Posts Tagged undressed

Sticking to the Plan

I had a Friday to myself, and I wasted it on hookups. I could have been doing something productive like going to the gym or grocery shopping, but instead, I spent the day inside trying to line up sex.

There was one man in particular who I’d exchanged messages with on He was a well-built guy with a sexy body. He had a nice amount of body hair, great muscles and a spectacular behind. We’d talked about hooking up a few times, but we’d never seemed to line our schedules up. I messaged him, but he didn’t respond.

I continued to search for other guys on the computer when he finally responded. He didn’t read my message until it was too late. We exchanged phone numbers, and he called and told me he had a lot of errands to run before his mother’s birthday the following day. He wasn’t able to see me until later, but suggested we Skype in the meantime. I had nothing to do, so I agreed.

He was even good-looking with bed head on the computer. I couldn’t imagine how sexy he was in person. Seeing him on the computer was just making me hornier, if that’s even possible. I tried so hard to convince him to come by before his errands and do them later. All he needed to do was time-shift his day. He kept telling me the only way it would work is if I came to his apartment. I couldn’t because it was raining, and I don’t ride the motorcycle in the rain. We pushed back and forth for some time to no avail. Of course there was some teasing with body parts on camera while all this was going on. I couldn’t wait to feel his sexy body. Alas, he had to go, so I said goodbye and we made tentative plans for later. I told him when I came by, he’d certainly have to wear his jockstrap for me. He gave me a disclaimer. He was up for almost anything, but he was not up for full penetration the first time meeting me. I was a little disappointed, but understandable.

That’s when I turned to the Mexican guy in the previous post. He was willing to come by right then, and I needed a release. I had immediate regret after that encounter.

Later in the day, my old roommate texted and asked if I was interested in meeting up for happy hour. After being cooped up in my apartment all day, I thought that sounded like a spectacular idea. No one ever invites me out for drinks either. It’s usually me doing the inviting, so it was a special treat. I texted the burly man from my morning Skype session to tell him I’d have to postpone. He called immediately protesting. I told him other things came up, and I wouldn’t be able to come by. He didn’t stop persisting to try to persuade me otherwise. I told him he could have solved the whole thing had he come by earlier in the day.

The clock reached 6:00, and I hadn’t heard from my old roommate. I reached out to burly man to see if he was still available. Indeed he was. I agreed to come to his place a few miles from my apartment. He told me he would be waiting for me in bed wearing nothing but a jock and would leave the door unlocked for me to just walk in.

I drove over there and texted him when I got to his neighborhood. I tried the door, but it was locked. I called him to tell him, and he said his upstairs renter must have left and locked the door behind him. He told me to back away so he could unlock the door. I did as I was told and gave him a minute to get back to his bed.

Warning: The following may be too graphic for some. I came in, undressed down to my boxer briefs and began kissing his back while pressing my body against his. It was as great as I imagined. His a$$ looked incredible in that jockstrap! I could barely resist him. We had a lot of fun together. There was a lot of groping, heavy petting, kissing, sucking, licking, biting, rubbing, etc. It was great. I was really enjoying the jockstrap as well. I was grinding on his backside, almost penetrating him, but never fully entering him. He really enjoyed it and was pushing me further, but in the end, he stopped himself.

He was begging for me to finish, and he brought me to the edge many times. He started orally pleasuring me. He thoroughly enjoyed this, and it was turning me on since he was enjoying it so much. Eventually, I finished in his mouth and all over my abdomen, and he loved it. He began to use his hand to pleasure himself. I helped by applying pressure to different areas until he finished all over his abdomen. We’d chatted about how each of us shoots on Skype, and it was interesting how different and how similar we were. His description was pretty spot on for what actually happened.

We both just laid there a minute and enjoyed the feeling pulsing through our bodies. I still couldn’t get over how amazing his a$$ was. I wanted to penetrate him so bad, but I knew that would have to wait for another day. He hopped out of bed and handed me a towel to clean up. While I stood there, I met two of his cats. They were very cool. This guy was quite into animals. He had a huge saltwater fish tank as well. He ran to the restroom while I got dressed. I also took the opportunity to snap two pictures. He came back and got dressed as well.

