Being a Dutiful Sissy Husband

Being a Dutiful Sissy Husband – Part 4

I got down between Ann's legs and started kissing the inside of her thighs, my hands moved up to her chest and started fondling her B cup titties and nipples. I continued to move my mouth slowly toward her pussy, continuing to kiss my way toward my goal. I gently kissed her pussy, using my tongue to part her lips and tasting the moistness that was growing inside. I then gave her a big lollipop like lick all the way up to her clit. Ann audibly groaned. "Mmmm, that's it you little faggot! Lick my pussy!"

As I settled in to pleasure my wife I couldn't help think about how lucky I was. Sucking a thick cock a couple of hours ago and now lapping up a juicy pussy. Awesome! It wasn't that long ago that my marriage was hanging in the balance when my wife found out about my proclivities. What a whirlwind it's been. Once again, my mind started wandering back to how I ended up in the position.

With two growing kids and dealing with family stuff, our sex life had grown stale and become basically non-existent. I had taken solace in masturbation as my sexual relief as my proclivity for porn grew. As mentioned previously, I liked visiting streaming sites like Xhamster. The next step on my journey was Reddit. My son was a Reddit user and I was enamored that there could be a narrow focus on various topics, e.g. golf, football, Star Wars, etc. Given my penchant for porn, it wasn't long after that I discovered the NSFW subreddits. Subreddits like Sissyhypno, cuckold, cumfronanal, deepthroat, femboys, traps, and massivecock were just a few of my favorites.

However, the next step down the rabbit hole was when I stumbled upon the subreddit, Randomactsofblowjob. This was a place where people were either looking to get or receive a blowjob. Are you kidding me? This was amazing! Over the course of several months I would fantasize about making a post and then getting to hook-up with a stranger and suck his dick. I would pretend to have real hook-ups by sucking on one of my dildos. It would inevitably lead to a mammoth orgasm. Afterwards, sanity would be reasserted and I would dismiss the idea of ever actually "doing it." But... the fantasy was persistent. The sissy hypnos were persistent. The lack of sex at home was persistent. It was inevitable that I would actually try to do it.

In order to hide my NSFW activities on Reddit, I had created another profile. I used this profile and created a post for the subreddit looking to suck a cock. Over the course of the next month, I had a few replies but it was mostly people that were also fantasizing but didn't have the nerve to actually go through with it. But, finally, I did get a response from a dude named Matt looking to get his dick sucked. This was in the second week November, 2018. We traded some messages, his wife wouldn't do oral and he really wanted to get a blowjob. With Thanksgiving coming up they were travelling to her family in Texas but she was leaving early because he was still working. This left him by himself in their condo. It was a perfect opportunity. I was so excited but yet filled with trepidation.

Was I really going to cheat on my wife? What about disease? We had both assured each other that we were std free but how can you trust a complete stranger? What if he was a Jeffrey Dahmer type guy? He could drug me, eat and mutilate me and no one would know. Honestly, these same thoughts run through my head for every first encounter with someone but it these thoughts loomed much larger since this was going to be the first time a tried this. After a couple of angst filled days, I finally told myself "Fuck it, let's do this." We arranged to meet a couple of days later, on a Sunday afternoon. I told my wife that I was going to watch football with some work friends.

When the day came, I was giddy with excitement yet still anxious about doing it. I sent Matt a text when I was heading out. Part of me hoped that he would cancel while another part of me was looking for a confirmation. As I started driving, my phone pinged and he said he was ready and waiting. I drove over to his place. The closest parking was a couple of blocks from his house. As I was walking over, I kept thinking that I should be nervous but I wasn't. I thought my conscience would be telling me that this was wrong but all I was feeling was anticipation. I had waited so long for this and I was really excited to get my lips on a dude's cock. I got to his apartment building and I messaged him that I was downstairs. He responded that he would come down to let me in. After a couple of anxious moments, the door opened and there he was... a regular dude. He looked like his picture and he introduced himself as Matt. I gave him my name, we shook hands and we headed inside. We got to the elevator and went up to his floor. There was some nervous silence as we waited for the elevator door to open. He was clearly as nervous as I was as he guided me down the hallway, the wrong way. He apologized and we turned around and went back to his unit. After this, I was much more relaxed now knowing that he was as anxious as I was. Getting inside, it was a nice apartment, a one bedroom that was tastefully decorated.

