Sunday, I made plans with my Superman — My Clark Kent. I was very excited and could hardly wait.
I barely knew him, but I could already tell we were quite a match. On top of that, we weren’t even done the first date before he planned to see me again. It was his suggestion for us to catch The Hunger Games Saturday morning while we had breakfast.
I texted him and invited him to come over to Hoboken. We would take the motorcycle out for a ride before the movie. I ran a lot of errands that morning in anticipation of his arrival later in the afternoon. As the day progressed, the weather looked like it would cooperate less and less. The sky was covered with clouds and the wind picked up significantly. It looked like it would rain any minute.
I texted CK and suggested we hold off on the ride, and I just come into the city to see the movie. It would make things less complicated, and it would give him something to look forward to in the future.

He agreed with the new plan. I met him at his apartment with plenty of time to catch the movie. He suggested we hit up the rooftop since I didn’t get to see it the first time I was there. How could I say no to that? When I got to his apartment, we went directly up to the roof. We spent time checking out the sights, cuddling and taking pictures like we’ve been a couple for a year already. I was crushing hard!
We sat and talked, and he suggested we catch a later showing so we could relax and not have to rush to the theater. I wasn’t going to object to anything at this point. I was so happy. I was just going to go with the flow.
We finally made our way to the theater. He insisted on buying my ticket. I protested since there was no reason I couldn’t pay for myself, but he continued to insist. He wanted this to be his treat. I relented, but was sure to pick up the tab for the pretzel bites and soda.
We made our way into the theater and got great seats. Almost immediately, the PDA began between us. It wasn’t gag yourself PDA. We were simply holding hands or caressing each other’s arms. It was my kind of PDA. I was quite enjoying myself!
When the movie was over, we made our way to the street and discussed the film while we walked. This was his second time seeing the movie. He expressed interest in reading the book, and I strongly encourage him to. I was already part of the way through the second book in the series of three.
We held hands while we walked and at times put our arms around each other. I could hear a lot of people making comments, and some even began to shout or hoot and holler at us. A few of the comments were jeers and a few were shouts of support. This was not something I was used to, but it was something I would have to learn to shrug off. I’d walked through the city being affectionate with other guys before, but it never gathered this type of reaction. At one point, CK acknowledged the comments, asking, “Are they still honking at us?” I told him I thought so, and we kept walking. Frankly, I was a little surprised by it all. We were in midtown west — Smack dab between Chelsea and HK, two of the gayest neighborhoods in NYC. I had a feeling a lot of the commenters were out-of-towners, and many of them were young guys.
When we got away from the crowds, he commented how he liked how I was into the hand holding. “Not all guys are into it. I’m glad you like it,” he added. I told him I liked little signs of affection, but I wasn’t into the far more obvious public displays. I told him I’m not much for making out in public.
He also mentioned the idea that had we planned better, I could have brought clothes to wear to work the next day and spent the night, however, he was happy we weren’t taking things for granted. He was happy with the pace of things, even though he wouldn’t have been opposed to sharing his bed with me.
We stopped by Pinkberry on the way back to his rooftop as per his request. We ordered ice cream and shared spoonfuls with each other as we walked up the street. When we got back to his place, we headed straight to the roof.
We laid on one of the outdoor couches together and got comfortable while we ate our ice cream. We talked for a while before we ended up making out. Things stepped up to the next level when he undid my belt and began orally pleasuring me with one eye on the door. It was risky but I wasn’t fully exposed. I liked his passion and excitement. I’d finally met my match in terms of a decent, normal guy with a healthy sexual appetite.
After some time, he asked, “You wanna continue this downstairs in my apartment?” I told him I was totally game, and we descended the stairs.
Warning: The following may be too graphic for some. It wasn’t long before we were both naked in his bed. There was significant foreplay before he asked if I wanted to penetrate him. I was completely engulfed in our passionate romp and nodded my head in definitive agreement. “Yes! Like no other!” I added.
Then, I’m not sure how things switched so quickly, but as I was grinding on his backside, and stopped to put on a condom, he turned to me and said, “Can I f*ck you?” A long time ago, I made a rule for myself I would not bottom for a guy unless we were in a relationship. It wasn’t something I really enjoyed, so only special guys would receive the privilege. I had very strong feelings for him. I wanted to share something special with him already. I could hear A’s voice in my head telling me no sex until the third date, but that voice in my head was no comparison to the passion of my other head. After all that thinking, I said, “Yes.”
