Cousin Waseem
- 2 years ago
- 42
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The First Time I Was Fucked free porn video
This is a follow-up to my first two stories. Please check them out if you want to read about my prior adventures.
After my encounter with Devontae, all I wanted to do was go deeper into the rabbit hole. While the hook-up with Devontae did not go perfectly (he never orgasmed), I was incredibly aroused having now sucked two different cocks and rimmed my first asshole. As I mentioned previously, I no longer had any interest in practicing with my toys. Now that I sampled the real thing, I had no interest in settling for anything less. After fantasizing for so long and watching sissy hypno videos during the same time, I was really feeling like a sissy slut and I wanted more.
I tried Reddit but it was now close to Christmas and the postings were not as numerous. In addition, the holiday season was a busy time at work and a busy time at home, there really wasn’t much of an opportunity to sneak away. Well, Christmas and New Year’s came and went and as we headed into 2019, I was really looking forward to continuing with my adventures. Unfortunately, I was not able to find anyone on the Reddit personals. It was slim pickings. I was getting really frustrated. I continued to watch sissy hypnos and continued to imagine what it would be like to be a woman. Not only being a woman but being a slutty woman. It was empowering and arousing to think about. Being able to take control of your own sex life and to hook-up with random dudes is the polar opposite of my conservative upbringing. It was really intoxicating to think about.
Right after the new year, a window of opportunity opened for me. I needed to travel down to Miami for work. Awesome! A few nights by myself in a hotel? Say no more, I was ready to go immediately. Since I was going to get some alone time, I thought about buying some clothes to dress-up. As I have mentioned previously, I am a pretty hairy dude and, being married for 19 years, shaving my body hair is not something that would go unnoticed at home. Instead, if I could buy some clothes that would cover up my body hair, that may provide a good illusion for me to immerse myself in all things sissy. After flying to Miami, I drove my rental car to the nearest Target and picked up the following: yoga pants, pull-over top, and three pairs of thong panties. As an aside, Target has a nice deal on undies where you get three pair for something like 12 bucks. The only struggle is sifting through the various bins to find the right style and size. I am sure any female readers can relate. I was a bit nervous going into the store to buy some lady’s garments but I quickly relaxed when I realized that no one cared. The employees are kind of zoned out, focused on their tasks. The other shoppers are also focused on their own thing. Nobody pays attention. I was finally able to find three thongs that were my size and I checked out. Target now has self-checkout, making it easy to pay for your items without having to interact with a cashier. It was easy peazy.
In advance of my trip, I tried posting on Reddit but Miami does not have the same number of active users as Chicago and I was not able to get a solid lead. I did connect with one dude and we traded pics (he had a nice cock) but he kept flaking out. He would stop communicating and then send a note at 2 am. Clearly, he must have liked thinking about getting a blowjob but it was a fantasy for him and he was not really serious about meeting. I was also frequenting a website, sissysocial.net. I had connected with an older sissy that lived in Ft. Lauderdale and we set-up a time to meet at my hotel during my stay. Unfortunately, something came up for him and he wasn’t able to make it.
I got into town on Monday afternoon and after going to Target, I checked into my hotel and proceeded to try on my things. Everything fit okay and it looked pretty good. I really liked the yoga pants. They hid the hair on my legs but still allowed me to show off my legs with their skin-tight fit. I felt so sexy! I did not have any work obligations on Tuesday morning and that is when I was supposed to hook-up with the sissy I met from sissysocial.net. Unfortunately, he cancelled on me and I was left feeling frustrated, rejected, and incredibly horny. I had a couple of meetings for work and I found it hard to concentrate. I kept thinking about wearing those feminine clothes. I had never done anything like that before and it was such an erotic feeling to think about. Dressing up as a gurl and wanting to submissively serve a man, what was I turning into? Whenever I had any self-doubt, those thoughts were quickly dismissed by my desire to continue on this journey.
