Inside the Mind of a Cocksucking Sissy
- 2 years ago
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Inside The Mind Of A Cocksucking Sissy, Part 2 free porn video
This is a follow-up to my last story that I posted several weeks ago. After I finished writing Part 1, I got ready for bed, butterflies in my stomach, feeling excited about my encounter the next day. I don’t know about all of you but as I have gotten older, the day to day emotional highs and lows start to flatten out, life loses some of its excitement. Maybe it has to do with having more life experiences – you get used to them. Maybe it has something to do with getting older and having less energy. Whatever the reason, there are times when I am just “meh” about my life and I kind of feel a little dead inside. Well, that night, I felt like an eight-year-old on Christmas Eve, all excited about the presents I would get the next day. I had a hard time falling asleep as all I could do was think about Jim’s cock and getting another chance to service him.
I finally fell asleep and the next morning I got up and did my morning ride. My adrenaline level was high and I powered my way through my work-out as I was thinking about my upcoming encounter. My dick was semi-hard as I was so turned-on thinking about this follow-up meeting. Of course, the inevitable happened. I got an e-mail from Jim apologizing, but that he would have to cancel. Cancel??? What the hell?? I was crushed. Jim said that he had to set-up an emergency dentist appointment for a toothache. Really, a toothache??? Well, fuck me. My mood changed dramatically. I went from excited anticipation to depressed. Part of me wanted to tell Jim to fuck off but that I knew that wasn’t appropriate. This wouldn’t be the first time a guy flaked on me and it probably wouldn’t be the last. Who knows, maybe we would hook-up again some other time. So, I just responded with “Ok, hope you get some relief. Lmk if you want to get together another time.” I started thinking about putting up my DoubleList post or maybe trying to seal the deal with someone on Sniffies. In any event, I went upstairs to shower and get dressed for the day.
By the time I got out of the shower, I got another e-mail from Jim. The butterflies came back as I anxiously opened his message. “Hey, my dentist can’t see me until later, are you still available?” What? Is this really happening? Talk about a roller coaster of emotions. I e-mailed back that I was available right now but that if he was in pain and wasn’t feeling it, we could do this another time. He quickly replied that he was horny and really wanted my mouth on his cock again. I then responded that I could get to his place in about 30 minutes. I got another immediate reply that he would be waiting for me. I finished getting dressed and headed out. While at first I was thinking about whether Jim was bullshitting about the toothache, I quickly put that out of my mind as it didn’t matter. All that mattered was that I was still on my way to his apartment to have my second encounter with this guy. I couldn’t wait. I put on some sissy hypno to listen while I drove to his place. By the time I got there, my mouth was drooling.
After parking and walking over to his building, I sent him a note that I was downstairs. It was a nice morning, sunny and warm – a really nice, fall day. I took in the sunshine, looking up and down the block, trying to contain my excitement as I waited for Jim to come down and let me in. After a couple of moments, Jim came outside to greet me and after saying our hellos, I followed him inside. His apartment is on the second floor and as we walked up the steps, I was looking at his ass, covered by his sweatpants. I had a smile on my face as I continued to follow him down the hallway to the entrance to his apartment. We went inside and he bolted the door behind us. “I am sorry to hear about your tooth but I am glad we could still meet.” He just smiled and said “No worries, I have been taking Advil and as long as I not chewing, it isn’t too bad.” I followed him into his bedroom and he turned to face me. “So, you’ve been looking forward to sucking my cock again?” I just smiled at him and dropped to my knees. I started rubbing his semi-hard dick through his sweatpants and looked up at him with lust in my eyes. I started kissing and licking his hardening tool through his pants while my hands caressed and squeezed his ass. After a couple of moments, I pulled down his sweats to free his cock. It was as sexy as I remembered. His cock is cut, has a nice sized head and is a nice thickness. I don’t think his dick is quite seven inches when fully hard but it is a nice cock and I was licking my lips in anticipation of sucking on it.
