lingerie 2.0

Posted by Scott Kashket on February 25th, 2019

Back story. I've been crossdressing for many years. The reasons for it are not really important however, I know I enjoy escaping being me, and getting to be softer, submissive and docile. My friend, Sir caught me crossdressing a long time ago, he has never really cared what I do as he has lots of women. We both enjoy hot teens stockings the friendship and no judgements about anything. Tonight was going to be like many other nights just two friends hanging out, laughing and joking. Me, getting all dolled up and feminine, him kicking back having a beer while we cook up food and hang out. I prepared for tonight by taking a nice hot bath and shaving everything that matters. To finish cleaning myself, I give myself an enema. A gurl has to be clean everywhere. Like all girls, I enjoy my skin feeling soft and moist, so I use some vanilla body lotion, topping it off with a little vanilla body spray. Next I put on my white bra with fake boobies. It's been a rough week so time to turn off / put away my brain. I tuck my little penis back and tape it in place. There's no need for it tonight, I want to feel completely like a gurl. This also means for the rest of the night I will have to sit down to pee like a normal girl. Once that's put away, to start my real transformation, I inject a little lubricant into my bottom. This allows a large plug to be inserted. The plug instantly pushes against my prostrate, giving me pleasure in ways you don't even normally experience. Part of those pleasures, is instantly feeling more feminine. A tight thong holds and covers all of that up. Slipping into a pair suntan oil sheen pantyhose, then a garter  As I rub my legs together, the smooth silky nylon rubbing back and forth is just heaven. A white body suit goes on next, and a white sundress with pink flowers completes my ensemble. I then put on a long brown wig, it mostly covers my face, except the bright red lipstick which just make my lips stand out. Lastly, I pull out a pair of 5 in nude heels. I now feel like a little submissive house wife. It's strange to transform this way, but it's so comfortable and refreshing. Checking myself out in the mirror, I can't help but love the way I look, so cute and feminine. The last little touch is a little anklet that says "SLUT" after all can't be a complete good gurl. It's not long thereafter, that sir shows up. He comes right in the house without waiting for me to answer the door, I know he's coming and he doesn't care what I'm really up to. I walk into the kitchen to find him standing there, his first words are "wow, you look pretty perfect girls in lingerie". I thank him, and proceed to give him a nice warm embrace. In our embrace, he pulls back and askes "New perfume?" I replied back with a smirk and yes. After our embrace, I tell him to go sit down so I can get him a beer. We proceed to catch up on the last couple of weeks, and our life stress. Through the course of the conversation I make a nice simple dinner. Sitting back after dinner, enjoying a Twinkie as a desert I see sir staring at me. I'm not sure why but the intensity of him watching me; made me joke around and slide the Twinkie in and out of my mouth, feigning sucking dick motion. I expected him to laugh at me, instead he said nothing and started rubbing his cock. Something about this a second ago seemed so innocent and funny. Through his loose gym shorts I can see his huge cock start to swell. Not sure why but I am not able to remove my eyes from what he was doing. Was he really seeing me as a girl? This is a first. Here we are sitting next to each other, him rubbing his cock while I suck on a Twinkie. It seemed so strange yet so natural. Without even thinking about it, I keep sucking the Twinkie, I can't stop watching him and he can't stop watching me. It's only a couple of minutes before he pulls his cock out, letting me see his monster in its full glory for the first time. It's so thick, veiny and long. No wonder the women he is with always have a smile on their face. With free hand he takes my dainty hand and places it on his snake. I know I should pull the hot girls in stockings but I'm completely mesmerized buy it. Wrapping my fingers around it, and start stroking, he leans back and moans. I'm not sure what I should be doing neither one of us likes guys but yet here we are. Should I stroke it, play with it or run away? My mental questions are answered not by me, but by him. Sir puts his hand on my head and starts pushing me down to his monster. While trying to protest, I'm not a girl and I shouldn't be doing this he calls me by my feminine name Stephanie. He proclaims "Stephanie, you are going to suck me off". There was something about his voice and the way he spoke. I knew I dare not object further. Besides what could I do or say? Here I am all dressed up, as a girl, painted nails, bright red lipstick and an anklet that says "SLUT". I've been sauntering around all night, sliding my legs together so I can hear the nylon rubbing, and swinging my hips back and forth. He's just an alpha male responding to what he sees; a feminine gurl. Accepting my new found position, I start licking his cock. As we are still sitting the hot girls in lingerie side by side it's incredibly difficult so slowly dropping to my knees in front of him. He spreads his legs to allow me more access. It is a struggle even at this angle to get his cock deep in my mouth. Not that I really know what I am doing, I'm just mimicking what women have done for me. Keeping my tongue engaged along the bottom of his shaft while sucking his cock in and out. Using one of my hands I cup his large balls, caressing them, with the other I stroke the part