Five More Dudes...and A Woman? free porn video

Wow, it has been a whirlwind since my last story. In the last few months, I have tried poppers, met a woman that caused me to rethink my interests, purged all of my femme stuff, went back down the rabbit hole and serviced three guys in less than 24 hours, and then reconnecting with this mysterious lady, I jerked off while I talked to her on the phone. If you are interested in these sordid details, please read on. In my last story, I recounted the first time I was bred. Dressed up as a sissy slut, I took a bbc raw and let him cum inside me. While this fulfilled one of my long time fantasies, back in the real world, I was worried about my health. As has been my history, after an encounter like this, I would recoil back and was not looking for any other hook-ups as I processed what my life was becoming. As a quick recap, I am a 49 year old, married dude, in a sexless marriage. Over the past year, I have started fulfilling some of my bi/sissy fantasies.

After that last encounter with Paul, I waited a month and then got an updated blood screen. Fortunately, everything came back negative. During this time, I continued to fantasize about being a sissy slut and continuing to hook-up with Paul, my semi-regular BBC. However, Paul did not seem to be interested in seeing me. I traded a couple of texts with him and he was pretty cool in his response. Maybe he wasn’t interested in me anymore? I am not sure but I was really starting to feel horny. Since I was not getting any positive response to Paul, I started trolling Reddit and Doublelist again. Over the course of the next couple of weeks I hooked-up with three different dudes. Just typing that, it really sinks in that I had turned into a real cock sucking slut and far from being embarrassed by it, I relished it.

The first encounter happened on a Thursday afternoon. I had a couple of morning meetings in the city (Chicago) but my afternoon was open. I connected with a guy on Doublelist looking to get his cock sucked. He lived in a condo building on the near north side. He indicated that he was about the same age and was looking for a little oral relief. In my limited experience, these encounters are pretty anonymous but in this case his building had a doorman and I had to ask for his unit by his name. There was something emboldening about walking into his building and asking for James Henderson (name changed). The doorman called up and, getting the okay, let me proceed to the elevators to go up to his place. Moments later, I was knocking on James’ door and he let me in. James is about my age, about 6’ and slim. After just a couple of moments of chatting as he took my coat to hang it up, I pegged him as gay – not that it matters to me anymore but I still find it interesting that I still cling to labels that I have judged people during my life. It got me wondering how people perceive me. I think I look like a non-descript guy, married with k**s. Can people guess that I have become an insatiable cock-sucker? Anyway, James told me that he works from home and was happy that I could stop by. He then told me that he would like us both to get naked and he would love for me to suck him off.

After getting undressed we climbed on his bed (it was a tall bed, the top of the mattress was at least four feet off the floor) and I crawled between his legs and started fondling his cock. He had an okay cock, it was not very thick, about six inches, cut. He was trimmed short with shaved balls. I started with my usual kissing and licking as he started hardening. God, I love the taste and smell of dick! In my limited experience, all cock tastes similar. Not identical but definitely consistent from one dick to the next. Jeez, I have had enough experience to warrant an opinion on the taste of dick – that gets me hard just thinking about it. Anyway, I then took him into my mouth and started sucking while cupping and caressing his hairless balls. His cock tasted nice and he really smelled good. I think he had taken a shower right before I came over. He got fully hard and started moaning in appreciation as I started deep throating him. Over the next 10 minutes, it was a constant battle for him not to cum. James clearly wanted this to last as long as possible. I wasn’t trying to rush him but I have turned into an insatiable cock gobbler. He was clearly enjoying my technique (which really turned me on) and would continually take my mouth off his cock in order to not to shoot. He would pull me up to hug him or have me suck on his nipples. Inevitably, I would make my way back to his cock and he would again have to shift away to prevent from shooting too quickly. This made me want to get him back in my mouth even faster as I really enjoyed the effect I was having on him. Well, he couldn’t hold out any longer and with my mouth nestled against his belly with his cock fully in my throat, James grunted that he was coming. I moved back up so that just the head was in my mouth and felt his cock start to spasm as my mouth started filling up with his cum. It is an incredible turn-on to have a guy cum in my mouth. It is a reward for a job well done while also serving as a reminder of my submission. He tasted great and I swallowed his spunk while I continued to suckle on the tip of his dick. He apologized for cumming so quickly. I looked up at him, smiled, and told him not to worry about it and went back to sucking on his now softening dick. After another couple of moments, I got up and started getting dressed. He thanked me for the great blowjob and I just smiled and told him the pleasure was mine. I got dressed and made my exit. The physical aspect of sucking cock coupled with the psychological aspect of giving another man pleasure continues to really turn me on. As I rode down the elevator I felt like I was glowing. I walked out of the elevator and as I was exiting the building I acknowledged the doorman, wondering if he knew what I had just done.