Before I could get my mouth on it, Jim pulled his pants fully off, stepped toward his bed while he also took off his sweatshirt. Now completely naked, he laid down on his bed and spread his legs, inviting my to crawl between them to start servicing his cock. I got on my hands and knees on his bed, between his legs, my mouth just inches from his cock. I gave his beautiful tool a couple of kisses while a caressed his thighs. Jim pulled out a little bottle, “Poppers?” I politely declined as he inhaled deeply and the smell of amyl-nitrate started filling the room. I opened my mouth and took his now hard cock head into my mouth. “Mmmm” I moaned as my tongue started swirling around the tip of his dick. I started caressing his balls as I started moving my mouth up and down on his hard pole, getting it wetter and wetter each time. Soon, I was deepthroating his tool as he grunted his approval. I dropped my mouth down and started sucking on his balls while I stroked his shaft with my right hand. Jim then pulled out a bottle of lube and said “let’s get this baby lubed-up! It’s water based so you can keep sucking it.” As I gripped the top of his dick, he squeezed some lube on the tip and I worked it over his entire shaft as I continued to stroke him. “God damn! That feels good!” You think that feels good? What till you feel this. I continued to stroke his cock but dropped down my mouth to start licking his ass. “My god, you are great!” Jim moaned as he lifted up his legs to give me better access to his asshole.
With his legs pulled up, his arms wrapped around the back of his knees, me still stroking his shaft, I was staring at his asshole. I then turned my gaze up to Jim and I locked eyes with him as I placed my mouth on his puckered hole and stuck my tongue inside and I began to rim him. “Jesus, that feels good!” I continued to rim his ass for a couple of minutes but soon, I was dying to get his cock back into my mouth. I left a trail with my tongue from his hole, through his taint, his balls, and all the way up his shaft until I took his cockhead back into my mouth. The lube was pretty tasteless and I immediately deepthroated him. Jim groaned in appreciation. I slid my head back up to the tip of his delicious cock and started sucking on him while I also stroked his shaft with my right hand. My left hand was caressing his thigh and I just felt so… content. I loved the feeling of his warm cock in my mouth. The sounds of me slurping on his dick coupled with his moans were incredibly arousing. Unfortunately, it was over too soon as he started bucking his hips and growled “Here it comes! Take my cum!” I greedily took his load as it filled my mouth and started sliding down my throat. It tasted wonderful. I continued to suckle him to make sure that I didn’t miss a drop but he started jumping everytime I nibbled his dick as it was so sensitive. It was clear that he was done with me. I gave his inner thigh a quick peck and got up. I asked him if I could use his bathroom to wash my hands as they had a mixture of lube and sweat that made them kind of sticky. Jim told me to help myself as he started getting dressed. We made small talk for a few moments and then I excused myself and left. As I walked out, I thanked him and reminded him that he could contact me anytime and that I would love to come back.
Just like the first time, my drive home was a dream. I was in a semi-euphoric state as I relived the encounter. Everything about it, driving to his house, being submissive, sucking his cock, rimming him, and finally swallowing his cum made for a fantastic experience. I could do this every day, all day. Needless to say, I again had some powerful jerk-off sessions after that encounter and hoped that I would hear from him again. The mental aspect of being another guy’s regular cocksucker was really scratching an itch that I didn’t know I had. It was great! Things were quiet for the rest of the week. The following week I had to go out of town for work and was fearful that I would miss another chance with Jim. At first I was happy that I didn’t get a note but then I was also kind of bummed that I didn’t. Was that it? Two times and he was done? Given my work, travel, and family obligations, I thankfully didn’t have a chance to dwell on it. But the following Monday morning, back at home, I was working out in the basement and was feeling a little randy. As I was doing a plank, I started thinking about Jim. What if I sent him a note? I wonder if he would like to see me again? I don’t know if it was karma but when I finished that rep, I went to my phone and what did I see? An e-mail from Jim. “Hey, are you available this morning? I have a huge load I would love to give you. Lmk.” I quickly responded and I told him I could be there within the hour. He asked me to hurry-up and that he would be waiting. I finished my work-out, showered and headed to his place, telling my wife that I had to go into the office.