We sat down on his couch and we just stared at each other. I said "I am not sure how this is supposed to go down, so I am just going to get started." I started rubbing his crotch and his cock sprang to attention. He was wearing a t-shirt and sweat pants and as I continued to rub his groin, his cock started tenting his sweats. I would like to say that my lips were watering at that point but I was so nervous, my mouth was dry. Matt stood up and I dropped to my knees. He pulled down his sweatpants as I continued to rub his crotch and then, for the first time, I was inches away from another dude's cock! I was entranced by his beautiful dick. He was closely shaved, with only a little hair on his abdomen. His cock was over seven inches, circumcised with a nice head. Not as big as I would have hoped but nice nonetheless. As I knelt in from of him, caressing his meat, I was thinking that I could not have gotten luckier with my first dick. I continued to rub his shaft and started thinking about all of the techniques I learned, emulated, and practiced over the past couple of years. The first thing I did was to softly kiss the head of his rock hard cock. His smell, the taste, the feel, all of it was heavenly. Everything about that first little taste just felt right, so natural. In the back of my mind I was wondering if I had always been destined to be a sissy cocksucker or whether my mind was warped by all of the porn I had watched. In any event, I was excited to get to work.

I kissed and licked every inch of his shaft. Slowly, I started to feel saliva beginning to form in my mouth and after a minute, I wrapped my lips around that beautiful head. I started slowly, going in and out just a little at a time to allow his cockhead to get nice and wet. I made sure to swirl my tongue around his head as well. As his cock become wetter, I started moving farther and farther down his shaft until I was deepthroating him. He let out an audible gasp and said that he had never been deepthroated before. I started moving my mouth up and down his shaft, from the tip to the base and continued to go faster and faster. I was intoxicated by the taste and smell of his man meat. He stopped me for a moment so that he could sit back down on his couch. I moved between his legs and continued to suck on him. I knew that I was hooked. As much as I wanted to deny it, I knew I was a sissy cocksucker and that all I wanted to do was to suck cock.

After only a few short minutes, he started groaning and told me he was going to cum. My first load! I was getting ready to swallow my first load of cum. This was great! Over the last 10 years, I have almost always swallowed my own cum when masturbating. I had really grown accustomed to the taste and couldn't wait to see what another man's cum tasted like. I kept sucking him. I would deepthroat him and then come back up to the tip and swirl my tongue around his head and then slide his cock back down into my throat with my lips pressed against his midsection. He then grunted "Here it comes!" and I moved my mouth back so that only the head of his cock was in my mouth. I knew he was coming as his cock started convulsing but I never felt the spurts inside my mouth. Instead, my tongue started tasting his cream as it filled my mouth up. He tasted great! I swallowed it all and then grabbed his shaft as I moved my mouth off of his dick. I then watched his cock slit as a little more cum was oozing out and then I put my lips back over the tip of his head and sucked the rest out. Seeing that in porn is such a turn-on for me and here I was doing the same thing to a dude I met less than 10 minutes ago.

