Breed Me Big Brother Chapter 1 Little Sister Begs to be Bred
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It has been awhile but I am back with an update. In this story, I will recount my two most recent experiences, the second one happened earlier today and I am still a bit unnerved by it. For those that don’t know, I am a middle aged dude (49), married with a family. Over the past couple of years, I have developed a secret, submissive sissy fetish. My first real encounter was about a year ago and that, along with my other activities, have been detailed in these stories. I have occasionally updated my profile page with some new pics and short vids to show that I am real. Anyway, I hope you enjoy my story.
The first experience I want to recount took place in early October. 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 still try to utilize Reddit (Floridar4r) but the subreddit is not nearly as active as in Chicago. So, I also use Doublelist to find hook-up partners. I have a couple of listings that I can post when I am down there. My standard one is 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. I travelled down on a Tuesday morning 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 the dude from my story “A Doubleheader with Doublelist.” This is a black 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 my 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 forgot 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 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, yesterday afternoon I found out that my schedule today 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 d**g 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 of 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 of 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 all of a sudden, 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 do 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 is rock hard as I type this so I guess I don’t have to really ask myself.
It was a quick come down 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. Until next time…
The first experience I want to recount took place in early October. 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 still try to utilize Reddit (Floridar4r) but the subreddit is not nearly as active as in Chicago. So, I also use Doublelist to find hook-up partners. I have a couple of listings that I can post when I am down there. My standard one is 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. I travelled down on a Tuesday morning 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 the dude from my story “A Doubleheader with Doublelist.” This is a black 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 my 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 forgot 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 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, yesterday afternoon I found out that my schedule today 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 d**g 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 of 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 of 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 all of a sudden, 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 do 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 is rock hard as I type this so I guess I don’t have to really ask myself.
It was a quick come down 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. Until next time…
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