While there was nothing physically spectacular about the encounter, James’ cock was normal sized and the whole interaction was less than 15 minutes, I was still amazingly turned on by what I had done and couldn’t wait to do it again. I really do love sucking cock! It is a thought that I couldn’t get out of my head. What a slut! I reveled in my debauchery. I was back on Doublelist the next morning. Fridays at work can be a hit or miss for me. Sometimes there is a ton of activity and I am swamped the entire day, other times it can be really slow and I have an opportunity to sneak out early. This was the latter. In addition to not being tied to the office, I was able to hook-up with a dude that was only about 10 minutes from my office. Apparently, he also works from home and has his condo to himself during the day while his wife works. This guy was at home doing poppers, watching porn, and looking for someone to suck him off. Still feeling the glow of the blowjob I gave the previous day, I jumped at the chance to suck another guy off. He gave me his address and 15 minutes later I was knocking on his door.

The door opened and the first thing that struck me was this dude’s size. He told me that he was 6’4”. I don’t think he was that tall (I am 6’2” and he didn’t look as tall as me) but he was big. He had to be at least 250 pounds. Not fat, per se, but very large. He was dressed in gym shorts and a t-shirt and escorted me back to his bedroom. Even though it was the middle of the afternoon, his bedroom was completely dark with the blinds on his windows closed. The only light was coming from his television with some gonzo porn playing with a chick being gangbanged by seven or eight dudes. He immediately undressed, got back on his bed and told me to strip and get to work. I undressed down to my underwear and crawled between his legs and started licking his cock.

A couple of things immediately struck me as I crawled between his legs. The first was listening to him start immediately huffing on poppers. I have never done poppers before and the chemical smell was very distinctive. The second thing was his smell, he was very raunchy and smelt of sweat. I started licking and sucking his already hard cock and he said “do you like that? I haven’t showered since yesterday morning, what do you think?” I just moaned and continued to suck on his nice cock. It was cut, decent thickness and a little more than six inches. It had a nice head and felt great as it slid down into my throat. This dude (we never exchanged names) was very talkative and liked to talk dirty. “Do you like my dick slut? Do you like sucking it?” I told him I did as I started stroking him while I dropped down and started sucking on his balls. His ball sack was really tiny, almost disappointingly so. I couldn’t help wondering if this guy took steroids as I hear taking steroids causes the testicles to shrink. I didn’t spend too much time thinking about it as I went back to sucking on his nice dick. After a couple of minutes, he told me to get off the bed and get on my knees. I complied and he came over and shoved his cock in my mouth and started face fucking me. “Oh, yeah! This feels great! I love fucking your face, do you like it?” I just mumbled as his cock moved rapidly in and out of my mouth. He then had me get back on the bed, laying on my stomach with my face at the edge. Once again he started fucking my mouth. He then reached down and started caressing my ass. “Ummm, nice ass!” Crack! He spanked my ass cheek. “Bend your knees, lift your feet.” I complied while he continued to fuck my face, saliva beginning to ooze out of the side of my mouth. “Umm, yes, I love feet! You have sexy feet.” Crack! Another spank on my cheek. I have never been into pain but, I have to admit, I liked him smacking my ass, it made me feel like a real whore.

