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Being a Dutiful Sissy Husband – Part 7
"I think I need another drink." Ann said. She got up, her robe hanging open and she squeezed her own tittles as she walked over and mixed another g&t and sat back down. "Well, keep going. I want to know it all."
"Okay." I responded as I started to think back about my prior encounters. As I have mentioned previously, I get to travel to Miami for work on a pretty regular basis. This has afforded me an opportunity to get some extracurricular playtime. I was still trying to utilize Reddit (Floridar4r) but the subreddit is not nearly as active as in Chicago. So, I was using Doublelist more to find hook-up partners. I had (and still have) a couple of listings that I can post when I am traveling. My standard one at the time was that I am a submissive, married dude, staying near the airport and looking to serve. I always forget to edit this listing as I end up with a bunch of responses of which airport? Fyi – the Miami airport. A couple of weeks after my last visit with Paul, I travelled down to Miami and put my post up just as I landed.
As usual, I got a mix of messages from various flakes, but I also got a few from some real dudes looking to hook-up. As I was going through the messages, I came across one that was very familiar. As I checked his e-mail message, sure enough, it was a black dude that I had hooked up with on an earlier visit. This is a dude, about 6'3" and 225 pounds. I would guess that he is a couple of years older than me and he was pretty cool during the last go around. I responded to his message and reminded him that we had hooked-up a few months ago. He was happy to come over again. Just like last time, he wanted me naked on the bed with the hotel door left ajar. Laying there for him to come up really heightened the experience as you just don't know who might walk in. I laid there, naked, waiting in anticipation and then I heard the door open and then shut completely. Laying in the bed, you cannot see the door as the wall of the bathroom blocks the view. My breath stopped as I waited and a moment later, he appeared from the doorway. It was a little unnerving since we had hooked up before. While I still don't know his name, the familiarity made it seem a little weird. Does that make sense?
Anyway, he came into the room, saw me, smiled, and immediately started undressing. He was only wearing a t-shirt, shorts, and flip flops. After undressing, he laid down next to me, smiled and said "Good to see you again" as he began to caress my chest and legs. My hand immediately went down to his groin and started fondling his hardening cock. I remembered that he wasn't especially large, probably around six inches but his dick was really curved upward. As he continued to harden, I started nibbling my way down from his chest to his nether region. I started kissing his dick and balls as I continued to gently caress the shaft. I then crawled between his legs and took his dick into my mouth. Again, not being overly long, he would not be hard to deepthroat. Unfortunately, the curve of his erection made it a little challenging as his dick was pointing in the opposite direction of my throat. I was able to adjust my position to take him all the way in. He groaned in appreciation as he slapped and rubbed my ass. After a few minutes of cock sucking, he pushed my head further down. Knowing what he wanted, I adjusted my position and lowered my head below his balls as he lifted his ass up. I stuck my tongue out and started licking his asshole and he groaned loudly. After a little bit of licking, he grabbed the back of my head and shoved my mouth against his hole. I started really going to town on his back door, kissing, slobbering, licking, and slurping his ass. While this was happening, I continued to stroke his cock.
After a few minutes of ass worship, he pulled me up to him and asked me to start sucking on his nipple. I did so. He then asked me to stick a couple of fingers into his ass. I complied. While I sucked on his nipple and finger fucked him, he started stroking his cock. He then started talking dirty to me. "Do you like eating my ass? How did it taste? Keep sucking my nipple! Oh yes! I am going to come!" With that, he shot his load all over his stomach. I can't lie, I was disappointed. This is the second time I had been with this dude and neither time did I get a chance to swallow his load. After he came, I removed my fingers from his ass, and he quickly got up and went into the bathroom to clean-up. I continued to lay in bed, and we traded small talk as I heard the water running from the sink. A few moments later, he reappeared and got dressed. He thanked me and said his goodbyes and left. While the experience was pretty hot, I was left disappointed but before I could really start thinking about it, I was in for one more bit of awkwardness. He left his sunglasses in my room. I sent him an e-mail and he also sent me one. A few minutes later, he was back at my door, and I opened it and handed him his sunglasses. It was an odd feeling. I don't know your name, but my fingers were just inside your ass, here's your sunglasses and have a good night...