of the shaft I am not able to get into my mouth. Sir is moaning my name "Stephanie", "Stephanie, suck me". Focusing on his moans and forgetting about the world around me I get lost in the pleasure of the whole situation. Here I am servicing Sir, providing him pleasure. As I was lost in the moment, I don't think it took very long before his balls tightened up, and he growled that he was cuming. A sense of success er comes me, I am about to make him cum as a gurl. Moments later, I could feel his shaft shooting large streams of cum right into my mouth. So much cum, I can't possibly keep it all. As result some of his nut leaks out of my mouth. Doing my best to not let any of it go to waste, I keep my mouth tightly locked onto his cock, using my fingers to keep stroking his cock. I want his orgasm to continue. Before long, he slumps back and relaxes. I do my best to slowly remove my mouth not letting any cum loose. But it's to no avail, some gets away from my mouth. I dutifully swallow every drop that I can the lingerie stockings. Surprisingly, the taste and texture is not as bad as I had imagined. Leaving him sitting there with his cock out; I get up, and go fetch a towel for him to clean up what mess I didn't catch. However, instead of handing him the warm towel. I instinctively drop back to my knees and gently clean his cock with the towel. After it's cleaned, I look up at him and he smiles "Thank you, that's enough" and he puts his cock away. I return to my place on the couch, not sure what to think about what just happened. So I quietly sit there. Eventually he speaks up, I needed that, but it's not going to happen again. Just a onetime thing. With a little bit of relief I agree with him. As much as I enjoyed it, it's probably not something I should do. I take my leave to refresh my lipstick and clean the last bit of his nut from my face. Once I get back we turn on a comedy show. Still sitting next to each other, he puts his hand on my leg and caresses my nylon clad legs. I don't know why, but his dominance tonight makes me feel so submissive, so gurly. Perhaps the feelings of ultimate submission has something to do with just sucking his cock off and swallowing his nut. I'm not sure, nor do I really care at this point I just lean my head against his arm moving my legs towards him. Granting him further room to rub my legs; as he seems to enjoy that. About half way into the show, I can see his cock starting to harden again. Through our laughing it's moving up and down r starts to rub his cock again, just like last time I can't stop watching him play with his cock. I get lost in what he's doing and forget about the show. From time to time, I can hear him laughing. For me my interest has changed I am completely focused on what his hand is rubbing. Thinking back to just a little bit ago it was so fascinating, submitting my mouth to a man for his pleasure. Somewhere while lost in my own world, I hear Sir say "Stephanie, Stephanie, I need another beer". The only words I can muster are "yes sir". As I get up, his hand caresses the back side of my leg, and sliding up under my dress. Hmmm, you do have a cute ass, he tells me; I smile and thank him. It feels so good to be treated as a girl. On return, I see his cock out of his shorts. I hand him his beer, no words need to be spoken. I just drop to my knees, and he slides down a little bit so I can the sexy girls in lingerie him off again. I can see the faint lipstick line of where my mouth got down to last time. This time I want to go deeper. I know I will never be able to deep throat all of his cock, but I want to try. Maybe little by little I will succeed arting again by licking his balls and all the way up the shaft; he moans. I'm off to a good start, keeping up with that I kiss, then lick his balls. I can feel they are still heavy with cum. caressing them with my hand, I work my tongue slowly up and down his shaft until it's completely covered in saliva. Once it's nice and wet, I take the plunge and start sucking it in and out. Slowly, and at a constant pace. Making sure the whole base is at the same motion with my other hand. I know a nice slow blow job is more pleasurable than a hurried one. His groans are also confirmation that I am doing it as correctly as I know how to. Just like last time, I get lost in the sensation of sucking his cock. I'm not sure how long it has been but he starts to moan, "Stephanie, here's your next treat". With that, I can feel his cock pulse and start shooting more and more cum into my awaiting mouth. It feels like he is shooting more this time. Again, I do my best to capture it all. Any good girl swallows the entire load. Once he's finished shooting his cum into my mouth, this time before I just swallow it, I open my mouth a little bit to show him I have it all and then swallow. He is clearly spent this time, just sitting back relaxing enjoying the afterglow. So I go fetch a fresh warm wet towel to clean him off. This time when I return I see his cock sitting there with a little bit of cum oozing out. Instead of letting it go to waste, I lick  Then gently clean my lipstick off his cock. This time I went deeper. Who knows what will happen if he keeps forcing me to pleasure him. For now, Sir puts his cock away and I take my place back on the couch next to him. This time there is no awkward silence, he looks over at me and says maybe for tonight you can suck my stress out... Four more times, I dropped to my knees to suck Sir off that night. By the end, his nuts where dry and he was smiling at the end of the night. I felt completely at ease in my feminine role. Providing relief. While he said this was only a onetime thing. I have a feeling he will be back when the need arises...