A Sissy Friend For Dee free porn video

*A Sissy Friend for Dee* *Part 1 - Bedroom with Cammi* "Say it!" "No! Never." "You think he's hot. What's wrong with that? I think a lot of my friends are hot and I tell therm all the time!" "It's different for a guy and you know it. Besides, you're bi anyway, but I'm definitely not!" "Bullshit. Say it." Cammi was stroking me, very slowly. She was spooning me from behind, pressed into my ass, her hand gently gripping my cock and very slowly moving up and down. It was maddening. I wanted to spin around and fuck her, but, well...what she was doing was really turning me on. "You wish Clarence was behind you right now, don't you, Dee? His hard cock pushing into your crack, his big, rough hand holding your cock. Maybe his other hand gently squeezing your balls. Licking your ear like this..." "OK, I admit it, he's hot. OK? Now let me go down on you, you know you want me to suck your clit..." "Oh I do, Dee, and you certainly will. I'm just soaked. Oh God, I'm gushing. Here, taste - see? I love to get you to admit stuff. Stuff like you find Clarence hot. So do I, and so do all my girlfriends. And now my boyfriend admits it as well! What do you find hot? Tell me." "No, you tell me first." "His steel gray eyes. His massive arms. His devastating smile." "Yeah right. " "Your turn, Dee!" Cammi slowed down her stroking so I knew I had to keep playing along. "OK! Don't stop. I, well...his ass. It's slim and hard, almost like a woman's ass. A bubble butt." "Yes! I knew it. You have a thing about asses. Especially mine! And I love you kissing my ass, stroking it. I've also grown to love you rimming me. I always wash carefully there now. You are so talented, Dee! So, Clarence's perfect ass. But what about that big bulge in front? I often wonder what it's like. Like yours, big and thick and cut? Big mushroom head? Or uncut, veiny and really long? Tell me what you think." "I...I don't! I don't think about other guy's cocks! I'm not gay." "Remember when you let me fuck you with my dildo? You really loved it. Imagine, Clarence kissing you, maybe sucking your cock, then flipping you over and slowly working his big cock into your ass. Your ass is easily a match for his, you know. My gay friend Steve at work always asks me about you. He'd definitely be up for fucking you. Damn that would be hot to watch!" I had to control my breathing, I didn't want this exquisite humiliation to end. "What if you told Clarence he could fuck you if he let me suck his cock first..." I knew that would blow her mind. "Oh my fucking God! Dee, I knew it! That would be so fucking hot! Watching you on your knees in front of him, kissing his perfect ass then he'd turn around and you'd slowly lick the head then suck him, his hands on your head as he pushed into your sissy mouth, your glossy lipsticked lips wrapped around his cock..." Cammi pulled me to her, gave me a savage kiss and quickly lowered herself onto my cock. She was so wet I went in all the way easily; usually it took a minute or so to ease myself in. Cammi sat up straight, fondled her generous breasts as she pushed down hard on my cock. Then she tilted forwards and held my wrists above my head. "Pretend I'm Clarence, sitting on your cock. He'll be saying 'Oh Dee, I can't believe how good your hard cock feels deep inside my ass. My turn next!' And I'm sitting next to you both, masturbating, furiously rubbing my clit as I watch you two fuck. Oh yes..." I carry on with, "Then after I come inside him, I put on my wig and makeup, my sheer neglig?e, and tease him until I get on all fours, put my head down and he fucks my sissy ass, slapping me as he fucks me, and I tell him that I'm his bitch now..." Cammi almost never comes just from intercourse but once again, I've had proof that the most powerful sexual organ is between the ears. She bites my bottom lip hard and shivers as she comes with my cock still inside her. She screams and bites my shoulder for good measure as she convulses on top of me. She pinches both my nipples hard, saying, "I want to see you being fucked, his hard cock inside your sissy ass!" That did it for me and I held onto her hips as my own bucked hard, up and down, and I let out a high-pitched scream as I came inside her, my own orgasm lasting much longer than usual. As I finally slowed down and my hips stopped moving of their own accord, my senses started to come back and I noticed the pungent odor of sex and cum, sweaty bodies and Cammi's perfume. But she wasn't done yet, far from it. "Fuck you, Dee. That was the best sex we've *ever* had. Why didn't you tell me earlier? What else is going around in that secret headspace of yours? Damn, I shared almost everything with you, and that's the first I've heard about your gay fantasies?" "I'm sorry Cammi, I thought, I...it's embarrassing, and..." "Shut up Dee. How's this one - I go out dressed as a complete slut, my ass hanging out, my tits on display, sky-high heels. You're left in a little apron, long-haired wig, cock cage and full makeup. I meet a couple of guys, go back to theirs and get thoroughly fucked. I come back, pull you to the bed and tell you all about it. You're excited but I won't take off your cage. Then you beg me to clean up what they left." "Wow! Not sure about it really happening, but..." "Beg me, sissy. You know you want to take their cum. To lick it from my steaming hot pussy, to lap it up all up, my swollen lips need a gentle tongue cleaning as well." "Please, Cammi. Let me clean you up. I know you're sore from being fucked by those guys with massive cocks. Let me lick you clean, lick up all their nasty hot cum from your pussy..." I reached over to stroke her slit but I definitely got that one wrong. Cammi pushed my head down. What? She couldn't mean, not really... "Good boy! You weren't there to suck their cocks, get them nice and hard to fuck me, so you can taste what they left inside of me. All wet and hot and gooey. Get going, sissy! Get that tongue working!" I tentatively stuck my tongue out. Not too bad, couldn't really taste myself. I'd tasted my own cum before, just to see what it was like, but never taken a load, so to speak. Cammi roughly shoved my head in hard, mashing my face into her crotch. "Don't be afraid, little sissy! Get your tongue inside! Clean it all out!" I did as ordered, expecting to gag but to my surprise it wasn't as bad as I thought. A little bit salty but not disgusting, and the more I licked and swallowed, the better it got. Soon I was thrusting my tongue in as far as I could, then backing out and flicking then sucking on Cammi's hard clit, then diving back in again. "Ahh, that's so good you