I continued to suckle on his dick for a couple of minutes and then got up and sat next to him on the couch. We relaxed for a bit and made small talk. He told me that I was a fantastic cocksucker and that he loved the feeling of being deepthroated. I thanked him for the compliment and told him I have been practicing for awhile. He then asked me to see my cock and I realized he was totally naked and I was still fully dressed. I undressed and he started caressing my cock. He gave me a look that made me think he wanted me to kiss him. I leaned over to give him a kiss but he put a hand up and said "I'm not ready for that." I apologized and told him that I was a very oral person and asked if I could suck his cock again. He eagerly agreed and sat back on the couch. I got down between his legs again and went back to work. This time, in addition to my mouth, I started using my right hand to stroke his shaft. I also occasionally dropped my mouth down to his balls and sucked them into my mouth. They felt wonderful! I wanted to lick his ass but I was too nervous and too reluctant to try. Instead, I worked his cock and tried to emulate my favorite porn clips. While he lasted longer the second time, it didn't take long before his legs started shaking and he told me he was going to cum again. I continued to stroke his shaft while sucking on his head and took his second load into my waiting mouth. Damn, he tasted good! Again, I continued to suckle and nibble at his cock head until I knew I had gotten every drop. At that point, I started getting dressed and thanked him for feeding me. He told me that he was the one that needed to give thanks as he never had his cock sucked so good before. Pride swelled up inside me as I thought that all of my practice may have paid off.

I got dressed and we said our goodbyes. I headed down the elevator and as I got off, two women got on and I wondered if they had any inkling of what I had just done. As I tried to leave the building, I found that I could not undo the latch on the entry door. It wouldn't budge. I started to get really nervous of being stuck in this building and not being able to get out. After a moment, another resident came and unlocked the door to enter, I made my way out and laughed to myself about being trapped for a moment. As I drove home, again, I was thinking that I was going to start feeling guilty about what I had done. My first gay experience. The first time I cheated on my wife. Tasting and swallowing another man's cum. What had I done? But, I never felt guilty. I just felt... good. I was content. I kept thinking about his beautiful dick and I started thinking about when I could do this again. What was I turning into? What would become of this? I wasn't sure at that point but I knew I wanted to be back down on my knees again. As I continued to drive home, I savored the taste of cum I had swallowed and it brought a smile to my face.

As I emerged from my reverie, the smile was still on my face as my wife started convulsing with her first orgasm. I continued to lick her clit as I felt her abs and her adductors (abductors? The muscles inside her thighs) contract right before she started shaking. Unlike some women, Ann can't keep going after an orgasm, her clit is way too sensitive and she needs a moment to settle down. I continued to lick and kiss her pussy lips and as her convulsions eased, I dropped down further to start licking her ass. Ann loved to get rimmed and it help her maintain her arousal as her clit recovered from her recent orgasm. As her ass got wetter and wetter from my tongue/spit, I continued to reminisce.

After that first experience, I was floating on cloud nine and couldn't wait to do it again. Matt, the guy I hooked up with, went out of town for Thanksgiving to be with family. I was hoping that he would contact me when he got back in town. I waited. And waited. And waited but no dice, I never heard from him. I eventually did try to reach out to him. We traded a couple of messages but it was pretty clear that he did not want to hook-up again. I couldn't believe it but I was actually feeling a little hurt. Why wouldn't he want to see me again? What was wrong with me? I had a better understanding of how some women feel after a one-night stand. Thinking about that actually cheered me up as I thought I was acting a kind of gurly.

Anyway, once I knew I was not going to get another chance with Matt, it was back to Reddit to see if I could find someone new. It was the usual mess of interactions, guys just hunting for pics, others titillated at the thought of a hook-up but never wanting to actually go through with it, and some others that I just didn't click with. All this time, I was getting more and more anxious. After sucking the real thing, I no longer had any interest in playing with my toys (other than some anal play...) I kept yearning for the real thing. Then, I got lucky and connected with a dude that was not too far from my house.

We exchanged some messages and, at first, I was concerned because his messages had a lot of spelling errors and the grammar was poor. This is usually a warning sign for me to be careful. However, we continued to chat and I really started believing he was genuine. Only after chatting for a while did we exchange pics. Boing! He was a BBC. What a cock! The picture made it look huge. He told me that he was over 9 inches. Whatever hesitation I had went out the window as I knew I had to get that beautiful black tool between my lips. However, after that, the other shoe fell. He lived with his mother in an apartment. He was available at 9:00 in the morning, after his mom went to work. I was really conflicted. The idea of hooking up with a young dude was an incredible turn-on but I was also leery of stepping into something that could lead to issues later. On multiple occasions, I made him confirm that he was over 18 and that this was something he really wanted to do. He assured me that he was 19 years old, in college (attending at night), and wanted to find out what it was like to have a dude suck his dick.