He walked me outside and chatted a bit while he smoked a cigarette. He didn’t live in the best of neighborhoods. An old woman so strung out on something walked by, and he engaged her in conversation for quite some time before finally offering her one of his cigarettes and sending her on her way. He told me about how his mother lived next door and his family’s ties with the city. He was a really nice guy. I could see myself seeing this guy again some time. He told me he was also kinda seeing some guy, but it was very casual and nothing serious. He mentioned the desire to see me again sometime, but we didn’t set up anything concrete.

I sped off on the motorcycle back home to shower and get ready to go out and meet up with friends. The only friend interested in going out was P. We agreed to hit up one of my favorite local spots where I know the owner, and he takes good care of me, Cooper’s Union in Hoboken. We had a relaxing night drinking and sitting at the bar. I told her about how I was getting out of control, and it was then I decided I was going on a Grindr diet. This had gone on far too long. I was realistic enough to know I couldn’t quit it cold turkey, but I also knew it was a great temptation for me. I was going to try to steer clear. I would only go on to see if someone messaged me. I would no longer cast out a net and would no longer have it running on my phone all day. I needed a break. I was addicted, and it was time for me to ween myself off the drug…

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Is This Going to Become a Trend?

Once again I had a Friday off from work, and once again I found my libido taking over my ability to reason. I woke up that morning feeling frisky, and of course I pulled up Grindr to see who was around.

I went through a lot of guys and even started acting like all the other guys I hate on Grindr. I was skipping the pleasantries and getting right to the point. I knew I needed to find a guy who was simply looking for one thing. I didn’t want a guy who would linger or keep calling. I just wanted my libido satisfied.

I finally found a guy who seemed to be interested. He was a black man who had an amazing body. When I gave him my proposition, he surprisingly responded with a reasonable response. He didn’t normally seek out hookups, but he understood the periodic need to satiate the animal within. He wasn’t completely comfortable with just coming to my apartment and jumping into bed. He wanted to meet me in person first. I learned we both went to NYSC, so we agreed to meet at the gym and take things from there.

I get no service when I’m at the gym since it’s completely underground. I texted him just before entering “the cave” telling him what I was wearing and that I’d arrived. I worked out for nearly an hour, and he hadn’t made an appearance. I assumed he stood me up. I actually walked upstairs until I got service to exchange a few texts with him. He was on his way. I informed him I was nearly done my workout. I guess my libido was slowly fading with the endorphins of working out.

I was doing my last circuit of abs before I was ready to head out when I finally saw him emerge from the locker room. He came right over to the mat. I smiled as he approached, and he laid down next to me. He started doing sit-ups at a rapid pace — So much so that his shirt began to lift and expose his abs and the tiny shorts that barely covered him, exposing a majority of his jock strap. It certainly wasn’t anything I’d attend the gym wearing, but I could tell he was a bit of an exhibitionist.

The whole time, I waited for him to get my attention and say something, but he never did. After a few sets, he got up and walked away. I assumed he wasn’t interested. Apparently, I’d just been rejected without a word. It was quite a blow to the ego. Maybe I needed to stay at the gym a little longer.

I made my way into the locker room to change when I discovered him getting undressed right next to my locker. He was standing there in his jock strap putting his clothes into his locker when he stepped back and removed the jock as well. He was quite the “gifted” man. Of course I was sneaking a peek every chance I got. It’d been a while since I’d seen someone so “gifted” in person. It was very difficult to hide my own excitement in my gym shorts. I needed to leave before I got really excited and someone took notice.

He grabbed a towel and made his way towards the showers. It was just the tease I needed to get my engine revving again. Looks like it was going to be the computer and me when I got home.

As I left, I texted him declaring my disappointment at his lack of interest. He responded back almost immediately, “Did you leave?” I explained to him I was done my workout and thought he wasn’t interested, so I was heading home. He told me he was definitely interested, and he just didn’t want to interrupt my rhythm. He told me he’d be over in a short bit.