little sissy. Eat it all up! Next time I'll have them fuck your sissy mouth and come all over your face!" I went to town on her clit, teasing and flicking it, shoving a couple of fingers into her messy, wet snatch, until Cammi came, trembling and pushing my head in ever harder, forcing out more cum. I let her finish then licked out the leftovers, making my way to her inner then outer lips, then carefully and lovingly licking her inner thighs. "Come here and give me a kiss, you cum-eater. Let me have a taste. Mmm, you really enjoyed that, didn't you Dee? I think you'd like it for real. But probably even more directly from the source, right? Look at this, already hard again. So tell me, now that I've come myself a few times, what's your sexual fantasies. Spill!" Cammi was gently fondling my balls, running the palm of her hand over the head of my cock, and generally ensuring that I stayed hard. I stared into her light blue eyes, her lips smiling at me, and told her. "It started a long time ago. Shemales. Woman with dicks. But these days these hold little interest, I'm not interested in the surgically altered chests and the unfeasibly large cocks. Well, not much anyway. I moved onto crossdressing, especially particularly feminine crossdressers. Sissies, I guess. Lately I've been looking for porn involving men who aren't remotely passable, but don wigs, makeup and woman's clothing and lingerie. I don't know why." "Because it's more real, that's why. You can more easily imagine yourself as one of them, can't you? All shaved and perfumed, a cheap wig and sloppy makeup, lying next to someone like yourself, rubbing your penis against his..." Cammi had to slow down her manipulations, sensing I was becoming too excited. "What about chastity? You interested in that?" "Honesty, no, at least not in a cage or whatever. Tease and denial, yes, humiliation, definitely. I have long edging sessions imagining a man teasing me, forcing to admit my desires before he'll, well..." "Before he'll let you suck his cock? Does he run his finger around the head of his cock, get it covered in his precum, then stick it in your mouth to suck?" Cammi did just that with mine, and I eagerly sucked her finger. "I'm so turned on again, Dee, I can't believe it. I remember my first year of college, I teased my roommate until she finally sucked me. I used to parade around the room in the sexiest outfits, asking her if she was sure she wouldn't like to touch my ass or my tits. Then one night it all came out, she was totally gay but never admitted it. What a year...I'm not gay but having a little lezzy sex slave was wonderful! Scissoring all night, oh those were great times. I can just picture you on your knees, a hard cock nearly touching your lips, and you begging for a taste..." "I'd love that. I guess what I really want is a sissy lover, someone to dress up with, tease each other, make fun of each other for being what we are..." I became all emotional for some reason and starting snuffling. I was so embarrassed, in the middle of having sex (sort of!) with my girlfriend, but I couldn't help it. Cammi stopped playing with my crotch and cuddled me. "There there, poor Dee. It's a huge emotional relief, unburdening all this to me, and I'm feeling very privileged that you feel safe enough with me to share it all. Suck on this, that's a good boy." Cammi stuck a breast in my face and I took advantage of it. She stroked my hair while telling me, "I know what you need. Meet Clarence, somewhere in public, and just chat with him, see what he's like. Ask him for a coffee or whatever. Couldn't hurt." Part 2 - Coffee with Clarence I'm Dee. Early 30s, normal guy, about 5-9, sort of short. Everyone says I have high cheekbones but otherwise I think I'd get lost in a crowd. Dirty blonde hair, kind of long, and keep fit with mainly cardio. I work in logistics, meaning I tell people where to go and what to take, basically. Cammi and I have been together for a few months. As you can tell, she's an enthusiastic lover with a great imagination and very kinky indeed. She still sees a couple of girlfriends, but it turns me on instead of making me jealous. And she tells me all about what she does with them, which really gets me going. She loves teasing me which sometimes pushes into humiliation. Being more or less a top herself, she understands this and uses it to spice up our relationship. Even shopping for food, she'll say, "Look at that guy, I'm getting wet just looking at his ass. I should invite him back to fuck me senseless. Oooh, I'm leaking now. Wonder how big he is? Maybe I should just ask him?" I've never been with a man but often fantasize about it. Never about, well, being with a guy as I am, in my imagination I'm always dressed as a woman, and mostly with the other man dressed similarly. Sometimes when I'm not with Cammi I'll spend a whole night edging myself, pretending I'm with another crossdresser, kissing and rubbing against him. "Let me take some photos and send them to your butch drivers where you work, I bet they'd line up to fuck your sweet ass," he'd whisper in my ear. Anyway, I'm daydreaming here in my little booth at this chain coffee shop. Clarence seemed eager for some reason when I asked him if he wanted to meet for coffee. I thought he'd ask me why or just say no, but when I called him yesterday, he said, "Sure! That'd be great." Clarence is a taller than me and beefier, looks like he works out a lot. Cammi and I know him from the gym and he's a friend of a friend so I've seen him at parties. I spent a long time figuring out a pretext for the invite. It was to get some tips on gym stuff - maybe if he could recommend a trainer or help me himself. Just a list of exercises and what weights to use would be a good start, I told him on the phone. He laughed and told me that I'm fine with what I'm doing, but was very happy to chat it through with me. I was early but Clarence came in exactly on time. He quickly saw me, smiled and sat down across from me. "Dee, this is great, I'm really glad you invited me. Let me get a coffee - you want another one? No? One sec." I was nervous but I tried to hide it. We chatted about the gym and catching up and what we were up to generally. Clarence lived alone in an apartment, was a freelance coder and generally worked at home. He knew about Cammi of course. Then out of the blue he said, "So Dee, I'm assuming that the real reason you invited me was to talk about crossdressing. Did you notice my woman's panties in the gym? Was that my giveaway?" "W-what? I, well, no! I didn't know, and, uh, well..." "No need to be embarrassed. I'm even thinking of going fulltime as a