed like a picturesque white family in Connecticut. He was very happy explaining his upbringing. I could tell there was a lot of love in that family. I was happy I had a real man in my bed and not just a body to hook up with. I’d never start a relationship with him, but at least this friend with benefits was an interesting guy with a big heart.
He again told me how much he missed me and being with me. He also told me he hoped we could find time to meet up again in the future. He encouraged me to come to his place some time since he lived alone and had a nice apartment. I told him I would certainly come to him next time. I learned he really wasn’t a creep, but a decent guy with a decent libido.
I once again took the opportunity to admire his body and tell him how hot he is. He was embarrassed by my compliments and talked about his need to take more care of his body. I insisted it was pretty amazing, and he directed the attention toward mine. He told me in detail how hot I was and how thrilled he was to have fun with me.
We continued to talk as her got dressed. I walked him to the door and gave him a kiss goodnight.
It was exactly what I needed right when I needed it. I had fun. I got an ego boost. And, I had a smile on my face for at least the rest of the night. I would sleep a very happy man that night!
Follow @onegayatatimeAm I Broken?
Posted by One Gay at a Time in Gay Dating on December 13, 2011
The following topic of conversation is very embarrassing and very personal. It’s not easy to talk about, but I have a strong feeling I am not the only one who suffers from the issue. Warning: It may make some of you uncomfortable. I am exposing myself in this post, but I feel I need to face my demons to be able to get over them. I also feel guilty writing about this, because it’s a bit of an invasion of privacy for others, but I also feel it’s necessary if I’m being honest with myself and this blog. I wonder if someone out there may have insight to help me and others with this predicament. I feel the need to shine a light on this issue, as no one is talking about it.
My intentions were obvious this time around with Smiles. My hand was down his pants fondling him until I was pushed away with a grunt. There was no misconstruing my intentions. After being denied sex yet again by Smiles, I felt the need to consult my council.
I called Boston for his take on the situation. I explained being denied sex on more than one occasion. His immediate response was, “Oooooo. That’s not good. Something isn’t right.”
I responded, “I know, right? I just wanted to make sure I wasn’t making a mountain out of a mole hill.”
We chatted about the issue, and he told me I needed to address the issue. “Sex is an important part of any relationship, and based on what I read in your blog, sex is important to you,” he added. We discussed the best way to bring it up. The main consensus was waiting until the relevant situation arose. He suggested I don’t bring it up over dinner. If I was denied again, I should bring it up immediately to find the root of the problem.
This was the point in the conversation where I made a small confession of my own. I was worried I may have been to blame for the quantity. I explained my climaxing issue to Boston for the first time in full detail. I told him, while I’d been with Smiles a few times, I had yet to climax. This was through no fault of Smiles. This was a common occurrence for me dating back to the days I was with Broadway. In fact, I feel it was a large part of the reason we broke up. It put a lot of strain on the relationship. He took it personally, even though I assured him it had nothing to do with him. I was still quite attracted to him and still received pleasure from sex, but I wasn’t finishing.
I never was able to find the root of my problem. For a while, I hoped it would fix itself. When it didn’t I explored a number of theories. The leading one being I hardwired my brain to function in a specific way in relation to sex.
For 16+ years, my main outlet for my sexual frustrations was viewing gay porn and pleasuring myself. I wasn’t dating men, and I wasn’t exactly a lady killer either. I would go home, open the laptop, and take care of myself. I worried my brain was hardwired to react only to that stimuli.
I wanted nothing more than to “fix” this issue. For some time, I masked it by prepping myself. If I knew Broadway and I would be having sex, I watched porn before I saw him to build up a “spank bank.” I referred to this when he got me close to finishing to get me over that last hill. It worked for some time, but eventually that solution lost its effectiveness. That’s when things got really bad. I got so stressed about it, when the moment came, there was nothing I could do but think about my lack of performance. I was so wrapped up in the issue, there was no unwinding me at that point.
I had many frank discussions with Broadway on the subject. After discussing it, we agreed not to talk about the issue for some time. It was the only way I was going to be able to relieve some of the pressure I was putting on myself. Eventually it did the trick, and I had my happy ending. However, it wasn’t a 100% solution. Most of the time, I was only able to cum after he performed oral sex. A majority of our relationship, I never climax from anal penetration. The issue was still there. It was just lessened.
It wasn’t as big an issue with San Francisco because we were an entire country apart. When I was physically with him out in San Francisco, I had no issue. When we Skyped, it took slightly longer, but eventually I climaxed. After San Francisco, I slept with a handful of guys. I specifically remember it being an issue with The Trainer. I know it’s not an issue of physical attraction, because he had a body like a god! However, I had to finish myself off that time, and it took some time.
