[Remorse]: I am a professional man in my 40s in a major city. I live in a suburb, but during periods of harsh weather my work rents hotel rooms for key players so that we can stay in the city if necessary. I had recently noticed this late teen (maybe 20-21 at most) sitting on the sidewalk on the route that I walk between my office and train station. Scruffy, clearly homeless (well, he had a coffee cup with a few coins in it on the sidewalk), and obviously just so damn cute with an apparently tight compact body under the grime and pain. One afternoon as I walked by, he looked up, we locked eyes and he begged "Please buy me something to eat. Please!" I took him across the street into a fast food place and asked him to order whatever he wanted. I had forgotten how much teen boys can eat! Objectively, I knew that I should have just left after paying for his food, but I really found him attractive and I was more than a little curious about his plight. Yes, yes, I know that technically anyone COULD end up homeless, but this kid was world's different from the typical person on the street. At least for my city; maybe not in Portland haha. Anyway, he gave me a puzzled look when I asked if I could sit with him while he ate, but he was not resistant. "If you're here at least they won't throw me out." In between fistfuls of food, he told me his full name, explained that he had been living in several states away with his family, but they had a "falling out" and he did not think that reconciling would be an option. He did not come right out and state it, but I got the feeling that he was gay and this was the source of conflict for his family. Although superficially open, he was still somewhat vague. He also seemed a little "off," but I did not think too much about that, at least not at the time. I asked his age, and he told me he was about to turn 19. He came to my city with what sounded to me like a sketchy job offer and housing opportunity, both of which fell apart, and he lost most of his cash and his phone. Everything he had was in a small backpack. I am going to skip over a few things, and cut to the chase. I was already going to be staying at a hotel in the city that night, so I decided to simply ask him if he wanted to spend the night in exchange for dinner, some clothes shopping, and, of course, a night off the streets in a very nice & warm hotel room. I did not mention sex or money. But I did throw in "I'm gay, by the way." I was feeling emboldened by my belief that if he freaked out or made a scene, I could just walk out and let him deal with the manager, police, whatever. I had paid cash for the food and he had no idea who I was. And while I hated myself for thinking it, I told myself that I knew good and well who would come out on top if there were an altercation. How we deceive ourselves, particularly those of us with privilege. He asked if I was serious about "the whole night," asking multiple times if that meant he could stay in the room until the next morning and not be "thrown out after an hour." I assured him that I really did mean the entire night, and that I would take him to dinner, and we could have breakfast the next morning or he could sleep in if he wanted. On the way to the hotel, I took him into a drugstore so that he could pick up whatever toiletries he might need. It felt especially wicked as we both reached for a box of extra-large condoms from the display. I asked, "How did you guess?" He tilted his head to side, looked at me quizzically, and stated, "I plan on wearing these." That should have been a hint. We went to the hotel and he took what had to have been the longest shower in history. I kept telling myself to just be patient, but I still couldn't help wishing that he would hurry it up. He finally emerged and I said I would shower next. He insisted on joining me. I was OK with that in the abstract, but in the shower he was very sexually assertive, bordering on aggressive. This was very surprising given how small and vulnerable he had seemed when he was shivering on the sidewalk in the single-digit temperatures. In bed, the aggressiveness from the shower was even more ramped up. Even through I was much taller and bigger, he was incredibly strong and was easily able to physically dominate me. At one point he whispered that he had wrestled in high school, and the way he said it seemed vaguely threatening. We did things I don't usually do, and one thing that I never do, but given his strength and aggressiveness I felt that I really had no choice and so I let him do it. "You let me do this, or I can make you let me." The weirdest part is that at some level I recognize that I had to have been enjoying it. Without getting graphic, I was physically responsive to everything he did, and maybe I too vague when expressing that I did not want to allow certain things. I thought I was being clear, but he kept saying things to the effect of "Oh come on, you know you like it rough" and "The more you talk, the longer I take." I thought he would never finish, but eventually he did. He then turned back into a sweet teen boy and curled up into the down comforter, drifting to sleep very quickly. I know what I did next was a violation of his privacy, but I was feeling a bit violated myself. I went over to his backpack and rifled through it until I found his drivers license. Name, age and home state all checked out with what he told be while eating. I snapped a quick photo of his license with my phone and emailed it to both my work and personal email accounts. In case something happened to me that night, I wanted some semblance of a trail. I also went through the rest of the backpack to make sure he had no weapons (he did not), or any drugs (no street drugs, but there was an empty Rx bottle of Abilify that had his name on it). I let him nap for an hour while I caught up on some emails and dreaded what he might be like upon