woman. I think it's the sexiest thing in the world, to dress up as a woman, to put on panties and hose, all the makeup, everything. I get so hard and drippy when I dress, I usually have to have a pad to catch it all. Some women love it when I dress, others, not so much. So, what about yourself?" "Look Clarence, I think...no, I know* there's been a huge misunderstanding here. I really just wanted to talk about gym stuff, this other thing, the crossdressing, well I had no idea, and, and..." I didn't know where to look, I was completely embarrassed. But of course I was rock hard. Wow! But I simply couldn't look Clarence in the eyes. I wanted to sink into the floor. "Dee. I'm looking for someone to share my hobby. A man. I've seen you watching me in the gym. Staring at me, at my ass, my, well, crotch. I'm always watching you as well, your strong legs on the bike and crosstrainer. If you're really embarrassed and don't want this to continue, fine, I'll walk away and we'll wave to each other at the gym and parties, no awkwardness and I apologize. But if you want me to show you how to dress as a woman, how to fix makeup and wigs, how to walk and...other things, then why not? Admit it, you're curious. I've never been with a man without being dressed as a woman, and it's not what I want, some hairy jock. Am I making sense? Again, if I'm smoking crack here, let me know and we'll shake hands and I'll disappear." I looked up into his gray eyes, his slight, kind smile, took a deep, tremulous breath and decided. "Clarence, I think you know me better than I know myself. If you have time, I'd love to go somewhere else to talk about your very exciting offer, but I don't think I can stand up without causing a commotion and complaints about a lack of decency." Clarence laughed, took my hand and said, "I knew it, Dee! It's best if you admit to yourself what you like, even what you are. I have, a long time ago, but it's very tricky to find someone with a shared interest that I can trust. Not some weird hookup from the internet, but a friend who can share a few laughs with me and maybe more... I thought I was going to come in my underwear. I gulped, my mouth suddenly dry, and put my other hand on our hands clasped together. "I'd love that, Clarence. Please teach me. Everything." We both leaned towards one another, gearing ourselves for a PDA in the coffee shop, when we saw a hand reach in to take our cups and saucers. "You two want a refill? Or maybe you want something to go instead?" A lovely redhead with twinkling eyes winked and smiled at us as she cleaned up. We both let out an embarrassed laugh, letting go of each other's hands, and told her thanks, we were fine. It broke the spell, my erection subsided and we gathered our things to leave. Part 3 - Teasing and Fulfillment "That was classic!" Clarence laughed as I followed him out of the shop. I couldn't help it of course, and was hypnotized by his ass. How did he get it looking like that? Did he use pads? "I know! Wow. So, what now?" I asked. "Given that it's Saturday, about 3:00, I'm free the rest of the day. You? What about Cammi?" What about Cammi, indeed? She's been texting me like mad, asking me how the meeting went. "She knows we're meeting, all good." I tried to remember to text her later. "OK, well I'm about 10 minutes' walk from here. That OK with you?" "Sure." I felt myself getting hard again and tried to think about sports. Anything. As it happens, we had a pleasant walk to Clarence's place, discussing the area and how it's changed over the last few years. I felt comfortable with Clarence, and that was saying a lot, as I was quite shy and not always very self-confident. Once reason I was with Cammi was that she understood me so well. Especially my own kinks and what strings to pull to get me going. We ended up at a high-end apartment building with a doorman. We went up to the seventh floor where Clarence showed me his large, modern place, two bedrooms, a living room and a walk-in kitchen/diner. I didn't know that coders made so much to afford this type of place. We ended up in the living room with a good bottle of Malbec and relaxed on the couch, sitting next to each other. "So Dee, you OK with a frank discussion? I don't want to surprise you again. Also, let me know if you're uncomfortable, and naturally if you want to leave at any time, I certainly won't keep you here against your will. OK?" "Sure, Clarence", I said, trying to be cool but already feeling that special tingle. Damn, I hope I could just be cool, calm and collected and not come across like some weird, repressed virgin. Which in his eyes, I might well be. "Great. Nice wine, right? Got it on a recent trip to Argentina, crazy client flew me over to sort out his IT system. Anyway, I can start. I'm not gay - at least now 100%, I get nothing from guys, I don't even look at them unless I'm dressed. Even then, I'm more interested in women and have had plenty of girlfriends. It's just that I'm constantly checking out what they're wearing. Unlike you checking me out, right?" Clarence laughed and sipped his wine. "Uh, no! Well, yeah, at the gym but just you. Seriously, Clarence, your backside is, well, somewhat out of proportion to the rest of you, at least for a guy. It's, well, amazing." "Ha! I've heard that before. But I've always been fascinated by women's clothes and started trying them on, borrowing a girlfriend's panties at first and moving on from there. I briefly dated a woman who said it turned her on and treated me as her doll, showing me how to do makeup and wigs and all that. She left me for some huge hunk, told me she wanted "a real man" which was a joke as she was the one who got me into dressing. I think it was only three weeks after that she tried to get back together but I'd moved on by then." "I'm afraid that I have almost zero experience with, well, dressing as a woman. I'm sure you can tell I'm a bit submissive; well, maybe more than a bit. Cammi takes advantage of that. In a good way, nothing bad, just...well, taking charge in bed. Anyway, I often fantasize about being dressed in women's clothes and being with another man who's also dressed. I'm not into being forced, I know a lot of people have rape fantasies or similar, but I imagine more of a loving relationship, kissing and cuddling and, well, more." Clarence was a great listener, nodding and making me understand that he was being very attentive without interrupting. He seemed to really get what I was talking about. "Dee, I totally get it. I started out differently, made dates with men who just used me and did nothing at all for me. Even going down on them, something I fantasized about, left