After work, I went back to my room and sulked. I dressed in my clothes and felt a little better but I really wanted to share this with someone. There was no action on Reddit, what could I do? Feeling as horny as I was, I again let my other head do the thinking and I proceeded to download the Grindr app. I had never used a dating app before and while I was a little leery, I had no idea what to expect. I indicated that I was in town for a couple of days and was looking to submissively serve someone. Since it was Grindr, I did not mention that I was an aspiring sissy, just a submissive. I was immediately bombarded with messages. Several were clear catfishing schemes, a couple were pic hunters but most were genuine dudes looking to find someone to fuck. I have to admit, I was a little taken aback given how forward everyone was. I was also concerned about safety and health. I did not want to hook-up either with some crazy dude or someone that was a live bacteria sample. It was a little odd, I was repulsed yet at the same time, strangely attracted to the activity. I sifted through the messages and chatted with about a half dozen dudes until I connected with Roberto. Roberto was a little more easy going than some of the other men and actually displayed a little personality in his responses. We agreed to continue chatting on Kik instead of Grindr so as to eliminate the messages that were continuing to bombard both of us.
Roberto told me that he was 42 (I am 48) and that he worked as a nurse at a local hospital. We chatted a little about my safety/health concerns. He assured me, as a health care worker, that he was clean and as for safety, he gave me his real name and the hospital he worked at if I wanted to confirm that he wasn’t some psycho. I gave him credit for his openness. We exchanged pics and he really put on the full court press to meet. I was still a little concerned and begged off and asked if I could think about it and see if we could connect the next night. He was cool with that. I really had a hard time sleeping that night. All I could think about was getting another opportunity to suck a cock. I woke up the next morning with a raging hard-on and knew that I had already decided. I texted Roberto that I was ready to give it a go that night. A couple of hours later he texted me that he was excited that I decided to go ahead and that he would come over to my hotel after his shift ended at 6:00.
It was another long day as all I could think about was getting together with a dude I met on Grindr. Wow, what a slut I was becoming! The feeling of wantoness and sexual freedom was really turning me on. At a little after 3, I received a text from Roberto asking if I had condoms. I responded as to why would we need condoms? “You want raw???” was his response. I texted back “We were only discussing oral, right?” He responded, “Okay, see you tonight.” I got a little indignant after that. Who does he think he is? We discussed oral only. Condoms. My ass, we don’t need condoms! I should just cancel this. What a jerk. I didn’t want to get fucked. Well…what about getting fucked? Wow, really? What are you thinking you little slut, you want to get fucked? I don’t know, it might be fun. I continued to have this argument with myself for the next couple of hours until I resolved that I should just stick to what I am comfortable with at this point.
Roberto texted me at about 6:15 to let me know he was on his way. The hospital was about 20 minutes from my hotel. I waited in anticipation. I did put on my thong, yoga pants and pullover. While it was feminine, it wasn’t over the top female. I laid in bed nervously waiting. My cock would get hard in anticipation and then soften as I worried about all the things that could go wrong. I had butterflies in my stomach and I was a little lightheaded. Finally, at about 6:50, there was a knock at my door. I opened it and let Roberto in. He was still wearing his scrubs from work but I could smell the soap emanating from him as he must have cleaned himself up before leaving the hospital. We introduced ourselves and sat down on the edge of the bed. I just looked at him and said “I am really nervous and am not sure what to do.” He told me to relax and leaned over and started kissing me. We smooched for a couple of moments and then I felt his tongue move between my lips and I started swooning.
Feeling his tongue inside my mouth really got me excited but it also relaxed me as I moved into sissy mode and just let him have his way with me. I placed my right hand on the back of his neck and caressed him while my left hand went to his thigh. I felt like such a gurl as he continued to kiss me. After several minutes of kissing, he moved back and stood up and started undressing. He asked me to do the same. Roberto was about 5’ 7” and 160 pounds. Dark skin (Mexican descent) with dark brown eyes. After we both undressed, I looked at his cock. It was rock hard. In some ways, it was a little disappointing as his dick was smaller than the first two I had been with. I would say his was about 6 inches and pretty normal girth. But, having said that, he was as hard as a rock which further excited me. I dropped down to my knees and started to suck his cock. He was easy to deep throat and I liked sucking him. As I bobbed up and down on his dick, my right hand was on his ass and my left hand caressed his ball sack. I was going to town on him and was looking forward to having him shoot in my mouth. However, Roberto had other ideas.