Well, I think you can guess with which head was doing my thinking. We agreed to meet and I went to his apartment on a late morning, when his mom wasn't home. I texted him when I got to his place and he came down to let me in. He was a little surprised when he first saw me and said "Boy, you are really tall." I am 6' 2" and Devontae was about 5' 9". He was a very nice kid and he showed me up to his apartment. He immediately apologized for how messy the place was but took me to his room where he had his Playstation running Netflix. I am not gonna lie, I was incredibly turned on. He was a little heavy but was cute, well groomed and very polite. However, I really felt uncomfortable given our differences in age (I was in my late 40s). We sat down on his bed and I couldn't help but begin to caress the bulge under his sweats. Without any warning, he leaned over and began to kiss me. Wow! I did not expect that, I let his tongue enter my mouth and swirl around with mine and my dick was instantly rock hard. Whatever reservations I had, they went right out the window.

I got up and undressed down to my underwear and crawled back between his legs and pulled his sweats down. I was greeted by the most beautiful big, black cock I could have ever had hoped to see. I don't believe it was 9 inches but it was every bit of 8 inches with a nice head and a big ball sack. I started licking his shaft, kissing the head, and caressing his thighs. After a couple of moments of teasing him (and myself), I wrapped my lips around his beautiful dick and started sucking. I was swooning! It was an incredible feeling. Slowly, I took more and more of his manhood into my mouth until his head was pushing against my throat. I slightly adjusted my position so that his cock would slide in easier and I deepthroated him. Devontae gasped. I just held my lips against the base of his cock as I felt his cock twitch inside my throat. It felt wonderful. Over the next 20 minutes, I continued to suck and deepthroat that wonderful cock. I would periodically move my mouth down to his balls and suckle on those while I continued to stroke his meat with my hand. It was an incredible experience. Unfortunately, I could not get him to come. What was up with that? He eventually stopped me and apologized, telling me that it takes him a really long time to cum. I surmised that he must have jerked off a few times in advance of our meet-up and that he was spent. I told him that I was happy to continue to suck on this cock. Instead, he asked me if he could see my cock. I removed my underwear and my rock hard 6.5" dick popped out. He wrapped his hand around it and stroked it a little and then made a weird request. He asked if I would jerk off my cock onto his big dick. "Can you shoot your load on my cock, please?" he asked. I figured, fuck it, why not. In order to get myself off as quickly as I could, I then did something else I had never done before. As I was stroking myself, I licked his shaft, sucked his balls, and kept moving my mouth down until I was licking his ass. I was licking his ass! What a dirty little slut I was. He lifted up his legs to give me better access and I jammed my mouth against his butthole and began licking. I felt so slutty, so raunchy. It was incredible! It is amazing that up to that point I never really considered licking someone's ass but subsequently, it became so natural that I am disappointed if I don't get to rim my partner. After only a couple of moments, I was ready to explode and I proceeded to shoot my load all over his dick and stomach. It was an incredible orgasm. I dropped back down and licked up all of my cum off of his cock and stomach and Devontae just smiled.

Afterward, we continued to chat for awhile and I told him that I was disappointed that I was not able to get him off. He told me not to worry about it and that we could take care of that next time for he really wanted to fuck my ass. I just smiled but I was thinking that I don't know whether I would be able to accommodate his mammoth tool. I eventually got dressed and left. We continued to chat over the next couple of days until he got banned from Reddit. After that, it was hard to communicate. I did have his e-mail and we did exchange a couple of notes but we never hooked up again. I was bummed but I was starting to think that this is just how these encounters went. In any event, my first two encounters left me emboldened for more. All I could think about is when I could find another hook-up partner. Eventually, that would lead me to getting fucked for the first time in my life.

