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That Tuesday, I woke to the sound of my alarm. I was going to go for a run, but the sound of my alarm wasn’t all I heard. It was raining outside. I turned off the alarm and looked out the window to see rain pouring down. I checked my phone to see if CK texted, but he hadn’t. Who knew what happened? I sure didn’t.
I wanted to text him when I got to work, but I decided against it. He knew where I was. He was the one who suggested plans that evening. He would be the one to hit me up and clue me in on those plans.
Finally, around noon I got a text: “Hey sexy.” I didn’t see it until a little later. I responded, “Hey. How was the rest of your night?” Apparently he’d gotten tipsy at the work event he called me from. He went home and passed out in all his clothes including his shoes. When he woke at 4:00am, he properly put himself to bed. The he apologized for not calling me back and asked how my night was. I mentioned my cancelled run, and he expressed interest in going for an early run with me sometime. Tthat would be the only way he’d do it since he’s not a morning person. I told him we’d both just stay in bed because I’d just be tempted to lie there with him.
I then asked him if we were still on for that night. “I’m game. What’s the plan?” he responded. I reminded him he set the plans, and I was waiting for the details. He decided he’d rather stay away from alcohol, and I asked what he wanted to do instead. He was eating his lunch, so he asked if he could get back to me later. 5:00 rolled around, and I still hadn’t heard back from him. I certainly wasn’t feeling very special anymore. That’s when the phone rang. I was heading into a meeting, so I sent him a text. When my meeting ended, I called him but got no answer. At 6:00, I finally got a call back. He was heading home and wanted a quiet night in with me. I wasn’t opposed, but I wasn’t thrilled either. I was beginning to wonder if it was all about sex with him. He needed time to straighten up his apartment, so I made my way over there around 7:00.
When I got to his apartment, I stood in the hall waiting for quite some time before he answered the door. I hadn’t called to tell him I’d arrived. A small part of me was surprising him on purpose. He just happened to be getting out of the shower.
He greeted me with a giant hug and a big kiss. I removed my shoes and got comfortable. He finished toweling off and joined me on the bed. We cuddled a bit until he asked me if everything was alright. I lied and said everything was fine. He pointed out I seemed short in my text messages. Big kudos to him for noticing the subtleties in my mood. We continued to hug until we discussed what we wanted to do for the evening. He mentioned watching the sunset, and I told him that’s exactly where my head was.
I had ulterior motives. When we got to the roof, I would find the appropriate time to bring up my concerns that arose since Sunday. He also asked if I wanted to smoke, and I shook my head yes. “Are you sure everything is cool?” he added. I told him I was short in my texts cause I was actually working all-day and apologized. I didn’t really think I was being all that short. We smoked and finally made our way up to the roof about a half hour later, Coronas in hand.
When we got to the roof, we continued snuggling on the outdoor couch. We talked about the surrounding buildings in an “I’m high” kinda way. The conversation never really had any direction. Then again, he brought up my mood and asked if everything was alright. I didn’t think I was being that obvious with him, but I also wasn’t being myself. That’s for sure. I didn’t know how to let myself be free with him anymore. I started to close myself off to ensure I wouldn’t get hurt. I was shoving distance in there with both fists.
I finally told him how I was feeling. I explained how I thought his sentiments came out of nowhere on Sunday. I told him I thought it was a bit early to have that conversation, but now that it’s been had, a few issues were brought to top of mind. I addressed my feelings regarding him being on Grindr and how that made me feel. I told him I felt as if I wasn’t enough for him. I told him I didn’t need to be on there, and while I wouldn’t dictate to him to not be as well, I just didn’t understand why he felt he needed to still explore it.
I was having a hard time expressing my feelings, but I think I got the point across eventually. I told him because of what he told me, I was afraid of getting hurt. I wasn’t able to be myself and give him the real me if I felt vulnerable to pain. I wanted to be myself with him. I wanted to give him the real me. I needed to feel safer than I did. “Since meeting you, you’ve made me feel incredibly special. Since you told me what you did on Sunday, I no longer felt special,” I told him.
He looked a bit shocked. “The last thing I want to do is make you worried or scare you. What I said to you on Sunday was not calculated. It was just how I felt at the time. You are incredibly special, and that hasn’t changed. You are… an aspirational boyfriend. I’d be insane to do anything to lose you. Baby, I think you’re incredible. Part of me knows how amazing you are and wants to dive in full force, but another part of me wonders if I still want my freedom. I’ve already started thinking of you less as something to schedule in my life and more as just part of my life.”