When he arrived, we sat on my bed chatting a bit. He was a freelance journalist over in New Jersey covering the Whitney Houston funeral. He seemed like a really intelligent down-to-earth guy. It made the hookup a little more relaxed and less transactional.

Warning: The following may be too graphic for some. Things started to get hot and heavy, and we both found ourselves naked enjoying each other’s embrace. After a short while, I took out a condom and some lube while he relaxed on his back. We were going at it for a little while when I accidentally slipped out of him. I wasn’t the only thing to fall out however. I sincerely hope my face didn’t show what was going through my mind at the time. This wasn’t as bad as the guy in San Francisco, but it certainly wasn’t pleasant. There was a pea-sized nugget laying on my sheets at the base of his behind. If this was going to keep happening, I was going to learn to be celibate.

I quickly improvised and suggested we continue our activities in the shower. We had some fun in there until we returned to the bed. I did my best to avoid the nugget while we both tried to finish ourselves off. Finally, I climaxed (I’m amazed I was able to with everything going on around me).

He informed me it would be a long time before he was able to finish himself. Apparently, he had similar issues to my own. I was happy in the realization my symptoms were finally lessening, and I was able to relax and finish more readily.

He got dressed, and I said goodbye to him. About ten minutes later, after immediately throwing my sheets into the washing machine, I received a text from him. He’d left a bracelet behind — And it was very important to him.

DAMNIT! I was going to have to see him again. I told him I’d bring it into the city sometime, but he suggested he would collect it over the weekend the next time we were both heading to the gym.

In the end, we needed to plan an evening for him to swing by and pick it up, but this time I told him, “No sex.” He stopped by for all of thirty seconds while I handed it to him through the door, never to be seen again.

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Valentine’s Letdown

Valentine’s Day had arrived. I managed to find myself single once again. I have yet to celebrate a Valentine’s Day. The one year it came while I was dating Broadway, we couldn’t be together because I got shipped off for work to the Midwest.

I ended my intense weeklong relationship with PR just the night before. I knew it was bad form to stick to our plans to go out for a romantic evening if I was just going to be faking it.

Just because I wasn’t going out for a romantic dinner doesn’t mean I wasn’t looking forward to the company of a man. For some unknown reason, I was exceptionally horny that day. Granted this has become the norm, and I’m starting to wonder if I may have a problem. However, I wasn’t stopping myself from exploring possibilities that day. I was single and ready to mingle.

I was all over Grindr and even pulled up the OKCupid app to see who was around my area. When this produced little results, I began to filter through all my previous Grindr,, OKCupid, and Manhunt contacts to see if there maybe something I missed or someone I wanted to revisit.

I messaged a few guys and asked what they were up to. The ones who I hadn’t spoken to in quite a while I asked how they’d been since we last spoke.

One guy hit me up on Grindr. I was pretty horny, so I wasn’t being picky. He was just offering to come over and give me a blowj*b.  I at the very least had a fallback. I was really looking to get it in, but I would settle for him if no candidates produced themselves.

I wasn’t happy with who I was becoming. Once again, I was letting myself get out of control. I needed to reign in my sex life, but that day, I just wanted to get it in. Tomorrow is another day.

I started chatting with the guy I’d gone on an awkward date with. We’d already talked about trying to figure something out about getting together again. I could tell he was more interested in sex than a relationship, but there was also still a glimmer of hope there for something to bud. I don’t claim to be a pro in the bedroom, but I do think, based on previous feedback, I am pretty damn good between the sheets. Maybe I could win him over that way.

We went back and forth for some time about him coming over. He wanted to go to the gym and hadn’t left work yet. Apparently I didn’t give him enough notice, but I could tell he was very interested. We talked about the logistics, and I made some great progress imploring him to come over. He told me he’d try to get his errands done and then he’d be in touch.

In the meantime, I had the blowjob on hold. I told him I had some work to do, and I would get back to him. He wasn’t thrilled, but he accepted my proposal of postponement. I told him I’d reach out to him as soon as I finished my work.