I continued trying Reddit but it was now close to Christmas and the postings were not as numerous. In addition, the holiday season was a busy time at work and a busy time at home, there really wasn't much of an opportunity to sneak away. Well, Christmas and New Year's came and went and as we headed into 2019, I was really looking forward to continuing with my adventures. Unfortunately, I was not able to find anyone on the Reddit personals. It was slim pickings. I was getting really frustrated. I continued to watch sissy hypnos and continued to imagine what it would be like to be a woman. Not only being a woman but being a slutty woman. It was empowering and arousing to think about. Being able to take control of your own sex life and to hook-up with random dudes is the polar opposite of my conservative upbringing. It was really intoxicating to think about.

Right after the new year, a window of opportunity opened for me. I needed to travel down to Miami for work. Awesome! A few nights by myself in a hotel? Say no more, I was ready to go immediately. Since I was going to get some alone time, I thought about buying some clothes to dress-up. As I have mentioned previously, I am a pretty hairy dude and, at that point in time, being married for 19 years, shaving my body hair is not something that would go unnoticed at home. Instead, if I could buy some clothes that would cover up my body hair, that may provide a good illusion for me to immerse myself in all things sissy. After flying to Miami, I drove my rental car to the nearest Target and picked up the following: yoga pants, pull-over top, and three pairs of thong panties. As an aside, Target has a nice deal on undies where you get three pair for something like 12 bucks. The only struggle is sifting through the various bins to find the right style and size. I am sure any female readers can relate. I was a bit nervous going into the store to buy some lady's garments but I quickly relaxed when I realized that no one cared. The employees are kind of zoned out, focused on their tasks. The other shoppers are also focused on their own thing. Nobody pays attention. I was finally able to find three thongs that were my size and I checked out. Target now has self-checkout, making it easy to pay for your items without having to interact with a cashier. It was easy peazy.

In advance of my trip, I tried posting on Reddit but Miami did not have the same number of active users as Chicago and I was not able to get a solid lead. I did connect with one dude and we traded pics (he had a nice cock) but he kept flaking out. He would stop communicating and then send a note at 2 am. Clearly, he must have liked thinking about getting a blowjob but it was a fantasy for him and he was not really serious about meeting. I was also frequenting a website, sissysocial.net. I had connected with an older sissy that lived in Ft. Lauderdale and we set-up a time to meet at my hotel during my stay. Unfortunately, something came up for him and he wasn't able to make it.

I got into town on Monday afternoon and after going to Target, I checked into my hotel and proceeded to try on my things. Everything fit okay and it looked pretty good. I really liked the yoga pants. They hid the hair on my legs but still allowed me to show off my legs with their skin-tight fit. I felt so sexy! I did not have any work obligations on Tuesday morning and that is when I was supposed to hook-up with the sissy I met from sissysocial.net. Unfortunately, he cancelled on me and I was left feeling frustrated, rejected, and incredibly horny. I had a couple of meetings for work and I found it hard to concentrate. I kept thinking about wearing those feminine clothes. It was such an erotic feeling to think about. Dressing up as a gurl and wanting to submissively serve a man, what was I turning into? Whenever I had any self-doubt, those thoughts were quickly dismissed by my desire to continue on this journey.