“Let’s get those boxers off.” He started pushing down my underwear. He then pulled out of my mouth and told me to roll over and to turn around. I followed his instruction and with my legs now hanging off the edge of the bed, he pulled off my underwear, dropped down and started licking my ass. “Mmmmmm!” I groaned in pleasure feeling his tongue in my ass. After rimming me for a few moments, he then stood up and started frotting our cocks. As he rubbed his against mine, he asked me, “Do you like getting fucked?” I told him I did but that I would want to be better “prepared” for that. He smiled, respected my wishes and climbed back on the bed and had me get back between his legs. Before I got back to work on his cock, he handed the poppers to me and told me to breathe in. I did so and a feeling of euphoria swept over me as I went back to town on his cock, alternatively deepthroating and stroking him. He wanted me to keep my feet raised and I felt like a sexy little whore by complying. “Have you ever been with two guys before?” “No” I gasped as I briefly took my mouth off of his manhood. “Would you like to? I have a buddy and I think he would also like you.” My cock, which was semi-erect during this encounter, immediately got rock hard at the idea. “I would love that!” “Cool, we will have to set something up, maybe get a hotel room.” As he said this, he grabbed my head and forced it all the way down on his cock. At the same time, with his other hand, he took his popper bottle and took a big whiff. A couple of minutes later, his thrusting increased and he said “I am going to cum! Where do you want it?” I lifted my head briefly and looked up at him and said “Feed me.” He closed his eyes as I dropped back down on his dick and he groaned. I started to feel his cock pulse as he grunted and, once again, less than 24 hours after my last encounter, my mouth was being filled with a strange man’s spunk. I swooned as I tasted his sperm. It was delicious! I eagerly swallowed it and continued to suck on his dick so that I would get it all.

As I was getting dressed this guy (still no name) told me he was heading to Amsterdam for work but on his return we should coordinate a threesome with his friend. I told him to count me in. When I got back to my car I was still feeling light headed, almost like a feeling of post orgasmic bliss. What a slut I had become. Again, no feelings of guilt, just a feeling of satisfaction. While this dude had to go to Europe, I was heading back to Miami the following week for work. As I boarded the plane, I reactivated one of my Doublelist posts and by the time I landed I had over a half dozen inquiries. I quickly sifted through them, responded, and by the time I got my rental car, I already had a hook-up for that night and another potential for the next night. I settled into my hotel room and waited for my next cock. At about 8:30, he sent me a note that he was in the parking lot and was on his way up. Less than five minutes later, he was knocking on my door. The actual act of sucking this guy off was nothing memorable. His cock was normal size and I was able to get him to cum in only a couple of minutes. Instead, the remarkable thing was how nervous he was when he entered my room. It didn’t take long to discern that he was new to man on man action and I kind of chuckled to myself realizing how far I had come over the past year. He was very fidgety at first, kind of pacing the room, nervously talking and giggling. I just laid on the bed in a pair of gym shorts and a t-shirt and tried to get him to relax. After hearing his life story, he finally got comfortable enough to let me pull his pants down and get to work. After he left, I laid in bed, savoring the taste of the cum I had just swallowed and thought about the encounter. Other than his nervousness, the only thing that stood out was that he had bad teeth. I didn’t really remember anything about him other than that. I wondered is this what it’s like to be a slut. The partners start fading and you only remember vague details about any specific encounter. That thought was both disconcerting as well as exciting. Prior to starting down this road, I had only five female partners. Being married for close to twenty years, I had not been with another woman in a really long time. However, in the past 14 months, I had now hooked up with nine (nine? I think so, I kind of lost count) different dudes. While this isn’t a huge number, it really made me feel like a cock-slut – and I liked it.