After sucking on him for a couple of minutes, Roberto pulled me up to him and started kissing me. He then pushed my down on the bed on all fours and proceeded to get behind me and started licking my ass. Wow!!! I never had that done to me before and immediately understood why people like it. It was an incredible feeling. I just melted as I felt his tongue enter my ass. All of a sudden, I didn’t understand why I had been arguing with myself all afternoon. Why wouldn’t I want to get fucked? This feels great! I told him how good it felt and that I was now disappointed that I didn’t get condoms. “You want me to fuck your ass?” He asked. He then got up went into his pants and pulled out a condom and without asking, started putting it on. I was immediately nervous again. I had never been fucked before. Maybe this wasn’t a good idea. But before I could say anything, I felt his cock pushing against my ass and before I knew it, he was inside me. At this point, I was grateful for his size. Anything larger may have been uncomfortable.
I am not going to get into many details of getting fucked suffice it to say it felt fantastic. I have played with my share of toys and liked ass play but had never experienced it with anyone else. Instead of getting into a detailed description of my deflowering, I want to share what was going through my mind. First and foremost, I chastised myself for being an awful lover. Roberto was incredibly attentive, gentle and caring in his lovemaking. It made me feel guilty for what I now concluded was my poor performance as a partner with my wife. Roberto would be fucking me and then would stop and ask me if I was okay? Do I like it? Did he want me to continue? Frankly, I learned a couple of things that I would be utilizing the next time my wife and I had sex. We switched positions a couple of times and when he had me on my back, I again just started thinking about what a little sissy slut I was. My legs were wrapped around his midsection and my arms were wrapped around his neck as I just gave myself to him. Every so often he would lean down and kiss me passionately. I just opened my mouth and let his tongue swirl around with mine. This was another experience of me being submissive and I loved it! Let me be an object for someone else’s pleasure. The fact that he was getting pleasure was a further turn on.
We continued to fuck for about 10 minutes until I had to make him stop. I had not “prepped” for getting fucked and I was worried that I was going to poop the bed. As he continued to bang me, I just felt my rectal cavity relax and, not having been fucked before, was worried that I was going to make a mess. I extricated myself from him and he removed his condom as I started again sucking his dick. He then pushed my head further down and I knew what he wanted…One good turn deserves another, so I dove between his ass cheeks and started rimming him. He started stroking himself and a few seconds later, he shot his load all over his stomach. Part of me was very pleased that I was able to give him pleasure to cum but part of me was disappointed that I didn’t get to taste him.
Afterward, we both laid back on the bed and proceeded to have a really nice conversation. I learned that while he was gay, he was in a similar sexless relationship. He and his partner were no longer intimate and he was bored and horny which was why he ventured on to Grindr. Despite our differences, we really had a lot in common. After about 45 minutes of chatting, Roberto indicated that he had to get going. He cleaned himself up, got dressed and gave me his cell phone number and asked me to call him whenever I was back in town.
After he left, I just laid in bed and thought about what had just happened. It was kind of unsettling for me. I was intimate with another man. This wasn’t some jerk-off fantasy or even an anonymous gloryhole encounter. He didn’t fuck me, he made love to me. This was not what I was looking for. First and foremost, this was the first of my three encounters that really made me feel like I cheated on my wife. Second, Roberto liked me because of who I was – a middle aged dude. I wasn’t a sissy to him. I got way more than I bargained for on this one and really needed to think about where I wanted to go from here. In the meantime, my cock was rock hard and it only took a couple of strokes before I was shooting my load. Apparently, my cock didn’t have the same reservations I did.