Like that, he started making out with me, and he had me on my back. While we were making out, I set the open condom down on the bed. He was already putting it on. I thought he was going to top me after I topped him. I didn’t realize I was giving up my position first. I was a little disappointed, but I let it happen anyway.
I told him it was a very long time for me since any guy had been inside me. I told him he’d have to go VERY slow. He began to slide in when I gripped his leg and implored him to stop. He told me to relax and just hold it there, but I insisted he pull out. I needed a break before we could continue. I know he thought it would be better if he simply held it there, but I was being painfully stretched. He wasn’t exactly a small guy — Quite the opposite. He pulled out, and I could see the disappointment on his face. He thought that was it, but I wasn’t giving up that easily. I just needed a second to relax again. He began kissing me in a caring way. It was as if it was his way of saying, “I never want to hurt you again.” When I regain composure, I directed him to begin again. Delight spread across his face at this news.
This time was much easier. He slid in with no problem, and began gyrating. It’d been some time since my prostate was stimulated like that, so part of it was discomfort and part was unexplainable pleasure. I never finish from bottoming, but I always have a full-body experience. I rarely can walk afterwards — Not because I’m so sore but more so because my legs go limp.
He continued until he was close, pulled out, ripped off the condom and shot all over my chest. It was very hot to watch him explode with gratification. He expressed how great everything felt, and we both laid there incapacitated. He told me how awesome he thought it was that I would flip so readily and let him top me. I told him I thought it was the best way for any healthy relationship. Both partners get to experience it all. Even though I didn’t always enjoy bottoming, I found it to be the ideal situation.
We cuddled for hours after that. We even dozed off for a period. When I woke, it was two am. I checked the schedule for the next PATH and made sure I was on it at 2:30. I said goodbye to him with a very passionate kiss, and we talked about when we’d get to see each other next. It was clear I couldn’t get enough of him. Now, the question was, did he feel the same way about me?
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Once again, today is another double post to make up for lost time. If you are just visiting for the first time today, scroll down to the previous story to keep up with the timeline. Enjoy!
It had been a long work trip. I didn’t have any spare time for anything fun other than work. The one hour I had free, I spent on the treadmill trying to get back in shape for the rapidly approaching warm weather.
After my meeting, I sped to the airport. I wanted to get home so I could start my weekend off right. I began texting everyone back home to see what they were up to so I could be efficient with my time when I landed. I sent out a flurry of texts and received a few responses before taking off. I knew at least a few people were up for drinks at the bar. I also decided to take care of my pre-game at 30,000 feet. I ordered two scotch on the rocks to help get me started.
When I landed, I got more responses to my texts. Some people were too lazy to go out. They received harassing phone calls from me urging them to sack up and join the able-bodied and willing. It was no use. I also texted my Grindr friend who recently moved to Hoboken from the city — Much closer to me. I asked him if he wanted to check out the Hoboken scene. I warned him it would be all straight bars, but he was down.
I picked up some food at the airport I could eat in the car on the way home. When I arrived, I quickly showered and got dressed. My friend took a little longer to get ready, so I had to wait for him a bit. I was getting messages from my sister and friend who were at the bar waiting for my arrival. I told them to keep their pants on… I was en route.
I met my friend on the corner and walked with him to my local watering hole, McSwiggans. I told him about the bar as we walked. He asked how my trip was, and we continued the small talk.
I hadn’t told anyone I was bringing a guy with me. They were a bit surprised. But, I wasn’t bringing him as a love interest. I was bringing him as a new neighbor and friend. He didn’t know Hoboken, so I thought I could show him around a bit. I also knew he was normal enough he would fit in. I introduced him to everyone, and we got beers. I spent a lot of the night chatting with him, but mixed in with my friends/sister as well. As the night progressed, my sister grew more and more intoxicated. She started rubbing her a$s on me like she does with people when she’s drunk. It took a lot to get her to stop.