me feeling cold and used. I was wrong, I had no feeling for them and it was a huge mistake. I only did it a few times then gave up, thinking that I'd just contend myself with edging to porn while dressed. I didn't trust the other men who I met on the Net, they all seemed so seedy and weird. But for the last six months or more I've been pretending that I'm with another man dressed up as a woman, very similar to how you described it. But you've never been with a man? Ever?" "No. I'd never do it. At least, well, you know...until I met you!" I blushed. "Uh, well, I mean, not as you are right now, you know, dressed, and..." I petered out, still blushing. "Ah, relax, Dee!" Clarence pulled me in for a hug. He was a lot bigger than me, and I felt safe in his muscled arms. "We can do some exploring together. What do you say?" I looked at him and he ran a finger around the outside of my lips. Then he slowly pushed his finger into my mouth. "Suck, Dee." I did, I licked it and sucked. God, he turned me on. "You like doing what you're told, don't you Dee?" "Yes Clarence." "Good. Before we start, I want you to lick my underarm. Kiss and lick." Clarence unbuttoned his shirt, displaying his large, muscled chest, flat stomach and tight abs. He had no hair anyway below his neck, and put his arm up, his hand on the back of his head. His underarm was also clean shaven. "You want to, don't you Dee? Your first taste of a man. Go ahead." I was rock hard again and squirming, and Clarence noticed and smiled. I leaned forward and Clarence put his hand on my chest, stopping me. "Tell me what you want, Dee." "I, I want to lick your underarm, Clarence." "Why?" "Because you asked me to." "Asked?" "Because you told me to." "But you want to do it anyway, don't you Dee? Tell me." "Yes, Clarence, I want to lick your underarm. I, I want to lick your bare skin, to taste you. To lick and kiss another man. To please you." With that, Clarence smiled and pulled my head into his underarm. I tentatively licked then kissed his skin, smooth and smelling clean, not like deodorant or anything like that. I gently bit his skin, kissing and licking, until he pulled my head back. "You're very eager, Dee. I thought about giving you a quick blowjob, relax you a little, but I changed my mind, I want to keep you on the edge. I love seeing you so desperate - desperate to please, and undoubtedly desperate for release. Do you and Cammi ever play games like this, tease and denial?" Clarence has a hand on my thigh and was gently squeezing it. "Not really. Sometimes she rolls over and tells me to finish myself then, then lick up my cum, but..." "Oh, that's delicious. She probably watches you stroking yourself...fun! Enough of this, let's get started!" With that Clarence stood up, showing an impressive bulge in his tight jeans. I followed him into a large bathroom with the latest gadgets, including a substantial walk-in shower with all sorts of knobs for jets and whatever. This guy seemed to be loaded. I was wondering what a 'coder' actually did, and if he wasn't telling me everything. "OK, first thing is hair. You want to look like a woman, Dee? Let's see what I'll be working with. Everything off." I blushed again and started to take off my shirt and pants. I was wearing skimpy underwear, men's but sexy. "No socks please Dee, this isn't some cheap porn movie you know. Good, now turn around. Bend over. Oh yes..." He started to fondle my ass, squeezing my cheeks and running his fingers into my crack. "I can't wait, Dee. Lovely. Now spin around and lose those sexy undies." I slowly peeled them off, my erection bouncing out and pointing straight ahead with a slight upwards tilt. Clarence ran his fingertips up and down it, making me whimper. "You are so perfect, Dee! Look at you, dripping onto the floor, naked in front of me, and I'm still dressed. This is so sexy! OK, let's not dawdle, into the shower. Quick soap and rinse, then use this smelly stuff to get rid of hair below your neck. Not on your crotch at all, unless you want to scream for an hour, we'll sort that out later. Let me know when you put it on and I'll tell you when to rinse it off. OK?" Clarence leaned in and fondled my ass, my hard cock pushing against him, but he was still in jeans and his unbuttoned shirt. "Yes Clarence. Whatever you say." "Mmm, that's good. In you go!" There was a little stool in the corner which was weird, but I figured out how to use the shower and got busy. The body gel was rose scented, and I used it and shampooed my hair, quickly rinsed off and started to put the pink gel all over but not on my crotch or ass. I told Clarence when it was on. After a few minutes Clarence said, "OK, long enough, rinse off Dee." I did and lost what little hair I had on my chest and legs. My underarms stung a little but not much. I turned off the shower and Clarence stepped in, this time in a pair of pale blue women's panties. "Time for the difficult part!" He has a can of shaving gel and a women's razor. He pulled the little metal stool out (so this is what it's for!) and had me sit on it. He lathered my crotch including my balls and started to shave me. "So this will itch like mad when it starts to grow out, but there's a very easy cure for this. Don't let it grow out! I'll show you this time, but you'll need to do it yourself from now on. Maybe every other day, it depends on how fast it grows. Mmm, looks like you enjoy this! Hold still, I wouldn't want to slip, as you're already circumcised!" Having Clarence even brush his hands by my aching erection was making me swoon. I moved to hold it out of his way. "No! Bad boy, don't touch. This is mine now, Dee. Hands to your sides." What with Clarence touching my private, sensitive parts and his monolog, I was getting seriously overheated but that appeared to be his intent. "Nearly done on the front. Yes, it makes it look bigger, but the real benefit is the sexy smoothness. Do you like it when I touch your smooth balls? With this gel, my fingers glide right over them. A little squeeze, like this? When we're dressed, you'll understand how we can take things very slowly and sensually. OK, this looks good! Now put your tummy on the stool and spread those legs." I turned around so Clarence could get to my ass and gave it a little wiggle. "Ha! So eager. Maybe it would be fun to go out hunting together, bring back a couple of men and give them our backsides while we kiss. I'd stroke your face and have you suck my tongue while your boyfriend was busy behind. You don't have much hair here really, and some of it is soft and blonde, but it's all got to go. Relax now..." Dee shaved the little hair there was