Next time, I would love to tell you about the time I sucked two different bbcs over the course of two days. Stay tuned!
After my encounter with Devontae, all I wanted to do was go deeper into the rabbit hole. While the hook-up with Devontae did not go perfectly (he never orgasmed), I was incredibly aroused having now sucked two different cocks and rimmed my first asshole. As I mentioned previously, I no longer had any interest in practicing with my toys. Now that I sampled the real thing, I had no interest in settling for anything less. After fantasizing for so long and watching sissy hypno videos during the same time, I was really feeling like a sissy slut and I wanted more.
I tried Reddit but it was now close to Christmas and the postings were not as numerous. In addition, the holiday season was a busy time at work and a busy time at home, there really wasn’t much of an opportunity to sneak away. Well, Christmas and New Year’s came and went and as we headed into 2019, I was really looking forward to continuing with my adventures. Unfortunately, I was not able to find anyone on the Reddit personals. It was slim pickings. I was getting really frustrated. I continued to watch sissy hypnos and continued to imagine what it would be like to be a woman. Not only being a woman but being a slutty woman. It was empowering and arousing to think about. Being able to take control of your own sex life and to hook-up with random dudes is the polar opposite of my conservative upbringing. It was really intoxicating to think about.
Right after the new year, a window of opportunity opened for me. I needed to travel down to Miami for work. Awesome! A few nights by myself in a hotel? Say no more, I was ready to go immediately. Since I was going to get some alone time, I thought about buying some clothes to dress-up. As I have mentioned previously, I am a pretty hairy dude and, being married for 19 years, shaving my body hair is not something that would go unnoticed at home. Instead, if I could buy some clothes that would cover up my body hair, that may provide a good illusion for me to immerse myself in all things sissy. After flying to Miami, I drove my rental car to the nearest Target and picked up the following: yoga pants, pull-over top, and three pairs of thong panties. As an aside, Target has a nice deal on undies where you get three pair for something like 12 bucks. The only struggle is sifting through the various bins to find the right style and size. I am sure any female readers can relate. I was a bit nervous going into the store to buy some lady’s garments but I quickly relaxed when I realized that no one cared. The employees are kind of zoned out, focused on their tasks. The other shoppers are also focused on their own thing. Nobody pays attention. I was finally able to find three thongs that were my size and I checked out. Target now has self-checkout, making it easy to pay for your items without having to interact with a cashier. It was easy peazy.
In advance of my trip, I tried posting on Reddit but Miami does not have the same number of active users as Chicago and I was not able to get a solid lead. I did connect with one dude and we traded pics (he had a nice cock) but he kept flaking out. He would stop communicating and then send a note at 2 am. Clearly, he must have liked thinking about getting a blowjob but it was a fantasy for him and he was not really serious about meeting. I was also frequenting a website, sissysocial.net. I had connected with an older sissy that lived in Ft. Lauderdale and we set-up a time to meet at my hotel during my stay. Unfortunately, something came up for him and he wasn’t able to make it.
I got into town on Monday afternoon and after going to Target, I checked into my hotel and proceeded to try on my things. Everything fit okay and it looked pretty good. I really liked the yoga pants. They hid the hair on my legs but still allowed me to show off my legs with their skin-tight fit. I felt so sexy! I did not have any work obligations on Tuesday morning and that is when I was supposed to hook-up with the sissy I met from sissysocial.net. Unfortunately, he cancelled on me and I was left feeling frustrated, rejected, and incredibly horny. I had a couple of meetings for work and I found it hard to concentrate. I kept thinking about wearing those feminine clothes. I had never done anything like that before and it was such an erotic feeling to think about. Dressing up as a gurl and wanting to submissively serve a man, what was I turning into? Whenever I had any self-doubt, those thoughts were quickly dismissed by my desire to continue on this journey.