After work, I went back to my room and sulked. I dressed in my clothes and felt a little better but I really wanted to share this with someone. There was no action on Reddit, what could I do? Feeling as horny as I was, I again let my other head do the thinking and I proceeded to download Grindr. I had never used a dating app before and while I was a little leery, I had no idea what to expect. I indicated that I was in town for a couple of days and was looking to submissively serve someone. Since it was Grindr, I did not mention that I was an aspiring sissy, just a submissive. I was immediately bombarded with messages. Several were clear catfishing schemes, a couple were pic hunters but most were genuine dudes looking to find someone to fuck. I have to admit, I was a little taken aback given how forward everyone was. I was also concerned about safety and health. I did not want to hook-up either with some crazy dude or someone that was a live bacteria sample. It was a little odd, I was repulsed yet at the same time, strangely attracted to the activity. I sifted through the messages and chatted with about a half dozen dudes until I connected with Roberto. Roberto was a little more easy going than some of the other men and actually displayed a little personality in his responses. We agreed to continue chatting on Kik instead of Grindr so as to eliminate the messages that were continuing to bombard both of us.

Roberto told me that he was 42 (I was 48) and that he worked as a nurse at a local hospital. We chatted a little about my safety/health concerns. He assured me, as a health care worker, that he was clean and as for safety, he gave me his real name and the hospital he worked at if I wanted to confirm that he wasn't some psycho. I gave him credit for his openness. We exchanged pics and he really put on the full court press to meet. I was still a little concerned and begged off and asked if I could think about it and see if we could connect the next night. He was cool with that. I really had a hard time sleeping that night. All I could think about was getting another opportunity to suck a cock. I woke up the next morning with a raging hard-on and knew that I had already decided. I texted Roberto that I was ready to give it a go that night. A couple of hours later he texted me that he was excited that I decided to go ahead and that he would come over to my hotel after his shift ended at 6:00.

It was another long day as all I could think about was getting together with a dude I met on Grindr. Wow, what a slut I was becoming! The feeling of wantoness and sexual freedom was really turning me on. At a little after 3, I received a text from Roberto asking if I had condoms. I responded as to why would we need condoms? "You want raw???" was his response. I texted back "We were only discussing oral, right?" He responded, "Okay, see you tonight." I got a little indignant after that. Who does he think he is? We discussed oral only. Condoms. My ass, we don't need condoms! I should just cancel this. What a jerk. I didn't want to get fucked. Well...what about getting fucked? Wow, really? What are you thinking you little slut, you want to get fucked? I don't know, it might be fun. I continued to have this argument with myself for the next couple of hours until I resolved that I should just stick to what I am comfortable with at this point.

Roberto texted me at about 6:15 to let me know he was on his way. The hospital was about 20 minutes from my hotel. I waited in anticipation. I did put on my thong, yoga pants and pullover. While it was feminine, it wasn't over the top female. I laid in bed nervously waiting. My cock would get hard in anticipation and then soften as I worried about all the things that could go wrong. I had butterflies in my stomach and I was a little lightheaded. Finally, at about 6:50, there was a knock at my door. I opened it and let Roberto in. He was still wearing his scrubs from work but I could smell the soap emanating from him as he must have cleaned himself up before leaving the hospital. We introduced ourselves and sat down on the edge of the bed. I just looked at him and said "I am really nervous and am not sure what to do." He told me to relax and leaned over and started kissing me. We smooched for a couple of moments and then I felt his tongue move between my lips and I started swooning.

Feeling his tongue inside my mouth really got me excited but it also relaxed me as I moved into sissy mode and just let him have his way with me. I placed my right hand on the back of his neck and caressed him while my left hand went to his thigh. I felt like such a gurl as he continued to kiss me. After several minutes of kissing, he moved back and stood up and started undressing. He asked me to do the same. Roberto was about 5' 7" and 160 pounds. Dark skin (Mexican descent) with dark brown eyes. After we both undressed, I looked at his cock. It was rock hard. In some ways, it was a little disappointing as his dick was smaller than the first two I had been with. I would say his was about 6 inches and pretty normal girth. But, having said that, he was as hard as a rock which further excited me. I dropped down to my knees and started to suck his cock. He was easy to deep throat and I liked sucking him. As I bobbed up and down on his dick, my right hand was on his ass and my left hand caressed his ball sack. I was going to town on him and was looking forward to having him shoot in my mouth. However, Roberto had other ideas.

