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Going full Sissy
After my last adventures (see my previous story, Two BBCs in Three days) I needed to catch my breath. What was happening to me? Here I am, a middle-aged guy, married with a couple of k**s, willingly getting down on my knees and sucking cock. However, instead of feeling repulsed and guilty, I felt content and satisfied. It was like a finally found myself. Once again, I found myself constantly thinking about the dicks I had sucked and thinking about sucking more. I had truly become a submissive cocksucker. Something still felt like it was missing. Yes, I was a submissive cocksucker but what I really wanted was to be a submissive, sissy cocksucker. I had played around dressing a little bit but not too much. Being married and in the closet, I don’t really have too many opportunities to indulge. In addition, I am pretty hairy and far from being femme in appearance. However, I do travel for work occasionally and have had an opportunity to dress up while I am out of town.
Anyway, after my experience with Paul, I waited anxiously for him to reach back out to me. After about 10 days, I couldn’t wait any longer and texted him. He texted back and we proceeded to chat over the next week. Paul is a pretty cool guy. He clearly wants to have a sub worship his big dick but he is not into humiliation. I felt like I was just another of his friends. I learned from him that he doesn’t really date – he’s just not into that scene. I also learned that he does have a couple of white married women with which he has had long term affairs. He told me that he gets an opportunity to get together with one or the other every couple of months and gets to have a weekend of non-stop sex. However, in the interim, if he gets horny, he likes having someone like me available to satisfy his immediate urges. Hearing about this was an incredible turn-on. I was his standby slut. Not only was I cool with that, it was incredibly arousing to think about. There is just something about being a submissive slut and being able to provide pleasure to a horny man…it really gets me going! We chatted a bit about me and why I liked doing this and eventually we started talking about me dressing up femme for him. This appeared to turn him on as much as me. I told him about my dress up when I am out of town and about my favorite clothes – yoga pants and thongs. He wanted to know if I would be willing to really dress up for him – i.e. wig, make-up, jewelry, clothes, etc. I told him that the idea was incredibly arousing. I admitted that I had fantasized about it but that I had never done any of that. He then asked me since I had fantasized about it, did I have a sissy name. Somewhat embarrassed, I told him that I did and it was Livia. He immediately responded that he really liked that moniker and that I would be his “Livy.” Paul further pressed me about giving this a try and he asked me to think about it.
Over the next several days, I had a constant hard-on as I thought about being a real crossdresser for Paul and servicing him while dressed femme. Despite my brain telling me that it was a bad idea, I knew I had to try it. I texted Paul and told him that this would be a work in process but I was happy to give it a shot. We agreed to meet the next weekend. I was able to get my stash of clothes out of their hiding place and headed to Paul’s place on a Saturday morning. I told my wife I had some work to do in the office (not unusual) and that I would be back after lunch. On the way to Paul’s I stopped at a costume shop and picked up a wig. I was worried that I would be embarrassed about shopping for one but it was no big deal. When I entered the store, a lady came up to me and asked me if I needed help. I told her that I was going to a costume party and needed a woman’s wig. She didn’t even bat an eye and asked me what I had in mind. I told her that I wanted something that was dark and long and she escorted me over to a section that had several examples. It didn’t take me long to pick one out and she happily wrapped it up, had me pay, and I was on my way.
I then proceeded to Paul’s place. While I was considerably less nervous than my last visit now that I had met him and had already hooked-up with him. I was a different type of nervous as I was taking another step toward sissydom by doing this. Was I sure this is what I wanted to do? Was I going to embarrass myself? How would I look? All of these things were running through my mind as I approached Paul’s place. As with my other encounters, I heard myself think, “Fuck it, let’s do this.” I parked the car and texted him that I was walking up to the front door. After a couple of minutes, he came downstairs and let me in. I felt a little awkward greeting him but he was totally cool and showed me inside. Once inside, he told me that I could dress-up in the bedroom or the bathroom. I excused myself to the bathroom and proceeded to get dressed. I put on my thong and yoga kaçak iddaa pants and felt my cock start to harden. I then put on the lady’s sweater/pullover that I also had. Lastly, I put on the wig. Looking in the mirror… I looked awful, like a middle-aged guy wearing a wig. I tried to style the wig a bit but did not have much luck. Feeling a bit disappointed, I prepared for the worst and exited the bathroom and walked into Paul’s living room.