Finally, I got a text message. It appeared we were going to have our “second date” after all. He was wrapping up a few things and then he’d be over. He informed me he was bringing his c*ckring and poppers. I told him that was fine, but I wouldn’t be partaking in the poppers.

I immediately hopped in the shower to clean up, shave and prep for his arrival. I also opened a bottle of wine so we could relax before just jumping in the sack. I wanted to seduce him a little.

When he arrived, he was slightly awkward. I poured him a glass of wine and we sat on the couch chatting and drinking. When I felt the moment was right, I made a move. I was all but on his lap kissing him. And that’s when I learned why he was still single.

He was the worst kisser I’d ever been with. I thought he was going to eat my face. All that time I spent staring longingly at his lips, and that’s how he chose to use them. It was a very sad Valentine’s Day. I tried to soldier on past it. I tried to lead him and make-do the best I could.

Finally, I stood up to take a break, took him by the hand and led him to my bedroom. We slowly undressed each other. I was enjoying peeling his clothes off one by one. As I did, I was groping his entire body. He had a very sexy body and great skin. I couldn’t stop feeling him up.

Warning: The following may be too graphic for some. We laid head to toe and began orally pleasing each other. Eventually, he stopped to put on his c*ckring and grab his poppers from his jeans pocket.

When he came back to the bed, I began orally pleasing his bottom. He had a great a$s and manscaped very well. I was enjoying myself, but it didn’t seem I was doing the best job for him. That’s when I learned he doesn’t really get anything out of it, he told me apologetically. I didn’t understand because long ago he told me he was a bottom. I also recalled how much stimulation he got from his nipples, so I concentrated on them. He went wild.

A short time later, we laid next to each other stimulating ourselves. It didn’t take long before I finished all over his chest per his request. For once it didn’t take me forever to climax. As soon as I finished, he too exploded on his chest.

After giving him a towel and we both cleaned up, we laid next to each other in bed. I wanted to cuddle, but he didn’t seem the type to I just put my hand on his inner thigh. We chatted about the most random things. He was staring at my bookcase, and we talked about some of the books on the shelf. I pointed out my only gay book on the shelf, Beaches. It’s a picture book I like to page through periodically. He told me all the gay books on his bookshelf deal with barebacking. A huge red flag went off in my brain! Was he into barebacking? I didn’t ask him to elaborate, but I wish I did.

That’s when I hopped on his back and began to give him a massage. I have very large and very strong hands. I like to put them to good use. Apparently he was a little more delicate that I anticipated. He asked me to lighten up a bit, but he was enjoying what I was doing. I noticed how he analyzed everything. He really was a headshrinker.

When I stopped, he started inspecting my skin. I recalled on our date how he wished he was a dermatologist. He was very complimentary of my skin and complexion. I appreciated the compliment, but the delivery was incredibly awkward. He was not an easygoing guy, and I started to realize how little I was attracted to him. On top of that, I was starting to get an irritation on my neck from where he was trying to eat it. I knew then this would not be a repeat offender.

With that, he got dressed, collected his things, and we said goodbye at the door. He left very unceremoniously. I had no plans to reach out to him again after that. We’d had such a long history, making it weird, but we’d only really known each other a short while. He too had no plans to reach out to me.

Ironically enough, he messaged me on Grindr the other night, but of course this went nowhere.

Now, the only question is when and if I unfriend him on Facebook and what are the consequences?

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Waking up with the feeling of dread is never a good thing. Upon opening my eyes, I immediately knew something was wrong. It all came crashing back. I remember the conversation I had with Smiles the night before in my bed. It didn’t go as well as I would have liked it.

I needed to reassess the situation and make a decision before proceeding. One thing was for sure; I was going to proceed with caution. No longer was I going to invest so much of myself into a one-sided relationship. Smiles was still interested, and I had optimism the relationship could still progress towards something good. However, I could no longer devote so much of myself to someone who wasn’t doing the same for me.

I had that day off, but I had to wake very early. I needed to get my friend’s car keys before he went to work so I could take Smiles to the airport. When I volunteered to take the day off from work, I thought it would be a perfect way to see him off. I wanted to be both helpful and selfish. I wasn’t going to get to see him for a week, let alone on Christmas. The next best thing I could get was sending him off at the airport.