I wasn’t expecting him to tell me he wouldn’t hook up with other guys and tell me we were exclusive. I think I just needed him to know how I felt and where my head was. I could see in his eyes that he understood what was in front of him. I would still be patient and let him figure it out on his own. I just wasn’t going to find myself in another Smiles relationship. He needed to know that eventually the Grindr would have to go, or I would have to go. He needed to know that I wanted a boyfriend and not a friend with benefits. I needed to hear from him I wasn’t just a hookup cuddle buddy. I needed to know I was different from the other guys he slept with from Grindr.
We kissed and embraced. I felt a lot better. It was really starting to weigh me down. I think I handled it very well to suit my needs. A large part of me wanted to ignore the conversation we had in the Sonic parking lot. The other part of me, my constantly overactive brain, wanted me to get some closure on the topic. I think I found the sweet spot.
Warning: The following may be too graphic for some. After kissing and embracing, he began to get a bit frisky. He started to undo my pants. There was high risk here. We were in plain sight of the doorway leading to downstairs. One neighbor had already come up to the roof once to smoke. He began blowing me, always keeping one ear out for signal of someone approaching. I undid his pants and began pleasuring his endowment with my hand. Finally, paranoia got to him, and he suggested we move to the far corner of the roof, out of sight of the door.
When we got over there, he pulled my pants down to my ankles and did the same with his. He was pleasuring himself while going down on me. He edged me many times, getting quite close to making me finish. I was picturing my seed all over his chest, just as he wanted it. Alas, I wasn’t able to fulfill his wish. I came close many times, but just couldn’t get over the hump. He stood and suggested we move downstairs. We got dressed and made our way downstairs. I was incapacitated and had a hard time descending the stairs. My legs were jello from the full-body orgasm he gave me. I may not have had the release, but I still received all the pleasure. He laughed at my struggle.
As we walked down the stairs, I realized he had a slight exhibitionist streak in him. The stunt on the roof, sex with the blinds always open… I had a bit of this in me, but in smaller quantity. He was expanding my comfort zone.
When we got downstairs, the fooling around continued until we took a break to order Thai food. It was 10:30. Once that was taken care of, we had sex. I had the first chance on top, and then we swapped. It wasn’t long before he finished all over my back. He was out of breath and in a daze from how amazing it was. I knew I was having a blast, but I was thrilled our time in bed was so enjoyable for him.
Like clockwork, the food arrived. We settled into bed and ate while we watched Smash. I convinced him he needed to see the show so I could talk to him about it. He really enjoyed it, so much so we watched two episodes, eventually switching to dessert. I passed out half way through the second episode. When it was over, we turned out all the lights and went to sleep. I was happy to have the weight off my back after telling him my concerns. I felt comfortable with him once again. I fell asleep with an amazing man in my arms and a smile across my face from ear to ear.Follow @onegayatatime
Another Monday. Another day at work. My staycation was officially over. Another day periodically checking Grindr.
I spent my vacation getting myself back. The only problem was I only repaired the physical me, not the mental and emotional me. I wasn’t on Grindr all day long, but I would periodically check it to see if anyone had messaged me. I was simply a Grindr fish. No longer would I be a fisherman.
I had a dermatologist appointment in the middle of the day. While walking to my appointment, I fired up Grindr. I was curious to see if anyone was scoping me out. I was also in a new neighborhood. I was hoping to find something new and unexpected. In the short window it took me to walk about twenty blocks, I’d managed to strike up a conversation with three different guys. All seemed to be quite level-headed. I told them all I was looking for dates, and all of them seemed excited at the prospect. It was difficult trying to keep three conversations going at the same time. I told them I was walking into my appointment and asked each of them for their phone numbers. I managed to pick up a lawyer, an actor and someone who worked for a magazine rating cruise ships. I asked each of them for their pictures to add to my roster and went to see my doctor about lightening up a scar.
When my appointment was over, I thought I’d make my walk seem shorter by checking messages on Grindr once again. A guy near my office was on and started messaging me. He seemed pretty hot and well fit. He was staying at a hotel near me and was anxious to give head. I told myself not to even continue the conversation, but once again, I found myself thinking with the wrong head. I entertained the idea and asked him what he was proposing specifically. He told me he had to catch a flight in a short while, but wanted some fun before leaving New York. I immediately knew which hotel he was staying at and his occupation. “You’re a flight attendant staying at the Radisson, aren’t you?” I asked. “Yea. How did you know?” he replied. “Not the first one I’ve talked to at that hotel. You guys love that hotel, and you guys love Grindr. So what exactly are you looking for?” I texted.