I was supposed to have another hook-up the next night but we weren’t able to coordinate a time and decided to try again the following night. Since I didn’t have anything planned, after work I stopped at a bar near my Miami office to have a beer. As I sat there, my life took a left turn. In walked this petite, gorgeous redhead. We made eye contact, smiled at each other, and after some small talk, we ended up sitting next to each other for the rest of the evening. This woman was amazingly gorgeous. Frankly, way out of my league. Why was she interested in me? Was she interested in me? This had never happened to me before. Her name was Sophia and I did learn that there was a little crazy (maybe a lot crazy) behind her sexy green eyes. I learned that she was going through a divorce (her third) from an abusive husband. While this was the last thing I was looking for that night, I have to admit that I was smitten. As much as I had developed a desire to suck cock, I was still attracted to pretty women. I tried to play it cool, thinking that she was just being nice and wanted someone to talk with. After a couple of hours at the bar, she said that she had to leave. I replied something corny about wishing I could see her again and she gave me her phone number and said “What about tomorrow night?” What about tomorrow night? Are you serious? I could not believe this was happening to me. I took her number and told her I would text her the next day to plan something for that night. I went back to my room and sent her the text “Had a blast hanging out with you, good night.” Just a couple of minutes later, she texted back “Good night, cutie.” What was happening? It goes without saying that I had conflicting thoughts swirling around in my head.

The next day, I tried to take stock of where I was at in my life. I had a wife and family at home. I was in a sexless marriage. I had now been sucking dick for over a year and had been experimenting with cross-dressing. Now this amazingly beautiful woman drops into my life. I have to admit, my pretty boring life had suddenly become pretty interesting. While I was contemplating what to do about Sophia, my postponed hook-up was messaging me about getting together that day. I didn’t know what to do. Finally, I said “fuck it” and texted Sophia to see if she wanted to go out to dinner. She immediately responded in the affirmative. I then told my guy from Doublelist that I wasn’t available anymore. He was perturbed and disappointed. The rest of the afternoon went by in a blur as I was looking forward to what would be my first date in over 20 years. We met at a nice resort and had drinks and dinner. Sophia was incredibly captivating. I couldn’t help but wonder just how crazy she must be to have gone through three husbands. After dinner, we went to a night club for a drink and then decided to call it a night. It was a very nice evening. I tried to act like a gentleman but I was incredibly turned on by this sexy woman. As we left the night club, it started raining and I offered to give her a lift home which she happily accepted. As I started driving, a downpour started and I pulled over to let the rain subside. After I put the car in park, I leaned over to her and gave her a kiss. That opened up the floodgates and we ended up making-out for the next hour. While we only made out, it was an incredible experience. I had forgotten what it was like to be with a woman and it was an incredible experience. We eventually stopped and I took her home. I flew home early the next day and I proceeded to start texting with Sophia on a daily basis.

I have to admit, I was totally smitten with her. So much so that I got rid of all of my toys and femme clothes. I no longer had the desire to masturbate as all I could think about was seeing Sophia again. Unfortunately, my work schedule was such that I was not going back to Miami for six weeks. Sophia and I texted and sexted regularly. We described all of the things, in graphic detail, we were going to do to each other when we got together again. Sophia could get pretty raunchy in her texts. It was incredibly erotic. It was a blissful time, all the way up to a week before my scheduled trip. I texted her on a Wednesday morning but didn’t hear back from her until Thursday which was very odd. When I did hear from her, she unloaded about everything happening in her life. Her, soon to be ex, husband had beaten her, her eldest daughter was mad at her, her ex-husband was physically abusing her younger daughters, she got into a fight with her sister, and on and on. It was a real shitshow. She then dropped the real bombshell – she was flying out to Phoenix the next Monday, to stay with her dad, the day that I was coming down to Miami. I was crushed. First, I didn’t know how much of what she told me was true or accurate but I really felt bad for her. Second, I was really hurt that she was leaving the day I was coming down. Was this just a story? Did she really not want to be with me? We had some tense texts on Friday that basically ended with me telling her to have good luck in her life, I was moving on. I jerked off to porn that night for the first time since my last trip to Miami. I was frustrated, angry, sad, and confused. All at the same time. I nutted three times that night and I still fell asleep with a hard-on.

The following Monday, I sent Sophia a text during the time she was flying. I apologized for the way I responded to her and I wished her good luck in her travels. Once again, before I boarded my flight, I reactivated my Doublelist post. Upon landing, I had several responses, including a dude that was ready to go as soon as I got to the hotel. Over the next 24 hours, I serviced three different dudes. While I still couldn’t sort out my feelings, I knew, despite my attraction to Sophia, I still liked cock. What am I doing with my life? I ask that to myself time and time again but that doesn’t change the course that I am on.