I climbed out of bed, put on clothes and rode my motorcycle over to my friend’s place. I swapped the bike for his car and drove back to my apartment. When I got back to my room, there were a few minutes left before Smiles was supposed to wake to get ready for his flight. I undressed and climbed back into bed.

Since we went to see the stage-show the night before, and he was working through the day before, he wasn’t able to pack yet. When my alarm went off, we woke and got ready to make our way into the city so he could pack.

I drove him through the Holland Tunnel and stopped in front of his apartment. There were no legal spots available, so I had to sit in the car while he got ready. When he got out of the car, Smiles checked out another street and texted me from his apartment: “If you wait another five minutes, you can park on the other street at the meters.” It was nice of him to check that out so I wouldn’t have to sit in the car alone the whole time.

I joined him upstairs and tried my best to assist. When he was ready, we got back into the car and set off for the airport.

My question from the night before was still in the back of my head. The car ride was rather quiet. It was as if we were both searching for something to talk about. I had yet another question burning a hole in the back of my mind. I had no New Year’s Eve plans, and all my friends did. I didn’t want to spend it alone, but Smiles hadn’t mentioned it to me. I had no idea what his plans were, but I wanted to spend it with him. The conversation from the night before didn’t change that. I was about to ask him if we could spend it together, but as we neared the airport, things got hectic because he wasn’t sure which terminal he was flying out of. That question would have to wait until later.

Once we had that settled, I found a space at curbside and helped him unload. We exchanged a very quick hug and kiss as he set off for home for the holidays. It was very unceremonious. I don’t know if he was self-conscious because we were in public or if it was because he still felt awkward, but I was very disappointed. That was not the way I wanted to be kissed by the man I was dating but not seeing on Christmas. That was not a proper goodbye.

As he walked away, he turned back and said, “I’ll call you later tonight.”

Since I had my friend’s car and the rest of the day off, I decided to run an errand I’d been neglecting. I took a route home that allowed me to stop by Michael’s to pick up a large panoramic photo I had framed. All that alone time is NOT good for me. It’s a sure to produce over-thinking and slight depression. I really didn’t know how to proceed. There was a fork in the road, and I wasn’t sure which road to take.

I decided to make a stronger effort to engulf myself with my friends. I wasn’t going to give so much of myself to Smiles, and in turn, I would fill that void with friendship. After I ran my errand, I went home and watched TV on the couch. I needed to distract myself with some form of entertainment, but it wasn’t working. I was still thinking about what I was going to do. I hopped on Facebook while watching TV and got a message from N: “I miss you buddy.” I hadn’t hung out with him since we broke up with the exception of my holiday party. Maybe it was time to give friendship with him another chance. I hit him up to see what he was up to. He was going out that night and told me he would keep me in the loop regarding his plans so we could hang out.

I know Smiles was settling in the with family, and I wouldn’t expect him to call. But, it would be nice if he called, even if just to let me know he landed safely. That night, I never heard from Smiles…

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Surprise Ending

When I got home from my dinner date with Smiles, I sent him a text asking if I could spend the following night with him at his place. I wasn’t sure if he’d already passed out, but I never got a response. I was hoping he’d answer me before I left for work in the morning so I knew if I should bring clothes for work the next day.

My office party was that Wednesday night at the Greenwich Village Country Club. We weren’t able to bring guests, but I was hoping I could see Smiles following the party. I wasn’t all that into it and was willing to leave early if need be.

Wednesday morning arrived, and I still had no answer. I decided to be on the safe side and bring clothes regardless. Maybe he’d answer me midday. When I didn’t get an answer, I asked the question again in a text.

He responded with an apology. He didn’t realize he didn’t respond the night before. “Yes. You can spend the night.” I explained the party, and he told me he had happy hour plans with his wealthy client friend and his partner.