After some time, I got a text from one of my teammates from college. He was in town at another bar, so I gathered everyone up, and we made our way to Black Bear. He was there with his new girlfriend and her friends. When we arrived, I needed to relieve myself immediately. He came down the stairs and joined me standing in line to hit up the bathroom. After we all finished using the facilities, we made our way upstairs. My group grabbed a table, and my friend dragged me over to meet his group. He introduced me while my Grindr friend followed me. His girlfriend was already three sheets to the wind and shouted into my ear, “Is this your boyfriend?” I explained he was just a friend, and we all continued chatting. When I realized I was neglecting my other friends, we made our way back to the other table.
By then my sister was wasted, and she needed to go home. Luckily, one of the guys in the group who is utterly chivalrous, volunteered to escort her home since they both lived uptown. I said goodbye to both and was left with P and my Grindr friend. When my Grindr friend went to the bathroom, I explained my predicament to her. Until this point, we were just friends, but I wasn’t sure if maybe we could be more. I asked her if I should make a move.
“Why not!? What do you have to lose?” she asked. I told her I liked having him as a friend, and if I crossed that line, I wouldn’t have a friend anymore. I wasn’t sure which I would rather have. A new friend or a new guy to date. She still suggested I go for it. I decided I would make a game time decision later.
I felt like it was mine for the taking. He always seemed interested but who could really tell? I was purposely putting out the friend vibe, but I think if I escalated things, he would be interested.
The night was dragging on, and I was tired. We closed our tab and made our way for the door. P lived in the opposite direction of my new neighbor and I. Furthermore, we decided to stop at Cluck U and get a late night snack before heading home. When he asked if we were eating there or somewhere else, I volunteered to go back to my place.
When we walked into my apartment, we sat at the counter eating and talking. When we finished, he needed to use the bathroom. I moved over to the couch in hopes he would as well when he came back into the room. He didn’t get the hint. He sat back down at the counter until I suggested he join me in the living room. When he did, he sat in the chair next to the couch. This was going to take some work.
We talked some more before I finally moved to the chair and said, “I hope this isn’t out of line, but…” and I laid a big kiss on him. He totally kissed me back. It was great. Taking the risk paid off. When I pulled back, I asked him, “Did I surprise you?” “Well… YEAH! Of course I was surprised. I just thought we were going to be friends,” he replied. “I know. I was putting out that vibe on purpose. I wasn’t sure what would come between us,” I told him. He just smiled, and we kissed again…
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New Year’s Day, Smiles woke me in the morning. I was in a complete fog. I immediately began wracking my brain to remember how the night ended. I knew we had sex, and once again, I could only remember a tiny flash of the intimate moment we shared the night before but no more than a flash. I could remember being p*ssed at Smiles on the walk home for walking five paces in front of me. And, I could remember smoking on the balcony.
I had now realized I completely wiped my phone, so anyone who texted the night before would certainly not be receiving a response from me.
Smiles was up and about walking around the apartment. I searched the room for my briefs, but couldn’t locate them. He came in the room and retrieved them for me from deep within the sheets. I had a massive headache, so he gave me some pain killers and water. It was sweet of him to take care of me in my still inebriated/hungover state. I asked Smiles about leaving the party, and he recounted the details for me. It was clear he wasn’t thrilled about it, but he also wasn’t holding it against me. The he uttered, “And I haven’t even gotten to the fun part yet!” he added.
He was going to leave it at that. I told him he couldn’t do that to me. He had to tell me what else I did. He asked if I really wanted to know, and I insisted. This is the “fun” part:
Apparently, the advances made by the guy on the balcony didn’t end there. Clearly he was persistent, and clearly I was vulnerable and well intoxicated. Smiles recounted a scene for me that drained all the blood from my face. “[The guy who sang my praises to Smiles] came up to me and asked me if you were okay. When I told him you were fine, he replied, ‘Are you sure? Because he’s making out with someone else on the couch.” I nearly passed out. I couldn’t believe it. Was I really capable of that? Could I really do that to another person after witnessing N do that to me? Was I that heartless?
I racked my brain trying to remember any bit of a make-out session on the couch. A vague image came to mind of this man kissing all over my neck. I remember asking him to stop, but also couldn’t remember putting up a strong fight. I’m not sure if my mind was making this up or if it was reality. Either way, my actions were deplorable.