Paul was naked, on the couch, watching porn. He smiled when he saw me and beckoned me over to him. I knelt down in front of him and apologized for my appearance. Paul shushed me and said “Livy, you look very sexy.” Emboldened by his kind words, I dropped down and immediately started sucking his cock. I wish I could say that the experience was as good as the first time but I would be lying if I did. I could not keep that damn wig from getting strands of hair in my mouth. It was so frustrating! I think I did a good job hiding my frustration as I eagerly sucked and swallowed Paul’s beautiful cock. If you did not read my prior stories, Paul has a magnificent BBC. It is almost nine inches long but incredibly thick at the base. As I was sucking him, he again reminded me to be careful with my teeth as I had a hard time getting my mouth opened up enough to fully engulf his beautiful black dick. While the wig continued to be getting in my way, I continued to stroke and suck him. He appeared to enjoy it and after about 10 minutes, he told me he was going to cum. I sped up my sucking and continued to stroke his shaft with my hand. He then grunted and I stopped moving my head and moved my mouth so that it just covered his head. I felt my mouth fill with his delicious jizz (along with a lot of wig hair) and then I swallowed. Just like the previous time, I sat back on the floor, with my back against his couch and we just chatted for a bit while he continued to have porn playing on his television. He told me that I was the best cocksucker he ever had and I swelled with pride. I told him that I had a hard time with the wig and that the strands kept getting in my mouth. He told me that “Rome wasn’t built in a day” and that I would continue to learn and get better dressing femme.
I told Paul that I was worried about buying more stuff and having to figure out where to hid it. He had a great idea. He told me to order what I wanted and just have it sent to his place. His apartment could be my experimental lab. What a great idea! While not perfect, it was far preferable than me trying to find a hiding place at home that my wife would not stumble across. As we chatted, I really felt uncomfortable about sitting there in that ridiculous get-up. However, Paul continued to treat me as if everything was normal. While that allowed me to relax a bit, I still felt awkward. I then excused myself to the bathroom and changed my clothes. After changing, Paul again walked me downstairs and we agreed to keep chatting about what to do next. The first thing I did when I got home was to start shopping for wigs. I am a bit ashamed to say that I learnt way more about wigs than I ever thought I would. Synthetic or real hair. Lace front or full lace. These were just a couple of things I learned about during my research. After a couple of days, I finally found some that were the styles I liked, had the appropriate features, and were not too expensive. As I have continued to indulge this fetish, one thing I have learned is that being a woman is expensive! I finally decided on a Haircube wig. It was only $25 and had some nice features that, hopefully, would make it look more realistic than the costume store one I had previously purchased. I also bought a wig grip head scarf to better hold the wig in place. In addition, I bought another pair of yoga pants and a matching long sleeve top. Again, whatever I could do to cover-up my body hair was a trade-off I was willing to make in order to try to appear as femme as I could. About a week later, I heard from Paul that all of the items had been delivered and he was anxious for me to come over and try them on. We arranged for another Saturday morning meet-up.
Once again, I arrived at his place and he showed me upstairs to his apartment. Inside, he gave me a bag with my new stuff and I excused myself to the bathroom to get dressed. This time, I had worn a thong on my drive to his house. I felt very kinky putting them on under my boxers and walking around at home with them under my clothes. I also felt naughty on the drive as I looked forward to getting his monster dick in my throat. I got dressed in my new clothes, the new yoga pants were a disappointment, I was hoping that they would be a little looser so that I could have them ride up my butt crack. Unfortunately, they were just loose fitting all over. I put on the wig grip and my new wig. I cautiously looked in the mirror and…it was not bad. The new wig had a very nice style kaçak bahis to it and I was able to brush it out so that it looked nice and full. It framed my face nicely and, while I would never be mistaken for a model, I thought I looked presentable. As I got ready to exit the bathroom, I started staring at myself and wondering what I would look like with make-up…Shit! Here I go deeper and deeper down this rabbit hole. Snapping myself back to reality, I walked out of the bathroom and once again, Paul was naked on the couch waiting for me. He too liked my new wig and I kneeled before him. He smiled and called me Livy, his cocksucking sissy.