I did not have any additional encounters on that trip, nor did I want any. I was left feeling confused about what I was doing. Was this what I really wanted? Was this still a turn-on? Getting back to Chicago, I would think about this periodically, but I was not able to come to any conclusions as both work and family got really busy. Over the next month, my libido really dropped as I had to concentrate on work as well as on things at home. During that month, I really started thinking about ditching this "hobby." While sex remains a non-starter with my wife, we have become much closer emotionally over the past several months and I was really feeling guilty about my prior activities and thought many times about giving it up. However, as is usually the case, it wasn't long before I was going back down the rabbit hole. The first thing I did as I was feeling a little randy was to purchase a few new items from Amazon. First, I bought a new wig. The style is very short, kind of pixie. I knew I wouldn't have to be worried about getting hair in my mouth anymore. I also purchased another pair of thong panties as the previous pair I had purchased were just too big. Lastly, I also purchased thigh high stockings. After getting a chance to try on my new things, my desire to suck a cock was as strong as ever and I reached out to my BBC, Paul.
Paul and I would trade messages, periodically. They would be short notes, usually with subreddit recommendations but we would also talk about getting together. Again, being as busy as I was, I was never able to suggest a day. Well, On one particular day I found out that my afternoon had suddenly opened up. I was supposed to have a couple of meetings with some customers from out of town, but their travel plans changed, and my calendar suddenly was wide open. I texted Paul to see if he wanted to get together today and he immediately jumped at the chance. My cock started hardening, thinking that someone finds me desirable as a submissive sissy. I was able to get my gurly stuff from the hiding place in my basement into my trunk without anyone noticing and I headed over to his place this morning.
Despite us hooking up several times, we still don't really know each other. We communicate by Kik, and I need to message him when I get to his apartment building. He then comes down and escorts me up. I arrived today and, as usual, he let me lock myself into his bathroom to transform into a sissy. I undressed out of my suit, hung up and/or folded my clothes as neatly as I could after I got naked, and I proceeded to get dressed. I started by inserting my butt plug which really felt good in my ass. I then put on my Calvin Klein thong panties and bra. I then put on my thigh highs and marveled at my legs for a moment. Damn! I have sexy legs. I just wish I could shave without arousing any suspicions at home. I then put on a dress, a simple blue cotton dress with long sleeves (again to hide the hair). I then put on my new wig. Wow, it was really cute! I brushed it out a little bit, but it really framed my head/face nicely. Feeling really good, I started putting on make-up. I can still count on one hand how many times I have done make-up, but I was able to do a decent job in very short order. A little primer, followed by a light layer of foundation really made me look different. I added a little blush and then applied some mascara. Oops! Still learning with the mascara as I got some underneath my eye and on my nose. I cleaned that up, finished applying the mascara and I was really liking how I was looking. Next up was eye shadow. My experience with eye shadow has been a disaster as I have not been able to blend colors. I just said, fuck it, picked a color that matched my lipstick and applied it to my eyelids. After a couple of minutes, I stood back and looked at myself in the mirror. Not bad! I was no supermodel, but I thought I looked pretty sexy. Mental note, keep it simple with the eye shadow. I then applied some lipstick and to finish my look off, I gave myself a couple of squirts of perfume that I had picked up at the drug store. I put on my high heels and walked out of the bathroom.
Sitting naked on his couch, Paul's eyes widened when he saw me, and a big smile grew on his face. "Wow!"
"Do you like?" I asked.
"You bet, I love your new wig" he responded. I then crawled down between his legs and started caressing his cock. It was already rock hard. God, it felt so good in my hands. I leaned down and kissed the tip. He groaned, "It has been so long, I thought you had given this up."
"No chance" I responded as I opened my lips to let his massive dick into my mouth. Paul's cock his huge, well over eight inches and incredibly girthy. I have a hard time keeping my teeth off his shaft when I deepthroat him. I continued to suck his dick while I caressed his balls in one hand and stroked his thigh with the other. Slowly, I took more and more into my mouth until I had the entire massive dick into my throat. Wow, I had forgotten how good that felt. His cock smelled great, felt great, and tasted great. I was back in sissy heaven.
Once I got his cock drenched with my spit, I would occasionally drop down and suck his balls as I continued to stroke his shaft. I would also stroke him with just the head of his dick in my mouth. I would then go back and deepthroat him again. After going through this routine, a couple of times, he stood up, grabbed the back of my head and started throat fucking me. I was gagging as I tried to keep my teeth off his mammoth shaft. I really like having his cock forced into my throat, what a feeling of submission! Paul then sat back down, and I was ready to really go to town as he would usually like me to start stroking and sucking really fast. Today, he told me to just gently kiss and suck his cock. Mmmmm, I started swooning as I slowly nibbled, licked, suckled and kissed his beautiful piece of meat. He whispered, "your mouth is incredible, this is so much better than edging." I just looked up into his eyes and smiled.