on my cheeks then pulled them apart to get inside. When he put the gel on, I jumped a little. "So sensitive back here! We'll investigate that later. Hold still now!" And finally he was done. "Wow! I can't believe it, so soft and silky. It feels wonderful, thank you Clarence." "I hope you were taking notes, remember minimum every two days, maybe every day at first. Trust me, you might not notice but it's better than having it start to grow back, and you do want to be smooth for me, don't you Dee?" "Yes Clarence. I'll remember. What's that?" "Moisturizer. I'll do it the first time, just make sure you don't add your own cream to this! Smells nice, doesn't it?" Clarence put it all over me from the neck down and it left me smelling like a rose garden and glistening. "My turn for the moisturizer. Here, go ahead, and don't miss anywhere." Clarence quickly took his panties off and I got the full effect of the man. Wow...muscular but not overly so, great legs and of course his perfect ass. Shoulders, chest and arms nice as well. I started at the top and worked down, skipped the crotch and went down to his feet and worked up from there. Clarence moaned as I massaged the cream into his thighs. His cock was nice, not massive but well-shaped and thick, cut with large, hanging balls. And everywhere was smooth, like me. "Dee, I've never, uh, you know, never touched anyone else's, and, uh..." Blushing again. "Oh, I forgot! A big moment for you, Dee! Go ahead, it's only a little bit hard, reach out and touch it. Take it in your hand. Soft and warm, right? That's it, getting harder now. Slowly move your hand up and down." "It's, well, I can't believe it. I'm finally touching someone else's..." "Penis? Say it. You're touching my penis. Another man. Tell me, Dee." "Yes, I'm touching your, your penis, Clarence. Another man's penis. Your hard cock. It's, it's, well, beautiful." "Think about it, Dee. You're what, 35? All your life, fully straight, red-blooded man. Fuck women. Have a steady girlfriend. Isn't touching another man's penis, sort of..." Damn. Clarence knew me so well already. I dripped more precum onto the floor of his bathroom, holding his hard, wet cock in my hand. I thought, what *does* it mean? Anything? "It's, well, it's gay." I thought I'd come right then and there. "It certainly is, Dee. And it looks like it really turns you on saying it, doesn't it? It is gay, yes. And?" "And, and, oh God, I..." I let go of Dee's penis and held my hands over my face. Dee moved to me and wrapped his arms around me, pushing into me, our bodies touching. Our erections pushed together and his hands moved down to my ass, pulling me in harder against him. "Yes, Dee, say it. Tell me. You're all shaved and smooth, you let another man shave you all over. Fondle you. I bet you want more, a lot more, don't you Dee. I'm very comfortable with what I am, but I want to hear you say it. Tell me, Dee." "I...I'm a sissy. I'm a fag, I want to dress up as a woman and play with another man also dressed up. I want to do gay things with him. I'm a pansy, a sissy fag, Clarence." "Own it, Dee. It's no longer an insult, be proud! It's like how women have changed the perception of 'slut'. Fag, pansy, sissy, all glorious things to be. Now kiss me, you fucking fag!" It was stupendous, a long, searching yet gentle soul kiss. We sucked on each other's tongues, we whimpered and cooed, all the time our hard cocks slithered against each other. Finally we broke for breath. Clarence said it first - "That was the best kiss ever, Dee. I knew it would be you, I was so sure, but I couldn't approach you, it had to be the other way around. And I'm so glad you did..." We kissed again but I broke it, gently pushing him away. "Let's, well, get dressed! Then we can really explore how we feel. I want to kiss your ass all wrapped up in panties." I knew I'd come from kissing him and I wanted to get all girly first. If I was an expert at anything, it was edging myself and knowing when to back off. Clarence smiled. "Definitely! My stuff might not be a perfect fit but it'll all work for now. There's a lot of shopping to come! I know great places where they love outfitting men. Even though I always get molested. I should start wearing pinch-proof pants!" We moved to Clarence's massive bedroom with a walk-in closet. "Clarence ...no one has walk-in closets in an apartment. What exactly do you do? This place is amazing!" "It's nice, I admit it. I'm a coder as I said, but I'm able to get a percent or so of sales for really difficult jobs, almost always rescues. I'm the best at this niche area so the industry knows that if they can't fix it and their usual go-to coders can't, they can always come to me but the price can be high. They see it as they won't have a product at all or will have to start from scratch, so it works out. Anyway, let's get started!" Clarence and I went into the closet together. I couldn't resist it - "I thought I was coming out of here, not back in!" After a theatrical eyeroll, Clarence quickly picked out two pairs of pink panties. "We should both be in pink. It's only fitting, two sissy girls together for the first time." He carefully pulled his up, gently fitting his considerable package inside, and I copied him. They felt so light and smooth against my shaven skin. No lace, just a thin band with little hearts and satin everywhere else, hot pink, semi-transparent. As I was hard again, I had to adjust to get my erection inside, but sideways wasn't working for me so I went with putting it sticking up towards my belly button, with the head sticking out. Clarence just laughed. "Close enough!" We both picked up light summer dresses, just above the knee, Clarence's white with flowers and mine, royal blue. We left them there and went back to the bathroom for the makeup. Clarence carried a couple of wigs but wouldn't show them to me, saying it would ruin the surprise. He did himself first with me watching closely, explaining each step. Although it looked like a lot went on (foundation and other layers), it looked great in the end. Then the eyes - no false lashes but mascara and then the colors. Dramatic but not clownish. He said that's where us 'gurls' often got it wrong, that less was better, but it still looked like magic to get it just right. Then what I liked best, lipstick, liner and gloss. Fire-engine red, just wow. The pi?ce de resistance was a lovely wig, blonde with little curls around the face. 