He asked me to come to his room. He would leave the door ajar. I would walk in, he would tear off my pants and just begin orally pleasuring me. I wouldn’t have to touch him or do anything to him. He just really wanted to blow someone. I knew better, but I still bit anyway. I figured, “What’s the harm?” Work had no idea how long my appointment would last, and it was a slow day at the office. I decided to take a detour, but I basically had to run to his apartment. Thank God I have long legs to get me there. He was anxious because his checkout was very soon.
I arrived at his hotel in time for an afternoon tryst. I hopped in the elevator and made my way to his room. I’d been here before. This wasn’t my first b.j. from a flight attendant at the Radisson. I really needed to stop making that a habit, but at the time, I was excited to get off in the middle of the afternoon. I arrived at his room, and the door was left ajar.
Warning: The following may be too graphic for some. I walked in and said hi. He immediately began lifting my shirt and sucking on my nipples. I lifted my shirt off, and he undid my pants. Just then, he turned to me and asked, “You’re really clean right?” I assured him I was. “You can never been too sure,” he added.
He began pleasuring me. After a few minutes, I made my way to the bed and laid back. I wanted to fully enjoy him. It wasn’t too long before he worked his magic, and I was able to conjure up exciting mental images. I shot in his mouth and all over his face and chest. He spit on my chest and began working on himself. Seconds later, he shot all over my leg. “Let me grab you a towel,” he said immediately. I wasn’t moving. I was quite anxious to get both of “us” off me.
I cleaned up and began to exchange small-talk with him. He was Austrian and was headed home that evening shortly after I would be departing his room. I needed to get back to the office, and he needed to finish getting ready for work. He told me how much he enjoyed himself, and with that, I made my way out the door.
Shamelessly, I had a smile from ear to ear. I was still high from the endorphins. It felt amazing. I was ashamed and proud in the same moment. I still knew I was broken inside and needed to stop having these trysts with strangers, but I was also enjoying my sexual liberation. Somewhere, there had to be a happy medium. It was up to me to find it…Follow @onegayatatime
FraI already started my morning off with a little frisky visit and some well appreciated service. It was time to join the real festivities.
I walked out into my kitchen to find my roommate with all her college friends and my other roommate with his girlfriend. I thought I pulled a fast one on all of them sneaking my visitor in the back door, but I was wrong. My male roommate saw him come in. He and his girlfriend questioned me on it, and I was completely honest with what happened. They were fascinated by how transactional it was. They couldn’t believe it, and his girl gave me a high-five.
I celebrated myself with a nice cold beer from the fridge. It was already 1:00 and I was well behind the rest of Hoboken. Before I finished my shower, I had four down. That would be enough to scratch the surface.
I got dressed and convinced my roommate and his girlfriend to come with me to a friend’s apartment. She was having her annual St. Patty’s Day bash. I was meeting D and K there as well. I was happy D was going to be in town. Since his car got a flat, he wouldn’t be visiting his girlfriend in Philly.
When I got there, the party was already well underway. I sat on the arm of the couch and conversed with my friends. I just took in the scene. For some reason, I wasn’t really feeling St. Patty’s Day this year like years passed. I didn’t feel the need to get sloppy drunk.
Of course, since my bladder has shrunk since college, I had to go to the bathroom. Since I was somewhat bored at the party, I was chatting with a sexy man I’d been chatting with for some time on Grindr. We’d talked about getting together so many times, but never did. Things were getting very flirtatious and leading toward an afternoon hookup. When I went to the bathroom, he suggested I come over. I took the opportunity to sneak out the door when I finished in the restroom instead of returning to the party. I’m sure it was just a matter of time before my friends realized I’d gone, but it wouldn’t be immediate.
I wasn’t even slightly drunk. I’d been anxious to see this guy for some time. I wasn’t about to let the opportunity pass. I quickly walked home, grabbed my helmet, hopped on my motorcycle and sped off uptown. Before I left the party, my Grindr friend asked me how I felt about glory holes. I told him I’d never used one before. When he sent me a picture of a sheet with a hole cut in it and a caption reading, “How would you feel about this?” I became excited. He told me he’d leave the door unlocked. I was to walk in, come to the sheet, unzip and let him take care of the rest.