After work, I went back to my room and sulked. I dressed in my clothes and felt a little better but I really wanted to share this with someone. There was no action on Reddit, what could I do? Feeling as horny as I was, I again let my other head do the thinking and I proceeded to download the Grindr app. I had never used a dating app before and while I was a little leery, I had no idea what to expect. I indicated that I was in town for a couple of days and was looking to submissively serve someone. Since it was Grindr, I did not mention that I was an aspiring sissy, just a submissive. I was immediately bombarded with messages. Several were clear catfishing schemes, a couple were pic hunters but most were genuine dudes looking to find someone to fuck. I have to admit, I was a little taken aback given how forward everyone was. I was also concerned about safety and health. I did not want to hook-up either with some crazy dude or someone that was a live bacteria sample. It was a little odd, I was repulsed yet at the same time, strangely attracted to the activity. I sifted through the messages and chatted with about a half dozen dudes until I connected with Roberto. Roberto was a little more easy going than some of the other men and actually displayed a little personality in his responses. We agreed to continue chatting on Kik instead of Grindr so as to eliminate the messages that were continuing to bombard both of us.
Roberto told me that he was 42 (I am 48) and that he worked as a nurse at a local hospital. We chatted a little about my safety/health concerns. He assured me, as a health care worker, that he was clean and as for safety, he gave me his real name and the hospital he worked at if I wanted to confirm that he wasn’t some psycho. I gave him credit for his openness. We exchanged pics and he really put on the full court press to meet. I was still a little concerned and begged off and asked if I could think about it and see if we could connect the next night. He was cool with that. I really had a hard time sleeping that night. All I could think about was getting another opportunity to suck a cock. I woke up the next morning with a raging hard-on and knew that I had already decided. I texted Roberto that I was ready to give it a go that night. A couple of hours later he texted me that he was excited that I decided to go ahead and that he would come over to my hotel after his shift ended at 6:00.
It was another long day as all I could think about was getting together with a dude I met on Grindr. Wow, what a slut I was becoming! The feeling of wantoness and sexual freedom was really turning me on. At a little after 3, I received a text from Roberto asking if I had condoms. I responded as to why would we need condoms? “You want raw???” was his response. I texted back “We were only discussing oral, right?” He responded, “Okay, see you tonight.” I got a little indignant after that. Who does he think he is? We discussed oral only. Condoms. My ass, we don’t need condoms! I should just cancel this. What a jerk. I didn’t want to get fucked. Well…what about getting fucked? Wow, really? What are you thinking you little slut, you want to get fucked? I don’t know, it might be fun. I continued to have this argument with myself for the next couple of hours until I resolved that I should just stick to what I am comfortable with at this point.
Roberto texted me at about 6:15 to let me know he was on his way. The hospital was about 20 minutes from my hotel. I waited in anticipation. I did put on my thong, yoga pants and pullover. While it was feminine, it wasn’t over the top female. I laid in bed nervously waiting. My cock would get hard in anticipation and then soften as I worried about all the things that could go wrong. I had butterflies in my stomach and I was a little lightheaded. Finally, at about 6:50, there was a knock at my door. I opened it and let Roberto in. He was still wearing his scrubs from work but I could smell the soap emanating from him as he must have cleaned himself up before leaving the hospital. We introduced ourselves and sat down on the edge of the bed. I just looked at him and said “I am really nervous and am not sure what to do.” He told me to relax and leaned over and started kissing me. We smooched for a couple of moments and then I felt his tongue move between my lips and I started swooning.
Feeling his tongue inside my mouth really got me excited but it also relaxed me as I moved into sissy mode and just let him have his way with me. I placed my right hand on the back of his neck and caressed him while my left hand went to his thigh. I felt like such a gurl as he continued to kiss me. After several minutes of kissing, he moved back and stood up and started undressing. He asked me to do the same. Roberto was about 5’ 7” and 160 pounds. Dark skin (Mexican descent) with dark brown eyes. After we both undressed, I looked at his cock. It was rock hard. In some ways, it was a little disappointing as his dick was smaller than the first two I had been with. I would say his was about 6 inches and pretty normal girth. But, having said that, he was as hard as a rock which further excited me. I dropped down to my knees and started to suck his cock. He was easy to deep throat and I liked sucking him. As I bobbed up and down on his dick, my right hand was on his ass and my left hand caressed his ball sack. I was going to town on him and was looking forward to having him shoot in my mouth. However, Roberto had other ideas.