When I was dating N, it took a long time, but I almost always finished. He started noticing my “condition” as time went on. We discussed it lightly, but I think he was under the impression it just took me a little longer than most guys to finish. As I’ve said before, I had to resort to my “spank bank.” Many times, what I was imagining involved the two of us. I wasn’t even imagining porn stars. It was the two of us in different scenario/locations other than in my bed.
Over the summer, it wasn’t really and issue for me. I had no strong connection to the guys I was sleeping with. It was purely recreation and my own need to get some crazy out of my system. I had no pressure or image to keep up. I was just having fun, and it worked.
The first time Smiles and I had sex, I bottomed. No matter who I have been with, I have never finished from bottoming. It has its pleasures, but it never had that effect on me — Hence my status as a preferred top. With Smiles, there was one time when I was very close during oral sex. I was right there, but I just couldn’t close that final gap. After we had sex other times, and I still didn’t finish, I began to morph my theory.
I have a very high pain threshold. Because of this, I wonder if I am in turn cursed with a high pleasure threshold. Maybe it takes more to get me off. I also wondered if my stimulation comes from something more visual. Maybe I need to witness the penetration to climax. Again, these are all just shots in the dark, no pun intended, but I want nothing more than to figure out this enigma. However, I haven’t been able to test my theory at this point.
Smiles expressed his interest early on to work with me to figure this out. It meant a great deal to hear him verbalize this to me. I need someone who can be understanding and patient with me if I’m going to lick this thing.
After I talked to Boston, after a drunk night at the bar, I discussed in length with D my issue. This was really tough for me because I am so embarrassed by the situation. It makes me feel like less of a man. He was helpful in our discussion and helped me feel more comfortable talking about it.
I also called to Broadway. I didn’t exactly feel comfortable talking to him about the details of my new relationship, nor did I think it was fair to him. But, he had experience with this issue. He knew what was going on with me, and maybe now that we weren’t together, he could help me find the key. When I told him I was being denied sex, he immediately said, “Something’s wrong! That’s not normal. You need to talk to him about it.” Everyone was telling me what I already knew, but not what I wanted to hear. In thinking I was partially responsible for the situation, I brought up my issue. Maybe he was avoiding sex with me because I couldn’t finish.
Broadway told me I needed to stop being so stupid about it. I was stressing myself out over it, and that wasn’t going to solve anything. I needed to acknowledge to myself the issue and go see someone about it. I told him I had been entertaining the idea of going to see a therapist, but it takes a very special type of therapist for such a sensitive issue. It wasn’t exactly the easiest thing to find in the yellowpages. He again just indicated I needed to talk to someone about it if I wanted to get over it. He also reminded me I needed to talk to Smiles directly about why we weren’t having sex more often.
The next morning when I woke, I sent Smiles a message detailing my desire for him to be in the bed next to me and how horny I was. He responded positively and seemed he would have been up for morning sex had he actually been there. I was surprised considering a few hours earlier I was denied.
We made plans for Sunday, and I went on with my pondering my issue for the rest of the day. Did he think I didn’t enjoy sex? That certainly isn’t the case. Even if I don’t finish, I still thoroughly enjoy sex and still get a body high from it. Did it bruise his ego to know I wasn’t being fully stimulated by him? I can assure him, it is me, not him. There were a million questions, but no solid answers.
One thing is clear. I need help. I cannot solve this problem on my own, but maybe talking about it with my therapist, Dr. WordPress, will help me face my demons head on and conquer them. Only time will tell…
Follow @onegayatatimeBack On Top
Posted by One Gay at a Time in Gay Dating on November 30, 2011
In unrelated news, I came across this video from my fellow blogger, http://www.ty-curious.com/. He shared it with me, and I think it’s spectacular. Totally safe for work! Hope you like it! Take the time to check out his blog too. Great guy!
On with the story…
After my ride back to Hoboken, Smiles and I chatted on Facebook.
He described his drunken night involving too much Patron and a lost iPhone. He hadn’t had a chance to track it down, so I offered my assistance to make some phone calls for him. He was grateful, but had it under control. While he described his night, I described my time out in the sticks with no power or technology. “Yeah… It was a real Amish paradise,” I said.
Once again, I had to facilitate plans with him. He typed, “Okay. Off to go get food. I’m starved.” I quickly replied, “What are you doing later?” I knew it would be difficult getting ahold of him the second he signed off for the day. It’d been a while since I’d seen him, and I was anxious to do so. “No plans, although I may go back to the bar tonight for a Halloween thing,” he declared. I wish he had the same desire to see me to invite me without provocation, but I’ll take what I can get. “Wanna try to get together later?” I asked.