Warning: The following may be too graphic for some. As I entered, I noticed how nice his place was. I was a little shocked. I walked straight to the sheet hanging in the bathroom door. I hadn’t even fully unzipped before he reached his hand around the sheet and began. It felt amazing! He continued for some time before I reached my hand around the sheet and began to stroke the back of his head. I could feel him, but I couldn’t see him. Finally, my curiosity got the best of me, and I just pushed the sheet to the side. I wanted to see him. He was very attractive in his pictures and even more so in person. On top of that, the only thing he was wearing was work boots.
After a little more time, he turned around and I began grinding myself against his backside. He was extremely hot and he knew how to use his body. I reached around and used my hand to pleasure him as well. He was VERY gifted. I hadn’t felt one like that since my friend in San Francisco.
He then requested we move things to the couch. I sat down, and he straddled my lap. It didn’t take long before he finished all over my chest and without warning. I had no idea it was coming. I tried to finish as well, but it was no use. Between my morning visit and the few beers I had, I sat there for quite some time without climaxing. He was so hot and he tried everything to help me finish, but it was no use. I gave up and apologized. I could tell he was very disappointed. He blamed the drinking, and I concurred that was to fault.
As he stood in front of me, I took all of him in. He had a spectacular body, and I let him know it. I asked him about his workout routine, and he told me he didn’t since his heart attack. He elaborated and told me it was no big deal, but I was a little worried. I could only think of him keeling over in front of me.
We chatted a little bit more while I got dressed and looked around a bit. He told me he had a roommate, but he wasn’t home. Something didn’t quite line up, but for some reason, I was buying the story. While we chatted, he stood in front of me in just his boots with his large gifts swinging back and forth. He was very proud of them as well. He put sweatpants on so he could walk the dog, and I could see his large bulge. I commented on it, and he commented how he loved how people would check it out, especially the guys with their girlfriends. I was so turned on. I also learned he managed a bar in the city, and he told me I should hit it up sometime.
We talked about meeting up again sometime soon. We both thought the other was thoroughly sexy and wanted a repeat. He was particularly looking for a sequel since he didn’t get a happy ending from our first encounter.
I said goodbye and made my way back downtown to my apartment…Follow @onegayatatime
After my tryst with the Armenian and the Asian, I decided to order some real dinner. This was the last night I was on the company dollar, so I ordered some room service. While I waited, I chatted with the guy who wanted to come by later in the night. I sat and ate my meal in bed with just the TV to keep me company. I was feeling lonely, which is such a strange emotional state to be in considering I’d just shared one of the most intimate acts with two other men.
When midnight arrived, I started texting my late night snack. I asked him what he thought his E.T.A. would be. He told me it was still up the air, but he was definitely coming by. He was out with friends and would swing by on his way home.
Finally, around 2:00am, he texted he was finding parking and would be by shortly. Ten minutes later, I had a knock at the door, for the third time in a matter of hours.
He was a very nice polite black man who was anxious to spend some time with me. He seemed very young and innocent. We chatted a bit while sitting on the bed before any action began. It was getting late, and as rude as this sounds, I was ready to get it in and go to bed. I wanted a nightcap so I could doze off soundly till the morning.
Warning: The following may be too graphic for some. We had A LOT of foreplay and prep before anything happened. He really wanted to cuddle for a long time before we could even get frisky. I was almost ready to call it quits and ask him to leave. It was getting late, and I was getting tired.
There was a lot of kissing. A lot of heavy petting. A lot of licking and sucking. Finally, he was ready and got into position for me to penetrate him. I could tell this wasn’t a guy who gave it up to just anyone. Normally, I’m really into the foreplay and making out, but I’d already had my engine warmed up earlier that evening. In fact, the car had been taken around the block a few times.
I’d saved my climax for him and quickly learned this was a big mistake. He was very bad. We didn’t go for very long because I really wasn’t getting anything out of it. Finally, I stopped and rolled onto my back. I tossed yet another condom in the trash and started taking care of myself. He laid next to me and asked me to finish on his chest. I obliged his request, and he followed suit shortly after.
I knew he was going to be a lingerer. I tried to cut that off at the pass. I humored him for a short bit of time before I finally spoke up and said how I needed to get to bed. It was past 3:00am. It was time for him to go! He got the hint and got dressed. While he did so, he asked if we could hang out again while I was in town. He told me how much he enjoyed himself. I didn’t shoot him down, but I didn’t exactly give him the answer he was looking for. I told him I’d have to see what my schedule allowed for. I told him I was trying to get the most out of my vacation in L.A.
With that, I said goodbye, shut the door, showered all the men of the night away, and climbed into bed to dream about the sunny sandy beach I would be visiting the following day.Follow @onegayatatime
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.
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.Follow @onegayatatime