'Transformative' was the word, as soon as it went on, Clarence was no longer a Clarence at all. "So, what do I call you now? You can't stay with Clarence." "Clair. Pleased to meet you, uh...I'm guessing you're good with Dee?" "Sure that works!" My turn next - I did my best with the patient and gentle assistance of Clarence (now Clair). It looked OK, not as good as Clair's of course, but a thousand times better than I could have done by myself. At last, the wig - a great light red/strawberry blonde number, about shoulder- length. As with Clair, it immediately helped me transform to a woman. A woman with a big Adam's apple, but the makeup covered any stubble and other skin issues. I couldn't stop pouting in the mirror but Clair dragged me away. We went to try on the dresses. Mine was a little bit big but it was OK. No bra, but Clair had a matching pink one with inserts. I was jealous, but he explained that we'd get some for me. They were so realistic and filled out the bust well. Shoes were last. Mine were a little too big but shiny, black pumps were fun. Clair had white strappy heels which went better with his dress. I would have preferred matching blue shoes but you can't have everything. At least not in terms of outfits. At last, I thought, we were all dressed up for the big event - each other! Clair and I walked to the foot of the bed and stood a few feet apart, staring at each other, admiring our handiwork. "Dee, well, wow! You're lovely. I knew you would be but seeing it like this, seriously, incredible." He (I just couldn't call Clair 'she', and it sort of turned me on to continue to refer to Clair as 'he') reached out and we held hands, looking into each other's eyes. "May I have this dance, you beautiful woman?" "Yes please, my darling. Music?" "Alexa - play "We've Only Just Begun" by The Carpenters." My turn for an eyeroll. "So cheesy! Really?" "I spent ages deciding on that, so that's what we'll dance to!" "Yes Ma'am." With that, Clair held me around the waist and we spun around the room. Lots of ass-grabbing and rubbing against each other but no kissing, both of us not wanting to ruin our makeup just yet. The music finished and Clair actually picked me up and carried me to his bed, putting me down and then laying next to me. We both lay on our sides facing each other. "So, Dee, here we are! But I don't want you to forget the power dynamic here. It makes it a bit more exciting for the both of us. That's why I carried you to the bed. Right now, right here, you are mine. All mine. My little sissy playmate. Does that turn you on?" Clair was right to point this out, this was what I wanted. I had to tell him. "Clair, yes and yes! This is what I want, to be yours. I trust you, I want to please you. Use me." "Dee, you're lying on a bed in a man's home, dressed as a woman, wearing pink panties, makeup and a wig. I know you're hard but let me check - oh yes, I'm glad you didn't release your sissy cream into your panties. You'd be punished for that. So hard and wet. You want me to touch you, don't you? Tell me that you want a man to touch you." "Please Clair, touch me, use me. I'm yours to serve." "Good boy. Take off my dress, then yours." Clair sat up and I carefully pulled his dress off, leaving his bra and panties and shoes. I quickly peeled off my dress leaving me in panties. "Now take off my shoes, then yours." I took off his white heels and kissed his toes, then took off my shoes. "Lay on your back, arms over your head." God this was good, dressed as a woman, in a bed with another man dressed the same, wigs and makeup, and best of all he was telling me what to do. Does life get any better? "Good boy. I'm going to climb on top of you. Wrap your legs around mine, spread them wide. Feel my weight on top of you. Crushing you. Dominating you. Do you like this, Dee? A man dominating you, pushing you down into the bed? My hard cock rubbing against yours?" Clair very slowly moved his hips in a small circle, grinding into me. I couldn't help it, I whimpered a little bit and made soft, high-pitched 'ahhh' noises. I would have squeezed his ass but he had my wrists together in one hand over my head. I felt equally dominated/subdued by this heavy, huge, sexy man, and thrilled and exhilarated by feeling him against me. His smooth, silky legs on mine, both of us shaved and moist. His hips pressing hard into mine, our penises separated by two very thing satin layers. His large, muscled chest complete with bra and breasts pressing into me. His large hand holding my wrists together over my head. I was his prisoner, captured and being taken. It was all I could do to stop myself squealing and filling my pink panties with my semen. "Oh yes very much, Clair. Crush me, push me down, make me your little slut slave." "Open those cock-sucking lips, Dee. Let me see inside." I thought Clair was going to kiss me, but instead he used his free hand to pinch my nipples, hard. I cried out as he pinched one then the other. Then he slowly pushed up off me and laid down on his back next to me again. His hand slowly moved over until it lay on my stomach. "Poor sissy Dee, what to do with you. Bend your knees and spread your legs. Not so much, yes that's better. You want a man to dress you as woman, dress himself that way, and kiss and fondle together? Is that right?" He was moving his fingers over my stomach, up to my nipples, then back down again. "Yes, Clair, please..." I reached to touch his hand but he slapped it away. "First tell me everything. Does Cammi touch you here?" Clair moved his hand down, over my hard cock, down to my balls then onto my ass. "Oooh, Clair, ahhh...uh, yes, not so much touching but she's fucked my ass with her dildo." "Kinky! Did you come that way?" "No, but it turned me on. Just one time. I love licking and tonguing her ass. Recently we fucked, then she pretended that she'd just been fucked by a couple of studs, then made me go down on her and eat all my cum out of her." "Wow! I'm impressed. Guess she doesn't reciprocate your love of kissing her ass? She has no interest in running her tongue around and into your little hole in back? Why's that?" I'd never thought about it. "I, I don't know. I've never asked her..." "You love it because it's degrading. It's like edging yourself, but so much better, your tongue in her hole. It would be even better if there was a dripping, hard, hot cock nearby, right?" Clair pulled the crotch to one side and circled his finger around my hole, running his fingertip right over it. "Ooooh, yes, that's so nice. I, I, yes, a cock, and, and..." I was incoherent, the sensory stimulation was overwhelming. Clair pushed his finger inside, not very deep, took it out and pushed it into my mouth. "So dirty, Dee, you're such a dirty boy, sucking my finger which was just up your ass. Who does that? A wicked, dirty pervert. A sissy gay boy begging for