This was going great, I couldn't wait to have him shoot into my mouth but suddenly, things took a turn. Paul whispered to me "do you think about getting fucked?"
"All the time" I huskily responded as I continued to worship him.
"Do you want me to fuck you now?" Wait, what? Fuck me, here? Now? I don't want to be fucked, I wanted to taste his cum. So, how did I respond?
"If you want to, I am willing to give it a try." What the fuck am I thinking??? Paul got up and pulled me onto the couch. I was on all fours with my knees on the couch and my forearms on the back of the couch with my ass wriggling. He went to get some lube and came back and started squirting lube on his dick as he pulled down my panties.
"What is this? A butt plug?" I blushed. He pulled out the plug and squirted some lube onto my ass. I kept thinking that I can't believe I am doing this. I shouldn't be doing this, right? All the time, my ass was shaking back in forth in anticipation of his huge cock. A moment later, I felt the tip against my hole. My god, how is this going to feel. I have been playing with some larger butt plugs, but it has been a few weeks, and I am pretty patient about getting them in. Paul was less than patient as he pushed his huge cock against my hole. Please don't hurt me, I silently prayed. He continued to push and then...he was inside me! My god, he is big! I groaned out loud. Paul asked, "Are you alright?" I nodded and he started to pull back out and push in again. Hmmmm, it felt so good. It only got a bit uncomfortable when he pushed all the way in. I don't think I was in the best position to accommodate his full length, but I didn't say anything as he started to fuck me. I squeezed one of my nipples as I pushed back against him each time he would thrust. Jeez, here I am dressed as a sissy, in a wig, make-up, and dress, getting fucked by a bbc on his couch. Unbelievable! It didn't take him long. "I am going to cum, okay?" What do you mean, okay? "Is it alright if I come inside you?"
Clearly, not thinking, I responded "Please give it to me!" He then grunted and shot his load inside my ass. I was just bred. What did I think about that? Well, my cock was rock hard as I recounted this, so I guess I don't have to really ask myself.
It was a quick comedown as Paul went into the bathroom to clean up and offered me the use of his shower. I thanked him as he gave me a towel and wash cloth. I went into the bathroom, sat on the toilet to allow anything left to leak out. I then removed my make-up, took a quick shower, and got dressed. I got out of the bathroom and told Paul that I took myself by surprise that I let him cum inside me. Did I need to have any health concerns? Paul assured me that he was clean and that he would not put anyone in a position to risk their well-being. I hope so, I thought, because I would love to do this again.
My wife just looked at me with her mouth open "You really are a whore, aren't you?"
"I guess." Was all I could respond.
"Wow. Just, wow. You are giving me a lot to process here. Okay, keep going."
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 from Paul, I started trolling Reddit and Doublelist again. Over the course of the next couple of weeks I hooked up with three different dudes. My wife just sighed as I got into the specifics.
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 kids. Can people guess that I have become an insatiable cocksucker? 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 impact 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 always 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 continued 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 weigh 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 lightheaded, 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 sized, 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 lay 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 if 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 previous 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.
My reverie was interrupted by my wife, "Sophia?? What the fuck is this!" I could see the anger building in my wife.
"Please, let me finish and then judge, okay?" She glared at me as I continued.
The next day, I tried to take stock of where I was 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 nightclub, 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.
"Too bad, you fucking asshole!" My wife spat at me. "You are the reason we have a sexless marriage. Jesus Christ! What a fucking loser you are!"
"I can't deny it. You are right. It is my fault." Ann was so angry, she started shaking.
"I can't believe this. Well, you have gone this far, keep going asshole."
I resumed my story. 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 washcloth 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 were 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 my 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 knockout. 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 to 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 proceeded to make small talk for a while, 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.
Shortly after that trip we all went into Covid-19 lockdown. I constantly thought about the dozen different cocks I had serviced in the prior 18 months. I became really disappointed that I had gotten rid of all of my femme stuff. But no one knew what was going to happen next.
"Well, I know what's going to happen next. You are going to be sleeping on the couch!" Ann was pissed.
"I get it, I am only trying to be completely honest with you." I responded.
"Unfortunately, honesty has not been very high on your priority list, has it?" She continued to glare at me. "Anyway, we will pick this up again tomorrow, as Heidi will be home from school soon. Enjoy the couch, asshole!" I was devastated by her comments but couldn't blame her.
Indeed, Heidi came home shortly thereafter and we went about our normal household business.