The route to his apartment was becoming familiar now and I started daydreaming about his beautiful dick. I couldn’t wait! Soon, I was back at the front of his apartment building, oozing with anticipation of having another go at Jim’s cock. What a cocksucker I have become! That thought just heightened my arousal. Soon, Jim was opening the door and back up to his place we went. This time, after we got into his apartment, he immediately started stripping off his clothes and dropped down on his bed, naked, with his semi-hard dick beckoning me to come closer. I crawled between his legs and immediately smelled a new scent. “Hmmm, you smell good.” I moaned. “You like it? I just showered, the soap is scented.” “Mmmmm” was my only response as I took his cock into my mouth. As I am servicing him, Jim likes to start talking really raunchy. He would ask if I think about sucking off my boss or other guys I work with? Would I like to see him fuck my wife? What other guys have I sucked off? Things like that. I have to admit, taking my mouth off of his cock so that I could respond, all the time making eye contact with him, filled me with a shameful warmth that was very arousing. When he asked me why I liked sucking his cock and I responded “Hmm, I love how hard it is. I love the head and swirling my tongue around it. Your cock tastes great and I love how warm it feels in my mouth.” I could feel myself blushing as I said these things, one part of me being embarrassed but another part of me embracing what I have become. I followed my tried and true routine. Sucking him, stroking him, suckling his balls, rimming his ass, caressing his legs all while trying to maintain as much eye contact as I could. Watching him watch me, added a whole other level to the experience and I tucked that knowledge away so that I would remember to do this as often as possible going forward. Jim also has kind of a fantasy of wanting to cum twice. “Are you ready to swallow two loads today? Do you want me to cum twice.” Having serviced him a couple of times already, while I would love to get him off twice, I presumed that he was just talking. Sure enough, I responded with “I would love to swallow your come as much as you want” as I continued stroking his shaft. He started groaning and shaking and he grabbed by head and pushed it back onto his cock as he shot his load. It was a nice one as it really filled my mouth. This was the first time that I was having a hard time keeping the load in my mouth while continuing to suck on a dick. I persevered as his body stopped shaking, I suckled the tip to make sure I got it all and then I swallowed. The thick, greasy load slowly slid down my throat while I smiled at Jim. “Do you want me to keep sucking?” I asked. Jim responded that he didn’t think he would be able, and I took that as my cue to make my exit.
I had the same euphoric drive home as I replayed the encounter in my head over and over again. This is awesome! God, I love sucking dick! Once again, I was on cloud nine for several days afterward. However, work got very busy and some family activities took precedence and I my cocksucking persona had to take a backseat for a bit. Over the course of the next couple of weeks, my libido waned as I had to focus on other things. I also did not get any messages from Jim which further diminished my sex drive. I finally had some downtime coming into this past weekend and my sex drive perked up. I started thinking about Jim, thinking about cock, and something that I had not thought about for some time, dressing femme. I spent the weekend, surfing Amazon for some new femme clothes as I had another work trip coming up and I thought that it would be fun to be able to dress-up. I also started thinking about sucking cock and was bummed that I had not heard from Jim recently – it had now been a couple of weeks. Well, yesterday, after having picked out a thong, thigh highs and a dress on Amazon, I sent Jim a note. I heard back from him later that day. “Hey, how’s things. I have been busy the last couple of weeks. I was in St. Louis for work and this past week I had a friend in town. Are you coming over tomorrow to suck me off?” How do you think I responded? Jim also told me that he created a Kik account so we started trading texts which made it much easier to communicate. I won’t get into all of the details as the encounter was similar to the first three. However, I was excited as this now matched the most number of encounters I have had with the same dude since my encounters with Paul. It was also interesting in that Jim had me strip for him as he wanted to see my dick while I sucked him. I gladly got naked for him. Once again, he didn’t last that long but he shot a wonderfully tasty load into my mouth and I greedily swallowed it all.
