A doubleheader with Doublelist
A doubleheader with DoublelistIt has been a very busy nine months for me. As I have mentioned in my other stories, I am a middle aged (48), married man. I went from never having any extramarital activity in our 20 years of marriage to becoming a wanton sissy slut. Please see my stories to read about my other activities. As I mentioned in my last story, Paul, a BBC dude that I get to service periodically, and I were not able to get together for a period of time due to our schedules. Part of the problem was my work. I was travelling a lot and was not available. However, since I was out of town, I thought it might give me a chance for some additional playtime.I only have a couple of pictures in my profile but they are from my last business trip. I was able to buy some additional clothes on my last trip. In addition to the make-up I had purchased previously, I had a nice bundle of goodies to play with. I purchased the clothes and jewelry on Amazon and had them shipped to an Amazon Locker near my hotel. How convenient! Now that I know this is available, I look forward to buying more stuff locally. Anyway, I got myself a dress, pantyhose, earrings, and a choker. I also remembered to buy make-up remover (see last story) and I was ready to go. After a long day of travel and work, I looked forward to getting femme on my first night. My make-up application went much better than my first time but I still have a long way to go. Eyes are tough. Kudos to the ladies that have mastered liner and eye shadow. In my room, all made-up, I was soooo horny. I really wanted to suck a cock. I tried my usual Reddit personals but Miami just doesn’t have the same type of activity as Chicago. I did not want to try Grindr again so I decided to give Doublelist a shot. It was a very frustrating evening as it took forever for my posting to be published. I am not sure what the moderation process is but I ended up going to bed irritated and horny. The next day, I was happy to see that my post was finally up:Married dude with a submissive bi side. In town for the night and able to host. I am clean, DDF and expect same. 6’2” 185 in good shape and want to have some fun.Over the course of the day, I received about a half dozen responses and I was quickly able to narrow them down to two. One was a white dude that was not very experienced and the other was from a black dude that was looking for a submissive. Either one would have been okay but my kinky side favored the black dude and we traded messages throughout the day. I wanted to make sure he was clean and needed to confirm the time we could meet. We then traded pics and after we were both okay with each other we talked about timing. I had a dinner party after work and asked if we could meet at 9:30. The rest of the day I had a hard time concentrating as I was only able to be thinking about my pending hook-up. Dinner was a long winded affair that I thought would never end. Finally, at about 8:45, I was able to make my exit and I headed back to the hotel. I anxiously awaited my… I don’t even know what to call him. We never exchanged names and we were just texting each other on Kik. Just thinking about the anonymity got me turned on. The thought of servicing a complete stranger continues to be extremely arousing for me. At about 9:15, he texted me to confirm my availability and to get my room number. I gave it to him. The next message I got really stopped me in my tracks. He told me to be completely naked on the bed – with the door to the room open. My dick was rock hard at güvenilir canlı bahis siteleri the thought of leaving my door open. I proceeded to get undressed and then I opened the door and slowly let it close without latching. I then laid down and hoped that no one else would decide to walk in. At a little after 9:30, the door to my room opened up and in walked this older black dude. When he saw me on the bed, he just smiled and started to undress. He was about 6’ tall with very broad shoulders. While he was a little overweight, he still looked very athletic. His head was completely shaved but he had a mustache and goatee, both of which were very gray. He was wearing a t-shirt, shorts and flip flops. Once naked, he climbed into bed next to me, grabbed me by the back of my neck and pulled me to him and started kissing me. He immediately forced his tongue inside my mouth and started swirling it around with mine. I just melted in his arms. After a couple of minutes, he directed me to his chest and I started to nibble and suck on his nipples. He groaned in appreciation and I continued to make my way down to his cock. His cock was normal sized, about six inches with okay girth but it was very hard and also very curved. The curvature of