After sucking on him for a couple of minutes, Roberto pulled me up to him and started kissing me. He then pushed my down on the bed on all fours and proceeded to get behind me and started licking my ass. Wow!!! I never had that done to me before and immediately understood why people like it. It was an incredible feeling. I just melted as I felt his tongue enter my ass. All of a sudden, I didn't understand why I had been arguing with myself all afternoon. Why wouldn't I want to get fucked? This feels great! I told him how good it felt and that I was now disappointed that I didn't get condoms. "You want me to fuck your ass?" He asked. He then got up went into his pants and pulled out a condom and without asking, started putting it on. I was immediately nervous again. I had never been fucked before. Maybe this wasn't a good idea. But before I could say anything, I felt his cock pushing against my ass and before I knew it, he was inside me. At this point, I was grateful for his size. Anything larger may have been uncomfortable.

I am not going to get into many details of getting fucked suffice it to say it felt fantastic. I have played with my share of toys and liked ass play but had never experienced it with anyone else. Instead of getting into a detailed description of my deflowering, I want to share what was going through my mind. First and foremost, I chastised myself because I came the realization that, as a man, I was an awful lover. Roberto was incredibly attentive, gentle and caring in his lovemaking. It made me feel guilty for what I now concluded was my poor performance as a partner with my wife. Roberto would be fucking me and then would stop and ask me if I was okay? Do I like it? Did he want me to continue? Frankly, I learned a couple of things that I would be utilizing in the future. We switched positions a couple of times and when he had me on my back, I again just started thinking about what a little sissy slut I was. My legs were wrapped around his midsection and my arms were wrapped around his neck as I just gave myself to him. Every so often he would lean down and kiss me passionately. I just opened my mouth and let his tongue swirl around with mine. This was another experience of me being submissive and I loved it! Let me be an object for someone else's pleasure. The fact that he was getting pleasure was a further turn on.

We continued to fuck for about 10 minutes until I had to make him stop. I had not "prepped" for getting fucked and I was worried that I was going to poop the bed. As he continued to bang me, I just felt my rectal cavity relax and, not having been fucked before, was worried that I was going to make a mess. I extricated myself from him and he removed his condom as I started again sucking his dick. He then pushed my head further down and I knew what he wanted...One good turn deserves another, so I dove between his ass cheeks and started rimming him. He started stroking himself and a few seconds later, he shot his load all over his stomach. Part of me was very pleased that I was able to give him pleasure to cum but part of me was disappointed that I didn't get to taste him.

Afterward, we both laid back on the bed and proceeded to have a really nice conversation. I learned that while he was gay, he was in a similar sexless relationship. He and his partner were no longer intimate and he was bored and horny which was why he ventured on to Grindr. Despite our differences, we really had a lot in common. After about 45 minutes of chatting, Roberto indicated that he had to get going. He cleaned himself up, got dressed and gave me his cell phone number and asked me to call him whenever I was back in town.

After he left, I just laid in bed and thought about what had just happened. It was kind of unsettling for me. I was intimate with another man. This wasn't some jerk-off fantasy or even an anonymous gloryhole encounter. He didn't fuck me, he made love to me. This was not what I was looking for. First and foremost, this was the first of my three encounters that really made me feel like I cheated on my wife. Second, Roberto liked me because of who I was – a middle aged dude. I wasn't a sissy to him. I got way more than I bargained for on this one and really needed to think about where I wanted to go from here. In the meantime, my cock was rock hard and it only took a couple of strokes before I was shooting my load. Apparently, my cock didn't have the same reservations I did.

Coming back to the present as I continued to rim my wife, I chuckled to myself about how naïve I was a few years ago and how far I had come since then. Ann, now ready to go again, grabbed my hair and pulled me back up to her pussy. "C'mon bitch, give me some more of that talented tongue of your."

"Absolutely, my love!" I again smiled to myself as I thought about all of the practice my tongue as had over the last few years.