The first guy, on Monday night, was into a little domination and he liked ordering me around. He was about 5’ 9”, skinny, with wavy gray hair and a goatee. He sat down on the couch, popped off his shoes and unbuttoned his jeans. “Get to work” he ordered. I dropped down to my knees and started rubbing his hardening cock inside his pants. I kissed and licked the outline of his cock in his jeans and felt him continue to get harder. I then unzipped his pants and pulled them off him. I felt so natural, kneeling in front of him and taking his clothes off. I continued to amaze myself at how far I had come. He had an average sized dick but wore a cockring and a band around his dick/balls. He was a bit of a dom and that really turned me on. He liked shoving my head all the way down on his dick and holding it there while I gagged. I was really aroused by the submissive aspect of this. He would shove my head down on his dick which was just long enough to get into my throat and stop my breathing. He would keep my head down for far longer than I would have on my own, my squirming giving his dickhead pleasure. While part of me was a little freaked out by the loss of control, I was really turned-on by the submission. While he professed to want to take it slow, he only lasted about 10 minutes. Between bouts of him holding my head down, he would let me stroke his dick while I licked and suckled the head. Like I said, his dick was not remarkable but it was still nice with a mushroom capped head that felt really good with my lips around it. When he was ready to cum, he grabbed the back of my head and shoved his dick all the way into my throat and proceeded to shoot his load directly into my stomach. It was my first throat pie. While I was disappointed that I didn’t taste his cum, I was quite turned-on by what happened. I continued to suckle his cock for a few minutes until he ordered me to get a wash cloth to clean him up. I dutifully obeyed and after cleaning him up, he got dressed. He told me that he really enjoyed it and that I had his contact info if I ever wanted to go again. What a sissy slut! I just laid on the floor next to the couch and thought about what I had just done.

The next afternoon, I hooked up with a latin dude. This dude was also about 5’9” but was about 240 pounds and very broad. He did not speak English very well but it wasn’t a problem. He came in, got undressed and laid down on the bed. He had a nice dick, about seven inches. The bonus was that he was uncircumcised. This was my first uncut cock! I was excited to give it a go and proceeded to go to town. I sucked his cock, licked his balls, and then rimmed him. This was the second latin dude I had been with. I have been with four different black dudes and five different white dudes. Amazingly, again, all dick tastes similar. More amazing is that I was really developing a yearning for the taste of cock. Despite my brief interlude with Sophia, I was really a confirmed sissy cocksucker. I smiled to myself as that went through my head as I continued to work on this guy. He loved my efforts as he got really hard. I liked deepthroating his cock and he seemed to really enjoy me taking him all the way into my throat. He then had me lay on my back and then he straddled by head, facing my feet, stuck his dick in my mouth and proceeded to face fuck me. It felt amazing! After a couple of minutes, he took his cock out of my mouth and put his ass over it and I started rimming, licking and tongue fucking his ass. After a couple of minutes he would switch back to fucking my face and then back to me licking his ass. I was in heaven! After some time, he climbed off of me and laid back down on the bed and I again crawled between his legs to continue servicing him. This dude took a long time to cum. I was working on him for about 30 minutes when he asked, in broken English, if I wanted him to fuck me. I politely declined and a couple of minutes later, he grabbed his cock and started stroking it while he held my head just above his cock. A moment later, he started to cum and I took him back into my mouth to swallow his spunk. He tasted very good. Again, I suckled him, making sure I got every drop. After a couple of minutes, he proceeded to get dressed, thanked me, and then left.