I froze. I didn’t know what to do. I didn’t know what to say. I couldn’t believe he was still speaking to me. I couldn’t believe he still had sex with me that night after that. I was mortified. What was going on? My head was spinning!
“What did you do? Did you come over and stop it?” I asked. He shook his head no.
“[Smiles], I don’t know how to apologize for that. I can’t believe I did that! I can’t believe your still speaking to me right now. I can’t believe you didn’t leave me there. I don’t have words for how sorry I am. I don’t remember any of that. At all!” I plead.
“It’s okay. You were drunk. It was New Year’s Eve. Don’t worry about it,” he said.
Don’t worry about it!? I made out with another guy in front of you, and you tell me don’t worry about it?! Should I be happy you’re not that upset about it, or should I be even more hurt that you’re not phased by it. “I still don’t know what to say. I can’t believe I did that,” I added. He just looked back at me with a face that said, “Yeah. You did that.” I wanted to slither away into darkness and forget the world.
We continued to get ready for brunch and walked out the door. As we walked, all I could think about was how disrespectful I was to the man I’d grown so fondly of. Sure we had our moments where I questioned our relationship, but what I did was unforgivable. I would not have been able to forgive myself for what I did. When N did it to me, it signaled the end of our relationship.
I did this in front of his friends — Many of which I told I was dating Smiles. I made myself look like a complete whore, and I made Smiles look like a fool. The man who was singing my praises was the man who witnessed my greatest downfall. This was one of the worst things I’ve ever done in my life, and there was no making up for it and no undoing it.
I continued to tell Smiles how bad I felt about the whole thing. He was trying to make conversation and ignore the subject, but it was all my mind could fixate on. “It’s fine. Stop worrying about it,” he kept saying. We ate breakfast and talked about a few things I can’t recall because my mind was completely elsewhere. I was crushed. I almost had to leave the restaurant, Extra Virgin — His favorite restaurant, so I could go outside and cry.
It was a gorgeous day, and Smiles told me he wanted to go for a bike ride. He asked what I had planned for the day. I couldn’t think. I had no plans. I was hoping to spend the day with Smiles, but clearly that wasn’t an option. I decided I was going to try to meet Boston before he left the city, even if it was at the bus stop. I had to tell him what I did. I knew he wouldn’t look favorably on me, but I also knew he wouldn’t judge me. I left Smiles with a kiss as he walked south, and I turned and walked north. I decided to walk off my disgrace.
As I pounded the pavement from 11th street to 43rd, I tried reaching Boston. He wasn’t answering the nearly twenty-five calls I made to him. I needed him. I needed someone to talk to. I decided to hit up my roommate and see what she was doing. Maybe we could curl up on the couch and watch a movie to help make the day pass by. I talked to her for a bit, but she had plans. I couldn’t bring myself to tell here what I did. I was too ashamed. I would tell her later.
I decided to call Smiles during my walk. I wanted to make sure he knew how broken up I was about it if we were to survive this. I reiterated how bad I felt and how wrong I was as I tried to choke back tears and a vocal quiver. “Listen. It’s okay. It’s in the past. It was New Year’s Eve. You were drunk. That was 2011. This is 2012. Don’t worry about it. It’s alright,” he assured me. I think he realized how upset this made me, and that was all I could do. My fate was in his hands…
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Superman Returns
Posted by One Gay at a Time in Gay Dating on May 30, 2012
Sunday, I made plans with my Superman — My Clark Kent. I was very excited and could hardly wait.
I texted him and invited him to come over to Hoboken. We would take the motorcycle out for a ride before the movie. I ran a lot of errands that morning in anticipation of his arrival later in the afternoon. As the day progressed, the weather looked like it would cooperate less and less. The sky was covered with clouds and the wind picked up significantly. It looked like it would rain any minute.
I texted CK and suggested we hold off on the ride, and I just come into the city to see the movie. It would make things less complicated, and it would give him something to look forward to in the future.
He agreed with the new plan. I met him at his apartment with plenty of time to catch the movie. He suggested we hit up the rooftop since I didn’t get to see it the first time I was there. How could I say no to that? When I got to his apartment, we went directly up to the roof. We spent time checking out the sights, cuddling and taking pictures like we’ve been a couple for a year already. I was crushing hard!