cock. One who pretends to be a woman. Who loves tongue- fucking his girlfriend and eating his own cum from her wet, messy pussy. What are you?" I was really close to losing it. "I'm a sissy fag! A pervert! An ass- licking dirtbag who wants to get fucked by another man!" Clair smiled, quickly peeled off my panties, got between my legs and swallowed my cock. I'm not huge but not small either, yet his ruby red lips were nearly on my balls as he took me in one quick movement, all the way down his throat. Then he backed off, put his hand on the base and started to stroke me, and his other hand played with my ass. I lasted maybe a minute, probably less, and I screamed, my hips moving up and down, and let go with a massive, thunderous orgasm down his throat and mouth. It seemed to go on forever and it felt like I passed out, but quickly came back as Clair pulled off and licked the head, stroking out of me whatever I had left. Clair moved up and we finally kissed, our lipsticked mouths pressing together as he moved my cum into my mouth, his tongue carrying it over. I couldn't believe it but I was already starting to get that tingling down below even though I had just cum like never before. He pulled back, stuck his tongue in my ear and breathed, "See, little Dee? I like giving you rewards. I can always tell when people are sincere and you certainly were! We're not teenagers but I'll gladly admit to being a dirtbag, at least when it comes to messy, smelly, wet, loud sex. You tell me that you like my ass, why don't you show me?" Clair pulled away, lay on her front and moved her knees in so her beautiful rear stuck up. I looked on in awe for a moment, then said, "Yes, Clair, whatever you want", and started at her feet. First I ran my fingertips up from her muscled, smooth calves, up her knees, then onto those large thighs. I ran both hands up his inner thighs, stopping at the beginning of his ass, then back down the other leg. Then both hands, one on each leg, up the inside until I reached his large balls. I weighed them in my palm, gave them a gentle squeeze then trailed my fingers up the crack of his ass to his lower back then back down. "You are such a tease, Dee! I'll remember this..." I leaned in. Another first for me. I licked his ball sack. It smelled and tasted musky, masculine and, frankly, delicious. I moaned as I carefully sucked one of Clair's big balls into my mouth, then the other. I was hard again, loving sucking on a man's testicles. "Oh, that's so nice, Dee. I'm just thinking how sexy it is to have another man suck on my balls. As a matter of fact, no one has even done this. For you especially, it must be so degrading, sucking another's man's ball sack. Leave my cock for now, move down to your target!" I slowly licked downwards, tonguing Clair's perineum, and circling his rosebud. I licked up his crack, squeezing his firm globes, then back again, spreading his cheeks and starting to tongue his hole. I had done this many times to Cammi but on Clair it was even more of a thrill, humiliating and exciting, dirty and...bliss. "I want Cammi to watch you do this to me, Dee. For her to watch her boyfriend lick and suck another man's ass. To put your tongue inside my ass while she rubs her pussy. It feels sooo good, I can't believe it. I get off on imagining her telling you, 'Dee, how could you do that? It's another man and you're tonguing his asshole! What sort of man does that?' I have an idea, have you fuck your ass on a dildo while you watch Cammi ride my cock. Yes, she'll lower his ass on my hard cock and ride me while you fuck yourself, then when I come inside her, she'll lay back, pull her knees up and have you suck it out of her ass, all my cum, wet and slimy. Oh God you're so good at that, keep going just like that Dee, ahhh...." Licking Clair's ass, fucking him with my tongue, was exciting enough but having him degrade me while doing it was pushing all my buttons. My wig was sort of in the way but it turned me on too much to get rid of it, so I pushed the hair out of my way and kept licking. All Clair's talk about Cammi was getting to me. I fondled Clair's balls as I licked. Everywhere was wet and warm and smooth, the bed and room stank of sweat and cum and ass along with our rose lotion, and my cock was painfully erect and dripping. "I want your girlfriend on her side, leg over mine, as I slowly fuck her wet, tight pussy. Your head will be pushing inside her crack, licking her ass as I'm inside her. Then you can switch and lick me while I'm inside Cammi, I'll go slow and deep so you can really rim me. You'd love that..." With that, Clair pushed my head away. I looked up and he laughed. "You should see yourself, Dee! All that work, well, I think you'll need to start again on the makeup. But for now, let's see if I can make it even worse. Let me move up to the headboard, here, and push my legs out. Come and say hello to my cock. It's been waiting to make your acquaintance." "Yes Clair. Hello, penis. Glad to meet you." I stroked it briefly like I was shaking hands. Cue eyeroll and laugh from Clair. "Have some respect, sissy! "Yes Clair." I took hold of it. Long, thick with a big mushroom head. Hard but soft. I put my face near and inhaled - musky, masculine, smelled of sex and cum. I licked my lips and ran my tongue over the spongy head. I've wanted to do this for years, all those fantasies, edging, just for this. "It's beautiful, Clair. So long and hard and ... intimidating." "Put the head in your mouth, Dee. Run your tongue all around it, into the hole, around the edges. God you look good with my cock in your mouth. A first for both of us, Dee. The bastards I was with never touched my cock. First time a man has had it in his mouth. Oooh, that's nice. Look up, Dee. Oh, that mascara is tragic! Next time we're definitely filming us together. Look up at me, think about what you're doing. A man's hard penis in your mouth. You've already licked my ass. Another step for you. For us, together. What does this make you?" I didn't want to stop but as I was learning, Clair had a way of enforcing obedience without physical methods or shouting. Force of will. "It means, it's, uh, I'm a cocksucker. A sissy fag cocksucker who likes sucking men." I looked Clair in his gray eyes and licked his cock from the base to the tip, then sucked the head inside again. I was surprised that in addition to feeling subseviant to the large, muscular Clair, I also felt powerful. He was hard because of me, he wants me, I turn him on, and right now I control his great big penis, I can tease and edge him or make him ejaculate. It was a weird feeling, very different from going down on Cammi. I