I smiled and went to work on his cock. The new wig was better than the cheap one I had purchased previously but only slightly. Hair continued to get in my mouth but at least it was easier to swipe it away. I again worked on Paul’s gorgeous manhood and lost myself as I focused on his big cock. I licked, suckled, and nibbled on his huge head and sucked him in deep into my throat. I caressed his balls with one hand while I stroked his huge shaft with my other. He commented about how he liked having Livy sucking his cock and he had me tell him how much I loved sucking it. “Does Livy like sucking this big dick?” “Oh, yes. Your dick is amazing! I love having it in my mouth.” After about five minutes, Paul did something different. He stood up and grabbed me by the back of my head and started fucking my mouth. It was incredible! First, by him standing up, my posture was more vertical, which allowed the wig hair to drop off and away from my face – no more hair in my mouth! Second, the submissiveness of allowing him to fuck my face and shove his cock into my throat was an incredible feeling. He would slowly pull my head toward him as his cock pushed passed the entrance to my throat. Once fully lodged inside me, he proceeded to rapidly move my head up and down on his massive meat. While the movements caused me to gag, the feeling of his cock sliding up and down my throat was fantastic. I was so turned on to be on my knees, just an instrument for his pleasure. Over the past couple of years, I had gotten pretty good at deepthroating by practicing on dildos. I would mentally prepare myself to take the toy all the way in my throat by taking a breath, breathing out and relaxing. But you don’t have that opportunity when your head is being forced down on the real thing. While a bit unsettling, it was also very arousing. Saliva started running out of the corners of my mouth as Paul continued to fuck my throat. I felt so wonderfully slutty. It took only a few moments before he stopped, held me against his abdomen while he shot his load directly into my stomach. I could feel his massive dick throb and quake in my throat. He slowly slid his cock out of my throat and I held the tip between my lips to lick up any remaining jizz that was oozing from his cock slit. I could not believe this. Here I was on my knees, wearing a wig and female clothes, feeling euphoric about the orgasm that someone else just had at my expense. I was incredibly turned on and knew that I would be having a massive orgasm when I jerked off at home later.
We again chatted for a bit. I was feeling much more comfortable sitting there in my outfit. I think I was just getting more comfortable being a crossdresser. As I sat there, I was turned on by the fact that Paul had shot his load directly into my throat/stomach. At the same time, I was disappointed that I didn’t get a full taste of his load. Oh well, I thought, there would be other times. After a bit, I excused myself and changed and then left. My cock was rock hard on the way home and I could not wait to relieve myself. I kept thinking about him holding my head with his huge cock fully in my mouth and throat. What a sissy cocksucker I had become. As I thought about this, a smile formed as, once again, a feeling of contentment swept through my body.
Paul and I were not able to connect for the next couple of months as our schedules didn’t line-up. However, we did continue to text each other. Paul continued to slowly push me toward becoming a full crossdresser as he asked me what I thought about make-up. I admitted that the idea of being fully made-up was quite arousing but very daunting as I had no idea of where to begin. I then began to watch Youtube make-up tutorials and downloaded the Youcam and Ulta apps on my phone and began to experiment with AR make-up applications. I slowly put together a list of items that I would need: primer, foundation, blush, lipstick, eye-liner, mascara, and eye shadow were the first things I picked out. There were additional things that I still needed to research like fake eye lases and eye brow pencils but I thought I had a good start. On a business trip, I stopped into Ulta – and was immediately lost. I had never paid attention to the fact that make-up was grouped by brand and not by product. güvenilir bahis I felt out of my depth. Before I knew what to do, a nice lady came up and asked if I needed help. I played dumb and showed her my list and asked if she could help me. “Is this all for your wife?” “Sure” I responded as she proceeded to escort me through the store and started grabbing my items. “Your wife has good taste” the lady said to me. I just smiled. After she help me get everything she asked if I needed brush applicators. I said I did and she picked me out what appeared to be a nice set. She then recommended a couple of sponges to apply the foundation, I readily accepted her suggestions. After everything was collected she took me up front and I checked out.