It has now been a couple of hours since this most recent encounter as I type this out. Recounting these experiences serves a couple of purposes for me. First, I want to make sure I remember and have a record of all the encounters I have had. It is kind of a turn-on to know that I have done this enough times that it is tough to keep track of everyone I have been with. It makes me feel kind of slutty, in a good way. Second, I like sharing my stories and hope that they are entertaining and informative for others with similar interests. As I mentioned above, I am going out of town next week and I hope that I can add another notch to my dicksucking belt. If I do, I will be sure to share my experience. Please share your thoughts and feedback on these stories. I love it when I hear from people that have read about my experiences.
I finally fell asleep and the next morning I got up and did my morning ride. My adrenaline level was high and I powered my way through my work-out as I was thinking about my upcoming encounter. My dick was semi-hard as I was so turned-on thinking about this follow-up meeting. Of course, the inevitable happened. I got an e-mail from Jim apologizing, but that he would have to cancel. Cancel??? What the hell?? I was crushed. Jim said that he had to set-up an emergency dentist appointment for a toothache. Really, a toothache??? Well, fuck me. My mood changed dramatically. I went from excited anticipation to depressed. Part of me wanted to tell Jim to fuck off but that I knew that wasn’t appropriate. This wouldn’t be the first time a guy flaked on me and it probably wouldn’t be the last. Who knows, maybe we would hook-up again some other time. So, I just responded with “Ok, hope you get some relief. Lmk if you want to get together another time.” I started thinking about putting up my DoubleList post or maybe trying to seal the deal with someone on Sniffies. In any event, I went upstairs to shower and get dressed for the day.
By the time I got out of the shower, I got another e-mail from Jim. The butterflies came back as I anxiously opened his message. “Hey, my dentist can’t see me until later, are you still available?” What? Is this really happening? Talk about a roller coaster of emotions. I e-mailed back that I was available right now but that if he was in pain and wasn’t feeling it, we could do this another time. He quickly replied that he was horny and really wanted my mouth on his cock again. I then responded that I could get to his place in about 30 minutes. I got another immediate reply that he would be waiting for me. I finished getting dressed and headed out. While at first I was thinking about whether Jim was bullshitting about the toothache, I quickly put that out of my mind as it didn’t matter. All that mattered was that I was still on my way to his apartment to have my second encounter with this guy. I couldn’t wait. I put on some sissy hypno to listen while I drove to his place. By the time I got there, my mouth was drooling.
After parking and walking over to his building, I sent him a note that I was downstairs. It was a nice morning, sunny and warm – a really nice, fall day. I took in the sunshine, looking up and down the block, trying to contain my excitement as I waited for Jim to come down and let me in. After a couple of moments, Jim came outside to greet me and after saying our hellos, I followed him inside. His apartment is on the second floor and as we walked up the steps, I was looking at his ass, covered by his sweatpants. I had a smile on my face as I continued to follow him down the hallway to the entrance to his apartment. We went inside and he bolted the door behind us. “I am sorry to hear about your tooth but I am glad we could still meet.” He just smiled and said “No worries, I have been taking Advil and as long as I not chewing, it isn’t too bad.” I followed him into his bedroom and he turned to face me. “So, you’ve been looking forward to sucking my cock again?” I just smiled at him and dropped to my knees. I started rubbing his semi-hard dick through his sweatpants and looked up at him with lust in my eyes. I started kissing and licking his hardening tool through his pants while my hands caressed and squeezed his ass. After a couple of moments, I pulled down his sweats to free his cock. It was as sexy as I remembered. His cock is cut, has a nice sized head and is a nice thickness. I don’t think his dick is quite seven inches when fully hard but it is a nice cock and I was licking my lips in anticipation of sucking on it.