awakening. Surprisingly, he awoke all charming and sweet, and suggested that he wanted to be topped. I asked if he was sure, given that he was so dominant earlier. He was quickly dismissive, stating something like "I just get really horny sometimes." He was so submissive and receptive at that point, the contrast was amazing. Afterward, we cleaned up and I suggested that we get him some new clothes. "You really meant that? I was going to be happy with just the hotel and some more food!" I told him that it was his choice, but he seemed to not have much clothing (I almost let slip "in your backpack") and if we went anywhere nice for dinner he would need some fresher clothes. Or, room service was certainly an option if he wanted to avoid the cold. We went shopping and brought his new clothes back. I noticed his body language changing right before he pushed me down on the bed and straddled my chest and arms, stating "I'm going to f--- you before dinner." I suggested that I would rather wait until after dinner. He let his weight settle onto me, looked me straight in the eyes, slapped me across the face, and calmly said "That was not a question." I asked him to please take it a little easier this round. He gave me the most incredulous look that I have ever seen and practically snarled, "You already showed me that you like it rough. Get undressed. Now." He got off of me, and I thought about just bolting from the room. But, he was between me and the door, and leaving him in the room that my work was paying for (and with my laptop, briefcase, overnight bag, house keys, wallet, phone, etc.) also seemed like a bad idea. I started undressing as ordered. "Lay down on your stomach" he commanded, while quickly stripping off his clothes and then rummaging around the bedside table where the condoms and lube were. He went right to his business, as roughly as before. I was focused on just being compliant so that he would get off ASAP. It was several minutes before I reached the sinking realization that he likely had not put on a condom. He had me completely immobilized and as soon as I asked "You're wearing a condom, right?" he slapped the back of my head, mashed my face into the pillow, and picked up his already brutal pace. "Just shut up! I can't finish with you talking." I just laid there and waited for the inevitable. After a loud and exuberant finish, he collapsed on my back and breathed heavily into the back of my neck. I was strangely turned on by the feeling of his heart pounding against my back. "That felt SO good!" he finally said, clearly elated. I looked back as he pulled out and got up to go to the bathroom. Definitely no condom. He re-emerged and I slinked into the bathroom. Paradoxically, we ended up having a very nice dinner at an upscale restaurant. He seemed truly impressed and kept repeating how it was the nicest restaurant he had even been to. My mind was in a whirlwind of emotions. Here I was actually enjoying dinner and conversation with an achingly cute and sweet 18 year-old boy... who had slapped me around and essentially raped me bareback not even an hour earlier. I thought about excusing myself to the restroom, quietly paying the bill, and going back to retrieve my belongings at the hotel and just going home, but his backpack and new clothes were still at the hotel and I just couldn't do that to him. I had gotten myself into whatever was going to happen, so I just had to ride it out. I did not see myself as a victim; I was a volunteer. The rest of the night was surprisingly pleasant. When we got back to the hotel room, he just keeping going on about how much he enjoyed the dinner, and about how I had been nicer to him than anyone, and how much he enjoyed having sex with me. He asked me to lay down on my back in bed, and he proceeded to give me the longest, most attentive, and simply greatest oral of my life. He then curled up in my arms and went into a deep sleep. I though about creeping out, but he looked so innocent and I just wanted to keep holding him. I slept sporadically, convinced that at any second I would be subjected to another bareback assault, or worse. At sunrise the next morning, I awoke and spent a good 20 min just looking at my little angel. His body was so firm and perfect. With a good night's sleep and in the soft morning light, he looked younger still, which made me feel a bit creepy. It seemed unreal that this boy had been so abusive to me, and I just wanted to cradle and protect him. I asked him if he wanted to get breakfast. He smiled and sleepily asked if it would be OK if he slept in for a while. Since the room was already reserved for the next night also, I said sure, there was no hurry. I told him that I needed to go to work, but I wrote down my mobile number in case he needed to reach me. I told him that I would be returning to the hotel room by 5:00pm. I asked him if he wanted a key to the room, but he said he wouldn't need one. I asked him if he wanted me to find out about a shelter or social services, but he calmly replied "I won't go that route." I asked if perhaps I should just get him a plane ticket back to his home. He gave me a disturbingly harsh glare, then looked away and whispered "no, but thank you." So, I gathered all of my things and left him there, wondering if he would just sleep for a while, or perhaps trash the hotel room, or lie in wait and really kill me the next time. I also put an envelope with $500 on top of his backpack. When I returned that afternoon, he was gone. There was a note on the bed: "Thank you so much for yesterday and thank you for the clothes and the money! You've really helped me out. Maybe I'll see you around?" That was the last I saw of him, nor has he called. I miss him, abusive behavior and all. I am ashamed of myself over this. And if he calls back, I know for certain that I will go to him. That scares me.
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