“Jump on the bike and come over and have brunch with me,” he finally stated. I explained the bike was snowed in with a dead battery, but I told him I’d meet him for brunch. I quickly made my way into the city to meet him at the Christopher Street PATH station. I arrived well before him and waited for him to show. I couldn’t call to find out what was keeping him, so I tried to occupy myself with my phone.
When he finally arrived, I wasn’t greeted with a kiss. I could have initiated the situation myself, but again, I was still in the mindset to play a little hard-to-get. We walked to a nice brunch spot neither of us have tried before, Barbuto. It was great. We got a nice seat next to the kitchen, which in most situations is a bad thing, but in this case, was entertaining.
Smiles ordered a beer after wavering between that and a bloody mary to help cure his hangover, and I ordered a glass of red wine. We took the time waiting for the food to arrive to catch up with each other. He was a little quiet, but I had plenty of stories to tell from my time home. We talked a bit about his family as well, and I started to get a better picture of the dynamic going on there.
Our food arrived, and we were both very pleased with the results. After we paid our tab, we decided to walk around a bit since the weather was so gorgeous. We walked to Doma Coffee Shop to grab coffees while we walked around. We had no plan for our day. After we grabbed caffeine, he turned to me and asked what I wanted to do. I told him I was just happy to be out, and it didn’t matter to me what we did. We started to walk around aimlessly. When we came upon Pleasure Chest sex shop, he suggested we pop in. This wasn’t the first time walking into a sex shop with him. I was game.
We looked at all the toys in the place and even asked one of the workers there to explain one of the feminine toys to us. We had more than a few laughs as we perused the store.
We spent the rest of the afternoon walking around SoHo looking for hats to replace the one he lost. I was happy to spend the day with him. We did some shopping for other things while we searched for hats. While I was checking out to pay for the flannel shirt I picked up, I could see in his eyes he was exhausted. He was fading fast. He suggested we go back to his place to take a nap. I myself wasn’t feeling very sleepy, but I rather liked the idea of napping with him.
We got back to his place and climbed into bed. I put on my new flannel and got comfortable. Surprisingly, I passed out rather quickly. He, on the other hand had a hard time falling asleep.
Warning: The following may be too graphic for some. After about an hour, we were both awake. He turned to face away from me, so I decided to make a move. I engulfed him in my arms and spooned with him. After some time passed, I gently began caressing him all over and slid my hand between his thighs. I began massaging him until he turned his head back to kiss me. It was on — FINALLY! Things only got more passionate from there. It wasn’t long before he pulled out a condom, put it on me, and climbed on top. I was finally getting my turn as top dog (even though I was on the bottom). The sex was good, and I enjoyed having sex facing him with the lights on. However, once again, he finished, and I wasn’t able to.
Embarrassment came flooding in. I was very attracted to him, and I enjoyed the sex, but something underlying wasn’t allowing me to relax and fully enjoy the moment. I was very close, but I just couldn’t get over that last hump (no pun intended). This wasn’t the first time this happened, but it certainly didn’t make it any easier to deal with.
After sex, we both showered and cleaned up. He had plans to meet friends at his favorite restaurant to say goodbye to a bartender friend who was leaving for another restaurant. I was a little curious why he didn’t extend an invitation, but I didn’t want to dwell on it. We made some progress, and I wanted to concentrate on the positive. I was doing my best to play hard-to-get, but I really liked him. I wanted this to continue. I wanted to get to know him more. I wanted to be closer to him physically. I wanted him.
We got dressed and walked towards the PATH and Extra Virgin, where he was headed. When we reached a crossroads, we said goodbye with a quick kiss and went on our separate ways.
Later that night, I got a message from him complaining about having to go to the bar to see if his phone was found. I sympathized with him and wished him luck.
When he got back from the bar, he messaged again to tell me he had no luck. I felt bad for him, but selfishly, all I could think about was how hard it was going to be to get ahold of him without a phone. The next couple of days would pose an interesting challenge.
Follow @onegayatatimeAt the ripe age of 26, I came to a life changing conclusion. I'm GAY!
It took me 26 years to realize this and come to terms with it, but coming out's been the best decision of my life.
This blog is about my dating life in NYC and what happens next...
One Gay at a Time 
Lazy Morning
Posted by One Gay at a Time in Gay Dating on February 3, 2012
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 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 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.
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 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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