We sat and talked, and he suggested we catch a later showing so we could relax and not have to rush to the theater. I wasn’t going to object to anything at this point. I was so happy. I was just going to go with the flow.
We finally made our way to the theater. He insisted on buying my ticket. I protested since there was no reason I couldn’t pay for myself, but he continued to insist. He wanted this to be his treat. I relented, but was sure to pick up the tab for the pretzel bites and soda.
We made our way into the theater and got great seats. Almost immediately, the PDA began between us. It wasn’t gag yourself PDA. We were simply holding hands or caressing each other’s arms. It was my kind of PDA. I was quite enjoying myself!
We held hands while we walked and at times put our arms around each other. I could hear a lot of people making comments, and some even began to shout or hoot and holler at us. A few of the comments were jeers and a few were shouts of support. This was not something I was used to, but it was something I would have to learn to shrug off. I’d walked through the city being affectionate with other guys before, but it never gathered this type of reaction. At one point, CK acknowledged the comments, asking, “Are they still honking at us?” I told him I thought so, and we kept walking. Frankly, I was a little surprised by it all. We were in midtown west — Smack dab between Chelsea and HK, two of the gayest neighborhoods in NYC. I had a feeling a lot of the commenters were out-of-towners, and many of them were young guys.
When we got away from the crowds, he commented how he liked how I was into the hand holding. “Not all guys are into it. I’m glad you like it,” he added. I told him I liked little signs of affection, but I wasn’t into the far more obvious public displays. I told him I’m not much for making out in public.
He also mentioned the idea that had we planned better, I could have brought clothes to wear to work the next day and spent the night, however, he was happy we weren’t taking things for granted. He was happy with the pace of things, even though he wouldn’t have been opposed to sharing his bed with me.
We laid on one of the outdoor couches together and got comfortable while we ate our ice cream. We talked for a while before we ended up making out. Things stepped up to the next level when he undid my belt and began orally pleasuring me with one eye on the door. It was risky but I wasn’t fully exposed. I liked his passion and excitement. I’d finally met my match in terms of a decent, normal guy with a healthy sexual appetite.
After some time, he asked, “You wanna continue this downstairs in my apartment?” I told him I was totally game, and we descended the stairs.
Warning: The following may be too graphic for some. It wasn’t long before we were both naked in his bed. There was significant foreplay before he asked if I wanted to penetrate him. I was completely engulfed in our passionate romp and nodded my head in definitive agreement. “Yes! Like no other!” I added.
Then, I’m not sure how things switched so quickly, but as I was grinding on his backside, and stopped to put on a condom, he turned to me and said, “Can I f*ck you?” A long time ago, I made a rule for myself I would not bottom for a guy unless we were in a relationship. It wasn’t something I really enjoyed, so only special guys would receive the privilege. I had very strong feelings for him. I wanted to share something special with him already. I could hear A’s voice in my head telling me no sex until the third date, but that voice in my head was no comparison to the passion of my other head. After all that thinking, I said, “Yes.”
Like that, he started making out with me, and he had me on my back. While we were making out, I set the open condom down on the bed. He was already putting it on. I thought he was going to top me after I topped him. I didn’t realize I was giving up my position first. I was a little disappointed, but I let it happen anyway.
This time was much easier. He slid in with no problem, and began gyrating. It’d been some time since my prostate was stimulated like that, so part of it was discomfort and part was unexplainable pleasure. I never finish from bottoming, but I always have a full-body experience. I rarely can walk afterwards — Not because I’m so sore but more so because my legs go limp.
He continued until he was close, pulled out, ripped off the condom and shot all over my chest. It was very hot to watch him explode with gratification. He expressed how great everything felt, and we both laid there incapacitated. He told me how awesome he thought it was that I would flip so readily and let him top me. I told him I thought it was the best way for any healthy relationship. Both partners get to experience it all. Even though I didn’t always enjoy bottoming, I found it to be the ideal situation.
We cuddled for hours after that. We even dozed off for a period. When I woke, it was two am. I checked the schedule for the next PATH and made sure I was on it at 2:30. I said goodbye to him with a very passionate kiss, and we talked about when we’d get to see each other next. It was clear I couldn’t get enough of him. Now, the question was, did he feel the same way about me?
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