Before I could get my mouth on it, Jim pulled his pants fully off, stepped toward his bed while he also took off his sweatshirt. Now completely naked, he laid down on his bed and spread his legs, inviting my to crawl between them to start servicing his cock. I got on my hands and knees on his bed, between his legs, my mouth just inches from his cock. I gave his beautiful tool a couple of kisses while a caressed his thighs. Jim pulled out a little bottle, “Poppers?” I politely declined as he inhaled deeply and the smell of amyl-nitrate started filling the room. I opened my mouth and took his now hard cock head into my mouth. “Mmmm” I moaned as my tongue started swirling around the tip of his dick. I started caressing his balls as I started moving my mouth up and down on his hard pole, getting it wetter and wetter each time. Soon, I was deepthroating his tool as he grunted his approval. I dropped my mouth down and started sucking on his balls while I stroked his shaft with my right hand. Jim then pulled out a bottle of lube and said “let’s get this baby lubed-up! It’s water based so you can keep sucking it.” As I gripped the top of his dick, he squeezed some lube on the tip and I worked it over his entire shaft as I continued to stroke him. “God damn! That feels good!” You think that feels good? What till you feel this. I continued to stroke his cock but dropped down my mouth to start licking his ass. “My god, you are great!” Jim moaned as he lifted up his legs to give me better access to his asshole.
With his legs pulled up, his arms wrapped around the back of his knees, me still stroking his shaft, I was staring at his asshole. I then turned my gaze up to Jim and I locked eyes with him as I placed my mouth on his puckered hole and stuck my tongue inside and I began to rim him. “Jesus, that feels good!” I continued to rim his ass for a couple of minutes but soon, I was dying to get his cock back into my mouth. I left a trail with my tongue from his hole, through his taint, his balls, and all the way up his shaft until I took his cockhead back into my mouth. The lube was pretty tasteless and I immediately deepthroated him. Jim groaned in appreciation. I slid my head back up to the tip of his delicious cock and started sucking on him while I also stroked his shaft with my right hand. My left hand was caressing his thigh and I just felt so… content. I loved the feeling of his warm cock in my mouth. The sounds of me slurping on his dick coupled with his moans were incredibly arousing. Unfortunately, it was over too soon as he started bucking his hips and growled “Here it comes! Take my cum!” I greedily took his load as it filled my mouth and started sliding down my throat. It tasted wonderful. I continued to suckle him to make sure that I didn’t miss a drop but he started jumping everytime I nibbled his dick as it was so sensitive. It was clear that he was done with me. I gave his inner thigh a quick peck and got up. I asked him if I could use his bathroom to wash my hands as they had a mixture of lube and sweat that made them kind of sticky. Jim told me to help myself as he started getting dressed. We made small talk for a few moments and then I excused myself and left. As I walked out, I thanked him and reminded him that he could contact me anytime and that I would love to come back.
Just like the first time, my drive home was a dream. I was in a semi-euphoric state as I relived the encounter. Everything about it, driving to his house, being submissive, sucking his cock, rimming him, and finally swallowing his cum made for a fantastic experience. I could do this every day, all day. Needless to say, I again had some powerful jerk-off sessions after that encounter and hoped that I would hear from him again. The mental aspect of being another guy’s regular cocksucker was really scratching an itch that I didn’t know I had. It was great! Things were quiet for the rest of the week. The following week I had to go out of town for work and was fearful that I would miss another chance with Jim. At first I was happy that I didn’t get a note but then I was also kind of bummed that I didn’t. Was that it? Two times and he was done? Given my work, travel, and family obligations, I thankfully didn’t have a chance to dwell on it. But the following Monday morning, back at home, I was working out in the basement and was feeling a little randy. As I was doing a plank, I started thinking about Jim. What if I sent him a note? I wonder if he would like to see me again? I don’t know if it was karma but when I finished that rep, I went to my phone and what did I see? An e-mail from Jim. “Hey, are you available this morning? I have a huge load I would love to give you. Lmk.” I quickly responded and I told him I could be there within the hour. He asked me to hurry-up and that he would be waiting. I finished my work-out, showered and headed to his place, telling my wife that I had to go into the office.