kept sucking the head and stroking the shaft, looking into his eyes, when it struck me - yes, I was now a cocksucker. This day and age, so what? But on a personal level, it was shocking. Dressed up with a wig and makeup, sucking another man's hard cock, tasting his precum, slurping all over it like a cheap whore...or like a sissy fag, a cock- loving homo. If this is what it meant, then give me more! I slowly went down further on his cock, breathing through my nose (all those edging sessions helped me get the details right), accepting but trying to push through the gag reflex. Which I failed to do and moved up, sputtering and coughing. "Ha! Don't worry Dee, practice makes perfect! Here, lay on your back." I did as I was told, and Clair kneeled over my head, feeding me his cock from above. He soon started moving his hips back and forth, not exactly fucking my mouth, but pushing in and out. "Oh yeah, that's it Dee, suck my cock. You're so good at it for a beginner. Suck it down, that's it. Yes..." Soon his hand moved over mine and controlled the stroking. I reached up and fondled his balls then his ass, teasing his hole with my fingertips. "Oh shit, that's it you fag, play with my ass...ahhh!" He pulled out of my mouth, stroked furiously and dumped a massive load all over my face - a lot got into my mouth but even more went on my cheeks, nose, forehead, all over. He kept swearing and grunting as he stroked, on and on, until he finally stopped and wiped the head of cock over my chin and mouth. "Clean it off, Dee. Suck the rest out." Which I did. Wow! A big fantasy comes true. He scooped up what didn't go in my mouth and fed me the rest, which I licked up and swallowed. I was sort of used to It by now after the session with Cammi, but Clair's tasted maybe a bit sweeter. Still, I didn't gag on it like I've seen on some videos, and what counted was watching Clair come all over my face. What a thrill! I was tingling all over. "I...I feel like such a fag, Clair. You came all over my face...and I liked it. I loved it. I need it..." "It's great when you give in, Dee. Give in to what you're feeling. It's wrong, dirty, perverted, unmanly, unnatural...kiss me, you fag, I want to taste my own cum in your mouth, I want you to share it with me..." Clair kissed me, a long, sexy kiss, sharing his cum back and forth. Wet and messy and...wonderful. I was so hard, leaking again, molding myself into his strong, massive arms and body. He finally pulled away and whispered in my ear, "Even hearing me say the word 'penis' turns you on, doesn't it? After all those hours or even days edging yourself to all that sissy porn, hypno stuff and everything online...admit it." "Yes Clair, I admit it. Oh God, I'm so horny all the time. Fuck me, fuck my sissy ass, take me..." Clair laughed. "Not yet, my little Dee. Lots of practicing first to open you up. Something for you to look forward to! Here, suck my finger. Get it wet. Now, spread those gorgeous legs. Oooh, you are just so sensitive there! Deep breaths, no panting. Better. Now, if I push in...see? So tight, my cock wouldn't go in very easily. It would take a long time, loads of lube and you'd still probably just be in pain. Get a series of different sized dildoes, work your way up, and we'll get there. Might be fun to get ready for me...I'm sure Cammi will help." "Oh God, that feels so good. Your finger up my ass. Ahh..." "Hump my hand. You are so desperate. Let's just cuddle like you wanted originally, remember?" Clair pulled his finger out of my ass and stuck it in my mouth. "So dirty! Now kiss again..." We kissed and cuddled for nearly an hour. I was desperate to come but it was like a super intense edging session, but a thousand times better. Clair knows my secret urges and how to exploit them all - which sounds unlikely but in reality he was just giving voice to his own. It was sensual and erotic, no filter as I pushed my cock into his lubed crack and moved up and down, my penis surrounded by his ass cheeks. Not allowed to finish, I had to go slowly. I honestly think it was even better when he did the same thing to me, pulling me tight against him, biting my neck, pinching my nipples and moving his cock up and down my wet crack. Licking my ear and whispering... "We need to bring Cammi in soon. I want her to watch your face as I fuck your ass, watch her masturbate with a dildo a few inches from your face as you pant and whimper as I slap your ass and push into your special spot with my big cock. I want her to hear you beg to suck my cock. I'm so hard and dripping now, here taste..." We were two slippery, wet, smooth girly boys, shaved and perfumed, molesting each other and teasing, our cocks hard and unfulfilled. It was heaven. Clair decided to get acrobatic, and put my head near the headboard, helping me get my back up against the board, my legs balanced over my head, my penis pointing towards my head. Sounds complicated but only because I'm describing it, basically I was on my shoulders with my own legs over me. "That's it, Dee, you look so sexy with your makeup ruined and your slutty mouth open to your own cum as it drips down. Now I'm going to reach up and fuck your ass with my fingers, one to start. If I can balance, yes...now if I point your cock right, ah, yes, you're dripping into your own face. Such a gay thing to do, don't you think? Let's see if I can hit that special spot..." I was happy I was supple as it was an awkward position, but his magic fingers pushed hard into my upturned ass. Clair was soon pushing against my prostate, banging it on each shove of what must have been at least two fingers, and I could feel what seemed like a slow wave pulling me over. My cock was dripping onto my face and mouth, and instead of the usual orgasm, I felt a slow, powerful wave after wave, a constant steam of cum falling into my face. It lasted a few minutes until I was trembling with both exhaustion and, I don't know, weird, complicated emotions. My first orgasm from being fucked, even if it was Clair's fingers and not his cock. All the dressing up, the teasing and humiliation, my admitting it all to Clair, it got a bit too much and I had a 'moment'. Clair gently got me lying flat on my back and hugged me. "All good, Dee. Let it out. It's OK, I'm here for you, it's just you and me. For now..." *** Phew! That was longer than my usual. To be continued, potentially with Cammi? Do let me know! And for those complaining about my use of 'abusive' terms, it's all part of the teasing and humiliation. I thought it was fairly obvious, but I do get complaints in the Comments! Please feel free to leave Comments, I read them all. Love, Lyon xxx