Returning to my hotel, I proceeded to start applying. Frankly, the primer, foundation and blush were all relatively easy to apply. The video tutorials I watched were very helpful. The same could not be said for my eyes. Liner and eye shadow are hard! I mean, really hard. After my first try, I looked in the mirror. Oh my God! I looked like a strung out heroin junkie. So much for my first effort. I felt reasonably good given how easy I was able to pick up the primer/foundation/blush work and thought I would try again with the eyes the next night. Oh well, let me clean this stuff off and get to bed. Uh oh, the make-up, especially the eye liner and mascara was not coming off with soap and water. Great, I forgot to buy make-up remover. Now what? I continued to wash and scrub my face until I got all of it off but not before I irritated the skin around my eyes from rubbing them with a wash cloth. What was a not great experience turned into a full fledged disaster when I felt how raw my skin was. Shit! Experience is a bitch of a teacher. I was not able nor was I willing to do any more “practicing” until my skin healed. When I returned from my business trip my wife asked me about my skin. I told her I accidentally touched my face with a magic marker and irritated my skin with the wash cloth. She just shook her head and walked away.
Just before the 4th of July, I was able to connect with Paul again. I had purchased a long sleeve dress and black pantyhose (pics in my gallery). I visited him, dressed, applied some lipstick and wore my wig. This time, I brought some hairspray and tried to style the wig so that I could keep the hair from getting into my mouth. Unfortunately, it didn’t work. I need more practice with the wig but since it is at Paul’s I have not had the chance. Once again, he was waiting for me on the couch and I went over to service him. This time, before I started sucking him, I kneeled in front of him and gently stroked his cock. It had been a couple of months since we had gotten together and I really missed his cock. I loved how it felt in my hand. The heat, the combination of spongy yet firmness, and how it looked all made my mouth water. I proceeded to give him a nice blowjob but the wig hair continued to get in my mouth. I started feeling discouraged. It is really hard to give a good blowjob when you keep getting hair in your mouth. I persevered and tried to make the best of the situation. It did not seem to bother Paul as he whispered how my mouth felt better than pussy and that I was the best cocksucker he ever had. I just groaned in acknowledgment as I continued to slide my mouth up and down his shaft. He again stood up and grabbed the back of my head. This time, though, he told me to grab his ass with both of my hands and once again proceeded to fuck my face. As he was getting ready to cum, he stopped and took his cock out of my mouth. He started stroking his dick with the slit inches away from my lips. “Does Livy want to be fed?” “Oh God, yes. Please feed me!” I opened my mouth and stuck my tongue out. He groaned and shot his seed onto my tongue and into my mouth. Hmmm, I had forgotten how delicious his cum tasted.
Despite how pleased Paul was, I was really irritated with my wig. I really need to figure out how to keep the hair out of my mouth. It is incredibly distracting. Since it was the holiday, I didn’t hang around and got up and changed. This time, I asked if I could take all of my things with me. One, I really need to figure out how to wear this wig effectively. Two, my femme clothes need to be washed. Paul understood and I took my stuff and left. Work has been busy since the holiday and I have not been able to get my femme clothes washed. This cost me a chance to see Paul as he told me he really wants Livy to service him. I understood his desire but being Livia was starting to be a lot of work. In addition, Paul indicated that he would like to see me wearing the following: bodystocking, choker, cage, and heels. Talk about going further down the rabbit hole. I was a little taken aback by his latest request but by the end of the day I was back on Amazon shopping for these new items and thinking about being fully made up while dressed in these new clothes. I looked down and my cock was rock hard. I guess I know where this is going…
I will keep you posted on my progress. However, my next story will be about my recent experiences with Doublelist.
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