For me, the office party was not all fun. Every year I get wrangled in to help with a few elements of the night. I performed my duties and then had fun drinking and dancing with my coworkers. It was a really good time — Better than I expected. However, I was more looking forward to seeing Smiles.

I texted him to see what he was up to. If he was still out, I was going to meet up with him. He told me he was wrapping up drinks and heading home shortly. I told him I would be leaving the party shortly as well and would come by.

I said my goodbyes and collected my coat. I wasn’t that far from his apartment, so I decided to walk. While I walked, I called his phone just to make sure he was home. I called about 10 times in a row with no answer. I sent text messages and heard nothing back as well. I wasn’t sure what to do, but I decided to continue on to his place. Finally, just as I was nearing his block, he picked up. His phone was on silent in the other room, but he was home.

He buzzed me in, and I came upstairs. I gave him a big kiss hello. I wasn’t drunk, but I was properly tipsy.

We talked about happy hour and the party while we hopped into bed. I undressed and hopped on “my side” of the bed, and he slid into his side.

Just recently, I made the switch back to briefs periodically. I decided I looked good in them since they showed off my legs — The same legs Smiles loved to compliment. So I knew what I was doing when I laid on my back in just briefs while talking to him. We chatted a bit before he made a big move. My seduction worked.

Warning: The following may be too graphic for some… As I laid on my back in my briefs, he started groping my crotch as he rolled over partially on top of me to make out. This was a bit out of character for Smiles, but I like it. Apparently he liked what he saw and went for it. I could get used to that.

Things got more heated and passionate and the clothes came off. I thought this was going to be the extent of our romp in the sheets, but apparently he was ready to escalate things. He proposed sex. I was a little apprehensive because he was still recovering from surgery. I didn’t want to further injure him. He detailed his limitations; he couldn’t top and he couldn’t put his legs up. I was still worried I may hurt him, but if he was good for it, I was game.

With that, he put a condom on me, and he climbed on top. It didn’t take long before I lost it. I’d been drinking the better portion of the night, and that really wasn’t helping at the moment. “I always lose you in this position,” he said. I found that ironic, because that was the position Broadway and I so often found ourselves in.

“Have you ever done poppers? he asked. I told him I’d never done them myself, but I’d witnessed them used. He told me it increased blood-flow and would produce one of two effects. Either it would make the problem worse or it would solve it. I figured it was worth a shot, so I agreed to partake.

He opened his nightstand drawer and pulled out a small vial. He held it up to my nose as I inhaled. Sadly, it had a negative effect.

“Let’s try one more thing. Stand up. It may help the circulation,” he told me. So I did what I was told. Magically, it worked. He turned, and I pressed my chest against his back. He lubed me up and bent over the bed, and we went at it. Finally, we were having great sex, even if it did get off to a rocky start. Apparently, he also was enjoying it as he finished on the floor. Just as he did, he turned around and said, “I wish I could make you cum.”

And it was over… I was close to finishing, but him pointing that out to me made me lose it immediately. My mind switched over immediately.

He walked to the shower, and I laid in the bed. I wanted to hop in the shower, but that wasn’t physically possible based on his setup. I thought we could have more fun and maybe I would finish. When he came back, I took off his towel and pulled him into the bed. I told him not to say things like that because it was a sure fire way to make sure I didn’t finish with him.

We cuddled for a bit, just laying in each others’ arms. Just as he was about to get up to go brush his teeth, I asked him if I could ask another question. I wanted to ask him where we stood. I wanted to know what I was to him. However, as he walked away, he responded, “No.”

I was a little crushed. I went from being so happy to finally be having great sex to utter disappointment. How was I supposed to be in a relationship with him if I couldn’t express how I was feeling.

He came back, and I was already prepped for bed. I curled up facing the wall ready for sleep. I wanted him to read my body language and realize how much I closed off, but I don’t know if he got the hint.

That night I had a dream about Smiles. I specifically remember him in the dream saying to me, “You know I like you, right?” It was the reassurance I wanted in reality, but this was a figment of my imagination. It was just that – A dream.

For the rest of the night, I didn’t sleep well. I tossed and turned like the inner turmoil I so wanted to release.

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