his dick made it challenging to get down my throat from between his legs. I continued to suck on him as I thought about changing my orientation so that I could get at his meat from a better angle. He had other ideas.Before I could move from my spot between his legs, he grabbed my head and shoved it down below his balls, clearly beckoning me to lick his ass. I eagerly complied and he let out a very satisfying moan. He let go of my head and started stroking his own cock as he lifted his legs higher to give me better access to his hole. He urged me to spread his cheeks with my hands and really get my mouth into his hole. I felt so slutty, it was amazing. I continued to tongue his asshole getting it soaking wet with my saliva. In the meantime, he continued to stroke himself all while continuing to encourage my rimming. After only a few moments he started to cum and shot his load all over his stomach and chest. I can’t lie, I was disappointed. As much as I enjoyed the submissiveness of licking his asshole, I really wanted that cum in my mouth. He didn’t waste any time as he got up and asked if he could use the bathroom. He went to the bathroom to clean himself up and I crawled back up to the top of the bed. He made small talk as he finished cleaning himself up and dressed. Before I knew it he was gone. I looked at my watch, it was 9:42. Fuck! That was it?? Well, that barely scratched the itch of my submissiveness.I got back on my laptop and started surfing Doublelist to see if I could find anyone else. Unfortunately, I was not able to make a connection. Miami is a challenging place. Because the traffic is so bad, people really want to stay near their neighborhoods. Being near the airport, there weren’t many people looking to make the trip to my room. I ended up just jerking off thinking about the night’s activity. While it was abbreviated, thinking about rimming that dude was a real turn-on. This was now the third time I rimmed a guy and I had to admit to myself, I really liked it. You whore, I thought to myself as I came into the palm of my hand and proceeded to lap up my own jizz. I settled down for the night and fell asleep with a smile on my face.The next morning I drove to the airport from my flight back home. While I was at the airport, güvenilir illegal bahis siteleri I was pleasantly surprised to get an e-mail from my tryst partner. It was a brief message that said “Last night was awesome, please keep in touch and contact me on your next trip down.” That really perked up my day. I spent most of the flight daydreaming about rimming that guy’s ass and then I started thinking about rimming other guys’ asses. Boy, my depravity seems to know no end. I got back home and went directly to the office. Because I had to make that trip, I had assigned a bunch of work to various folks on my team. They were doing a tremendous job and it looked like the next day (Friday) was going to be pretty open. On Friday morning, I started surfing Doublelist to see if there were any opportunities available. There were several and I started chatting with some folks. Before long I had three possibilities lined up. As usual, the interactions started eliminating the choices and soon I was down to one option. An older dude in the southwest suburbs was looking to “play” that afternoon. He seemed like an okay dude and before long we agreed to meet at his house at 3:00. I was able to complete my work and sneak out a little early and I headed to his house.Just after 3, I pulled up to his house and walked up to the door and rang the doorbell. Almost immediately, the door opened and I was greeted by another dude with a goatee and mustache. What’s with goatees? This guy, however, was an older white dude, short – about 5’ 8”, and very skinny. I would guess that he was in his mid fifties. He was wearing only a t-shirt and a jockstrap. Wow, this will be interesting. He introduced himself as Danny and he showed me inside and asked me if I was ready to play. I smiled and said I was and he showed me upstairs to his bedroom. Once in his bedroom, he stripped off his t-shirt and jockstrap and stepped up to me and started kissing me. He smirked and said “Why do we do this?” I simply responded, “because it is fun?” He smiled, kissed me again, this time with an open mouth and our tongues danced together. He started undressing me and I helped him. Once I was undressed, he started caressing my cock and I started caressing his. What a cock! His was about seven inches, cut, with a mammoth mushroom head. It was gorgeous. My mouth watered at the thought of taking that into my mouth. We continued to kiss and stroke each other’s cocks. I then dropped down on my knees and took that beautiful dick into my mouth. It tasted wonderful as I bobbed