Over the course of the day, I had been texting with Sophia. She had sent me a text, thanking me for my kind words the day before. I apologized for my cold comments and told her it was just my disappointment at not being able to see her on my visit. As we continued to chat, I reminded her that I had previously requested a picture of her but she had never sent one. She promised that she would send one soon. Since she had told me that before, I just assumed that she would not follow through. In any event, less than 45 minutes later, I met up with dude number three. This guy was older than me, had a shaved head and was about 6’1” and 200 pounds. He was in pretty good shape for his age with a little belly. This encounter was very disarming, similar to the first time I got fucked. This dude didn’t just want to get off, he wanted to have a relationship with me. At times, I felt like an escort as I humored him with my responses about my personal life. There was some things I really liked, he also liked to shove my head down on his cock, making me gag with his 6” in my throat. He also liked getting his ass licked. At one point, just like with my latin dude earlier, he had me lay on my back while he straddled me, facing my feet. He would alternate, first shoving his dick down my throat and then rubbing his asshole across my lips. It was actually pretty cool. I just wish he would have kept his mouth shut. We played for about 45 minutes and, I have to admit, I was getting bored/tired. This was my third dude and all I wanted at this point was to drink his cum and be left alone. After what seemed like an interminable amount of time (and unnecessary dialog), he was ready to shoot. Like the last guy, he grabbed his dick and started stroking it while he held my head just above it. This time, when he was ready to shoot, he shoved his head onto his cock and filled my mouth with his cum. Once again, I continued to suckle him, making sure that I didn’t miss a drop of his cum. Thinking that we were done, this dude then proceeded to tell me his life story. I didn’t know what to do. I did not want to be rude, so I just laid next to him while he prattled on for about 20 minutes. During that time, my watch buzzed a couple of times, indicating that I had received some texts. They were from Sophia. At that point, I really wanted this dude to leave. He then asked if he could use my shower. Sure, why not, do you also want me to get you dinner? I didn’t say anything and let him use my shower. After he finished his shower, he continued to talk. At that point, I politely told him that my wife was expecting me to call her. He was cool with that, got dressed and got ready to leave. He also told me that he had a great time and wanted to get together again before I went back to Chicago. I thanked him for his kind words but told him I was not going to have any time before my flight leaves on Thursday morning. After he finally left, I decided that I really needed a drink. I got dressed and went down to the hotel bar.

On my way down to the bar, I finally checked my messages. Holy shit! Sophia sent me a picture of her in a tight shirt, bare midriff and tight jeans. She looked like a knock-out. She also sent a note, apologizing for not being very photogenic. Bullshit! She looked like a model. We proceeded to chat for the next hour as I had a few beers at the bar. I had told her that, not having her picture, I had convinced myself that she wasn’t as good looking as I remembered, tempering my disappointment at not getting to see her. However, the pic she sent dispelled that notion and got me incredibly turned-on. I then proceeded to tell her that I was going to jack-off in my room that night while looking at her pic. So how does she respond that? She demanded that I call her so that she could listen to me masturbate. Wow, this woman really is twisted! How did I get so lucky? I quickly finished my beer and headed upstairs. I sent her another note, confirming that she really wanted me to call her. She told me to hang tight, she was cleaning up after dinner and she would call me. Sure enough, 10 minutes later, she calls. We proceed to make small talk for awhile, basically getting reacquainted since we hadn’t actually spoke to each other in weeks. Finally, she asks me if I am going to play with myself. I sheepishly admit that I had actually was already stroking myself while we were talking. Her voice got very husky as she told me that it made her pussy wet thinking about me jerking off to her. We then basically had phone sex for the next 10 minutes until I couldn’t take it anymore and shot a load all over my stomach. Then, guess what happens next? Sophia asked me to take a picture of my cock and stomach covered with cum and send it to her. My cock stayed hard after hearing that request.

So, a few weeks later, I am typing this while we are all in Covid-19 lockdown. I still text Sophia every couple of days – she really wants me to visit her in Arizona. I also constantly think about the dozen different cocks I have serviced in the last 18 months. Part of me is really yearning to see Sophia and another part of me has been starving for another cock to suck. Meanwhile, I am now really disappointed that I had gotten rid of all of my femme stuff (not that I could “play” given that I am stuck at home with my family). Where do I go from here? I am not sure. I hope everyone is staying safe and that we get out of the pandemic as quickly as possible. Once we do, I think I will continue to do what I have been doing – follow my urges on to the next encounter. Stay tuned!