The route to his apartment was becoming familiar now and I started daydreaming about his beautiful dick. I couldn’t wait! Soon, I was back at the front of his apartment building, oozing with anticipation of having another go at Jim’s cock. What a cocksucker I have become! That thought just heightened my arousal. Soon, Jim was opening the door and back up to his place we went. This time, after we got into his apartment, he immediately started stripping off his clothes and dropped down on his bed, naked, with his semi-hard dick beckoning me to come closer. I crawled between his legs and immediately smelled a new scent. “Hmmm, you smell good.” I moaned. “You like it? I just showered, the soap is scented.” “Mmmmm” was my only response as I took his cock into my mouth. As I am servicing him, Jim likes to start talking really raunchy. He would ask if I think about sucking off my boss or other guys I work with? Would I like to see him fuck my wife? What other guys have I sucked off? Things like that. I have to admit, taking my mouth off of his cock so that I could respond, all the time making eye contact with him, filled me with a shameful warmth that was very arousing. When he asked me why I liked sucking his cock and I responded “Hmm, I love how hard it is. I love the head and swirling my tongue around it. Your cock tastes great and I love how warm it feels in my mouth.” I could feel myself blushing as I said these things, one part of me being embarrassed but another part of me embracing what I have become. I followed my tried and true routine. Sucking him, stroking him, suckling his balls, rimming his ass, caressing his legs all while trying to maintain as much eye contact as I could. Watching him watch me, added a whole other level to the experience and I tucked that knowledge away so that I would remember to do this as often as possible going forward. Jim also has kind of a fantasy of wanting to cum twice. “Are you ready to swallow two loads today? Do you want me to cum twice.” Having serviced him a couple of times already, while I would love to get him off twice, I presumed that he was just talking. Sure enough, I responded with “I would love to swallow your come as much as you want” as I continued stroking his shaft. He started groaning and shaking and he grabbed by head and pushed it back onto his cock as he shot his load. It was a nice one as it really filled my mouth. This was the first time that I was having a hard time keeping the load in my mouth while continuing to suck on a dick. I persevered as his body stopped shaking, I suckled the tip to make sure I got it all and then I swallowed. The thick, greasy load slowly slid down my throat while I smiled at Jim. “Do you want me to keep sucking?” I asked. Jim responded that he didn’t think he would be able, and I took that as my cue to make my exit.
I had the same euphoric drive home as I replayed the encounter in my head over and over again. This is awesome! God, I love sucking dick! Once again, I was on cloud nine for several days afterward. However, work got very busy and some family activities took precedence and I my cocksucking persona had to take a backseat for a bit. Over the course of the next couple of weeks, my libido waned as I had to focus on other things. I also did not get any messages from Jim which further diminished my sex drive. I finally had some downtime coming into this past weekend and my sex drive perked up. I started thinking about Jim, thinking about cock, and something that I had not thought about for some time, dressing femme. I spent the weekend, surfing Amazon for some new femme clothes as I had another work trip coming up and I thought that it would be fun to be able to dress-up. I also started thinking about sucking cock and was bummed that I had not heard from Jim recently – it had now been a couple of weeks. Well, yesterday, after having picked out a thong, thigh highs and a dress on Amazon, I sent Jim a note. I heard back from him later that day. “Hey, how’s things. I have been busy the last couple of weeks. I was in St. Louis for work and this past week I had a friend in town. Are you coming over tomorrow to suck me off?” How do you think I responded? Jim also told me that he created a Kik account so we started trading texts which made it much easier to communicate. I won’t get into all of the details as the encounter was similar to the first three. However, I was excited as this now matched the most number of encounters I have had with the same dude since my encounters with Paul. It was also interesting in that Jim had me strip for him as he wanted to see my dick while I sucked him. I gladly got naked for him. Once again, he didn’t last that long but he shot a wonderfully tasty load into my mouth and I greedily swallowed it all.
It has now been a couple of hours since this most recent encounter as I type this out. Recounting these experiences serves a couple of purposes for me. First, I want to make sure I remember and have a record of all the encounters I have had. It is kind of a turn-on to know that I have done this enough times that it is tough to keep track of everyone I have been with. It makes me feel kind of slutty, in a good way. Second, I like sharing my stories and hope that they are entertaining and informative for others with similar interests. As I mentioned above, I am going out of town next week and I hope that I can add another notch to my dicksucking belt. If I do, I will be sure to share my experience. Please share your thoughts and feedback on these stories. I love it when I hear from people that have read about my experiences.
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