After sucking on him for a couple of minutes, Roberto pulled me up to him and started kissing me. He then pushed my down on the bed on all fours and proceeded to get behind me and started licking my ass. Wow!!! I never had that done to me before and immediately understood why people like it. It was an incredible feeling. I just melted as I felt his tongue enter my ass. All of a sudden, I didn’t understand why I had been arguing with myself all afternoon. Why wouldn’t I want to get fucked? This feels great! I told him how good it felt and that I was now disappointed that I didn’t get condoms. “You want me to fuck your ass?” He asked. He then got up went into his pants and pulled out a condom and without asking, started putting it on. I was immediately nervous again. I had never been fucked before. Maybe this wasn’t a good idea. But before I could say anything, I felt his cock pushing against my ass and before I knew it, he was inside me. At this point, I was grateful for his size. Anything larger may have been uncomfortable.
I am not going to get into many details of getting fucked suffice it to say it felt fantastic. I have played with my share of toys and liked ass play but had never experienced it with anyone else. Instead of getting into a detailed description of my deflowering, I want to share what was going through my mind. First and foremost, I chastised myself for being an awful lover. Roberto was incredibly attentive, gentle and caring in his lovemaking. It made me feel guilty for what I now concluded was my poor performance as a partner with my wife. Roberto would be fucking me and then would stop and ask me if I was okay? Do I like it? Did he want me to continue? Frankly, I learned a couple of things that I would be utilizing the next time my wife and I had sex. We switched positions a couple of times and when he had me on my back, I again just started thinking about what a little sissy slut I was. My legs were wrapped around his midsection and my arms were wrapped around his neck as I just gave myself to him. Every so often he would lean down and kiss me passionately. I just opened my mouth and let his tongue swirl around with mine. This was another experience of me being submissive and I loved it! Let me be an object for someone else’s pleasure. The fact that he was getting pleasure was a further turn on.
We continued to fuck for about 10 minutes until I had to make him stop. I had not “prepped” for getting fucked and I was worried that I was going to poop the bed. As he continued to bang me, I just felt my rectal cavity relax and, not having been fucked before, was worried that I was going to make a mess. I extricated myself from him and he removed his condom as I started again sucking his dick. He then pushed my head further down and I knew what he wanted…One good turn deserves another, so I dove between his ass cheeks and started rimming him. He started stroking himself and a few seconds later, he shot his load all over his stomach. Part of me was very pleased that I was able to give him pleasure to cum but part of me was disappointed that I didn’t get to taste him.
Afterward, we both laid back on the bed and proceeded to have a really nice conversation. I learned that while he was gay, he was in a similar sexless relationship. He and his partner were no longer intimate and he was bored and horny which was why he ventured on to Grindr. Despite our differences, we really had a lot in common. After about 45 minutes of chatting, Roberto indicated that he had to get going. He cleaned himself up, got dressed and gave me his cell phone number and asked me to call him whenever I was back in town.
After he left, I just laid in bed and thought about what had just happened. It was kind of unsettling for me. I was intimate with another man. This wasn’t some jerk-off fantasy or even an anonymous gloryhole encounter. He didn’t fuck me, he made love to me. This was not what I was looking for. First and foremost, this was the first of my three encounters that really made me feel like I cheated on my wife. Second, Roberto liked me because of who I was – a middle aged dude. I wasn’t a sissy to him. I got way more than I bargained for on this one and really needed to think about where I wanted to go from here. In the meantime, my cock was rock hard and it only took a couple of strokes before I was shooting my load. Apparently, my cock didn’t have the same reservations I did.
Next time, I would love to tell you about the time I sucked two different bbcs over the course of two days. Stay tuned!
Elissa
- 24.06.2021
- 34
- 0