my head up and down on his meat. Soon I was taking him all the way to the base and he was moaning like mad. He stopped me shortly thereafter and told me he did not want to come so quickly. He then had me get on the bed on my hands and knees. He then proceeded to start eating out my ass. Ummm, it felt wonderful. After a couple of minutes, I felt him stick a finger inside me. And then another. And then another. It felt great. He asked me if I wanted to get fucked. “Yes, please” was all I could say.Danny flipped me over onto my back and then said “Hold on a minute.” I presumed he was going to get a condom. Instead, he brought out a towel, raised my ass and stuck it under me. “We don’t want any messes.” He then proceeded to stick his bulbous head against the crack of my ass and started pushing. Am I about to get fucked raw? I shouldn’t be doing this, I told myself. What are you thinking? Clearly I wasn’t as I just laid there, yearning for his hard cock to be güvenilir bahis şirketleri inside me. He then spit into his hand and rubbed it over the head of his cock, lifted my legs and pushed that fuck meat inside of me. I can’t tell you how good it felt. It was fantastic. He pushed the whole thing inside me and then stopped to let me get used to it. He leaned down and kissed me, his tongue forcing its way into the back of my mouth. I just moaned, wrapped my arms around his neck and my legs around his midsection. While I came to his house dressed as a normal dude, I never felt more like a sissy than at that moment. He then proceeded to start fucking me. Boy did he fuck me. Up to that point, I thought Danny was just a high energy guy. However, as he really started to pound me, I started thinking that he was on speed. He was going a mile a minute – and I loved it. His cock in my ass felt great. After about five minutes he pulled out and turned me over. I had my legs on the ground and was bent over the bed as he rammed his hard cock back into me. I laid on my stomach, my arms outstretched and just thought about all of the sissy videos I had watched of women getting fucked exactly like this. I was in heaven! I was able to maintain at least some sanity and knew that I couldn’t have him cum inside me. I wasn’t willing to take that chance. After some time, I stopped him and had him pull out. I then dropped to my knees and experienced another first, ass to mouth. I started sucking and deepthroating his cock tasting my ass and loving the experience. After a couple of minutes, Danny stopped me, again telling me that he did not want to come yet. I then had him get on the bed and crawled between his legs, lifted his legs up and dropped down and started licking his ass. He let out a moan. He started stroking his cock and told me how good my mouth felt on his hole. He then asked me to start squeezing his nipples. “Harder!” he yelled and I started squeezing and twisting his nips as hard as I could while my mouth was glued to his ass and my tongue danced around his hole. He really started groaning. Remembering what happened in my last encounter, I moved from his ass and got my mouth back around his cock and sucked him for all I was worth. Shortly thereafter, he grunted and filled my mouth with his spunk. It was delicious. God, I love the taste of cum! I continued to suck him to make sure I got any remaining drops from his gorgeous cock. After a couple of minutes he pushed me away, telling me that his cock was ultra sensitive. We both started to get dressed. At this point, I was convinced he was on some sort of amphetamine as he could not stop talking. I learned about his ex-wife, his current girlfriend, his girlfriend’s son, and even his “other” girlfriend – a former high school classmate that he sees on the side. I couldn’t get a word in edgewise so I just kept my mouth shut and continued to get dressed. Once dressed I started walking toward the door. Danny followed me all the while continuing to prattle about the various women in his life. I thanked him for the good time and left.On the way home, my feelings were mixed. I had a couple of new experiences that were amazing and really scratched my submissive itch but I was also concerned about having unprotected sex. As I drove home, I reconciled with myself that I can be a slutty submissive sissy but that doesn’t mean I can’t also protect my health. I told myself that if I wanted to continue with these kinds of encounters, I needed to be more careful so that I don’t run into any unwanted hiccups. As I look back on these experiences, I continue to relish the ATM, the ass licking, and the cum swallowing and eagerly look forward to more. If you have read all of my stories, thanks for following along in my adventures. I hope to have some new ones to share soon!